# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
2,2'-[(1E,1'E)-2,2'-(2,5-Dibutoxy-1,4-phenylene)bis(ethene-
2,1-diyl)]dipyridine
;
_chemical_name_common
;2,2'-((1E,1'E)-2,2'-(2,5-Dibutoxy-1,4-phenylene)bis(ethene-
2,1-diyl))dipyridine
;
_chemical_formula_moiety 'C28 H32 N2 O2'
_chemical_formula_sum 'C28 H32 N2 O2'
_chemical_formula_iupac 'C28 H32 N2 O2'
_chemical_formula_weight 428.56
_chemical_melting_point ?
_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 8.882(5)
_cell_length_b 13.892(5)
_cell_length_c 10.387(5)
_cell_angle_alpha 90.000(5)
_cell_angle_beta 107.392(5)
_cell_angle_gamma 90.000(5)
_cell_volume 1223.0(10)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 1446
_cell_measurement_theta_min 2.52
_cell_measurement_theta_max 21.77
_cell_measurement_temperature 298(2)
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.164
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 460
_exptl_absorpt_coefficient_mu 0.073
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min 0.9644
_exptl_absorpt_correction_T_max 0.9856
_exptl_special_details
;
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71069
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART CCD area-detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 8512
_diffrn_reflns_av_R_equivalents 0.0395
_diffrn_reflns_av_sigmaI/netI 0.0368
_diffrn_reflns_theta_min 2.40
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 12
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_reflns_number_total 2162
_reflns_number_gt 1385
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0817
_refine_ls_R_factor_gt 0.0488
_refine_ls_wR_factor_gt 0.1317
_refine_ls_wR_factor_ref 0.1539
_refine_ls_goodness_of_fit_ref 1.032
_refine_ls_restrained_S_all 1.032
_refine_ls_number_reflns 2162
_refine_ls_number_parameters 146
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0821P)^2^+0.0525P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.162
_refine_diff_density_min -0.156
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_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^ >
\s(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.
;
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'
_computing_data_collection 'SMART (Bruker, 2007)'
_computing_cell_refinement 'SAINT (Bruker, 2007)'
_computing_data_reduction 'SAINT (Bruker, 2007)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2008)'
_computing_publication_material 'SHELXL97 (Sheldrick, 2008)'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.10160(17) 0.50961(9) 0.22161(12) 0.0589(4) Uani d . 1 1 . .
C C2 0.0431(2) 0.57863(13) 0.43825(17) 0.0477(5) Uani d . 1 1 . .
H H2 0.0725 0.6313 0.3960 0.057 Uiso calc R 1 1 . .
C C1 -0.0472(2) 0.50707(13) 0.36022(17) 0.0458(5) Uani d . 1 1 . .
C C5 0.2548(2) 0.72369(13) 0.61936(18) 0.0491(5) Uani d . 1 1 . .
H H5 0.2324 0.7310 0.5265 0.059 Uiso calc R 1 1 . .
C C4 0.1898(2) 0.64922(13) 0.66286(18) 0.0487(5) Uani d . 1 1 . .
H H4 0.2083 0.6442 0.7556 0.058 Uiso calc R 1 1 . .
C C6 0.3587(2) 0.79507(14) 0.70512(19) 0.0500(5) Uani d . 1 1 . .
C C3 0.0919(2) 0.57414(13) 0.57915(17) 0.0447(5) Uani d . 1 1 . .
N N1 0.3841(2) 0.78919(14) 0.83829(17) 0.0781(6) Uani d . 1 1 . .
C C7 0.4305(3) 0.86549(15) 0.6486(2) 0.0617(6) Uani d . 1 1 . .
H H7 0.4106 0.8689 0.5556 0.074 Uiso calc R 1 1 . .
C C11 -0.0751(3) 0.59382(15) 0.15295(19) 0.0620(6) Uani d . 1 1 . .
H H11A 0.0359 0.5996 0.1601 0.074 Uiso calc R 1 1 . .
H H11B -0.1069 0.6507 0.1922 0.074 Uiso calc R 1 1 . .
C C12 -0.1717(3) 0.58404(16) 0.00746(18) 0.0639(6) Uani d . 1 1 . .
H H12A -0.1503 0.5217 -0.0253 0.077 Uiso calc R 1 1 . .
H H12B -0.2826 0.5857 0.0020 0.077 Uiso calc R 1 1 . .
C C8 0.5312(3) 0.93013(17) 0.7318(3) 0.0770(7) Uani d . 1 1 . .
H H8 0.5797 0.9780 0.6957 0.092 Uiso calc R 1 1 . .
C C10 0.4832(3) 0.8533(2) 0.9145(2) 0.0988(10) Uani d . 1 1 . .
H H10 0.5018 0.8498 1.0074 0.119 Uiso calc R 1 1 . .
C C9 0.5588(3) 0.9232(2) 0.8671(3) 0.0907(9) Uani d . 1 1 . .
H H9 0.6277 0.9652 0.9258 0.109 Uiso calc R 1 1 . .
C C13 -0.1405(4) 0.6606(2) -0.0831(2) 0.0963(9) Uani d . 1 1 . .
H H13A -0.0302 0.6582 -0.0795 0.116 Uiso calc R 1 1 . .
H H13B -0.1603 0.7231 -0.0499 0.116 Uiso calc R 1 1 . .
C C14 -0.2407(4) 0.6502(2) -0.2276(2) 0.0996(10) Uani d . 1 1 . .
H H14A -0.2273 0.5868 -0.2594 0.149 Uiso calc R 1 1 . .
H H14B -0.2092 0.6972 -0.2822 0.149 Uiso calc R 1 1 . .
H H14C -0.3496 0.6599 -0.2335 0.149 Uiso calc R 1 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0777(10) 0.0571(9) 0.0353(8) -0.0123(7) 0.0069(7) -0.0006(6)
C2 0.0541(12) 0.0462(10) 0.0408(11) -0.0014(9) 0.0111(9) -0.0001(8)
C1 0.0492(11) 0.0514(11) 0.0330(10) 0.0032(9) 0.0066(9) -0.0017(8)
C5 0.0514(12) 0.0543(12) 0.0386(11) 0.0007(9) 0.0090(9) -0.0031(9)
C4 0.0550(12) 0.0529(11) 0.0346(11) -0.0021(9) 0.0081(9) -0.0050(8)
C6 0.0510(12) 0.0529(12) 0.0467(12) -0.0029(9) 0.0155(10) -0.0073(9)
C3 0.0466(11) 0.0463(11) 0.0387(10) 0.0006(8) 0.0090(9) -0.0034(8)
N1 0.0928(15) 0.0965(15) 0.0456(11) -0.0454(12) 0.0215(10) -0.0188(10)
C7 0.0672(14) 0.0618(13) 0.0568(13) -0.0111(11) 0.0194(11) -0.0026(10)
C11 0.0807(16) 0.0550(13) 0.0478(12) -0.0075(11) 0.0154(11) 0.0028(10)
C12 0.0770(16) 0.0679(14) 0.0421(12) -0.0073(11) 0.0107(11) 0.0048(10)
C8 0.0811(17) 0.0685(15) 0.0898(19) -0.0262(13) 0.0385(14) -0.0114(13)
C10 0.115(2) 0.129(2) 0.0536(15) -0.067(2) 0.0270(15) -0.0310(15)
C9 0.0903(19) 0.105(2) 0.0823(19) -0.0484(16) 0.0338(15) -0.0386(16)
C13 0.131(2) 0.0873(18) 0.0572(16) -0.0271(17) 0.0078(16) 0.0158(13)
C14 0.125(3) 0.108(2) 0.0532(15) -0.0132(18) 0.0064(15) 0.0242(14)
_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.375(2) ?
O1 C11 . 1.426(2) ?
C2 C1 . 1.379(3) ?
C2 C3 . 1.398(2) ?
C2 H2 . 0.9300 ?
C1 C3 3_566 1.406(3) ?
C5 C4 . 1.328(3) ?
C5 C6 . 1.462(3) ?
C5 H5 . 0.9300 ?
C4 C3 . 1.466(3) ?
C4 H4 . 0.9300 ?
C6 N1 . 1.336(2) ?
C6 C7 . 1.390(3) ?
C3 C1 3_566 1.406(3) ?
N1 C10 . 1.334(3) ?
C7 C8 . 1.375(3) ?
C7 H7 . 0.9300 ?
C11 C12 . 1.504(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.499(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C8 C9 . 1.356(3) ?
C8 H8 . 0.9300 ?
C10 C9 . 1.353(3) ?
C10 H10 . 0.9300 ?
C9 H9 . 0.9300 ?
C13 C14 . 1.506(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C11 . . 119.07(14) ?
C1 C2 C3 . . 121.80(18) ?
C1 C2 H2 . . 119.1 ?
C3 C2 H2 . . 119.1 ?
O1 C1 C2 . . 123.88(17) ?
O1 C1 C3 . 3_566 115.58(15) ?
C2 C1 C3 . 3_566 120.53(17) ?
C4 C5 C6 . . 125.48(18) ?
C4 C5 H5 . . 117.3 ?
C6 C5 H5 . . 117.3 ?
C5 C4 C3 . . 126.43(18) ?
C5 C4 H4 . . 116.8 ?
C3 C4 H4 . . 116.8 ?
N1 C6 C7 . . 121.57(18) ?
N1 C6 C5 . . 118.03(18) ?
C7 C6 C5 . . 120.38(18) ?
C2 C3 C1 . 3_566 117.66(16) ?
C2 C3 C4 . . 122.17(17) ?
C1 C3 C4 3_566 . 120.15(16) ?
C10 N1 C6 . . 116.8(2) ?
C8 C7 C6 . . 119.3(2) ?
C8 C7 H7 . . 120.4 ?
C6 C7 H7 . . 120.4 ?
O1 C11 C12 . . 107.37(16) ?
O1 C11 H11A . . 110.2 ?
C12 C11 H11A . . 110.2 ?
O1 C11 H11B . . 110.2 ?
C12 C11 H11B . . 110.2 ?
H11A C11 H11B . . 108.5 ?
C13 C12 C11 . . 114.19(19) ?
C13 C12 H12A . . 108.7 ?
C11 C12 H12A . . 108.7 ?
C13 C12 H12B . . 108.7 ?
C11 C12 H12B . . 108.7 ?
H12A C12 H12B . . 107.6 ?
C9 C8 C7 . . 119.1(2) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
N1 C10 C9 . . 125.0(2) ?
N1 C10 H10 . . 117.5 ?
C9 C10 H10 . . 117.5 ?
C10 C9 C8 . . 118.2(2) ?
C10 C9 H9 . . 120.9 ?
C8 C9 H9 . . 120.9 ?
C12 C13 C14 . . 113.1(2) ?
C12 C13 H13A . . 109.0 ?
C14 C13 H13A . . 109.0 ?
C12 C13 H13B . . 109.0 ?
C14 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 N1 4_575 0.93 2.70 3.446(3) 138
_database_code_depnum_ccdc_archive 'CCDC 737793'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_liu
#TrackingRef 'web_deposit_cif_file_0_zhaodiliu_1322483613.liu.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C28 H32 N2 O2'
_chemical_formula_weight 428.56
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'
_symmetry_cell_setting ?
_symmetry_space_group_name_H-M ?
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 9.0577(16)
_cell_length_b 8.8169(15)
_cell_length_c 16.292(3)
_cell_angle_alpha 90.00
_cell_angle_beta 113.972(8)
_cell_angle_gamma 90.00
_cell_volume 1188.9(4)
_cell_formula_units_Z 2
_cell_measurement_temperature 298(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description ?
_exptl_crystal_colour ?
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.197
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 460
_exptl_absorpt_coefficient_mu 0.075
_exptl_absorpt_correction_type ?
_exptl_absorpt_correction_T_min 0.9851
_exptl_absorpt_correction_T_max 0.9925
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298(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 ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 6699
_diffrn_reflns_av_R_equivalents 0.0318
_diffrn_reflns_av_sigmaI/netI 0.0344
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.46
_diffrn_reflns_theta_max 25.50
_reflns_number_total 2209
_reflns_number_gt 1621
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0571P)^2^+0.1620P] 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 2209
_refine_ls_number_parameters 146
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0624
_refine_ls_R_factor_gt 0.0443
_refine_ls_wR_factor_ref 0.1217
_refine_ls_wR_factor_gt 0.1087
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_restrained_S_all 1.046
_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
O1 O 0.71198(12) 0.34411(14) 0.92013(7) 0.0526(3) Uani 1 1 d . . .
N1 N 0.79694(17) 0.67393(18) 1.26984(10) 0.0603(4) Uani 1 1 d . . .
C1 C 0.83124(18) 0.58228(18) 1.21420(11) 0.0459(4) Uani 1 1 d . . .
C2 C 0.9624(2) 0.4852(2) 1.24509(11) 0.0549(5) Uani 1 1 d . . .
H2 H 0.9824 0.4212 1.2053 0.066 Uiso 1 1 calc R . .
C3 C 1.0635(2) 0.4838(2) 1.33520(13) 0.0658(5) Uani 1 1 d . . .
H3 H 1.1518 0.4187 1.3570 0.079 Uiso 1 1 calc R . .
C4 C 1.0314(3) 0.5803(3) 1.39218(13) 0.0739(6) Uani 1 1 d . . .
H4 H 1.0987 0.5837 1.4530 0.089 Uiso 1 1 calc R . .
C5 C 0.8979(3) 0.6710(3) 1.35708(13) 0.0715(6) Uani 1 1 d . . .
H5 H 0.8757 0.7348 1.3961 0.086 Uiso 1 1 calc R . .
C6 C 0.71290(19) 0.58706(19) 1.12035(11) 0.0500(4) Uani 1 1 d . . .
H6 H 0.6101 0.6179 1.1130 0.060 Uiso 1 1 calc R . .
C7 C 0.72690(18) 0.55502(19) 1.04390(10) 0.0478(4) Uani 1 1 d . . .
H7 H 0.6294 0.5523 0.9936 0.057 Uiso 1 1 calc R . .
C8 C 0.87001(17) 0.52310(17) 1.02515(9) 0.0399(4) Uani 1 1 d . . .
C9 C 0.85617(16) 0.42196(17) 0.95625(9) 0.0396(4) Uani 1 1 d . . .
C10 C 0.98394(17) 0.39976(17) 0.93194(9) 0.0421(4) Uani 1 1 d . . .
H10 H 0.9725 0.3320 0.8860 0.050 Uiso 1 1 calc R . .
C11 C 0.66846(19) 0.26690(19) 0.83590(10) 0.0507(4) Uani 1 1 d . . .
H11A H 0.5813 0.1965 0.8277 0.061 Uiso 1 1 calc R . .
H11B H 0.7604 0.2085 0.8375 0.061 Uiso 1 1 calc R . .
C12 C 0.6162(2) 0.3733(2) 0.75755(11) 0.0554(5) Uani 1 1 d . . .
H12A H 0.7051 0.4404 0.7639 0.066 Uiso 1 1 calc R . .
H12B H 0.5275 0.4352 0.7573 0.066 Uiso 1 1 calc R . .
C13 C 0.5634(3) 0.2895(2) 0.66945(12) 0.0777(6) Uani 1 1 d . . .
H13A H 0.6558 0.2366 0.6675 0.093 Uiso 1 1 calc R . .
H13B H 0.4838 0.2139 0.6668 0.093 Uiso 1 1 calc R . .
C14 C 0.4927(3) 0.3894(3) 0.58863(14) 0.1032(9) Uani 1 1 d . . .
H14A H 0.3910 0.4290 0.5843 0.155 Uiso 1 1 calc R . .
H14B H 0.4763 0.3316 0.5357 0.155 Uiso 1 1 calc R . .
H14C H 0.5653 0.4718 0.5940 0.155 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
O1 0.0457(6) 0.0707(8) 0.0430(7) -0.0123(6) 0.0196(5) -0.0164(5)
N1 0.0642(9) 0.0696(10) 0.0558(9) -0.0165(8) 0.0334(7) -0.0087(7)
C1 0.0474(9) 0.0543(10) 0.0455(9) -0.0072(7) 0.0285(7) -0.0102(7)
C2 0.0600(11) 0.0627(11) 0.0496(10) -0.0004(8) 0.0302(8) -0.0002(9)
C3 0.0649(12) 0.0765(13) 0.0544(11) 0.0125(10) 0.0225(9) -0.0030(10)
C4 0.0818(14) 0.0907(16) 0.0443(11) -0.0056(11) 0.0205(10) -0.0228(12)
C5 0.0854(14) 0.0809(14) 0.0544(12) -0.0235(10) 0.0347(11) -0.0185(12)
C6 0.0415(8) 0.0637(11) 0.0509(10) -0.0062(8) 0.0248(7) -0.0009(8)
C7 0.0388(8) 0.0626(11) 0.0410(9) -0.0030(8) 0.0154(7) -0.0021(7)
C8 0.0403(8) 0.0506(9) 0.0298(8) 0.0038(6) 0.0153(6) 0.0003(7)
C9 0.0378(8) 0.0492(9) 0.0300(7) 0.0020(6) 0.0120(6) -0.0045(6)
C10 0.0464(8) 0.0508(9) 0.0301(8) -0.0035(7) 0.0166(6) -0.0012(7)
C11 0.0475(9) 0.0565(10) 0.0451(10) -0.0111(8) 0.0159(7) -0.0114(8)
C12 0.0572(10) 0.0577(11) 0.0472(10) -0.0062(8) 0.0171(8) -0.0052(8)
C13 0.1038(16) 0.0720(13) 0.0495(12) -0.0088(10) 0.0231(11) -0.0034(12)
C14 0.141(2) 0.0980(18) 0.0499(13) 0.0026(12) 0.0172(13) -0.0293(16)
_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
O1 C9 1.3779(17) . ?
O1 C11 1.4362(18) . ?
N1 C1 1.342(2) . ?
N1 C5 1.342(2) . ?
C1 C2 1.383(2) . ?
C1 C6 1.469(2) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.332(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.475(2) . ?
C7 H7 0.9300 . ?
C8 C10 1.396(2) 3_767 ?
C8 C9 1.399(2) . ?
C9 C10 1.381(2) . ?
C10 C8 1.396(2) 3_767 ?
C10 H10 0.9300 . ?
C11 C12 1.498(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.509(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.495(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
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
C9 O1 C11 119.26(12) . . ?
C1 N1 C5 117.30(17) . . ?
N1 C1 C2 121.85(16) . . ?
N1 C1 C6 114.50(15) . . ?
C2 C1 C6 123.53(15) . . ?
C3 C2 C1 119.57(17) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 118.85(19) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 118.27(18) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 124.12(19) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C7 C6 C1 131.35(15) . . ?
C7 C6 H6 114.3 . . ?
C1 C6 H6 114.3 . . ?
C6 C7 C8 131.27(14) . . ?
C6 C7 H7 114.4 . . ?
C8 C7 H7 114.4 . . ?
C10 C8 C9 118.04(13) 3_767 . ?
C10 C8 C7 122.48(14) 3_767 . ?
C9 C8 C7 119.22(13) . . ?
O1 C9 C10 124.49(14) . . ?
O1 C9 C8 114.88(13) . . ?
C10 C9 C8 120.54(13) . . ?
C9 C10 C8 121.41(14) . 3_767 ?
C9 C10 H10 119.3 . . ?
C8 C10 H10 119.3 3_767 . ?
O1 C11 C12 112.74(14) . . ?
O1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
O1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 111.86(15) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 113.97(18) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 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 N1 C1 C2 1.8(2) . . . . ?
C5 N1 C1 C6 177.92(16) . . . . ?
N1 C1 C2 C3 -1.3(3) . . . . ?
C6 C1 C2 C3 -177.15(16) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
C3 C4 C5 N1 -1.1(3) . . . . ?
N1 C1 C6 C7 155.45(19) . . . . ?
C2 C1 C6 C7 -28.5(3) . . . . ?
C1 C6 C7 C8 -9.3(3) . . . . ?
C6 C7 C8 C10 -38.7(3) . . . 3_767 ?
C6 C7 C8 C9 147.25(18) . . . . ?
C11 O1 C9 C10 -18.6(2) . . . . ?
C11 O1 C9 C8 164.78(13) . . . . ?
C10 C8 C9 O1 176.79(13) 3_767 . . . ?
C7 C8 C9 O1 -8.9(2) . . . . ?
C10 C8 C9 C10 0.0(2) 3_767 . . . ?
C7 C8 C9 C10 174.37(14) . . . . ?
O1 C9 C10 C8 -176.46(13) . . . 3_767 ?
C8 C9 C10 C8 -0.1(2) . . . 3_767 ?
C9 O1 C11 C12 -74.09(18) . . . . ?
O1 C11 C12 C13 -177.22(14) . . . . ?
C11 C12 C13 C14 173.52(18) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.167
_refine_diff_density_min -0.181
_refine_diff_density_rms 0.046
_database_code_depnum_ccdc_archive 'CCDC 855787'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_110520_dimei_0m
#TrackingRef 'web_deposit_cif_file_1_zhaodiliu_1322483613.110520_DIMEI_0m.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C30 H36 N2 O2'
_chemical_formula_weight 456.61
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'
_symmetry_cell_setting ?
_symmetry_space_group_name_H-M ?
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 9.2930(15)
_cell_length_b 14.162(2)
_cell_length_c 10.4495(18)
_cell_angle_alpha 90.00
_cell_angle_beta 104.566(2)
_cell_angle_gamma 90.00
_cell_volume 1331.1(4)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description ?
_exptl_crystal_colour ?
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.139
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 492
_exptl_absorpt_coefficient_mu 0.071
_exptl_absorpt_correction_type ?
_exptl_absorpt_correction_T_min 0.9860
_exptl_absorpt_correction_T_max 0.9929
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(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 ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 6620
_diffrn_reflns_av_R_equivalents 0.0238
_diffrn_reflns_av_sigmaI/netI 0.0313
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.01
_diffrn_reflns_theta_max 25.00
_reflns_number_total 4008
_reflns_number_gt 3614
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.1381P)^2^+0.2472P] 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 0.027(7)
_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(2)
_refine_ls_number_reflns 4008
_refine_ls_number_parameters 318
_refine_ls_number_restraints 40
_refine_ls_R_factor_all 0.0718
_refine_ls_R_factor_gt 0.0665
_refine_ls_wR_factor_ref 0.2037
_refine_ls_wR_factor_gt 0.1950
_refine_ls_goodness_of_fit_ref 1.045
_refine_ls_restrained_S_all 1.075
_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 0.6117(3) 1.0384(3) 0.8629(3) 0.0640(9) Uani 1 1 d . . .
C2 C 0.5105(4) 1.0798(3) 0.7595(4) 0.0747(11) Uani 1 1 d . . .
H2 H 0.4714 1.0454 0.6829 0.090 Uiso 1 1 calc R . .
C3 C 0.4664(5) 1.1719(3) 0.7683(4) 0.0816(12) Uani 1 1 d . . .
H3 H 0.3981 1.2005 0.6986 0.098 Uiso 1 1 calc R . .
C4 C 0.5273(5) 1.2208(4) 0.8844(5) 0.0896(13) Uani 1 1 d . . .
H4 H 0.5005 1.2830 0.8955 0.108 Uiso 1 1 calc R . .
C5 C 0.6273(5) 1.1745(4) 0.9811(4) 0.0921(14) Uani 1 1 d . . .
H5 H 0.6677 1.2077 1.0586 0.110 Uiso 1 1 calc R . .
C6 C 0.6627(4) 0.9418(4) 0.8603(4) 0.0782(11) Uani 1 1 d . . .
H6 H 0.7648 0.9330 0.8906 0.094 Uiso 1 1 calc R . .
C7 C 0.5845(4) 0.8650(3) 0.8210(4) 0.0744(10) Uani 1 1 d . . .
H7 H 0.6393 0.8103 0.8189 0.089 Uiso 1 1 calc R . .
C8 C 0.4214(3) 0.8538(3) 0.7797(3) 0.0581(8) Uani 1 1 d . . .
C9 C 0.3581(4) 0.7819(3) 0.6914(3) 0.0610(8) Uani 1 1 d . . .
C10 C 0.2042(4) 0.7703(2) 0.6555(3) 0.0600(8) Uani 1 1 d . . .
H10 H 0.1635 0.7220 0.5973 0.072 Uiso 1 1 calc R . .
C11 C 0.1095(3) 0.8287(2) 0.7037(3) 0.0564(7) Uani 1 1 d . . .
C12 C 0.1741(3) 0.9019(2) 0.7895(3) 0.0532(7) Uani 1 1 d . . .
C13 C 0.3267(3) 0.9108(2) 0.8283(3) 0.0564(7) Uani 1 1 d . . .
H13 H 0.3676 0.9571 0.8898 0.068 Uiso 1 1 calc R . .
C14 C -0.0528(4) 0.8228(3) 0.6585(4) 0.0728(10) Uani 1 1 d . . .
H14 H -0.1030 0.8801 0.6517 0.087 Uiso 1 1 calc R . .
C15 C -0.1387(4) 0.7463(3) 0.6255(4) 0.0745(10) Uani 1 1 d . . .
H15 H -0.2394 0.7592 0.5929 0.089 Uiso 1 1 calc R . .
C16 C -0.1013(4) 0.6462(3) 0.6319(3) 0.0625(9) Uani 1 1 d . . .
C17 C 0.0045(4) 0.6063(3) 0.7372(4) 0.0726(10) Uani 1 1 d . . .
H17 H 0.0551 0.6438 0.8071 0.087 Uiso 1 1 calc R . .
C18 C 0.0330(6) 0.5118(4) 0.7364(5) 0.0896(13) Uani 1 1 d . . .
H18 H 0.1046 0.4838 0.8042 0.108 Uiso 1 1 calc R . .
C19 C -0.0470(6) 0.4595(4) 0.6328(5) 0.0969(14) Uani 1 1 d . . .
H19 H -0.0307 0.3949 0.6301 0.116 Uiso 1 1 calc R . .
C20 C -0.1508(5) 0.5017(4) 0.5330(4) 0.0877(13) Uani 1 1 d . . .
H20 H -0.2033 0.4646 0.4634 0.105 Uiso 1 1 calc R . .
C21 C 0.4151(7) 0.6415(4) 0.5849(5) 0.1044(17) Uani 1 1 d . . .
H21A H 0.4828 0.6237 0.5319 0.125 Uiso 1 1 calc R . .
H21B H 0.3161 0.6459 0.5265 0.125 Uiso 1 1 calc R . .
C22 C 0.4164(6) 0.5684(4) 0.6837(5) 0.0985(13) Uani 1 1 d DU . .
C23 C 0.3690(9) 0.4702(6) 0.6187(8) 0.150(2) Uani 1 1 d DU . .
H23A H 0.3437 0.4301 0.6850 0.180 Uiso 1 1 calc R . .
H23B H 0.2788 0.4793 0.5492 0.180 Uiso 1 1 calc R . .
C24 C 0.4675(12) 0.4219(8) 0.5655(10) 0.203(4) Uani 1 1 d DU . .
H24A H 0.4724 0.4509 0.4838 0.304 Uiso 1 1 calc R . .
H24B H 0.4350 0.3576 0.5494 0.304 Uiso 1 1 calc R . .
H24C H 0.5641 0.4231 0.6262 0.304 Uiso 1 1 calc R . .
C25 C 0.5610(6) 0.5574(6) 0.7862(5) 0.124(2) Uani 1 1 d . . .
H25A H 0.6380 0.5410 0.7439 0.186 Uiso 1 1 calc R . .
H25B H 0.5516 0.5084 0.8471 0.186 Uiso 1 1 calc R . .
H25C H 0.5859 0.6158 0.8333 0.186 Uiso 1 1 calc R . .
C26 C 0.1360(4) 1.0523(3) 0.8768(4) 0.0722(10) Uani 1 1 d . . .
H26A H 0.2035 1.0740 0.8257 0.087 Uiso 1 1 calc R . .
H26B H 0.1918 1.0471 0.9683 0.087 Uiso 1 1 calc R . .
C27 C 0.0149(4) 1.1230(3) 0.8666(3) 0.0605(8) Uani 1 1 d . . .
C28 C 0.0796(5) 1.2135(3) 0.9316(5) 0.0846(11) Uani 1 1 d . . .
H28A H 0.1366 1.1991 1.0207 0.102 Uiso 1 1 calc R . .
H28B H 0.1483 1.2383 0.8838 0.102 Uiso 1 1 calc R . .
C29 C -0.0305(5) 1.2894(4) 0.9393(6) 0.1002(14) Uani 1 1 d . . .
H29A H -0.0801 1.3097 0.8516 0.150 Uiso 1 1 calc R . .
H29B H 0.0205 1.3421 0.9884 0.150 Uiso 1 1 calc R . .
H29C H -0.1024 1.2652 0.9826 0.150 Uiso 1 1 calc R . .
C30 C -0.0766(6) 1.1332(4) 0.7257(5) 0.1022(16) Uani 1 1 d . . .
H30A H -0.1670 1.1664 0.7248 0.153 Uiso 1 1 calc R . .
H30B H -0.1000 1.0718 0.6873 0.153 Uiso 1 1 calc R . .
H30C H -0.0210 1.1680 0.6755 0.153 Uiso 1 1 calc R . .
H22 H 0.321(4) 0.588(4) 0.702(5) 0.123 Uiso 1 1 d D . .
H27 H -0.035(6) 1.116(5) 0.918(6) 0.123 Uiso 1 1 d . . .
N1 N 0.6717(3) 1.0874(3) 0.9748(3) 0.0805(11) Uani 1 1 d . . .
N2 N -0.1799(3) 0.5940(3) 0.5315(3) 0.0747(9) Uani 1 1 d . . .
O1 O 0.0794(2) 0.96124(18) 0.8297(3) 0.0680(6) Uani 1 1 d . . .
O2 O 0.4565(3) 0.7296(3) 0.6418(3) 0.0906(9) 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
C1 0.0506(16) 0.074(3) 0.067(2) -0.0086(17) 0.0137(15) -0.0151(16)
C2 0.080(2) 0.080(3) 0.0590(18) -0.0032(18) 0.0081(17) -0.021(2)
C3 0.089(2) 0.069(3) 0.079(2) 0.008(2) 0.007(2) -0.014(2)
C4 0.106(3) 0.071(3) 0.094(3) -0.012(2) 0.029(3) -0.013(3)
C5 0.098(3) 0.099(4) 0.078(3) -0.032(3) 0.018(2) -0.013(3)
C6 0.0481(16) 0.097(3) 0.082(2) -0.011(2) 0.0034(16) -0.004(2)
C7 0.0569(18) 0.075(3) 0.085(2) -0.005(2) 0.0070(17) 0.0066(18)
C8 0.0573(16) 0.055(2) 0.0572(16) 0.0088(15) 0.0058(13) 0.0035(15)
C9 0.0686(18) 0.054(2) 0.0595(16) 0.0050(15) 0.0135(14) 0.0059(16)
C10 0.0720(19) 0.0471(19) 0.0553(16) 0.0014(14) 0.0054(14) -0.0035(15)
C11 0.0628(17) 0.0418(17) 0.0607(16) 0.0043(14) 0.0079(14) -0.0036(14)
C12 0.0565(15) 0.0446(18) 0.0555(15) 0.0054(13) 0.0081(12) -0.0003(14)
C13 0.0595(15) 0.051(2) 0.0537(15) 0.0018(14) 0.0041(12) -0.0070(15)
C14 0.064(2) 0.058(2) 0.088(2) -0.0017(18) 0.0018(17) 0.0006(17)
C15 0.0560(17) 0.074(3) 0.084(2) -0.0126(19) 0.0000(16) -0.0025(18)
C16 0.0593(18) 0.065(2) 0.0622(18) -0.0081(15) 0.0137(15) -0.0133(16)
C17 0.074(2) 0.072(3) 0.0650(19) 0.0005(18) 0.0047(16) -0.0186(19)
C18 0.097(3) 0.075(3) 0.091(3) 0.020(2) 0.014(2) -0.007(2)
C19 0.118(3) 0.064(3) 0.107(3) -0.006(3) 0.026(3) -0.003(3)
C20 0.103(3) 0.076(3) 0.080(3) -0.027(2) 0.014(2) -0.013(3)
C21 0.125(4) 0.104(4) 0.073(2) -0.029(3) 0.005(2) 0.029(3)
C22 0.0981(16) 0.0980(16) 0.0989(16) -0.0025(10) 0.0239(10) 0.0009(10)
C23 0.149(3) 0.150(3) 0.151(3) -0.0022(10) 0.0368(12) 0.0001(10)
C24 0.203(4) 0.203(4) 0.202(4) -0.0007(11) 0.0516(14) -0.0006(11)
C25 0.102(3) 0.163(6) 0.095(3) 0.014(4) 0.002(3) 0.036(4)
C26 0.0634(19) 0.055(2) 0.090(2) -0.0177(19) 0.0029(17) -0.0009(17)
C27 0.0554(16) 0.055(2) 0.0668(18) -0.0023(14) 0.0083(13) -0.0049(14)
C28 0.084(2) 0.055(2) 0.111(3) -0.021(2) 0.018(2) -0.0018(19)
C29 0.105(3) 0.074(3) 0.130(4) -0.016(3) 0.046(3) -0.001(3)
C30 0.115(3) 0.086(3) 0.087(3) -0.013(2) -0.009(3) 0.018(3)
N1 0.0650(16) 0.106(3) 0.0663(18) -0.0201(18) 0.0084(13) -0.0132(19)
N2 0.0753(17) 0.079(3) 0.0640(16) -0.0160(15) 0.0062(14) -0.0121(17)
O1 0.0582(11) 0.0541(15) 0.0902(16) -0.0077(12) 0.0161(11) -0.0060(11)
O2 0.0860(17) 0.094(2) 0.0883(17) -0.0279(16) 0.0152(14) 0.0189(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
C1 N1 1.354(5) . ?
C1 C2 1.372(5) . ?
C1 C6 1.450(6) . ?
C2 C3 1.378(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(7) . ?
C4 H4 0.9300 . ?
C5 N1 1.308(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.316(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.476(5) . ?
C7 H7 0.9300 . ?
C8 C13 1.382(5) . ?
C8 C9 1.401(5) . ?
C9 O2 1.376(4) . ?
C9 C10 1.393(5) . ?
C10 C11 1.392(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.402(4) . ?
C11 C14 1.465(5) . ?
C12 O1 1.358(4) . ?
C12 C13 1.379(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.339(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.457(6) . ?
C15 H15 0.9300 . ?
C16 N2 1.340(4) . ?
C16 C17 1.397(5) . ?
C17 C18 1.366(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(7) . ?
C19 H19 0.9300 . ?
C20 N2 1.334(6) . ?
C20 H20 0.9300 . ?
C21 O2 1.394(6) . ?
C21 C22 1.460(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C25 1.502(7) . ?
C22 C23 1.561(9) . ?
C22 H22 0.99(2) . ?
C23 C24 1.368(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 O1 1.432(4) . ?
C26 C27 1.490(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.504(5) . ?
C27 C30 1.510(6) . ?
C27 H27 0.80(6) . ?
C28 C29 1.500(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
N1 C1 C2 120.8(4) . . ?
N1 C1 C6 115.7(4) . . ?
C2 C1 C6 123.4(3) . . ?
C1 C2 C3 120.6(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 117.9(4) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 117.5(5) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
N1 C5 C4 125.7(4) . . ?
N1 C5 H5 117.1 . . ?
C4 C5 H5 117.1 . . ?
C7 C6 C1 129.0(3) . . ?
C7 C6 H6 115.5 . . ?
C1 C6 H6 115.5 . . ?
C6 C7 C8 128.7(4) . . ?
C6 C7 H7 115.6 . . ?
C8 C7 H7 115.6 . . ?
C13 C8 C9 117.8(3) . . ?
C13 C8 C7 122.1(3) . . ?
C9 C8 C7 120.1(3) . . ?
O2 C9 C10 124.7(3) . . ?
O2 C9 C8 115.5(3) . . ?
C10 C9 C8 119.7(3) . . ?
C11 C10 C9 122.1(3) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 117.6(3) . . ?
C10 C11 C14 122.8(3) . . ?
C12 C11 C14 119.3(3) . . ?
O1 C12 C13 123.4(3) . . ?
O1 C12 C11 116.7(3) . . ?
C13 C12 C11 119.9(3) . . ?
C12 C13 C8 122.8(3) . . ?
C12 C13 H13 118.6 . . ?
C8 C13 H13 118.6 . . ?
C15 C14 C11 129.0(4) . . ?
C15 C14 H14 115.5 . . ?
C11 C14 H14 115.5 . . ?
C14 C15 C16 131.0(3) . . ?
C14 C15 H15 114.5 . . ?
C16 C15 H15 114.5 . . ?
N2 C16 C17 122.0(4) . . ?
N2 C16 C15 115.1(3) . . ?
C17 C16 C15 122.8(3) . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 117.9(4) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C18 C19 C20 120.5(5) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
N2 C20 C19 122.6(4) . . ?
N2 C20 H20 118.7 . . ?
C19 C20 H20 118.7 . . ?
O2 C21 C22 112.4(4) . . ?
O2 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
O2 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C25 115.2(5) . . ?
C21 C22 C23 111.9(5) . . ?
C25 C22 C23 108.8(5) . . ?
C21 C22 H22 95(3) . . ?
C25 C22 H22 125(3) . . ?
C23 C22 H22 100(3) . . ?
C24 C23 C22 118.6(7) . . ?
C24 C23 H23A 107.7 . . ?
C22 C23 H23A 107.7 . . ?
C24 C23 H23B 107.7 . . ?
C22 C23 H23B 107.7 . . ?
H23A C23 H23B 107.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1 C26 C27 112.0(3) . . ?
O1 C26 H26A 109.2 . . ?
C27 C26 H26A 109.2 . . ?
O1 C26 H26B 109.2 . . ?
C27 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C26 C27 C28 109.4(3) . . ?
C26 C27 C30 111.3(4) . . ?
C28 C27 C30 115.0(4) . . ?
C26 C27 H27 115(4) . . ?
C28 C27 H27 92(5) . . ?
C30 C27 H27 112(4) . . ?
C29 C28 C27 115.8(3) . . ?
C29 C28 H28A 108.3 . . ?
C27 C28 H28A 108.3 . . ?
C29 C28 H28B 108.3 . . ?
C27 C28 H28B 108.3 . . ?
H28A C28 H28B 107.4 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C5 N1 C1 117.4(4) . . ?
C20 N2 C16 117.5(4) . . ?
C12 O1 C26 117.0(3) . . ?
C9 O2 C21 120.3(4) . . ?
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
N1 C1 C2 C3 -0.8(5) . . . . ?
C6 C1 C2 C3 179.9(4) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 N1 -0.1(7) . . . . ?
N1 C1 C6 C7 135.1(4) . . . . ?
C2 C1 C6 C7 -45.6(6) . . . . ?
C1 C6 C7 C8 -6.2(8) . . . . ?
C6 C7 C8 C13 -29.0(6) . . . . ?
C6 C7 C8 C9 153.0(4) . . . . ?
C13 C8 C9 O2 177.5(3) . . . . ?
C7 C8 C9 O2 -4.4(5) . . . . ?
C13 C8 C9 C10 0.2(5) . . . . ?
C7 C8 C9 C10 178.4(3) . . . . ?
O2 C9 C10 C11 -176.5(3) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
C9 C10 C11 C14 174.6(3) . . . . ?
C10 C11 C12 O1 176.5(3) . . . . ?
C14 C11 C12 O1 2.6(4) . . . . ?
C10 C11 C12 C13 -3.3(4) . . . . ?
C14 C11 C12 C13 -177.2(3) . . . . ?
O1 C12 C13 C8 -175.5(3) . . . . ?
C11 C12 C13 C8 4.2(4) . . . . ?
C9 C8 C13 C12 -2.6(5) . . . . ?
C7 C8 C13 C12 179.3(3) . . . . ?
C10 C11 C14 C15 36.6(6) . . . . ?
C12 C11 C14 C15 -149.9(4) . . . . ?
C11 C14 C15 C16 4.6(8) . . . . ?
C14 C15 C16 N2 -142.5(4) . . . . ?
C14 C15 C16 C17 39.9(7) . . . . ?
N2 C16 C17 C18 2.2(6) . . . . ?
C15 C16 C17 C18 179.7(4) . . . . ?
C16 C17 C18 C19 -1.6(6) . . . . ?
C17 C18 C19 C20 0.7(7) . . . . ?
C18 C19 C20 N2 -0.4(8) . . . . ?
O2 C21 C22 C25 -55.4(7) . . . . ?
O2 C21 C22 C23 179.7(5) . . . . ?
C21 C22 C23 C24 74.2(9) . . . . ?
C25 C22 C23 C24 -54.2(9) . . . . ?
O1 C26 C27 C28 173.5(4) . . . . ?
O1 C26 C27 C30 -58.3(5) . . . . ?
C26 C27 C28 C29 -175.2(4) . . . . ?
C30 C27 C28 C29 58.6(6) . . . . ?
C4 C5 N1 C1 -0.8(7) . . . . ?
C2 C1 N1 C5 1.2(5) . . . . ?
C6 C1 N1 C5 -179.4(4) . . . . ?
C19 C20 N2 C16 1.0(6) . . . . ?
C17 C16 N2 C20 -1.9(5) . . . . ?
C15 C16 N2 C20 -179.5(4) . . . . ?
C13 C12 O1 C26 21.0(5) . . . . ?
C11 C12 O1 C26 -158.7(3) . . . . ?
C27 C26 O1 C12 157.0(3) . . . . ?
C10 C9 O2 C21 -21.2(6) . . . . ?
C8 C9 O2 C21 161.7(3) . . . . ?
C22 C21 O2 C9 -76.3(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.424
_refine_diff_density_min -0.302
_refine_diff_density_rms 0.048
_database_code_depnum_ccdc_archive 'CCDC 855788'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_3
#TrackingRef 'web_deposit_cif_file_3_zhaodiliu_1322483613.L.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C30 H36 N2 O2'
_chemical_formula_weight 456.61
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'
_symmetry_cell_setting ?
_symmetry_space_group_name_H-M ?
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 9.735(7)
_cell_length_b 13.866(10)
_cell_length_c 10.782(8)
_cell_angle_alpha 90.00
_cell_angle_beta 113.771(9)
_cell_angle_gamma 90.00
_cell_volume 1331.9(17)
_cell_formula_units_Z 2
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description ?
_exptl_crystal_colour ?
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.139
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 492
_exptl_absorpt_coefficient_mu 0.071
_exptl_absorpt_correction_type ?
_exptl_absorpt_correction_T_min 0.9860
_exptl_absorpt_correction_T_max 0.9930
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(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 ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 7263
_diffrn_reflns_av_R_equivalents 0.0372
_diffrn_reflns_av_sigmaI/netI 0.0386
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.29
_diffrn_reflns_theta_max 25.00
_reflns_number_total 2339
_reflns_number_gt 1641
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.1702P)^2^+1.5007P] 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 0.038(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 2339
_refine_ls_number_parameters 160
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.1279
_refine_ls_R_factor_gt 0.1059
_refine_ls_wR_factor_ref 0.3449
_refine_ls_wR_factor_gt 0.3294
_refine_ls_goodness_of_fit_ref 1.099
_refine_ls_restrained_S_all 1.098
_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 0.1333(5) 0.2839(3) 0.2640(4) 0.0557(11) Uani 1 1 d . . .
C2 C 0.0441(6) 0.3385(4) 0.3078(5) 0.0798(16) Uani 1 1 d . . .
H2 H 0.0557 0.3347 0.3976 0.096 Uiso 1 1 calc R . .
C3 C -0.0626(8) 0.3990(5) 0.2191(6) 0.102(2) Uani 1 1 d . . .
H3 H -0.1265 0.4342 0.2468 0.122 Uiso 1 1 calc R . .
C4 C -0.0723(7) 0.4060(4) 0.0892(6) 0.097(2) Uani 1 1 d . . .
H4 H -0.1426 0.4462 0.0263 0.116 Uiso 1 1 calc R . .
C5 C 0.0244(7) 0.3522(4) 0.0547(5) 0.0904(18) Uani 1 1 d . . .
H5 H 0.0193 0.3586 -0.0329 0.108 Uiso 1 1 calc R . .
C6 C 0.2359(5) 0.2129(3) 0.3551(4) 0.0583(12) Uani 1 1 d . . .
H6 H 0.2540 0.2175 0.4464 0.070 Uiso 1 1 calc R . .
C7 C 0.3055(5) 0.1430(3) 0.3203(4) 0.0555(11) Uani 1 1 d . . .
H7 H 0.2911 0.1398 0.2297 0.067 Uiso 1 1 calc R . .
C8 C 0.4037(4) 0.0696(3) 0.4121(4) 0.0511(10) Uani 1 1 d . . .
C9 C 0.4510(5) -0.0103(3) 0.3605(4) 0.0523(11) Uani 1 1 d . . .
C10 C 0.5449(5) -0.0778(3) 0.4472(4) 0.0562(11) Uani 1 1 d . . .
H10 H 0.5750 -0.1305 0.4110 0.067 Uiso 1 1 calc R . .
C11 C 0.4352(7) -0.0960(4) 0.1613(4) 0.0797(16) Uani 1 1 d . . .
H11A H 0.4117 -0.1561 0.1945 0.096 Uiso 1 1 calc R . .
H11B H 0.5422 -0.0944 0.1839 0.096 Uiso 1 1 calc R . .
C12 C 0.3492(7) -0.0893(4) 0.0100(5) 0.0874(18) Uani 1 1 d D . .
C13 C 0.4141(11) -0.1598(6) -0.0605(7) 0.131(3) Uani 1 1 d . . .
H13A H 0.4029 -0.2256 -0.0357 0.157 Uiso 1 1 calc R . .
H13B H 0.5199 -0.1470 -0.0356 0.157 Uiso 1 1 calc R . .
C14 C 0.324(2) -0.1438(11) -0.2147(12) 0.239(7) Uani 1 1 d . . .
H14A H 0.2864 -0.2046 -0.2578 0.359 Uiso 1 1 calc R . .
H14B H 0.3876 -0.1156 -0.2531 0.359 Uiso 1 1 calc R . .
H14C H 0.2407 -0.1014 -0.2286 0.359 Uiso 1 1 calc R . .
C15 C 0.1800(10) -0.0998(7) -0.0273(7) 0.141(3) Uani 1 1 d . . .
H15A H 0.1261 -0.0920 -0.1233 0.211 Uiso 1 1 calc R . .
H15B H 0.1483 -0.0514 0.0192 0.211 Uiso 1 1 calc R . .
H15C H 0.1599 -0.1626 -0.0009 0.211 Uiso 1 1 calc R . .
H12 H 0.373(11) -0.031(4) -0.027(8) 0.169 Uiso 1 1 d D . .
N1 N 0.1250(5) 0.2913(3) 0.1370(4) 0.0717(12) Uani 1 1 d . . .
O1 O 0.3937(4) -0.0166(2) 0.2219(3) 0.0677(10) 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
C1 0.059(2) 0.057(2) 0.048(2) 0.0050(18) 0.0194(19) 0.0003(19)
C2 0.095(4) 0.088(4) 0.060(3) 0.017(3) 0.034(3) 0.032(3)
C3 0.118(5) 0.108(5) 0.088(4) 0.029(3) 0.050(4) 0.058(4)
C4 0.108(5) 0.090(4) 0.083(4) 0.026(3) 0.028(3) 0.048(4)
C5 0.114(4) 0.095(4) 0.053(3) 0.020(3) 0.024(3) 0.032(4)
C6 0.059(2) 0.069(3) 0.045(2) 0.0072(19) 0.0184(19) 0.006(2)
C7 0.059(2) 0.060(3) 0.043(2) 0.0039(17) 0.0150(18) 0.004(2)
C8 0.051(2) 0.052(2) 0.046(2) 0.0052(17) 0.0146(17) -0.0002(18)
C9 0.056(2) 0.058(2) 0.0379(19) 0.0014(17) 0.0129(17) -0.0012(19)
C10 0.062(2) 0.055(2) 0.047(2) 0.0025(18) 0.0175(19) 0.005(2)
C11 0.102(4) 0.073(3) 0.054(3) -0.004(2) 0.020(3) 0.020(3)
C12 0.107(4) 0.084(4) 0.052(3) -0.005(2) 0.011(3) 0.020(3)
C13 0.186(8) 0.123(6) 0.076(4) -0.012(4) 0.044(5) 0.026(6)
C14 0.38(2) 0.225(14) 0.158(10) -0.020(10) 0.155(12) 0.021(15)
C15 0.140(7) 0.161(8) 0.087(4) -0.023(5) 0.011(4) -0.025(6)
N1 0.087(3) 0.073(3) 0.054(2) 0.0142(18) 0.027(2) 0.024(2)
O1 0.082(2) 0.070(2) 0.0400(15) 0.0024(13) 0.0136(14) 0.0203(16)
_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 N1 1.343(5) . ?
C1 C2 1.372(7) . ?
C1 C6 1.463(6) . ?
C2 C3 1.377(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(8) . ?
C4 H4 0.9300 . ?
C5 N1 1.326(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.321(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.472(6) . ?
C7 H7 0.9300 . ?
C8 C10 1.397(6) 3_656 ?
C8 C9 1.399(6) . ?
C9 O1 1.371(5) . ?
C9 C10 1.377(6) . ?
C10 C8 1.397(6) 3_656 ?
C10 H10 0.9300 . ?
C11 O1 1.420(6) . ?
C11 C12 1.506(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.523(9) . ?
C12 C15 1.538(11) . ?
C12 H12 0.97(2) . ?
C13 C14 1.552(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
N1 C1 C2 121.5(4) . . ?
N1 C1 C6 118.7(4) . . ?
C2 C1 C6 119.7(4) . . ?
C1 C2 C3 120.2(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 118.4(5) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 118.0(5) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N1 C5 C4 124.7(5) . . ?
N1 C5 H5 117.6 . . ?
C4 C5 H5 117.6 . . ?
C7 C6 C1 126.3(4) . . ?
C7 C6 H6 116.8 . . ?
C1 C6 H6 116.8 . . ?
C6 C7 C8 125.8(4) . . ?
C6 C7 H7 117.1 . . ?
C8 C7 H7 117.1 . . ?
C10 C8 C9 117.7(4) 3_656 . ?
C10 C8 C7 121.7(4) 3_656 . ?
C9 C8 C7 120.6(4) . . ?
O1 C9 C10 124.3(4) . . ?
O1 C9 C8 115.4(3) . . ?
C10 C9 C8 120.2(4) . . ?
C9 C10 C8 122.1(4) . 3_656 ?
C9 C10 H10 119.0 . . ?
C8 C10 H10 119.0 3_656 . ?
O1 C11 C12 108.3(4) . . ?
O1 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O1 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C11 C12 C13 109.8(5) . . ?
C11 C12 C15 110.2(6) . . ?
C13 C12 C15 115.2(6) . . ?
C11 C12 H12 112(5) . . ?
C13 C12 H12 97(5) . . ?
C15 C12 H12 112(6) . . ?
C12 C13 C14 105.8(7) . . ?
C12 C13 H13A 110.6 . . ?
C14 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
C14 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 N1 C1 117.1(4) . . ?
C9 O1 C11 119.0(3) . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 1.001
_refine_diff_density_min -0.375
_refine_diff_density_rms 0.068
_database_code_depnum_ccdc_archive 'CCDC 855789'