# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full 'Dalton Trans.'
_journal_coden_Cambridge 0222
_publ_contact_author_name 'Barron, Andrew'
_publ_contact_author_email arb@rice.edu
_publ_section_title
;
Synthesis and Characterization of Aryl Substituted Bis(2-pyridyl)amines
and their Copper Olefin Complexes: Investigation of Remote Steric Control
over Olefin Binding
;
loop_
_publ_author_name
J.Allen
C.Hamilton
A.Barron
data_mstdpa
_database_code_depnum_ccdc_archive 'CCDC 720335'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
Flack, H.D. & Bernardinelli, G. Acta Cryst., 1999, A55,
908-915.
Flack, H.D. & Bernardinelli, G.J. Appl. Cryst., 2000, 33,
1143-1148.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
N-(2,4,6-trimethylphenyl)-N,N-(2,2'-dipyridyl)amine
_chemical_name_common
N-(2,4,6-trimethylphenyl)-N,N-(2,2'-dipyridyl)amine
_chemical_melting_point 416
_chemical_formula_moiety 'C19 H19 N3'
_chemical_formula_sum 'C19 H19 N3'
_chemical_formula_weight 289.37
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_int_tables_number 19
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 7.2638(15)
_cell_length_b 13.053(3)
_cell_length_c 17.072(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1618.7(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 2866
_cell_measurement_theta_min 2.38
_cell_measurement_theta_max 20.18
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 1.61
_exptl_crystal_size_mid 0.85
_exptl_crystal_size_min 0.31
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.187
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 616
_exptl_absorpt_coefficient_mu 0.071
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6184
_exptl_absorpt_correction_T_max 0.7457
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 19614
_diffrn_reflns_av_R_equivalents 0.0684
_diffrn_reflns_av_sigmaI/netI 0.0599
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_theta_min 1.96
_diffrn_reflns_theta_max 28.41
_reflns_number_total 2274
_reflns_number_gt 1323
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.0731P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.064(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 2274
_refine_ls_number_parameters 204
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1016
_refine_ls_R_factor_gt 0.0444
_refine_ls_wR_factor_ref 0.1418
_refine_ls_wR_factor_gt 0.1112
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_restrained_S_all 1.036
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8484(3) 0.91042(16) 0.21410(12) 0.0574(6) Uani 1 1 d . . .
N2 N 0.6521(4) 0.90387(18) 0.32229(13) 0.0723(7) Uani 1 1 d . . .
N3 N 0.7508(4) 0.84314(19) 0.09636(12) 0.0706(7) Uani 1 1 d . . .
C1 C 0.8138(4) 0.9334(2) 0.29270(14) 0.0591(7) Uani 1 1 d . . .
C2 C 0.9416(5) 0.9880(3) 0.33548(17) 0.0770(9) Uani 1 1 d . . .
H2B H 1.0538 1.0065 0.3134 0.092 Uiso 1 1 calc R . .
C3 C 0.8999(7) 1.0148(3) 0.41146(19) 0.0921(12) Uani 1 1 d . . .
H3B H 0.9826 1.0534 0.4407 0.111 Uiso 1 1 calc R . .
C4 C 0.7378(7) 0.9845(3) 0.44349(18) 0.0912(12) Uani 1 1 d . . .
H4A H 0.7081 1.0004 0.4951 0.109 Uiso 1 1 calc R . .
C5 C 0.6207(6) 0.9303(3) 0.3977(2) 0.0836(10) Uani 1 1 d . . .
H5A H 0.5100 0.9096 0.4200 0.100 Uiso 1 1 calc R . .
C6 C 0.7653(4) 0.8285(2) 0.17336(15) 0.0536(6) Uani 1 1 d . . .
C7 C 0.7120(4) 0.7383(2) 0.20927(17) 0.0634(8) Uani 1 1 d . . .
H7A H 0.7225 0.7304 0.2632 0.076 Uiso 1 1 calc R . .
C8 C 0.6432(5) 0.6607(2) 0.1636(2) 0.0734(8) Uani 1 1 d . . .
H8A H 0.6064 0.5993 0.1863 0.088 Uiso 1 1 calc R . .
C9 C 0.6294(5) 0.6745(3) 0.0847(2) 0.0838(10) Uani 1 1 d . . .
H9A H 0.5827 0.6230 0.0527 0.101 Uiso 1 1 calc R . .
C10 C 0.6854(5) 0.7653(3) 0.05387(19) 0.0837(10) Uani 1 1 d . . .
H10A H 0.6778 0.7737 -0.0001 0.100 Uiso 1 1 calc R . .
C11 C 0.9690(4) 0.97696(19) 0.17075(13) 0.0512(6) Uani 1 1 d . . .
C12 C 1.1422(4) 0.9410(2) 0.14836(15) 0.0590(7) Uani 1 1 d . . .
C13 C 1.2537(4) 1.0045(2) 0.10399(16) 0.0647(7) Uani 1 1 d . . .
H13A H 1.3683 0.9808 0.0878 0.078 Uiso 1 1 calc R . .
C14 C 1.1992(4) 1.1026(2) 0.08301(15) 0.0626(7) Uani 1 1 d . . .
C15 C 1.0317(4) 1.1373(2) 0.10917(15) 0.0618(8) Uani 1 1 d . . .
H15A H 0.9965 1.2041 0.0977 0.074 Uiso 1 1 calc R . .
C16 C 0.9133(4) 1.0759(2) 0.15210(14) 0.0565(7) Uani 1 1 d . . .
C17 C 1.2079(5) 0.8356(3) 0.1722(2) 0.0875(10) Uani 1 1 d . . .
H17A H 1.3330 0.8264 0.1555 0.131 Uiso 1 1 calc R . .
H17B H 1.1314 0.7846 0.1481 0.131 Uiso 1 1 calc R . .
H17C H 1.2011 0.8290 0.2281 0.131 Uiso 1 1 calc R . .
C18 C 1.3202(5) 1.1700(3) 0.0340(2) 0.0924(11) Uani 1 1 d . . .
H18A H 1.2456 1.2186 0.0062 0.139 Uiso 1 1 calc R . .
H18B H 1.3873 1.1288 -0.0027 0.139 Uiso 1 1 calc R . .
H18C H 1.4051 1.2059 0.0673 0.139 Uiso 1 1 calc R . .
C19 C 0.7271(4) 1.1153(3) 0.1766(2) 0.0801(9) Uani 1 1 d . . .
H19B H 0.7034 1.1795 0.1510 0.120 Uiso 1 1 calc R . .
H19A H 0.7250 1.1249 0.2323 0.120 Uiso 1 1 calc R . .
H19C H 0.6342 1.0666 0.1619 0.120 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0719(14) 0.0594(13) 0.0409(10) -0.0022(9) 0.0036(10) -0.0098(12)
N2 0.0943(18) 0.0635(14) 0.0592(14) 0.0015(11) 0.0210(14) 0.0008(14)
N3 0.0953(18) 0.0713(15) 0.0451(12) -0.0026(10) -0.0017(12) -0.0198(15)
C1 0.0789(19) 0.0557(15) 0.0427(13) 0.0035(12) 0.0036(14) 0.0041(15)
C2 0.096(2) 0.089(2) 0.0464(14) -0.0026(15) -0.0069(16) -0.004(2)
C3 0.138(3) 0.090(2) 0.0478(17) -0.0039(17) -0.009(2) 0.001(3)
C4 0.152(4) 0.075(2) 0.0459(16) 0.0019(15) 0.010(2) 0.026(2)
C5 0.116(3) 0.0691(19) 0.0656(19) 0.0072(17) 0.0334(19) 0.018(2)
C6 0.0553(15) 0.0547(15) 0.0508(14) 0.0003(12) 0.0033(13) -0.0040(12)
C7 0.0730(19) 0.0558(16) 0.0615(15) 0.0073(13) 0.0020(14) 0.0000(15)
C8 0.079(2) 0.0550(16) 0.086(2) -0.0046(15) 0.0178(18) -0.0089(16)
C9 0.091(2) 0.075(2) 0.086(2) -0.0224(18) 0.0088(19) -0.023(2)
C10 0.104(3) 0.084(2) 0.0630(17) -0.0114(17) -0.0033(18) -0.021(2)
C11 0.0642(16) 0.0518(14) 0.0375(12) -0.0027(11) -0.0003(12) -0.0074(13)
C12 0.0681(17) 0.0553(15) 0.0535(14) -0.0002(12) 0.0021(14) -0.0029(15)
C13 0.0639(16) 0.0704(18) 0.0597(15) -0.0028(14) 0.0073(14) -0.0063(15)
C14 0.0744(19) 0.0640(17) 0.0493(14) 0.0018(13) -0.0009(13) -0.0167(16)
C15 0.079(2) 0.0560(15) 0.0502(14) 0.0062(12) -0.0131(15) -0.0065(15)
C16 0.0635(16) 0.0573(16) 0.0487(14) -0.0043(12) -0.0075(13) -0.0021(14)
C17 0.090(2) 0.068(2) 0.104(2) 0.0090(19) 0.009(2) 0.0121(19)
C18 0.100(3) 0.089(2) 0.088(2) 0.0178(19) 0.011(2) -0.028(2)
C19 0.080(2) 0.073(2) 0.087(2) 0.0021(17) -0.0014(18) 0.0118(17)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.398(3) . ?
N1 C6 1.411(3) . ?
N1 C11 1.439(3) . ?
N2 C1 1.335(4) . ?
N2 C5 1.353(4) . ?
N3 C6 1.333(3) . ?
N3 C10 1.336(4) . ?
C1 C2 1.380(4) . ?
C2 C3 1.377(5) . ?
C2 H2B 0.9300 . ?
C3 C4 1.357(6) . ?
C3 H3B 0.9300 . ?
C4 C5 1.354(5) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.383(4) . ?
C7 C8 1.373(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.363(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.359(4) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C16 1.391(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.385(4) . ?
C12 C17 1.512(4) . ?
C13 C14 1.387(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.373(4) . ?
C14 C18 1.499(4) . ?
C15 C16 1.385(4) . ?
C15 H15A 0.9300 . ?
C16 C19 1.506(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 124.0(2) . . ?
C1 N1 C11 118.3(2) . . ?
C6 N1 C11 117.65(19) . . ?
C1 N2 C5 115.8(3) . . ?
C6 N3 C10 117.1(3) . . ?
N2 C1 C2 122.7(3) . . ?
N2 C1 N1 117.3(3) . . ?
C2 C1 N1 119.9(3) . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2B 120.6 . . ?
C1 C2 H2B 120.6 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3B 120.1 . . ?
C2 C3 H3B 120.1 . . ?
C5 C4 C3 117.7(3) . . ?
C5 C4 H4A 121.2 . . ?
C3 C4 H4A 121.2 . . ?
N2 C5 C4 125.2(4) . . ?
N2 C5 H5A 117.4 . . ?
C4 C5 H5A 117.4 . . ?
N3 C6 C7 122.5(2) . . ?
N3 C6 N1 114.3(2) . . ?
C7 C6 N1 123.1(2) . . ?
C8 C7 C6 118.6(3) . . ?
C8 C7 H7A 120.7 . . ?
C6 C7 H7A 120.7 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9A 120.8 . . ?
C8 C9 H9A 120.8 . . ?
N3 C10 C9 124.0(3) . . ?
N3 C10 H10A 118.0 . . ?
C9 C10 H10A 118.0 . . ?
C16 C11 C12 120.8(2) . . ?
C16 C11 N1 120.1(2) . . ?
C12 C11 N1 119.1(2) . . ?
C13 C12 C11 118.4(3) . . ?
C13 C12 C17 120.5(3) . . ?
C11 C12 C17 121.1(3) . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 H13A 119.1 . . ?
C14 C13 H13A 119.1 . . ?
C15 C14 C13 118.2(3) . . ?
C15 C14 C18 120.5(3) . . ?
C13 C14 C18 121.2(3) . . ?
C14 C15 C16 122.1(3) . . ?
C14 C15 H15A 118.9 . . ?
C16 C15 H15A 118.9 . . ?
C15 C16 C11 118.6(3) . . ?
C15 C16 C19 120.5(3) . . ?
C11 C16 C19 121.0(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C1 C2 -0.5(4) . . . . ?
C5 N2 C1 N1 -177.9(3) . . . . ?
C6 N1 C1 N2 -25.5(4) . . . . ?
C11 N1 C1 N2 151.4(2) . . . . ?
C6 N1 C1 C2 157.0(3) . . . . ?
C11 N1 C1 C2 -26.1(4) . . . . ?
N2 C1 C2 C3 -1.0(5) . . . . ?
N1 C1 C2 C3 176.3(3) . . . . ?
C1 C2 C3 C4 2.0(5) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C1 N2 C5 C4 1.1(5) . . . . ?
C3 C4 C5 N2 -0.2(5) . . . . ?
C10 N3 C6 C7 -1.5(4) . . . . ?
C10 N3 C6 N1 175.3(3) . . . . ?
C1 N1 C6 N3 152.8(3) . . . . ?
C11 N1 C6 N3 -24.1(4) . . . . ?
C1 N1 C6 C7 -30.4(4) . . . . ?
C11 N1 C6 C7 152.7(3) . . . . ?
N3 C6 C7 C8 0.7(5) . . . . ?
N1 C6 C7 C8 -175.9(3) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C6 N3 C10 C9 1.8(5) . . . . ?
C8 C9 C10 N3 -1.2(6) . . . . ?
C1 N1 C11 C16 -69.3(3) . . . . ?
C6 N1 C11 C16 107.8(3) . . . . ?
C1 N1 C11 C12 110.2(3) . . . . ?
C6 N1 C11 C12 -72.7(3) . . . . ?
C16 C11 C12 C13 -3.0(4) . . . . ?
N1 C11 C12 C13 177.5(2) . . . . ?
C16 C11 C12 C17 176.6(3) . . . . ?
N1 C11 C12 C17 -2.9(4) . . . . ?
C11 C12 C13 C14 1.4(4) . . . . ?
C17 C12 C13 C14 -178.3(3) . . . . ?
C12 C13 C14 C15 1.7(4) . . . . ?
C12 C13 C14 C18 -179.1(3) . . . . ?
C13 C14 C15 C16 -3.2(4) . . . . ?
C18 C14 C15 C16 177.6(3) . . . . ?
C14 C15 C16 C11 1.6(4) . . . . ?
C14 C15 C16 C19 -177.2(3) . . . . ?
C12 C11 C16 C15 1.6(3) . . . . ?
N1 C11 C16 C15 -178.9(2) . . . . ?
C12 C11 C16 C19 -179.6(2) . . . . ?
N1 C11 C16 C19 -0.1(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full 28.41
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max 0.136
_refine_diff_density_min -0.141
_refine_diff_density_rms 0.032
_diffrn_ambient_pressure 101.33
_exptl_crystal_recrystallization_method
'cooled sat. solution of hexanes to -12 deg. C for several days'
# Attachment 'NapDPA.CIF'
data_napdpa
_database_code_depnum_ccdc_archive 'CCDC 720337'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic N-(napthyl)-N,N-(2,2'-dipyridyl)amine
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H15 N3'
_chemical_formula_sum 'C20 H15 N3'
_chemical_formula_weight 297.35
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 7.8253(16)
_cell_length_b 11.121(2)
_cell_length_c 17.574(4)
_cell_angle_alpha 90.00
_cell_angle_beta 92.04(3)
_cell_angle_gamma 90.00
_cell_volume 1528.4(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 4173
_cell_measurement_theta_min 2.17
_cell_measurement_theta_max 25.13
_exptl_crystal_description 'rectangular block'
_exptl_crystal_colour colorless
_exptl_crystal_size_max 1.85
_exptl_crystal_size_mid 0.88
_exptl_crystal_size_min 0.42
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.292
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 624
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.8691
_exptl_absorpt_correction_T_max 0.9680
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 17948
_diffrn_reflns_av_R_equivalents 0.0416
_diffrn_reflns_av_sigmaI/netI 0.0410
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 2.17
_diffrn_reflns_theta_max 28.31
_reflns_number_total 3704
_reflns_number_gt 2206
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.2599P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.045(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 3704
_refine_ls_number_parameters 209
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0875
_refine_ls_R_factor_gt 0.0417
_refine_ls_wR_factor_ref 0.1217
_refine_ls_wR_factor_gt 0.0984
_refine_ls_goodness_of_fit_ref 0.992
_refine_ls_restrained_S_all 0.992
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.24327(15) 0.81383(11) 0.26673(6) 0.0466(3) Uani 1 1 d . . .
N2 N 0.36562(16) 0.86058(11) 0.15086(7) 0.0509(3) Uani 1 1 d . . .
N3 N 0.29813(17) 0.90834(12) 0.38127(7) 0.0514(3) Uani 1 1 d . . .
C1 C 0.24883(18) 0.79888(13) 0.18710(8) 0.0454(4) Uani 1 1 d . . .
C2 C 0.1333(2) 0.72104(15) 0.14986(9) 0.0583(4) Uani 1 1 d . . .
H2B H 0.0527 0.6787 0.1768 0.070 Uiso 1 1 calc R . .
C3 C 0.1418(2) 0.70872(17) 0.07227(9) 0.0670(5) Uani 1 1 d . . .
H3B H 0.0670 0.6572 0.0460 0.080 Uiso 1 1 calc R . .
C4 C 0.2607(2) 0.77240(16) 0.03376(9) 0.0651(5) Uani 1 1 d . . .
H4A H 0.2683 0.7653 -0.0187 0.078 Uiso 1 1 calc R . .
C5 C 0.3678(2) 0.84677(16) 0.07479(9) 0.0580(4) Uani 1 1 d . . .
H5A H 0.4477 0.8908 0.0484 0.070 Uiso 1 1 calc R . .
C6 C 0.28623(17) 0.92094(13) 0.30592(7) 0.0426(3) Uani 1 1 d . . .
C7 C 0.3057(2) 1.03162(14) 0.27033(8) 0.0504(4) Uani 1 1 d . . .
H7A H 0.3006 1.0378 0.2175 0.060 Uiso 1 1 calc R . .
C8 C 0.3327(2) 1.13146(15) 0.31505(9) 0.0593(4) Uani 1 1 d . . .
H8A H 0.3462 1.2065 0.2927 0.071 Uiso 1 1 calc R . .
C9 C 0.3397(2) 1.12033(16) 0.39323(10) 0.0648(5) Uani 1 1 d . . .
H9A H 0.3555 1.1870 0.4246 0.078 Uiso 1 1 calc R . .
C10 C 0.3225(2) 1.00765(16) 0.42288(9) 0.0600(4) Uani 1 1 d . . .
H10A H 0.3283 0.9996 0.4756 0.072 Uiso 1 1 calc R . .
C11 C 0.17069(19) 0.71811(13) 0.31056(7) 0.0453(4) Uani 1 1 d . . .
C12 C 0.00775(18) 0.73464(13) 0.34192(7) 0.0442(3) Uani 1 1 d . . .
C13 C -0.0935(2) 0.83922(14) 0.32935(9) 0.0525(4) Uani 1 1 d . . .
H13A H -0.0527 0.9010 0.2993 0.063 Uiso 1 1 calc R . .
C14 C -0.2492(2) 0.85038(17) 0.36053(10) 0.0658(5) Uani 1 1 d . . .
H14A H -0.3142 0.9192 0.3512 0.079 Uiso 1 1 calc R . .
C15 C -0.3124(2) 0.75931(19) 0.40641(10) 0.0690(5) Uani 1 1 d . . .
H15A H -0.4186 0.7681 0.4279 0.083 Uiso 1 1 calc R . .
C16 C -0.2194(2) 0.65817(17) 0.41976(9) 0.0614(5) Uani 1 1 d . . .
H16A H -0.2625 0.5989 0.4511 0.074 Uiso 1 1 calc R . .
C17 C -0.0584(2) 0.64044(13) 0.38726(8) 0.0482(4) Uani 1 1 d . . .
C18 C 0.0346(2) 0.53276(15) 0.39594(9) 0.0571(4) Uani 1 1 d . . .
H18A H -0.0087 0.4706 0.4250 0.069 Uiso 1 1 calc R . .
C19 C 0.1876(2) 0.51845(15) 0.36225(9) 0.0612(4) Uani 1 1 d . . .
H19A H 0.2463 0.4460 0.3673 0.073 Uiso 1 1 calc R . .
C20 C 0.2567(2) 0.61273(14) 0.32003(9) 0.0538(4) Uani 1 1 d . . .
H20A H 0.3625 0.6030 0.2983 0.065 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0550(8) 0.0507(7) 0.0345(6) 0.0000(5) 0.0079(5) -0.0083(6)
N2 0.0536(8) 0.0594(8) 0.0403(7) 0.0045(6) 0.0112(6) 0.0054(6)
N3 0.0564(8) 0.0614(8) 0.0363(6) 0.0017(6) 0.0006(5) -0.0109(6)
C1 0.0464(8) 0.0534(9) 0.0366(7) -0.0009(6) 0.0050(6) 0.0057(7)
C2 0.0603(10) 0.0659(11) 0.0488(9) -0.0070(7) 0.0030(7) -0.0041(8)
C3 0.0738(12) 0.0757(12) 0.0509(10) -0.0160(9) -0.0074(9) 0.0076(10)
C4 0.0772(12) 0.0801(12) 0.0381(8) -0.0057(8) 0.0032(8) 0.0272(10)
C5 0.0644(11) 0.0679(11) 0.0425(8) 0.0070(7) 0.0155(7) 0.0192(8)
C6 0.0372(8) 0.0532(9) 0.0376(7) 0.0010(6) 0.0028(5) -0.0042(6)
C7 0.0541(9) 0.0578(9) 0.0392(8) 0.0043(7) 0.0010(6) -0.0053(7)
C8 0.0665(11) 0.0530(10) 0.0583(10) 0.0035(8) 0.0014(8) -0.0100(8)
C9 0.0741(12) 0.0637(11) 0.0566(10) -0.0123(8) 0.0013(8) -0.0193(9)
C10 0.0667(11) 0.0753(11) 0.0378(8) -0.0053(8) -0.0016(7) -0.0188(9)
C11 0.0516(9) 0.0483(9) 0.0362(7) -0.0013(6) 0.0045(6) -0.0055(7)
C12 0.0480(8) 0.0500(8) 0.0347(7) -0.0048(6) 0.0008(6) -0.0074(7)
C13 0.0510(9) 0.0547(9) 0.0518(9) -0.0002(7) 0.0037(7) -0.0022(7)
C14 0.0524(10) 0.0754(12) 0.0700(11) -0.0060(9) 0.0058(8) 0.0061(9)
C15 0.0533(11) 0.0883(14) 0.0664(11) -0.0155(10) 0.0162(8) -0.0079(10)
C16 0.0635(11) 0.0717(12) 0.0497(9) -0.0060(8) 0.0137(8) -0.0206(9)
C17 0.0547(9) 0.0535(9) 0.0363(7) -0.0025(6) 0.0018(6) -0.0133(7)
C18 0.0711(12) 0.0527(10) 0.0476(9) 0.0035(7) 0.0020(8) -0.0146(8)
C19 0.0770(12) 0.0464(9) 0.0598(10) 0.0030(7) -0.0026(9) 0.0029(8)
C20 0.0550(10) 0.0556(9) 0.0512(9) -0.0025(7) 0.0089(7) 0.0022(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.4107(18) . ?
N1 C1 1.4114(17) . ?
N1 C11 1.4423(18) . ?
N2 C1 1.3241(19) . ?
N2 C5 1.3464(19) . ?
N3 C6 1.3314(18) . ?
N3 C10 1.334(2) . ?
C1 C2 1.398(2) . ?
C2 C3 1.374(2) . ?
C2 H2B 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3B 0.9300 . ?
C4 C5 1.365(3) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.392(2) . ?
C7 C8 1.372(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.379(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.366(2) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C20 1.359(2) . ?
C11 C12 1.419(2) . ?
C12 C13 1.420(2) . ?
C12 C17 1.425(2) . ?
C13 C14 1.359(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.396(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.355(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.416(2) . ?
C16 H16A 0.9300 . ?
C17 C18 1.407(2) . ?
C18 C19 1.363(2) . ?
C18 H18A 0.9300 . ?
C19 C20 1.404(2) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C1 124.64(12) . . ?
C6 N1 C11 117.00(11) . . ?
C1 N1 C11 117.98(12) . . ?
C1 N2 C5 116.87(14) . . ?
C6 N3 C10 117.48(13) . . ?
N2 C1 C2 122.82(13) . . ?
N2 C1 N1 117.51(13) . . ?
C2 C1 N1 119.67(13) . . ?
C3 C2 C1 118.21(16) . . ?
C3 C2 H2B 120.9 . . ?
C1 C2 H2B 120.9 . . ?
C4 C3 C2 119.83(17) . . ?
C4 C3 H3B 120.1 . . ?
C2 C3 H3B 120.1 . . ?
C5 C4 C3 117.91(15) . . ?
C5 C4 H4A 121.0 . . ?
C3 C4 H4A 121.0 . . ?
N2 C5 C4 124.35(16) . . ?
N2 C5 H5A 117.8 . . ?
C4 C5 H5A 117.8 . . ?
N3 C6 C7 122.36(13) . . ?
N3 C6 N1 113.81(12) . . ?
C7 C6 N1 123.74(12) . . ?
C8 C7 C6 118.38(14) . . ?
C8 C7 H7A 120.8 . . ?
C6 C7 H7A 120.8 . . ?
C7 C8 C9 119.86(15) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C10 C9 C8 117.50(15) . . ?
C10 C9 H9A 121.3 . . ?
C8 C9 H9A 121.3 . . ?
N3 C10 C9 124.36(14) . . ?
N3 C10 H10A 117.8 . . ?
C9 C10 H10A 117.8 . . ?
C20 C11 C12 120.81(13) . . ?
C20 C11 N1 119.95(14) . . ?
C12 C11 N1 119.22(13) . . ?
C11 C12 C13 123.35(13) . . ?
C11 C12 C17 118.13(14) . . ?
C13 C12 C17 118.51(14) . . ?
C14 C13 C12 121.01(15) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C15 120.50(17) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C16 C15 C14 120.22(16) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 121.71(16) . . ?
C15 C16 H16A 119.1 . . ?
C17 C16 H16A 119.1 . . ?
C18 C17 C16 122.65(15) . . ?
C18 C17 C12 119.31(14) . . ?
C16 C17 C12 118.01(15) . . ?
C19 C18 C17 120.75(15) . . ?
C19 C18 H18A 119.6 . . ?
C17 C18 H18A 119.6 . . ?
C18 C19 C20 120.20(16) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C11 C20 C19 120.69(15) . . ?
C11 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C1 C2 0.9(2) . . . . ?
C5 N2 C1 N1 -179.07(12) . . . . ?
C6 N1 C1 N2 31.5(2) . . . . ?
C11 N1 C1 N2 -155.78(13) . . . . ?
C6 N1 C1 C2 -148.46(15) . . . . ?
C11 N1 C1 C2 24.2(2) . . . . ?
N2 C1 C2 C3 -0.1(2) . . . . ?
N1 C1 C2 C3 179.86(14) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C1 N2 C5 C4 -1.3(2) . . . . ?
C3 C4 C5 N2 0.8(3) . . . . ?
C10 N3 C6 C7 2.8(2) . . . . ?
C10 N3 C6 N1 -173.89(13) . . . . ?
C1 N1 C6 N3 -169.69(13) . . . . ?
C11 N1 C6 N3 17.56(18) . . . . ?
C1 N1 C6 C7 13.6(2) . . . . ?
C11 N1 C6 C7 -159.13(14) . . . . ?
N3 C6 C7 C8 -2.1(2) . . . . ?
N1 C6 C7 C8 174.27(14) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C7 C8 C9 C10 1.3(3) . . . . ?
C6 N3 C10 C9 -1.5(3) . . . . ?
C8 C9 C10 N3 -0.6(3) . . . . ?
C6 N1 C11 C20 -115.59(15) . . . . ?
C1 N1 C11 C20 71.17(18) . . . . ?
C6 N1 C11 C12 65.79(17) . . . . ?
C1 N1 C11 C12 -107.45(15) . . . . ?
C20 C11 C12 C13 -175.32(14) . . . . ?
N1 C11 C12 C13 3.3(2) . . . . ?
C20 C11 C12 C17 3.6(2) . . . . ?
N1 C11 C12 C17 -177.79(12) . . . . ?
C11 C12 C13 C14 179.75(15) . . . . ?
C17 C12 C13 C14 0.8(2) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 C18 -175.38(15) . . . . ?
C15 C16 C17 C12 2.4(2) . . . . ?
C11 C12 C17 C18 -3.39(19) . . . . ?
C13 C12 C17 C18 175.58(13) . . . . ?
C11 C12 C17 C16 178.73(13) . . . . ?
C13 C12 C17 C16 -2.29(19) . . . . ?
C16 C17 C18 C19 178.53(15) . . . . ?
C12 C17 C18 C19 0.8(2) . . . . ?
C17 C18 C19 C20 1.8(2) . . . . ?
C12 C11 C20 C19 -1.1(2) . . . . ?
N1 C11 C20 C19 -179.73(13) . . . . ?
C18 C19 C20 C11 -1.6(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full 28.31
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max 0.136
_refine_diff_density_min -0.139
_refine_diff_density_rms 0.034
_exptl_crystal_recrystallization_method
'sat. soln. in 1:1 DCM and hexanes cooled to -12 deg. C for several days'
_diffrn_ambient_pressure 101.33
# Attachment 'Ph(Et2)DPA.CIF'
data_etphdpa
_database_code_depnum_ccdc_archive 'CCDC 720338'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
N-(2,6-diethylphenyl)-N,N-(2,2'-dipyridyl)amine
_chemical_name_common (diethylphenyl)(dipyridyl)amine
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H21 N3'
_chemical_formula_sum 'C20 H21 N3'
_chemical_formula_weight 303.40
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21'
_symmetry_int_tables_number 4
_symmetry_space_group_name_Hall 'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 8.5458(17)
_cell_length_b 17.299(4)
_cell_length_c 11.402(2)
_cell_angle_alpha 90.00
_cell_angle_beta 92.17(3)
_cell_angle_gamma 90.00
_cell_volume 1684.4(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 2282
_cell_measurement_theta_min 2.35
_cell_measurement_theta_max 20.12
_exptl_crystal_description prism
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.67
_exptl_crystal_size_mid 0.59
_exptl_crystal_size_min 0.37
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.196
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 648
_exptl_absorpt_coefficient_mu 0.072
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9535
_exptl_absorpt_correction_T_max 0.9740
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 20449
_diffrn_reflns_av_R_equivalents 0.0623
_diffrn_reflns_av_sigmaI/netI 0.1176
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_k_max 23
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 1.79
_diffrn_reflns_theta_max 28.31
_reflns_number_total 7962
_reflns_number_gt 3288
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.00
_refine_ls_number_reflns 7962
_refine_ls_number_parameters 420
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.1735
_refine_ls_R_factor_gt 0.0486
_refine_ls_wR_factor_ref 0.1562
_refine_ls_wR_factor_gt 0.1098
_refine_ls_goodness_of_fit_ref 0.936
_refine_ls_restrained_S_all 0.936
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N -0.6609(3) -0.06163(14) -0.4151(2) 0.0526(7) Uani 1 1 d . . .
N2A N -0.5724(3) -0.17656(15) -0.3355(2) 0.0645(8) Uani 1 1 d . . .
N3A N -0.4975(4) 0.04713(17) -0.4020(3) 0.0699(8) Uani 1 1 d . . .
C1A C -0.5883(3) -0.10070(18) -0.3198(3) 0.0510(8) Uani 1 1 d . . .
C2A C -0.5437(4) -0.0639(2) -0.2160(3) 0.0597(9) Uani 1 1 d . . .
H2AB H -0.5572 -0.0110 -0.2072 0.072 Uiso 1 1 calc R . .
C3A C -0.4792(4) -0.1077(2) -0.1270(3) 0.0716(10) Uani 1 1 d . . .
H3AB H -0.4461 -0.0843 -0.0570 0.086 Uiso 1 1 calc R . .
C4A C -0.4631(4) -0.1856(2) -0.1404(3) 0.0742(11) Uani 1 1 d . . .
H4AA H -0.4220 -0.2163 -0.0797 0.089 Uiso 1 1 calc R . .
C5A C -0.5098(5) -0.2175(2) -0.2467(3) 0.0751(10) Uani 1 1 d . . .
H5AA H -0.4968 -0.2704 -0.2570 0.090 Uiso 1 1 calc R . .
C6A C -0.6342(4) 0.01654(18) -0.4404(3) 0.0571(9) Uani 1 1 d . . .
C7A C -0.7440(4) 0.0583(2) -0.5058(3) 0.0682(9) Uani 1 1 d . . .
H7AA H -0.8379 0.0359 -0.5318 0.082 Uiso 1 1 calc R . .
C8A C -0.7101(6) 0.1341(2) -0.5313(4) 0.0919(13) Uani 1 1 d . . .
H8AA H -0.7819 0.1636 -0.5753 0.110 Uiso 1 1 calc R . .
C9A C -0.5711(7) 0.1666(3) -0.4923(4) 0.0951(14) Uani 1 1 d . . .
H9AA H -0.5461 0.2175 -0.5097 0.114 Uiso 1 1 calc R . .
C10A C -0.4722(5) 0.1214(2) -0.4276(4) 0.0833(12) Uani 1 1 d . . .
H10A H -0.3795 0.1437 -0.3985 0.100 Uiso 1 1 calc R . .
C11A C -0.7578(4) -0.10623(17) -0.4962(3) 0.0550(8) Uani 1 1 d . . .
C12A C -0.6963(5) -0.1277(2) -0.6017(3) 0.0679(10) Uani 1 1 d . . .
C13A C -0.7913(7) -0.1703(2) -0.6778(4) 0.0919(13) Uani 1 1 d . . .
H13A H -0.7542 -0.1848 -0.7502 0.110 Uiso 1 1 calc R . .
C14A C -0.9394(7) -0.1916(2) -0.6486(4) 0.0924(13) Uani 1 1 d . . .
H14A H -1.0007 -0.2211 -0.7007 0.111 Uiso 1 1 calc R . .
C15A C -0.9978(5) -0.1699(2) -0.5435(4) 0.0798(11) Uani 1 1 d . . .
H15A H -1.0984 -0.1849 -0.5248 0.096 Uiso 1 1 calc R . .
C16A C -0.9083(4) -0.12580(19) -0.4645(3) 0.0624(9) Uani 1 1 d . . .
C17A C -0.5318(6) -0.1074(3) -0.6303(4) 0.0966(13) Uani 1 1 d . . .
H17A H -0.5273 -0.0518 -0.6410 0.116 Uiso 1 1 calc R . .
H17D H -0.4651 -0.1197 -0.5622 0.116 Uiso 1 1 calc R . .
C18A C -0.9669(4) -0.1011(2) -0.3471(3) 0.0781(11) Uani 1 1 d . . .
H18A H -0.8961 -0.1218 -0.2864 0.094 Uiso 1 1 calc R . .
H18D H -0.9607 -0.0452 -0.3426 0.094 Uiso 1 1 calc R . .
C19A C -0.4618(7) -0.1437(3) -0.7336(5) 0.149(2) Uani 1 1 d . . .
H19A H -0.3545 -0.1278 -0.7377 0.223 Uiso 1 1 calc R . .
H19B H -0.5188 -0.1279 -0.8037 0.223 Uiso 1 1 calc R . .
H19C H -0.4666 -0.1989 -0.7263 0.223 Uiso 1 1 calc R . .
C20A C -1.1310(5) -0.1249(3) -0.3195(5) 0.1193(17) Uani 1 1 d . . .
H20A H -1.1560 -0.1056 -0.2436 0.179 Uiso 1 1 calc R . .
H20B H -1.1384 -0.1803 -0.3197 0.179 Uiso 1 1 calc R . .
H20C H -1.2034 -0.1041 -0.3777 0.179 Uiso 1 1 calc R . .
N1B N -0.9813(3) 0.02338(14) 0.0801(2) 0.0554(7) Uani 1 1 d . . .
N2B N -1.0563(3) 0.13685(14) 0.1675(2) 0.0638(8) Uani 1 1 d . . .
N3B N -1.1254(3) -0.09207(14) 0.0895(2) 0.0596(7) Uani 1 1 d . . .
C1B C -1.0458(4) 0.05991(17) 0.1766(3) 0.0518(8) Uani 1 1 d . . .
C2B C -1.0873(4) 0.02124(19) 0.2772(3) 0.0614(9) Uani 1 1 d . . .
H2BB H -1.0770 -0.0322 0.2829 0.074 Uiso 1 1 calc R . .
C3B C -1.1435(4) 0.0630(2) 0.3677(3) 0.0699(10) Uani 1 1 d . . .
H3BB H -1.1741 0.0378 0.4352 0.084 Uiso 1 1 calc R . .
C4B C -1.1554(4) 0.1419(2) 0.3601(3) 0.0764(11) Uani 1 1 d . . .
H4BA H -1.1925 0.1713 0.4216 0.092 Uiso 1 1 calc R . .
C5B C -1.1104(5) 0.1756(2) 0.2583(4) 0.0748(11) Uani 1 1 d . . .
H5BA H -1.1181 0.2290 0.2521 0.090 Uiso 1 1 calc R . .
C6B C -0.9944(4) -0.05694(17) 0.0585(3) 0.0493(7) Uani 1 1 d . . .
C7B C -0.8751(4) -0.09487(18) 0.0039(3) 0.0622(9) Uani 1 1 d . . .
H7BA H -0.7852 -0.0685 -0.0163 0.075 Uiso 1 1 calc R . .
C8B C -0.8918(4) -0.1721(2) -0.0198(3) 0.0688(10) Uani 1 1 d . . .
H8BA H -0.8134 -0.1990 -0.0568 0.083 Uiso 1 1 calc R . .
C9B C -1.0261(5) -0.20944(19) 0.0117(3) 0.0686(10) Uani 1 1 d . . .
H9BA H -1.0412 -0.2617 -0.0041 0.082 Uiso 1 1 calc R . .
C10B C -1.1352(4) -0.16758(19) 0.0664(3) 0.0634(9) Uani 1 1 d . . .
H10B H -1.2242 -0.1935 0.0897 0.076 Uiso 1 1 calc R . .
C11B C -0.8980(4) 0.06747(17) -0.0042(3) 0.0552(8) Uani 1 1 d . . .
C12B C -0.9678(4) 0.08138(17) -0.1151(3) 0.0598(9) Uani 1 1 d . . .
C13B C -0.8812(5) 0.1181(2) -0.1966(3) 0.0735(10) Uani 1 1 d . . .
H13B H -0.9247 0.1265 -0.2716 0.088 Uiso 1 1 calc R . .
C14B C -0.7306(5) 0.1432(2) -0.1700(4) 0.0777(11) Uani 1 1 d . . .
H14B H -0.6736 0.1684 -0.2264 0.093 Uiso 1 1 calc R . .
C15B C -0.6658(4) 0.1306(2) -0.0602(4) 0.0724(10) Uani 1 1 d . . .
H15B H -0.5648 0.1483 -0.0428 0.087 Uiso 1 1 calc R . .
C16B C -0.7455(4) 0.09258(18) 0.0258(3) 0.0621(9) Uani 1 1 d . . .
C17B C -1.1356(5) 0.0599(2) -0.1444(4) 0.0862(12) Uani 1 1 d . . .
H17B H -1.1426 0.0392 -0.2235 0.103 Uiso 1 1 calc R . .
H17C H -1.1668 0.0193 -0.0914 0.103 Uiso 1 1 calc R . .
C18B C -0.6726(4) 0.0772(3) 0.1461(4) 0.0883(12) Uani 1 1 d . . .
H18B H -0.7026 0.1188 0.1975 0.106 Uiso 1 1 calc R . .
H18C H -0.7179 0.0300 0.1757 0.106 Uiso 1 1 calc R . .
C19B C -1.2462(5) 0.1251(3) -0.1364(6) 0.136(2) Uani 1 1 d . . .
H19D H -1.3513 0.1068 -0.1504 0.204 Uiso 1 1 calc R . .
H19E H -1.2227 0.1634 -0.1941 0.204 Uiso 1 1 calc R . .
H19F H -1.2366 0.1477 -0.0595 0.204 Uiso 1 1 calc R . .
C20B C -0.4977(5) 0.0694(3) 0.1554(5) 0.1098(15) Uani 1 1 d . . .
H20D H -0.4651 0.0611 0.2359 0.165 Uiso 1 1 calc R . .
H20E H -0.4502 0.1158 0.1272 0.165 Uiso 1 1 calc R . .
H20F H -0.4658 0.0262 0.1090 0.165 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1A 0.0602(17) 0.0427(15) 0.0544(16) 0.0004(13) -0.0037(13) -0.0024(12)
N2A 0.076(2) 0.0474(17) 0.0701(19) 0.0018(15) -0.0030(15) 0.0043(14)
N3A 0.079(2) 0.057(2) 0.074(2) -0.0020(15) 0.0116(16) -0.0125(16)
C1A 0.0459(18) 0.050(2) 0.057(2) 0.0048(17) 0.0009(16) -0.0015(15)
C2A 0.061(2) 0.058(2) 0.060(2) -0.0045(19) -0.0030(17) 0.0020(17)
C3A 0.068(2) 0.079(3) 0.067(2) 0.001(2) -0.0064(19) -0.011(2)
C4A 0.074(3) 0.074(3) 0.073(3) 0.014(2) -0.015(2) -0.001(2)
C5A 0.090(3) 0.058(2) 0.076(3) 0.009(2) -0.016(2) 0.004(2)
C6A 0.072(2) 0.046(2) 0.054(2) -0.0034(17) 0.0061(18) 0.0014(18)
C7A 0.084(3) 0.056(2) 0.064(2) 0.0051(18) -0.0009(19) 0.010(2)
C8A 0.140(4) 0.061(3) 0.075(3) 0.013(2) 0.006(3) 0.018(3)
C9A 0.155(5) 0.063(3) 0.069(3) 0.005(2) 0.028(3) -0.013(3)
C10A 0.104(3) 0.070(3) 0.077(3) -0.006(2) 0.023(2) -0.028(2)
C11A 0.067(2) 0.0441(18) 0.053(2) 0.0031(15) -0.0037(17) 0.0012(16)
C12A 0.092(3) 0.055(2) 0.057(2) -0.0048(18) 0.004(2) 0.0035(19)
C13A 0.137(4) 0.075(3) 0.064(3) -0.009(2) -0.001(3) 0.009(3)
C14A 0.124(4) 0.072(3) 0.078(3) -0.007(2) -0.034(3) -0.009(3)
C15A 0.077(3) 0.071(2) 0.090(3) 0.007(2) -0.016(2) -0.011(2)
C16A 0.068(2) 0.0479(19) 0.070(2) 0.0044(17) -0.0098(19) -0.0041(17)
C17A 0.119(4) 0.087(3) 0.087(3) -0.014(2) 0.038(3) -0.002(3)
C18A 0.068(2) 0.080(3) 0.087(3) -0.002(2) 0.012(2) -0.011(2)
C19A 0.186(6) 0.126(5) 0.141(5) -0.022(4) 0.090(4) 0.005(4)
C20A 0.081(3) 0.121(4) 0.159(5) -0.020(3) 0.035(3) -0.020(3)
N1B 0.0598(18) 0.0431(16) 0.0642(18) -0.0039(13) 0.0152(14) -0.0022(12)
N2B 0.078(2) 0.0460(18) 0.068(2) -0.0057(14) 0.0116(15) -0.0005(14)
N3B 0.0602(18) 0.0471(17) 0.0716(19) -0.0015(13) 0.0049(14) -0.0075(14)
C1B 0.0499(19) 0.045(2) 0.061(2) -0.0012(17) 0.0067(16) -0.0028(15)
C2B 0.072(2) 0.054(2) 0.059(2) 0.0027(18) 0.0079(18) 0.0004(17)
C3B 0.076(2) 0.075(3) 0.058(2) 0.002(2) 0.0121(19) -0.002(2)
C4B 0.083(3) 0.077(3) 0.071(3) -0.018(2) 0.016(2) 0.003(2)
C5B 0.088(3) 0.056(2) 0.081(3) -0.009(2) 0.017(2) 0.0040(19)
C6B 0.055(2) 0.0396(18) 0.0536(19) -0.0002(15) 0.0061(15) -0.0013(16)
C7B 0.062(2) 0.049(2) 0.077(2) -0.0033(17) 0.0164(18) 0.0005(17)
C8B 0.081(3) 0.056(2) 0.070(2) -0.0044(19) 0.014(2) 0.011(2)
C9B 0.099(3) 0.0398(19) 0.067(2) -0.0065(18) 0.005(2) -0.002(2)
C10B 0.073(2) 0.055(2) 0.063(2) -0.0023(19) 0.0030(19) -0.0135(19)
C11B 0.059(2) 0.0398(17) 0.068(2) -0.0007(16) 0.0178(18) -0.0042(15)
C12B 0.070(2) 0.046(2) 0.064(2) 0.0044(17) 0.0111(19) 0.0011(17)
C13B 0.093(3) 0.061(2) 0.067(2) 0.0049(19) 0.014(2) 0.010(2)
C14B 0.102(3) 0.059(2) 0.075(3) 0.006(2) 0.038(3) 0.007(2)
C15B 0.069(2) 0.058(2) 0.092(3) -0.007(2) 0.029(2) -0.0082(18)
C16B 0.063(2) 0.053(2) 0.071(2) -0.0078(18) 0.014(2) -0.0035(17)
C17B 0.085(3) 0.081(3) 0.093(3) 0.013(2) -0.010(2) -0.014(2)
C18B 0.067(3) 0.102(3) 0.096(3) -0.005(3) -0.003(2) -0.020(2)
C19B 0.076(3) 0.144(5) 0.186(6) -0.018(4) -0.021(3) 0.009(3)
C20B 0.082(3) 0.116(4) 0.131(4) -0.007(3) -0.013(3) 0.001(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C6A 1.403(4) . ?
N1A C1A 1.404(4) . ?
N1A C11A 1.442(4) . ?
N2A C5A 1.331(4) . ?
N2A C1A 1.332(4) . ?
N3A C10A 1.338(5) . ?
N3A C6A 1.340(4) . ?
C1A C2A 1.384(4) . ?
C2A C3A 1.365(5) . ?
C2A H2AB 0.9300 . ?
C3A C4A 1.364(5) . ?
C3A H3AB 0.9300 . ?
C4A C5A 1.377(5) . ?
C4A H4AA 0.9300 . ?
C5A H5AA 0.9300 . ?
C6A C7A 1.380(5) . ?
C7A C8A 1.377(6) . ?
C7A H7AA 0.9300 . ?
C8A C9A 1.373(6) . ?
C8A H8AA 0.9300 . ?
C9A C10A 1.349(6) . ?
C9A H9AA 0.9300 . ?
C10A H10A 0.9300 . ?
C11A C12A 1.381(4) . ?
C11A C16A 1.392(5) . ?
C12A C13A 1.379(6) . ?
C12A C17A 1.497(6) . ?
C13A C14A 1.372(6) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.367(6) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.388(5) . ?
C15A H15A 0.9300 . ?
C16A C18A 1.508(5) . ?
C17A C19A 1.480(6) . ?
C17A H17A 0.9700 . ?
C17A H17D 0.9700 . ?
C18A C20A 1.507(5) . ?
C18A H18A 0.9700 . ?
C18A H18D 0.9700 . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
N1B C1B 1.400(4) . ?
N1B C6B 1.415(4) . ?
N1B C11B 1.438(4) . ?
N2B C5B 1.331(4) . ?
N2B C1B 1.338(4) . ?
N3B C6B 1.334(4) . ?
N3B C10B 1.335(4) . ?
C1B C2B 1.386(4) . ?
C2B C3B 1.362(5) . ?
C2B H2BB 0.9300 . ?
C3B C4B 1.371(5) . ?
C3B H3BB 0.9300 . ?
C4B C5B 1.367(5) . ?
C4B H4BA 0.9300 . ?
C5B H5BA 0.9300 . ?
C6B C7B 1.381(4) . ?
C7B C8B 1.370(4) . ?
C7B H7BA 0.9300 . ?
C8B C9B 1.377(5) . ?
C8B H8BA 0.9300 . ?
C9B C10B 1.351(5) . ?
C9B H9BA 0.9300 . ?
C10B H10B 0.9300 . ?
C11B C12B 1.398(4) . ?
C11B C16B 1.404(5) . ?
C12B C13B 1.367(5) . ?
C12B C17B 1.507(5) . ?
C13B C14B 1.380(5) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.367(5) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.381(5) . ?
C15B H15B 0.9300 . ?
C16B C18B 1.509(5) . ?
C17B C19B 1.477(6) . ?
C17B H17B 0.9700 . ?
C17B H17C 0.9700 . ?
C18B C20B 1.501(6) . ?
C18B H18B 0.9700 . ?
C18B H18C 0.9700 . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6A N1A C1A 123.5(3) . . ?
C6A N1A C11A 118.6(2) . . ?
C1A N1A C11A 117.7(2) . . ?
C5A N2A C1A 117.5(3) . . ?
C10A N3A C6A 117.0(3) . . ?
N2A C1A C2A 122.8(3) . . ?
N2A C1A N1A 114.5(3) . . ?
C2A C1A N1A 122.7(3) . . ?
C3A C2A C1A 118.1(3) . . ?
C3A C2A H2AB 120.9 . . ?
C1A C2A H2AB 120.9 . . ?
C4A C3A C2A 120.3(4) . . ?
C4A C3A H3AB 119.9 . . ?
C2A C3A H3AB 119.9 . . ?
C3A C4A C5A 117.8(3) . . ?
C3A C4A H4AA 121.1 . . ?
C5A C4A H4AA 121.1 . . ?
N2A C5A C4A 123.5(3) . . ?
N2A C5A H5AA 118.3 . . ?
C4A C5A H5AA 118.3 . . ?
N3A C6A C7A 122.4(3) . . ?
N3A C6A N1A 117.4(3) . . ?
C7A C6A N1A 120.2(3) . . ?
C8A C7A C6A 117.9(4) . . ?
C8A C7A H7AA 121.0 . . ?
C6A C7A H7AA 121.0 . . ?
C9A C8A C7A 120.5(4) . . ?
C9A C8A H8AA 119.8 . . ?
C7A C8A H8AA 119.8 . . ?
C10A C9A C8A 117.2(4) . . ?
C10A C9A H9AA 121.4 . . ?
C8A C9A H9AA 121.4 . . ?
N3A C10A C9A 124.9(4) . . ?
N3A C10A H10A 117.5 . . ?
C9A C10A H10A 117.5 . . ?
C12A C11A C16A 123.2(3) . . ?
C12A C11A N1A 118.3(3) . . ?
C16A C11A N1A 118.5(3) . . ?
C13A C12A C11A 117.2(4) . . ?
C13A C12A C17A 121.5(4) . . ?
C11A C12A C17A 121.2(3) . . ?
C14A C13A C12A 121.1(4) . . ?
C14A C13A H13A 119.4 . . ?
C12A C13A H13A 119.4 . . ?
C15A C14A C13A 120.7(4) . . ?
C15A C14A H14A 119.7 . . ?
C13A C14A H14A 119.7 . . ?
C14A C15A C16A 120.6(4) . . ?
C14A C15A H15A 119.7 . . ?
C16A C15A H15A 119.7 . . ?
C15A C16A C11A 117.2(3) . . ?
C15A C16A C18A 122.6(4) . . ?
C11A C16A C18A 120.2(3) . . ?
C19A C17A C12A 119.0(4) . . ?
C19A C17A H17A 107.6 . . ?
C12A C17A H17A 107.6 . . ?
C19A C17A H17D 107.6 . . ?
C12A C17A H17D 107.6 . . ?
H17A C17A H17D 107.0 . . ?
C20A C18A C16A 116.8(4) . . ?
C20A C18A H18A 108.1 . . ?
C16A C18A H18A 108.1 . . ?
C20A C18A H18D 108.1 . . ?
C16A C18A H18D 108.1 . . ?
H18A C18A H18D 107.3 . . ?
C17A C19A H19A 109.5 . . ?
C17A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C17A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C18A C20A H20A 109.5 . . ?
C18A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C18A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C1B N1B C6B 123.4(2) . . ?
C1B N1B C11B 120.4(2) . . ?
C6B N1B C11B 116.2(2) . . ?
C5B N2B C1B 117.7(3) . . ?
C6B N3B C10B 116.1(3) . . ?
N2B C1B C2B 121.8(3) . . ?
N2B C1B N1B 114.5(3) . . ?
C2B C1B N1B 123.6(3) . . ?
C3B C2B C1B 118.7(3) . . ?
C3B C2B H2BB 120.7 . . ?
C1B C2B H2BB 120.7 . . ?
C2B C3B C4B 120.5(3) . . ?
C2B C3B H3BB 119.7 . . ?
C4B C3B H3BB 119.7 . . ?
C5B C4B C3B 117.0(3) . . ?
C5B C4B H4BA 121.5 . . ?
C3B C4B H4BA 121.5 . . ?
N2B C5B C4B 124.3(3) . . ?
N2B C5B H5BA 117.8 . . ?
C4B C5B H5BA 117.8 . . ?
N3B C6B C7B 123.0(3) . . ?
N3B C6B N1B 117.6(3) . . ?
C7B C6B N1B 119.4(3) . . ?
C8B C7B C6B 118.7(3) . . ?
C8B C7B H7BA 120.7 . . ?
C6B C7B H7BA 120.7 . . ?
C7B C8B C9B 119.2(3) . . ?
C7B C8B H8BA 120.4 . . ?
C9B C8B H8BA 120.4 . . ?
C10B C9B C8B 117.8(3) . . ?
C10B C9B H9BA 121.1 . . ?
C8B C9B H9BA 121.1 . . ?
N3B C10B C9B 125.2(3) . . ?
N3B C10B H10B 117.4 . . ?
C9B C10B H10B 117.4 . . ?
C12B C11B C16B 121.8(3) . . ?
C12B C11B N1B 119.4(3) . . ?
C16B C11B N1B 118.7(3) . . ?
C13B C12B C11B 118.1(3) . . ?
C13B C12B C17B 119.9(4) . . ?
C11B C12B C17B 121.9(3) . . ?
C12B C13B C14B 121.4(4) . . ?
C12B C13B H13B 119.3 . . ?
C14B C13B H13B 119.3 . . ?
C15B C14B C13B 119.6(4) . . ?
C15B C14B H14B 120.2 . . ?
C13B C14B H14B 120.2 . . ?
C14B C15B C16B 122.1(4) . . ?
C14B C15B H15B 118.9 . . ?
C16B C15B H15B 118.9 . . ?
C15B C16B C11B 116.9(3) . . ?
C15B C16B C18B 122.1(3) . . ?
C11B C16B C18B 120.9(3) . . ?
C19B C17B C12B 113.8(4) . . ?
C19B C17B H17B 108.8 . . ?
C12B C17B H17B 108.8 . . ?
C19B C17B H17C 108.8 . . ?
C12B C17B H17C 108.8 . . ?
H17B C17B H17C 107.7 . . ?
C20B C18B C16B 117.1(4) . . ?
C20B C18B H18B 108.0 . . ?
C16B C18B H18B 108.0 . . ?
C20B C18B H18C 108.0 . . ?
C16B C18B H18C 108.0 . . ?
H18B C18B H18C 107.3 . . ?
C17B C19B H19D 109.5 . . ?
C17B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C17B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C18B C20B H20D 109.5 . . ?
C18B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C18B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5A N2A C1A C2A -0.4(5) . . . . ?
C5A N2A C1A N1A -177.6(3) . . . . ?
C6A N1A C1A N2A -152.8(3) . . . . ?
C11A N1A C1A N2A 22.0(4) . . . . ?
C6A N1A C1A C2A 30.1(5) . . . . ?
C11A N1A C1A C2A -155.2(3) . . . . ?
N2A C1A C2A C3A 0.7(5) . . . . ?
N1A C1A C2A C3A 177.6(3) . . . . ?
C1A C2A C3A C4A -1.4(5) . . . . ?
C2A C3A C4A C5A 1.8(6) . . . . ?
C1A N2A C5A C4A 0.8(6) . . . . ?
C3A C4A C5A N2A -1.5(6) . . . . ?
C10A N3A C6A C7A 1.5(5) . . . . ?
C10A N3A C6A N1A 179.3(3) . . . . ?
C1A N1A C6A N3A 25.1(4) . . . . ?
C11A N1A C6A N3A -149.6(3) . . . . ?
C1A N1A C6A C7A -157.1(3) . . . . ?
C11A N1A C6A C7A 28.2(4) . . . . ?
N3A C6A C7A C8A -0.3(5) . . . . ?
N1A C6A C7A C8A -178.0(3) . . . . ?
C6A C7A C8A C9A -0.1(6) . . . . ?
C7A C8A C9A C10A -0.9(6) . . . . ?
C6A N3A C10A C9A -2.5(6) . . . . ?
C8A C9A C10A N3A 2.2(7) . . . . ?
C6A N1A C11A C12A 73.7(4) . . . . ?
C1A N1A C11A C12A -101.3(3) . . . . ?
C6A N1A C11A C16A -106.5(3) . . . . ?
C1A N1A C11A C16A 78.5(4) . . . . ?
C16A C11A C12A C13A 0.3(5) . . . . ?
N1A C11A C12A C13A -180.0(3) . . . . ?
C16A C11A C12A C17A -178.1(3) . . . . ?
N1A C11A C12A C17A 1.7(5) . . . . ?
C11A C12A C13A C14A -1.3(6) . . . . ?
C17A C12A C13A C14A 177.0(4) . . . . ?
C12A C13A C14A C15A 1.1(6) . . . . ?
C13A C14A C15A C16A 0.1(6) . . . . ?
C14A C15A C16A C11A -1.1(5) . . . . ?
C14A C15A C16A C18A -179.4(3) . . . . ?
C12A C11A C16A C15A 0.9(5) . . . . ?
N1A C11A C16A C15A -178.9(3) . . . . ?
C12A C11A C16A C18A 179.2(3) . . . . ?
N1A C11A C16A C18A -0.5(4) . . . . ?
C13A C12A C17A C19A -9.5(6) . . . . ?
C11A C12A C17A C19A 168.8(4) . . . . ?
C15A C16A C18A C20A -1.6(5) . . . . ?
C11A C16A C18A C20A -179.8(4) . . . . ?
C5B N2B C1B C2B -0.9(5) . . . . ?
C5B N2B C1B N1B -177.2(3) . . . . ?
C6B N1B C1B N2B -164.0(3) . . . . ?
C11B N1B C1B N2B 15.3(4) . . . . ?
C6B N1B C1B C2B 19.8(5) . . . . ?
C11B N1B C1B C2B -160.9(3) . . . . ?
N2B C1B C2B C3B 1.5(5) . . . . ?
N1B C1B C2B C3B 177.5(3) . . . . ?
C1B C2B C3B C4B -1.4(5) . . . . ?
C2B C3B C4B C5B 0.7(6) . . . . ?
C1B N2B C5B C4B 0.2(6) . . . . ?
C3B C4B C5B N2B -0.1(6) . . . . ?
C10B N3B C6B C7B 0.9(5) . . . . ?
C10B N3B C6B N1B 179.1(3) . . . . ?
C1B N1B C6B N3B 33.5(4) . . . . ?
C11B N1B C6B N3B -145.8(3) . . . . ?
C1B N1B C6B C7B -148.2(3) . . . . ?
C11B N1B C6B C7B 32.5(4) . . . . ?
N3B C6B C7B C8B 0.2(5) . . . . ?
N1B C6B C7B C8B -177.9(3) . . . . ?
C6B C7B C8B C9B -0.3(5) . . . . ?
C7B C8B C9B C10B -0.7(5) . . . . ?
C6B N3B C10B C9B -2.0(5) . . . . ?
C8B C9B C10B N3B 2.0(5) . . . . ?
C1B N1B C11B C12B -106.8(3) . . . . ?
C6B N1B C11B C12B 72.5(4) . . . . ?
C1B N1B C11B C16B 75.9(4) . . . . ?
C6B N1B C11B C16B -104.8(3) . . . . ?
C16B C11B C12B C13B 2.3(5) . . . . ?
N1B C11B C12B C13B -174.9(3) . . . . ?
C16B C11B C12B C17B -175.2(3) . . . . ?
N1B C11B C12B C17B 7.5(5) . . . . ?
C11B C12B C13B C14B -1.9(5) . . . . ?
C17B C12B C13B C14B 175.7(3) . . . . ?
C12B C13B C14B C15B 0.4(5) . . . . ?
C13B C14B C15B C16B 0.8(5) . . . . ?
C14B C15B C16B C11B -0.5(5) . . . . ?
C14B C15B C16B C18B 178.6(3) . . . . ?
C12B C11B C16B C15B -1.1(5) . . . . ?
N1B C11B C16B C15B 176.1(3) . . . . ?
C12B C11B C16B C18B 179.8(3) . . . . ?
N1B C11B C16B C18B -2.9(5) . . . . ?
C13B C12B C17B C19B -79.0(5) . . . . ?
C11B C12B C17B C19B 98.5(4) . . . . ?
C15B C16B C18B C20B -27.9(6) . . . . ?
C11B C16B C18B C20B 151.1(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full 28.31
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max 0.248
_refine_diff_density_min -0.161
_refine_diff_density_rms 0.034
_exptl_crystal_recrystallization_method
'sat. soln. in CHCl3 cooled to -12 deg. C for several days'
_diffrn_ambient_pressure 101.33
# Attachment 'Ph(iPr)1DPA.CIF'
data_ipr1dpa
_database_code_depnum_ccdc_archive 'CCDC 720339'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
N-(2-isopropylphenyl)-N,N-(2,2'-dipyridyl)amine
_chemical_name_common ?
_chemical_melting_point 374
_chemical_formula_moiety 'C19 H19 N3'
_chemical_formula_sum 'C19 H19 N3'
_chemical_formula_weight 289.37
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_int_tables_number 33
_symmetry_space_group_name_Hall 'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
_cell_length_a 14.616(3)
_cell_length_b 8.8915(18)
_cell_length_c 24.367(5)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 3166.8(11)
_cell_formula_units_Z 8
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 4860
_cell_measurement_theta_min 2.44
_cell_measurement_theta_max 23.02
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.68
_exptl_crystal_size_mid 0.64
_exptl_crystal_size_min 0.47
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.214
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1232
_exptl_absorpt_coefficient_mu 0.073
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9518
_exptl_absorpt_correction_T_max 0.9667
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 37351
_diffrn_reflns_av_R_equivalents 0.0626
_diffrn_reflns_av_sigmaI/netI 0.0409
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -31
_diffrn_reflns_limit_l_max 31
_diffrn_reflns_theta_min 1.67
_diffrn_reflns_theta_max 28.30
_reflns_number_total 3996
_reflns_number_gt 2240
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The disordered isopropyl group of the second molecule was refined as having
50:50 site occupancy disorder of methyl groups. Constraints were placed on
initial refinement cycles (DFIX 1.53) for C-C bond lengths and (DANG 2.48)
for the distance between corresponding methyl C atoms. Methyl H atoms were
placed in idealized positions for a disorder methyl group (HFIX 123).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0868P)^2^+0.2396P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.0098(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 3996
_refine_ls_number_parameters 417
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.1129
_refine_ls_R_factor_gt 0.0517
_refine_ls_wR_factor_ref 0.1588
_refine_ls_wR_factor_gt 0.1225
_refine_ls_goodness_of_fit_ref 1.022
_refine_ls_restrained_S_all 1.021
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.94976(19) 0.4561(3) 0.38023(13) 0.0468(7) Uani 1 1 d . . .
N2 N 0.8880(3) 0.2311(4) 0.41315(19) 0.0590(11) Uani 1 1 d . . .
N3 N 1.0514(2) 0.4478(4) 0.30753(14) 0.0557(8) Uani 1 1 d . . .
C1 C 0.8884(2) 0.3805(4) 0.41484(16) 0.0456(8) Uani 1 1 d . . .
C2 C 0.8313(3) 0.4607(5) 0.44896(17) 0.0553(10) Uani 1 1 d . . .
H2A H 0.8326 0.5652 0.4490 0.066 Uiso 1 1 calc R . .
C3 C 0.7726(3) 0.3845(5) 0.48281(19) 0.0697(12) Uani 1 1 d . . .
H3A H 0.7335 0.4371 0.5060 0.084 Uiso 1 1 calc R . .
C4 C 0.7718(4) 0.2300(6) 0.4823(3) 0.0718(16) Uani 1 1 d . . .
H4A H 0.7335 0.1761 0.5056 0.086 Uiso 1 1 calc R . .
C5 C 0.8292(3) 0.1575(5) 0.4464(2) 0.0702(12) Uani 1 1 d . . .
H5A H 0.8275 0.0531 0.4449 0.084 Uiso 1 1 calc R . .
C6 C 1.0259(2) 0.3868(4) 0.35521(15) 0.0454(8) Uani 1 1 d . . .
C7 C 1.0757(3) 0.2723(5) 0.3796(2) 0.0557(12) Uani 1 1 d . . .
H7A H 1.0580 0.2334 0.4134 0.067 Uiso 1 1 calc R . .
C8 C 1.1510(3) 0.2174(5) 0.3533(2) 0.0642(12) Uani 1 1 d . . .
H8A H 1.1848 0.1400 0.3691 0.077 Uiso 1 1 calc R . .
C9 C 1.1769(4) 0.2758(5) 0.3039(3) 0.0655(14) Uani 1 1 d . . .
H9A H 1.2270 0.2377 0.2849 0.079 Uiso 1 1 calc R . .
C10 C 1.1266(3) 0.3922(5) 0.28332(19) 0.0663(11) Uani 1 1 d . . .
H10A H 1.1457 0.4356 0.2505 0.080 Uiso 1 1 calc R . .
C11 C 0.9289(3) 0.6092(4) 0.36485(17) 0.0461(9) Uani 1 1 d . . .
C12 C 0.8594(3) 0.6350(5) 0.3274(2) 0.0538(11) Uani 1 1 d . . .
H12A H 0.8277 0.5542 0.3124 0.065 Uiso 1 1 calc R . .
C13 C 0.8369(3) 0.7784(5) 0.3124(2) 0.0599(13) Uani 1 1 d . . .
H13A H 0.7897 0.7948 0.2875 0.072 Uiso 1 1 calc R . .
C14 C 0.8836(3) 0.8971(5) 0.3339(2) 0.0616(12) Uani 1 1 d . . .
H14A H 0.8685 0.9946 0.3235 0.074 Uiso 1 1 calc R . .
C15 C 0.9529(3) 0.8733(4) 0.3707(2) 0.0565(11) Uani 1 1 d . . .
H15A H 0.9841 0.9558 0.3848 0.068 Uiso 1 1 calc R . .
C16 C 0.9782(3) 0.7293(4) 0.3876(2) 0.0482(11) Uani 1 1 d . . .
C17 C 1.0545(3) 0.7051(5) 0.42883(19) 0.0586(10) Uani 1 1 d . . .
H17A H 1.0502 0.6010 0.4418 0.070 Uiso 1 1 calc R . .
C18 C 1.0462(4) 0.8076(8) 0.4789(3) 0.0991(19) Uani 1 1 d . . .
H18A H 1.0953 0.7868 0.5039 0.149 Uiso 1 1 calc R . .
H18B H 0.9887 0.7897 0.4968 0.149 Uiso 1 1 calc R . .
H18C H 1.0494 0.9107 0.4674 0.149 Uiso 1 1 calc R . .
C19 C 1.1469(4) 0.7234(8) 0.4020(3) 0.093(2) Uani 1 1 d . . .
H19A H 1.1515 0.6563 0.3713 0.139 Uiso 1 1 calc R . .
H19B H 1.1941 0.7004 0.4281 0.139 Uiso 1 1 calc R . .
H19C H 1.1538 0.8253 0.3896 0.139 Uiso 1 1 calc R . .
N4 N 0.30003(19) 0.9437(3) 0.15759(13) 0.0476(7) Uani 1 1 d . . .
N5 N 0.3609(3) 0.7211(4) 0.12265(19) 0.0579(10) Uani 1 1 d . . .
N6 N 0.1946(2) 0.9426(4) 0.22780(14) 0.0567(8) Uani 1 1 d . . .
C20 C 0.3591(2) 0.8701(4) 0.12158(15) 0.0446(8) Uani 1 1 d . . .
C21 C 0.4164(3) 0.9525(5) 0.08729(17) 0.0559(10) Uani 1 1 d . . .
H21A H 0.4153 1.0571 0.0877 0.067 Uiso 1 1 calc R . .
C22 C 0.4747(3) 0.8763(6) 0.05288(19) 0.0694(12) Uani 1 1 d . . .
H22A H 0.5130 0.9294 0.0294 0.083 Uiso 1 1 calc R . .
C23 C 0.4764(4) 0.7232(7) 0.0531(3) 0.0730(15) Uani 1 1 d . . .
H23A H 0.5158 0.6698 0.0302 0.088 Uiso 1 1 calc R . .
C24 C 0.4189(3) 0.6519(5) 0.0877(2) 0.0720(13) Uani 1 1 d . . .
H24A H 0.4193 0.5473 0.0875 0.086 Uiso 1 1 calc R . .
C25 C 0.2217(2) 0.8777(4) 0.18184(15) 0.0448(8) Uani 1 1 d . . .
C26 C 0.1739(3) 0.7597(4) 0.1571(3) 0.0540(13) Uani 1 1 d . . .
H26A H 0.1938 0.7164 0.1245 0.065 Uiso 1 1 calc R . .
C27 C 0.0955(3) 0.7103(5) 0.1832(2) 0.0681(14) Uani 1 1 d . . .
H27A H 0.0616 0.6324 0.1679 0.082 Uiso 1 1 calc R . .
C28 C 0.0670(4) 0.7747(6) 0.2315(3) 0.0655(14) Uani 1 1 d . . .
H28A H 0.0152 0.7404 0.2498 0.079 Uiso 1 1 calc R . .
C29 C 0.1174(3) 0.8903(5) 0.25120(19) 0.0646(11) Uani 1 1 d . . .
H29A H 0.0974 0.9369 0.2832 0.077 Uiso 1 1 calc R . .
C30 C 0.3177(2) 1.1003(4) 0.17096(17) 0.0457(9) Uani 1 1 d . . .
C31 C 0.2666(3) 1.2147(5) 0.1481(2) 0.0512(11) Uani 1 1 d . B .
C32 C 0.2903(3) 1.3606(5) 0.1624(2) 0.0641(12) Uani 1 1 d . . .
H32A H 0.2577 1.4401 0.1471 0.077 Uiso 1 1 calc R . .
C33 C 0.3605(4) 1.3919(5) 0.1984(2) 0.0692(14) Uani 1 1 d . . .
H33A H 0.3743 1.4911 0.2072 0.083 Uiso 1 1 calc R . .
C34 C 0.4099(4) 1.2770(5) 0.2212(3) 0.0627(14) Uani 1 1 d . . .
H34A H 0.4571 1.2975 0.2457 0.075 Uiso 1 1 calc R . .
C35 C 0.3888(3) 1.1300(5) 0.2074(2) 0.0515(10) Uani 1 1 d . . .
H35A H 0.4222 1.0511 0.2224 0.062 Uiso 1 1 calc R . .
C36 C 0.1883(3) 1.1806(5) 0.10865(19) 0.0665(12) Uani 1 1 d . . .
H36A H 0.1678 1.0802 0.1165 0.080 Uiso 0.50 1 d PR A 1
H36B H 0.1930 1.0764 0.0987 0.080 Uiso 0.50 1 d PR A 2
C37A C 0.2130(14) 1.183(2) 0.0504(8) 0.104(7) Uani 0.50 1 d P B 1
H37A H 0.1602 1.1593 0.0286 0.156 Uiso 0.25 1 calc PR B 1
H37B H 0.2601 1.1101 0.0436 0.156 Uiso 0.25 1 calc PR B 1
H37C H 0.2350 1.2813 0.0407 0.156 Uiso 0.25 1 calc PR B 1
H37D H 0.2767 1.2078 0.0467 0.156 Uiso 0.25 1 calc PR B 1
H37E H 0.1768 1.2571 0.0317 0.156 Uiso 0.25 1 calc PR B 1
H37F H 0.2019 1.0858 0.0346 0.156 Uiso 0.25 1 calc PR B 1
C38A C 0.1025(11) 1.290(2) 0.1216(9) 0.119(7) Uani 0.50 1 d P B 1
H38A H 0.0880 1.2851 0.1600 0.178 Uiso 0.25 1 calc PR B 1
H38B H 0.0504 1.2584 0.1005 0.178 Uiso 0.25 1 calc PR B 1
H38C H 0.1181 1.3915 0.1120 0.178 Uiso 0.25 1 calc PR B 1
H38D H 0.0830 1.3383 0.0884 0.178 Uiso 0.25 1 calc PR B 1
H38E H 0.1206 1.3649 0.1478 0.178 Uiso 0.25 1 calc PR B 1
H38F H 0.0529 1.2318 0.1364 0.178 Uiso 0.25 1 calc PR B 1
C37B C 0.2039(12) 1.272(2) 0.0563(7) 0.102(6) Uani 0.50 1 d P B 2
H37G H 0.2644 1.2525 0.0426 0.153 Uiso 0.25 1 calc PR B 2
H37H H 0.1974 1.3768 0.0642 0.153 Uiso 0.25 1 calc PR B 2
H37I H 0.1597 1.2427 0.0291 0.153 Uiso 0.25 1 calc PR B 2
H37J H 0.1499 1.3288 0.0480 0.153 Uiso 0.25 1 calc PR B 2
H37K H 0.2169 1.2045 0.0264 0.153 Uiso 0.25 1 calc PR B 2
H37L H 0.2546 1.3387 0.0615 0.153 Uiso 0.25 1 calc PR B 2
C38B C 0.0985(9) 1.1998(15) 0.1304(7) 0.077(4) Uani 0.50 1 d P B 2
H38G H 0.0541 1.1746 0.1029 0.115 Uiso 0.25 1 calc PR B 2
H38H H 0.0903 1.3026 0.1415 0.115 Uiso 0.25 1 calc PR B 2
H38I H 0.0906 1.1351 0.1616 0.115 Uiso 0.25 1 calc PR B 2
H38J H 0.1026 1.2336 0.1678 0.115 Uiso 0.25 1 calc PR B 2
H38K H 0.0664 1.1057 0.1292 0.115 Uiso 0.25 1 calc PR B 2
H38L H 0.0661 1.2731 0.1090 0.115 Uiso 0.25 1 calc PR B 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0453(15) 0.0369(14) 0.0583(18) -0.0008(14) 0.0114(15) 0.0018(13)
N2 0.054(2) 0.0522(19) 0.071(3) 0.0032(19) 0.012(2) -0.0049(15)
N3 0.0549(18) 0.0540(17) 0.058(2) 0.0000(16) 0.0085(16) 0.0045(15)
C1 0.0401(19) 0.0439(19) 0.053(2) 0.0019(18) 0.0011(17) -0.0034(15)
C2 0.055(2) 0.054(2) 0.057(2) -0.0048(19) 0.0123(19) -0.0013(18)
C3 0.067(3) 0.079(3) 0.063(3) -0.002(3) 0.021(2) -0.002(2)
C4 0.062(3) 0.080(3) 0.073(4) 0.014(3) 0.021(3) -0.005(2)
C5 0.070(3) 0.057(3) 0.084(3) 0.014(2) 0.013(3) -0.010(2)
C6 0.0427(19) 0.0415(18) 0.052(2) -0.0037(16) 0.0022(16) -0.0021(15)
C7 0.052(3) 0.056(2) 0.059(3) 0.009(2) 0.004(3) 0.0037(18)
C8 0.053(3) 0.062(2) 0.078(3) -0.001(3) -0.005(2) 0.013(2)
C9 0.055(3) 0.070(3) 0.071(4) -0.011(3) 0.013(3) 0.010(2)
C10 0.064(3) 0.072(3) 0.063(2) 0.000(2) 0.016(2) 0.009(2)
C11 0.045(2) 0.0407(19) 0.053(2) 0.0019(17) 0.0091(19) 0.0026(15)
C12 0.046(2) 0.056(3) 0.060(3) -0.005(2) 0.005(2) -0.0027(19)
C13 0.056(3) 0.062(3) 0.062(3) 0.004(2) 0.002(2) 0.013(2)
C14 0.063(3) 0.052(2) 0.070(3) 0.008(2) 0.009(3) 0.009(2)
C15 0.064(3) 0.043(2) 0.062(3) -0.0068(19) 0.010(2) -0.011(2)
C16 0.045(2) 0.051(2) 0.048(3) 0.0024(18) 0.005(2) 0.0001(17)
C17 0.054(2) 0.060(2) 0.062(3) 0.001(2) -0.001(2) -0.0053(19)
C18 0.083(4) 0.146(5) 0.068(4) -0.025(4) -0.004(3) 0.003(4)
C19 0.048(3) 0.132(5) 0.098(5) -0.015(4) -0.014(3) -0.004(3)
N4 0.0445(15) 0.0395(14) 0.0587(19) -0.0023(14) 0.0082(14) -0.0035(13)
N5 0.053(2) 0.0529(19) 0.068(3) -0.0026(18) 0.013(2) 0.0058(17)
N6 0.0552(19) 0.0582(19) 0.0567(19) -0.0022(16) 0.0092(16) -0.0062(15)
C20 0.0398(19) 0.048(2) 0.046(2) 0.0009(18) 0.0026(16) -0.0005(15)
C21 0.052(2) 0.060(2) 0.056(2) 0.004(2) 0.0077(19) -0.0004(18)
C22 0.061(3) 0.090(4) 0.057(3) -0.001(3) 0.015(2) -0.002(2)
C23 0.062(3) 0.091(4) 0.066(4) -0.018(3) 0.014(3) 0.013(3)
C24 0.069(3) 0.059(3) 0.088(3) -0.012(3) 0.011(3) 0.008(2)
C25 0.0396(19) 0.0432(19) 0.052(2) 0.0071(17) 0.0028(16) 0.0024(15)
C26 0.046(3) 0.053(2) 0.064(3) -0.0047(18) 0.004(3) -0.0056(16)
C27 0.051(3) 0.060(2) 0.093(4) 0.001(3) 0.002(3) -0.015(2)
C28 0.050(3) 0.074(3) 0.073(4) 0.010(3) 0.018(3) -0.011(2)
C29 0.062(3) 0.070(3) 0.061(2) 0.002(2) 0.020(2) -0.005(2)
C30 0.038(2) 0.0447(19) 0.054(2) 0.0004(17) 0.0087(18) -0.0039(15)
C31 0.046(2) 0.053(2) 0.055(3) 0.003(2) 0.005(2) 0.0043(18)
C32 0.071(3) 0.048(2) 0.073(3) 0.009(2) 0.015(3) 0.005(2)
C33 0.085(3) 0.042(2) 0.080(3) -0.012(2) 0.017(3) -0.010(2)
C34 0.058(3) 0.061(3) 0.069(4) -0.009(2) -0.001(3) -0.014(2)
C35 0.049(2) 0.050(2) 0.055(3) 0.0004(19) 0.003(2) -0.0016(18)
C36 0.062(3) 0.065(3) 0.072(3) 0.013(2) -0.008(2) 0.005(2)
C37A 0.089(8) 0.141(15) 0.082(9) -0.048(11) -0.009(6) 0.029(10)
C38A 0.066(8) 0.166(16) 0.125(16) -0.076(15) -0.022(9) 0.044(12)
C37B 0.075(9) 0.173(17) 0.057(10) 0.036(11) -0.014(7) -0.018(11)
C38B 0.041(5) 0.093(9) 0.096(9) 0.003(8) 0.010(5) -0.001(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.403(4) . ?
N1 C6 1.411(4) . ?
N1 C11 1.445(5) . ?
N2 C1 1.328(5) . ?
N2 C5 1.350(6) . ?
N3 C6 1.335(5) . ?
N3 C10 1.343(5) . ?
C1 C2 1.377(5) . ?
C2 C3 1.369(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.374(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(7) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.385(6) . ?
C7 C8 1.365(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.365(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.364(7) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.384(6) . ?
C11 C16 1.403(6) . ?
C12 C13 1.366(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.362(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.369(7) . ?
C14 H14A 0.9300 . ?
C15 C16 1.395(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.517(6) . ?
C17 C19 1.509(8) . ?
C17 C18 1.527(8) . ?
C17 H17A 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N4 C20 1.395(4) . ?
N4 C25 1.416(4) . ?
N4 C30 1.453(4) . ?
N5 C20 1.325(5) . ?
N5 C24 1.350(6) . ?
N6 C25 1.321(5) . ?
N6 C29 1.346(5) . ?
C20 C21 1.392(5) . ?
C21 C22 1.374(6) . ?
C21 H21A 0.9300 . ?
C22 C23 1.362(7) . ?
C22 H22A 0.9300 . ?
C23 C24 1.350(8) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 C26 1.398(6) . ?
C26 C27 1.383(7) . ?
C26 H26A 0.9300 . ?
C27 C28 1.373(8) . ?
C27 H27A 0.9300 . ?
C28 C29 1.353(7) . ?
C28 H28A 0.9300 . ?
C29 H29A 0.9300 . ?
C30 C31 1.379(6) . ?
C30 C35 1.392(6) . ?
C31 C32 1.387(6) . ?
C31 C36 1.526(7) . ?
C32 C33 1.379(7) . ?
C32 H32A 0.9300 . ?
C33 C34 1.368(7) . ?
C33 H33A 0.9300 . ?
C34 C35 1.384(6) . ?
C34 H34A 0.9300 . ?
C35 H35A 0.9300 . ?
C36 C38B 1.426(14) . ?
C36 C37A 1.465(19) . ?
C36 C37B 1.528(17) . ?
C36 C38A 1.619(16) . ?
C36 H36A 0.9601 . ?
C36 H36B 0.9600 . ?
C37A H37A 0.9600 . ?
C37A H37B 0.9600 . ?
C37A H37C 0.9600 . ?
C37A H37D 0.9600 . ?
C37A H37E 0.9600 . ?
C37A H37F 0.9600 . ?
C38A H38A 0.9600 . ?
C38A H38B 0.9600 . ?
C38A H38C 0.9600 . ?
C38A H38D 0.9600 . ?
C38A H38E 0.9600 . ?
C38A H38F 0.9600 . ?
C37B H37G 0.9600 . ?
C37B H37H 0.9600 . ?
C37B H37I 0.9600 . ?
C37B H37J 0.9600 . ?
C37B H37K 0.9600 . ?
C37B H37L 0.9600 . ?
C38B H38G 0.9600 . ?
C38B H38H 0.9600 . ?
C38B H38I 0.9600 . ?
C38B H38J 0.9600 . ?
C38B H38K 0.9600 . ?
C38B H38L 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 123.7(3) . . ?
C1 N1 C11 118.2(3) . . ?
C6 N1 C11 117.8(3) . . ?
C1 N2 C5 117.9(4) . . ?
C6 N3 C10 117.4(3) . . ?
N2 C1 C2 122.3(4) . . ?
N2 C1 N1 117.6(3) . . ?
C2 C1 N1 120.1(3) . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C5 C4 C3 118.0(5) . . ?
C5 C4 H4A 121.0 . . ?
C3 C4 H4A 121.0 . . ?
N2 C5 C4 123.0(4) . . ?
N2 C5 H5A 118.5 . . ?
C4 C5 H5A 118.5 . . ?
N3 C6 C7 121.8(4) . . ?
N3 C6 N1 114.7(3) . . ?
C7 C6 N1 123.3(4) . . ?
C8 C7 C6 119.0(5) . . ?
C8 C7 H7A 120.5 . . ?
C6 C7 H7A 120.5 . . ?
C9 C8 C7 120.1(5) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C10 C9 C8 117.6(5) . . ?
C10 C9 H9A 121.2 . . ?
C8 C9 H9A 121.2 . . ?
N3 C10 C9 124.0(4) . . ?
N3 C10 H10A 118.0 . . ?
C9 C10 H10A 118.0 . . ?
C12 C11 C16 120.8(4) . . ?
C12 C11 N1 118.8(3) . . ?
C16 C11 N1 120.4(4) . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 120.0(5) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C14 C15 C16 122.1(4) . . ?
C14 C15 H15A 118.9 . . ?
C16 C15 H15A 118.9 . . ?
C15 C16 C11 116.4(4) . . ?
C15 C16 C17 121.4(4) . . ?
C11 C16 C17 122.1(4) . . ?
C19 C17 C16 110.8(4) . . ?
C19 C17 C18 110.7(4) . . ?
C16 C17 C18 112.7(4) . . ?
C19 C17 H17A 107.5 . . ?
C16 C17 H17A 107.5 . . ?
C18 C17 H17A 107.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 N4 C25 124.6(3) . . ?
C20 N4 C30 118.7(3) . . ?
C25 N4 C30 116.6(3) . . ?
C20 N5 C24 117.1(4) . . ?
C25 N6 C29 117.4(3) . . ?
N5 C20 C21 121.8(4) . . ?
N5 C20 N4 118.0(3) . . ?
C21 C20 N4 120.2(3) . . ?
C22 C21 C20 118.6(4) . . ?
C22 C21 H21A 120.7 . . ?
C20 C21 H21A 120.7 . . ?
C23 C22 C21 120.2(4) . . ?
C23 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
C24 C23 C22 117.4(5) . . ?
C24 C23 H23A 121.3 . . ?
C22 C23 H23A 121.3 . . ?
C23 C24 N5 124.9(4) . . ?
C23 C24 H24A 117.6 . . ?
N5 C24 H24A 117.6 . . ?
N6 C25 C26 122.9(4) . . ?
N6 C25 N4 114.5(3) . . ?
C26 C25 N4 122.4(4) . . ?
C27 C26 C25 117.0(5) . . ?
C27 C26 H26A 121.5 . . ?
C25 C26 H26A 121.5 . . ?
C28 C27 C26 120.9(5) . . ?
C28 C27 H27A 119.5 . . ?
C26 C27 H27A 119.5 . . ?
C29 C28 C27 117.1(5) . . ?
C29 C28 H28A 121.4 . . ?
C27 C28 H28A 121.4 . . ?
N6 C29 C28 124.6(4) . . ?
N6 C29 H29A 117.7 . . ?
C28 C29 H29A 117.7 . . ?
C31 C30 C35 121.5(4) . . ?
C31 C30 N4 121.3(4) . . ?
C35 C30 N4 117.2(3) . . ?
C30 C31 C32 117.0(4) . . ?
C30 C31 C36 121.0(4) . . ?
C32 C31 C36 122.1(4) . . ?
C33 C32 C31 122.2(4) . . ?
C33 C32 H32A 118.9 . . ?
C31 C32 H32A 118.9 . . ?
C34 C33 C32 120.0(4) . . ?
C34 C33 H33A 120.0 . . ?
C32 C33 H33A 120.0 . . ?
C33 C34 C35 119.2(5) . . ?
C33 C34 H34A 120.4 . . ?
C35 C34 H34A 120.4 . . ?
C34 C35 C30 120.0(4) . . ?
C34 C35 H35A 120.0 . . ?
C30 C35 H35A 120.0 . . ?
C38B C36 C37A 125.9(11) . . ?
C38B C36 C31 115.6(8) . . ?
C37A C36 C31 115.0(9) . . ?
C38B C36 C37B 112.6(10) . . ?
C31 C36 C37B 108.0(8) . . ?
C37A C36 C38A 111.8(11) . . ?
C31 C36 C38A 109.8(7) . . ?
C37A C36 H36A 106.5 . . ?
C31 C36 H36A 107.0 . . ?
C37B C36 H36A 134.8 . . ?
C38A C36 H36A 106.2 . . ?
C38B C36 H36B 106.0 . . ?
C37A C36 H36B 75.6 . . ?
C31 C36 H36B 107.3 . . ?
C37B C36 H36B 106.8 . . ?
C38A C36 H36B 133.2 . . ?
C36 C37A H37A 109.5 . . ?
C36 C37A H37B 109.5 . . ?
H36B C37A H37B 81.5 . . ?
H37A C37A H37B 109.5 . . ?
C36 C37A H37C 109.5 . . ?
H36B C37A H37C 144.2 . . ?
H37A C37A H37C 109.5 . . ?
H37B C37A H37C 109.5 . . ?
C36 C37A H37D 109.5 . . ?
H37A C37A H37D 141.1 . . ?
H37B C37A H37D 56.3 . . ?
H37C C37A H37D 56.3 . . ?
C36 C37A H37E 109.5 . . ?
H36B C37A H37E 132.8 . . ?
H37A C37A H37E 56.3 . . ?
H37B C37A H37E 141.1 . . ?
H37C C37A H37E 56.3 . . ?
H37D C37A H37E 109.5 . . ?
C36 C37A H37F 109.5 . . ?
H36B C37A H37F 73.7 . . ?
H37A C37A H37F 56.3 . . ?
H37B C37A H37F 56.3 . . ?
H37C C37A H37F 141.1 . . ?
H37D C37A H37F 109.5 . . ?
H37E C37A H37F 109.5 . . ?
C36 C38A H38A 109.5 . . ?
C36 C38A H38B 109.5 . . ?
H38A C38A H38B 109.5 . . ?
C36 C38A H38C 109.5 . . ?
H38A C38A H38C 109.5 . . ?
H38B C38A H38C 109.5 . . ?
C36 C38A H38D 109.5 . . ?
H38A C38A H38D 141.1 . . ?
H38B C38A H38D 56.3 . . ?
H38C C38A H38D 56.3 . . ?
C36 C38A H38E 109.5 . . ?
H38A C38A H38E 56.3 . . ?
H38B C38A H38E 141.1 . . ?
H38C C38A H38E 56.3 . . ?
H38D C38A H38E 109.5 . . ?
C36 C38A H38F 109.5 . . ?
H38A C38A H38F 56.3 . . ?
H38B C38A H38F 56.3 . . ?
H38C C38A H38F 141.1 . . ?
H38D C38A H38F 109.5 . . ?
H38E C38A H38F 109.5 . . ?
C36 C37B H37G 109.5 . . ?
C36 C37B H37H 109.5 . . ?
H37G C37B H37H 109.5 . . ?
C36 C37B H37I 109.5 . . ?
H37G C37B H37I 109.5 . . ?
H37H C37B H37I 109.5 . . ?
C36 C37B H37J 109.5 . . ?
H37G C37B H37J 141.1 . . ?
H37H C37B H37J 56.3 . . ?
H37I C37B H37J 56.3 . . ?
C36 C37B H37K 109.5 . . ?
H37G C37B H37K 56.3 . . ?
H37H C37B H37K 141.1 . . ?
H37I C37B H37K 56.3 . . ?
H37J C37B H37K 109.5 . . ?
C36 C37B H37L 109.5 . . ?
H37G C37B H37L 56.3 . . ?
H37H C37B H37L 56.3 . . ?
H37I C37B H37L 141.1 . . ?
H37J C37B H37L 109.5 . . ?
H37K C37B H37L 109.5 . . ?
C36 C38B H38G 109.5 . . ?
C36 C38B H38H 109.5 . . ?
H38G C38B H38H 109.5 . . ?
C36 C38B H38I 109.5 . . ?
H36A C38B H38I 80.6 . . ?
H38G C38B H38I 109.5 . . ?
H38H C38B H38I 109.5 . . ?
C36 C38B H38J 109.5 . . ?
H38G C38B H38J 141.1 . . ?
H38H C38B H38J 56.3 . . ?
H38I C38B H38J 56.3 . . ?
C36 C38B H38K 109.5 . . ?
H38G C38B H38K 56.3 . . ?
H38H C38B H38K 141.1 . . ?
H38I C38B H38K 56.3 . . ?
H38J C38B H38K 109.5 . . ?
C36 C38B H38L 109.5 . . ?
H38G C38B H38L 56.3 . . ?
H38H C38B H38L 56.3 . . ?
H38I C38B H38L 141.1 . . ?
H38J C38B H38L 109.5 . . ?
H38K C38B H38L 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C1 C2 0.0(6) . . . . ?
C5 N2 C1 N1 179.9(4) . . . . ?
C6 N1 C1 N2 -17.4(5) . . . . ?
C11 N1 C1 N2 156.1(4) . . . . ?
C6 N1 C1 C2 162.6(3) . . . . ?
C11 N1 C1 C2 -23.9(5) . . . . ?
N2 C1 C2 C3 0.7(6) . . . . ?
N1 C1 C2 C3 -179.3(4) . . . . ?
C1 C2 C3 C4 0.2(7) . . . . ?
C2 C3 C4 C5 -1.6(8) . . . . ?
C1 N2 C5 C4 -1.5(8) . . . . ?
C3 C4 C5 N2 2.3(9) . . . . ?
C10 N3 C6 C7 1.1(6) . . . . ?
C10 N3 C6 N1 176.3(3) . . . . ?
C1 N1 C6 N3 151.5(3) . . . . ?
C11 N1 C6 N3 -22.0(5) . . . . ?
C1 N1 C6 C7 -33.5(5) . . . . ?
C11 N1 C6 C7 153.0(4) . . . . ?
N3 C6 C7 C8 -2.1(7) . . . . ?
N1 C6 C7 C8 -176.8(4) . . . . ?
C6 C7 C8 C9 0.5(7) . . . . ?
C7 C8 C9 C10 1.9(8) . . . . ?
C6 N3 C10 C9 1.5(7) . . . . ?
C8 C9 C10 N3 -3.0(8) . . . . ?
C1 N1 C11 C12 -73.3(5) . . . . ?
C6 N1 C11 C12 100.5(4) . . . . ?
C1 N1 C11 C16 106.6(4) . . . . ?
C6 N1 C11 C16 -79.5(5) . . . . ?
C16 C11 C12 C13 -0.7(6) . . . . ?
N1 C11 C12 C13 179.2(4) . . . . ?
C11 C12 C13 C14 0.7(8) . . . . ?
C12 C13 C14 C15 -0.3(8) . . . . ?
C13 C14 C15 C16 -0.1(7) . . . . ?
C14 C15 C16 C11 0.0(7) . . . . ?
C14 C15 C16 C17 -179.4(4) . . . . ?
C12 C11 C16 C15 0.4(6) . . . . ?
N1 C11 C16 C15 -179.6(3) . . . . ?
C12 C11 C16 C17 179.8(4) . . . . ?
N1 C11 C16 C17 -0.1(6) . . . . ?
C15 C16 C17 C19 -77.3(6) . . . . ?
C11 C16 C17 C19 103.3(5) . . . . ?
C15 C16 C17 C18 47.3(6) . . . . ?
C11 C16 C17 C18 -132.1(5) . . . . ?
C24 N5 C20 C21 -1.9(6) . . . . ?
C24 N5 C20 N4 -179.6(4) . . . . ?
C25 N4 C20 N5 -21.9(5) . . . . ?
C30 N4 C20 N5 159.3(4) . . . . ?
C25 N4 C20 C21 160.4(3) . . . . ?
C30 N4 C20 C21 -18.4(5) . . . . ?
N5 C20 C21 C22 1.5(6) . . . . ?
N4 C20 C21 C22 179.1(4) . . . . ?
C20 C21 C22 C23 -0.7(7) . . . . ?
C21 C22 C23 C24 0.4(8) . . . . ?
C22 C23 C24 N5 -1.0(9) . . . . ?
C20 N5 C24 C23 1.8(8) . . . . ?
C29 N6 C25 C26 0.3(6) . . . . ?
C29 N6 C25 N4 176.3(3) . . . . ?
C20 N4 C25 N6 156.9(3) . . . . ?
C30 N4 C25 N6 -24.3(5) . . . . ?
C20 N4 C25 C26 -27.1(5) . . . . ?
C30 N4 C25 C26 151.7(4) . . . . ?
N6 C25 C26 C27 -0.7(7) . . . . ?
N4 C25 C26 C27 -176.4(4) . . . . ?
C25 C26 C27 C28 -0.3(8) . . . . ?
C26 C27 C28 C29 1.7(8) . . . . ?
C25 N6 C29 C28 1.2(7) . . . . ?
C27 C28 C29 N6 -2.2(8) . . . . ?
C20 N4 C30 C31 103.8(4) . . . . ?
C25 N4 C30 C31 -75.1(5) . . . . ?
C20 N4 C30 C35 -75.7(5) . . . . ?
C25 N4 C30 C35 105.4(4) . . . . ?
C35 C30 C31 C32 1.1(7) . . . . ?
N4 C30 C31 C32 -178.3(3) . . . . ?
C35 C30 C31 C36 -179.5(4) . . . . ?
N4 C30 C31 C36 1.1(6) . . . . ?
C30 C31 C32 C33 -1.1(7) . . . . ?
C36 C31 C32 C33 179.5(5) . . . . ?
C31 C32 C33 C34 0.4(8) . . . . ?
C32 C33 C34 C35 0.4(9) . . . . ?
C33 C34 C35 C30 -0.4(8) . . . . ?
C31 C30 C35 C34 -0.4(7) . . . . ?
N4 C30 C35 C34 179.1(4) . . . . ?
C30 C31 C36 C38B 106.1(7) . . . . ?
C32 C31 C36 C38B -74.5(8) . . . . ?
C30 C31 C36 C37A -93.7(9) . . . . ?
C32 C31 C36 C37A 85.7(9) . . . . ?
C30 C31 C36 C37B -126.7(9) . . . . ?
C32 C31 C36 C37B 52.7(10) . . . . ?
C30 C31 C36 C38A 139.1(10) . . . . ?
C32 C31 C36 C38A -41.5(11) . . . . ?
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full 28.30
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.319
_refine_diff_density_min -0.198
_refine_diff_density_rms 0.045
_exptl_crystal_recrystallization_method
'slow evap. of 4:1 hexanes:CH2Cl2 solution'
_diffrn_ambient_pressure 101.33
# Attachment 'Ph(iPr)2DPA.CIF'
data_iprphdpa
_database_code_depnum_ccdc_archive 'CCDC 720340'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
N-(2,6-diisopropyl)phenyl-N,N-(2,2'-dipyridyl)amine
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C22 H25 N3'
_chemical_formula_sum 'C22 H25 N3'
_chemical_formula_weight 331.45
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_int_tables_number 2
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.3660(17)
_cell_length_b 14.390(3)
_cell_length_c 16.817(3)
_cell_angle_alpha 100.90(3)
_cell_angle_beta 100.91(3)
_cell_angle_gamma 95.05(3)
_cell_volume 1935.8(7)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 2758
_cell_measurement_theta_min 2.50
_cell_measurement_theta_max 22.02
_exptl_crystal_description block
_exptl_crystal_colour 'light yellow'
_exptl_crystal_size_max 1.08
_exptl_crystal_size_mid 0.69
_exptl_crystal_size_min 0.63
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.137
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 712
_exptl_absorpt_coefficient_mu 0.068
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9305
_exptl_absorpt_correction_T_max 0.9586
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 22485
_diffrn_reflns_av_R_equivalents 0.0897
_diffrn_reflns_av_sigmaI/netI 0.1958
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_theta_min 1.26
_diffrn_reflns_theta_max 28.50
_reflns_number_total 9008
_reflns_number_gt 2967
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0942P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.024(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 9008
_refine_ls_number_parameters 460
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.2040
_refine_ls_R_factor_gt 0.0608
_refine_ls_wR_factor_ref 0.1920
_refine_ls_wR_factor_gt 0.1460
_refine_ls_goodness_of_fit_ref 0.821
_refine_ls_restrained_S_all 0.821
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6109(2) 0.75542(14) 0.20015(11) 0.0371(5) Uani 1 1 d . . .
N2 N 0.7453(3) 0.89677(17) 0.18847(14) 0.0629(7) Uani 1 1 d . . .
N3 N 0.4501(3) 0.66004(15) 0.07940(12) 0.0495(6) Uani 1 1 d . . .
C1 C 0.6073(3) 0.83944(17) 0.16909(14) 0.0380(6) Uani 1 1 d . . .
C2 C 0.4624(4) 0.86224(19) 0.12519(15) 0.0483(7) Uani 1 1 d . . .
H2B H 0.3651 0.8208 0.1129 0.058 Uiso 1 1 calc R . .
C3 C 0.4685(5) 0.9486(2) 0.10072(16) 0.0617(9) Uani 1 1 d . . .
H3B H 0.3746 0.9655 0.0704 0.074 Uiso 1 1 calc R . .
C4 C 0.6103(5) 1.0087(2) 0.12059(18) 0.0732(10) Uani 1 1 d . . .
H4A H 0.6153 1.0674 0.1050 0.088 Uiso 1 1 calc R . .
C5 C 0.7466(5) 0.9807(2) 0.1644(2) 0.0828(11) Uani 1 1 d . . .
H5A H 0.8446 1.0217 0.1780 0.099 Uiso 1 1 calc R . .
C6 C 0.5163(3) 0.66936(17) 0.16003(15) 0.0367(6) Uani 1 1 d . . .
C7 C 0.4922(3) 0.59531(19) 0.20031(16) 0.0508(7) Uani 1 1 d . . .
H7A H 0.5374 0.6033 0.2565 0.061 Uiso 1 1 calc R . .
C8 C 0.4035(4) 0.5116(2) 0.15831(18) 0.0616(9) Uani 1 1 d . . .
H8A H 0.3880 0.4616 0.1851 0.074 Uiso 1 1 calc R . .
C9 C 0.3357(4) 0.5011(2) 0.07477(19) 0.0660(9) Uani 1 1 d . . .
H9A H 0.2741 0.4445 0.0439 0.079 Uiso 1 1 calc R . .
C10 C 0.3632(4) 0.5775(2) 0.04003(18) 0.0645(9) Uani 1 1 d . . .
H10A H 0.3172 0.5711 -0.0159 0.077 Uiso 1 1 calc R . .
C11 C 0.7380(3) 0.75546(17) 0.27228(14) 0.0395(7) Uani 1 1 d . . .
C12 C 0.8756(4) 0.71182(19) 0.26118(15) 0.0475(7) Uani 1 1 d . . .
C13 C 0.9911(4) 0.7089(2) 0.33151(18) 0.0660(9) Uani 1 1 d . . .
H13A H 1.0836 0.6790 0.3258 0.079 Uiso 1 1 calc R . .
C14 C 0.9719(4) 0.7490(2) 0.40906(18) 0.0742(10) Uani 1 1 d . . .
H14A H 1.0508 0.7461 0.4553 0.089 Uiso 1 1 calc R . .
C15 C 0.8364(4) 0.7933(2) 0.41846(16) 0.0618(9) Uani 1 1 d . . .
H15A H 0.8249 0.8210 0.4714 0.074 Uiso 1 1 calc R . .
C16 C 0.7154(4) 0.79752(18) 0.35036(15) 0.0469(7) Uani 1 1 d . . .
C17 C 0.9080(4) 0.6706(2) 0.17679(17) 0.0604(8) Uani 1 1 d . . .
H17A H 0.8139 0.6786 0.1352 0.072 Uiso 1 1 calc R . .
C18 C 0.5683(4) 0.8479(2) 0.36350(16) 0.0578(8) Uani 1 1 d . . .
H18A H 0.4952 0.8407 0.3092 0.069 Uiso 1 1 calc R . .
C19 C 1.0589(4) 0.7251(3) 0.1615(2) 0.0942(12) Uani 1 1 d . . .
H19A H 1.0458 0.7915 0.1678 0.141 Uiso 1 1 calc R . .
H19B H 1.0725 0.7006 0.1063 0.141 Uiso 1 1 calc R . .
H19C H 1.1540 0.7176 0.2006 0.141 Uiso 1 1 calc R . .
C20 C 0.4720(5) 0.8047(3) 0.4183(3) 0.1132(14) Uani 1 1 d . . .
H20A H 0.4465 0.7371 0.3975 0.170 Uiso 1 1 calc R . .
H20B H 0.3721 0.8328 0.4185 0.170 Uiso 1 1 calc R . .
H20C H 0.5365 0.8170 0.4738 0.170 Uiso 1 1 calc R . .
C21 C 0.9216(5) 0.5641(2) 0.1649(2) 0.0929(12) Uani 1 1 d . . .
H21A H 0.9450 0.5414 0.1114 0.139 Uiso 1 1 calc R . .
H21B H 0.8199 0.5305 0.1686 0.139 Uiso 1 1 calc R . .
H21C H 1.0085 0.5534 0.2071 0.139 Uiso 1 1 calc R . .
C22 C 0.6178(5) 0.9541(2) 0.3984(2) 0.0993(12) Uani 1 1 d . . .
H22A H 0.6735 0.9814 0.3617 0.149 Uiso 1 1 calc R . .
H22B H 0.6896 0.9635 0.4518 0.149 Uiso 1 1 calc R . .
H22C H 0.5214 0.9844 0.4037 0.149 Uiso 1 1 calc R . .
N1A N 1.2930(3) 1.25115(14) 0.29359(11) 0.0412(6) Uani 1 1 d . . .
N2A N 1.2740(3) 1.41179(16) 0.30733(13) 0.0605(7) Uani 1 1 d . . .
N3A N 1.1243(3) 1.15708(16) 0.35065(13) 0.0552(6) Uani 1 1 d . . .
C1A C 1.2735(3) 1.33775(18) 0.34344(15) 0.0422(7) Uani 1 1 d . . .
C2A C 1.2658(4) 1.3477(2) 0.42652(16) 0.0648(9) Uani 1 1 d . . .
H2AB H 1.2659 1.2950 0.4512 0.078 Uiso 1 1 calc R . .
C3A C 1.2581(5) 1.4358(2) 0.47072(19) 0.0834(11) Uani 1 1 d . . .
H3AB H 1.2532 1.4437 0.5263 0.100 Uiso 1 1 calc R . .
C4A C 1.2576(5) 1.5131(2) 0.4346(2) 0.0883(12) Uani 1 1 d . . .
H4AA H 1.2507 1.5737 0.4639 0.106 Uiso 1 1 calc R . .
C5A C 1.2675(5) 1.4969(2) 0.3531(2) 0.0801(11) Uani 1 1 d . . .
H5AA H 1.2699 1.5491 0.3279 0.096 Uiso 1 1 calc R . .
C6A C 1.2344(3) 1.16077(18) 0.30355(14) 0.0392(7) Uani 1 1 d . . .
C7A C 1.2887(4) 1.07956(19) 0.26603(16) 0.0570(8) Uani 1 1 d . . .
H7AA H 1.3686 1.0842 0.2348 0.068 Uiso 1 1 calc R . .
C8A C 1.2254(4) 0.9924(2) 0.27475(19) 0.0679(9) Uani 1 1 d . . .
H8AA H 1.2595 0.9372 0.2483 0.081 Uiso 1 1 calc R . .
C9A C 1.1109(4) 0.9868(2) 0.32288(19) 0.0666(9) Uani 1 1 d . . .
H9AA H 1.0667 0.9285 0.3308 0.080 Uiso 1 1 calc R . .
C10A C 1.0653(4) 1.0705(2) 0.35841(17) 0.0672(9) Uani 1 1 d . . .
H10B H 0.9869 1.0673 0.3907 0.081 Uiso 1 1 calc R . .
C11A C 1.3732(3) 1.25640(17) 0.22498(14) 0.0385(7) Uani 1 1 d . . .
C12A C 1.2784(3) 1.23585(17) 0.14413(15) 0.0431(7) Uani 1 1 d . . .
C13A C 1.3613(4) 1.23797(18) 0.08015(15) 0.0491(7) Uani 1 1 d . . .
H13B H 1.3017 1.2239 0.0258 0.059 Uiso 1 1 calc R . .
C14A C 1.5275(4) 1.26008(19) 0.09472(16) 0.0530(8) Uani 1 1 d . . .
H14B H 1.5799 1.2606 0.0507 0.064 Uiso 1 1 calc R . .
C15A C 1.6173(4) 1.28162(19) 0.17474(17) 0.0549(8) Uani 1 1 d . . .
H15B H 1.7305 1.2973 0.1843 0.066 Uiso 1 1 calc R . .
C16A C 1.5427(4) 1.28040(18) 0.24149(15) 0.0461(7) Uani 1 1 d . . .
C17A C 1.0933(4) 1.2158(2) 0.12469(16) 0.0583(8) Uani 1 1 d . . .
H17B H 1.0587 1.2108 0.1764 0.070 Uiso 1 1 calc R . .
C18A C 1.6489(4) 1.3048(2) 0.32964(16) 0.0643(9) Uani 1 1 d . . .
H18B H 1.5785 1.3288 0.3673 0.077 Uiso 1 1 calc R . .
C19A C 1.0304(5) 1.1219(3) 0.0631(2) 0.1038(13) Uani 1 1 d . . .
H19D H 1.0800 1.0711 0.0837 0.156 Uiso 1 1 calc R . .
H19E H 1.0583 1.1257 0.0109 0.156 Uiso 1 1 calc R . .
H19F H 0.9133 1.1096 0.0557 0.156 Uiso 1 1 calc R . .
C20A C 1.7076(6) 1.2158(3) 0.3540(3) 0.156(2) Uani 1 1 d . . .
H20D H 1.7656 1.2310 0.4108 0.234 Uiso 1 1 calc R . .
H20E H 1.7795 1.1913 0.3192 0.234 Uiso 1 1 calc R . .
H20F H 1.6149 1.1686 0.3476 0.234 Uiso 1 1 calc R . .
C21A C 1.0192(4) 1.2993(3) 0.0944(2) 0.0873(11) Uani 1 1 d . . .
H21D H 1.0556 1.3566 0.1361 0.131 Uiso 1 1 calc R . .
H21E H 0.9016 1.2867 0.0835 0.131 Uiso 1 1 calc R . .
H21F H 1.0537 1.3070 0.0445 0.131 Uiso 1 1 calc R . .
C22A C 1.7919(5) 1.3809(3) 0.3422(2) 0.1212(15) Uani 1 1 d . . .
H22D H 1.8426 1.3990 0.4000 0.182 Uiso 1 1 calc R . .
H22E H 1.7540 1.4355 0.3231 0.182 Uiso 1 1 calc R . .
H22F H 1.8705 1.3566 0.3114 0.182 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0509(14) 0.0403(13) 0.0209(11) 0.0146(10) 0.0009(10) 0.0073(11)
N2 0.0783(19) 0.0605(16) 0.0479(15) 0.0327(13) -0.0059(14) -0.0061(15)
N3 0.0737(17) 0.0476(14) 0.0243(13) 0.0122(11) 0.0025(12) -0.0013(13)
C1 0.0540(19) 0.0414(16) 0.0180(13) 0.0093(12) 0.0036(13) 0.0043(15)
C2 0.0589(19) 0.0541(18) 0.0343(16) 0.0148(13) 0.0058(15) 0.0165(15)
C3 0.096(3) 0.064(2) 0.0316(17) 0.0187(15) 0.0079(17) 0.035(2)
C4 0.121(3) 0.055(2) 0.045(2) 0.0277(16) 0.004(2) 0.010(2)
C5 0.103(3) 0.068(2) 0.074(2) 0.0381(19) -0.001(2) -0.015(2)
C6 0.0472(17) 0.0422(16) 0.0257(15) 0.0153(12) 0.0099(13) 0.0105(13)
C7 0.066(2) 0.0556(19) 0.0333(16) 0.0220(14) 0.0054(15) 0.0025(16)
C8 0.088(2) 0.0527(19) 0.052(2) 0.0265(16) 0.0197(18) 0.0021(17)
C9 0.089(2) 0.0515(19) 0.055(2) 0.0089(16) 0.0171(19) -0.0060(17)
C10 0.090(3) 0.056(2) 0.0398(18) 0.0077(16) 0.0041(17) -0.0075(18)
C11 0.0528(18) 0.0473(16) 0.0196(14) 0.0169(12) 0.0000(13) 0.0081(14)
C12 0.0581(19) 0.0593(18) 0.0267(16) 0.0155(13) 0.0018(14) 0.0173(16)
C13 0.066(2) 0.084(2) 0.047(2) 0.0174(17) -0.0031(17) 0.0344(18)
C14 0.089(3) 0.099(3) 0.0329(19) 0.0239(17) -0.0085(18) 0.031(2)
C15 0.084(2) 0.083(2) 0.0204(15) 0.0185(14) 0.0044(16) 0.018(2)
C16 0.0637(19) 0.0573(17) 0.0245(15) 0.0203(13) 0.0076(14) 0.0122(15)
C17 0.057(2) 0.081(2) 0.0420(18) 0.0064(16) 0.0078(16) 0.0188(18)
C18 0.069(2) 0.082(2) 0.0272(16) 0.0158(15) 0.0127(15) 0.0184(18)
C19 0.086(3) 0.127(3) 0.070(2) 0.006(2) 0.033(2) 0.010(2)
C20 0.106(3) 0.135(3) 0.130(4) 0.055(3) 0.068(3) 0.033(3)
C21 0.108(3) 0.085(3) 0.072(2) -0.010(2) 0.005(2) 0.027(2)
C22 0.107(3) 0.082(3) 0.111(3) 0.012(2) 0.029(3) 0.028(2)
N1A 0.0635(15) 0.0449(13) 0.0232(11) 0.0126(10) 0.0192(11) 0.0158(11)
N2A 0.098(2) 0.0534(16) 0.0428(14) 0.0225(13) 0.0263(14) 0.0281(14)
N3A 0.0675(17) 0.0620(16) 0.0402(14) 0.0110(12) 0.0242(13) 0.0015(13)
C1A 0.0587(19) 0.0463(17) 0.0278(15) 0.0130(13) 0.0148(13) 0.0168(14)
C2A 0.110(3) 0.061(2) 0.0297(17) 0.0150(15) 0.0240(17) 0.0154(18)
C3A 0.144(3) 0.074(2) 0.0400(19) 0.0071(18) 0.039(2) 0.025(2)
C4A 0.148(4) 0.063(2) 0.062(2) 0.0051(19) 0.043(2) 0.033(2)
C5A 0.138(3) 0.053(2) 0.064(2) 0.0222(17) 0.036(2) 0.038(2)
C6A 0.0513(18) 0.0476(17) 0.0225(14) 0.0135(12) 0.0084(13) 0.0118(14)
C7A 0.078(2) 0.0530(19) 0.0497(18) 0.0177(15) 0.0266(17) 0.0163(17)
C8A 0.093(3) 0.049(2) 0.066(2) 0.0154(16) 0.021(2) 0.0142(18)
C9A 0.089(3) 0.057(2) 0.053(2) 0.0236(17) 0.0051(19) -0.0037(18)
C10A 0.082(2) 0.078(2) 0.0428(19) 0.0194(18) 0.0182(18) -0.011(2)
C11A 0.0573(19) 0.0483(16) 0.0206(14) 0.0158(11) 0.0207(13) 0.0176(14)
C12A 0.062(2) 0.0476(16) 0.0256(15) 0.0139(12) 0.0158(14) 0.0090(14)
C13A 0.071(2) 0.0578(18) 0.0220(15) 0.0145(13) 0.0102(15) 0.0118(16)
C14A 0.072(2) 0.070(2) 0.0296(17) 0.0216(14) 0.0259(16) 0.0190(17)
C15A 0.059(2) 0.074(2) 0.0422(18) 0.0193(15) 0.0251(16) 0.0185(16)
C16A 0.057(2) 0.0585(18) 0.0317(16) 0.0154(13) 0.0187(15) 0.0199(15)
C17A 0.060(2) 0.084(2) 0.0305(16) 0.0208(16) 0.0066(15) -0.0035(17)
C18A 0.057(2) 0.110(3) 0.0285(17) 0.0153(17) 0.0082(15) 0.026(2)
C19A 0.107(3) 0.104(3) 0.077(3) 0.000(2) 0.005(2) -0.036(2)
C20A 0.182(5) 0.141(4) 0.110(4) 0.041(3) -0.077(3) 0.034(4)
C21A 0.063(2) 0.132(3) 0.081(3) 0.053(2) 0.013(2) 0.026(2)
C22A 0.126(4) 0.148(4) 0.060(3) -0.009(2) 0.000(2) -0.033(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.387(3) . ?
N1 C1 1.405(3) . ?
N1 C11 1.454(3) . ?
N2 C1 1.307(3) . ?
N2 C5 1.345(3) . ?
N3 C10 1.321(3) . ?
N3 C6 1.341(3) . ?
C1 C2 1.395(3) . ?
C2 C3 1.380(4) . ?
C2 H2B 0.9300 . ?
C3 C4 1.352(4) . ?
C3 H3B 0.9300 . ?
C4 C5 1.371(4) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.386(3) . ?
C7 C8 1.351(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.386(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.360(4) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.386(3) . ?
C11 C16 1.393(3) . ?
C12 C13 1.388(4) . ?
C12 C17 1.515(4) . ?
C13 C14 1.367(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.369(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.392(4) . ?
C15 H15A 0.9300 . ?
C16 C18 1.512(4) . ?
C17 C19 1.517(4) . ?
C17 C21 1.524(4) . ?
C17 H17A 0.9800 . ?
C18 C20 1.515(4) . ?
C18 C22 1.519(4) . ?
C18 H18A 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1A C6A 1.400(3) . ?
N1A C1A 1.405(3) . ?
N1A C11A 1.451(3) . ?
N2A C1A 1.322(3) . ?
N2A C5A 1.330(3) . ?
N3A C6A 1.328(3) . ?
N3A C10A 1.338(3) . ?
C1A C2A 1.392(3) . ?
C2A C3A 1.357(4) . ?
C2A H2AB 0.9300 . ?
C3A C4A 1.364(4) . ?
C3A H3AB 0.9300 . ?
C4A C5A 1.365(4) . ?
C4A H4AA 0.9300 . ?
C5A H5AA 0.9300 . ?
C6A C7A 1.376(3) . ?
C7A C8A 1.362(4) . ?
C7A H7AA 0.9300 . ?
C8A C9A 1.373(4) . ?
C8A H8AA 0.9300 . ?
C9A C10A 1.359(4) . ?
C9A H9AA 0.9300 . ?
C10A H10B 0.9300 . ?
C11A C16A 1.391(4) . ?
C11A C12A 1.401(3) . ?
C12A C13A 1.390(3) . ?
C12A C17A 1.510(4) . ?
C13A C14A 1.363(4) . ?
C13A H13B 0.9300 . ?
C14A C15A 1.375(4) . ?
C14A H14B 0.9300 . ?
C15A C16A 1.386(3) . ?
C15A H15B 0.9300 . ?
C16A C18A 1.536(4) . ?
C17A C19A 1.522(4) . ?
C17A C21A 1.526(4) . ?
C17A H17B 0.9800 . ?
C18A C22A 1.503(5) . ?
C18A C20A 1.511(5) . ?
C18A H18B 0.9800 . ?
C19A H19D 0.9600 . ?
C19A H19E 0.9600 . ?
C19A H19F 0.9600 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C1 124.00(19) . . ?
C6 N1 C11 117.89(18) . . ?
C1 N1 C11 117.5(2) . . ?
C1 N2 C5 118.2(3) . . ?
C10 N3 C6 117.4(2) . . ?
N2 C1 C2 122.7(2) . . ?
N2 C1 N1 115.7(2) . . ?
C2 C1 N1 121.5(2) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2B 121.2 . . ?
C1 C2 H2B 121.2 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3B 119.8 . . ?
C2 C3 H3B 119.8 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 H4A 120.9 . . ?
N2 C5 C4 123.1(3) . . ?
N2 C5 H5A 118.5 . . ?
C4 C5 H5A 118.5 . . ?
N3 C6 C7 120.9(2) . . ?
N3 C6 N1 116.9(2) . . ?
C7 C6 N1 122.2(2) . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C9 119.1(3) . . ?
C7 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
C10 C9 C8 117.0(3) . . ?
C10 C9 H9A 121.5 . . ?
C8 C9 H9A 121.5 . . ?
N3 C10 C9 125.2(3) . . ?
N3 C10 H10A 117.4 . . ?
C9 C10 H10A 117.4 . . ?
C12 C11 C16 122.3(2) . . ?
C12 C11 N1 118.9(2) . . ?
C16 C11 N1 118.8(2) . . ?
C11 C12 C13 117.6(2) . . ?
C11 C12 C17 123.4(2) . . ?
C13 C12 C17 119.0(3) . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15A 119.4 . . ?
C16 C15 H15A 119.4 . . ?
C15 C16 C11 117.4(3) . . ?
C15 C16 C18 119.5(2) . . ?
C11 C16 C18 123.0(2) . . ?
C12 C17 C19 111.0(3) . . ?
C12 C17 C21 112.3(2) . . ?
C19 C17 C21 111.2(3) . . ?
C12 C17 H17A 107.4 . . ?
C19 C17 H17A 107.4 . . ?
C21 C17 H17A 107.4 . . ?
C16 C18 C20 112.5(3) . . ?
C16 C18 C22 111.5(3) . . ?
C20 C18 C22 110.1(3) . . ?
C16 C18 H18A 107.5 . . ?
C20 C18 H18A 107.5 . . ?
C22 C18 H18A 107.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C6A N1A C1A 124.5(2) . . ?
C6A N1A C11A 118.03(19) . . ?
C1A N1A C11A 117.37(19) . . ?
C1A N2A C5A 117.8(2) . . ?
C6A N3A C10A 116.9(2) . . ?
N2A C1A C2A 121.6(2) . . ?
N2A C1A N1A 115.1(2) . . ?
C2A C1A N1A 123.2(2) . . ?
C3A C2A C1A 118.5(3) . . ?
C3A C2A H2AB 120.7 . . ?
C1A C2A H2AB 120.7 . . ?
C2A C3A C4A 120.8(3) . . ?
C2A C3A H3AB 119.6 . . ?
C4A C3A H3AB 119.6 . . ?
C3A C4A C5A 116.7(3) . . ?
C3A C4A H4AA 121.7 . . ?
C5A C4A H4AA 121.7 . . ?
N2A C5A C4A 124.5(3) . . ?
N2A C5A H5AA 117.7 . . ?
C4A C5A H5AA 117.7 . . ?
N3A C6A C7A 121.7(2) . . ?
N3A C6A N1A 117.0(2) . . ?
C7A C6A N1A 121.3(2) . . ?
C8A C7A C6A 119.9(3) . . ?
C8A C7A H7AA 120.0 . . ?
C6A C7A H7AA 120.0 . . ?
C7A C8A C9A 119.4(3) . . ?
C7A C8A H8AA 120.3 . . ?
C9A C8A H8AA 120.3 . . ?
C10A C9A C8A 116.9(3) . . ?
C10A C9A H9AA 121.6 . . ?
C8A C9A H9AA 121.6 . . ?
N3A C10A C9A 125.1(3) . . ?
N3A C10A H10B 117.4 . . ?
C9A C10A H10B 117.4 . . ?
C16A C11A C12A 122.0(2) . . ?
C16A C11A N1A 118.8(2) . . ?
C12A C11A N1A 119.2(2) . . ?
C13A C12A C11A 117.1(3) . . ?
C13A C12A C17A 119.7(2) . . ?
C11A C12A C17A 123.2(2) . . ?
C14A C13A C12A 121.9(3) . . ?
C14A C13A H13B 119.0 . . ?
C12A C13A H13B 119.0 . . ?
C13A C14A C15A 119.7(3) . . ?
C13A C14A H14B 120.1 . . ?
C15A C14A H14B 120.1 . . ?
C14A C15A C16A 121.4(3) . . ?
C14A C15A H15B 119.3 . . ?
C16A C15A H15B 119.3 . . ?
C15A C16A C11A 117.8(2) . . ?
C15A C16A C18A 119.3(3) . . ?
C11A C16A C18A 122.9(2) . . ?
C12A C17A C19A 112.2(3) . . ?
C12A C17A C21A 110.0(2) . . ?
C19A C17A C21A 111.6(3) . . ?
C12A C17A H17B 107.6 . . ?
C19A C17A H17B 107.6 . . ?
C21A C17A H17B 107.6 . . ?
C22A C18A C20A 110.2(3) . . ?
C22A C18A C16A 114.2(3) . . ?
C20A C18A C16A 110.3(3) . . ?
C22A C18A H18B 107.3 . . ?
C20A C18A H18B 107.3 . . ?
C16A C18A H18B 107.3 . . ?
C17A C19A H19D 109.5 . . ?
C17A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C17A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C18A C20A H20D 109.5 . . ?
C18A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C18A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C17A C21A H21D 109.5 . . ?
C17A C21A H21E 109.5 . . ?
H21D C21A H21E 109.5 . . ?
C17A C21A H21F 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C18A C22A H22D 109.5 . . ?
C18A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
C18A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C1 C2 -0.4(4) . . . . ?
C5 N2 C1 N1 -176.3(2) . . . . ?
C6 N1 C1 N2 -148.5(2) . . . . ?
C11 N1 C1 N2 22.3(3) . . . . ?
C6 N1 C1 C2 35.6(3) . . . . ?
C11 N1 C1 C2 -153.6(2) . . . . ?
N2 C1 C2 C3 1.1(4) . . . . ?
N1 C1 C2 C3 176.7(2) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C1 N2 C5 C4 0.0(5) . . . . ?
C3 C4 C5 N2 -0.2(5) . . . . ?
C10 N3 C6 C7 -0.8(4) . . . . ?
C10 N3 C6 N1 178.3(2) . . . . ?
C1 N1 C6 N3 17.0(3) . . . . ?
C11 N1 C6 N3 -153.8(2) . . . . ?
C1 N1 C6 C7 -164.0(2) . . . . ?
C11 N1 C6 C7 25.3(3) . . . . ?
N3 C6 C7 C8 1.1(4) . . . . ?
N1 C6 C7 C8 -177.9(2) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C6 N3 C10 C9 -0.1(4) . . . . ?
C8 C9 C10 N3 0.6(5) . . . . ?
C6 N1 C11 C12 70.2(3) . . . . ?
C1 N1 C11 C12 -101.2(3) . . . . ?
C6 N1 C11 C16 -108.4(3) . . . . ?
C1 N1 C11 C16 80.3(3) . . . . ?
C16 C11 C12 C13 1.6(4) . . . . ?
N1 C11 C12 C13 -176.9(2) . . . . ?
C16 C11 C12 C17 -176.4(2) . . . . ?
N1 C11 C12 C17 5.1(4) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C17 C12 C13 C14 176.9(3) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
C14 C15 C16 C11 -0.3(4) . . . . ?
C14 C15 C16 C18 -179.5(3) . . . . ?
C12 C11 C16 C15 -0.9(4) . . . . ?
N1 C11 C16 C15 177.6(2) . . . . ?
C12 C11 C16 C18 178.2(2) . . . . ?
N1 C11 C16 C18 -3.3(4) . . . . ?
C11 C12 C17 C19 114.6(3) . . . . ?
C13 C12 C17 C19 -63.3(4) . . . . ?
C11 C12 C17 C21 -120.2(3) . . . . ?
C13 C12 C17 C21 61.8(4) . . . . ?
C15 C16 C18 C20 -59.1(4) . . . . ?
C11 C16 C18 C20 121.8(3) . . . . ?
C15 C16 C18 C22 65.1(3) . . . . ?
C11 C16 C18 C22 -113.9(3) . . . . ?
C5A N2A C1A C2A 0.3(5) . . . . ?
C5A N2A C1A N1A -175.4(3) . . . . ?
C6A N1A C1A N2A -153.6(2) . . . . ?
C11A N1A C1A N2A 23.6(3) . . . . ?
C6A N1A C1A C2A 30.8(4) . . . . ?
C11A N1A C1A C2A -152.0(3) . . . . ?
N2A C1A C2A C3A 0.2(5) . . . . ?
N1A C1A C2A C3A 175.6(3) . . . . ?
C1A C2A C3A C4A 0.1(6) . . . . ?
C2A C3A C4A C5A -0.9(6) . . . . ?
C1A N2A C5A C4A -1.2(5) . . . . ?
C3A C4A C5A N2A 1.5(6) . . . . ?
C10A N3A C6A C7A -1.6(4) . . . . ?
C10A N3A C6A N1A 178.3(2) . . . . ?
C1A N1A C6A N3A 15.2(4) . . . . ?
C11A N1A C6A N3A -162.0(2) . . . . ?
C1A N1A C6A C7A -164.9(2) . . . . ?
C11A N1A C6A C7A 17.9(4) . . . . ?
N3A C6A C7A C8A 2.1(4) . . . . ?
N1A C6A C7A C8A -177.9(2) . . . . ?
C6A C7A C8A C9A -1.7(4) . . . . ?
C7A C8A C9A C10A 1.1(4) . . . . ?
C6A N3A C10A C9A 0.9(4) . . . . ?
C8A C9A C10A N3A -0.7(5) . . . . ?
C6A N1A C11A C16A -107.0(3) . . . . ?
C1A N1A C11A C16A 75.6(3) . . . . ?
C6A N1A C11A C12A 72.1(3) . . . . ?
C1A N1A C11A C12A -105.3(3) . . . . ?
C16A C11A C12A C13A 1.6(4) . . . . ?
N1A C11A C12A C13A -177.4(2) . . . . ?
C16A C11A C12A C17A -175.9(2) . . . . ?
N1A C11A C12A C17A 5.0(3) . . . . ?
C11A C12A C13A C14A -0.7(4) . . . . ?
C17A C12A C13A C14A 176.9(2) . . . . ?
C12A C13A C14A C15A -0.4(4) . . . . ?
C13A C14A C15A C16A 0.7(4) . . . . ?
C14A C15A C16A C11A 0.1(4) . . . . ?
C14A C15A C16A C18A 179.9(3) . . . . ?
C12A C11A C16A C15A -1.3(4) . . . . ?
N1A C11A C16A C15A 177.7(2) . . . . ?
C12A C11A C16A C18A 179.0(2) . . . . ?
N1A C11A C16A C18A -2.0(4) . . . . ?
C13A C12A C17A C19A 56.1(3) . . . . ?
C11A C12A C17A C19A -126.4(3) . . . . ?
C13A C12A C17A C21A -68.7(3) . . . . ?
C11A C12A C17A C21A 108.8(3) . . . . ?
C15A C16A C18A C22A 35.8(4) . . . . ?
C11A C16A C18A C22A -144.5(3) . . . . ?
C15A C16A C18A C20A -89.0(4) . . . . ?
C11A C16A C18A C20A 90.7(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_theta_full 28.50
_diffrn_measured_fraction_theta_full 0.917
_refine_diff_density_max 0.267
_refine_diff_density_min -0.288
_refine_diff_density_rms 0.060
_exptl_crystal_recrystallization_method
'vapor diffusion of n-pentane into saturated chloroform solution'
_diffrn_ambient_pressure 101.33
# Attachment 'Ph(iPr)N(H)Py.CIF'
data_iprnhpy
_database_code_depnum_ccdc_archive 'CCDC 720342'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic N-((2-isopropyl)phenyl)-N-(2-pyridyl)amine
_chemical_name_common ?
_chemical_melting_point 413
_chemical_formula_moiety 'C14 H16 N2'
_chemical_formula_sum 'C14 H16 N2'
_chemical_formula_weight 212.29
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 10.327(2)
_cell_length_b 10.601(2)
_cell_length_c 12.450(3)
_cell_angle_alpha 90.00
_cell_angle_beta 112.81(3)
_cell_angle_gamma 90.00
_cell_volume 1256.5(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 3358
_cell_measurement_theta_min 2.19
_cell_measurement_theta_max 23.58
_exptl_crystal_description prism
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.86
_exptl_crystal_size_mid 0.56
_exptl_crystal_size_min 0.45
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.122
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 456
_exptl_absorpt_coefficient_mu 0.067
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9447
_exptl_absorpt_correction_T_max 0.9705
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 15089
_diffrn_reflns_av_R_equivalents 0.0369
_diffrn_reflns_av_sigmaI/netI 0.0310
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.19
_diffrn_reflns_theta_max 28.29
_reflns_number_total 3042
_reflns_number_gt 1876
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.2685P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.073(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 3042
_refine_ls_number_parameters 146
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0846
_refine_ls_R_factor_gt 0.0480
_refine_ls_wR_factor_ref 0.1436
_refine_ls_wR_factor_gt 0.1189
_refine_ls_goodness_of_fit_ref 1.004
_refine_ls_restrained_S_all 1.004
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.16863(12) 0.91214(12) 0.01848(10) 0.0508(3) Uani 1 1 d . . .
H1A H 0.0962 0.9152 0.0364 0.061 Uiso 1 1 calc R . .
N2 N 0.07621(12) 1.08708(11) -0.09100(10) 0.0467(3) Uani 1 1 d . . .
C1 C 0.18344(14) 1.00612(13) -0.05054(11) 0.0439(3) Uani 1 1 d . . .
C2 C 0.30331(18) 1.02066(18) -0.07606(16) 0.0651(5) Uani 1 1 d . . .
H2A H 0.3760 0.9622 -0.0494 0.078 Uiso 1 1 calc R . .
C3 C 0.3118(2) 1.1217(2) -0.14056(19) 0.0798(6) Uani 1 1 d . . .
H3A H 0.3912 1.1331 -0.1574 0.096 Uiso 1 1 calc R . .
C4 C 0.2030(2) 1.20694(18) -0.18084(17) 0.0729(5) Uani 1 1 d . . .
H4A H 0.2076 1.2771 -0.2241 0.088 Uiso 1 1 calc R . .
C5 C 0.08797(18) 1.18452(15) -0.15485(14) 0.0584(4) Uani 1 1 d . . .
H5A H 0.0131 1.2406 -0.1834 0.070 Uiso 1 1 calc R . .
C6 C 0.26254(14) 0.80961(13) 0.06342(13) 0.0462(4) Uani 1 1 d . . .
C7 C 0.32809(14) 0.79107(13) 0.18386(12) 0.0456(4) Uani 1 1 d . . .
C8 C 0.41540(17) 0.68577(15) 0.22147(15) 0.0574(4) Uani 1 1 d . . .
H8A H 0.4592 0.6702 0.3010 0.069 Uiso 1 1 calc R . .
C9 C 0.4387(2) 0.60454(17) 0.14486(17) 0.0693(5) Uani 1 1 d . . .
H9A H 0.4984 0.5359 0.1728 0.083 Uiso 1 1 calc R . .
C10 C 0.3736(2) 0.62474(19) 0.02697(18) 0.0757(6) Uani 1 1 d . . .
H10A H 0.3895 0.5703 -0.0252 0.091 Uiso 1 1 calc R . .
C11 C 0.28448(19) 0.72621(17) -0.01340(15) 0.0634(5) Uani 1 1 d . . .
H11A H 0.2385 0.7388 -0.0932 0.076 Uiso 1 1 calc R . .
C12 C 0.30948(17) 0.88388(15) 0.26896(13) 0.0552(4) Uani 1 1 d . . .
H12A H 0.2142 0.9183 0.2327 0.066 Uiso 1 1 calc R . .
C13 C 0.3232(3) 0.8251(2) 0.38418(17) 0.0888(7) Uani 1 1 d . . .
H13A H 0.2581 0.7563 0.3698 0.133 Uiso 1 1 calc R . .
H13B H 0.3029 0.8874 0.4314 0.133 Uiso 1 1 calc R . .
H13C H 0.4172 0.7943 0.4241 0.133 Uiso 1 1 calc R . .
C14 C 0.4109(2) 0.99349(19) 0.2899(2) 0.0895(7) Uani 1 1 d . . .
H14A H 0.4017 1.0294 0.2165 0.134 Uiso 1 1 calc R . .
H14B H 0.5053 0.9639 0.3302 0.134 Uiso 1 1 calc R . .
H14C H 0.3898 1.0564 0.3362 0.134 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0444(7) 0.0610(8) 0.0522(7) 0.0180(6) 0.0245(6) 0.0138(6)
N2 0.0488(7) 0.0483(7) 0.0448(6) 0.0043(5) 0.0200(5) 0.0069(5)
C1 0.0423(7) 0.0508(8) 0.0385(7) 0.0013(6) 0.0154(6) 0.0025(6)
C2 0.0498(9) 0.0749(11) 0.0776(11) 0.0188(10) 0.0322(8) 0.0088(8)
C3 0.0705(12) 0.0881(14) 0.0998(15) 0.0227(12) 0.0537(11) 0.0005(11)
C4 0.0894(14) 0.0643(11) 0.0797(12) 0.0205(10) 0.0488(11) 0.0027(10)
C5 0.0702(11) 0.0517(9) 0.0586(9) 0.0111(7) 0.0307(8) 0.0102(8)
C6 0.0416(7) 0.0487(8) 0.0501(8) 0.0079(7) 0.0198(6) 0.0063(6)
C7 0.0426(7) 0.0448(8) 0.0483(8) 0.0072(6) 0.0166(6) 0.0011(6)
C8 0.0585(9) 0.0538(9) 0.0571(9) 0.0142(7) 0.0194(7) 0.0110(7)
C9 0.0737(12) 0.0576(10) 0.0809(13) 0.0142(9) 0.0345(10) 0.0231(9)
C10 0.0867(14) 0.0702(12) 0.0784(13) -0.0030(10) 0.0411(11) 0.0232(10)
C11 0.0666(11) 0.0729(11) 0.0530(9) 0.0034(8) 0.0257(8) 0.0157(9)
C12 0.0570(9) 0.0543(9) 0.0491(8) 0.0027(7) 0.0148(7) 0.0074(7)
C13 0.1238(19) 0.0892(15) 0.0565(11) 0.0066(10) 0.0383(11) 0.0151(13)
C14 0.0970(16) 0.0652(13) 0.1008(16) -0.0183(11) 0.0323(13) -0.0141(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3624(18) . ?
N1 C6 1.4193(18) . ?
N1 H1A 0.8600 . ?
N2 C1 1.3358(18) . ?
N2 C5 1.3375(19) . ?
C1 C2 1.401(2) . ?
C2 C3 1.362(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.368(2) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C11 1.384(2) . ?
C6 C7 1.399(2) . ?
C7 C8 1.397(2) . ?
C7 C12 1.512(2) . ?
C8 C9 1.374(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.374(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.377(2) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C14 1.518(3) . ?
C12 C13 1.520(2) . ?
C12 H12A 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 125.59(12) . . ?
C1 N1 H1A 117.2 . . ?
C6 N1 H1A 117.2 . . ?
C1 N2 C5 117.87(13) . . ?
N2 C1 N1 115.36(12) . . ?
N2 C1 C2 121.34(14) . . ?
N1 C1 C2 123.28(13) . . ?
C3 C2 C1 119.00(16) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 120.10(16) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 117.45(16) . . ?
C5 C4 H4A 121.3 . . ?
C3 C4 H4A 121.3 . . ?
N2 C5 C4 124.20(16) . . ?
N2 C5 H5A 117.9 . . ?
C4 C5 H5A 117.9 . . ?
C11 C6 C7 120.66(14) . . ?
C11 C6 N1 119.12(13) . . ?
C7 C6 N1 120.18(13) . . ?
C8 C7 C6 116.92(14) . . ?
C8 C7 C12 121.74(13) . . ?
C6 C7 C12 121.30(13) . . ?
C9 C8 C7 122.15(15) . . ?
C9 C8 H8A 118.9 . . ?
C7 C8 H8A 118.9 . . ?
C8 C9 C10 119.95(16) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C9 C10 C11 119.51(17) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C10 C11 C6 120.78(16) . . ?
C10 C11 H11A 119.6 . . ?
C6 C11 H11A 119.6 . . ?
C7 C12 C14 110.60(15) . . ?
C7 C12 C13 113.82(14) . . ?
C14 C12 C13 110.27(16) . . ?
C7 C12 H12A 107.3 . . ?
C14 C12 H12A 107.3 . . ?
C13 C12 H12A 107.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C1 N1 177.01(13) . . . . ?
C5 N2 C1 C2 -1.4(2) . . . . ?
C6 N1 C1 N2 174.46(13) . . . . ?
C6 N1 C1 C2 -7.1(2) . . . . ?
N2 C1 C2 C3 2.0(3) . . . . ?
N1 C1 C2 C3 -176.32(16) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C1 N2 C5 C4 -0.4(2) . . . . ?
C3 C4 C5 N2 1.5(3) . . . . ?
C1 N1 C6 C11 -61.4(2) . . . . ?
C1 N1 C6 C7 120.81(16) . . . . ?
C11 C6 C7 C8 0.1(2) . . . . ?
N1 C6 C7 C8 177.89(13) . . . . ?
C11 C6 C7 C12 177.71(15) . . . . ?
N1 C6 C7 C12 -4.5(2) . . . . ?
C6 C7 C8 C9 1.1(2) . . . . ?
C12 C7 C8 C9 -176.56(16) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C6 1.6(3) . . . . ?
C7 C6 C11 C10 -1.4(3) . . . . ?
N1 C6 C11 C10 -179.22(16) . . . . ?
C8 C7 C12 C14 94.06(18) . . . . ?
C6 C7 C12 C14 -83.44(18) . . . . ?
C8 C7 C12 C13 -30.7(2) . . . . ?
C6 C7 C12 C13 151.76(16) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.86 2.14 2.9962(18) 176 3_575
_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full 28.29
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max 0.152
_refine_diff_density_min -0.155
_refine_diff_density_rms 0.035
_exptl_crystal_recrystallization_method 'slow evaporation of MeOH soln'
_diffrn_ambient_pressure 101.33
# Attachment '[Cu(NapDPA)(Cl)(mu-Cl)]2MeOH.CIF'
data_cundpacl
_database_code_depnum_ccdc_archive 'CCDC 720343'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C40 H30 Cl4 Cu2 N6, 2(C H4 O)'
_chemical_formula_sum 'C42 H38 Cl4 Cu2 N6 O2'
_chemical_formula_weight 927.66
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 8.9968(18)
_cell_length_b 8.0607(16)
_cell_length_c 28.486(6)
_cell_angle_alpha 90.00
_cell_angle_beta 98.00(3)
_cell_angle_gamma 90.00
_cell_volume 2045.7(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 6179
_cell_measurement_theta_min 2.49
_cell_measurement_theta_max 23.98
_exptl_crystal_description plate
_exptl_crystal_colour green
_exptl_crystal_size_max 0.52
_exptl_crystal_size_mid 0.51
_exptl_crystal_size_min 0.15
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.506
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 948
_exptl_absorpt_coefficient_mu 1.345
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.5413
_exptl_absorpt_correction_T_max 0.8237
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 24044
_diffrn_reflns_av_R_equivalents 0.0591
_diffrn_reflns_av_sigmaI/netI 0.0594
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -37
_diffrn_reflns_limit_l_max 37
_diffrn_reflns_theta_min 1.44
_diffrn_reflns_theta_max 28.36
_reflns_number_total 4985
_reflns_number_gt 3528
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0886P)^2^+13.2506P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.0146(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 4985
_refine_ls_number_parameters 254
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1152
_refine_ls_R_factor_gt 0.0870
_refine_ls_wR_factor_ref 0.2628
_refine_ls_wR_factor_gt 0.2496
_refine_ls_goodness_of_fit_ref 1.150
_refine_ls_restrained_S_all 1.150
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.62174(9) 0.53795(11) 0.05265(3) 0.0388(3) Uani 1 1 d . . .
Cl1 Cl 0.4764(2) 0.3134(2) 0.02647(6) 0.0481(5) Uani 1 1 d . . .
Cl2 Cl 0.4634(2) 0.6094(3) 0.10549(7) 0.0617(6) Uani 1 1 d . . .
N1 N 0.9337(6) 0.5329(7) 0.11197(19) 0.0386(12) Uani 1 1 d . . .
N2 N 0.8121(6) 0.4242(7) 0.03988(19) 0.0385(12) Uani 1 1 d . . .
N3 N 0.7549(6) 0.7259(7) 0.0773(2) 0.0399(13) Uani 1 1 d . . .
C1 C 0.9342(7) 0.4282(8) 0.0721(2) 0.0358(14) Uani 1 1 d . . .
C2 C 1.0595(8) 0.3317(10) 0.0678(3) 0.0478(17) Uani 1 1 d . . .
H2A H 1.1429 0.3334 0.0911 0.057 Uiso 1 1 calc R . .
C3 C 1.0572(9) 0.2326(10) 0.0278(3) 0.0519(19) Uani 1 1 d . . .
H3A H 1.1385 0.1641 0.0246 0.062 Uiso 1 1 calc R . .
C4 C 0.9376(10) 0.2352(10) -0.0065(3) 0.0537(19) Uani 1 1 d . . .
H4A H 0.9367 0.1734 -0.0341 0.064 Uiso 1 1 calc R . .
C5 C 0.8165(9) 0.3325(10) 0.0006(3) 0.0494(18) Uani 1 1 d . . .
H5A H 0.7338 0.3349 -0.0230 0.059 Uiso 1 1 calc R . .
C6 C 0.8758(7) 0.6950(8) 0.1088(2) 0.0374(14) Uani 1 1 d . . .
C7 C 0.9447(10) 0.8198(10) 0.1371(3) 0.054(2) Uani 1 1 d . . .
H7A H 1.0271 0.7965 0.1597 0.065 Uiso 1 1 calc R . .
C8 C 0.8902(11) 0.9787(11) 0.1316(3) 0.062(2) Uani 1 1 d . . .
H8A H 0.9352 1.0637 0.1506 0.074 Uiso 1 1 calc R . .
C9 C 0.7689(11) 1.0123(10) 0.0979(3) 0.061(2) Uani 1 1 d . . .
H9A H 0.7321 1.1197 0.0931 0.073 Uiso 1 1 calc R . .
C10 C 0.7055(9) 0.8845(10) 0.0722(3) 0.0483(17) Uani 1 1 d . . .
H10A H 0.6230 0.9062 0.0495 0.058 Uiso 1 1 calc R . .
C11 C 1.0155(8) 0.4790(8) 0.1575(2) 0.0385(14) Uani 1 1 d . . .
C12 C 0.9266(8) 0.4006(8) 0.1887(2) 0.0404(15) Uani 1 1 d . . .
C13 C 0.7704(9) 0.3731(10) 0.1782(3) 0.0505(18) Uani 1 1 d . . .
H13A H 0.7194 0.4069 0.1491 0.061 Uiso 1 1 calc R . .
C14 C 0.6940(12) 0.2975(13) 0.2102(4) 0.071(3) Uani 1 1 d . . .
H14A H 0.5916 0.2777 0.2025 0.085 Uiso 1 1 calc R . .
C15 C 0.7691(17) 0.2482(14) 0.2555(4) 0.088(4) Uani 1 1 d . . .
H15A H 0.7151 0.2007 0.2776 0.105 Uiso 1 1 calc R . .
C16 C 0.9165(17) 0.2705(14) 0.2660(3) 0.083(3) Uani 1 1 d . . .
H16A H 0.9646 0.2340 0.2952 0.099 Uiso 1 1 calc R . .
C17 C 1.0028(11) 0.3477(10) 0.2341(3) 0.055(2) Uani 1 1 d . . .
C18 C 1.1584(12) 0.3750(13) 0.2440(3) 0.071(3) Uani 1 1 d . . .
H18A H 1.2091 0.3388 0.2729 0.085 Uiso 1 1 calc R . .
C19 C 1.2353(10) 0.4498(13) 0.2140(4) 0.068(3) Uani 1 1 d . . .
H19A H 1.3379 0.4666 0.2222 0.081 Uiso 1 1 calc R . .
C20 C 1.1633(9) 0.5049(10) 0.1693(3) 0.0528(19) Uani 1 1 d . . .
H20A H 1.2179 0.5585 0.1484 0.063 Uiso 1 1 calc R . .
O1S O 0.2778(12) 0.9450(18) 0.1143(7) 0.182(7) Uani 1 1 d . . .
H1SA H 0.3283 0.8615 0.1121 0.219 Uiso 1 1 calc R . .
C1S C 0.3636(16) 1.0637(19) 0.1332(5) 0.104(4) Uani 1 1 d . . .
H1SD H 0.3045 1.1615 0.1358 0.156 Uiso 1 1 calc R . .
H1SB H 0.4398 1.0868 0.1136 0.156 Uiso 1 1 calc R . .
H1SC H 0.4100 1.0305 0.1642 0.156 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0383(5) 0.0413(5) 0.0370(5) 0.0000(4) 0.0058(3) 0.0008(3)
Cl1 0.0510(10) 0.0470(10) 0.0446(9) 0.0066(8) 0.0010(7) -0.0081(8)
Cl2 0.0514(11) 0.0915(17) 0.0452(10) -0.0080(10) 0.0169(8) 0.0023(11)
N1 0.042(3) 0.041(3) 0.032(3) 0.003(2) 0.003(2) 0.004(2)
N2 0.042(3) 0.041(3) 0.033(3) 0.001(2) 0.008(2) 0.002(2)
N3 0.036(3) 0.040(3) 0.043(3) -0.001(2) 0.004(2) 0.006(2)
C1 0.035(3) 0.037(3) 0.037(3) 0.005(3) 0.012(3) 0.000(3)
C2 0.037(4) 0.052(4) 0.055(4) -0.013(4) 0.010(3) 0.006(3)
C3 0.053(4) 0.045(4) 0.060(5) -0.003(4) 0.017(4) 0.008(3)
C4 0.067(5) 0.050(4) 0.047(4) -0.010(4) 0.021(4) 0.004(4)
C5 0.051(4) 0.053(4) 0.045(4) -0.005(3) 0.005(3) -0.002(3)
C6 0.037(3) 0.038(3) 0.040(3) 0.003(3) 0.015(3) 0.002(3)
C7 0.058(5) 0.047(4) 0.055(5) -0.011(4) -0.003(4) -0.003(4)
C8 0.069(6) 0.045(4) 0.067(5) -0.010(4) -0.002(4) -0.002(4)
C9 0.078(6) 0.032(4) 0.073(6) 0.006(4) 0.013(5) 0.005(4)
C10 0.055(4) 0.045(4) 0.043(4) -0.001(3) 0.000(3) 0.007(3)
C11 0.048(4) 0.034(3) 0.033(3) 0.003(3) 0.004(3) 0.004(3)
C12 0.056(4) 0.031(3) 0.034(3) 0.001(3) 0.007(3) 0.006(3)
C13 0.060(5) 0.045(4) 0.048(4) -0.002(3) 0.013(4) 0.002(4)
C14 0.070(6) 0.064(6) 0.084(7) -0.002(5) 0.033(5) -0.013(5)
C15 0.133(11) 0.066(7) 0.072(7) 0.022(6) 0.045(7) -0.003(7)
C16 0.140(11) 0.066(6) 0.044(5) 0.023(5) 0.018(6) 0.014(7)
C17 0.091(6) 0.040(4) 0.034(4) 0.003(3) 0.004(4) 0.012(4)
C18 0.094(7) 0.065(6) 0.046(5) 0.002(4) -0.020(5) 0.020(5)
C19 0.049(5) 0.081(7) 0.067(6) -0.004(5) -0.016(4) 0.007(5)
C20 0.045(4) 0.049(4) 0.063(5) 0.001(4) 0.003(4) 0.002(3)
O1S 0.087(7) 0.155(12) 0.30(2) -0.058(13) -0.011(9) 0.026(8)
C1S 0.105(10) 0.099(10) 0.104(10) 0.018(8) -0.001(8) 0.008(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.998(6) . ?
Cu1 N2 2.020(6) . ?
Cu1 Cl2 2.285(2) . ?
Cu1 Cl1 2.296(2) . ?
Cu1 Cl1 2.596(2) 3_665 ?
Cl1 Cu1 2.596(2) 3_665 ?
N1 C6 1.404(9) . ?
N1 C1 1.415(9) . ?
N1 C11 1.466(8) . ?
N2 C1 1.330(9) . ?
N2 C5 1.347(9) . ?
N3 C6 1.333(9) . ?
N3 C10 1.355(9) . ?
C1 C2 1.389(9) . ?
C2 C3 1.391(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.350(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(11) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.382(10) . ?
C7 C8 1.373(12) . ?
C7 H7A 0.9300 . ?
C8 C9 1.376(13) . ?
C8 H8A 0.9300 . ?
C9 C10 1.344(12) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C20 1.342(10) . ?
C11 C12 1.423(10) . ?
C12 C13 1.413(11) . ?
C12 C17 1.443(10) . ?
C13 C14 1.362(12) . ?
C13 H13A 0.9300 . ?
C14 C15 1.426(16) . ?
C14 H14A 0.9300 . ?
C15 C16 1.331(17) . ?
C15 H15A 0.9300 . ?
C16 C17 1.417(14) . ?
C16 H16A 0.9300 . ?
C17 C18 1.407(14) . ?
C18 C19 1.319(15) . ?
C18 H18A 0.9300 . ?
C19 C20 1.416(12) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
O1S C1S 1.298(17) . ?
O1S H1SA 0.8200 . ?
C1S H1SD 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N2 85.7(2) . . ?
N3 Cu1 Cl2 88.59(18) . . ?
N2 Cu1 Cl2 148.75(17) . . ?
N3 Cu1 Cl1 177.24(18) . . ?
N2 Cu1 Cl1 92.44(18) . . ?
Cl2 Cu1 Cl1 91.92(9) . . ?
N3 Cu1 Cl1 94.03(18) . 3_665 ?
N2 Cu1 Cl1 104.32(17) . 3_665 ?
Cl2 Cu1 Cl1 106.72(8) . 3_665 ?
Cl1 Cu1 Cl1 88.41(7) . 3_665 ?
Cu1 Cl1 Cu1 91.59(7) . 3_665 ?
C6 N1 C1 123.1(6) . . ?
C6 N1 C11 118.0(6) . . ?
C1 N1 C11 118.4(5) . . ?
C1 N2 C5 118.0(6) . . ?
C1 N2 Cu1 120.3(4) . . ?
C5 N2 Cu1 121.5(5) . . ?
C6 N3 C10 118.3(6) . . ?
C6 N3 Cu1 119.2(5) . . ?
C10 N3 Cu1 120.4(5) . . ?
N2 C1 C2 121.8(7) . . ?
N2 C1 N1 118.3(6) . . ?
C2 C1 N1 119.9(6) . . ?
C1 C2 C3 118.3(7) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C4 C3 C2 120.3(7) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 118.0(7) . . ?
C3 C4 H4A 121.0 . . ?
C5 C4 H4A 121.0 . . ?
N2 C5 C4 123.3(7) . . ?
N2 C5 H5A 118.3 . . ?
C4 C5 H5A 118.3 . . ?
N3 C6 C7 120.9(7) . . ?
N3 C6 N1 118.5(6) . . ?
C7 C6 N1 120.5(7) . . ?
C8 C7 C6 119.3(8) . . ?
C8 C7 H7A 120.4 . . ?
C6 C7 H7A 120.4 . . ?
C7 C8 C9 120.0(8) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C10 C9 C8 117.7(8) . . ?
C10 C9 H9A 121.2 . . ?
C8 C9 H9A 121.2 . . ?
C9 C10 N3 123.8(7) . . ?
C9 C10 H10A 118.1 . . ?
N3 C10 H10A 118.1 . . ?
C20 C11 C12 122.4(7) . . ?
C20 C11 N1 122.3(7) . . ?
C12 C11 N1 115.3(6) . . ?
C13 C12 C11 124.5(6) . . ?
C13 C12 C17 118.5(7) . . ?
C11 C12 C17 116.9(7) . . ?
C14 C13 C12 120.5(8) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 120.8(10) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C16 C15 C14 119.8(9) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C17 122.2(10) . . ?
C15 C16 H16A 118.9 . . ?
C17 C16 H16A 118.9 . . ?
C18 C17 C16 124.0(9) . . ?
C18 C17 C12 117.9(8) . . ?
C16 C17 C12 118.0(9) . . ?
C19 C18 C17 122.6(8) . . ?
C19 C18 H18A 118.7 . . ?
C17 C18 H18A 118.7 . . ?
C18 C19 C20 120.7(9) . . ?
C18 C19 H19A 119.6 . . ?
C20 C19 H19A 119.6 . . ?
C11 C20 C19 119.3(8) . . ?
C11 C20 H20A 120.3 . . ?
C19 C20 H20A 120.3 . . ?
C1S O1S H1SA 109.5 . . ?
O1S C1S H1SD 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
H1SD C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SD C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Cu1 Cl1 Cu1 -104.27(17) . . . 3_665 ?
Cl2 Cu1 Cl1 Cu1 106.68(8) . . . 3_665 ?
Cl1 Cu1 Cl1 Cu1 0.0 3_665 . . 3_665 ?
N3 Cu1 N2 C1 43.9(5) . . . . ?
Cl2 Cu1 N2 C1 -36.3(7) . . . . ?
Cl1 Cu1 N2 C1 -134.0(5) . . . . ?
Cl1 Cu1 N2 C1 137.0(5) 3_665 . . . ?
N3 Cu1 N2 C5 -141.1(6) . . . . ?
Cl2 Cu1 N2 C5 138.7(5) . . . . ?
Cl1 Cu1 N2 C5 40.9(6) . . . . ?
Cl1 Cu1 N2 C5 -48.1(6) 3_665 . . . ?
N2 Cu1 N3 C6 -49.9(5) . . . . ?
Cl2 Cu1 N3 C6 99.3(5) . . . . ?
Cl1 Cu1 N3 C6 -154.0(5) 3_665 . . . ?
N2 Cu1 N3 C10 146.8(6) . . . . ?
Cl2 Cu1 N3 C10 -63.9(6) . . . . ?
Cl1 Cu1 N3 C10 42.7(6) 3_665 . . . ?
C5 N2 C1 C2 -4.9(10) . . . . ?
Cu1 N2 C1 C2 170.3(5) . . . . ?
C5 N2 C1 N1 175.9(6) . . . . ?
Cu1 N2 C1 N1 -9.0(8) . . . . ?
C6 N1 C1 N2 -42.6(9) . . . . ?
C11 N1 C1 N2 146.1(6) . . . . ?
C6 N1 C1 C2 138.1(7) . . . . ?
C11 N1 C1 C2 -33.1(9) . . . . ?
N2 C1 C2 C3 1.9(11) . . . . ?
N1 C1 C2 C3 -178.8(7) . . . . ?
C1 C2 C3 C4 2.2(12) . . . . ?
C2 C3 C4 C5 -3.0(13) . . . . ?
C1 N2 C5 C4 4.0(11) . . . . ?
Cu1 N2 C5 C4 -171.1(6) . . . . ?
C3 C4 C5 N2 -0.1(13) . . . . ?
C10 N3 C6 C7 3.1(10) . . . . ?
Cu1 N3 C6 C7 -160.4(6) . . . . ?
C10 N3 C6 N1 -175.7(6) . . . . ?
Cu1 N3 C6 N1 20.7(8) . . . . ?
C1 N1 C6 N3 36.1(9) . . . . ?
C11 N1 C6 N3 -152.6(6) . . . . ?
C1 N1 C6 C7 -142.7(7) . . . . ?
C11 N1 C6 C7 28.6(9) . . . . ?
N3 C6 C7 C8 -2.0(12) . . . . ?
N1 C6 C7 C8 176.8(8) . . . . ?
C6 C7 C8 C9 -0.5(14) . . . . ?
C7 C8 C9 C10 1.7(15) . . . . ?
C8 C9 C10 N3 -0.5(14) . . . . ?
C6 N3 C10 C9 -1.9(12) . . . . ?
Cu1 N3 C10 C9 161.5(7) . . . . ?
C6 N1 C11 C20 -87.4(9) . . . . ?
C1 N1 C11 C20 84.3(9) . . . . ?
C6 N1 C11 C12 91.3(7) . . . . ?
C1 N1 C11 C12 -97.0(7) . . . . ?
C20 C11 C12 C13 178.9(7) . . . . ?
N1 C11 C12 C13 0.2(10) . . . . ?
C20 C11 C12 C17 -0.5(11) . . . . ?
N1 C11 C12 C17 -179.2(6) . . . . ?
C11 C12 C13 C14 -179.7(8) . . . . ?
C17 C12 C13 C14 -0.3(12) . . . . ?
C12 C13 C14 C15 1.6(14) . . . . ?
C13 C14 C15 C16 -2.6(17) . . . . ?
C14 C15 C16 C17 2.3(18) . . . . ?
C15 C16 C17 C18 179.3(11) . . . . ?
C15 C16 C17 C12 -1.1(16) . . . . ?
C13 C12 C17 C18 179.6(8) . . . . ?
C11 C12 C17 C18 -0.9(11) . . . . ?
C13 C12 C17 C16 0.1(11) . . . . ?
C11 C12 C17 C16 179.5(8) . . . . ?
C16 C17 C18 C19 -178.8(10) . . . . ?
C12 C17 C18 C19 1.6(14) . . . . ?
C17 C18 C19 C20 -0.9(16) . . . . ?
C12 C11 C20 C19 1.3(12) . . . . ?
N1 C11 C20 C19 179.9(7) . . . . ?
C18 C19 C20 C11 -0.6(14) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1S H1SA Cl2 0.82 2.39 3.208(13) 177 .
_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full 28.36
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max 1.697
_refine_diff_density_min -0.553
_refine_diff_density_rms 0.137
_exptl_crystal_recrystallization_method 'slow evaporation of MeOH solution'
_diffrn_ambient_pressure 101.33
# Attachment '[Cu(PhDPA)(Cl)(mu-Cl)]2.CIF'
data_cuphdpa
_database_code_depnum_ccdc_archive 'CCDC 720344'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
(dichloro)-di-(mu-chloro)-bis(N-Phenyl-N,N-(2,2-dipyridyl)amine)-dicopper(II)
_chemical_name_common ?
_chemical_melting_point 538
_chemical_formula_moiety 'C32 H26 Cl4 Cu2 N6'
_chemical_formula_sum 'C32 H26 Cl4 Cu2 N6'
_chemical_formula_weight 763.47
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_int_tables_number 15
_symmetry_space_group_name_Hall '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 16.282(3)
_cell_length_b 7.3669(15)
_cell_length_c 27.085(5)
_cell_angle_alpha 90.00
_cell_angle_beta 101.28(3)
_cell_angle_gamma 90.00
_cell_volume 3186.0(11)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 5781
_cell_measurement_theta_min 2.5512
_cell_measurement_theta_max 26.7103
_exptl_crystal_description plate
_exptl_crystal_colour 'dark green'
_exptl_crystal_size_max 0.57
_exptl_crystal_size_mid 0.31
_exptl_crystal_size_min 0.19
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.592
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1544
_exptl_absorpt_coefficient_mu 1.704
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6786
_exptl_absorpt_correction_T_max 0.8621
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 19085
_diffrn_reflns_av_R_equivalents 0.0348
_diffrn_reflns_av_sigmaI/netI 0.0289
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -35
_diffrn_reflns_limit_l_max 35
_diffrn_reflns_theta_min 1.53
_diffrn_reflns_theta_max 28.30
_reflns_number_total 3900
_reflns_number_gt 3139
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+2.3737P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.00453(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 3900
_refine_ls_number_parameters 200
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0425
_refine_ls_R_factor_gt 0.0286
_refine_ls_wR_factor_ref 0.0747
_refine_ls_wR_factor_gt 0.0686
_refine_ls_goodness_of_fit_ref 1.048
_refine_ls_restrained_S_all 1.048
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.025997(14) 0.01426(3) 0.437126(8) 0.02869(9) Uani 1 1 d . . .
N1 N 0.15900(10) 0.0803(2) 0.37712(6) 0.0348(4) Uani 1 1 d . . .
N2 N 0.04580(10) 0.2379(2) 0.39755(6) 0.0324(3) Uani 1 1 d . . .
N3 N 0.15226(10) 0.00303(19) 0.46024(6) 0.0286(3) Uani 1 1 d . . .
C1 C 0.10541(12) 0.2342(3) 0.37002(7) 0.0331(4) Uani 1 1 d . . .
C2 C 0.11634(15) 0.3736(3) 0.33789(9) 0.0468(5) Uani 1 1 d . . .
H2A H 0.1585 0.3682 0.3192 0.056 Uiso 1 1 calc R . .
C3 C 0.06334(18) 0.5211(3) 0.33407(10) 0.0535(6) Uani 1 1 d . . .
H3A H 0.0683 0.6152 0.3119 0.064 Uiso 1 1 calc R . .
C4 C 0.00275(17) 0.5283(3) 0.36340(9) 0.0507(6) Uani 1 1 d . . .
H4A H -0.0326 0.6280 0.3619 0.061 Uiso 1 1 calc R . .
C5 C -0.00393(14) 0.3857(3) 0.39452(8) 0.0437(5) Uani 1 1 d . . .
H5A H -0.0444 0.3906 0.4144 0.052 Uiso 1 1 calc R . .
C6 C 0.20114(12) 0.0477(2) 0.42742(7) 0.0300(4) Uani 1 1 d . . .
C7 C 0.28672(12) 0.0680(3) 0.44213(9) 0.0400(5) Uani 1 1 d . . .
H7A H 0.3189 0.1052 0.4191 0.048 Uiso 1 1 calc R . .
C8 C 0.32387(13) 0.0323(3) 0.49150(9) 0.0416(5) Uani 1 1 d . . .
H8A H 0.3816 0.0408 0.5020 0.050 Uiso 1 1 calc R . .
C9 C 0.27401(14) -0.0161(3) 0.52498(9) 0.0401(5) Uani 1 1 d . . .
H9A H 0.2977 -0.0417 0.5583 0.048 Uiso 1 1 calc R . .
C10 C 0.18858(13) -0.0262(3) 0.50845(8) 0.0349(4) Uani 1 1 d . . .
H10A H 0.1550 -0.0542 0.5315 0.042 Uiso 1 1 calc R . .
C11 C 0.17232(13) -0.0253(3) 0.33572(8) 0.0337(4) Uani 1 1 d . . .
C12 C 0.11724(15) -0.0123(3) 0.28987(8) 0.0412(5) Uani 1 1 d . . .
H12A H 0.0723 0.0676 0.2864 0.049 Uiso 1 1 calc R . .
C13 C 0.12816(16) -0.1166(3) 0.24908(8) 0.0494(6) Uani 1 1 d . . .
H13A H 0.0910 -0.1050 0.2185 0.059 Uiso 1 1 calc R . .
C14 C 0.19362(17) -0.2373(3) 0.25363(9) 0.0555(6) Uani 1 1 d . . .
H14A H 0.2013 -0.3067 0.2262 0.067 Uiso 1 1 calc R . .
C15 C 0.24747(16) -0.2541(3) 0.29924(10) 0.0560(6) Uani 1 1 d . . .
H15A H 0.2915 -0.3365 0.3026 0.067 Uiso 1 1 calc R . .
C16 C 0.23754(14) -0.1505(3) 0.34031(8) 0.0449(5) Uani 1 1 d . . .
H16A H 0.2744 -0.1645 0.3710 0.054 Uiso 1 1 calc R . .
Cl1 Cl 0.00678(3) -0.22625(6) 0.486347(19) 0.03434(12) Uani 1 1 d . . .
Cl2 Cl -0.09756(3) -0.02755(8) 0.38393(2) 0.04405(14) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.02579(13) 0.03232(14) 0.02829(14) 0.00475(9) 0.00608(9) 0.00288(9)
N1 0.0387(9) 0.0373(9) 0.0309(8) 0.0039(7) 0.0133(7) 0.0110(7)
N2 0.0340(8) 0.0321(8) 0.0326(8) 0.0047(7) 0.0105(7) 0.0083(7)
N3 0.0261(8) 0.0292(8) 0.0308(8) 0.0016(6) 0.0066(6) 0.0014(6)
C1 0.0394(11) 0.0296(9) 0.0319(10) 0.0020(8) 0.0108(8) 0.0050(8)
C2 0.0574(14) 0.0396(11) 0.0492(13) 0.0094(10) 0.0250(11) 0.0019(10)
C3 0.0738(17) 0.0349(12) 0.0546(15) 0.0145(10) 0.0193(13) 0.0055(11)
C4 0.0680(16) 0.0349(11) 0.0501(14) 0.0073(10) 0.0139(12) 0.0193(10)
C5 0.0487(12) 0.0428(12) 0.0417(12) 0.0062(10) 0.0143(10) 0.0169(10)
C6 0.0297(9) 0.0279(9) 0.0341(10) -0.0003(7) 0.0108(8) 0.0041(7)
C7 0.0315(10) 0.0375(11) 0.0540(13) -0.0002(10) 0.0157(9) -0.0013(8)
C8 0.0261(10) 0.0390(11) 0.0574(14) -0.0066(10) 0.0023(9) -0.0014(8)
C9 0.0382(11) 0.0393(11) 0.0383(11) -0.0032(9) -0.0037(9) 0.0017(8)
C10 0.0347(10) 0.0383(10) 0.0319(10) 0.0011(8) 0.0070(8) 0.0024(8)
C11 0.0398(11) 0.0323(10) 0.0326(10) 0.0050(8) 0.0164(9) 0.0013(8)
C12 0.0482(13) 0.0396(11) 0.0371(11) 0.0045(9) 0.0113(10) 0.0065(9)
C13 0.0664(15) 0.0487(13) 0.0331(11) 0.0037(10) 0.0100(11) -0.0012(11)
C14 0.0760(17) 0.0558(15) 0.0404(13) -0.0077(11) 0.0255(12) 0.0066(13)
C15 0.0601(15) 0.0563(15) 0.0559(15) -0.0069(12) 0.0217(12) 0.0195(12)
C16 0.0474(13) 0.0487(13) 0.0398(12) 0.0003(10) 0.0117(10) 0.0141(10)
Cl1 0.0365(2) 0.0300(2) 0.0377(3) 0.00469(19) 0.01033(19) -0.00052(18)
Cl2 0.0380(3) 0.0576(3) 0.0326(3) -0.0021(2) -0.0028(2) 0.0029(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.0254(16) . ?
Cu1 N3 2.0301(17) . ?
Cu1 Cl2 2.2546(9) . ?
Cu1 Cl1 2.2754(6) . ?
Cu1 Cl1 2.7300(7) 5_556 ?
Cu1 Cu1 3.6728(9) 5_556 ?
N1 C11 1.416(3) . ?
N1 C1 1.421(2) . ?
N1 C6 1.421(3) . ?
N2 C1 1.335(2) . ?
N2 C5 1.350(2) . ?
N3 C10 1.341(3) . ?
N3 C6 1.345(2) . ?
C1 C2 1.380(3) . ?
C2 C3 1.379(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.364(3) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.380(3) . ?
C7 C8 1.381(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.377(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.377(3) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.385(3) . ?
C11 C16 1.394(3) . ?
C12 C13 1.385(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.373(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.384(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
Cl1 Cu1 2.7300(7) 5_556 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N3 86.55(6) . . ?
N2 Cu1 Cl2 89.28(5) . . ?
N3 Cu1 Cl2 156.14(5) . . ?
N2 Cu1 Cl1 176.19(5) . . ?
N3 Cu1 Cl1 91.98(5) . . ?
Cl2 Cu1 Cl1 93.46(3) . . ?
N2 Cu1 Cl1 90.66(5) . 5_556 ?
N3 Cu1 Cl1 97.23(5) . 5_556 ?
Cl2 Cu1 Cl1 106.31(3) . 5_556 ?
Cl1 Cu1 Cl1 86.04(2) . 5_556 ?
C11 N1 C1 121.10(16) . . ?
C11 N1 C6 123.13(16) . . ?
C1 N1 C6 115.67(15) . . ?
C1 N2 C5 118.39(17) . . ?
C1 N2 Cu1 119.17(12) . . ?
C5 N2 Cu1 122.19(14) . . ?
C10 N3 C6 118.53(17) . . ?
C10 N3 Cu1 122.26(13) . . ?
C6 N3 Cu1 118.74(13) . . ?
N2 C1 C2 122.32(18) . . ?
N2 C1 N1 115.79(16) . . ?
C2 C1 N1 121.85(18) . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
N2 C5 C4 122.6(2) . . ?
N2 C5 H5A 118.7 . . ?
C4 C5 H5A 118.7 . . ?
N3 C6 C7 122.02(19) . . ?
N3 C6 N1 115.97(16) . . ?
C7 C6 N1 121.96(18) . . ?
C6 C7 C8 119.0(2) . . ?
C6 C7 H7A 120.5 . . ?
C8 C7 H7A 120.5 . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C8 C9 C10 119.2(2) . . ?
C8 C9 H9A 120.4 . . ?
C10 C9 H9A 120.4 . . ?
N3 C10 C9 122.2(2) . . ?
N3 C10 H10A 118.9 . . ?
C9 C10 H10A 118.9 . . ?
C12 C11 C16 118.29(19) . . ?
C12 C11 N1 119.95(18) . . ?
C16 C11 N1 121.68(19) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 H14A 120.5 . . ?
C13 C14 H14A 120.5 . . ?
C14 C15 C16 121.3(2) . . ?
C14 C15 H15A 119.4 . . ?
C16 C15 H15A 119.4 . . ?
C15 C16 C11 120.0(2) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
Cu1 Cl1 Cu1 93.96(2) . 5_556 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cu1 N2 C1 46.29(15) . . . . ?
Cl2 Cu1 N2 C1 -110.21(15) . . . . ?
Cl1 Cu1 N2 C1 113.8(6) . . . . ?
N3 Cu1 N2 C5 -139.55(17) . . . . ?
Cl2 Cu1 N2 C5 63.95(16) . . . . ?
Cl1 Cu1 N2 C5 -72.0(7) . . . . ?
N2 Cu1 N3 C10 134.57(15) . . . . ?
Cl2 Cu1 N3 C10 -145.06(13) . . . . ?
Cl1 Cu1 N3 C10 -41.91(14) . . . . ?
Cl1 Cu1 N3 C10 44.35(14) 5_556 . . . ?
N2 Cu1 N3 C6 -37.34(14) . . . . ?
Cl2 Cu1 N3 C6 43.0(2) . . . . ?
Cl1 Cu1 N3 C6 146.18(13) . . . . ?
Cl1 Cu1 N3 C6 -127.57(13) 5_556 . . . ?
C5 N2 C1 C2 -1.6(3) . . . . ?
Cu1 N2 C1 C2 172.76(17) . . . . ?
C5 N2 C1 N1 176.28(18) . . . . ?
Cu1 N2 C1 N1 -9.3(2) . . . . ?
C11 N1 C1 N2 127.5(2) . . . . ?
C6 N1 C1 N2 -56.0(2) . . . . ?
C11 N1 C1 C2 -54.6(3) . . . . ?
C6 N1 C1 C2 121.9(2) . . . . ?
N2 C1 C2 C3 -0.3(3) . . . . ?
N1 C1 C2 C3 -178.1(2) . . . . ?
C1 C2 C3 C4 2.0(4) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C1 N2 C5 C4 2.0(3) . . . . ?
Cu1 N2 C5 C4 -172.17(18) . . . . ?
C3 C4 C5 N2 -0.4(4) . . . . ?
C10 N3 C6 C7 -1.5(3) . . . . ?
Cu1 N3 C6 C7 170.75(15) . . . . ?
C10 N3 C6 N1 -178.88(16) . . . . ?
Cu1 N3 C6 N1 -6.7(2) . . . . ?
C11 N1 C6 N3 -117.87(19) . . . . ?
C1 N1 C6 N3 65.8(2) . . . . ?
C11 N1 C6 C7 64.7(3) . . . . ?
C1 N1 C6 C7 -111.6(2) . . . . ?
N3 C6 C7 C8 3.4(3) . . . . ?
N1 C6 C7 C8 -179.34(18) . . . . ?
C6 C7 C8 C9 -2.3(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C6 N3 C10 C9 -1.5(3) . . . . ?
Cu1 N3 C10 C9 -173.47(14) . . . . ?
C8 C9 C10 N3 2.5(3) . . . . ?
C1 N1 C11 C12 -17.6(3) . . . . ?
C6 N1 C11 C12 166.20(18) . . . . ?
C1 N1 C11 C16 165.70(19) . . . . ?
C6 N1 C11 C16 -10.4(3) . . . . ?
C16 C11 C12 C13 -2.1(3) . . . . ?
N1 C11 C12 C13 -178.86(19) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 C11 -0.5(4) . . . . ?
C12 C11 C16 C15 1.9(3) . . . . ?
N1 C11 C16 C15 178.6(2) . . . . ?
N3 Cu1 Cl1 Cu1 97.11(5) . . . 5_556 ?
Cl2 Cu1 Cl1 Cu1 -106.13(3) . . . 5_556 ?
N3 Cu1 Cu1 N2 -89.12(7) . . 5_556 5_556 ?
N3 Cu1 Cu1 Cl2 11.69(5) . . 5_556 5_556 ?
N1 Cu1 Cu1 Cl2 -3.14(6) . . 5_556 5_556 ?
Cl1 Cl1 N3 N2 -56.49(5) 5_556 . . . ?
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full 28.30
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max 0.287
_refine_diff_density_min -0.452
_refine_diff_density_rms 0.065
_exptl_crystal_recrystallization_method
'sat. soln in MeOH cooled to -12 deg C for several days'
_diffrn_ambient_pressure 101.33
# Attachment '[Cu(mu-OH)(H2O)(MDPA)]2[BF4]2(MeOH)2.CIF'
data_comdpa
_database_code_depnum_ccdc_archive 'CCDC 720346'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C38 H44 Cu2 N6 O4, 2(B F4), 2(C H4 O)'
_chemical_formula_sum 'C40 H52 B2 Cu2 F8 N6 O6'
_chemical_formula_weight 1013.58
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 12.762(3)
_cell_length_b 7.7754(16)
_cell_length_c 23.501(5)
_cell_angle_alpha 90.00
_cell_angle_beta 100.72(3)
_cell_angle_gamma 90.00
_cell_volume 2291.4(8)
_cell_formula_units_Z 2
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 2813
_cell_measurement_theta_min 2.76
_cell_measurement_theta_max 20.70
_exptl_crystal_description prism
_exptl_crystal_colour dark-blue
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.469
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1044
_exptl_absorpt_coefficient_mu 1.012
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6589
_exptl_absorpt_correction_T_max 0.8217
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 27141
_diffrn_reflns_av_R_equivalents 0.0686
_diffrn_reflns_av_sigmaI/netI 0.0680
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -31
_diffrn_reflns_limit_l_max 30
_diffrn_reflns_theta_min 1.76
_diffrn_reflns_theta_max 28.31
_reflns_number_total 5577
_reflns_number_gt 3355
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+2.1475P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 5577
_refine_ls_number_parameters 336
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1096
_refine_ls_R_factor_gt 0.0520
_refine_ls_wR_factor_ref 0.1367
_refine_ls_wR_factor_gt 0.1118
_refine_ls_goodness_of_fit_ref 1.013
_refine_ls_restrained_S_all 1.013
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.58436(3) 0.40623(5) 0.040057(16) 0.03243(14) Uani 1 1 d . . .
O1 O 1.4642(2) 0.5605(4) 0.04300(11) 0.0365(6) Uani 1 1 d . . .
H1A H 1.425(3) 0.530(5) 0.0519(17) 0.037(14) Uiso 1 1 d . . .
O2 O 1.4922(3) 0.1633(5) 0.03885(14) 0.0543(8) Uani 1 1 d . . .
H2B H 1.511(3) 0.089(5) 0.0532(15) 0.023(12) Uiso 1 1 d . . .
H2C H 1.423(4) 0.164(6) 0.041(2) 0.084(17) Uiso 1 1 d . . .
N1 N 1.8130(2) 0.4815(4) 0.11381(11) 0.0327(6) Uani 1 1 d . . .
N2 N 1.6375(2) 0.4081(4) 0.12504(11) 0.0335(6) Uani 1 1 d . . .
N3 N 1.7268(2) 0.3187(4) 0.03282(11) 0.0340(6) Uani 1 1 d . . .
C1 C 1.7352(3) 0.4646(4) 0.14863(13) 0.0333(7) Uani 1 1 d . . .
C2 C 1.7601(3) 0.5049(5) 0.20775(15) 0.0452(9) Uani 1 1 d . . .
H2A H 1.8262 0.5516 0.2236 0.054 Uiso 1 1 calc R . .
C3 C 1.6862(3) 0.4748(6) 0.24203(16) 0.0538(10) Uani 1 1 d . . .
H3A H 1.7020 0.5006 0.2813 0.065 Uiso 1 1 calc R . .
C4 C 1.5882(3) 0.4063(5) 0.21813(16) 0.0504(10) Uani 1 1 d . . .
H4A H 1.5382 0.3804 0.2410 0.060 Uiso 1 1 calc R . .
C5 C 1.5672(3) 0.3778(5) 0.16016(16) 0.0455(9) Uani 1 1 d . . .
H5A H 1.5003 0.3350 0.1437 0.055 Uiso 1 1 calc R . .
C6 C 1.8168(2) 0.3852(4) 0.06358(13) 0.0325(7) Uani 1 1 d . . .
C7 C 1.9149(3) 0.3579(5) 0.04645(16) 0.0478(10) Uani 1 1 d . . .
H7A H 1.9767 0.4094 0.0664 0.057 Uiso 1 1 calc R . .
C8 C 1.9180(3) 0.2535(6) -0.00049(17) 0.0556(11) Uani 1 1 d . . .
H8A H 1.9826 0.2343 -0.0124 0.067 Uiso 1 1 calc R . .
C9 C 1.8275(3) 0.1778(5) -0.02977(16) 0.0479(9) Uani 1 1 d . . .
H9A H 1.8295 0.1036 -0.0606 0.057 Uiso 1 1 calc R . .
C10 C 1.7333(3) 0.2148(5) -0.01224(15) 0.0425(9) Uani 1 1 d . . .
H10A H 1.6709 0.1657 -0.0325 0.051 Uiso 1 1 calc R . .
C11 C 1.9073(2) 0.5801(4) 0.13778(14) 0.0340(7) Uani 1 1 d . . .
C12 C 1.9922(3) 0.5007(5) 0.17454(15) 0.0392(8) Uani 1 1 d . . .
C13 C 2.0810(3) 0.5993(5) 0.19460(16) 0.0478(9) Uani 1 1 d . . .
H13A H 2.1379 0.5494 0.2196 0.057 Uiso 1 1 calc R . .
C14 C 2.0889(3) 0.7687(5) 0.17913(16) 0.0485(10) Uani 1 1 d . . .
C15 C 2.0035(3) 0.8432(5) 0.14228(16) 0.0456(9) Uani 1 1 d . . .
H15A H 2.0082 0.9573 0.1312 0.055 Uiso 1 1 calc R . .
C16 C 1.9111(3) 0.7509(5) 0.12159(14) 0.0376(8) Uani 1 1 d . . .
C17 C 1.9890(3) 0.3136(5) 0.19086(18) 0.0556(11) Uani 1 1 d . . .
H17A H 2.0394 0.2931 0.2259 0.083 Uiso 1 1 calc R . .
H17B H 2.0069 0.2439 0.1603 0.083 Uiso 1 1 calc R . .
H17C H 1.9187 0.2846 0.1967 0.083 Uiso 1 1 calc R . .
C18 C 2.1888(4) 0.8715(7) 0.2016(2) 0.0814(16) Uani 1 1 d . . .
H18A H 2.1800 0.9868 0.1869 0.122 Uiso 1 1 calc R . .
H18B H 2.2486 0.8188 0.1890 0.122 Uiso 1 1 calc R . .
H18C H 2.2011 0.8740 0.2431 0.122 Uiso 1 1 calc R . .
C19 C 1.8186(3) 0.8353(6) 0.08229(19) 0.0626(12) Uani 1 1 d . . .
H19A H 1.8083 0.7822 0.0448 0.094 Uiso 1 1 calc R . .
H19B H 1.8333 0.9554 0.0787 0.094 Uiso 1 1 calc R . .
H19C H 1.7552 0.8219 0.0984 0.094 Uiso 1 1 calc R . .
O1S O 1.5424(3) 0.8609(5) 0.09768(17) 0.0707(11) Uani 1 1 d . . .
H1S4 H 1.528(4) 0.787(6) 0.085(2) 0.065(19) Uiso 1 1 d . . .
C1S C 1.5131(5) 0.8569(7) 0.1520(2) 0.099(2) Uani 1 1 d . . .
H1S1 H 1.5674 0.7993 0.1791 0.148 Uiso 1 1 calc R . .
H1S2 H 1.4468 0.7962 0.1493 0.148 Uiso 1 1 calc R . .
H1S3 H 1.5049 0.9723 0.1650 0.148 Uiso 1 1 calc R . .
B1 B 2.2579(4) 0.2926(10) 0.1021(3) 0.0741(17) Uani 1 1 d . . .
F1 F 2.1573(3) 0.2614(7) 0.0973(2) 0.169(2) Uani 1 1 d . A .
F2 F 2.3077(7) 0.1664(16) 0.0816(8) 0.123(4) Uani 0.50 1 d P A 1
F3 F 2.255(2) 0.424(3) 0.0748(14) 0.41(2) Uani 0.50 1 d P A 1
F4 F 2.2752(11) 0.315(3) 0.1558(5) 0.223(8) Uani 0.50 1 d P A 1
F2A F 2.3052(6) 0.4483(11) 0.1150(5) 0.097(3) Uani 0.50 1 d P A 2
F3A F 2.3192(8) 0.182(2) 0.1350(11) 0.206(9) Uani 0.50 1 d P A 2
F4A F 2.2921(7) 0.301(3) 0.0514(4) 0.153(5) Uani 0.50 1 d P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0276(2) 0.0383(2) 0.0306(2) -0.00017(19) 0.00308(15) 0.00109(19)
O1 0.0306(14) 0.0470(17) 0.0324(13) 0.0008(11) 0.0071(11) 0.0037(12)
O2 0.056(2) 0.0433(19) 0.065(2) 0.0053(17) 0.0161(16) -0.0057(16)
N1 0.0257(14) 0.0415(16) 0.0306(14) -0.0054(13) 0.0045(11) -0.0021(12)
N2 0.0269(14) 0.0424(16) 0.0314(14) 0.0016(13) 0.0064(11) -0.0018(13)
N3 0.0294(14) 0.0414(17) 0.0306(15) -0.0028(13) 0.0041(12) 0.0028(12)
C1 0.0330(18) 0.0376(19) 0.0295(17) 0.0027(14) 0.0066(14) 0.0028(15)
C2 0.042(2) 0.059(3) 0.0335(19) -0.0053(18) 0.0053(16) -0.0026(19)
C3 0.060(3) 0.071(3) 0.0319(19) -0.0032(19) 0.0138(18) 0.003(2)
C4 0.046(2) 0.070(3) 0.039(2) 0.006(2) 0.0183(17) 0.000(2)
C5 0.0321(18) 0.061(3) 0.043(2) 0.0099(19) 0.0078(16) -0.0032(17)
C6 0.0295(16) 0.039(2) 0.0292(16) 0.0000(15) 0.0046(13) 0.0008(15)
C7 0.0308(19) 0.064(3) 0.049(2) -0.0112(19) 0.0088(16) -0.0024(17)
C8 0.042(2) 0.075(3) 0.054(2) -0.013(2) 0.0197(19) 0.005(2)
C9 0.051(2) 0.054(2) 0.040(2) -0.0127(18) 0.0121(18) 0.002(2)
C10 0.041(2) 0.045(2) 0.039(2) -0.0054(17) -0.0004(16) 0.0010(17)
C11 0.0301(16) 0.040(2) 0.0315(17) -0.0020(15) 0.0055(13) -0.0019(15)
C12 0.0351(19) 0.041(2) 0.040(2) 0.0011(16) 0.0013(15) 0.0030(16)
C13 0.0316(19) 0.061(3) 0.046(2) -0.003(2) -0.0044(16) 0.0025(19)
C14 0.040(2) 0.061(3) 0.045(2) -0.011(2) 0.0070(17) -0.0122(19)
C15 0.056(2) 0.038(2) 0.045(2) -0.0061(17) 0.0154(19) -0.0074(18)
C16 0.0366(19) 0.042(2) 0.0350(18) 0.0018(16) 0.0085(15) 0.0026(16)
C17 0.054(2) 0.047(3) 0.062(3) 0.007(2) 0.002(2) 0.012(2)
C18 0.063(3) 0.095(4) 0.082(4) -0.009(3) 0.001(3) -0.038(3)
C19 0.062(3) 0.058(3) 0.064(3) 0.019(2) 0.003(2) 0.008(2)
O1S 0.091(3) 0.055(2) 0.062(2) -0.0085(19) 0.0048(18) -0.0049(19)
C1S 0.170(6) 0.072(4) 0.048(3) -0.007(3) 0.004(3) 0.014(4)
B1 0.047(3) 0.103(5) 0.076(4) 0.005(4) 0.019(3) 0.000(3)
F1 0.057(2) 0.205(5) 0.254(6) -0.021(4) 0.054(3) -0.008(3)
F2 0.072(6) 0.102(7) 0.216(13) -0.045(8) 0.080(9) -0.007(5)
F3 0.63(4) 0.24(2) 0.48(4) 0.29(3) 0.38(4) 0.21(2)
F4 0.226(14) 0.36(2) 0.075(6) -0.042(10) 0.015(8) 0.097(16)
F2A 0.060(4) 0.077(5) 0.156(10) -0.012(6) 0.022(4) -0.024(3)
F3A 0.074(6) 0.214(14) 0.33(2) 0.204(15) 0.039(10) 0.029(8)
F4A 0.067(5) 0.291(18) 0.104(6) 0.028(9) 0.027(4) -0.039(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.952(3) 3_865 ?
Cu1 O1 1.959(3) . ?
Cu1 N3 1.977(3) . ?
Cu1 N2 1.986(3) . ?
Cu1 O2 2.222(3) . ?
Cu1 Cu1 2.9665(11) 3_865 ?
O1 Cu1 1.952(3) 3_865 ?
O1 H1A 0.62(4) . ?
O2 H2B 0.69(3) . ?
O2 H2C 0.89(5) . ?
N1 C1 1.405(4) . ?
N1 C6 1.407(4) . ?
N1 C11 1.450(4) . ?
N2 C1 1.341(4) . ?
N2 C5 1.348(4) . ?
N3 C6 1.342(4) . ?
N3 C10 1.347(4) . ?
C1 C2 1.402(4) . ?
C2 C3 1.370(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.357(5) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.400(4) . ?
C7 C8 1.376(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.364(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.371(5) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C16 1.385(5) . ?
C11 C12 1.397(5) . ?
C12 C13 1.377(5) . ?
C12 C17 1.507(5) . ?
C13 C14 1.375(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.386(5) . ?
C14 C18 1.514(5) . ?
C15 C16 1.389(5) . ?
C15 H15A 0.9300 . ?
C16 C19 1.507(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O1S C1S 1.396(6) . ?
O1S H1S4 0.66(5) . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?
B1 F3 1.202(15) . ?
B1 F4 1.252(11) . ?
B1 F1 1.291(6) . ?
B1 F2 1.309(10) . ?
B1 F3A 1.311(11) . ?
B1 F4A 1.345(10) . ?
B1 F2A 1.362(10) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 81.33(12) 3_865 . ?
O1 Cu1 N3 94.90(11) 3_865 . ?
O1 Cu1 N3 162.21(12) . . ?
O1 Cu1 N2 171.89(12) 3_865 . ?
O1 Cu1 N2 94.76(11) . . ?
N3 Cu1 N2 86.67(11) . . ?
O1 Cu1 O2 91.77(13) 3_865 . ?
O1 Cu1 O2 96.04(14) . . ?
N3 Cu1 O2 101.47(13) . . ?
N2 Cu1 O2 95.72(12) . . ?
O1 Cu1 Cu1 40.75(8) 3_865 3_865 ?
O1 Cu1 Cu1 40.58(8) . 3_865 ?
N3 Cu1 Cu1 133.23(8) . 3_865 ?
N2 Cu1 Cu1 134.93(8) . 3_865 ?
O2 Cu1 Cu1 95.15(11) . 3_865 ?
Cu1 O1 Cu1 98.67(12) 3_865 . ?
Cu1 O1 H1A 105(4) 3_865 . ?
Cu1 O1 H1A 118(4) . . ?
Cu1 O2 H2B 125(3) . . ?
Cu1 O2 H2C 121(3) . . ?
H2B O2 H2C 103(4) . . ?
C1 N1 C6 125.3(3) . . ?
C1 N1 C11 116.7(3) . . ?
C6 N1 C11 116.9(2) . . ?
C1 N2 C5 118.5(3) . . ?
C1 N2 Cu1 122.3(2) . . ?
C5 N2 Cu1 118.2(2) . . ?
C6 N3 C10 118.8(3) . . ?
C6 N3 Cu1 122.0(2) . . ?
C10 N3 Cu1 117.8(2) . . ?
N2 C1 C2 120.3(3) . . ?
N2 C1 N1 119.6(3) . . ?
C2 C1 N1 120.1(3) . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 H4A 121.1 . . ?
C3 C4 H4A 121.1 . . ?
N2 C5 C4 123.8(3) . . ?
N2 C5 H5A 118.1 . . ?
C4 C5 H5A 118.1 . . ?
N3 C6 C7 120.6(3) . . ?
N3 C6 N1 119.8(3) . . ?
C7 C6 N1 119.6(3) . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H7A 120.6 . . ?
C6 C7 H7A 120.6 . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C8 C9 C10 117.7(3) . . ?
C8 C9 H9A 121.1 . . ?
C10 C9 H9A 121.1 . . ?
N3 C10 C9 123.3(3) . . ?
N3 C10 H10A 118.4 . . ?
C9 C10 H10A 118.4 . . ?
C16 C11 C12 122.1(3) . . ?
C16 C11 N1 118.0(3) . . ?
C12 C11 N1 119.9(3) . . ?
C13 C12 C11 117.4(3) . . ?
C13 C12 C17 120.7(3) . . ?
C11 C12 C17 121.9(3) . . ?
C14 C13 C12 122.6(3) . . ?
C14 C13 H13A 118.7 . . ?
C12 C13 H13A 118.7 . . ?
C13 C14 C15 118.5(3) . . ?
C13 C14 C18 120.8(4) . . ?
C15 C14 C18 120.7(4) . . ?
C14 C15 C16 121.4(4) . . ?
C14 C15 H15A 119.3 . . ?
C16 C15 H15A 119.3 . . ?
C11 C16 C15 118.0(3) . . ?
C11 C16 C19 121.5(3) . . ?
C15 C16 C19 120.5(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1S O1S H1S4 107(5) . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
F3 B1 F4 113.7(17) . . ?
F3 B1 F1 100.7(15) . . ?
F4 B1 F1 95.7(8) . . ?
F3 B1 F2 114.0(13) . . ?
F4 B1 F2 118.0(11) . . ?
F1 B1 F2 111.7(7) . . ?
F1 B1 F3A 113.8(7) . . ?
F1 B1 F4A 114.4(6) . . ?
F3A B1 F4A 107.3(11) . . ?
F1 B1 F2A 125.4(7) . . ?
F3A B1 F2A 105.0(10) . . ?
F4A B1 F2A 87.2(10) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 O1 Cu1 0.0 3_865 . . 3_865 ?
N3 Cu1 O1 Cu1 78.9(4) . . . 3_865 ?
N2 Cu1 O1 Cu1 172.84(12) . . . 3_865 ?
O2 Cu1 O1 Cu1 -90.88(14) . . . 3_865 ?
O1 Cu1 N2 C1 -119.5(3) . . . . ?
N3 Cu1 N2 C1 42.8(3) . . . . ?
O2 Cu1 N2 C1 144.0(3) . . . . ?
Cu1 Cu1 N2 C1 -112.9(2) 3_865 . . . ?
O1 Cu1 N2 C5 49.6(3) . . . . ?
N3 Cu1 N2 C5 -148.2(3) . . . . ?
O2 Cu1 N2 C5 -47.0(3) . . . . ?
Cu1 Cu1 N2 C5 56.2(3) 3_865 . . . ?
O1 Cu1 N3 C6 128.2(3) 3_865 . . . ?
O1 Cu1 N3 C6 51.4(5) . . . . ?
N2 Cu1 N3 C6 -43.8(3) . . . . ?
O2 Cu1 N3 C6 -138.9(3) . . . . ?
Cu1 Cu1 N3 C6 112.6(2) 3_865 . . . ?
O1 Cu1 N3 C10 -38.2(3) 3_865 . . . ?
O1 Cu1 N3 C10 -115.1(4) . . . . ?
N2 Cu1 N3 C10 149.7(3) . . . . ?
O2 Cu1 N3 C10 54.6(3) . . . . ?
Cu1 Cu1 N3 C10 -53.9(3) 3_865 . . . ?
C5 N2 C1 C2 -5.3(5) . . . . ?
Cu1 N2 C1 C2 163.8(3) . . . . ?
C5 N2 C1 N1 174.0(3) . . . . ?
Cu1 N2 C1 N1 -17.0(4) . . . . ?
C6 N1 C1 N2 -27.2(5) . . . . ?
C11 N1 C1 N2 165.8(3) . . . . ?
C6 N1 C1 C2 152.1(3) . . . . ?
C11 N1 C1 C2 -14.9(5) . . . . ?
N2 C1 C2 C3 4.4(6) . . . . ?
N1 C1 C2 C3 -174.8(4) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 -2.8(6) . . . . ?
C1 N2 C5 C4 2.1(6) . . . . ?
Cu1 N2 C5 C4 -167.4(3) . . . . ?
C3 C4 C5 N2 2.0(6) . . . . ?
C10 N3 C6 C7 4.9(5) . . . . ?
Cu1 N3 C6 C7 -161.4(3) . . . . ?
C10 N3 C6 N1 -174.4(3) . . . . ?
Cu1 N3 C6 N1 19.3(4) . . . . ?
C1 N1 C6 N3 26.0(5) . . . . ?
C11 N1 C6 N3 -167.0(3) . . . . ?
C1 N1 C6 C7 -153.3(3) . . . . ?
C11 N1 C6 C7 13.7(5) . . . . ?
N3 C6 C7 C8 -3.7(6) . . . . ?
N1 C6 C7 C8 175.6(4) . . . . ?
C6 C7 C8 C9 -0.1(6) . . . . ?
C7 C8 C9 C10 2.5(6) . . . . ?
C6 N3 C10 C9 -2.4(5) . . . . ?
Cu1 N3 C10 C9 164.5(3) . . . . ?
C8 C9 C10 N3 -1.3(6) . . . . ?
C1 N1 C11 C16 -97.5(4) . . . . ?
C6 N1 C11 C16 94.3(4) . . . . ?
C1 N1 C11 C12 84.5(4) . . . . ?
C6 N1 C11 C12 -83.6(4) . . . . ?
C16 C11 C12 C13 0.2(5) . . . . ?
N1 C11 C12 C13 178.1(3) . . . . ?
C16 C11 C12 C17 -178.4(3) . . . . ?
N1 C11 C12 C17 -0.5(5) . . . . ?
C11 C12 C13 C14 -1.0(6) . . . . ?
C17 C12 C13 C14 177.6(4) . . . . ?
C12 C13 C14 C15 0.6(6) . . . . ?
C12 C13 C14 C18 -179.1(4) . . . . ?
C13 C14 C15 C16 0.7(6) . . . . ?
C18 C14 C15 C16 -179.6(4) . . . . ?
C12 C11 C16 C15 1.0(5) . . . . ?
N1 C11 C16 C15 -176.9(3) . . . . ?
C12 C11 C16 C19 -179.5(3) . . . . ?
N1 C11 C16 C19 2.6(5) . . . . ?
C14 C15 C16 C11 -1.4(5) . . . . ?
C14 C15 C16 C19 179.1(4) . . . . ?
N3 Cu1 Cu1 N2 34.39(17) . . 3_865 3_865 ?
N3 Cu1 Cu1 O2 -68.98(15) . . 3_865 3_865 ?
N1 Cu1 Cu1 O2 3.20(12) . . 3_865 3_865 ?
O1 O1 N3 N2 -170.0(2) 3_865 . . . ?
Cu1 O1 Cu1 O2 -95.84(14) . . 3_865 3_865 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A F2A 0.62(4) 2.41(4) 3.003(10) 162(5) 1_455
O1 H1A F4A 0.62(4) 2.46(4) 3.016(14) 150(5) 1_455
O1 H1A F3 0.62(4) 2.47(4) 3.09(2) 172(5) 1_455
O2 H2B O1S 0.69(3) 2.06(4) 2.742(5) 171(4) 1_545
O2 H2C F2 0.89(5) 1.89(5) 2.728(9) 154(4) 1_455
O2 H2C F4A 0.89(5) 2.03(5) 2.835(15) 149(5) 1_455
O1S H1S4 O1 0.66(5) 2.11(5) 2.761(5) 174(6) .
_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full 28.31
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max 0.690
_refine_diff_density_min -0.569
_refine_diff_density_rms 0.074
_exptl_crystal_recrystallization_method
'sat. soln in MeOH cooled to -12 deg. C for several days'
_diffrn_ambient_pressure 101.33
# Attachment '[H(MstDPA)]BF4.CIF'
data_hmdpabf
_database_code_depnum_ccdc_archive 'CCDC 720347'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
"N-(2,4,6-trimethyl)phenyl-N,N-(2,2'-dipyridyl)amine hydrogen tetrafluoroborate"
_chemical_name_common
"N-mesityl-N,N-(2,2'-dipyridyl)amine hydrogen tetrafluoroborate"
_chemical_melting_point 501
_chemical_formula_moiety 'C19 H20 N3, B F4'
_chemical_formula_sum 'C19 H20 B F4 N3'
_chemical_formula_weight 377.19
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 8.7303(17)
_cell_length_b 10.151(2)
_cell_length_c 21.326(4)
_cell_angle_alpha 90.00
_cell_angle_beta 93.43(3)
_cell_angle_gamma 90.00
_cell_volume 1886.5(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 2352
_cell_measurement_theta_min 19.15
_cell_measurement_theta_max 2.22
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.29
_exptl_crystal_size_min 0.21
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.328
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 784
_exptl_absorpt_coefficient_mu 0.107
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9647
_exptl_absorpt_correction_T_max 0.9780
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 22802
_diffrn_reflns_av_R_equivalents 0.0615
_diffrn_reflns_av_sigmaI/netI 0.0623
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 1.91
_diffrn_reflns_theta_max 28.35
_reflns_number_total 4646
_reflns_number_gt 1996
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+0.1418P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 4646
_refine_ls_number_parameters 276
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1502
_refine_ls_R_factor_gt 0.0590
_refine_ls_wR_factor_ref 0.1894
_refine_ls_wR_factor_gt 0.1503
_refine_ls_goodness_of_fit_ref 1.061
_refine_ls_restrained_S_all 1.061
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0389(2) 0.28162(17) -0.13319(8) 0.0550(5) Uani 1 1 d . . .
N2 N 0.0378(2) 0.06613(19) -0.09218(9) 0.0593(5) Uani 1 1 d . . .
N3 N -0.1885(2) 0.22138(18) -0.08686(9) 0.0573(5) Uani 1 1 d . . .
H1A H -0.071(4) 0.098(3) -0.0823(13) 0.102(9) Uiso 1 1 d . . .
C1 C 0.1142(3) 0.1634(2) -0.11862(10) 0.0543(6) Uani 1 1 d . . .
C2 C 0.2662(3) 0.1425(2) -0.13259(12) 0.0688(7) Uani 1 1 d . . .
H2A H 0.3207 0.2079 -0.1522 0.083 Uiso 1 1 calc R . .
C3 C 0.3346(3) 0.0243(3) -0.11705(14) 0.0787(8) Uani 1 1 d . . .
H3A H 0.4364 0.0099 -0.1257 0.094 Uiso 1 1 calc R . .
C4 C 0.2539(3) -0.0732(3) -0.08875(13) 0.0759(8) Uani 1 1 d . . .
H4A H 0.3002 -0.1533 -0.0780 0.091 Uiso 1 1 calc R . .
C5 C 0.1053(3) -0.0500(2) -0.07677(12) 0.0706(7) Uani 1 1 d . . .
H5A H 0.0492 -0.1150 -0.0577 0.085 Uiso 1 1 calc R . .
C6 C -0.1131(2) 0.3115(2) -0.11794(10) 0.0513(6) Uani 1 1 d . . .
C7 C -0.1794(3) 0.4318(2) -0.13485(12) 0.0649(7) Uani 1 1 d . . .
H7A H -0.1259 0.4938 -0.1571 0.078 Uiso 1 1 calc R . .
C8 C -0.3252(3) 0.4569(3) -0.11794(13) 0.0711(7) Uani 1 1 d . . .
H8A H -0.3718 0.5368 -0.1286 0.085 Uiso 1 1 calc R . .
C9 C -0.4032(3) 0.3635(3) -0.08510(12) 0.0700(7) Uani 1 1 d . . .
H9A H -0.5023 0.3798 -0.0733 0.084 Uiso 1 1 calc R . .
C10 C -0.3323(3) 0.2479(3) -0.07053(11) 0.0648(7) Uani 1 1 d . . .
H10A H -0.3844 0.1846 -0.0485 0.078 Uiso 1 1 calc R . .
C11 C 0.1258(2) 0.3830(2) -0.16349(10) 0.0509(6) Uani 1 1 d . . .
C12 C 0.1382(3) 0.3762(2) -0.22836(11) 0.0612(6) Uani 1 1 d . . .
C13 C 0.2284(3) 0.4697(3) -0.25584(12) 0.0672(7) Uani 1 1 d . . .
H13A H 0.2388 0.4663 -0.2990 0.081 Uiso 1 1 calc R . .
C14 C 0.3032(3) 0.5675(2) -0.22125(11) 0.0606(6) Uani 1 1 d . . .
C15 C 0.2849(2) 0.5721(2) -0.15720(11) 0.0566(6) Uani 1 1 d . . .
H15A H 0.3340 0.6386 -0.1337 0.068 Uiso 1 1 calc R . .
C16 C 0.1969(2) 0.4819(2) -0.12689(10) 0.0509(6) Uani 1 1 d . . .
C17 C 0.0570(4) 0.2700(3) -0.26770(13) 0.0967(10) Uani 1 1 d . . .
H17A H -0.0002 0.2145 -0.2411 0.145 Uiso 0.50 1 calc PR . .
H17B H 0.1314 0.2180 -0.2880 0.145 Uiso 0.50 1 calc PR . .
H17C H -0.0117 0.3103 -0.2989 0.145 Uiso 0.50 1 calc PR . .
H17D H 0.0799 0.2807 -0.3109 0.145 Uiso 0.50 1 calc PR . .
H17E H -0.0518 0.2772 -0.2640 0.145 Uiso 0.50 1 calc PR . .
H17F H 0.0914 0.1849 -0.2531 0.145 Uiso 0.50 1 calc PR . .
C18 C 0.4048(3) 0.6669(3) -0.25210(14) 0.0899(9) Uani 1 1 d . . .
H18A H 0.4048 0.6490 -0.2963 0.135 Uiso 0.50 1 calc PR . .
H18B H 0.5076 0.6604 -0.2337 0.135 Uiso 0.50 1 calc PR . .
H18C H 0.3663 0.7542 -0.2458 0.135 Uiso 0.50 1 calc PR . .
H18D H 0.4477 0.7267 -0.2209 0.135 Uiso 0.50 1 calc PR . .
H18E H 0.3449 0.7153 -0.2835 0.135 Uiso 0.50 1 calc PR . .
H18F H 0.4862 0.6215 -0.2714 0.135 Uiso 0.50 1 calc PR . .
C19 C 0.1781(3) 0.4929(3) -0.05771(11) 0.0709(7) Uani 1 1 d . . .
H19A H 0.1149 0.4220 -0.0444 0.106 Uiso 0.50 1 calc PR . .
H19B H 0.1305 0.5756 -0.0488 0.106 Uiso 0.50 1 calc PR . .
H19C H 0.2770 0.4883 -0.0355 0.106 Uiso 0.50 1 calc PR . .
H19D H 0.2333 0.5686 -0.0415 0.106 Uiso 0.50 1 calc PR . .
H19E H 0.2178 0.4150 -0.0370 0.106 Uiso 0.50 1 calc PR . .
H19F H 0.0713 0.5023 -0.0503 0.106 Uiso 0.50 1 calc PR . .
B1 B -0.3046(4) -0.1882(3) -0.06556(17) 0.0709(9) Uani 1 1 d . . .
F1 F -0.2738(3) -0.05695(18) -0.06774(12) 0.1390(8) Uani 1 1 d . A .
F2A F -0.3914(8) -0.2185(7) -0.0191(3) 0.151(2) Uani 0.75 1 d P A 1
F3A F -0.1741(3) -0.2623(3) -0.0639(3) 0.1004(10) Uani 0.75 1 d P A 1
F4A F -0.3872(6) -0.2113(4) -0.1202(2) 0.1234(14) Uani 0.75 1 d P A 1
F2B F -0.275(4) -0.2421(12) -0.1206(10) 0.233(13) Uani 0.25 1 d P A 2
F3B F -0.4296(19) -0.2489(17) -0.0530(11) 0.149(9) Uani 0.25 1 d P A 2
F4B F -0.192(2) -0.2127(16) -0.0217(8) 0.182(7) Uani 0.25 1 d P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0508(11) 0.0480(11) 0.0671(12) 0.0052(9) 0.0121(9) 0.0023(9)
N2 0.0600(13) 0.0487(12) 0.0698(13) 0.0060(10) 0.0081(10) 0.0034(10)
N3 0.0503(11) 0.0573(12) 0.0652(12) 0.0036(9) 0.0124(9) -0.0020(9)
C1 0.0545(14) 0.0491(13) 0.0594(14) -0.0016(11) 0.0048(11) 0.0013(11)
C2 0.0571(15) 0.0563(16) 0.0942(19) 0.0020(13) 0.0145(13) 0.0050(12)
C3 0.0598(16) 0.0698(18) 0.108(2) -0.0016(16) 0.0134(15) 0.0115(14)
C4 0.0782(19) 0.0518(15) 0.098(2) -0.0017(14) 0.0036(15) 0.0135(14)
C5 0.0783(19) 0.0515(15) 0.0826(18) 0.0048(13) 0.0086(14) 0.0045(13)
C6 0.0475(13) 0.0508(13) 0.0560(13) -0.0019(11) 0.0058(10) 0.0006(11)
C7 0.0557(15) 0.0558(15) 0.0838(17) 0.0073(13) 0.0097(12) 0.0029(12)
C8 0.0575(16) 0.0585(16) 0.097(2) -0.0033(14) 0.0000(14) 0.0099(13)
C9 0.0497(14) 0.0769(19) 0.0837(19) -0.0132(14) 0.0057(13) 0.0063(14)
C10 0.0547(15) 0.0728(17) 0.0673(16) 0.0000(13) 0.0082(12) -0.0034(13)
C11 0.0495(12) 0.0480(13) 0.0561(14) 0.0038(11) 0.0098(10) 0.0000(10)
C12 0.0647(15) 0.0619(15) 0.0571(15) -0.0044(12) 0.0052(11) -0.0068(12)
C13 0.0680(16) 0.0783(18) 0.0564(15) 0.0031(13) 0.0129(12) -0.0064(14)
C14 0.0540(14) 0.0630(15) 0.0655(16) 0.0103(13) 0.0086(12) 0.0000(12)
C15 0.0559(14) 0.0505(13) 0.0635(16) -0.0017(11) 0.0043(11) -0.0008(11)
C16 0.0523(13) 0.0477(13) 0.0528(14) 0.0016(10) 0.0049(10) 0.0041(10)
C17 0.116(2) 0.102(2) 0.0724(19) -0.0162(16) 0.0068(17) -0.0404(19)
C18 0.087(2) 0.094(2) 0.090(2) 0.0230(17) 0.0127(16) -0.0236(17)
C19 0.0820(18) 0.0749(18) 0.0564(15) -0.0055(12) 0.0096(13) -0.0024(14)
B1 0.077(2) 0.059(2) 0.077(3) 0.0017(16) 0.005(2) -0.0037(17)
F1 0.1431(18) 0.0666(12) 0.210(2) -0.0035(13) 0.0314(16) -0.0106(11)
F2A 0.163(6) 0.170(5) 0.128(4) 0.039(3) 0.093(4) 0.005(4)
F3A 0.0746(16) 0.0762(18) 0.151(3) 0.025(2) 0.015(2) 0.0070(13)
F4A 0.135(3) 0.121(3) 0.110(3) -0.018(2) -0.024(3) 0.014(2)
F2B 0.45(3) 0.098(9) 0.174(16) -0.004(9) 0.22(2) -0.015(14)
F3B 0.079(7) 0.112(7) 0.26(3) -0.028(13) 0.060(12) -0.030(5)
F4B 0.204(16) 0.192(14) 0.141(10) 0.030(9) -0.070(11) -0.051(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.394(3) . ?
N1 C6 1.417(3) . ?
N1 C11 1.453(3) . ?
N2 C1 1.335(3) . ?
N2 C5 1.350(3) . ?
N2 H1A 1.04(3) . ?
N3 C6 1.327(3) . ?
N3 C10 1.350(3) . ?
C1 C2 1.394(3) . ?
C2 C3 1.372(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.358(4) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.390(3) . ?
C7 C8 1.367(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.382(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.355(3) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C16 1.395(3) . ?
C11 C12 1.396(3) . ?
C12 C13 1.386(3) . ?
C12 C17 1.515(4) . ?
C13 C14 1.378(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.385(3) . ?
C14 C18 1.520(3) . ?
C15 C16 1.380(3) . ?
C15 H15A 0.9300 . ?
C16 C19 1.498(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17D 0.9600 . ?
C17 H17E 0.9600 . ?
C17 H17F 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 H18D 0.9600 . ?
C18 H18E 0.9600 . ?
C18 H18F 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19D 0.9600 . ?
C19 H19E 0.9600 . ?
C19 H19F 0.9600 . ?
B1 F3B 1.295(15) . ?
B1 F2A 1.319(6) . ?
B1 F2B 1.336(13) . ?
B1 F4B 1.340(13) . ?
B1 F4A 1.353(5) . ?
B1 F1 1.360(4) . ?
B1 F3A 1.364(4) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 124.63(18) . . ?
C1 N1 C11 117.16(17) . . ?
C6 N1 C11 118.14(17) . . ?
C1 N2 C5 121.8(2) . . ?
C1 N2 H1A 109.8(16) . . ?
C5 N2 H1A 128.2(16) . . ?
C6 N3 C10 119.2(2) . . ?
N2 C1 C2 118.9(2) . . ?
N2 C1 N1 119.3(2) . . ?
C2 C1 N1 121.7(2) . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
N2 C5 C4 120.9(2) . . ?
N2 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
N3 C6 C7 121.6(2) . . ?
N3 C6 N1 117.81(19) . . ?
C7 C6 N1 120.6(2) . . ?
C8 C7 C6 118.3(2) . . ?
C8 C7 H7A 120.8 . . ?
C6 C7 H7A 120.8 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C10 C9 C8 118.5(2) . . ?
C10 C9 H9A 120.7 . . ?
C8 C9 H9A 120.7 . . ?
N3 C10 C9 122.2(2) . . ?
N3 C10 H10A 118.9 . . ?
C9 C10 H10A 118.9 . . ?
C16 C11 C12 122.15(19) . . ?
C16 C11 N1 119.20(19) . . ?
C12 C11 N1 118.63(19) . . ?
C13 C12 C11 117.7(2) . . ?
C13 C12 C17 120.8(2) . . ?
C11 C12 C17 121.5(2) . . ?
C14 C13 C12 122.0(2) . . ?
C14 C13 H13A 119.0 . . ?
C12 C13 H13A 119.0 . . ?
C13 C14 C15 118.3(2) . . ?
C13 C14 C18 121.1(2) . . ?
C15 C14 C18 120.6(2) . . ?
C16 C15 C14 122.6(2) . . ?
C16 C15 H15A 118.7 . . ?
C14 C15 H15A 118.7 . . ?
C15 C16 C11 117.2(2) . . ?
C15 C16 C19 120.5(2) . . ?
C11 C16 C19 122.3(2) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C17 H17D 109.5 . . ?
H17A C17 H17D 141.1 . . ?
H17B C17 H17D 56.3 . . ?
H17C C17 H17D 56.3 . . ?
C12 C17 H17E 109.5 . . ?
H17A C17 H17E 56.3 . . ?
H17B C17 H17E 141.1 . . ?
H17C C17 H17E 56.3 . . ?
H17D C17 H17E 109.5 . . ?
C12 C17 H17F 109.5 . . ?
H17A C17 H17F 56.3 . . ?
H17B C17 H17F 56.3 . . ?
H17C C17 H17F 141.1 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C14 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C14 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C19 H19D 109.5 . . ?
H19A C19 H19D 141.1 . . ?
H19B C19 H19D 56.3 . . ?
H19C C19 H19D 56.3 . . ?
C16 C19 H19E 109.5 . . ?
H19A C19 H19E 56.3 . . ?
H19B C19 H19E 141.1 . . ?
H19C C19 H19E 56.3 . . ?
H19D C19 H19E 109.5 . . ?
C16 C19 H19F 109.5 . . ?
H19A C19 H19F 56.3 . . ?
H19B C19 H19F 56.3 . . ?
H19C C19 H19F 141.1 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
F3B B1 F2B 101.5(13) . . ?
F3B B1 F4B 111.1(12) . . ?
F2B B1 F4B 111.3(16) . . ?
F2A B1 F4A 107.8(4) . . ?
F3B B1 F1 130.1(8) . . ?
F2A B1 F1 112.2(4) . . ?
F2B B1 F1 108.8(6) . . ?
F4B B1 F1 93.9(7) . . ?
F4A B1 F1 103.7(3) . . ?
F2A B1 F3A 111.6(4) . . ?
F4A B1 F3A 109.1(4) . . ?
F1 B1 F3A 112.0(3) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C1 C2 2.2(3) . . . . ?
C5 N2 C1 N1 -179.6(2) . . . . ?
C6 N1 C1 N2 4.7(3) . . . . ?
C11 N1 C1 N2 -178.33(19) . . . . ?
C6 N1 C1 C2 -177.2(2) . . . . ?
C11 N1 C1 C2 -0.2(3) . . . . ?
N2 C1 C2 C3 -2.0(4) . . . . ?
N1 C1 C2 C3 179.9(2) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C1 N2 C5 C4 -1.2(4) . . . . ?
C3 C4 C5 N2 -0.1(4) . . . . ?
C10 N3 C6 C7 -0.9(3) . . . . ?
C10 N3 C6 N1 178.67(19) . . . . ?
C1 N1 C6 N3 0.9(3) . . . . ?
C11 N1 C6 N3 -175.99(19) . . . . ?
C1 N1 C6 C7 -179.5(2) . . . . ?
C11 N1 C6 C7 3.6(3) . . . . ?
N3 C6 C7 C8 0.8(4) . . . . ?
N1 C6 C7 C8 -178.7(2) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C6 N3 C10 C9 0.4(3) . . . . ?
C8 C9 C10 N3 0.2(4) . . . . ?
C1 N1 C11 C16 -96.2(2) . . . . ?
C6 N1 C11 C16 80.9(3) . . . . ?
C1 N1 C11 C12 82.4(3) . . . . ?
C6 N1 C11 C12 -100.5(2) . . . . ?
C16 C11 C12 C13 2.0(3) . . . . ?
N1 C11 C12 C13 -176.6(2) . . . . ?
C16 C11 C12 C17 -178.4(2) . . . . ?
N1 C11 C12 C17 3.0(3) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C17 C12 C13 C14 179.8(3) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C12 C13 C14 C18 178.4(2) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C18 C14 C15 C16 -178.4(2) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C14 C15 C16 C19 -178.7(2) . . . . ?
C12 C11 C16 C15 -1.9(3) . . . . ?
N1 C11 C16 C15 176.65(18) . . . . ?
C12 C11 C16 C19 177.2(2) . . . . ?
N1 C11 C16 C19 -4.2(3) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1A N3 1.04(3) 1.61(3) 2.535(3) 145(2) .
N2 H1A F1 1.04(3) 2.40(3) 3.066(3) 121(2) .
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full 28.35
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max 0.352
_refine_diff_density_min -0.183
_refine_diff_density_rms 0.039
_diffrn_ambient_pressure 101.33
_exptl_crystal_recrystallization_method
'cooled sat. soln in methanol to -12 deg. C for several days'
data_comdps
_database_code_depnum_ccdc_archive 'CCDC 724009'
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common
'(N-(mesityl)dipyridylamine)(\h2-styrene)copper(I) tetrafluoroborate'
_chemical_melting_point 448
_chemical_formula_moiety 'C27 H27 Cu N3, B F4'
_chemical_formula_sum 'C27 H27 B Cu F4 N3'
_chemical_formula_weight 543.87
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 13.001(3)
_cell_length_b 17.616(4)
_cell_length_c 23.608(5)
_cell_angle_alpha 90.00
_cell_angle_beta 105.69(3)
_cell_angle_gamma 90.00
_cell_volume 5205.1(18)
_cell_formula_units_Z 8
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 3680
_cell_measurement_theta_min 2.36
_cell_measurement_theta_max 16.40
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.53
_exptl_crystal_size_mid 0.41
_exptl_crystal_size_min 0.19
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.388
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2240
_exptl_absorpt_coefficient_mu 0.888
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6504
_exptl_absorpt_correction_T_max 0.8494
_exptl_absorpt_process_details 'SADABS v2.10 (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 63241
_diffrn_reflns_av_R_equivalents 0.1166
_diffrn_reflns_av_sigmaI/netI 0.1339
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_k_max 23
_diffrn_reflns_limit_l_min -31
_diffrn_reflns_limit_l_max 31
_diffrn_reflns_theta_min 1.46
_diffrn_reflns_theta_max 28.31
_reflns_number_total 12690
_reflns_number_gt 4306
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0975P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 12690
_refine_ls_number_parameters 721
_refine_ls_number_restraints 12
_refine_ls_R_factor_all 0.2229
_refine_ls_R_factor_gt 0.0616
_refine_ls_wR_factor_ref 0.2092
_refine_ls_wR_factor_gt 0.1381
_refine_ls_goodness_of_fit_ref 0.920
_refine_ls_restrained_S_all 0.922
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.70415(5) 0.78665(3) 0.17922(3) 0.0738(2) Uani 1 1 d . . .
N1 N 0.8596(3) 0.9115(2) 0.15373(15) 0.0572(9) Uani 1 1 d . . .
N2 N 0.6780(3) 0.8720(2) 0.12331(16) 0.0656(10) Uani 1 1 d . . .
N3 N 0.8542(3) 0.7810(2) 0.17957(17) 0.0690(10) Uani 1 1 d . . .
C1 C 0.7511(4) 0.9268(3) 0.12676(17) 0.0560(11) Uani 1 1 d . . .
C2 C 0.7205(4) 0.9972(3) 0.1030(2) 0.0709(13) Uani 1 1 d . . .
H2A H 0.7718 1.0348 0.1054 0.085 Uiso 1 1 calc R . .
C3 C 0.6159(5) 1.0127(3) 0.0758(2) 0.0852(16) Uani 1 1 d . . .
H3A H 0.5954 1.0611 0.0612 0.102 Uiso 1 1 calc R . .
C4 C 0.5404(4) 0.9553(4) 0.0702(2) 0.0840(16) Uani 1 1 d . . .
H4A H 0.4690 0.9634 0.0507 0.101 Uiso 1 1 calc R . .
C5 C 0.5753(4) 0.8869(3) 0.0945(2) 0.0760(14) Uani 1 1 d . . .
H5A H 0.5255 0.8481 0.0911 0.091 Uiso 1 1 calc R . .
C6 C 0.9074(4) 0.8399(3) 0.16494(18) 0.0616(12) Uani 1 1 d . . .
C7 C 1.0124(4) 0.8313(3) 0.1620(2) 0.0725(13) Uani 1 1 d . . .
H7A H 1.0491 0.8728 0.1528 0.087 Uiso 1 1 calc R . .
C8 C 1.0621(4) 0.7619(3) 0.1728(3) 0.0865(16) Uani 1 1 d . . .
H8A H 1.1320 0.7560 0.1706 0.104 Uiso 1 1 calc R . .
C9 C 1.0075(5) 0.7014(3) 0.1868(2) 0.0907(17) Uani 1 1 d . . .
H9A H 1.0391 0.6538 0.1943 0.109 Uiso 1 1 calc R . .
C10 C 0.9052(5) 0.7134(3) 0.1894(2) 0.0895(16) Uani 1 1 d . . .
H10A H 0.8679 0.6722 0.1986 0.107 Uiso 1 1 calc R . .
C11 C 0.9303(3) 0.9762(2) 0.1720(2) 0.0578(11) Uani 1 1 d . . .
C12 C 0.9726(4) 1.0143(3) 0.1322(2) 0.0719(13) Uani 1 1 d . . .
C13 C 1.0355(4) 1.0777(3) 0.1528(3) 0.0863(16) Uani 1 1 d . . .
H13A H 1.0637 1.1049 0.1267 0.104 Uiso 1 1 calc R . .
C14 C 1.0574(4) 1.1015(3) 0.2104(3) 0.0908(17) Uani 1 1 d . . .
C15 C 1.0168(4) 1.0615(3) 0.2479(2) 0.0819(15) Uani 1 1 d . . .
H15A H 1.0328 1.0769 0.2870 0.098 Uiso 1 1 calc R . .
C16 C 0.9521(4) 0.9980(3) 0.2307(2) 0.0635(12) Uani 1 1 d . . .
C17 C 0.9519(5) 0.9902(3) 0.0688(2) 0.0966(18) Uani 1 1 d . . .
H17A H 0.9884 1.0239 0.0489 0.145 Uiso 0.50 1 calc PR . .
H17B H 0.8765 0.9920 0.0501 0.145 Uiso 0.50 1 calc PR . .
H17C H 0.9775 0.9394 0.0671 0.145 Uiso 0.50 1 calc PR . .
H17D H 0.9065 0.9462 0.0619 0.145 Uiso 0.50 1 calc PR . .
H17E H 1.0184 0.9782 0.0606 0.145 Uiso 0.50 1 calc PR . .
H17F H 0.9175 1.0308 0.0436 0.145 Uiso 0.50 1 calc PR . .
C18 C 1.1256(6) 1.1719(4) 0.2302(4) 0.150(3) Uani 1 1 d . . .
H18A H 1.1471 1.1925 0.1975 0.225 Uiso 0.50 1 calc PR . .
H18B H 1.1878 1.1585 0.2610 0.225 Uiso 0.50 1 calc PR . .
H18C H 1.0849 1.2091 0.2445 0.225 Uiso 0.50 1 calc PR . .
H18D H 1.1328 1.1809 0.2712 0.225 Uiso 0.50 1 calc PR . .
H18E H 1.0921 1.2149 0.2077 0.225 Uiso 0.50 1 calc PR . .
H18F H 1.1950 1.1643 0.2242 0.225 Uiso 0.50 1 calc PR . .
C19 C 0.9082(4) 0.9546(3) 0.2740(2) 0.0902(16) Uani 1 1 d . . .
H19A H 0.9316 0.9781 0.3120 0.135 Uiso 0.50 1 calc PR . .
H19B H 0.9336 0.9032 0.2764 0.135 Uiso 0.50 1 calc PR . .
H19C H 0.8316 0.9548 0.2611 0.135 Uiso 0.50 1 calc PR . .
H19D H 0.8662 0.9126 0.2543 0.135 Uiso 0.50 1 calc PR . .
H19E H 0.8643 0.9875 0.2899 0.135 Uiso 0.50 1 calc PR . .
H19F H 0.9663 0.9359 0.3052 0.135 Uiso 0.50 1 calc PR . .
C20 C 0.5705(5) 0.7634(3) 0.2000(3) 0.0925(17) Uani 1 1 d . . .
H20A H 0.5386 0.8049 0.2163 0.111 Uiso 1 1 calc R . .
H20B H 0.5186 0.7329 0.1720 0.111 Uiso 1 1 calc R . .
C21 C 0.6510(5) 0.7246(3) 0.2387(3) 0.0887(16) Uani 1 1 d . . .
H21A H 0.6501 0.6697 0.2322 0.106 Uiso 1 1 calc R . .
C22 C 0.6999(4) 0.7477(3) 0.3001(3) 0.0738(14) Uani 1 1 d . . .
C23 C 0.7397(6) 0.6943(4) 0.3434(4) 0.123(2) Uani 1 1 d . . .
H23A H 0.7398 0.6434 0.3330 0.148 Uiso 1 1 calc R . .
C24 C 0.7792(7) 0.7149(5) 0.4015(4) 0.137(3) Uani 1 1 d . . .
H24A H 0.8048 0.6774 0.4296 0.165 Uiso 1 1 calc R . .
C25 C 0.7817(5) 0.7859(5) 0.4184(3) 0.1004(18) Uani 1 1 d . . .
H25A H 0.8076 0.7983 0.4580 0.120 Uiso 1 1 calc R . .
C26 C 0.7462(5) 0.8415(4) 0.3777(3) 0.0964(18) Uani 1 1 d . . .
H26A H 0.7499 0.8923 0.3890 0.116 Uiso 1 1 calc R . .
C27 C 0.7048(5) 0.8213(4) 0.3200(3) 0.0929(17) Uani 1 1 d . . .
H27A H 0.6787 0.8596 0.2927 0.111 Uiso 1 1 calc R . .
Cu2 Cu 0.31215(5) 0.36541(4) 0.05003(3) 0.0820(3) Uani 1 1 d . . .
N4 N 0.1330(3) 0.4295(2) 0.10214(15) 0.0599(10) Uani 1 1 d . . .
N5 N 0.2866(3) 0.4685(2) 0.07320(17) 0.0704(11) Uani 1 1 d . . .
N6 N 0.1601(3) 0.3388(2) 0.03343(17) 0.0631(10) Uani 1 1 d . . .
C28 C 0.2021(4) 0.4871(3) 0.09157(19) 0.0617(12) Uani 1 1 d . . .
C29 C 0.1806(4) 0.5625(3) 0.1024(2) 0.0803(15) Uani 1 1 d . . .
H29A H 0.1219 0.5748 0.1159 0.096 Uiso 1 1 calc R . .
C30 C 0.2468(5) 0.6176(3) 0.0927(2) 0.0915(17) Uani 1 1 d . . .
H30A H 0.2324 0.6683 0.0985 0.110 Uiso 1 1 calc R . .
C31 C 0.3346(5) 0.5988(4) 0.0744(2) 0.0895(17) Uani 1 1 d . . .
H31A H 0.3814 0.6360 0.0686 0.107 Uiso 1 1 calc R . .
C32 C 0.3519(4) 0.5255(4) 0.0651(2) 0.0880(16) Uani 1 1 d . . .
H32A H 0.4115 0.5130 0.0524 0.106 Uiso 1 1 calc R . .
C33 C 0.1047(4) 0.3614(3) 0.0697(2) 0.0610(12) Uani 1 1 d . . .
C34 C 0.0158(4) 0.3209(3) 0.0765(2) 0.0771(14) Uani 1 1 d . . .
H34A H -0.0197 0.3359 0.1040 0.093 Uiso 1 1 calc R . .
C35 C -0.0176(5) 0.2582(3) 0.0413(3) 0.0938(18) Uani 1 1 d . . .
H35A H -0.0758 0.2297 0.0448 0.113 Uiso 1 1 calc R . .
C36 C 0.0363(5) 0.2386(3) 0.0011(3) 0.0907(17) Uani 1 1 d . . .
H36A H 0.0129 0.1980 -0.0243 0.109 Uiso 1 1 calc R . .
C37 C 0.1228(4) 0.2779(3) -0.0015(2) 0.0783(15) Uani 1 1 d . . .
H37A H 0.1592 0.2630 -0.0285 0.094 Uiso 1 1 calc R . .
C38 C 0.0758(4) 0.4489(2) 0.1450(2) 0.0581(11) Uani 1 1 d . . .
C39 C -0.0243(4) 0.4820(3) 0.12697(19) 0.0615(12) Uani 1 1 d . . .
C40 C -0.0746(4) 0.5014(3) 0.1697(2) 0.0701(13) Uani 1 1 d . . .
H40A H -0.1420 0.5235 0.1584 0.084 Uiso 1 1 calc R . .
C41 C -0.0270(5) 0.4885(3) 0.2287(2) 0.0720(14) Uani 1 1 d . . .
C42 C 0.0708(5) 0.4544(3) 0.2447(2) 0.0789(15) Uani 1 1 d . . .
H42A H 0.1020 0.4448 0.2844 0.095 Uiso 1 1 calc R . .
C43 C 0.1259(4) 0.4334(3) 0.2040(2) 0.0673(13) Uani 1 1 d . . .
C44 C -0.0806(4) 0.4973(3) 0.0633(2) 0.0830(15) Uani 1 1 d . . .
H44A H -0.1487 0.5203 0.0605 0.124 Uiso 0.50 1 calc PR . .
H44B H -0.0910 0.4503 0.0418 0.124 Uiso 0.50 1 calc PR . .
H44C H -0.0380 0.5308 0.0469 0.124 Uiso 0.50 1 calc PR . .
H44D H -0.0364 0.4807 0.0390 0.124 Uiso 0.50 1 calc PR . .
H44E H -0.0941 0.5507 0.0577 0.124 Uiso 0.50 1 calc PR . .
H44F H -0.1471 0.4701 0.0526 0.124 Uiso 0.50 1 calc PR . .
C45 C -0.0836(5) 0.5117(4) 0.2750(2) 0.111(2) Uani 1 1 d . . .
H45A H -0.1510 0.5348 0.2560 0.167 Uiso 0.50 1 calc PR . .
H45B H -0.0400 0.5474 0.3018 0.167 Uiso 0.50 1 calc PR . .
H45C H -0.0953 0.4676 0.2963 0.167 Uiso 0.50 1 calc PR . .
H45D H -0.0398 0.4984 0.3134 0.167 Uiso 0.50 1 calc PR . .
H45E H -0.1509 0.4858 0.2676 0.167 Uiso 0.50 1 calc PR . .
H45F H -0.0956 0.5656 0.2731 0.167 Uiso 0.50 1 calc PR . .
C46 C 0.2351(5) 0.3976(4) 0.2233(3) 0.107(2) Uani 1 1 d . . .
H46A H 0.2602 0.3871 0.1894 0.161 Uiso 0.50 1 calc PR . .
H46B H 0.2309 0.3511 0.2438 0.161 Uiso 0.50 1 calc PR . .
H46C H 0.2836 0.4318 0.2490 0.161 Uiso 0.50 1 calc PR . .
H46D H 0.2563 0.3929 0.2654 0.161 Uiso 0.50 1 calc PR . .
H46E H 0.2856 0.4289 0.2110 0.161 Uiso 0.50 1 calc PR . .
H46F H 0.2329 0.3482 0.2058 0.161 Uiso 0.50 1 calc PR . .
C47 C 0.4656(5) 0.3379(4) 0.0711(4) 0.138(3) Uani 1 1 d . . .
H47A H 0.5088 0.3627 0.0489 0.166 Uiso 1 1 calc R . .
H47B H 0.5011 0.3336 0.1128 0.166 Uiso 1 1 calc R . .
C48 C 0.4073(5) 0.2756(4) 0.0449(3) 0.1029(19) Uani 1 1 d . . .
H48A H 0.4126 0.2647 0.0051 0.124 Uiso 1 1 calc R . .
C49 C 0.3754(5) 0.2097(4) 0.0752(3) 0.0842(16) Uani 1 1 d . . .
C50 C 0.3314(5) 0.1483(4) 0.0414(3) 0.0995(19) Uani 1 1 d . . .
H50A H 0.3239 0.1495 0.0011 0.119 Uiso 1 1 calc R . .
C51 C 0.2975(5) 0.0840(4) 0.0663(4) 0.117(2) Uani 1 1 d . . .
H51A H 0.2690 0.0426 0.0429 0.141 Uiso 1 1 calc R . .
C52 C 0.3063(7) 0.0828(5) 0.1240(5) 0.137(3) Uani 1 1 d . . .
H52A H 0.2813 0.0413 0.1408 0.164 Uiso 1 1 calc R . .
C53 C 0.3516(8) 0.1418(7) 0.1577(4) 0.149(3) Uani 1 1 d . . .
H53A H 0.3614 0.1392 0.1981 0.179 Uiso 1 1 calc R . .
C54 C 0.3834(6) 0.2051(5) 0.1344(4) 0.124(2) Uani 1 1 d . . .
H54A H 0.4110 0.2459 0.1588 0.148 Uiso 1 1 calc R . .
B1 B 0.3493(8) 0.3881(6) -0.0920(5) 0.102(2) Uani 1 1 d . . .
F1 F 0.4076(14) 0.4467(14) -0.0640(9) 0.199(9) Uani 0.50 1 d P A -1
F2 F 0.4039(16) 0.3193(9) -0.0902(7) 0.140(7) Uani 0.50 1 d P A -1
F3 F 0.2678(9) 0.3790(8) -0.0675(5) 0.105(5) Uani 0.50 1 d P A -1
F4 F 0.3063(13) 0.4088(12) -0.1526(8) 0.106(5) Uani 0.50 1 d P A -1
F1A F 0.2743(14) 0.3408(15) -0.0904(8) 0.217(9) Uani 0.50 1 d P A -2
F2A F 0.354(2) 0.4363(14) -0.0488(10) 0.246(10) Uani 0.50 1 d P A -2
F3A F 0.4372(14) 0.3538(13) -0.0775(11) 0.195(10) Uani 0.50 1 d P A -2
F4A F 0.334(2) 0.4196(15) -0.1416(13) 0.210(13) Uani 0.50 1 d P A -2
B2 B 0.2662(7) 0.8525(5) 0.0777(5) 0.096(2) Uani 1 1 d . . .
F11 F 0.202(2) 0.8233(14) 0.0967(14) 0.34(2) Uani 0.50 1 d PD B -1
F12 F 0.3266(10) 0.7942(5) 0.0653(6) 0.164(4) Uani 0.50 1 d PD B -1
F13 F 0.3311(12) 0.8985(6) 0.1112(7) 0.149(5) Uani 0.50 1 d PD B -1
F14 F 0.2163(18) 0.8837(10) 0.0280(7) 0.244(10) Uani 0.50 1 d PD B -1
F11A F 0.3279(15) 0.8391(15) 0.1263(7) 0.293(12) Uani 0.50 1 d PD B -2
F12A F 0.2112(18) 0.7934(8) 0.0617(8) 0.235(10) Uani 0.50 1 d PD B -2
F13A F 0.1960(13) 0.8967(7) 0.0980(9) 0.240(8) Uani 0.50 1 d PD B -2
F14A F 0.2998(10) 0.8870(8) 0.0380(6) 0.158(5) Uani 0.50 1 d PD B -2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0817(5) 0.0691(4) 0.0768(4) 0.0055(3) 0.0318(3) -0.0056(3)
N1 0.059(2) 0.054(2) 0.058(2) -0.0018(18) 0.0145(19) 0.002(2)
N2 0.058(3) 0.076(3) 0.064(3) 0.002(2) 0.018(2) -0.002(2)
N3 0.073(3) 0.057(3) 0.079(3) 0.007(2) 0.024(2) 0.003(2)
C1 0.064(3) 0.063(3) 0.042(3) -0.003(2) 0.016(2) 0.003(3)
C2 0.069(3) 0.067(3) 0.073(3) 0.003(3) 0.013(3) 0.000(3)
C3 0.096(4) 0.084(4) 0.069(4) 0.005(3) 0.012(3) 0.012(4)
C4 0.070(4) 0.113(5) 0.062(3) 0.011(3) 0.007(3) 0.009(4)
C5 0.066(4) 0.100(4) 0.062(3) 0.003(3) 0.018(3) -0.010(3)
C6 0.065(3) 0.069(3) 0.049(3) -0.008(2) 0.014(2) 0.006(3)
C7 0.069(3) 0.061(3) 0.087(4) -0.004(3) 0.020(3) 0.000(3)
C8 0.073(4) 0.076(4) 0.106(4) -0.011(3) 0.017(3) 0.008(3)
C9 0.095(5) 0.064(4) 0.107(5) -0.002(3) 0.017(4) 0.019(3)
C10 0.096(5) 0.058(4) 0.115(5) 0.003(3) 0.032(4) -0.001(3)
C11 0.062(3) 0.053(3) 0.058(3) -0.007(2) 0.015(2) 0.000(2)
C12 0.076(3) 0.071(3) 0.073(4) -0.002(3) 0.028(3) -0.002(3)
C13 0.088(4) 0.075(4) 0.105(5) -0.002(3) 0.041(3) -0.019(3)
C14 0.073(4) 0.080(4) 0.124(5) -0.032(4) 0.035(4) -0.018(3)
C15 0.071(3) 0.093(4) 0.079(4) -0.035(3) 0.018(3) -0.002(3)
C16 0.062(3) 0.063(3) 0.067(3) -0.001(3) 0.019(3) 0.003(3)
C17 0.120(5) 0.101(4) 0.082(4) 0.000(3) 0.049(4) -0.013(4)
C18 0.136(6) 0.116(6) 0.212(8) -0.059(6) 0.072(6) -0.053(5)
C19 0.109(4) 0.101(4) 0.061(3) -0.012(3) 0.023(3) 0.005(3)
C20 0.087(4) 0.105(4) 0.092(4) 0.005(4) 0.037(4) -0.021(4)
C21 0.104(4) 0.075(4) 0.097(5) 0.018(4) 0.044(4) -0.008(3)
C22 0.080(4) 0.064(4) 0.089(4) 0.012(3) 0.043(3) 0.001(3)
C23 0.187(7) 0.066(4) 0.118(6) 0.018(4) 0.043(5) 0.014(4)
C24 0.195(8) 0.107(6) 0.097(6) 0.018(5) 0.017(5) 0.021(6)
C25 0.094(4) 0.123(6) 0.089(5) 0.002(5) 0.034(4) -0.002(4)
C26 0.095(4) 0.097(5) 0.105(5) -0.011(4) 0.040(4) 0.014(4)
C27 0.103(5) 0.082(4) 0.098(5) 0.011(4) 0.035(4) 0.023(3)
Cu2 0.0631(4) 0.0759(5) 0.1112(6) -0.0024(4) 0.0308(4) 0.0054(3)
N4 0.065(2) 0.056(2) 0.063(2) 0.003(2) 0.025(2) -0.002(2)
N5 0.060(2) 0.073(3) 0.084(3) -0.002(2) 0.028(2) -0.003(2)
N6 0.058(2) 0.059(2) 0.074(3) -0.004(2) 0.021(2) 0.005(2)
C28 0.074(3) 0.058(3) 0.054(3) 0.001(2) 0.019(2) -0.008(3)
C29 0.088(4) 0.064(3) 0.100(4) -0.002(3) 0.045(3) -0.006(3)
C30 0.114(5) 0.066(4) 0.103(4) -0.008(3) 0.044(4) -0.014(3)
C31 0.091(4) 0.081(4) 0.100(4) 0.006(3) 0.031(3) -0.028(3)
C32 0.075(4) 0.086(4) 0.112(5) -0.004(3) 0.040(3) -0.016(3)
C33 0.062(3) 0.056(3) 0.064(3) 0.003(2) 0.014(2) -0.001(2)
C34 0.078(3) 0.064(3) 0.100(4) -0.017(3) 0.043(3) -0.013(3)
C35 0.089(4) 0.074(4) 0.126(5) -0.025(4) 0.043(4) -0.023(3)
C36 0.084(4) 0.081(4) 0.107(5) -0.031(3) 0.025(4) -0.009(3)
C37 0.071(4) 0.084(4) 0.082(4) -0.019(3) 0.025(3) 0.004(3)
C38 0.069(3) 0.054(3) 0.057(3) -0.001(2) 0.026(3) -0.006(2)
C39 0.073(3) 0.065(3) 0.051(3) 0.004(2) 0.024(3) -0.003(3)
C40 0.078(3) 0.067(3) 0.073(4) 0.000(3) 0.032(3) -0.005(3)
C41 0.095(4) 0.063(3) 0.066(4) -0.007(3) 0.036(3) -0.022(3)
C42 0.103(4) 0.082(4) 0.050(3) 0.004(3) 0.018(3) -0.020(3)
C43 0.073(3) 0.064(3) 0.059(3) 0.006(3) 0.009(3) -0.012(3)
C44 0.088(4) 0.102(4) 0.060(3) 0.012(3) 0.022(3) 0.019(3)
C45 0.147(6) 0.126(5) 0.083(4) -0.015(4) 0.069(4) -0.027(4)
C46 0.101(5) 0.121(5) 0.088(4) 0.019(4) 0.005(4) 0.009(4)
C47 0.055(4) 0.127(6) 0.232(9) -0.012(6) 0.039(5) 0.020(4)
C48 0.079(4) 0.102(5) 0.139(6) -0.004(5) 0.048(4) 0.028(4)
C49 0.086(4) 0.089(5) 0.077(4) 0.001(4) 0.022(3) 0.034(3)
C50 0.124(5) 0.097(5) 0.074(4) -0.007(4) 0.021(4) 0.032(4)
C51 0.109(5) 0.092(6) 0.129(7) -0.002(5) -0.005(5) 0.027(4)
C52 0.143(7) 0.124(7) 0.138(8) 0.044(6) 0.028(6) 0.036(6)
C53 0.201(10) 0.164(9) 0.076(6) 0.026(6) 0.023(6) 0.052(8)
C54 0.152(7) 0.108(6) 0.091(6) -0.008(5) 0.000(5) 0.032(5)
B1 0.085(7) 0.114(8) 0.123(8) -0.018(7) 0.055(7) -0.013(6)
F1 0.144(11) 0.261(18) 0.226(15) -0.144(12) 0.108(9) -0.116(13)
F2 0.20(2) 0.115(9) 0.124(7) -0.015(6) 0.077(9) 0.042(9)
F3 0.079(7) 0.153(10) 0.103(8) 0.032(7) 0.057(7) 0.045(8)
F4 0.097(6) 0.120(10) 0.109(10) -0.020(8) 0.042(6) -0.001(6)
F1A 0.150(16) 0.33(2) 0.156(13) 0.042(14) 0.024(9) -0.128(16)
F2A 0.26(3) 0.24(2) 0.221(18) -0.131(16) 0.048(16) 0.04(2)
F3A 0.100(9) 0.23(2) 0.29(2) 0.033(16) 0.108(11) 0.067(13)
F4A 0.29(3) 0.150(15) 0.26(3) 0.074(19) 0.20(2) 0.010(16)
B2 0.070(5) 0.096(7) 0.123(8) -0.004(6) 0.030(6) -0.025(6)
F11 0.32(3) 0.26(2) 0.56(5) -0.21(3) 0.34(3) -0.20(2)
F12 0.150(9) 0.096(7) 0.245(14) -0.042(7) 0.055(9) 0.006(7)
F13 0.160(10) 0.121(7) 0.153(12) -0.052(7) 0.023(8) -0.076(8)
F14 0.31(2) 0.193(15) 0.148(11) 0.004(10) -0.079(16) 0.065(18)
F11A 0.217(19) 0.47(4) 0.129(11) -0.05(2) -0.060(12) 0.04(3)
F12A 0.27(2) 0.123(10) 0.251(16) -0.020(10) -0.038(15) -0.091(12)
F13A 0.231(14) 0.139(9) 0.43(3) 0.051(12) 0.230(17) 0.047(10)
F14A 0.147(9) 0.188(12) 0.161(13) 0.019(10) 0.080(10) -0.040(10)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.951(4) . ?
Cu1 N2 1.968(4) . ?
Cu1 C20 1.972(5) . ?
Cu1 C21 2.042(5) . ?
N1 C6 1.400(5) . ?
N1 C1 1.408(5) . ?
N1 C11 1.455(5) . ?
N2 C1 1.342(5) . ?
N2 C5 1.350(6) . ?
N3 C6 1.342(6) . ?
N3 C10 1.353(6) . ?
C1 C2 1.376(6) . ?
C2 C3 1.365(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.391(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.358(7) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.393(6) . ?
C7 C8 1.375(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.369(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.365(7) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.384(6) . ?
C11 C16 1.391(6) . ?
C12 C13 1.392(7) . ?
C12 C17 1.507(7) . ?
C13 C14 1.377(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.346(7) . ?
C14 C18 1.523(8) . ?
C15 C16 1.393(7) . ?
C15 H15A 0.9300 . ?
C16 C19 1.506(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17D 0.9600 . ?
C17 H17E 0.9600 . ?
C17 H17F 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 H18D 0.9600 . ?
C18 H18E 0.9600 . ?
C18 H18F 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19D 0.9600 . ?
C19 H19E 0.9600 . ?
C19 H19F 0.9600 . ?
C20 C21 1.372(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.473(8) . ?
C21 H21A 0.9800 . ?
C22 C27 1.375(7) . ?
C22 C23 1.382(8) . ?
C23 C24 1.379(9) . ?
C23 H23A 0.9300 . ?
C24 C25 1.311(8) . ?
C24 H24A 0.9300 . ?
C25 C26 1.361(8) . ?
C25 H25A 0.9300 . ?
C26 C27 1.371(8) . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?
Cu2 N5 1.951(4) . ?
Cu2 N6 1.965(4) . ?
Cu2 C47 1.981(6) . ?
Cu2 C48 2.032(6) . ?
N4 C33 1.417(5) . ?
N4 C28 1.422(5) . ?
N4 C38 1.449(5) . ?
N5 C28 1.328(5) . ?
N5 C32 1.361(6) . ?
N6 C33 1.322(5) . ?
N6 C37 1.359(6) . ?
C28 C29 1.395(6) . ?
C29 C30 1.358(7) . ?
C29 H29A 0.9300 . ?
C30 C31 1.366(7) . ?
C30 H30A 0.9300 . ?
C31 C32 1.338(7) . ?
C31 H31A 0.9300 . ?
C32 H32A 0.9300 . ?
C33 C34 1.404(6) . ?
C34 C35 1.381(7) . ?
C34 H34A 0.9300 . ?
C35 C36 1.366(7) . ?
C35 H35A 0.9300 . ?
C36 C37 1.335(7) . ?
C36 H36A 0.9300 . ?
C37 H37A 0.9300 . ?
C38 C39 1.384(6) . ?
C38 C43 1.395(6) . ?
C39 C40 1.385(6) . ?
C39 C44 1.508(6) . ?
C40 C41 1.381(7) . ?
C40 H40A 0.9300 . ?
C41 C42 1.364(7) . ?
C41 C45 1.530(7) . ?
C42 C43 1.396(7) . ?
C42 H42A 0.9300 . ?
C43 C46 1.507(7) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C44 H44D 0.9600 . ?
C44 H44E 0.9600 . ?
C44 H44F 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C45 H45D 0.9600 . ?
C45 H45E 0.9600 . ?
C45 H45F 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C46 H46D 0.9600 . ?
C46 H46E 0.9600 . ?
C46 H46F 0.9600 . ?
C47 C48 1.381(8) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 C49 1.479(8) . ?
C48 H48A 0.9800 . ?
C49 C54 1.374(9) . ?
C49 C50 1.374(8) . ?
C50 C51 1.401(9) . ?
C50 H50A 0.9300 . ?
C51 C52 1.336(10) . ?
C51 H51A 0.9300 . ?
C52 C53 1.345(11) . ?
C52 H52A 0.9300 . ?
C53 C54 1.356(11) . ?
C53 H53A 0.9300 . ?
C54 H54A 0.9300 . ?
B1 F3A 1.255(19) . ?
B1 F4A 1.26(3) . ?
B1 F1A 1.291(18) . ?
B1 F2A 1.317(19) . ?
B1 F1 1.35(2) . ?
B1 F3 1.347(15) . ?
B1 F2 1.398(19) . ?
B1 F4 1.43(2) . ?
B2 F11 1.171(16) . ?
B2 F11A 1.232(16) . ?
B2 F12A 1.261(14) . ?
B2 F13 1.279(14) . ?
B2 F14A 1.287(15) . ?
B2 F14 1.298(16) . ?
B2 F12 1.371(12) . ?
B2 F13A 1.381(13) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N2 91.88(17) . . ?
N3 Cu1 C20 159.4(2) . . ?
N2 Cu1 C20 108.7(2) . . ?
N3 Cu1 C21 119.6(2) . . ?
N2 Cu1 C21 147.2(2) . . ?
C20 Cu1 C21 39.9(2) . . ?
C6 N1 C1 126.7(4) . . ?
C6 N1 C11 116.0(4) . . ?
C1 N1 C11 117.3(4) . . ?
C1 N2 C5 118.6(4) . . ?
C1 N2 Cu1 121.2(3) . . ?
C5 N2 Cu1 117.0(3) . . ?
C6 N3 C10 117.5(4) . . ?
C6 N3 Cu1 123.0(3) . . ?
C10 N3 Cu1 119.2(4) . . ?
N2 C1 C2 120.1(4) . . ?
N2 C1 N1 119.8(4) . . ?
C2 C1 N1 120.1(4) . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C2 C3 C4 119.1(5) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 117.4(5) . . ?
C5 C4 H4A 121.3 . . ?
C3 C4 H4A 121.3 . . ?
N2 C5 C4 123.8(5) . . ?
N2 C5 H5A 118.1 . . ?
C4 C5 H5A 118.1 . . ?
N3 C6 C7 120.6(4) . . ?
N3 C6 N1 120.7(4) . . ?
C7 C6 N1 118.6(5) . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C9 C8 C7 119.2(5) . . ?
C9 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
C10 C9 C8 117.8(5) . . ?
C10 C9 H9A 121.1 . . ?
C8 C9 H9A 121.1 . . ?
N3 C10 C9 124.5(5) . . ?
N3 C10 H10A 117.8 . . ?
C9 C10 H10A 117.8 . . ?
C12 C11 C16 122.2(4) . . ?
C12 C11 N1 120.9(4) . . ?
C16 C11 N1 116.9(4) . . ?
C11 C12 C13 117.1(5) . . ?
C11 C12 C17 122.7(5) . . ?
C13 C12 C17 120.2(5) . . ?
C14 C13 C12 122.3(5) . . ?
C14 C13 H13A 118.8 . . ?
C12 C13 H13A 118.8 . . ?
C15 C14 C13 118.5(5) . . ?
C15 C14 C18 121.6(6) . . ?
C13 C14 C18 119.9(6) . . ?
C14 C15 C16 122.9(5) . . ?
C14 C15 H15A 118.6 . . ?
C16 C15 H15A 118.6 . . ?
C11 C16 C15 117.1(4) . . ?
C11 C16 C19 121.6(4) . . ?
C15 C16 C19 121.3(5) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C17 H17D 109.5 . . ?
H17A C17 H17D 141.1 . . ?
H17B C17 H17D 56.3 . . ?
H17C C17 H17D 56.3 . . ?
C12 C17 H17E 109.5 . . ?
H17A C17 H17E 56.3 . . ?
H17B C17 H17E 141.1 . . ?
H17C C17 H17E 56.3 . . ?
H17D C17 H17E 109.5 . . ?
C12 C17 H17F 109.5 . . ?
H17A C17 H17F 56.3 . . ?
H17B C17 H17F 56.3 . . ?
H17C C17 H17F 141.1 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C14 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C14 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C19 H19D 109.5 . . ?
H19A C19 H19D 141.1 . . ?
H19B C19 H19D 56.3 . . ?
H19C C19 H19D 56.3 . . ?
C16 C19 H19E 109.5 . . ?
H19A C19 H19E 56.3 . . ?
H19B C19 H19E 141.1 . . ?
H19C C19 H19E 56.3 . . ?
H19D C19 H19E 109.5 . . ?
C16 C19 H19F 109.5 . . ?
H19A C19 H19F 56.3 . . ?
H19B C19 H19F 56.3 . . ?
H19C C19 H19F 141.1 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
C21 C20 Cu1 72.8(3) . . ?
C21 C20 H20A 116.3 . . ?
Cu1 C20 H20A 116.3 . . ?
C21 C20 H20B 116.3 . . ?
Cu1 C20 H20B 116.3 . . ?
H20A C20 H20B 113.3 . . ?
C20 C21 C22 124.5(5) . . ?
C20 C21 Cu1 67.3(3) . . ?
C22 C21 Cu1 113.1(4) . . ?
C20 C21 H21A 114.3 . . ?
C22 C21 H21A 114.3 . . ?
Cu1 C21 H21A 114.3 . . ?
C27 C22 C23 114.6(6) . . ?
C27 C22 C21 124.3(5) . . ?
C23 C22 C21 121.0(6) . . ?
C24 C23 C22 121.4(6) . . ?
C24 C23 H23A 119.3 . . ?
C22 C23 H23A 119.3 . . ?
C25 C24 C23 121.7(7) . . ?
C25 C24 H24A 119.1 . . ?
C23 C24 H24A 119.1 . . ?
C24 C25 C26 119.8(7) . . ?
C24 C25 H25A 120.1 . . ?
C26 C25 H25A 120.1 . . ?
C25 C26 C27 118.8(6) . . ?
C25 C26 H26A 120.6 . . ?
C27 C26 H26A 120.6 . . ?
C26 C27 C22 123.6(6) . . ?
C26 C27 H27A 118.2 . . ?
C22 C27 H27A 118.2 . . ?
N5 Cu2 N6 92.29(16) . . ?
N5 Cu2 C47 113.2(3) . . ?
N6 Cu2 C47 151.8(3) . . ?
N5 Cu2 C48 153.4(2) . . ?
N6 Cu2 C48 113.4(2) . . ?
C47 Cu2 C48 40.2(2) . . ?
C33 N4 C28 126.5(4) . . ?
C33 N4 C38 118.0(4) . . ?
C28 N4 C38 115.0(4) . . ?
C28 N5 C32 117.7(4) . . ?
C28 N5 Cu2 122.7(3) . . ?
C32 N5 Cu2 119.2(4) . . ?
C33 N6 C37 117.6(4) . . ?
C33 N6 Cu2 119.6(3) . . ?
C37 N6 Cu2 119.0(3) . . ?
N5 C28 C29 121.3(4) . . ?
N5 C28 N4 119.9(4) . . ?
C29 C28 N4 118.7(4) . . ?
C30 C29 C28 118.9(5) . . ?
C30 C29 H29A 120.6 . . ?
C28 C29 H29A 120.6 . . ?
C29 C30 C31 120.1(5) . . ?
C29 C30 H30A 120.0 . . ?
C31 C30 H30A 120.0 . . ?
C32 C31 C30 118.6(5) . . ?
C32 C31 H31A 120.7 . . ?
C30 C31 H31A 120.7 . . ?
C31 C32 N5 123.4(5) . . ?
C31 C32 H32A 118.3 . . ?
N5 C32 H32A 118.3 . . ?
N6 C33 C34 122.1(4) . . ?
N6 C33 N4 119.8(4) . . ?
C34 C33 N4 118.0(4) . . ?
C35 C34 C33 118.1(5) . . ?
C35 C34 H34A 120.9 . . ?
C33 C34 H34A 120.9 . . ?
C36 C35 C34 118.9(5) . . ?
C36 C35 H35A 120.6 . . ?
C34 C35 H35A 120.6 . . ?
C37 C36 C35 119.8(5) . . ?
C37 C36 H36A 120.1 . . ?
C35 C36 H36A 120.1 . . ?
C36 C37 N6 123.2(5) . . ?
C36 C37 H37A 118.4 . . ?
N6 C37 H37A 118.4 . . ?
C39 C38 C43 122.4(4) . . ?
C39 C38 N4 120.2(4) . . ?
C43 C38 N4 117.5(4) . . ?
C38 C39 C40 118.0(4) . . ?
C38 C39 C44 123.0(4) . . ?
C40 C39 C44 119.0(5) . . ?
C41 C40 C39 121.6(5) . . ?
C41 C40 H40A 119.2 . . ?
C39 C40 H40A 119.2 . . ?
C42 C41 C40 118.8(5) . . ?
C42 C41 C45 120.8(5) . . ?
C40 C41 C45 120.5(6) . . ?
C41 C42 C43 122.7(5) . . ?
C41 C42 H42A 118.7 . . ?
C43 C42 H42A 118.7 . . ?
C38 C43 C42 116.6(5) . . ?
C38 C43 C46 122.1(5) . . ?
C42 C43 C46 121.3(5) . . ?
C39 C44 H44A 109.5 . . ?
C39 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C39 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C39 C44 H44D 109.5 . . ?
H44A C44 H44D 141.1 . . ?
H44B C44 H44D 56.3 . . ?
H44C C44 H44D 56.3 . . ?
C39 C44 H44E 109.5 . . ?
H44A C44 H44E 56.3 . . ?
H44B C44 H44E 141.1 . . ?
H44C C44 H44E 56.3 . . ?
H44D C44 H44E 109.5 . . ?
C39 C44 H44F 109.5 . . ?
H44A C44 H44F 56.3 . . ?
H44B C44 H44F 56.3 . . ?
H44C C44 H44F 141.1 . . ?
H44D C44 H44F 109.5 . . ?
H44E C44 H44F 109.5 . . ?
C41 C45 H45A 109.5 . . ?
C41 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C41 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C41 C45 H45D 109.5 . . ?
H45A C45 H45D 141.1 . . ?
H45B C45 H45D 56.3 . . ?
H45C C45 H45D 56.3 . . ?
C41 C45 H45E 109.5 . . ?
H45A C45 H45E 56.3 . . ?
H45B C45 H45E 141.1 . . ?
H45C C45 H45E 56.3 . . ?
H45D C45 H45E 109.5 . . ?
C41 C45 H45F 109.5 . . ?
H45A C45 H45F 56.3 . . ?
H45B C45 H45F 56.3 . . ?
H45C C45 H45F 141.1 . . ?
H45D C45 H45F 109.5 . . ?
H45E C45 H45F 109.5 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C43 C46 H46D 109.5 . . ?
H46A C46 H46D 141.1 . . ?
H46B C46 H46D 56.3 . . ?
H46C C46 H46D 56.3 . . ?
C43 C46 H46E 109.5 . . ?
H46A C46 H46E 56.3 . . ?
H46B C46 H46E 141.1 . . ?
H46C C46 H46E 56.3 . . ?
H46D C46 H46E 109.5 . . ?
C43 C46 H46F 109.5 . . ?
H46A C46 H46F 56.3 . . ?
H46B C46 H46F 56.3 . . ?
H46C C46 H46F 141.1 . . ?
H46D C46 H46F 109.5 . . ?
H46E C46 H46F 109.5 . . ?
C48 C47 Cu2 71.8(4) . . ?
C48 C47 H47A 116.4 . . ?
Cu2 C47 H47A 116.4 . . ?
C48 C47 H47B 116.4 . . ?
Cu2 C47 H47B 116.4 . . ?
H47A C47 H47B 113.4 . . ?
C47 C48 C49 126.8(7) . . ?
C47 C48 Cu2 67.9(3) . . ?
C49 C48 Cu2 109.1(4) . . ?
C47 C48 H48A 114.3 . . ?
C49 C48 H48A 114.3 . . ?
Cu2 C48 H48A 114.3 . . ?
C54 C49 C50 116.6(7) . . ?
C54 C49 C48 125.7(7) . . ?
C50 C49 C48 117.6(6) . . ?
C49 C50 C51 121.4(6) . . ?
C49 C50 H50A 119.3 . . ?
C51 C50 H50A 119.3 . . ?
C52 C51 C50 119.4(8) . . ?
C52 C51 H51A 120.3 . . ?
C50 C51 H51A 120.3 . . ?
C51 C52 C53 119.5(9) . . ?
C51 C52 H52A 120.2 . . ?
C53 C52 H52A 120.2 . . ?
C52 C53 C54 122.0(8) . . ?
C52 C53 H53A 119.0 . . ?
C54 C53 H53A 119.0 . . ?
C53 C54 C49 120.9(7) . . ?
C53 C54 H54A 119.5 . . ?
C49 C54 H54A 119.5 . . ?
F3A B1 F4A 111.5(17) . . ?
F3A B1 F1A 108.7(16) . . ?
F4A B1 F1A 112.5(17) . . ?
F3A B1 F2A 104.4(16) . . ?
F4A B1 F2A 113(2) . . ?
F1A B1 F2A 105.8(15) . . ?
F1 B1 F3 106.5(11) . . ?
F1 B1 F2 115.8(14) . . ?
F3 B1 F2 109.6(12) . . ?
F1 B1 F4 108.2(15) . . ?
F3 B1 F4 108.6(11) . . ?
F2 B1 F4 108.0(12) . . ?
F11A B2 F12A 107.1(16) . . ?
F11 B2 F13 117.4(16) . . ?
F11A B2 F14A 120.3(14) . . ?
F12A B2 F14A 116.7(15) . . ?
F11 B2 F14 107.3(19) . . ?
F13 B2 F14 112.1(12) . . ?
F11 B2 F12 105.2(15) . . ?
F13 B2 F12 106.7(10) . . ?
F14 B2 F12 107.5(13) . . ?
F11A B2 F13A 96.2(14) . . ?
F12A B2 F13A 101.2(14) . . ?
F14A B2 F13A 111.8(11) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cu1 N2 C1 -38.2(3) . . . . ?
C20 Cu1 N2 C1 140.5(4) . . . . ?
C21 Cu1 N2 C1 126.3(5) . . . . ?
N3 Cu1 N2 C5 162.4(4) . . . . ?
C20 Cu1 N2 C5 -18.9(4) . . . . ?
C21 Cu1 N2 C5 -33.2(6) . . . . ?
N2 Cu1 N3 C6 22.9(4) . . . . ?
C20 Cu1 N3 C6 -153.7(6) . . . . ?
C21 Cu1 N3 C6 -147.5(4) . . . . ?
N2 Cu1 N3 C10 -150.6(4) . . . . ?
C20 Cu1 N3 C10 32.9(8) . . . . ?
C21 Cu1 N3 C10 39.0(5) . . . . ?
C5 N2 C1 C2 2.1(6) . . . . ?
Cu1 N2 C1 C2 -157.0(3) . . . . ?
C5 N2 C1 N1 -176.6(4) . . . . ?
Cu1 N2 C1 N1 24.3(5) . . . . ?
C6 N1 C1 N2 17.9(6) . . . . ?
C11 N1 C1 N2 -162.2(4) . . . . ?
C6 N1 C1 C2 -160.8(4) . . . . ?
C11 N1 C1 C2 19.1(6) . . . . ?
N2 C1 C2 C3 0.2(7) . . . . ?
N1 C1 C2 C3 178.9(4) . . . . ?
C1 C2 C3 C4 -2.6(7) . . . . ?
C2 C3 C4 C5 2.4(8) . . . . ?
C1 N2 C5 C4 -2.3(7) . . . . ?
Cu1 N2 C5 C4 157.7(4) . . . . ?
C3 C4 C5 N2 0.0(8) . . . . ?
C10 N3 C6 C7 -2.0(6) . . . . ?
Cu1 N3 C6 C7 -175.6(3) . . . . ?
C10 N3 C6 N1 179.6(4) . . . . ?
Cu1 N3 C6 N1 6.0(6) . . . . ?
C1 N1 C6 N3 -35.0(6) . . . . ?
C11 N1 C6 N3 145.1(4) . . . . ?
C1 N1 C6 C7 146.6(4) . . . . ?
C11 N1 C6 C7 -33.3(5) . . . . ?
N3 C6 C7 C8 1.6(7) . . . . ?
N1 C6 C7 C8 180.0(4) . . . . ?
C6 C7 C8 C9 -0.5(8) . . . . ?
C7 C8 C9 C10 0.0(8) . . . . ?
C6 N3 C10 C9 1.6(8) . . . . ?
Cu1 N3 C10 C9 175.4(4) . . . . ?
C8 C9 C10 N3 -0.5(9) . . . . ?
C6 N1 C11 C12 97.6(5) . . . . ?
C1 N1 C11 C12 -82.3(5) . . . . ?
C6 N1 C11 C16 -82.9(5) . . . . ?
C1 N1 C11 C16 97.2(5) . . . . ?
C16 C11 C12 C13 -2.3(7) . . . . ?
N1 C11 C12 C13 177.1(4) . . . . ?
C16 C11 C12 C17 178.5(5) . . . . ?
N1 C11 C12 C17 -2.1(7) . . . . ?
C11 C12 C13 C14 1.3(8) . . . . ?
C17 C12 C13 C14 -179.5(5) . . . . ?
C12 C13 C14 C15 0.4(9) . . . . ?
C12 C13 C14 C18 -179.3(5) . . . . ?
C13 C14 C15 C16 -1.3(9) . . . . ?
C18 C14 C15 C16 178.4(5) . . . . ?
C12 C11 C16 C15 1.5(7) . . . . ?
N1 C11 C16 C15 -177.9(4) . . . . ?
C12 C11 C16 C19 -178.1(4) . . . . ?
N1 C11 C16 C19 2.5(6) . . . . ?
C14 C15 C16 C11 0.3(7) . . . . ?
C14 C15 C16 C19 180.0(5) . . . . ?
N3 Cu1 C20 C21 8.4(8) . . . . ?
N2 Cu1 C20 C21 -168.0(3) . . . . ?
Cu1 C20 C21 C22 103.3(5) . . . . ?
N3 Cu1 C21 C20 -176.6(3) . . . . ?
N2 Cu1 C21 C20 21.3(6) . . . . ?
N3 Cu1 C21 C22 64.1(5) . . . . ?
N2 Cu1 C21 C22 -97.9(6) . . . . ?
C20 Cu1 C21 C22 -119.2(6) . . . . ?
C20 C21 C22 C27 -27.3(8) . . . . ?
Cu1 C21 C22 C27 50.3(7) . . . . ?
C20 C21 C22 C23 149.1(6) . . . . ?
Cu1 C21 C22 C23 -133.4(5) . . . . ?
C27 C22 C23 C24 0.9(10) . . . . ?
C21 C22 C23 C24 -175.7(7) . . . . ?
C22 C23 C24 C25 -0.6(13) . . . . ?
C23 C24 C25 C26 -1.1(12) . . . . ?
C24 C25 C26 C27 2.4(10) . . . . ?
C25 C26 C27 C22 -2.0(9) . . . . ?
C23 C22 C27 C26 0.4(8) . . . . ?
C21 C22 C27 C26 176.9(5) . . . . ?
N6 Cu2 N5 C28 22.9(4) . . . . ?
C47 Cu2 N5 C28 -144.8(4) . . . . ?
C48 Cu2 N5 C28 -142.7(5) . . . . ?
N6 Cu2 N5 C32 -150.6(4) . . . . ?
C47 Cu2 N5 C32 41.7(5) . . . . ?
C48 Cu2 N5 C32 43.9(7) . . . . ?
N5 Cu2 N6 C33 -41.9(4) . . . . ?
C47 Cu2 N6 C33 113.5(6) . . . . ?
C48 Cu2 N6 C33 131.0(4) . . . . ?
N5 Cu2 N6 C37 160.6(4) . . . . ?
C47 Cu2 N6 C37 -43.9(7) . . . . ?
C48 Cu2 N6 C37 -26.4(4) . . . . ?
C32 N5 C28 C29 -0.1(7) . . . . ?
Cu2 N5 C28 C29 -173.7(4) . . . . ?
C32 N5 C28 N4 -178.4(4) . . . . ?
Cu2 N5 C28 N4 8.0(6) . . . . ?
C33 N4 C28 N5 -35.8(6) . . . . ?
C38 N4 C28 N5 153.4(4) . . . . ?
C33 N4 C28 C29 145.8(4) . . . . ?
C38 N4 C28 C29 -24.9(6) . . . . ?
N5 C28 C29 C30 1.2(7) . . . . ?
N4 C28 C29 C30 179.6(5) . . . . ?
C28 C29 C30 C31 -2.0(8) . . . . ?
C29 C30 C31 C32 1.5(9) . . . . ?
C30 C31 C32 N5 -0.4(9) . . . . ?
C28 N5 C32 C31 -0.3(8) . . . . ?
Cu2 N5 C32 C31 173.5(5) . . . . ?
C37 N6 C33 C34 5.6(7) . . . . ?
Cu2 N6 C33 C34 -152.1(4) . . . . ?
C37 N6 C33 N4 -172.8(4) . . . . ?
Cu2 N6 C33 N4 29.5(5) . . . . ?
C28 N4 C33 N6 14.5(6) . . . . ?
C38 N4 C33 N6 -175.0(4) . . . . ?
C28 N4 C33 C34 -164.0(4) . . . . ?
C38 N4 C33 C34 6.6(6) . . . . ?
N6 C33 C34 C35 -3.9(7) . . . . ?
N4 C33 C34 C35 174.5(4) . . . . ?
C33 C34 C35 C36 -0.6(8) . . . . ?
C34 C35 C36 C37 3.1(9) . . . . ?
C35 C36 C37 N6 -1.4(9) . . . . ?
C33 N6 C37 C36 -3.0(7) . . . . ?
Cu2 N6 C37 C36 154.9(4) . . . . ?
C33 N4 C38 C39 -80.2(5) . . . . ?
C28 N4 C38 C39 91.4(5) . . . . ?
C33 N4 C38 C43 100.3(5) . . . . ?
C28 N4 C38 C43 -88.1(5) . . . . ?
C43 C38 C39 C40 1.2(7) . . . . ?
N4 C38 C39 C40 -178.3(4) . . . . ?
C43 C38 C39 C44 -178.5(4) . . . . ?
N4 C38 C39 C44 2.1(7) . . . . ?
C38 C39 C40 C41 0.2(7) . . . . ?
C44 C39 C40 C41 179.8(4) . . . . ?
C39 C40 C41 C42 -1.4(7) . . . . ?
C39 C40 C41 C45 178.9(4) . . . . ?
C40 C41 C42 C43 1.4(7) . . . . ?
C45 C41 C42 C43 -179.0(5) . . . . ?
C39 C38 C43 C42 -1.2(7) . . . . ?
N4 C38 C43 C42 178.3(4) . . . . ?
C39 C38 C43 C46 -179.8(5) . . . . ?
N4 C38 C43 C46 -0.3(7) . . . . ?
C41 C42 C43 C38 -0.1(7) . . . . ?
C41 C42 C43 C46 178.5(5) . . . . ?
N5 Cu2 C47 C48 178.5(4) . . . . ?
N6 Cu2 C47 C48 25.3(9) . . . . ?
Cu2 C47 C48 C49 -98.0(5) . . . . ?
N5 Cu2 C48 C47 -3.1(8) . . . . ?
N6 Cu2 C48 C47 -167.3(5) . . . . ?
N5 Cu2 C48 C49 119.8(5) . . . . ?
N6 Cu2 C48 C49 -44.4(5) . . . . ?
C47 Cu2 C48 C49 122.9(7) . . . . ?
C47 C48 C49 C54 11.3(9) . . . . ?
Cu2 C48 C49 C54 -64.9(7) . . . . ?
C47 C48 C49 C50 -170.5(6) . . . . ?
Cu2 C48 C49 C50 113.3(5) . . . . ?
C54 C49 C50 C51 -0.7(9) . . . . ?
C48 C49 C50 C51 -179.0(5) . . . . ?
C49 C50 C51 C52 1.2(10) . . . . ?
C50 C51 C52 C53 -2.7(12) . . . . ?
C51 C52 C53 C54 3.8(14) . . . . ?
C52 C53 C54 C49 -3.3(13) . . . . ?
C50 C49 C54 C53 1.7(10) . . . . ?
C48 C49 C54 C53 179.9(7) . . . . ?
N3 N2 C20 C21 11.1(4) . . . . ?
N6 N5 C47 C48 7.3(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full 28.31
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max 0.358
_refine_diff_density_min -0.269
_refine_diff_density_rms 0.063
_exptl_crystal_recrystallization_method
'cooled sat. solution in 2-butanol to -12 deg. C for several days'
_diffrn_ambient_pressure 101.33
# Attachment '[Cu(Phdpa)(sty)]BF4EtOH.CIF'
data_phdpasty
_database_code_depnum_ccdc_archive 'CCDC 724010'
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C24 H21 Cu N3, C2 H6 O, B F4'
_chemical_formula_sum 'C26 H27 B Cu F4 N3 O'
_chemical_formula_weight 547.86
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 13.340(3)
_cell_length_b 11.237(2)
_cell_length_c 17.596(4)
_cell_angle_alpha 90.00
_cell_angle_beta 103.57(3)
_cell_angle_gamma 90.00
_cell_volume 2563.9(9)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 5363
_cell_measurement_theta_min 2.17
_cell_measurement_theta_max 21.96
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.62
_exptl_crystal_size_mid 0.44
_exptl_crystal_size_min 0.13
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.419
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1128
_exptl_absorpt_coefficient_mu 0.905
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6039
_exptl_absorpt_correction_T_max 0.8914
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 30675
_diffrn_reflns_av_R_equivalents 0.0413
_diffrn_reflns_av_sigmaI/netI 0.0399
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 2.17
_diffrn_reflns_theta_max 28.35
_reflns_number_total 6243
_reflns_number_gt 3551
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1180P)^2^+0.7482P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.0069(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 6243
_refine_ls_number_parameters 328
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1104
_refine_ls_R_factor_gt 0.0605
_refine_ls_wR_factor_ref 0.2136
_refine_ls_wR_factor_gt 0.1768
_refine_ls_goodness_of_fit_ref 1.032
_refine_ls_restrained_S_all 1.032
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.38757(3) 1.09575(4) 1.19367(3) 0.0639(2) Uani 1 1 d . . .
N1 N 1.2633(2) 0.8837(3) 1.09074(18) 0.0631(8) Uani 1 1 d . . .
N2 N 1.2486(2) 1.0325(3) 1.18435(18) 0.0650(8) Uani 1 1 d . . .
N3 N 1.4290(2) 0.9759(2) 1.12691(16) 0.0568(7) Uani 1 1 d . . .
C1 C 1.2110(3) 0.9357(4) 1.1430(2) 0.0666(9) Uani 1 1 d . . .
C2 C 1.1179(4) 0.8863(6) 1.1507(4) 0.116(2) Uani 1 1 d . . .
H2A H 1.0928 0.8176 1.1232 0.139 Uiso 1 1 calc R . .
C3 C 1.0633(4) 0.9389(6) 1.1989(4) 0.121(2) Uani 1 1 d . . .
H3A H 1.0018 0.9054 1.2046 0.145 Uiso 1 1 calc R . .
C4 C 1.0998(3) 1.0405(5) 1.2382(3) 0.0932(14) Uani 1 1 d . . .
H4A H 1.0628 1.0795 1.2693 0.112 Uiso 1 1 calc R . .
C5 C 1.1916(4) 1.0824(4) 1.2303(3) 0.0827(12) Uani 1 1 d . . .
H5A H 1.2176 1.1503 1.2583 0.099 Uiso 1 1 calc R . .
C6 C 1.3660(3) 0.8948(3) 1.08490(19) 0.0550(8) Uani 1 1 d . . .
C7 C 1.4028(3) 0.8187(3) 1.0345(2) 0.0643(9) Uani 1 1 d . . .
H7A H 1.3584 0.7635 1.0047 0.077 Uiso 1 1 calc R . .
C8 C 1.5026(3) 0.8243(3) 1.0287(2) 0.0688(9) Uani 1 1 d . . .
H8A H 1.5265 0.7741 0.9948 0.083 Uiso 1 1 calc R . .
C9 C 1.5682(3) 0.9060(3) 1.0743(2) 0.0632(9) Uani 1 1 d . . .
H9A H 1.6371 0.9111 1.0724 0.076 Uiso 1 1 calc R . .
C10 C 1.5292(3) 0.9774(3) 1.1211(2) 0.0640(9) Uani 1 1 d . . .
H10A H 1.5735 1.0318 1.1518 0.077 Uiso 1 1 calc R . .
C11 C 1.1999(3) 0.7992(4) 1.0358(2) 0.0691(10) Uani 1 1 d . . .
C12 C 1.1448(4) 0.8380(5) 0.9657(3) 0.0943(14) Uani 1 1 d . . .
H12A H 1.1478 0.9174 0.9513 0.113 Uiso 1 1 calc R . .
C13 C 1.0831(4) 0.7568(7) 0.9153(3) 0.1131(19) Uani 1 1 d . . .
H13A H 1.0456 0.7814 0.8664 0.136 Uiso 1 1 calc R . .
C14 C 1.0781(4) 0.6419(8) 0.9380(5) 0.122(2) Uani 1 1 d . . .
H14A H 1.0352 0.5886 0.9051 0.146 Uiso 1 1 calc R . .
C15 C 1.1335(5) 0.6051(5) 1.0061(5) 0.117(2) Uani 1 1 d . . .
H15A H 1.1300 0.5256 1.0201 0.140 Uiso 1 1 calc R . .
C16 C 1.1968(4) 0.6820(4) 1.0573(3) 0.0910(13) Uani 1 1 d . . .
H16A H 1.2361 0.6551 1.1050 0.109 Uiso 1 1 calc R . .
C17 C 1.4121(3) 1.2239(4) 1.2734(2) 0.0779(11) Uani 1 1 d . . .
H17A H 1.3742 1.2974 1.2589 0.094 Uiso 1 1 calc R . .
H17B H 1.4150 1.1996 1.3268 0.094 Uiso 1 1 calc R . .
C18 C 1.5021(3) 1.2112(4) 1.2482(2) 0.0689(10) Uani 1 1 d . . .
H18A H 1.5581 1.1728 1.2864 0.083 Uiso 1 1 calc R . .
C19 C 1.5376(3) 1.2932(3) 1.1952(2) 0.0689(10) Uani 1 1 d . . .
C20 C 1.4754(4) 1.3838(4) 1.1549(3) 0.0799(12) Uani 1 1 d . . .
H20A H 1.4078 1.3921 1.1596 0.096 Uiso 1 1 calc R . .
C21 C 1.5145(6) 1.4612(5) 1.1080(3) 0.1084(17) Uani 1 1 d . . .
H21A H 1.4723 1.5207 1.0808 0.130 Uiso 1 1 calc R . .
C22 C 1.6137(6) 1.4518(6) 1.1009(4) 0.114(2) Uani 1 1 d . . .
H22A H 1.6390 1.5057 1.0698 0.137 Uiso 1 1 calc R . .
C23 C 1.6752(5) 1.3655(6) 1.1383(4) 0.110(2) Uani 1 1 d . . .
H23A H 1.7424 1.3591 1.1324 0.132 Uiso 1 1 calc R . .
C24 C 1.6389(3) 1.2844(5) 1.1866(3) 0.0891(14) Uani 1 1 d . . .
H24A H 1.6822 1.2250 1.2127 0.107 Uiso 1 1 calc R . .
B1 B 1.8119(4) 0.9771(6) 1.2681(4) 0.0962(18) Uani 1 1 d . . .
F1 F 1.8899(3) 1.0468(4) 1.2993(3) 0.1589(17) Uani 1 1 d . . .
F2 F 1.7229(2) 1.0099(4) 1.2802(2) 0.1365(13) Uani 1 1 d . . .
F3 F 1.8376(6) 0.8792(5) 1.3042(7) 0.351(7) Uani 1 1 d . . .
F4 F 1.8003(4) 0.9469(10) 1.1969(4) 0.305(5) Uani 1 1 d . . .
O1 O 1.8320(14) 0.7291(11) 1.0665(8) 0.352(7) Uani 1 1 d . . .
H1A H 1.7888 0.6760 1.0626 0.528 Uiso 1 1 calc R . .
C25 C 1.8146(11) 0.7947(11) 0.9938(8) 0.208(4) Uani 1 1 d . . .
H25A H 1.7983 0.8769 1.0028 0.250 Uiso 1 1 calc R . .
H25B H 1.8767 0.7937 0.9741 0.250 Uiso 1 1 calc R . .
C26 C 1.7359(10) 0.7454(11) 0.9406(8) 0.241(6) Uani 1 1 d . . .
H26A H 1.7539 0.7409 0.8910 0.361 Uiso 1 1 calc R . .
H26B H 1.6752 0.7933 0.9357 0.361 Uiso 1 1 calc R . .
H26C H 1.7228 0.6668 0.9574 0.361 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0746(4) 0.0561(3) 0.0629(3) -0.01048(19) 0.0198(2) -0.0070(2)
N1 0.0654(18) 0.0610(18) 0.0624(18) -0.0116(13) 0.0143(14) -0.0083(14)
N2 0.0731(19) 0.0631(19) 0.0611(17) -0.0029(14) 0.0205(14) 0.0007(15)
N3 0.0616(17) 0.0516(16) 0.0560(15) -0.0020(12) 0.0117(13) -0.0020(13)
C1 0.063(2) 0.074(2) 0.062(2) -0.0054(18) 0.0140(17) -0.0048(18)
C2 0.090(3) 0.135(5) 0.135(5) -0.067(4) 0.050(3) -0.043(3)
C3 0.081(3) 0.168(6) 0.128(5) -0.053(4) 0.052(3) -0.034(4)
C4 0.074(3) 0.120(4) 0.093(3) -0.016(3) 0.035(2) 0.000(3)
C5 0.090(3) 0.078(3) 0.085(3) -0.016(2) 0.031(2) -0.003(2)
C6 0.063(2) 0.0513(19) 0.0471(17) 0.0040(14) 0.0061(14) -0.0023(15)
C7 0.071(2) 0.060(2) 0.061(2) -0.0108(16) 0.0125(17) -0.0077(17)
C8 0.082(3) 0.063(2) 0.064(2) -0.0047(17) 0.0212(18) 0.0061(19)
C9 0.062(2) 0.064(2) 0.065(2) 0.0060(17) 0.0157(17) 0.0057(17)
C10 0.065(2) 0.058(2) 0.065(2) 0.0016(16) 0.0093(17) -0.0023(17)
C11 0.065(2) 0.074(3) 0.067(2) -0.0150(19) 0.0122(18) -0.0095(18)
C12 0.094(3) 0.094(3) 0.082(3) -0.009(3) -0.006(2) 0.010(3)
C13 0.086(3) 0.145(6) 0.088(3) -0.031(4) -0.018(3) 0.011(4)
C14 0.080(4) 0.150(6) 0.134(6) -0.073(5) 0.023(3) -0.031(4)
C15 0.115(5) 0.100(4) 0.147(6) -0.041(4) 0.055(4) -0.047(3)
C16 0.100(3) 0.080(3) 0.093(3) -0.010(2) 0.025(3) -0.032(3)
C17 0.101(3) 0.075(3) 0.063(2) -0.0217(19) 0.029(2) -0.017(2)
C18 0.076(2) 0.064(2) 0.060(2) -0.0153(17) 0.0033(17) -0.0068(18)
C19 0.073(2) 0.064(2) 0.068(2) -0.0232(18) 0.0144(18) -0.0115(19)
C20 0.088(3) 0.074(3) 0.080(3) -0.007(2) 0.023(2) -0.006(2)
C21 0.161(6) 0.078(3) 0.095(4) -0.006(3) 0.048(4) -0.016(3)
C22 0.156(6) 0.097(4) 0.106(4) -0.029(3) 0.066(4) -0.050(4)
C23 0.100(4) 0.119(5) 0.124(5) -0.057(4) 0.054(4) -0.045(4)
C24 0.074(3) 0.087(3) 0.106(3) -0.038(3) 0.021(2) -0.013(2)
B1 0.070(3) 0.093(4) 0.121(5) -0.034(4) 0.014(3) 0.003(3)
F1 0.098(2) 0.189(4) 0.204(4) -0.076(3) 0.064(2) -0.052(2)
F2 0.0743(18) 0.174(4) 0.162(3) -0.030(3) 0.0290(19) 0.001(2)
F3 0.239(7) 0.132(4) 0.566(17) 0.105(7) -0.140(9) -0.014(4)
F4 0.138(4) 0.596(15) 0.189(5) -0.195(8) 0.055(4) -0.062(6)
O1 0.47(2) 0.201(10) 0.313(12) 0.055(9) -0.055(12) -0.004(9)
C25 0.257(13) 0.167(10) 0.225(12) -0.011(9) 0.105(10) -0.005(9)
C26 0.251(13) 0.207(11) 0.250(13) -0.064(10) 0.033(10) -0.092(10)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.951(3) . ?
Cu1 N2 1.956(3) . ?
Cu1 C17 1.984(4) . ?
Cu1 C18 2.061(4) . ?
N1 C6 1.402(5) . ?
N1 C1 1.405(5) . ?
N1 C11 1.473(5) . ?
N2 C1 1.339(5) . ?
N2 C5 1.354(5) . ?
N3 C6 1.339(4) . ?
N3 C10 1.364(5) . ?
C1 C2 1.396(6) . ?
C2 C3 1.374(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.365(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.349(7) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.402(5) . ?
C7 C8 1.360(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.386(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.339(5) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.351(6) . ?
C11 C16 1.373(6) . ?
C12 C13 1.399(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.358(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.319(10) . ?
C14 H14A 0.9300 . ?
C15 C16 1.384(7) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.382(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.467(6) . ?
C18 H18A 0.9800 . ?
C19 C20 1.397(6) . ?
C19 C24 1.398(6) . ?
C20 C21 1.383(7) . ?
C20 H20A 0.9300 . ?
C21 C22 1.363(9) . ?
C21 H21A 0.9300 . ?
C22 C23 1.339(9) . ?
C22 H22A 0.9300 . ?
C23 C24 1.407(8) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
B1 F4 1.272(8) . ?
B1 F3 1.277(9) . ?
B1 F2 1.308(6) . ?
B1 F1 1.315(7) . ?
O1 C25 1.447(14) . ?
O1 H1A 0.8200 . ?
C25 C26 1.350(13) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N2 95.49(12) . . ?
N3 Cu1 C17 154.73(16) . . ?
N2 Cu1 C17 108.60(16) . . ?
N3 Cu1 C18 115.52(15) . . ?
N2 Cu1 C18 148.43(15) . . ?
C17 Cu1 C18 39.88(16) . . ?
C6 N1 C1 130.8(3) . . ?
C6 N1 C11 115.4(3) . . ?
C1 N1 C11 113.6(3) . . ?
C1 N2 C5 118.1(4) . . ?
C1 N2 Cu1 124.6(3) . . ?
C5 N2 Cu1 116.9(3) . . ?
C6 N3 C10 117.8(3) . . ?
C6 N3 Cu1 124.9(2) . . ?
C10 N3 Cu1 117.3(2) . . ?
N2 C1 C2 119.9(4) . . ?
N2 C1 N1 120.9(3) . . ?
C2 C1 N1 119.2(4) . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C5 C4 C3 117.7(4) . . ?
C5 C4 H4A 121.2 . . ?
C3 C4 H4A 121.2 . . ?
C4 C5 N2 124.5(4) . . ?
C4 C5 H5A 117.8 . . ?
N2 C5 H5A 117.8 . . ?
N3 C6 C7 119.7(3) . . ?
N3 C6 N1 121.2(3) . . ?
C7 C6 N1 119.0(3) . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C7 C8 C9 118.8(4) . . ?
C7 C8 H8A 120.6 . . ?
C9 C8 H8A 120.6 . . ?
C10 C9 C8 118.0(4) . . ?
C10 C9 H9A 121.0 . . ?
C8 C9 H9A 121.0 . . ?
C9 C10 N3 124.6(3) . . ?
C9 C10 H10A 117.7 . . ?
N3 C10 H10A 117.7 . . ?
C12 C11 C16 121.1(4) . . ?
C12 C11 N1 119.8(4) . . ?
C16 C11 N1 119.1(4) . . ?
C11 C12 C13 118.8(5) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
C14 C13 C12 119.8(5) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C15 C14 C13 120.6(5) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C14 C15 C16 121.5(6) . . ?
C14 C15 H15A 119.3 . . ?
C16 C15 H15A 119.3 . . ?
C11 C16 C15 118.2(5) . . ?
C11 C16 H16A 120.9 . . ?
C15 C16 H16A 120.9 . . ?
C18 C17 Cu1 73.1(2) . . ?
C18 C17 H17A 116.2 . . ?
Cu1 C17 H17A 116.2 . . ?
C18 C17 H17B 116.2 . . ?
Cu1 C17 H17B 116.2 . . ?
H17A C17 H17B 113.2 . . ?
C17 C18 C19 125.0(4) . . ?
C17 C18 Cu1 67.1(2) . . ?
C19 C18 Cu1 114.5(2) . . ?
C17 C18 H18A 113.9 . . ?
C19 C18 H18A 113.9 . . ?
Cu1 C18 H18A 113.9 . . ?
C20 C19 C24 118.1(4) . . ?
C20 C19 C18 122.6(4) . . ?
C24 C19 C18 119.2(4) . . ?
C21 C20 C19 120.0(5) . . ?
C21 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?
C22 C21 C20 121.1(6) . . ?
C22 C21 H21A 119.5 . . ?
C20 C21 H21A 119.5 . . ?
C23 C22 C21 120.4(6) . . ?
C23 C22 H22A 119.8 . . ?
C21 C22 H22A 119.8 . . ?
C22 C23 C24 120.6(5) . . ?
C22 C23 H23A 119.7 . . ?
C24 C23 H23A 119.7 . . ?
C19 C24 C23 119.8(5) . . ?
C19 C24 H24A 120.1 . . ?
C23 C24 H24A 120.1 . . ?
F4 B1 F3 102.6(8) . . ?
F4 B1 F2 109.3(6) . . ?
F3 B1 F2 108.0(8) . . ?
F4 B1 F1 118.1(7) . . ?
F3 B1 F1 102.2(6) . . ?
F2 B1 F1 115.1(5) . . ?
C25 O1 H1A 109.5 . . ?
C26 C25 O1 109.9(12) . . ?
C26 C25 H25A 109.7 . . ?
O1 C25 H25A 109.7 . . ?
C26 C25 H25B 109.7 . . ?
O1 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cu1 N2 C1 0.7(3) . . . . ?
C17 Cu1 N2 C1 -171.5(3) . . . . ?
C18 Cu1 N2 C1 -168.8(3) . . . . ?
N3 Cu1 N2 C5 172.8(3) . . . . ?
C17 Cu1 N2 C5 0.5(4) . . . . ?
C18 Cu1 N2 C5 3.3(5) . . . . ?
N2 Cu1 N3 C6 7.9(3) . . . . ?
C17 Cu1 N3 C6 170.5(4) . . . . ?
C18 Cu1 N3 C6 -178.2(3) . . . . ?
N2 Cu1 N3 C10 -174.1(2) . . . . ?
C17 Cu1 N3 C10 -11.5(5) . . . . ?
C18 Cu1 N3 C10 -0.2(3) . . . . ?
C5 N2 C1 C2 -2.8(7) . . . . ?
Cu1 N2 C1 C2 169.1(4) . . . . ?
C5 N2 C1 N1 176.3(4) . . . . ?
Cu1 N2 C1 N1 -11.8(5) . . . . ?
C6 N1 C1 N2 18.4(6) . . . . ?
C11 N1 C1 N2 -164.9(3) . . . . ?
C6 N1 C1 C2 -162.5(5) . . . . ?
C11 N1 C1 C2 14.2(6) . . . . ?
N2 C1 C2 C3 2.0(9) . . . . ?
N1 C1 C2 C3 -177.1(6) . . . . ?
C1 C2 C3 C4 0.9(11) . . . . ?
C2 C3 C4 C5 -2.8(10) . . . . ?
C3 C4 C5 N2 1.9(8) . . . . ?
C1 N2 C5 C4 0.9(7) . . . . ?
Cu1 N2 C5 C4 -171.6(4) . . . . ?
C10 N3 C6 C7 -2.7(5) . . . . ?
Cu1 N3 C6 C7 175.3(2) . . . . ?
C10 N3 C6 N1 176.7(3) . . . . ?
Cu1 N3 C6 N1 -5.2(4) . . . . ?
C1 N1 C6 N3 -9.1(6) . . . . ?
C11 N1 C6 N3 174.3(3) . . . . ?
C1 N1 C6 C7 170.4(4) . . . . ?
C11 N1 C6 C7 -6.3(5) . . . . ?
N3 C6 C7 C8 1.3(5) . . . . ?
N1 C6 C7 C8 -178.2(3) . . . . ?
C6 C7 C8 C9 0.7(6) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C8 C9 C10 N3 -0.4(6) . . . . ?
C6 N3 C10 C9 2.3(5) . . . . ?
Cu1 N3 C10 C9 -175.8(3) . . . . ?
C6 N1 C11 C12 -91.7(5) . . . . ?
C1 N1 C11 C12 91.1(5) . . . . ?
C6 N1 C11 C16 89.3(5) . . . . ?
C1 N1 C11 C16 -87.9(5) . . . . ?
C16 C11 C12 C13 0.6(8) . . . . ?
N1 C11 C12 C13 -178.4(5) . . . . ?
C11 C12 C13 C14 1.3(9) . . . . ?
C12 C13 C14 C15 -2.3(10) . . . . ?
C13 C14 C15 C16 1.3(10) . . . . ?
C12 C11 C16 C15 -1.6(7) . . . . ?
N1 C11 C16 C15 177.4(4) . . . . ?
C14 C15 C16 C11 0.6(9) . . . . ?
N3 Cu1 C17 C18 16.1(5) . . . . ?
N2 Cu1 C17 C18 177.7(2) . . . . ?
Cu1 C17 C18 C19 104.6(3) . . . . ?
N3 Cu1 C18 C17 -172.5(2) . . . . ?
N2 Cu1 C18 C17 -4.1(4) . . . . ?
N3 Cu1 C18 C19 68.1(3) . . . . ?
N2 Cu1 C18 C19 -123.5(3) . . . . ?
C17 Cu1 C18 C19 -119.5(4) . . . . ?
C17 C18 C19 C20 -10.2(6) . . . . ?
Cu1 C18 C19 C20 68.0(4) . . . . ?
C17 C18 C19 C24 167.0(4) . . . . ?
Cu1 C18 C19 C24 -114.7(3) . . . . ?
C24 C19 C20 C21 0.2(6) . . . . ?
C18 C19 C20 C21 177.6(4) . . . . ?
C19 C20 C21 C22 -0.8(7) . . . . ?
C20 C21 C22 C23 1.2(9) . . . . ?
C21 C22 C23 C24 -1.0(9) . . . . ?
C20 C19 C24 C23 -0.1(6) . . . . ?
C18 C19 C24 C23 -177.5(4) . . . . ?
C22 C23 C24 C19 0.5(7) . . . . ?
N3 N2 C17 C18 3.0(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full 28.35
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max 0.671
_refine_diff_density_min -0.582
_refine_diff_density_rms 0.064
_exptl_crystal_recrystallization_method
'sat. soln in EtOH cooled to -12 deg. C for several days'
_diffrn_ambient_pressure 101.33
data_mdpanbn
_database_code_depnum_ccdc_archive 'CCDC 728875'
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C26 H29 Cu N3, F6 P, C H4 O'
_chemical_formula_sum 'C27 H33 Cu F6 N3 O P'
_chemical_formula_weight 624.07
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 10.770(2)
_cell_length_b 14.380(3)
_cell_length_c 18.831(4)
_cell_angle_alpha 90.00
_cell_angle_beta 102.61(3)
_cell_angle_gamma 90.00
_cell_volume 2846.0(10)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 7233
_cell_measurement_theta_min 2.22
_cell_measurement_theta_max 22.20
_exptl_crystal_description prism
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.67
_exptl_crystal_size_mid 0.53
_exptl_crystal_size_min 0.43
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.456
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1288
_exptl_absorpt_coefficient_mu 0.888
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.5875
_exptl_absorpt_correction_T_max 0.7012
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 34349
_diffrn_reflns_av_R_equivalents 0.0452
_diffrn_reflns_av_sigmaI/netI 0.0433
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 1.80
_diffrn_reflns_theta_max 28.36
_reflns_number_total 6948
_reflns_number_gt 3747
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Site occupancies of disordered PF6 fluorine atoms F(3A)-F(6A) and F(3B)-
F(6B) were determined to be 50:50 using the free variable FVAR.
SHELXTL weighting scheme: 0.0809, 1.3538.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+1.3538P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.0078(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 6948
_refine_ls_number_parameters 397
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1096
_refine_ls_R_factor_gt 0.0500
_refine_ls_wR_factor_ref 0.1700
_refine_ls_wR_factor_gt 0.1333
_refine_ls_goodness_of_fit_ref 1.006
_refine_ls_restrained_S_all 1.006
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.70678(4) 0.64035(3) 0.45632(2) 0.06285(19) Uani 1 1 d . . .
N1 N 0.7128(2) 0.52769(17) 0.60157(13) 0.0523(6) Uani 1 1 d . . .
N2 N 0.7039(3) 0.50660(19) 0.47498(14) 0.0600(7) Uani 1 1 d . . .
N3 N 0.6498(3) 0.67410(19) 0.54499(15) 0.0599(7) Uani 1 1 d . . .
C1 C 0.7095(3) 0.4696(2) 0.54103(16) 0.0526(7) Uani 1 1 d . . .
C2 C 0.7153(3) 0.3741(2) 0.5509(2) 0.0654(9) Uani 1 1 d . . .
H2A H 0.7215 0.3491 0.5971 0.078 Uiso 1 1 calc R . .
C3 C 0.7119(4) 0.3161(3) 0.4922(2) 0.0756(10) Uani 1 1 d . . .
H3A H 0.7151 0.2520 0.4985 0.091 Uiso 1 1 calc R . .
C4 C 0.7039(4) 0.3535(3) 0.4249(2) 0.0804(11) Uani 1 1 d . . .
H4A H 0.7011 0.3155 0.3846 0.097 Uiso 1 1 calc R . .
C5 C 0.7003(4) 0.4471(3) 0.41802(19) 0.0730(10) Uani 1 1 d . . .
H5A H 0.6950 0.4724 0.3720 0.088 Uiso 1 1 calc R . .
C6 C 0.6667(3) 0.6192(2) 0.60384(17) 0.0524(7) Uani 1 1 d . . .
C7 C 0.6416(3) 0.6507(2) 0.66949(19) 0.0644(9) Uani 1 1 d . . .
H7A H 0.6516 0.6113 0.7095 0.077 Uiso 1 1 calc R . .
C8 C 0.6018(4) 0.7409(3) 0.6738(2) 0.0779(11) Uani 1 1 d . . .
H8A H 0.5868 0.7634 0.7175 0.093 Uiso 1 1 calc R . .
C9 C 0.5842(4) 0.7980(3) 0.6139(2) 0.0801(11) Uani 1 1 d . . .
H9A H 0.5574 0.8592 0.6161 0.096 Uiso 1 1 calc R . .
C10 C 0.6071(4) 0.7621(3) 0.5513(2) 0.0784(11) Uani 1 1 d . . .
H10A H 0.5927 0.7999 0.5103 0.094 Uiso 1 1 calc R . .
C11 C 0.7802(3) 0.4889(2) 0.67139(15) 0.0524(7) Uani 1 1 d . . .
C12 C 0.7161(3) 0.4339(2) 0.71246(18) 0.0620(8) Uani 1 1 d . . .
C13 C 0.7885(4) 0.3944(3) 0.7753(2) 0.0735(10) Uani 1 1 d . . .
H13A H 0.7482 0.3563 0.8032 0.088 Uiso 1 1 calc R . .
C14 C 0.9170(4) 0.4092(3) 0.79802(19) 0.0745(10) Uani 1 1 d . . .
C15 C 0.9755(4) 0.4674(3) 0.75642(19) 0.0683(9) Uani 1 1 d . . .
H15A H 1.0620 0.4795 0.7718 0.082 Uiso 1 1 calc R . .
C16 C 0.9089(3) 0.5079(2) 0.69285(16) 0.0558(7) Uani 1 1 d . . .
C17 C 0.5739(4) 0.4156(3) 0.6902(3) 0.0840(11) Uani 1 1 d . . .
H17A H 0.5483 0.3768 0.7259 0.126 Uiso 0.50 1 calc PR . .
H17B H 0.5549 0.3848 0.6438 0.126 Uiso 0.50 1 calc PR . .
H17C H 0.5287 0.4735 0.6866 0.126 Uiso 0.50 1 calc PR . .
H17D H 0.5397 0.4466 0.6450 0.126 Uiso 0.50 1 calc PR . .
H17E H 0.5331 0.4386 0.7271 0.126 Uiso 0.50 1 calc PR . .
H17F H 0.5593 0.3499 0.6843 0.126 Uiso 0.50 1 calc PR . .
C18 C 0.9929(6) 0.3648(3) 0.8670(3) 0.1184(19) Uani 1 1 d . . .
H18A H 1.0804 0.3833 0.8742 0.178 Uiso 0.50 1 calc PR . .
H18B H 0.9869 0.2983 0.8626 0.178 Uiso 0.50 1 calc PR . .
H18C H 0.9594 0.3846 0.9077 0.178 Uiso 0.50 1 calc PR . .
H18D H 0.9374 0.3275 0.8889 0.178 Uiso 0.50 1 calc PR . .
H18E H 1.0309 0.4125 0.9004 0.178 Uiso 0.50 1 calc PR . .
H18F H 1.0584 0.3262 0.8553 0.178 Uiso 0.50 1 calc PR . .
C19 C 0.9762(4) 0.5711(3) 0.6491(2) 0.0770(10) Uani 1 1 d . . .
H19A H 1.0645 0.5757 0.6728 0.116 Uiso 0.50 1 calc PR . .
H19B H 0.9382 0.6317 0.6457 0.116 Uiso 0.50 1 calc PR . .
H19C H 0.9688 0.5458 0.6012 0.116 Uiso 0.50 1 calc PR . .
H19D H 0.9165 0.5932 0.6070 0.116 Uiso 0.50 1 calc PR . .
H19E H 1.0428 0.5371 0.6341 0.116 Uiso 0.50 1 calc PR . .
H19F H 1.0122 0.6230 0.6786 0.116 Uiso 0.50 1 calc PR . .
C20 C 0.7742(4) 0.6746(3) 0.36739(18) 0.0714(10) Uani 1 1 d . . .
H20A H 0.7277 0.6536 0.3194 0.086 Uiso 1 1 calc R . .
C21 C 0.7329(3) 0.7518(3) 0.39715(18) 0.0697(9) Uani 1 1 d . . .
H21A H 0.6579 0.7846 0.3696 0.084 Uiso 1 1 calc R . .
C22 C 0.8493(4) 0.8074(3) 0.4301(2) 0.0764(10) Uani 1 1 d . . .
H22A H 0.8394 0.8526 0.4675 0.092 Uiso 1 1 calc R . .
C23 C 0.8969(5) 0.8472(3) 0.3640(3) 0.0964(14) Uani 1 1 d . . .
H23A H 0.8286 0.8779 0.3300 0.116 Uiso 1 1 calc R . .
H23B H 0.9662 0.8908 0.3796 0.116 Uiso 1 1 calc R . .
C24 C 0.9415(5) 0.7607(4) 0.3306(3) 0.1051(15) Uani 1 1 d . . .
H24A H 1.0311 0.7650 0.3299 0.126 Uiso 1 1 calc R . .
H24B H 0.8929 0.7511 0.2814 0.126 Uiso 1 1 calc R . .
C25 C 0.9171(4) 0.6820(3) 0.3817(2) 0.0838(11) Uani 1 1 d . . .
H25A H 0.9632 0.6237 0.3793 0.101 Uiso 1 1 calc R . .
C26 C 0.9465(4) 0.7319(3) 0.4544(2) 0.0814(11) Uani 1 1 d . . .
H26A H 0.930(3) 0.692(3) 0.493(2) 0.081(12) Uiso 1 1 d . . .
H26B H 1.028(4) 0.758(3) 0.470(2) 0.095(13) Uiso 1 1 d . . .
P1 P 0.63681(10) 0.39738(8) 0.17894(6) 0.0733(3) Uani 1 1 d . . .
F1 F 0.6793(4) 0.4774(3) 0.2356(2) 0.1738(17) Uani 1 1 d . A .
F2 F 0.5943(4) 0.3191(3) 0.1240(2) 0.1728(17) Uani 1 1 d . A .
F3A F 0.669(3) 0.4735(6) 0.1296(8) 0.195(6) Uani 0.50 1 d P A 1
F4A F 0.600(2) 0.3271(10) 0.2297(9) 0.213(8) Uani 0.50 1 d P A 1
F5A F 0.5074(12) 0.4438(14) 0.1707(12) 0.208(7) Uani 0.50 1 d P A 1
F6A F 0.7601(10) 0.3538(11) 0.1810(13) 0.212(8) Uani 0.50 1 d P A 1
F3B F 0.5652(15) 0.4458(10) 0.1132(7) 0.183(5) Uani 0.50 1 d P A 2
F4B F 0.717(2) 0.3471(10) 0.2429(6) 0.200(5) Uani 0.50 1 d P A 2
F5B F 0.5116(16) 0.3884(15) 0.2051(10) 0.188(9) Uani 0.50 1 d P A 2
F6B F 0.7635(11) 0.4113(15) 0.1533(8) 0.162(6) Uani 0.50 1 d P A 2
O1S O 0.7939(9) 0.4280(7) 0.0054(5) 0.286(4) Uani 1 1 d . . .
H1SA H 0.7787 0.4271 0.0462 0.343 Uiso 1 1 calc R . .
C1S C 0.7018(8) 0.4644(8) -0.0386(5) 0.204(4) Uani 1 1 d . . .
H1SB H 0.7196 0.4654 -0.0864 0.306 Uiso 1 1 calc R . .
H1SC H 0.6895 0.5268 -0.0234 0.306 Uiso 1 1 calc R . .
H1SD H 0.6262 0.4287 -0.0395 0.306 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0637(3) 0.0715(3) 0.0539(3) 0.00796(19) 0.01386(19) 0.0020(2)
N1 0.0583(15) 0.0501(14) 0.0467(13) -0.0027(11) 0.0078(11) 0.0055(12)
N2 0.0631(17) 0.0659(17) 0.0510(14) -0.0068(13) 0.0124(12) 0.0002(13)
N3 0.0619(16) 0.0588(16) 0.0607(16) 0.0077(13) 0.0172(13) 0.0116(13)
C1 0.0445(16) 0.0599(19) 0.0511(16) -0.0039(14) 0.0057(13) 0.0025(13)
C2 0.073(2) 0.059(2) 0.060(2) -0.0050(16) 0.0075(17) 0.0045(16)
C3 0.075(2) 0.066(2) 0.081(3) -0.017(2) 0.0046(19) 0.0031(19)
C4 0.077(3) 0.089(3) 0.071(2) -0.030(2) 0.0080(19) 0.001(2)
C5 0.078(2) 0.087(3) 0.0538(19) -0.0108(19) 0.0136(17) 0.001(2)
C6 0.0459(16) 0.0573(19) 0.0527(17) -0.0007(14) 0.0077(13) 0.0021(13)
C7 0.073(2) 0.066(2) 0.0533(18) -0.0077(15) 0.0122(16) 0.0103(17)
C8 0.083(3) 0.077(3) 0.073(2) -0.020(2) 0.016(2) 0.009(2)
C9 0.089(3) 0.058(2) 0.095(3) -0.006(2) 0.024(2) 0.0160(19)
C10 0.087(3) 0.065(2) 0.088(3) 0.018(2) 0.030(2) 0.019(2)
C11 0.0598(19) 0.0503(17) 0.0454(15) -0.0010(13) 0.0079(13) 0.0063(14)
C12 0.071(2) 0.0588(19) 0.0592(19) 0.0024(16) 0.0204(16) -0.0013(16)
C13 0.101(3) 0.061(2) 0.063(2) 0.0102(17) 0.027(2) 0.003(2)
C14 0.103(3) 0.062(2) 0.054(2) 0.0019(17) 0.007(2) 0.017(2)
C15 0.069(2) 0.068(2) 0.061(2) -0.0097(17) -0.0015(17) 0.0122(18)
C16 0.0599(19) 0.0525(17) 0.0538(17) -0.0052(14) 0.0099(15) 0.0012(15)
C17 0.076(3) 0.082(3) 0.100(3) 0.009(2) 0.033(2) -0.009(2)
C18 0.161(5) 0.111(4) 0.068(3) 0.022(3) -0.009(3) 0.039(3)
C19 0.067(2) 0.076(2) 0.087(3) 0.005(2) 0.0147(19) -0.0064(19)
C20 0.090(3) 0.077(2) 0.0466(17) 0.0037(17) 0.0132(17) -0.011(2)
C21 0.064(2) 0.084(3) 0.0588(19) 0.0201(18) 0.0087(16) 0.0133(19)
C22 0.098(3) 0.062(2) 0.068(2) 0.0041(18) 0.014(2) 0.001(2)
C23 0.105(3) 0.089(3) 0.093(3) 0.024(2) 0.017(3) -0.017(3)
C24 0.103(3) 0.124(4) 0.102(3) 0.019(3) 0.051(3) -0.004(3)
C25 0.086(3) 0.080(3) 0.096(3) 0.009(2) 0.043(2) 0.014(2)
C26 0.066(3) 0.092(3) 0.081(3) 0.018(2) 0.005(2) -0.003(2)
P1 0.0739(6) 0.0794(7) 0.0683(6) -0.0098(5) 0.0191(5) -0.0100(5)
F1 0.180(4) 0.181(4) 0.168(3) -0.095(3) 0.057(3) -0.061(3)
F2 0.188(4) 0.157(3) 0.178(4) -0.098(3) 0.050(3) -0.048(3)
F3A 0.36(2) 0.086(5) 0.181(11) 0.022(6) 0.152(14) -0.015(9)
F4A 0.29(2) 0.165(9) 0.232(14) 0.060(9) 0.172(15) -0.030(11)
F5A 0.117(9) 0.235(15) 0.262(19) -0.057(12) 0.019(9) 0.075(10)
F6A 0.083(6) 0.177(11) 0.39(3) -0.007(13) 0.081(10) 0.046(6)
F3B 0.155(9) 0.229(14) 0.149(8) 0.084(10) -0.004(7) 0.070(9)
F4B 0.232(14) 0.238(13) 0.101(6) 0.054(7) -0.025(8) 0.037(12)
F5B 0.164(12) 0.248(18) 0.199(13) -0.124(13) 0.144(12) -0.126(13)
F6B 0.103(7) 0.232(15) 0.174(9) -0.106(11) 0.078(6) -0.075(9)
O1S 0.282(10) 0.386(13) 0.207(7) -0.010(8) 0.089(7) 0.096(9)
C1S 0.167(8) 0.258(11) 0.164(8) 0.063(7) -0.015(6) 0.030(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.957(3) . ?
Cu1 N3 1.962(3) . ?
Cu1 C21 2.006(4) . ?
Cu1 C20 2.026(3) . ?
N1 C1 1.407(4) . ?
N1 C6 1.410(4) . ?
N1 C11 1.466(4) . ?
N2 C1 1.342(4) . ?
N2 C5 1.366(4) . ?
N3 C6 1.340(4) . ?
N3 C10 1.360(4) . ?
C1 C2 1.386(5) . ?
C2 C3 1.378(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.363(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.352(5) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.397(4) . ?
C7 C8 1.374(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.376(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.357(5) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C16 1.384(4) . ?
C11 C12 1.390(4) . ?
C12 C13 1.389(5) . ?
C12 C17 1.519(5) . ?
C13 C14 1.373(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.388(5) . ?
C14 C18 1.516(5) . ?
C15 C16 1.383(5) . ?
C15 H15A 0.9300 . ?
C16 C19 1.513(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17D 0.9600 . ?
C17 H17E 0.9600 . ?
C17 H17F 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 H18D 0.9600 . ?
C18 H18E 0.9600 . ?
C18 H18F 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19D 0.9600 . ?
C19 H19E 0.9600 . ?
C19 H19F 0.9600 . ?
C20 C21 1.361(5) . ?
C20 C25 1.507(6) . ?
C20 H20A 0.9800 . ?
C21 C22 1.503(5) . ?
C21 H21A 0.9800 . ?
C22 C26 1.508(6) . ?
C22 C23 1.556(6) . ?
C22 H22A 0.9800 . ?
C23 C24 1.518(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.546(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.516(6) . ?
C25 H25A 0.9800 . ?
C26 H26A 0.97(4) . ?
C26 H26B 0.94(4) . ?
P1 F6A 1.461(9) . ?
P1 F3B 1.481(8) . ?
P1 F4A 1.503(9) . ?
P1 F4B 1.504(8) . ?
P1 F5A 1.522(10) . ?
P1 F3A 1.524(8) . ?
P1 F2 1.529(3) . ?
P1 F5B 1.539(9) . ?
P1 F6B 1.556(8) . ?
P1 F1 1.568(3) . ?
O1S C1S 1.258(9) . ?
O1S H1SA 0.8200 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
C1S H1SD 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N3 94.02(11) . . ?
N2 Cu1 C21 153.44(14) . . ?
N3 Cu1 C21 112.52(14) . . ?
N2 Cu1 C20 114.21(14) . . ?
N3 Cu1 C20 151.47(15) . . ?
C21 Cu1 C20 39.45(15) . . ?
C1 N1 C6 129.2(2) . . ?
C1 N1 C11 114.9(2) . . ?
C6 N1 C11 115.9(2) . . ?
C1 N2 C5 117.9(3) . . ?
C1 N2 Cu1 123.8(2) . . ?
C5 N2 Cu1 118.3(3) . . ?
C6 N3 C10 117.6(3) . . ?
C6 N3 Cu1 123.1(2) . . ?
C10 N3 Cu1 118.6(2) . . ?
N2 C1 C2 120.6(3) . . ?
N2 C1 N1 120.2(3) . . ?
C2 C1 N1 119.2(3) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
C4 C5 N2 123.6(4) . . ?
C4 C5 H5A 118.2 . . ?
N2 C5 H5A 118.2 . . ?
N3 C6 C7 121.5(3) . . ?
N3 C6 N1 120.7(3) . . ?
C7 C6 N1 117.8(3) . . ?
C8 C7 C6 118.8(3) . . ?
C8 C7 H7A 120.6 . . ?
C6 C7 H7A 120.6 . . ?
C7 C8 C9 120.2(4) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 H9A 121.1 . . ?
C8 C9 H9A 121.1 . . ?
C9 C10 N3 124.0(4) . . ?
C9 C10 H10A 118.0 . . ?
N3 C10 H10A 118.0 . . ?
C16 C11 C12 122.5(3) . . ?
C16 C11 N1 117.0(3) . . ?
C12 C11 N1 120.4(3) . . ?
C13 C12 C11 116.9(3) . . ?
C13 C12 C17 120.6(3) . . ?
C11 C12 C17 122.5(3) . . ?
C14 C13 C12 122.8(4) . . ?
C14 C13 H13A 118.6 . . ?
C12 C13 H13A 118.6 . . ?
C13 C14 C15 118.0(3) . . ?
C13 C14 C18 121.3(4) . . ?
C15 C14 C18 120.7(4) . . ?
C16 C15 C14 122.0(4) . . ?
C16 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?
C15 C16 C11 117.8(3) . . ?
C15 C16 C19 120.3(3) . . ?
C11 C16 C19 121.9(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C17 H17D 109.5 . . ?
H17A C17 H17D 141.1 . . ?
H17B C17 H17D 56.3 . . ?
H17C C17 H17D 56.3 . . ?
C12 C17 H17E 109.5 . . ?
H17A C17 H17E 56.3 . . ?
H17B C17 H17E 141.1 . . ?
H17C C17 H17E 56.3 . . ?
H17D C17 H17E 109.5 . . ?
C12 C17 H17F 109.5 . . ?
H17A C17 H17F 56.3 . . ?
H17B C17 H17F 56.3 . . ?
H17C C17 H17F 141.1 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C14 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C14 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C19 H19D 109.5 . . ?
H19A C19 H19D 141.1 . . ?
H19B C19 H19D 56.3 . . ?
H19C C19 H19D 56.3 . . ?
C16 C19 H19E 109.5 . . ?
H19A C19 H19E 56.3 . . ?
H19B C19 H19E 141.1 . . ?
H19C C19 H19E 56.3 . . ?
H19D C19 H19E 109.5 . . ?
C16 C19 H19F 109.5 . . ?
H19A C19 H19F 56.3 . . ?
H19B C19 H19F 56.3 . . ?
H19C C19 H19F 141.1 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
C21 C20 C25 106.4(3) . . ?
C21 C20 Cu1 69.5(2) . . ?
C25 C20 Cu1 113.9(3) . . ?
C21 C20 H20A 118.9 . . ?
C25 C20 H20A 118.9 . . ?
Cu1 C20 H20A 118.9 . . ?
C20 C21 C22 106.6(3) . . ?
C20 C21 Cu1 71.1(2) . . ?
C22 C21 Cu1 113.6(2) . . ?
C20 C21 H21A 118.7 . . ?
C22 C21 H21A 118.7 . . ?
Cu1 C21 H21A 118.7 . . ?
C21 C22 C26 101.7(3) . . ?
C21 C22 C23 104.8(3) . . ?
C26 C22 C23 100.3(4) . . ?
C21 C22 H22A 115.9 . . ?
C26 C22 H22A 115.9 . . ?
C23 C22 H22A 115.9 . . ?
C24 C23 C22 102.7(3) . . ?
C24 C23 H23A 111.2 . . ?
C22 C23 H23A 111.2 . . ?
C24 C23 H23B 111.2 . . ?
C22 C23 H23B 111.2 . . ?
H23A C23 H23B 109.1 . . ?
C23 C24 C25 103.3(3) . . ?
C23 C24 H24A 111.1 . . ?
C25 C24 H24A 111.1 . . ?
C23 C24 H24B 111.1 . . ?
C25 C24 H24B 111.1 . . ?
H24A C24 H24B 109.1 . . ?
C20 C25 C26 101.5(3) . . ?
C20 C25 C24 104.2(4) . . ?
C26 C25 C24 100.7(4) . . ?
C20 C25 H25A 116.1 . . ?
C26 C25 H25A 116.1 . . ?
C24 C25 H25A 116.1 . . ?
C22 C26 C25 94.2(3) . . ?
C22 C26 H26A 115(2) . . ?
C25 C26 H26A 111(2) . . ?
C22 C26 H26B 110(3) . . ?
C25 C26 H26B 118(3) . . ?
H26A C26 H26B 109(3) . . ?
F6A P1 F3B 121.9(9) . . ?
F6A P1 F4A 93.4(10) . . ?
F3B P1 F4A 133.3(10) . . ?
F6A P1 F4B 54.1(8) . . ?
F3B P1 F4B 176.0(8) . . ?
F4A P1 F4B 49.7(7) . . ?
F6A P1 F5A 175.8(11) . . ?
F3B P1 F5A 53.9(7) . . ?
F4A P1 F5A 89.8(9) . . ?
F4B P1 F5A 130.1(9) . . ?
F6A P1 F3A 89.8(8) . . ?
F3B P1 F3A 45.6(7) . . ?
F4A P1 F3A 176.2(8) . . ?
F4B P1 F3A 131.7(11) . . ?
F5A P1 F3A 87.1(10) . . ?
F6A P1 F2 80.7(7) . . ?
F3B P1 F2 75.9(6) . . ?
F4A P1 F2 81.6(7) . . ?
F4B P1 F2 102.9(6) . . ?
F5A P1 F2 97.0(6) . . ?
F3A P1 F2 101.0(5) . . ?
F6A P1 F5B 144.1(10) . . ?
F3B P1 F5B 88.5(9) . . ?
F4A P1 F5B 50.8(7) . . ?
F4B P1 F5B 95.3(9) . . ?
F5A P1 F5B 39.0(8) . . ?
F3A P1 F5B 126.1(11) . . ?
F2 P1 F5B 90.1(4) . . ?
F6A P1 F6B 37.9(7) . . ?
F3B P1 F6B 90.7(7) . . ?
F4A P1 F6B 130.9(11) . . ?
F4B P1 F6B 85.5(9) . . ?
F5A P1 F6B 139.2(10) . . ?
F3A P1 F6B 52.1(7) . . ?
F2 P1 F6B 92.2(4) . . ?
F5B P1 F6B 177.4(8) . . ?
F6A P1 F1 99.7(7) . . ?
F3B P1 F1 104.2(6) . . ?
F4A P1 F1 98.0(7) . . ?
F4B P1 F1 77.1(5) . . ?
F5A P1 F1 82.6(6) . . ?
F3A P1 F1 79.4(5) . . ?
F2 P1 F1 179.5(2) . . ?
F5B P1 F1 89.4(4) . . ?
F6B P1 F1 88.4(4) . . ?
C1S O1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
O1S C1S H1SD 109.5 . . ?
H1SB C1S H1SD 109.5 . . ?
H1SC C1S H1SD 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cu1 N2 C1 -21.5(3) . . . . ?
C21 Cu1 N2 C1 160.4(3) . . . . ?
C20 Cu1 N2 C1 154.3(2) . . . . ?
N3 Cu1 N2 C5 160.8(3) . . . . ?
C21 Cu1 N2 C5 -17.3(4) . . . . ?
C20 Cu1 N2 C5 -23.5(3) . . . . ?
N2 Cu1 N3 C6 24.3(3) . . . . ?
C21 Cu1 N3 C6 -156.6(3) . . . . ?
C20 Cu1 N3 C6 -147.6(3) . . . . ?
N2 Cu1 N3 C10 -165.1(3) . . . . ?
C21 Cu1 N3 C10 14.0(3) . . . . ?
C20 Cu1 N3 C10 23.0(4) . . . . ?
C5 N2 C1 C2 1.9(4) . . . . ?
Cu1 N2 C1 C2 -175.8(2) . . . . ?
C5 N2 C1 N1 -179.7(3) . . . . ?
Cu1 N2 C1 N1 2.6(4) . . . . ?
C6 N1 C1 N2 25.5(5) . . . . ?
C11 N1 C1 N2 -150.7(3) . . . . ?
C6 N1 C1 C2 -156.1(3) . . . . ?
C11 N1 C1 C2 27.7(4) . . . . ?
N2 C1 C2 C3 -1.7(5) . . . . ?
N1 C1 C2 C3 179.9(3) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 N2 -0.1(6) . . . . ?
C1 N2 C5 C4 -1.0(5) . . . . ?
Cu1 N2 C5 C4 176.8(3) . . . . ?
C10 N3 C6 C7 0.0(5) . . . . ?
Cu1 N3 C6 C7 170.7(2) . . . . ?
C10 N3 C6 N1 -178.9(3) . . . . ?
Cu1 N3 C6 N1 -8.2(4) . . . . ?
C1 N1 C6 N3 -22.4(5) . . . . ?
C11 N1 C6 N3 153.8(3) . . . . ?
C1 N1 C6 C7 158.6(3) . . . . ?
C11 N1 C6 C7 -25.2(4) . . . . ?
N3 C6 C7 C8 -1.7(5) . . . . ?
N1 C6 C7 C8 177.3(3) . . . . ?
C6 C7 C8 C9 1.6(6) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 N3 -2.0(6) . . . . ?
C6 N3 C10 C9 1.9(6) . . . . ?
Cu1 N3 C10 C9 -169.2(3) . . . . ?
C1 N1 C11 C16 90.6(3) . . . . ?
C6 N1 C11 C16 -86.1(3) . . . . ?
C1 N1 C11 C12 -88.0(3) . . . . ?
C6 N1 C11 C12 95.3(3) . . . . ?
C16 C11 C12 C13 -3.0(5) . . . . ?
N1 C11 C12 C13 175.5(3) . . . . ?
C16 C11 C12 C17 178.0(3) . . . . ?
N1 C11 C12 C17 -3.5(5) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?
C17 C12 C13 C14 -179.6(4) . . . . ?
C12 C13 C14 C15 0.9(6) . . . . ?
C12 C13 C14 C18 -179.9(4) . . . . ?
C13 C14 C15 C16 -1.7(5) . . . . ?
C18 C14 C15 C16 179.2(4) . . . . ?
C14 C15 C16 C11 0.2(5) . . . . ?
C14 C15 C16 C19 179.9(3) . . . . ?
C12 C11 C16 C15 2.3(5) . . . . ?
N1 C11 C16 C15 -176.3(3) . . . . ?
C12 C11 C16 C19 -177.5(3) . . . . ?
N1 C11 C16 C19 4.0(4) . . . . ?
N2 Cu1 C20 C21 175.7(2) . . . . ?
N3 Cu1 C20 C21 -13.2(4) . . . . ?
N2 Cu1 C20 C25 -84.9(3) . . . . ?
N3 Cu1 C20 C25 86.2(4) . . . . ?
C21 Cu1 C20 C25 99.4(4) . . . . ?
C25 C20 C21 C22 0.0(4) . . . . ?
Cu1 C20 C21 C22 109.9(2) . . . . ?
C25 C20 C21 Cu1 -109.9(3) . . . . ?
N2 Cu1 C21 C20 -8.9(4) . . . . ?
N3 Cu1 C21 C20 173.2(2) . . . . ?
N2 Cu1 C21 C22 -109.2(3) . . . . ?
N3 Cu1 C21 C22 72.9(3) . . . . ?
C20 Cu1 C21 C22 -100.3(3) . . . . ?
C20 C21 C22 C26 -32.9(4) . . . . ?
Cu1 C21 C22 C26 43.3(4) . . . . ?
C20 C21 C22 C23 71.3(4) . . . . ?
Cu1 C21 C22 C23 147.4(3) . . . . ?
C21 C22 C23 C24 -68.1(4) . . . . ?
C26 C22 C23 C24 37.1(4) . . . . ?
C22 C23 C24 C25 -1.0(5) . . . . ?
C21 C20 C25 C26 32.7(4) . . . . ?
Cu1 C20 C25 C26 -41.7(4) . . . . ?
C21 C20 C25 C24 -71.5(4) . . . . ?
Cu1 C20 C25 C24 -145.9(3) . . . . ?
C23 C24 C25 C20 69.6(5) . . . . ?
C23 C24 C25 C26 -35.2(5) . . . . ?
C21 C22 C26 C25 49.7(4) . . . . ?
C23 C22 C26 C25 -57.9(4) . . . . ?
C20 C25 C26 C22 -49.7(4) . . . . ?
C24 C25 C26 C22 57.4(4) . . . . ?
N3 N2 C20 C21 -7.1(2) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1S H1SA F6B 0.82 2.07 2.885(16) 171 .
_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full 28.36
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max 0.389
_refine_diff_density_min -0.392
_refine_diff_density_rms 0.060
_exptl_crystal_recrystallization_method
'cooled sat. soln. in MeOH to -12 deg. C for several weeks'
_diffrn_ambient_pressure 101.33
data_ipr1cl
_database_code_depnum_ccdc_archive 'CCDC 733833'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
Flack, H.D. & Bernardinelli, G. Acta Cryst., 1999, A55,
908-915.
Flack, H.D. & Bernardinelli, G.J. Appl. Cryst., 2000, 33,
1143-1148.
Clegg, W. Acta Cryst. 2003, E59,
e2-e5.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_formula_moiety 'C38 H38 Cl4 Cu2 N6'
_chemical_formula_sum 'C38 H38 Cl4 Cu2 N6'
_exptl_crystal_recrystallization_method 'slow evap. of MeOH solution'
_chemical_melting_point ?
_exptl_crystal_description needle
_exptl_crystal_colour green
_diffrn_ambient_temperature 298(2)
_diffrn_ambient_pressure 101.33
_chemical_formula_weight 847.62
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_int_tables_number 33
_chemical_absolute_configuration ad
_symmetry_space_group_name_Hall 'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
_cell_length_a 15.295(3)
_cell_length_b 9.0595(18)
_cell_length_c 26.601(5)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 3686.0(13)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 5118
_cell_measurement_theta_min 2.37
_cell_measurement_theta_max 21.78
_exptl_crystal_size_max 0.56
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.13
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.527
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1736
_exptl_absorpt_coefficient_mu 1.481
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.4909
_exptl_absorpt_correction_T_max 0.8307
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 43741
_diffrn_reflns_av_R_equivalents 0.0924
_diffrn_reflns_av_sigmaI/netI 0.0892
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_limit_l_max 34
_diffrn_reflns_theta_min 1.53
_diffrn_reflns_theta_max 28.31
_reflns_number_total 9011
_reflns_number_gt 5711
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
SHELXTL weights: 0.0515, 0
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.44(11)
_refine_ls_number_reflns 9011
_refine_ls_number_parameters 456
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.1020
_refine_ls_R_factor_gt 0.0476
_refine_ls_wR_factor_ref 0.1216
_refine_ls_wR_factor_gt 0.1002
_refine_ls_goodness_of_fit_ref 1.000
_refine_ls_restrained_S_all 1.000
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.13750(4) 0.84336(6) 0.24641(2) 0.03396(16) Uani 1 1 d . . .
Cl1 Cl 0.02762(8) 0.70864(15) 0.21050(5) 0.0436(3) Uani 1 1 d . . .
Cl3 Cl 0.17027(11) 0.66274(14) 0.30196(6) 0.0540(4) Uani 1 1 d . . .
N1 N 0.1320(2) 1.1357(5) 0.30539(18) 0.0311(10) Uani 1 1 d . . .
N2 N 0.2355(2) 0.9648(4) 0.27541(16) 0.0339(10) Uani 1 1 d . . .
N3 N 0.0823(2) 1.0385(4) 0.22816(13) 0.0333(10) Uani 1 1 d . . .
C1 C 0.2167(3) 1.0777(5) 0.30649(19) 0.0323(11) Uani 1 1 d . . .
C2 C 0.2809(4) 1.1360(6) 0.3380(2) 0.0451(13) Uani 1 1 d . . .
H2A H 0.2678 1.2124 0.3601 0.054 Uiso 1 1 calc R . .
C3 C 0.3629(3) 1.0789(7) 0.3357(2) 0.0508(15) Uani 1 1 d . . .
H3A H 0.4060 1.1159 0.3569 0.061 Uiso 1 1 calc R . .
C4 C 0.3834(3) 0.9687(6) 0.3030(2) 0.0414(13) Uani 1 1 d . . .
H4A H 0.4400 0.9321 0.3007 0.050 Uiso 1 1 calc R . .
C5 C 0.3172(3) 0.9135(6) 0.2736(2) 0.0396(12) Uani 1 1 d . . .
H5A H 0.3299 0.8370 0.2514 0.048 Uiso 1 1 calc R . .
C6 C 0.0847(3) 1.1536(5) 0.26020(17) 0.0288(11) Uani 1 1 d . . .
C7 C 0.0425(3) 1.2839(6) 0.2497(2) 0.0374(12) Uani 1 1 d . . .
H7A H 0.0442 1.3611 0.2728 0.045 Uiso 1 1 calc R . .
C8 C -0.0018(4) 1.3001(7) 0.2058(2) 0.0427(14) Uani 1 1 d . . .
H8A H -0.0311 1.3876 0.1987 0.051 Uiso 1 1 calc R . .
C9 C -0.0028(4) 1.1846(6) 0.1719(2) 0.0449(14) Uani 1 1 d . . .
H9A H -0.0319 1.1940 0.1414 0.054 Uiso 1 1 calc R . .
C10 C 0.0388(3) 1.0582(6) 0.18368(19) 0.0410(14) Uani 1 1 d . . .
H10A H 0.0381 0.9811 0.1606 0.049 Uiso 1 1 calc R . .
C11 C 0.0936(3) 1.1923(6) 0.35136(19) 0.0320(12) Uani 1 1 d . . .
C12 C 0.0368(3) 1.1025(5) 0.3789(2) 0.0348(12) Uani 1 1 d . . .
C13 C 0.0037(3) 1.1597(7) 0.4236(2) 0.0442(14) Uani 1 1 d . . .
H13A H -0.0340 1.1023 0.4428 0.053 Uiso 1 1 calc R . .
C14 C 0.0252(4) 1.2980(8) 0.4400(2) 0.0459(15) Uani 1 1 d . . .
H14A H 0.0038 1.3313 0.4707 0.055 Uiso 1 1 calc R . .
C15 C 0.0776(4) 1.3879(6) 0.4119(2) 0.0473(15) Uani 1 1 d . . .
H15A H 0.0896 1.4835 0.4227 0.057 Uiso 1 1 calc R . .
C16 C 0.1131(3) 1.3357(5) 0.3670(2) 0.0381(13) Uani 1 1 d . . .
H16A H 0.1493 1.3957 0.3477 0.046 Uiso 1 1 calc R . .
C17 C 0.0089(4) 0.9522(6) 0.3596(2) 0.0479(14) Uani 1 1 d . . .
H17A H 0.0515 0.9220 0.3341 0.057 Uiso 1 1 calc R . .
C18 C 0.0073(4) 0.8325(6) 0.3997(3) 0.0558(16) Uani 1 1 d . . .
H18A H 0.0626 0.8302 0.4168 0.084 Uiso 1 1 calc R . .
H18B H -0.0033 0.7385 0.3842 0.084 Uiso 1 1 calc R . .
H18C H -0.0383 0.8532 0.4235 0.084 Uiso 1 1 calc R . .
C19 C -0.0800(4) 0.9648(7) 0.3335(3) 0.070(2) Uani 1 1 d . . .
H19A H -0.1226 1.0009 0.3570 0.104 Uiso 1 1 calc R . .
H19B H -0.0976 0.8694 0.3215 0.104 Uiso 1 1 calc R . .
H19C H -0.0756 1.0319 0.3057 0.104 Uiso 1 1 calc R . .
Cu2 Cu 0.12138(4) 0.66071(6) 0.12681(2) 0.03342(15) Uani 1 1 d . . .
Cl2 Cl 0.22917(9) 0.80401(16) 0.16078(5) 0.0444(3) Uani 1 1 d . . .
Cl4 Cl 0.08065(10) 0.83628(15) 0.07093(5) 0.0531(4) Uani 1 1 d . . .
N4 N 0.1345(2) 0.3631(5) 0.07104(17) 0.0301(10) Uani 1 1 d . . .
N5 N 0.1814(2) 0.4704(4) 0.14727(14) 0.0325(9) Uani 1 1 d . . .
N6 N 0.0270(2) 0.5295(4) 0.09847(15) 0.0296(9) Uani 1 1 d . . .
C20 C 0.1812(3) 0.3528(5) 0.11692(17) 0.0275(11) Uani 1 1 d . . .
C21 C 0.2237(3) 0.2229(6) 0.1294(3) 0.0394(13) Uani 1 1 d . . .
H21A H 0.2215 0.1420 0.1079 0.047 Uiso 1 1 calc R . .
C22 C 0.2689(4) 0.2150(7) 0.1738(2) 0.0462(15) Uani 1 1 d . . .
H22A H 0.2996 0.1300 0.1822 0.055 Uiso 1 1 calc R . .
C23 C 0.2681(4) 0.3339(6) 0.2056(2) 0.0456(14) Uani 1 1 d . . .
H23A H 0.2971 0.3298 0.2363 0.055 Uiso 1 1 calc R . .
C24 C 0.2244(3) 0.4581(6) 0.19164(19) 0.0406(13) Uani 1 1 d . . .
H24A H 0.2240 0.5381 0.2135 0.049 Uiso 1 1 calc R . .
C25 C 0.0487(3) 0.4175(5) 0.06876(18) 0.0301(11) Uani 1 1 d . . .
C26 C -0.0119(3) 0.3539(6) 0.0365(2) 0.0393(12) Uani 1 1 d . . .
H26A H 0.0044 0.2785 0.0147 0.047 Uiso 1 1 calc R . .
C27 C -0.0963(3) 0.4043(6) 0.0373(2) 0.0465(14) Uani 1 1 d . . .
H27A H -0.1376 0.3636 0.0158 0.056 Uiso 1 1 calc R . .
C28 C -0.1202(3) 0.5153(6) 0.0700(2) 0.0407(13) Uani 1 1 d . . .
H28A H -0.1777 0.5483 0.0718 0.049 Uiso 1 1 calc R . .
C29 C -0.0571(3) 0.5743(6) 0.0994(2) 0.0384(12) Uani 1 1 d . . .
H29A H -0.0725 0.6497 0.1215 0.046 Uiso 1 1 calc R . .
C30 C 0.1751(3) 0.3065(5) 0.02553(17) 0.0286(11) Uani 1 1 d . . .
C31 C 0.2252(3) 0.4026(6) -0.00305(19) 0.0338(12) Uani 1 1 d . . .
C32 C 0.2577(3) 0.3485(7) -0.0489(2) 0.0458(14) Uani 1 1 d . . .
H32A H 0.2891 0.4116 -0.0698 0.055 Uiso 1 1 calc R . .
C33 C 0.2443(4) 0.2048(9) -0.0638(2) 0.0491(16) Uani 1 1 d . . .
H33A H 0.2662 0.1717 -0.0945 0.059 Uiso 1 1 calc R . .
C34 C 0.1986(4) 0.1106(7) -0.0332(2) 0.0483(15) Uani 1 1 d . . .
H34A H 0.1916 0.0123 -0.0425 0.058 Uiso 1 1 calc R . .
C35 C 0.1630(4) 0.1609(6) 0.0111(2) 0.0390(13) Uani 1 1 d . . .
H35A H 0.1307 0.0973 0.0313 0.047 Uiso 1 1 calc R . .
C36 C 0.2488(4) 0.5558(6) 0.0157(2) 0.0467(14) Uani 1 1 d . . .
H36A H 0.2061 0.5827 0.0416 0.056 Uiso 1 1 calc R . .
C37 C 0.2452(5) 0.6746(7) -0.0252(3) 0.071(2) Uani 1 1 d . . .
H37A H 0.2861 0.6509 -0.0513 0.107 Uiso 1 1 calc R . .
H37B H 0.2598 0.7687 -0.0109 0.107 Uiso 1 1 calc R . .
H37C H 0.1872 0.6787 -0.0390 0.107 Uiso 1 1 calc R . .
C38 C 0.3378(4) 0.5521(8) 0.0405(3) 0.074(2) Uani 1 1 d . . .
H38A H 0.3385 0.4772 0.0661 0.111 Uiso 1 1 calc R . .
H38B H 0.3499 0.6463 0.0555 0.111 Uiso 1 1 calc R . .
H38C H 0.3817 0.5303 0.0158 0.111 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0414(3) 0.0265(3) 0.0340(3) 0.0002(3) -0.0029(3) -0.0029(2)
Cl1 0.0431(7) 0.0422(7) 0.0455(8) -0.0047(7) 0.0043(6) -0.0136(6)
Cl3 0.0862(11) 0.0350(7) 0.0408(7) 0.0084(7) -0.0068(8) -0.0025(7)
N1 0.035(2) 0.030(2) 0.028(2) -0.0020(19) 0.0009(17) -0.0020(16)
N2 0.032(2) 0.032(2) 0.037(2) 0.000(2) -0.0050(18) 0.0021(17)
N3 0.036(2) 0.031(2) 0.033(2) -0.0034(18) -0.0022(19) -0.0041(17)
C1 0.036(3) 0.032(3) 0.030(3) 0.007(2) 0.004(2) -0.005(2)
C2 0.040(3) 0.053(3) 0.042(3) -0.014(3) -0.005(3) -0.005(3)
C3 0.038(3) 0.062(4) 0.052(3) -0.002(3) -0.006(3) -0.003(3)
C4 0.026(3) 0.048(3) 0.050(3) -0.001(3) 0.000(3) 0.003(2)
C5 0.042(3) 0.039(3) 0.038(3) -0.005(2) -0.001(2) 0.005(2)
C6 0.027(2) 0.029(2) 0.029(3) 0.003(2) 0.0049(19) -0.007(2)
C7 0.043(3) 0.034(3) 0.035(3) -0.004(3) -0.004(3) 0.007(2)
C8 0.040(3) 0.035(3) 0.053(4) 0.005(3) -0.003(3) 0.001(2)
C9 0.044(3) 0.054(4) 0.038(3) 0.014(3) -0.005(3) 0.006(3)
C10 0.048(3) 0.046(4) 0.029(3) -0.004(2) -0.003(2) -0.004(3)
C11 0.031(3) 0.037(3) 0.027(3) -0.001(2) -0.002(2) 0.002(2)
C12 0.032(3) 0.033(3) 0.040(3) 0.000(2) 0.005(2) 0.000(2)
C13 0.038(3) 0.058(4) 0.037(3) 0.010(3) 0.007(3) -0.002(3)
C14 0.044(3) 0.058(4) 0.035(3) -0.013(3) 0.006(3) 0.009(3)
C15 0.055(4) 0.043(3) 0.043(3) -0.018(3) -0.009(3) 0.012(3)
C16 0.045(3) 0.028(3) 0.042(3) 0.000(2) -0.006(2) -0.003(2)
C17 0.050(3) 0.046(3) 0.048(3) -0.005(3) 0.015(3) -0.004(3)
C18 0.045(3) 0.043(3) 0.080(5) 0.013(3) 0.010(3) -0.002(3)
C19 0.081(5) 0.052(4) 0.075(5) 0.013(4) -0.023(4) -0.029(3)
Cu2 0.0374(3) 0.0274(3) 0.0354(3) -0.0012(3) -0.0023(3) -0.0033(2)
Cl2 0.0424(8) 0.0453(8) 0.0456(8) -0.0079(7) 0.0040(6) -0.0142(6)
Cl4 0.0724(10) 0.0399(8) 0.0472(8) 0.0117(7) -0.0060(8) -0.0029(7)
N4 0.030(2) 0.033(2) 0.027(2) -0.0031(19) -0.0012(17) -0.0009(16)
N5 0.036(2) 0.033(2) 0.029(2) 0.0010(18) -0.0009(18) -0.0025(18)
N6 0.031(2) 0.025(2) 0.032(2) -0.0009(18) 0.0011(17) 0.0003(16)
C20 0.023(2) 0.032(3) 0.027(3) 0.004(2) 0.0011(19) -0.0073(19)
C21 0.042(3) 0.028(2) 0.048(4) 0.005(3) -0.002(3) 0.003(2)
C22 0.038(3) 0.045(3) 0.055(4) 0.010(3) -0.003(3) 0.005(3)
C23 0.044(3) 0.056(4) 0.037(3) 0.008(3) -0.007(3) -0.002(3)
C24 0.046(3) 0.045(3) 0.031(3) -0.004(2) -0.004(2) 0.002(3)
C25 0.030(3) 0.032(3) 0.028(3) 0.002(2) 0.002(2) -0.003(2)
C26 0.036(3) 0.044(3) 0.038(3) -0.012(2) 0.000(2) 0.001(2)
C27 0.034(3) 0.054(4) 0.052(3) -0.005(3) -0.008(3) -0.006(2)
C28 0.025(3) 0.047(3) 0.051(3) 0.007(3) -0.005(2) 0.001(2)
C29 0.041(3) 0.033(3) 0.041(3) 0.001(2) 0.004(2) 0.006(2)
C30 0.033(3) 0.029(3) 0.024(2) -0.002(2) 0.001(2) 0.000(2)
C31 0.031(3) 0.038(3) 0.033(3) 0.003(2) 0.003(2) -0.001(2)
C32 0.038(3) 0.059(4) 0.040(3) 0.005(3) 0.013(3) 0.004(3)
C33 0.046(3) 0.073(5) 0.029(3) -0.007(3) -0.003(3) 0.015(3)
C34 0.041(3) 0.045(3) 0.058(4) -0.018(3) -0.009(3) 0.009(3)
C35 0.033(3) 0.037(3) 0.047(3) -0.002(3) 0.002(3) -0.003(2)
C36 0.056(3) 0.037(3) 0.047(3) -0.002(3) 0.018(3) -0.010(3)
C37 0.080(5) 0.054(4) 0.079(5) 0.011(4) 0.014(4) -0.002(3)
C38 0.066(4) 0.066(5) 0.091(5) 0.001(4) -0.016(4) -0.021(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.013(4) . ?
Cu1 N3 2.018(4) . ?
Cu1 Cl3 2.2610(15) . ?
Cu1 Cl1 2.2862(15) . ?
Cu1 Cl2 2.6985(16) . ?
Cl1 Cu2 2.6835(16) . ?
N1 C1 1.399(6) . ?
N1 C6 1.412(7) . ?
N1 C11 1.450(7) . ?
N2 C5 1.334(6) . ?
N2 C1 1.346(6) . ?
N3 C6 1.347(6) . ?
N3 C10 1.369(6) . ?
C1 C2 1.395(7) . ?
C2 C3 1.359(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.360(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(7) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.374(7) . ?
C7 C8 1.359(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.381(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.347(7) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C16 1.396(7) . ?
C11 C12 1.397(7) . ?
C12 C13 1.393(8) . ?
C12 C17 1.517(7) . ?
C13 C14 1.367(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.366(8) . ?
C14 H14A 0.9300 . ?
C15 C16 1.395(8) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.523(8) . ?
C17 C19 1.531(8) . ?
C17 H17A 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Cu2 N6 2.016(4) . ?
Cu2 N5 2.028(4) . ?
Cu2 Cl4 2.2644(15) . ?
Cu2 Cl2 2.2848(14) . ?
N4 C25 1.403(6) . ?
N4 C20 1.417(6) . ?
N4 C30 1.454(6) . ?
N5 C20 1.337(6) . ?
N5 C24 1.356(6) . ?
N6 C25 1.328(6) . ?
N6 C29 1.349(6) . ?
C20 C21 1.385(7) . ?
C21 C22 1.370(9) . ?
C21 H21A 0.9300 . ?
C22 C23 1.369(8) . ?
C22 H22A 0.9300 . ?
C23 C24 1.360(7) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 C26 1.388(7) . ?
C26 C27 1.368(7) . ?
C26 H26A 0.9300 . ?
C27 C28 1.379(8) . ?
C27 H27A 0.9300 . ?
C28 C29 1.353(7) . ?
C28 H28A 0.9300 . ?
C29 H29A 0.9300 . ?
C30 C35 1.386(7) . ?
C30 C31 1.387(7) . ?
C31 C32 1.406(8) . ?
C31 C36 1.519(7) . ?
C32 C33 1.377(9) . ?
C32 H32A 0.9300 . ?
C33 C34 1.371(9) . ?
C33 H33A 0.9300 . ?
C34 C35 1.377(8) . ?
C34 H34A 0.9300 . ?
C35 H35A 0.9300 . ?
C36 C38 1.514(8) . ?
C36 C37 1.531(8) . ?
C36 H36A 0.9800 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N3 85.68(16) . . ?
N2 Cu1 Cl3 88.86(12) . . ?
N3 Cu1 Cl3 152.10(12) . . ?
N2 Cu1 Cl1 177.82(13) . . ?
N3 Cu1 Cl1 93.42(11) . . ?
Cl3 Cu1 Cl1 92.85(6) . . ?
N2 Cu1 Cl2 90.51(12) . . ?
N3 Cu1 Cl2 97.47(11) . . ?
Cl3 Cu1 Cl2 109.93(6) . . ?
Cl1 Cu1 Cl2 87.64(5) . . ?
Cu1 Cl1 Cu2 92.30(5) . . ?
C1 N1 C6 122.4(4) . . ?
C1 N1 C11 119.3(4) . . ?
C6 N1 C11 118.1(4) . . ?
C5 N2 C1 119.1(4) . . ?
C5 N2 Cu1 119.5(3) . . ?
C1 N2 Cu1 119.4(3) . . ?
C6 N3 C10 117.3(4) . . ?
C6 N3 Cu1 121.0(3) . . ?
C10 N3 Cu1 121.7(4) . . ?
N2 C1 C2 120.4(5) . . ?
N2 C1 N1 118.1(4) . . ?
C2 C1 N1 121.5(5) . . ?
C3 C2 C1 118.6(5) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 C4 121.4(5) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 C5 117.5(5) . . ?
C3 C4 H4A 121.3 . . ?
C5 C4 H4A 121.3 . . ?
N2 C5 C4 122.9(5) . . ?
N2 C5 H5A 118.6 . . ?
C4 C5 H5A 118.6 . . ?
N3 C6 C7 121.6(5) . . ?
N3 C6 N1 117.6(4) . . ?
C7 C6 N1 120.7(5) . . ?
C8 C7 C6 120.1(6) . . ?
C8 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
C7 C8 C9 119.0(5) . . ?
C7 C8 H8A 120.5 . . ?
C9 C8 H8A 120.5 . . ?
C10 C9 C8 119.2(5) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
C9 C10 N3 122.8(5) . . ?
C9 C10 H10A 118.6 . . ?
N3 C10 H10A 118.6 . . ?
C16 C11 C12 121.2(5) . . ?
C16 C11 N1 119.6(5) . . ?
C12 C11 N1 119.2(5) . . ?
C13 C12 C11 117.2(5) . . ?
C13 C12 C17 121.4(5) . . ?
C11 C12 C17 121.3(5) . . ?
C14 C13 C12 121.8(5) . . ?
C14 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 119.7(5) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
C15 C16 C11 119.2(5) . . ?
C15 C16 H16A 120.4 . . ?
C11 C16 H16A 120.4 . . ?
C12 C17 C18 114.0(5) . . ?
C12 C17 C19 109.7(5) . . ?
C18 C17 C19 110.9(5) . . ?
C12 C17 H17A 107.3 . . ?
C18 C17 H17A 107.3 . . ?
C19 C17 H17A 107.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N6 Cu2 N5 85.60(15) . . ?
N6 Cu2 Cl4 88.38(12) . . ?
N5 Cu2 Cl4 153.89(12) . . ?
N6 Cu2 Cl2 178.22(12) . . ?
N5 Cu2 Cl2 92.87(12) . . ?
Cl4 Cu2 Cl2 93.39(6) . . ?
N6 Cu2 Cl1 91.32(11) . . ?
N5 Cu2 Cl1 99.03(11) . . ?
Cl4 Cu2 Cl1 106.50(6) . . ?
Cl2 Cu2 Cl1 88.03(5) . . ?
Cu2 Cl2 Cu1 91.95(5) . . ?
C25 N4 C20 122.1(4) . . ?
C25 N4 C30 119.2(4) . . ?
C20 N4 C30 118.6(4) . . ?
C20 N5 C24 117.5(4) . . ?
C20 N5 Cu2 120.9(3) . . ?
C24 N5 Cu2 121.6(4) . . ?
C25 N6 C29 118.6(4) . . ?
C25 N6 Cu2 119.6(3) . . ?
C29 N6 Cu2 119.9(3) . . ?
N5 C20 C21 122.1(5) . . ?
N5 C20 N4 118.0(4) . . ?
C21 C20 N4 120.0(5) . . ?
C22 C21 C20 119.2(6) . . ?
C22 C21 H21A 120.4 . . ?
C20 C21 H21A 120.4 . . ?
C23 C22 C21 119.1(6) . . ?
C23 C22 H22A 120.4 . . ?
C21 C22 H22A 120.4 . . ?
C24 C23 C22 119.1(5) . . ?
C24 C23 H23A 120.4 . . ?
C22 C23 H23A 120.4 . . ?
N5 C24 C23 123.0(5) . . ?
N5 C24 H24A 118.5 . . ?
C23 C24 H24A 118.5 . . ?
N6 C25 C26 121.2(4) . . ?
N6 C25 N4 118.4(4) . . ?
C26 C25 N4 120.4(4) . . ?
C27 C26 C25 118.8(5) . . ?
C27 C26 H26A 120.6 . . ?
C25 C26 H26A 120.6 . . ?
C26 C27 C28 120.3(5) . . ?
C26 C27 H27A 119.9 . . ?
C28 C27 H27A 119.9 . . ?
C29 C28 C27 117.6(5) . . ?
C29 C28 H28A 121.2 . . ?
C27 C28 H28A 121.2 . . ?
N6 C29 C28 123.4(5) . . ?
N6 C29 H29A 118.3 . . ?
C28 C29 H29A 118.3 . . ?
C35 C30 C31 121.3(5) . . ?
C35 C30 N4 120.6(5) . . ?
C31 C30 N4 118.1(4) . . ?
C30 C31 C32 116.9(5) . . ?
C30 C31 C36 121.7(5) . . ?
C32 C31 C36 121.3(5) . . ?
C33 C32 C31 121.8(5) . . ?
C33 C32 H32A 119.1 . . ?
C31 C32 H32A 119.1 . . ?
C34 C33 C32 119.6(6) . . ?
C34 C33 H33A 120.2 . . ?
C32 C33 H33A 120.2 . . ?
C33 C34 C35 120.3(6) . . ?
C33 C34 H34A 119.9 . . ?
C35 C34 H34A 119.9 . . ?
C34 C35 C30 120.0(5) . . ?
C34 C35 H35A 120.0 . . ?
C30 C35 H35A 120.0 . . ?
C38 C36 C31 109.7(5) . . ?
C38 C36 C37 111.0(5) . . ?
C31 C36 C37 113.6(5) . . ?
C38 C36 H36A 107.4 . . ?
C31 C36 H36A 107.4 . . ?
C37 C36 H36A 107.4 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cu1 Cl1 Cu2 99.42(11) . . . . ?
Cl3 Cu1 Cl1 Cu2 -107.77(6) . . . . ?
Cl2 Cu1 Cl1 Cu2 2.08(6) . . . . ?
N3 Cu1 N2 C5 -146.7(4) . . . . ?
Cl3 Cu1 N2 C5 60.7(4) . . . . ?
Cl2 Cu1 N2 C5 -49.3(4) . . . . ?
N3 Cu1 N2 C1 49.0(4) . . . . ?
Cl3 Cu1 N2 C1 -103.7(4) . . . . ?
Cl2 Cu1 N2 C1 146.4(4) . . . . ?
N2 Cu1 N3 C6 -40.8(3) . . . . ?
Cl3 Cu1 N3 C6 38.5(5) . . . . ?
Cl1 Cu1 N3 C6 141.1(3) . . . . ?
Cl2 Cu1 N3 C6 -130.8(3) . . . . ?
N2 Cu1 N3 C10 141.2(4) . . . . ?
Cl3 Cu1 N3 C10 -139.5(3) . . . . ?
Cl1 Cu1 N3 C10 -36.8(4) . . . . ?
Cl2 Cu1 N3 C10 51.2(4) . . . . ?
C5 N2 C1 C2 -2.8(7) . . . . ?
Cu1 N2 C1 C2 161.6(4) . . . . ?
C5 N2 C1 N1 176.0(4) . . . . ?
Cu1 N2 C1 N1 -19.6(6) . . . . ?
C6 N1 C1 N2 -39.1(6) . . . . ?
C11 N1 C1 N2 146.6(5) . . . . ?
C6 N1 C1 C2 139.7(5) . . . . ?
C11 N1 C1 C2 -34.6(7) . . . . ?
N2 C1 C2 C3 1.6(8) . . . . ?
N1 C1 C2 C3 -177.1(5) . . . . ?
C1 C2 C3 C4 1.0(9) . . . . ?
C2 C3 C4 C5 -2.2(9) . . . . ?
C1 N2 C5 C4 1.5(8) . . . . ?
Cu1 N2 C5 C4 -162.9(4) . . . . ?
C3 C4 C5 N2 1.0(8) . . . . ?
C10 N3 C6 C7 2.4(7) . . . . ?
Cu1 N3 C6 C7 -175.6(4) . . . . ?
C10 N3 C6 N1 -177.9(4) . . . . ?
Cu1 N3 C6 N1 4.1(5) . . . . ?
C1 N1 C6 N3 48.0(6) . . . . ?
C11 N1 C6 N3 -137.7(4) . . . . ?
C1 N1 C6 C7 -132.3(5) . . . . ?
C11 N1 C6 C7 42.0(6) . . . . ?
N3 C6 C7 C8 -1.1(8) . . . . ?
N1 C6 C7 C8 179.2(5) . . . . ?
C6 C7 C8 C9 -0.7(9) . . . . ?
C7 C8 C9 C10 1.1(9) . . . . ?
C8 C9 C10 N3 0.2(9) . . . . ?
C6 N3 C10 C9 -2.0(7) . . . . ?
Cu1 N3 C10 C9 176.0(4) . . . . ?
C1 N1 C11 C16 82.7(6) . . . . ?
C6 N1 C11 C16 -91.8(6) . . . . ?
C1 N1 C11 C12 -98.1(5) . . . . ?
C6 N1 C11 C12 87.4(6) . . . . ?
C16 C11 C12 C13 -2.7(8) . . . . ?
N1 C11 C12 C13 178.0(4) . . . . ?
C16 C11 C12 C17 174.3(5) . . . . ?
N1 C11 C12 C17 -5.0(7) . . . . ?
C11 C12 C13 C14 0.3(8) . . . . ?
C17 C12 C13 C14 -176.7(5) . . . . ?
C12 C13 C14 C15 2.6(9) . . . . ?
C13 C14 C15 C16 -3.0(9) . . . . ?
C14 C15 C16 C11 0.6(8) . . . . ?
C12 C11 C16 C15 2.4(8) . . . . ?
N1 C11 C16 C15 -178.4(5) . . . . ?
C13 C12 C17 C18 -45.0(7) . . . . ?
C11 C12 C17 C18 138.1(5) . . . . ?
C13 C12 C17 C19 80.0(7) . . . . ?
C11 C12 C17 C19 -96.9(6) . . . . ?
Cu1 Cl1 Cu2 N6 175.90(11) . . . . ?
Cu1 Cl1 Cu2 N5 90.15(12) . . . . ?
Cu1 Cl1 Cu2 Cl4 -95.40(6) . . . . ?
Cu1 Cl1 Cu2 Cl2 -2.45(7) . . . . ?
N5 Cu2 Cl2 Cu1 -96.87(11) . . . . ?
Cl4 Cu2 Cl2 Cu1 108.49(6) . . . . ?
Cl1 Cu2 Cl2 Cu1 2.08(6) . . . . ?
N2 Cu1 Cl2 Cu2 178.70(12) . . . . ?
N3 Cu1 Cl2 Cu2 -95.59(12) . . . . ?
Cl3 Cu1 Cl2 Cu2 89.73(6) . . . . ?
Cl1 Cu1 Cl2 Cu2 -2.44(7) . . . . ?
N6 Cu2 N5 C20 39.7(3) . . . . ?
Cl4 Cu2 N5 C20 -37.6(5) . . . . ?
Cl2 Cu2 N5 C20 -141.3(3) . . . . ?
Cl1 Cu2 N5 C20 130.3(3) . . . . ?
N6 Cu2 N5 C24 -141.4(4) . . . . ?
Cl4 Cu2 N5 C24 141.4(3) . . . . ?
Cl2 Cu2 N5 C24 37.7(4) . . . . ?
Cl1 Cu2 N5 C24 -50.8(4) . . . . ?
N5 Cu2 N6 C25 -49.3(4) . . . . ?
Cl4 Cu2 N6 C25 105.3(3) . . . . ?
Cl1 Cu2 N6 C25 -148.3(3) . . . . ?
N5 Cu2 N6 C29 146.5(4) . . . . ?
Cl4 Cu2 N6 C29 -58.9(4) . . . . ?
Cl1 Cu2 N6 C29 47.5(4) . . . . ?
C24 N5 C20 C21 -0.7(7) . . . . ?
Cu2 N5 C20 C21 178.2(4) . . . . ?
C24 N5 C20 N4 178.4(4) . . . . ?
Cu2 N5 C20 N4 -2.6(5) . . . . ?
C25 N4 C20 N5 -48.1(6) . . . . ?
C30 N4 C20 N5 136.1(4) . . . . ?
C25 N4 C20 C21 131.1(5) . . . . ?
C30 N4 C20 C21 -44.8(6) . . . . ?
N5 C20 C21 C22 -1.3(8) . . . . ?
N4 C20 C21 C22 179.6(5) . . . . ?
C20 C21 C22 C23 2.5(9) . . . . ?
C21 C22 C23 C24 -1.7(9) . . . . ?
C20 N5 C24 C23 1.6(7) . . . . ?
Cu2 N5 C24 C23 -177.4(4) . . . . ?
C22 C23 C24 N5 -0.4(8) . . . . ?
C29 N6 C25 C26 4.6(7) . . . . ?
Cu2 N6 C25 C26 -159.8(4) . . . . ?
C29 N6 C25 N4 -174.7(4) . . . . ?
Cu2 N6 C25 N4 20.9(6) . . . . ?
C20 N4 C25 N6 37.7(7) . . . . ?
C30 N4 C25 N6 -146.4(4) . . . . ?
C20 N4 C25 C26 -141.6(5) . . . . ?
C30 N4 C25 C26 34.3(7) . . . . ?
N6 C25 C26 C27 -2.9(8) . . . . ?
N4 C25 C26 C27 176.4(5) . . . . ?
C25 C26 C27 C28 -0.6(8) . . . . ?
C26 C27 C28 C29 2.2(8) . . . . ?
C25 N6 C29 C28 -3.0(7) . . . . ?
Cu2 N6 C29 C28 161.4(4) . . . . ?
C27 C28 C29 N6 -0.4(8) . . . . ?
C25 N4 C30 C35 -86.0(6) . . . . ?
C20 N4 C30 C35 90.0(6) . . . . ?
C25 N4 C30 C31 93.3(5) . . . . ?
C20 N4 C30 C31 -90.7(6) . . . . ?
C35 C30 C31 C32 4.4(7) . . . . ?
N4 C30 C31 C32 -174.9(4) . . . . ?
C35 C30 C31 C36 -171.9(5) . . . . ?
N4 C30 C31 C36 8.8(7) . . . . ?
C30 C31 C32 C33 -3.1(8) . . . . ?
C36 C31 C32 C33 173.1(5) . . . . ?
C31 C32 C33 C34 -0.4(9) . . . . ?
C32 C33 C34 C35 2.8(9) . . . . ?
C33 C34 C35 C30 -1.6(8) . . . . ?
C31 C30 C35 C34 -2.1(8) . . . . ?
N4 C30 C35 C34 177.1(5) . . . . ?
C30 C31 C36 C38 94.8(6) . . . . ?
C32 C31 C36 C38 -81.3(7) . . . . ?
C30 C31 C36 C37 -140.3(5) . . . . ?
C32 C31 C36 C37 43.6(7) . . . . ?
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.481
_refine_diff_density_min -0.450
_refine_diff_density_rms 0.083
data_ipr1dph
_database_code_depnum_ccdc_archive 'CCDC 735399'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
"N-(2-isopropyl)phenyl-N,N-(2,2'-dipyridyl)amine hydrogen tetrafluoroborate"
_chemical_name_common ?
_chemical_formula_moiety 'C19 H20 N3, B F4'
_chemical_formula_sum 'C19 H20 B F4 N3'
_exptl_crystal_recrystallization_method
'cooled sat. soln in iPrOH to -12 deg. C for several days'
_chemical_melting_point ?
_exptl_crystal_description block
_exptl_crystal_colour colorless
_diffrn_ambient_temperature 298(2)
_diffrn_ambient_pressure 101.33
_chemical_formula_weight 377.19
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 8.8407(18)
_cell_length_b 19.190(4)
_cell_length_c 11.776(2)
_cell_angle_alpha 90.00
_cell_angle_beta 94.00(3)
_cell_angle_gamma 90.00
_cell_volume 1993.0(7)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 1701
_cell_measurement_theta_min 2.54
_cell_measurement_theta_max 20.48
_exptl_crystal_size_max 0.54
_exptl_crystal_size_mid 0.38
_exptl_crystal_size_min 0.37
_exptl_crystal_density_diffrn 1.257
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 784
_exptl_absorpt_coefficient_mu 0.101
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9376
_exptl_absorpt_correction_T_max 0.9656
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 5093
_diffrn_reflns_av_R_equivalents 0.0000
_diffrn_reflns_av_sigmaI/netI 0.0912
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.03
_diffrn_reflns_theta_max 29.15
_reflns_number_total 5093
_reflns_number_gt 1755
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Disordered fluorine atoms F(1A)-F(4A) and F(1B)-F(4B) were refined as having
60:40 site occupancy disorder. The disorder is a C2 rotation about an axis
slightly tilted from the B(1)-F(1A) bond. The SQUEEZE function in the
program PLATON was used to refine data free of solvent accessible voids...
details are given below.
SHELXTL weighting scheme: 0.087900, 1.460200.
;
_platon_squeeze_details
;
Note: Data are Listed for all Voids in the P1 Unit Cell
i.e. Centre of Gravity, Solvent Accessible Volume,
Recovered number of Electrons in the Void and
Details about the Squeezed Material
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.136 0.359 0.554 41 1 .
2 0.364 0.859 0.946 41 1 .
3 0.636 0.141 0.054 41 1 .
4 0.864 0.641 0.446 41 1 .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0879P)^2^+1.4602P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 5093
_refine_ls_number_parameters 284
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1970
_refine_ls_R_factor_gt 0.0642
_refine_ls_wR_factor_ref 0.2095
_refine_ls_wR_factor_gt 0.1670
_refine_ls_goodness_of_fit_ref 0.716
_refine_ls_restrained_S_all 0.716
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1068(2) 0.10103(10) 0.76406(16) 0.0627(5) Uani 1 1 d . . .
N2 N 0.0906(2) -0.00477(10) 0.66334(16) 0.0657(5) Uani 1 1 d . . .
N3 N -0.1324(2) 0.07675(11) 0.67479(17) 0.0698(6) Uani 1 1 d . . .
H1 H -0.040(4) 0.0216(16) 0.649(2) 0.118(10) Uiso 1 1 d . . .
C1 C 0.1754(3) 0.04107(12) 0.72648(18) 0.0616(6) Uani 1 1 d . . .
C2 C 0.3276(3) 0.02646(14) 0.7529(2) 0.0787(7) Uani 1 1 d . . .
H2A H 0.3878 0.0571 0.7974 0.094 Uiso 1 1 calc R . .
C3 C 0.3881(3) -0.03370(15) 0.7127(3) 0.0885(8) Uani 1 1 d . . .
H3A H 0.4905 -0.0433 0.7284 0.106 Uiso 1 1 calc R . .
C4 C 0.2978(4) -0.08035(14) 0.6487(3) 0.0853(8) Uani 1 1 d . . .
H4A H 0.3377 -0.1218 0.6227 0.102 Uiso 1 1 calc R . .
C5 C 0.1509(3) -0.06404(14) 0.6254(2) 0.0775(7) Uani 1 1 d . . .
H5A H 0.0892 -0.0946 0.5818 0.093 Uiso 1 1 calc R . .
C6 C -0.0449(3) 0.12022(13) 0.73960(19) 0.0637(6) Uani 1 1 d . . .
C7 C -0.1040(3) 0.18117(14) 0.7821(2) 0.0787(7) Uani 1 1 d . . .
H7A H -0.0431 0.2111 0.8275 0.094 Uiso 1 1 calc R . .
C8 C -0.2527(3) 0.19634(18) 0.7558(3) 0.0978(9) Uani 1 1 d . . .
H8A H -0.2939 0.2369 0.7840 0.117 Uiso 1 1 calc R . .
C9 C -0.3432(4) 0.15222(19) 0.6879(3) 0.0980(9) Uani 1 1 d . . .
H9A H -0.4446 0.1627 0.6692 0.118 Uiso 1 1 calc R . .
C10 C -0.2796(3) 0.09308(17) 0.6493(2) 0.0846(8) Uani 1 1 d . . .
H10A H -0.3393 0.0628 0.6038 0.102 Uiso 1 1 calc R . .
C11 C 0.2011(3) 0.14794(12) 0.8351(2) 0.0653(6) Uani 1 1 d . . .
C12 C 0.2142(3) 0.13902(14) 0.9518(2) 0.0797(8) Uani 1 1 d . . .
C121 C 0.1291(4) 0.08309(18) 1.0116(2) 0.1007(10) Uani 1 1 d . . .
H12G H 0.0713 0.0560 0.9529 0.121 Uiso 1 1 calc R . .
C122 C 0.2356(5) 0.0331(2) 1.0776(3) 0.1498(17) Uani 1 1 d . . .
H12A H 0.1774 -0.0015 1.1141 0.225 Uiso 0.50 1 d PR A 1
H12B H 0.2966 0.0585 1.1342 0.225 Uiso 0.50 1 d PR A 1
H12C H 0.3001 0.0108 1.0263 0.225 Uiso 0.50 1 d PR A 1
H12D H 0.3387 0.0467 1.0689 0.225 Uiso 0.50 1 d PR A 2
H12E H 0.2195 -0.0133 1.0489 0.225 Uiso 0.50 1 d PR A 2
H12F H 0.2160 0.0344 1.1567 0.225 Uiso 0.50 1 d PR A 2
C123 C 0.0154(5) 0.1152(2) 1.0885(3) 0.1510(17) Uani 1 1 d . . .
H12H H -0.0372 0.0787 1.1254 0.226 Uiso 0.50 1 d PR B 1
H12I H -0.0563 0.1430 1.0435 0.226 Uiso 0.50 1 d PR B 1
H12J H 0.0682 0.1439 1.1450 0.226 Uiso 0.50 1 d PR B 1
H12K H 0.0203 0.1651 1.0839 0.226 Uiso 0.50 1 d PR B 2
H12L H 0.0395 0.1008 1.1657 0.226 Uiso 0.50 1 d PR B 2
H12M H -0.0851 0.0999 1.0643 0.226 Uiso 0.50 1 d PR B 2
C13 C 0.3100(4) 0.18500(17) 1.0147(3) 0.1025(10) Uani 1 1 d . . .
H13A H 0.3218 0.1805 1.0934 0.123 Uiso 1 1 calc R . .
C14 C 0.3867(4) 0.23655(17) 0.9623(3) 0.1039(10) Uani 1 1 d . . .
H14A H 0.4504 0.2663 1.0057 0.125 Uiso 1 1 calc R . .
C15 C 0.3704(3) 0.24467(15) 0.8469(3) 0.0943(9) Uani 1 1 d . . .
H15A H 0.4221 0.2801 0.8123 0.113 Uiso 1 1 calc R . .
C16 C 0.2771(3) 0.20032(13) 0.7816(3) 0.0795(8) Uani 1 1 d . . .
H16A H 0.2656 0.2055 0.7029 0.095 Uiso 1 1 calc R . .
B1 B -0.2803(5) -0.1250(2) 0.5590(3) 0.0834(9) Uani 1 1 d . . .
F1A F -0.3431(9) -0.1478(3) 0.6559(6) 0.176(3) Uani 0.60 1 d P C 1
F2A F -0.1977(12) -0.1647(6) 0.5243(9) 0.283(6) Uani 0.60 1 d P C 1
F3A F -0.3887(6) -0.1064(6) 0.4910(5) 0.204(4) Uani 0.60 1 d P C 1
F4A F -0.2073(10) -0.0679(5) 0.5880(10) 0.270(5) Uani 0.60 1 d P C 1
F1B F -0.2178(14) -0.1374(5) 0.6599(5) 0.176(4) Uani 0.40 1 d P C 2
F2B F -0.321(2) -0.0645(5) 0.5386(12) 0.224(7) Uani 0.40 1 d P C 2
F3B F -0.1526(7) -0.1422(6) 0.4894(6) 0.124(3) Uani 0.40 1 d P C 2
F4B F -0.3692(11) -0.1790(5) 0.5316(8) 0.188(4) Uani 0.40 1 d P C 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0598(12) 0.0671(12) 0.0611(12) -0.0054(9) 0.0025(9) -0.0007(10)
N2 0.0724(13) 0.0662(12) 0.0585(11) -0.0044(10) 0.0047(10) -0.0013(11)
N3 0.0601(12) 0.0843(14) 0.0648(12) -0.0036(11) 0.0043(10) -0.0015(11)
C1 0.0641(15) 0.0665(14) 0.0542(13) -0.0019(11) 0.0043(11) -0.0030(12)
C2 0.0695(17) 0.0783(17) 0.0863(18) -0.0081(14) -0.0083(14) 0.0044(14)
C3 0.0723(18) 0.0854(19) 0.107(2) -0.0010(17) 0.0000(16) 0.0126(15)
C4 0.090(2) 0.0715(17) 0.095(2) -0.0070(15) 0.0084(16) 0.0066(16)
C5 0.087(2) 0.0720(17) 0.0734(17) -0.0070(13) 0.0041(14) -0.0034(15)
C6 0.0605(15) 0.0764(16) 0.0550(13) 0.0004(12) 0.0090(11) -0.0022(13)
C7 0.0721(18) 0.0788(17) 0.0855(18) -0.0107(14) 0.0073(14) 0.0038(14)
C8 0.077(2) 0.104(2) 0.113(2) -0.0158(19) 0.0118(17) 0.0131(18)
C9 0.0697(18) 0.119(3) 0.105(2) -0.008(2) 0.0040(17) 0.0149(18)
C10 0.0651(17) 0.107(2) 0.0805(19) -0.0027(16) -0.0006(14) -0.0012(16)
C11 0.0629(14) 0.0648(14) 0.0684(15) -0.0094(12) 0.0057(12) -0.0076(12)
C12 0.0795(18) 0.0853(18) 0.0735(17) -0.0111(14) 0.0004(14) -0.0201(15)
C121 0.117(3) 0.119(2) 0.0647(17) 0.0056(17) -0.0054(17) -0.049(2)
C122 0.179(4) 0.141(3) 0.123(3) 0.045(3) -0.036(3) -0.051(3)
C123 0.156(4) 0.201(5) 0.101(3) -0.001(3) 0.047(3) -0.058(3)
C13 0.105(2) 0.110(2) 0.090(2) -0.0239(18) -0.0030(18) -0.032(2)
C14 0.094(2) 0.096(2) 0.121(3) -0.034(2) 0.006(2) -0.0260(18)
C15 0.084(2) 0.0734(18) 0.129(3) -0.0136(18) 0.0310(19) -0.0135(15)
C16 0.0769(17) 0.0702(16) 0.0937(19) -0.0073(14) 0.0215(15) -0.0036(14)
B1 0.087(2) 0.080(2) 0.082(2) -0.0114(19) -0.005(2) 0.006(2)
F1A 0.194(5) 0.166(5) 0.176(6) 0.063(4) 0.072(5) 0.045(4)
F2A 0.281(11) 0.259(10) 0.332(12) 0.003(8) 0.184(8) 0.118(9)
F3A 0.104(3) 0.367(12) 0.133(4) 0.048(6) -0.043(3) 0.045(6)
F4A 0.218(8) 0.219(8) 0.361(12) -0.050(8) -0.067(7) -0.104(7)
F1B 0.253(10) 0.210(8) 0.057(3) 0.006(4) -0.034(5) -0.063(8)
F2B 0.358(19) 0.087(5) 0.245(14) 0.068(6) 0.155(13) 0.118(9)
F3B 0.072(3) 0.200(7) 0.104(4) -0.015(4) 0.028(3) 0.025(3)
F4B 0.195(8) 0.193(7) 0.163(7) 0.052(6) -0.072(7) -0.105(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.388(3) . ?
N1 C6 1.401(3) . ?
N1 C11 1.452(3) . ?
N2 C5 1.345(3) . ?
N2 C1 1.346(3) . ?
N3 C6 1.340(3) . ?
N3 C10 1.351(3) . ?
C1 C2 1.388(3) . ?
C2 C3 1.371(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.386(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.346(4) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.388(3) . ?
C7 C8 1.361(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.381(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.359(4) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.382(3) . ?
C11 C16 1.385(3) . ?
C12 C13 1.399(4) . ?
C12 C121 1.512(4) . ?
C121 C122 1.519(5) . ?
C121 C123 1.529(5) . ?
C121 H12G 0.9800 . ?
C122 H12A 0.9599 . ?
C122 H12B 0.9600 . ?
C122 H12C 0.9600 . ?
C122 H12D 0.9600 . ?
C122 H12E 0.9599 . ?
C122 H12F 0.9600 . ?
C123 H12H 0.9600 . ?
C123 H12I 0.9600 . ?
C123 H12J 0.9601 . ?
C123 H12K 0.9601 . ?
C123 H12L 0.9600 . ?
C123 H12M 0.9600 . ?
C13 C14 1.370(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.365(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.381(4) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
B1 F2A 1.150(8) . ?
B1 F2B 1.232(7) . ?
B1 F3A 1.257(6) . ?
B1 F1B 1.297(7) . ?
B1 F4A 1.305(7) . ?
B1 F4B 1.326(7) . ?
B1 F1A 1.376(6) . ?
B1 F3B 1.478(8) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 125.88(19) . . ?
C1 N1 C11 116.84(19) . . ?
C6 N1 C11 117.28(19) . . ?
C5 N2 C1 121.2(2) . . ?
C6 N3 C10 119.4(2) . . ?
N2 C1 N1 118.6(2) . . ?
N2 C1 C2 119.1(2) . . ?
N1 C1 C2 122.3(2) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
N2 C5 C4 121.8(3) . . ?
N2 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
N3 C6 C7 120.9(2) . . ?
N3 C6 N1 117.4(2) . . ?
C7 C6 N1 121.7(2) . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H7A 120.7 . . ?
C6 C7 H7A 120.7 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 H9A 121.0 . . ?
C8 C9 H9A 121.0 . . ?
N3 C10 C9 122.3(3) . . ?
N3 C10 H10A 118.8 . . ?
C9 C10 H10A 118.8 . . ?
C12 C11 C16 122.2(2) . . ?
C12 C11 N1 120.1(2) . . ?
C16 C11 N1 117.7(2) . . ?
C11 C12 C13 117.0(3) . . ?
C11 C12 C121 122.8(2) . . ?
C13 C12 C121 120.3(3) . . ?
C12 C121 C122 112.0(3) . . ?
C12 C121 C123 111.0(3) . . ?
C122 C121 C123 111.2(3) . . ?
C12 C121 H12G 107.5 . . ?
C122 C121 H12G 107.5 . . ?
C123 C121 H12G 107.5 . . ?
C121 C122 H12A 109.5 . . ?
C121 C122 H12B 109.5 . . ?
H12A C122 H12B 109.5 . . ?
C121 C122 H12C 109.5 . . ?
H12A C122 H12C 109.5 . . ?
H12B C122 H12C 109.5 . . ?
C121 C122 H12D 109.5 . . ?
H12A C122 H12D 141.1 . . ?
H12B C122 H12D 56.2 . . ?
H12C C122 H12D 56.3 . . ?
C121 C122 H12E 109.5 . . ?
H12A C122 H12E 56.3 . . ?
H12B C122 H12E 141.1 . . ?
H12C C122 H12E 56.3 . . ?
H12D C122 H12E 109.5 . . ?
C121 C122 H12F 109.5 . . ?
H12A C122 H12F 56.3 . . ?
H12B C122 H12F 56.3 . . ?
H12C C122 H12F 141.1 . . ?
H12D C122 H12F 109.5 . . ?
H12E C122 H12F 109.5 . . ?
C121 C123 H12H 109.5 . . ?
C121 C123 H12I 109.5 . . ?
H12H C123 H12I 109.5 . . ?
C121 C123 H12J 109.5 . . ?
H12H C123 H12J 109.5 . . ?
H12I C123 H12J 109.5 . . ?
C121 C123 H12K 109.5 . . ?
H12H C123 H12K 141.1 . . ?
H12I C123 H12K 56.2 . . ?
H12J C123 H12K 56.2 . . ?
C121 C123 H12L 109.5 . . ?
H12H C123 H12L 56.3 . . ?
H12I C123 H12L 141.1 . . ?
H12J C123 H12L 56.3 . . ?
H12K C123 H12L 109.5 . . ?
C121 C123 H12M 109.5 . . ?
H12H C123 H12M 56.3 . . ?
H12I C123 H12M 56.3 . . ?
H12J C123 H12M 141.1 . . ?
H12K C123 H12M 109.5 . . ?
H12L C123 H12M 109.5 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 118.9(3) . . ?
C15 C16 H16A 120.6 . . ?
C11 C16 H16A 120.6 . . ?
F2A B1 F3A 115.9(8) . . ?
F2B B1 F1B 116.8(9) . . ?
F2A B1 F4A 109.6(8) . . ?
F3A B1 F4A 105.6(6) . . ?
F2B B1 F4B 121.9(10) . . ?
F1B B1 F4B 106.6(6) . . ?
F2A B1 F1A 112.8(6) . . ?
F3A B1 F1A 106.5(5) . . ?
F4A B1 F1A 105.7(7) . . ?
F2B B1 F3B 109.0(7) . . ?
F1B B1 F3B 100.0(7) . . ?
F4B B1 F3B 98.8(7) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C1 N1 -179.4(2) . . . . ?
C5 N2 C1 C2 -0.2(3) . . . . ?
C6 N1 C1 N2 -2.0(3) . . . . ?
C11 N1 C1 N2 177.98(19) . . . . ?
C6 N1 C1 C2 178.8(2) . . . . ?
C11 N1 C1 C2 -1.2(3) . . . . ?
N2 C1 C2 C3 1.0(4) . . . . ?
N1 C1 C2 C3 -179.8(2) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C1 N2 C5 C4 0.1(4) . . . . ?
C3 C4 C5 N2 -0.8(4) . . . . ?
C10 N3 C6 C7 0.9(4) . . . . ?
C10 N3 C6 N1 179.8(2) . . . . ?
C1 N1 C6 N3 0.5(3) . . . . ?
C11 N1 C6 N3 -179.5(2) . . . . ?
C1 N1 C6 C7 179.4(2) . . . . ?
C11 N1 C6 C7 -0.6(3) . . . . ?
N3 C6 C7 C8 -0.5(4) . . . . ?
N1 C6 C7 C8 -179.4(2) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C6 N3 C10 C9 -0.5(4) . . . . ?
C8 C9 C10 N3 -0.3(5) . . . . ?
C1 N1 C11 C12 -88.5(3) . . . . ?
C6 N1 C11 C12 91.5(3) . . . . ?
C1 N1 C11 C16 90.7(3) . . . . ?
C6 N1 C11 C16 -89.3(3) . . . . ?
C16 C11 C12 C13 -0.8(4) . . . . ?
N1 C11 C12 C13 178.4(2) . . . . ?
C16 C11 C12 C121 178.6(3) . . . . ?
N1 C11 C12 C121 -2.2(4) . . . . ?
C11 C12 C121 C122 120.0(3) . . . . ?
C13 C12 C121 C122 -60.6(4) . . . . ?
C11 C12 C121 C123 -115.0(3) . . . . ?
C13 C12 C121 C123 64.3(4) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C121 C12 C13 C14 -179.2(3) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C11 0.1(4) . . . . ?
C12 C11 C16 C15 0.7(4) . . . . ?
N1 C11 C16 C15 -178.5(2) . . . . ?
N2 C1 C6 N3 -1.33(18) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1 F4A 1.26(3) 2.34(3) 2.977(7) 107.4(18) .
N3 H1 F4A 1.38(3) 2.34(3) 3.015(8) 105.1(17) .
N2 H1 N3 1.26(3) 1.38(3) 2.528(3) 146(2) .
_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.263
_refine_diff_density_min -0.173
_refine_diff_density_rms 0.041
data_ipr1sty
_database_code_depnum_ccdc_archive 'CCDC 740151'
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_formula_moiety 'C27 H27 B Cu F4 N3'
_chemical_formula_sum 'C27 H27 B Cu F4 N3'
_chemical_properties_physical air-sensitive
_exptl_crystal_recrystallization_method
'cooled sat. soln in iPrOH to -12 deg. C for several days'
_chemical_melting_point ?
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_diffrn_ambient_temperature 298(2)
_diffrn_ambient_pressure 101.33
_chemical_formula_weight 543.87
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 14.162(3)
_cell_length_b 14.028(3)
_cell_length_c 14.353(3)
_cell_angle_alpha 90.00
_cell_angle_beta 110.06(3)
_cell_angle_gamma 90.00
_cell_volume 2678.4(11)
_cell_formula_units_Z 4
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 2518
_cell_measurement_theta_min 2.27
_cell_measurement_theta_max 17.35
_exptl_crystal_size_max 0.58
_exptl_crystal_size_mid 0.48
_exptl_crystal_size_min 0.15
_exptl_crystal_density_diffrn 1.349
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1120
_exptl_absorpt_coefficient_mu 0.863
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6345
_exptl_absorpt_correction_T_max 0.8815
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 34735
_diffrn_reflns_av_R_equivalents 0.1051
_diffrn_reflns_av_sigmaI/netI 0.1358
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 1.53
_diffrn_reflns_theta_max 29.10
_reflns_number_total 6707
_reflns_number_gt 2459
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Disordered fluorine atoms F(2A)-F(4A) and F(2B)-F(4B) were refined as having
50:50 site occupancy disorder. The disorder is a C2 rotation about the axis
of the B(1)-F(1) bond. The SQUEEZE function in the program PLATON was used
to refine data free of solvent accessible voids... details are given below.
SHELXTL weighting scheme: 0.0846, 0.
;
_platon_squeeze_details
;
Note: Data are Listed for all Voids in the P1 Unit Cell
i.e. Centre of Gravity, Solvent Accessible Volume,
Recovered number of Electrons in the Void and
Details about the Squeezed Material
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.743 0.132 0.687 8 1 ' '
2 0.403 0.250 0.319 7 1 ' '
3 0.403 0.250 0.819 7 1 ' '
4 0.743 0.368 0.187 8 1 ' '
5 0.257 0.632 0.812 8 1 ' '
6 0.597 0.750 0.181 7 1 ' '
7 0.597 0.750 0.681 7 1 ' '
8 0.257 0.868 0.312 8 1 ' '
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0846P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 6707
_refine_ls_number_parameters 354
_refine_ls_number_restraints 66
_refine_ls_R_factor_all 0.2029
_refine_ls_R_factor_gt 0.0678
_refine_ls_wR_factor_ref 0.1965
_refine_ls_wR_factor_gt 0.1577
_refine_ls_goodness_of_fit_ref 0.927
_refine_ls_restrained_S_all 0.954
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.27123(4) -0.44690(4) 0.47378(4) 0.0698(3) Uani 1 1 d . . .
N1 N -0.1450(2) -0.6321(2) 0.5318(2) 0.0593(9) Uani 1 1 d . . .
N2 N -0.2119(3) -0.5099(3) 0.6028(2) 0.0653(10) Uani 1 1 d . . .
N3 N -0.1682(3) -0.4999(3) 0.4241(3) 0.0606(9) Uani 1 1 d . . .
C1 C -0.1618(3) -0.5915(3) 0.6142(3) 0.0571(11) Uani 1 1 d . . .
C2 C -0.1287(4) -0.6371(3) 0.7049(4) 0.0774(13) Uani 1 1 d . . .
H2A H -0.0959 -0.6954 0.7114 0.093 Uiso 1 1 calc R . .
C3 C -0.1441(4) -0.5963(4) 0.7857(3) 0.0842(15) Uani 1 1 d . . .
H3A H -0.1207 -0.6264 0.8471 0.101 Uiso 1 1 calc R . .
C4 C -0.1934(4) -0.5123(4) 0.7754(4) 0.0863(15) Uani 1 1 d . . .
H4A H -0.2049 -0.4839 0.8291 0.104 Uiso 1 1 calc R . .
C5 C -0.2259(4) -0.4699(3) 0.6836(4) 0.0793(14) Uani 1 1 d . . .
H5A H -0.2588 -0.4116 0.6763 0.095 Uiso 1 1 calc R . .
C6 C -0.1264(3) -0.5851(3) 0.4534(3) 0.0562(10) Uani 1 1 d . . .
C7 C -0.0641(3) -0.6253(3) 0.4077(3) 0.0696(12) Uani 1 1 d . . .
H7A H -0.0346 -0.6843 0.4285 0.083 Uiso 1 1 calc R . .
C8 C -0.0461(4) -0.5782(4) 0.3318(4) 0.0771(14) Uani 1 1 d . . .
H8A H -0.0052 -0.6056 0.3005 0.092 Uiso 1 1 calc R . .
C9 C -0.0881(4) -0.4915(4) 0.3024(3) 0.0756(13) Uani 1 1 d . . .
H9A H -0.0764 -0.4582 0.2513 0.091 Uiso 1 1 calc R . .
C10 C -0.1478(4) -0.4550(3) 0.3501(3) 0.0718(13) Uani 1 1 d . . .
H10A H -0.1764 -0.3954 0.3305 0.086 Uiso 1 1 calc R . .
C11 C -0.1404(4) -0.7360(3) 0.5318(3) 0.0659(12) Uani 1 1 d . . .
C12 C -0.2259(5) -0.7862(4) 0.4918(4) 0.0756(14) Uani 1 1 d . . .
C121 C -0.3244(5) -0.7386(5) 0.4357(6) 0.116(2) Uani 1 1 d . . .
H12A H -0.3102 -0.6700 0.4422 0.139 Uiso 1 1 calc R . .
C122 C -0.3576(6) -0.7588(7) 0.3255(6) 0.202(5) Uani 1 1 d . . .
H12B H -0.3079 -0.7355 0.2996 0.303 Uiso 1 1 calc R . .
H12C H -0.4206 -0.7275 0.2924 0.303 Uiso 1 1 calc R . .
H12D H -0.3656 -0.8263 0.3145 0.303 Uiso 1 1 calc R . .
C123 C -0.4028(8) -0.7540(8) 0.4806(10) 0.264(6) Uani 1 1 d . . .
H12E H -0.3721 -0.7574 0.5514 0.396 Uiso 1 1 calc R . .
H12F H -0.4375 -0.8126 0.4562 0.396 Uiso 1 1 calc R . .
H12G H -0.4497 -0.7020 0.4633 0.396 Uiso 1 1 calc R . .
C13 C -0.2217(7) -0.8840(5) 0.4970(5) 0.116(2) Uani 1 1 d . . .
H13A H -0.2803 -0.9195 0.4707 0.139 Uiso 1 1 calc R . .
C14 C -0.1307(10) -0.9300(5) 0.5414(6) 0.139(4) Uani 1 1 d . . .
H14A H -0.1287 -0.9962 0.5452 0.167 Uiso 1 1 calc R . .
C15 C -0.0458(7) -0.8798(6) 0.5787(5) 0.127(3) Uani 1 1 d . . .
H15A H 0.0153 -0.9112 0.6064 0.152 Uiso 1 1 calc R . .
C16 C -0.0487(5) -0.7808(4) 0.5759(4) 0.0934(16) Uani 1 1 d . . .
H16A H 0.0098 -0.7454 0.6032 0.112 Uiso 1 1 calc R . .
C17 C -0.4004(4) -0.3816(4) 0.4582(4) 0.0997(18) Uani 1 1 d . . .
H17A H -0.4540 -0.4211 0.4646 0.120 Uiso 1 1 calc R . .
H17B H -0.3957 -0.3197 0.4896 0.120 Uiso 1 1 calc R . .
C18 C -0.3867(4) -0.3834(4) 0.3660(5) 0.0875(16) Uani 1 1 d . . .
H18A H -0.3704 -0.3216 0.3434 0.105 Uiso 1 1 calc R . .
C19 C -0.4347(4) -0.4519(4) 0.2865(4) 0.0876(16) Uani 1 1 d . . .
C20 C -0.4033(5) -0.4562(5) 0.2042(5) 0.116(2) Uani 1 1 d . . .
H20A H -0.3533 -0.4151 0.2002 0.139 Uiso 1 1 calc R . .
C21 C -0.4454(7) -0.5205(7) 0.1297(5) 0.149(3) Uani 1 1 d . . .
H21A H -0.4192 -0.5272 0.0788 0.178 Uiso 1 1 calc R . .
C22 C -0.5242(7) -0.5738(7) 0.1295(7) 0.147(3) Uani 1 1 d . . .
H22A H -0.5566 -0.6136 0.0763 0.176 Uiso 1 1 calc R . .
C23 C -0.5553(6) -0.5684(6) 0.2081(8) 0.135(3) Uani 1 1 d . . .
H23A H -0.6086 -0.6064 0.2094 0.162 Uiso 1 1 calc R . .
C24 C -0.5110(5) -0.5091(5) 0.2856(5) 0.1095(19) Uani 1 1 d . . .
H24A H -0.5339 -0.5082 0.3391 0.131 Uiso 1 1 calc R . .
B1 B -0.1735(6) -0.2108(5) 0.5732(7) 0.128(3) Uani 1 1 d D . .
F1 F -0.1717(3) -0.2958(3) 0.5352(4) 0.1680(19) Uani 1 1 d D A .
F2A F -0.2106(11) -0.1623(12) 0.4836(9) 0.226(7) Uani 0.50 1 d PDU A 1
F3A F -0.2449(11) -0.2092(11) 0.6112(13) 0.213(7) Uani 0.50 1 d PDU A 1
F4A F -0.0897(9) -0.1783(14) 0.6267(12) 0.199(10) Uani 0.50 1 d PDU A 1
F2B F -0.1572(16) -0.2535(12) 0.6672(11) 0.280(8) Uani 0.50 1 d PDU A 2
F3B F -0.2479(10) -0.1536(11) 0.5585(18) 0.231(10) Uani 0.50 1 d PDU A 2
F4B F -0.0871(8) -0.1634(9) 0.5940(13) 0.141(6) Uani 0.50 1 d PDU A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0709(4) 0.0674(4) 0.0719(4) 0.0035(3) 0.0254(3) 0.0104(3)
N1 0.072(2) 0.052(2) 0.054(2) -0.0015(18) 0.0222(18) 0.0013(17)
N2 0.083(3) 0.061(2) 0.056(2) -0.0048(19) 0.029(2) 0.008(2)
N3 0.068(2) 0.057(2) 0.063(2) 0.0055(19) 0.0290(18) -0.0005(19)
C1 0.059(3) 0.056(3) 0.055(3) -0.002(2) 0.018(2) -0.005(2)
C2 0.096(4) 0.073(3) 0.069(3) 0.009(3) 0.036(3) 0.012(3)
C3 0.103(4) 0.096(4) 0.057(3) 0.006(3) 0.033(3) 0.003(3)
C4 0.116(4) 0.086(4) 0.066(4) -0.010(3) 0.044(3) 0.002(3)
C5 0.090(4) 0.073(3) 0.083(4) -0.004(3) 0.040(3) 0.011(3)
C6 0.060(3) 0.054(3) 0.055(3) 0.001(2) 0.020(2) -0.005(2)
C7 0.074(3) 0.068(3) 0.074(3) 0.004(3) 0.034(3) 0.009(2)
C8 0.081(3) 0.088(4) 0.072(3) 0.006(3) 0.039(3) 0.004(3)
C9 0.082(3) 0.089(4) 0.064(3) 0.013(3) 0.034(3) -0.008(3)
C10 0.075(3) 0.067(3) 0.070(3) 0.009(3) 0.019(3) 0.002(2)
C11 0.090(4) 0.055(3) 0.059(3) 0.006(2) 0.033(3) 0.006(3)
C12 0.103(4) 0.053(3) 0.088(4) -0.010(3) 0.055(3) -0.004(3)
C121 0.092(4) 0.105(5) 0.167(6) -0.056(5) 0.066(5) -0.032(4)
C122 0.148(7) 0.221(10) 0.181(9) -0.077(7) -0.016(6) 0.066(7)
C123 0.212(10) 0.243(12) 0.434(19) 0.033(12) 0.234(13) 0.022(10)
C13 0.189(7) 0.075(5) 0.121(6) -0.010(4) 0.102(6) -0.014(5)
C14 0.311(15) 0.053(4) 0.088(5) 0.007(4) 0.114(8) -0.002(6)
C15 0.213(9) 0.096(6) 0.079(4) 0.029(4) 0.059(5) 0.085(6)
C16 0.122(5) 0.086(4) 0.069(3) 0.013(3) 0.030(3) 0.025(4)
C17 0.075(4) 0.103(5) 0.122(5) -0.007(4) 0.035(3) 0.023(3)
C18 0.071(3) 0.079(4) 0.109(4) 0.023(3) 0.026(3) 0.031(3)
C19 0.066(4) 0.103(4) 0.083(4) 0.009(4) 0.012(3) 0.017(3)
C20 0.087(4) 0.166(7) 0.084(4) 0.014(5) 0.014(4) 0.008(4)
C21 0.110(6) 0.224(9) 0.088(5) -0.032(6) 0.004(5) 0.018(6)
C22 0.110(7) 0.176(8) 0.125(7) -0.038(6) 0.002(6) 0.013(6)
C23 0.096(5) 0.146(7) 0.156(7) -0.010(6) 0.035(6) 0.006(5)
C24 0.099(5) 0.114(5) 0.108(5) -0.010(4) 0.026(4) 0.006(4)
B1 0.145(9) 0.065(6) 0.184(11) 0.009(6) 0.071(9) 0.010(6)
F1 0.132(3) 0.093(3) 0.269(6) -0.069(3) 0.056(3) -0.013(2)
F2A 0.169(12) 0.216(14) 0.232(14) 0.074(12) -0.010(10) -0.019(10)
F3A 0.196(13) 0.177(15) 0.31(2) -0.074(14) 0.146(14) 0.054(10)
F4A 0.128(11) 0.208(18) 0.195(15) -0.091(13) -0.027(9) -0.043(10)
F2B 0.39(2) 0.206(15) 0.299(19) 0.011(13) 0.187(19) -0.052(17)
F3B 0.148(10) 0.134(11) 0.38(3) 0.002(13) 0.048(12) 0.083(9)
F4B 0.151(11) 0.062(5) 0.235(14) -0.015(7) 0.099(11) -0.029(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.961(4) . ?
Cu1 N3 1.976(3) . ?
Cu1 C17 1.988(5) . ?
Cu1 C18 2.031(5) . ?
N1 C1 1.404(5) . ?
N1 C6 1.405(5) . ?
N1 C11 1.459(6) . ?
N2 C1 1.327(5) . ?
N2 C5 1.363(5) . ?
N3 C6 1.335(5) . ?
N3 C10 1.349(5) . ?
C1 C2 1.380(6) . ?
C2 C3 1.375(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.352(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.373(6) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.387(5) . ?
C7 C8 1.370(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.356(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.357(6) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.348(7) . ?
C11 C16 1.385(7) . ?
C12 C13 1.374(8) . ?
C12 C121 1.506(8) . ?
C121 C123 1.478(9) . ?
C121 C122 1.516(9) . ?
C121 H12A 0.9800 . ?
C122 H12B 0.9600 . ?
C122 H12C 0.9600 . ?
C122 H12D 0.9600 . ?
C123 H12E 0.9600 . ?
C123 H12F 0.9600 . ?
C123 H12G 0.9600 . ?
C13 C14 1.386(11) . ?
C13 H13A 0.9300 . ?
C14 C15 1.337(10) . ?
C14 H14A 0.9300 . ?
C15 C16 1.389(9) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.402(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.468(8) . ?
C18 H18A 0.9800 . ?
C19 C24 1.342(8) . ?
C19 C20 1.399(8) . ?
C20 C21 1.370(9) . ?
C20 H20A 0.9300 . ?
C21 C22 1.344(11) . ?
C21 H21A 0.9300 . ?
C22 C23 1.346(10) . ?
C22 H22A 0.9300 . ?
C23 C24 1.358(9) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
B1 F4A 1.257(11) . ?
B1 F3B 1.283(10) . ?
B1 F3A 1.303(10) . ?
B1 F1 1.316(8) . ?
B1 F4B 1.332(11) . ?
B1 F2A 1.390(11) . ?
B1 F2B 1.420(12) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N3 92.31(15) . . ?
N2 Cu1 C17 113.2(2) . . ?
N3 Cu1 C17 153.8(2) . . ?
N2 Cu1 C18 152.8(2) . . ?
N3 Cu1 C18 113.0(2) . . ?
C17 Cu1 C18 40.81(19) . . ?
C1 N1 C6 128.1(3) . . ?
C1 N1 C11 115.2(3) . . ?
C6 N1 C11 116.6(3) . . ?
C1 N2 C5 118.5(4) . . ?
C1 N2 Cu1 122.9(3) . . ?
C5 N2 Cu1 118.5(3) . . ?
C6 N3 C10 118.3(4) . . ?
C6 N3 Cu1 121.7(3) . . ?
C10 N3 Cu1 119.5(3) . . ?
N2 C1 C2 120.7(4) . . ?
N2 C1 N1 118.9(4) . . ?
C2 C1 N1 120.4(4) . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 H4A 120.9 . . ?
N2 C5 C4 122.7(5) . . ?
N2 C5 H5A 118.6 . . ?
C4 C5 H5A 118.6 . . ?
N3 C6 C7 120.0(4) . . ?
N3 C6 N1 119.2(4) . . ?
C7 C6 N1 120.8(4) . . ?
C8 C7 C6 120.1(4) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C10 117.6(4) . . ?
C8 C9 H9A 121.2 . . ?
C10 C9 H9A 121.2 . . ?
N3 C10 C9 124.0(4) . . ?
N3 C10 H10A 118.0 . . ?
C9 C10 H10A 118.0 . . ?
C12 C11 C16 121.5(5) . . ?
C12 C11 N1 119.2(4) . . ?
C16 C11 N1 119.2(5) . . ?
C11 C12 C13 118.9(6) . . ?
C11 C12 C121 121.9(5) . . ?
C13 C12 C121 119.1(6) . . ?
C123 C121 C12 113.5(7) . . ?
C123 C121 C122 114.6(8) . . ?
C12 C121 C122 111.9(5) . . ?
C123 C121 H12A 105.2 . . ?
C12 C121 H12A 105.2 . . ?
C122 C121 H12A 105.2 . . ?
C121 C122 H12B 109.5 . . ?
C121 C122 H12C 109.5 . . ?
H12B C122 H12C 109.5 . . ?
C121 C122 H12D 109.5 . . ?
H12B C122 H12D 109.5 . . ?
H12C C122 H12D 109.5 . . ?
C121 C123 H12E 109.5 . . ?
C121 C123 H12F 109.5 . . ?
H12E C123 H12F 109.5 . . ?
C121 C123 H12G 109.5 . . ?
H12E C123 H12G 109.5 . . ?
H12F C123 H12G 109.5 . . ?
C12 C13 C14 120.4(8) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C15 C14 C13 120.4(7) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 120.0(8) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C11 C16 C15 118.8(6) . . ?
C11 C16 H16A 120.6 . . ?
C15 C16 H16A 120.6 . . ?
C18 C17 Cu1 71.2(3) . . ?
C18 C17 H17A 116.5 . . ?
Cu1 C17 H17A 116.5 . . ?
C18 C17 H17B 116.5 . . ?
Cu1 C17 H17B 116.5 . . ?
H17A C17 H17B 113.5 . . ?
C17 C18 C19 124.6(6) . . ?
C17 C18 Cu1 68.0(3) . . ?
C19 C18 Cu1 110.0(3) . . ?
C17 C18 H18A 114.9 . . ?
C19 C18 H18A 114.9 . . ?
Cu1 C18 H18A 114.9 . . ?
C24 C19 C20 117.0(6) . . ?
C24 C19 C18 123.8(6) . . ?
C20 C19 C18 119.1(6) . . ?
C21 C20 C19 120.6(7) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C22 C21 C20 120.5(8) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C21 C22 C23 118.5(8) . . ?
C21 C22 H22A 120.7 . . ?
C23 C22 H22A 120.7 . . ?
C22 C23 C24 121.9(8) . . ?
C22 C23 H23A 119.0 . . ?
C24 C23 H23A 119.0 . . ?
C19 C24 C23 121.3(7) . . ?
C19 C24 H24A 119.4 . . ?
C23 C24 H24A 119.4 . . ?
F4A B1 F3A 116.4(11) . . ?
F4A B1 F1 115.7(11) . . ?
F3B B1 F1 129.0(12) . . ?
F3A B1 F1 108.5(8) . . ?
F3B B1 F4B 111.3(10) . . ?
F1 B1 F4B 113.5(9) . . ?
F4A B1 F2A 111.5(11) . . ?
F3A B1 F2A 106.1(10) . . ?
F1 B1 F2A 96.5(11) . . ?
F3B B1 F2B 106.1(12) . . ?
F1 B1 F2B 89.6(9) . . ?
F4B B1 F2B 99.2(10) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cu1 N2 C1 -29.3(4) . . . . ?
C17 Cu1 N2 C1 144.7(4) . . . . ?
C18 Cu1 N2 C1 129.8(5) . . . . ?
N3 Cu1 N2 C5 153.2(4) . . . . ?
C17 Cu1 N2 C5 -32.9(4) . . . . ?
C18 Cu1 N2 C5 -47.7(6) . . . . ?
N2 Cu1 N3 C6 31.9(3) . . . . ?
C17 Cu1 N3 C6 -135.4(5) . . . . ?
C18 Cu1 N3 C6 -137.8(3) . . . . ?
N2 Cu1 N3 C10 -156.2(3) . . . . ?
C17 Cu1 N3 C10 36.5(6) . . . . ?
C18 Cu1 N3 C10 34.0(4) . . . . ?
C5 N2 C1 C2 3.0(6) . . . . ?
Cu1 N2 C1 C2 -174.6(3) . . . . ?
C5 N2 C1 N1 -178.5(4) . . . . ?
Cu1 N2 C1 N1 4.0(5) . . . . ?
C6 N1 C1 N2 35.1(6) . . . . ?
C11 N1 C1 N2 -148.9(4) . . . . ?
C6 N1 C1 C2 -146.3(4) . . . . ?
C11 N1 C1 C2 29.7(6) . . . . ?
N2 C1 C2 C3 -2.4(7) . . . . ?
N1 C1 C2 C3 179.0(4) . . . . ?
C1 C2 C3 C4 1.2(8) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C1 N2 C5 C4 -2.3(7) . . . . ?
Cu1 N2 C5 C4 175.3(4) . . . . ?
C3 C4 C5 N2 1.1(8) . . . . ?
C10 N3 C6 C7 -0.2(6) . . . . ?
Cu1 N3 C6 C7 171.8(3) . . . . ?
C10 N3 C6 N1 178.6(4) . . . . ?
Cu1 N3 C6 N1 -9.5(5) . . . . ?
C1 N1 C6 N3 -31.9(6) . . . . ?
C11 N1 C6 N3 152.2(4) . . . . ?
C1 N1 C6 C7 146.9(4) . . . . ?
C11 N1 C6 C7 -29.1(6) . . . . ?
N3 C6 C7 C8 -0.7(6) . . . . ?
N1 C6 C7 C8 -179.4(4) . . . . ?
C6 C7 C8 C9 1.0(7) . . . . ?
C7 C8 C9 C10 -0.4(7) . . . . ?
C6 N3 C10 C9 0.8(7) . . . . ?
Cu1 N3 C10 C9 -171.4(4) . . . . ?
C8 C9 C10 N3 -0.4(8) . . . . ?
C1 N1 C11 C12 88.2(5) . . . . ?
C6 N1 C11 C12 -95.3(5) . . . . ?
C1 N1 C11 C16 -89.6(5) . . . . ?
C6 N1 C11 C16 86.9(5) . . . . ?
C16 C11 C12 C13 1.4(7) . . . . ?
N1 C11 C12 C13 -176.3(4) . . . . ?
C16 C11 C12 C121 -174.5(5) . . . . ?
N1 C11 C12 C121 7.8(7) . . . . ?
C11 C12 C121 C123 -119.2(7) . . . . ?
C13 C12 C121 C123 64.9(9) . . . . ?
C11 C12 C121 C122 109.1(7) . . . . ?
C13 C12 C121 C122 -66.8(8) . . . . ?
C11 C12 C13 C14 -1.0(8) . . . . ?
C121 C12 C13 C14 175.0(6) . . . . ?
C12 C13 C14 C15 -0.7(10) . . . . ?
C13 C14 C15 C16 2.0(11) . . . . ?
C12 C11 C16 C15 0.0(7) . . . . ?
N1 C11 C16 C15 177.6(4) . . . . ?
C14 C15 C16 C11 -1.7(9) . . . . ?
N2 Cu1 C17 C18 -169.6(3) . . . . ?
N3 Cu1 C17 C18 -3.5(7) . . . . ?
Cu1 C17 C18 C19 99.8(5) . . . . ?
N2 Cu1 C18 C17 21.2(7) . . . . ?
N3 Cu1 C18 C17 178.3(3) . . . . ?
N2 Cu1 C18 C19 -99.1(6) . . . . ?
N3 Cu1 C18 C19 58.0(4) . . . . ?
C17 Cu1 C18 C19 -120.3(6) . . . . ?
C17 C18 C19 C24 12.7(8) . . . . ?
Cu1 C18 C19 C24 89.2(6) . . . . ?
C17 C18 C19 C20 -170.0(5) . . . . ?
Cu1 C18 C19 C20 -93.6(5) . . . . ?
C24 C19 C20 C21 -3.7(9) . . . . ?
C18 C19 C20 C21 178.8(6) . . . . ?
C19 C20 C21 C22 6.6(12) . . . . ?
C20 C21 C22 C23 -5.5(13) . . . . ?
C21 C22 C23 C24 1.7(13) . . . . ?
C20 C19 C24 C23 0.0(9) . . . . ?
C18 C19 C24 C23 177.3(5) . . . . ?
C22 C23 C24 C19 1.0(11) . . . . ?
N3 N2 C17 C18 5.8(4) . . . . ?
N2 C1 C6 N3 2.8(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.932
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.665
_refine_diff_density_min -0.237
_refine_diff_density_rms 0.061
data_ndpasty
_database_code_depnum_ccdc_archive 'CCDC 743482'
_publ_section_references
;
Bruker AXS. SMARTv5.050; Bruker Molecular Analysis Research Tool, Bruker
AXS Inc., Madison, WI, 1999b.
Bruker AXS. SAINTv6.06. Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI, 1999a.
Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections.
Bruker AXSInc., Madison, WI, based onmethod described in: Blessing, R. H.
ActaCrystallogr. 1995, A51, 33--38.
Bruker. SHELXTLv 5.10; The Complete Software Package for Single Crystal
StructureDetermination. Bruker AXS Inc., Madison, WI, 1997.
;
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_formula_moiety 'C28 H23 Cu N3, B F4'
_chemical_formula_sum 'C28 H23 B Cu F4 N3'
_chemical_properties_physical air-sensitive
_exptl_crystal_recrystallization_method
'cooled soln. in MeOH to -12 deg. C for several days'
_chemical_melting_point ?
_exptl_crystal_description prism
_exptl_crystal_colour colorless
_diffrn_ambient_temperature 298(2)
_diffrn_ambient_pressure 101.33
_chemical_formula_weight 551.84
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_int_tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 25.745(5)
_cell_length_b 13.345(3)
_cell_length_c 15.876(3)
_cell_angle_alpha 90.00
_cell_angle_beta 102.30(3)
_cell_angle_gamma 90.00
_cell_volume 5329.3(19)
_cell_formula_units_Z 8
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used 8013
_cell_measurement_theta_min 2.22
_cell_measurement_theta_max 20.52
_exptl_crystal_size_max 0.55
_exptl_crystal_size_mid 0.45
_exptl_crystal_size_min 0.35
_exptl_crystal_density_diffrn 1.376
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2256
_exptl_absorpt_coefficient_mu 0.869
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.498
_exptl_absorpt_correction_T_max 0.746
_exptl_absorpt_process_details 'SADABS (Bruker-AXS, 2003)'
_exptl_special_details
;
?
;
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_type 'Bruker SMART CCD'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_diffrn_reflns_number 65597
_diffrn_reflns_av_R_equivalents 0.0792
_diffrn_reflns_av_sigmaI/netI 0.1004
_diffrn_reflns_limit_h_min -33
_diffrn_reflns_limit_h_max 33
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_theta_min 1.62
_diffrn_reflns_theta_max 27.77
_reflns_number_total 12485
_reflns_number_gt 5082
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)'
_computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)'
_computing_structure_refinement 'SHELXTL v5.1'
_computing_molecular_graphics 'SHELXTL v5.1'
_computing_publication_material 'SHELXTL v5.1'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The SQUEEZE function in the program PLATON was used to refine data free of
solvent accessible voids... details of which are given below.
SHELXTL weighting scheme: 0.0956, 0.
;
_platon_squeeze_details
;
Note: Data are Listed for all Voids in the P1 Unit Cell
i.e. Centre of Gravity, Solvent Accessible Volume,
Recovered number of Electrons in the Void and
Details about the Squeezed Material
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.315 0.223 0.108 84 20 ' '
2 0.182 0.166 0.822 11 0 ' '
3 0.315 0.277 0.608 84 20 ' '
4 0.182 0.334 0.322 11 0 ' '
5 0.685 0.723 0.392 84 19 ' '
6 0.818 0.666 0.678 11 0 ' '
7 0.685 0.777 0.892 84 19 ' '
8 0.818 0.834 0.178 11 0 ' '
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0956P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_number_reflns 12485
_refine_ls_number_parameters 667
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1416
_refine_ls_R_factor_gt 0.0602
_refine_ls_wR_factor_ref 0.1910
_refine_ls_wR_factor_gt 0.1657
_refine_ls_goodness_of_fit_ref 0.928
_refine_ls_restrained_S_all 0.928
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.488314(18) 0.47382(4) 0.19240(3) 0.06797(19) Uani 1 1 d . . .
N1 N 0.39249(11) 0.5440(2) 0.27487(19) 0.0566(8) Uani 1 1 d . . .
N2 N 0.41326(12) 0.4945(3) 0.1415(2) 0.0691(9) Uani 1 1 d . . .
N3 N 0.48666(12) 0.5560(2) 0.2947(2) 0.0624(8) Uani 1 1 d . . .
C1 C 0.37768(14) 0.5304(3) 0.1845(2) 0.0592(9) Uani 1 1 d . . .
C2 C 0.32581(16) 0.5501(3) 0.1419(3) 0.0761(12) Uani 1 1 d . . .
H2A H 0.3015 0.5750 0.1723 0.091 Uiso 1 1 calc R . .
C3 C 0.31063(17) 0.5333(4) 0.0564(3) 0.0905(15) Uani 1 1 d . . .
H3A H 0.2756 0.5456 0.0284 0.109 Uiso 1 1 calc R . .
C4 C 0.3460(2) 0.4985(4) 0.0107(3) 0.1009(16) Uani 1 1 d . . .
H4A H 0.3361 0.4884 -0.0485 0.121 Uiso 1 1 calc R . .
C5 C 0.39713(18) 0.4788(4) 0.0558(3) 0.0921(15) Uani 1 1 d . . .
H5A H 0.4216 0.4535 0.0257 0.111 Uiso 1 1 calc R . .
C6 C 0.44294(14) 0.5660(3) 0.3263(2) 0.0544(9) Uani 1 1 d . . .
C7 C 0.44673(16) 0.5973(3) 0.4112(3) 0.0677(10) Uani 1 1 d . . .
H7A H 0.4162 0.6011 0.4334 0.081 Uiso 1 1 calc R . .
C8 C 0.49424(16) 0.6223(3) 0.4617(3) 0.0717(11) Uani 1 1 d . . .
H8A H 0.4964 0.6432 0.5182 0.086 Uiso 1 1 calc R . .
C9 C 0.53974(16) 0.6161(3) 0.4278(3) 0.0729(11) Uani 1 1 d . . .
H9A H 0.5729 0.6342 0.4603 0.087 Uiso 1 1 calc R . .
C10 C 0.53390(15) 0.5829(3) 0.3462(3) 0.0712(11) Uani 1 1 d . . .
H10A H 0.5642 0.5780 0.3234 0.085 Uiso 1 1 calc R . .
C11 C 0.34921(15) 0.5312(3) 0.3205(2) 0.0637(10) Uani 1 1 d . . .
C12 C 0.31852(14) 0.6141(3) 0.3348(2) 0.0626(10) Uani 1 1 d . . .
C13 C 0.32653(15) 0.7120(3) 0.3095(2) 0.0686(10) Uani 1 1 d . . .
H13A H 0.3539 0.7256 0.2813 0.082 Uiso 1 1 calc R . .
C14 C 0.29490(17) 0.7871(4) 0.3256(3) 0.0816(12) Uani 1 1 d . . .
H14A H 0.3007 0.8519 0.3079 0.098 Uiso 1 1 calc R . .
C15 C 0.25332(18) 0.7690(5) 0.3685(3) 0.0971(16) Uani 1 1 d . . .
H15A H 0.2314 0.8211 0.3784 0.117 Uiso 1 1 calc R . .
C16 C 0.24567(18) 0.6752(5) 0.3952(3) 0.0890(14) Uani 1 1 d . . .
H16A H 0.2186 0.6639 0.4245 0.107 Uiso 1 1 calc R . .
C17 C 0.27683(15) 0.5951(4) 0.3806(2) 0.0722(11) Uani 1 1 d . . .
C18 C 0.26919(19) 0.4944(5) 0.4072(3) 0.0924(16) Uani 1 1 d . . .
H18A H 0.2426 0.4812 0.4372 0.111 Uiso 1 1 calc R . .
C19 C 0.2998(2) 0.4186(4) 0.3895(3) 0.0958(14) Uani 1 1 d . . .
H19A H 0.2942 0.3536 0.4067 0.115 Uiso 1 1 calc R . .
C20 C 0.33922(17) 0.4378(3) 0.3461(3) 0.0777(12) Uani 1 1 d . . .
H20A H 0.3599 0.3848 0.3337 0.093 Uiso 1 1 calc R . .
C21 C 0.52040(18) 0.3714(4) 0.1292(3) 0.0915(14) Uani 1 1 d . . .
H21A H 0.5102 0.3024 0.1362 0.110 Uiso 1 1 calc R . .
H21B H 0.5224 0.3879 0.0704 0.110 Uiso 1 1 calc R . .
C22 C 0.55962(16) 0.4100(3) 0.1932(3) 0.0762(12) Uani 1 1 d . . .
H22A H 0.5846 0.4540 0.1723 0.091 Uiso 1 1 calc R . .
C23 C 0.58135(17) 0.3645(3) 0.2779(3) 0.0689(11) Uani 1 1 d . . .
C24 C 0.5555(2) 0.2911(4) 0.3128(3) 0.0847(13) Uani 1 1 d . . .
H24A H 0.5226 0.2679 0.2831 0.102 Uiso 1 1 calc R . .
C25 C 0.5788(3) 0.2510(4) 0.3931(5) 0.116(2) Uani 1 1 d . . .
H25A H 0.5616 0.2013 0.4179 0.139 Uiso 1 1 calc R . .
C26 C 0.6292(4) 0.2875(6) 0.4361(4) 0.127(2) Uani 1 1 d . . .
H26A H 0.6455 0.2613 0.4895 0.153 Uiso 1 1 calc R . .
C27 C 0.6534(3) 0.3595(6) 0.4004(4) 0.120(2) Uani 1 1 d . . .
H27A H 0.6865 0.3832 0.4286 0.145 Uiso 1 1 calc R . .
C28 C 0.62952(19) 0.3977(4) 0.3233(3) 0.0890(14) Uani 1 1 d . . .
H28A H 0.6465 0.4488 0.2999 0.107 Uiso 1 1 calc R . .
B1 B 0.5831(3) 0.6843(6) 0.1327(5) 0.1047(19) Uani 1 1 d . . .
F1 F 0.54069(14) 0.6252(2) 0.1006(2) 0.1331(11) Uani 1 1 d . . .
F2 F 0.6042(2) 0.7247(3) 0.0714(3) 0.197(2) Uani 1 1 d . . .
F3 F 0.57410(16) 0.7511(4) 0.1880(3) 0.195(2) Uani 1 1 d . . .
F4 F 0.62439(16) 0.6229(3) 0.1744(3) 0.1644(14) Uani 1 1 d . . .
Cu2 Cu 0.064048(18) 0.96780(3) 0.24162(3) 0.06082(18) Uani 1 1 d . . .
N4 N 0.12164(11) 1.0773(2) 0.41068(17) 0.0537(7) Uani 1 1 d . . .
N5 N 0.13464(12) 1.0289(2) 0.2719(2) 0.0587(8) Uani 1 1 d . . .
N6 N 0.03486(11) 1.03902(19) 0.32905(18) 0.0496(7) Uani 1 1 d . . .
C29 C 0.15307(14) 1.0736(3) 0.3470(3) 0.0597(9) Uani 1 1 d . . .
C30 C 0.20398(17) 1.1149(4) 0.3662(3) 0.0886(14) Uani 1 1 d . . .
H30A H 0.2169 1.1452 0.4193 0.106 Uiso 1 1 calc R . .
C31 C 0.23458(18) 1.1101(4) 0.3060(4) 0.1040(17) Uani 1 1 d . . .
H31A H 0.2689 1.1360 0.3183 0.125 Uiso 1 1 calc R . .
C32 C 0.2149(2) 1.0673(4) 0.2273(3) 0.0913(14) Uani 1 1 d . . .
H32A H 0.2350 1.0654 0.1852 0.110 Uiso 1 1 calc R . .
C33 C 0.16541(18) 1.0278(3) 0.2126(3) 0.0771(12) Uani 1 1 d . . .
H33A H 0.1519 0.9986 0.1592 0.093 Uiso 1 1 calc R . .
C34 C 0.06600(13) 1.0816(2) 0.3985(2) 0.0483(8) Uani 1 1 d . . .
C35 C 0.04361(15) 1.1275(3) 0.4602(2) 0.0652(10) Uani 1 1 d . . .
H35A H 0.0652 1.1572 0.5082 0.078 Uiso 1 1 calc R . .
C36 C -0.01035(17) 1.1293(3) 0.4507(3) 0.0751(11) Uani 1 1 d . . .
H36A H -0.0256 1.1596 0.4924 0.090 Uiso 1 1 calc R . .
C37 C -0.04204(15) 1.0863(3) 0.3793(3) 0.0647(10) Uani 1 1 d . . .
H37A H -0.0789 1.0869 0.3717 0.078 Uiso 1 1 calc R . .
C38 C -0.01828(14) 1.0434(3) 0.3207(2) 0.0580(9) Uani 1 1 d . . .
H38A H -0.0397 1.0153 0.2719 0.070 Uiso 1 1 calc R . .
C39 C 0.15025(14) 1.0692(3) 0.4986(2) 0.0570(9) Uani 1 1 d . . .
C40 C 0.15917(13) 0.9715(3) 0.5335(2) 0.0549(9) Uani 1 1 d . . .
C41 C 0.14314(13) 0.8834(3) 0.4859(3) 0.0618(10) Uani 1 1 d . . .
H41A H 0.1255 0.8888 0.4285 0.074 Uiso 1 1 calc R . .
C42 C 0.15278(16) 0.7907(3) 0.5218(3) 0.0770(12) Uani 1 1 d . . .
H42A H 0.1424 0.7337 0.4888 0.092 Uiso 1 1 calc R . .
C43 C 0.17810(19) 0.7820(5) 0.6077(4) 0.1022(18) Uani 1 1 d . . .
H43A H 0.1843 0.7186 0.6321 0.123 Uiso 1 1 calc R . .
C44 C 0.19392(16) 0.8631(5) 0.6564(3) 0.0905(15) Uani 1 1 d . . .
H44A H 0.2113 0.8550 0.7137 0.109 Uiso 1 1 calc R . .
C45 C 0.18461(14) 0.9601(4) 0.6219(3) 0.0696(11) Uani 1 1 d . . .
C46 C 0.20078(17) 1.0462(5) 0.6702(3) 0.0922(15) Uani 1 1 d . . .
H46A H 0.2172 1.0397 0.7280 0.111 Uiso 1 1 calc R . .
C47 C 0.19316(18) 1.1397(5) 0.6349(3) 0.0978(15) Uani 1 1 d . . .
H47A H 0.2050 1.1959 0.6682 0.117 Uiso 1 1 calc R . .
C48 C 0.16737(16) 1.1506(3) 0.5483(3) 0.0788(12) Uani 1 1 d . . .
H48A H 0.1619 1.2144 0.5244 0.095 Uiso 1 1 calc R . .
C49 C 0.0604(2) 0.8597(4) 0.1536(3) 0.0969(15) Uani 1 1 d . . .
H49A H 0.0585 0.8812 0.0946 0.116 Uiso 1 1 calc R . .
H49B H 0.0833 0.8022 0.1701 0.116 Uiso 1 1 calc R . .
C50 C 0.01301(18) 0.8611(3) 0.1826(3) 0.0738(11) Uani 1 1 d . . .
H50A H -0.0176 0.8870 0.1406 0.089 Uiso 1 1 calc R . .
C51 C -0.00066(18) 0.7958(3) 0.2487(3) 0.0688(11) Uani 1 1 d . . .
C52 C 0.0375(2) 0.7394(3) 0.3055(3) 0.0813(12) Uani 1 1 d . . .
H52A H 0.0729 0.7418 0.3015 0.098 Uiso 1 1 calc R . .
C53 C 0.0223(3) 0.6801(4) 0.3674(3) 0.1019(17) Uani 1 1 d . . .
H53A H 0.0477 0.6430 0.4053 0.122 Uiso 1 1 calc R . .
C54 C -0.0308(4) 0.6756(5) 0.3733(4) 0.116(2) Uani 1 1 d . . .
H54A H -0.0410 0.6343 0.4141 0.140 Uiso 1 1 calc R . .
C55 C -0.0675(3) 0.7314(4) 0.3197(4) 0.1035(18) Uani 1 1 d . . .
H55A H -0.1029 0.7295 0.3246 0.124 Uiso 1 1 calc R . .
C56 C -0.05280(18) 0.7910(3) 0.2579(3) 0.0820(13) Uani 1 1 d . . .
H56A H -0.0785 0.8288 0.2215 0.098 Uiso 1 1 calc R . .
B2 B -0.1286(3) 0.9659(5) 0.0365(5) 0.0974(19) Uani 1 1 d . . .
F5 F -0.12174(17) 0.9909(4) 0.1200(2) 0.1794(17) Uani 1 1 d . . .
F6 F -0.15804(19) 1.0376(3) -0.0090(2) 0.1689(16) Uani 1 1 d . . .
F7 F -0.08266(17) 0.9685(4) 0.0111(3) 0.203(2) Uani 1 1 d . . .
F8 F -0.1510(3) 0.8855(3) 0.0196(5) 0.296(4) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0568(3) 0.0744(4) 0.0730(3) -0.0121(2) 0.0145(2) 0.0122(2)
N1 0.0443(16) 0.068(2) 0.0590(19) 0.0012(15) 0.0152(14) 0.0036(14)
N2 0.0535(19) 0.096(2) 0.058(2) -0.0082(17) 0.0129(16) 0.0070(17)
N3 0.0490(19) 0.064(2) 0.075(2) -0.0078(16) 0.0138(16) 0.0053(15)
C1 0.050(2) 0.067(3) 0.061(2) 0.0053(19) 0.0125(18) 0.0031(18)
C2 0.053(2) 0.110(4) 0.065(3) -0.001(2) 0.012(2) 0.004(2)
C3 0.057(3) 0.147(5) 0.062(3) 0.001(3) -0.002(2) 0.008(3)
C4 0.079(3) 0.157(5) 0.062(3) -0.010(3) 0.003(3) 0.017(3)
C5 0.070(3) 0.127(4) 0.078(3) -0.032(3) 0.013(2) 0.002(3)
C6 0.049(2) 0.054(2) 0.060(2) 0.0015(18) 0.0127(18) 0.0061(17)
C7 0.065(3) 0.073(3) 0.066(3) -0.002(2) 0.017(2) 0.007(2)
C8 0.068(3) 0.078(3) 0.067(2) -0.008(2) 0.009(2) 0.004(2)
C9 0.058(2) 0.074(3) 0.083(3) -0.014(2) 0.006(2) 0.006(2)
C10 0.050(2) 0.071(3) 0.093(3) -0.013(2) 0.015(2) 0.012(2)
C11 0.054(2) 0.071(3) 0.067(2) 0.001(2) 0.0131(19) 0.000(2)
C12 0.054(2) 0.079(3) 0.057(2) 0.000(2) 0.0173(18) -0.008(2)
C13 0.061(2) 0.074(3) 0.077(3) 0.003(2) 0.027(2) 0.003(2)
C14 0.071(3) 0.094(3) 0.080(3) -0.013(2) 0.016(2) 0.005(2)
C15 0.070(3) 0.134(5) 0.088(3) -0.032(3) 0.019(3) 0.024(3)
C16 0.066(3) 0.131(5) 0.071(3) -0.006(3) 0.018(2) -0.001(3)
C17 0.049(2) 0.110(4) 0.059(2) -0.006(2) 0.0132(18) -0.006(2)
C18 0.069(3) 0.139(5) 0.072(3) 0.020(3) 0.022(2) -0.036(3)
C19 0.101(4) 0.094(4) 0.094(4) 0.016(3) 0.025(3) -0.013(3)
C20 0.080(3) 0.079(3) 0.076(3) 0.016(2) 0.020(2) -0.005(2)
C21 0.085(3) 0.107(4) 0.083(3) -0.028(3) 0.018(3) 0.031(3)
C22 0.066(3) 0.085(3) 0.083(3) -0.014(3) 0.028(2) 0.016(2)
C23 0.066(3) 0.065(3) 0.079(3) -0.016(2) 0.023(2) 0.014(2)
C24 0.092(3) 0.071(3) 0.094(4) -0.006(3) 0.029(3) 0.024(3)
C25 0.161(6) 0.081(4) 0.128(5) 0.005(4) 0.080(5) 0.033(4)
C26 0.150(7) 0.141(6) 0.088(4) -0.011(4) 0.019(4) 0.063(5)
C27 0.110(5) 0.148(6) 0.096(5) -0.029(4) 0.004(4) 0.028(4)
C28 0.076(3) 0.099(4) 0.091(4) -0.026(3) 0.014(3) 0.012(3)
B1 0.120(6) 0.101(5) 0.097(5) 0.014(4) 0.031(4) -0.007(5)
F1 0.128(3) 0.126(3) 0.128(2) -0.006(2) -0.0103(19) -0.020(2)
F2 0.346(6) 0.128(3) 0.151(3) -0.006(2) 0.127(4) -0.054(3)
F3 0.140(3) 0.248(5) 0.219(4) -0.129(4) 0.088(3) -0.057(3)
F4 0.127(3) 0.155(3) 0.197(4) 0.025(3) 0.004(3) -0.012(3)
Cu2 0.0688(3) 0.0592(3) 0.0603(3) -0.0049(2) 0.0269(2) -0.0046(2)
N4 0.0492(17) 0.0615(18) 0.0515(18) 0.0027(14) 0.0132(14) 0.0037(14)
N5 0.0575(19) 0.0599(19) 0.065(2) 0.0040(16) 0.0269(16) 0.0016(15)
N6 0.0497(17) 0.0434(16) 0.0563(18) 0.0020(13) 0.0123(14) 0.0005(13)
C29 0.057(2) 0.055(2) 0.070(3) 0.012(2) 0.0197(19) 0.0046(18)
C30 0.067(3) 0.119(4) 0.083(3) 0.009(3) 0.024(2) -0.020(3)
C31 0.058(3) 0.140(5) 0.120(4) 0.030(4) 0.030(3) -0.015(3)
C32 0.077(3) 0.114(4) 0.095(4) 0.020(3) 0.044(3) 0.007(3)
C33 0.075(3) 0.081(3) 0.086(3) 0.006(2) 0.042(2) 0.005(2)
C34 0.053(2) 0.0392(19) 0.055(2) 0.0084(16) 0.0178(17) 0.0061(16)
C35 0.058(2) 0.079(3) 0.059(2) -0.0116(19) 0.0118(18) 0.0084(19)
C36 0.069(3) 0.085(3) 0.080(3) 0.001(2) 0.035(2) 0.014(2)
C37 0.048(2) 0.066(3) 0.085(3) 0.005(2) 0.025(2) 0.0068(19)
C38 0.054(2) 0.057(2) 0.066(2) 0.0018(18) 0.0181(18) -0.0029(17)
C39 0.050(2) 0.059(2) 0.061(2) -0.002(2) 0.0097(18) 0.0050(18)
C40 0.0345(18) 0.076(3) 0.056(2) -0.002(2) 0.0136(16) 0.0039(17)
C41 0.047(2) 0.070(3) 0.072(2) 0.006(2) 0.0214(18) 0.0035(19)
C42 0.061(3) 0.066(3) 0.111(4) 0.017(3) 0.034(3) 0.010(2)
C43 0.058(3) 0.102(4) 0.149(6) 0.060(4) 0.028(3) 0.011(3)
C44 0.045(2) 0.132(5) 0.090(3) 0.043(4) 0.005(2) 0.006(3)
C45 0.040(2) 0.097(3) 0.068(3) 0.006(3) 0.0031(19) 0.004(2)
C46 0.058(3) 0.149(5) 0.063(3) -0.008(3) -0.003(2) 0.002(3)
C47 0.077(3) 0.118(5) 0.086(4) -0.029(3) -0.010(3) 0.001(3)
C48 0.074(3) 0.066(3) 0.089(3) -0.009(2) 0.001(2) -0.005(2)
C49 0.143(4) 0.083(3) 0.078(3) -0.031(2) 0.054(3) -0.033(3)
C50 0.092(3) 0.072(3) 0.062(2) -0.015(2) 0.026(2) -0.018(2)
C51 0.084(3) 0.056(2) 0.071(3) -0.022(2) 0.026(2) -0.015(2)
C52 0.094(3) 0.073(3) 0.080(3) -0.017(2) 0.023(3) -0.012(3)
C53 0.161(6) 0.066(3) 0.070(3) -0.012(2) 0.006(3) -0.019(3)
C54 0.190(7) 0.091(4) 0.087(4) -0.031(3) 0.073(5) -0.060(5)
C55 0.121(5) 0.085(4) 0.124(5) -0.035(3) 0.070(4) -0.043(3)
C56 0.090(3) 0.066(3) 0.098(3) -0.024(2) 0.038(3) -0.015(2)
B2 0.087(4) 0.098(5) 0.111(5) -0.022(4) 0.030(4) 0.031(4)
F5 0.165(4) 0.289(5) 0.094(3) -0.023(3) 0.048(2) 0.004(3)
F6 0.226(4) 0.163(3) 0.128(3) 0.032(2) 0.061(3) 0.088(3)
F7 0.139(4) 0.325(7) 0.167(4) -0.032(4) 0.083(3) 0.037(3)
F8 0.406(9) 0.100(3) 0.391(9) -0.080(4) 0.105(7) -0.090(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.949(3) . ?
Cu1 N3 1.968(3) . ?
Cu1 C21 1.978(4) . ?
Cu1 C22 2.021(4) . ?
N1 C6 1.410(4) . ?
N1 C1 1.416(5) . ?
N1 C11 1.463(5) . ?
N2 C1 1.341(5) . ?
N2 C5 1.352(5) . ?
N3 C6 1.333(4) . ?
N3 C10 1.360(5) . ?
C1 C2 1.388(5) . ?
C2 C3 1.348(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.361(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(6) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.394(5) . ?
C7 C8 1.354(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.392(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.348(5) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C20 1.352(5) . ?
C11 C12 1.407(5) . ?
C12 C13 1.395(5) . ?
C12 C17 1.441(5) . ?
C13 C14 1.349(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.407(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.350(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.385(6) . ?
C16 H16A 0.9300 . ?
C17 C18 1.435(7) . ?
C18 C19 1.349(7) . ?
C18 H18A 0.9300 . ?
C19 C20 1.366(6) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C22 1.371(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.474(6) . ?
C22 H22A 0.9800 . ?
C23 C24 1.366(6) . ?
C23 C28 1.369(6) . ?
C24 C25 1.395(7) . ?
C24 H24A 0.9300 . ?
C25 C26 1.417(9) . ?
C25 H25A 0.9300 . ?
C26 C27 1.335(9) . ?
C26 H26A 0.9300 . ?
C27 C28 1.347(7) . ?
C27 H27A 0.9300 . ?
C28 H28A 0.9300 . ?
B1 F3 1.306(8) . ?
B1 F2 1.326(7) . ?
B1 F1 1.356(7) . ?
B1 F4 1.392(8) . ?
Cu2 N5 1.956(3) . ?
Cu2 N6 1.959(3) . ?
Cu2 C49 1.997(4) . ?
Cu2 C50 2.027(4) . ?
N4 C34 1.405(4) . ?
N4 C29 1.423(4) . ?
N4 C39 1.437(4) . ?
N5 C29 1.328(5) . ?
N5 C33 1.353(5) . ?
N6 C34 1.344(4) . ?
N6 C38 1.348(4) . ?
C29 C30 1.394(5) . ?
C30 C31 1.364(6) . ?
C30 H30A 0.9300 . ?
C31 C32 1.368(7) . ?
C31 H31A 0.9300 . ?
C32 C33 1.352(6) . ?
C32 H32A 0.9300 . ?
C33 H33A 0.9300 . ?
C34 C35 1.381(5) . ?
C35 C36 1.365(5) . ?
C35 H35A 0.9300 . ?
C36 C37 1.373(5) . ?
C36 H36A 0.9300 . ?
C37 C38 1.346(5) . ?
C37 H37A 0.9300 . ?
C38 H38A 0.9300 . ?
C39 C48 1.359(5) . ?
C39 C40 1.416(5) . ?
C40 C41 1.411(5) . ?
C40 C45 1.425(5) . ?
C41 C42 1.362(5) . ?
C41 H41A 0.9300 . ?
C42 C43 1.386(7) . ?
C42 H42A 0.9300 . ?
C43 C44 1.343(7) . ?
C43 H43A 0.9300 . ?
C44 C45 1.406(6) . ?
C44 H44A 0.9300 . ?
C45 C46 1.394(6) . ?
C46 C47 1.364(7) . ?
C46 H46A 0.9300 . ?
C47 C48 1.402(6) . ?
C47 H47A 0.9300 . ?
C48 H48A 0.9300 . ?
C49 C50 1.393(6) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C51 1.465(5) . ?
C50 H50A 0.9800 . ?
C51 C56 1.382(5) . ?
C51 C52 1.402(6) . ?
C52 C53 1.381(6) . ?
C52 H52A 0.9300 . ?
C53 C54 1.390(8) . ?
C53 H53A 0.9300 . ?
C54 C55 1.354(8) . ?
C54 H54A 0.9300 . ?
C55 C56 1.377(7) . ?
C55 H55A 0.9300 . ?
C56 H56A 0.9300 . ?
B2 F8 1.221(7) . ?
B2 F7 1.328(7) . ?
B2 F6 1.333(7) . ?
B2 F5 1.342(7) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N3 93.98(13) . . ?
N2 Cu1 C21 111.84(17) . . ?
N3 Cu1 C21 152.74(16) . . ?
N2 Cu1 C22 151.79(16) . . ?
N3 Cu1 C22 114.14(15) . . ?
C21 Cu1 C22 40.09(16) . . ?
C6 N1 C1 129.0(3) . . ?
C6 N1 C11 116.2(3) . . ?
C1 N1 C11 114.7(3) . . ?
C1 N2 C5 118.1(3) . . ?
C1 N2 Cu1 124.3(3) . . ?
C5 N2 Cu1 117.4(3) . . ?
C6 N3 C10 117.8(3) . . ?
C6 N3 Cu1 122.3(3) . . ?
C10 N3 Cu1 117.9(2) . . ?
N2 C1 C2 120.7(4) . . ?
N2 C1 N1 119.7(3) . . ?
C2 C1 N1 119.6(3) . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 C5 117.4(4) . . ?
C3 C4 H4A 121.3 . . ?
C5 C4 H4A 121.3 . . ?
N2 C5 C4 123.1(4) . . ?
N2 C5 H5A 118.5 . . ?
C4 C5 H5A 118.5 . . ?
N3 C6 C7 120.2(3) . . ?
N3 C6 N1 120.6(3) . . ?
C7 C6 N1 119.3(3) . . ?
C8 C7 C6 121.0(4) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C7 C8 C9 119.0(4) . . ?
C7 C8 H8A 120.5 . . ?
C9 C8 H8A 120.5 . . ?
C10 C9 C8 117.4(4) . . ?
C10 C9 H9A 121.3 . . ?
C8 C9 H9A 121.3 . . ?
C9 C10 N3 124.5(4) . . ?
C9 C10 H10A 117.8 . . ?
N3 C10 H10A 117.8 . . ?
C20 C11 C12 121.8(4) . . ?
C20 C11 N1 118.1(4) . . ?
C12 C11 N1 120.1(3) . . ?
C13 C12 C11 124.6(3) . . ?
C13 C12 C17 118.8(4) . . ?
C11 C12 C17 116.6(4) . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 121.1(5) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C16 C15 C14 119.2(5) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
C15 C16 C17 122.3(4) . . ?
C15 C16 H16A 118.9 . . ?
C17 C16 H16A 118.9 . . ?
C16 C17 C18 123.5(4) . . ?
C16 C17 C12 118.0(4) . . ?
C18 C17 C12 118.5(4) . . ?
C19 C18 C17 121.2(4) . . ?
C19 C18 H18A 119.4 . . ?
C17 C18 H18A 119.4 . . ?
C18 C19 C20 119.6(5) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C11 C20 C19 122.2(5) . . ?
C11 C20 H20A 118.9 . . ?
C19 C20 H20A 118.9 . . ?
C22 C21 Cu1 71.7(2) . . ?
C22 C21 H21A 116.4 . . ?
Cu1 C21 H21A 116.4 . . ?
C22 C21 H21B 116.4 . . ?
Cu1 C21 H21B 116.4 . . ?
H21A C21 H21B 113.4 . . ?
C21 C22 C23 126.7(4) . . ?
C21 C22 Cu1 68.2(2) . . ?
C23 C22 Cu1 110.3(3) . . ?
C21 C22 H22A 114.0 . . ?
C23 C22 H22A 114.0 . . ?
Cu1 C22 H22A 114.0 . . ?
C24 C23 C28 118.9(5) . . ?
C24 C23 C22 122.9(4) . . ?
C28 C23 C22 118.2(4) . . ?
C23 C24 C25 119.6(5) . . ?
C23 C24 H24A 120.2 . . ?
C25 C24 H24A 120.2 . . ?
C24 C25 C26 118.7(6) . . ?
C24 C25 H25A 120.7 . . ?
C26 C25 H25A 120.7 . . ?
C27 C26 C25 120.3(6) . . ?
C27 C26 H26A 119.8 . . ?
C25 C26 H26A 119.8 . . ?
C26 C27 C28 119.6(7) . . ?
C26 C27 H27A 120.2 . . ?
C28 C27 H27A 120.2 . . ?
C27 C28 C23 122.9(6) . . ?
C27 C28 H28A 118.6 . . ?
C23 C28 H28A 118.6 . . ?
F3 B1 F2 112.1(6) . . ?
F3 B1 F1 113.9(6) . . ?
F2 B1 F1 112.5(6) . . ?
F3 B1 F4 108.0(6) . . ?
F2 B1 F4 101.4(6) . . ?
F1 B1 F4 108.0(6) . . ?
N5 Cu2 N6 95.77(12) . . ?
N5 Cu2 C49 112.06(17) . . ?
N6 Cu2 C49 151.43(16) . . ?
N5 Cu2 C50 152.02(15) . . ?
N6 Cu2 C50 111.09(14) . . ?
C49 Cu2 C50 40.48(16) . . ?
C34 N4 C29 128.4(3) . . ?
C34 N4 C39 115.6(3) . . ?
C29 N4 C39 115.8(3) . . ?
C29 N5 C33 118.7(3) . . ?
C29 N5 Cu2 122.9(2) . . ?
C33 N5 Cu2 118.4(3) . . ?
C34 N6 C38 118.5(3) . . ?
C34 N6 Cu2 122.3(2) . . ?
C38 N6 Cu2 119.1(2) . . ?
N5 C29 C30 120.8(3) . . ?
N5 C29 N4 120.3(3) . . ?
C30 C29 N4 118.8(4) . . ?
C31 C30 C29 119.0(5) . . ?
C31 C30 H30A 120.5 . . ?
C29 C30 H30A 120.5 . . ?
C30 C31 C32 120.1(4) . . ?
C30 C31 H31A 119.9 . . ?
C32 C31 H31A 119.9 . . ?
C33 C32 C31 118.2(4) . . ?
C33 C32 H32A 120.9 . . ?
C31 C32 H32A 120.9 . . ?
C32 C33 N5 123.0(4) . . ?
C32 C33 H33A 118.5 . . ?
N5 C33 H33A 118.5 . . ?
N6 C34 C35 120.3(3) . . ?
N6 C34 N4 120.5(3) . . ?
C35 C34 N4 119.2(3) . . ?
C36 C35 C34 119.8(4) . . ?
C36 C35 H35A 120.1 . . ?
C34 C35 H35A 120.1 . . ?
C35 C36 C37 119.8(4) . . ?
C35 C36 H36A 120.1 . . ?
C37 C36 H36A 120.1 . . ?
C38 C37 C36 118.1(3) . . ?
C38 C37 H37A 121.0 . . ?
C36 C37 H37A 121.0 . . ?
C37 C38 N6 123.5(4) . . ?
C37 C38 H38A 118.2 . . ?
N6 C38 H38A 118.2 . . ?
C48 C39 C40 120.2(4) . . ?
C48 C39 N4 122.6(4) . . ?
C40 C39 N4 117.1(3) . . ?
C41 C40 C39 123.6(3) . . ?
C41 C40 C45 117.3(4) . . ?
C39 C40 C45 119.1(4) . . ?
C42 C41 C40 121.8(4) . . ?
C42 C41 H41A 119.1 . . ?
C40 C41 H41A 119.1 . . ?
C41 C42 C43 119.6(5) . . ?
C41 C42 H42A 120.2 . . ?
C43 C42 H42A 120.2 . . ?
C44 C43 C42 121.4(5) . . ?
C44 C43 H43A 119.3 . . ?
C42 C43 H43A 119.3 . . ?
C43 C44 C45 120.8(5) . . ?
C43 C44 H44A 119.6 . . ?
C45 C44 H44A 119.6 . . ?
C46 C45 C44 122.6(5) . . ?
C46 C45 C40 118.3(4) . . ?
C44 C45 C40 119.1(4) . . ?
C47 C46 C45 121.9(5) . . ?
C47 C46 H46A 119.0 . . ?
C45 C46 H46A 119.1 . . ?
C46 C47 C48 119.6(5) . . ?
C46 C47 H47A 120.2 . . ?
C48 C47 H47A 120.2 . . ?
C39 C48 C47 120.9(4) . . ?
C39 C48 H48A 119.6 . . ?
C47 C48 H48A 119.6 . . ?
C50 C49 Cu2 70.9(2) . . ?
C50 C49 H49A 116.5 . . ?
Cu2 C49 H49A 116.5 . . ?
C50 C49 H49B 116.5 . . ?
Cu2 C49 H49B 116.5 . . ?
H49A C49 H49B 113.5 . . ?
C49 C50 C51 126.2(4) . . ?
C49 C50 Cu2 68.6(2) . . ?
C51 C50 Cu2 108.5(3) . . ?
C49 C50 H50A 114.5 . . ?
C51 C50 H50A 114.5 . . ?
Cu2 C50 H50A 114.5 . . ?
C56 C51 C52 118.0(4) . . ?
C56 C51 C50 119.4(4) . . ?
C52 C51 C50 122.6(4) . . ?
C53 C52 C51 120.0(5) . . ?
C53 C52 H52A 120.0 . . ?
C51 C52 H52A 120.0 . . ?
C52 C53 C54 120.2(6) . . ?
C52 C53 H53A 119.9 . . ?
C54 C53 H53A 119.9 . . ?
C55 C54 C53 120.0(6) . . ?
C55 C54 H54A 120.0 . . ?
C53 C54 H54A 120.0 . . ?
C54 C55 C56 120.2(5) . . ?
C54 C55 H55A 119.9 . . ?
C56 C55 H55A 119.9 . . ?
C55 C56 C51 121.5(5) . . ?
C55 C56 H56A 119.2 . . ?
C51 C56 H56A 119.2 . . ?
F8 B2 F7 111.5(6) . . ?
F8 B2 F6 108.9(7) . . ?
F7 B2 F6 104.9(6) . . ?
F8 B2 F5 113.1(7) . . ?
F7 B2 F5 110.8(6) . . ?
F6 B2 F5 107.2(5) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cu1 N2 C1 -15.2(3) . . . . ?
C21 Cu1 N2 C1 155.8(3) . . . . ?
C22 Cu1 N2 C1 160.5(4) . . . . ?
N3 Cu1 N2 C5 159.5(3) . . . . ?
C21 Cu1 N2 C5 -29.5(4) . . . . ?
C22 Cu1 N2 C5 -24.8(5) . . . . ?
N2 Cu1 N3 C6 29.0(3) . . . . ?
C21 Cu1 N3 C6 -132.6(4) . . . . ?
C22 Cu1 N3 C6 -148.8(3) . . . . ?
N2 Cu1 N3 C10 -167.2(3) . . . . ?
C21 Cu1 N3 C10 31.2(5) . . . . ?
C22 Cu1 N3 C10 15.0(3) . . . . ?
C5 N2 C1 C2 0.4(6) . . . . ?
Cu1 N2 C1 C2 175.0(3) . . . . ?
C5 N2 C1 N1 177.5(4) . . . . ?
Cu1 N2 C1 N1 -7.9(5) . . . . ?
C6 N1 C1 N2 29.4(5) . . . . ?
C11 N1 C1 N2 -149.1(3) . . . . ?
C6 N1 C1 C2 -153.5(4) . . . . ?
C11 N1 C1 C2 28.0(5) . . . . ?
N2 C1 C2 C3 -0.1(6) . . . . ?
N1 C1 C2 C3 -177.1(4) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C2 C3 C4 C5 1.7(8) . . . . ?
C1 N2 C5 C4 0.3(7) . . . . ?
Cu1 N2 C5 C4 -174.7(4) . . . . ?
C3 C4 C5 N2 -1.4(8) . . . . ?
C10 N3 C6 C7 -3.8(5) . . . . ?
Cu1 N3 C6 C7 160.1(3) . . . . ?
C10 N3 C6 N1 176.9(3) . . . . ?
Cu1 N3 C6 N1 -19.2(5) . . . . ?
C1 N1 C6 N3 -14.3(5) . . . . ?
C11 N1 C6 N3 164.2(3) . . . . ?
C1 N1 C6 C7 166.4(3) . . . . ?
C11 N1 C6 C7 -15.1(5) . . . . ?
N3 C6 C7 C8 2.9(6) . . . . ?
N1 C6 C7 C8 -177.8(3) . . . . ?
C6 C7 C8 C9 -0.1(6) . . . . ?
C7 C8 C9 C10 -1.5(6) . . . . ?
C8 C9 C10 N3 0.6(6) . . . . ?
C6 N3 C10 C9 2.1(6) . . . . ?
Cu1 N3 C10 C9 -162.5(3) . . . . ?
C6 N1 C11 C20 -91.5(4) . . . . ?
C1 N1 C11 C20 87.3(4) . . . . ?
C6 N1 C11 C12 90.1(4) . . . . ?
C1 N1 C11 C12 -91.2(4) . . . . ?
C20 C11 C12 C13 -179.5(4) . . . . ?
N1 C11 C12 C13 -1.1(6) . . . . ?
C20 C11 C12 C17 1.8(6) . . . . ?
N1 C11 C12 C17 -179.8(3) . . . . ?
C11 C12 C13 C14 179.6(4) . . . . ?
C17 C12 C13 C14 -1.7(6) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C14 C15 C16 1.1(7) . . . . ?
C14 C15 C16 C17 -1.2(7) . . . . ?
C15 C16 C17 C18 -179.1(4) . . . . ?
C15 C16 C17 C12 -0.2(6) . . . . ?
C13 C12 C17 C16 1.6(5) . . . . ?
C11 C12 C17 C16 -179.6(4) . . . . ?
C13 C12 C17 C18 -179.3(4) . . . . ?
C11 C12 C17 C18 -0.6(5) . . . . ?
C16 C17 C18 C19 178.4(4) . . . . ?
C12 C17 C18 C19 -0.6(6) . . . . ?
C17 C18 C19 C20 0.6(7) . . . . ?
C12 C11 C20 C19 -1.9(6) . . . . ?
N1 C11 C20 C19 179.6(4) . . . . ?
C18 C19 C20 C11 0.6(7) . . . . ?
N2 Cu1 C21 C22 176.6(3) . . . . ?
N3 Cu1 C21 C22 -23.3(6) . . . . ?
Cu1 C21 C22 C23 99.7(4) . . . . ?
N2 Cu1 C22 C21 -6.8(5) . . . . ?
N3 Cu1 C22 C21 168.6(3) . . . . ?
N2 Cu1 C22 C23 -129.4(3) . . . . ?
N3 Cu1 C22 C23 46.0(3) . . . . ?
C21 Cu1 C22 C23 -122.6(5) . . . . ?
C21 C22 C23 C24 -18.3(6) . . . . ?
Cu1 C22 C23 C24 59.2(4) . . . . ?
C21 C22 C23 C28 161.8(4) . . . . ?
Cu1 C22 C23 C28 -120.8(3) . . . . ?
C28 C23 C24 C25 -0.6(6) . . . . ?
C22 C23 C24 C25 179.5(4) . . . . ?
C23 C24 C25 C26 -0.5(7) . . . . ?
C24 C25 C26 C27 0.6(8) . . . . ?
C25 C26 C27 C28 0.3(9) . . . . ?
C26 C27 C28 C23 -1.4(8) . . . . ?
C24 C23 C28 C27 1.5(6) . . . . ?
C22 C23 C28 C27 -178.5(4) . . . . ?
N6 Cu2 N5 C29 18.6(3) . . . . ?
C49 Cu2 N5 C29 -154.8(3) . . . . ?
C50 Cu2 N5 C29 -145.3(3) . . . . ?
N6 Cu2 N5 C33 -159.5(3) . . . . ?
C49 Cu2 N5 C33 27.1(3) . . . . ?
C50 Cu2 N5 C33 36.6(5) . . . . ?
N5 Cu2 N6 C34 -19.6(3) . . . . ?
C49 Cu2 N6 C34 147.6(4) . . . . ?
C50 Cu2 N6 C34 152.4(3) . . . . ?
N5 Cu2 N6 C38 162.3(2) . . . . ?
C49 Cu2 N6 C38 -30.6(5) . . . . ?
C50 Cu2 N6 C38 -25.7(3) . . . . ?
C33 N5 C29 C30 -2.8(5) . . . . ?
Cu2 N5 C29 C30 179.1(3) . . . . ?
C33 N5 C29 N4 179.3(3) . . . . ?
Cu2 N5 C29 N4 1.2(5) . . . . ?
C34 N4 C29 N5 -31.5(5) . . . . ?
C39 N4 C29 N5 144.2(3) . . . . ?
C34 N4 C29 C30 150.6(4) . . . . ?
C39 N4 C29 C30 -33.8(5) . . . . ?
N5 C29 C30 C31 1.0(6) . . . . ?
N4 C29 C30 C31 179.0(4) . . . . ?
C29 C30 C31 C32 1.4(8) . . . . ?
C30 C31 C32 C33 -1.9(8) . . . . ?
C31 C32 C33 N5 0.0(7) . . . . ?
C29 N5 C33 C32 2.3(6) . . . . ?
Cu2 N5 C33 C32 -179.5(3) . . . . ?
C38 N6 C34 C35 0.8(5) . . . . ?
Cu2 N6 C34 C35 -177.4(3) . . . . ?
C38 N6 C34 N4 178.9(3) . . . . ?
Cu2 N6 C34 N4 0.7(4) . . . . ?
C29 N4 C34 N6 30.3(5) . . . . ?
C39 N4 C34 N6 -145.3(3) . . . . ?
C29 N4 C34 C35 -151.6(4) . . . . ?
C39 N4 C34 C35 32.8(4) . . . . ?
N6 C34 C35 C36 0.3(5) . . . . ?
N4 C34 C35 C36 -177.9(3) . . . . ?
C34 C35 C36 C37 -0.7(6) . . . . ?
C35 C36 C37 C38 0.0(6) . . . . ?
C36 C37 C38 N6 1.1(5) . . . . ?
C34 N6 C38 C37 -1.5(5) . . . . ?
Cu2 N6 C38 C37 176.7(3) . . . . ?
C34 N4 C39 C48 -90.7(4) . . . . ?
C29 N4 C39 C48 93.1(4) . . . . ?
C34 N4 C39 C40 87.8(4) . . . . ?
C29 N4 C39 C40 -88.4(4) . . . . ?
C48 C39 C40 C41 -179.3(3) . . . . ?
N4 C39 C40 C41 2.2(5) . . . . ?
C48 C39 C40 C45 2.2(5) . . . . ?
N4 C39 C40 C45 -176.4(3) . . . . ?
C39 C40 C41 C42 179.6(3) . . . . ?
C45 C40 C41 C42 -1.9(5) . . . . ?
C40 C41 C42 C43 1.2(6) . . . . ?
C41 C42 C43 C44 -0.7(6) . . . . ?
C42 C43 C44 C45 0.9(7) . . . . ?
C43 C44 C45 C46 -179.5(4) . . . . ?
C43 C44 C45 C40 -1.5(6) . . . . ?
C41 C40 C45 C46 180.0(3) . . . . ?
C39 C40 C45 C46 -1.4(5) . . . . ?
C41 C40 C45 C44 1.9(5) . . . . ?
C39 C40 C45 C44 -179.4(3) . . . . ?
C44 C45 C46 C47 177.6(4) . . . . ?
C40 C45 C46 C47 -0.4(6) . . . . ?
C45 C46 C47 C48 1.4(7) . . . . ?
C40 C39 C48 C47 -1.2(6) . . . . ?
N4 C39 C48 C47 177.2(4) . . . . ?
C46 C47 C48 C39 -0.6(7) . . . . ?
N5 Cu2 C49 C50 173.2(3) . . . . ?
N6 Cu2 C49 C50 6.9(6) . . . . ?
Cu2 C49 C50 C51 -97.8(4) . . . . ?
N5 Cu2 C50 C49 -13.6(5) . . . . ?
N6 Cu2 C50 C49 -176.5(3) . . . . ?
N5 Cu2 C50 C51 108.9(3) . . . . ?
N6 Cu2 C50 C51 -53.9(3) . . . . ?
C49 Cu2 C50 C51 122.5(5) . . . . ?
C49 C50 C51 C56 -166.3(4) . . . . ?
Cu2 C50 C51 C56 117.1(3) . . . . ?
C49 C50 C51 C52 15.6(6) . . . . ?
Cu2 C50 C51 C52 -61.0(4) . . . . ?
C56 C51 C52 C53 1.0(6) . . . . ?
C50 C51 C52 C53 179.1(3) . . . . ?
C51 C52 C53 C54 0.4(6) . . . . ?
C52 C53 C54 C55 -1.7(7) . . . . ?
C53 C54 C55 C56 1.5(8) . . . . ?
C54 C55 C56 C51 0.0(7) . . . . ?
C52 C51 C56 C55 -1.2(6) . . . . ?
C50 C51 C56 C55 -179.4(4) . . . . ?
N3 N2 C21 C22 -9.7(3) . . . . ?
N2 C1 C6 N3 13.1(3) . . . . ?
N6 N5 C49 C50 -2.1(3) . . . . ?
N5 C29 C34 N6 -1.1(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.590
_refine_diff_density_min -0.378
_refine_diff_density_rms 0.068