# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email tcwmak@cuhk.edu.hk _publ_contact_author_name 'Thomas Mak' _publ_contact_author_address ; Prof Thomas C. W. Mak Department of Chemistry The Chinese University of Hong Kong Hong Kong 852 CHINA ; _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Lin-Ping Zhang' 'Wen-Jie Lu' T.C.W.Mak _publ_section_title ; Controlled crystallization of mixed-ligand complexes of 1,3-bis(4-pyridyl)propane-N,N'-dioxide with metal(II) thiocyanates: isostructurality in coordination networks bearing different mono- and di-nuclear nodes ; data_L _database_code_CSD 214073 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 N2 O2' _chemical_formula_weight 230.26 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 Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 9.1586(16) _cell_length_b 7.7990(14) _cell_length_c 16.794(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1199.5(4) _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 block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.95 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type Sadabs _exptl_absorpt_correction_T_min 0.4634 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7739 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 27.99 _reflns_number_total 1548 _reflns_number_gt 1134 _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^)+(0.0836P)^2^+0.1227P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1548 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 O1 O 0.29243(17) 0.2500 1.21795(8) 0.0632(4) Uani 1 2 d S . . N1 N 0.37768(18) 0.2500 1.15496(9) 0.0489(4) Uani 1 2 d S . . C1 C 0.3202(2) 0.2500 1.08089(12) 0.0630(6) Uani 1 2 d S . . H1A H 0.2193 0.2500 1.0747 0.076 Uiso 1 2 calc SR . . C2 C 0.4077(2) 0.2500 1.01478(11) 0.0655(7) Uani 1 2 d S . . H2A H 0.3647 0.2500 0.9646 0.079 Uiso 1 2 calc SR . . C3 C 0.5589(2) 0.2500 1.02071(10) 0.0502(5) Uani 1 2 d S . . C4 C 0.6145(2) 0.2500 1.09767(10) 0.0494(5) Uani 1 2 d S . . H4A H 0.7151 0.2500 1.1050 0.059 Uiso 1 2 calc SR . . C5 C 0.5248(2) 0.2500 1.16334(11) 0.0522(5) Uani 1 2 d S . . H5A H 0.5656 0.2500 1.2141 0.063 Uiso 1 2 calc SR . . C6 C 0.6613(2) 0.2500 0.95056(11) 0.0615(6) Uani 1 2 d S . . H6A H 0.7236 0.1499 0.9549 0.074 Uiso 1 1 d R . . C7 C 0.5943(2) 0.2500 0.86791(10) 0.0512(5) Uani 1 2 d S . . H7A H 0.5334 0.1493 0.8614 0.061 Uiso 1 1 d R . . C8 C 0.7142(2) 0.2500 0.80471(11) 0.0609(6) Uani 1 2 d S . . H8A H 0.7751 0.1495 0.8122 0.073 Uiso 1 1 d R . . C9 C 0.6556(2) 0.2500 0.72054(10) 0.0505(5) Uani 1 2 d S . . C10 C 0.62691(15) 0.09842(19) 0.68024(8) 0.0534(4) Uani 1 1 d . . . H10A H 0.6441 -0.0059 0.7054 0.064 Uiso 1 1 calc R . . C11 C 0.57331(15) 0.09993(19) 0.60345(7) 0.0507(4) Uani 1 1 d . . . H11A H 0.5543 -0.0031 0.5776 0.061 Uiso 1 1 calc R . . N2 N 0.54822(15) 0.2500 0.56550(8) 0.0441(4) Uani 1 2 d S . . O2 O 0.50030(16) 0.2500 0.49131(7) 0.0530(4) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0627(9) 0.0827(11) 0.0441(7) 0.000 0.0116(6) 0.000 N1 0.0478(9) 0.0584(10) 0.0403(8) 0.000 0.0001(6) 0.000 C1 0.0413(11) 0.1011(18) 0.0465(11) 0.000 -0.0057(8) 0.000 C2 0.0439(11) 0.1140(19) 0.0386(9) 0.000 -0.0091(8) 0.000 C3 0.0428(11) 0.0686(13) 0.0390(9) 0.000 -0.0049(7) 0.000 C4 0.0395(10) 0.0659(12) 0.0430(10) 0.000 -0.0090(7) 0.000 C5 0.0525(11) 0.0653(13) 0.0389(9) 0.000 -0.0099(8) 0.000 C6 0.0432(11) 0.1000(17) 0.0413(10) 0.000 -0.0028(8) 0.000 C7 0.0436(10) 0.0703(13) 0.0398(9) 0.000 -0.0022(8) 0.000 C8 0.0458(11) 0.0973(17) 0.0397(9) 0.000 -0.0023(8) 0.000 C9 0.0375(9) 0.0756(13) 0.0384(9) 0.000 0.0031(7) 0.000 C10 0.0543(8) 0.0621(9) 0.0438(7) 0.0061(6) 0.0026(6) 0.0061(6) C11 0.0522(8) 0.0553(8) 0.0446(7) -0.0016(6) 0.0017(6) 0.0023(6) N2 0.0367(8) 0.0599(9) 0.0355(7) 0.000 0.0045(6) 0.000 O2 0.0534(8) 0.0717(10) 0.0339(6) 0.000 -0.0021(5) 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 O1 N1 1.315(2) . ? N1 C1 1.351(2) . ? N1 C5 1.355(3) . ? C1 C2 1.369(3) . ? C2 C3 1.389(3) . ? C3 C4 1.389(2) . ? C3 C6 1.506(3) . ? C4 C5 1.375(3) . ? C6 C7 1.517(2) . ? C7 C8 1.527(3) . ? C8 C9 1.512(2) . ? C9 C10 1.3873(18) 7_565 ? C9 C10 1.3873(18) . ? C10 C11 1.3798(18) . ? C11 N2 1.3524(16) . ? N2 O2 1.3210(18) . ? N2 C11 1.3524(16) 7_565 ? 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 N1 C1 120.63(16) . . ? O1 N1 C5 120.47(15) . . ? C1 N1 C5 118.90(16) . . ? N1 C1 C2 121.24(19) . . ? C1 C2 C3 121.70(18) . . ? C2 C3 C4 115.61(18) . . ? C2 C3 C6 124.40(17) . . ? C4 C3 C6 119.99(17) . . ? C5 C4 C3 121.83(18) . . ? N1 C5 C4 120.71(16) . . ? C3 C6 C7 117.65(17) . . ? C6 C7 C8 110.20(16) . . ? C9 C8 C7 113.24(16) . . ? C10 C9 C10 116.89(17) 7_565 . ? C10 C9 C8 121.55(8) 7_565 . ? C10 C9 C8 121.55(8) . . ? C11 C10 C9 121.06(13) . . ? N2 C11 C10 120.55(13) . . ? O2 N2 C11 120.07(8) . 7_565 ? O2 N2 C11 120.07(8) . . ? C11 N2 C11 119.87(16) 7_565 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.190 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.052 #=============================================END data_compd1 _database_code_CSD 214074 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 Co N4 O3 S2' _chemical_formula_weight 423.37 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' Co Co 0.3494 0.9721 '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 12.510(7) _cell_length_b 12.446(7) _cell_length_c 13.185(8) _cell_angle_alpha 90.00 _cell_angle_beta 114.400(10) _cell_angle_gamma 90.00 _cell_volume 1869.5(19) _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 block _exptl_crystal_colour 'dark purple' _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 1.162 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.7135 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12512 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.21 _reflns_number_total 4556 _reflns_number_gt 3202 _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^)+(0.0592P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4556 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 Co1 Co 0.01670(3) 0.91911(2) 0.60849(3) 0.03228(11) Uani 1 1 d . . . O1W O 0.03561(16) 1.07328(13) 0.69237(14) 0.0431(4) Uani 1 1 d . . . H1WA H 0.1084 1.0968 0.7501 0.065 Uiso 1 1 d R . . H1WB H 0.0237 1.1216 0.6319 0.065 Uiso 1 1 d R . . S1 S -0.28099(7) 0.70704(6) 0.63522(7) 0.0578(2) Uani 1 1 d . . . C14 C -0.1799(2) 0.7948(2) 0.6483(2) 0.0386(6) Uani 1 1 d . . . N3 N -0.10600(19) 0.85628(17) 0.65857(18) 0.0436(5) Uani 1 1 d . . . S2 S 0.38519(8) 0.79648(9) 0.88101(8) 0.0846(3) Uani 1 1 d . . . C15 C 0.2574(2) 0.8332(2) 0.7903(2) 0.0412(6) Uani 1 1 d . . . N4 N 0.1659(2) 0.86025(18) 0.72796(18) 0.0451(5) Uani 1 1 d . . . O1 O -0.01097(16) 0.79520(13) 0.48882(14) 0.0404(4) Uani 1 1 d . . . O2 O 0.89157(14) 0.49676(13) 0.97660(13) 0.0373(4) Uani 1 1 d . . . N1 N 0.04738(17) 0.70183(15) 0.51950(15) 0.0331(4) Uani 1 1 d . . . N2 N 0.77371(16) 0.49966(15) 0.94011(15) 0.0325(4) Uani 1 1 d . . . C1 C 0.1018(2) 0.6614(2) 0.4584(2) 0.0391(6) Uani 1 1 d . . . H1A H 0.0980 0.6976 0.3953 0.047 Uiso 1 1 calc R . . C2 C 0.1627(2) 0.5670(2) 0.4895(2) 0.0402(6) Uani 1 1 d . . . H2A H 0.2008 0.5397 0.4476 0.048 Uiso 1 1 calc R . . C3 C 0.1682(2) 0.51135(18) 0.58299(19) 0.0330(5) Uani 1 1 d . . . C4 C 0.1094(2) 0.55471(19) 0.6421(2) 0.0351(5) Uani 1 1 d . . . H4A H 0.1104 0.5189 0.7044 0.042 Uiso 1 1 calc R . . C5 C 0.0495(2) 0.64982(19) 0.60977(19) 0.0353(5) Uani 1 1 d . . . H5A H 0.0105 0.6784 0.6502 0.042 Uiso 1 1 calc R . . C6 C 0.2365(2) 0.40922(19) 0.6183(2) 0.0409(6) Uani 1 1 d . . . H6A H 0.2228 0.3660 0.5528 0.049 Uiso 1 1 calc R . . H6B H 0.2085 0.3690 0.6655 0.049 Uiso 1 1 calc R . . C7 C 0.3682(2) 0.4287(2) 0.6813(2) 0.0478(7) Uani 1 1 d . . . H7A H 0.4083 0.3600 0.6962 0.057 Uiso 1 1 calc R . . H7B H 0.3956 0.4698 0.6342 0.057 Uiso 1 1 calc R . . C8 C 0.4014(2) 0.4883(2) 0.7912(2) 0.0473(7) Uani 1 1 d . . . H8A H 0.3674 0.5597 0.7769 0.057 Uiso 1 1 calc R . . H8B H 0.3704 0.4503 0.8374 0.057 Uiso 1 1 calc R . . C9 C 0.5324(2) 0.4963(2) 0.8508(2) 0.0413(6) Uani 1 1 d . . . C10 C 0.5938(2) 0.5837(2) 0.8386(3) 0.0532(7) Uani 1 1 d . . . H10A H 0.5528 0.6433 0.7988 0.064 Uiso 1 1 calc R . . C11 C 0.7148(2) 0.5845(2) 0.8842(2) 0.0456(6) Uani 1 1 d . . . H11A H 0.7548 0.6443 0.8757 0.055 Uiso 1 1 calc R . . C12 C 0.5987(2) 0.4132(2) 0.9147(3) 0.0528(7) Uani 1 1 d . . . H12A H 0.5613 0.3540 0.9284 0.063 Uiso 1 1 calc R . . C13 C 0.7186(2) 0.4161(2) 0.9584(2) 0.0492(7) Uani 1 1 d . . . H13B H 0.7617 0.3590 1.0013 0.059 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 Co1 0.03084(18) 0.03237(19) 0.03345(18) 0.00285(13) 0.01311(13) 0.00086(13) O1W 0.0504(11) 0.0397(10) 0.0402(9) -0.0035(8) 0.0199(8) -0.0038(8) S1 0.0528(5) 0.0571(5) 0.0648(5) -0.0052(4) 0.0258(4) -0.0160(3) C14 0.0452(15) 0.0391(14) 0.0370(13) 0.0017(11) 0.0224(12) 0.0078(11) N3 0.0457(13) 0.0429(13) 0.0492(13) 0.0028(10) 0.0268(11) -0.0029(10) S2 0.0486(5) 0.1167(9) 0.0768(6) 0.0395(6) 0.0142(5) 0.0241(5) C15 0.0455(15) 0.0420(14) 0.0392(14) 0.0084(11) 0.0206(12) 0.0007(12) N4 0.0437(13) 0.0485(14) 0.0385(12) 0.0067(10) 0.0122(10) 0.0048(10) O1 0.0516(11) 0.0276(9) 0.0386(9) 0.0041(7) 0.0154(8) 0.0073(7) O2 0.0234(8) 0.0447(10) 0.0419(9) -0.0094(8) 0.0116(7) -0.0005(7) N1 0.0367(11) 0.0272(10) 0.0333(10) 0.0008(8) 0.0123(9) -0.0006(8) N2 0.0255(10) 0.0352(11) 0.0360(10) -0.0019(8) 0.0117(8) -0.0001(8) C1 0.0508(15) 0.0347(13) 0.0364(13) 0.0000(10) 0.0227(12) -0.0028(11) C2 0.0451(15) 0.0401(14) 0.0407(13) -0.0031(11) 0.0231(12) 0.0020(11) C3 0.0286(12) 0.0317(12) 0.0350(12) -0.0055(9) 0.0096(10) -0.0037(9) C4 0.0365(13) 0.0339(13) 0.0359(13) 0.0052(10) 0.0161(11) 0.0003(10) C5 0.0389(13) 0.0336(13) 0.0371(13) 0.0033(10) 0.0193(11) 0.0016(10) C6 0.0402(14) 0.0358(13) 0.0424(14) -0.0035(11) 0.0128(11) 0.0050(11) C7 0.0363(14) 0.0488(16) 0.0566(17) -0.0040(13) 0.0176(13) 0.0102(12) C8 0.0273(13) 0.0566(17) 0.0536(16) -0.0099(13) 0.0121(12) -0.0009(11) C9 0.0312(13) 0.0433(15) 0.0485(14) -0.0056(12) 0.0154(11) -0.0010(10) C10 0.0383(15) 0.0420(15) 0.0716(19) 0.0166(14) 0.0150(14) 0.0081(12) C11 0.0334(13) 0.0352(14) 0.0648(17) 0.0101(12) 0.0170(13) -0.0007(11) C12 0.0379(15) 0.0456(16) 0.072(2) 0.0179(14) 0.0203(14) -0.0056(12) C13 0.0395(15) 0.0435(15) 0.0599(17) 0.0192(13) 0.0159(13) 0.0016(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 Co1 N4 2.018(2) . ? Co1 N3 2.059(2) . ? Co1 O2 2.0789(17) 4_475 ? Co1 O1 2.1299(19) . ? Co1 O2 2.1385(17) 2_656 ? Co1 O1W 2.178(2) . ? S1 C14 1.625(3) . ? C14 N3 1.164(3) . ? S2 C15 1.617(3) . ? C15 N4 1.150(3) . ? O1 N1 1.343(3) . ? O2 N2 1.349(2) . ? O2 Co1 2.0789(17) 4_676 ? O2 Co1 2.1385(17) 2_646 ? N1 C5 1.345(3) . ? N1 C1 1.349(3) . ? N2 C11 1.324(3) . ? N2 C13 1.324(3) . ? C1 C2 1.367(3) . ? C2 C3 1.391(3) . ? C3 C4 1.384(3) . ? C3 C6 1.495(3) . ? C4 C5 1.371(3) . ? C6 C7 1.526(4) . ? C7 C8 1.524(4) . ? C8 C9 1.500(3) . ? C9 C12 1.375(4) . ? C9 C10 1.379(4) . ? C10 C11 1.378(4) . ? C12 C13 1.367(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 N4 Co1 N3 100.57(10) . . ? N4 Co1 O2 165.89(8) . 4_475 ? N3 Co1 O2 93.21(9) . 4_475 ? N4 Co1 O1 97.49(8) . . ? N3 Co1 O1 92.75(8) . . ? O2 Co1 O1 84.79(8) 4_475 . ? N4 Co1 O2 92.86(9) . 2_656 ? N3 Co1 O2 166.50(7) . 2_656 ? O2 Co1 O2 73.46(8) 4_475 2_656 ? O1 Co1 O2 84.08(7) . 2_656 ? N4 Co1 O1W 92.98(9) . . ? N3 Co1 O1W 96.36(8) . . ? O2 Co1 O1W 82.38(8) 4_475 . ? O1 Co1 O1W 164.64(6) . . ? O2 Co1 O1W 84.21(7) 2_656 . ? N3 C14 S1 178.8(3) . . ? C14 N3 Co1 150.9(2) . . ? N4 C15 S2 178.3(3) . . ? C15 N4 Co1 172.3(2) . . ? N1 O1 Co1 120.11(13) . . ? N2 O2 Co1 128.25(13) . 4_676 ? N2 O2 Co1 124.69(13) . 2_646 ? Co1 O2 Co1 106.54(8) 4_676 2_646 ? O1 N1 C5 119.52(19) . . ? O1 N1 C1 119.29(19) . . ? C5 N1 C1 121.2(2) . . ? C11 N2 C13 121.0(2) . . ? C11 N2 O2 119.68(19) . . ? C13 N2 O2 119.27(19) . . ? N1 C1 C2 119.9(2) . . ? C1 C2 C3 120.7(2) . . ? C4 C3 C2 117.5(2) . . ? C4 C3 C6 121.7(2) . . ? C2 C3 C6 120.8(2) . . ? C5 C4 C3 120.7(2) . . ? N1 C5 C4 120.0(2) . . ? C3 C6 C7 112.6(2) . . ? C8 C7 C6 113.8(2) . . ? C9 C8 C7 109.9(2) . . ? C12 C9 C10 116.1(2) . . ? C12 C9 C8 121.6(2) . . ? C10 C9 C8 122.1(2) . . ? C11 C10 C9 121.2(2) . . ? N2 C11 C10 119.8(2) . . ? C13 C12 C9 121.2(2) . . ? N2 C13 C12 120.5(2) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.642 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.073 #=============================================END data_compd2 _database_code_CSD 214075 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 Cd N4 O3 S2' _chemical_formula_weight 476.84 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' Cd Cd -0.8075 1.2024 '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 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 15.3748(15) _cell_length_b 14.9260(15) _cell_length_c 8.1696(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.079(2) _cell_angle_gamma 90.00 _cell_volume 1874.5(3) _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 block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.409 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.7250 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12357 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 28.01 _reflns_number_total 4514 _reflns_number_gt 3785 _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^)+(0.0561P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0005(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4514 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0877 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 Cd1 Cd -0.080164(11) 0.521147(13) 0.17408(2) 0.03500(9) Uani 1 1 d . . . S1 S 0.02834(6) 0.63951(5) 0.70685(10) 0.0589(2) Uani 1 1 d . . . O1 O 0.06079(11) 0.54105(14) 0.0836(2) 0.0424(4) Uani 1 1 d . . . O2 O 0.80442(13) 0.78714(14) 0.2710(3) 0.0545(5) Uani 1 1 d . . . N1 N 0.12468(12) 0.56843(14) 0.1865(2) 0.0325(4) Uani 1 1 d . . . N2 N 0.72849(13) 0.76292(16) 0.3315(3) 0.0418(5) Uani 1 1 d . . . C1 C 0.13750(18) 0.65628(19) 0.2051(4) 0.0456(6) Uani 1 1 d . . . H1A H 0.1030 0.6969 0.1470 0.055 Uiso 1 1 calc R . . C2 C 0.20227(19) 0.6866(2) 0.3109(4) 0.0531(7) Uani 1 1 d . . . H2A H 0.2113 0.7479 0.3234 0.064 Uiso 1 1 calc R . . C3 C 0.25339(17) 0.6271(2) 0.3978(3) 0.0499(7) Uani 1 1 d . . . C4 C 0.23658(19) 0.5368(2) 0.3749(4) 0.0533(8) Uani 1 1 d . . . H4A H 0.2698 0.4949 0.4324 0.064 Uiso 1 1 calc R . . C5 C 0.17206(19) 0.5078(2) 0.2691(4) 0.0447(6) Uani 1 1 d . . . H5A H 0.1615 0.4469 0.2552 0.054 Uiso 1 1 calc R . . C6 C 0.32644(19) 0.6575(3) 0.5105(4) 0.0745(12) Uani 1 1 d . . . H6A H 0.3336 0.6144 0.5986 0.089 Uiso 1 1 calc R . . H6B H 0.3108 0.7146 0.5588 0.089 Uiso 1 1 calc R . . C7 C 0.41228(17) 0.6678(3) 0.4240(4) 0.0537(8) Uani 1 1 d . . . H7A H 0.4072 0.7150 0.3429 0.064 Uiso 1 1 calc R . . H7B H 0.4258 0.6125 0.3675 0.064 Uiso 1 1 calc R . . C8 C 0.48567(18) 0.6901(3) 0.5444(4) 0.0738(12) Uani 1 1 d . . . H8A H 0.4674 0.7394 0.6129 0.089 Uiso 1 1 calc R . . H8B H 0.4958 0.6387 0.6150 0.089 Uiso 1 1 calc R . . C9 C 0.57043(17) 0.7151(3) 0.4651(4) 0.0525(8) Uani 1 1 d . . . C10 C 0.59706(19) 0.8029(3) 0.4562(4) 0.0607(9) Uani 1 1 d . . . H10A H 0.5616 0.8477 0.4973 0.073 Uiso 1 1 calc R . . C11 C 0.67445(19) 0.8256(2) 0.3883(4) 0.0568(8) Uani 1 1 d . . . H11A H 0.6900 0.8857 0.3813 0.068 Uiso 1 1 calc R . . C12 C 0.7045(2) 0.6769(2) 0.3355(4) 0.0585(8) Uani 1 1 d . . . H12A H 0.7411 0.6330 0.2942 0.070 Uiso 1 1 calc R . . C13 C 0.6256(2) 0.6529(2) 0.4010(5) 0.0640(9) Uani 1 1 d . . . H13A H 0.6095 0.5928 0.4014 0.077 Uiso 1 1 calc R . . O1W O -0.11153(16) 0.66277(16) 0.0718(3) 0.0539(6) Uani 1 1 d . . . H1WA H -0.117(2) 0.679(2) -0.028(5) 0.056(10) Uiso 1 1 d . . . H1WB H -0.136(2) 0.693(3) 0.122(5) 0.058(12) Uiso 1 1 d . . . C14 C -0.01773(19) 0.61183(17) 0.5315(3) 0.0406(6) Uani 1 1 d . . . C15 C -0.28843(19) 0.4641(2) 0.1059(4) 0.0468(7) Uani 1 1 d . . . N4 N -0.22077(17) 0.4825(2) 0.1543(4) 0.0590(7) Uani 1 1 d . . . S2 S -0.38639(7) 0.44188(10) 0.04237(17) 0.0993(4) Uani 1 1 d . . . N3 N -0.05259(18) 0.59280(17) 0.4112(3) 0.0533(6) 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 Cd1 0.02616(11) 0.04545(14) 0.03331(12) -0.00459(7) -0.00154(7) -0.00009(7) S1 0.0838(6) 0.0398(4) 0.0520(5) -0.0014(3) -0.0252(4) -0.0073(4) O1 0.0241(8) 0.0631(12) 0.0399(10) -0.0159(9) -0.0044(7) -0.0051(8) O2 0.0402(10) 0.0572(12) 0.0667(14) -0.0069(11) 0.0151(9) -0.0059(10) N1 0.0232(9) 0.0415(11) 0.0328(10) -0.0070(9) -0.0017(7) -0.0024(9) N2 0.0321(11) 0.0467(13) 0.0465(13) -0.0062(10) 0.0003(9) -0.0013(10) C1 0.0441(15) 0.0383(14) 0.0540(17) -0.0042(12) -0.0076(12) 0.0035(12) C2 0.0500(16) 0.0493(16) 0.0598(19) -0.0144(14) -0.0006(14) -0.0115(14) C3 0.0310(13) 0.085(2) 0.0335(14) -0.0059(14) 0.0002(10) -0.0174(14) C4 0.0362(15) 0.069(2) 0.0545(19) 0.0168(15) -0.0139(13) -0.0016(14) C5 0.0372(15) 0.0414(14) 0.0553(18) 0.0039(12) -0.0033(12) -0.0001(11) C6 0.0384(16) 0.143(4) 0.0415(17) -0.017(2) -0.0020(13) -0.035(2) C7 0.0336(13) 0.089(2) 0.0389(15) -0.0066(15) -0.0044(11) -0.0151(15) C8 0.0344(15) 0.143(4) 0.0437(17) -0.004(2) -0.0042(12) -0.0266(19) C9 0.0293(13) 0.089(2) 0.0393(15) -0.0026(15) -0.0068(11) -0.0074(14) C10 0.0344(14) 0.075(2) 0.072(2) -0.0232(18) 0.0016(14) 0.0061(15) C11 0.0449(16) 0.0505(17) 0.075(2) -0.0161(16) 0.0036(15) 0.0008(14) C12 0.0456(16) 0.0465(16) 0.084(3) -0.0072(16) 0.0112(15) 0.0021(14) C13 0.0532(19) 0.0575(19) 0.082(3) 0.0033(17) 0.0056(17) -0.0131(16) O1W 0.0711(15) 0.0517(13) 0.0390(12) 0.0008(10) 0.0049(11) 0.0185(11) C14 0.0496(15) 0.0332(12) 0.0391(14) 0.0014(11) 0.0028(11) 0.0029(12) C15 0.0370(15) 0.0503(16) 0.0531(17) 0.0044(13) 0.0025(12) -0.0084(12) N4 0.0346(14) 0.0737(19) 0.0687(19) -0.0009(14) 0.0035(12) -0.0073(12) S2 0.0556(6) 0.1219(10) 0.1190(10) 0.0315(8) -0.0354(6) -0.0388(6) N3 0.0705(17) 0.0515(14) 0.0374(13) -0.0042(11) -0.0114(12) 0.0078(13) _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 Cd1 N4 2.240(3) . ? Cd1 N3 2.246(2) . ? Cd1 O1W 2.320(2) . ? Cd1 O1 2.3220(18) . ? Cd1 O1 2.3250(18) 3_565 ? Cd1 S1 2.7022(8) 3_566 ? S1 C14 1.639(3) . ? S1 Cd1 2.7022(8) 3_566 ? O1 N1 1.345(2) . ? O1 Cd1 2.3250(18) 3_565 ? O2 N2 1.326(3) . ? N1 C1 1.334(3) . ? N1 C5 1.336(3) . ? N2 C12 1.337(4) . ? N2 C11 1.340(4) . ? C1 C2 1.383(4) . ? C2 C3 1.375(5) . ? C3 C4 1.384(5) . ? C3 C6 1.509(4) . ? C4 C5 1.373(4) . ? C6 C7 1.516(4) . ? C7 C8 1.520(4) . ? C8 C9 1.513(4) . ? C9 C13 1.369(5) . ? C9 C10 1.375(5) . ? C10 C11 1.365(4) . ? C12 C13 1.383(4) . ? C14 N3 1.146(3) . ? C15 N4 1.140(4) . ? C15 S2 1.618(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 N4 Cd1 N3 110.55(11) . . ? N4 Cd1 O1W 90.85(10) . . ? N3 Cd1 O1W 84.91(9) . . ? N4 Cd1 O1 156.21(9) . . ? N3 Cd1 O1 92.96(9) . . ? O1W Cd1 O1 87.58(8) . . ? N4 Cd1 O1 88.38(9) . 3_565 ? N3 Cd1 O1 161.03(9) . 3_565 ? O1W Cd1 O1 93.84(8) . 3_565 ? O1 Cd1 O1 68.07(7) . 3_565 ? N4 Cd1 S1 94.31(8) . 3_566 ? N3 Cd1 S1 93.58(7) . 3_566 ? O1W Cd1 S1 174.83(7) . 3_566 ? O1 Cd1 S1 87.56(6) . 3_566 ? O1 Cd1 S1 85.97(6) 3_565 3_566 ? C14 S1 Cd1 102.16(9) . 3_566 ? N1 O1 Cd1 120.99(14) . . ? N1 O1 Cd1 125.68(13) . 3_565 ? Cd1 O1 Cd1 111.93(7) . 3_565 ? C1 N1 C5 122.0(2) . . ? C1 N1 O1 118.3(2) . . ? C5 N1 O1 119.7(2) . . ? O2 N2 C12 121.0(2) . . ? O2 N2 C11 119.7(2) . . ? C12 N2 C11 119.3(2) . . ? N1 C1 C2 119.7(3) . . ? C3 C2 C1 120.6(3) . . ? C2 C3 C4 117.1(3) . . ? C2 C3 C6 122.2(3) . . ? C4 C3 C6 120.7(3) . . ? C5 C4 C3 121.5(3) . . ? N1 C5 C4 119.0(3) . . ? C3 C6 C7 113.0(2) . . ? C6 C7 C8 111.2(3) . . ? C9 C8 C7 114.3(3) . . ? C13 C9 C10 116.1(3) . . ? C13 C9 C8 122.7(3) . . ? C10 C9 C8 121.2(3) . . ? C11 C10 C9 121.4(3) . . ? N2 C11 C10 121.2(3) . . ? N2 C12 C13 120.2(3) . . ? C9 C13 C12 121.8(3) . . ? N3 C14 S1 177.7(3) . . ? N4 C15 S2 177.2(3) . . ? C15 N4 Cd1 163.8(3) . . ? C14 N3 Cd1 159.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Cd1 O1 N1 -175.7(2) . . . . ? N3 Cd1 O1 N1 12.91(19) . . . . ? O1W Cd1 O1 N1 97.68(19) . . . . ? O1 Cd1 O1 N1 -167.2(2) 3_565 . . . ? S1 Cd1 O1 N1 -80.56(18) 3_566 . . . ? N4 Cd1 O1 Cd1 -8.5(3) . . . 3_565 ? N3 Cd1 O1 Cd1 -179.90(10) . . . 3_565 ? O1W Cd1 O1 Cd1 -95.12(10) . . . 3_565 ? O1 Cd1 O1 Cd1 0.0 3_565 . . 3_565 ? S1 Cd1 O1 Cd1 86.63(8) 3_566 . . 3_565 ? Cd1 O1 N1 C1 -88.7(3) . . . . ? Cd1 O1 N1 C1 106.0(2) 3_565 . . . ? Cd1 O1 N1 C5 90.1(2) . . . . ? Cd1 O1 N1 C5 -75.2(3) 3_565 . . . ? C5 N1 C1 C2 0.8(4) . . . . ? O1 N1 C1 C2 179.5(2) . . . . ? N1 C1 C2 C3 -0.3(5) . . . . ? C1 C2 C3 C4 -0.4(5) . . . . ? C1 C2 C3 C6 178.1(3) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C6 C3 C4 C5 -178.1(3) . . . . ? C1 N1 C5 C4 -0.8(4) . . . . ? O1 N1 C5 C4 -179.4(3) . . . . ? C3 C4 C5 N1 0.1(5) . . . . ? C2 C3 C6 C7 -88.6(4) . . . . ? C4 C3 C6 C7 89.8(4) . . . . ? C3 C6 C7 C8 -174.8(4) . . . . ? C6 C7 C8 C9 -171.1(4) . . . . ? C7 C8 C9 C13 -77.8(5) . . . . ? C7 C8 C9 C10 103.3(4) . . . . ? C13 C9 C10 C11 -0.5(5) . . . . ? C8 C9 C10 C11 178.4(3) . . . . ? O2 N2 C11 C10 -177.8(3) . . . . ? C12 N2 C11 C10 2.7(5) . . . . ? C9 C10 C11 N2 -1.7(5) . . . . ? O2 N2 C12 C13 179.2(3) . . . . ? C11 N2 C12 C13 -1.4(5) . . . . ? C10 C9 C13 C12 1.8(5) . . . . ? C8 C9 C13 C12 -177.1(3) . . . . ? N2 C12 C13 C9 -0.9(6) . . . . ? Cd1 S1 C14 N3 102(7) 3_566 . . . ? S2 C15 N4 Cd1 -125(6) . . . . ? N3 Cd1 N4 C15 153.4(10) . . . . ? O1W Cd1 N4 C15 68.5(10) . . . . ? O1 Cd1 N4 C15 -17.4(11) . . . . ? O1 Cd1 N4 C15 -25.3(10) 3_565 . . . ? S1 Cd1 N4 C15 -111.1(10) 3_566 . . . ? S1 C14 N3 Cd1 -141(6) . . . . ? N4 Cd1 N3 C14 134.4(7) . . . . ? O1W Cd1 N3 C14 -136.6(7) . . . . ? O1 Cd1 N3 C14 -49.3(7) . . . . ? O1 Cd1 N3 C14 -49.6(8) 3_565 . . . ? S1 Cd1 N3 C14 38.5(7) 3_566 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O2 0.86(4) 2.08(4) 2.854(3) 150(3) 4_475 O1W H1WB O2 0.72(4) 2.08(4) 2.801(3) 174(4) 1_455 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.849 _refine_diff_density_min -0.712 _refine_diff_density_rms 0.109 #=============================================END data_compd3 _database_code_CSD 214076 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 Mn N4 O3 S2' _chemical_formula_weight 419.38 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' Mn Mn 0.3368 0.7283 '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 12.544(3) _cell_length_b 12.644(3) _cell_length_c 13.219(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.18(3) _cell_angle_gamma 90.00 _cell_volume 1912.5(7) _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 block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 0.929 _exptl_absorpt_correction_type PSI-SCAN _exptl_absorpt_correction_T_min 0.7990 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3523 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0779 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3361 _reflns_number_gt 2204 _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^)+(0.0441P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3361 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0947 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1260 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 Mn1 Mn 0.01758(5) 0.91768(5) 0.61397(5) 0.03715(18) Uani 1 1 d . . . O1W O 0.0402(3) 1.0796(3) 0.6954(3) 0.0490(8) Uani 1 1 d . . . H1WA H 0.091(4) 1.102(4) 0.742(4) 0.055(17) Uiso 1 1 d . . . H1WB H 0.033(5) 1.124(5) 0.644(5) 0.11(2) Uiso 1 1 d . . . S1 S -0.28694(11) 0.70567(10) 0.63345(11) 0.0654(4) Uani 1 1 d . . . C14 C -0.1852(4) 0.7930(3) 0.6506(3) 0.0431(10) Uani 1 1 d . . . N3 N -0.1122(3) 0.8544(3) 0.6633(3) 0.0528(9) Uani 1 1 d . . . S2 S 0.39104(12) 0.79479(15) 0.88526(13) 0.0955(6) Uani 1 1 d . . . C15 C 0.2646(4) 0.8310(3) 0.7955(3) 0.0469(10) Uani 1 1 d . . . N4 N 0.1738(3) 0.8583(3) 0.7340(3) 0.0567(10) Uani 1 1 d . . . O1 O -0.0106(2) 0.7916(2) 0.4878(2) 0.0466(7) Uani 1 1 d . . . O2 O 0.8890(2) 0.4967(2) 0.9783(2) 0.0421(6) Uani 1 1 d . . . N1 N 0.0471(3) 0.6995(2) 0.5180(2) 0.0384(8) Uani 1 1 d . . . N2 N 0.7715(3) 0.4996(2) 0.9405(2) 0.0380(7) Uani 1 1 d . . . C1 C 0.1037(4) 0.6604(3) 0.4590(3) 0.0437(10) Uani 1 1 d . . . H1A H 0.1014 0.6964 0.3967 0.052 Uiso 1 1 calc R . . C2 C 0.1645(4) 0.5680(3) 0.4906(3) 0.0468(10) Uani 1 1 d . . . H2A H 0.2041 0.5423 0.4497 0.056 Uiso 1 1 calc R . . C3 C 0.1688(3) 0.5112(3) 0.5820(3) 0.0385(9) Uani 1 1 d . . . C4 C 0.1083(3) 0.5538(3) 0.6391(3) 0.0403(9) Uani 1 1 d . . . H4A H 0.1082 0.5185 0.7008 0.048 Uiso 1 1 calc R . . C5 C 0.0482(3) 0.6473(3) 0.6067(3) 0.0406(9) Uani 1 1 d . . . H5A H 0.0080 0.6745 0.6464 0.049 Uiso 1 1 calc R . . C6 C 0.2372(3) 0.4102(3) 0.6174(3) 0.0457(10) Uani 1 1 d . . . H6A H 0.2243 0.3678 0.5523 0.055 Uiso 1 1 calc R . . H6B H 0.2088 0.3705 0.6641 0.055 Uiso 1 1 calc R . . C7 C 0.3685(3) 0.4300(4) 0.6809(4) 0.0528(11) Uani 1 1 d . . . H7A H 0.4088 0.3626 0.6955 0.063 Uiso 1 1 calc R . . H7B H 0.3960 0.4710 0.6344 0.063 Uiso 1 1 calc R . . C8 C 0.4005(3) 0.4880(4) 0.7903(4) 0.0520(11) Uani 1 1 d . . . H8A H 0.3662 0.5581 0.7764 0.062 Uiso 1 1 calc R . . H8B H 0.3695 0.4499 0.8360 0.062 Uiso 1 1 calc R . . C9 C 0.5314(3) 0.4966(3) 0.8502(3) 0.0454(10) Uani 1 1 d . . . C10 C 0.5921(4) 0.5823(3) 0.8389(4) 0.0564(12) Uani 1 1 d . . . H10A H 0.5516 0.6411 0.7997 0.068 Uiso 1 1 calc R . . C11 C 0.7131(4) 0.5828(3) 0.8849(4) 0.0525(11) Uani 1 1 d . . . H11A H 0.7532 0.6417 0.8766 0.063 Uiso 1 1 calc R . . C12 C 0.5955(4) 0.4142(4) 0.9131(4) 0.0584(12) Uani 1 1 d . . . H12A H 0.5574 0.3560 0.9258 0.070 Uiso 1 1 calc R . . C13 C 0.7153(4) 0.4168(3) 0.9575(4) 0.0531(11) Uani 1 1 d . . . H13B H 0.7577 0.3602 0.9999 0.064 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 Mn1 0.0345(3) 0.0393(3) 0.0380(3) 0.0025(3) 0.0152(3) 0.0003(3) O1W 0.059(2) 0.0460(18) 0.0440(18) -0.0045(17) 0.0236(17) -0.0060(17) S1 0.0557(8) 0.0685(8) 0.0713(9) -0.0049(6) 0.0254(7) -0.0174(6) C14 0.046(2) 0.046(2) 0.041(2) 0.0047(19) 0.022(2) 0.007(2) N3 0.055(2) 0.053(2) 0.059(2) 0.0000(19) 0.0334(19) -0.005(2) S2 0.0530(9) 0.1337(15) 0.0889(11) 0.0487(10) 0.0181(8) 0.0270(9) C15 0.047(3) 0.054(3) 0.045(2) 0.010(2) 0.026(2) 0.003(2) N4 0.050(2) 0.068(3) 0.045(2) 0.0074(19) 0.0127(19) 0.007(2) O1 0.0569(18) 0.0353(15) 0.0443(16) 0.0050(12) 0.0174(14) 0.0098(13) O2 0.0235(14) 0.0513(16) 0.0488(16) -0.0110(13) 0.0121(12) -0.0026(12) N1 0.0413(19) 0.0374(18) 0.0360(18) -0.0040(14) 0.0152(15) -0.0010(15) N2 0.0290(17) 0.0418(18) 0.0421(18) -0.0003(15) 0.0133(14) -0.0005(15) C1 0.055(3) 0.042(2) 0.040(2) 0.0044(18) 0.024(2) -0.001(2) C2 0.051(3) 0.048(3) 0.050(2) -0.007(2) 0.030(2) -0.003(2) C3 0.035(2) 0.037(2) 0.039(2) -0.0078(17) 0.0107(17) -0.0051(17) C4 0.042(2) 0.040(2) 0.040(2) 0.0044(17) 0.0168(19) 0.0006(18) C5 0.042(2) 0.041(2) 0.043(2) 0.0009(18) 0.0226(19) 0.0006(18) C6 0.041(2) 0.039(2) 0.051(2) -0.0047(19) 0.0126(19) 0.0012(19) C7 0.035(2) 0.062(3) 0.061(3) -0.006(2) 0.019(2) 0.009(2) C8 0.031(2) 0.066(3) 0.057(3) -0.008(2) 0.016(2) -0.003(2) C9 0.028(2) 0.052(3) 0.054(2) -0.005(2) 0.0146(18) -0.0002(19) C10 0.038(2) 0.049(3) 0.076(3) 0.016(2) 0.018(2) 0.008(2) C11 0.043(2) 0.040(2) 0.077(3) 0.014(2) 0.026(2) 0.001(2) C12 0.034(2) 0.059(3) 0.081(3) 0.018(2) 0.022(2) -0.004(2) C13 0.038(2) 0.048(2) 0.065(3) 0.019(2) 0.013(2) 0.001(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 Mn1 N4 2.091(4) . ? Mn1 N3 2.141(3) . ? Mn1 O2 2.150(3) 4_475 ? Mn1 O1 2.229(3) . ? Mn1 O2 2.243(3) 2_656 ? Mn1 O1W 2.276(3) . ? S1 C14 1.631(5) . ? C14 N3 1.159(5) . ? S2 C15 1.610(5) . ? C15 N4 1.148(5) . ? O1 N1 1.342(4) . ? O2 N2 1.349(4) . ? O2 Mn1 2.150(3) 4_676 ? O2 Mn1 2.243(3) 2_646 ? N1 C5 1.341(5) . ? N1 C1 1.346(5) . ? N2 C11 1.320(5) . ? N2 C13 1.331(5) . ? C1 C2 1.364(5) . ? C2 C3 1.388(5) . ? C3 C4 1.381(5) . ? C3 C6 1.501(5) . ? C4 C5 1.372(5) . ? C6 C7 1.532(5) . ? C7 C8 1.521(6) . ? C8 C9 1.507(5) . ? C9 C10 1.368(6) . ? C9 C12 1.369(6) . ? C10 C11 1.385(5) . ? C12 C13 1.372(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 N4 Mn1 N3 103.17(14) . . ? N4 Mn1 O2 164.48(12) . 4_475 ? N3 Mn1 O2 92.16(12) . 4_475 ? N4 Mn1 O1 97.06(12) . . ? N3 Mn1 O1 93.04(12) . . ? O2 Mn1 O1 84.34(10) 4_475 . ? N4 Mn1 O2 92.09(12) . 2_656 ? N3 Mn1 O2 164.54(12) . 2_656 ? O2 Mn1 O2 72.71(10) 4_475 2_656 ? O1 Mn1 O2 82.52(10) . 2_656 ? N4 Mn1 O1W 93.89(15) . . ? N3 Mn1 O1W 98.92(13) . . ? O2 Mn1 O1W 81.19(13) 4_475 . ? O1 Mn1 O1W 161.51(11) . . ? O2 Mn1 O1W 82.24(11) 2_656 . ? N3 C14 S1 179.5(4) . . ? C14 N3 Mn1 149.3(3) . . ? N4 C15 S2 178.0(4) . . ? C15 N4 Mn1 173.9(4) . . ? N1 O1 Mn1 119.8(2) . . ? N2 O2 Mn1 128.9(2) . 4_676 ? N2 O2 Mn1 123.1(2) . 2_646 ? Mn1 O2 Mn1 107.29(10) 4_676 2_646 ? C5 N1 O1 119.9(3) . . ? C5 N1 C1 120.5(3) . . ? O1 N1 C1 119.6(3) . . ? C11 N2 C13 120.6(3) . . ? C11 N2 O2 120.0(3) . . ? C13 N2 O2 119.3(3) . . ? N1 C1 C2 119.9(4) . . ? C1 C2 C3 121.9(4) . . ? C4 C3 C2 116.1(4) . . ? C4 C3 C6 122.2(4) . . ? C2 C3 C6 121.7(4) . . ? C5 C4 C3 121.3(4) . . ? N1 C5 C4 120.4(3) . . ? C3 C6 C7 112.4(3) . . ? C8 C7 C6 113.9(3) . . ? C9 C8 C7 110.0(3) . . ? C10 C9 C12 117.0(4) . . ? C10 C9 C8 122.4(4) . . ? C12 C9 C8 120.4(4) . . ? C9 C10 C11 121.0(4) . . ? N2 C11 C10 119.9(4) . . ? C9 C12 C13 120.6(4) . . ? N2 C13 C12 120.6(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.336 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.068 #=============================================END data_compd4 _database_code_CSD 214077 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 N4 O3 S2 Zn' _chemical_formula_weight 429.81 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)/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 12.555(3) _cell_length_b 12.529(3) _cell_length_c 13.159(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.779(5) _cell_angle_gamma 90.00 _cell_volume 1879.4(7) _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 block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 1.550 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.6407 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12649 _diffrn_reflns_av_R_equivalents 0.0663 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 28.08 _reflns_number_total 4535 _reflns_number_gt 2338 _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^)+(0.0484P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4535 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1147 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _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 0.01399(4) 0.91739(4) 0.61163(4) 0.03680(16) Uani 1 1 d . . . O1W O 0.0342(3) 1.0767(2) 0.6944(2) 0.0472(7) Uani 1 1 d . . . H1WA H 0.0915 1.0930 0.7341 0.071 Uiso 1 1 d R . . H1WB H 0.0185 1.1085 0.6321 0.071 Uiso 1 1 d R . . S1 S -0.28469(12) 0.70790(10) 0.63061(11) 0.0628(4) Uani 1 1 d . . . C14 C -0.1827(4) 0.7957(3) 0.6462(3) 0.0413(10) Uani 1 1 d . . . N3 N -0.1099(3) 0.8569(3) 0.6585(3) 0.0477(9) Uani 1 1 d . . . S2 S 0.38414(14) 0.79802(14) 0.87779(14) 0.0921(6) Uani 1 1 d . . . C15 C 0.2558(4) 0.8352(3) 0.7890(4) 0.0436(11) Uani 1 1 d . . . N4 N 0.1646(3) 0.8621(3) 0.7273(3) 0.0490(9) Uani 1 1 d . . . O1 O -0.0126(3) 0.79326(19) 0.4867(2) 0.0414(7) Uani 1 1 d . . . O2 O 0.8935(2) 0.4986(2) 0.9777(2) 0.0365(6) Uani 1 1 d . . . N1 N 0.0467(3) 0.7010(2) 0.5187(3) 0.0342(8) Uani 1 1 d . . . N2 N 0.7767(3) 0.5011(2) 0.9411(2) 0.0317(7) Uani 1 1 d . . . C1 C 0.1024(4) 0.6612(3) 0.4593(3) 0.0398(10) Uani 1 1 d . . . H1A H 0.1002 0.6978 0.3970 0.048 Uiso 1 1 calc R . . C2 C 0.1625(4) 0.5667(3) 0.4907(3) 0.0419(10) Uani 1 1 d . . . H2A H 0.1994 0.5395 0.4480 0.050 Uiso 1 1 calc R . . C3 C 0.1697(3) 0.5110(3) 0.5834(3) 0.0345(9) Uani 1 1 d . . . C4 C 0.1094(4) 0.5541(3) 0.6414(3) 0.0360(10) Uani 1 1 d . . . H4A H 0.1097 0.5182 0.7034 0.043 Uiso 1 1 calc R . . C5 C 0.0494(4) 0.6488(3) 0.6089(3) 0.0390(10) Uani 1 1 d . . . H5A H 0.0106 0.6768 0.6495 0.047 Uiso 1 1 calc R . . C6 C 0.2378(4) 0.4088(3) 0.6202(3) 0.0421(10) Uani 1 1 d . . . H6A H 0.2233 0.3649 0.5550 0.050 Uiso 1 1 calc R . . H6B H 0.2103 0.3700 0.6683 0.050 Uiso 1 1 calc R . . C7 C 0.3680(4) 0.4278(3) 0.6822(4) 0.0470(11) Uani 1 1 d . . . H7A H 0.3946 0.4677 0.6340 0.056 Uiso 1 1 calc R . . H7B H 0.4078 0.3594 0.6974 0.056 Uiso 1 1 calc R . . C8 C 0.4045(4) 0.4883(4) 0.7928(4) 0.0506(11) Uani 1 1 d . . . H8A H 0.3706 0.5593 0.7781 0.061 Uiso 1 1 calc R . . H8B H 0.3745 0.4514 0.8402 0.061 Uiso 1 1 calc R . . C9 C 0.5343(4) 0.4967(3) 0.8520(3) 0.0406(10) Uani 1 1 d . . . C10 C 0.5957(4) 0.5829(3) 0.8378(4) 0.0544(12) Uani 1 1 d . . . H10A H 0.5545 0.6416 0.7969 0.065 Uiso 1 1 calc R . . C11 C 0.7157(4) 0.5838(3) 0.8825(4) 0.0482(11) Uani 1 1 d . . . H11A H 0.7547 0.6428 0.8718 0.058 Uiso 1 1 calc R . . C12 C 0.6016(4) 0.4155(4) 0.9180(4) 0.0537(12) Uani 1 1 d . . . H12A H 0.5650 0.3573 0.9337 0.064 Uiso 1 1 calc R . . C13 C 0.7211(4) 0.4186(3) 0.9611(4) 0.0506(11) Uani 1 1 d . . . H13B H 0.7645 0.3622 1.0050 0.061 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 0.0377(3) 0.0399(3) 0.0326(3) 0.0046(2) 0.0145(2) 0.0023(2) O1W 0.059(2) 0.0494(17) 0.0355(16) -0.0011(14) 0.0218(16) -0.0003(14) S1 0.0616(9) 0.0649(8) 0.0648(9) -0.0079(7) 0.0292(8) -0.0180(6) C14 0.048(3) 0.045(3) 0.037(2) 0.006(2) 0.024(2) 0.013(2) N3 0.054(3) 0.047(2) 0.051(2) -0.0006(19) 0.031(2) -0.0055(19) S2 0.0536(10) 0.1298(15) 0.0815(11) 0.0432(10) 0.0171(9) 0.0248(9) C15 0.053(3) 0.046(3) 0.037(3) 0.010(2) 0.024(3) 0.000(2) N4 0.048(3) 0.056(2) 0.037(2) 0.0044(19) 0.012(2) 0.0026(19) O1 0.059(2) 0.0307(15) 0.0339(16) 0.0055(12) 0.0189(15) 0.0090(13) O2 0.0239(16) 0.0480(16) 0.0357(15) -0.0102(13) 0.0105(13) -0.0014(12) N1 0.041(2) 0.0291(18) 0.0305(18) -0.0006(14) 0.0131(17) -0.0002(14) N2 0.027(2) 0.0351(18) 0.0314(18) -0.0005(15) 0.0105(16) -0.0010(14) C1 0.058(3) 0.037(2) 0.031(2) 0.0021(18) 0.025(2) -0.005(2) C2 0.047(3) 0.046(3) 0.039(2) -0.007(2) 0.024(2) -0.002(2) C3 0.032(2) 0.036(2) 0.033(2) -0.0078(18) 0.011(2) -0.0039(17) C4 0.038(3) 0.037(2) 0.033(2) 0.0086(17) 0.015(2) -0.0013(17) C5 0.050(3) 0.039(2) 0.036(2) 0.0058(19) 0.026(2) 0.0024(19) C6 0.045(3) 0.037(2) 0.039(2) -0.0059(19) 0.012(2) 0.0048(19) C7 0.037(3) 0.054(3) 0.048(3) -0.002(2) 0.016(2) 0.008(2) C8 0.033(3) 0.062(3) 0.051(3) -0.004(2) 0.013(2) 0.001(2) C9 0.029(3) 0.048(3) 0.043(3) -0.005(2) 0.012(2) 0.0003(19) C10 0.035(3) 0.049(3) 0.068(3) 0.018(2) 0.011(2) 0.009(2) C11 0.038(3) 0.038(2) 0.066(3) 0.012(2) 0.019(2) 0.001(2) C12 0.043(3) 0.053(3) 0.064(3) 0.017(2) 0.021(3) -0.005(2) C13 0.040(3) 0.049(3) 0.054(3) 0.021(2) 0.011(2) 0.004(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 N4 1.989(4) . ? Zn1 N3 2.044(4) . ? Zn1 O2 2.066(3) 4_475 ? Zn1 O1 2.184(3) . ? Zn1 O2 2.217(2) 2_656 ? Zn1 O1W 2.237(3) . ? S1 C14 1.634(5) . ? C14 N3 1.151(5) . ? S2 C15 1.612(5) . ? C15 N4 1.143(5) . ? O1 N1 1.343(4) . ? O2 N2 1.338(4) . ? O2 Zn1 2.066(3) 4_676 ? O2 Zn1 2.217(2) 2_646 ? N1 C5 1.343(4) . ? N1 C1 1.344(4) . ? N2 C11 1.326(5) . ? N2 C13 1.334(5) . ? C1 C2 1.371(5) . ? C2 C3 1.375(5) . ? C3 C4 1.391(5) . ? C3 C6 1.503(5) . ? C4 C5 1.373(5) . ? C6 C7 1.509(6) . ? C7 C8 1.531(6) . ? C8 C9 1.487(5) . ? C9 C12 1.374(6) . ? C9 C10 1.385(6) . ? C10 C11 1.368(6) . ? C12 C13 1.363(6) . ? 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 N4 Zn1 N3 103.84(15) . . ? N4 Zn1 O2 162.07(12) . 4_475 ? N3 Zn1 O2 93.91(13) . 4_475 ? N4 Zn1 O1 97.14(13) . . ? N3 Zn1 O1 93.84(12) . . ? O2 Zn1 O1 83.95(10) 4_475 . ? N4 Zn1 O2 91.40(12) . 2_656 ? N3 Zn1 O2 164.71(13) . 2_656 ? O2 Zn1 O2 70.92(11) 4_475 2_656 ? O1 Zn1 O2 82.91(9) . 2_656 ? N4 Zn1 O1W 93.50(13) . . ? N3 Zn1 O1W 97.44(12) . . ? O2 Zn1 O1W 81.58(10) 4_475 . ? O1 Zn1 O1W 162.19(9) . . ? O2 Zn1 O1W 82.58(9) 2_656 . ? N3 C14 S1 179.1(5) . . ? C14 N3 Zn1 149.8(3) . . ? N4 C15 S2 179.1(4) . . ? C15 N4 Zn1 174.0(4) . . ? N1 O1 Zn1 119.1(2) . . ? N2 O2 Zn1 126.58(19) . 4_676 ? N2 O2 Zn1 123.9(2) . 2_646 ? Zn1 O2 Zn1 109.08(11) 4_676 2_646 ? C5 N1 O1 120.1(3) . . ? C5 N1 C1 120.4(3) . . ? O1 N1 C1 119.5(3) . . ? C11 N2 C13 119.8(4) . . ? C11 N2 O2 120.5(3) . . ? C13 N2 O2 119.7(3) . . ? N1 C1 C2 120.0(3) . . ? C1 C2 C3 121.9(4) . . ? C2 C3 C4 116.2(4) . . ? C2 C3 C6 122.4(3) . . ? C4 C3 C6 121.4(3) . . ? C5 C4 C3 121.2(3) . . ? N1 C5 C4 120.3(3) . . ? C3 C6 C7 112.4(3) . . ? C6 C7 C8 114.7(3) . . ? C9 C8 C7 111.0(3) . . ? C12 C9 C10 115.7(4) . . ? C12 C9 C8 121.9(4) . . ? C10 C9 C8 122.3(4) . . ? C11 C10 C9 121.5(4) . . ? N2 C11 C10 120.5(4) . . ? C13 C12 C9 121.3(4) . . ? N2 C13 C12 121.0(4) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.08 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.477 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.082 #=============================================END data_compd5 _database_code_CSD 214078 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 Co N6 O4 S2' _chemical_formula_weight 635.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 '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 6.9245(14) _cell_length_b 22.460(5) _cell_length_c 9.6878(19) _cell_angle_alpha 90.00 _cell_angle_beta 98.24(3) _cell_angle_gamma 90.00 _cell_volume 1491.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 658 _exptl_absorpt_coefficient_mu 0.759 _exptl_absorpt_correction_type PSI-SCAN _exptl_absorpt_correction_T_min 0.9073 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2860 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0614 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2633 _reflns_number_gt 1873 _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^)+(0.0516P)^2^+0.9451P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0014(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2633 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1176 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Co1 Co 0.0000 0.5000 0.5000 0.0365(2) Uani 1 2 d S . . O1 O 0.2462(4) 0.46773(10) 0.4210(3) 0.0520(7) Uani 1 1 d . . . O2 O 0.1846(4) -0.03279(10) 0.1781(3) 0.0501(7) Uani 1 1 d . . . N1 N 0.2912(4) 0.40994(13) 0.4173(3) 0.0436(7) Uani 1 1 d . . . N2 N 0.2670(4) 0.00703(12) 0.2713(3) 0.0419(7) Uani 1 1 d . . . C1 C 0.1556(6) 0.36948(17) 0.3683(4) 0.0534(10) Uani 1 1 d . . . H1A H 0.0286 0.3816 0.3367 0.064 Uiso 1 1 calc R . . C2 C 0.2039(6) 0.31033(18) 0.3646(5) 0.0579(11) Uani 1 1 d . . . H2A H 0.1086 0.2828 0.3307 0.069 Uiso 1 1 calc R . . C3 C 0.3921(6) 0.29093(17) 0.4105(4) 0.0483(10) Uani 1 1 d . . . C4 C 0.5269(6) 0.33430(17) 0.4572(4) 0.0523(10) Uani 1 1 d . . . H4A H 0.6555 0.3233 0.4875 0.063 Uiso 1 1 calc R . . C5 C 0.4758(6) 0.39290(17) 0.4600(4) 0.0490(10) Uani 1 1 d . . . H5A H 0.5696 0.4212 0.4918 0.059 Uiso 1 1 calc R . . C6 C 0.4486(7) 0.22571(17) 0.4097(4) 0.0567(11) Uani 1 1 d . . . H6A H 0.3624 0.2051 0.3375 0.068 Uiso 1 1 calc R . . H6B H 0.5808 0.2222 0.3884 0.068 Uiso 1 1 calc R . . C7 C 0.4361(10) 0.19729(18) 0.5482(5) 0.0782(16) Uani 1 1 d . . . H7A H 0.2999 0.1938 0.5602 0.094 Uiso 1 1 calc R . . H7B H 0.4992 0.2231 0.6215 0.094 Uiso 1 1 calc R . . C8 C 0.5318(10) 0.13480(19) 0.5652(5) 0.0853(18) Uani 1 1 d . . . H8A H 0.6681 0.1383 0.5535 0.102 Uiso 1 1 calc R . . H8B H 0.5264 0.1206 0.6591 0.102 Uiso 1 1 calc R . . C9 C 0.4355(8) 0.08953(17) 0.4628(4) 0.0571(12) Uani 1 1 d . . . C10 C 0.5318(7) 0.06837(17) 0.3573(4) 0.0568(11) Uani 1 1 d . . . H10A H 0.6563 0.0824 0.3503 0.068 Uiso 1 1 calc R . . C11 C 0.4475(6) 0.02697(17) 0.2625(4) 0.0482(9) Uani 1 1 d . . . H11A H 0.5152 0.0129 0.1928 0.058 Uiso 1 1 calc R . . C12 C 0.1694(7) 0.02654(19) 0.3716(5) 0.0597(11) Uani 1 1 d . . . H12A H 0.0441 0.0125 0.3763 0.072 Uiso 1 1 calc R . . C13 C 0.2527(8) 0.0670(2) 0.4673(5) 0.0672(13) Uani 1 1 d . . . H13A H 0.1835 0.0795 0.5375 0.081 Uiso 1 1 calc R . . N3 N 0.0431(5) 0.57962(13) 0.4004(4) 0.0480(8) Uani 1 1 d . . . C14 C 0.0559(5) 0.62085(17) 0.3331(5) 0.0526(10) Uani 1 1 d . . . S1 S 0.0794(2) 0.67854(6) 0.2339(2) 0.1093(7) 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 Co1 0.0335(4) 0.0232(3) 0.0529(4) 0.0037(3) 0.0061(3) -0.0014(3) O1 0.0473(15) 0.0263(13) 0.087(2) 0.0004(13) 0.0243(14) 0.0006(11) O2 0.0560(16) 0.0296(13) 0.0601(16) -0.0053(12) -0.0078(13) 0.0020(12) N1 0.0411(17) 0.0307(15) 0.062(2) 0.0002(14) 0.0170(15) 0.0000(13) N2 0.0500(18) 0.0283(15) 0.0454(17) 0.0025(13) -0.0003(14) 0.0046(14) C1 0.046(2) 0.040(2) 0.074(3) -0.007(2) 0.008(2) 0.0000(18) C2 0.058(3) 0.039(2) 0.077(3) -0.016(2) 0.010(2) -0.0072(19) C3 0.059(2) 0.034(2) 0.053(2) 0.0009(17) 0.0126(19) 0.0040(18) C4 0.048(2) 0.042(2) 0.067(3) -0.0026(19) 0.006(2) 0.0075(18) C5 0.045(2) 0.038(2) 0.064(3) -0.0031(18) 0.0101(19) -0.0002(17) C6 0.073(3) 0.036(2) 0.062(3) -0.0031(19) 0.014(2) 0.007(2) C7 0.149(5) 0.035(2) 0.049(3) -0.0094(19) 0.008(3) 0.000(3) C8 0.155(5) 0.037(2) 0.052(3) -0.002(2) -0.022(3) 0.001(3) C9 0.094(3) 0.031(2) 0.041(2) 0.0042(17) -0.007(2) 0.007(2) C10 0.062(3) 0.041(2) 0.062(3) -0.002(2) -0.008(2) -0.0008(19) C11 0.053(2) 0.041(2) 0.050(2) -0.0054(18) 0.0065(19) 0.0047(19) C12 0.069(3) 0.051(2) 0.063(3) 0.003(2) 0.024(2) 0.001(2) C13 0.104(4) 0.050(3) 0.050(3) -0.004(2) 0.023(3) 0.008(3) N3 0.0489(19) 0.0299(16) 0.065(2) 0.0054(15) 0.0058(16) -0.0041(14) C14 0.036(2) 0.036(2) 0.085(3) 0.013(2) 0.0035(19) -0.0015(17) S1 0.0762(9) 0.0684(9) 0.1780(17) 0.0760(11) 0.0002(10) -0.0067(7) _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 Co1 N3 2.074(3) 3_566 ? Co1 N3 2.074(3) . ? Co1 O1 2.095(2) . ? Co1 O1 2.095(2) 3_566 ? Co1 O2 2.126(3) 4_566 ? Co1 O2 2.126(3) 2 ? O1 N1 1.337(4) . ? O2 N2 1.339(4) . ? O2 Co1 2.126(3) 2_545 ? N1 C5 1.341(5) . ? N1 C1 1.343(5) . ? N2 C12 1.335(5) . ? N2 C11 1.342(5) . ? C1 C2 1.372(5) . ? C2 C3 1.385(6) . ? C3 C4 1.380(6) . ? C3 C6 1.517(5) . ? C4 C5 1.364(5) . ? C6 C7 1.500(6) . ? C7 C8 1.551(6) . ? C8 C9 1.507(6) . ? C9 C13 1.370(7) . ? C9 C10 1.382(6) . ? C10 C11 1.377(5) . ? C12 C13 1.365(6) . ? N3 C14 1.144(5) . ? C14 S1 1.635(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 N3 Co1 N3 180.00(8) 3_566 . ? N3 Co1 O1 92.89(11) 3_566 . ? N3 Co1 O1 87.11(11) . . ? N3 Co1 O1 87.11(11) 3_566 3_566 ? N3 Co1 O1 92.89(11) . 3_566 ? O1 Co1 O1 180.000(1) . 3_566 ? N3 Co1 O2 91.78(11) 3_566 4_566 ? N3 Co1 O2 88.22(11) . 4_566 ? O1 Co1 O2 89.44(11) . 4_566 ? O1 Co1 O2 90.56(11) 3_566 4_566 ? N3 Co1 O2 88.22(11) 3_566 2 ? N3 Co1 O2 91.78(11) . 2 ? O1 Co1 O2 90.56(11) . 2 ? O1 Co1 O2 89.44(11) 3_566 2 ? O2 Co1 O2 180.00(12) 4_566 2 ? N1 O1 Co1 123.4(2) . . ? N2 O2 Co1 117.66(19) . 2_545 ? O1 N1 C5 119.0(3) . . ? O1 N1 C1 120.8(3) . . ? C5 N1 C1 120.2(3) . . ? C12 N2 O2 119.9(3) . . ? C12 N2 C11 120.7(3) . . ? O2 N2 C11 119.4(3) . . ? N1 C1 C2 120.2(4) . . ? C1 C2 C3 121.2(4) . . ? C4 C3 C2 116.4(4) . . ? C4 C3 C6 121.4(4) . . ? C2 C3 C6 122.3(4) . . ? C5 C4 C3 121.5(4) . . ? N1 C5 C4 120.5(4) . . ? C7 C6 C3 111.0(3) . . ? C6 C7 C8 113.7(4) . . ? C9 C8 C7 113.5(4) . . ? C13 C9 C10 116.3(4) . . ? C13 C9 C8 123.5(5) . . ? C10 C9 C8 120.2(5) . . ? C11 C10 C9 121.5(4) . . ? N2 C11 C10 119.5(4) . . ? N2 C12 C13 120.3(4) . . ? C12 C13 C9 121.8(4) . . ? C14 N3 Co1 172.7(3) . . ? N3 C14 S1 178.0(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.783 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.064 #=============================================END data_compd6 _database_code_CSD 214079 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Cd0.50 N3 O2 S' _chemical_formula_weight 344.54 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' Cd Cd -0.8075 1.2024 '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 7.1151(12) _cell_length_b 22.521(4) _cell_length_c 9.7076(17) _cell_angle_alpha 90.00 _cell_angle_beta 99.210(3) _cell_angle_gamma 90.00 _cell_volume 1535.5(5) _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 block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 0.890 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.6973 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10405 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.07 _reflns_number_total 3723 _reflns_number_gt 2944 _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^)+(0.0815P)^2^+0.4493P] 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 3723 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 Cd1 Cd 0.0000 0.5000 0.5000 0.04108(13) Uani 1 2 d S . . O1 O 0.2648(3) 0.46768(9) 0.4141(3) 0.0621(6) Uani 1 1 d . . . O2 O 0.1930(3) -0.03520(9) 0.1983(2) 0.0596(6) Uani 1 1 d . . . N1 N 0.3075(3) 0.41030(10) 0.4125(3) 0.0490(6) Uani 1 1 d . . . N2 N 0.2750(5) 0.00634(10) 0.2844(3) 0.0485(6) Uani 1 1 d . . . C1 C 0.1749(5) 0.37032(14) 0.3612(4) 0.0565(8) Uani 1 1 d . . . H1A H 0.0518 0.3829 0.3270 0.068 Uiso 1 1 calc R . . C2 C 0.2190(5) 0.31135(14) 0.3586(4) 0.0602(8) Uani 1 1 d . . . H2A H 0.1251 0.2841 0.3236 0.072 Uiso 1 1 calc R . . C3 C 0.4025(5) 0.29159(13) 0.4077(3) 0.0528(7) Uani 1 1 d . . . C4 C 0.5343(5) 0.33440(15) 0.4583(4) 0.0598(8) Uani 1 1 d . . . H4A H 0.6591 0.3231 0.4915 0.072 Uiso 1 1 calc R . . C5 C 0.4853(4) 0.39311(16) 0.4605(4) 0.0563(7) Uani 1 1 d . . . H5A H 0.5764 0.4212 0.4958 0.068 Uiso 1 1 calc R . . C6 C 0.4572(6) 0.22702(15) 0.4090(4) 0.0621(9) Uani 1 1 d . . . H6A H 0.3704 0.2060 0.3383 0.074 Uiso 1 1 calc R . . H6B H 0.5845 0.2233 0.3861 0.074 Uiso 1 1 calc R . . C7 C 0.4519(9) 0.19923(16) 0.5487(4) 0.0861(14) Uani 1 1 d . . . H7A H 0.3203 0.1960 0.5626 0.103 Uiso 1 1 calc R . . H7B H 0.5169 0.2252 0.6207 0.103 Uiso 1 1 calc R . . C8 C 0.5440(9) 0.13741(17) 0.5658(4) 0.0963(17) Uani 1 1 d . . . H8A H 0.6753 0.1406 0.5512 0.116 Uiso 1 1 calc R . . H8B H 0.5447 0.1240 0.6609 0.116 Uiso 1 1 calc R . . C9 C 0.4439(7) 0.09124(15) 0.4665(3) 0.0664(10) Uani 1 1 d . . . C10 C 0.5306(6) 0.06962(15) 0.3600(4) 0.0655(9) Uani 1 1 d . . . H10A H 0.6501 0.0838 0.3492 0.079 Uiso 1 1 calc R . . C11 C 0.4440(5) 0.02745(14) 0.2696(3) 0.0551(7) Uani 1 1 d . . . H11A H 0.5043 0.0136 0.1977 0.066 Uiso 1 1 calc R . . C12 C 0.1864(6) 0.02682(19) 0.3844(4) 0.0707(10) Uani 1 1 d . . . H12A H 0.0659 0.0126 0.3922 0.085 Uiso 1 1 calc R . . C13 C 0.2699(8) 0.06879(18) 0.4765(4) 0.0798(12) Uani 1 1 d . . . H13A H 0.2061 0.0821 0.5471 0.096 Uiso 1 1 calc R . . N3 N 0.0335(4) 0.58690(12) 0.3927(3) 0.0621(7) Uani 1 1 d . . . C14 C 0.0470(5) 0.62536(14) 0.3214(4) 0.0616(9) Uani 1 1 d . . . S1 S 0.07586(19) 0.67876(6) 0.2148(2) 0.1252(7) 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 Cd1 0.03414(18) 0.03259(17) 0.0568(2) 0.00172(10) 0.00802(12) -0.00104(9) O1 0.0507(12) 0.0367(11) 0.1063(19) 0.0010(11) 0.0350(13) 0.0001(9) O2 0.0640(14) 0.0389(10) 0.0689(13) 0.0011(10) -0.0102(11) 0.0000(10) N1 0.0435(13) 0.0382(11) 0.0701(16) -0.0012(10) 0.0238(12) 0.0003(10) N2 0.0563(17) 0.0378(12) 0.0493(13) 0.0063(9) 0.0022(12) 0.0080(10) C1 0.0439(17) 0.0488(16) 0.078(2) -0.0061(15) 0.0116(15) 0.0020(13) C2 0.060(2) 0.0428(16) 0.079(2) -0.0113(14) 0.0140(17) -0.0045(14) C3 0.0631(19) 0.0425(15) 0.0554(16) -0.0005(12) 0.0172(14) 0.0048(13) C4 0.0522(18) 0.0530(18) 0.0740(19) 0.0008(16) 0.0091(16) 0.0056(14) C5 0.0461(17) 0.0501(17) 0.0745(19) -0.0004(16) 0.0152(15) -0.0025(13) C6 0.080(2) 0.0494(17) 0.0584(18) -0.0034(14) 0.0168(17) 0.0120(16) C7 0.158(5) 0.0470(19) 0.0502(17) -0.0062(16) 0.008(2) 0.005(2) C8 0.166(5) 0.0472(19) 0.058(2) -0.0063(16) -0.035(3) 0.011(2) C9 0.110(3) 0.0400(16) 0.0410(14) 0.0022(12) -0.0125(18) 0.0139(19) C10 0.067(2) 0.0539(18) 0.072(2) -0.0006(16) -0.0026(17) -0.0016(16) C11 0.0602(19) 0.0457(17) 0.0598(18) -0.0066(13) 0.0106(15) 0.0058(14) C12 0.079(3) 0.067(2) 0.071(2) 0.0049(19) 0.027(2) 0.001(2) C13 0.118(4) 0.070(2) 0.057(2) -0.0027(17) 0.029(2) 0.009(2) N3 0.0695(18) 0.0425(13) 0.0729(17) 0.0041(12) 0.0076(14) -0.0114(13) C14 0.0406(17) 0.0467(17) 0.096(3) 0.0135(17) 0.0075(17) 0.0017(13) S1 0.0762(8) 0.0916(9) 0.2061(17) 0.0917(11) 0.0180(9) 0.0012(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 Cd1 N3 2.247(3) 3_566 ? Cd1 N3 2.247(3) . ? Cd1 O1 2.297(2) 3_566 ? Cd1 O1 2.297(2) . ? Cd1 O2 2.318(2) 2 ? Cd1 O2 2.318(2) 4_566 ? O1 N1 1.328(3) . ? O2 N2 1.326(3) . ? O2 Cd1 2.318(2) 2_545 ? N1 C5 1.333(4) . ? N1 C1 1.341(4) . ? N2 C11 1.322(5) . ? N2 C12 1.322(5) . ? C1 C2 1.366(4) . ? C2 C3 1.389(5) . ? C3 C4 1.379(5) . ? C3 C6 1.505(4) . ? C4 C5 1.369(5) . ? C6 C7 1.500(6) . ? C7 C8 1.536(6) . ? C8 C9 1.516(5) . ? C9 C13 1.355(6) . ? C9 C10 1.375(5) . ? C10 C11 1.371(5) . ? C12 C13 1.370(6) . ? N3 C14 1.123(4) . ? C14 S1 1.621(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 N3 Cd1 N3 180.00(7) 3_566 . ? N3 Cd1 O1 87.36(10) 3_566 3_566 ? N3 Cd1 O1 92.64(10) . 3_566 ? N3 Cd1 O1 92.64(10) 3_566 . ? N3 Cd1 O1 87.36(10) . . ? O1 Cd1 O1 180.0 3_566 . ? N3 Cd1 O2 89.68(9) 3_566 2 ? N3 Cd1 O2 90.32(9) . 2 ? O1 Cd1 O2 89.92(9) 3_566 2 ? O1 Cd1 O2 90.08(9) . 2 ? N3 Cd1 O2 90.32(9) 3_566 4_566 ? N3 Cd1 O2 89.68(9) . 4_566 ? O1 Cd1 O2 90.08(9) 3_566 4_566 ? O1 Cd1 O2 89.92(9) . 4_566 ? O2 Cd1 O2 180.000(1) 2 4_566 ? N1 O1 Cd1 121.02(16) . . ? N2 O2 Cd1 115.12(16) . 2_545 ? O1 N1 C5 119.0(3) . . ? O1 N1 C1 120.6(3) . . ? C5 N1 C1 120.4(3) . . ? C11 N2 C12 120.2(3) . . ? C11 N2 O2 120.1(3) . . ? C12 N2 O2 119.7(3) . . ? N1 C1 C2 120.7(3) . . ? C1 C2 C3 120.7(3) . . ? C4 C3 C2 116.5(3) . . ? C4 C3 C6 120.8(3) . . ? C2 C3 C6 122.7(3) . . ? C5 C4 C3 121.4(3) . . ? N1 C5 C4 120.3(3) . . ? C7 C6 C3 111.5(3) . . ? C6 C7 C8 113.8(4) . . ? C9 C8 C7 113.8(4) . . ? C13 C9 C10 116.5(4) . . ? C13 C9 C8 123.5(4) . . ? C10 C9 C8 120.0(5) . . ? C11 C10 C9 121.1(4) . . ? N2 C11 C10 120.2(3) . . ? N2 C12 C13 120.8(4) . . ? C9 C13 C12 121.1(4) . . ? C14 N3 Cd1 169.6(3) . . ? N3 C14 S1 176.7(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.07 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.253 _refine_diff_density_min -0.775 _refine_diff_density_rms 0.088 #=============================================END data_compd7 _database_code_CSD 214080 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Mn0.50 N3 O3 S' _chemical_formula_weight 333.83 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' Mn Mn 0.3368 0.7283 '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 12.773(3) _cell_length_b 14.033(3) _cell_length_c 8.7340(17) _cell_angle_alpha 90.00 _cell_angle_beta 94.66(3) _cell_angle_gamma 90.00 _cell_volume 1560.4(5) _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 block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 694 _exptl_absorpt_coefficient_mu 0.607 _exptl_absorpt_correction_type PSI-SCAN _exptl_absorpt_correction_T_min 0.8169 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2958 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2760 _reflns_number_gt 2138 _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^)+(0.0397P)^2^+0.3244P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0323(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2760 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Mn1 Mn 0.5000 0.5000 0.0000 0.03765(19) Uani 1 2 d S . . O1 O 0.52096(14) 0.51274(15) 0.2445(2) 0.0554(5) Uani 1 1 d . . . O2 O -0.35630(13) 0.75394(14) 0.2299(2) 0.0502(5) Uani 1 1 d . . . N1 N 0.44447(16) 0.54543(17) 0.3267(2) 0.0435(5) Uani 1 1 d . . . N2 N -0.25504(16) 0.73663(15) 0.2692(2) 0.0417(5) Uani 1 1 d . . . C1 C 0.3755(2) 0.4843(2) 0.3789(3) 0.0508(7) Uani 1 1 d . . . H1A H 0.3794 0.4198 0.3560 0.061 Uiso 1 1 calc R . . C2 C 0.2986(2) 0.5175(2) 0.4668(3) 0.0571(8) Uani 1 1 d . . . H2A H 0.2504 0.4746 0.5018 0.069 Uiso 1 1 calc R . . C3 C 0.2909(2) 0.6125(2) 0.5045(3) 0.0483(7) Uani 1 1 d . . . C4 C 0.3628(2) 0.6717(2) 0.4464(4) 0.0568(8) Uani 1 1 d . . . H4A H 0.3604 0.7366 0.4676 0.068 Uiso 1 1 calc R . . C5 C 0.4384(2) 0.6377(2) 0.3576(4) 0.0577(8) Uani 1 1 d . . . H5A H 0.4859 0.6798 0.3187 0.069 Uiso 1 1 calc R . . C6 C 0.2093(2) 0.6478(3) 0.6067(3) 0.0710(10) Uani 1 1 d . . . H6A H 0.2226 0.7146 0.6292 0.085 Uiso 1 1 calc R . . H6B H 0.2175 0.6133 0.7032 0.085 Uiso 1 1 calc R . . C7 C 0.0959(2) 0.6370(3) 0.5389(4) 0.0662(9) Uani 1 1 d . . . H7A H 0.0814 0.5700 0.5198 0.079 Uiso 1 1 calc R . . H7B H 0.0491 0.6590 0.6135 0.079 Uiso 1 1 calc R . . C8 C 0.0731(2) 0.6913(2) 0.3921(4) 0.0576(8) Uani 1 1 d . . . H8A H 0.1038 0.6576 0.3098 0.069 Uiso 1 1 calc R . . H8B H 0.1065 0.7533 0.4024 0.069 Uiso 1 1 calc R . . C9 C -0.0427(2) 0.7050(2) 0.3488(3) 0.0486(7) Uani 1 1 d . . . C10 C -0.1071(2) 0.6351(2) 0.2803(3) 0.0542(7) Uani 1 1 d . . . H10A H -0.0789 0.5759 0.2599 0.065 Uiso 1 1 calc R . . C11 C -0.2121(2) 0.6516(2) 0.2420(3) 0.0503(7) Uani 1 1 d . . . H11A H -0.2538 0.6033 0.1967 0.060 Uiso 1 1 calc R . . C12 C -0.1946(2) 0.8055(2) 0.3356(4) 0.0560(8) Uani 1 1 d . . . H12A H -0.2242 0.8643 0.3553 0.067 Uiso 1 1 calc R . . C13 C -0.0899(2) 0.7907(2) 0.3749(4) 0.0580(8) Uani 1 1 d . . . H13A H -0.0498 0.8400 0.4204 0.070 Uiso 1 1 calc R . . S1 S 0.87461(5) 0.45240(6) -0.03529(11) 0.0603(3) Uani 1 1 d . . . C14 C 0.74932(19) 0.44890(18) -0.0158(3) 0.0392(6) Uani 1 1 d . . . N3 N 0.66043(17) 0.4487(2) 0.0000(3) 0.0566(6) Uani 1 1 d . . . O1W O 0.43999(15) 0.34957(13) 0.0203(2) 0.0529(5) Uani 1 1 d . . . H1WB H 0.4039 0.3183 -0.0617 0.079 Uiso 1 1 d R . . H1WA H 0.4194 0.3178 0.0990 0.079 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 Mn1 0.0253(3) 0.0462(3) 0.0412(3) -0.0048(3) 0.0011(2) 0.0003(2) O1 0.0404(11) 0.0820(15) 0.0431(10) -0.0114(10) -0.0002(8) 0.0136(10) O2 0.0379(10) 0.0530(11) 0.0586(12) -0.0102(9) -0.0021(9) -0.0020(9) N1 0.0364(11) 0.0576(14) 0.0359(11) -0.0044(10) -0.0018(9) 0.0040(10) N2 0.0397(11) 0.0427(12) 0.0427(12) -0.0070(10) 0.0046(10) -0.0028(10) C1 0.0576(18) 0.0467(16) 0.0472(16) 0.0026(13) -0.0017(13) 0.0016(13) C2 0.0581(18) 0.066(2) 0.0479(16) 0.0074(14) 0.0103(14) -0.0096(15) C3 0.0371(14) 0.073(2) 0.0346(14) -0.0032(13) -0.0026(11) 0.0030(13) C4 0.0540(17) 0.0518(17) 0.0655(19) -0.0146(15) 0.0107(15) 0.0010(14) C5 0.0532(17) 0.0540(18) 0.068(2) -0.0097(15) 0.0178(15) -0.0122(14) C6 0.0536(18) 0.120(3) 0.0403(16) -0.0057(18) 0.0075(14) 0.0136(19) C7 0.0458(16) 0.101(3) 0.0539(19) 0.0083(17) 0.0171(14) 0.0115(17) C8 0.0466(16) 0.069(2) 0.0578(18) -0.0014(15) 0.0095(14) 0.0049(14) C9 0.0441(15) 0.0600(18) 0.0424(15) -0.0019(13) 0.0072(12) -0.0006(13) C10 0.0585(18) 0.0460(16) 0.0578(18) -0.0051(14) 0.0030(14) 0.0103(13) C11 0.0564(17) 0.0423(15) 0.0510(16) -0.0075(13) -0.0027(13) -0.0050(13) C12 0.0456(15) 0.0463(16) 0.076(2) -0.0225(15) 0.0030(14) -0.0036(13) C13 0.0425(15) 0.0597(19) 0.071(2) -0.0218(16) -0.0002(14) -0.0074(14) S1 0.0310(4) 0.0608(5) 0.0897(6) -0.0014(4) 0.0096(4) 0.0040(3) C14 0.0361(14) 0.0390(14) 0.0415(14) -0.0015(11) -0.0033(11) 0.0067(11) N3 0.0313(12) 0.0754(18) 0.0631(16) 0.0010(13) 0.0039(11) 0.0085(11) O1W 0.0598(12) 0.0482(11) 0.0502(11) -0.0005(9) 0.0015(9) -0.0139(9) _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 Mn1 O1 2.1382(19) 3_665 ? Mn1 O1 2.1382(19) . ? Mn1 N3 2.172(2) . ? Mn1 N3 2.172(2) 3_665 ? Mn1 O1W 2.2578(19) 3_665 ? Mn1 O1W 2.2578(19) . ? O1 N1 1.339(3) . ? O2 N2 1.333(3) . ? N1 C5 1.327(4) . ? N1 C1 1.336(4) . ? N2 C12 1.340(3) . ? N2 C11 1.343(3) . ? C1 C2 1.376(4) . ? C2 C3 1.378(4) . ? C3 C4 1.367(4) . ? C3 C6 1.510(4) . ? C4 C5 1.373(4) . ? C6 C7 1.528(4) . ? C7 C8 1.500(4) . ? C8 C9 1.509(4) . ? C9 C13 1.373(4) . ? C9 C10 1.384(4) . ? C10 C11 1.374(4) . ? C12 C13 1.368(4) . ? S1 C14 1.624(3) . ? C14 N3 1.155(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 Mn1 O1 180.0 3_665 . ? O1 Mn1 N3 90.80(9) 3_665 . ? O1 Mn1 N3 89.20(9) . . ? O1 Mn1 N3 89.20(9) 3_665 3_665 ? O1 Mn1 N3 90.80(9) . 3_665 ? N3 Mn1 N3 180.00(14) . 3_665 ? O1 Mn1 O1W 90.88(8) 3_665 3_665 ? O1 Mn1 O1W 89.12(8) . 3_665 ? N3 Mn1 O1W 89.07(9) . 3_665 ? N3 Mn1 O1W 90.93(9) 3_665 3_665 ? O1 Mn1 O1W 89.12(8) 3_665 . ? O1 Mn1 O1W 90.88(8) . . ? N3 Mn1 O1W 90.93(9) . . ? N3 Mn1 O1W 89.07(9) 3_665 . ? O1W Mn1 O1W 180.0 3_665 . ? N1 O1 Mn1 121.74(14) . . ? C5 N1 C1 120.4(2) . . ? C5 N1 O1 120.0(2) . . ? C1 N1 O1 119.6(2) . . ? O2 N2 C12 119.6(2) . . ? O2 N2 C11 121.2(2) . . ? C12 N2 C11 119.2(2) . . ? N1 C1 C2 119.6(3) . . ? C1 C2 C3 121.9(3) . . ? C4 C3 C2 115.9(3) . . ? C4 C3 C6 122.5(3) . . ? C2 C3 C6 121.6(3) . . ? C3 C4 C5 121.6(3) . . ? N1 C5 C4 120.6(3) . . ? C3 C6 C7 114.6(3) . . ? C8 C7 C6 113.1(3) . . ? C7 C8 C9 113.4(2) . . ? C13 C9 C10 116.0(3) . . ? C13 C9 C8 120.3(3) . . ? C10 C9 C8 123.7(3) . . ? C11 C10 C9 121.4(3) . . ? N2 C11 C10 120.7(3) . . ? N2 C12 C13 121.1(3) . . ? C12 C13 C9 121.6(3) . . ? N3 C14 S1 178.2(3) . . ? C14 N3 Mn1 159.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mn1 O1 N1 -91(100) 3_665 . . . ? N3 Mn1 O1 N1 178.9(2) . . . . ? N3 Mn1 O1 N1 -1.1(2) 3_665 . . . ? O1W Mn1 O1 N1 89.8(2) 3_665 . . . ? O1W Mn1 O1 N1 -90.2(2) . . . . ? Mn1 O1 N1 C5 -91.3(3) . . . . ? Mn1 O1 N1 C1 89.6(3) . . . . ? C5 N1 C1 C2 -0.8(4) . . . . ? O1 N1 C1 C2 178.3(2) . . . . ? N1 C1 C2 C3 -0.7(5) . . . . ? C1 C2 C3 C4 1.4(4) . . . . ? C1 C2 C3 C6 -177.3(3) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C6 C3 C4 C5 177.9(3) . . . . ? C1 N1 C5 C4 1.5(4) . . . . ? O1 N1 C5 C4 -177.6(3) . . . . ? C3 C4 C5 N1 -0.7(5) . . . . ? C4 C3 C6 C7 116.1(4) . . . . ? C2 C3 C6 C7 -65.3(4) . . . . ? C3 C6 C7 C8 -60.9(4) . . . . ? C6 C7 C8 C9 -163.2(3) . . . . ? C7 C8 C9 C13 101.7(4) . . . . ? C7 C8 C9 C10 -79.1(4) . . . . ? C13 C9 C10 C11 -0.2(4) . . . . ? C8 C9 C10 C11 -179.5(3) . . . . ? O2 N2 C11 C10 178.7(3) . . . . ? C12 N2 C11 C10 -0.5(4) . . . . ? C9 C10 C11 N2 0.4(5) . . . . ? O2 N2 C12 C13 -178.8(3) . . . . ? C11 N2 C12 C13 0.5(5) . . . . ? N2 C12 C13 C9 -0.3(5) . . . . ? C10 C9 C13 C12 0.2(5) . . . . ? C8 C9 C13 C12 179.4(3) . . . . ? S1 C14 N3 Mn1 46(9) . . . . ? O1 Mn1 N3 C14 75.6(7) 3_665 . . . ? O1 Mn1 N3 C14 -104.4(7) . . . . ? N3 Mn1 N3 C14 156(10) 3_665 . . . ? O1W Mn1 N3 C14 -15.3(7) 3_665 . . . ? O1W Mn1 N3 C14 164.7(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WB O2 0.93 1.85 2.766(3) 169.2 3_565 O1W H1WA O2 0.88 1.97 2.843(3) 173.0 2_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.249 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.046 #=============================================END data_compd8 _database_code_CSD 214081 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N3 O3 S Zn0.50' _chemical_formula_weight 339.04 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)/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 12.564(3) _cell_length_b 14.136(3) _cell_length_c 8.7786(18) _cell_angle_alpha 90.00 _cell_angle_beta 94.28(3) _cell_angle_gamma 90.00 _cell_volume 1554.8(5) _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 block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.975 _exptl_absorpt_correction_type REQAB _exptl_absorpt_correction_T_min 0.6414 _exptl_absorpt_correction_T_max 0.7586 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4834 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.53 _reflns_number_total 2761 _reflns_number_gt 2637 _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^)+(0.0437P)^2^+0.3357P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.030(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2761 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.5000 0.5000 0.0000 0.05538(17) Uani 1 2 d S . . O1 O 0.52790(12) 0.51525(12) 0.23537(18) 0.0674(4) Uani 1 1 d . . . O2 O -0.35698(11) 0.75603(11) 0.21940(19) 0.0650(4) Uani 1 1 d . . . N1 N 0.45018(12) 0.54645(13) 0.31884(19) 0.0555(4) Uani 1 1 d . . . N2 N -0.25497(13) 0.73803(12) 0.26240(19) 0.0554(4) Uani 1 1 d . . . C1 C 0.3830(2) 0.48395(16) 0.3754(3) 0.0642(6) Uani 1 1 d . . . H1A H 0.3890 0.4199 0.3538 0.077 Uiso 1 1 calc R . . C2 C 0.3056(2) 0.51525(18) 0.4653(3) 0.0690(6) Uani 1 1 d . . . H2A H 0.2587 0.4716 0.5028 0.083 Uiso 1 1 calc R . . C3 C 0.29517(16) 0.60990(18) 0.5019(2) 0.0615(5) Uani 1 1 d . . . C4 C 0.36523(18) 0.67098(17) 0.4395(3) 0.0694(6) Uani 1 1 d . . . H4A H 0.3607 0.7354 0.4593 0.083 Uiso 1 1 calc R . . C5 C 0.44159(18) 0.63875(17) 0.3486(3) 0.0684(6) Uani 1 1 d . . . H5A H 0.4878 0.6815 0.3073 0.082 Uiso 1 1 calc R . . C6 C 0.21316(18) 0.6435(2) 0.6062(3) 0.0846(8) Uani 1 1 d . . . H6A H 0.2274 0.7093 0.6319 0.101 Uiso 1 1 calc R . . H6B H 0.2209 0.6073 0.7002 0.101 Uiso 1 1 calc R . . C7 C 0.09768(19) 0.6347(2) 0.5378(3) 0.0817(7) Uani 1 1 d . . . H7A H 0.0824 0.5687 0.5155 0.098 Uiso 1 1 calc R . . H7B H 0.0499 0.6554 0.6129 0.098 Uiso 1 1 calc R . . C8 C 0.07571(17) 0.69169(19) 0.3940(3) 0.0710(6) Uani 1 1 d . . . H8A H 0.1088 0.6603 0.3113 0.085 Uiso 1 1 calc R . . H8B H 0.1090 0.7533 0.4084 0.085 Uiso 1 1 calc R . . C9 C -0.04110(17) 0.70547(17) 0.3477(3) 0.0629(5) Uani 1 1 d . . . C10 C -0.10670(18) 0.63566(17) 0.2800(3) 0.0682(6) Uani 1 1 d . . . H10A H -0.0782 0.5763 0.2626 0.082 Uiso 1 1 calc R . . C11 C -0.21233(18) 0.65227(15) 0.2383(3) 0.0637(5) Uani 1 1 d . . . H11A H -0.2546 0.6044 0.1934 0.076 Uiso 1 1 calc R . . C12 C -0.19421(17) 0.80676(17) 0.3287(3) 0.0706(6) Uani 1 1 d . . . H12A H -0.2242 0.8656 0.3456 0.085 Uiso 1 1 calc R . . C13 C -0.08873(18) 0.79140(18) 0.3718(3) 0.0739(6) Uani 1 1 d . . . H13A H -0.0484 0.8400 0.4184 0.089 Uiso 1 1 calc R . . S1 S 0.87221(4) 0.45228(5) -0.03586(9) 0.0742(2) Uani 1 1 d . . . C14 C 0.74496(15) 0.45218(14) -0.0180(2) 0.0514(4) Uani 1 1 d . . . N3 N 0.65509(14) 0.45468(15) -0.0033(2) 0.0666(5) Uani 1 1 d . . . O1W O 0.44487(12) 0.35011(11) 0.02761(18) 0.0690(4) Uani 1 1 d . . . H1WB H 0.4087 0.3188 -0.0544 0.103 Uiso 1 1 d R . . H1WA H 0.4242 0.3183 0.1063 0.103 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 Zn1 0.0379(2) 0.0699(3) 0.0583(2) -0.00729(15) 0.00300(14) 0.00421(13) O1 0.0491(8) 0.0917(11) 0.0612(9) -0.0111(8) 0.0025(7) 0.0142(7) O2 0.0515(7) 0.0628(9) 0.0802(10) -0.0095(8) 0.0005(7) -0.0029(7) N1 0.0470(8) 0.0664(11) 0.0528(9) -0.0043(8) 0.0022(7) 0.0028(8) N2 0.0524(9) 0.0534(9) 0.0607(10) -0.0066(8) 0.0062(7) -0.0036(7) C1 0.0712(14) 0.0581(12) 0.0628(13) 0.0012(10) 0.0026(11) -0.0010(10) C2 0.0658(14) 0.0784(15) 0.0636(14) 0.0081(11) 0.0108(11) -0.0103(11) C3 0.0508(10) 0.0824(15) 0.0509(11) -0.0025(10) 0.0014(8) 0.0028(10) C4 0.0664(13) 0.0632(13) 0.0796(15) -0.0125(12) 0.0115(11) 0.0008(11) C5 0.0623(13) 0.0653(14) 0.0793(14) -0.0084(12) 0.0174(11) -0.0103(10) C6 0.0614(13) 0.134(3) 0.0590(13) -0.0071(15) 0.0102(10) 0.0119(14) C7 0.0625(13) 0.114(2) 0.0704(15) 0.0084(14) 0.0195(11) 0.0118(13) C8 0.0580(12) 0.0796(15) 0.0766(14) -0.0010(12) 0.0129(10) 0.0044(11) C9 0.0569(11) 0.0719(14) 0.0608(12) -0.0047(11) 0.0102(9) 0.0003(10) C10 0.0714(14) 0.0584(13) 0.0747(14) -0.0066(11) 0.0047(11) 0.0080(11) C11 0.0675(13) 0.0524(12) 0.0705(13) -0.0083(10) 0.0005(10) -0.0035(10) C12 0.0578(12) 0.0585(12) 0.0951(17) -0.0216(12) 0.0024(11) -0.0035(10) C13 0.0563(12) 0.0710(14) 0.0944(17) -0.0236(13) 0.0047(11) -0.0066(11) S1 0.0428(3) 0.0731(4) 0.1077(5) 0.0002(3) 0.0122(3) 0.0054(2) C14 0.0451(10) 0.0513(11) 0.0575(11) -0.0025(9) 0.0019(8) 0.0045(8) N3 0.0460(10) 0.0834(13) 0.0704(12) -0.0032(10) 0.0046(8) 0.0083(9) O1W 0.0771(10) 0.0625(9) 0.0669(9) -0.0008(7) 0.0031(7) -0.0120(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 N3 2.0534(17) 3_665 ? Zn1 N3 2.0534(17) . ? Zn1 O1 2.0810(16) . ? Zn1 O1 2.0810(16) 3_665 ? Zn1 O1W 2.2480(15) . ? Zn1 O1W 2.2480(15) 3_665 ? O1 N1 1.338(2) . ? O2 N2 1.333(2) . ? N1 C5 1.337(3) . ? N1 C1 1.342(3) . ? N2 C12 1.341(3) . ? N2 C11 1.348(3) . ? C1 C2 1.371(3) . ? C2 C3 1.385(4) . ? C3 C4 1.376(3) . ? C3 C6 1.506(3) . ? C4 C5 1.371(3) . ? C6 C7 1.533(3) . ? C7 C8 1.506(4) . ? C8 C9 1.506(3) . ? C9 C13 1.378(3) . ? C9 C10 1.390(3) . ? C10 C11 1.370(3) . ? C12 C13 1.368(3) . ? S1 C14 1.618(2) . ? C14 N3 1.147(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 N3 Zn1 N3 180.00(11) 3_665 . ? N3 Zn1 O1 92.49(7) 3_665 . ? N3 Zn1 O1 87.51(7) . . ? N3 Zn1 O1 87.51(7) 3_665 3_665 ? N3 Zn1 O1 92.49(7) . 3_665 ? O1 Zn1 O1 180.0 . 3_665 ? N3 Zn1 O1W 89.55(7) 3_665 . ? N3 Zn1 O1W 90.45(7) . . ? O1 Zn1 O1W 91.21(6) . . ? O1 Zn1 O1W 88.79(6) 3_665 . ? N3 Zn1 O1W 90.45(7) 3_665 3_665 ? N3 Zn1 O1W 89.55(7) . 3_665 ? O1 Zn1 O1W 88.79(6) . 3_665 ? O1 Zn1 O1W 91.21(6) 3_665 3_665 ? O1W Zn1 O1W 180.00(8) . 3_665 ? N1 O1 Zn1 120.13(12) . . ? C5 N1 O1 120.10(18) . . ? C5 N1 C1 120.52(19) . . ? O1 N1 C1 119.35(19) . . ? O2 N2 C12 119.25(17) . . ? O2 N2 C11 120.79(17) . . ? C12 N2 C11 119.96(18) . . ? N1 C1 C2 119.6(2) . . ? C1 C2 C3 121.9(2) . . ? C4 C3 C2 116.1(2) . . ? C4 C3 C6 122.1(2) . . ? C2 C3 C6 121.8(2) . . ? C5 C4 C3 121.3(2) . . ? N1 C5 C4 120.6(2) . . ? C3 C6 C7 114.0(2) . . ? C8 C7 C6 113.2(2) . . ? C7 C8 C9 114.17(19) . . ? C13 C9 C10 116.2(2) . . ? C13 C9 C8 119.9(2) . . ? C10 C9 C8 123.9(2) . . ? C11 C10 C9 121.6(2) . . ? N2 C11 C10 120.0(2) . . ? N2 C12 C13 120.9(2) . . ? C12 C13 C9 121.3(2) . . ? N3 C14 S1 178.0(2) . . ? C14 N3 Zn1 162.69(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Zn1 O1 N1 -0.25(16) 3_665 . . . ? N3 Zn1 O1 N1 179.75(16) . . . . ? O1 Zn1 O1 N1 159.8(7) 3_665 . . . ? O1W Zn1 O1 N1 -89.85(15) . . . . ? O1W Zn1 O1 N1 90.15(15) 3_665 . . . ? Zn1 O1 N1 C5 -92.6(2) . . . . ? Zn1 O1 N1 C1 89.2(2) . . . . ? C5 N1 C1 C2 -0.5(3) . . . . ? O1 N1 C1 C2 177.8(2) . . . . ? N1 C1 C2 C3 -1.0(4) . . . . ? C1 C2 C3 C4 1.7(4) . . . . ? C1 C2 C3 C6 -177.3(2) . . . . ? C2 C3 C4 C5 -1.0(4) . . . . ? C6 C3 C4 C5 177.9(2) . . . . ? O1 N1 C5 C4 -177.1(2) . . . . ? C1 N1 C5 C4 1.1(4) . . . . ? C3 C4 C5 N1 -0.3(4) . . . . ? C4 C3 C6 C7 112.3(3) . . . . ? C2 C3 C6 C7 -68.8(3) . . . . ? C3 C6 C7 C8 -60.8(4) . . . . ? C6 C7 C8 C9 -164.6(2) . . . . ? C7 C8 C9 C13 104.2(3) . . . . ? C7 C8 C9 C10 -75.9(3) . . . . ? C13 C9 C10 C11 0.8(4) . . . . ? C8 C9 C10 C11 -179.2(2) . . . . ? O2 N2 C11 C10 178.5(2) . . . . ? C12 N2 C11 C10 -0.7(3) . . . . ? C9 C10 C11 N2 0.1(4) . . . . ? O2 N2 C12 C13 -178.8(2) . . . . ? C11 N2 C12 C13 0.4(4) . . . . ? N2 C12 C13 C9 0.6(4) . . . . ? C10 C9 C13 C12 -1.1(4) . . . . ? C8 C9 C13 C12 178.8(2) . . . . ? S1 C14 N3 Zn1 45(6) . . . . ? N3 Zn1 N3 C14 -12(11) 3_665 . . . ? O1 Zn1 N3 C14 -102.1(6) . . . . ? O1 Zn1 N3 C14 77.9(6) 3_665 . . . ? O1W Zn1 N3 C14 166.7(6) . . . . ? O1W Zn1 N3 C14 -13.3(6) 3_665 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WB O2 0.93 1.87 2.796(2) 170.4 3_565 O1W H1WA O2 0.88 2.01 2.879(2) 171.6 2_545 _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.53 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.174 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.038 #=============================================END