Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Chang, SeChin' 'Goldberg, David P.' 'Rheingold, Arnold' 'Sommer, Roger D.' _publ_contact_author_name 'Dr David P Goldberg' _publ_contact_author_address ; Dr David P Goldberg Department of Chemistry The John Hopkins University 3400 N. Charles Street Baltimore MD 21218 UNITED STATES OF AMERICA ; _publ_contact_author_email 'DPG@JHU.EDU' _publ_section_title ; A model complex of a possible intermediate in the mechanism of aciton of pepride deformylase: first example of an (N2S)Zn(II)-formate complex ; data_gold10 _database_code_CSD 169231 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H20 N2 O2 S Zn' _chemical_formula_weight 333.74 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 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 8.3772(4) _cell_length_b 15.7976(8) _cell_length_c 11.6276(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.0170(10) _cell_angle_gamma 90.00 _cell_volume 1536.66(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description colorless _exptl_crystal_colour block _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 1.733 _exptl_absorpt_correction_type 'Empirical from SADABS' _exptl_absorpt_correction_T_min 0.5440 _exptl_absorpt_correction_T_max 0.7231 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 7382 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.25 _reflns_number_total 3449 _reflns_number_gt 2959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0838P)^2^+2.9194P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3449 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 0.650 _refine_ls_restrained_S_all 0.650 _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 0.18866(3) 0.179650(16) 0.62889(2) 0.02406(10) Uani 1 1 d . . . N1 N -0.0137(2) 0.10628(12) 0.61350(14) 0.0240(4) Uani 1 1 d . . . N2 N 0.0811(2) 0.30029(12) 0.65263(15) 0.0249(4) Uani 1 1 d . . . O1 O 0.2876(3) 0.15945(13) 0.78728(17) 0.0500(5) Uani 1 1 d . . . O2 O 0.3590(2) 0.04688(14) 0.6901(2) 0.0554(6) Uani 1 1 d . . . S1 S 0.31900(7) 0.22609(4) 0.47622(5) 0.03252(14) Uani 1 1 d . . . C1 C -0.0087(3) 0.02343(14) 0.64183(18) 0.0272(4) Uani 1 1 d . . . H1 H 0.0910 -0.0007 0.6669 0.033 Uiso 1 1 calc R . . C2 C -0.1429(3) -0.02777(16) 0.6358(2) 0.0327(5) Uani 1 1 d . . . H2 H -0.1356 -0.0859 0.6562 0.039 Uiso 1 1 calc R . . C3 C -0.2877(3) 0.00754(17) 0.5996(2) 0.0359(5) Uani 1 1 d . . . H3 H -0.3817 -0.0261 0.5943 0.043 Uiso 1 1 calc R . . C4 C -0.2943(3) 0.09249(17) 0.5711(2) 0.0349(5) Uani 1 1 d . . . H4 H -0.3934 0.1177 0.5469 0.042 Uiso 1 1 calc R . . C5 C -0.1551(3) 0.14089(15) 0.57808(18) 0.0265(4) Uani 1 1 d . . . C6 C -0.1578(3) 0.23302(15) 0.5451(2) 0.0321(5) Uani 1 1 d . . . H6A H -0.2688 0.2490 0.5209 0.038 Uiso 1 1 calc R . . H6B H -0.0913 0.2408 0.4779 0.038 Uiso 1 1 calc R . . C7 C -0.0970(3) 0.29303(15) 0.6415(2) 0.0310(5) Uani 1 1 d . . . H7A H -0.1430 0.3500 0.6266 0.037 Uiso 1 1 calc R . . H7B H -0.1359 0.2727 0.7155 0.037 Uiso 1 1 calc R . . C8 C 0.1254(3) 0.33640(16) 0.7682(2) 0.0346(5) Uani 1 1 d . . . H8A H 0.2418 0.3425 0.7772 0.052 Uiso 1 1 calc R . . H8B H 0.0885 0.2985 0.8280 0.052 Uiso 1 1 calc R . . H8C H 0.0750 0.3920 0.7755 0.052 Uiso 1 1 calc R . . C9 C 0.1365(3) 0.35568(14) 0.55916(19) 0.0289(4) Uani 1 1 d . . . H9A H 0.1328 0.4151 0.5860 0.035 Uiso 1 1 calc R . . H9B H 0.0594 0.3505 0.4920 0.035 Uiso 1 1 calc R . . C10 C 0.3047(3) 0.33843(15) 0.5180(2) 0.0298(5) Uani 1 1 d . . . C11 C 0.4391(3) 0.3607(2) 0.6071(2) 0.0444(6) Uani 1 1 d . . . H11A H 0.4213 0.4177 0.6373 0.067 Uiso 1 1 calc R . . H11B H 0.5419 0.3590 0.5707 0.067 Uiso 1 1 calc R . . H11C H 0.4401 0.3198 0.6704 0.067 Uiso 1 1 calc R . . C12 C 0.3248(4) 0.39306(19) 0.4101(2) 0.0482(7) Uani 1 1 d . . . H12A H 0.2395 0.3796 0.3520 0.072 Uiso 1 1 calc R . . H12B H 0.4288 0.3813 0.3788 0.072 Uiso 1 1 calc R . . H12C H 0.3187 0.4531 0.4307 0.072 Uiso 1 1 calc R . . C13 C 0.3599(4) 0.09079(19) 0.7775(3) 0.0516(8) Uani 1 1 d . . . H13 H 0.4208 0.0708 0.8433 0.062 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 0.02256(14) 0.02381(15) 0.02582(15) 0.00029(9) 0.00146(9) -0.00161(9) N1 0.0229(8) 0.0278(9) 0.0213(8) -0.0003(7) 0.0010(6) -0.0025(7) N2 0.0278(9) 0.0254(9) 0.0219(8) -0.0010(7) 0.0066(7) -0.0005(7) O1 0.0683(13) 0.0409(11) 0.0386(10) -0.0033(8) -0.0185(9) 0.0040(10) O2 0.0373(10) 0.0398(11) 0.0890(17) -0.0085(11) 0.0028(10) -0.0003(9) S1 0.0350(3) 0.0298(3) 0.0342(3) -0.0047(2) 0.0150(2) -0.0015(2) C1 0.0271(10) 0.0286(11) 0.0260(10) -0.0025(8) 0.0021(8) -0.0025(8) C2 0.0387(12) 0.0299(12) 0.0296(11) -0.0012(9) 0.0034(9) -0.0099(10) C3 0.0299(11) 0.0431(14) 0.0348(12) -0.0046(10) 0.0018(9) -0.0130(10) C4 0.0259(10) 0.0446(14) 0.0338(12) -0.0016(10) -0.0018(9) -0.0009(10) C5 0.0270(10) 0.0309(11) 0.0215(10) -0.0013(8) 0.0004(8) -0.0017(9) C6 0.0275(10) 0.0335(12) 0.0347(12) 0.0043(9) -0.0033(9) 0.0033(9) C7 0.0278(10) 0.0290(11) 0.0370(12) 0.0004(9) 0.0078(9) 0.0023(9) C8 0.0453(14) 0.0336(12) 0.0258(11) -0.0073(9) 0.0089(10) -0.0056(10) C9 0.0350(11) 0.0239(11) 0.0285(11) 0.0034(8) 0.0082(9) 0.0012(9) C10 0.0339(11) 0.0261(11) 0.0305(11) 0.0009(9) 0.0109(9) -0.0036(9) C11 0.0336(12) 0.0502(16) 0.0498(15) -0.0121(13) 0.0070(11) -0.0104(12) C12 0.0619(17) 0.0441(16) 0.0409(14) 0.0127(12) 0.0238(12) 0.0001(13) C13 0.0490(16) 0.0379(15) 0.0646(19) 0.0095(14) -0.0301(14) -0.0079(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.0050(19) . ? Zn1 N1 2.0537(17) . ? Zn1 N2 2.1323(19) . ? Zn1 S1 2.2552(6) . ? Zn1 C13 2.599(3) . ? N1 C5 1.349(3) . ? N1 C1 1.350(3) . ? N2 C9 1.488(3) . ? N2 C8 1.489(3) . ? N2 C7 1.495(3) . ? O1 C13 1.250(4) . ? O2 C13 1.231(4) . ? S1 C10 1.845(2) . ? C1 C2 1.384(3) . ? C2 C3 1.380(4) . ? C3 C4 1.383(4) . ? C4 C5 1.393(3) . ? C5 C6 1.505(3) . ? C6 C7 1.535(3) . ? C9 C10 1.536(3) . ? C10 C11 1.530(3) . ? C10 C12 1.540(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 106.85(8) . . ? O1 Zn1 N2 100.40(8) . . ? N1 Zn1 N2 99.39(7) . . ? O1 Zn1 S1 125.51(7) . . ? N1 Zn1 S1 123.14(5) . . ? N2 Zn1 S1 92.09(5) . . ? O1 Zn1 C13 27.89(10) . . ? N1 Zn1 C13 100.22(8) . . ? N2 Zn1 C13 128.24(9) . . ? S1 Zn1 C13 115.21(8) . . ? C5 N1 C1 118.86(19) . . ? C5 N1 Zn1 120.36(15) . . ? C1 N1 Zn1 120.75(14) . . ? C9 N2 C8 111.19(18) . . ? C9 N2 C7 109.27(17) . . ? C8 N2 C7 107.92(17) . . ? C9 N2 Zn1 106.31(13) . . ? C8 N2 Zn1 111.86(14) . . ? C7 N2 Zn1 110.29(14) . . ? C13 O1 Zn1 103.51(18) . . ? C10 S1 Zn1 93.71(7) . . ? N1 C1 C2 122.7(2) . . ? C3 C2 C1 118.5(2) . . ? C2 C3 C4 119.3(2) . . ? C3 C4 C5 119.7(2) . . ? N1 C5 C4 120.9(2) . . ? N1 C5 C6 118.07(19) . . ? C4 C5 C6 121.0(2) . . ? C5 C6 C7 114.28(19) . . ? N2 C7 C6 113.70(18) . . ? N2 C9 C10 116.71(19) . . ? C11 C10 C9 113.7(2) . . ? C11 C10 C12 108.4(2) . . ? C9 C10 C12 107.2(2) . . ? C11 C10 S1 110.13(18) . . ? C9 C10 S1 109.01(16) . . ? C12 C10 S1 108.24(18) . . ? O2 C13 O1 125.6(3) . . ? O2 C13 Zn1 77.04(17) . . ? O1 C13 Zn1 48.60(13) . . ? _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 0.325 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.057 #===END data_gold13 _database_code_CSD 169232 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H22 N2 S Zn' _chemical_formula_weight 303.76 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' '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 7.9486(7) _cell_length_b 15.0809(15) _cell_length_c 12.1088(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.958(2) _cell_angle_gamma 90.00 _cell_volume 1451.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4654 _cell_measurement_theta_min 28.276 _cell_measurement_theta_max 2.6995 _exptl_crystal_description colorless _exptl_crystal_colour block _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 1.818 _exptl_absorpt_correction_type 'Empirical from SADABS' _exptl_absorpt_correction_T_min 0.6116 _exptl_absorpt_correction_T_max 0.7126 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 6942 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3276 _reflns_number_gt 2878 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0259P)^2^+0.7666P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3276 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0697 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _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 0.20525(3) 0.193255(16) 0.13873(2) 0.02134(8) Uani 1 1 d . . . S1 S 0.29614(7) 0.23889(4) -0.03115(5) 0.02720(13) Uani 1 1 d . . . N2 N 0.0659(2) 0.31573(11) 0.15225(15) 0.0214(4) Uani 1 1 d . . . N1 N -0.0094(2) 0.11077(12) 0.12023(14) 0.0216(4) Uani 1 1 d . . . C7 C -0.1189(3) 0.29870(15) 0.15200(19) 0.0265(5) Uani 1 1 d . . . H7A H -0.1788 0.3560 0.1443 0.032 Uiso 1 1 calc R . . H7B H -0.1495 0.2727 0.2240 0.032 Uiso 1 1 calc R . . C6 C -0.1793(3) 0.23646(15) 0.05967(19) 0.0278(5) Uani 1 1 d . . . H6A H -0.2994 0.2489 0.0432 0.033 Uiso 1 1 calc R . . H6B H -0.1154 0.2498 -0.0078 0.033 Uiso 1 1 calc R . . C5 C -0.1606(2) 0.13980(15) 0.08561(17) 0.0233(4) Uani 1 1 d . . . C4 C -0.2956(3) 0.08147(17) 0.0730(2) 0.0324(5) Uani 1 1 d . . . H4A H -0.4028 0.1028 0.0494 0.039 Uiso 1 1 calc R . . C1 C 0.0097(3) 0.02438(15) 0.14383(18) 0.0272(5) Uani 1 1 d . . . H1A H 0.1164 0.0046 0.1703 0.033 Uiso 1 1 calc R . . C2 C -0.1166(3) -0.03667(16) 0.13167(19) 0.0331(5) Uani 1 1 d . . . H2A H -0.0976 -0.0975 0.1479 0.040 Uiso 1 1 calc R . . C3 C -0.2722(3) -0.00744(17) 0.0952(2) 0.0367(6) Uani 1 1 d . . . H3A H -0.3624 -0.0481 0.0853 0.044 Uiso 1 1 calc R . . C9 C 0.1084(3) 0.37370(14) 0.05757(18) 0.0237(4) Uani 1 1 d . . . H9A H 0.1051 0.4361 0.0828 0.028 Uiso 1 1 calc R . . H9B H 0.0200 0.3666 -0.0003 0.028 Uiso 1 1 calc R . . C10 C 0.2792(3) 0.35685(14) 0.00530(18) 0.0234(4) Uani 1 1 d . . . C8 C 0.1127(3) 0.35835(16) 0.25843(19) 0.0317(5) Uani 1 1 d . . . H8A H 0.0505 0.4140 0.2660 0.048 Uiso 1 1 calc R . . H8B H 0.2338 0.3706 0.2602 0.048 Uiso 1 1 calc R . . H8C H 0.0849 0.3186 0.3195 0.048 Uiso 1 1 calc R . . C12 C 0.2840(3) 0.41186(17) -0.1012(2) 0.0345(5) Uani 1 1 d . . . H12A H 0.2750 0.4750 -0.0830 0.052 Uiso 1 1 calc R . . H12B H 0.1898 0.3947 -0.1499 0.052 Uiso 1 1 calc R . . H12C H 0.3903 0.4010 -0.1388 0.052 Uiso 1 1 calc R . . C11 C 0.4270(3) 0.38493(16) 0.0802(2) 0.0306(5) Uani 1 1 d . . . H11A H 0.4161 0.4479 0.0986 0.046 Uiso 1 1 calc R . . H11B H 0.5329 0.3752 0.0417 0.046 Uiso 1 1 calc R . . H11C H 0.4266 0.3496 0.1481 0.046 Uiso 1 1 calc R . . C13 C 0.3308(3) 0.14999(19) 0.2713(2) 0.0401(6) Uani 1 1 d . . . H13A H 0.2513 0.1362 0.3299 0.060 Uiso 1 1 calc R . . H13B H 0.4091 0.1960 0.2972 0.060 Uiso 1 1 calc R . . H13C H 0.3939 0.0964 0.2523 0.060 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 0.02014(12) 0.01975(14) 0.02408(14) -0.00001(10) -0.00126(9) -0.00027(10) S1 0.0318(3) 0.0219(3) 0.0282(3) -0.0057(2) 0.0104(2) -0.0044(2) N2 0.0223(8) 0.0193(9) 0.0228(9) -0.0017(7) 0.0041(7) -0.0015(7) N1 0.0243(8) 0.0191(9) 0.0214(9) -0.0002(7) 0.0026(7) -0.0026(7) C7 0.0221(9) 0.0230(11) 0.0348(12) -0.0001(9) 0.0081(9) 0.0017(9) C6 0.0190(9) 0.0288(12) 0.0355(13) 0.0041(10) -0.0043(9) -0.0011(9) C5 0.0243(10) 0.0255(11) 0.0201(10) -0.0003(8) 0.0024(8) -0.0038(9) C4 0.0259(10) 0.0395(14) 0.0320(13) -0.0036(10) 0.0023(9) -0.0085(10) C1 0.0364(11) 0.0223(11) 0.0228(11) 0.0003(9) 0.0024(9) -0.0008(9) C2 0.0497(14) 0.0227(12) 0.0272(12) -0.0004(9) 0.0077(11) -0.0088(11) C3 0.0424(13) 0.0350(14) 0.0330(13) -0.0069(11) 0.0084(11) -0.0206(11) C9 0.0253(10) 0.0187(10) 0.0270(11) 0.0019(8) 0.0019(8) -0.0015(8) C10 0.0263(10) 0.0199(11) 0.0240(11) 0.0016(8) 0.0031(8) -0.0052(8) C8 0.0378(12) 0.0302(13) 0.0272(12) -0.0089(10) 0.0056(10) -0.0057(10) C12 0.0390(12) 0.0325(13) 0.0321(13) 0.0069(10) 0.0055(10) -0.0095(11) C11 0.0260(10) 0.0287(12) 0.0371(14) -0.0044(10) 0.0001(10) -0.0060(9) C13 0.0412(13) 0.0409(15) 0.0378(15) 0.0031(12) -0.0138(11) 0.0034(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 C13 1.987(2) . ? Zn1 N1 2.1201(17) . ? Zn1 N2 2.1612(17) . ? Zn1 S1 2.2971(6) . ? S1 C10 1.838(2) . ? N2 C8 1.479(3) . ? N2 C9 1.485(3) . ? N2 C7 1.492(3) . ? N1 C5 1.340(3) . ? N1 C1 1.342(3) . ? C7 C6 1.531(3) . ? C6 C5 1.498(3) . ? C5 C4 1.394(3) . ? C4 C3 1.379(4) . ? C1 C2 1.368(3) . ? C2 C3 1.379(4) . ? C9 C10 1.529(3) . ? C10 C11 1.532(3) . ? C10 C12 1.535(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 C13 Zn1 N1 106.56(9) . . ? C13 Zn1 N2 118.07(10) . . ? N1 Zn1 N2 95.57(6) . . ? C13 Zn1 S1 131.37(8) . . ? N1 Zn1 S1 110.23(5) . . ? N2 Zn1 S1 88.92(5) . . ? C10 S1 Zn1 92.84(7) . . ? C8 N2 C9 110.97(17) . . ? C8 N2 C7 108.06(16) . . ? C9 N2 C7 109.67(17) . . ? C8 N2 Zn1 108.39(14) . . ? C9 N2 Zn1 108.73(12) . . ? C7 N2 Zn1 111.02(13) . . ? C5 N1 C1 118.77(19) . . ? C5 N1 Zn1 123.87(14) . . ? C1 N1 Zn1 117.36(15) . . ? N2 C7 C6 113.82(17) . . ? C5 C6 C7 114.49(19) . . ? N1 C5 C4 120.9(2) . . ? N1 C5 C6 117.99(18) . . ? C4 C5 C6 121.1(2) . . ? C3 C4 C5 119.4(2) . . ? N1 C1 C2 123.4(2) . . ? C1 C2 C3 118.2(2) . . ? C2 C3 C4 119.4(2) . . ? N2 C9 C10 115.90(17) . . ? C9 C10 C11 112.74(18) . . ? C9 C10 C12 107.03(18) . . ? C11 C10 C12 108.57(18) . . ? C9 C10 S1 109.23(14) . . ? C11 C10 S1 110.57(15) . . ? C12 C10 S1 108.56(16) . . ? _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 0.318 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.061