# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_HsalH-4-CN #TrackingRef 'web_deposit_cif_file_0_Jing-YunWu_1366794164.HsalH-4-CN.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 N2 O' _chemical_formula_weight 222.24 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.075(6) _cell_length_b 5.7634(12) _cell_length_c 14.427(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.082(10) _cell_angle_gamma 90.00 _cell_volume 2192.4(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2001 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 25.01 _exptl_crystal_description plate _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6772 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7165 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1911 _reflns_number_gt 1462 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0449P)^2^+0.8844P] 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 1911 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.17498(5) 0.2637(3) 0.35298(9) 0.0163(3) Uani 1 1 d . . . C2 C 0.16250(5) 0.0516(3) 0.38809(9) 0.0164(4) Uani 1 1 d . . . C3 C 0.11256(5) 0.0068(3) 0.37964(10) 0.0189(4) Uani 1 1 d . . . H3 H 0.1043 -0.1328 0.4027 0.023 Uiso 1 1 calc R . . C4 C 0.07516(6) 0.1690(3) 0.33714(10) 0.0205(4) Uani 1 1 d . . . H4 H 0.0418 0.1374 0.3317 0.025 Uiso 1 1 calc R . . C5 C 0.08680(5) 0.3793(3) 0.30227(10) 0.0204(4) Uani 1 1 d . . . H5 H 0.0614 0.4875 0.2735 0.025 Uiso 1 1 calc R . . C6 C 0.13620(5) 0.4251(3) 0.31083(9) 0.0182(4) Uani 1 1 d . . . H6 H 0.1441 0.5661 0.2882 0.022 Uiso 1 1 calc R . . C7 C 0.22617(5) 0.3156(3) 0.35795(9) 0.0173(4) Uani 1 1 d . . . H7 H 0.2334 0.4615 0.3388 0.021 Uiso 1 1 calc R . . C8 C 0.31213(5) 0.2076(3) 0.39187(9) 0.0159(4) Uani 1 1 d . . . C9 C 0.32828(5) 0.4056(3) 0.35512(10) 0.0185(4) Uani 1 1 d . . . H9 H 0.3051 0.5221 0.3254 0.022 Uiso 1 1 calc R . . C10 C 0.37832(5) 0.4291(3) 0.36265(10) 0.0186(4) Uani 1 1 d . . . H10 H 0.3890 0.5619 0.3387 0.022 Uiso 1 1 calc R . . C11 C 0.41299(5) 0.2538(3) 0.40616(10) 0.0175(4) Uani 1 1 d . . . C12 C 0.39727(5) 0.0554(3) 0.44280(10) 0.0192(4) Uani 1 1 d . . . H12 H 0.4204 -0.0614 0.4722 0.023 Uiso 1 1 calc R . . C13 C 0.34706(5) 0.0336(3) 0.43510(10) 0.0180(4) Uani 1 1 d . . . H13 H 0.3365 -0.0991 0.4591 0.022 Uiso 1 1 calc R . . C14 C 0.46488(6) 0.2742(3) 0.41100(10) 0.0213(4) Uani 1 1 d . . . N1 N 0.26191(4) 0.1643(2) 0.38833(8) 0.0171(3) Uani 1 1 d . . . N2 N 0.50621(5) 0.2861(2) 0.41342(10) 0.0312(4) Uani 1 1 d . . . O1 O 0.19835(4) -0.11128(18) 0.43048(7) 0.0214(3) Uani 1 1 d . . . H101 H 0.2282 -0.0509 0.4240 0.032 Uiso 1 1 d 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 C1 0.0180(8) 0.0174(8) 0.0138(7) -0.0030(6) 0.0061(6) -0.0013(7) C2 0.0192(8) 0.0158(9) 0.0136(7) -0.0019(6) 0.0049(6) 0.0015(7) C3 0.0212(9) 0.0185(9) 0.0183(7) -0.0005(6) 0.0084(6) -0.0054(7) C4 0.0173(8) 0.0259(10) 0.0188(7) -0.0026(6) 0.0066(6) -0.0026(7) C5 0.0194(8) 0.0222(9) 0.0193(7) 0.0013(7) 0.0062(6) 0.0031(7) C6 0.0216(8) 0.0178(9) 0.0156(7) 0.0001(6) 0.0070(6) -0.0008(7) C7 0.0209(8) 0.0167(8) 0.0149(7) -0.0008(6) 0.0067(6) -0.0033(7) C8 0.0172(8) 0.0177(9) 0.0133(7) -0.0023(6) 0.0061(6) -0.0022(7) C9 0.0185(8) 0.0184(9) 0.0179(7) 0.0015(6) 0.0054(6) 0.0018(7) C10 0.0203(8) 0.0185(9) 0.0176(7) 0.0004(6) 0.0073(6) -0.0036(7) C11 0.0161(8) 0.0217(9) 0.0152(7) -0.0028(6) 0.0061(6) -0.0016(7) C12 0.0181(8) 0.0197(9) 0.0188(7) 0.0007(6) 0.0051(6) 0.0021(7) C13 0.0221(8) 0.0157(9) 0.0165(7) 0.0001(6) 0.0069(6) -0.0014(7) C14 0.0222(9) 0.0191(9) 0.0216(8) 0.0031(6) 0.0064(6) 0.0011(7) N1 0.0153(6) 0.0187(7) 0.0171(6) -0.0001(5) 0.0054(5) -0.0016(6) N2 0.0211(8) 0.0307(9) 0.0425(8) 0.0095(7) 0.0118(6) 0.0007(7) O1 0.0177(6) 0.0184(6) 0.0285(5) 0.0046(5) 0.0084(4) -0.0003(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.402(2) . ? C1 C2 1.413(2) . ? C1 C7 1.445(2) . ? C2 O1 1.3583(17) . ? C2 C3 1.389(2) . ? C3 C4 1.382(2) . ? C4 C5 1.394(2) . ? C5 C6 1.375(2) . ? C7 N1 1.2873(18) . ? C8 C13 1.391(2) . ? C8 C9 1.398(2) . ? C8 N1 1.4152(18) . ? C9 C10 1.378(2) . ? C10 C11 1.394(2) . ? C11 C12 1.394(2) . ? C11 C14 1.439(2) . ? C12 C13 1.381(2) . ? C14 N2 1.1509(19) . ? 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 118.58(13) . . ? C6 C1 C7 119.68(14) . . ? C2 C1 C7 121.73(13) . . ? O1 C2 C3 118.72(13) . . ? O1 C2 C1 121.53(13) . . ? C3 C2 C1 119.76(13) . . ? C4 C3 C2 120.22(14) . . ? C3 C4 C5 120.80(14) . . ? C6 C5 C4 119.25(14) . . ? C5 C6 C1 121.39(14) . . ? N1 C7 C1 121.49(14) . . ? C13 C8 C9 119.20(13) . . ? C13 C8 N1 115.43(13) . . ? C9 C8 N1 125.37(13) . . ? C10 C9 C8 120.33(14) . . ? C9 C10 C11 119.98(14) . . ? C10 C11 C12 120.16(13) . . ? C10 C11 C14 120.10(14) . . ? C12 C11 C14 119.72(13) . . ? C13 C12 C11 119.43(14) . . ? C12 C13 C8 120.90(14) . . ? N2 C14 C11 178.41(17) . . ? C7 N1 C8 122.92(13) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.190 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 935863' ####################################################################### # # 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_HsalOMe-4-CN #TrackingRef 'web_deposit_cif_file_1_Jing-YunWu_1366794164.HsalOMe-4-CN.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N2 O2' _chemical_formula_weight 252.27 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 Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 13.2684(16) _cell_length_b 6.2747(6) _cell_length_c 29.454(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2452.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1841 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 24.93 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5861 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8020 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.07 _reflns_number_total 2124 _reflns_number_gt 1413 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0653P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2124 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.10688(13) 0.6802(3) 0.78000(6) 0.0192(4) Uani 1 1 d . . . C2 C 0.14068(13) 0.4664(3) 0.78314(6) 0.0213(5) Uani 1 1 d . . . C3 C 0.15770(13) 0.3792(3) 0.82505(6) 0.0235(5) Uani 1 1 d . . . H3 H 0.1795 0.2386 0.8271 0.028 Uiso 1 1 calc R . . C4 C 0.14333(13) 0.4948(3) 0.86434(6) 0.0238(5) Uani 1 1 d . . . H4 H 0.1560 0.4328 0.8924 0.029 Uiso 1 1 calc R . . C5 C 0.10960(14) 0.7059(3) 0.86182(6) 0.0222(5) Uani 1 1 d . . . C6 C 0.09135(13) 0.7940(3) 0.81993(6) 0.0217(5) Uani 1 1 d . . . H6 H 0.0680 0.9335 0.8182 0.026 Uiso 1 1 calc R . . C7 C 0.09695(14) 0.7870(3) 0.73691(6) 0.0223(5) Uani 1 1 d . . . H7 H 0.0801 0.9309 0.7367 0.027 Uiso 1 1 calc R . . C8 C 0.11255(13) 0.8102(3) 0.65813(6) 0.0214(4) Uani 1 1 d . . . C9 C 0.15363(13) 1.0154(3) 0.65614(6) 0.0231(5) Uani 1 1 d . . . H9 H 0.1784 1.0794 0.6824 0.028 Uiso 1 1 calc R . . C10 C 0.15744(13) 1.1225(3) 0.61549(6) 0.0248(5) Uani 1 1 d . . . H10 H 0.1843 1.2593 0.6143 0.030 Uiso 1 1 calc R . . C11 C 0.12162(14) 1.0279(3) 0.57629(6) 0.0241(5) Uani 1 1 d . . . C12 C 0.08120(14) 0.8218(3) 0.57776(6) 0.0254(5) Uani 1 1 d . . . H12 H 0.0568 0.7579 0.5515 0.030 Uiso 1 1 calc R . . C13 C 0.07795(14) 0.7147(3) 0.61854(6) 0.0245(5) Uani 1 1 d . . . H13 H 0.0523 0.5768 0.6196 0.029 Uiso 1 1 calc R . . C14 C 0.12498(15) 1.1430(3) 0.53411(7) 0.0283(5) Uani 1 1 d . . . C15 C 0.13212(16) 0.7644(3) 0.94132(6) 0.0322(5) Uani 1 1 d . . . H15A H 0.0958 0.6393 0.9505 0.048 Uiso 1 1 calc R . . H15B H 0.1232 0.8745 0.9636 0.048 Uiso 1 1 calc R . . H15C H 0.2025 0.7310 0.9386 0.048 Uiso 1 1 calc R . . N1 N 0.11042(11) 0.6914(2) 0.69884(5) 0.0214(4) Uani 1 1 d . . . N2 N 0.12671(14) 1.2368(3) 0.50051(6) 0.0394(5) Uani 1 1 d . . . O1 O 0.15612(9) 0.34702(19) 0.74531(4) 0.0271(4) Uani 1 1 d . . . H101 H 0.1434 0.4264 0.7204 0.041 Uiso 1 1 d R . . O2 O 0.09476(10) 0.83609(19) 0.89859(4) 0.0284(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0144(10) 0.0192(10) 0.0241(11) 0.0018(8) 0.0003(8) -0.0022(7) C2 0.0188(11) 0.0187(10) 0.0264(11) -0.0029(8) -0.0009(9) -0.0022(7) C3 0.0209(11) 0.0172(10) 0.0324(12) -0.0003(8) -0.0022(9) -0.0009(8) C4 0.0215(11) 0.0228(10) 0.0272(11) 0.0031(8) -0.0024(9) -0.0015(8) C5 0.0197(11) 0.0248(10) 0.0221(11) -0.0017(8) 0.0017(8) -0.0011(8) C6 0.0204(10) 0.0166(10) 0.0281(12) -0.0008(8) 0.0006(9) 0.0010(8) C7 0.0191(11) 0.0177(10) 0.0299(12) -0.0024(8) -0.0016(9) 0.0011(8) C8 0.0200(10) 0.0205(10) 0.0238(11) -0.0012(8) 0.0020(9) 0.0038(7) C9 0.0228(11) 0.0206(10) 0.0260(11) -0.0047(8) -0.0027(9) 0.0020(7) C10 0.0249(11) 0.0183(10) 0.0312(12) -0.0004(8) 0.0005(9) 0.0008(8) C11 0.0232(11) 0.0219(10) 0.0271(12) -0.0001(8) 0.0002(9) 0.0004(8) C12 0.0257(11) 0.0261(10) 0.0244(11) -0.0038(8) -0.0032(9) 0.0000(8) C13 0.0248(11) 0.0205(10) 0.0282(12) -0.0020(8) 0.0002(9) 0.0000(8) C14 0.0275(12) 0.0281(11) 0.0292(12) -0.0019(9) -0.0023(10) -0.0020(8) C15 0.0390(14) 0.0317(12) 0.0259(12) -0.0001(9) -0.0028(10) 0.0020(9) N1 0.0199(9) 0.0206(9) 0.0239(9) -0.0016(7) 0.0000(7) -0.0007(6) N2 0.0478(13) 0.0365(11) 0.0340(12) 0.0038(9) -0.0017(10) -0.0049(8) O1 0.0340(9) 0.0191(7) 0.0283(8) -0.0031(5) -0.0027(6) 0.0034(6) O2 0.0396(9) 0.0249(8) 0.0207(7) -0.0021(6) -0.0010(6) 0.0053(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.391(2) . ? C1 C2 1.417(2) . ? C1 C7 1.441(2) . ? C2 O1 1.358(2) . ? C2 C3 1.369(2) . ? C3 C4 1.379(2) . ? C4 C5 1.400(3) . ? C5 O2 1.371(2) . ? C5 C6 1.374(2) . ? C7 N1 1.284(2) . ? C8 C13 1.389(2) . ? C8 C9 1.400(2) . ? C8 N1 1.412(2) . ? C9 C10 1.374(2) . ? C10 C11 1.382(3) . ? C11 C12 1.401(3) . ? C11 C14 1.438(3) . ? C12 C13 1.377(2) . ? C14 N2 1.152(2) . ? C15 O2 1.426(2) . ? 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 118.52(16) . . ? C6 C1 C7 119.48(17) . . ? C2 C1 C7 121.76(16) . . ? O1 C2 C3 119.64(17) . . ? O1 C2 C1 121.07(16) . . ? C3 C2 C1 119.29(17) . . ? C2 C3 C4 121.57(18) . . ? C3 C4 C5 119.84(17) . . ? O2 C5 C6 116.38(16) . . ? O2 C5 C4 124.61(16) . . ? C6 C5 C4 118.99(17) . . ? C5 C6 C1 121.77(17) . . ? N1 C7 C1 122.63(18) . . ? C13 C8 C9 119.37(17) . . ? C13 C8 N1 118.60(17) . . ? C9 C8 N1 121.93(16) . . ? C10 C9 C8 120.04(17) . . ? C9 C10 C11 120.35(18) . . ? C10 C11 C12 120.15(17) . . ? C10 C11 C14 119.69(17) . . ? C12 C11 C14 120.16(16) . . ? C13 C12 C11 119.30(17) . . ? C12 C13 C8 120.77(18) . . ? N2 C14 C11 179.2(2) . . ? C7 N1 C8 119.87(17) . . ? C5 O2 C15 117.34(14) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.188 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 935864' ####################################################################### # # 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_cpd1 #TrackingRef 'web_deposit_cif_file_2_Jing-YunWu_1366794164.cpd 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H25 Cl2 N3 O Zn' _chemical_formula_weight 459.70 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1423(2) _cell_length_b 13.0443(5) _cell_length_c 23.0388(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.2670(10) _cell_angle_gamma 90.00 _cell_volume 2140.49(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8627 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 24.85 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6486 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13248 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 24.85 _reflns_number_total 3687 _reflns_number_gt 3391 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0247P)^2^+0.9418P] 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 3687 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0224 _refine_ls_R_factor_gt 0.0197 _refine_ls_wR_factor_ref 0.0526 _refine_ls_wR_factor_gt 0.0512 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.002 _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 0.03329(2) 0.529772(13) 0.348128(7) 0.01681(7) Uani 1 1 d . . . Cl1 Cl -0.26286(5) 0.55170(3) 0.372292(17) 0.02273(10) Uani 1 1 d . . . Cl2 Cl 0.10899(6) 0.63541(3) 0.277458(16) 0.02221(10) Uani 1 1 d . . . O1 O 0.10109(16) 0.38757(8) 0.33196(4) 0.0203(2) Uani 1 1 d . . . N1 N 0.20277(18) 0.53758(9) 0.42367(5) 0.0164(3) Uani 1 1 d . . . N2 N 0.3783(2) 0.98588(11) 0.56705(6) 0.0277(3) Uani 1 1 d . . . N3 N 0.66624(18) 0.66230(10) 0.75802(5) 0.0187(3) Uani 1 1 d . . . H101 H 0.7528 0.6522 0.7340 0.028 Uiso 1 1 d R . . C1 C 0.2067(2) 0.35036(12) 0.43226(7) 0.0172(3) Uani 1 1 d . . . C2 C 0.1314(2) 0.32146(12) 0.37551(7) 0.0173(3) Uani 1 1 d . . . C3 C 0.0965(2) 0.21679(12) 0.36528(7) 0.0215(4) Uani 1 1 d . . . H3 H 0.0485 0.1957 0.3286 0.026 Uiso 1 1 calc R . . C4 C 0.1319(2) 0.14464(13) 0.40850(7) 0.0246(4) Uani 1 1 d . . . H4 H 0.1079 0.0759 0.4003 0.030 Uiso 1 1 calc R . . C5 C 0.2029(2) 0.17281(13) 0.46409(7) 0.0245(4) Uani 1 1 d . . . H5 H 0.2240 0.1239 0.4932 0.029 Uiso 1 1 calc R . . C6 C 0.2413(2) 0.27446(13) 0.47509(7) 0.0219(4) Uani 1 1 d . . . H6 H 0.2914 0.2936 0.5119 0.026 Uiso 1 1 calc R . . C7 C 0.2494(2) 0.45374(12) 0.45071(7) 0.0176(3) Uani 1 1 d . . . H7 H 0.3187 0.4609 0.4863 0.021 Uiso 1 1 calc R . . C8 C 0.2420(2) 0.63217(12) 0.45340(7) 0.0168(3) Uani 1 1 d . . . C9 C 0.2265(2) 0.64000(12) 0.51316(7) 0.0187(3) Uani 1 1 d . . . H9 H 0.1931 0.5829 0.5342 0.022 Uiso 1 1 calc R . . C10 C 0.2606(2) 0.73199(12) 0.54112(7) 0.0189(3) Uani 1 1 d . . . H10 H 0.2504 0.7369 0.5810 0.023 Uiso 1 1 calc R . . C11 C 0.3104(2) 0.81773(12) 0.50986(7) 0.0187(3) Uani 1 1 d . . . C12 C 0.3240(2) 0.81074(12) 0.44986(7) 0.0226(4) Uani 1 1 d . . . H12 H 0.3564 0.8680 0.4288 0.027 Uiso 1 1 calc R . . C13 C 0.2892(2) 0.71812(13) 0.42197(7) 0.0221(4) Uani 1 1 d . . . H13 H 0.2973 0.7133 0.3820 0.027 Uiso 1 1 calc R . . C14 C 0.3482(2) 0.91262(13) 0.54075(7) 0.0215(4) Uani 1 1 d . . . C15 C 0.7644(2) 0.66964(13) 0.81800(7) 0.0226(4) Uani 1 1 d . . . H15A H 0.8337 0.7336 0.8213 0.027 Uiso 1 1 calc R . . H15B H 0.6711 0.6708 0.8465 0.027 Uiso 1 1 calc R . . C16 C 0.8974(2) 0.58211(14) 0.83159(7) 0.0278(4) Uani 1 1 d . . . H16A H 0.8272 0.5200 0.8352 0.042 Uiso 1 1 calc R . . H16B H 0.9702 0.5956 0.8675 0.042 Uiso 1 1 calc R . . H16C H 0.9797 0.5748 0.8008 0.042 Uiso 1 1 calc R . . C17 C 0.5432(2) 0.56886(13) 0.74914(7) 0.0235(4) Uani 1 1 d . . . H17A H 0.6194 0.5081 0.7567 0.028 Uiso 1 1 calc R . . H17B H 0.4939 0.5664 0.7088 0.028 Uiso 1 1 calc R . . C18 C 0.3811(3) 0.56642(15) 0.78755(8) 0.0330(4) Uani 1 1 d . . . H18A H 0.4282 0.5579 0.8274 0.049 Uiso 1 1 calc R . . H18B H 0.2996 0.5102 0.7763 0.049 Uiso 1 1 calc R . . H18C H 0.3123 0.6296 0.7835 0.049 Uiso 1 1 calc R . . C19 C 0.5662(2) 0.76221(13) 0.74435(7) 0.0247(4) Uani 1 1 d . . . H19A H 0.6587 0.8166 0.7439 0.030 Uiso 1 1 calc R . . H19B H 0.4851 0.7773 0.7752 0.030 Uiso 1 1 calc R . . C20 C 0.4495(3) 0.76234(15) 0.68680(7) 0.0305(4) Uani 1 1 d . . . H20A H 0.5248 0.7389 0.6566 0.046 Uiso 1 1 calc R . . H20B H 0.4060 0.8307 0.6781 0.046 Uiso 1 1 calc R . . H20C H 0.3438 0.7175 0.6892 0.046 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 0.02052(11) 0.01624(11) 0.01343(10) 0.00098(7) -0.00030(7) 0.00035(7) Cl1 0.0204(2) 0.0260(2) 0.0217(2) 0.00344(16) 0.00125(15) 0.00006(16) Cl2 0.0266(2) 0.0234(2) 0.01677(19) 0.00515(15) 0.00246(15) 0.00047(16) O1 0.0276(6) 0.0174(6) 0.0158(5) -0.0007(4) 0.0012(5) 0.0014(5) N1 0.0175(7) 0.0162(7) 0.0155(6) -0.0007(5) 0.0011(5) -0.0014(5) N2 0.0381(9) 0.0195(8) 0.0255(8) -0.0014(6) 0.0027(6) -0.0029(7) N3 0.0189(7) 0.0203(7) 0.0170(7) -0.0013(5) 0.0019(5) 0.0021(6) C1 0.0151(8) 0.0164(8) 0.0200(8) 0.0001(6) 0.0010(6) 0.0007(6) C2 0.0156(8) 0.0177(8) 0.0188(8) -0.0001(6) 0.0033(6) 0.0010(6) C3 0.0213(8) 0.0211(9) 0.0218(8) -0.0054(7) -0.0002(7) -0.0007(7) C4 0.0252(9) 0.0145(8) 0.0340(10) -0.0015(7) 0.0005(7) 0.0003(7) C5 0.0258(9) 0.0174(8) 0.0294(9) 0.0049(7) -0.0032(7) 0.0030(7) C6 0.0190(8) 0.0237(9) 0.0220(8) 0.0000(7) -0.0044(6) 0.0022(7) C7 0.0148(8) 0.0223(8) 0.0154(8) -0.0010(6) -0.0008(6) 0.0006(6) C8 0.0142(7) 0.0173(8) 0.0186(8) 0.0000(6) -0.0013(6) 0.0001(6) C9 0.0194(8) 0.0170(8) 0.0196(8) 0.0031(6) 0.0015(6) -0.0006(6) C10 0.0203(8) 0.0210(8) 0.0155(8) -0.0003(6) 0.0016(6) 0.0005(7) C11 0.0180(8) 0.0163(8) 0.0214(8) -0.0007(6) -0.0014(6) 0.0000(6) C12 0.0289(9) 0.0173(8) 0.0211(8) 0.0042(7) -0.0005(7) -0.0042(7) C13 0.0282(9) 0.0221(9) 0.0158(8) 0.0018(7) 0.0002(7) -0.0034(7) C14 0.0236(9) 0.0204(9) 0.0204(8) 0.0040(7) 0.0014(7) 0.0000(7) C15 0.0258(9) 0.0237(9) 0.0177(8) -0.0011(7) -0.0023(7) -0.0022(7) C16 0.0251(9) 0.0323(10) 0.0254(9) 0.0033(8) -0.0021(7) 0.0025(8) C17 0.0228(9) 0.0218(9) 0.0256(9) -0.0061(7) -0.0005(7) -0.0016(7) C18 0.0268(10) 0.0285(10) 0.0445(11) -0.0041(9) 0.0085(8) -0.0050(8) C19 0.0270(9) 0.0231(9) 0.0240(9) 0.0018(7) 0.0014(7) 0.0067(7) C20 0.0300(10) 0.0379(11) 0.0235(9) 0.0029(8) 0.0010(7) 0.0114(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9598(11) . ? Zn1 N1 2.0471(13) . ? Zn1 Cl2 2.2300(4) . ? Zn1 Cl1 2.2452(4) . ? O1 C2 1.3284(18) . ? N1 C7 1.290(2) . ? N1 C8 1.4289(19) . ? N2 C14 1.143(2) . ? N3 C15 1.5054(19) . ? N3 C17 1.508(2) . ? N3 C19 1.508(2) . ? C1 C6 1.407(2) . ? C1 C2 1.427(2) . ? C1 C7 1.440(2) . ? C2 C3 1.405(2) . ? C3 C4 1.380(2) . ? C4 C5 1.392(2) . ? C5 C6 1.374(2) . ? C8 C13 1.390(2) . ? C8 C9 1.393(2) . ? C9 C10 1.375(2) . ? C10 C11 1.391(2) . ? C11 C12 1.396(2) . ? C11 C14 1.443(2) . ? C12 C13 1.382(2) . ? C15 C16 1.503(2) . ? C17 C18 1.509(2) . ? C19 C20 1.513(2) . ? 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 N1 94.00(5) . . ? O1 Zn1 Cl2 111.68(3) . . ? N1 Zn1 Cl2 115.45(4) . . ? O1 Zn1 Cl1 114.73(4) . . ? N1 Zn1 Cl1 106.93(4) . . ? Cl2 Zn1 Cl1 112.728(16) . . ? C2 O1 Zn1 119.98(9) . . ? C7 N1 C8 117.78(13) . . ? C7 N1 Zn1 118.92(10) . . ? C8 N1 Zn1 122.20(10) . . ? C15 N3 C17 113.76(12) . . ? C15 N3 C19 108.53(12) . . ? C17 N3 C19 114.07(12) . . ? C6 C1 C2 119.43(14) . . ? C6 C1 C7 115.46(14) . . ? C2 C1 C7 125.10(14) . . ? O1 C2 C3 119.17(14) . . ? O1 C2 C1 123.35(14) . . ? C3 C2 C1 117.42(14) . . ? C4 C3 C2 121.41(15) . . ? C3 C4 C5 121.26(15) . . ? C6 C5 C4 118.60(15) . . ? C5 C6 C1 121.86(15) . . ? N1 C7 C1 127.59(14) . . ? C13 C8 C9 119.73(14) . . ? C13 C8 N1 119.55(13) . . ? C9 C8 N1 120.68(14) . . ? C10 C9 C8 120.18(14) . . ? C9 C10 C11 120.15(14) . . ? C10 C11 C12 119.97(14) . . ? C10 C11 C14 118.67(14) . . ? C12 C11 C14 121.35(14) . . ? C13 C12 C11 119.61(15) . . ? C12 C13 C8 120.34(14) . . ? N2 C14 C11 177.55(17) . . ? C16 C15 N3 112.76(13) . . ? N3 C17 C18 113.73(14) . . ? N3 C19 C20 113.93(14) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.85 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.303 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 935865' ####################################################################### # # 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_cpd2 #TrackingRef 'web_deposit_cif_file_3_Jing-YunWu_1366794164.cpd 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 Cl3 N3 O Zn' _chemical_formula_weight 494.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7224(4) _cell_length_b 12.2159(6) _cell_length_c 23.6010(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.2300(10) _cell_angle_gamma 90.00 _cell_volume 2217.16(19) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7555 _cell_measurement_theta_min 2.405 _cell_measurement_theta_max 26.016 _exptl_crystal_description prism _exptl_crystal_colour orange-yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.57 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 1.485 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.815512 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12175 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 26.02 _reflns_number_total 4368 _reflns_number_gt 3882 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0354P)^2^+0.5522P] 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 4368 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0686 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn -0.02744(3) 0.881105(16) 0.137762(8) 0.03703(8) Uani 1 1 d . . . Cl1 Cl 0.10877(7) 0.87247(4) 0.22506(2) 0.05415(13) Uani 1 1 d . . . Cl2 Cl -0.25784(7) 0.99195(5) 0.12765(2) 0.06382(16) Uani 1 1 d . . . Cl3 Cl -0.11886(7) 0.56823(5) -0.12169(2) 0.05768(14) Uani 1 1 d . . . O1 O -0.10029(17) 0.73482(10) 0.11181(5) 0.0436(3) Uani 1 1 d . . . N1 N 0.11772(17) 0.91301(11) 0.07128(6) 0.0322(3) Uani 1 1 d . . . N2 N 0.6170(3) 1.37196(16) 0.08716(11) 0.0776(6) Uani 1 1 d . . . N3 N 0.6732(2) 0.64764(12) 0.18780(6) 0.0403(3) Uani 1 1 d . . . H101 H 0.7354 0.6758 0.1610 0.061 Uiso 1 1 d R . . C1 C -0.0016(2) 0.75307(13) 0.01790(7) 0.0320(3) Uani 1 1 d . . . C2 C -0.0958(2) 0.70014(13) 0.05936(7) 0.0338(3) Uani 1 1 d . . . C3 C -0.1880(2) 0.60433(14) 0.04236(8) 0.0411(4) Uani 1 1 d . . . H3 H -0.2469 0.5670 0.0691 0.049 Uiso 1 1 calc R . . C4 C -0.1943(2) 0.56400(14) -0.01190(8) 0.0420(4) Uani 1 1 d . . . H4 H -0.2581 0.5012 -0.0218 0.050 Uiso 1 1 calc R . . C5 C -0.1044(2) 0.61778(14) -0.05218(7) 0.0383(4) Uani 1 1 d . . . C6 C -0.0086(2) 0.70894(14) -0.03771(7) 0.0365(4) Uani 1 1 d . . . H6 H 0.0532 0.7427 -0.0649 0.044 Uiso 1 1 calc R . . C7 C 0.0999(2) 0.85101(14) 0.02645(7) 0.0351(3) Uani 1 1 d . . . H7 H 0.1606 0.8728 -0.0039 0.042 Uiso 1 1 calc R . . C8 C 0.2231(2) 1.00962(13) 0.07141(7) 0.0329(3) Uani 1 1 d . . . C9 C 0.3032(2) 1.04731(14) 0.02475(8) 0.0392(4) Uani 1 1 d . . . H9 H 0.2890 1.0093 -0.0095 0.047 Uiso 1 1 calc R . . C10 C 0.4036(2) 1.14091(15) 0.02898(9) 0.0445(4) Uani 1 1 d . . . H10 H 0.4575 1.1652 -0.0024 0.053 Uiso 1 1 calc R . . C11 C 0.4247(2) 1.19901(14) 0.07950(8) 0.0413(4) Uani 1 1 d . . . C12 C 0.3427(3) 1.16368(15) 0.12587(8) 0.0462(4) Uani 1 1 d . . . H12 H 0.3542 1.2034 0.1596 0.055 Uiso 1 1 calc R . . C13 C 0.2440(2) 1.06963(15) 0.12203(8) 0.0430(4) Uani 1 1 d . . . H13 H 0.1904 1.0457 0.1535 0.052 Uiso 1 1 calc R . . C14 C 0.5316(3) 1.29576(16) 0.08380(10) 0.0527(5) Uani 1 1 d . . . C15 C 0.7629(3) 0.54661(16) 0.21248(8) 0.0479(4) Uani 1 1 d . . . H15A H 0.6964 0.5174 0.2420 0.057 Uiso 1 1 calc R . . H15B H 0.7643 0.4917 0.1828 0.057 Uiso 1 1 calc R . . C16 C 0.9456(3) 0.5668(2) 0.23720(10) 0.0630(6) Uani 1 1 d . . . H16A H 1.0076 0.6063 0.2103 0.095 Uiso 1 1 calc R . . H16B H 1.0023 0.4980 0.2457 0.095 Uiso 1 1 calc R . . H16C H 0.9441 0.6090 0.2715 0.095 Uiso 1 1 calc R . . C17 C 0.6657(3) 0.74034(16) 0.22953(9) 0.0534(5) Uani 1 1 d . . . H17A H 0.6206 0.8048 0.2092 0.064 Uiso 1 1 calc R . . H17B H 0.7830 0.7569 0.2455 0.064 Uiso 1 1 calc R . . C18 C 0.5551(4) 0.7172(2) 0.27755(10) 0.0777(7) Uani 1 1 d . . . H18A H 0.4374 0.7040 0.2624 0.117 Uiso 1 1 calc R . . H18B H 0.5583 0.7791 0.3027 0.117 Uiso 1 1 calc R . . H18C H 0.5992 0.6539 0.2982 0.117 Uiso 1 1 calc R . . C19 C 0.4989(3) 0.61736(18) 0.15887(10) 0.0551(5) Uani 1 1 d . . . H19A H 0.5125 0.5543 0.1347 0.066 Uiso 1 1 calc R . . H19B H 0.4229 0.5962 0.1875 0.066 Uiso 1 1 calc R . . C20 C 0.4143(3) 0.7078(2) 0.12357(12) 0.0813(8) Uani 1 1 d . . . H20A H 0.3922 0.7686 0.1477 0.122 Uiso 1 1 calc R . . H20B H 0.3065 0.6822 0.1047 0.122 Uiso 1 1 calc R . . H20C H 0.4900 0.7306 0.0957 0.122 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 0.04341(13) 0.03688(12) 0.03183(12) -0.00248(8) 0.00903(8) -0.00344(8) Cl1 0.0624(3) 0.0618(3) 0.0371(2) 0.0039(2) -0.0019(2) -0.0057(2) Cl2 0.0609(3) 0.0827(4) 0.0474(3) -0.0104(3) 0.0024(2) 0.0279(3) Cl3 0.0736(3) 0.0616(3) 0.0383(2) -0.0152(2) 0.0080(2) -0.0126(3) O1 0.0602(8) 0.0389(6) 0.0337(6) -0.0039(5) 0.0152(5) -0.0125(6) N1 0.0345(7) 0.0308(7) 0.0318(7) 0.0015(5) 0.0057(6) -0.0009(5) N2 0.0670(13) 0.0526(12) 0.1158(19) -0.0113(11) 0.0224(12) -0.0225(10) N3 0.0484(8) 0.0385(8) 0.0357(8) 0.0020(6) 0.0122(6) -0.0041(6) C1 0.0313(8) 0.0335(8) 0.0315(8) 0.0004(6) 0.0047(6) 0.0021(6) C2 0.0390(8) 0.0307(8) 0.0320(8) 0.0006(6) 0.0056(7) 0.0017(7) C3 0.0503(10) 0.0329(9) 0.0415(10) 0.0015(7) 0.0112(8) -0.0050(7) C4 0.0488(10) 0.0330(9) 0.0439(10) -0.0050(7) 0.0031(8) -0.0046(8) C5 0.0432(9) 0.0389(9) 0.0329(9) -0.0048(7) 0.0035(7) 0.0034(7) C6 0.0370(8) 0.0401(9) 0.0332(8) 0.0009(7) 0.0073(7) 0.0004(7) C7 0.0349(8) 0.0385(9) 0.0330(8) 0.0019(7) 0.0095(7) -0.0011(7) C8 0.0311(8) 0.0310(8) 0.0364(8) 0.0033(6) 0.0028(6) 0.0008(6) C9 0.0433(9) 0.0368(9) 0.0382(9) 0.0008(7) 0.0081(7) -0.0021(7) C10 0.0415(9) 0.0420(10) 0.0520(11) 0.0082(8) 0.0147(8) -0.0018(8) C11 0.0334(8) 0.0327(9) 0.0572(11) 0.0041(8) 0.0011(8) -0.0004(7) C12 0.0535(11) 0.0394(10) 0.0445(10) -0.0026(8) -0.0011(8) -0.0057(9) C13 0.0531(11) 0.0402(10) 0.0364(9) 0.0009(7) 0.0073(8) -0.0078(8) C14 0.0436(10) 0.0424(11) 0.0731(14) -0.0003(10) 0.0098(9) -0.0047(9) C15 0.0586(12) 0.0404(10) 0.0459(10) 0.0028(8) 0.0114(9) 0.0000(9) C16 0.0649(14) 0.0682(14) 0.0545(13) 0.0003(11) -0.0030(10) 0.0057(12) C17 0.0706(13) 0.0440(11) 0.0473(11) -0.0044(8) 0.0142(9) 0.0013(10) C18 0.107(2) 0.0765(17) 0.0546(14) -0.0006(12) 0.0367(13) 0.0191(15) C19 0.0494(11) 0.0587(13) 0.0573(12) -0.0012(10) 0.0054(9) -0.0060(9) C20 0.0669(15) 0.0849(19) 0.0895(19) 0.0090(15) -0.0079(14) 0.0147(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9551(12) . ? Zn1 N1 2.0473(13) . ? Zn1 Cl1 2.2287(5) . ? Zn1 Cl2 2.2313(6) . ? Cl3 C5 1.7426(17) . ? O1 C2 1.3118(19) . ? N1 C7 1.298(2) . ? N1 C8 1.434(2) . ? N2 C14 1.139(3) . ? N3 C19 1.499(3) . ? N3 C17 1.505(2) . ? N3 C15 1.506(2) . ? C1 C6 1.415(2) . ? C1 C2 1.426(2) . ? C1 C7 1.435(2) . ? C2 C3 1.409(2) . ? C3 C4 1.369(2) . ? C4 C5 1.392(3) . ? C5 C6 1.363(2) . ? C8 C9 1.390(2) . ? C8 C13 1.398(2) . ? C9 C10 1.380(2) . ? C10 C11 1.384(3) . ? C11 C12 1.382(3) . ? C11 C14 1.440(3) . ? C12 C13 1.377(3) . ? C15 C16 1.497(3) . ? C17 C18 1.507(3) . ? C19 C20 1.497(3) . ? 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 N1 95.50(5) . . ? O1 Zn1 Cl1 110.15(4) . . ? N1 Zn1 Cl1 118.18(4) . . ? O1 Zn1 Cl2 108.50(4) . . ? N1 Zn1 Cl2 106.83(4) . . ? Cl1 Zn1 Cl2 115.60(2) . . ? C2 O1 Zn1 124.00(10) . . ? C7 N1 C8 120.00(14) . . ? C7 N1 Zn1 119.26(11) . . ? C8 N1 Zn1 120.37(10) . . ? C19 N3 C17 113.42(16) . . ? C19 N3 C15 109.66(15) . . ? C17 N3 C15 114.02(15) . . ? C6 C1 C2 118.99(15) . . ? C6 C1 C7 114.97(14) . . ? C2 C1 C7 126.02(14) . . ? O1 C2 C3 118.74(14) . . ? O1 C2 C1 124.05(14) . . ? C3 C2 C1 117.21(15) . . ? C4 C3 C2 122.64(16) . . ? C3 C4 C5 119.44(16) . . ? C6 C5 C4 120.50(16) . . ? C6 C5 Cl3 120.44(14) . . ? C4 C5 Cl3 119.05(13) . . ? C5 C6 C1 121.17(15) . . ? N1 C7 C1 128.11(15) . . ? C9 C8 C13 118.58(15) . . ? C9 C8 N1 124.38(15) . . ? C13 C8 N1 117.03(14) . . ? C10 C9 C8 120.32(16) . . ? C9 C10 C11 120.55(17) . . ? C12 C11 C10 119.69(16) . . ? C12 C11 C14 120.09(18) . . ? C10 C11 C14 120.22(17) . . ? C13 C12 C11 119.94(17) . . ? C12 C13 C8 120.89(17) . . ? N2 C14 C11 179.6(3) . . ? C16 C15 N3 113.58(17) . . ? N3 C17 C18 114.15(18) . . ? C20 C19 N3 113.54(19) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.369 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 935866' ####################################################################### # # 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_cpd3 #TrackingRef 'web_deposit_cif_file_4_Jing-YunWu_1366794164.cpd 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 Br Cl2 N3 O Zn' _chemical_formula_weight 538.60 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.786(2) _cell_length_b 12.174(3) _cell_length_c 23.664(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.371(11) _cell_angle_gamma 90.00 _cell_volume 2233.3(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7340 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 25.07 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 3.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6797 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14686 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.07 _reflns_number_total 3935 _reflns_number_gt 3377 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0239P)^2^+0.9283P] 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 3935 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0563 _refine_ls_wR_factor_gt 0.0540 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn -0.02476(3) 0.11599(2) 0.137848(10) 0.03642(8) Uani 1 1 d . . . Br1 Br -0.12683(3) 0.43626(2) -0.125079(10) 0.05253(9) Uani 1 1 d . . . Cl1 Cl -0.25237(9) 0.00433(6) 0.12685(3) 0.0639(2) Uani 1 1 d . . . Cl2 Cl 0.11038(9) 0.12402(6) 0.22477(3) 0.05472(17) Uani 1 1 d . . . O1 O -0.0978(2) 0.26314(12) 0.11267(6) 0.0418(4) Uani 1 1 d . . . N1 N 0.1185(2) 0.08542(13) 0.07170(7) 0.0311(4) Uani 1 1 d . . . N2 N 0.6192(3) -0.3715(2) 0.08644(12) 0.0770(8) Uani 1 1 d . . . N3 N 0.6773(2) 0.34832(15) 0.18802(7) 0.0388(4) Uani 1 1 d . . . H101 H 0.7427 0.3231 0.1567 0.058 Uiso 1 1 d R . . C1 C -0.0025(3) 0.24623(17) 0.01929(8) 0.0312(5) Uani 1 1 d . . . C2 C -0.0956(3) 0.29827(17) 0.06060(9) 0.0333(5) Uani 1 1 d . . . C3 C -0.1876(3) 0.39365(18) 0.04398(9) 0.0405(5) Uani 1 1 d . . . H3 H -0.2457 0.4305 0.0709 0.049 Uiso 1 1 calc R . . C4 C -0.1960(3) 0.43488(18) -0.00968(9) 0.0402(5) Uani 1 1 d . . . H4 H -0.2604 0.4976 -0.0192 0.048 Uiso 1 1 calc R . . C5 C -0.1072(3) 0.38191(18) -0.04995(9) 0.0358(5) Uani 1 1 d . . . C6 C -0.0116(3) 0.29090(18) -0.03587(9) 0.0352(5) Uani 1 1 d . . . H6 H 0.0491 0.2574 -0.0632 0.042 Uiso 1 1 calc R . . C7 C 0.0991(3) 0.14789(17) 0.02754(9) 0.0338(5) Uani 1 1 d . . . H7 H 0.1586 0.1266 -0.0029 0.041 Uiso 1 1 calc R . . C8 C 0.2248(3) -0.01084(17) 0.07185(9) 0.0325(5) Uani 1 1 d . . . C9 C 0.3038(3) -0.04710(18) 0.02519(10) 0.0390(5) Uani 1 1 d . . . H9 H 0.2890 -0.0085 -0.0088 0.047 Uiso 1 1 calc R . . C10 C 0.4042(3) -0.14034(18) 0.02918(11) 0.0441(6) Uani 1 1 d . . . H10 H 0.4577 -0.1639 -0.0022 0.053 Uiso 1 1 calc R . . C11 C 0.4266(3) -0.19916(18) 0.07910(10) 0.0405(5) Uani 1 1 d . . . C12 C 0.3457(3) -0.16482(19) 0.12523(10) 0.0452(6) Uani 1 1 d . . . H12 H 0.3582 -0.2048 0.1589 0.054 Uiso 1 1 calc R . . C13 C 0.2461(3) -0.07123(19) 0.12157(10) 0.0421(6) Uani 1 1 d . . . H13 H 0.1923 -0.0482 0.1530 0.051 Uiso 1 1 calc R . . C14 C 0.5340(3) -0.2958(2) 0.08316(12) 0.0526(6) Uani 1 1 d . . . C15 C 0.7637(3) 0.45050(19) 0.21281(10) 0.0457(6) Uani 1 1 d . . . H15A H 0.7685 0.5047 0.1830 0.055 Uiso 1 1 calc R . . H15B H 0.6942 0.4808 0.2410 0.055 Uiso 1 1 calc R . . C16 C 0.9429(3) 0.4303(2) 0.23988(11) 0.0602(7) Uani 1 1 d . . . H16A H 0.9373 0.3888 0.2742 0.090 Uiso 1 1 calc R . . H16B H 0.9988 0.4993 0.2486 0.090 Uiso 1 1 calc R . . H16C H 1.0072 0.3898 0.2142 0.090 Uiso 1 1 calc R . . C17 C 0.6703(4) 0.2558(2) 0.22957(10) 0.0531(7) Uani 1 1 d . . . H17A H 0.7866 0.2396 0.2458 0.064 Uiso 1 1 calc R . . H17B H 0.6261 0.1908 0.2094 0.064 Uiso 1 1 calc R . . C18 C 0.5600(4) 0.2795(3) 0.27683(12) 0.0771(9) Uani 1 1 d . . . H18A H 0.5991 0.3458 0.2959 0.116 Uiso 1 1 calc R . . H18B H 0.5681 0.2196 0.3033 0.116 Uiso 1 1 calc R . . H18C H 0.4422 0.2883 0.2615 0.116 Uiso 1 1 calc R . . C19 C 0.5051(3) 0.3777(2) 0.15848(11) 0.0530(7) Uani 1 1 d . . . H19A H 0.5187 0.4408 0.1343 0.064 Uiso 1 1 calc R . . H19B H 0.4286 0.3988 0.1867 0.064 Uiso 1 1 calc R . . C20 C 0.4227(4) 0.2863(3) 0.12313(14) 0.0811(10) Uani 1 1 d . . . H20A H 0.4987 0.2636 0.0956 0.122 Uiso 1 1 calc R . . H20B H 0.3158 0.3114 0.1040 0.122 Uiso 1 1 calc R . . H20C H 0.4009 0.2253 0.1472 0.122 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 0.04381(16) 0.03620(15) 0.03020(14) 0.00296(11) 0.00854(11) 0.00368(11) Br1 0.06429(17) 0.05866(18) 0.03532(14) 0.01353(12) 0.00823(11) 0.01185(13) Cl1 0.0619(4) 0.0812(5) 0.0482(4) 0.0113(3) 0.0025(3) -0.0278(4) Cl2 0.0640(4) 0.0636(4) 0.0353(3) -0.0043(3) -0.0019(3) 0.0072(3) O1 0.0593(10) 0.0372(9) 0.0310(8) 0.0043(7) 0.0149(7) 0.0116(7) N1 0.0343(10) 0.0296(9) 0.0299(10) -0.0016(8) 0.0051(7) 0.0015(7) N2 0.0657(16) 0.0533(15) 0.115(2) 0.0092(15) 0.0212(15) 0.0217(13) N3 0.0470(11) 0.0378(11) 0.0329(10) -0.0005(8) 0.0112(8) 0.0044(9) C1 0.0314(11) 0.0308(11) 0.0315(11) -0.0006(9) 0.0036(9) -0.0037(9) C2 0.0380(12) 0.0301(12) 0.0323(12) -0.0010(9) 0.0060(9) -0.0035(9) C3 0.0511(14) 0.0347(13) 0.0374(13) -0.0010(10) 0.0131(11) 0.0065(11) C4 0.0488(14) 0.0305(12) 0.0411(13) 0.0031(10) 0.0033(11) 0.0048(10) C5 0.0424(13) 0.0360(12) 0.0291(12) 0.0043(10) 0.0037(10) -0.0026(10) C6 0.0352(12) 0.0394(13) 0.0319(12) -0.0006(10) 0.0083(9) -0.0004(10) C7 0.0335(12) 0.0381(12) 0.0306(12) -0.0019(10) 0.0074(9) 0.0019(10) C8 0.0316(11) 0.0301(11) 0.0353(12) -0.0033(9) 0.0013(9) -0.0021(9) C9 0.0418(13) 0.0367(13) 0.0395(13) 0.0006(10) 0.0099(10) 0.0005(10) C10 0.0421(13) 0.0394(14) 0.0527(15) -0.0074(11) 0.0148(11) 0.0013(11) C11 0.0319(12) 0.0324(12) 0.0564(15) -0.0051(11) -0.0003(10) 0.0006(10) C12 0.0546(15) 0.0371(13) 0.0424(14) 0.0020(11) -0.0033(11) 0.0062(12) C13 0.0522(14) 0.0402(13) 0.0343(13) -0.0015(10) 0.0064(10) 0.0066(11) C14 0.0453(15) 0.0413(15) 0.0717(18) 0.0005(13) 0.0081(13) 0.0043(12) C15 0.0568(15) 0.0399(14) 0.0417(14) -0.0038(11) 0.0122(11) -0.0015(11) C16 0.0645(18) 0.0650(18) 0.0498(16) 0.0015(14) -0.0014(13) -0.0065(14) C17 0.0736(18) 0.0409(14) 0.0464(15) 0.0080(12) 0.0142(13) -0.0032(13) C18 0.110(3) 0.071(2) 0.0556(18) 0.0032(16) 0.0369(17) -0.0203(18) C19 0.0480(15) 0.0585(17) 0.0527(16) -0.0011(13) 0.0047(12) 0.0048(12) C20 0.068(2) 0.084(2) 0.088(2) -0.0133(19) -0.0092(17) -0.0133(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 Zn1 O1 1.9555(15) . ? Zn1 N1 2.0393(17) . ? Zn1 Cl2 2.2233(8) . ? Zn1 Cl1 2.2293(8) . ? Br1 C5 1.890(2) . ? O1 C2 1.306(2) . ? N1 C7 1.290(3) . ? N1 C8 1.435(3) . ? N2 C14 1.134(3) . ? N3 C19 1.496(3) . ? N3 C17 1.500(3) . ? N3 C15 1.506(3) . ? C1 C6 1.410(3) . ? C1 C2 1.420(3) . ? C1 C7 1.438(3) . ? C2 C3 1.402(3) . ? C3 C4 1.361(3) . ? C4 C5 1.388(3) . ? C5 C6 1.359(3) . ? C8 C13 1.384(3) . ? C8 C9 1.386(3) . ? C9 C10 1.377(3) . ? C10 C11 1.378(3) . ? C11 C12 1.376(3) . ? C11 C14 1.441(3) . ? C12 C13 1.376(3) . ? C15 C16 1.500(3) . ? C17 C18 1.501(4) . ? C19 C20 1.500(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 O1 Zn1 N1 95.60(6) . . ? O1 Zn1 Cl2 109.91(5) . . ? N1 Zn1 Cl2 118.21(6) . . ? O1 Zn1 Cl1 108.52(5) . . ? N1 Zn1 Cl1 106.55(5) . . ? Cl2 Zn1 Cl1 115.92(3) . . ? C2 O1 Zn1 123.94(13) . . ? C7 N1 C8 120.48(17) . . ? C7 N1 Zn1 118.91(14) . . ? C8 N1 Zn1 120.27(13) . . ? C19 N3 C17 113.56(19) . . ? C19 N3 C15 109.41(18) . . ? C17 N3 C15 114.04(18) . . ? C6 C1 C2 118.73(19) . . ? C6 C1 C7 115.24(18) . . ? C2 C1 C7 126.00(19) . . ? O1 C2 C3 118.98(19) . . ? O1 C2 C1 123.81(19) . . ? C3 C2 C1 117.21(19) . . ? C4 C3 C2 123.1(2) . . ? C3 C4 C5 119.1(2) . . ? C6 C5 C4 120.5(2) . . ? C6 C5 Br1 120.70(17) . . ? C4 C5 Br1 118.79(16) . . ? C5 C6 C1 121.4(2) . . ? N1 C7 C1 128.46(19) . . ? C13 C8 C9 118.8(2) . . ? C13 C8 N1 117.33(19) . . ? C9 C8 N1 123.87(19) . . ? C10 C9 C8 120.0(2) . . ? C9 C10 C11 120.8(2) . . ? C12 C11 C10 119.4(2) . . ? C12 C11 C14 120.1(2) . . ? C10 C11 C14 120.5(2) . . ? C11 C12 C13 119.9(2) . . ? C12 C13 C8 121.0(2) . . ? N2 C14 C11 179.6(3) . . ? C16 C15 N3 113.2(2) . . ? N3 C17 C18 113.7(2) . . ? N3 C19 C20 113.7(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.283 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 935867' ####################################################################### # # 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_cpd4 #TrackingRef 'web_deposit_cif_file_5_Jing-YunWu_1366794164.cpd 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 Cl2 N3 O2 Zn' _chemical_formula_weight 489.73 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' Cl Cl 0.1484 0.1585 '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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 46.342(5) _cell_length_b 7.1190(8) _cell_length_c 27.418(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.348(5) _cell_angle_gamma 90.00 _cell_volume 9042.9(17) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9930 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.14 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4064 _exptl_absorpt_coefficient_mu 1.344 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5854 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25280 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -55 _diffrn_reflns_limit_h_max 54 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 0.88 _diffrn_reflns_theta_max 25.17 _reflns_number_total 7741 _reflns_number_gt 6646 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0000P)^2^+1044.9961P] 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 7741 _refine_ls_number_parameters 525 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1191 _refine_ls_R_factor_gt 0.1085 _refine_ls_wR_factor_ref 0.3087 _refine_ls_wR_factor_gt 0.3045 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _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 Zn1 Zn 0.07059(3) 0.5351(2) 0.46603(5) 0.0158(4) Uani 1 1 d . . . Zn2 Zn 0.18037(3) 0.4221(2) 0.21244(5) 0.0158(4) Uani 1 1 d . . . Cl1 Cl 0.05438(7) 0.2406(5) 0.45408(12) 0.0210(7) Uani 1 1 d . . . Cl2 Cl 0.10571(6) 0.6140(5) 0.41532(11) 0.0218(7) Uani 1 1 d . . . Cl3 Cl 0.14503(7) 0.5724(6) 0.17190(12) 0.0256(8) Uani 1 1 d . . . Cl4 Cl 0.19121(7) 0.1355(5) 0.18409(12) 0.0236(7) Uani 1 1 d . . . O1 O 0.08498(17) 0.5922(14) 0.5318(3) 0.019(2) Uani 1 1 d . . . O2 O 0.01322(19) 0.6143(15) 0.6901(3) 0.024(2) Uani 1 1 d . . . O3 O 0.16993(18) 0.4185(14) 0.2812(3) 0.019(2) Uani 1 1 d . . . O4 O 0.23437(19) 0.6363(16) 0.4437(3) 0.026(2) Uani 1 1 d . . . N1 N 0.0343(2) 0.6995(15) 0.4732(4) 0.014(2) Uani 1 1 d . . . N2 N -0.0451(3) 0.927(2) 0.2694(4) 0.031(3) Uani 1 1 d . . . N3 N 0.1286(2) 0.8604(16) 0.5400(4) 0.019(2) Uani 1 1 d . . . H101 H 0.1166 0.7737 0.5440 0.023 Uiso 1 1 d R . . N4 N 0.2186(2) 0.5573(16) 0.2234(4) 0.015(2) Uani 1 1 d . . . N5 N 0.2927(2) 0.6645(19) 0.0149(4) 0.026(3) Uani 1 1 d . . . N6 N 0.3788(2) 0.7020(16) 0.2115(4) 0.015(2) Uani 1 1 d . . . H102 H 0.3633 0.7633 0.2092 0.018 Uiso 1 1 d R . . C1 C 0.0376(3) 0.668(2) 0.5623(4) 0.017(3) Uani 1 1 d . . . C2 C 0.0665(3) 0.600(2) 0.5680(5) 0.020(3) Uani 1 1 d . . . C3 C 0.0752(3) 0.541(2) 0.6153(5) 0.021(3) Uani 1 1 d . . . H3 H 0.0937 0.4921 0.6200 0.025 Uiso 1 1 calc R . . C4 C 0.0577(3) 0.553(2) 0.6540(5) 0.021(3) Uani 1 1 d . . . H4 H 0.0647 0.5184 0.6848 0.025 Uiso 1 1 calc R . . C5 C 0.0292(3) 0.617(2) 0.6484(5) 0.020(3) Uani 1 1 d . . . C6 C 0.0195(3) 0.6780(19) 0.6032(4) 0.016(3) Uani 1 1 d . . . H6 H 0.0009 0.7261 0.5995 0.020 Uiso 1 1 calc R . . C7 C 0.0247(2) 0.7268(18) 0.5169(4) 0.013(3) Uani 1 1 d . . . H7 H 0.0074 0.7924 0.5188 0.016 Uiso 1 1 calc R . . C8 C 0.0169(3) 0.7538(18) 0.4321(4) 0.015(3) Uani 1 1 d . . . C9 C -0.0128(3) 0.7956(19) 0.4339(5) 0.0169(19) Uani 1 1 d . . . H9 H -0.0221 0.7928 0.4636 0.020 Uiso 1 1 calc R . . C10 C -0.0279(3) 0.8402(19) 0.3921(4) 0.017(3) Uani 1 1 d . . . H10 H -0.0475 0.8673 0.3937 0.021 Uiso 1 1 calc R . . C11 C -0.0147(3) 0.846(2) 0.3476(5) 0.021(3) Uani 1 1 d . . . C12 C 0.0150(3) 0.806(2) 0.3446(4) 0.020(3) Uani 1 1 d . . . H12 H 0.0240 0.8102 0.3147 0.023 Uiso 1 1 calc R . . C13 C 0.0304(3) 0.7606(19) 0.3864(4) 0.0169(19) Uani 1 1 d . . . H13 H 0.0500 0.7342 0.3846 0.020 Uiso 1 1 calc R . . C14 C -0.0317(3) 0.893(2) 0.3035(5) 0.022(3) Uani 1 1 d . . . C15 C -0.0158(3) 0.674(2) 0.6863(5) 0.022(3) Uani 1 1 d . . . H15A H -0.0164 0.8059 0.6792 0.033 Uiso 1 1 calc R . . H15B H -0.0252 0.6504 0.7165 0.033 Uiso 1 1 calc R . . H15C H -0.0255 0.6059 0.6605 0.033 Uiso 1 1 calc R . . C16 C 0.1147(3) 0.998(2) 0.5045(6) 0.031(4) Uani 1 1 d . . . H16A H 0.1128 0.9386 0.4728 0.037 Uiso 1 1 calc R . . H16B H 0.0954 1.0266 0.5153 0.037 Uiso 1 1 calc R . . C17 C 0.1308(3) 1.175(3) 0.4994(8) 0.053(5) Uani 1 1 d . . . H17A H 0.1318 1.2386 0.5303 0.079 Uiso 1 1 calc R . . H17B H 0.1210 1.2540 0.4758 0.079 Uiso 1 1 calc R . . H17C H 0.1499 1.1486 0.4887 0.079 Uiso 1 1 calc R . . C18 C 0.1555(3) 0.776(2) 0.5190(5) 0.021(3) Uani 1 1 d . . . H18A H 0.1510 0.7292 0.4864 0.025 Uiso 1 1 calc R . . H18B H 0.1701 0.8722 0.5164 0.025 Uiso 1 1 calc R . . C19 C 0.1671(3) 0.617(2) 0.5500(5) 0.025(3) Uani 1 1 d . . . H19A H 0.1723 0.6639 0.5818 0.037 Uiso 1 1 calc R . . H19B H 0.1838 0.5650 0.5350 0.037 Uiso 1 1 calc R . . H19C H 0.1526 0.5219 0.5528 0.037 Uiso 1 1 calc R . . C20 C 0.1337(3) 0.934(3) 0.5902(5) 0.031(4) Uani 1 1 d . . . H20A H 0.1489 1.0280 0.5896 0.038 Uiso 1 1 calc R . . H20B H 0.1404 0.8322 0.6111 0.038 Uiso 1 1 calc R . . C21 C 0.1073(3) 1.020(3) 0.6116(7) 0.045(5) Uani 1 1 d . . . H21A H 0.0918 0.9295 0.6107 0.067 Uiso 1 1 calc R . . H21B H 0.1017 1.1285 0.5931 0.067 Uiso 1 1 calc R . . H21C H 0.1114 1.0554 0.6448 0.067 Uiso 1 1 calc R . . C22 C 0.2154(3) 0.5514(19) 0.3127(4) 0.014(3) Uani 1 1 d . . . C23 C 0.1863(3) 0.4826(18) 0.3179(4) 0.014(3) Uani 1 1 d . . . C24 C 0.1756(3) 0.486(2) 0.3650(5) 0.022(3) Uani 1 1 d . . . H24 H 0.1564 0.4503 0.3689 0.027 Uiso 1 1 calc R . . C25 C 0.1909(3) 0.537(2) 0.4051(5) 0.017(3) Uani 1 1 d . . . H25 H 0.1825 0.5363 0.4356 0.020 Uiso 1 1 calc R . . C26 C 0.2206(3) 0.593(2) 0.4002(4) 0.018(3) Uani 1 1 d . . . C27 C 0.2315(3) 0.6018(19) 0.3549(4) 0.018(3) Uani 1 1 d . . . H27 H 0.2504 0.6427 0.3515 0.021 Uiso 1 1 calc R . . C28 C 0.2291(3) 0.5840(19) 0.2673(4) 0.015(3) Uani 1 1 d . . . H28 H 0.2479 0.6301 0.2694 0.018 Uiso 1 1 calc R . . C29 C 0.2354(3) 0.5914(18) 0.1815(4) 0.014(3) Uani 1 1 d . . . C30 C 0.2654(3) 0.5578(19) 0.1819(5) 0.016(3) Uani 1 1 d . . . H30 H 0.2752 0.5221 0.2104 0.019 Uiso 1 1 calc R . . C31 C 0.2797(3) 0.580(2) 0.1385(5) 0.020(3) Uani 1 1 d . . . H31 H 0.2994 0.5551 0.1379 0.024 Uiso 1 1 calc R . . C32 C 0.2655(3) 0.637(2) 0.0961(5) 0.018(3) Uani 1 1 d . . . C33 C 0.2360(3) 0.678(2) 0.0961(5) 0.020(3) Uani 1 1 d . . . H33 H 0.2265 0.7205 0.0679 0.024 Uiso 1 1 calc R . . C34 C 0.2210(3) 0.653(2) 0.1392(4) 0.018(3) Uani 1 1 d . . . H34 H 0.2013 0.6788 0.1397 0.021 Uiso 1 1 calc R . . C35 C 0.2809(3) 0.653(2) 0.0508(5) 0.019(3) Uani 1 1 d . . . C36 C 0.2648(3) 0.684(2) 0.4393(5) 0.022(3) Uani 1 1 d . . . H36A H 0.2750 0.5790 0.4262 0.034 Uiso 1 1 calc R . . H36B H 0.2728 0.7155 0.4708 0.034 Uiso 1 1 calc R . . H36C H 0.2666 0.7901 0.4178 0.034 Uiso 1 1 calc R . . C37 C 0.4010(3) 0.8195(19) 0.2399(5) 0.017(3) Uani 1 1 d . . . H37A H 0.3942 0.8406 0.2727 0.020 Uiso 1 1 calc R . . H37B H 0.4190 0.7496 0.2427 0.020 Uiso 1 1 calc R . . C38 C 0.4068(3) 1.007(2) 0.2162(5) 0.027(3) Uani 1 1 d . . . H38A H 0.4173 0.9876 0.1868 0.041 Uiso 1 1 calc R . . H38B H 0.4180 1.0842 0.2383 0.041 Uiso 1 1 calc R . . H38C H 0.3888 1.0679 0.2084 0.041 Uiso 1 1 calc R . . C39 C 0.3877(3) 0.658(2) 0.1600(4) 0.019(3) Uani 1 1 d . . . H39A H 0.3716 0.5984 0.1429 0.022 Uiso 1 1 calc R . . H39B H 0.3916 0.7753 0.1434 0.022 Uiso 1 1 calc R . . C40 C 0.4135(3) 0.534(2) 0.1569(5) 0.027(3) Uani 1 1 d . . . H40A H 0.4293 0.5877 0.1754 0.040 Uiso 1 1 calc R . . H40B H 0.4188 0.5214 0.1234 0.040 Uiso 1 1 calc R . . H40C H 0.4091 0.4121 0.1698 0.040 Uiso 1 1 calc R . . C41 C 0.3717(3) 0.530(2) 0.2404(5) 0.018(3) Uani 1 1 d . . . H41A H 0.3657 0.5683 0.2725 0.022 Uiso 1 1 calc R . . H41B H 0.3890 0.4546 0.2444 0.022 Uiso 1 1 calc R . . C42 C 0.3479(3) 0.411(2) 0.2163(5) 0.026(3) Uani 1 1 d . . . H42A H 0.3310 0.4868 0.2106 0.039 Uiso 1 1 calc R . . H42B H 0.3432 0.3083 0.2375 0.039 Uiso 1 1 calc R . . H42C H 0.3544 0.3624 0.1859 0.039 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 0.0113(7) 0.0172(8) 0.0188(8) -0.0014(6) -0.0015(5) 0.0020(6) Zn2 0.0100(7) 0.0207(9) 0.0166(7) -0.0018(6) -0.0016(5) -0.0028(6) Cl1 0.0168(15) 0.0194(18) 0.0267(17) -0.0023(14) -0.0015(12) 0.0002(13) Cl2 0.0155(15) 0.029(2) 0.0211(16) 0.0008(14) 0.0019(12) 0.0028(14) Cl3 0.0148(15) 0.037(2) 0.0245(17) 0.0017(15) -0.0053(12) 0.0008(15) Cl4 0.0193(15) 0.0205(19) 0.0310(18) -0.0058(14) 0.0025(13) -0.0014(14) O1 0.009(4) 0.031(6) 0.017(4) -0.004(4) -0.004(3) -0.003(4) O2 0.020(5) 0.033(6) 0.020(5) -0.001(4) 0.002(4) -0.003(4) O3 0.016(4) 0.032(6) 0.010(4) -0.002(4) 0.000(3) -0.001(4) O4 0.019(5) 0.043(7) 0.015(5) -0.003(4) -0.002(4) -0.010(5) N1 0.016(5) 0.010(6) 0.014(5) -0.001(4) -0.007(4) -0.004(4) N2 0.031(7) 0.036(8) 0.025(7) 0.001(6) -0.011(5) 0.000(6) N3 0.010(5) 0.014(6) 0.034(6) -0.001(5) -0.005(4) -0.002(5) N4 0.015(5) 0.015(6) 0.014(5) 0.000(4) -0.002(4) 0.000(5) N5 0.025(6) 0.031(8) 0.023(6) -0.002(5) 0.001(5) 0.002(6) N6 0.008(5) 0.019(6) 0.019(5) 0.002(5) -0.003(4) 0.001(4) C1 0.018(6) 0.020(7) 0.013(6) -0.001(5) -0.006(5) -0.010(6) C2 0.020(7) 0.020(8) 0.019(7) -0.004(6) 0.001(5) -0.006(6) C3 0.009(6) 0.024(8) 0.029(7) -0.004(6) -0.006(5) 0.009(6) C4 0.024(7) 0.018(8) 0.020(7) 0.002(6) -0.009(5) -0.007(6) C5 0.020(7) 0.019(8) 0.022(7) -0.008(6) -0.001(5) -0.002(6) C6 0.020(6) 0.015(7) 0.014(6) -0.005(5) -0.004(5) -0.003(5) C7 0.011(6) 0.010(7) 0.018(6) 0.001(5) -0.001(5) -0.004(5) C8 0.022(6) 0.010(7) 0.013(6) -0.004(5) -0.004(5) -0.001(5) C9 0.016(4) 0.016(5) 0.019(5) -0.001(4) 0.000(4) -0.005(4) C10 0.019(6) 0.014(7) 0.019(7) -0.004(5) -0.004(5) 0.006(5) C11 0.026(7) 0.021(8) 0.016(7) 0.003(6) -0.010(5) 0.002(6) C12 0.025(7) 0.023(8) 0.010(6) -0.001(5) -0.002(5) -0.003(6) C13 0.016(4) 0.016(5) 0.019(5) -0.001(4) 0.000(4) -0.005(4) C14 0.018(6) 0.023(8) 0.024(7) -0.002(6) 0.001(6) 0.002(6) C15 0.017(6) 0.022(8) 0.028(7) -0.003(6) 0.006(5) -0.003(6) C16 0.021(7) 0.024(9) 0.047(9) 0.001(7) -0.008(6) 0.016(6) C17 0.018(8) 0.034(11) 0.106(16) 0.016(11) -0.004(9) 0.009(8) C18 0.013(6) 0.034(9) 0.016(6) -0.001(6) -0.004(5) 0.000(6) C19 0.015(6) 0.018(8) 0.041(8) -0.006(6) -0.002(6) 0.007(6) C20 0.018(7) 0.046(11) 0.031(8) -0.013(7) 0.000(6) -0.005(7) C21 0.031(9) 0.050(12) 0.053(11) -0.016(9) -0.001(8) 0.004(8) C22 0.014(6) 0.014(7) 0.015(6) 0.000(5) -0.002(5) 0.003(5) C23 0.015(6) 0.009(7) 0.019(6) 0.000(5) -0.007(5) 0.002(5) C24 0.012(6) 0.038(9) 0.017(7) 0.002(6) -0.001(5) -0.001(6) C25 0.012(6) 0.018(7) 0.021(7) -0.005(5) 0.003(5) 0.002(5) C26 0.013(6) 0.030(8) 0.011(6) 0.003(6) -0.005(5) 0.000(6) C27 0.016(6) 0.017(7) 0.020(7) 0.000(5) -0.004(5) 0.004(5) C28 0.014(6) 0.011(7) 0.021(7) 0.001(5) -0.005(5) -0.002(5) C29 0.012(6) 0.008(6) 0.023(7) -0.001(5) 0.000(5) -0.005(5) C30 0.011(6) 0.016(7) 0.022(7) 0.001(5) -0.004(5) 0.002(5) C31 0.021(7) 0.016(7) 0.022(7) -0.004(6) -0.002(5) -0.006(6) C32 0.018(6) 0.018(8) 0.019(7) -0.008(5) 0.002(5) -0.003(6) C33 0.021(7) 0.020(8) 0.019(7) -0.004(6) -0.006(5) 0.001(6) C34 0.014(6) 0.026(8) 0.012(6) -0.002(5) -0.001(5) -0.001(6) C35 0.022(7) 0.020(8) 0.015(7) 0.000(5) -0.003(5) 0.004(6) C36 0.013(6) 0.023(8) 0.031(8) 0.001(6) -0.004(5) -0.004(6) C37 0.011(6) 0.013(7) 0.025(7) -0.005(5) -0.001(5) 0.003(5) C38 0.026(7) 0.028(9) 0.027(8) 0.002(6) -0.010(6) -0.003(7) C39 0.019(6) 0.026(8) 0.011(6) 0.001(5) -0.009(5) -0.005(6) C40 0.032(8) 0.027(9) 0.022(7) -0.001(6) 0.005(6) 0.011(7) C41 0.012(6) 0.017(7) 0.026(7) 0.001(6) -0.003(5) 0.004(5) C42 0.026(7) 0.021(8) 0.031(8) 0.004(6) -0.005(6) 0.000(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.950(8) . ? Zn1 N1 2.062(11) . ? Zn1 Cl2 2.237(3) . ? Zn1 Cl1 2.249(4) . ? Zn2 O3 1.957(8) . ? Zn2 N4 2.031(10) . ? Zn2 Cl3 2.231(4) . ? Zn2 Cl4 2.244(4) . ? O1 C2 1.328(15) . ? O2 C5 1.377(16) . ? O2 C15 1.410(16) . ? O3 C23 1.327(15) . ? O4 C26 1.373(15) . ? O4 C36 1.457(15) . ? N1 C7 1.303(15) . ? N1 C8 1.425(15) . ? N2 C14 1.138(17) . ? N3 C20 1.487(17) . ? N3 C18 1.509(16) . ? N3 C16 1.515(18) . ? N4 C28 1.301(15) . ? N4 C29 1.425(16) . ? N5 C35 1.140(17) . ? N6 C41 1.496(17) . ? N6 C39 1.512(16) . ? N6 C37 1.528(16) . ? C1 C6 1.418(18) . ? C1 C2 1.427(19) . ? C1 C7 1.432(17) . ? C2 C3 1.414(18) . ? C3 C4 1.353(19) . ? C4 C5 1.405(19) . ? C5 C6 1.378(18) . ? C8 C9 1.408(18) . ? C8 C13 1.415(17) . ? C9 C10 1.367(18) . ? C10 C11 1.379(18) . ? C11 C12 1.406(19) . ? C11 C14 1.466(18) . ? C12 C13 1.376(18) . ? C16 C17 1.47(2) . ? C18 C19 1.504(19) . ? C20 C21 1.50(2) . ? C22 C27 1.410(17) . ? C22 C28 1.429(17) . ? C22 C23 1.443(17) . ? C23 C24 1.396(18) . ? C24 C25 1.347(18) . ? C25 C26 1.438(17) . ? C26 C27 1.356(17) . ? C29 C34 1.396(17) . ? C29 C30 1.410(17) . ? C30 C31 1.386(18) . ? C31 C32 1.386(19) . ? C32 C33 1.398(18) . ? C32 C35 1.452(18) . ? C33 C34 1.396(18) . ? C37 C38 1.51(2) . ? C39 C40 1.494(19) . ? C41 C42 1.533(18) . ? 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 N1 93.2(4) . . ? O1 Zn1 Cl2 106.5(3) . . ? N1 Zn1 Cl2 121.6(3) . . ? O1 Zn1 Cl1 115.8(3) . . ? N1 Zn1 Cl1 105.8(3) . . ? Cl2 Zn1 Cl1 112.88(14) . . ? O3 Zn2 N4 95.6(4) . . ? O3 Zn2 Cl3 106.9(3) . . ? N4 Zn2 Cl3 118.2(3) . . ? O3 Zn2 Cl4 112.6(3) . . ? N4 Zn2 Cl4 106.3(3) . . ? Cl3 Zn2 Cl4 115.55(14) . . ? C2 O1 Zn1 119.1(8) . . ? C5 O2 C15 117.5(10) . . ? C23 O3 Zn2 125.1(8) . . ? C26 O4 C36 114.4(10) . . ? C7 N1 C8 119.1(11) . . ? C7 N1 Zn1 118.0(8) . . ? C8 N1 Zn1 121.9(8) . . ? C20 N3 C18 112.3(10) . . ? C20 N3 C16 115.0(12) . . ? C18 N3 C16 110.9(11) . . ? C28 N4 C29 121.3(11) . . ? C28 N4 Zn2 120.9(8) . . ? C29 N4 Zn2 116.9(8) . . ? C41 N6 C39 113.1(10) . . ? C41 N6 C37 109.3(9) . . ? C39 N6 C37 113.2(9) . . ? C6 C1 C2 120.1(11) . . ? C6 C1 C7 115.4(11) . . ? C2 C1 C7 124.5(11) . . ? O1 C2 C3 119.8(12) . . ? O1 C2 C1 123.5(11) . . ? C3 C2 C1 116.7(11) . . ? C4 C3 C2 122.4(12) . . ? C3 C4 C5 121.0(12) . . ? O2 C5 C6 125.6(12) . . ? O2 C5 C4 115.3(12) . . ? C6 C5 C4 119.1(12) . . ? C5 C6 C1 120.6(12) . . ? N1 C7 C1 127.5(12) . . ? C9 C8 C13 118.6(11) . . ? C9 C8 N1 124.4(11) . . ? C13 C8 N1 117.0(11) . . ? C10 C9 C8 120.0(12) . . ? C9 C10 C11 121.3(12) . . ? C10 C11 C12 120.0(11) . . ? C10 C11 C14 119.5(12) . . ? C12 C11 C14 120.4(12) . . ? C13 C12 C11 119.3(12) . . ? C12 C13 C8 120.8(12) . . ? N2 C14 C11 178.9(17) . . ? C17 C16 N3 113.9(12) . . ? C19 C18 N3 111.9(11) . . ? N3 C20 C21 113.0(12) . . ? C27 C22 C28 115.8(11) . . ? C27 C22 C23 118.9(11) . . ? C28 C22 C23 125.2(11) . . ? O3 C23 C24 119.8(11) . . ? O3 C23 C22 124.1(11) . . ? C24 C23 C22 116.1(11) . . ? C25 C24 C23 124.5(12) . . ? C24 C25 C26 119.2(11) . . ? C27 C26 O4 127.4(12) . . ? C27 C26 C25 118.5(11) . . ? O4 C26 C25 114.1(10) . . ? C26 C27 C22 122.5(12) . . ? N4 C28 C22 128.0(12) . . ? C34 C29 C30 120.8(11) . . ? C34 C29 N4 117.7(11) . . ? C30 C29 N4 121.5(11) . . ? C31 C30 C29 117.9(11) . . ? C30 C31 C32 121.7(12) . . ? C31 C32 C33 120.5(12) . . ? C31 C32 C35 120.5(12) . . ? C33 C32 C35 119.0(12) . . ? C34 C33 C32 118.7(12) . . ? C29 C34 C33 120.3(12) . . ? N5 C35 C32 179.0(15) . . ? C38 C37 N6 112.8(10) . . ? C40 C39 N6 114.4(10) . . ? N6 C41 C42 113.0(10) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 25.17 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 2.121 _refine_diff_density_min -1.064 _refine_diff_density_rms 0.233 _database_code_depnum_ccdc_archive 'CCDC 935868' ####################################################################### # # 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_cpd5 #TrackingRef 'web_deposit_cif_file_6_Jing-YunWu_1366794164.cpd 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H29 Cl2 N3 O Zn' _chemical_formula_weight 487.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.1246(7) _cell_length_b 10.1242(6) _cell_length_c 18.2879(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.496(2) _cell_angle_gamma 90.00 _cell_volume 2290.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 1.323 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6402 _exptl_absorpt_correction_T_max 0.8468 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14577 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4010 _reflns_number_gt 3382 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0505P)^2^+0.2541P] 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 4010 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0900 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0584(2) 0.4942(2) 0.17474(14) 0.0305(6) Uani 1 1 d . . . C2 C 0.9741(2) 0.4519(2) 0.20237(14) 0.0291(5) Uani 1 1 d . . . C3 C 1.0015(2) 0.3551(2) 0.26186(14) 0.0350(6) Uani 1 1 d . . . H3 H 0.9480 0.3274 0.2830 0.042 Uiso 1 1 calc R . . C4 C 1.1023(2) 0.3004(2) 0.28971(15) 0.0412(7) Uani 1 1 d . . . H4 H 1.1170 0.2349 0.3290 0.049 Uiso 1 1 calc R . . C5 C 1.1840(2) 0.3396(3) 0.26121(16) 0.0460(7) Uani 1 1 d . . . H5 H 1.2537 0.3004 0.2801 0.055 Uiso 1 1 calc R . . C6 C 1.1612(2) 0.4360(3) 0.20528(15) 0.0397(6) Uani 1 1 d . . . H6 H 1.2169 0.4645 0.1865 0.048 Uiso 1 1 calc R . . C7 C 1.0466(2) 0.5922(2) 0.11571(14) 0.0291(5) Uani 1 1 d . . . H7 H 1.1105 0.6143 0.1049 0.035 Uiso 1 1 calc R . . C8 C 0.96265(19) 0.7424(2) 0.01521(13) 0.0265(5) Uani 1 1 d . . . C9 C 1.0367(2) 0.7301(2) -0.02360(15) 0.0346(6) Uani 1 1 d . . . H9 H 1.0895 0.6620 -0.0095 0.042 Uiso 1 1 calc R . . C10 C 1.0339(2) 0.8164(2) -0.08260(15) 0.0353(6) Uani 1 1 d . . . H10 H 1.0849 0.8077 -0.1089 0.042 Uiso 1 1 calc R . . C11 C 0.9570(2) 0.9158(2) -0.10372(14) 0.0314(6) Uani 1 1 d . . . C12 C 0.8807(2) 0.9270(2) -0.06649(15) 0.0361(6) Uani 1 1 d . . . H12 H 0.8268 0.9936 -0.0817 0.043 Uiso 1 1 calc R . . C13 C 0.8838(2) 0.8409(2) -0.00742(15) 0.0334(6) Uani 1 1 d . . . H13 H 0.8319 0.8486 0.0181 0.040 Uiso 1 1 calc R . . C14 C 0.9561(2) 1.0084(3) -0.16399(16) 0.0393(6) Uani 1 1 d . . . C15 C 0.5400(2) 0.3724(2) 0.07697(13) 0.0257(5) Uani 1 1 d . . . H15A H 0.5806 0.3969 0.0421 0.031 Uiso 1 1 calc R . . H15B H 0.4629 0.3633 0.0447 0.031 Uiso 1 1 calc R . . C16 C 0.5501(2) 0.4828(2) 0.13409(15) 0.0367(6) Uani 1 1 d . . . H16A H 0.5221 0.5647 0.1060 0.055 Uiso 1 1 calc R . . H16B H 0.6264 0.4947 0.1654 0.055 Uiso 1 1 calc R . . H16C H 0.5086 0.4609 0.1681 0.055 Uiso 1 1 calc R . . C17 C 0.70075(19) 0.2497(2) 0.15870(14) 0.0292(5) Uani 1 1 d . . . H17A H 0.7374 0.2894 0.1247 0.035 Uiso 1 1 calc R . . H17B H 0.7109 0.3103 0.2030 0.035 Uiso 1 1 calc R . . C18 C 0.7552(2) 0.1194(2) 0.18940(16) 0.0375(6) Uani 1 1 d . . . H18A H 0.8322 0.1346 0.2172 0.056 Uiso 1 1 calc R . . H18B H 0.7470 0.0589 0.1460 0.056 Uiso 1 1 calc R . . H18C H 0.7216 0.0806 0.2248 0.056 Uiso 1 1 calc R . . C19 C 0.5230(2) 0.1970(2) 0.16906(14) 0.0297(5) Uani 1 1 d . . . H19A H 0.5482 0.1073 0.1884 0.036 Uiso 1 1 calc R . . H19B H 0.5445 0.2574 0.2142 0.036 Uiso 1 1 calc R . . C20 C 0.4007(2) 0.1952(2) 0.13538(16) 0.0371(6) Uani 1 1 d . . . H20A H 0.3708 0.1671 0.1754 0.056 Uiso 1 1 calc R . . H20B H 0.3778 0.1333 0.0917 0.056 Uiso 1 1 calc R . . H20C H 0.3743 0.2839 0.1173 0.056 Uiso 1 1 calc R . . C21 C 0.5592(2) 0.1376(2) 0.04931(14) 0.0301(6) Uani 1 1 d . . . H21A H 0.4813 0.1403 0.0182 0.036 Uiso 1 1 calc R . . H21B H 0.5749 0.0489 0.0732 0.036 Uiso 1 1 calc R . . C22 C 0.6239(2) 0.1553(3) -0.00510(15) 0.0424(7) Uani 1 1 d . . . H22A H 0.6042 0.0860 -0.0448 0.064 Uiso 1 1 calc R . . H22B H 0.7013 0.1492 0.0245 0.064 Uiso 1 1 calc R . . H22C H 0.6082 0.2421 -0.0301 0.064 Uiso 1 1 calc R . . N1 N 0.95944(16) 0.65432(17) 0.07525(11) 0.0266(4) Uani 1 1 d . . . N2 N 0.9563(2) 1.0838(2) -0.21047(15) 0.0550(7) Uani 1 1 d . . . N3 N 0.58079(15) 0.23941(17) 0.11356(10) 0.0234(4) Uani 1 1 d . . . O1 O 0.87506(14) 0.49601(16) 0.17698(10) 0.0335(4) Uani 1 1 d . . . Cl1 Cl 0.73075(5) 0.49030(5) -0.02111(3) 0.03172(16) Uani 1 1 d . . . Cl2 Cl 0.71209(5) 0.77073(6) 0.10895(4) 0.04010(18) Uani 1 1 d . . . Zn1 Zn 0.81488(2) 0.60856(2) 0.087405(16) 0.02813(11) 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 0.0324(14) 0.0308(12) 0.0278(14) -0.0024(10) 0.0092(11) -0.0015(10) C2 0.0368(15) 0.0257(12) 0.0246(13) -0.0055(10) 0.0099(11) -0.0044(11) C3 0.0487(17) 0.0325(13) 0.0259(14) -0.0018(10) 0.0152(12) -0.0034(12) C4 0.0549(18) 0.0368(14) 0.0298(15) 0.0052(11) 0.0112(14) 0.0039(13) C5 0.0432(17) 0.0475(16) 0.0435(18) 0.0089(13) 0.0095(14) 0.0126(14) C6 0.0342(15) 0.0467(15) 0.0390(16) 0.0060(12) 0.0134(13) 0.0027(12) C7 0.0255(13) 0.0331(13) 0.0298(14) -0.0021(10) 0.0106(11) -0.0038(10) C8 0.0279(13) 0.0254(11) 0.0260(13) -0.0027(9) 0.0087(11) -0.0070(10) C9 0.0358(14) 0.0333(13) 0.0388(15) -0.0003(11) 0.0178(13) 0.0029(11) C10 0.0374(15) 0.0392(14) 0.0354(15) -0.0007(11) 0.0201(13) -0.0019(12) C11 0.0378(15) 0.0306(12) 0.0264(13) 0.0007(10) 0.0114(12) -0.0064(11) C12 0.0313(14) 0.0375(14) 0.0397(16) 0.0063(11) 0.0120(13) 0.0002(11) C13 0.0265(13) 0.0397(14) 0.0383(15) 0.0044(11) 0.0166(12) -0.0016(11) C14 0.0393(16) 0.0465(16) 0.0345(15) 0.0014(13) 0.0156(13) -0.0016(12) C15 0.0287(13) 0.0255(11) 0.0224(12) 0.0033(9) 0.0078(10) -0.0001(10) C16 0.0441(16) 0.0252(12) 0.0372(15) -0.0021(10) 0.0090(13) -0.0002(11) C17 0.0245(13) 0.0327(12) 0.0274(13) -0.0014(10) 0.0046(11) -0.0043(10) C18 0.0307(14) 0.0412(14) 0.0382(16) 0.0092(12) 0.0084(12) 0.0061(11) C19 0.0346(14) 0.0307(12) 0.0269(13) 0.0033(10) 0.0142(11) -0.0030(11) C20 0.0340(15) 0.0372(13) 0.0455(16) 0.0028(12) 0.0205(13) -0.0032(11) C21 0.0337(14) 0.0254(11) 0.0289(14) -0.0072(10) 0.0076(11) -0.0064(10) C22 0.0582(19) 0.0397(14) 0.0347(16) -0.0104(11) 0.0225(14) -0.0083(13) N1 0.0283(11) 0.0255(10) 0.0272(11) -0.0013(8) 0.0109(9) -0.0049(9) N2 0.0644(18) 0.0588(15) 0.0517(17) 0.0189(13) 0.0323(15) 0.0052(13) N3 0.0246(10) 0.0243(9) 0.0207(10) 0.0000(7) 0.0069(8) -0.0032(8) O1 0.0330(10) 0.0394(10) 0.0306(10) 0.0046(7) 0.0140(8) -0.0027(8) Cl1 0.0285(3) 0.0322(3) 0.0343(4) -0.0030(2) 0.0103(3) -0.0007(2) Cl2 0.0425(4) 0.0342(3) 0.0505(4) -0.0031(3) 0.0246(3) 0.0039(3) Zn1 0.02782(18) 0.02758(17) 0.03133(19) 0.00072(11) 0.01300(13) -0.00126(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.406(4) . ? C1 C2 1.427(3) . ? C1 C7 1.436(3) . ? C2 O1 1.304(3) . ? C2 C3 1.418(3) . ? C3 C4 1.366(4) . ? C3 H3 0.9500 . ? C4 C5 1.397(4) . ? C4 H4 0.9500 . ? C5 C6 1.373(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.299(3) . ? C7 H7 0.9500 . ? C8 C9 1.387(3) . ? C8 C13 1.397(3) . ? C8 N1 1.426(3) . ? C9 C10 1.379(3) . ? C9 H9 0.9500 . ? C10 C11 1.386(4) . ? C10 H10 0.9500 . ? C11 C12 1.390(3) . ? C11 C14 1.444(3) . ? C12 C13 1.378(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N2 1.143(3) . ? C15 C16 1.505(3) . ? C15 N3 1.520(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.515(3) . ? C17 N3 1.518(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.515(3) . ? C19 N3 1.518(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 N3 1.517(3) . ? C21 C22 1.519(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 Zn1 2.0360(19) . ? O1 Zn1 1.9345(16) . ? Cl1 Zn1 2.2646(6) . ? Cl2 Zn1 2.2418(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.2(2) . . ? C6 C1 C7 115.9(2) . . ? C2 C1 C7 124.9(2) . . ? O1 C2 C3 118.5(2) . . ? O1 C2 C1 124.7(2) . . ? C3 C2 C1 116.8(2) . . ? C4 C3 C2 122.1(2) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 118.4(3) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C1 122.4(3) . . ? C5 C6 H6 118.8 . . ? C1 C6 H6 118.8 . . ? N1 C7 C1 128.0(2) . . ? N1 C7 H7 116.0 . . ? C1 C7 H7 116.0 . . ? C9 C8 C13 119.2(2) . . ? C9 C8 N1 123.0(2) . . ? C13 C8 N1 117.7(2) . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 119.9(2) . . ? C10 C11 C14 120.3(2) . . ? C12 C11 C14 119.8(2) . . ? C13 C12 C11 119.7(2) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C8 120.6(2) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? N2 C14 C11 178.5(3) . . ? C16 C15 N3 114.57(19) . . ? C16 C15 H15A 108.6 . . ? N3 C15 H15A 108.6 . . ? C16 C15 H15B 108.6 . . ? N3 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 N3 114.66(19) . . ? C18 C17 H17A 108.6 . . ? N3 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? N3 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 N3 115.5(2) . . ? C20 C19 H19A 108.4 . . ? N3 C19 H19A 108.4 . . ? C20 C19 H19B 108.4 . . ? N3 C19 H19B 108.4 . . ? H19A C19 H19B 107.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 C22 115.26(19) . . ? N3 C21 H21A 108.5 . . ? C22 C21 H21A 108.5 . . ? N3 C21 H21B 108.5 . . ? C22 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C7 N1 C8 119.6(2) . . ? C7 N1 Zn1 120.23(16) . . ? C8 N1 Zn1 119.63(15) . . ? C21 N3 C17 111.07(18) . . ? C21 N3 C19 108.67(17) . . ? C17 N3 C19 108.36(17) . . ? C21 N3 C15 108.27(16) . . ? C17 N3 C15 109.17(17) . . ? C19 N3 C15 111.32(17) . . ? C2 O1 Zn1 125.45(15) . . ? O1 Zn1 N1 95.42(7) . . ? O1 Zn1 Cl2 112.47(5) . . ? N1 Zn1 Cl2 119.33(5) . . ? O1 Zn1 Cl1 111.87(5) . . ? N1 Zn1 Cl1 102.96(6) . . ? Cl2 Zn1 Cl1 113.28(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.347 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 935869'