# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/2130 data_bsh41' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H24 N4 O2 S Zn' _chemical_formula_weight 401.82 _chemical_melting_point ? _chemical_compound_source ? 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' 'S' 'S' 0.1246 0.1234 '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 Orthorhombic _symmetry_space_group_name_H-M Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 11.889(2) _cell_length_b 11.694(2) _cell_length_c 13.953(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1939.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 5.63 _cell_measurement_theta_max 12.55 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method ? _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.389 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 832 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 24.98 _reflns_number_total 828 _reflns_number_observed 812 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+1.0766P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0149(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 826 _refine_ls_number_parameters 122 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_obs 0.0303 _refine_ls_wR_factor_all 0.0973 _refine_ls_wR_factor_obs 0.0810 _refine_ls_goodness_of_fit_all 0.914 _refine_ls_goodness_of_fit_obs 0.910 _refine_ls_restrained_S_all 1.081 _refine_ls_restrained_S_obs 0.909 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn1 Zn 0.0000 0.77866(5) 0.45120(3) 0.0390(3) Uani 1 d S . S1 S 0.0000 0.7473(2) 0.6098(2) 0.0486(5) Uani 1 d S . O1 O 0.0000 0.6547(4) 0.3601(4) 0.0464(14) Uani 1 d S . O2 O 0.0000 0.7828(5) 0.2452(6) 0.068(2) Uani 1 d S . N2 N 0.1001(3) 0.9912(3) 0.5074(3) 0.0363(9) Uani 1 d . . N1 N 0.1231(2) 0.9019(3) 0.4492(4) 0.0386(8) Uani 1 d . . C1 C 0.2747(4) 0.8431(5) 0.3410(5) 0.0607(15) Uani 1 d . . H1A H 0.2254(4) 0.7793(5) 0.3308(5) 0.091 Uiso 1 calc R . H1B H 0.3454(4) 0.8163(5) 0.3654(5) 0.091 Uiso 1 calc R . H1C H 0.2868(4) 0.8822(5) 0.2813(5) 0.091 Uiso 1 calc R . C2 C 0.2230(4) 0.9230(4) 0.4111(4) 0.0447(12) Uani 1 d . . C3 C 0.2646(3) 1.0253(4) 0.4464(6) 0.0524(12) Uani 1 d . . H3A H 0.3333(3) 1.0587(4) 0.4309(6) 0.063 Uiso 1 calc R . C4 C 0.1858(4) 1.0680(4) 0.5082(4) 0.0453(12) Uani 1 d . . C5 C 0.1822(5) 1.1754(5) 0.5640(5) 0.066(2) Uani 1 d . . H5A H 0.1138(5) 1.1782(5) 0.6005(5) 0.099 Uiso 1 calc R . H5B H 0.1849(5) 1.2395(5) 0.5210(5) 0.099 Uiso 1 calc R . H5C H 0.2454(5) 1.1783(5) 0.6067(5) 0.099 Uiso 1 calc R . C6 C 0.0000 0.9899(5) 0.5680(5) 0.0328(15) Uani 1 d S . H6B H 0.0000 1.0635(5) 0.6015(5) 0.039 Uiso 1 calc SR . C7 C 0.0000 0.8975(5) 0.6479(6) 0.042(2) Uani 1 d S . C8 C -0.1046(6) 0.9188(5) 0.7079(5) 0.068(2) Uani 1 d . . H8A H -0.1704(6) 0.9052(5) 0.6696(5) 0.102 Uiso 1 calc R . H8B H -0.1048(6) 0.9966(5) 0.7299(5) 0.102 Uiso 1 calc R . H8C H -0.1048(6) 0.8682(5) 0.7620(5) 0.102 Uiso 1 calc R . C9 C 0.0000 0.6847(7) 0.2718(7) 0.047(2) Uani 1 d S . C10 C 0.0000 0.5883(8) 0.2013(9) 0.094(4) Uani 1 d S . H10A H 0.0000 0.5168(8) 0.2350(9) 0.141 Uiso 1 calc SR . H10B H 0.0659 0.5931(8) 0.1617(9) 0.141 Uiso 0.50 calc PR . H10C H -0.0659 0.5931(8) 0.1617(9) 0.141 Uiso 0.50 calc PR . 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 0.0327(4) 0.0341(4) 0.0502(6) -0.0009(3) 0.000 0.000 S1 0.0558(10) 0.0370(7) 0.0531(15) 0.0100(10) 0.000 0.000 O1 0.048(3) 0.036(2) 0.055(5) -0.003(2) 0.000 0.000 O2 0.087(4) 0.057(4) 0.061(5) 0.008(3) 0.000 0.000 N2 0.029(2) 0.036(2) 0.044(3) -0.001(2) 0.003(2) -0.0063(15) N1 0.0299(13) 0.038(2) 0.048(2) -0.002(2) 0.001(2) 0.0009(12) C1 0.045(3) 0.070(3) 0.067(4) -0.002(3) 0.016(3) 0.004(2) C2 0.032(2) 0.049(3) 0.052(3) 0.004(2) 0.006(2) 0.002(2) C3 0.038(2) 0.059(3) 0.060(3) 0.003(3) 0.013(3) -0.015(2) C4 0.037(2) 0.047(2) 0.052(3) 0.001(2) 0.003(2) -0.011(2) C5 0.062(3) 0.059(3) 0.077(5) -0.015(3) 0.014(3) -0.026(3) C6 0.029(2) 0.036(3) 0.034(5) 0.000(2) 0.000 0.000 C7 0.041(3) 0.037(3) 0.047(5) 0.006(3) 0.000 0.000 C8 0.086(4) 0.057(3) 0.061(4) 0.013(3) 0.034(3) 0.011(3) C9 0.046(4) 0.048(4) 0.047(6) -0.004(4) 0.000 0.000 C10 0.142(11) 0.065(5) 0.075(9) -0.018(5) 0.000 0.000 _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 1.928(5) . ? Zn1 N1 2.054(3) . ? Zn1 N1 2.054(3) 4 ? Zn1 S1 2.242(2) . ? S1 C7 1.835(7) . ? O1 C9 1.281(11) . ? O2 C9 1.206(11) . ? N2 N1 1.350(6) . ? N2 C4 1.359(5) . ? N2 C6 1.460(5) . ? N1 C2 1.324(6) . ? C1 C2 1.486(8) . ? C2 C3 1.385(8) . ? C3 C4 1.368(8) . ? C4 C5 1.478(8) . ? C6 N2 1.460(5) 4 ? C6 C7 1.554(9) . ? C7 C8 1.519(7) 4 ? C7 C8 1.519(7) . ? C9 C10 1.497(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 N1 121.2(2) . . ? O1 Zn1 N1 121.2(2) . 4 ? N1 Zn1 N1 90.8(2) . 4 ? O1 Zn1 S1 121.8(2) . . ? N1 Zn1 S1 97.4(2) . . ? N1 Zn1 S1 97.4(2) 4 . ? C7 S1 Zn1 97.5(3) . . ? C9 O1 Zn1 115.3(5) . . ? N1 N2 C4 111.4(3) . . ? N1 N2 C6 120.3(4) . . ? C4 N2 C6 127.8(4) . . ? C2 N1 N2 106.2(4) . . ? C2 N1 Zn1 140.8(4) . . ? N2 N1 Zn1 113.0(3) . . ? N1 C2 C3 109.8(5) . . ? N1 C2 C1 121.2(5) . . ? C3 C2 C1 129.0(5) . . ? C4 C3 C2 107.2(4) . . ? N2 C4 C3 105.5(4) . . ? N2 C4 C5 123.0(4) . . ? C3 C4 C5 131.5(4) . . ? N2 C6 N2 109.2(5) 4 . ? N2 C6 C7 115.0(3) 4 . ? N2 C6 C7 115.0(3) . . ? C8 C7 C8 109.9(8) 4 . ? C8 C7 C6 106.3(4) 4 . ? C8 C7 C6 106.3(4) . . ? C8 C7 S1 108.5(3) 4 . ? C8 C7 S1 108.5(4) . . ? C6 C7 S1 117.2(5) . . ? O2 C9 O1 123.9(8) . . ? O2 C9 C10 120.9(9) . . ? O1 C9 C10 115.2(8) . . ? _refine_diff_density_max 0.338 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.070 data_bsh49 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H42 N8 S2 Zn' _chemical_formula_weight 620.19 _chemical_melting_point ? _chemical_compound_source ? 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' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7338(2) _cell_length_b 14.6710(5) _cell_length_c 24.6109(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.225(2) _cell_angle_gamma 90.00 _cell_volume 3134.89(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method ? _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.948 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17232 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4884 _reflns_number_observed 4001 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 251 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+4.6452P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4633 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_obs 0.0418 _refine_ls_wR_factor_all 0.1173 _refine_ls_wR_factor_obs 0.1077 _refine_ls_goodness_of_fit_all 1.047 _refine_ls_goodness_of_fit_obs 1.088 _refine_ls_restrained_S_all 1.064 _refine_ls_restrained_S_obs 1.088 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn1 Zn 0.77839(5) 0.19579(2) 0.028779(13) 0.0232(2) Uani 1 d . . S1 S 0.53952(13) 0.25942(7) 0.01914(3) 0.0344(3) Uani 1 d . . S2 S 0.91704(12) 0.15148(5) 0.10570(3) 0.0250(3) Uani 1 d . . N1 N 0.7468(4) 0.1204(2) -0.04261(10) 0.0245(7) Uani 1 d . . N2 N 0.6908(4) 0.1692(2) -0.08815(9) 0.0245(8) Uani 1 d . . N3 N 0.8867(4) 0.2921(2) -0.01640(9) 0.0216(7) Uani 1 d . . N4 N 0.8072(4) 0.3137(2) -0.06596(9) 0.0199(7) Uani 1 d . . N5 N 0.8661(4) 0.2402(2) 0.25478(9) 0.0230(7) Uani 1 d . . N6 N 0.8043(3) 0.2651(2) 0.20331(9) 0.0192(7) Uani 1 d . . N7 N 0.5468(4) 0.1205(2) 0.23527(10) 0.0263(9) Uani 1 d . . N8 N 0.5584(4) 0.1900(2) 0.19850(10) 0.0212(8) Uani 1 d . . C1 C 0.8063(5) -0.0398(2) -0.01935(14) 0.0331(10) Uani 1 d . . H1A H 0.8304(5) -0.0142(2) 0.01645(14) 0.050 Uiso 1 calc R . H1B H 0.8955(5) -0.0702(2) -0.03022(14) 0.050 Uiso 1 calc R . H1C H 0.7237(5) -0.0828(2) -0.01874(14) 0.050 Uiso 1 calc R . C2 C 0.7586(4) 0.0345(2) -0.05906(13) 0.0250(9) Uani 1 d . . C3 C 0.7128(5) 0.0284(2) -0.11510(13) 0.0306(10) Uani 1 d . . H3A H 0.7123(5) -0.0240(2) -0.13641(13) 0.037 Uiso 1 calc R . C4 C 0.6690(5) 0.1136(2) -0.13275(12) 0.0267(9) Uani 1 d . . C5 C 0.5969(5) 0.1453(3) -0.18748(12) 0.0390(11) Uani 1 d . . H5B H 0.5812(5) 0.2100(3) -0.18657(12) 0.059 Uiso 1 calc R . H5C H 0.4997(5) 0.1152(3) -0.19618(12) 0.059 Uiso 1 calc R . H5D H 0.6638(5) 0.1309(3) -0.21479(12) 0.059 Uiso 1 calc R . C6 C 0.6644(4) 0.2668(2) -0.08462(11) 0.0225(9) Uani 1 d . . H6A H 0.6370(4) 0.2872(2) -0.12234(11) 0.027 Uiso 1 calc R . C7 C 0.5254(5) 0.2939(2) -0.05327(12) 0.0255(9) Uani 1 d . . C8 C 0.3822(5) 0.2493(3) -0.08333(14) 0.0370(11) Uani 1 d . . H8A H 0.2937(5) 0.2642(3) -0.06509(14) 0.056 Uiso 1 calc R . H8B H 0.3956(5) 0.1843(3) -0.08351(14) 0.056 Uiso 1 calc R . H8C H 0.3674(5) 0.2713(3) -0.12027(14) 0.056 Uiso 1 calc R . C9 C 0.5102(5) 0.3979(2) -0.05577(15) 0.0406(11) Uani 1 d . . H9A H 0.6008(5) 0.4252(2) -0.03696(15) 0.061 Uiso 1 calc R . H9B H 0.4215(5) 0.4163(2) -0.03868(15) 0.061 Uiso 1 calc R . H9C H 0.4989(5) 0.4173(2) -0.09325(15) 0.061 Uiso 1 calc R . C10 C 0.8780(5) 0.3824(2) -0.09080(12) 0.0259(9) Uani 1 d . . C11 C 0.8183(5) 0.4210(2) -0.14519(12) 0.0351(10) Uani 1 d . . H11A H 0.7259(5) 0.3896(2) -0.15901(12) 0.053 Uiso 1 calc R . H11B H 0.8944(5) 0.4137(2) -0.17021(12) 0.053 Uiso 1 calc R . H11C H 0.7963(5) 0.4847(2) -0.14128(12) 0.053 Uiso 1 calc R . C12 C 1.0065(5) 0.4046(2) -0.05599(12) 0.0286(10) Uani 1 d . . H12A H 1.0786(5) 0.4493(2) -0.06157(12) 0.034 Uiso 1 calc R . C13 C 1.0080(5) 0.3472(2) -0.01067(12) 0.0235(9) Uani 1 d . . C14 C 1.1254(5) 0.3418(2) 0.03828(13) 0.0294(9) Uani 1 d . . H14A H 1.0958(5) 0.2956(2) 0.06270(13) 0.044 Uiso 1 calc R . H14B H 1.1318(5) 0.3996(2) 0.05673(13) 0.044 Uiso 1 calc R . H14C H 1.2240(5) 0.3268(2) 0.02681(13) 0.044 Uiso 1 calc R . C15 C 0.7716(4) 0.1165(2) 0.15137(11) 0.0226(9) Uani 1 d . . C16 C 0.6483(5) 0.0575(2) 0.12064(13) 0.0315(10) Uani 1 d . . H16A H 0.5921(5) 0.0928(2) 0.09230(13) 0.047 Uiso 1 calc R . H16B H 0.5790(5) 0.0358(2) 0.14549(13) 0.047 Uiso 1 calc R . H16C H 0.6958(5) 0.0065(2) 0.10469(13) 0.047 Uiso 1 calc R . C17 C 0.8622(5) 0.0602(2) 0.19681(12) 0.0302(10) Uani 1 d . . H17A H 0.9401(5) 0.0977(2) 0.21613(12) 0.045 Uiso 1 calc R . H17B H 0.9098(5) 0.0092(2) 0.18090(12) 0.045 Uiso 1 calc R . H17C H 0.7931(5) 0.0386(2) 0.22176(12) 0.045 Uiso 1 calc R . C18 C 0.6967(4) 0.2045(2) 0.17118(11) 0.0195(9) Uani 1 d . . H18A H 0.6621(4) 0.2386(2) 0.13786(11) 0.023 Uiso 1 calc R . C19 C 0.4250(5) 0.2398(2) 0.19020(12) 0.0261(10) Uani 1 d . . C20 C 0.4053(5) 0.3222(3) 0.15497(14) 0.0381(11) Uani 1 d . . H20A H 0.4975(5) 0.3324(3) 0.13781(14) 0.057 Uiso 1 calc R . H20B H 0.3858(5) 0.3742(3) 0.17693(14) 0.057 Uiso 1 calc R . H20C H 0.3201(5) 0.3134(3) 0.12743(14) 0.057 Uiso 1 calc R . C21 C 0.3246(5) 0.2005(2) 0.22185(13) 0.0299(10) Uani 1 d . . H21A H 0.2238(5) 0.2185(2) 0.22499(13) 0.036 Uiso 1 calc R . C22 C 0.4040(6) 0.1277(2) 0.24870(13) 0.0276(10) Uani 1 d . . C23 C 0.3443(5) 0.0605(3) 0.28703(14) 0.0421(11) Uani 1 d . . H23A H 0.4243(5) 0.0180(3) 0.29918(14) 0.063 Uiso 1 calc R . H23B H 0.2583(5) 0.0283(3) 0.26852(14) 0.063 Uiso 1 calc R . H23C H 0.3121(5) 0.0922(3) 0.31797(14) 0.063 Uiso 1 calc R . C24 C 0.8620(4) 0.3461(2) 0.18786(12) 0.0217(9) Uani 1 d . . C25 C 0.8152(5) 0.3909(2) 0.13359(12) 0.0289(10) Uani 1 d . . H25A H 0.7411(5) 0.3533(2) 0.11240(12) 0.043 Uiso 1 calc R . H25B H 0.9042(5) 0.3986(2) 0.11432(12) 0.043 Uiso 1 calc R . H25C H 0.7705(5) 0.4494(2) 0.13941(12) 0.043 Uiso 1 calc R . C26 C 0.9625(5) 0.3746(2) 0.23038(12) 0.0276(9) Uani 1 d . . H26A H 1.0201(5) 0.4280(2) 0.23229(12) 0.033 Uiso 1 calc R . C27 C 0.9623(5) 0.3072(2) 0.27097(12) 0.0249(9) Uani 1 d . . C28 C 1.0506(5) 0.3046(3) 0.32689(14) 0.0380(11) Uani 1 d . . H28A H 1.0256(5) 0.2498(3) 0.34531(14) 0.057 Uiso 1 calc R . H28B H 1.0234(5) 0.3566(3) 0.34754(14) 0.057 Uiso 1 calc R . H28C H 1.1590(5) 0.3059(3) 0.32352(14) 0.057 Uiso 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 0.0230(4) 0.0278(2) 0.0185(2) -0.00050(13) 0.0006(2) 0.0001(2) S1 0.0241(9) 0.0570(6) 0.0222(4) 0.0015(4) 0.0025(4) 0.0081(5) S2 0.0223(8) 0.0310(4) 0.0213(3) 0.0008(3) 0.0011(3) 0.0035(4) N1 0.024(2) 0.0268(13) 0.0227(12) -0.0017(10) 0.0012(12) -0.0026(13) N2 0.026(2) 0.0281(13) 0.0190(11) -0.0027(10) -0.0011(12) -0.0046(13) N3 0.016(2) 0.0279(13) 0.0201(11) -0.0011(10) 0.0006(11) -0.0010(13) N4 0.013(2) 0.0275(13) 0.0195(11) -0.0012(10) 0.0005(11) -0.0022(13) N5 0.022(2) 0.0259(13) 0.0205(11) 0.0021(10) -0.0019(12) 0.0013(13) N6 0.016(2) 0.0204(12) 0.0204(11) 0.0008(9) 0.0002(11) -0.0019(12) N7 0.023(3) 0.0292(14) 0.0260(13) 0.0053(11) 0.0007(14) -0.0063(15) N8 0.015(3) 0.0258(13) 0.0231(12) 0.0012(10) 0.0044(12) -0.0039(14) C1 0.030(3) 0.028(2) 0.042(2) -0.0022(14) 0.007(2) 0.002(2) C2 0.015(3) 0.029(2) 0.032(2) -0.0051(13) 0.0065(15) -0.005(2) C3 0.029(3) 0.031(2) 0.032(2) -0.0115(13) 0.006(2) -0.009(2) C4 0.023(3) 0.034(2) 0.0228(14) -0.0072(12) 0.0044(15) -0.013(2) C5 0.053(4) 0.043(2) 0.0203(15) -0.0064(14) 0.001(2) -0.015(2) C6 0.017(3) 0.029(2) 0.0205(13) -0.0013(12) -0.0021(14) -0.004(2) C7 0.015(3) 0.035(2) 0.0244(14) -0.0006(13) -0.0028(14) 0.000(2) C8 0.015(3) 0.062(3) 0.033(2) -0.004(2) -0.003(2) -0.002(2) C9 0.040(4) 0.040(2) 0.042(2) 0.000(2) 0.005(2) 0.011(2) C10 0.028(3) 0.025(2) 0.0243(14) -0.0006(12) 0.0042(15) -0.002(2) C11 0.043(3) 0.036(2) 0.026(2) 0.0047(13) -0.001(2) -0.010(2) C12 0.027(3) 0.030(2) 0.029(2) 0.0009(13) 0.004(2) -0.008(2) C13 0.015(3) 0.029(2) 0.0267(15) -0.0047(12) 0.0029(14) 0.000(2) C14 0.019(3) 0.039(2) 0.030(2) -0.0002(14) -0.001(2) -0.005(2) C15 0.025(3) 0.0202(14) 0.0218(13) 0.0015(11) -0.0004(14) -0.0006(15) C16 0.035(3) 0.029(2) 0.031(2) -0.0033(13) 0.003(2) -0.008(2) C17 0.040(3) 0.024(2) 0.0267(15) 0.0030(12) 0.003(2) 0.009(2) C18 0.017(3) 0.0216(14) 0.0197(13) 0.0022(11) -0.0016(14) -0.0029(14) C19 0.017(3) 0.038(2) 0.0235(14) -0.0030(13) 0.0000(15) 0.003(2) C20 0.034(3) 0.049(2) 0.032(2) 0.006(2) 0.007(2) 0.014(2) C21 0.011(3) 0.046(2) 0.033(2) -0.0042(15) 0.006(2) -0.003(2) C22 0.022(4) 0.033(2) 0.029(2) -0.0046(13) 0.005(2) -0.012(2) C23 0.047(4) 0.044(2) 0.038(2) -0.003(2) 0.015(2) -0.018(2) C24 0.020(3) 0.0204(14) 0.0253(14) 0.0004(11) 0.0039(14) 0.0021(15) C25 0.040(3) 0.0213(15) 0.0254(14) 0.0026(12) 0.005(2) -0.005(2) C26 0.027(3) 0.026(2) 0.030(2) -0.0018(13) 0.001(2) -0.007(2) C27 0.020(3) 0.027(2) 0.0272(15) -0.0022(12) -0.0009(15) 0.002(2) C28 0.037(3) 0.039(2) 0.034(2) 0.0024(15) -0.014(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N1 2.069(2) . ? Zn1 N3 2.087(3) . ? Zn1 S2 2.2306(8) . ? Zn1 S1 2.2744(11) . ? S1 C7 1.844(3) . ? S2 C15 1.858(4) . ? N1 C2 1.332(4) . ? N1 N2 1.374(3) . ? N2 C4 1.364(4) . ? N2 C6 1.455(4) . ? N3 C13 1.327(5) . ? N3 N4 1.374(3) . ? N4 C10 1.362(4) . ? N4 C6 1.454(4) . ? N5 C27 1.326(4) . ? N5 N6 1.371(3) . ? N6 C24 1.362(4) . ? N6 C18 1.462(4) . ? N7 C22 1.329(5) . ? N7 N8 1.374(3) . ? N8 C19 1.372(5) . ? N8 C18 1.460(5) . ? C1 C2 1.492(5) . ? C2 C3 1.397(4) . ? C3 C4 1.364(5) . ? C4 C5 1.498(4) . ? C6 C7 1.559(5) . ? C7 C8 1.530(5) . ? C7 C9 1.532(5) . ? C10 C12 1.374(5) . ? C10 C11 1.495(4) . ? C12 C13 1.396(4) . ? C13 C14 1.497(5) . ? C15 C16 1.518(5) . ? C15 C17 1.538(4) . ? C15 C18 1.550(4) . ? C19 C21 1.362(5) . ? C19 C20 1.487(5) . ? C21 C22 1.400(5) . ? C22 C23 1.496(5) . ? C24 C26 1.357(5) . ? C24 C25 1.505(4) . ? C26 C27 1.406(4) . ? C27 C28 1.503(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 N1 Zn1 N3 86.31(10) . . ? N1 Zn1 S2 125.11(8) . . ? N3 Zn1 S2 114.44(8) . . ? N1 Zn1 S1 95.42(9) . . ? N3 Zn1 S1 97.48(9) . . ? S2 Zn1 S1 127.99(3) . . ? C7 S1 Zn1 100.25(13) . . ? C15 S2 Zn1 104.48(11) . . ? C2 N1 N2 106.1(2) . . ? C2 N1 Zn1 139.2(2) . . ? N2 N1 Zn1 114.7(2) . . ? C4 N2 N1 110.6(3) . . ? C4 N2 C6 128.9(3) . . ? N1 N2 C6 120.5(2) . . ? C13 N3 N4 106.0(2) . . ? C13 N3 Zn1 139.3(2) . . ? N4 N3 Zn1 114.5(2) . . ? C10 N4 N3 111.0(3) . . ? C10 N4 C6 128.6(3) . . ? N3 N4 C6 120.4(2) . . ? C27 N5 N6 104.7(2) . . ? C24 N6 N5 111.7(2) . . ? C24 N6 C18 128.0(2) . . ? N5 N6 C18 120.2(2) . . ? C22 N7 N8 104.1(3) . . ? C19 N8 N7 111.8(3) . . ? C19 N8 C18 125.8(3) . . ? N7 N8 C18 122.4(3) . . ? N1 C2 C3 109.7(3) . . ? N1 C2 C1 121.2(3) . . ? C3 C2 C1 129.0(3) . . ? C4 C3 C2 107.3(3) . . ? C3 C4 N2 106.3(3) . . ? C3 C4 C5 130.3(3) . . ? N2 C4 C5 123.1(3) . . ? N2 C6 N4 110.4(3) . . ? N2 C6 C7 114.7(3) . . ? N4 C6 C7 114.2(2) . . ? C8 C7 C6 106.9(3) . . ? C8 C7 C9 110.1(3) . . ? C6 C7 C9 107.6(3) . . ? C8 C7 S1 108.4(3) . . ? C6 C7 S1 115.7(2) . . ? C9 C7 S1 108.0(2) . . ? N4 C10 C12 106.0(3) . . ? N4 C10 C11 123.5(3) . . ? C12 C10 C11 130.6(3) . . ? C10 C12 C13 107.0(3) . . ? N3 C13 C12 110.1(3) . . ? N3 C13 C14 121.5(3) . . ? C12 C13 C14 128.4(3) . . ? C16 C15 C17 109.7(3) . . ? C16 C15 C18 109.3(3) . . ? C17 C15 C18 114.8(2) . . ? C16 C15 S2 110.5(2) . . ? C17 C15 S2 104.9(3) . . ? C18 C15 S2 107.5(2) . . ? N6 C18 N8 110.8(2) . . ? N6 C18 C15 114.1(3) . . ? N8 C18 C15 115.0(2) . . ? N8 C19 C21 106.2(3) . . ? N8 C19 C20 124.2(3) . . ? C21 C19 C20 129.6(4) . . ? C19 C21 C22 106.0(4) . . ? N7 C22 C21 111.9(3) . . ? N7 C22 C23 120.4(3) . . ? C21 C22 C23 127.7(4) . . ? C26 C24 N6 106.4(3) . . ? C26 C24 C25 129.8(3) . . ? N6 C24 C25 123.8(3) . . ? C24 C26 C27 106.3(3) . . ? N5 C27 C26 110.9(3) . . ? N5 C27 C28 120.1(3) . . ? C26 C27 C28 128.9(3) . . ? _refine_diff_density_max 0.513 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.063 data_bsh50 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H21 Cl N4 S Zn' _chemical_formula_weight 378.23 _chemical_melting_point ? _chemical_compound_source ? 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' 'S' 'S' 0.1246 0.1234 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.905(2) _cell_length_b 13.758(2) _cell_length_c 14.787(3) _cell_angle_alpha 67.815(12) _cell_angle_beta 87.213(14) _cell_angle_gamma 71.473(14) _cell_volume 1763.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 4.83 _cell_measurement_theta_max 12.54 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method ? _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 1.661 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4499 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 22.50 _reflns_number_total 4198 _reflns_number_observed 3534 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+1.7231P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4194 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_obs 0.0371 _refine_ls_wR_factor_all 0.1035 _refine_ls_wR_factor_obs 0.0940 _refine_ls_goodness_of_fit_all 1.059 _refine_ls_goodness_of_fit_obs 1.079 _refine_ls_restrained_S_all 1.082 _refine_ls_restrained_S_obs 1.079 _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn1 Zn 0.45309(5) 0.26255(4) 0.24923(4) 0.0394(2) Uani 1 d . . Zn2 Zn -0.03837(5) 0.74945(4) 0.26970(4) 0.0407(2) Uani 1 d . . Cl1 Cl 0.5590(2) 0.26889(14) 0.37258(11) 0.0762(4) Uani 1 d . . Cl2 Cl -0.1937(2) 0.72567(14) 0.18661(12) 0.0807(5) Uani 1 d . . S1 S 0.27945(14) 0.19014(10) 0.24797(9) 0.0493(3) Uani 1 d . . S2 S 0.12199(12) 0.84106(9) 0.22573(8) 0.0420(3) Uani 1 d . . N1 N 0.5834(3) 0.2014(3) 0.1553(2) 0.0335(8) Uani 1 d . . N2 N 0.5108(3) 0.2143(3) 0.0727(2) 0.0323(8) Uani 1 d . . N3 N 0.3709(3) 0.4090(3) 0.1276(2) 0.0357(8) Uani 1 d . . N4 N 0.3427(3) 0.3937(3) 0.0452(2) 0.0324(8) Uani 1 d . . N5 N 0.0908(4) 0.6040(3) 0.3756(3) 0.0374(9) Uani 1 d . . N6 N 0.1515(3) 0.6202(3) 0.4470(2) 0.0334(8) Uani 1 d . . N7 N -0.1173(3) 0.8047(3) 0.3811(2) 0.0335(8) Uani 1 d . . N8 N -0.0120(3) 0.7921(3) 0.4447(2) 0.0309(8) Uani 1 d . . C1 C 0.3538(6) 0.5653(4) 0.1756(4) 0.0625(15) Uani 1 d . . H1A H 0.3905(6) 0.5060(4) 0.2379(4) 0.094 Uiso 1 calc R . H1B H 0.2623(6) 0.6130(4) 0.1819(4) 0.094 Uiso 1 calc R . H1C H 0.4187(6) 0.6071(4) 0.1542(4) 0.094 Uiso 1 calc R . C2 C 0.3385(4) 0.5183(3) 0.1024(3) 0.0412(11) Uani 1 d . . C3 C 0.2893(5) 0.5720(4) 0.0037(4) 0.0487(12) Uani 1 d . . H3A H 0.2594(5) 0.6482(4) -0.0319(4) 0.058 Uiso 1 calc R . C4 C 0.2929(4) 0.4931(3) -0.0312(3) 0.0415(11) Uani 1 d . . C5 C 0.2514(6) 0.5046(4) -0.1314(4) 0.0648(15) Uani 1 d . . H5A H 0.2661(6) 0.4324(4) -0.1320(4) 0.097 Uiso 1 calc R . H5B H 0.3090(6) 0.5404(4) -0.1777(4) 0.097 Uiso 1 calc R . H5C H 0.1525(6) 0.5483(4) -0.1490(4) 0.097 Uiso 1 calc R . C6 C 0.5515(5) 0.1576(4) -0.0720(4) 0.0550(13) Uani 1 d . . H6A H 0.4520(5) 0.1999(4) -0.0887(4) 0.082 Uiso 1 calc R . H6B H 0.5660(5) 0.0824(4) -0.0640(4) 0.082 Uiso 1 calc R . H6C H 0.6062(5) 0.1893(4) -0.1235(4) 0.082 Uiso 1 calc R . C7 C 0.5985(5) 0.1597(3) 0.0210(3) 0.0399(11) Uani 1 d . . C8 C 0.7298(5) 0.1109(4) 0.0729(3) 0.0460(12) Uani 1 d . . H8A H 0.8122(5) 0.0678(4) 0.0560(3) 0.055 Uiso 1 calc R . C9 C 0.7170(4) 0.1376(3) 0.1551(3) 0.0405(11) Uani 1 d . . C10 C 0.8277(5) 0.1093(4) 0.2342(4) 0.0563(13) Uani 1 d . . H10A H 0.7846(5) 0.1401(4) 0.2811(4) 0.084 Uiso 1 calc R . H10B H 0.9020(5) 0.1396(4) 0.2061(4) 0.084 Uiso 1 calc R . H10C H 0.8675(5) 0.0302(4) 0.2661(4) 0.084 Uiso 1 calc R . C11 C 0.3594(4) 0.2826(3) 0.0496(3) 0.0292(9) Uani 1 d . . H11A H 0.3356(4) 0.2919(3) -0.0174(3) 0.035 Uiso 1 calc R . C12 C 0.2554(4) 0.2267(3) 0.1142(3) 0.0383(10) Uani 1 d . . C13 C 0.2729(6) 0.1200(4) 0.0986(4) 0.0567(14) Uani 1 d . . H13A H 0.3676(6) 0.0692(4) 0.1224(4) 0.085 Uiso 1 calc R . H13B H 0.2579(6) 0.1367(4) 0.0299(4) 0.085 Uiso 1 calc R . H13C H 0.2042(6) 0.0869(4) 0.1335(4) 0.085 Uiso 1 calc R . C14 C 0.1034(5) 0.3085(4) 0.0773(4) 0.065(2) Uani 1 d . . H14A H 0.0931(5) 0.3751(4) 0.0879(4) 0.098 Uiso 1 calc R . H14B H 0.0350(5) 0.2752(4) 0.1124(4) 0.098 Uiso 1 calc R . H14C H 0.0872(5) 0.3262(4) 0.0086(4) 0.098 Uiso 1 calc R . C15 C -0.3787(5) 0.8911(4) 0.3522(4) 0.0611(15) Uani 1 d . . H15A H -0.3632(5) 0.8636(4) 0.3004(4) 0.092 Uiso 1 calc R . H15B H -0.4216(5) 0.9703(4) 0.3248(4) 0.092 Uiso 1 calc R . H15C H -0.4411(5) 0.8585(4) 0.3961(4) 0.092 Uiso 1 calc R . C16 C -0.2393(4) 0.8610(3) 0.4069(3) 0.0397(11) Uani 1 d . . C17 C -0.2113(5) 0.8831(4) 0.4870(4) 0.0457(12) Uani 1 d . . H17A H -0.2783(5) 0.9211(4) 0.5186(4) 0.055 Uiso 1 calc R . C18 C -0.0661(4) 0.8383(3) 0.5112(3) 0.0355(10) Uani 1 d . . C19 C 0.0226(5) 0.8346(4) 0.5907(3) 0.0523(13) Uani 1 d . . H19A H 0.1210(5) 0.7965(4) 0.5867(3) 0.078 Uiso 1 calc R . H19B H -0.0074(5) 0.7960(4) 0.6529(3) 0.078 Uiso 1 calc R . H19C H 0.0119(5) 0.9088(4) 0.5842(3) 0.078 Uiso 1 calc R . C20 C 0.3118(5) 0.5137(4) 0.6030(4) 0.0607(14) Uani 1 d . . H20A H 0.2958(5) 0.5868(4) 0.6017(4) 0.091 Uiso 1 calc R . H20B H 0.4121(5) 0.4785(4) 0.6015(4) 0.091 Uiso 1 calc R . H20C H 0.2786(5) 0.4707(4) 0.6617(4) 0.091 Uiso 1 calc R . C21 C 0.2326(4) 0.5217(3) 0.5160(3) 0.0416(11) Uani 1 d . . C22 C 0.2223(5) 0.4413(4) 0.4867(4) 0.0522(13) Uani 1 d . . H22A H 0.2663(5) 0.3653(4) 0.5187(4) 0.063 Uiso 1 calc R . C23 C 0.1336(5) 0.4940(4) 0.3995(4) 0.0447(12) Uani 1 d . . C24 C 0.0873(6) 0.4456(4) 0.3369(4) 0.065(2) Uani 1 d . . H24A H 0.0265(6) 0.5041(4) 0.2817(4) 0.098 Uiso 1 calc R . H24B H 0.0360(6) 0.3970(4) 0.3743(4) 0.098 Uiso 1 calc R . H24C H 0.1697(6) 0.4044(4) 0.3142(4) 0.098 Uiso 1 calc R . C25 C 0.1381(4) 0.7318(3) 0.4381(3) 0.0290(9) Uani 1 d . . H25A H 0.1906(4) 0.7227(3) 0.4968(3) 0.035 Uiso 1 calc R . C26 C 0.2092(4) 0.7966(3) 0.3493(3) 0.0317(10) Uani 1 d . . C27 C 0.2118(5) 0.9001(4) 0.3647(3) 0.0463(11) Uani 1 d . . H27A H 0.1156(5) 0.9477(4) 0.3613(3) 0.069 Uiso 1 calc R . H27B H 0.2622(5) 0.9391(4) 0.3145(3) 0.069 Uiso 1 calc R . H27C H 0.2590(5) 0.8784(4) 0.4278(3) 0.069 Uiso 1 calc R . C28 C 0.3630(4) 0.7196(4) 0.3547(3) 0.0469(12) Uani 1 d . . H28A H 0.3607(4) 0.6548(4) 0.3452(3) 0.070 Uiso 1 calc R . H28B H 0.4105(4) 0.6977(4) 0.4177(3) 0.070 Uiso 1 calc R . H28C H 0.4138(4) 0.7581(4) 0.3044(3) 0.070 Uiso 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 0.0461(3) 0.0397(3) 0.0332(3) -0.0165(2) 0.0042(2) -0.0121(2) Zn2 0.0430(3) 0.0444(3) 0.0392(3) -0.0189(2) -0.0017(2) -0.0160(2) Cl1 0.0799(10) 0.0994(11) 0.0597(9) -0.0462(8) -0.0107(8) -0.0209(8) Cl2 0.0858(11) 0.1015(12) 0.0734(10) -0.0388(9) -0.0188(8) -0.0441(9) S1 0.0616(8) 0.0574(8) 0.0408(7) -0.0216(6) 0.0208(6) -0.0337(6) S2 0.0447(7) 0.0471(7) 0.0329(6) -0.0113(5) 0.0045(5) -0.0184(5) N1 0.034(2) 0.030(2) 0.035(2) -0.013(2) 0.000(2) -0.006(2) N2 0.030(2) 0.033(2) 0.034(2) -0.016(2) 0.004(2) -0.007(2) N3 0.037(2) 0.030(2) 0.042(2) -0.017(2) 0.007(2) -0.010(2) N4 0.034(2) 0.031(2) 0.033(2) -0.014(2) 0.002(2) -0.008(2) N5 0.042(2) 0.031(2) 0.045(2) -0.020(2) 0.011(2) -0.014(2) N6 0.035(2) 0.025(2) 0.037(2) -0.013(2) 0.002(2) -0.005(2) N7 0.027(2) 0.031(2) 0.040(2) -0.014(2) -0.001(2) -0.0057(15) N8 0.024(2) 0.034(2) 0.036(2) -0.018(2) 0.002(2) -0.0054(15) C1 0.074(4) 0.049(3) 0.082(4) -0.043(3) 0.019(3) -0.023(3) C2 0.036(2) 0.035(3) 0.058(3) -0.023(2) 0.011(2) -0.013(2) C3 0.051(3) 0.025(2) 0.062(3) -0.009(2) 0.008(2) -0.010(2) C4 0.037(2) 0.034(3) 0.040(3) -0.004(2) 0.002(2) -0.005(2) C5 0.078(4) 0.047(3) 0.047(3) -0.004(2) -0.006(3) -0.008(3) C6 0.057(3) 0.062(3) 0.058(3) -0.040(3) 0.020(3) -0.017(3) C7 0.045(3) 0.038(2) 0.041(3) -0.023(2) 0.012(2) -0.012(2) C8 0.036(3) 0.043(3) 0.058(3) -0.027(2) 0.008(2) -0.002(2) C9 0.034(2) 0.030(2) 0.049(3) -0.010(2) 0.000(2) -0.006(2) C10 0.042(3) 0.049(3) 0.065(3) -0.015(3) -0.007(3) -0.004(2) C11 0.028(2) 0.028(2) 0.032(2) -0.015(2) 0.001(2) -0.006(2) C12 0.033(2) 0.040(2) 0.043(3) -0.016(2) 0.007(2) -0.013(2) C13 0.076(4) 0.056(3) 0.057(3) -0.029(3) 0.017(3) -0.039(3) C14 0.031(3) 0.077(4) 0.073(4) -0.013(3) 0.004(3) -0.016(3) C15 0.031(3) 0.057(3) 0.081(4) -0.015(3) -0.006(3) -0.009(2) C16 0.030(2) 0.032(2) 0.052(3) -0.011(2) 0.004(2) -0.010(2) C17 0.034(3) 0.043(3) 0.061(3) -0.028(2) 0.015(2) -0.006(2) C18 0.039(3) 0.033(2) 0.037(3) -0.018(2) 0.009(2) -0.011(2) C19 0.048(3) 0.068(3) 0.052(3) -0.040(3) 0.012(3) -0.013(2) C20 0.055(3) 0.045(3) 0.054(3) -0.002(2) -0.014(3) 0.002(2) C21 0.035(2) 0.033(3) 0.044(3) -0.007(2) 0.007(2) -0.003(2) C22 0.052(3) 0.024(2) 0.072(4) -0.016(2) 0.012(3) -0.006(2) C23 0.045(3) 0.036(3) 0.063(3) -0.027(2) 0.021(3) -0.018(2) C24 0.075(4) 0.054(3) 0.092(4) -0.048(3) 0.025(3) -0.031(3) C25 0.027(2) 0.029(2) 0.030(2) -0.013(2) 0.001(2) -0.005(2) C26 0.028(2) 0.034(2) 0.036(2) -0.018(2) 0.004(2) -0.008(2) C27 0.050(3) 0.042(3) 0.051(3) -0.017(2) 0.005(2) -0.022(2) C28 0.029(2) 0.056(3) 0.051(3) -0.021(2) 0.007(2) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N3 2.078(3) . ? Zn1 N1 2.079(3) . ? Zn1 Cl1 2.1907(14) . ? Zn1 S1 2.2488(13) . ? Zn2 N5 2.073(3) . ? Zn2 N7 2.084(3) . ? Zn2 Cl2 2.1889(14) . ? Zn2 S2 2.2555(13) . ? S1 C12 1.855(4) . ? S2 C26 1.853(4) . ? N1 C9 1.336(5) . ? N1 N2 1.371(5) . ? N2 C7 1.363(5) . ? N2 C11 1.470(5) . ? N3 C2 1.336(5) . ? N3 N4 1.368(5) . ? N4 C4 1.359(5) . ? N4 C11 1.461(5) . ? N5 C23 1.340(5) . ? N5 N6 1.361(5) . ? N6 C21 1.367(5) . ? N6 C25 1.453(5) . ? N7 C16 1.338(5) . ? N7 N8 1.364(5) . ? N8 C18 1.365(5) . ? N8 C25 1.473(5) . ? C1 C2 1.490(6) . ? C2 C3 1.393(7) . ? C3 C4 1.357(6) . ? C4 C5 1.494(7) . ? C6 C7 1.486(6) . ? C7 C8 1.372(6) . ? C8 C9 1.386(6) . ? C9 C10 1.494(6) . ? C11 C12 1.555(5) . ? C12 C13 1.526(6) . ? C12 C14 1.540(6) . ? C15 C16 1.492(6) . ? C16 C17 1.389(6) . ? C17 C18 1.377(6) . ? C18 C19 1.479(6) . ? C20 C21 1.490(7) . ? C21 C22 1.364(6) . ? C22 C23 1.399(7) . ? C23 C24 1.487(7) . ? C25 C26 1.563(5) . ? C26 C27 1.532(6) . ? C26 C28 1.540(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Zn1 N1 86.65(13) . . ? N3 Zn1 Cl1 118.11(11) . . ? N1 Zn1 Cl1 117.16(11) . . ? N3 Zn1 S1 97.41(10) . . ? N1 Zn1 S1 98.13(10) . . ? Cl1 Zn1 S1 129.67(6) . . ? N5 Zn2 N7 88.54(13) . . ? N5 Zn2 Cl2 114.07(11) . . ? N7 Zn2 Cl2 115.90(10) . . ? N5 Zn2 S2 98.49(10) . . ? N7 Zn2 S2 96.52(9) . . ? Cl2 Zn2 S2 133.35(6) . . ? C12 S1 Zn1 98.99(14) . . ? C26 S2 Zn2 98.04(13) . . ? C9 N1 N2 105.9(3) . . ? C9 N1 Zn1 139.4(3) . . ? N2 N1 Zn1 113.8(2) . . ? N1 N2 C7 110.9(3) . . ? N1 N2 C11 120.0(3) . . ? C7 N2 C11 129.1(3) . . ? C2 N3 N4 106.6(3) . . ? C2 N3 Zn1 139.3(3) . . ? N4 N3 Zn1 114.1(2) . . ? C4 N4 N3 110.2(3) . . ? C4 N4 C11 129.4(4) . . ? N3 N4 C11 120.3(3) . . ? C23 N5 N6 106.2(4) . . ? C23 N5 Zn2 140.1(3) . . ? N6 N5 Zn2 113.6(2) . . ? N5 N6 C21 111.1(3) . . ? N5 N6 C25 120.4(3) . . ? C21 N6 C25 128.2(4) . . ? C16 N7 N8 105.9(3) . . ? C16 N7 Zn2 140.7(3) . . ? N8 N7 Zn2 112.9(2) . . ? N7 N8 C18 111.5(3) . . ? N7 N8 C25 120.6(3) . . ? C18 N8 C25 127.9(3) . . ? N3 C2 C3 108.9(4) . . ? N3 C2 C1 121.2(4) . . ? C3 C2 C1 129.9(4) . . ? C4 C3 C2 107.7(4) . . ? N4 C4 C3 106.6(4) . . ? N4 C4 C5 123.3(4) . . ? C3 C4 C5 130.1(4) . . ? N2 C7 C8 105.9(4) . . ? N2 C7 C6 123.9(4) . . ? C8 C7 C6 130.2(4) . . ? C7 C8 C9 107.4(4) . . ? N1 C9 C8 109.9(4) . . ? N1 C9 C10 120.3(4) . . ? C8 C9 C10 129.8(4) . . ? N4 C11 N2 109.5(3) . . ? N4 C11 C12 115.0(3) . . ? N2 C11 C12 114.3(3) . . ? C13 C12 C14 110.0(4) . . ? C13 C12 C11 107.8(3) . . ? C14 C12 C11 106.7(3) . . ? C13 C12 S1 107.6(3) . . ? C14 C12 S1 108.0(3) . . ? C11 C12 S1 116.7(3) . . ? N7 C16 C17 109.8(4) . . ? N7 C16 C15 120.9(4) . . ? C17 C16 C15 129.2(4) . . ? C18 C17 C16 107.4(4) . . ? N8 C18 C17 105.5(4) . . ? N8 C18 C19 123.5(4) . . ? C17 C18 C19 131.1(4) . . ? N6 C21 C22 105.9(4) . . ? N6 C21 C20 123.1(4) . . ? C22 C21 C20 130.9(4) . . ? C21 C22 C23 107.6(4) . . ? N5 C23 C22 109.1(4) . . ? N5 C23 C24 121.1(5) . . ? C22 C23 C24 129.8(4) . . ? N6 C25 N8 109.8(3) . . ? N6 C25 C26 114.8(3) . . ? N8 C25 C26 114.4(3) . . ? C27 C26 C28 109.9(3) . . ? C27 C26 C25 106.8(3) . . ? C28 C26 C25 106.3(3) . . ? C27 C26 S2 108.3(3) . . ? C28 C26 S2 108.6(3) . . ? C25 C26 S2 116.7(3) . . ? _refine_diff_density_max 0.363 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.074 data_bsh46 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C30 H50 F5 N4 O S2 Zn' _chemical_formula_weight 707.23 _chemical_melting_point ? _chemical_compound_source ? 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 '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 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 8.563(2) _cell_length_b 33.701(5) _cell_length_c 9.454(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.58(2) _cell_angle_gamma 90.00 _cell_volume 2722.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 5.39 _cell_measurement_theta_max 12.55 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method ? _exptl_crystal_F_000 1492 _exptl_absorpt_coefficient_mu 1.127 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3561 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 22.50 _reflns_number_total 3297 _reflns_number_observed 2455 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 33 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1451P)^2^+11.3825P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3264 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1039 _refine_ls_R_factor_obs 0.0717 _refine_ls_wR_factor_all 0.3360 _refine_ls_wR_factor_obs 0.2177 _refine_ls_goodness_of_fit_all 1.069 _refine_ls_goodness_of_fit_obs 1.070 _refine_ls_restrained_S_all 1.438 _refine_ls_restrained_S_obs 1.070 _refine_ls_shift/esd_max 0.558 _refine_ls_shift/esd_mean 0.019 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn1 Zn 0.75852(13) 0.34143(3) 0.60363(11) 0.0519(5) Uani 1 d . . S1 S 0.7231(3) 0.27461(8) 0.6161(3) 0.0648(8) Uani 1 d . . S2 S 0.6087(3) 0.37126(8) 0.4305(3) 0.0640(8) Uani 1 d . . N1 N 0.7581(9) 0.3510(2) 0.8210(8) 0.052(2) Uani 1 d . . N2 N 0.8556(9) 0.3262(2) 0.8981(8) 0.048(2) Uani 1 d . . N3 N 0.9964(9) 0.3421(2) 0.6230(8) 0.052(2) Uani 1 d . . N4 N 1.0605(9) 0.3214(2) 0.7370(8) 0.051(2) Uani 1 d . . C1 C 0.9249(15) 0.3071(3) 1.1516(11) 0.078(3) Uani 1 d . . H1A H 0.9953(15) 0.2894(3) 1.1080(11) 0.117 Uiso 1 calc R . H1B H 0.8547(15) 0.2921(3) 1.2061(11) 0.117 Uiso 1 calc R . H1C H 0.9836(15) 0.3252(3) 1.2127(11) 0.117 Uiso 1 calc R . C2 C 0.8322(12) 0.3301(3) 1.0385(10) 0.053(2) Uani 1 d . . C3 C 0.7199(13) 0.3583(3) 1.0471(11) 0.062(3) Uani 1 d . . H3A H 0.6787(13) 0.3675(3) 1.1297(11) 0.074 Uiso 1 calc R . C4 C 0.6778(12) 0.3710(3) 0.9105(11) 0.057(3) Uani 1 d . . C5 C 0.5640(14) 0.4030(3) 0.8654(12) 0.077(3) Uani 1 d . . H5A H 0.5585(14) 0.4053(3) 0.7640(12) 0.115 Uiso 1 calc R . H5B H 0.5982(14) 0.4277(3) 0.9070(12) 0.115 Uiso 1 calc R . H5C H 0.4625(14) 0.3964(3) 0.8964(12) 0.115 Uiso 1 calc R . C6 C 1.3218(13) 0.3052(4) 0.8570(15) 0.092(4) Uani 1 d . . H6A H 1.2603(13) 0.2911(4) 0.9220(15) 0.138 Uiso 1 calc R . H6B H 1.3796(13) 0.3259(4) 0.9068(15) 0.138 Uiso 1 calc R . H6C H 1.3933(13) 0.2873(4) 0.8160(15) 0.138 Uiso 1 calc R . C7 C 1.2185(11) 0.3228(3) 0.7447(11) 0.060(3) Uani 1 d . . C8 C 1.2599(13) 0.3455(3) 0.6297(12) 0.073(3) Uani 1 d . . H8A H 1.3606(13) 0.3516(3) 0.6047(12) 0.088 Uiso 1 calc R . C9 C 1.1179(13) 0.3575(3) 0.5592(10) 0.061(3) Uani 1 d . . C10 C 1.0915(14) 0.3823(4) 0.4283(12) 0.080(4) Uani 1 d . . H10A H 0.9812(14) 0.3855(4) 0.4066(12) 0.120 Uiso 1 calc R . H10B H 1.1378(14) 0.3695(4) 0.3504(12) 0.120 Uiso 1 calc R . H10C H 1.1388(14) 0.4079(4) 0.4441(12) 0.120 Uiso 1 calc R . C11 C 0.9591(11) 0.2987(3) 0.8293(9) 0.048(2) Uani 1 d . . H11A H 1.0293(11) 0.2879(3) 0.9054(9) 0.058 Uiso 1 calc R . C13 C 0.7973(14) 0.2393(3) 0.8717(12) 0.074(3) Uani 1 d . . H13A H 0.7171(14) 0.2555(3) 0.9088(12) 0.111 Uiso 1 calc R . H13B H 0.8734(14) 0.2325(3) 0.9467(12) 0.111 Uiso 1 calc R . H13C H 0.7514(14) 0.2155(3) 0.8319(12) 0.111 Uiso 1 calc R . C14 C 1.0031(13) 0.2370(3) 0.6956(13) 0.077(3) Uani 1 d . . H14A H 1.0526(13) 0.2517(3) 0.6237(13) 0.116 Uiso 1 calc R . H14B H 0.9567(13) 0.2134(3) 0.6548(13) 0.116 Uiso 1 calc R . H14C H 1.0796(13) 0.2300(3) 0.7698(13) 0.116 Uiso 1 calc R . C15 C 0.6431(12) 0.4220(3) 0.4235(10) 0.061(3) Uani 1 d . . C16 C 0.5595(16) 0.4449(4) 0.3172(12) 0.080(3) Uani 1 d . . C17 C 0.5817(21) 0.4845(5) 0.3052(17) 0.112(5) Uani 1 d . . C18 C 0.6822(21) 0.5051(4) 0.3953(18) 0.102(5) Uani 1 d . . C19 C 0.7590(17) 0.4849(4) 0.5022(15) 0.086(4) Uani 1 d . . C20 C 0.7403(14) 0.4449(3) 0.5148(11) 0.068(3) Uani 1 d . . F1 F 0.4620(10) 0.4256(2) 0.2225(8) 0.106(3) Uani 1 d . . F2 F 0.4984(15) 0.5041(3) 0.1990(12) 0.174(5) Uani 1 d . . F3 F 0.6947(16) 0.5444(2) 0.3846(12) 0.161(4) Uani 1 d . . F4 F 0.8563(12) 0.5046(2) 0.5940(10) 0.126(3) Uani 1 d . . F5 F 0.8247(9) 0.4253(2) 0.6209(7) 0.092(2) Uani 1 d . . C12 C 0.8772(11) 0.2624(3) 0.7561(9) 0.052(2) Uani 1 d . . O1 O 0.0966(29) 0.4238(12) -0.0084(29) 0.432(23) Uani 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 Zn1 0.0547(8) 0.0580(7) 0.0432(7) 0.0015(5) 0.0044(5) -0.0039(5) S1 0.067(2) 0.057(2) 0.069(2) -0.0036(13) -0.0110(14) -0.0100(13) S2 0.070(2) 0.073(2) 0.0489(15) 0.0072(13) -0.0047(13) -0.0069(14) N1 0.049(5) 0.063(5) 0.044(5) 0.002(4) 0.007(4) 0.007(4) N2 0.050(5) 0.053(4) 0.041(5) -0.003(4) 0.011(4) -0.001(4) N3 0.054(5) 0.053(5) 0.049(5) 0.005(4) 0.013(4) -0.012(4) N4 0.043(5) 0.061(5) 0.052(5) 0.009(4) 0.010(4) -0.007(4) C1 0.107(10) 0.080(8) 0.047(6) 0.000(5) 0.001(6) 0.024(7) C2 0.061(6) 0.062(6) 0.038(6) -0.001(4) 0.016(5) 0.004(5) C3 0.072(7) 0.065(6) 0.050(6) -0.006(5) 0.019(5) 0.013(6) C4 0.050(6) 0.066(6) 0.055(6) 0.000(5) 0.005(5) 0.006(5) C5 0.081(8) 0.079(8) 0.071(7) 0.003(6) 0.017(6) 0.025(6) C6 0.045(7) 0.117(10) 0.112(11) 0.037(8) 0.001(7) -0.002(7) C7 0.044(6) 0.074(7) 0.063(7) 0.000(6) 0.012(5) -0.006(5) C8 0.055(7) 0.091(8) 0.075(8) -0.003(6) 0.016(6) -0.014(6) C9 0.066(7) 0.074(7) 0.046(6) -0.004(5) 0.012(6) -0.014(6) C10 0.081(8) 0.102(9) 0.059(7) 0.008(6) 0.019(6) -0.038(7) C11 0.051(6) 0.052(5) 0.042(5) 0.003(4) 0.007(5) 0.003(4) C13 0.080(8) 0.068(7) 0.075(7) 0.015(6) 0.006(6) -0.031(6) C14 0.076(8) 0.076(7) 0.079(8) -0.020(6) -0.001(6) 0.020(6) C15 0.067(7) 0.071(7) 0.044(6) 0.007(5) 0.009(5) 0.006(5) C16 0.101(10) 0.074(8) 0.064(7) 0.010(6) -0.001(7) 0.009(7) C17 0.150(15) 0.084(10) 0.101(11) 0.032(9) -0.011(10) 0.035(10) C18 0.136(13) 0.060(8) 0.110(12) 0.012(8) -0.006(10) 0.000(8) C19 0.107(10) 0.063(8) 0.090(9) -0.003(7) 0.010(8) -0.011(7) C20 0.076(8) 0.073(7) 0.057(7) 0.006(6) 0.015(6) -0.007(6) F1 0.127(6) 0.096(5) 0.090(5) 0.005(4) -0.042(5) 0.019(5) F2 0.235(12) 0.102(6) 0.173(10) 0.052(6) -0.068(9) 0.025(7) F3 0.241(12) 0.072(6) 0.166(10) 0.019(5) -0.027(9) -0.001(6) F4 0.152(8) 0.095(6) 0.127(7) -0.020(5) -0.019(6) -0.028(5) F5 0.111(5) 0.087(5) 0.075(4) 0.014(4) -0.027(4) -0.022(4) C12 0.055(6) 0.057(6) 0.045(5) 0.004(4) 0.008(5) 0.000(5) O1 0.237(23) 0.772(63) 0.286(29) 0.070(33) 0.002(20) -0.304(34) _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 N3 2.034(8) . ? Zn1 N1 2.080(8) . ? Zn1 S2 2.252(3) . ? Zn1 S1 2.276(3) . ? S1 C12 1.856(10) . ? S2 C15 1.738(11) . ? N1 C4 1.309(12) . ? N1 N2 1.360(10) . ? N2 C2 1.361(11) . ? N2 C11 1.462(12) . ? N3 C9 1.339(13) . ? N3 N4 1.369(11) . ? N4 C7 1.351(12) . ? N4 C11 1.481(12) . ? C1 C2 1.506(14) . ? C2 C3 1.358(14) . ? C3 C4 1.385(14) . ? C4 C5 1.498(14) . ? C6 C7 1.46(2) . ? C7 C8 1.395(15) . ? C8 C9 1.409(15) . ? C9 C10 1.500(15) . ? C11 C12 1.553(13) . ? C13 C12 1.537(14) . ? C14 C12 1.515(14) . ? C15 C20 1.393(15) . ? C15 C16 1.424(15) . ? C16 F1 1.352(14) . ? C16 C17 1.35(2) . ? C17 C18 1.36(2) . ? C17 F2 1.37(2) . ? C18 F3 1.33(2) . ? C18 C19 1.35(2) . ? C19 F4 1.341(14) . ? C19 C20 1.37(2) . ? C20 F5 1.369(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Zn1 N1 88.4(3) . . ? N3 Zn1 S2 125.6(2) . . ? N1 Zn1 S2 127.8(2) . . ? N3 Zn1 S1 98.2(2) . . ? N1 Zn1 S1 95.4(2) . . ? S2 Zn1 S1 114.04(11) . . ? C12 S1 Zn1 99.5(3) . . ? C15 S2 Zn1 112.1(4) . . ? C4 N1 N2 107.4(7) . . ? C4 N1 Zn1 138.7(7) . . ? N2 N1 Zn1 113.3(6) . . ? C2 N2 N1 109.9(7) . . ? C2 N2 C11 128.7(8) . . ? N1 N2 C11 121.3(7) . . ? C9 N3 N4 105.5(8) . . ? C9 N3 Zn1 139.9(7) . . ? N4 N3 Zn1 114.5(5) . . ? C7 N4 N3 112.1(8) . . ? C7 N4 C11 127.4(8) . . ? N3 N4 C11 120.4(7) . . ? N2 C2 C3 105.9(8) . . ? N2 C2 C1 122.6(9) . . ? C3 C2 C1 131.4(9) . . ? C2 C3 C4 107.6(9) . . ? N1 C4 C3 109.2(9) . . ? N1 C4 C5 123.0(9) . . ? C3 C4 C5 127.8(10) . . ? N4 C7 C8 106.2(9) . . ? N4 C7 C6 125.7(10) . . ? C8 C7 C6 128.0(10) . . ? C7 C8 C9 105.7(9) . . ? N3 C9 C8 110.4(9) . . ? N3 C9 C10 120.5(10) . . ? C8 C9 C10 129.1(10) . . ? N2 C11 N4 109.2(7) . . ? N2 C11 C12 115.4(8) . . ? N4 C11 C12 114.2(7) . . ? C20 C15 C16 113.1(10) . . ? C20 C15 S2 128.0(8) . . ? C16 C15 S2 118.8(9) . . ? F1 C16 C17 120.2(12) . . ? F1 C16 C15 118.0(10) . . ? C17 C16 C15 121.7(13) . . ? C18 C17 C16 122.5(13) . . ? C18 C17 F2 119.5(14) . . ? C16 C17 F2 117.9(15) . . ? C17 C18 F3 120.7(14) . . ? C17 C18 C19 117.9(13) . . ? F3 C18 C19 121.2(15) . . ? C18 C19 F4 119.2(12) . . ? C18 C19 C20 120.5(13) . . ? F4 C19 C20 120.3(12) . . ? F5 C20 C19 118.7(11) . . ? F5 C20 C15 117.1(9) . . ? C19 C20 C15 124.1(11) . . ? C14 C12 C13 110.0(9) . . ? C14 C12 C11 107.5(8) . . ? C13 C12 C11 106.9(8) . . ? C14 C12 S1 110.3(7) . . ? C13 C12 S1 106.9(7) . . ? C11 C12 S1 115.1(6) . . ? _refine_diff_density_max 0.997 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.111