Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Prof Seth Cohen' _publ_contact_author_address ; Dept. of Chemistry and Biochemistry University of California, San Diego 9500 Gilman Drive La Jolla CA 92093-0358 USA ; _publ_contact_author_email SCOHEN@UCSD.EDU _publ_section_title ; Synthesis, Structure, and Spectroscopy of New Thiopyrone and Hydroxypyridinethione Transition Metal Complexes ; loop_ _publ_author_name 'Seth Cohen' 'David Hendrickson' 'Jana A. Lewis' 'David T. Puerta' 'Evan Rumberger' ; B.L.Tran ; data_[Cu(thiomaltolato)2] _database_code_depnum_ccdc_archive 'CCDC 246105' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cu O5 S2' _chemical_formula_weight 363.88 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' 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 8.1794(11) _cell_length_b 11.3535(15) _cell_length_c 14.2539(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.253(2) _cell_angle_gamma 90.00 _cell_volume 1315.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2938 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.837 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 1.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.824464 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5413 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1503 _reflns_number_gt 1229 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+19.0223P] 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 1503 _refine_ls_number_parameters 94 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1629 _refine_ls_wR_factor_gt 0.1556 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 Cu1 Cu 0.7500 0.2500 0.0000 0.0160(3) Uani 1 2 d S . . S1 S 0.60573(16) 0.25054(12) 0.12678(8) 0.0244(3) Uani 1 1 d . . . O1 O 0.9380(4) 0.3210(3) 0.0721(2) 0.0248(8) Uani 1 1 d . . . O2 O 1.3152(4) 0.4537(3) 0.0184(3) 0.0253(8) Uani 1 1 d . . . O3 O 0.5000 0.6853(6) 0.2500 0.0347(13) Uani 1 2 d S . . C1 C 0.4440(6) 0.1726(4) 0.0736(3) 0.0196(10) Uani 1 1 d . . . C2 C 0.3119(6) 0.1327(5) 0.1221(4) 0.0235(10) Uani 1 1 d . . . H2 H 0.3101 0.1497 0.1872 0.028 Uiso 1 1 calc R . . C3 C 0.1905(6) 0.0712(5) 0.0753(3) 0.0241(11) Uani 1 1 d . . . H3 H 0.1040 0.0434 0.1089 0.029 Uiso 1 1 calc R . . C4 C 1.1924(6) 0.4162(5) 0.0665(4) 0.0261(12) Uani 1 1 d . . . C5 C 1.2220(7) 0.4448(5) 0.1696(3) 0.0268(11) Uani 1 1 d . . . H5A H 1.2913 0.3836 0.2021 0.040 Uiso 1 1 calc R . . H5B H 1.1166 0.4482 0.1962 0.040 Uiso 1 1 calc R . . H5C H 1.2775 0.5212 0.1779 0.040 Uiso 1 1 calc R . . C6 C 1.0581(5) 0.3548(4) 0.0246(3) 0.0157(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0130(4) 0.0215(5) 0.0134(4) -0.0008(3) 0.0017(3) -0.0006(3) S1 0.0231(6) 0.0317(7) 0.0186(6) -0.0023(5) 0.0026(5) -0.0041(5) O1 0.0196(17) 0.034(2) 0.0214(17) -0.0043(15) 0.0039(13) -0.0027(15) O2 0.0210(17) 0.027(2) 0.0277(19) 0.0004(16) 0.0024(14) -0.0017(15) O3 0.036(3) 0.040(4) 0.028(3) 0.000 0.004(2) 0.000 C1 0.019(2) 0.020(2) 0.020(2) 0.0000(19) 0.0017(18) 0.0013(19) C2 0.022(2) 0.028(3) 0.021(2) 0.002(2) 0.0069(19) 0.003(2) C3 0.028(3) 0.028(3) 0.017(2) 0.0046(19) 0.0065(19) 0.002(2) C4 0.021(3) 0.022(3) 0.035(3) 0.000(2) 0.000(2) 0.0017(19) C5 0.035(3) 0.026(3) 0.019(2) -0.002(2) -0.001(2) 0.003(2) C6 0.0127(19) 0.017(2) 0.017(2) 0.0007(17) -0.0001(16) 0.0014(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.930(4) 7_655 ? Cu1 O1 1.930(4) . ? Cu1 S1 2.2634(12) . ? Cu1 S1 2.2634(12) 7_655 ? S1 C1 1.700(5) . ? O1 C6 1.309(6) . ? O2 C4 1.346(6) . ? O2 C3 1.360(6) 7_655 ? C1 C2 1.419(7) . ? C1 C6 1.433(6) 7_655 ? C2 C3 1.333(8) . ? C3 O2 1.360(6) 7_655 ? C4 C6 1.381(7) . ? C4 C5 1.498(7) . ? C6 C1 1.433(6) 7_655 ? 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 Cu1 O1 180.0 7_655 . ? O1 Cu1 S1 88.38(11) 7_655 . ? O1 Cu1 S1 91.62(11) . . ? O1 Cu1 S1 91.62(11) 7_655 7_655 ? O1 Cu1 S1 88.38(11) . 7_655 ? S1 Cu1 S1 180.0 . 7_655 ? C1 S1 Cu1 95.20(17) . . ? C6 O1 Cu1 116.5(3) . . ? C4 O2 C3 119.2(4) . 7_655 ? C2 C1 C6 118.6(4) . 7_655 ? C2 C1 S1 123.1(4) . . ? C6 C1 S1 118.3(4) 7_655 . ? C3 C2 C1 119.3(5) . . ? C2 C3 O2 122.9(5) . 7_655 ? O2 C4 C6 122.8(5) . . ? O2 C4 C5 112.5(4) . . ? C6 C4 C5 124.7(5) . . ? O1 C6 C4 122.1(4) . . ? O1 C6 C1 120.8(4) . 7_655 ? C4 C6 C1 117.2(4) . 7_655 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.463 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.147 #===END data_[Zn(thiomaltolato)2] _database_code_depnum_ccdc_archive 'CCDC 246106' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 O4 S2 Zn' _chemical_formula_weight 347.69 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' 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 7.4514(7) _cell_length_b 23.556(2) _cell_length_c 7.3272(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.579(2) _cell_angle_gamma 90.00 _cell_volume 1285.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4823 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 2.240 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.722765 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8046 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2923 _reflns_number_gt 2618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0266P)^2^+1.5817P] 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 2923 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.24964(4) 0.623833(12) 0.60974(4) 0.01363(10) Uani 1 1 d . . . S1 S 0.37313(9) 0.55660(3) 0.80898(9) 0.01453(15) Uani 1 1 d . . . S2 S 0.02650(9) 0.68817(3) 0.68032(9) 0.01541(15) Uani 1 1 d . . . O1 O 0.1921(2) 0.56298(7) 0.4352(2) 0.0153(4) Uani 1 1 d . . . O2 O 0.2469(2) 0.41246(7) 0.4277(2) 0.0160(4) Uani 1 1 d . . . O3 O 0.4033(2) 0.68728(7) 0.5374(2) 0.0146(4) Uani 1 1 d . . . O4 O 0.3769(2) 0.83838(7) 0.5747(2) 0.0161(4) Uani 1 1 d . . . C1 C 0.3229(3) 0.50126(10) 0.6649(3) 0.0130(5) Uani 1 1 d . . . C2 C 0.3648(3) 0.44437(11) 0.7099(4) 0.0169(5) Uani 1 1 d . . . H2 H 0.4211 0.4357 0.8244 0.020 Uiso 1 1 calc R . . C3 C 0.3253(4) 0.40246(11) 0.5909(4) 0.0182(6) Uani 1 1 d . . . H3 H 0.3540 0.3645 0.6238 0.022 Uiso 1 1 calc R . . C4 C 0.2047(3) 0.46591(11) 0.3761(4) 0.0147(5) Uani 1 1 d . . . C5 C 0.1281(4) 0.47048(12) 0.1883(4) 0.0192(6) Uani 1 1 d . . . H5A H 0.2162 0.4881 0.1093 0.029 Uiso 1 1 calc R . . H5B H 0.0193 0.4938 0.1891 0.029 Uiso 1 1 calc R . . H5C H 0.0982 0.4325 0.1421 0.029 Uiso 1 1 calc R . . C6 C 0.2376(3) 0.51184(10) 0.4903(4) 0.0130(5) Uani 1 1 d . . . C7 C 0.1620(4) 0.74534(10) 0.6418(3) 0.0136(5) Uani 1 1 d . . . C8 C 0.1048(4) 0.80132(11) 0.6766(4) 0.0160(5) Uani 1 1 d . . . H8 H -0.0110 0.8078 0.7237 0.019 Uiso 1 1 calc R . . C9 C 0.2137(4) 0.84566(11) 0.6432(3) 0.0171(5) Uani 1 1 d . . . H9 H 0.1737 0.8830 0.6690 0.020 Uiso 1 1 calc R . . C10 C 0.4402(4) 0.78559(10) 0.5392(4) 0.0145(5) Uani 1 1 d . . . C11 C 0.6217(4) 0.78591(11) 0.4619(4) 0.0199(6) Uani 1 1 d . . . H11A H 0.6112 0.7847 0.3284 0.030 Uiso 1 1 calc R . . H11B H 0.6888 0.7527 0.5061 0.030 Uiso 1 1 calc R . . H11C H 0.6851 0.8206 0.5001 0.030 Uiso 1 1 calc R . . C12 C 0.3375(3) 0.73762(10) 0.5710(3) 0.0130(5) 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 Zn1 0.01633(16) 0.00906(15) 0.01547(17) 0.00037(11) -0.00017(11) -0.00049(11) S1 0.0177(3) 0.0119(3) 0.0138(3) 0.0001(2) -0.0025(2) -0.0003(2) S2 0.0147(3) 0.0136(3) 0.0181(3) 0.0005(2) 0.0024(3) -0.0010(2) O1 0.0204(10) 0.0104(8) 0.0150(9) 0.0020(7) -0.0029(7) -0.0010(7) O2 0.0188(9) 0.0112(8) 0.0181(10) -0.0015(7) 0.0028(8) -0.0020(7) O3 0.0139(9) 0.0110(8) 0.0191(10) 0.0003(7) 0.0016(7) 0.0006(7) O4 0.0231(10) 0.0104(8) 0.0147(10) 0.0003(7) 0.0000(8) -0.0023(7) C1 0.0140(12) 0.0139(12) 0.0113(12) 0.0000(10) 0.0044(10) -0.0009(9) C2 0.0147(13) 0.0170(13) 0.0190(14) 0.0055(10) 0.0024(10) 0.0039(10) C3 0.0172(13) 0.0133(12) 0.0243(15) 0.0027(11) 0.0044(11) 0.0024(10) C4 0.0133(12) 0.0138(12) 0.0171(14) 0.0007(10) 0.0042(10) -0.0023(9) C5 0.0209(14) 0.0194(13) 0.0175(14) -0.0027(11) 0.0021(11) -0.0048(10) C6 0.0117(12) 0.0120(12) 0.0156(13) 0.0010(10) 0.0041(10) -0.0015(9) C7 0.0194(13) 0.0129(12) 0.0083(12) 0.0011(9) -0.0025(10) 0.0012(10) C8 0.0179(13) 0.0175(13) 0.0126(13) -0.0031(10) -0.0003(10) 0.0028(10) C9 0.0276(15) 0.0119(12) 0.0116(13) -0.0025(10) -0.0010(11) 0.0044(10) C10 0.0205(13) 0.0109(12) 0.0120(13) -0.0001(9) -0.0032(10) -0.0002(10) C11 0.0204(14) 0.0196(13) 0.0197(15) 0.0011(11) -0.0004(11) -0.0047(11) C12 0.0163(13) 0.0135(12) 0.0089(13) 0.0002(9) -0.0038(10) -0.0002(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 Zn1 O1 1.9606(18) . ? Zn1 O3 1.9643(17) . ? Zn1 S2 2.3187(7) . ? Zn1 S1 2.3264(7) . ? S1 C1 1.712(3) . ? S2 C7 1.711(3) . ? O1 C6 1.312(3) . ? O2 C3 1.337(3) . ? O2 C4 1.349(3) . ? O3 C12 1.309(3) . ? O4 C9 1.339(3) . ? O4 C10 1.358(3) . ? C1 C2 1.413(3) . ? C1 C6 1.434(4) . ? C2 C3 1.344(4) . ? C4 C6 1.385(3) . ? C4 C5 1.479(4) . ? C7 C8 1.411(3) . ? C7 C12 1.432(4) . ? C8 C9 1.349(4) . ? C10 C12 1.388(3) . ? C10 C11 1.480(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O3 119.92(8) . . ? O1 Zn1 S2 118.57(6) . . ? O3 Zn1 S2 89.41(5) . . ? O1 Zn1 S1 89.27(5) . . ? O3 Zn1 S1 117.64(6) . . ? S2 Zn1 S1 125.36(3) . . ? C1 S1 Zn1 93.17(9) . . ? C7 S2 Zn1 92.74(9) . . ? C6 O1 Zn1 114.86(16) . . ? C3 O2 C4 120.5(2) . . ? C12 O3 Zn1 114.48(16) . . ? C9 O4 C10 120.9(2) . . ? C2 C1 C6 117.5(2) . . ? C2 C1 S1 122.4(2) . . ? C6 C1 S1 120.11(19) . . ? C3 C2 C1 120.1(2) . . ? O2 C3 C2 122.2(2) . . ? O2 C4 C6 121.6(2) . . ? O2 C4 C5 114.2(2) . . ? C6 C4 C5 124.2(2) . . ? O1 C6 C4 119.4(2) . . ? O1 C6 C1 122.6(2) . . ? C4 C6 C1 118.0(2) . . ? C8 C7 C12 117.9(2) . . ? C8 C7 S2 121.5(2) . . ? C12 C7 S2 120.57(19) . . ? C9 C8 C7 120.3(3) . . ? O4 C9 C8 121.7(2) . . ? O4 C10 C12 121.2(2) . . ? O4 C10 C11 113.2(2) . . ? C12 C10 C11 125.6(2) . . ? O3 C12 C10 119.7(2) . . ? O3 C12 C7 122.3(2) . . ? C10 C12 C7 118.1(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.461 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.090 #===END data_[Co(thiomaltolato)2] _database_code_depnum_ccdc_archive 'CCDC 246107' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Co O4 S2' _chemical_formula_weight 341.25 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' 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 7.4626(8) _cell_length_b 23.583(3) _cell_length_c 7.2977(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.154(2) _cell_angle_gamma 90.00 _cell_volume 1284.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6215 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 27.52 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.765 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.666 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.776631 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10787 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.53 _reflns_number_total 2945 _reflns_number_gt 2603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+11.0546P] 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 2945 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1683 _refine_ls_wR_factor_gt 0.1656 _refine_ls_goodness_of_fit_ref 1.291 _refine_ls_restrained_S_all 1.291 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 C5 C 0.6252(8) 0.7871(3) -0.0357(9) 0.0232(12) Uani 1 1 d . . . H5A H 0.6165 0.7893 -0.1697 0.035 Uiso 1 1 calc R . . H5B H 0.6882 0.7523 0.0004 0.035 Uiso 1 1 calc R . . H5C H 0.6915 0.8201 0.0115 0.035 Uiso 1 1 calc R . . C11 C 0.1283(8) 0.4698(3) -0.3133(8) 0.0218(12) Uani 1 1 d . . . H11A H 0.2171 0.4868 -0.3937 0.033 Uiso 1 1 calc R . . H11B H 0.0208 0.4937 -0.3124 0.033 Uiso 1 1 calc R . . H11C H 0.0965 0.4319 -0.3583 0.033 Uiso 1 1 calc R . . C9 C 0.3229(8) 0.4018(3) 0.0918(8) 0.0217(12) Uani 1 1 d . . . H9 H 0.3486 0.3637 0.1259 0.026 Uiso 1 1 calc R . . C8 C 0.3653(8) 0.4436(2) 0.2092(8) 0.0180(11) Uani 1 1 d . . . H8 H 0.4236 0.4349 0.3227 0.022 Uiso 1 1 calc R . . C4 C 0.4429(8) 0.7868(2) 0.0407(8) 0.0186(11) Uani 1 1 d . . . C2 C 0.1048(8) 0.8017(3) 0.1780(8) 0.0196(12) Uani 1 1 d . . . H2 H -0.0110 0.8081 0.2255 0.024 Uiso 1 1 calc R . . C3 C 0.2144(9) 0.8458(2) 0.1425(8) 0.0202(12) Uani 1 1 d . . . H3 H 0.1731 0.8831 0.1660 0.024 Uiso 1 1 calc R . . C6 C 0.3411(7) 0.7385(2) 0.0741(7) 0.0157(11) Uani 1 1 d . . . C1 C 0.1655(8) 0.7458(2) 0.1432(7) 0.0161(11) Uani 1 1 d . . . C10 C 0.2049(8) 0.4654(2) -0.1238(8) 0.0184(11) Uani 1 1 d . . . C12 C 0.2372(7) 0.5113(2) -0.0083(8) 0.0153(11) Uani 1 1 d . . . O2 O 0.3780(6) 0.83903(16) 0.0761(5) 0.0194(8) Uani 1 1 d . . . C7 C 0.3238(7) 0.5007(2) 0.1652(8) 0.0152(11) Uani 1 1 d . . . O4 O 0.2456(5) 0.41192(16) -0.0721(6) 0.0171(8) Uani 1 1 d . . . O3 O 0.1927(6) 0.56265(16) -0.0621(5) 0.0187(8) Uani 1 1 d . . . O1 O 0.4081(5) 0.68790(17) 0.0415(6) 0.0186(8) Uani 1 1 d . . . Co1 Co 0.25522(10) 0.62394(3) 0.10472(10) 0.0150(2) Uani 1 1 d . . . S2 S 0.37232(19) 0.55663(6) 0.30613(19) 0.0170(3) Uani 1 1 d . . . S1 S 0.03359(19) 0.68784(6) 0.1820(2) 0.0181(3) 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 C5 0.024(3) 0.020(3) 0.026(3) 0.002(2) 0.002(2) -0.003(2) C11 0.024(3) 0.020(3) 0.021(3) -0.004(2) 0.001(2) -0.003(2) C9 0.025(3) 0.015(3) 0.025(3) 0.003(2) 0.006(2) 0.002(2) C8 0.017(3) 0.014(3) 0.022(3) 0.004(2) 0.003(2) 0.005(2) C4 0.026(3) 0.010(2) 0.019(3) 0.000(2) -0.002(2) -0.001(2) C2 0.023(3) 0.021(3) 0.015(3) -0.004(2) 0.003(2) 0.002(2) C3 0.034(3) 0.010(2) 0.016(3) 0.000(2) -0.001(2) 0.003(2) C6 0.018(3) 0.012(3) 0.016(3) 0.002(2) -0.002(2) 0.001(2) C1 0.021(3) 0.013(3) 0.015(2) 0.003(2) 0.000(2) -0.001(2) C10 0.017(3) 0.015(3) 0.023(3) -0.001(2) 0.006(2) -0.002(2) C12 0.015(3) 0.011(2) 0.019(3) 0.001(2) 0.003(2) 0.000(2) O2 0.028(2) 0.0102(18) 0.020(2) 0.0018(15) 0.0004(17) -0.0023(16) C7 0.016(3) 0.012(2) 0.018(3) -0.003(2) 0.006(2) 0.000(2) O4 0.019(2) 0.0091(17) 0.024(2) -0.0022(15) 0.0038(16) 0.0000(15) O3 0.029(2) 0.0101(18) 0.0165(19) -0.0007(15) -0.0028(16) -0.0028(16) O1 0.0177(19) 0.0138(19) 0.024(2) -0.0003(16) 0.0059(16) 0.0004(15) Co1 0.0185(4) 0.0081(3) 0.0184(4) 0.0004(3) 0.0013(3) -0.0008(3) S2 0.0201(7) 0.0134(6) 0.0175(6) -0.0006(5) -0.0006(5) -0.0002(5) S1 0.0185(7) 0.0144(6) 0.0216(7) 0.0002(5) 0.0033(5) -0.0010(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C5 C4 1.481(8) . ? C11 C10 1.489(8) . ? C9 O4 1.339(7) . ? C9 C8 1.341(9) . ? C8 C7 1.417(7) . ? C4 O2 1.351(7) . ? C4 C6 1.392(8) . ? C2 C3 1.350(8) . ? C2 C1 1.420(8) . ? C3 O2 1.332(8) . ? C6 O1 1.318(7) . ? C6 C1 1.424(8) . ? C1 S1 1.710(6) . ? C10 O4 1.349(7) . ? C10 C12 1.390(8) . ? C12 O3 1.315(7) . ? C12 C7 1.432(8) . ? C7 S2 1.707(6) . ? O3 Co1 1.940(4) . ? O1 Co1 1.952(4) . ? Co1 S1 2.3157(16) . ? Co1 S2 2.3221(16) . ? 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 O4 C9 C8 122.1(5) . . ? C9 C8 C7 120.4(5) . . ? O2 C4 C6 120.9(5) . . ? O2 C4 C5 113.8(5) . . ? C6 C4 C5 125.4(5) . . ? C3 C2 C1 119.0(5) . . ? O2 C3 C2 122.7(5) . . ? O1 C6 C4 119.9(5) . . ? O1 C6 C1 121.8(5) . . ? C4 C6 C1 118.3(5) . . ? C2 C1 C6 118.2(5) . . ? C2 C1 S1 121.8(4) . . ? C6 C1 S1 120.0(4) . . ? O4 C10 C12 121.5(5) . . ? O4 C10 C11 113.9(5) . . ? C12 C10 C11 124.6(5) . . ? O3 C12 C10 119.8(5) . . ? O3 C12 C7 122.1(5) . . ? C10 C12 C7 118.1(5) . . ? C3 O2 C4 120.9(5) . . ? C8 C7 C12 117.3(5) . . ? C8 C7 S2 123.7(5) . . ? C12 C7 S2 119.0(4) . . ? C9 O4 C10 120.5(5) . . ? C12 O3 Co1 116.3(3) . . ? C6 O1 Co1 115.6(3) . . ? O3 Co1 O1 124.16(17) . . ? O3 Co1 S1 118.28(14) . . ? O1 Co1 S1 88.76(12) . . ? O3 Co1 S2 88.31(12) . . ? O1 Co1 S2 117.61(13) . . ? S1 Co1 S2 123.52(6) . . ? C7 S2 Co1 94.3(2) . . ? C1 S1 Co1 93.6(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.928 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.149 #===END data_[Ni(maltolato)2(H2O)2] _database_code_depnum_ccdc_archive 'CCDC 246108' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H26 Ni O14' _chemical_formula_weight 453.04 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 4.8648(3) _cell_length_b 16.7242(12) _cell_length_c 23.6399(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1923.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 6135 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.40 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.828743 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15280 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2215 _reflns_number_gt 1820 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+1.4095P] 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 2215 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0703 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.002 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 Ni1 Ni 1.0000 1.0000 0.0000 0.01090(10) Uani 1 2 d S . . O1 O 0.7762(2) 1.01938(7) 0.07165(5) 0.0125(3) Uani 1 1 d . . . O3 O 1.1462(3) 0.90503(7) 0.04602(5) 0.0144(3) Uani 1 1 d . . . O5 O 0.0050(3) 0.84099(9) 0.89068(6) 0.0192(3) Uani 1 1 d . . . O4 O 0.6892(3) 0.92548(8) -0.02985(6) 0.0147(3) Uani 1 1 d . . . O2 O 0.7434(3) 0.89355(8) 0.19595(5) 0.0193(3) Uani 1 1 d . . . C6 C 0.8188(4) 0.95971(11) 0.10802(8) 0.0133(4) Uani 1 1 d . . . O6 O 0.5269(4) 0.77239(10) 0.02628(7) 0.0245(3) Uani 1 1 d . . . C4 C 0.6889(4) 0.95477(11) 0.15905(8) 0.0155(4) Uani 1 1 d . . . C1 C 1.0202(4) 0.89953(11) 0.09274(8) 0.0143(4) Uani 1 1 d . . . C3 C 0.9288(4) 0.83751(12) 0.18205(9) 0.0207(4) Uani 1 1 d . . . C2 C 1.0668(4) 0.83741(12) 0.13299(8) 0.0186(4) Uani 1 1 d . . . C5 C 0.4860(4) 1.01244(13) 0.18202(9) 0.0209(4) Uani 1 1 d . . . O7 O 1.0510(3) 0.18196(11) 0.22429(7) 0.0292(4) Uani 1 1 d . . . H3 H 0.944(4) 0.7983(13) 0.2104(9) 0.021(6) Uiso 1 1 d . . . H7 H 0.751(5) 0.9000(14) -0.0549(10) 0.027(7) Uiso 1 1 d . . . H12 H 1.031(5) 0.1745(16) 0.1922(12) 0.036(8) Uiso 1 1 d . . . H8 H 0.109(5) 0.8766(15) 0.8999(10) 0.031(7) Uiso 1 1 d . . . H11 H 0.489(6) 0.816(2) 0.0257(13) 0.049(10) Uiso 1 1 d . . . H6 H 0.546(5) 0.9502(15) -0.0428(10) 0.032(7) Uiso 1 1 d . . . H9 H 0.036(5) 0.8055(16) 0.9113(11) 0.030(7) Uiso 1 1 d . . . H13 H 0.911(7) 0.1784(17) 0.2384(12) 0.047(9) Uiso 1 1 d . . . H5B H 0.340(6) 0.9852(16) 0.1968(11) 0.043(8) Uiso 1 1 d . . . H5C H 0.429(6) 1.0456(18) 0.1547(12) 0.053(9) Uiso 1 1 d . . . H2 H 1.190(5) 0.7988(13) 0.1263(9) 0.025(6) Uiso 1 1 d . . . H5A H 0.560(6) 1.0432(17) 0.2110(12) 0.046(8) Uiso 1 1 d . . . H10 H 0.670(7) 0.7676(17) 0.0102(12) 0.046(9) Uiso 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 Ni1 0.01030(15) 0.01148(16) 0.01091(16) 0.00118(12) 0.00081(13) 0.00081(13) O1 0.0125(6) 0.0123(6) 0.0127(6) 0.0017(5) 0.0009(5) 0.0013(5) O3 0.0143(6) 0.0143(6) 0.0147(6) 0.0015(5) 0.0007(5) 0.0027(5) O5 0.0247(7) 0.0166(7) 0.0165(7) -0.0005(6) -0.0025(6) -0.0022(7) O4 0.0124(6) 0.0158(7) 0.0159(7) -0.0008(6) -0.0005(6) 0.0021(5) O2 0.0227(7) 0.0213(7) 0.0140(6) 0.0047(5) 0.0018(6) 0.0011(6) C6 0.0126(8) 0.0131(9) 0.0141(9) -0.0004(7) -0.0018(7) -0.0034(7) O6 0.0272(8) 0.0173(8) 0.0292(8) 0.0036(6) 0.0014(7) 0.0025(7) C4 0.0157(9) 0.0154(9) 0.0155(9) 0.0025(7) -0.0022(7) -0.0021(7) C1 0.0138(8) 0.0141(8) 0.0149(9) -0.0009(7) -0.0027(7) -0.0028(7) C3 0.0257(10) 0.0157(10) 0.0208(10) 0.0052(8) -0.0022(8) 0.0009(8) C2 0.0203(10) 0.0146(9) 0.0209(10) 0.0026(8) -0.0016(8) 0.0034(8) C5 0.0211(10) 0.0254(11) 0.0162(9) 0.0002(8) 0.0022(9) 0.0016(9) O7 0.0224(8) 0.0488(11) 0.0164(8) -0.0044(7) -0.0003(7) -0.0010(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 Ni1 O1 2.0395(12) 5_775 ? Ni1 O1 2.0395(12) . ? Ni1 O3 2.0525(12) 5_775 ? Ni1 O3 2.0525(12) . ? Ni1 O4 2.0826(13) . ? Ni1 O4 2.0826(13) 5_775 ? O1 C6 1.333(2) . ? O3 C1 1.267(2) . ? O2 C3 1.342(2) . ? O2 C4 1.371(2) . ? C6 C4 1.364(3) . ? C6 C1 1.450(3) . ? C4 C5 1.483(3) . ? C1 C2 1.427(3) . ? C3 C2 1.340(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 Ni1 O1 180.0 5_775 . ? O1 Ni1 O3 82.40(5) 5_775 5_775 ? O1 Ni1 O3 97.60(5) . 5_775 ? O1 Ni1 O3 97.60(5) 5_775 . ? O1 Ni1 O3 82.40(5) . . ? O3 Ni1 O3 180.00(6) 5_775 . ? O1 Ni1 O4 90.63(5) 5_775 . ? O1 Ni1 O4 89.37(5) . . ? O3 Ni1 O4 91.83(5) 5_775 . ? O3 Ni1 O4 88.17(5) . . ? O1 Ni1 O4 89.37(5) 5_775 5_775 ? O1 Ni1 O4 90.63(5) . 5_775 ? O3 Ni1 O4 88.17(5) 5_775 5_775 ? O3 Ni1 O4 91.83(5) . 5_775 ? O4 Ni1 O4 180.00(7) . 5_775 ? C6 O1 Ni1 109.48(10) . . ? C1 O3 Ni1 110.52(11) . . ? C3 O2 C4 119.72(15) . . ? O1 C6 C4 122.92(16) . . ? O1 C6 C1 117.64(16) . . ? C4 C6 C1 119.40(16) . . ? C6 C4 O2 121.23(17) . . ? C6 C4 C5 126.34(17) . . ? O2 C4 C5 112.42(16) . . ? O3 C1 C2 123.86(17) . . ? O3 C1 C6 119.59(16) . . ? C2 C1 C6 116.54(16) . . ? C2 C3 O2 123.35(18) . . ? C3 C2 C1 119.76(18) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.385 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.065 #===END data_[Co(3,4-HOPTO)3] _database_code_depnum_ccdc_archive 'CCDC 246109' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '[Co(3,4-HOPTO)3]' _chemical_formula_sum 'C25 H36 Co1 N3 O5 S5' _chemical_formula_weight 677.80 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3244(14) _cell_length_b 15.860(2) _cell_length_c 17.356(2) _cell_angle_alpha 88.703(2) _cell_angle_beta 81.334(2) _cell_angle_gamma 78.963(2) _cell_volume 3024.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5214 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.53 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 0.952 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.677863 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; The disordered dimethylsulfoxide solvate molecules were treated by SQUEEZE. Corrections of the X-ray data by SQUEEZE (349 electrons/cell) were close to the required values of 336 electrons/cell for eight molecules of DMSO per cell. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19654 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_av_sigmaI/netI 0.1243 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 24.00 _reflns_number_total 9400 _reflns_number_gt 4979 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0902P)^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 9400 _refine_ls_number_parameters 559 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1189 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.1748 _refine_ls_wR_factor_gt 0.1603 _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_restrained_S_all 0.899 _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 0.37547(9) 0.76039(5) 0.16628(5) 0.0372(3) Uani 1 1 d . . . Co2 Co 0.57836(9) 0.23364(5) 0.33613(5) 0.0371(3) Uani 1 1 d . . . S1 S 0.28398(17) 0.74250(10) 0.28608(11) 0.0441(5) Uani 1 1 d . . . S2 S 0.25217(17) 0.88621(10) 0.15932(11) 0.0429(5) Uani 1 1 d . . . S3 S 0.24590(19) 0.69525(12) 0.11890(12) 0.0537(6) Uani 1 1 d . . . S4 S 0.71036(18) 0.32052(10) 0.33731(11) 0.0460(5) Uani 1 1 d . . . S5 S 0.45184(17) 0.33356(9) 0.28278(10) 0.0412(5) Uani 1 1 d . . . S6 S 0.66335(18) 0.18338(10) 0.21862(10) 0.0420(5) Uani 1 1 d . . . O1 O 0.4936(4) 0.8109(2) 0.2117(3) 0.0388(11) Uani 1 1 d . . . O2 O 0.4614(4) 0.7828(2) 0.0639(2) 0.0405(12) Uani 1 1 d . . . O3 O 0.4868(4) 0.6495(3) 0.1638(3) 0.0444(12) Uani 1 1 d . . . O4 O 0.5041(4) 0.2751(3) 0.4393(2) 0.0434(12) Uani 1 1 d . . . O5 O 0.4598(4) 0.1594(2) 0.3412(2) 0.0365(11) Uani 1 1 d . . . O6 O 0.6855(4) 0.1405(3) 0.3800(2) 0.0384(11) Uani 1 1 d . . . N1 N 0.5206(6) 0.8770(3) 0.4033(3) 0.0431(15) Uani 1 1 d . . . N2 N 0.4375(6) 0.9567(3) -0.0739(3) 0.0477(17) Uani 1 1 d . . . N3 N 0.4923(9) 0.4388(4) 0.0906(4) 0.070(2) Uani 1 1 d . . . N4 N 0.5531(7) 0.4250(3) 0.5769(4) 0.059(2) Uani 1 1 d . . . N5 N 0.1808(6) 0.1656(3) 0.2682(4) 0.0585(19) Uani 1 1 d . . . N6 N 0.9247(5) -0.0335(4) 0.3041(4) 0.0484(16) Uani 1 1 d . . . C1 C 0.3689(6) 0.7995(4) 0.3330(4) 0.0368(17) Uani 1 1 d . . . C2 C 0.3451(7) 0.8186(4) 0.4120(4) 0.0443(18) Uani 1 1 d . . . H2A H 0.2751 0.8043 0.4429 0.053 Uiso 1 1 calc R . . C3 C 0.4219(7) 0.8576(4) 0.4454(4) 0.0442(19) Uani 1 1 d . . . H3A H 0.4045 0.8711 0.4994 0.053 Uiso 1 1 calc R . . C4 C 0.6054(7) 0.9136(4) 0.4443(4) 0.057(2) Uani 1 1 d . . . H4A H 0.5727 0.9204 0.4998 0.085 Uiso 1 1 calc R . . H4B H 0.6147 0.9698 0.4221 0.085 Uiso 1 1 calc R . . H4C H 0.6849 0.8749 0.4379 0.085 Uiso 1 1 calc R . . C5 C 0.5478(7) 0.8622(4) 0.3247(4) 0.0419(18) Uani 1 1 d . . . C6 C 0.6656(6) 0.8817(4) 0.2818(4) 0.049(2) Uani 1 1 d . . . H6A H 0.7073 0.9076 0.3179 0.074 Uiso 1 1 calc R . . H6B H 0.6482 0.9219 0.2393 0.074 Uiso 1 1 calc R . . H6C H 0.7177 0.8284 0.2602 0.074 Uiso 1 1 calc R . . C7 C 0.4700(6) 0.8250(4) 0.2875(4) 0.0342(16) Uani 1 1 d . . . C8 C 0.3193(6) 0.9133(4) 0.0691(4) 0.0408(18) Uani 1 1 d . . . C9 C 0.2803(7) 0.9908(4) 0.0311(4) 0.0441(19) Uani 1 1 d . . . H9A H 0.2107 1.0299 0.0548 0.053 Uiso 1 1 calc R . . C10 C 0.3399(7) 1.0111(4) -0.0389(5) 0.050(2) Uani 1 1 d . . . H10A H 0.3121 1.0641 -0.0630 0.060 Uiso 1 1 calc R . . C11 C 0.5017(8) 0.9787(5) -0.1501(4) 0.061(2) Uani 1 1 d . . . H11A H 0.4622 1.0355 -0.1662 0.092 Uiso 1 1 calc R . . H11B H 0.4988 0.9357 -0.1891 0.092 Uiso 1 1 calc R . . H11C H 0.5866 0.9796 -0.1455 0.092 Uiso 1 1 calc R . . C12 C 0.4795(7) 0.8776(4) -0.0407(4) 0.0417(18) Uani 1 1 d . . . C13 C 0.5871(7) 0.8206(4) -0.0832(4) 0.053(2) Uani 1 1 d . . . H13A H 0.6066 0.7679 -0.0534 0.079 Uiso 1 1 calc R . . H13B H 0.6565 0.8500 -0.0902 0.079 Uiso 1 1 calc R . . H13C H 0.5694 0.8061 -0.1344 0.079 Uiso 1 1 calc R . . C14 C 0.4214(6) 0.8566(4) 0.0297(4) 0.0343(16) Uani 1 1 d . . . C15 C 0.3389(8) 0.5950(4) 0.1097(4) 0.049(2) Uani 1 1 d . . . C16 C 0.3043(10) 0.5235(5) 0.0766(5) 0.074(3) Uani 1 1 d . . . H16A H 0.2257 0.5290 0.0619 0.089 Uiso 1 1 calc R . . C17 C 0.3822(11) 0.4493(6) 0.0665(5) 0.083(3) Uani 1 1 d . . . H17A H 0.3603 0.4028 0.0419 0.100 Uiso 1 1 calc R . . C18 C 0.5807(10) 0.3558(5) 0.0764(5) 0.100(4) Uani 1 1 d . . . H18A H 0.5435 0.3149 0.0514 0.150 Uiso 1 1 calc R . . H18B H 0.6025 0.3324 0.1262 0.150 Uiso 1 1 calc R . . H18C H 0.6540 0.3656 0.0424 0.150 Uiso 1 1 calc R . . C19 C 0.5307(8) 0.5044(4) 0.1257(4) 0.055(2) Uani 1 1 d . . . C20 C 0.6509(8) 0.4877(5) 0.1530(5) 0.075(3) Uani 1 1 d . . . H20A H 0.6909 0.4279 0.1414 0.113 Uiso 1 1 calc R . . H20B H 0.6398 0.4978 0.2093 0.113 Uiso 1 1 calc R . . H20C H 0.7016 0.5263 0.1262 0.113 Uiso 1 1 calc R . . C21 C 0.4505(7) 0.5853(4) 0.1344(4) 0.0454(19) Uani 1 1 d . . . C22 C 0.6520(7) 0.3631(4) 0.4297(4) 0.0396(18) Uani 1 1 d . . . C23 C 0.7017(8) 0.4260(4) 0.4656(5) 0.057(2) Uani 1 1 d . . . H23A H 0.7690 0.4482 0.4394 0.069 Uiso 1 1 calc R . . C24 C 0.6482(9) 0.4530(4) 0.5393(5) 0.055(2) Uani 1 1 d . . . H24A H 0.6812 0.4937 0.5645 0.067 Uiso 1 1 calc R . . C25 C 0.5039(8) 0.4578(4) 0.6565(4) 0.067(3) Uani 1 1 d . . . H25A H 0.5520 0.4985 0.6711 0.101 Uiso 1 1 calc R . . H25B H 0.5081 0.4097 0.6931 0.101 Uiso 1 1 calc R . . H25C H 0.4190 0.4869 0.6582 0.101 Uiso 1 1 calc R . . C26 C 0.4985(8) 0.3661(4) 0.5449(4) 0.047(2) Uani 1 1 d . . . C27 C 0.3887(8) 0.3401(4) 0.5886(4) 0.061(2) Uani 1 1 d . . . H27A H 0.3675 0.3700 0.6391 0.092 Uiso 1 1 calc R . . H27B H 0.4051 0.2779 0.5971 0.092 Uiso 1 1 calc R . . H27C H 0.3209 0.3552 0.5587 0.092 Uiso 1 1 calc R . . C28 C 0.5520(8) 0.3347(4) 0.4702(4) 0.047(2) Uani 1 1 d . . . C29 C 0.3439(7) 0.2721(4) 0.2758(4) 0.0419(18) Uani 1 1 d . . . C30 C 0.2397(7) 0.2996(4) 0.2411(4) 0.052(2) Uani 1 1 d . . . H30A H 0.2248 0.3556 0.2196 0.062 Uiso 1 1 calc R . . C31 C 0.1601(8) 0.2465(4) 0.2381(5) 0.072(3) Uani 1 1 d . . . H31A H 0.0891 0.2658 0.2148 0.086 Uiso 1 1 calc R . . C32 C 0.0885(8) 0.1125(5) 0.2642(6) 0.089(3) Uani 1 1 d . . . H32A H 0.1139 0.0563 0.2875 0.134 Uiso 1 1 calc R . . H32B H 0.0801 0.1046 0.2096 0.134 Uiso 1 1 calc R . . H32C H 0.0103 0.1411 0.2927 0.134 Uiso 1 1 calc R . . C33 C 0.2802(7) 0.1358(4) 0.3010(4) 0.0416(18) Uani 1 1 d . . . C34 C 0.2940(7) 0.0470(4) 0.3361(4) 0.053(2) Uani 1 1 d . . . H34A H 0.2277 0.0197 0.3252 0.080 Uiso 1 1 calc R . . H34B H 0.2912 0.0515 0.3926 0.080 Uiso 1 1 calc R . . H34C H 0.3722 0.0123 0.3134 0.080 Uiso 1 1 calc R . . C35 C 0.3645(6) 0.1877(4) 0.3086(4) 0.0330(16) Uani 1 1 d . . . C36 C 0.7619(6) 0.0979(4) 0.2494(4) 0.0360(16) Uani 1 1 d . . . C37 C 0.8402(6) 0.0361(4) 0.1985(4) 0.0445(18) Uani 1 1 d . . . H37A H 0.8373 0.0389 0.1441 0.053 Uiso 1 1 calc R . . C38 C 0.9193(7) -0.0272(5) 0.2275(5) 0.053(2) Uani 1 1 d . . . H38A H 0.9723 -0.0681 0.1928 0.064 Uiso 1 1 calc R . . C39 C 1.0156(7) -0.1019(5) 0.3328(5) 0.072(3) Uani 1 1 d . . . H39A H 1.0628 -0.1368 0.2887 0.108 Uiso 1 1 calc R . . H39B H 0.9739 -0.1385 0.3694 0.108 Uiso 1 1 calc R . . H39C H 1.0704 -0.0759 0.3593 0.108 Uiso 1 1 calc R . . C40 C 0.8485(6) 0.0231(5) 0.3569(4) 0.0433(18) Uani 1 1 d . . . C41 C 0.8625(7) 0.0160(5) 0.4408(4) 0.057(2) Uani 1 1 d . . . H41A H 0.9257 -0.0338 0.4483 0.085 Uiso 1 1 calc R . . H41B H 0.7852 0.0090 0.4717 0.085 Uiso 1 1 calc R . . H41C H 0.8859 0.0683 0.4577 0.085 Uiso 1 1 calc R . . C42 C 0.7640(6) 0.0895(4) 0.3313(4) 0.0348(17) 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 0.0478(6) 0.0185(4) 0.0473(6) 0.0032(4) -0.0112(5) -0.0082(4) Co2 0.0612(7) 0.0175(4) 0.0371(6) -0.0008(4) -0.0180(5) -0.0103(4) S1 0.0466(12) 0.0277(9) 0.0572(13) 0.0105(8) -0.0041(9) -0.0094(8) S2 0.0494(12) 0.0237(9) 0.0565(12) 0.0039(8) -0.0109(9) -0.0072(8) S3 0.0661(14) 0.0369(10) 0.0657(14) 0.0068(9) -0.0240(11) -0.0186(10) S4 0.0693(14) 0.0284(9) 0.0486(12) -0.0009(8) -0.0217(10) -0.0195(9) S5 0.0662(13) 0.0182(8) 0.0450(11) -0.0033(7) -0.0222(9) -0.0114(8) S6 0.0676(14) 0.0243(9) 0.0372(11) 0.0003(7) -0.0184(9) -0.0085(8) O1 0.060(3) 0.026(2) 0.034(3) 0.004(2) -0.011(2) -0.017(2) O2 0.056(3) 0.021(2) 0.046(3) 0.005(2) -0.011(2) -0.007(2) O3 0.057(3) 0.021(2) 0.054(3) 0.002(2) -0.009(3) -0.006(2) O4 0.071(4) 0.024(2) 0.037(3) -0.004(2) -0.013(2) -0.010(2) O5 0.050(3) 0.021(2) 0.044(3) 0.000(2) -0.020(2) -0.009(2) O6 0.051(3) 0.027(2) 0.037(3) -0.001(2) -0.019(2) 0.002(2) N1 0.058(4) 0.030(3) 0.040(4) -0.003(3) -0.006(3) -0.006(3) N2 0.092(5) 0.029(3) 0.037(4) 0.011(3) -0.032(3) -0.033(4) N3 0.146(8) 0.015(3) 0.040(4) 0.005(3) 0.009(4) -0.012(4) N4 0.113(6) 0.018(3) 0.048(4) -0.001(3) -0.032(4) 0.000(4) N5 0.070(5) 0.028(3) 0.091(5) -0.006(3) -0.042(4) -0.020(3) N6 0.033(4) 0.041(4) 0.065(5) 0.016(3) -0.004(3) 0.005(3) C1 0.041(5) 0.025(3) 0.041(4) 0.012(3) -0.005(3) 0.000(3) C2 0.049(5) 0.033(4) 0.045(5) 0.014(3) -0.001(4) 0.001(3) C3 0.062(6) 0.034(4) 0.029(4) 0.006(3) -0.003(4) 0.006(4) C4 0.087(6) 0.040(4) 0.046(5) -0.001(4) -0.023(4) -0.011(4) C5 0.059(5) 0.022(3) 0.047(5) 0.008(3) -0.019(4) -0.008(3) C6 0.063(6) 0.039(4) 0.048(5) -0.002(3) -0.008(4) -0.013(4) C7 0.037(4) 0.026(3) 0.039(4) 0.006(3) -0.010(3) 0.001(3) C8 0.043(5) 0.039(4) 0.051(5) -0.006(3) -0.034(4) -0.013(3) C9 0.054(5) 0.025(4) 0.055(5) 0.005(3) -0.019(4) -0.004(3) C10 0.066(6) 0.021(4) 0.070(6) 0.008(4) -0.028(5) -0.012(4) C11 0.111(7) 0.041(4) 0.046(5) 0.012(4) -0.031(5) -0.039(5) C12 0.073(6) 0.023(3) 0.036(4) 0.000(3) -0.017(4) -0.020(4) C13 0.082(6) 0.041(4) 0.041(5) 0.004(4) -0.012(4) -0.024(4) C14 0.046(5) 0.017(3) 0.044(4) 0.002(3) -0.019(4) -0.007(3) C15 0.082(6) 0.027(4) 0.043(5) 0.007(3) -0.009(4) -0.027(4) C16 0.138(9) 0.028(5) 0.070(6) 0.007(4) -0.035(6) -0.032(5) C17 0.155(11) 0.038(6) 0.067(7) 0.005(5) -0.020(7) -0.041(7) C18 0.178(11) 0.032(5) 0.072(7) 0.003(4) 0.005(7) 0.004(6) C19 0.093(7) 0.025(4) 0.034(5) 0.010(3) 0.020(4) -0.003(4) C20 0.103(8) 0.041(5) 0.068(6) 0.004(4) 0.000(6) 0.012(5) C21 0.064(6) 0.033(4) 0.038(4) 0.011(3) -0.006(4) -0.009(4) C22 0.059(5) 0.022(3) 0.041(4) 0.001(3) -0.023(4) -0.003(3) C23 0.094(7) 0.024(4) 0.067(6) 0.008(4) -0.047(5) -0.016(4) C24 0.112(8) 0.019(4) 0.048(5) -0.004(4) -0.052(5) -0.011(4) C25 0.139(8) 0.024(4) 0.039(5) -0.006(3) -0.038(5) 0.003(4) C26 0.082(6) 0.013(3) 0.046(5) -0.006(3) -0.023(4) -0.002(4) C27 0.107(7) 0.030(4) 0.038(5) -0.006(3) -0.011(5) 0.010(4) C28 0.084(6) 0.014(3) 0.044(5) 0.003(3) -0.024(4) -0.003(4) C29 0.065(5) 0.015(3) 0.049(5) -0.005(3) -0.017(4) -0.006(3) C30 0.075(6) 0.026(4) 0.059(5) -0.004(3) -0.024(4) -0.008(4) C31 0.089(7) 0.025(4) 0.115(8) -0.001(4) -0.059(6) -0.013(4) C32 0.082(7) 0.047(5) 0.160(10) 0.001(6) -0.069(7) -0.028(5) C33 0.054(5) 0.025(3) 0.053(5) -0.004(3) -0.029(4) -0.008(3) C34 0.093(6) 0.015(3) 0.057(5) 0.002(3) -0.025(4) -0.014(4) C35 0.049(5) 0.018(3) 0.036(4) -0.005(3) -0.017(3) -0.009(3) C36 0.031(4) 0.033(4) 0.049(5) 0.003(3) -0.017(3) -0.010(3) C37 0.046(5) 0.040(4) 0.049(5) -0.002(4) -0.001(4) -0.016(4) C38 0.049(5) 0.049(5) 0.057(6) -0.002(4) 0.004(4) -0.008(4) C39 0.055(6) 0.058(5) 0.091(7) 0.029(5) 0.001(5) 0.011(4) C40 0.034(4) 0.056(5) 0.043(5) 0.013(4) -0.009(4) -0.013(4) C41 0.062(6) 0.057(5) 0.054(5) 0.025(4) -0.022(4) -0.010(4) C42 0.023(4) 0.025(3) 0.062(5) 0.002(3) -0.019(4) -0.009(3) _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 O2 1.953(4) . ? Co1 O1 1.952(4) . ? Co1 O3 1.955(4) . ? Co1 S3 2.209(2) . ? Co1 S1 2.217(2) . ? Co1 S2 2.2180(19) . ? Co2 O4 1.932(4) . ? Co2 O6 1.942(4) . ? Co2 O5 1.940(4) . ? Co2 S5 2.2104(19) . ? Co2 S6 2.216(2) . ? Co2 S4 2.2210(19) . ? S1 C1 1.735(7) . ? S2 C8 1.717(7) . ? S3 C15 1.727(7) . ? S4 C22 1.739(7) . ? S5 C29 1.722(7) . ? S6 C36 1.714(6) . ? O1 C7 1.318(7) . ? O2 C14 1.333(7) . ? O3 C21 1.309(8) . ? O4 C28 1.334(8) . ? O5 C35 1.294(7) . ? O6 C42 1.299(7) . ? N1 C3 1.324(9) . ? N1 C5 1.367(8) . ? N1 C4 1.485(8) . ? N2 C10 1.338(9) . ? N2 C12 1.398(8) . ? N2 C11 1.478(9) . ? N3 C17 1.354(11) . ? N3 C19 1.387(10) . ? N3 C18 1.493(10) . ? N4 C24 1.319(10) . ? N4 C26 1.383(9) . ? N4 C25 1.476(9) . ? N5 C33 1.339(8) . ? N5 C31 1.366(9) . ? N5 C32 1.473(8) . ? N6 C38 1.341(9) . ? N6 C40 1.376(9) . ? N6 C39 1.479(8) . ? C1 C2 1.386(9) . ? C1 C7 1.409(9) . ? C2 C3 1.359(9) . ? C5 C7 1.390(9) . ? C5 C6 1.509(9) . ? C8 C9 1.409(8) . ? C8 C14 1.416(9) . ? C9 C10 1.361(10) . ? C12 C14 1.363(9) . ? C12 C13 1.478(10) . ? C15 C21 1.375(10) . ? C15 C16 1.427(9) . ? C16 C17 1.326(12) . ? C19 C21 1.420(10) . ? C19 C20 1.483(11) . ? C22 C28 1.386(10) . ? C22 C23 1.431(9) . ? C23 C24 1.371(10) . ? C26 C28 1.405(10) . ? C26 C27 1.480(10) . ? C29 C30 1.396(9) . ? C29 C35 1.434(8) . ? C30 C31 1.353(10) . ? C33 C35 1.395(8) . ? C33 C34 1.512(8) . ? C36 C37 1.412(9) . ? C36 C42 1.429(9) . ? C37 C38 1.354(9) . ? C40 C42 1.394(9) . ? C40 C41 1.488(9) . ? 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 O2 Co1 O1 87.62(18) . . ? O2 Co1 O3 87.53(18) . . ? O1 Co1 O3 88.56(18) . . ? O2 Co1 S3 94.24(14) . . ? O1 Co1 S3 176.20(13) . . ? O3 Co1 S3 88.22(15) . . ? O2 Co1 S1 175.69(14) . . ? O1 Co1 S1 88.37(14) . . ? O3 Co1 S1 93.96(14) . . ? S3 Co1 S1 89.85(8) . . ? O2 Co1 S2 88.45(13) . . ? O1 Co1 S2 92.98(13) . . ? O3 Co1 S2 175.64(15) . . ? S3 Co1 S2 90.38(8) . . ? S1 Co1 S2 90.17(7) . . ? O4 Co2 O6 90.86(18) . . ? O4 Co2 O5 88.24(18) . . ? O6 Co2 O5 88.13(18) . . ? O4 Co2 S5 90.86(14) . . ? O6 Co2 S5 176.47(13) . . ? O5 Co2 S5 88.83(13) . . ? O4 Co2 S6 178.84(14) . . ? O6 Co2 S6 88.31(14) . . ? O5 Co2 S6 90.92(14) . . ? S5 Co2 S6 89.92(7) . . ? O4 Co2 S4 88.55(14) . . ? O6 Co2 S4 91.47(14) . . ? O5 Co2 S4 176.76(14) . . ? S5 Co2 S4 91.66(7) . . ? S6 Co2 S4 92.28(8) . . ? C1 S1 Co1 96.3(2) . . ? C8 S2 Co1 96.1(2) . . ? C15 S3 Co1 96.1(3) . . ? C22 S4 Co2 96.0(3) . . ? C29 S5 Co2 96.4(2) . . ? C36 S6 Co2 96.6(2) . . ? C7 O1 Co1 116.2(4) . . ? C14 O2 Co1 117.5(4) . . ? C21 O3 Co1 115.8(4) . . ? C28 O4 Co2 116.9(5) . . ? C35 O5 Co2 116.4(4) . . ? C42 O6 Co2 117.2(4) . . ? C3 N1 C5 122.3(6) . . ? C3 N1 C4 118.0(6) . . ? C5 N1 C4 119.7(6) . . ? C10 N2 C12 121.3(6) . . ? C10 N2 C11 120.2(6) . . ? C12 N2 C11 118.5(7) . . ? C17 N3 C19 122.4(7) . . ? C17 N3 C18 120.4(8) . . ? C19 N3 C18 117.1(9) . . ? C24 N4 C26 122.6(7) . . ? C24 N4 C25 118.4(7) . . ? C26 N4 C25 119.0(7) . . ? C33 N5 C31 121.5(6) . . ? C33 N5 C32 121.0(6) . . ? C31 N5 C32 117.4(6) . . ? C38 N6 C40 121.5(6) . . ? C38 N6 C39 119.5(7) . . ? C40 N6 C39 119.0(6) . . ? C2 C1 C7 119.0(6) . . ? C2 C1 S1 123.9(6) . . ? C7 C1 S1 117.1(5) . . ? C3 C2 C1 120.1(7) . . ? N1 C3 C2 120.7(7) . . ? N1 C5 C7 119.1(7) . . ? N1 C5 C6 119.0(6) . . ? C7 C5 C6 121.8(7) . . ? O1 C7 C5 120.3(6) . . ? O1 C7 C1 121.1(6) . . ? C5 C7 C1 118.6(7) . . ? C9 C8 C14 116.5(7) . . ? C9 C8 S2 123.9(6) . . ? C14 C8 S2 119.7(5) . . ? C10 C9 C8 121.7(7) . . ? N2 C10 C9 120.3(6) . . ? C14 C12 N2 119.1(7) . . ? C14 C12 C13 122.7(6) . . ? N2 C12 C13 118.2(6) . . ? O2 C14 C12 120.5(6) . . ? O2 C14 C8 118.3(6) . . ? C12 C14 C8 121.1(6) . . ? C21 C15 C16 119.7(7) . . ? C21 C15 S3 118.0(5) . . ? C16 C15 S3 122.3(7) . . ? C17 C16 C15 119.8(9) . . ? C16 C17 N3 121.0(8) . . ? N3 C19 C21 117.4(8) . . ? N3 C19 C20 119.6(7) . . ? C21 C19 C20 123.0(7) . . ? O3 C21 C15 121.8(6) . . ? O3 C21 C19 118.7(7) . . ? C15 C21 C19 119.5(7) . . ? C28 C22 C23 118.7(7) . . ? C28 C22 S4 118.0(5) . . ? C23 C22 S4 123.3(6) . . ? C24 C23 C22 117.3(8) . . ? N4 C24 C23 123.1(7) . . ? N4 C26 C28 116.5(7) . . ? N4 C26 C27 120.0(7) . . ? C28 C26 C27 123.5(6) . . ? O4 C28 C22 120.6(7) . . ? O4 C28 C26 117.7(7) . . ? C22 C28 C26 121.7(6) . . ? C30 C29 C35 119.3(6) . . ? C30 C29 S5 124.2(5) . . ? C35 C29 S5 116.5(5) . . ? C31 C30 C29 120.0(7) . . ? C30 C31 N5 120.7(7) . . ? N5 C33 C35 121.1(6) . . ? N5 C33 C34 118.4(6) . . ? C35 C33 C34 120.3(6) . . ? O5 C35 C33 121.2(5) . . ? O5 C35 C29 121.4(6) . . ? C33 C35 C29 117.3(6) . . ? C37 C36 C42 118.9(6) . . ? C37 C36 S6 123.8(5) . . ? C42 C36 S6 117.4(5) . . ? C38 C37 C36 119.8(7) . . ? N6 C38 C37 121.5(7) . . ? N6 C40 C42 120.2(6) . . ? N6 C40 C41 119.3(6) . . ? C42 C40 C41 120.4(7) . . ? O6 C42 C40 121.6(6) . . ? O6 C42 C36 120.3(6) . . ? C40 C42 C36 118.1(6) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.670 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.090 #===END data_[Fe(3,4-HOPTO)3] _database_code_depnum_ccdc_archive 'CCDC 246110' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 Fe N3 O3 S3' _chemical_formula_weight 518.46 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' _cell_length_a 15.6574(18) _cell_length_b 15.6574(18) _cell_length_c 15.540(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3299.3(9) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4831 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.53 _exptl_crystal_description needle _exptl_crystal_colour navy_blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1614 _exptl_absorpt_coefficient_mu 1.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.834877 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6528 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.53 _reflns_number_total 1585 _reflns_number_gt 1531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0289P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.020(19) _refine_ls_number_reflns 1585 _refine_ls_number_parameters 96 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0612 _refine_ls_wR_factor_gt 0.0608 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.160 _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 Fe1 Fe 1.0000 1.0000 0.76649(4) 0.01236(12) Uani 1 3 d S . . S1 S 0.87875(4) 0.87326(4) 0.86476(4) 0.01702(12) Uani 1 1 d . . . O1 O 0.87671(11) 0.95991(11) 0.69836(9) 0.0141(3) Uani 1 1 d . . . N1 N 0.61950(14) 0.87031(14) 0.74004(12) 0.0163(4) Uani 1 1 d . . . C1 C 0.77849(16) 0.87439(15) 0.81983(15) 0.0153(4) Uani 1 1 d . . . C2 C 0.68754(17) 0.83573(16) 0.86100(15) 0.0179(5) Uani 1 1 d . . . H2 H 0.6795 0.8097 0.9175 0.021 Uiso 1 1 calc R . . C3 C 0.60948(17) 0.83512(16) 0.82016(16) 0.0186(5) Uani 1 1 d . . . H3 H 0.5480 0.8096 0.8489 0.022 Uiso 1 1 calc R . . C4 C 0.53214(17) 0.8648(2) 0.69838(16) 0.0250(5) Uani 1 1 d . . . H4A H 0.4745 0.8286 0.7357 0.037 Uiso 1 1 calc R . . H4B H 0.5202 0.8305 0.6431 0.037 Uiso 1 1 calc R . . H4C H 0.5437 0.9316 0.6887 0.037 Uiso 1 1 calc R . . C5 C 0.70722(17) 0.91105(16) 0.69599(14) 0.0146(4) Uani 1 1 d . . . C6 C 0.70964(17) 0.94574(18) 0.60606(15) 0.0183(5) Uani 1 1 d . . . H6A H 0.6636 0.8900 0.5703 0.027 Uiso 1 1 calc R . . H6B H 0.7765 0.9735 0.5828 0.027 Uiso 1 1 calc R . . H6C H 0.6904 0.9965 0.6060 0.027 Uiso 1 1 calc R . . C7 C 0.79019(16) 0.91752(16) 0.73661(14) 0.0133(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01137(15) 0.01137(15) 0.0143(2) 0.000 0.000 0.00569(8) S1 0.0156(3) 0.0168(3) 0.0178(3) 0.0035(2) -0.0006(2) 0.0075(2) O1 0.0116(7) 0.0150(7) 0.0159(8) 0.0008(6) 0.0002(6) 0.0069(6) N1 0.0123(9) 0.0162(9) 0.0202(10) -0.0046(7) -0.0005(7) 0.0069(8) C1 0.0148(11) 0.0117(10) 0.0194(11) -0.0028(8) -0.0011(9) 0.0067(8) C2 0.0205(13) 0.0147(10) 0.0155(12) -0.0002(9) 0.0021(9) 0.0065(10) C3 0.0155(11) 0.0169(11) 0.0208(11) -0.0031(9) 0.0028(9) 0.0062(9) C4 0.0187(12) 0.0331(14) 0.0270(14) -0.0065(10) -0.0033(10) 0.0158(11) C5 0.0138(10) 0.0120(10) 0.0188(11) -0.0038(8) -0.0001(8) 0.0070(9) C6 0.0171(11) 0.0208(11) 0.0186(12) -0.0041(9) -0.0027(8) 0.0107(9) C7 0.0141(10) 0.0106(10) 0.0155(11) -0.0028(7) 0.0004(8) 0.0064(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 Fe1 O1 2.0073(15) 2_765 ? Fe1 O1 2.0074(15) 3_675 ? Fe1 O1 2.0074(15) . ? Fe1 S1 2.4711(7) 2_765 ? Fe1 S1 2.4712(7) 3_675 ? Fe1 S1 2.4712(7) . ? S1 C1 1.726(2) . ? O1 C7 1.315(2) . ? N1 C3 1.339(3) . ? N1 C5 1.373(3) . ? N1 C4 1.476(3) . ? C1 C2 1.393(3) . ? C1 C7 1.428(3) . ? C2 C3 1.373(4) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C7 1.402(3) . ? C5 C6 1.493(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? 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 Fe1 O1 94.74(6) 2_765 3_675 ? O1 Fe1 O1 94.74(6) 2_765 . ? O1 Fe1 O1 94.74(6) 3_675 . ? O1 Fe1 S1 80.93(5) 2_765 2_765 ? O1 Fe1 S1 99.72(4) 3_675 2_765 ? O1 Fe1 S1 165.18(5) . 2_765 ? O1 Fe1 S1 165.19(5) 2_765 3_675 ? O1 Fe1 S1 80.93(5) 3_675 3_675 ? O1 Fe1 S1 99.72(4) . 3_675 ? S1 Fe1 S1 85.82(3) 2_765 3_675 ? O1 Fe1 S1 99.72(4) 2_765 . ? O1 Fe1 S1 165.18(5) 3_675 . ? O1 Fe1 S1 80.93(5) . . ? S1 Fe1 S1 85.82(3) 2_765 . ? S1 Fe1 S1 85.82(3) 3_675 . ? C1 S1 Fe1 94.54(8) . . ? C7 O1 Fe1 120.41(13) . . ? C3 N1 C5 122.61(19) . . ? C3 N1 C4 117.99(19) . . ? C5 N1 C4 119.4(2) . . ? C2 C1 C7 118.9(2) . . ? C2 C1 S1 123.15(18) . . ? C7 C1 S1 117.97(16) . . ? C3 C2 C1 120.2(2) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? N1 C3 C2 120.4(2) . . ? N1 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 C7 119.0(2) . . ? N1 C5 C6 118.24(19) . . ? C7 C5 C6 122.8(2) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O1 C7 C5 121.10(19) . . ? O1 C7 C1 120.28(19) . . ? C5 C7 C1 118.60(19) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.347 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.064 #===END data_[Ni(3,4-HOPTO)2] _database_code_depnum_ccdc_archive 'CCDC 246111' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 N2 Ni O3 S2' _chemical_formula_weight 399.16 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.4626(7) _cell_length_b 19.3473(18) _cell_length_c 22.730(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3281.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 27.52 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 1.452 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.785266 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26647 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3766 _reflns_number_gt 3025 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+1.9028P] 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 3766 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.0970 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 Ni1 Ni 0.09529(5) 0.349914(18) 0.397950(15) 0.01156(11) Uani 1 1 d . . . S1 S 0.09408(10) 0.34968(4) 0.49291(3) 0.01507(16) Uani 1 1 d . . . S2 S -0.03478(10) 0.25099(4) 0.39579(3) 0.01444(16) Uani 1 1 d . . . O1 O 0.2114(3) 0.43637(10) 0.39807(8) 0.0140(4) Uani 1 1 d . . . O2 O 0.0966(3) 0.35297(10) 0.31536(8) 0.0159(4) Uani 1 1 d . . . O3 O 1.0472(3) 0.52675(13) 0.31565(11) 0.0271(6) Uani 1 1 d . . . N1 N -0.0316(3) 0.23658(12) 0.19924(10) 0.0126(5) Uani 1 1 d . . . N2 N 0.3131(3) 0.56455(12) 0.50712(10) 0.0133(5) Uani 1 1 d . . . C1 C 0.1741(4) 0.43289(15) 0.50152(12) 0.0126(6) Uani 1 1 d . . . C2 C 0.1850(4) 0.46793(15) 0.55490(12) 0.0148(6) Uani 1 1 d . . . H2 H 0.1449 0.4464 0.5901 0.018 Uiso 1 1 calc R . . C3 C 0.2534(4) 0.53329(15) 0.55645(12) 0.0164(6) Uani 1 1 d . . . H3A H 0.2590 0.5572 0.5929 0.020 Uiso 1 1 calc R . . C4 C 0.3813(4) 0.63583(15) 0.51195(13) 0.0179(7) Uani 1 1 d . . . H4A H 0.3561 0.6538 0.5514 0.027 Uiso 1 1 calc R . . H4B H 0.3221 0.6650 0.4826 0.027 Uiso 1 1 calc R . . H4C H 0.5109 0.6361 0.5051 0.027 Uiso 1 1 calc R . . C5 C 0.3054(3) 0.53297(14) 0.45377(12) 0.0116(6) Uani 1 1 d . . . C6 C 0.3733(4) 0.56953(15) 0.40031(12) 0.0160(6) Uani 1 1 d . . . H6A H 0.2839 0.6032 0.3871 0.024 Uiso 1 1 calc R . . H6B H 0.3951 0.5358 0.3689 0.024 Uiso 1 1 calc R . . H6C H 0.4853 0.5935 0.4098 0.024 Uiso 1 1 calc R . . C7 C 0.2304(4) 0.46706(15) 0.44948(12) 0.0125(6) Uani 1 1 d . . . C8 C -0.0334(4) 0.24127(15) 0.32024(12) 0.0148(6) Uani 1 1 d . . . C9 C -0.0943(4) 0.18301(15) 0.28996(13) 0.0167(6) Uani 1 1 d . . . H9 H -0.1389 0.1443 0.3112 0.020 Uiso 1 1 calc R . . C10 C -0.0900(4) 0.18161(15) 0.23009(13) 0.0159(6) Uani 1 1 d . . . H10 H -0.1286 0.1413 0.2098 0.019 Uiso 1 1 calc R . . C11 C -0.0278(4) 0.23194(16) 0.13426(12) 0.0184(7) Uani 1 1 d . . . H11A H -0.0697 0.1862 0.1220 0.028 Uiso 1 1 calc R . . H11B H 0.0950 0.2391 0.1203 0.028 Uiso 1 1 calc R . . H11C H -0.1063 0.2675 0.1175 0.028 Uiso 1 1 calc R . . C12 C 0.0281(4) 0.29541(14) 0.22612(12) 0.0125(6) Uani 1 1 d . . . C13 C 0.0857(4) 0.35514(15) 0.18929(12) 0.0157(6) Uani 1 1 d . . . H13A H 0.1824 0.3406 0.1629 0.024 Uiso 1 1 calc R . . H13B H 0.1287 0.3925 0.2148 0.024 Uiso 1 1 calc R . . H13C H -0.0161 0.3717 0.1660 0.024 Uiso 1 1 calc R . . C14 C 0.0331(4) 0.29824(14) 0.28737(12) 0.0127(6) Uani 1 1 d . . . C15 C 0.8944(4) 0.50924(17) 0.28199(14) 0.0252(7) Uani 1 1 d . . . H15A H 0.7892 0.5070 0.3077 0.038 Uiso 1 1 calc R . . H15B H 0.9130 0.4642 0.2633 0.038 Uiso 1 1 calc R . . H15C H 0.8750 0.5444 0.2516 0.038 Uiso 1 1 calc R . . H3B H 1.080(5) 0.496(2) 0.3312(17) 0.033(12) Uiso 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 Ni1 0.01416(19) 0.01016(19) 0.01035(18) 0.00047(15) -0.00036(14) -0.00069(14) S1 0.0177(4) 0.0154(4) 0.0121(3) 0.0026(3) -0.0005(3) -0.0026(3) S2 0.0180(4) 0.0118(3) 0.0135(3) 0.0011(3) 0.0000(3) -0.0018(3) O1 0.0174(10) 0.0127(10) 0.0120(10) -0.0002(8) 0.0008(8) -0.0024(8) O2 0.0239(11) 0.0125(10) 0.0112(10) -0.0024(8) -0.0003(8) -0.0029(9) O3 0.0273(14) 0.0222(14) 0.0319(14) 0.0124(11) -0.0065(10) -0.0001(10) N1 0.0120(12) 0.0129(13) 0.0128(12) -0.0019(9) 0.0015(9) -0.0003(9) N2 0.0124(12) 0.0139(13) 0.0137(12) -0.0009(10) 0.0001(9) -0.0005(10) C1 0.0074(14) 0.0154(16) 0.0150(14) 0.0010(11) -0.0009(10) 0.0018(11) C2 0.0118(14) 0.0198(16) 0.0128(14) 0.0009(12) 0.0004(11) 0.0010(11) C3 0.0161(15) 0.0209(16) 0.0124(14) -0.0039(12) -0.0008(11) 0.0016(12) C4 0.0215(17) 0.0120(16) 0.0203(16) -0.0070(12) -0.0005(12) -0.0046(12) C5 0.0082(13) 0.0145(15) 0.0121(14) -0.0004(11) 0.0004(10) 0.0023(11) C6 0.0191(15) 0.0145(15) 0.0143(15) 0.0027(12) -0.0002(12) -0.0026(11) C7 0.0108(13) 0.0139(15) 0.0127(14) -0.0011(11) 0.0005(11) 0.0020(10) C8 0.0167(15) 0.0142(15) 0.0135(14) 0.0007(12) 0.0005(11) 0.0020(11) C9 0.0166(15) 0.0106(14) 0.0229(16) 0.0019(12) -0.0007(12) -0.0010(12) C10 0.0149(15) 0.0126(15) 0.0202(15) -0.0042(12) -0.0022(12) -0.0013(11) C11 0.0207(16) 0.0225(18) 0.0120(15) -0.0055(12) 0.0008(12) -0.0040(12) C12 0.0119(14) 0.0134(15) 0.0122(14) -0.0026(11) 0.0002(10) 0.0020(11) C13 0.0192(15) 0.0149(15) 0.0132(14) -0.0003(11) -0.0005(11) -0.0022(12) C14 0.0107(13) 0.0136(15) 0.0139(15) -0.0006(11) 0.0005(10) 0.0026(11) C15 0.0291(19) 0.0199(17) 0.0267(18) -0.0018(13) -0.0015(14) -0.0006(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O2 1.8782(19) . ? Ni1 O1 1.8840(19) . ? Ni1 S2 2.1466(8) . ? Ni1 S1 2.1584(8) . ? S1 C1 1.728(3) . ? S2 C8 1.728(3) . ? O1 C7 1.318(3) . ? O2 C14 1.323(3) . ? O3 C15 1.415(4) . ? N1 C10 1.347(4) . ? N1 C12 1.366(3) . ? N1 C11 1.480(3) . ? N2 C3 1.350(4) . ? N2 C5 1.359(3) . ? N2 C4 1.474(4) . ? C1 C2 1.392(4) . ? C1 C7 1.419(4) . ? C2 C3 1.364(4) . ? C5 C7 1.396(4) . ? C5 C6 1.494(4) . ? C8 C9 1.397(4) . ? C8 C14 1.421(4) . ? C9 C10 1.361(4) . ? C12 C14 1.394(4) . ? C12 C13 1.490(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 O2 Ni1 O1 88.34(8) . . ? O2 Ni1 S2 90.44(6) . . ? O1 Ni1 S2 178.68(6) . . ? O2 Ni1 S1 178.32(6) . . ? O1 Ni1 S1 90.13(6) . . ? S2 Ni1 S1 91.09(3) . . ? C1 S1 Ni1 96.31(10) . . ? C8 S2 Ni1 96.72(10) . . ? C7 O1 Ni1 116.78(17) . . ? C14 O2 Ni1 116.97(18) . . ? C10 N1 C12 122.0(2) . . ? C10 N1 C11 118.6(2) . . ? C12 N1 C11 119.4(2) . . ? C3 N2 C5 121.7(2) . . ? C3 N2 C4 118.1(2) . . ? C5 N2 C4 120.1(2) . . ? C2 C1 C7 118.9(3) . . ? C2 C1 S1 124.9(2) . . ? C7 C1 S1 116.2(2) . . ? C3 C2 C1 119.7(3) . . ? N2 C3 C2 121.2(3) . . ? N2 C5 C7 119.3(2) . . ? N2 C5 C6 119.9(2) . . ? C7 C5 C6 120.8(2) . . ? O1 C7 C5 121.1(2) . . ? O1 C7 C1 119.8(3) . . ? C5 C7 C1 119.1(3) . . ? C9 C8 C14 118.7(3) . . ? C9 C8 S2 125.2(2) . . ? C14 C8 S2 116.1(2) . . ? C10 C9 C8 120.1(3) . . ? N1 C10 C9 120.8(3) . . ? N1 C12 C14 119.2(3) . . ? N1 C12 C13 119.3(2) . . ? C14 C12 C13 121.5(3) . . ? O2 C14 C12 121.4(3) . . ? O2 C14 C8 119.5(3) . . ? C12 C14 C8 119.0(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.672 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.091 #===END data_[Cu(3,2-HOPTO)2] _database_code_depnum_ccdc_archive 'CCDC 246112' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cu N2 O2 S2' _chemical_formula_weight 343.90 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.0152(6) _cell_length_b 14.9663(13) _cell_length_c 12.7659(11) _cell_angle_alpha 90.00 _cell_angle_beta 105.9180(10) _cell_angle_gamma 90.00 _cell_volume 1288.92(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7585 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 2.015 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.547804 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10823 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.55 _reflns_number_total 2948 _reflns_number_gt 2727 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+2.8967P] 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 2948 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 Cu1 Cu 0.16373(5) 0.23493(3) 0.96961(3) 0.01816(13) Uani 1 1 d . . . S1 S 0.23388(13) 0.09060(5) 0.94423(6) 0.02390(19) Uani 1 1 d . . . S2 S 0.12519(12) 0.21133(5) 1.13530(6) 0.02274(18) Uani 1 1 d . . . O1 O 0.1399(3) 0.25505(15) 0.81773(18) 0.0206(4) Uani 1 1 d . . . O2 O 0.1531(3) 0.36287(14) 0.99902(17) 0.0195(4) Uani 1 1 d . . . N1 N 0.2130(4) 0.03025(18) 0.7423(2) 0.0221(5) Uani 1 1 d . . . N2 N 0.1743(4) 0.3466(2) 1.2793(2) 0.0242(6) Uani 1 1 d . . . C1 C 0.1977(4) 0.1013(2) 0.8053(2) 0.0192(6) Uani 1 1 d . . . C2 C 0.2565(5) -0.0587(2) 0.7919(3) 0.0282(7) Uani 1 1 d . . . H2A H 0.3773 -0.0558 0.8526 0.042 Uiso 1 1 calc R . . H2B H 0.2757 -0.1012 0.7373 0.042 Uiso 1 1 calc R . . H2C H 0.1454 -0.0784 0.8190 0.042 Uiso 1 1 calc R . . C3 C 0.1877(5) 0.0385(2) 0.6333(3) 0.0252(7) Uani 1 1 d . . . H3 H 0.1984 -0.0126 0.5911 0.030 Uiso 1 1 calc R . . C4 C 0.1470(5) 0.1200(2) 0.5844(3) 0.0238(6) Uani 1 1 d . . . H4 H 0.1302 0.1255 0.5083 0.029 Uiso 1 1 calc R . . C5 C 0.1299(5) 0.1954(2) 0.6455(3) 0.0218(6) Uani 1 1 d . . . H5 H 0.1017 0.2519 0.6109 0.026 Uiso 1 1 calc R . . C6 C 0.1540(4) 0.1880(2) 0.7574(2) 0.0194(6) Uani 1 1 d . . . C7 C 0.1581(4) 0.3224(2) 1.1744(2) 0.0201(6) Uani 1 1 d . . . C8 C 0.1666(5) 0.2779(3) 1.3599(3) 0.0304(8) Uani 1 1 d . . . H8A H 0.1949 0.3052 1.4323 0.046 Uiso 1 1 calc R . . H8B H 0.2655 0.2317 1.3599 0.046 Uiso 1 1 calc R . . H8C H 0.0342 0.2510 1.3412 0.046 Uiso 1 1 calc R . . C9 C 0.1961(5) 0.4327(3) 1.3116(3) 0.0279(7) Uani 1 1 d . . . H9 H 0.2093 0.4479 1.3855 0.033 Uiso 1 1 calc R . . C10 C 0.1989(5) 0.4988(2) 1.2357(3) 0.0287(7) Uani 1 1 d . . . H10 H 0.2120 0.5597 1.2576 0.034 Uiso 1 1 calc R . . C11 C 0.1830(5) 0.4766(2) 1.1283(3) 0.0267(7) Uani 1 1 d . . . H11 H 0.1830 0.5225 1.0768 0.032 Uiso 1 1 calc R . . C12 C 0.1668(5) 0.3877(2) 1.0953(3) 0.0220(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 Cu1 0.0194(2) 0.0200(2) 0.01434(19) -0.00294(13) 0.00344(14) 0.00088(13) S1 0.0332(4) 0.0205(4) 0.0182(4) 0.0002(3) 0.0075(3) 0.0037(3) S2 0.0296(4) 0.0206(4) 0.0189(4) 0.0022(3) 0.0081(3) -0.0007(3) O1 0.0248(11) 0.0203(11) 0.0165(10) 0.0000(8) 0.0052(8) -0.0007(8) O2 0.0231(11) 0.0110(10) 0.0194(10) 0.0007(8) -0.0028(8) -0.0008(8) N1 0.0232(13) 0.0218(14) 0.0230(13) -0.0059(10) 0.0092(10) -0.0026(10) N2 0.0210(13) 0.0325(15) 0.0192(13) 0.0004(11) 0.0057(10) 0.0011(11) C1 0.0184(14) 0.0196(15) 0.0209(14) -0.0038(11) 0.0073(11) -0.0024(11) C2 0.0367(18) 0.0167(15) 0.0350(18) -0.0040(13) 0.0164(15) -0.0007(13) C3 0.0240(15) 0.0300(17) 0.0238(15) -0.0102(13) 0.0106(12) -0.0051(13) C4 0.0227(15) 0.0325(18) 0.0179(14) -0.0037(12) 0.0084(11) -0.0030(13) C5 0.0214(15) 0.0241(16) 0.0201(14) -0.0003(12) 0.0060(11) -0.0017(12) C6 0.0175(14) 0.0210(15) 0.0196(14) -0.0007(12) 0.0047(11) -0.0024(11) C7 0.0171(14) 0.0276(16) 0.0157(13) -0.0052(12) 0.0043(10) 0.0000(12) C8 0.0283(17) 0.046(2) 0.0175(15) 0.0099(14) 0.0079(12) 0.0046(15) C9 0.0236(16) 0.040(2) 0.0208(15) -0.0127(14) 0.0068(12) -0.0032(14) C10 0.0270(17) 0.0253(17) 0.0360(18) -0.0101(14) 0.0125(14) -0.0047(13) C11 0.0281(17) 0.0259(17) 0.0278(16) 0.0003(13) 0.0102(13) -0.0021(13) C12 0.0195(14) 0.0230(16) 0.0239(15) 0.0009(12) 0.0070(11) 0.0006(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 Cu1 O1 1.924(2) . ? Cu1 O2 1.957(2) . ? Cu1 S2 2.2328(8) . ? Cu1 S1 2.2584(9) . ? S1 C1 1.729(3) . ? S2 C7 1.733(3) . ? O1 C6 1.285(4) . ? O2 C12 1.263(4) . ? N1 C1 1.355(4) . ? N1 C3 1.358(4) . ? N1 C2 1.470(4) . ? N2 C9 1.349(5) . ? N2 C7 1.361(4) . ? N2 C8 1.466(4) . ? C1 C6 1.431(4) . ? C3 C4 1.365(5) . ? C4 C5 1.395(5) . ? C5 C6 1.396(4) . ? C7 C12 1.417(4) . ? C9 C10 1.390(5) . ? C10 C11 1.384(5) . ? C11 C12 1.392(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 O1 Cu1 O2 92.45(9) . . ? O1 Cu1 S2 168.53(7) . . ? O2 Cu1 S2 87.26(7) . . ? O1 Cu1 S1 88.12(7) . . ? O2 Cu1 S1 169.99(7) . . ? S2 Cu1 S1 94.16(3) . . ? C1 S1 Cu1 94.74(11) . . ? C7 S2 Cu1 94.57(10) . . ? C6 O1 Cu1 118.8(2) . . ? C12 O2 Cu1 118.5(2) . . ? C1 N1 C3 121.8(3) . . ? C1 N1 C2 119.7(3) . . ? C3 N1 C2 118.5(3) . . ? C9 N2 C7 121.8(3) . . ? C9 N2 C8 118.5(3) . . ? C7 N2 C8 119.7(3) . . ? N1 C1 C6 120.0(3) . . ? N1 C1 S1 121.6(2) . . ? C6 C1 S1 118.4(2) . . ? N1 C3 C4 120.1(3) . . ? C3 C4 C5 120.4(3) . . ? C4 C5 C6 120.2(3) . . ? O1 C6 C5 122.9(3) . . ? O1 C6 C1 119.7(3) . . ? C5 C6 C1 117.4(3) . . ? N2 C7 C12 120.6(3) . . ? N2 C7 S2 120.4(2) . . ? C12 C7 S2 119.0(2) . . ? N2 C9 C10 119.3(3) . . ? C11 C10 C9 120.5(3) . . ? C10 C11 C12 120.4(3) . . ? O2 C12 C11 123.6(3) . . ? O2 C12 C7 118.9(3) . . ? C11 C12 C7 117.4(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.554 _refine_diff_density_min -0.716 _refine_diff_density_rms 0.125 #===END data_[Zn(3,2-HOPTO)2] _database_code_depnum_ccdc_archive 'CCDC 246113' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 N2 O2 S2 Zn' _chemical_formula_weight 345.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 25.738(3) _cell_length_b 8.2241(9) _cell_length_c 12.2965(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2602.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4872 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 27.54 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.765 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 2.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.715473 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5326 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.54 _reflns_number_total 1486 _reflns_number_gt 1455 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.0437P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.058(14) _refine_ls_number_reflns 1486 _refine_ls_number_parameters 88 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.2500 0.2500 0.43597(4) 0.02495(14) Uani 1 2 d S . . S1 S 0.17619(3) 0.15690(9) 0.52273(5) 0.02886(18) Uani 1 1 d . . . O1 O 0.20666(8) 0.3846(3) 0.34023(16) 0.0306(4) Uani 1 1 d . . . N1 N 0.08343(9) 0.2553(3) 0.4475(3) 0.0256(5) Uani 1 1 d . . . C1 C 0.13610(10) 0.2670(3) 0.4362(4) 0.0231(5) Uani 1 1 d . . . C2 C 0.06129(11) 0.1462(3) 0.5312(3) 0.0321(6) Uani 1 1 d . . . H2A H 0.0234 0.1590 0.5331 0.048 Uiso 1 1 calc R . . H2B H 0.0758 0.1740 0.6025 0.048 Uiso 1 1 calc R . . H2C H 0.0699 0.0332 0.5135 0.048 Uiso 1 1 calc R . . C3 C 0.04991(12) 0.3386(4) 0.3827(3) 0.0331(6) Uani 1 1 d . . . H3 H 0.0135 0.3302 0.3944 0.040 Uiso 1 1 calc R . . C4 C 0.06877(12) 0.4347(4) 0.3005(3) 0.0351(7) Uani 1 1 d . . . H4 H 0.0455 0.4916 0.2542 0.042 Uiso 1 1 calc R . . C5 C 0.12186(11) 0.4483(4) 0.2855(3) 0.0306(6) Uani 1 1 d . . . H5 H 0.1345 0.5133 0.2274 0.037 Uiso 1 1 calc R . . C6 C 0.15781(13) 0.3685(4) 0.3541(3) 0.0284(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 Zn1 0.0159(2) 0.0335(2) 0.0254(2) 0.000 0.000 -0.00003(17) S1 0.0237(3) 0.0356(4) 0.0273(3) 0.0031(3) 0.0017(3) 0.0000(3) O1 0.0239(10) 0.0395(11) 0.0283(10) 0.0061(8) 0.0011(8) -0.0022(9) N1 0.0189(10) 0.0276(10) 0.0302(13) -0.0047(9) 0.0030(12) -0.0009(9) C1 0.0193(11) 0.0242(11) 0.0257(11) -0.0059(11) -0.0039(15) 0.0020(9) C2 0.0228(12) 0.0349(15) 0.0384(17) 0.0017(14) 0.0054(14) -0.0044(11) C3 0.0195(13) 0.0412(17) 0.0386(15) -0.0001(14) -0.0007(12) -0.0002(12) C4 0.0253(14) 0.0400(17) 0.0401(18) 0.0032(14) -0.0030(13) 0.0043(13) C5 0.0250(13) 0.0357(13) 0.0312(14) 0.0009(12) 0.0016(13) 0.0001(12) C6 0.0328(15) 0.0226(12) 0.0298(14) -0.0053(11) 0.0116(12) -0.0004(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.964(2) . ? Zn1 O1 1.964(2) 14 ? Zn1 S1 2.3093(8) . ? Zn1 S1 2.3093(8) 14 ? S1 C1 1.737(3) . ? O1 C6 1.276(4) . ? N1 C3 1.359(4) . ? N1 C1 1.366(3) . ? N1 C2 1.480(4) . ? C1 C6 1.424(5) . ? C3 C4 1.372(5) . ? C4 C5 1.383(4) . ? C5 C6 1.414(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 O1 Zn1 O1 106.33(13) . 14 ? O1 Zn1 S1 89.81(7) . . ? O1 Zn1 S1 123.87(7) 14 . ? O1 Zn1 S1 123.87(7) . 14 ? O1 Zn1 S1 89.80(7) 14 14 ? S1 Zn1 S1 124.97(4) . 14 ? C1 S1 Zn1 91.89(12) . . ? C6 O1 Zn1 114.9(2) . . ? C3 N1 C1 122.4(3) . . ? C3 N1 C2 117.9(3) . . ? C1 N1 C2 119.7(3) . . ? N1 C1 C6 120.2(3) . . ? N1 C1 S1 119.4(3) . . ? C6 C1 S1 120.4(2) . . ? N1 C3 C4 119.8(3) . . ? C3 C4 C5 119.7(3) . . ? C4 C5 C6 121.9(3) . . ? O1 C6 C5 121.1(3) . . ? O1 C6 C1 122.9(3) . . ? C5 C6 C1 116.0(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.810 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.113