# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full 'Dalton Trans.'
_journal_coden_cambridge 0222
_journal_year ?
_journal_volume ?
_journal_page_first ?
_publ_contact_author_name 'M. Fatima C. Guedes da Silva'
_publ_contact_author_email fatima.guedes@ist.utl.pt
loop_
_publ_author_name
M.N.Kopylovich
T.C.O.M.Leod
K.T.Mahmudov
M.F.C.G.d.Silva
;
A.J.L.Pombeiro
;
data_Compound5
_database_code_depnum_ccdc_archive 'CCDC 797547'
#TrackingRef 'Compound5.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C24 H28 N4 O8 Zn2'
_chemical_formula_sum 'C24 H28 N4 O8 Zn2'
_chemical_formula_weight 631.24
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'
Zn Zn 0.2839 1.4301 '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_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.0218(4)
_cell_length_b 8.8006(3)
_cell_length_c 10.3280(5)
_cell_angle_alpha 93.178(2)
_cell_angle_beta 103.423(3)
_cell_angle_gamma 111.763(2)
_cell_volume 650.52(5)
_cell_formula_units_Z 1
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 1847
_cell_measurement_theta_min 2.84
_cell_measurement_theta_max 25.93
_exptl_crystal_description prism
_exptl_crystal_colour orange
_exptl_crystal_size_max 0.26
_exptl_crystal_size_mid 0.09
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.611
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 324
_exptl_absorpt_coefficient_mu 1.899
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6381
_exptl_absorpt_correction_T_max 0.8629
_exptl_absorpt_process_details sadabs
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 6173
_diffrn_reflns_av_R_equivalents 0.0415
_diffrn_reflns_av_sigmaI/netI 0.0545
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.84
_diffrn_reflns_theta_max 25.35
_reflns_number_total 2320
_reflns_number_gt 1915
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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^)+(0.0423P)^2^+0.0048P] 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 2320
_refine_ls_number_parameters 178
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0468
_refine_ls_R_factor_gt 0.0337
_refine_ls_wR_factor_ref 0.0793
_refine_ls_wR_factor_gt 0.0734
_refine_ls_goodness_of_fit_ref 0.969
_refine_ls_restrained_S_all 0.969
_refine_ls_shift/su_max 0.003
_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
Zn1 Zn 0.41933(5) 0.33715(4) 0.39891(4) 0.01735(13) Uani 1 1 d . . .
O1 O 0.3615(3) 0.5353(2) 0.4263(2) 0.0183(5) Uani 1 1 d . . .
O2 O -0.1598(3) -0.3006(3) 0.3005(2) 0.0305(6) Uani 1 1 d . . .
O3 O 0.1913(3) 0.1724(2) 0.2593(2) 0.0212(5) Uani 1 1 d . . .
O4 O 0.5886(3) 0.3976(3) 0.2771(2) 0.0244(5) Uani 1 1 d . . .
H4 H 0.664(5) 0.486(4) 0.286(4) 0.029 Uiso 1 1 d . . .
N1 N 0.3854(3) 0.1553(3) 0.5136(3) 0.0162(5) Uani 1 1 d . . .
N2 N 0.2556(3) 0.0101(3) 0.4950(3) 0.0177(6) Uani 1 1 d . . .
C1 C 0.1105(4) -0.0521(3) 0.3814(3) 0.0174(7) Uani 1 1 d . . .
C2 C -0.0162(4) -0.2179(4) 0.3906(3) 0.0208(7) Uani 1 1 d . . .
C3 C 0.0325(4) -0.2896(4) 0.5158(4) 0.0258(8) Uani 1 1 d . . .
H3A H -0.0718 -0.3930 0.5151 0.039 Uiso 1 1 calc R . .
H3B H 0.0570 -0.2104 0.5954 0.039 Uiso 1 1 calc R . .
H3C H 0.1440 -0.3120 0.5185 0.039 Uiso 1 1 calc R . .
C4 C 0.0795(4) 0.0301(4) 0.2681(3) 0.0192(7) Uani 1 1 d . . .
C5 C -0.0920(4) -0.0475(4) 0.1517(4) 0.0299(8) Uani 1 1 d . . .
H5A H -0.0911 0.0295 0.0866 0.045 Uiso 1 1 calc R . .
H5B H -0.2032 -0.0728 0.1844 0.045 Uiso 1 1 calc R . .
H5C H -0.0938 -0.1500 0.1079 0.045 Uiso 1 1 calc R . .
C6 C 0.5212(4) 0.1998(4) 0.6401(3) 0.0175(7) Uani 1 1 d . . .
C7 C 0.6514(4) 0.3652(4) 0.6677(3) 0.0168(7) Uani 1 1 d . . .
C8 C 0.7905(4) 0.4203(4) 0.7898(3) 0.0233(7) Uani 1 1 d . . .
H8 H 0.8800 0.5314 0.8101 0.028 Uiso 1 1 calc R . .
C9 C 0.7971(5) 0.3122(4) 0.8811(4) 0.0294(8) Uani 1 1 d . . .
H9 H 0.8917 0.3502 0.9642 0.035 Uiso 1 1 calc R . .
C10 C 0.6696(4) 0.1509(4) 0.8539(3) 0.0272(8) Uani 1 1 d . . .
H10 H 0.6768 0.0787 0.9181 0.033 Uiso 1 1 calc R . .
C11 C 0.5305(4) 0.0929(4) 0.7333(3) 0.0228(7) Uani 1 1 d . . .
H11 H 0.4422 -0.0187 0.7145 0.027 Uiso 1 1 calc R . .
C12 C 0.5325(6) 0.3484(5) 0.1349(4) 0.0542(12) Uani 1 1 d . . .
H12A H 0.4711 0.2274 0.1136 0.081 Uiso 1 1 calc R . .
H12B H 0.6423 0.3870 0.1000 0.081 Uiso 1 1 calc R . .
H12C H 0.4454 0.3971 0.0930 0.081 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
Zn1 0.0178(2) 0.0111(2) 0.0191(2) 0.00258(14) 0.00400(14) 0.00185(15)
O1 0.0196(10) 0.0114(11) 0.0196(12) 0.0026(9) 0.0027(9) 0.0029(9)
O2 0.0230(12) 0.0179(12) 0.0385(16) 0.0001(11) 0.0066(12) -0.0038(10)
O3 0.0209(11) 0.0128(11) 0.0224(13) 0.0016(9) 0.0017(9) 0.0012(9)
O4 0.0250(12) 0.0151(12) 0.0251(14) 0.0008(10) 0.0083(10) -0.0016(10)
N1 0.0170(12) 0.0113(13) 0.0194(15) 0.0024(11) 0.0069(11) 0.0034(11)
N2 0.0164(12) 0.0125(13) 0.0261(16) 0.0028(11) 0.0102(11) 0.0051(11)
C1 0.0149(15) 0.0097(15) 0.0249(18) -0.0014(13) 0.0065(13) 0.0018(13)
C2 0.0168(16) 0.0138(16) 0.032(2) -0.0004(14) 0.0130(15) 0.0035(14)
C3 0.0271(17) 0.0144(17) 0.037(2) 0.0060(15) 0.0152(16) 0.0059(14)
C4 0.0182(15) 0.0145(17) 0.0261(19) -0.0003(14) 0.0101(14) 0.0058(14)
C5 0.0188(16) 0.0220(18) 0.035(2) 0.0043(16) 0.0002(15) -0.0026(14)
C6 0.0169(15) 0.0149(16) 0.0218(18) -0.0005(13) 0.0072(13) 0.0067(13)
C7 0.0196(15) 0.0169(16) 0.0165(17) 0.0024(13) 0.0077(13) 0.0084(13)
C8 0.0225(16) 0.0146(17) 0.0264(19) -0.0009(14) 0.0021(14) 0.0036(14)
C9 0.0337(19) 0.029(2) 0.0227(19) 0.0000(15) -0.0003(15) 0.0149(16)
C10 0.0327(18) 0.0252(19) 0.024(2) 0.0090(15) 0.0045(15) 0.0133(16)
C11 0.0249(16) 0.0151(17) 0.030(2) 0.0048(14) 0.0099(15) 0.0085(14)
C12 0.064(3) 0.043(3) 0.026(2) -0.0066(19) 0.019(2) -0.014(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
Zn1 O1 1.986(2) . ?
Zn1 O4 2.011(2) . ?
Zn1 N1 2.019(2) . ?
Zn1 O3 2.025(2) . ?
Zn1 O1 2.109(2) 2_666 ?
Zn1 Zn1 3.0955(7) 2_666 ?
O1 C7 1.354(3) 2_666 ?
O1 Zn1 2.109(2) 2_666 ?
O2 C2 1.236(4) . ?
O3 C4 1.264(3) . ?
O4 C12 1.423(4) . ?
O4 H4 0.77(4) . ?
N1 N2 1.283(3) . ?
N1 C6 1.419(4) . ?
N2 C1 1.361(4) . ?
C1 C4 1.431(4) . ?
C1 C2 1.460(4) . ?
C2 C3 1.503(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.500(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.392(4) . ?
C6 C7 1.407(4) . ?
C7 O1 1.354(3) 2_666 ?
C7 C8 1.396(4) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
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 Zn1 O4 103.86(9) . . ?
O1 Zn1 N1 126.31(9) . . ?
O4 Zn1 N1 127.15(9) . . ?
O1 Zn1 O3 104.79(8) . . ?
O4 Zn1 O3 96.89(9) . . ?
N1 Zn1 O3 86.38(9) . . ?
O1 Zn1 O1 81.84(8) . 2_666 ?
O4 Zn1 O1 93.10(8) . 2_666 ?
N1 Zn1 O1 80.03(9) . 2_666 ?
O3 Zn1 O1 166.23(8) . 2_666 ?
O1 Zn1 Zn1 42.41(6) . 2_666 ?
O4 Zn1 Zn1 100.98(7) . 2_666 ?
N1 Zn1 Zn1 105.19(8) . 2_666 ?
O3 Zn1 Zn1 145.65(6) . 2_666 ?
O1 Zn1 Zn1 39.43(5) 2_666 2_666 ?
C7 O1 Zn1 123.89(19) 2_666 . ?
C7 O1 Zn1 111.93(17) 2_666 2_666 ?
Zn1 O1 Zn1 98.16(8) . 2_666 ?
C4 O3 Zn1 129.8(2) . . ?
C12 O4 Zn1 125.4(2) . . ?
C12 O4 H4 103(3) . . ?
Zn1 O4 H4 121(3) . . ?
N2 N1 C6 114.6(2) . . ?
N2 N1 Zn1 130.9(2) . . ?
C6 N1 Zn1 114.39(19) . . ?
N1 N2 C1 122.9(3) . . ?
N2 C1 C4 126.4(3) . . ?
N2 C1 C2 110.4(3) . . ?
C4 C1 C2 123.3(3) . . ?
O2 C2 C1 122.9(3) . . ?
O2 C2 C3 119.3(3) . . ?
C1 C2 C3 117.8(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O3 C4 C1 123.1(3) . . ?
O3 C4 C5 115.4(3) . . ?
C1 C4 C5 121.5(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 120.5(3) . . ?
C11 C6 N1 124.6(3) . . ?
C7 C6 N1 114.9(3) . . ?
O1 C7 C8 122.4(3) 2_666 . ?
O1 C7 C6 118.6(3) 2_666 . ?
C8 C7 C6 119.0(3) . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C6 C11 H11 120.3 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full 25.35
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max 0.404
_refine_diff_density_min -0.395
_refine_diff_density_rms 0.082
# Attachment 'Compound6.cif'
data_Compound6
_database_code_depnum_ccdc_archive 'CCDC 797548'
#TrackingRef 'Compound6.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H17 N3 O7 S Zn'
_chemical_formula_sum 'C13 H17 N3 O7 S Zn'
_chemical_formula_weight 424.73
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.782(6)
_cell_length_b 10.621(9)
_cell_length_c 10.703(9)
_cell_angle_alpha 115.83(2)
_cell_angle_beta 106.16(2)
_cell_angle_gamma 90.23(3)
_cell_volume 854.0(12)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 481
_cell_measurement_theta_min 2.29
_cell_measurement_theta_max 19.04
_exptl_crystal_description plate
_exptl_crystal_colour orange
_exptl_crystal_size_min 0.08
_exptl_crystal_size_mid 0.13
_exptl_crystal_size_max 0.45
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.652
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 436
_exptl_absorpt_coefficient_mu 1.602
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.7741
_exptl_absorpt_correction_T_max 0.8745
_exptl_absorpt_process_details sadabs
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71069
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 4652
_diffrn_reflns_av_R_equivalents 0.0813
_diffrn_reflns_av_sigmaI/netI 0.1877
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.74
_diffrn_reflns_theta_max 25.35
_reflns_number_total 2859
_reflns_number_gt 1321
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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^)+(0.0213P)^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 0.0030(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 2859
_refine_ls_number_parameters 231
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1659
_refine_ls_R_factor_gt 0.0603
_refine_ls_wR_factor_ref 0.0979
_refine_ls_wR_factor_gt 0.0797
_refine_ls_goodness_of_fit_ref 0.839
_refine_ls_restrained_S_all 0.839
_refine_ls_shift/su_max 0.009
_refine_ls_shift/su_mean 0.001
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
C1 C 0.6401(7) -0.0448(6) 0.7823(7) 0.0306(17) Uani 1 1 d . . .
C2 C 0.6380(7) 0.0510(6) 0.9220(6) 0.0269(16) Uani 1 1 d . . .
C3 C 0.7322(8) 0.0428(7) 1.0429(7) 0.043(2) Uani 1 1 d . . .
H3 H 0.7292 0.1091 1.1367 0.051 Uiso 1 1 calc R . .
C4 C 0.8326(8) -0.0603(7) 1.0320(7) 0.0404(19) Uani 1 1 d . . .
H4 H 0.8972 -0.0660 1.1163 0.049 Uiso 1 1 calc R . .
C5 C 0.8344(8) -0.1516(7) 0.8972(8) 0.0377(19) Uani 1 1 d . . .
C6 C 0.7392(8) -0.1493(7) 0.7690(7) 0.0407(19) Uani 1 1 d . . .
H6 H 0.7422 -0.2170 0.6758 0.049 Uiso 1 1 calc R . .
C11 C 0.2319(8) 0.4912(7) 0.9895(7) 0.054(2) Uani 1 1 d . . .
H11A H 0.3045 0.5810 1.0459 0.081 Uiso 1 1 calc R . .
H11B H 0.1646 0.4841 1.0461 0.081 Uiso 1 1 calc R . .
H11C H 0.1638 0.4869 0.8976 0.081 Uiso 1 1 calc R . .
C12 C 0.3288(8) 0.3700(7) 0.9568(7) 0.0379(18) Uani 1 1 d . . .
C13 C 0.4472(8) 0.3534(7) 1.0697(7) 0.0372(19) Uani 1 1 d . . .
C14 C 0.4856(9) 0.4528(7) 1.2234(7) 0.046(2) Uani 1 1 d . . .
C15 C 0.6171(9) 0.4325(8) 1.3351(7) 0.076(3) Uani 1 1 d . . .
H15A H 0.6353 0.5133 1.4313 0.114 Uiso 1 1 calc R . .
H15B H 0.7159 0.4254 1.3082 0.114 Uiso 1 1 calc R . .
H15C H 0.5859 0.3456 1.3383 0.114 Uiso 1 1 calc R . .
C21 C 0.0060(9) -0.2636(8) 0.4901(8) 0.083(3) Uani 1 1 d . . .
H21A H 0.0068 -0.2526 0.5861 0.124 Uiso 1 1 calc R . .
H21B H -0.0077 -0.3644 0.4223 0.124 Uiso 1 1 calc R . .
H21C H -0.0827 -0.2208 0.4529 0.124 Uiso 1 1 calc R . .
C22 C 0.1335(9) -0.1832(8) 0.3337(7) 0.076(3) Uani 1 1 d . . .
H22A H 0.0454 -0.1280 0.3257 0.114 Uiso 1 1 calc R . .
H22B H 0.0986 -0.2812 0.2577 0.114 Uiso 1 1 calc R . .
H22C H 0.2253 -0.1426 0.3212 0.114 Uiso 1 1 calc R . .
N1 N 0.5350(6) 0.1530(5) 0.9227(5) 0.0314(14) Uani 1 1 d . . .
N2 N 0.5424(6) 0.2483(6) 1.0504(5) 0.0355(15) Uani 1 1 d . . .
N5 N 0.9351(7) -0.2644(7) 0.8779(8) 0.0538(18) Uani 1 1 d . . .
O1 O 0.1939(5) -0.0242(5) 0.6129(5) 0.0546(15) Uani 1 1 d . . .
O2 O 0.2990(5) 0.2845(5) 0.8253(5) 0.0479(14) Uani 1 1 d . . .
O4 O 0.4101(6) 0.5527(5) 1.2690(5) 0.0714(18) Uani 1 1 d . . .
O5 O 0.9427(7) -0.3435(6) 0.7572(6) 0.086(2) Uani 1 1 d . . .
O6 O 1.0157(7) -0.2687(6) 0.9896(6) 0.0765(19) Uani 1 1 d . . .
O10 O 0.4148(6) 0.1890(5) 0.5805(4) 0.0518(14) Uani 1 1 d . . .
O11 O 0.5493(5) -0.0346(5) 0.6663(4) 0.0474(14) Uani 1 1 d . . .
Zn1 Zn 0.39845(11) 0.11170(9) 0.71797(8) 0.0401(3) Uani 1 1 d . . .
S1 S 0.1894(2) -0.1791(2) 0.5063(2) 0.0573(7) Uani 1 1 d . . .
H10A H 0.4571 0.1227 0.5074 0.086 Uiso 1 1 d . . .
H10B H 0.4886 0.2768 0.6349 0.086 Uiso 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
C1 0.028(4) 0.031(4) 0.045(4) 0.022(4) 0.020(3) 0.004(4)
C2 0.024(4) 0.034(4) 0.028(4) 0.017(3) 0.012(3) 0.005(3)
C3 0.043(5) 0.052(5) 0.027(4) 0.011(4) 0.014(3) 0.007(4)
C4 0.034(5) 0.052(5) 0.044(5) 0.028(4) 0.013(4) 0.008(4)
C5 0.035(5) 0.041(5) 0.056(5) 0.034(4) 0.020(4) 0.022(4)
C6 0.043(5) 0.035(5) 0.040(4) 0.012(4) 0.017(4) 0.014(4)
C11 0.053(6) 0.045(5) 0.059(5) 0.018(4) 0.022(4) 0.029(4)
C12 0.038(5) 0.037(5) 0.042(4) 0.018(4) 0.017(4) 0.003(4)
C13 0.042(5) 0.030(4) 0.035(4) 0.007(3) 0.020(4) 0.012(4)
C14 0.052(6) 0.041(5) 0.034(4) 0.005(4) 0.019(4) -0.005(4)
C15 0.093(7) 0.074(6) 0.033(5) 0.005(4) 0.010(5) 0.028(6)
C21 0.064(6) 0.108(8) 0.069(6) 0.041(6) 0.010(5) -0.025(5)
C22 0.071(7) 0.095(7) 0.059(6) 0.028(5) 0.028(5) 0.001(5)
N1 0.031(4) 0.038(4) 0.026(3) 0.012(3) 0.015(3) 0.008(3)
N2 0.030(4) 0.043(4) 0.033(3) 0.016(3) 0.011(3) 0.006(3)
N5 0.044(5) 0.058(5) 0.083(5) 0.047(4) 0.029(4) 0.020(4)
O1 0.043(3) 0.053(3) 0.044(3) 0.005(3) 0.009(2) 0.005(3)
O2 0.063(4) 0.048(3) 0.030(3) 0.014(3) 0.015(2) 0.028(3)
O4 0.081(4) 0.049(4) 0.055(4) -0.002(3) 0.020(3) 0.028(3)
O5 0.099(5) 0.092(5) 0.089(5) 0.046(4) 0.054(4) 0.067(4)
O6 0.083(5) 0.091(5) 0.084(4) 0.064(4) 0.026(3) 0.049(4)
O10 0.082(4) 0.045(3) 0.033(3) 0.017(2) 0.027(3) 0.023(3)
O11 0.057(4) 0.061(3) 0.025(3) 0.018(2) 0.016(2) 0.033(3)
Zn1 0.0413(6) 0.0455(6) 0.0267(5) 0.0113(4) 0.0092(4) 0.0148(4)
S1 0.0510(15) 0.0567(15) 0.0522(14) 0.0202(12) 0.0063(11) 0.0091(12)
_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
C1 O11 1.326(6) . ?
C1 C6 1.396(8) . ?
C1 C2 1.401(8) . ?
C2 C3 1.367(8) . ?
C2 N1 1.413(7) . ?
C3 C4 1.394(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.348(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(8) . ?
C5 N5 1.468(8) . ?
C6 H6 0.9500 . ?
C11 C12 1.511(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O2 1.246(7) . ?
C12 C13 1.436(8) . ?
C13 N2 1.375(7) . ?
C13 C14 1.452(8) . ?
C14 O4 1.240(7) . ?
C14 C15 1.506(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C21 S1 1.768(8) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 S1 1.755(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 N2 1.281(6) . ?
N1 Zn1 2.032(5) . ?
N5 O5 1.217(7) . ?
N5 O6 1.228(7) . ?
O1 S1 1.532(4) . ?
O1 Zn1 2.004(5) . ?
O2 Zn1 2.046(4) . ?
O10 Zn1 2.007(4) . ?
O10 H10A 0.964 . ?
O10 H10B 0.970 . ?
O11 Zn1 2.037(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
O11 C1 C6 121.5(6) . . ?
O11 C1 C2 119.8(6) . . ?
C6 C1 C2 118.7(6) . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 N1 125.5(6) . . ?
C1 C2 N1 113.9(5) . . ?
C2 C3 C4 121.6(6) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.4(6) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C4 C5 C6 123.6(6) . . ?
C4 C5 N5 120.1(6) . . ?
C6 C5 N5 116.3(6) . . ?
C1 C6 C5 118.2(6) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 121.8(6) . . ?
O2 C12 C11 115.8(6) . . ?
C13 C12 C11 122.4(6) . . ?
N2 C13 C12 126.5(6) . . ?
N2 C13 C14 110.7(6) . . ?
C12 C13 C14 122.8(6) . . ?
O4 C14 C13 122.7(7) . . ?
O4 C14 C15 117.4(6) . . ?
C13 C14 C15 119.8(6) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 N1 C2 114.4(5) . . ?
N2 N1 Zn1 133.4(4) . . ?
C2 N1 Zn1 112.2(4) . . ?
N1 N2 C13 121.5(5) . . ?
O5 N5 O6 122.9(7) . . ?
O5 N5 C5 120.5(7) . . ?
O6 N5 C5 116.5(7) . . ?
S1 O1 Zn1 121.6(3) . . ?
C12 O2 Zn1 132.9(4) . . ?
Zn1 O10 H10A 109.2 . . ?
Zn1 O10 H10B 108.9 . . ?
H10A O10 H10B 108.3 . . ?
C1 O11 Zn1 112.3(4) . . ?
O1 Zn1 O10 104.3(2) . . ?
O1 Zn1 N1 122.3(2) . . ?
O10 Zn1 N1 133.3(2) . . ?
O1 Zn1 O11 96.9(2) . . ?
O10 Zn1 O11 97.13(19) . . ?
N1 Zn1 O11 80.74(18) . . ?
O1 Zn1 O2 96.2(2) . . ?
O10 Zn1 O2 89.23(18) . . ?
N1 Zn1 O2 83.86(19) . . ?
O11 Zn1 O2 163.56(17) . . ?
O1 S1 C22 104.5(3) . . ?
O1 S1 C21 103.8(3) . . ?
C22 S1 C21 98.0(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
O11 C1 C2 C3 -179.3(6) . . . . ?
C6 C1 C2 C3 0.5(9) . . . . ?
O11 C1 C2 N1 -0.4(8) . . . . ?
C6 C1 C2 N1 179.3(6) . . . . ?
C1 C2 C3 C4 -0.2(10) . . . . ?
N1 C2 C3 C4 -178.9(6) . . . . ?
C2 C3 C4 C5 0.5(10) . . . . ?
C3 C4 C5 C6 -1.2(11) . . . . ?
C3 C4 C5 N5 -178.8(6) . . . . ?
O11 C1 C6 C5 178.7(6) . . . . ?
C2 C1 C6 C5 -1.1(10) . . . . ?
C4 C5 C6 C1 1.5(11) . . . . ?
N5 C5 C6 C1 179.2(6) . . . . ?
O2 C12 C13 N2 1.4(11) . . . . ?
C11 C12 C13 N2 -179.0(6) . . . . ?
O2 C12 C13 C14 179.1(6) . . . . ?
C11 C12 C13 C14 -1.2(10) . . . . ?
N2 C13 C14 O4 -176.1(7) . . . . ?
C12 C13 C14 O4 5.8(11) . . . . ?
N2 C13 C14 C15 1.1(9) . . . . ?
C12 C13 C14 C15 -176.9(7) . . . . ?
C3 C2 N1 N2 4.4(9) . . . . ?
C1 C2 N1 N2 -174.3(5) . . . . ?
C3 C2 N1 Zn1 -173.3(5) . . . . ?
C1 C2 N1 Zn1 8.0(6) . . . . ?
C2 N1 N2 C13 -178.6(6) . . . . ?
Zn1 N1 N2 C13 -1.6(9) . . . . ?
C12 C13 N2 N1 1.6(10) . . . . ?
C14 C13 N2 N1 -176.4(5) . . . . ?
C4 C5 N5 O5 -176.9(7) . . . . ?
C6 C5 N5 O5 5.3(10) . . . . ?
C4 C5 N5 O6 -0.5(10) . . . . ?
C6 C5 N5 O6 -178.3(6) . . . . ?
C13 C12 O2 Zn1 -4.4(10) . . . . ?
C11 C12 O2 Zn1 175.9(4) . . . . ?
C6 C1 O11 Zn1 172.9(5) . . . . ?
C2 C1 O11 Zn1 -7.3(7) . . . . ?
S1 O1 Zn1 O10 87.6(3) . . . . ?
S1 O1 Zn1 N1 -95.0(3) . . . . ?
S1 O1 Zn1 O11 -11.6(3) . . . . ?
S1 O1 Zn1 O2 178.4(3) . . . . ?
N2 N1 Zn1 O1 -93.9(6) . . . . ?
C2 N1 Zn1 O1 83.3(4) . . . . ?
N2 N1 Zn1 O10 82.7(6) . . . . ?
C2 N1 Zn1 O10 -100.2(5) . . . . ?
N2 N1 Zn1 O11 173.8(6) . . . . ?
C2 N1 Zn1 O11 -9.1(4) . . . . ?
N2 N1 Zn1 O2 -0.4(6) . . . . ?
C2 N1 Zn1 O2 176.7(4) . . . . ?
C1 O11 Zn1 O1 -112.9(4) . . . . ?
C1 O11 Zn1 O10 141.7(4) . . . . ?
C1 O11 Zn1 N1 8.9(4) . . . . ?
C1 O11 Zn1 O2 29.6(10) . . . . ?
C12 O2 Zn1 O1 125.5(6) . . . . ?
C12 O2 Zn1 O10 -130.1(6) . . . . ?
C12 O2 Zn1 N1 3.6(6) . . . . ?
C12 O2 Zn1 O11 -17.0(12) . . . . ?
Zn1 O1 S1 C22 -95.8(4) . . . . ?
Zn1 O1 S1 C21 162.0(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_theta_full 25.35
_diffrn_measured_fraction_theta_full 0.912
_refine_diff_density_max 0.539
_refine_diff_density_min -0.419
_refine_diff_density_rms 0.092
data_Compound7
_database_code_depnum_ccdc_archive 'CCDC 797549'
#TrackingRef '- Compound7_corrected.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C28 H32 N4 O8 Zn2'
_chemical_formula_sum 'C28 H32 N4 O8 Zn2'
_chemical_formula_weight 683.32
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'
Zn Zn 0.2839 1.4301 '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_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 6.8688(3)
_cell_length_b 9.8233(5)
_cell_length_c 11.9184(6)
_cell_angle_alpha 106.825(2)
_cell_angle_beta 105.369(3)
_cell_angle_gamma 95.625(2)
_cell_volume 728.81(6)
_cell_formula_units_Z 1
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 1828
_cell_measurement_theta_min 2.38
_cell_measurement_theta_max 25.10
_exptl_crystal_description prism
_exptl_crystal_colour orange
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.557
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 352
_exptl_absorpt_coefficient_mu 1.701
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6473
_exptl_absorpt_correction_T_max 0.8219
_exptl_absorpt_process_details sadabs
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71069
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 4919
_diffrn_reflns_av_R_equivalents 0.0283
_diffrn_reflns_av_sigmaI/netI 0.0467
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 3.12
_diffrn_reflns_theta_max 25.32
_reflns_number_total 2601
_reflns_number_gt 2154
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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 hydrogen atoms H10A and H10C from the coordinated water molecule O10 were
located in the subsequent difference Fourier maps, refined and geometrically
restrained to the same distance (DFIX command of SHELXL97).
The atomic positions of the C13, C14, C15, C17 and C18 carbon atoms were subtly
disordered and the anisotropy of the ADPs were not strong
enough for SHELXL to generate a second set of peaks in the difference Fourier
Map. Therefore, the same initial coordinates for those sites of split atoms
were used (one of the two sites slightly changed by hand, to avoid a mathematical
singularity) and SHELXL separated them during the refinement. In spite of this,
the disordered C14 carbon atom had to be refined isotropically.
The positions of the hydrogen atoms bonded to the dissordered carbon atoms
were included in calculated positions by using the PART instructions
in SHELXL and treated as riding atoms.
;
_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^)+(0.0387P)^2^+0.4071P] 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 2601
_refine_ls_number_parameters 223
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0482
_refine_ls_R_factor_gt 0.0359
_refine_ls_wR_factor_ref 0.0870
_refine_ls_wR_factor_gt 0.0819
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_restrained_S_all 1.049
_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
C1 C 0.1257(4) 0.4379(3) 0.1050(3) 0.0151(6) Uani 1 1 d . . .
C2 C 0.3016(4) 0.5481(3) 0.1517(3) 0.0170(6) Uani 1 1 d . . .
C3 C 0.3178(5) 0.6665(3) 0.2537(3) 0.0219(7) Uani 1 1 d . . .
H3 H 0.4374 0.7405 0.2876 0.026 Uiso 1 1 calc R . .
C4 C 0.1613(5) 0.6769(3) 0.3057(3) 0.0294(8) Uani 1 1 d . . .
H4 H 0.1735 0.7581 0.3756 0.035 Uiso 1 1 calc R . .
C5 C -0.0151(5) 0.5695(4) 0.2568(3) 0.0349(9) Uani 1 1 d . . .
H5 H -0.1235 0.5786 0.2925 0.042 Uiso 1 1 calc R . .
C6 C -0.0324(5) 0.4510(3) 0.1576(3) 0.0250(7) Uani 1 1 d . . .
H6 H -0.1526 0.3776 0.1247 0.030 Uiso 1 1 calc R . .
C11 C -0.0343(4) 0.0919(3) -0.1309(3) 0.0177(6) Uani 1 1 d . A .
C12 C 0.0938(5) 0.0739(3) -0.2084(3) 0.0299(8) Uani 1 1 d . . .
C13B C 0.088(3) -0.0783(18) -0.2970(16) 0.024(3) Uani 0.47(2) 1 d P A 2
H13A H 0.1790 -0.1294 -0.2511 0.029 Uiso 0.47(2) 1 calc PR A 2
H13B H 0.1425 -0.0671 -0.3636 0.029 Uiso 0.47(2) 1 calc PR A 2
C14B C -0.1232(19) -0.1680(8) -0.3530(7) 0.019(2) Uiso 0.47(2) 1 d P A 2
C15 C -0.2183(5) -0.1688(3) -0.2468(3) 0.0273(7) Uani 1 1 d . . .
H15A H -0.3548 -0.2283 -0.2648 0.033 Uiso 1 1 calc R A 1
H15B H -0.1120 -0.2205 -0.2139 0.033 Uiso 1 1 calc R A 1
C16 C -0.1981(4) -0.0254(3) -0.1519(3) 0.0189(6) Uani 1 1 d . A .
C17B C -0.266(3) -0.1014(13) -0.4325(12) 0.039(3) Uani 0.47(2) 1 d P A 2
H17A H -0.2729 -0.0044 -0.3826 0.059 Uiso 0.47(2) 1 calc PR A 2
H17B H -0.4035 -0.1621 -0.4664 0.059 Uiso 0.47(2) 1 calc PR A 2
H17C H -0.2139 -0.0943 -0.5000 0.059 Uiso 0.47(2) 1 calc PR A 2
C18B C -0.116(3) -0.3201(14) -0.4296(13) 0.032(3) Uani 0.47(2) 1 d P A 2
H18A H -0.0196 -0.3619 -0.3785 0.047 Uiso 0.47(2) 1 calc PR A 2
H18B H -0.0692 -0.3155 -0.4996 0.047 Uiso 0.47(2) 1 calc PR A 2
H18C H -0.2530 -0.3806 -0.4599 0.047 Uiso 0.47(2) 1 calc PR A 2
N1 N 0.1250(3) 0.3194(2) 0.0039(2) 0.0157(5) Uani 1 1 d . A .
N2 N -0.0254(3) 0.2130(2) -0.0348(2) 0.0157(5) Uani 1 1 d . . .
O1 O 0.4514(3) 0.5320(2) 0.0991(2) 0.0280(5) Uani 1 1 d . . .
O2 O 0.2411(4) 0.1675(2) -0.1985(2) 0.0392(7) Uani 1 1 d . A .
O3 O -0.3194(3) -0.0126(2) -0.0902(2) 0.0281(5) Uani 1 1 d . . .
O10 O 0.5504(3) 0.2125(2) 0.0410(2) 0.0330(6) Uani 1 1 d D A .
Zn1 Zn 0.38901(6) 0.33668(4) -0.04481(4) 0.02843(15) Uani 1 1 d . . .
C18A C -0.203(2) -0.2998(13) -0.4527(13) 0.035(3) Uani 0.53(2) 1 d P A 1
H18D H -0.3419 -0.3573 -0.4790 0.052 Uiso 0.53(2) 1 calc PR A 1
H18E H -0.1042 -0.3488 -0.4111 0.052 Uiso 0.53(2) 1 calc PR A 1
H18F H -0.1685 -0.2895 -0.5249 0.052 Uiso 0.53(2) 1 calc PR A 1
C13A C 0.026(2) -0.0565(17) -0.3224(16) 0.027(3) Uani 0.53(2) 1 d P A 1
H13C H 0.0392 -0.0235 -0.3915 0.032 Uiso 0.53(2) 1 calc PR A 1
H13D H 0.1259 -0.1215 -0.3117 0.032 Uiso 0.53(2) 1 calc PR A 1
C17A C -0.355(2) -0.0753(11) -0.4252(10) 0.032(2) Uani 0.53(2) 1 d P A 1
H17D H -0.4925 -0.1313 -0.4449 0.048 Uiso 0.53(2) 1 calc PR A 1
H17E H -0.3311 -0.0686 -0.5012 0.048 Uiso 0.53(2) 1 calc PR A 1
H17F H -0.3431 0.0222 -0.3688 0.048 Uiso 0.53(2) 1 calc PR A 1
C14A C -0.1943(16) -0.1506(7) -0.3642(6) 0.016(2) Uiso 0.53(2) 1 d P A 1
H10A H 0.477(4) 0.161(3) 0.067(3) 0.023 Uiso 1 1 d D . .
H10C H 0.606(4) 0.160(3) -0.006(3) 0.023 Uiso 1 1 d 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
C1 0.0153(14) 0.0131(14) 0.0154(15) 0.0043(12) 0.0032(12) 0.0014(11)
C2 0.0168(14) 0.0176(15) 0.0194(15) 0.0089(12) 0.0072(13) 0.0025(12)
C3 0.0233(16) 0.0162(15) 0.0199(16) 0.0014(12) 0.0048(13) -0.0052(12)
C4 0.040(2) 0.0190(16) 0.0262(18) -0.0034(14) 0.0203(16) -0.0046(14)
C5 0.040(2) 0.0242(18) 0.043(2) 0.0002(16) 0.0320(18) -0.0034(15)
C6 0.0194(16) 0.0210(16) 0.0308(18) 0.0011(14) 0.0129(14) -0.0042(13)
C11 0.0231(16) 0.0124(14) 0.0158(15) 0.0034(12) 0.0061(13) -0.0009(12)
C12 0.045(2) 0.0187(16) 0.0232(17) -0.0006(14) 0.0191(16) -0.0069(15)
C13B 0.047(9) 0.010(5) 0.022(7) 0.003(4) 0.023(6) 0.008(5)
C15 0.0396(19) 0.0143(16) 0.0256(17) 0.0024(13) 0.0144(15) -0.0052(14)
C16 0.0201(15) 0.0159(15) 0.0187(15) 0.0054(12) 0.0032(13) 0.0023(12)
C17B 0.049(9) 0.026(5) 0.031(5) 0.006(4) -0.002(6) 0.000(5)
C18B 0.047(8) 0.020(5) 0.027(6) -0.001(4) 0.021(6) 0.000(5)
N1 0.0165(12) 0.0122(12) 0.0185(13) 0.0048(10) 0.0072(11) -0.0006(10)
N2 0.0147(12) 0.0135(12) 0.0183(13) 0.0042(10) 0.0054(10) 0.0017(10)
O1 0.0251(12) 0.0143(11) 0.0441(14) -0.0016(10) 0.0255(11) -0.0055(9)
O2 0.0552(16) 0.0236(13) 0.0382(14) -0.0052(11) 0.0371(13) -0.0114(12)
O3 0.0225(12) 0.0147(11) 0.0457(14) 0.0016(10) 0.0189(11) -0.0004(9)
O10 0.0233(12) 0.0139(12) 0.0629(17) 0.0009(11) 0.0295(12) -0.0011(9)
Zn1 0.0291(2) 0.0146(2) 0.0426(3) -0.00112(16) 0.02735(19) -0.00426(15)
C18A 0.040(7) 0.028(5) 0.031(5) -0.002(4) 0.017(6) 0.000(5)
C13A 0.039(8) 0.017(6) 0.033(7) 0.010(4) 0.020(6) 0.006(4)
C17A 0.038(6) 0.025(5) 0.025(4) 0.009(3) -0.002(5) 0.000(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
C1 C6 1.390(4) . ?
C1 C2 1.407(4) . ?
C1 N1 1.410(3) . ?
C2 O1 1.339(3) . ?
C2 C3 1.388(4) . ?
C3 C4 1.374(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.367(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C11 N2 1.375(4) . ?
C11 C12 1.423(4) . ?
C11 C16 1.444(4) . ?
C12 O2 1.255(4) . ?
C12 C13A 1.498(17) . ?
C12 C13B 1.551(16) . ?
C13B C14B 1.491(19) . ?
C13B H13A 0.9900 . ?
C13B H13B 0.9900 . ?
C14B C15 1.573(8) . ?
C14B C18B 1.522(14) . ?
C14B C17B 1.510(13) . ?
C15 C16 1.496(4) . ?
C15 C14A 1.510(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O3 1.242(4) . ?
C17B H17A 0.9800 . ?
C17B H17B 0.9800 . ?
C17B H17C 0.9800 . ?
C18B H18A 0.9800 . ?
C18B H18B 0.9800 . ?
C18B H18C 0.9800 . ?
N1 N2 1.276(3) . ?
N1 Zn1 2.052(2) . ?
O1 Zn1 1.966(2) 2_665 ?
O1 Zn1 2.086(2) . ?
O2 Zn1 2.018(2) . ?
O10 Zn1 2.038(3) . ?
O10 H10A 0.858(18) . ?
O10 H10C 0.842(18) . ?
Zn1 O1 1.967(2) 2_665 ?
Zn1 Zn1 3.1551(7) 2_665 ?
C18A C14A 1.523(13) . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C13A C14A 1.567(17) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C17A C14A 1.528(11) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
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 C1 C2 120.1(3) . . ?
C6 C1 N1 124.6(2) . . ?
C2 C1 N1 115.3(2) . . ?
O1 C2 C3 122.3(3) . . ?
O1 C2 C1 118.6(3) . . ?
C3 C2 C1 119.0(3) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N2 C11 C12 127.5(3) . . ?
N2 C11 C16 112.9(2) . . ?
C12 C11 C16 119.6(3) . . ?
O2 C12 C11 125.2(3) . . ?
O2 C12 C13A 117.1(6) . . ?
C11 C12 C13A 116.9(6) . . ?
O2 C12 C13B 113.3(7) . . ?
C11 C12 C13B 120.4(7) . . ?
C12 C13B C14B 112.7(10) . . ?
C12 C13B H13A 109.1 . . ?
C14B C13B H13A 109.1 . . ?
C12 C13B H13B 109.1 . . ?
C14B C13B H13B 109.1 . . ?
H13A C13B H13B 107.8 . . ?
C15 C14B C18B 112.2(7) . . ?
C15 C14B C17B 104.6(7) . . ?
C18B C14B C17B 109.6(8) . . ?
C15 C14B C13B 108.5(8) . . ?
C18B C14B C13B 110.0(9) . . ?
C17B C14B C13B 111.7(8) . . ?
C14B C15 C16 116.7(3) . . ?
C16 C15 C14A 111.3(3) . . ?
C14B C15 H15A 120.8 . . ?
C16 C15 H15A 109.4 . . ?
C14A C15 H15A 109.4 . . ?
C14B C15 H15B 90.0 . . ?
C16 C15 H15B 109.4 . . ?
C14A C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O3 C16 C11 121.9(3) . . ?
O3 C16 C15 118.5(3) . . ?
C11 C16 C15 119.5(3) . . ?
C14B C17B H17A 109.5 . . ?
C14B C17B H17B 109.5 . . ?
H17A C17B H17B 109.5 . . ?
C14B C17B H17C 109.5 . . ?
H17A C17B H17C 109.5 . . ?
H17B C17B H17C 109.5 . . ?
C14B C18B H18A 109.5 . . ?
C14B C18B H18B 109.5 . . ?
H18A C18B H18B 109.5 . . ?
C14B C18B H18C 109.5 . . ?
H18A C18B H18C 109.5 . . ?
H18B C18B H18C 109.5 . . ?
N2 N1 C1 116.7(2) . . ?
N2 N1 Zn1 129.60(18) . . ?
C1 N1 Zn1 113.24(17) . . ?
N1 N2 C11 120.2(2) . . ?
C2 O1 Zn1 132.52(19) . 2_665 ?
C2 O1 Zn1 113.06(17) . . ?
Zn1 O1 Zn1 102.22(9) 2_665 . ?
C12 O2 Zn1 124.9(2) . . ?
Zn1 O10 H10A 113(2) . . ?
Zn1 O10 H10C 110(2) . . ?
H10A O10 H10C 111(3) . . ?
O1 Zn1 O2 105.11(9) 2_665 . ?
O1 Zn1 O10 115.87(9) 2_665 . ?
O2 Zn1 O10 93.55(10) . . ?
O1 Zn1 N1 139.39(9) 2_665 . ?
O2 Zn1 N1 87.05(9) . . ?
O10 Zn1 N1 101.47(9) . . ?
O1 Zn1 O1 77.78(9) 2_665 . ?
O2 Zn1 O1 161.60(10) . . ?
O10 Zn1 O1 101.54(10) . . ?
N1 Zn1 O1 79.74(8) . . ?
O1 Zn1 Zn1 40.25(6) 2_665 2_665 ?
O2 Zn1 Zn1 142.17(7) . 2_665 ?
O10 Zn1 Zn1 113.84(7) . 2_665 ?
N1 Zn1 Zn1 110.82(7) . 2_665 ?
O1 Zn1 Zn1 37.53(6) . 2_665 ?
C14A C18A H18D 109.5 . . ?
C14A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C14A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C14A C13A C12 120.2(10) . . ?
C14A C13A H13C 107.3 . . ?
C12 C13A H13C 107.3 . . ?
C14A C13A H13D 107.3 . . ?
C12 C13A H13D 107.3 . . ?
H13C C13A H13D 106.9 . . ?
C14A C17A H17D 109.5 . . ?
C14A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C14A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C13A C14A C17A 110.3(7) . . ?
C13A C14A C18A 110.2(8) . . ?
C17A C14A C18A 110.3(7) . . ?
C13A C14A C15 103.8(7) . . ?
C17A C14A C15 113.9(6) . . ?
C18A C14A C15 108.1(6) . . ?
_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full 25.32
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max 0.393
_refine_diff_density_min -0.362
_refine_diff_density_rms 0.072
# Attachment '- Compound8_corrected.cif'
data_Compound8
_database_code_depnum_ccdc_archive 'CCDC 797550'
#TrackingRef '- Compound8_corrected.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C14 H19 N3 O8 Zn'
_chemical_formula_sum 'C14 H19 N3 O8 Zn'
_chemical_formula_weight 422.69
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'
Zn Zn 0.2839 1.4301 '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_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 6.5844(11)
_cell_length_b 15.743(3)
_cell_length_c 16.287(3)
_cell_angle_alpha 90.00
_cell_angle_beta 96.006(10)
_cell_angle_gamma 90.00
_cell_volume 1679.0(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 275
_cell_measurement_theta_min 2.83
_cell_measurement_theta_max 17.92
_exptl_crystal_description plate
_exptl_crystal_colour red
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.672
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 872
_exptl_absorpt_coefficient_mu 1.513
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.608
_exptl_absorpt_correction_T_max 0.735
_exptl_absorpt_process_details sadabs
_exptl_special_details
;
The quality of the data was poor due to the crystal quality and also the crystal is
weakly diffracting. Therefore, a large proportion of "unobserved" reflections
were used in the refinement.
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 8485
_diffrn_reflns_av_R_equivalents 0.1851
_diffrn_reflns_av_sigmaI/netI 0.2776
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.59
_diffrn_reflns_theta_max 25.35
_reflns_number_total 2936
_reflns_number_gt 1304
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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.
A twin law was found and applied, even though the overlap of the components
were poor (BASF of ca. 0.05) and consequently the drop of R factor not effective.
The hydrogen atoms of the crystalization water molecule were inserted in
calculated positions which were found by using the CALC-OH option of WINGX;
their coordinates were blocked during the refinement process and the isotropic
thermal parameter was set at 1.5 times the average thermal parameter of the
oxygen atom.
The hydrogen atoms of the coordinated water molecules were also inserted in
calculated positions and their coordinates were also blocked during the refinement
process and the isotropic thermal parameter set at 1.5 times the average
thermal parameter of the attached O atom.
The ellipsoid of C2, O5 and O10 were restrained to more appropriate values.
;
_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^)+(0.1438P)^2^+4.5671P] 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 2936
_refine_ls_number_parameters 237
_refine_ls_number_restraints 24
_refine_ls_R_factor_all 0.2334
_refine_ls_R_factor_gt 0.1032
_refine_ls_wR_factor_ref 0.3351
_refine_ls_wR_factor_gt 0.2737
_refine_ls_goodness_of_fit_ref 1.089
_refine_ls_restrained_S_all 1.086
_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
C1 C 1.122(2) 0.1524(11) 0.9046(9) 0.024(4) Uani 1 1 d . . .
C2 C 0.982(2) 0.2052(10) 0.8513(9) 0.017(4) Uani 1 1 d U . .
C3 C 1.033(3) 0.2852(11) 0.8312(10) 0.026(4) Uani 1 1 d . . .
H3 H 0.9359 0.3193 0.7990 0.031 Uiso 1 1 calc R . .
C4 C 1.225(2) 0.3185(11) 0.8566(11) 0.028(4) Uani 1 1 d . . .
H4 H 1.2630 0.3739 0.8409 0.034 Uiso 1 1 calc R . .
C5 C 1.360(3) 0.2661(11) 0.9066(10) 0.022(4) Uani 1 1 d . . .
C6 C 1.311(2) 0.1879(10) 0.9327(10) 0.023(4) Uani 1 1 d . . .
H6 H 1.4051 0.1572 0.9698 0.028 Uiso 1 1 calc R . .
N5 N 1.568(2) 0.2993(10) 0.9335(9) 0.029(4) Uani 1 1 d . . .
C11 C 0.493(2) 0.1683(11) 0.7413(9) 0.018(4) Uani 1 1 d . . .
C12 C 0.369(2) 0.2257(11) 0.6849(9) 0.019(4) Uani 1 1 d . . .
C13 C 0.167(2) 0.1924(10) 0.6438(10) 0.026(4) Uani 1 1 d . . .
H13A H 0.0574 0.2080 0.6783 0.031 Uiso 1 1 calc R . .
H13B H 0.1366 0.2210 0.5898 0.031 Uiso 1 1 calc R . .
C14 C 0.160(2) 0.0981(11) 0.6301(9) 0.021(4) Uani 1 1 d . . .
C15 C 0.228(2) 0.0544(11) 0.7108(9) 0.022(4) Uani 1 1 d . . .
H15A H 0.1163 0.0597 0.7470 0.026 Uiso 1 1 calc R . .
H15B H 0.2445 -0.0068 0.6995 0.026 Uiso 1 1 calc R . .
C16 C 0.420(2) 0.0858(11) 0.7575(10) 0.022(4) Uani 1 1 d . . .
C17 C -0.056(2) 0.0702(12) 0.6001(11) 0.033(5) Uani 1 1 d . . .
H17A H -0.0580 0.0088 0.5905 0.050 Uiso 1 1 calc R . .
H17B H -0.1018 0.0997 0.5485 0.050 Uiso 1 1 calc R . .
H17C H -0.1473 0.0842 0.6419 0.050 Uiso 1 1 calc R . .
C18 C 0.301(3) 0.0708(12) 0.5664(11) 0.036(5) Uani 1 1 d . . .
H18A H 0.4409 0.0896 0.5843 0.054 Uiso 1 1 calc R . .
H18B H 0.2551 0.0965 0.5129 0.054 Uiso 1 1 calc R . .
H18C H 0.2988 0.0088 0.5612 0.054 Uiso 1 1 calc R . .
N1 N 0.7957(18) 0.1625(9) 0.8260(7) 0.017(3) Uani 1 1 d . . .
N2 N 0.674(2) 0.2024(8) 0.7721(8) 0.021(3) Uani 1 1 d . . .
O1 O 1.0664(15) 0.0731(8) 0.9238(6) 0.025(3) Uani 1 1 d . . .
O2 O 0.5037(14) 0.0356(7) 0.8128(6) 0.019(3) Uani 1 1 d U . .
O3 O 0.4234(16) 0.2987(7) 0.6738(7) 0.024(3) Uani 1 1 d . . .
O5 O 1.6737(18) 0.2578(8) 0.9862(7) 0.035(3) Uani 1 1 d U . .
O6 O 1.6206(18) 0.3657(8) 0.9032(9) 0.043(4) Uani 1 1 d . . .
O10 O 0.232(3) 0.8812(11) 0.8543(10) 0.081(5) Uani 1 1 d U . .
O11 O 0.8487(17) -0.0723(7) 0.8402(8) 0.038(3) Uani 1 1 d . . .
O12 O 0.6929(16) 0.0255(6) 0.9912(6) 0.019(3) Uani 1 1 d . . .
Zn1 Zn 0.7804(3) 0.04399(13) 0.87921(11) 0.0196(6) Uani 1 1 d . . .
H10B H 0.3547 0.8869 0.8466 0.029 Uiso 1 1 d . . .
H10C H 0.2090 0.8390 0.8871 0.029 Uiso 1 1 d . . .
H11A H 0.7712 -0.1139 0.8707 0.029 Uiso 1 1 d . . .
H11B H 0.9907 -0.0835 0.8553 0.029 Uiso 1 1 d . . .
H12A H 0.7654 -0.0220 1.0166 0.029 Uiso 1 1 d . . .
H12B H 0.7258 0.0757 1.0244 0.029 Uiso 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
C1 0.026(10) 0.029(11) 0.014(8) 0.002(8) -0.009(7) 0.011(9)
C2 0.016(7) 0.020(7) 0.014(6) -0.013(6) -0.004(6) 0.000(6)
C3 0.031(10) 0.023(10) 0.023(9) 0.008(8) 0.003(8) -0.006(8)
C4 0.022(9) 0.016(9) 0.044(11) -0.008(9) -0.005(8) -0.003(8)
C5 0.034(10) 0.017(9) 0.017(8) -0.006(8) 0.009(8) -0.003(8)
C6 0.021(9) 0.016(9) 0.032(10) 0.008(8) 0.007(8) -0.007(8)
N5 0.024(8) 0.036(10) 0.030(9) -0.006(8) 0.011(7) 0.001(8)
C11 0.014(8) 0.024(9) 0.016(8) -0.001(8) 0.003(7) -0.008(8)
C12 0.015(8) 0.031(11) 0.010(8) 0.005(8) -0.001(7) 0.006(8)
C13 0.029(10) 0.024(10) 0.023(9) -0.002(8) 0.000(8) 0.014(8)
C14 0.023(9) 0.025(10) 0.016(8) -0.008(8) 0.008(7) -0.005(8)
C15 0.022(8) 0.024(10) 0.019(8) 0.005(8) 0.005(7) -0.008(8)
C16 0.020(9) 0.022(9) 0.025(9) 0.009(8) 0.009(8) -0.002(8)
C17 0.022(9) 0.036(12) 0.038(11) 0.009(9) -0.006(8) -0.004(9)
C18 0.036(11) 0.038(12) 0.035(11) 0.003(9) 0.007(9) 0.007(9)
N1 0.014(7) 0.028(8) 0.010(6) -0.004(6) 0.002(6) 0.006(6)
N2 0.026(8) 0.017(8) 0.020(7) -0.011(6) 0.002(6) 0.006(6)
O1 0.011(5) 0.039(8) 0.025(6) 0.008(6) 0.004(5) 0.003(5)
O2 0.020(5) 0.017(5) 0.020(5) 0.014(5) -0.006(4) -0.003(5)
O3 0.024(6) 0.019(7) 0.032(7) 0.011(6) 0.010(5) 0.000(6)
O5 0.033(3) 0.037(4) 0.035(3) 0.000(2) 0.002(2) 0.000(2)
O6 0.033(8) 0.028(8) 0.067(10) -0.001(8) 0.008(7) -0.012(7)
O10 0.080(6) 0.082(6) 0.080(6) -0.001(2) 0.007(2) 0.003(2)
O11 0.023(6) 0.023(7) 0.070(9) -0.009(7) 0.010(6) 0.008(6)
O12 0.025(6) 0.017(6) 0.015(5) 0.005(5) -0.004(5) -0.001(5)
Zn1 0.0161(9) 0.0221(10) 0.0205(9) 0.0022(10) 0.0011(7) 0.0019(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
C1 O1 1.347(19) . ?
C1 C6 1.40(2) . ?
C1 C2 1.46(2) . ?
C2 C3 1.35(2) . ?
C2 N1 1.422(19) . ?
C3 C4 1.39(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.41(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.35(2) . ?
C5 N5 1.49(2) . ?
C6 H6 0.9500 . ?
N5 O5 1.233(17) . ?
N5 O6 1.220(17) . ?
C11 N2 1.357(19) . ?
C11 C16 1.42(2) . ?
C11 C12 1.47(2) . ?
C12 O3 1.222(18) . ?
C12 C13 1.52(2) . ?
C13 C14 1.50(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.51(2) . ?
C14 C17 1.52(2) . ?
C14 C18 1.53(2) . ?
C15 C16 1.49(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O2 1.279(18) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 N2 1.287(17) . ?
N1 Zn1 2.065(14) . ?
O1 Zn1 1.999(10) . ?
O2 Zn1 2.024(9) . ?
O10 H10B 0.837 . ?
O10 H10C 0.875 . ?
O11 Zn1 2.004(12) . ?
O11 H11A 0.995 . ?
O11 H11B 0.958 . ?
O12 Zn1 1.990(10) . ?
O12 H12A 0.958 . ?
O12 H12B 0.970 . ?
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 C1 C6 123.3(14) . . ?
O1 C1 C2 119.8(14) . . ?
C6 C1 C2 116.9(15) . . ?
C3 C2 N1 126.8(15) . . ?
C3 C2 C1 121.2(15) . . ?
N1 C2 C1 112.0(14) . . ?
C2 C3 C4 121.3(16) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 116.9(16) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 H4 121.6 . . ?
C6 C5 C4 123.8(16) . . ?
C6 C5 N5 118.0(15) . . ?
C4 C5 N5 118.2(15) . . ?
C5 C6 C1 119.6(16) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O5 N5 O6 125.1(15) . . ?
O5 N5 C5 116.9(14) . . ?
O6 N5 C5 118.0(14) . . ?
N2 C11 C16 126.5(14) . . ?
N2 C11 C12 113.4(14) . . ?
C16 C11 C12 120.1(14) . . ?
O3 C12 C11 121.1(14) . . ?
O3 C12 C13 121.1(14) . . ?
C11 C12 C13 117.7(15) . . ?
C14 C13 C12 114.7(13) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 108.6(13) . . ?
C13 C14 C17 110.2(14) . . ?
C15 C14 C17 109.3(13) . . ?
C13 C14 C18 111.6(14) . . ?
C15 C14 C18 108.6(14) . . ?
C17 C14 C18 108.5(14) . . ?
C16 C15 C14 116.8(14) . . ?
C16 C15 H15A 108.1 . . ?
C14 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
C14 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
O2 C16 C11 124.5(14) . . ?
O2 C16 C15 115.9(14) . . ?
C11 C16 C15 119.6(14) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 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 . . ?
N2 N1 C2 115.1(13) . . ?
N2 N1 Zn1 132.3(10) . . ?
C2 N1 Zn1 112.6(10) . . ?
N1 N2 C11 121.3(14) . . ?
C1 O1 Zn1 113.4(9) . . ?
C16 O2 Zn1 129.5(10) . . ?
H10B O10 H10C 113.7 . . ?
Zn1 O11 H11A 107.5 . . ?
Zn1 O11 H11B 109.4 . . ?
H11A O11 H11B 106.7 . . ?
Zn1 O12 H12A 109.4 . . ?
Zn1 O12 H12B 108.8 . . ?
H12A O12 H12B 108.8 . . ?
O12 Zn1 O11 104.6(5) . . ?
O12 Zn1 O1 93.0(4) . . ?
O11 Zn1 O1 95.2(5) . . ?
O12 Zn1 O2 98.6(4) . . ?
O11 Zn1 O2 89.4(5) . . ?
O1 Zn1 O2 166.0(4) . . ?
O12 Zn1 N1 123.3(5) . . ?
O11 Zn1 N1 132.1(5) . . ?
O1 Zn1 N1 81.9(5) . . ?
O2 Zn1 N1 85.1(4) . . ?
_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full 25.35
_diffrn_measured_fraction_theta_full 0.950
_refine_diff_density_max 2.654
_refine_diff_density_min -0.963
_refine_diff_density_rms 0.221