# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'D.Parker' 'Aileen Cogreve' 'Ritu Kataky' 'Mark Knell' 'Horst Puschmann' 'Kanthi Senanayake' 'Lisa Wylie' _publ_contact_author_name 'Prof David Parker' _publ_contact_author_address ; Department of Chemistry University of Durham Sough Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email DAVID.PARKER@DUR.AC.UK _journal_name_full 'New Journal of Chemistry' _publ_section_title ; Examination of Cobalt, Nickel, Copper and Zinc(II) complex geometry and binding affinity in aqueous media using simple pyridylsulfonamide ligands ; data_L1 _database_code_CSD 186296 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N2 O2 S,(H2 O)0.5' _chemical_formula_sum 'C13 H15 N2 O2.50 S' _chemical_formula_weight 271.33 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' _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 26.831(4) _cell_length_b 5.9583(8) _cell_length_c 16.576(2) _cell_angle_alpha 90 _cell_angle_beta 99.967(3) _cell_angle_gamma 90 _cell_volume 2610.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 888 _cell_measurement_theta_min 12.04 _cell_measurement_theta_max 25.59 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.6 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.87448 _exptl_absorpt_correction_T_max 0.97589 _exptl_absorpt_process_details 'XPREP (SHELXTL,1997), R(int)=0.035 before correction' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (15 s exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 110(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 '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 13742 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2993 _reflns_number_gt 2707 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0308P)^2^+3.8043P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2993 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.212 _refine_ls_restrained_S_all 1.212 _refine_ls_shift/su_max 0.003 _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 S1 S 0.368843(15) 0.07482(7) 0.11638(2) 0.01919(12) Uani 1 1 d . . . O1 O 0.36575(5) -0.1654(2) 0.10763(8) 0.0271(3) Uani 1 1 d . . . O2 O 0.34758(4) 0.2163(2) 0.04928(7) 0.0254(3) Uani 1 1 d . . . N1 N 0.42869(5) 0.1305(2) 0.13906(9) 0.0205(3) Uani 1 1 d . . . H1N H 0.4434(9) 0.044(4) 0.1728(15) 0.035(6) Uiso 1 1 d . . . N2 N 0.52050(5) 0.5829(2) 0.13220(9) 0.0227(3) Uani 1 1 d . . . C1 C 0.27697(8) 0.3198(4) 0.41386(12) 0.0331(4) Uani 1 1 d . . . H1C H 0.2962(11) 0.265(5) 0.4623(19) 0.064(9) Uiso 1 1 d . . . H1B H 0.2425(11) 0.279(5) 0.4084(16) 0.053(7) Uiso 1 1 d . . . H1A H 0.2768(11) 0.480(6) 0.4244(19) 0.070(9) Uiso 1 1 d . . . C2 C 0.29988(6) 0.2603(3) 0.33997(10) 0.0230(4) Uani 1 1 d . . . C3 C 0.29902(6) 0.4124(3) 0.27601(11) 0.0236(4) Uani 1 1 d . . . H3 H 0.2846(8) 0.557(4) 0.2791(13) 0.028(5) Uiso 1 1 d . . . C4 C 0.31954(6) 0.3591(3) 0.20684(11) 0.0212(3) Uani 1 1 d . . . H4 H 0.3187(7) 0.460(4) 0.1642(13) 0.024(5) Uiso 1 1 d . . . C5 C 0.34082(6) 0.1479(3) 0.20163(10) 0.0181(3) Uani 1 1 d . . . C6 C 0.34212(6) -0.0073(3) 0.26493(11) 0.0225(3) Uani 1 1 d . . . H6 H 0.3561(8) -0.148(4) 0.2603(13) 0.027(5) Uiso 1 1 d . . . C7 C 0.32162(6) 0.0499(3) 0.33342(11) 0.0248(4) Uani 1 1 d . . . H7 H 0.3225(8) -0.054(4) 0.3761(14) 0.033(6) Uiso 1 1 d . . . C8 C 0.44711(6) 0.3618(3) 0.14721(10) 0.0192(3) Uani 1 1 d . . . H8B H 0.4509(7) 0.414(3) 0.2046(13) 0.022(5) Uiso 1 1 d . . . H8A H 0.4225(8) 0.462(3) 0.1162(12) 0.022(5) Uiso 1 1 d . . . C9 C 0.49754(6) 0.3830(3) 0.11801(9) 0.0179(3) Uani 1 1 d . . . C10 C 0.51823(6) 0.2110(3) 0.07800(10) 0.0229(3) Uani 1 1 d . . . H10 H 0.5018(8) 0.069(4) 0.0716(12) 0.024(5) Uiso 1 1 d . . . C11 C 0.56336(7) 0.2489(3) 0.04962(11) 0.0264(4) Uani 1 1 d . . . H11 H 0.5775(8) 0.128(4) 0.0213(14) 0.034(6) Uiso 1 1 d . . . C12 C 0.58649(6) 0.4566(3) 0.06220(11) 0.0253(4) Uani 1 1 d . . . H12 H 0.6160(9) 0.489(4) 0.0428(13) 0.032(6) Uiso 1 1 d . . . C13 C 0.56400(6) 0.6164(3) 0.10426(11) 0.0259(4) Uani 1 1 d . . . H13 H 0.5795(8) 0.760(4) 0.1146(13) 0.032(6) Uiso 1 1 d . . . O1W O 0.5000 0.8823(3) 0.2500 0.0233(4) Uani 1 2 d S . . H1W H 0.5069(9) 0.795(4) 0.2129(14) 0.043(7) 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 S1 0.01900(19) 0.0196(2) 0.0200(2) -0.00198(16) 0.00649(14) -0.00255(15) O1 0.0299(6) 0.0213(6) 0.0329(7) -0.0059(5) 0.0131(5) -0.0042(5) O2 0.0235(6) 0.0323(7) 0.0205(6) 0.0023(5) 0.0037(5) -0.0025(5) N1 0.0180(6) 0.0187(7) 0.0257(7) 0.0026(6) 0.0063(5) 0.0000(5) N2 0.0208(7) 0.0200(7) 0.0266(7) -0.0005(6) 0.0025(5) -0.0017(5) C1 0.0258(9) 0.0498(13) 0.0257(9) -0.0077(9) 0.0099(7) -0.0013(9) C2 0.0158(7) 0.0316(9) 0.0219(8) -0.0049(7) 0.0039(6) -0.0018(7) C3 0.0201(8) 0.0228(9) 0.0281(9) -0.0045(7) 0.0048(6) 0.0019(6) C4 0.0203(7) 0.0204(8) 0.0231(8) 0.0028(7) 0.0044(6) 0.0004(6) C5 0.0152(7) 0.0206(8) 0.0192(7) -0.0011(6) 0.0051(6) -0.0021(6) C6 0.0216(8) 0.0197(8) 0.0266(8) 0.0023(7) 0.0056(6) 0.0017(6) C7 0.0241(8) 0.0293(9) 0.0217(8) 0.0052(7) 0.0055(6) -0.0021(7) C8 0.0189(7) 0.0189(8) 0.0206(8) -0.0026(6) 0.0059(6) -0.0008(6) C9 0.0172(7) 0.0205(8) 0.0153(7) 0.0013(6) 0.0014(6) -0.0006(6) C10 0.0229(8) 0.0240(9) 0.0232(8) -0.0039(7) 0.0076(6) -0.0035(7) C11 0.0251(8) 0.0319(10) 0.0240(9) -0.0024(7) 0.0090(7) 0.0010(7) C12 0.0174(7) 0.0352(10) 0.0233(8) 0.0088(7) 0.0037(6) -0.0019(7) C13 0.0208(8) 0.0242(9) 0.0312(9) 0.0046(7) 0.0002(7) -0.0049(7) O1W 0.0271(9) 0.0176(8) 0.0254(9) 0.000 0.0051(7) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 0.00 0.00 0.050 -1.00 0.00 0.00 0.050 0.00 0.00 1.00 0.120 0.00 0.00 -1.00 0.120 2.00 1.00 0.00 0.300 0.00 -1.00 0.00 0.300 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 S1 O2 1.4328(13) . ? S1 O1 1.4397(13) . ? S1 N1 1.6189(14) . ? S1 C5 1.7664(16) . ? N1 C8 1.462(2) . ? N2 C9 1.343(2) . ? N2 C13 1.343(2) . ? C1 C2 1.505(2) . ? C2 C3 1.392(3) . ? C2 C7 1.395(3) . ? C3 C4 1.392(2) . ? C4 C5 1.391(2) . ? C5 C6 1.394(2) . ? C6 C7 1.387(2) . ? C8 C9 1.519(2) . ? C9 C10 1.388(2) . ? C10 C11 1.391(2) . ? C11 C12 1.384(3) . ? C12 C13 1.379(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 O2 S1 O1 119.89(8) . . ? O2 S1 N1 107.78(8) . . ? O1 S1 N1 105.35(8) . . ? O2 S1 C5 107.97(8) . . ? O1 S1 C5 107.50(8) . . ? N1 S1 C5 107.83(8) . . ? C8 N1 S1 121.36(12) . . ? C9 N2 C13 118.10(15) . . ? C3 C2 C7 118.56(15) . . ? C3 C2 C1 120.75(18) . . ? C7 C2 C1 120.68(17) . . ? C4 C3 C2 121.47(17) . . ? C5 C4 C3 118.87(16) . . ? C4 C5 C6 120.68(15) . . ? C4 C5 S1 120.59(13) . . ? C6 C5 S1 118.68(13) . . ? C7 C6 C5 119.42(16) . . ? C6 C7 C2 120.99(17) . . ? N1 C8 C9 110.74(13) . . ? N2 C9 C10 121.96(15) . . ? N2 C9 C8 115.13(14) . . ? C10 C9 C8 122.90(15) . . ? C9 C10 C11 119.03(17) . . ? C12 C11 C10 119.23(17) . . ? C13 C12 C11 117.98(16) . . ? N2 C13 C12 123.66(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1W 0.81(2) 2.05(2) 2.8306(18) 162(2) 1_545 O1W H1W N2 0.85(2) 1.92(2) 2.7695(19) 177(2) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.357 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.051 data_ZnL1 _database_code_CSD 186297 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H30 N4 O5 S2 Zn' _chemical_formula_weight 620.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 30.505(2) _cell_length_b 8.0095(5) _cell_length_c 27.3093(18) _cell_angle_alpha 90 _cell_angle_beta 123.815(3) _cell_angle_gamma 90 _cell_volume 5543.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 992 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 22.08 _exptl_crystal_description irregular _exptl_crystal_colour translucent_colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2576 _exptl_absorpt_coefficient_mu 1.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15s exposure) covering 0.3\% in \w. Crystal to detector distance 4.5 cm. ; _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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29895 _diffrn_reflns_av_R_equivalents 0.0830 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6372 _reflns_number_gt 4627 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0344P)^2^+19.0197P] 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 6372 _refine_ls_number_parameters 472 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.126610(14) 0.29496(5) 0.019211(16) 0.01251(10) Uani 1 1 d . . . S11 S 0.05428(3) 0.20912(10) -0.11498(3) 0.01417(17) Uani 1 1 d . . . O11 O 0.03971(9) 0.0655(3) -0.15340(10) 0.0218(5) Uani 1 1 d . . . N11 N 0.19799(10) 0.1818(3) 0.05171(12) 0.0143(6) Uani 1 1 d . . . S12 S 0.15141(3) 0.68075(10) 0.03754(3) 0.01316(17) Uani 1 1 d . . . O12 O 0.01601(9) 0.2643(3) -0.10234(10) 0.0186(5) Uani 1 1 d . . . N12 N 0.10797(10) 0.1843(3) -0.05323(11) 0.0142(6) Uani 1 1 d . . . C12 C 0.19987(12) 0.0970(4) 0.01041(14) 0.0145(7) Uani 1 1 d . . . C14 C 0.28962(14) 0.0203(5) 0.08035(17) 0.0242(8) Uani 1 1 d . . . H14 H 0.3200(17) -0.038(5) 0.0906(18) 0.033(12) Uiso 1 1 d . . . C15 C 0.28773(14) 0.1060(5) 0.12307(17) 0.0224(8) Uani 1 1 d . . . H15 H 0.3154(15) 0.106(5) 0.1613(18) 0.025(10) Uiso 1 1 d . . . C16 C 0.24155(13) 0.1850(5) 0.10741(16) 0.0206(7) Uani 1 1 d . . . H16 H 0.2357(16) 0.241(5) 0.1318(18) 0.029(11) Uiso 1 1 d . . . C17 C 0.15037(13) 0.0949(4) -0.05152(15) 0.0159(7) Uani 1 1 d . . . H17B H 0.1420(14) -0.022(5) -0.0597(15) 0.017(9) Uiso 1 1 d . . . H17A H 0.1587(14) 0.139(5) -0.0811(16) 0.023(10) Uiso 1 1 d . . . C18 C 0.06198(12) 0.3786(4) -0.15129(13) 0.0134(6) Uani 1 1 d . . . C19 C 0.06281(13) 0.3545(5) -0.20112(14) 0.0172(7) Uani 1 1 d . . . H19 H 0.0618(15) 0.257(5) -0.2153(17) 0.022(10) Uiso 1 1 d . . . O21 O 0.11677(9) 0.8253(3) 0.01291(10) 0.0173(5) Uani 1 1 d . . . N21 N 0.08137(10) 0.2454(3) 0.05156(11) 0.0119(5) Uani 1 1 d . . . O22 O 0.17780(9) 0.6281(3) 0.00974(10) 0.0189(5) Uani 1 1 d . . . N22 N 0.12186(11) 0.5239(3) 0.04079(12) 0.0152(6) Uani 1 1 d . . . C22 C 0.06673(12) 0.3831(4) 0.06711(13) 0.0116(6) Uani 1 1 d . . . C23 C 0.03325(13) 0.3727(4) 0.08665(14) 0.0152(7) Uani 1 1 d . . . H23 H 0.0234(13) 0.477(5) 0.0975(15) 0.016(9) Uiso 1 1 d . . . C24 C 0.01557(13) 0.2174(5) 0.09059(14) 0.0179(7) Uani 1 1 d . . . H24 H -0.0047(13) 0.209(4) 0.1043(14) 0.010(8) Uiso 1 1 d . . . C25 C 0.03085(13) 0.0765(5) 0.07465(15) 0.0183(7) Uani 1 1 d . . . H25 H 0.0187(14) -0.027(5) 0.0754(15) 0.017(10) Uiso 1 1 d . . . C26 C 0.06330(12) 0.0950(4) 0.05480(14) 0.0149(7) Uani 1 1 d . . . H26 H 0.0756(13) 0.007(4) 0.0428(14) 0.009(8) Uiso 1 1 d . . . C27 C 0.08842(13) 0.5484(4) 0.06305(14) 0.0126(6) Uani 1 1 d . . . H27B H 0.0589(13) 0.621(4) 0.0380(15) 0.010(8) Uiso 1 1 d . . . H27A H 0.1095(13) 0.603(4) 0.1022(15) 0.011(8) Uiso 1 1 d . . . C28 C 0.20174(12) 0.7363(4) 0.11137(14) 0.0139(6) Uani 1 1 d . . . C29 C 0.19141(14) 0.8494(4) 0.14240(15) 0.0196(7) Uani 1 1 d . . . H29 H 0.1587(13) 0.909(4) 0.1246(14) 0.007(8) Uiso 1 1 d . . . C13 C 0.24511(14) 0.0159(5) 0.02342(16) 0.0194(7) Uani 1 1 d . . . H14' H 0.2454(15) -0.036(5) -0.0035(17) 0.022(10) Uiso 1 1 d . . . C110 C 0.06732(13) 0.4931(5) -0.22905(15) 0.0185(7) Uani 1 1 d . . . H110 H 0.0680(14) 0.479(5) -0.2622(17) 0.021(10) Uiso 1 1 d . . . C111 C 0.06958(12) 0.6535(4) -0.20874(15) 0.0173(7) Uani 1 1 d . . . C112 C 0.06968(13) 0.6749(4) -0.15771(15) 0.0163(7) Uani 1 1 d . . . H112 H 0.0709(15) 0.774(5) -0.1433(17) 0.028(11) Uiso 1 1 d . . . C113 C 0.06630(13) 0.5391(4) -0.12892(15) 0.0142(7) Uani 1 1 d . . . H113 H 0.0683(14) 0.549(5) -0.0931(17) 0.022(10) Uiso 1 1 d . . . C114 C 0.07009(16) 0.8039(5) -0.24144(18) 0.0250(8) Uani 1 1 d . . . H14A H 0.0799(14) 0.776(5) -0.2679(16) 0.018(9) Uiso 1 1 d . . . H14B H 0.0373(16) 0.855(5) -0.2645(17) 0.027(11) Uiso 1 1 d . . . H14C H 0.0924(18) 0.891(6) -0.215(2) 0.047(14) Uiso 1 1 d . . . C210 C 0.23077(14) 0.8880(5) 0.20067(16) 0.0244(8) Uani 1 1 d . . . H210 H 0.2250(14) 0.972(5) 0.2224(17) 0.023(10) Uiso 1 1 d . . . C211 C 0.28021(14) 0.8150(5) 0.22902(15) 0.0234(8) Uani 1 1 d . . . C212 C 0.28928(14) 0.7009(5) 0.19703(16) 0.0266(8) Uani 1 1 d . . . H212 H 0.3204(14) 0.652(4) 0.2136(15) 0.010(9) Uiso 1 1 d . . . C213 C 0.25106(14) 0.6614(5) 0.13919(16) 0.0211(8) Uani 1 1 d . . . H213 H 0.2563(14) 0.590(5) 0.1184(16) 0.021(10) Uiso 1 1 d . . . C214 C 0.32317(18) 0.8576(6) 0.29173(19) 0.0344(10) Uani 1 1 d . . . H24A H 0.349(2) 0.919(7) 0.294(2) 0.055(15) Uiso 1 1 d . . . H24B H 0.3115(19) 0.926(6) 0.310(2) 0.051(15) Uiso 1 1 d . . . H24C H 0.342(2) 0.755(8) 0.316(3) 0.075(19) Uiso 1 1 d . . . O1W O 0.09398(11) 0.7095(4) 0.17716(12) 0.0282(6) Uani 1 1 d . . . C1W C 0.1192(2) 1.1558(6) -0.28379(19) 0.0342(10) Uani 1 1 d . . . H1W H 0.3831(16) 0.453(6) 0.3051(19) 0.036(12) Uiso 1 1 d . . . H2W H 0.1149(18) 0.143(6) -0.251(2) 0.051(14) Uiso 1 1 d . . . H3W H 0.157(2) 0.815(7) 0.242(2) 0.064(17) Uiso 1 1 d . . . H4W H 0.0608(19) 0.729(6) 0.159(2) 0.042(13) 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 Zn1 0.01237(18) 0.01228(19) 0.01450(18) -0.00083(15) 0.00847(15) 0.00170(15) S11 0.0138(4) 0.0104(4) 0.0162(4) 0.0002(3) 0.0071(3) 0.0004(3) O11 0.0243(13) 0.0136(12) 0.0200(12) -0.0025(10) 0.0077(11) -0.0014(10) N11 0.0129(13) 0.0099(14) 0.0204(14) 0.0022(11) 0.0095(11) 0.0015(10) S12 0.0139(4) 0.0124(4) 0.0141(4) -0.0007(3) 0.0084(3) -0.0005(3) O12 0.0154(11) 0.0172(13) 0.0243(12) 0.0018(10) 0.0118(10) 0.0001(9) N12 0.0138(13) 0.0147(14) 0.0107(12) -0.0020(11) 0.0048(11) 0.0021(11) C12 0.0144(16) 0.0139(16) 0.0198(16) 0.0040(13) 0.0123(14) 0.0002(13) C14 0.0133(17) 0.022(2) 0.037(2) 0.0028(16) 0.0140(17) 0.0037(15) C15 0.0124(16) 0.025(2) 0.0234(19) 0.0020(15) 0.0058(15) 0.0009(15) C16 0.0183(17) 0.0177(18) 0.0236(18) -0.0024(15) 0.0104(15) -0.0046(14) C17 0.0167(16) 0.0151(18) 0.0196(17) 0.0002(13) 0.0124(14) 0.0033(13) C18 0.0084(14) 0.0128(16) 0.0139(15) -0.0001(12) 0.0031(12) 0.0010(12) C19 0.0148(16) 0.0166(18) 0.0162(16) -0.0039(14) 0.0061(14) 0.0003(13) O21 0.0188(12) 0.0127(12) 0.0190(12) 0.0021(9) 0.0096(10) 0.0015(9) N21 0.0134(13) 0.0107(13) 0.0122(12) -0.0009(10) 0.0075(11) 0.0010(10) O22 0.0177(12) 0.0229(13) 0.0217(12) -0.0046(10) 0.0144(10) -0.0020(10) N22 0.0187(14) 0.0099(14) 0.0223(15) -0.0026(11) 0.0147(12) -0.0027(11) C22 0.0094(14) 0.0121(16) 0.0116(14) -0.0003(12) 0.0047(12) 0.0006(12) C23 0.0147(16) 0.0181(17) 0.0171(16) -0.0023(13) 0.0115(14) -0.0003(13) C24 0.0148(16) 0.0247(19) 0.0189(16) 0.0019(14) 0.0124(14) -0.0012(14) C25 0.0159(17) 0.0169(18) 0.0186(17) 0.0040(14) 0.0074(14) -0.0008(14) C26 0.0129(16) 0.0106(16) 0.0189(16) -0.0008(13) 0.0075(14) 0.0007(13) C27 0.0129(16) 0.0113(16) 0.0155(16) -0.0002(12) 0.0091(14) 0.0021(13) C28 0.0126(15) 0.0130(16) 0.0136(15) -0.0001(12) 0.0056(13) -0.0027(12) C29 0.0165(17) 0.0197(18) 0.0189(17) -0.0005(14) 0.0075(14) 0.0012(14) C13 0.0185(18) 0.0183(18) 0.0273(19) 0.0020(15) 0.0163(16) 0.0020(14) C110 0.0157(17) 0.0240(19) 0.0186(18) 0.0016(14) 0.0112(15) 0.0055(14) C111 0.0088(15) 0.0201(18) 0.0230(17) 0.0063(14) 0.0089(13) 0.0013(13) C112 0.0140(16) 0.0113(17) 0.0208(17) -0.0009(13) 0.0079(14) 0.0003(13) C113 0.0135(16) 0.0109(16) 0.0178(17) -0.0009(12) 0.0084(14) -0.0006(12) C114 0.025(2) 0.023(2) 0.030(2) 0.0093(17) 0.0162(17) 0.0006(17) C210 0.0241(19) 0.026(2) 0.0227(18) -0.0083(15) 0.0126(16) -0.0024(16) C211 0.0208(18) 0.026(2) 0.0181(17) -0.0006(15) 0.0074(14) -0.0120(15) C212 0.0143(17) 0.031(2) 0.0246(18) 0.0047(17) 0.0047(15) 0.0054(17) C213 0.0196(18) 0.0177(19) 0.0242(18) 0.0019(15) 0.0111(15) 0.0002(14) C214 0.027(2) 0.039(3) 0.026(2) -0.0039(19) 0.0088(18) -0.013(2) O1W 0.0215(14) 0.0304(15) 0.0309(14) -0.0069(12) 0.0135(12) 0.0023(12) C1W 0.048(3) 0.033(2) 0.029(2) 0.0120(18) 0.026(2) 0.015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N12 1.942(3) . ? Zn1 N22 1.956(3) . ? Zn1 N21 2.049(3) . ? Zn1 N11 2.049(3) . ? S11 O11 1.450(2) . ? S11 O12 1.458(2) . ? S11 N12 1.578(3) . ? S11 C18 1.772(3) . ? N11 C12 1.345(4) . ? N11 C16 1.353(4) . ? S12 O22 1.443(2) . ? S12 O21 1.456(2) . ? S12 N22 1.577(3) . ? S12 C28 1.782(3) . ? N12 C17 1.456(4) . ? C12 C13 1.381(5) . ? C12 C17 1.516(5) . ? C14 C15 1.382(5) . ? C14 C13 1.383(5) . ? C15 C16 1.377(5) . ? C18 C19 1.388(5) . ? C18 C113 1.398(4) . ? C19 C110 1.396(5) . ? N21 C22 1.344(4) . ? N21 C26 1.348(4) . ? N22 C27 1.462(4) . ? C22 C23 1.393(4) . ? C22 C27 1.512(4) . ? C23 C24 1.384(5) . ? C24 C25 1.380(5) . ? C25 C26 1.376(5) . ? C28 C213 1.389(5) . ? C28 C29 1.391(5) . ? C29 C210 1.394(5) . ? C110 C111 1.386(5) . ? C111 C112 1.402(5) . ? C111 C114 1.505(5) . ? C112 C113 1.379(5) . ? C210 C211 1.384(5) . ? C211 C212 1.395(6) . ? C211 C214 1.506(5) . ? C212 C213 1.380(5) . ? O1W C1W 1.407(5) 6_576 ? C1W O1W 1.407(5) 6_575 ? 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 N12 Zn1 N22 134.92(11) . . ? N12 Zn1 N21 117.73(11) . . ? N22 Zn1 N21 82.59(10) . . ? N12 Zn1 N11 82.96(11) . . ? N22 Zn1 N11 121.54(11) . . ? N21 Zn1 N11 122.40(10) . . ? O11 S11 O12 116.64(14) . . ? O11 S11 N12 113.02(14) . . ? O12 S11 N12 106.07(14) . . ? O11 S11 C18 106.58(15) . . ? O12 S11 C18 105.86(14) . . ? N12 S11 C18 108.20(14) . . ? C12 N11 C16 118.6(3) . . ? C12 N11 Zn1 113.0(2) . . ? C16 N11 Zn1 128.4(2) . . ? O22 S12 O21 117.62(14) . . ? O22 S12 N22 107.48(14) . . ? O21 S12 N22 111.65(14) . . ? O22 S12 C28 106.66(15) . . ? O21 S12 C28 105.71(14) . . ? N22 S12 C28 107.14(15) . . ? C17 N12 S11 118.1(2) . . ? C17 N12 Zn1 116.1(2) . . ? S11 N12 Zn1 124.91(16) . . ? N11 C12 C13 121.7(3) . . ? N11 C12 C17 117.4(3) . . ? C13 C12 C17 120.9(3) . . ? C15 C14 C13 119.0(3) . . ? C16 C15 C14 118.8(3) . . ? N11 C16 C15 122.4(3) . . ? N12 C17 C12 110.2(3) . . ? C19 C18 C113 120.5(3) . . ? C19 C18 S11 121.5(3) . . ? C113 C18 S11 118.0(2) . . ? C18 C19 C110 119.1(3) . . ? C22 N21 C26 119.5(3) . . ? C22 N21 Zn1 113.5(2) . . ? C26 N21 Zn1 126.8(2) . . ? C27 N22 S12 118.0(2) . . ? C27 N22 Zn1 115.9(2) . . ? S12 N22 Zn1 126.10(16) . . ? N21 C22 C23 121.0(3) . . ? N21 C22 C27 117.3(3) . . ? C23 C22 C27 121.6(3) . . ? C24 C23 C22 118.9(3) . . ? C25 C24 C23 119.7(3) . . ? C26 C25 C24 118.7(3) . . ? N21 C26 C25 122.1(3) . . ? N22 C27 C22 110.4(3) . . ? C213 C28 C29 119.5(3) . . ? C213 C28 S12 120.0(3) . . ? C29 C28 S12 120.5(2) . . ? C28 C29 C210 119.8(3) . . ? C12 C13 C14 119.5(3) . . ? C111 C110 C19 121.1(3) . . ? C110 C111 C112 118.9(3) . . ? C110 C111 C114 121.3(3) . . ? C112 C111 C114 119.8(3) . . ? C113 C112 C111 120.7(3) . . ? C112 C113 C18 119.7(3) . . ? C211 C210 C29 121.6(3) . . ? C210 C211 C212 117.4(3) . . ? C210 C211 C214 121.9(4) . . ? C212 C211 C214 120.7(4) . . ? C213 C212 C211 122.1(3) . . ? C212 C213 C28 119.7(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.453 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.098 data_ZnL2 _database_code_CSD 186298 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 F6 N4 O4 S2 Zn' _chemical_formula_weight 543.77 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.2956(8) _cell_length_b 9.7213(10) _cell_length_c 13.0352(13) _cell_angle_alpha 93.193(4) _cell_angle_beta 95.817(4) _cell_angle_gamma 107.145(4) _cell_volume 995.27(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 989 _cell_measurement_theta_min 2.5915 _cell_measurement_theta_max 27.4765 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.814 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 1.529 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.573 _exptl_absorpt_correction_T_max 0.922 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15s exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 10670 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4547 _reflns_number_gt 4166 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0320P)^2^+0.7948P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens diffmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4547 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_ref 0.0685 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Zn Zn 0.67951(3) 0.72819(2) 0.781830(15) 0.01479(7) Uani 1 1 d . . . S11 S 0.67519(5) 1.02235(5) 0.69829(3) 0.01502(10) Uani 1 1 d . . . S21 S 1.03486(6) 0.67874(5) 0.77393(3) 0.01620(10) Uani 1 1 d . . . F11 F 0.76556(16) 1.01150(14) 0.51106(9) 0.0298(3) Uani 1 1 d . . . F12 F 0.89113(19) 1.21346(15) 0.60294(11) 0.0402(3) Uani 1 1 d . . . F13 F 0.96615(17) 1.02340(18) 0.63365(11) 0.0390(3) Uani 1 1 d . . . F21 F 1.1149(2) 0.51841(16) 0.91526(10) 0.0390(3) Uani 1 1 d . . . F22 F 1.13232(19) 0.44443(15) 0.75842(11) 0.0372(3) Uani 1 1 d . . . F23 F 0.8877(2) 0.41019(15) 0.81238(15) 0.0505(4) Uani 1 1 d . . . N11 N 0.50803(19) 0.56921(17) 0.68629(11) 0.0148(3) Uani 1 1 d . . . N12 N 0.60645(19) 0.85457(17) 0.68611(12) 0.0158(3) Uani 1 1 d . . . N21 N 0.6615(2) 0.77477(18) 0.93425(12) 0.0181(3) Uani 1 1 d . . . N22 N 0.9061(2) 0.72218(18) 0.83854(12) 0.0170(3) Uani 1 1 d . . . O1 O 0.96261(19) 0.64512(18) 0.66739(11) 0.0285(3) Uani 1 1 d . . . O2 O 1.20865(17) 0.76763(16) 0.79903(11) 0.0229(3) Uani 1 1 d . . . O11 O 0.55243(18) 1.09345(15) 0.66350(11) 0.0227(3) Uani 1 1 d . . . O12 O 0.77641(17) 1.07045(15) 0.79754(10) 0.0213(3) Uani 1 1 d . . . C11 C 0.4787(2) 0.4247(2) 0.68807(14) 0.0178(4) Uani 1 1 d . . . C12 C 0.3599(2) 0.3258(2) 0.61747(14) 0.0178(4) Uani 1 1 d . . . C13 C 0.2666(2) 0.3768(2) 0.54128(14) 0.0179(4) Uani 1 1 d . . . C14 C 0.2966(2) 0.5245(2) 0.53853(14) 0.0162(3) Uani 1 1 d . . . C15 C 0.4198(2) 0.6191(2) 0.61189(13) 0.0144(3) Uani 1 1 d . . . C16 C 0.4578(2) 0.7812(2) 0.60977(14) 0.0156(3) Uani 1 1 d . . . C17 C 0.8332(3) 1.0705(2) 0.60636(16) 0.0230(4) Uani 1 1 d . . . C21 C 0.5253(3) 0.7961(2) 0.97427(16) 0.0247(4) Uani 1 1 d . . . C22 C 0.5316(3) 0.8416(3) 1.07726(16) 0.0264(4) Uani 1 1 d . . . C23 C 0.6844(3) 0.8680(2) 1.14127(15) 0.0223(4) Uani 1 1 d . . . C24 C 0.8237(3) 0.8459(2) 1.10104(14) 0.0192(4) Uani 1 1 d . . . C25 C 0.8088(2) 0.79971(19) 0.99597(13) 0.0150(3) Uani 1 1 d . . . C26 C 0.9600(2) 0.7793(2) 0.94777(14) 0.0165(3) Uani 1 1 d . . . C27 C 1.0414(3) 0.5028(2) 0.81643(17) 0.0270(4) Uani 1 1 d . . . H11 H 0.545(3) 0.396(2) 0.7389(18) 0.019(5) Uiso 1 1 d . . . H12 H 0.341(3) 0.228(3) 0.6201(17) 0.018(5) Uiso 1 1 d . . . H13 H 0.184(3) 0.311(2) 0.4927(17) 0.015(5) Uiso 1 1 d . . . H14 H 0.239(3) 0.562(2) 0.4887(18) 0.019(6) Uiso 1 1 d . . . H16A H 0.356(3) 0.806(2) 0.6274(16) 0.013(5) Uiso 1 1 d . . . H16B H 0.482(3) 0.810(2) 0.5403(17) 0.014(5) Uiso 1 1 d . . . H21 H 0.430(3) 0.780(3) 0.927(2) 0.030(7) Uiso 1 1 d . . . H22 H 0.434(4) 0.858(3) 1.103(2) 0.039(7) Uiso 1 1 d . . . H23 H 0.692(3) 0.902(3) 1.212(2) 0.038(7) Uiso 1 1 d . . . H24 H 0.930(3) 0.863(3) 1.1433(19) 0.027(6) Uiso 1 1 d . . . H26A H 1.050(3) 0.867(3) 0.9576(18) 0.021(6) Uiso 1 1 d . . . H26B H 1.000(3) 0.711(3) 0.9881(19) 0.026(6) 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 Zn 0.01424(11) 0.01828(11) 0.01184(10) -0.00043(7) -0.00156(7) 0.00627(8) S11 0.0141(2) 0.0158(2) 0.0154(2) -0.00096(15) 0.00156(16) 0.00530(16) S21 0.0151(2) 0.0212(2) 0.0133(2) 0.00137(16) 0.00129(16) 0.00722(17) F11 0.0327(7) 0.0340(7) 0.0183(6) -0.0005(5) 0.0074(5) 0.0023(6) F12 0.0427(8) 0.0253(7) 0.0420(8) 0.0030(6) 0.0145(6) -0.0088(6) F13 0.0208(6) 0.0623(10) 0.0385(8) 0.0045(7) 0.0099(6) 0.0176(6) F21 0.0631(10) 0.0411(8) 0.0283(7) 0.0156(6) 0.0143(7) 0.0343(7) F22 0.0482(8) 0.0381(8) 0.0389(7) 0.0046(6) 0.0208(6) 0.0287(7) F23 0.0397(9) 0.0222(7) 0.0887(13) 0.0023(7) 0.0258(8) 0.0026(6) N11 0.0147(7) 0.0172(7) 0.0136(7) 0.0009(6) 0.0024(6) 0.0060(6) N12 0.0155(7) 0.0161(7) 0.0147(7) 0.0011(6) -0.0023(6) 0.0043(6) N21 0.0165(8) 0.0232(8) 0.0153(7) 0.0001(6) -0.0002(6) 0.0078(6) N22 0.0156(7) 0.0234(8) 0.0129(7) -0.0013(6) -0.0010(6) 0.0089(6) O1 0.0264(8) 0.0471(10) 0.0149(7) -0.0045(6) -0.0026(6) 0.0183(7) O2 0.0165(7) 0.0286(8) 0.0219(7) 0.0030(6) 0.0037(5) 0.0034(6) O11 0.0213(7) 0.0201(7) 0.0288(7) 0.0006(6) 0.0006(6) 0.0106(6) O12 0.0200(7) 0.0232(7) 0.0180(7) -0.0041(5) -0.0013(5) 0.0047(6) C11 0.0187(9) 0.0205(9) 0.0158(8) 0.0032(7) 0.0015(7) 0.0084(7) C12 0.0195(9) 0.0167(9) 0.0177(9) 0.0008(7) 0.0039(7) 0.0060(7) C13 0.0167(9) 0.0201(9) 0.0146(8) -0.0013(7) 0.0022(7) 0.0025(7) C14 0.0145(8) 0.0216(9) 0.0125(8) 0.0018(7) -0.0002(6) 0.0058(7) C15 0.0133(8) 0.0189(9) 0.0129(8) 0.0024(6) 0.0035(6) 0.0068(7) C16 0.0143(8) 0.0172(9) 0.0143(8) 0.0010(6) -0.0015(6) 0.0046(7) C17 0.0193(9) 0.0243(10) 0.0227(9) -0.0002(8) 0.0040(7) 0.0025(8) C21 0.0189(10) 0.0372(12) 0.0197(9) -0.0012(8) -0.0010(8) 0.0127(9) C22 0.0238(10) 0.0376(12) 0.0216(10) -0.0003(8) 0.0054(8) 0.0149(9) C23 0.0276(10) 0.0265(10) 0.0142(9) 0.0015(7) 0.0027(7) 0.0105(8) C24 0.0207(9) 0.0216(9) 0.0137(8) 0.0009(7) -0.0007(7) 0.0052(8) C25 0.0171(8) 0.0135(8) 0.0135(8) 0.0022(6) -0.0006(6) 0.0041(7) C26 0.0140(8) 0.0202(9) 0.0146(8) 0.0001(7) -0.0010(6) 0.0052(7) C27 0.0279(11) 0.0231(10) 0.0346(11) 0.0035(8) 0.0150(9) 0.0109(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 Zn N22 1.9674(15) . ? Zn N12 1.9723(15) . ? Zn N11 2.0232(16) . ? Zn N21 2.0432(16) . ? S11 O11 1.4411(14) . ? S11 O12 1.4417(13) . ? S11 N12 1.5541(16) . ? S11 C17 1.842(2) . ? S21 O1 1.4353(14) . ? S21 O2 1.4390(14) . ? S21 N22 1.5612(16) . ? S21 C27 1.841(2) . ? F11 C17 1.333(2) . ? F12 C17 1.335(2) . ? F13 C17 1.338(2) . ? F21 C27 1.349(3) . ? F22 C27 1.335(2) . ? F23 C27 1.320(3) . ? N11 C15 1.352(2) . ? N11 C11 1.355(2) . ? N12 C16 1.474(2) . ? N21 C25 1.343(2) . ? N21 C21 1.355(3) . ? N22 C26 1.474(2) . ? C11 C12 1.379(3) . ? C12 C13 1.398(3) . ? C13 C14 1.386(3) . ? C14 C15 1.398(2) . ? C15 C16 1.516(3) . ? C21 C22 1.381(3) . ? C22 C23 1.392(3) . ? C23 C24 1.383(3) . ? C24 C25 1.399(2) . ? C25 C26 1.517(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 N22 Zn N12 131.99(7) . . ? N22 Zn N11 124.75(6) . . ? N12 Zn N11 83.12(6) . . ? N22 Zn N21 82.44(6) . . ? N12 Zn N21 114.93(7) . . ? N11 Zn N21 124.98(6) . . ? O11 S11 O12 119.25(9) . . ? O11 S11 N12 114.42(9) . . ? O12 S11 N12 109.68(8) . . ? O11 S11 C17 103.05(9) . . ? O12 S11 C17 103.06(9) . . ? N12 S11 C17 105.50(9) . . ? O1 S21 O2 119.39(9) . . ? O1 S21 N22 109.47(9) . . ? O2 S21 N22 114.81(9) . . ? O1 S21 C27 103.59(10) . . ? O2 S21 C27 102.73(10) . . ? N22 S21 C27 104.85(9) . . ? C15 N11 C11 119.12(16) . . ? C15 N11 Zn 113.43(12) . . ? C11 N11 Zn 127.42(12) . . ? C16 N12 S11 119.77(12) . . ? C16 N12 Zn 115.10(11) . . ? S11 N12 Zn 124.35(9) . . ? C25 N21 C21 119.38(16) . . ? C25 N21 Zn 113.47(12) . . ? C21 N21 Zn 126.79(13) . . ? C26 N22 S21 119.44(13) . . ? C26 N22 Zn 115.28(12) . . ? S21 N22 Zn 124.90(9) . . ? N11 C11 C12 122.38(17) . . ? C11 C12 C13 118.70(18) . . ? C14 C13 C12 119.29(17) . . ? C13 C14 C15 119.18(17) . . ? N11 C15 C14 121.31(17) . . ? N11 C15 C16 118.23(16) . . ? C14 C15 C16 120.46(15) . . ? N12 C16 C15 109.11(14) . . ? F11 C17 F12 107.94(17) . . ? F11 C17 F13 107.91(17) . . ? F12 C17 F13 107.94(17) . . ? F11 C17 S11 110.88(13) . . ? F12 C17 S11 111.21(14) . . ? F13 C17 S11 110.83(14) . . ? N21 C21 C22 122.30(19) . . ? C21 C22 C23 118.39(19) . . ? C24 C23 C22 119.62(18) . . ? C23 C24 C25 119.08(18) . . ? N21 C25 C24 121.22(17) . . ? N21 C25 C26 117.92(15) . . ? C24 C25 C26 120.84(16) . . ? N22 C26 C25 109.33(14) . . ? F23 C27 F22 108.44(18) . . ? F23 C27 F21 107.28(18) . . ? F22 C27 F21 107.34(18) . . ? F23 C27 S21 111.92(16) . . ? F22 C27 S21 111.20(15) . . ? F21 C27 S21 110.47(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.658 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.066 data_ZnL3 _database_code_CSD 186299 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 F6 N4 O4 S2 Zn' _chemical_formula_weight 571.82 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9725(2) _cell_length_b 9.4317(2) _cell_length_c 14.7462(4) _cell_angle_alpha 81.9840(10) _cell_angle_beta 81.1300(10) _cell_angle_gamma 81.7440(10) _cell_volume 1076.38(5) _cell_formula_units_Z 2 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 4932 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 27.98 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas Not_measured _exptl_crystal_density_diffrn 1.764 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 1.419 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.6135 _exptl_absorpt_correction_T_max 0.8076 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15s exposure) covering 0.3\% in \w. Crystal to detector distance 4.5 cm. ; _diffrn_ambient_temperature 105(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 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 12528 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5190 _reflns_number_gt 4867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0478P)^2^+0.8519P] 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 5190 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.10453(2) 0.20964(2) 0.744149(13) 0.01524(7) Uani 1 1 d . . . S10 S 0.19450(6) 0.47688(5) 0.82329(3) 0.01787(10) Uani 1 1 d . . . S2 S 0.47040(5) 0.04129(5) 0.68998(3) 0.01736(10) Uani 1 1 d . . . F11 F 0.29547(17) 0.41580(14) 0.98755(8) 0.0297(3) Uani 1 1 d . . . F13 F 0.47021(16) 0.31984(14) 0.87979(9) 0.0300(3) Uani 1 1 d . . . O12 O 0.28802(18) 0.49197(16) 0.73151(9) 0.0240(3) Uani 1 1 d . . . F23 F 0.33436(16) -0.18719(14) 0.77509(9) 0.0312(3) Uani 1 1 d . . . N11 N -0.05836(19) 0.10844(17) 0.84560(10) 0.0173(3) Uani 1 1 d . . . O22 O 0.48768(19) 0.06900(16) 0.78137(10) 0.0256(3) Uani 1 1 d . . . O11 O 0.09022(19) 0.60053(15) 0.85886(10) 0.0253(3) Uani 1 1 d . . . O21 O 0.61055(17) 0.05624(15) 0.61641(10) 0.0239(3) Uani 1 1 d . . . N22 N 0.2931(2) 0.11352(18) 0.66313(11) 0.0210(3) Uani 1 1 d . . . F12 F 0.4563(2) 0.54729(15) 0.88893(11) 0.0403(3) Uani 1 1 d . . . F22 F 0.60305(16) -0.23064(14) 0.72464(12) 0.0382(3) Uani 1 1 d . . . N21 N 0.0026(2) 0.27311(17) 0.62277(11) 0.0183(3) Uani 1 1 d . . . N12 N 0.1027(2) 0.33820(17) 0.83841(11) 0.0186(3) Uani 1 1 d . . . F21 F 0.4165(2) -0.19578(15) 0.62917(10) 0.0369(3) Uani 1 1 d . . . C27 C 0.4551(2) -0.1537(2) 0.70570(14) 0.0230(4) Uani 1 1 d . . . C15 C -0.1001(2) 0.1783(2) 0.92123(12) 0.0190(3) Uani 1 1 d . . . C16 C -0.0322(3) 0.3209(2) 0.91836(13) 0.0216(4) Uani 1 1 d . . . H16A H -0.1263 0.4011 0.9130 0.026 Uiso 1 1 calc R . . H16B H 0.0153 0.3236 0.9762 0.026 Uiso 1 1 calc R . . C11 C -0.1204(2) -0.0177(2) 0.84326(13) 0.0209(4) Uani 1 1 d . . . C24 C 0.0556(3) 0.2486(3) 0.46080(14) 0.0291(4) Uani 1 1 d . . . H24A H 0.1273 0.2103 0.4100 0.035 Uiso 1 1 calc R . . C12 C -0.2260(3) -0.0762(2) 0.91915(15) 0.0279(4) Uani 1 1 d . . . H12B H -0.2690 -0.1645 0.9174 0.033 Uiso 1 1 calc R . . C111 C -0.0731(3) -0.0860(2) 0.75521(15) 0.0245(4) Uani 1 1 d . . . H11B H 0.0015 -0.0272 0.7110 0.037 Uiso 1 1 calc R . . H11C H -0.1771 -0.0921 0.7289 0.037 Uiso 1 1 calc R . . H11D H -0.0129 -0.1831 0.7683 0.037 Uiso 1 1 calc R . . C13 C -0.2684(3) -0.0050(3) 0.99757(15) 0.0290(4) Uani 1 1 d . . . H13A H -0.3398 -0.0446 1.0498 0.035 Uiso 1 1 calc R . . C25 C 0.1025(3) 0.2207(2) 0.54945(13) 0.0222(4) Uani 1 1 d . . . C14 C -0.2055(2) 0.1243(2) 0.99886(13) 0.0247(4) Uani 1 1 d . . . H14A H -0.2336 0.1750 1.0516 0.030 Uiso 1 1 calc R . . C21 C -0.1490(2) 0.3555(2) 0.61115(14) 0.0229(4) Uani 1 1 d . . . C17 C 0.3642(3) 0.4375(2) 0.89863(14) 0.0223(4) Uani 1 1 d . . . C22 C -0.2007(3) 0.3877(2) 0.52399(16) 0.0294(4) Uani 1 1 d . . . H22B H -0.3059 0.4465 0.5162 0.035 Uiso 1 1 calc R . . C211 C -0.2550(3) 0.4064(3) 0.69638(16) 0.0336(5) Uani 1 1 d . . . H21B H -0.1951 0.3715 0.7500 0.050 Uiso 1 1 calc R . . H21C H -0.3655 0.3688 0.7058 0.050 Uiso 1 1 calc R . . H21D H -0.2736 0.5121 0.6891 0.050 Uiso 1 1 calc R . . C26 C 0.2693(3) 0.1282(3) 0.56500(14) 0.0360(5) Uani 1 1 d . . . H26A H 0.2690 0.0315 0.5462 0.043 Uiso 1 1 calc R . . H26B H 0.3656 0.1727 0.5265 0.043 Uiso 1 1 calc R . . C23 C -0.0985(3) 0.3338(3) 0.44835(15) 0.0313(5) Uani 1 1 d . . . H23A H -0.1334 0.3549 0.3887 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01497(11) 0.01885(11) 0.01132(11) -0.00397(7) -0.00088(7) 0.00089(7) S10 0.0205(2) 0.0178(2) 0.0155(2) -0.00224(15) -0.00462(16) -0.00063(16) S2 0.0154(2) 0.0199(2) 0.0164(2) -0.00506(15) -0.00180(15) 0.00154(15) F11 0.0366(7) 0.0354(7) 0.0172(6) -0.0050(5) -0.0089(5) 0.0019(5) F13 0.0251(6) 0.0337(7) 0.0303(6) -0.0067(5) -0.0078(5) 0.0066(5) O12 0.0256(7) 0.0286(7) 0.0176(6) 0.0004(5) -0.0032(5) -0.0056(6) F23 0.0255(6) 0.0318(6) 0.0313(7) 0.0053(5) 0.0040(5) -0.0039(5) N11 0.0156(7) 0.0209(7) 0.0150(7) -0.0014(5) -0.0037(5) 0.0002(5) O22 0.0270(7) 0.0306(7) 0.0199(7) -0.0083(6) -0.0087(6) 0.0052(6) O11 0.0304(7) 0.0190(6) 0.0258(7) -0.0048(5) -0.0055(6) 0.0028(5) O21 0.0177(6) 0.0268(7) 0.0251(7) -0.0035(5) 0.0024(5) -0.0016(5) N22 0.0185(7) 0.0291(8) 0.0135(7) -0.0055(6) -0.0028(6) 0.0069(6) F12 0.0477(8) 0.0344(7) 0.0468(8) 0.0068(6) -0.0276(7) -0.0206(6) F22 0.0219(6) 0.0222(6) 0.0664(10) -0.0023(6) -0.0030(6) 0.0054(5) N21 0.0182(7) 0.0205(7) 0.0158(7) -0.0013(6) -0.0031(6) -0.0010(6) N12 0.0191(7) 0.0216(7) 0.0152(7) -0.0061(6) 0.0019(6) -0.0034(6) F21 0.0476(8) 0.0339(7) 0.0337(7) -0.0138(6) -0.0008(6) -0.0154(6) C27 0.0181(8) 0.0226(9) 0.0272(10) -0.0043(7) 0.0005(7) -0.0014(7) C15 0.0152(8) 0.0247(9) 0.0156(8) -0.0008(7) -0.0022(6) 0.0011(6) C16 0.0228(9) 0.0254(9) 0.0157(8) -0.0077(7) 0.0038(7) -0.0018(7) C11 0.0179(8) 0.0227(9) 0.0227(9) 0.0019(7) -0.0101(7) -0.0015(7) C24 0.0325(11) 0.0391(11) 0.0166(9) -0.0030(8) -0.0076(8) -0.0040(9) C12 0.0234(9) 0.0312(10) 0.0296(10) 0.0084(8) -0.0113(8) -0.0088(8) C111 0.0244(9) 0.0225(9) 0.0291(10) -0.0050(7) -0.0106(8) -0.0021(7) C13 0.0202(9) 0.0408(12) 0.0229(10) 0.0108(8) -0.0037(7) -0.0066(8) C25 0.0223(9) 0.0284(9) 0.0156(8) -0.0027(7) -0.0042(7) -0.0005(7) C14 0.0192(9) 0.0361(11) 0.0157(8) 0.0007(7) -0.0005(7) 0.0007(8) C21 0.0201(9) 0.0221(9) 0.0260(10) 0.0006(7) -0.0058(7) -0.0019(7) C17 0.0255(9) 0.0217(9) 0.0213(9) -0.0022(7) -0.0080(7) -0.0029(7) C22 0.0248(10) 0.0298(10) 0.0336(11) 0.0037(8) -0.0137(8) -0.0002(8) C211 0.0229(10) 0.0397(12) 0.0337(12) -0.0051(9) -0.0048(8) 0.0128(9) C26 0.0306(11) 0.0592(15) 0.0141(9) -0.0119(9) -0.0047(8) 0.0172(10) C23 0.0352(11) 0.0390(12) 0.0219(10) 0.0044(8) -0.0143(8) -0.0083(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 N12 1.9650(15) . ? Zn1 N22 1.9661(15) . ? Zn1 N11 2.0480(16) . ? Zn1 N21 2.0573(16) . ? S10 O12 1.4400(14) . ? S10 O11 1.4436(14) . ? S10 N12 1.5619(16) . ? S10 C17 1.846(2) . ? S2 O22 1.4384(14) . ? S2 O21 1.4402(14) . ? S2 N22 1.5622(16) . ? S2 C27 1.841(2) . ? F11 C17 1.341(2) . ? F13 C17 1.329(2) . ? F23 C27 1.329(2) . ? N11 C15 1.348(2) . ? N11 C11 1.359(2) . ? N22 C26 1.473(2) . ? F12 C17 1.333(2) . ? F22 C27 1.340(2) . ? N21 C25 1.348(2) . ? N21 C21 1.360(2) . ? N12 C16 1.476(2) . ? F21 C27 1.339(2) . ? C15 C14 1.392(3) . ? C15 C16 1.513(3) . ? C11 C12 1.391(3) . ? C11 C111 1.502(3) . ? C24 C23 1.390(3) . ? C24 C25 1.395(3) . ? C12 C13 1.390(3) . ? C13 C14 1.387(3) . ? C25 C26 1.513(3) . ? C21 C22 1.390(3) . ? C21 C211 1.499(3) . ? C22 C23 1.388(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 N12 Zn1 N22 131.73(7) . . ? N12 Zn1 N11 82.81(6) . . ? N22 Zn1 N11 125.79(7) . . ? N12 Zn1 N21 123.81(7) . . ? N22 Zn1 N21 83.32(6) . . ? N11 Zn1 N21 113.20(6) . . ? O12 S10 O11 119.76(9) . . ? O12 S10 N12 109.72(8) . . ? O11 S10 N12 113.90(9) . . ? O12 S10 C17 103.54(9) . . ? O11 S10 C17 102.66(9) . . ? N12 S10 C17 105.39(9) . . ? O22 S2 O21 119.83(9) . . ? O22 S2 N22 110.27(8) . . ? O21 S2 N22 114.02(9) . . ? O22 S2 C27 102.74(9) . . ? O21 S2 C27 103.11(9) . . ? N22 S2 C27 104.71(9) . . ? C15 N11 C11 120.12(16) . . ? C15 N11 Zn1 113.12(12) . . ? C11 N11 Zn1 126.75(13) . . ? C26 N22 S2 117.71(13) . . ? C26 N22 Zn1 115.20(12) . . ? S2 N22 Zn1 126.64(9) . . ? C25 N21 C21 119.80(17) . . ? C25 N21 Zn1 112.62(12) . . ? C21 N21 Zn1 127.56(13) . . ? C16 N12 S10 118.28(12) . . ? C16 N12 Zn1 114.54(12) . . ? S10 N12 Zn1 125.06(9) . . ? F23 C27 F21 108.09(16) . . ? F23 C27 F22 107.82(17) . . ? F21 C27 F22 107.70(17) . . ? F23 C27 S2 110.79(13) . . ? F21 C27 S2 110.93(14) . . ? F22 C27 S2 111.36(13) . . ? N11 C15 C14 121.80(18) . . ? N11 C15 C16 117.64(16) . . ? C14 C15 C16 120.55(17) . . ? N12 C16 C15 109.47(15) . . ? N11 C11 C12 120.26(19) . . ? N11 C11 C111 116.82(17) . . ? C12 C11 C111 122.90(18) . . ? C23 C24 C25 118.5(2) . . ? C13 C12 C11 119.8(2) . . ? C14 C13 C12 119.41(18) . . ? N21 C25 C24 121.92(19) . . ? N21 C25 C26 118.42(17) . . ? C24 C25 C26 119.65(18) . . ? C13 C14 C15 118.60(19) . . ? N21 C21 C22 120.49(19) . . ? N21 C21 C211 116.62(18) . . ? C22 C21 C211 122.89(19) . . ? F13 C17 F12 108.03(17) . . ? F13 C17 F11 107.59(15) . . ? F12 C17 F11 107.97(16) . . ? F13 C17 S10 111.90(13) . . ? F12 C17 S10 110.86(13) . . ? F11 C17 S10 110.35(14) . . ? C23 C22 C21 119.9(2) . . ? N22 C26 C25 110.41(16) . . ? C22 C23 C24 119.32(19) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.712 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.103 data_ZnL4 _database_code_CSD 186300 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H30 N4 O4 S2 Zn' _chemical_formula_weight 616.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 28.1286(5) _cell_length_b 12.0327(2) _cell_length_c 16.7257(3) _cell_angle_alpha 90 _cell_angle_beta 91.7010(10) _cell_angle_gamma 90 _cell_volume 5658.54(17) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8265 _cell_measurement_theta_min 2.4365 _cell_measurement_theta_max 28.4525 _exptl_crystal_description block _exptl_crystal_colour clear_colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2560 _exptl_absorpt_coefficient_mu 1.057 _exptl_absorpt_correction_T_max 0.827 _exptl_absorpt_correction_T_min 0.666 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (5s exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(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 'Bruker SMART CCD 6K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 18139 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.51 _reflns_number_total 3757 _reflns_number_gt 3292 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0242P)^2^+7.4532P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3757 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0710 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.422168(8) -0.006425(19) 0.721651(13) 0.01960(7) Uani 1 1 d . . . S11 S 0.401258(19) 0.23223(8) 0.65990(3) 0.0251(3) Uani 1 1 d . . . N11 N 0.4215(3) 0.0000(7) 0.8441(4) 0.0187(9) Uani 1 1 d . . . N12 N 0.39817(7) 0.14532(15) 0.73055(10) 0.0260(4) Uani 1 1 d . . . N21 N 0.49023(6) -0.02719(15) 0.67724(10) 0.0200(3) Uani 1 1 d . . . O11 O 0.40763(6) 0.16777(14) 0.58779(9) 0.0328(4) Uani 1 1 d . . . C15 C 0.41300(8) 0.10328(18) 0.87126(12) 0.0241(4) Uani 1 1 d . . . O12 O 0.43541(6) 0.32009(14) 0.67662(10) 0.0330(4) Uani 1 1 d . . . C11 C 0.43521(8) -0.08055(18) 0.89551(13) 0.0264(4) Uani 1 1 d . . . C14 C 0.41761(8) 0.12933(19) 0.95225(13) 0.0279(5) Uani 1 1 d . . . H14 H 0.4108 0.2004 0.9704 0.034 Uiso 1 1 calc R . . O22 O 0.3675(2) -0.3153(5) 0.6435(3) 0.0427(16) Uani 1 1 d . . . S21 S 0.35994(8) -0.1958(2) 0.64433(11) 0.0268(2) Uani 1 1 d . . . C24 C 0.52804(8) -0.09950(19) 0.56240(13) 0.0283(5) Uani 1 1 d . . . H24 H 0.5262 -0.1415 0.5157 0.034 Uiso 1 1 calc R . . N22 N 0.40815(6) -0.12859(16) 0.65013(11) 0.0239(4) Uani 1 1 d . . . C26 C 0.44418(8) -0.15467(18) 0.59263(12) 0.0247(4) Uani 1 1 d . . . H26A H 0.4325 -0.1359 0.5392 0.030 Uiso 1 1 calc R . . H26B H 0.4509 -0.2337 0.5940 0.030 Uiso 1 1 calc R . . O21 O 0.33041(6) -0.15124(18) 0.70580(11) 0.0401(4) Uani 1 1 d . . . C23 C 0.56942(8) -0.0443(2) 0.58452(15) 0.0331(5) Uani 1 1 d . . . H23 H 0.5961 -0.0482 0.5532 0.040 Uiso 1 1 calc R . . C25 C 0.48906(7) -0.09087(17) 0.61157(12) 0.0216(4) Uani 1 1 d . . . C106 C 0.30405(9) 0.2338(4) 0.64991(18) 0.0411(11) Uani 1 1 d . . . H106 H 0.3058 0.1576 0.6585 0.049 Uiso 1 1 calc R . . C103 C 0.29806(9) 0.4622(2) 0.62683(15) 0.0314(5) Uani 1 1 d . . . H103 H 0.2964 0.5387 0.6197 0.038 Uiso 1 1 calc R . . C101 C 0.34516(8) 0.29820(18) 0.65008(12) 0.0241(4) Uani 1 1 d . . . C201 C 0.33436(8) -0.1624(2) 0.54882(14) 0.0282(4) Uani 1 1 d . . . C102 C 0.34201(8) 0.41256(19) 0.64097(13) 0.0273(4) Uani 1 1 d . . . H102 H 0.3694 0.4559 0.6444 0.033 Uiso 1 1 calc R . . C12 C 0.44092(10) -0.0583(2) 0.97641(14) 0.0345(5) Uani 1 1 d . . . H12 H 0.4504 -0.1145 1.0116 0.041 Uiso 1 1 calc R . . C16 C 0.39864(10) 0.19165(18) 0.81144(13) 0.0318(5) Uani 1 1 d . . . H16A H 0.3673 0.2196 0.8232 0.038 Uiso 1 1 calc R . . H16B H 0.4209 0.2532 0.8151 0.038 Uiso 1 1 calc R . . C13 C 0.43247(10) 0.0476(2) 1.00472(13) 0.0337(5) Uani 1 1 d . . . H13 H 0.4368 0.0634 1.0589 0.040 Uiso 1 1 calc R . . C104 C 0.25676(9) 0.4004(2) 0.62311(17) 0.0400(6) Uani 1 1 d . . . C105 C 0.26023(10) 0.2860(2) 0.6366(2) 0.0525(8) Uani 1 1 d . . . H105 H 0.2326 0.2435 0.6367 0.063 Uiso 1 1 calc R . . C206 C 0.32256(9) -0.0527(2) 0.53268(16) 0.0380(6) Uani 1 1 d . . . H206 H 0.3257 0.0011 0.5724 0.046 Uiso 1 1 calc R . . C21 C 0.53090(8) 0.02606(18) 0.70012(13) 0.0247(4) Uani 1 1 d . . . C211 C 0.52977(8) 0.0921(2) 0.77555(14) 0.0311(5) Uani 1 1 d . . . H21A H 0.5075 0.1521 0.7689 0.047 Uiso 1 1 calc R . . H21B H 0.5609 0.1216 0.7877 0.047 Uiso 1 1 calc R . . H21C H 0.5202 0.0451 0.8186 0.047 Uiso 1 1 calc R . . C111 C 0.44457(10) -0.19283(18) 0.86078(14) 0.0344(5) Uani 1 1 d . . . H11A H 0.4184 -0.2139 0.8260 0.052 Uiso 1 1 calc R . . H11B H 0.4482 -0.2462 0.9032 0.052 Uiso 1 1 calc R . . H11C H 0.4732 -0.1903 0.8310 0.052 Uiso 1 1 calc R . . C204 C 0.30179(9) -0.1024(3) 0.39562(16) 0.0412(6) Uani 1 1 d . . . C205 C 0.30592(10) -0.0242(3) 0.45648(18) 0.0443(7) Uani 1 1 d . . . H205 H 0.2973 0.0491 0.4459 0.053 Uiso 1 1 calc R . . C203 C 0.31418(11) -0.2108(3) 0.41306(17) 0.0506(8) Uani 1 1 d . . . H203 H 0.3116 -0.2646 0.3732 0.061 Uiso 1 1 calc R . . C107 C 0.20912(11) 0.4562(3) 0.6088(3) 0.0622(9) Uani 1 1 d . . . H10A H 0.1944 0.4685 0.6591 0.093 Uiso 1 1 calc R . . H10B H 0.1891 0.4094 0.5758 0.093 Uiso 1 1 calc R . . H10C H 0.2136 0.5261 0.5825 0.093 Uiso 1 1 calc R . . C22 C 0.5700(4) 0.0165(10) 0.6542(7) 0.0310(18) Uani 1 1 d . . . H22 H 0.5979 0.0524 0.6705 0.037 Uiso 1 1 calc R . . C207 C 0.28479(11) -0.0698(4) 0.31257(18) 0.0599(10) Uani 1 1 d . . . H20A H 0.3004 -0.1150 0.2740 0.090 Uiso 1 1 calc R . . H20B H 0.2921 0.0070 0.3034 0.090 Uiso 1 1 calc R . . H20C H 0.2510 -0.0806 0.3074 0.090 Uiso 1 1 calc R . . C202 C 0.33051(9) -0.241(2) 0.48943(15) 0.041(2) Uani 1 1 d . . . H202 H 0.3388 -0.3144 0.5002 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02368(13) 0.01792(12) 0.01732(12) -0.00133(8) 0.00271(9) 0.00131(9) S11 0.0300(2) 0.0245(8) 0.02090(19) 0.0052(2) 0.00427(16) 0.0043(2) N11 0.018(3) 0.021(2) 0.0176(13) 0.0045(11) 0.0043(13) 0.0024(17) N12 0.0400(10) 0.0197(8) 0.0184(8) 0.0027(7) 0.0042(7) 0.0069(7) N21 0.0212(8) 0.0198(8) 0.0192(8) 0.0015(6) 0.0005(6) -0.0002(6) O11 0.0442(10) 0.0336(9) 0.0211(7) 0.0035(6) 0.0075(7) 0.0120(7) C15 0.0318(11) 0.0207(10) 0.0201(9) 0.0007(8) 0.0048(8) 0.0002(8) O12 0.0293(8) 0.0316(9) 0.0379(9) 0.0094(7) -0.0010(7) -0.0008(7) C11 0.0353(12) 0.0206(10) 0.0235(10) 0.0035(9) 0.0028(8) 0.0014(9) C14 0.0400(13) 0.0219(10) 0.0222(10) -0.0037(8) 0.0061(9) 0.0007(9) O22 0.047(3) 0.0244(19) 0.055(2) 0.0087(14) -0.0154(18) -0.013(2) S21 0.0225(4) 0.0297(5) 0.0280(5) 0.0020(4) -0.0038(3) -0.0053(3) C24 0.0301(11) 0.0286(11) 0.0265(10) 0.0017(9) 0.0070(8) 0.0073(9) N22 0.0214(8) 0.0262(9) 0.0242(8) -0.0057(7) 0.0019(7) -0.0015(7) C26 0.0265(10) 0.0253(10) 0.0223(10) -0.0051(8) 0.0015(8) 0.0023(8) O21 0.0253(8) 0.0624(13) 0.0328(9) 0.0023(9) 0.0029(7) -0.0035(8) C23 0.0256(11) 0.0334(12) 0.0409(13) 0.0108(11) 0.0116(10) 0.0054(9) C25 0.0250(10) 0.0187(9) 0.0212(9) 0.0015(7) 0.0013(7) 0.0027(8) C106 0.0406(11) 0.011(3) 0.0720(16) -0.0022(11) 0.0052(11) -0.0029(10) C103 0.0358(12) 0.0225(10) 0.0359(12) 0.0035(9) 0.0010(10) 0.0036(9) C101 0.0297(11) 0.0197(9) 0.0229(10) 0.0008(8) 0.0005(8) 0.0028(8) C201 0.0219(10) 0.0320(12) 0.0305(11) -0.0001(9) -0.0022(8) -0.0028(9) C102 0.0297(11) 0.0210(10) 0.0311(11) 0.0026(8) 0.0005(9) -0.0007(8) C12 0.0548(15) 0.0272(12) 0.0214(10) 0.0058(9) -0.0004(10) 0.0049(11) C16 0.0523(14) 0.0220(11) 0.0212(10) -0.0005(8) 0.0059(9) 0.0094(10) C13 0.0494(14) 0.0331(12) 0.0186(10) -0.0014(9) 0.0021(9) 0.0007(11) C104 0.0319(12) 0.0384(14) 0.0494(15) -0.0050(12) -0.0046(11) 0.0066(11) C105 0.0311(13) 0.0357(14) 0.091(2) -0.0089(13) 0.0010(14) -0.0067(10) C206 0.0410(14) 0.0379(14) 0.0348(13) -0.0018(11) -0.0022(11) 0.0103(11) C21 0.0259(10) 0.0200(9) 0.0280(10) 0.0046(8) -0.0024(8) -0.0023(8) C211 0.0317(12) 0.0306(12) 0.0307(11) -0.0007(9) -0.0053(9) -0.0108(9) C111 0.0525(15) 0.0206(11) 0.0300(11) 0.0027(9) 0.0018(10) 0.0074(10) C204 0.0228(11) 0.0663(19) 0.0345(13) 0.0095(13) -0.0022(9) -0.0064(11) C205 0.0375(14) 0.0517(17) 0.0435(15) 0.0115(13) -0.0008(11) 0.0116(12) C203 0.0555(17) 0.0579(18) 0.0375(13) -0.0080(12) -0.0128(12) -0.0130(13) C107 0.0350(15) 0.060(2) 0.091(3) -0.0029(19) -0.0119(16) 0.0116(14) C22 0.017(3) 0.028(3) 0.048(2) 0.0026(19) -0.0003(17) 0.001(2) C207 0.0404(16) 0.102(3) 0.0366(15) 0.0230(17) -0.0072(12) -0.0077(17) C202 0.0507(12) 0.032(6) 0.0408(11) 0.001(2) -0.0125(9) -0.006(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 Zn1 N22 1.9286(18) . ? Zn1 N12 1.9540(18) . ? Zn1 N11 2.050(7) . ? Zn1 N21 2.0889(17) . ? S11 O11 1.4496(17) . ? S11 O12 1.4500(19) . ? S11 N12 1.5822(19) . ? S11 C101 1.770(2) . ? N11 C11 1.344(7) . ? N11 C15 1.347(9) . ? N12 C16 1.463(3) . ? N21 C25 1.339(3) . ? N21 C21 1.356(3) . ? C15 C14 1.393(3) . ? C15 C16 1.507(3) . ? C11 C12 1.384(3) . ? C11 C111 1.497(3) . ? C14 C13 1.375(3) . ? O22 S21 1.454(4) . ? S21 O21 1.444(3) . ? S21 N22 1.579(3) . ? S21 C201 1.778(3) . ? C24 C23 1.381(3) . ? C24 C25 1.394(3) . ? N22 C26 1.452(3) . ? C26 C25 1.503(3) . ? C23 C22 1.376(12) . ? C106 C101 1.392(4) . ? C106 C105 1.395(4) . ? C103 C104 1.379(4) . ? C103 C102 1.387(3) . ? C101 C102 1.387(3) . ? C201 C202 1.373(17) . ? C201 C206 1.385(4) . ? C12 C13 1.383(4) . ? C104 C105 1.398(4) . ? C104 C107 1.512(4) . ? C206 C205 1.388(4) . ? C21 C22 1.365(10) . ? C21 C211 1.492(3) . ? C204 C203 1.379(4) . ? C204 C205 1.389(4) . ? C204 C207 1.508(4) . ? C203 C202 1.392(8) . ? 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 N22 Zn1 N12 134.01(8) . . ? N22 Zn1 N11 129.8(3) . . ? N12 Zn1 N11 82.8(2) . . ? N22 Zn1 N21 82.01(7) . . ? N12 Zn1 N21 117.47(8) . . ? N11 Zn1 N21 113.3(2) . . ? O11 S11 O12 116.93(11) . . ? O11 S11 N12 106.18(11) . . ? O12 S11 N12 112.87(10) . . ? O11 S11 C101 107.14(10) . . ? O12 S11 C101 105.94(11) . . ? N12 S11 C101 107.29(10) . . ? C11 N11 C15 120.0(5) . . ? C11 N11 Zn1 126.9(5) . . ? C15 N11 Zn1 112.2(4) . . ? C16 N12 S11 116.08(15) . . ? C16 N12 Zn1 115.65(13) . . ? S11 N12 Zn1 122.28(10) . . ? C25 N21 C21 120.12(18) . . ? C25 N21 Zn1 111.09(13) . . ? C21 N21 Zn1 128.12(15) . . ? N11 C15 C14 121.6(3) . . ? N11 C15 C16 118.3(3) . . ? C14 C15 C16 120.15(19) . . ? N11 C11 C12 120.6(4) . . ? N11 C11 C111 116.9(4) . . ? C12 C11 C111 122.5(2) . . ? C13 C14 C15 118.5(2) . . ? O21 S21 O22 117.5(3) . . ? O21 S21 N22 106.09(18) . . ? O22 S21 N22 112.5(4) . . ? O21 S21 C201 109.24(18) . . ? O22 S21 C201 105.7(3) . . ? N22 S21 C201 105.25(14) . . ? C23 C24 C25 118.5(2) . . ? C26 N22 S21 117.62(17) . . ? C26 N22 Zn1 116.21(14) . . ? S21 N22 Zn1 126.00(13) . . ? N22 C26 C25 110.39(17) . . ? C22 C23 C24 118.1(5) . . ? N21 C25 C24 121.7(2) . . ? N21 C25 C26 117.71(17) . . ? C24 C25 C26 120.54(19) . . ? C101 C106 C105 118.7(4) . . ? C104 C103 C102 121.4(2) . . ? C102 C101 C106 120.1(3) . . ? C102 C101 S11 120.60(18) . . ? C106 C101 S11 119.3(2) . . ? C202 C201 C206 120.1(8) . . ? C202 C201 S21 121.0(7) . . ? C206 C201 S21 118.6(2) . . ? C103 C102 C101 120.0(2) . . ? C13 C12 C11 119.8(2) . . ? N12 C16 C15 109.88(17) . . ? C14 C13 C12 119.5(2) . . ? C103 C104 C105 118.0(2) . . ? C103 C104 C107 120.6(3) . . ? C105 C104 C107 121.4(3) . . ? C106 C105 C104 121.7(3) . . ? C201 C206 C205 119.1(3) . . ? N21 C21 C22 119.2(5) . . ? N21 C21 C211 116.82(19) . . ? C22 C21 C211 124.0(5) . . ? C203 C204 C205 118.1(2) . . ? C203 C204 C207 120.8(3) . . ? C205 C204 C207 121.1(3) . . ? C206 C205 C204 121.6(3) . . ? C204 C203 C202 121.0(10) . . ? C21 C22 C23 122.1(9) . . ? C201 C202 C203 120.1(17) . . ? _diffrn_measured_fraction_theta_max 0.523 _diffrn_reflns_theta_full 28.51 _diffrn_measured_fraction_theta_full 0.523 _refine_diff_density_max 0.399 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.038 data_CuL1 _database_code_CSD 186301 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 Cu N4 O4 S2' _chemical_formula_weight 586.17 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)/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 9.9115(7) _cell_length_b 17.0894(11) _cell_length_c 7.2934(6) _cell_angle_alpha 90 _cell_angle_beta 99.177(4) _cell_angle_gamma 90 _cell_volume 1219.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 919 _cell_measurement_theta_min 12.06542 _cell_measurement_theta_max 26.09368 _exptl_crystal_description block _exptl_crystal_colour translucent-light-brown _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 1.11 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15s exposure) covering 0.3\% in \w. Crystal to detector distance 4.5 cm. ; _cell_measurement_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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 919 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 21 _diffrn_reflns_limit_k_max -22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 28.51 _reflns_number_total 3090 _reflns_number_gt 2867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.1000P)^2^+0.1000P] 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 3090 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.1197 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Cu1 Cu 0.5000 0.5000 0.0000 0.01297(13) Uani 1 2 d S . . S1 S 0.31944(6) 0.45824(2) 0.24806(4) 0.01403(14) Uani 1 1 d . . . N1 N 0.3925(2) 0.40437(8) -0.09840(14) 0.0143(3) Uani 1 1 d . . . O1 O 0.34827(19) 0.43653(7) 0.39153(12) 0.0192(3) Uani 1 1 d . . . O2 O 0.18697(18) 0.41253(8) 0.15580(13) 0.0185(3) Uani 1 1 d . . . N2 N 0.48759(19) 0.54224(8) -0.18899(14) 0.0144(3) Uani 1 1 d . . . C2 C 0.3194(2) 0.41759(10) -0.23037(16) 0.0147(3) Uani 1 1 d . . . C3 C 0.2455(2) 0.35705(11) -0.31627(17) 0.0172(3) Uani 1 1 d . . . H3 H 0.204(3) 0.3715(14) -0.409(2) 0.020(5) Uiso 1 1 d . . . C4 C 0.2534(2) 0.28106(10) -0.26535(18) 0.0182(3) Uani 1 1 d . . . C5 C 0.3339(2) 0.26712(10) -0.12995(18) 0.0171(3) Uani 1 1 d . . . H5 H 0.346(3) 0.2188(15) -0.092(2) 0.016(5) Uiso 1 1 d . . . C6 C 0.3990(2) 0.33084(10) -0.04890(17) 0.0158(3) Uani 1 1 d . . . C7 C 0.3322(3) 0.50146(9) -0.2764(2) 0.0173(4) Uani 1 1 d . . . H7 H 0.336(3) 0.5079(12) -0.369(2) 0.011(5) Uiso 1 1 d . . . C8 C 0.2403(2) 0.55685(10) 0.23805(16) 0.0138(3) Uani 1 1 d . . . C9 C 0.1455(2) 0.58497(10) 0.11285(17) 0.0152(3) Uani 1 1 d . . . H9 H 0.103(3) 0.5491(14) 0.039(2) 0.019(5) Uiso 1 1 d . . . C10 C 0.1124(2) 0.66500(10) 0.09664(17) 0.0167(3) Uani 1 1 d . . . H10 H 0.039(3) 0.6851(17) 0.009(2) 0.024(6) Uiso 1 1 d . . . C11 C 0.1736(2) 0.71799(10) 0.20221(18) 0.0158(3) Uani 1 1 d . . . C12 C 0.2620(2) 0.68799(11) 0.32704(17) 0.0175(3) Uani 1 1 d . . . H12 H 0.307(4) 0.7241(15) 0.406(3) 0.023(6) Uiso 1 1 d . . . C13 C 0.2956(2) 0.60811(10) 0.34596(17) 0.0161(3) Uani 1 1 d . . . H13 H 0.361(3) 0.5878(14) 0.432(2) 0.015(5) Uiso 1 1 d . . . C14 C 0.1485(3) 0.80504(11) 0.1821(2) 0.0220(4) Uani 1 1 d . . . H142 H 0.088(5) 0.809(2) 0.098(4) 0.068(11) Uiso 1 1 d . . . H141 H 0.103(4) 0.829(2) 0.257(3) 0.064(10) Uiso 1 1 d . . . H4 H 0.209(4) 0.2422(16) -0.323(3) 0.027(6) Uiso 1 1 d . . . H6 H 0.463(3) 0.3209(15) 0.051(2) 0.023(6) Uiso 1 1 d . . . H72 H 0.217(3) 0.5292(15) -0.270(2) 0.018(5) Uiso 1 1 d . . . H143 H 0.263(5) 0.827(2) 0.182(3) 0.061(10) 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 Cu1 0.01790(19) 0.00902(19) 0.01163(18) -0.00041(8) 0.00123(12) -0.00130(9) S1 0.0201(2) 0.0099(2) 0.0118(2) 0.00060(12) 0.00173(16) -0.00180(13) N1 0.0179(7) 0.0115(7) 0.0134(6) -0.0009(5) 0.0022(5) -0.0005(5) O1 0.0300(7) 0.0147(6) 0.0129(5) 0.0034(4) 0.0039(5) -0.0007(5) O2 0.0210(6) 0.0142(6) 0.0196(6) -0.0019(4) 0.0012(5) -0.0049(5) N2 0.0173(7) 0.0120(6) 0.0132(6) -0.0002(5) 0.0000(5) -0.0007(5) C2 0.0159(7) 0.0145(8) 0.0140(7) -0.0014(5) 0.0030(6) -0.0010(6) C3 0.0190(8) 0.0168(8) 0.0160(7) -0.0026(6) 0.0036(6) -0.0024(6) C4 0.0198(8) 0.0143(8) 0.0214(8) -0.0064(6) 0.0059(6) -0.0044(6) C5 0.0189(8) 0.0108(8) 0.0229(8) -0.0013(6) 0.0072(6) -0.0011(6) C6 0.0183(8) 0.0132(8) 0.0164(7) -0.0001(6) 0.0043(6) -0.0001(6) C7 0.0201(9) 0.0154(9) 0.0149(8) 0.0004(5) -0.0015(7) -0.0012(5) C8 0.0167(7) 0.0112(8) 0.0136(7) 0.0009(5) 0.0030(6) -0.0005(6) C9 0.0162(8) 0.0149(8) 0.0142(7) -0.0009(6) 0.0015(6) -0.0009(6) C10 0.0170(7) 0.0167(8) 0.0159(7) 0.0022(6) 0.0011(6) 0.0015(6) C11 0.0143(7) 0.0133(8) 0.0207(8) 0.0005(6) 0.0056(6) 0.0005(6) C12 0.0181(7) 0.0156(8) 0.0192(8) -0.0039(6) 0.0040(6) -0.0012(6) C13 0.0176(7) 0.0157(8) 0.0150(7) -0.0004(6) 0.0029(6) -0.0004(6) C14 0.0245(9) 0.0147(8) 0.0272(9) 0.0018(7) 0.0054(7) 0.0014(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 Cu1 N2 1.9959(14) . ? Cu1 N2 1.9959(14) 3_665 ? Cu1 N1 1.9981(14) . ? Cu1 N1 1.9981(14) 3_665 ? S1 O2 1.4485(12) . ? S1 O1 1.4521(12) . ? S1 N2 1.6083(15) 3_665 ? S1 C8 1.7789(17) . ? N1 C6 1.347(2) . ? N1 C2 1.350(2) . ? N2 C7 1.485(2) . ? N2 S1 1.6083(15) 3_665 ? C2 C3 1.393(2) . ? C2 C7 1.512(2) . ? C3 C4 1.391(2) . ? C4 C5 1.397(3) . ? C5 C6 1.391(2) . ? C8 C13 1.391(2) . ? C8 C9 1.406(2) . ? C9 C10 1.394(2) . ? C10 C11 1.402(2) . ? C11 C12 1.398(2) . ? C11 C14 1.508(2) . ? C12 C13 1.394(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N2 180.00(7) . 3_665 ? N2 Cu1 N1 83.23(6) . . ? N2 Cu1 N1 96.77(6) 3_665 . ? N2 Cu1 N1 96.77(6) . 3_665 ? N2 Cu1 N1 83.23(6) 3_665 3_665 ? N1 Cu1 N1 180.00(8) . 3_665 ? O2 S1 O1 117.28(8) . . ? O2 S1 N2 107.56(8) . 3_665 ? O1 S1 N2 110.90(8) . 3_665 ? O2 S1 C8 107.34(8) . . ? O1 S1 C8 106.96(8) . . ? N2 S1 C8 106.22(8) 3_665 . ? C6 N1 C2 119.63(14) . . ? C6 N1 Cu1 126.65(11) . . ? C2 N1 Cu1 113.54(11) . . ? C7 N2 S1 114.56(12) . 3_665 ? C7 N2 Cu1 107.10(10) . . ? S1 N2 Cu1 115.37(7) 3_665 . ? N1 C2 C3 121.49(16) . . ? N1 C2 C7 114.66(15) . . ? C3 C2 C7 123.81(16) . . ? C2 C3 C4 118.82(16) . . ? C5 C4 C3 119.64(15) . . ? C6 C5 C4 118.28(16) . . ? N1 C6 C5 122.07(16) . . ? N2 C7 C2 110.29(14) . . ? C13 C8 C9 120.32(15) . . ? C13 C8 S1 120.12(13) . . ? C9 C8 S1 118.87(12) . . ? C10 C9 C8 119.28(15) . . ? C9 C10 C11 121.28(15) . . ? C12 C11 C10 118.08(16) . . ? C12 C11 C14 120.52(17) . . ? C10 C11 C14 121.39(16) . . ? C13 C12 C11 121.62(16) . . ? C12 C13 C8 119.33(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 2.38 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.456 _refine_diff_density_min -1.001 _refine_diff_density_rms 0.075 data_CuL2 _database_code_CSD 186302 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cu F6 N4 O4 S2' _chemical_formula_weight 541.94 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 9.0349(11) _cell_length_b 10.2869(14) _cell_length_c 20.698(3) _cell_angle_alpha 90 _cell_angle_beta 91.706(5) _cell_angle_gamma 90 _cell_volume 1922.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5235 _cell_measurement_theta_min 2.4256 _cell_measurement_theta_max 28.6427 _exptl_crystal_description block _exptl_crystal_colour clear_light_blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.872 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 1.442 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6789 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15s exposure) covering 0.3\% in \w. Crystal to detector distance 4.5 cm. ; _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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method 'w\-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 11846 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 0.98 _diffrn_reflns_theta_max 27.45 _reflns_number_total 7978 _reflns_number_gt 7248 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0731P)^2^+135.9643P] 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 0.08(5) _refine_ls_number_reflns 7978 _refine_ls_number_parameters 560 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1521 _refine_ls_R_factor_gt 0.1409 _refine_ls_wR_factor_ref 0.3680 _refine_ls_wR_factor_gt 0.3597 _refine_ls_goodness_of_fit_ref 1.197 _refine_ls_restrained_S_all 1.196 _refine_ls_shift/su_max 1.684 _refine_ls_shift/su_mean 0.032 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 0.6463(3) 0.5904(2) 0.56548(12) 0.0122(5) Uani 1 1 d . . . Cu2 Cu 0.1535(3) 0.9744(2) 0.70958(12) 0.0123(5) Uani 1 1 d . . . S4 S 0.7055(6) 0.3844(5) 0.4642(3) 0.0145(10) Uani 1 1 d . . . S5 S 0.3207(5) 0.6453(5) 0.6023(3) 0.0148(10) Uani 1 1 d . . . S3 S 0.2241(6) 1.1793(5) 0.8111(3) 0.0142(10) Uani 1 1 d . . . S6 S -0.1772(6) 0.9200(5) 0.6739(3) 0.0172(11) Uani 1 1 d . . . F2 F -0.185(2) 1.0655(13) 0.7776(7) 0.033(4) Uani 1 1 d . . . F3 F -0.2893(17) 0.8801(16) 0.7867(6) 0.031(4) Uani 1 1 d . . . F1 F -0.3952(17) 1.036(2) 0.7318(9) 0.053(6) Uani 1 1 d . . . F4 F 0.4819(19) 1.0993(18) 0.8589(7) 0.039(4) Uani 1 1 d . . . F12 F 0.9483(17) 0.4661(15) 0.4121(7) 0.030(3) Uani 1 1 d . . . F11 F 0.9738(15) 0.2825(17) 0.4578(8) 0.034(4) Uani 1 1 d . . . F9 F 0.1767(17) 0.6937(16) 0.4923(7) 0.033(4) Uani 1 1 d . . . F10 F 0.8527(16) 0.3000(16) 0.3649(6) 0.030(4) Uani 1 1 d . . . F6 F 0.391(2) 1.2612(17) 0.9073(8) 0.046(5) Uani 1 1 d . . . F5 F 0.487(2) 1.286(2) 0.8158(7) 0.045(5) Uani 1 1 d . . . F7 F 0.284(2) 0.510(2) 0.4959(9) 0.051(5) Uani 1 1 d . . . F8 F 0.088(2) 0.536(2) 0.5476(10) 0.061(7) Uani 1 1 d . . . N1 N 0.6966(17) 0.7337(18) 0.5093(7) 0.009(3) Uani 1 1 d . . . N4 N 0.7522(19) 0.4432(15) 0.5340(10) 0.018(4) Uani 1 1 d . . . N3 N 0.685(2) 0.4986(16) 0.6493(9) 0.014(4) Uani 1 1 d . . . N2 N 0.471(2) 0.695(2) 0.5783(9) 0.021(4) Uani 1 1 d . . . N8 N 0.1735(19) 1.0648(18) 0.6263(8) 0.015(4) Uani 1 1 d . . . N5 N 0.2160(18) 0.8292(17) 0.7678(8) 0.012(3) Uani 1 1 d . . . N9 N -0.018(2) 0.8689(16) 0.6958(9) 0.017(4) Uani 1 1 d . . . N7 N 0.266(3) 1.1230(19) 0.7442(9) 0.022(4) Uani 1 1 d . . . C2 C 0.7727(19) 0.3936(18) 0.6482(9) 0.007(3) Uani 1 1 d . . . C9 C 0.655(3) 0.960(3) 0.4881(10) 0.025(5) Uani 1 1 d . . . C11 C 0.853(2) 0.853(2) 0.4408(10) 0.017(5) Uani 1 1 d . . . C3 C 0.838(3) 0.335(2) 0.7025(11) 0.023(5) Uani 1 1 d . . . C7 C 0.609(3) 0.841(2) 0.5166(10) 0.018(5) Uani 1 1 d . . . C5 C 0.699(3) 0.487(3) 0.7642(11) 0.024(5) Uani 1 1 d . . . C6 C 0.640(2) 0.5460(18) 0.7050(10) 0.010(4) Uani 1 1 d . . . C1 C 0.807(3) 0.349(2) 0.5806(11) 0.027(6) Uani 1 1 d . . . C8 C 0.475(2) 0.829(2) 0.5561(11) 0.017(4) Uani 1 1 d . . . C4 C 0.791(2) 0.3844(19) 0.7611(10) 0.014(4) Uani 1 1 d . . . C10 C 0.773(3) 0.965(2) 0.4494(13) 0.026(5) Uani 1 1 d . . . C13 C 0.880(3) 0.358(2) 0.4228(9) 0.020(5) Uani 1 1 d . . . C12 C 0.821(2) 0.7373(19) 0.4723(12) 0.018(5) Uani 1 1 d . . . C20 C 0.270(2) 1.1677(18) 0.6264(10) 0.015(4) Uani 1 1 d . . . C17 C 0.162(2) 0.610(2) 0.7948(12) 0.017(5) Uani 1 1 d . . . C18 C 0.137(2) 0.724(2) 0.7640(10) 0.012(4) Uani 1 1 d . . . C21 C 0.324(3) 1.223(3) 0.5722(12) 0.036(7) Uani 1 1 d . . . C16 C 0.299(2) 0.608(2) 0.8282(12) 0.020(5) Uani 1 1 d . . . C24 C 0.139(3) 1.017(2) 0.5676(11) 0.024(5) Uani 1 1 d . . . C22 C 0.286(3) 1.173(3) 0.5128(15) 0.041(8) Uani 1 1 d . . . C26 C -0.268(3) 0.979(3) 0.7475(11) 0.023(5) Uani 1 1 d . . . C15 C 0.387(2) 0.715(2) 0.8372(13) 0.025(5) Uani 1 1 d . . . C23 C 0.186(3) 1.0687(19) 0.5098(9) 0.014(4) Uani 1 1 d . . . C19 C -0.015(3) 0.736(2) 0.7181(12) 0.022(5) Uani 1 1 d . . . C25 C 0.317(3) 1.214(3) 0.6920(10) 0.032(7) Uani 1 1 d . . . C14 C 0.339(3) 0.825(3) 0.8022(9) 0.024(6) Uani 1 1 d . . . C28 C 0.208(4) 0.587(3) 0.5303(14) 0.038(7) Uani 1 1 d . . . C27 C 0.405(3) 1.212(2) 0.8504(12) 0.029(6) Uani 1 1 d . . . O2 O 0.6351(18) 0.4870(14) 0.4266(8) 0.019(3) Uani 1 1 d . . . O1 O 0.6469(16) 0.2542(17) 0.4679(8) 0.016(3) Uani 1 1 d . . . O5 O -0.2735(16) 0.8153(16) 0.6547(8) 0.019(3) Uani 1 1 d . . . O4 O 0.159(2) 1.0836(15) 0.8484(8) 0.022(4) Uani 1 1 d . . . O3 O 0.163(2) 1.3098(16) 0.8112(9) 0.030(4) Uani 1 1 d . . . O6 O -0.163(2) 1.0362(16) 0.6364(8) 0.024(4) Uani 1 1 d . . . O7 O 0.2276(17) 0.7542(19) 0.6239(9) 0.023(4) Uani 1 1 d . . . O8 O 0.3398(19) 0.5324(17) 0.6367(9) 0.027(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 Cu1 0.0187(13) 0.0066(10) 0.0114(11) 0.0011(10) 0.0018(9) 0.0066(10) Cu2 0.0171(12) 0.0078(10) 0.0118(11) 0.0029(10) -0.0016(9) 0.0034(10) S4 0.019(2) 0.006(2) 0.018(2) 0.000(2) -0.003(2) 0.0058(19) S5 0.008(2) 0.016(2) 0.021(2) 0.000(2) 0.0014(19) 0.002(2) S3 0.008(2) 0.012(2) 0.022(3) -0.001(2) -0.0082(19) 0.0045(19) S6 0.013(2) 0.019(3) 0.020(2) 0.007(2) -0.002(2) 0.001(2) F2 0.057(10) 0.012(6) 0.031(8) -0.001(6) 0.017(7) 0.009(7) F3 0.031(8) 0.043(9) 0.019(7) 0.015(7) 0.016(6) 0.019(7) F1 0.022(8) 0.069(13) 0.070(12) 0.029(11) 0.020(8) 0.055(9) F4 0.046(10) 0.045(10) 0.026(7) -0.007(8) -0.016(7) 0.023(9) F12 0.028(8) 0.031(8) 0.033(8) -0.009(7) 0.013(6) 0.006(6) F11 0.013(7) 0.052(10) 0.038(8) 0.005(8) 0.009(6) 0.018(7) F9 0.027(8) 0.036(9) 0.034(8) 0.009(7) -0.019(7) -0.007(7) F10 0.030(8) 0.043(9) 0.018(6) -0.025(7) 0.001(6) 0.006(7) F6 0.072(13) 0.038(10) 0.027(8) -0.028(8) 0.002(8) -0.007(9) F5 0.048(10) 0.066(13) 0.020(7) -0.003(8) -0.004(7) -0.017(10) F7 0.068(13) 0.051(11) 0.035(9) -0.028(9) -0.007(9) -0.037(10) F8 0.038(10) 0.083(15) 0.060(12) 0.048(12) -0.030(9) -0.038(11) N1 0.004(7) 0.018(9) 0.004(7) -0.001(7) -0.012(5) 0.000(6) N4 0.012(8) 0.000(7) 0.039(11) 0.016(8) -0.028(8) -0.014(6) N3 0.014(9) 0.003(7) 0.026(9) -0.006(7) 0.002(7) 0.000(7) N2 0.012(9) 0.028(11) 0.021(9) -0.007(9) -0.015(7) 0.005(8) N8 0.011(8) 0.020(9) 0.016(8) 0.011(7) 0.025(7) 0.012(7) N5 0.008(8) 0.010(8) 0.017(8) -0.009(7) -0.004(6) 0.002(6) N9 0.025(9) 0.000(7) 0.027(9) 0.003(7) 0.015(8) -0.011(7) N7 0.036(11) 0.018(10) 0.013(8) 0.000(8) 0.014(8) -0.003(9) C2 0.000(7) 0.005(8) 0.016(9) 0.002(7) -0.003(6) -0.002(6) C9 0.044(15) 0.025(12) 0.006(9) 0.009(9) -0.007(9) 0.005(12) C11 0.015(10) 0.028(12) 0.008(9) 0.018(9) -0.001(7) 0.007(9) C3 0.027(12) 0.024(12) 0.019(11) -0.009(10) -0.001(9) -0.020(10) C7 0.023(11) 0.020(11) 0.011(9) -0.013(9) 0.010(8) 0.012(9) C5 0.027(13) 0.031(13) 0.013(9) 0.010(10) -0.009(9) 0.010(11) C6 0.013(9) 0.005(8) 0.011(8) 0.010(8) -0.010(7) 0.015(8) C1 0.062(17) 0.010(10) 0.011(9) 0.014(9) 0.014(10) 0.020(11) C8 0.013(10) 0.009(9) 0.029(11) 0.005(9) -0.002(9) -0.001(8) C4 0.016(10) 0.007(9) 0.019(10) -0.008(8) -0.010(8) 0.009(8) C10 0.021(12) 0.019(11) 0.039(14) 0.027(11) -0.002(10) 0.001(9) C13 0.025(12) 0.033(13) 0.004(8) -0.016(9) 0.015(8) -0.002(10) C12 0.011(9) 0.001(8) 0.042(13) 0.011(9) -0.001(9) -0.014(7) C20 0.021(11) 0.003(8) 0.021(10) -0.009(8) 0.012(9) 0.006(8) C17 0.005(9) 0.016(10) 0.030(12) -0.007(10) -0.016(8) -0.002(8) C18 0.013(10) 0.009(9) 0.015(9) 0.010(8) 0.010(8) 0.004(7) C21 0.056(19) 0.028(13) 0.026(13) 0.015(11) 0.033(13) -0.003(13) C16 0.007(9) 0.023(11) 0.031(11) -0.013(10) -0.001(8) -0.007(9) C24 0.029(12) 0.027(12) 0.017(10) 0.010(11) -0.003(9) 0.032(11) C22 0.038(16) 0.039(16) 0.046(16) 0.027(14) 0.002(13) 0.038(14) C26 0.016(11) 0.030(13) 0.024(11) 0.016(10) 0.004(9) -0.014(10) C15 0.007(10) 0.027(13) 0.042(14) 0.015(12) -0.001(10) 0.010(9) C23 0.030(12) 0.006(9) 0.006(8) 0.001(7) -0.003(8) 0.017(9) C19 0.026(12) 0.011(10) 0.029(12) 0.006(9) 0.014(10) 0.018(9) C25 0.049(16) 0.041(15) 0.007(9) 0.015(11) -0.020(10) -0.027(14) C14 0.039(14) 0.033(13) 0.000(8) -0.006(9) -0.016(8) 0.019(11) C28 0.061(19) 0.018(12) 0.034(14) 0.022(12) -0.031(14) 0.005(13) C27 0.044(15) 0.017(11) 0.028(12) 0.013(10) 0.024(11) 0.019(11) O2 0.027(9) 0.003(6) 0.026(9) -0.004(6) -0.004(7) 0.018(6) O1 0.007(7) 0.020(8) 0.020(8) 0.003(7) -0.002(6) -0.002(6) O5 0.005(6) 0.017(7) 0.034(9) -0.018(7) 0.000(6) -0.003(6) O4 0.035(10) 0.012(8) 0.018(8) -0.005(7) 0.000(7) -0.016(7) O3 0.043(11) 0.011(8) 0.036(10) -0.010(8) -0.002(9) 0.021(8) O6 0.035(9) 0.014(7) 0.022(8) 0.018(7) -0.002(7) 0.013(7) O7 0.005(7) 0.032(9) 0.034(9) 0.003(8) 0.020(6) -0.005(6) O8 0.024(9) 0.015(8) 0.039(10) 0.008(8) -0.021(8) -0.005(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 Cu1 N4 1.92(2) . ? Cu1 N1 1.940(18) . ? Cu1 N2 1.939(19) . ? Cu1 N3 1.998(19) . ? Cu2 N9 1.906(18) . ? Cu2 N5 1.990(18) . ? Cu2 N8 1.971(17) . ? Cu2 N7 1.96(2) . ? S4 O1 1.442(17) . ? S4 O2 1.448(15) . ? S4 N4 1.611(19) . ? S4 C13 1.83(2) . ? S5 O8 1.370(17) . ? S5 O7 1.477(18) . ? S5 N2 1.55(2) . ? S5 C28 1.88(3) . ? S3 O4 1.392(16) . ? S3 O3 1.451(16) . ? S3 N7 1.560(19) . ? S3 C27 1.83(3) . ? S6 O6 1.434(16) . ? S6 O5 1.433(16) . ? S6 N9 1.59(2) . ? S6 C26 1.85(3) . ? F2 C26 1.31(3) . ? F3 C26 1.32(3) . ? F1 C26 1.32(3) . ? F4 C27 1.36(3) . ? F12 C13 1.29(3) . ? F11 C13 1.35(3) . ? F9 C28 1.37(3) . ? F10 C13 1.35(2) . ? F6 C27 1.29(3) . ? F5 C27 1.29(3) . ? F7 C28 1.29(4) . ? F8 C28 1.27(4) . ? N1 C12 1.38(3) . ? N1 C7 1.37(3) . ? N4 C1 1.44(3) . ? N3 C2 1.34(2) . ? N3 C6 1.33(3) . ? N2 C8 1.44(3) . ? N8 C24 1.34(3) . ? N8 C20 1.37(3) . ? N5 C18 1.30(3) . ? N5 C14 1.30(3) . ? N9 C19 1.44(3) . ? N7 C25 1.51(3) . ? C2 C3 1.39(3) . ? C2 C1 1.51(3) . ? C9 C10 1.35(4) . ? C9 C7 1.42(3) . ? C11 C10 1.38(3) . ? C11 C12 1.39(3) . ? C3 C4 1.39(3) . ? C7 C8 1.48(3) . ? C5 C4 1.35(3) . ? C5 C6 1.46(3) . ? C20 C21 1.36(3) . ? C20 C25 1.49(3) . ? C17 C18 1.35(3) . ? C17 C16 1.40(3) . ? C18 C19 1.65(3) . ? C21 C22 1.37(4) . ? C16 C15 1.37(3) . ? C24 C23 1.39(3) . ? C22 C23 1.41(4) . ? C15 C14 1.40(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N1 105.6(7) . . ? N4 Cu1 N2 154.7(7) . . ? N1 Cu1 N2 82.3(8) . . ? N4 Cu1 N3 81.0(7) . . ? N1 Cu1 N3 147.3(7) . . ? N2 Cu1 N3 105.6(8) . . ? N9 Cu2 N5 83.0(7) . . ? N9 Cu2 N8 103.5(8) . . ? N5 Cu2 N8 148.3(7) . . ? N9 Cu2 N7 155.6(8) . . ? N5 Cu2 N7 103.2(8) . . ? N8 Cu2 N7 83.8(8) . . ? O1 S4 O2 123.3(10) . . ? O1 S4 N4 112.9(9) . . ? O2 S4 N4 107.9(9) . . ? O1 S4 C13 102.2(10) . . ? O2 S4 C13 102.9(11) . . ? N4 S4 C13 105.6(10) . . ? O8 S5 O7 123.4(12) . . ? O8 S5 N2 110.5(11) . . ? O7 S5 N2 111.0(11) . . ? O8 S5 C28 101.6(11) . . ? O7 S5 C28 100.4(12) . . ? N2 S5 C28 108.1(13) . . ? O4 S3 O3 119.1(12) . . ? O4 S3 N7 110.4(10) . . ? O3 S3 N7 116.6(11) . . ? O4 S3 C27 105.7(11) . . ? O3 S3 C27 99.3(11) . . ? N7 S3 C27 102.9(12) . . ? O6 S6 O5 122.7(11) . . ? O6 S6 N9 109.6(10) . . ? O5 S6 N9 111.6(9) . . ? O6 S6 C26 102.9(11) . . ? O5 S6 C26 101.1(10) . . ? N9 S6 C26 107.1(11) . . ? C12 N1 C7 121.6(18) . . ? C12 N1 Cu1 124.3(14) . . ? C7 N1 Cu1 113.5(14) . . ? C1 N4 S4 115.0(15) . . ? C1 N4 Cu1 117.8(16) . . ? S4 N4 Cu1 118.8(9) . . ? C2 N3 C6 120.6(18) . . ? C2 N3 Cu1 117.1(14) . . ? C6 N3 Cu1 121.9(13) . . ? C8 N2 S5 116.6(15) . . ? C8 N2 Cu1 117.1(15) . . ? S5 N2 Cu1 125.8(13) . . ? C24 N8 C20 114.6(19) . . ? C24 N8 Cu2 126.5(16) . . ? C20 N8 Cu2 116.0(15) . . ? C18 N5 C14 118(2) . . ? C18 N5 Cu2 116.3(14) . . ? C14 N5 Cu2 125.3(17) . . ? C19 N9 S6 114.3(15) . . ? C19 N9 Cu2 119.1(17) . . ? S6 N9 Cu2 125.5(10) . . ? C25 N7 S3 119.6(17) . . ? C25 N7 Cu2 112.7(14) . . ? S3 N7 Cu2 118.3(11) . . ? N3 C2 C3 125(2) . . ? N3 C2 C1 113.4(17) . . ? C3 C2 C1 121.6(19) . . ? C10 C9 C7 122(2) . . ? C10 C11 C12 123(2) . . ? C4 C3 C2 115(2) . . ? N1 C7 C9 118(2) . . ? N1 C7 C8 118(2) . . ? C9 C7 C8 124(2) . . ? C4 C5 C6 120(2) . . ? N3 C6 C5 117.4(17) . . ? N4 C1 C2 109.9(18) . . ? N2 C8 C7 106.7(18) . . ? C5 C4 C3 122(2) . . ? C9 C10 C11 118(2) . . ? F12 C13 F10 107.7(18) . . ? F12 C13 F11 107(2) . . ? F10 C13 F11 108.1(19) . . ? F12 C13 S4 112.2(16) . . ? F10 C13 S4 110.2(16) . . ? F11 C13 S4 111.7(14) . . ? N1 C12 C11 118(2) . . ? N8 C20 C21 124(2) . . ? N8 C20 C25 114.3(19) . . ? C21 C20 C25 121(2) . . ? C18 C17 C16 112(2) . . ? N5 C18 C17 128(2) . . ? N5 C18 C19 114.8(17) . . ? C17 C18 C19 117.6(18) . . ? C22 C21 C20 120(3) . . ? C15 C16 C17 124(2) . . ? N8 C24 C23 125(2) . . ? C21 C22 C23 118(2) . . ? F2 C26 F1 107(2) . . ? F2 C26 F3 109(2) . . ? F1 C26 F3 110.8(18) . . ? F2 C26 S6 110.4(15) . . ? F1 C26 S6 110.2(17) . . ? F3 C26 S6 109.3(18) . . ? C14 C15 C16 114(2) . . ? C24 C23 C22 118(2) . . ? N9 C19 C18 105.1(19) . . ? N7 C25 C20 112(2) . . ? N5 C14 C15 124(3) . . ? F8 C28 F7 112(3) . . ? F8 C28 F9 109(2) . . ? F7 C28 F9 107(2) . . ? F8 C28 S5 111(2) . . ? F7 C28 S5 110(2) . . ? F9 C28 S5 107.4(18) . . ? F5 C27 F6 110(2) . . ? F5 C27 F4 106(2) . . ? F6 C27 F4 106(2) . . ? F5 C27 S3 112.3(19) . . ? F6 C27 S3 111.5(18) . . ? F4 C27 S3 110.2(19) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 3.151 _refine_diff_density_min -3.750 _refine_diff_density_rms 0.720 data_CuL3 _database_code_CSD 186303 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Cu F6 N4 O4 S2' _chemical_formula_weight 569.99 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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)/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 10.4495(3) _cell_length_b 14.0233(4) _cell_length_c 15.1965(4) _cell_angle_alpha 90 _cell_angle_beta 106.2210(10) _cell_angle_gamma 90 _cell_volume 2138.19(10) _cell_formula_units_Z 4 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 4824 _cell_measurement_theta_min 2.4955 _cell_measurement_theta_max 27.4635 _exptl_crystal_description block _exptl_crystal_colour clear_light_green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.771 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_absorpt_coefficient_mu 1.301 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.74347 _exptl_absorpt_correction_T_max 0.94005 _exptl_absorpt_process_details 'XPREP (Bruker, 1999)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (12s exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 105(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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 25767 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4905 _reflns_number_gt 4016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0379P)^2^+2.7643P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4905 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.85043(3) 0.65333(2) 0.216585(19) 0.01252(9) Uani 1 1 d . . . S10 S 0.75670(6) 0.56798(4) 0.37274(4) 0.01329(13) Uani 1 1 d . . . S20 S 0.79828(6) 0.48932(5) 0.06859(4) 0.01578(14) Uani 1 1 d . . . O11 O 0.79679(17) 0.47957(13) 0.42111(12) 0.0179(4) Uani 1 1 d . . . N21 N 0.69395(19) 0.73723(15) 0.18515(14) 0.0137(4) Uani 1 1 d . . . O22 O 0.94027(18) 0.48363(14) 0.08601(13) 0.0226(4) Uani 1 1 d . . . F22 F 0.63818(18) 0.39180(13) 0.14394(13) 0.0346(4) Uani 1 1 d . . . F11 F 0.82074(18) 0.64940(15) 0.53452(12) 0.0384(5) Uani 1 1 d . . . F12 F 0.61641(16) 0.60155(13) 0.48850(11) 0.0293(4) Uani 1 1 d . . . F21 F 0.8000(2) 0.31013(12) 0.11895(13) 0.0360(4) Uani 1 1 d . . . O21 O 0.71215(18) 0.46099(14) -0.01941(12) 0.0221(4) Uani 1 1 d . . . N12 N 0.87184(19) 0.62185(15) 0.34644(14) 0.0138(4) Uani 1 1 d . . . N11 N 1.04581(19) 0.63485(14) 0.24955(14) 0.0131(4) Uani 1 1 d . . . F23 F 0.83887(19) 0.40961(13) 0.23191(11) 0.0331(4) Uani 1 1 d . . . O12 O 0.63634(17) 0.57062(14) 0.29830(12) 0.0210(4) Uani 1 1 d . . . N22 N 0.7565(2) 0.58657(15) 0.10290(14) 0.0140(4) Uani 1 1 d . . . F13 F 0.6760(2) 0.72850(13) 0.43026(14) 0.0458(5) Uani 1 1 d . . . C25 C 0.5903(2) 0.70189(18) 0.11930(17) 0.0151(5) Uani 1 1 d . . . C21 C 0.6805(3) 0.81837(18) 0.23016(18) 0.0177(5) Uani 1 1 d . . . C26 C 0.6137(2) 0.61174(19) 0.07180(17) 0.0173(5) Uani 1 1 d . . . H26A H 0.5596 0.5592 0.0863 0.021 Uiso 1 1 calc R . . H26B H 0.5862 0.6215 0.0046 0.021 Uiso 1 1 calc R . . C12 C 1.2605(2) 0.62626(19) 0.22402(18) 0.0180(5) Uani 1 1 d . . . H12B H 1.3150 0.6330 0.1838 0.022 Uiso 1 1 calc R . . C17 C 0.7150(3) 0.6414(2) 0.46076(19) 0.0239(6) Uani 1 1 d . . . C24 C 0.4663(2) 0.74627(19) 0.09647(18) 0.0194(5) Uani 1 1 d . . . H24A H 0.3943 0.7217 0.0489 0.023 Uiso 1 1 calc R . . C15 C 1.1005(2) 0.60635(17) 0.33741(16) 0.0135(5) Uani 1 1 d . . . C211 C 0.8034(3) 0.8585(2) 0.29756(19) 0.0236(6) Uani 1 1 d . . . H21B H 0.8793 0.8162 0.3011 0.035 Uiso 1 1 calc R . . H21C H 0.7882 0.8635 0.3582 0.035 Uiso 1 1 calc R . . H21D H 0.8225 0.9219 0.2772 0.035 Uiso 1 1 calc R . . C11 C 1.1254(2) 0.64704(18) 0.19336(17) 0.0155(5) Uani 1 1 d . . . C13 C 1.3159(2) 0.59571(19) 0.31345(18) 0.0187(5) Uani 1 1 d . . . H13A H 1.4083 0.5814 0.3347 0.022 Uiso 1 1 calc R . . C27 C 0.7663(3) 0.3959(2) 0.14525(18) 0.0227(6) Uani 1 1 d . . . C16 C 1.0098(2) 0.6010(2) 0.39920(17) 0.0182(5) Uani 1 1 d . . . H16A H 1.0147 0.5365 0.4264 0.022 Uiso 1 1 calc R . . H16B H 1.0393 0.6477 0.4497 0.022 Uiso 1 1 calc R . . C22 C 0.5576(3) 0.86376(19) 0.21132(19) 0.0212(6) Uani 1 1 d . . . H22B H 0.5474 0.9197 0.2440 0.025 Uiso 1 1 calc R . . C14 C 1.2353(2) 0.58634(18) 0.37137(17) 0.0164(5) Uani 1 1 d . . . H14A H 1.2716 0.5666 0.4331 0.020 Uiso 1 1 calc R . . C23 C 0.4500(3) 0.82704(19) 0.1447(2) 0.0222(6) Uani 1 1 d . . . H23A H 0.3654 0.8572 0.1320 0.027 Uiso 1 1 calc R . . C111 C 1.0648(3) 0.6880(2) 0.09979(18) 0.0215(6) Uani 1 1 d . . . H11B H 0.9691 0.6976 0.0905 0.032 Uiso 1 1 calc R . . H11C H 1.0787 0.6438 0.0533 0.032 Uiso 1 1 calc R . . H11D H 1.1072 0.7492 0.0944 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01021(14) 0.01463(16) 0.01271(15) 0.00062(11) 0.00318(11) 0.00191(11) S10 0.0111(3) 0.0162(3) 0.0132(3) -0.0006(2) 0.0045(2) -0.0017(2) S20 0.0158(3) 0.0169(3) 0.0147(3) -0.0021(2) 0.0043(2) 0.0020(2) O11 0.0185(9) 0.0181(10) 0.0170(9) 0.0023(7) 0.0051(7) -0.0026(7) N21 0.0120(9) 0.0138(10) 0.0165(10) 0.0032(8) 0.0057(8) 0.0011(8) O22 0.0168(9) 0.0242(11) 0.0269(10) -0.0058(8) 0.0064(8) 0.0042(8) F22 0.0342(9) 0.0293(10) 0.0445(11) 0.0089(8) 0.0181(8) -0.0034(8) F11 0.0357(10) 0.0542(13) 0.0288(9) -0.0229(9) 0.0149(8) -0.0155(9) F12 0.0246(8) 0.0408(11) 0.0293(9) 0.0000(8) 0.0188(7) -0.0011(7) F21 0.0569(12) 0.0149(8) 0.0362(10) 0.0007(7) 0.0132(9) 0.0084(8) O21 0.0229(9) 0.0238(10) 0.0183(9) -0.0063(8) 0.0036(8) 0.0003(8) N12 0.0108(9) 0.0181(11) 0.0135(10) 0.0022(8) 0.0049(8) -0.0014(8) N11 0.0113(9) 0.0122(10) 0.0165(10) 0.0002(8) 0.0051(8) -0.0003(8) F23 0.0488(11) 0.0294(10) 0.0185(8) 0.0054(7) 0.0054(8) 0.0072(8) O12 0.0124(8) 0.0299(11) 0.0197(9) 0.0029(8) 0.0029(7) -0.0035(7) N22 0.0123(9) 0.0143(10) 0.0147(10) -0.0016(8) 0.0027(8) 0.0012(8) F13 0.0742(14) 0.0237(10) 0.0572(13) 0.0026(9) 0.0473(12) 0.0129(10) C25 0.0142(11) 0.0157(13) 0.0160(12) 0.0063(10) 0.0054(9) 0.0012(9) C21 0.0186(12) 0.0148(12) 0.0211(13) 0.0036(10) 0.0076(10) 0.0003(10) C26 0.0121(11) 0.0192(13) 0.0182(12) -0.0004(10) 0.0003(9) 0.0013(10) C12 0.0152(11) 0.0188(13) 0.0232(13) -0.0005(10) 0.0107(10) -0.0013(10) C17 0.0269(14) 0.0240(15) 0.0256(14) -0.0026(11) 0.0151(12) -0.0012(11) C24 0.0140(11) 0.0209(14) 0.0228(13) 0.0057(11) 0.0042(10) 0.0016(10) C15 0.0135(11) 0.0130(12) 0.0145(11) -0.0003(9) 0.0045(9) -0.0023(9) C211 0.0238(13) 0.0177(14) 0.0279(14) -0.0047(11) 0.0048(11) -0.0005(11) C11 0.0176(12) 0.0126(12) 0.0174(12) -0.0002(10) 0.0069(10) -0.0005(10) C13 0.0111(11) 0.0177(13) 0.0270(14) -0.0010(10) 0.0044(10) 0.0017(10) C27 0.0287(14) 0.0181(14) 0.0211(13) -0.0009(11) 0.0066(11) 0.0026(11) C16 0.0103(11) 0.0278(15) 0.0158(12) 0.0022(10) 0.0025(9) -0.0021(10) C22 0.0230(13) 0.0136(13) 0.0305(15) 0.0018(11) 0.0133(11) 0.0038(10) C14 0.0131(11) 0.0180(13) 0.0158(12) 0.0016(10) 0.0000(9) -0.0003(10) C23 0.0165(12) 0.0187(14) 0.0337(15) 0.0078(11) 0.0106(11) 0.0053(10) C111 0.0203(13) 0.0269(15) 0.0200(13) 0.0058(11) 0.0100(11) 0.0013(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 Cu1 N21 1.962(2) . ? Cu1 N22 1.969(2) . ? Cu1 N12 1.973(2) . ? Cu1 N11 1.9786(19) . ? S10 O12 1.4380(18) . ? S10 O11 1.4426(19) . ? S10 N12 1.564(2) . ? S10 C17 1.834(3) . ? S20 O22 1.4348(19) . ? S20 O21 1.4436(19) . ? S20 N22 1.565(2) . ? S20 C27 1.845(3) . ? N21 C25 1.347(3) . ? N21 C21 1.355(3) . ? F22 C27 1.335(3) . ? F11 C17 1.341(3) . ? F12 C17 1.339(3) . ? F21 C27 1.345(3) . ? N12 C16 1.470(3) . ? N11 C15 1.357(3) . ? N11 C11 1.359(3) . ? F23 C27 1.337(3) . ? N22 C26 1.477(3) . ? F13 C17 1.330(3) . ? C25 C24 1.391(3) . ? C25 C26 1.509(4) . ? C21 C22 1.390(4) . ? C21 C211 1.510(4) . ? C12 C13 1.388(4) . ? C12 C11 1.388(3) . ? C24 C23 1.385(4) . ? C15 C14 1.387(3) . ? C15 C16 1.511(3) . ? C11 C111 1.500(3) . ? C13 C14 1.384(4) . ? C22 C23 1.385(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 N21 Cu1 N22 83.92(8) . . ? N21 Cu1 N12 103.40(8) . . ? N22 Cu1 N12 131.34(9) . . ? N21 Cu1 N11 150.57(9) . . ? N22 Cu1 N11 112.72(8) . . ? N12 Cu1 N11 84.07(8) . . ? O12 S10 O11 119.25(11) . . ? O12 S10 N12 110.66(11) . . ? O11 S10 N12 114.25(11) . . ? O12 S10 C17 103.04(12) . . ? O11 S10 C17 101.83(12) . . ? N12 S10 C17 105.77(12) . . ? O22 S20 O21 120.04(11) . . ? O22 S20 N22 110.94(11) . . ? O21 S20 N22 112.87(11) . . ? O22 S20 C27 101.79(12) . . ? O21 S20 C27 102.33(12) . . ? N22 S20 C27 106.97(12) . . ? C25 N21 C21 120.6(2) . . ? C25 N21 Cu1 113.76(17) . . ? C21 N21 Cu1 125.27(17) . . ? C16 N12 S10 118.17(17) . . ? C16 N12 Cu1 114.19(15) . . ? S10 N12 Cu1 118.90(11) . . ? C15 N11 C11 119.4(2) . . ? C15 N11 Cu1 114.14(15) . . ? C11 N11 Cu1 126.42(17) . . ? C26 N22 S20 116.92(17) . . ? C26 N22 Cu1 112.26(15) . . ? S20 N22 Cu1 126.11(12) . . ? N21 C25 C24 121.4(2) . . ? N21 C25 C26 117.3(2) . . ? C24 C25 C26 121.3(2) . . ? N21 C21 C22 120.0(2) . . ? N21 C21 C211 117.8(2) . . ? C22 C21 C211 122.1(2) . . ? N22 C26 C25 109.3(2) . . ? C13 C12 C11 120.0(2) . . ? F13 C17 F12 107.7(2) . . ? F13 C17 F11 108.4(2) . . ? F12 C17 F11 107.4(2) . . ? F13 C17 S10 111.94(19) . . ? F12 C17 S10 110.86(19) . . ? F11 C17 S10 110.43(19) . . ? C23 C24 C25 118.5(2) . . ? N11 C15 C14 122.0(2) . . ? N11 C15 C16 117.4(2) . . ? C14 C15 C16 120.5(2) . . ? N11 C11 C12 120.4(2) . . ? N11 C11 C111 118.3(2) . . ? C12 C11 C111 121.2(2) . . ? C14 C13 C12 119.4(2) . . ? F22 C27 F23 108.1(2) . . ? F22 C27 F21 107.6(2) . . ? F23 C27 F21 107.3(2) . . ? F22 C27 S20 112.27(19) . . ? F23 C27 S20 111.53(19) . . ? F21 C27 S20 109.81(18) . . ? N12 C16 C15 110.0(2) . . ? C23 C22 C21 119.7(2) . . ? C13 C14 C15 118.7(2) . . ? C24 C23 C22 119.8(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.542 _refine_diff_density_min -0.692 _refine_diff_density_rms 0.086 data_CuL4 _database_code_CSD 186304 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H31 Cu N4 O4.50 S2' _chemical_formula_weight 623.23 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)/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 26.6725(9) _cell_length_b 14.5387(4) _cell_length_c 14.9797(5) _cell_angle_alpha 90 _cell_angle_beta 102.051(1) _cell_angle_gamma 90 _cell_volume 5680.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 8745 _cell_measurement_theta_min 2.4155 _cell_measurement_theta_max 28.5323 _exptl_crystal_description block _exptl_crystal_colour translucent_light_brown _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 0.959 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15s exposure) covering 0.3\% in \w. Crystal to detector distance 4.5 cm. ; _diffrn_ambient_temperature 110(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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 54427 _diffrn_reflns_av_R_equivalents 0.1503 _diffrn_reflns_av_sigmaI/netI 0.1062 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 0.78 _diffrn_reflns_theta_max 26.00 _reflns_number_total 11165 _reflns_number_gt 6571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0528P)^2^+31.6809P] 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 11165 _refine_ls_number_parameters 705 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1437 _refine_ls_R_factor_gt 0.0732 _refine_ls_wR_factor_ref 0.1856 _refine_ls_wR_factor_gt 0.1597 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 C161 C 0.3691(3) 0.7519(4) 0.1766(4) 0.0194(14) Uani 1 1 d . . . Cu1 Cu 0.44701(3) 0.51430(5) 0.24455(5) 0.01491(19) Uani 1 1 d . . . Cu2 Cu 0.06297(3) 0.98161(5) 0.27088(5) 0.01478(19) Uani 1 1 d . . . S21 S 0.35275(6) 0.42225(11) 0.13792(11) 0.0176(3) Uani 1 1 d . . . S11 S 0.43506(6) 0.72438(11) 0.19529(11) 0.0171(3) Uani 1 1 d . . . S31 S 0.07926(6) 0.77324(11) 0.31852(11) 0.0175(3) Uani 1 1 d . . . S41 S 0.14654(6) 1.12683(11) 0.35599(11) 0.0176(3) Uani 1 1 d . . . O21 O 0.33314(17) 0.4589(3) 0.2139(3) 0.0251(11) Uani 1 1 d . . . O12 O 0.44408(18) 0.6867(3) 0.1107(3) 0.0223(10) Uani 1 1 d . . . O11 O 0.46257(17) 0.8069(3) 0.2286(3) 0.0202(10) Uani 1 1 d . . . O22 O 0.33925(17) 0.4708(3) 0.0514(3) 0.0240(10) Uani 1 1 d . . . O32 O 0.07238(18) 0.8114(3) 0.4042(3) 0.0245(11) Uani 1 1 d . . . O42 O 0.17606(17) 1.0633(3) 0.3130(3) 0.0250(11) Uani 1 1 d . . . O31 O 0.05054(17) 0.6914(3) 0.2856(3) 0.0230(10) Uani 1 1 d . . . O41 O 0.14538(17) 1.2222(3) 0.3267(3) 0.0234(11) Uani 1 1 d . . . O1W O 0.2864(2) 0.4729(4) 0.8618(4) 0.0373(13) Uiso 1 1 d D . . N21 N 0.50147(19) 0.4943(3) 0.1710(3) 0.0136(11) Uani 1 1 d . . . N11 N 0.43618(18) 0.5042(3) 0.3769(3) 0.0128(11) Uani 1 1 d . . . N12 N 0.4446(2) 0.6439(4) 0.2679(4) 0.0179(12) Uani 1 1 d . . . N22 N 0.4126(2) 0.4124(4) 0.1729(3) 0.0157(11) Uani 1 1 d . . . N31 N 0.06762(18) 0.9943(3) 0.1354(3) 0.0150(11) Uani 1 1 d . . . N42 N 0.09094(19) 1.0829(4) 0.3473(4) 0.0176(12) Uani 1 1 d . . . N41 N 0.00087(19) 1.0033(3) 0.3299(3) 0.0141(11) Uani 1 1 d . . . N32 N 0.0698(2) 0.8537(3) 0.2455(4) 0.0171(12) Uani 1 1 d . . . C211 C 0.5592(3) 0.6166(5) 0.2466(5) 0.0235(15) Uani 1 1 d . . . H21B H 0.5313 0.6239 0.2774 0.035 Uiso 1 1 calc R . . H21C H 0.5639 0.6725 0.2153 0.035 Uiso 1 1 calc R . . H21D H 0.5900 0.6025 0.2904 0.035 Uiso 1 1 calc R . . C12 C 0.4187(3) 0.4341(5) 0.5116(5) 0.0232(15) Uani 1 1 d . . . H12B H 0.4136 0.3810 0.5430 0.028 Uiso 1 1 calc R . . C2X C 0.5238(2) 0.3994(4) 0.0545(5) 0.0189(14) Uani 1 1 d . . . H24A H 0.5148 0.3525 0.0120 0.023 Uiso 1 1 calc R . . C16 C 0.4439(3) 0.6702(4) 0.3624(4) 0.0197(14) Uani 1 1 d . . . H16A H 0.4171 0.7153 0.3624 0.024 Uiso 1 1 calc R . . H16B H 0.4764 0.6981 0.3904 0.024 Uiso 1 1 calc R . . C25 C 0.4912(2) 0.4244(4) 0.1106(4) 0.0172(14) Uani 1 1 d . . . C15 C 0.4346(2) 0.5877(4) 0.4167(4) 0.0171(14) Uani 1 1 d . . . C26 C 0.4416(2) 0.3744(5) 0.1073(5) 0.0202(14) Uani 1 1 d . . . H26A H 0.4208 0.3785 0.0461 0.024 Uiso 1 1 calc R . . H26B H 0.4487 0.3099 0.1208 0.024 Uiso 1 1 calc R . . C13 C 0.4163(3) 0.5201(5) 0.5518(5) 0.0301(17) Uani 1 1 d . . . H13A H 0.4087 0.5254 0.6095 0.036 Uiso 1 1 calc R . . C262 C 0.3205(2) 0.2510(5) 0.1852(5) 0.0226(15) Uani 1 1 d . . . H26C H 0.3298 0.2699 0.2457 0.027 Uiso 1 1 calc R . . C21 C 0.5473(2) 0.5390(4) 0.1784(4) 0.0177(14) Uani 1 1 d . . . C14 C 0.4254(3) 0.5979(5) 0.5031(5) 0.0222(15) Uani 1 1 d . . . H14A H 0.4253 0.6561 0.5288 0.027 Uiso 1 1 calc R . . C11 C 0.4289(2) 0.4279(4) 0.4245(4) 0.0179(14) Uani 1 1 d . . . C261 C 0.3278(2) 0.3093(4) 0.1146(4) 0.0179(14) Uani 1 1 d . . . C24 C 0.5820(2) 0.5147(5) 0.1254(5) 0.0229(15) Uani 1 1 d . . . H24B H 0.6132 0.5453 0.1323 0.027 Uiso 1 1 calc R . . C166 C 0.3329(3) 0.6940(5) 0.1250(5) 0.0247(16) Uani 1 1 d . . . H16C H 0.3435 0.6409 0.0997 0.030 Uiso 1 1 calc R . . C165 C 0.2818(3) 0.7145(5) 0.1112(5) 0.0284(17) Uani 1 1 d . . . H16D H 0.2581 0.6750 0.0762 0.034 Uiso 1 1 calc R . . C111 C 0.4349(3) 0.3356(4) 0.3827(5) 0.0219(15) Uani 1 1 d . . . H11B H 0.4417 0.3440 0.3228 0.033 Uiso 1 1 calc R . . H11C H 0.4038 0.3008 0.3783 0.033 Uiso 1 1 calc R . . H11D H 0.4628 0.3030 0.4202 0.033 Uiso 1 1 calc R . . C266 C 0.3150(3) 0.2783(5) 0.0246(5) 0.0326(18) Uani 1 1 d . . . H26D H 0.3202 0.3163 -0.0227 0.039 Uiso 1 1 calc R . . C162 C 0.3520(3) 0.8314(5) 0.2148(5) 0.0249(16) Uani 1 1 d . . . H16E H 0.3756 0.8713 0.2494 0.030 Uiso 1 1 calc R . . C23 C 0.5699(3) 0.4447(4) 0.0622(5) 0.0215(15) Uani 1 1 d . . . H23A H 0.5925 0.4283 0.0253 0.026 Uiso 1 1 calc R . . C163 C 0.3008(3) 0.8499(5) 0.2012(5) 0.0289(17) Uani 1 1 d . . . H16F H 0.2900 0.9020 0.2279 0.035 Uiso 1 1 calc R . . C164 C 0.2645(3) 0.7932(6) 0.1486(5) 0.0351(19) Uani 1 1 d . . . C265 C 0.2947(3) 0.1910(5) 0.0052(6) 0.045(2) Uani 1 1 d . . . H26E H 0.2870 0.1706 -0.0549 0.054 Uiso 1 1 calc R . . C263 C 0.2993(3) 0.1645(5) 0.1633(6) 0.037(2) Uani 1 1 d . . . H26F H 0.2941 0.1260 0.2101 0.044 Uiso 1 1 calc R . . C264 C 0.2856(3) 0.1338(5) 0.0738(7) 0.044(2) Uani 1 1 d . . . C46 C 0.0543(2) 1.1354(4) 0.3861(5) 0.0179(14) Uani 1 1 d . . . H46A H 0.0445 1.1906 0.3503 0.021 Uiso 1 1 calc R . . H46B H 0.0697 1.1536 0.4480 0.021 Uiso 1 1 calc R . . C45 C 0.0078(2) 1.0773(4) 0.3861(4) 0.0176(14) Uani 1 1 d . . . C34 C 0.0752(3) 0.9041(5) 0.0048(5) 0.0253(16) Uani 1 1 d . . . H34A H 0.0778 0.8465 -0.0208 0.030 Uiso 1 1 calc R . . C361 C 0.1449(3) 0.7419(5) 0.3323(4) 0.0213(15) Uani 1 1 d . . . C44 C -0.0270(2) 1.1006(4) 0.4393(4) 0.0181(14) Uani 1 1 d . . . H44A H -0.0211 1.1512 0.4782 0.022 Uiso 1 1 calc R . . C42 C -0.0786(2) 0.9733(5) 0.3736(4) 0.0211(14) Uani 1 1 d . . . H42B H -0.1081 0.9376 0.3678 0.025 Uiso 1 1 calc R . . C36 C 0.0692(3) 0.8273(4) 0.1519(4) 0.0193(14) Uani 1 1 d . . . H36A H 0.0380 0.7934 0.1274 0.023 Uiso 1 1 calc R . . H36B H 0.0982 0.7878 0.1500 0.023 Uiso 1 1 calc R . . C463 C 0.2119(2) 1.0504(5) 0.6136(5) 0.0226(15) Uani 1 1 d . . . H46C H 0.2268 0.9975 0.6427 0.027 Uiso 1 1 calc R . . C35 C 0.0717(2) 0.9121(4) 0.0950(4) 0.0166(14) Uani 1 1 d . . . C311 C 0.0589(3) 1.1624(4) 0.1285(5) 0.0195(14) Uani 1 1 d . . . H31B H 0.0568 1.1515 0.1908 0.029 Uiso 1 1 calc R . . H31C H 0.0277 1.1907 0.0967 0.029 Uiso 1 1 calc R . . H31D H 0.0873 1.2024 0.1268 0.029 Uiso 1 1 calc R . . C32 C 0.0706(3) 1.0675(5) -0.0060(5) 0.0238(16) Uani 1 1 d . . . H32B H 0.0707 1.1212 -0.0397 0.029 Uiso 1 1 calc R . . C43 C -0.0707(2) 1.0474(5) 0.4335(5) 0.0219(15) Uani 1 1 d . . . H43A H -0.0943 1.0611 0.4692 0.026 Uiso 1 1 calc R . . C465 C 0.1870(2) 1.2077(5) 0.6199(5) 0.0235(15) Uani 1 1 d . . . H46D H 0.1843 1.2609 0.6531 0.028 Uiso 1 1 calc R . . C464 C 0.2081(2) 1.1274(5) 0.6651(5) 0.0231(15) Uani 1 1 d . . . C466 C 0.1700(2) 1.2077(5) 0.5256(5) 0.0223(15) Uani 1 1 d . . . H46E H 0.1567 1.2613 0.4958 0.027 Uiso 1 1 calc R . . C41 C -0.0419(2) 0.9528(4) 0.3222(4) 0.0171(14) Uani 1 1 d . . . C31 C 0.0664(2) 1.0726(5) 0.0834(5) 0.0203(15) Uani 1 1 d . . . C411 C -0.0496(3) 0.8727(4) 0.2573(5) 0.0199(14) Uani 1 1 d . . . H41B H -0.0209 0.8681 0.2282 0.030 Uiso 1 1 calc R . . H41C H -0.0804 0.8817 0.2119 0.030 Uiso 1 1 calc R . . H41D H -0.0524 0.8171 0.2905 0.030 Uiso 1 1 calc R . . C362 C 0.1826(3) 0.8092(5) 0.3599(5) 0.0282(17) Uani 1 1 d . . . H36C H 0.1733 0.8696 0.3690 0.034 Uiso 1 1 calc R . . C363 C 0.2335(3) 0.7853(6) 0.3734(5) 0.038(2) Uani 1 1 d . . . H36D H 0.2584 0.8303 0.3906 0.045 Uiso 1 1 calc R . . C364 C 0.2486(3) 0.6948(7) 0.3621(5) 0.040(2) Uani 1 1 d . . . C365 C 0.2109(3) 0.6311(6) 0.3321(6) 0.042(2) Uani 1 1 d . . . H36E H 0.2204 0.5712 0.3213 0.051 Uiso 1 1 calc R . . C461 C 0.1728(2) 1.1276(4) 0.4754(5) 0.0196(14) Uani 1 1 d . . . C366 C 0.1592(3) 0.6523(5) 0.3171(5) 0.0297(17) Uani 1 1 d . . . H36F H 0.1346 0.6074 0.2974 0.036 Uiso 1 1 calc R . . C33 C 0.0748(3) 0.9828(5) -0.0468(5) 0.0296(17) Uani 1 1 d . . . H33A H 0.0773 0.9792 -0.1077 0.036 Uiso 1 1 calc R . . C462 C 0.1944(2) 1.0488(4) 0.5197(5) 0.0192(14) Uani 1 1 d . . . H46F H 0.1970 0.9954 0.4868 0.023 Uiso 1 1 calc R . . C47 C 0.2260(3) 1.1277(6) 0.7664(5) 0.0317(18) Uani 1 1 d . . . H47A H 0.2392 1.0681 0.7863 0.047 Uiso 1 1 calc R . . H47B H 0.1977 1.1421 0.7945 0.047 Uiso 1 1 calc R . . H47C H 0.2524 1.1730 0.7834 0.047 Uiso 1 1 calc R . . C27 C 0.2599(5) 0.0411(6) 0.0512(8) 0.083(4) Uani 1 1 d . . . H27A H 0.2563 0.0110 0.1066 0.124 Uiso 1 1 calc R . . H27B H 0.2805 0.0037 0.0200 0.124 Uiso 1 1 calc R . . H27C H 0.2266 0.0499 0.0128 0.124 Uiso 1 1 calc R . . C17 C 0.2083(3) 0.8149(6) 0.1306(6) 0.043(2) Uiso 1 1 d . . . H17A H 0.1895 0.7675 0.0932 0.064 Uiso 1 1 calc R . . H17B H 0.2022 0.8729 0.0995 0.064 Uiso 1 1 calc R . . H17C H 0.1971 0.8182 0.1874 0.064 Uiso 1 1 calc R . . C37 C 0.3045(4) 0.6698(7) 0.3767(7) 0.057(3) Uiso 1 1 d . . . H37A H 0.3250 0.7229 0.3975 0.085 Uiso 1 1 calc R . . H37B H 0.3121 0.6487 0.3202 0.085 Uiso 1 1 calc R . . H37C H 0.3120 0.6219 0.4216 0.085 Uiso 1 1 calc R . . H1WA H 0.289(2) 0.424(2) 0.837(4) 0.004(15) Uiso 1 1 d D . . H1WB H 0.2541(12) 0.463(8) 0.845(8) 0.09(4) Uiso 1 1 d 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 C161 0.028(4) 0.013(3) 0.019(4) -0.003(3) 0.008(3) -0.002(3) Cu1 0.0199(4) 0.0112(4) 0.0152(4) -0.0018(3) 0.0072(3) -0.0023(3) Cu2 0.0212(4) 0.0097(4) 0.0152(4) -0.0015(3) 0.0080(3) -0.0009(3) S21 0.0198(8) 0.0109(8) 0.0223(9) -0.0029(6) 0.0047(7) -0.0024(6) S11 0.0253(8) 0.0107(8) 0.0169(8) 0.0003(6) 0.0079(7) -0.0005(6) S31 0.0232(8) 0.0125(8) 0.0186(9) 0.0018(6) 0.0087(7) 0.0015(6) S41 0.0184(8) 0.0162(8) 0.0185(8) -0.0006(6) 0.0044(6) -0.0027(6) O21 0.020(2) 0.027(3) 0.031(3) -0.014(2) 0.011(2) -0.0029(19) O12 0.036(3) 0.018(3) 0.017(2) 0.0005(19) 0.014(2) 0.001(2) O11 0.027(2) 0.012(2) 0.022(3) -0.0028(19) 0.007(2) -0.0053(18) O22 0.030(3) 0.018(3) 0.023(3) 0.001(2) 0.004(2) 0.001(2) O32 0.036(3) 0.021(3) 0.021(3) 0.000(2) 0.016(2) 0.002(2) O42 0.026(3) 0.034(3) 0.017(3) -0.006(2) 0.011(2) -0.002(2) O31 0.031(3) 0.013(2) 0.027(3) 0.0001(19) 0.009(2) -0.0038(19) O41 0.028(3) 0.019(3) 0.023(3) 0.006(2) 0.007(2) -0.007(2) N21 0.019(3) 0.009(3) 0.013(3) 0.000(2) 0.004(2) 0.005(2) N11 0.015(2) 0.010(3) 0.015(3) 0.003(2) 0.005(2) 0.0043(19) N12 0.023(3) 0.017(3) 0.015(3) 0.004(2) 0.007(2) 0.000(2) N22 0.025(3) 0.014(3) 0.010(3) -0.001(2) 0.009(2) -0.002(2) N31 0.015(3) 0.013(3) 0.018(3) -0.002(2) 0.005(2) 0.003(2) N42 0.016(3) 0.024(3) 0.014(3) -0.001(2) 0.008(2) 0.001(2) N41 0.017(3) 0.014(3) 0.011(3) 0.001(2) 0.003(2) -0.001(2) N32 0.024(3) 0.011(3) 0.017(3) -0.002(2) 0.008(2) 0.000(2) C211 0.024(4) 0.018(4) 0.029(4) -0.001(3) 0.007(3) -0.004(3) C12 0.039(4) 0.017(4) 0.018(4) 0.003(3) 0.015(3) -0.001(3) C2X 0.019(3) 0.019(4) 0.020(4) 0.004(3) 0.005(3) 0.007(3) C16 0.025(4) 0.018(4) 0.014(3) -0.003(3) 0.001(3) -0.001(3) C25 0.022(3) 0.011(3) 0.019(3) 0.000(3) 0.005(3) 0.000(3) C15 0.017(3) 0.016(3) 0.016(3) 0.004(3) 0.002(3) 0.003(3) C26 0.027(4) 0.015(3) 0.021(4) -0.004(3) 0.010(3) -0.003(3) C13 0.048(4) 0.034(4) 0.013(3) -0.001(3) 0.015(3) 0.008(4) C262 0.015(3) 0.026(4) 0.025(4) 0.002(3) -0.001(3) 0.000(3) C21 0.017(3) 0.013(3) 0.020(3) 0.002(3) -0.002(3) -0.002(2) C14 0.033(4) 0.018(4) 0.017(4) -0.007(3) 0.006(3) 0.002(3) C11 0.020(3) 0.016(3) 0.018(4) -0.001(3) 0.005(3) 0.000(3) C261 0.023(3) 0.009(3) 0.019(3) 0.003(3) -0.001(3) -0.001(3) C24 0.017(3) 0.017(3) 0.035(4) 0.011(3) 0.005(3) 0.001(3) C166 0.032(4) 0.011(3) 0.030(4) 0.003(3) 0.005(3) -0.002(3) C165 0.030(4) 0.029(4) 0.024(4) 0.010(3) 0.002(3) -0.006(3) C111 0.035(4) 0.016(4) 0.016(3) 0.001(3) 0.008(3) -0.001(3) C266 0.041(4) 0.020(4) 0.035(5) -0.001(3) 0.004(4) -0.002(3) C162 0.038(4) 0.016(4) 0.022(4) 0.005(3) 0.008(3) -0.001(3) C23 0.030(4) 0.019(4) 0.020(4) 0.006(3) 0.016(3) 0.009(3) C163 0.041(4) 0.028(4) 0.019(4) 0.011(3) 0.011(3) 0.012(3) C164 0.027(4) 0.046(5) 0.032(4) 0.021(4) 0.005(3) 0.008(4) C265 0.064(6) 0.023(4) 0.036(5) -0.005(4) -0.015(4) -0.003(4) C263 0.030(4) 0.021(4) 0.057(6) 0.021(4) 0.003(4) -0.003(3) C264 0.038(5) 0.016(4) 0.062(6) 0.004(4) -0.023(4) -0.006(3) C46 0.021(3) 0.012(3) 0.022(4) -0.002(3) 0.006(3) 0.004(3) C45 0.019(3) 0.018(3) 0.016(3) 0.005(3) 0.004(3) 0.002(3) C34 0.040(4) 0.015(4) 0.022(4) -0.007(3) 0.009(3) 0.005(3) C361 0.026(4) 0.023(4) 0.018(4) 0.008(3) 0.010(3) 0.001(3) C44 0.022(3) 0.016(4) 0.016(3) 0.001(3) 0.005(3) 0.003(3) C42 0.021(3) 0.025(4) 0.019(4) 0.001(3) 0.009(3) -0.004(3) C36 0.032(4) 0.011(3) 0.016(3) -0.002(3) 0.007(3) 0.002(3) C463 0.017(3) 0.023(4) 0.028(4) 0.003(3) 0.005(3) 0.001(3) C35 0.018(3) 0.012(3) 0.018(3) 0.001(3) 0.000(3) 0.001(2) C311 0.027(4) 0.015(3) 0.017(3) 0.002(3) 0.006(3) 0.004(3) C32 0.041(4) 0.012(4) 0.021(4) 0.007(3) 0.012(3) 0.005(3) C43 0.021(3) 0.023(4) 0.023(4) 0.002(3) 0.008(3) 0.006(3) C465 0.020(3) 0.023(4) 0.026(4) -0.011(3) 0.003(3) 0.003(3) C464 0.014(3) 0.029(4) 0.026(4) -0.005(3) 0.005(3) -0.002(3) C466 0.021(3) 0.021(4) 0.024(4) -0.005(3) 0.003(3) 0.000(3) C41 0.017(3) 0.018(3) 0.015(3) -0.001(3) -0.001(3) 0.002(2) C31 0.018(3) 0.020(4) 0.023(4) 0.003(3) 0.004(3) -0.001(3) C411 0.024(3) 0.013(3) 0.023(4) 0.000(3) 0.003(3) -0.005(3) C362 0.029(4) 0.029(4) 0.026(4) -0.003(3) 0.006(3) -0.005(3) C363 0.028(4) 0.053(6) 0.030(4) 0.008(4) 0.001(3) -0.011(4) C364 0.029(4) 0.066(6) 0.027(4) 0.021(4) 0.009(3) 0.005(4) C365 0.051(5) 0.027(5) 0.054(6) 0.021(4) 0.025(4) 0.016(4) C461 0.018(3) 0.016(3) 0.025(4) -0.007(3) 0.005(3) -0.005(3) C366 0.033(4) 0.020(4) 0.041(5) 0.009(3) 0.019(4) 0.002(3) C33 0.049(5) 0.024(4) 0.019(4) 0.000(3) 0.012(3) 0.008(3) C462 0.020(3) 0.015(3) 0.024(4) -0.006(3) 0.007(3) -0.002(3) C47 0.031(4) 0.044(5) 0.020(4) -0.006(3) 0.005(3) 0.006(3) C27 0.103(9) 0.019(5) 0.096(9) 0.006(5) -0.049(7) -0.025(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 C161 C166 1.388(9) . ? C161 C162 1.407(9) . ? C161 S11 1.770(7) . ? Cu1 N12 1.920(5) . ? Cu1 N22 1.944(5) . ? Cu1 N21 2.019(5) . ? Cu1 N11 2.067(5) . ? Cu2 N32 1.914(5) . ? Cu2 N42 1.918(5) . ? Cu2 N41 2.058(5) . ? Cu2 N31 2.067(5) . ? S21 O21 1.450(5) . ? S21 O22 1.454(5) . ? S21 N22 1.579(5) . ? S21 C261 1.778(6) . ? S11 O11 1.440(4) . ? S11 O12 1.446(5) . ? S11 N12 1.582(5) . ? S31 O32 1.445(5) . ? S31 O31 1.446(5) . ? S31 N32 1.585(5) . ? S31 C361 1.778(7) . ? S41 O42 1.450(5) . ? S41 O41 1.453(5) . ? S41 N42 1.595(5) . ? S41 C461 1.780(7) . ? N21 C25 1.350(8) . ? N21 C21 1.368(8) . ? N11 C11 1.355(8) . ? N11 C15 1.357(8) . ? N12 C16 1.470(8) . ? N22 C26 1.480(8) . ? N31 C35 1.353(8) . ? N31 C31 1.376(8) . ? N42 C46 1.453(8) . ? N41 C41 1.342(8) . ? N41 C45 1.355(8) . ? N32 C36 1.451(8) . ? C211 C21 1.510(9) . ? C12 C11 1.389(9) . ? C12 C13 1.396(10) . ? C2X C23 1.378(9) . ? C2X C25 1.379(9) . ? C16 C15 1.499(9) . ? C25 C26 1.500(9) . ? C15 C14 1.375(9) . ? C13 C14 1.395(10) . ? C262 C263 1.390(10) . ? C262 C261 1.400(9) . ? C21 C24 1.386(9) . ? C11 C111 1.504(9) . ? C261 C266 1.396(10) . ? C24 C23 1.382(10) . ? C166 C165 1.367(10) . ? C165 C164 1.394(11) . ? C266 C265 1.386(10) . ? C162 C163 1.364(10) . ? C163 C164 1.386(11) . ? C164 C17 1.501(11) . ? C265 C264 1.382(12) . ? C263 C264 1.387(12) . ? C264 C27 1.519(11) . ? C46 C45 1.501(9) . ? C45 C44 1.386(9) . ? C34 C35 1.378(10) . ? C34 C33 1.381(10) . ? C361 C366 1.390(10) . ? C361 C362 1.403(9) . ? C44 C43 1.386(9) . ? C42 C43 1.390(9) . ? C42 C41 1.398(9) . ? C36 C35 1.509(9) . ? C463 C464 1.377(10) . ? C463 C462 1.386(9) . ? C311 C31 1.502(9) . ? C32 C31 1.370(10) . ? C32 C33 1.389(10) . ? C465 C466 1.390(9) . ? C465 C464 1.407(10) . ? C464 C47 1.492(10) . ? C466 C461 1.396(9) . ? C41 C411 1.503(9) . ? C362 C363 1.374(11) . ? C363 C364 1.398(12) . ? C364 C365 1.373(12) . ? C364 C37 1.504(12) . ? C365 C366 1.384(11) . ? C461 C462 1.388(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 C166 C161 C162 118.6(6) . . ? C166 C161 S11 120.3(5) . . ? C162 C161 S11 121.1(5) . . ? N12 Cu1 N22 145.0(2) . . ? N12 Cu1 N21 107.2(2) . . ? N22 Cu1 N21 84.2(2) . . ? N12 Cu1 N11 83.0(2) . . ? N22 Cu1 N11 109.3(2) . . ? N21 Cu1 N11 140.66(19) . . ? N32 Cu2 N42 145.4(2) . . ? N32 Cu2 N41 110.6(2) . . ? N42 Cu2 N41 82.7(2) . . ? N32 Cu2 N31 82.2(2) . . ? N42 Cu2 N31 115.0(2) . . ? N41 Cu2 N31 128.82(19) . . ? O21 S21 O22 117.3(3) . . ? O21 S21 N22 106.2(3) . . ? O22 S21 N22 112.7(3) . . ? O21 S21 C261 108.2(3) . . ? O22 S21 C261 105.1(3) . . ? N22 S21 C261 107.0(3) . . ? O11 S11 O12 117.0(3) . . ? O11 S11 N12 112.3(3) . . ? O12 S11 N12 106.9(3) . . ? O11 S11 C161 106.5(3) . . ? O12 S11 C161 106.8(3) . . ? N12 S11 C161 106.8(3) . . ? O32 S31 O31 117.5(3) . . ? O32 S31 N32 107.3(3) . . ? O31 S31 N32 112.1(3) . . ? O32 S31 C361 107.4(3) . . ? O31 S31 C361 105.5(3) . . ? N32 S31 C361 106.3(3) . . ? O42 S41 O41 117.0(3) . . ? O42 S41 N42 106.9(3) . . ? O41 S41 N42 113.4(3) . . ? O42 S41 C461 108.3(3) . . ? O41 S41 C461 106.0(3) . . ? N42 S41 C461 104.4(3) . . ? C25 N21 C21 117.8(5) . . ? C25 N21 Cu1 113.9(4) . . ? C21 N21 Cu1 128.3(4) . . ? C11 N11 C15 118.7(5) . . ? C11 N11 Cu1 128.9(4) . . ? C15 N11 Cu1 112.4(4) . . ? C16 N12 S11 115.9(4) . . ? C16 N12 Cu1 116.0(4) . . ? S11 N12 Cu1 127.4(3) . . ? C26 N22 S21 116.5(4) . . ? C26 N22 Cu1 113.5(4) . . ? S21 N22 Cu1 116.2(3) . . ? C35 N31 C31 118.2(6) . . ? C35 N31 Cu2 112.8(4) . . ? C31 N31 Cu2 129.0(4) . . ? C46 N42 S41 116.7(4) . . ? C46 N42 Cu2 115.6(4) . . ? S41 N42 Cu2 126.5(3) . . ? C41 N41 C45 119.4(5) . . ? C41 N41 Cu2 128.8(4) . . ? C45 N41 Cu2 111.7(4) . . ? C36 N32 S31 116.1(4) . . ? C36 N32 Cu2 117.8(4) . . ? S31 N32 Cu2 126.0(3) . . ? C11 C12 C13 120.0(6) . . ? C23 C2X C25 119.3(6) . . ? N12 C16 C15 110.5(5) . . ? N21 C25 C2X 122.7(6) . . ? N21 C25 C26 116.2(6) . . ? C2X C25 C26 121.1(6) . . ? N11 C15 C14 122.6(6) . . ? N11 C15 C16 117.0(6) . . ? C14 C15 C16 120.4(6) . . ? N22 C26 C25 112.1(5) . . ? C14 C13 C12 118.1(6) . . ? C263 C262 C261 118.9(7) . . ? N21 C21 C24 121.7(6) . . ? N21 C21 C211 117.9(6) . . ? C24 C21 C211 120.4(6) . . ? C15 C14 C13 119.4(6) . . ? N11 C11 C12 121.3(6) . . ? N11 C11 C111 118.1(6) . . ? C12 C11 C111 120.5(6) . . ? C266 C261 C262 119.3(6) . . ? C266 C261 S21 119.6(5) . . ? C262 C261 S21 121.1(5) . . ? C23 C24 C21 119.5(6) . . ? C165 C166 C161 120.5(7) . . ? C166 C165 C164 121.4(7) . . ? C265 C266 C261 120.3(7) . . ? C163 C162 C161 119.9(7) . . ? C2X C23 C24 119.1(6) . . ? C162 C163 C164 121.8(7) . . ? C163 C164 C165 117.7(7) . . ? C163 C164 C17 122.1(8) . . ? C165 C164 C17 120.2(7) . . ? C264 C265 C266 121.1(8) . . ? C264 C263 C262 122.1(7) . . ? C265 C264 C263 118.3(7) . . ? C265 C264 C27 120.6(9) . . ? C263 C264 C27 121.1(9) . . ? N42 C46 C45 109.2(5) . . ? N41 C45 C44 122.0(6) . . ? N41 C45 C46 116.9(6) . . ? C44 C45 C46 121.0(6) . . ? C35 C34 C33 119.0(6) . . ? C366 C361 C362 119.8(6) . . ? C366 C361 S31 121.3(5) . . ? C362 C361 S31 118.9(5) . . ? C45 C44 C43 118.8(6) . . ? C43 C42 C41 119.4(6) . . ? N32 C36 C35 109.7(5) . . ? C464 C463 C462 122.3(6) . . ? N31 C35 C34 122.8(6) . . ? N31 C35 C36 116.8(6) . . ? C34 C35 C36 120.3(6) . . ? C31 C32 C33 120.7(6) . . ? C44 C43 C42 119.1(6) . . ? C466 C465 C464 120.2(6) . . ? C463 C464 C465 118.3(6) . . ? C463 C464 C47 121.8(7) . . ? C465 C464 C47 119.9(6) . . ? C465 C466 C461 120.2(6) . . ? N41 C41 C42 121.2(6) . . ? N41 C41 C411 118.5(6) . . ? C42 C41 C411 120.3(6) . . ? C32 C31 N31 120.7(6) . . ? C32 C31 C311 122.2(6) . . ? N31 C31 C311 117.0(6) . . ? C363 C362 C361 119.5(7) . . ? C362 C363 C364 121.5(7) . . ? C365 C364 C363 117.6(7) . . ? C365 C364 C37 121.5(9) . . ? C363 C364 C37 120.8(8) . . ? C364 C365 C366 122.7(8) . . ? C462 C461 C466 119.7(6) . . ? C462 C461 S41 120.8(5) . . ? C466 C461 S41 119.5(5) . . ? C365 C366 C361 118.8(7) . . ? C34 C33 C32 118.6(6) . . ? C463 C462 C461 119.3(6) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.006 _refine_diff_density_min -0.763 _refine_diff_density_rms 0.132 data_NiL1 _database_code_CSD 186305 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 N4 Ni O4 S2' _chemical_formula_weight 581.34 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 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 7.3347(3) _cell_length_b 17.0575(6) _cell_length_c 9.8220(3) _cell_angle_alpha 90 _cell_angle_beta 99.1390(10) _cell_angle_gamma 90 _cell_volume 1213.25(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2805 _cell_measurement_theta_min 2.388 _cell_measurement_theta_max 23.2125 _exptl_crystal_description plate _exptl_crystal_colour fluorescent_orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 1.015 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_correction_T_min 0.856 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (10s exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(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 'Bruker SMART CCD 6K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 9114 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 23.27 _reflns_number_total 1735 _reflns_number_gt 1494 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0943P)^2^+12.0173P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 1735 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.2108 _refine_ls_wR_factor_gt 0.2024 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.5000 0.5000 0.5000 0.0293(5) Uani 1 2 d S . . S1 S 0.3160(2) 0.45928(9) 0.74719(16) 0.0159(5) Uani 1 1 d . . . O1 O 0.3518(7) 0.4380(3) 0.8919(5) 0.0206(11) Uani 1 1 d . . . O2 O 0.1830(6) 0.4130(3) 0.6564(5) 0.0199(11) Uani 1 1 d . . . N1 N 0.4023(7) 0.4057(3) 0.4086(5) 0.0142(12) Uani 1 1 d . . . N2 N 0.5067(8) 0.4572(3) 0.6859(5) 0.0152(12) Uani 1 1 d . . . C1 C 0.4107(9) 0.3319(4) 0.4572(7) 0.0191(15) Uani 1 1 d . . . H1 H 0.4627 0.3231 0.5508 0.023 Uiso 1 1 calc R . . C2 C 0.3469(10) 0.2688(4) 0.3767(7) 0.0207(16) Uani 1 1 d . . . H2 H 0.3583 0.2172 0.4131 0.025 Uiso 1 1 calc R . . C3 C 0.2654(10) 0.2820(4) 0.2411(7) 0.0225(16) Uani 1 1 d . . . H3 H 0.2184 0.2394 0.1838 0.027 Uiso 1 1 calc R . . C4 C 0.2534(9) 0.3579(4) 0.1902(7) 0.0178(15) Uani 1 1 d . . . H4 H 0.1960 0.3683 0.0983 0.021 Uiso 1 1 calc R . . C5 C 0.3270(8) 0.4185(4) 0.2763(7) 0.0139(14) Uani 1 1 d . . . C6 C 0.6636(10) 0.4976(4) 0.7681(9) 0.0177(17) Uani 1 1 d . . . H61 H 0.732(12) 0.480(5) 0.761(9) 0.021 Uiso 1 1 d . . . H62 H 0.659(9) 0.495(4) 0.853(8) 0.003(16) Uiso 1 1 d . . . C7 C 0.2388(9) 0.5576(3) 0.7374(6) 0.0137(14) Uani 1 1 d . . . C8 C 0.1432(9) 0.5855(4) 0.6133(7) 0.0151(14) Uani 1 1 d . . . H8 H 0.1033 0.5501 0.5398 0.018 Uiso 1 1 calc R . . C9 C 0.1061(9) 0.6652(4) 0.5968(7) 0.0170(14) Uani 1 1 d . . . H9 H 0.0388 0.6840 0.5125 0.020 Uiso 1 1 calc R . . C10 C 0.1671(9) 0.7178(4) 0.7034(7) 0.0162(14) Uani 1 1 d . . . C11 C 0.2567(9) 0.6883(4) 0.8281(7) 0.0172(15) Uani 1 1 d . . . H11 H 0.2942 0.7233 0.9025 0.021 Uiso 1 1 calc R . . C12 C 0.2927(9) 0.6089(4) 0.8463(7) 0.0171(14) Uani 1 1 d . . . H12 H 0.3536 0.5897 0.9325 0.021 Uiso 1 1 calc R . . C13 C 0.1379(10) 0.8059(4) 0.6829(7) 0.0204(15) Uani 1 1 d . . . H13A H 0.2540 0.8304 0.6683 0.031 Uiso 1 1 calc R . . H13B H 0.0979 0.8285 0.7650 0.031 Uiso 1 1 calc R . . H13C H 0.0431 0.8152 0.6024 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0399(9) 0.0207(8) 0.0266(9) -0.0005(5) 0.0035(6) -0.0016(6) S1 0.0261(10) 0.0058(8) 0.0142(9) 0.0022(6) -0.0014(7) -0.0017(6) O1 0.032(3) 0.012(2) 0.016(2) 0.0054(19) 0.000(2) -0.002(2) O2 0.026(3) 0.009(2) 0.022(3) -0.0008(18) -0.003(2) -0.0048(19) N1 0.019(3) 0.011(3) 0.013(3) 0.000(2) 0.002(2) -0.002(2) N2 0.023(3) 0.007(3) 0.014(3) -0.002(2) -0.003(2) 0.000(2) C1 0.022(4) 0.015(3) 0.020(4) 0.007(3) 0.003(3) 0.004(3) C2 0.026(4) 0.009(3) 0.029(4) 0.005(3) 0.013(3) -0.001(3) C3 0.022(4) 0.016(4) 0.032(4) -0.011(3) 0.012(3) -0.006(3) C4 0.023(4) 0.016(3) 0.014(3) 0.000(3) 0.000(3) -0.002(3) C5 0.014(3) 0.010(3) 0.019(4) -0.001(3) 0.007(3) -0.001(3) C6 0.022(4) 0.012(4) 0.019(5) 0.002(3) 0.002(3) 0.002(3) C7 0.023(4) 0.004(3) 0.014(3) 0.000(3) 0.004(3) -0.004(3) C8 0.019(3) 0.011(3) 0.016(3) -0.003(3) 0.003(3) -0.003(3) C9 0.018(3) 0.015(3) 0.018(3) 0.003(3) 0.004(3) 0.001(3) C10 0.017(3) 0.008(3) 0.025(4) 0.002(3) 0.008(3) -0.002(3) C11 0.023(4) 0.013(3) 0.016(3) -0.003(3) 0.004(3) -0.002(3) C12 0.020(3) 0.017(3) 0.013(3) 0.003(3) 0.000(3) 0.002(3) C13 0.026(4) 0.009(3) 0.027(4) 0.000(3) 0.004(3) 0.003(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 Ni1 N1 1.924(5) . ? Ni1 N1 1.924(5) 3_666 ? Ni1 N2 1.960(5) 3_666 ? Ni1 N2 1.960(5) . ? S1 O2 1.447(5) . ? S1 O1 1.450(5) . ? S1 N2 1.608(6) . ? S1 C7 1.768(6) . ? N1 C1 1.345(8) . ? N1 C5 1.346(8) . ? N2 C6 1.468(9) . ? C1 C2 1.372(10) . ? C2 C3 1.388(10) . ? C3 C4 1.386(10) . ? C4 C5 1.390(9) . ? C5 C6 1.501(10) 3_666 ? C6 C5 1.501(10) 3_666 ? C7 C12 1.389(9) . ? C7 C8 1.390(9) . ? C8 C9 1.391(9) . ? C9 C10 1.397(9) . ? C10 C11 1.390(9) . ? C10 C13 1.526(9) . ? C11 C12 1.386(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 N1 Ni1 N1 180.00(17) . 3_666 ? N1 Ni1 N2 85.6(2) . 3_666 ? N1 Ni1 N2 94.4(2) 3_666 3_666 ? N1 Ni1 N2 94.4(2) . . ? N1 Ni1 N2 85.6(2) 3_666 . ? N2 Ni1 N2 180.0(3) 3_666 . ? O2 S1 O1 117.8(3) . . ? O2 S1 N2 107.4(3) . . ? O1 S1 N2 109.2(3) . . ? O2 S1 C7 107.8(3) . . ? O1 S1 C7 107.3(3) . . ? N2 S1 C7 106.9(3) . . ? C1 N1 C5 118.9(5) . . ? C1 N1 Ni1 128.6(5) . . ? C5 N1 Ni1 112.4(4) . . ? C6 N2 S1 115.9(5) . . ? C6 N2 Ni1 103.8(4) . . ? S1 N2 Ni1 116.5(3) . . ? N1 C1 C2 122.5(6) . . ? C1 C2 C3 118.8(6) . . ? C4 C3 C2 119.3(6) . . ? C3 C4 C5 118.6(6) . . ? N1 C5 C4 121.8(6) . . ? N1 C5 C6 113.8(6) . 3_666 ? C4 C5 C6 124.3(6) . 3_666 ? N2 C6 C5 110.8(6) . 3_666 ? C12 C7 C8 120.2(6) . . ? C12 C7 S1 120.3(5) . . ? C8 C7 S1 119.0(5) . . ? C7 C8 C9 119.9(6) . . ? C8 C9 C10 120.5(6) . . ? C11 C10 C9 118.5(6) . . ? C11 C10 C13 120.7(6) . . ? C9 C10 C13 120.8(6) . . ? C12 C11 C10 121.5(6) . . ? C11 C12 C7 119.3(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.754 _refine_diff_density_min -1.456 _refine_diff_density_rms 0.149 data_NiL2 _database_code_CSD 186306 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14.40 H19.20 F4.80 N3.20 Ni0.80 O4.80 S1.60' _chemical_formula_weight 503.39 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 10.4583(14) _cell_length_b 16.052(2) _cell_length_c 29.546(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4960.1(11) _cell_formula_units_Z 10 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6328 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.49 _exptl_crystal_description plate _exptl_crystal_colour clear_light_blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2576 _exptl_absorpt_coefficient_mu 1.038 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.812 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15s exposure) covering 0.3\% in \w. Crystal to detector distance 4.5 cm. ; _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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 55495 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 28.51 _reflns_number_total 6285 _reflns_number_gt 5268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0671P)^2^+28.7426P] 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 6285 _refine_ls_number_parameters 342 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1676 _refine_ls_wR_factor_gt 0.1589 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.78925(4) 0.15613(3) 0.369924(16) 0.01432(13) Uani 1 1 d . . . S11 S 1.00171(9) 0.00995(6) 0.34547(3) 0.0188(2) Uani 1 1 d . . . S21 S 0.49649(9) 0.21068(7) 0.40063(3) 0.0222(2) Uani 1 1 d . . . F11 F 1.2231(3) 0.0653(2) 0.31697(12) 0.0462(8) Uani 1 1 d . . . F12 F 1.2366(3) -0.04197(19) 0.36135(11) 0.0394(7) Uani 1 1 d . . . F13 F 1.1917(3) 0.0781(2) 0.38988(12) 0.0444(8) Uani 1 1 d . . . F21 F 0.3339(3) 0.1631(2) 0.46377(10) 0.0419(7) Uani 1 1 d . . . F22 F 0.5046(3) 0.22181(17) 0.48919(9) 0.0352(6) Uani 1 1 d . . . F23 F 0.5123(3) 0.09596(17) 0.46363(10) 0.0365(6) Uani 1 1 d . . . N11 N 0.7763(3) 0.21444(19) 0.30685(11) 0.0169(6) Uani 1 1 d . . . N12 N 0.9403(3) 0.0958(2) 0.33487(11) 0.0191(6) Uani 1 1 d . . . N21 N 0.8946(3) 0.2540(2) 0.39530(11) 0.0167(6) Uani 1 1 d . . . N22 N 0.6421(3) 0.2271(2) 0.39901(12) 0.0217(7) Uani 1 1 d . . . O11 O 1.0014(3) -0.04936(19) 0.30901(11) 0.0305(7) Uani 1 1 d . . . O12 O 0.9620(3) -0.01986(17) 0.38906(10) 0.0240(6) Uani 1 1 d . . . O21 O 0.4178(3) 0.2854(2) 0.39877(13) 0.0363(8) Uani 1 1 d . . . O22 O 0.4624(3) 0.1428(2) 0.37172(11) 0.0326(7) Uani 1 1 d . . . C11 C 0.6909(4) 0.2745(2) 0.29616(14) 0.0204(7) Uani 1 1 d . . . H11B H 0.6320 0.2923 0.3186 0.025 Uiso 1 1 calc R . . C12 C 0.6860(4) 0.3111(3) 0.25401(15) 0.0273(9) Uani 1 1 d . . . H12B H 0.6253 0.3535 0.2477 0.033 Uiso 1 1 calc R . . C13 C 0.7714(4) 0.2848(3) 0.22078(14) 0.0284(9) Uani 1 1 d . . . H13A H 0.7693 0.3086 0.1913 0.034 Uiso 1 1 calc R . . C14 C 0.8595(4) 0.2234(3) 0.23147(13) 0.0232(8) Uani 1 1 d . . . H14A H 0.9186 0.2041 0.2094 0.028 Uiso 1 1 calc R . . C15 C 0.8597(4) 0.1905(2) 0.27501(13) 0.0181(7) Uani 1 1 d . . . C16 C 0.9576(4) 0.1249(3) 0.28768(14) 0.0254(8) Uani 1 1 d . . . H16A H 0.9497 0.0769 0.2668 0.030 Uiso 1 1 calc R . . H16B H 1.0446 0.1484 0.2842 0.030 Uiso 1 1 calc R . . C17 C 1.1732(4) 0.0293(3) 0.35415(16) 0.0281(9) Uani 1 1 d . . . C21 C 1.0242(3) 0.2599(2) 0.39181(13) 0.0188(7) Uani 1 1 d . . . H21B H 1.0707 0.2142 0.3797 0.023 Uiso 1 1 calc R . . C22 C 1.0896(4) 0.3298(2) 0.40526(14) 0.0206(7) Uani 1 1 d . . . H22B H 1.1802 0.3316 0.4034 0.025 Uiso 1 1 calc R . . C23 C 1.0222(4) 0.3978(2) 0.42156(14) 0.0215(8) Uani 1 1 d . . . H23A H 1.0655 0.4475 0.4299 0.026 Uiso 1 1 calc R . . C24 C 0.8904(4) 0.3920(2) 0.42557(14) 0.0218(8) Uani 1 1 d . . . H24A H 0.8421 0.4377 0.4368 0.026 Uiso 1 1 calc R . . C25 C 0.8297(4) 0.3185(2) 0.41298(13) 0.0190(7) Uani 1 1 d . . . C26 C 0.6867(4) 0.3076(3) 0.41853(17) 0.0275(9) Uani 1 1 d . . . H26A H 0.6647 0.3095 0.4511 0.033 Uiso 1 1 calc R . . H26B H 0.6419 0.3542 0.4033 0.033 Uiso 1 1 calc R . . C27 C 0.4594(4) 0.1706(3) 0.45702(14) 0.0253(8) Uani 1 1 d . . . O31 O 0.6721(3) 0.05413(19) 0.35054(10) 0.0246(6) Uani 1 1 d D . . O41 O 0.8002(3) 0.08564(18) 0.42970(9) 0.0207(6) Uani 1 1 d D . . C31 C 0.6646(4) 0.0192(3) 0.30595(14) 0.0257(8) Uani 1 1 d . . . H31A H 0.7493 -0.0031 0.2972 0.031 Uiso 1 1 calc R . . H31B H 0.6411 0.0634 0.2841 0.031 Uiso 1 1 calc R . . C32 C 0.5666(4) -0.0498(3) 0.30404(15) 0.0291(9) Uani 1 1 d . . . H32A H 0.5635 -0.0727 0.2733 0.044 Uiso 1 1 calc R . . H32B H 0.4824 -0.0275 0.3121 0.044 Uiso 1 1 calc R . . H32C H 0.5903 -0.0938 0.3254 0.044 Uiso 1 1 calc R . . C41 C 0.8464(4) 0.1157(3) 0.47277(14) 0.0263(9) Uani 1 1 d . . . H41A H 0.7986 0.1665 0.4813 0.032 Uiso 1 1 calc R . . H41B H 0.9379 0.1307 0.4700 0.032 Uiso 1 1 calc R . . C42 C 0.8307(5) 0.0508(4) 0.50921(15) 0.0358(11) Uani 1 1 d . . . H42A H 0.8624 0.0730 0.5380 0.054 Uiso 1 1 calc R . . H42B H 0.8795 0.0009 0.5011 0.054 Uiso 1 1 calc R . . H42C H 0.7400 0.0364 0.5122 0.054 Uiso 1 1 calc R . . H41 H 0.855(6) 0.049(4) 0.424(3) 0.08(3) Uiso 1 1 d D . . H31 H 0.598(3) 0.068(4) 0.359(2) 0.06(2) Uiso 1 1 d 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 0.0141(2) 0.0136(2) 0.0153(2) 0.00128(17) 0.00075(16) 0.00105(16) S11 0.0190(4) 0.0155(4) 0.0218(4) -0.0007(3) -0.0012(3) 0.0007(3) S21 0.0120(4) 0.0378(6) 0.0167(4) 0.0031(4) 0.0009(3) -0.0004(4) F11 0.0216(13) 0.0559(19) 0.061(2) 0.0256(16) 0.0107(13) 0.0005(13) F12 0.0281(14) 0.0364(15) 0.0536(18) 0.0091(13) -0.0063(13) 0.0141(12) F13 0.0316(15) 0.0442(17) 0.058(2) -0.0140(15) -0.0196(14) -0.0011(13) F21 0.0272(14) 0.060(2) 0.0383(16) 0.0025(14) 0.0141(12) -0.0059(13) F22 0.0500(17) 0.0341(14) 0.0215(12) -0.0081(11) 0.0024(12) -0.0035(13) F23 0.0502(17) 0.0245(13) 0.0347(15) 0.0026(11) 0.0085(13) 0.0028(12) N11 0.0162(14) 0.0157(14) 0.0187(15) 0.0013(12) -0.0011(11) 0.0018(11) N12 0.0197(15) 0.0176(15) 0.0200(15) 0.0011(12) -0.0013(12) 0.0041(12) N21 0.0125(13) 0.0167(14) 0.0210(15) 0.0021(12) -0.0008(11) 0.0023(11) N22 0.0133(14) 0.0232(16) 0.0286(17) 0.0013(13) 0.0026(13) 0.0022(12) O11 0.0361(17) 0.0248(15) 0.0308(16) -0.0078(13) -0.0043(13) 0.0059(13) O12 0.0286(15) 0.0166(13) 0.0268(15) 0.0071(11) 0.0035(12) 0.0035(11) O21 0.0180(14) 0.0428(19) 0.048(2) 0.0121(16) 0.0036(14) 0.0081(14) O22 0.0201(14) 0.054(2) 0.0239(15) -0.0091(14) 0.0011(12) -0.0075(14) C11 0.0168(17) 0.0184(17) 0.0261(19) 0.0012(15) 0.0012(14) 0.0015(14) C12 0.026(2) 0.026(2) 0.029(2) 0.0048(17) -0.0070(17) 0.0055(16) C13 0.031(2) 0.034(2) 0.0206(19) 0.0105(17) -0.0040(16) -0.0014(18) C14 0.0225(19) 0.031(2) 0.0161(17) 0.0034(15) 0.0018(14) 0.0002(16) C15 0.0165(16) 0.0193(17) 0.0185(17) -0.0012(14) -0.0014(14) -0.0008(14) C16 0.028(2) 0.029(2) 0.0186(18) 0.0064(16) 0.0054(16) 0.0083(17) C17 0.0221(19) 0.026(2) 0.037(2) 0.0064(18) -0.0026(17) 0.0032(16) C21 0.0135(16) 0.0182(17) 0.0247(18) 0.0004(14) -0.0007(14) 0.0005(13) C22 0.0151(17) 0.0209(18) 0.0258(19) 0.0001(15) -0.0012(14) -0.0023(14) C23 0.0230(18) 0.0175(17) 0.0241(19) -0.0019(14) -0.0010(15) -0.0020(14) C24 0.0244(19) 0.0183(17) 0.0227(18) -0.0010(14) 0.0024(15) 0.0036(15) C25 0.0174(17) 0.0209(17) 0.0189(17) 0.0045(14) 0.0014(14) 0.0038(14) C26 0.0197(19) 0.0199(19) 0.043(3) -0.0039(17) 0.0051(17) 0.0020(15) C27 0.027(2) 0.026(2) 0.0235(19) -0.0013(16) 0.0039(16) -0.0018(16) O31 0.0293(16) 0.0258(15) 0.0188(14) -0.0023(11) -0.0027(12) -0.0067(12) O41 0.0233(14) 0.0222(14) 0.0167(13) 0.0031(11) -0.0037(11) -0.0025(11) C31 0.0249(19) 0.035(2) 0.0168(18) -0.0024(16) -0.0013(15) -0.0073(17) C32 0.029(2) 0.033(2) 0.025(2) -0.0063(17) 0.0017(17) -0.0102(18) C41 0.031(2) 0.028(2) 0.0200(19) -0.0022(16) -0.0066(16) 0.0020(17) C42 0.034(2) 0.054(3) 0.019(2) 0.005(2) -0.0020(18) 0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N21 2.060(3) . ? Ni1 N11 2.090(3) . ? Ni1 N22 2.099(3) . ? Ni1 O41 2.101(3) . ? Ni1 N12 2.123(3) . ? Ni1 O31 2.124(3) . ? S11 O12 1.435(3) . ? S11 O11 1.438(3) . ? S11 N12 1.552(3) . ? S11 C17 1.838(5) . ? S21 O22 1.430(3) . ? S21 O21 1.456(3) . ? S21 N22 1.546(3) . ? S21 C27 1.828(4) . ? F11 C17 1.346(5) . ? F12 C17 1.339(5) . ? F13 C17 1.328(6) . ? F21 C27 1.333(5) . ? F22 C27 1.343(5) . ? F23 C27 1.334(5) . ? N11 C15 1.339(5) . ? N11 C11 1.352(5) . ? N12 C16 1.481(5) . ? N21 C25 1.343(5) . ? N21 C21 1.362(5) . ? N22 C26 1.490(5) . ? C11 C12 1.377(6) . ? C12 C13 1.393(7) . ? C13 C14 1.385(6) . ? C14 C15 1.391(5) . ? C15 C16 1.516(5) . ? C21 C22 1.373(5) . ? C22 C23 1.385(5) . ? C23 C24 1.386(6) . ? C24 C25 1.391(6) . ? C25 C26 1.515(5) . ? O31 C31 1.434(5) . ? O41 C41 1.444(5) . ? C31 C32 1.509(6) . ? C41 C42 1.507(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N21 Ni1 N11 91.01(12) . . ? N21 Ni1 N22 80.18(13) . . ? N11 Ni1 N22 94.27(13) . . ? N21 Ni1 O41 94.33(12) . . ? N11 Ni1 O41 174.01(12) . . ? N22 Ni1 O41 89.32(13) . . ? N21 Ni1 N12 97.31(13) . . ? N11 Ni1 N12 79.48(12) . . ? N22 Ni1 N12 173.27(13) . . ? O41 Ni1 N12 97.12(12) . . ? N21 Ni1 O31 174.06(12) . . ? N11 Ni1 O31 93.87(12) . . ? N22 Ni1 O31 96.06(13) . . ? O41 Ni1 O31 80.97(11) . . ? N12 Ni1 O31 86.92(13) . . ? O12 S11 O11 116.81(19) . . ? O12 S11 N12 110.94(18) . . ? O11 S11 N12 115.85(19) . . ? O12 S11 C17 102.3(2) . . ? O11 S11 C17 102.6(2) . . ? N12 S11 C17 106.36(19) . . ? O22 S21 O21 117.7(2) . . ? O22 S21 N22 110.91(19) . . ? O21 S21 N22 114.5(2) . . ? O22 S21 C27 102.9(2) . . ? O21 S21 C27 101.8(2) . . ? N22 S21 C27 107.3(2) . . ? C15 N11 C11 118.1(3) . . ? C15 N11 Ni1 117.1(2) . . ? C11 N11 Ni1 124.8(3) . . ? C16 N12 S11 114.8(3) . . ? C16 N12 Ni1 114.0(2) . . ? S11 N12 Ni1 127.90(19) . . ? C25 N21 C21 118.6(3) . . ? C25 N21 Ni1 117.3(3) . . ? C21 N21 Ni1 123.9(3) . . ? C26 N22 S21 116.4(3) . . ? C26 N22 Ni1 113.6(2) . . ? S21 N22 Ni1 130.0(2) . . ? N11 C11 C12 122.7(4) . . ? C11 C12 C13 119.0(4) . . ? C14 C13 C12 118.7(4) . . ? C13 C14 C15 118.9(4) . . ? N11 C15 C14 122.7(4) . . ? N11 C15 C16 117.8(3) . . ? C14 C15 C16 119.6(3) . . ? N12 C16 C15 111.6(3) . . ? F13 C17 F12 107.8(4) . . ? F13 C17 F11 109.8(4) . . ? F12 C17 F11 107.7(4) . . ? F13 C17 S11 110.7(3) . . ? F12 C17 S11 111.2(3) . . ? F11 C17 S11 109.7(3) . . ? N21 C21 C22 122.0(4) . . ? C21 C22 C23 119.4(4) . . ? C22 C23 C24 118.9(4) . . ? C23 C24 C25 119.2(4) . . ? N21 C25 C24 121.8(4) . . ? N21 C25 C26 116.9(4) . . ? C24 C25 C26 121.3(4) . . ? N22 C26 C25 111.5(3) . . ? F21 C27 F23 107.8(4) . . ? F21 C27 F22 107.2(4) . . ? F23 C27 F22 107.5(4) . . ? F21 C27 S21 112.2(3) . . ? F23 C27 S21 111.2(3) . . ? F22 C27 S21 110.8(3) . . ? C31 O31 Ni1 125.5(2) . . ? C41 O41 Ni1 125.4(2) . . ? O31 C31 C32 111.0(3) . . ? O41 C41 C42 111.3(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.259 _refine_diff_density_min -0.838 _refine_diff_density_rms 0.129 data_NiL3 _database_code_CSD 186307 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 F6 N4 Ni O4 S2' _chemical_formula_weight 565.16 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' 0.3393 1.1124 '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 7.9362(3) _cell_length_b 9.4498(3) _cell_length_c 14.7162(5) _cell_angle_alpha 80.5190(10) _cell_angle_beta 80.6090(10) _cell_angle_gamma 81.5480(10) _cell_volume 1065.77(6) _cell_formula_units_Z 2 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 4317 _cell_measurement_theta_min 2.441 _cell_measurement_theta_max 27.489 _exptl_crystal_description block _exptl_crystal_colour translucent_purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 1.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.783 _exptl_absorpt_correction_T_max 0.888 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15s exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 11845 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4867 _reflns_number_gt 4379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0581P)^2^+0.6429P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4867 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.61888(3) 0.71743(3) 0.743772(16) 0.01621(9) Uani 1 1 d . . . S20 S 0.97863(6) 0.54848(5) 0.68841(3) 0.01913(12) Uani 1 1 d . . . S10 S 0.69509(7) 0.98089(5) 0.82373(3) 0.01927(12) Uani 1 1 d . . . O12 O 0.7922(2) 0.99821(17) 0.73202(10) 0.0252(3) Uani 1 1 d . . . O21 O 0.9968(2) 0.57988(18) 0.77833(11) 0.0273(3) Uani 1 1 d . . . F11 F 0.78873(18) 0.91239(15) 0.99040(9) 0.0296(3) Uani 1 1 d . . . F21 F 0.84288(18) 0.32077(16) 0.78228(9) 0.0315(3) Uani 1 1 d . . . F13 F 0.9526(2) 1.04851(16) 0.89310(11) 0.0407(4) Uani 1 1 d . . . F12 F 0.96958(17) 0.82191(16) 0.88301(10) 0.0306(3) Uani 1 1 d . . . F23 F 0.9220(2) 0.30809(16) 0.63608(10) 0.0353(3) Uani 1 1 d . . . N11 N 0.4505(2) 0.61471(19) 0.84132(12) 0.0183(3) Uani 1 1 d . . . O11 O 0.5882(2) 1.10318(17) 0.85816(11) 0.0272(3) Uani 1 1 d . . . O22 O 1.11798(19) 0.56137(18) 0.61300(11) 0.0256(3) Uani 1 1 d . . . C16 C 0.4653(3) 0.8212(2) 0.91812(14) 0.0229(4) Uani 1 1 d . . . H16A H 0.3701 0.9010 0.9121 0.028 Uiso 1 1 calc R . . H16B H 0.5102 0.8216 0.9770 0.028 Uiso 1 1 calc R . . C15 C 0.4008(3) 0.6788(2) 0.91914(14) 0.0205(4) Uani 1 1 d . . . F22 F 1.11230(18) 0.27722(16) 0.72976(12) 0.0387(4) Uani 1 1 d . . . C26 C 0.7718(3) 0.6290(3) 0.56400(15) 0.0335(6) Uani 1 1 d . . . H26A H 0.7686 0.5310 0.5493 0.040 Uiso 1 1 calc R . . H26B H 0.8675 0.6718 0.5217 0.040 Uiso 1 1 calc R . . N22 N 0.7995(2) 0.6202(2) 0.66116(12) 0.0219(4) Uani 1 1 d . . . C21 C 0.3578(3) 0.8589(2) 0.61656(16) 0.0247(4) Uani 1 1 d . . . N21 N 0.5105(2) 0.77512(19) 0.62538(12) 0.0195(3) Uani 1 1 d . . . C24 C 0.5472(3) 0.7485(3) 0.46378(16) 0.0311(5) Uani 1 1 d . . . H24A H 0.6141 0.7088 0.4122 0.037 Uiso 1 1 calc R . . C11 C 0.3920(3) 0.4883(2) 0.83662(15) 0.0223(4) Uani 1 1 d . . . N12 N 0.6035(2) 0.84129(19) 0.83850(12) 0.0197(3) Uani 1 1 d . . . C27 C 0.9631(3) 0.3529(2) 0.71016(15) 0.0238(4) Uani 1 1 d . . . C25 C 0.6038(3) 0.7216(2) 0.55048(14) 0.0230(4) Uani 1 1 d . . . C17 C 0.8618(3) 0.9384(2) 0.90143(15) 0.0230(4) Uani 1 1 d . . . C22 C 0.2980(3) 0.8894(3) 0.53079(18) 0.0308(5) Uani 1 1 d . . . H22B H 0.1917 0.9487 0.5249 0.037 Uiso 1 1 calc R . . C111 C 0.4445(3) 0.4252(2) 0.74746(16) 0.0252(4) Uani 1 1 d . . . H11B H 0.5195 0.4869 0.7039 0.038 Uiso 1 1 calc R . . H11C H 0.3417 0.4194 0.7200 0.038 Uiso 1 1 calc R . . H11D H 0.5064 0.3281 0.7604 0.038 Uiso 1 1 calc R . . C12 C 0.2850(3) 0.4232(3) 0.91132(17) 0.0282(5) Uani 1 1 d . . . H12B H 0.2460 0.3342 0.9078 0.034 Uiso 1 1 calc R . . C14 C 0.2927(3) 0.6181(3) 0.99495(15) 0.0259(5) Uani 1 1 d . . . H14A H 0.2588 0.6650 1.0486 0.031 Uiso 1 1 calc R . . C23 C 0.3924(3) 0.8338(3) 0.45402(17) 0.0336(5) Uani 1 1 d . . . H23A H 0.3514 0.8539 0.3955 0.040 Uiso 1 1 calc R . . C211 C 0.2587(3) 0.9131(3) 0.70193(18) 0.0336(5) Uani 1 1 d . . . H21B H 0.3231 0.8796 0.7545 0.050 Uiso 1 1 calc R . . H21C H 0.1467 0.8763 0.7159 0.050 Uiso 1 1 calc R . . H21D H 0.2412 1.0191 0.6915 0.050 Uiso 1 1 calc R . . C13 C 0.2352(3) 0.4882(3) 0.99101(16) 0.0306(5) Uani 1 1 d . . . H13A H 0.1624 0.4440 1.0423 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01517(14) 0.02085(15) 0.01187(13) -0.00403(10) 0.00041(9) -0.00057(10) S20 0.0159(2) 0.0222(2) 0.0186(2) -0.00538(19) -0.00015(18) -0.00009(18) S10 0.0217(3) 0.0199(2) 0.0161(2) -0.00193(18) -0.00378(18) -0.00169(19) O12 0.0265(8) 0.0307(8) 0.0173(7) 0.0009(6) -0.0018(6) -0.0065(6) O21 0.0268(8) 0.0324(9) 0.0241(8) -0.0107(7) -0.0075(6) 0.0037(7) F11 0.0357(8) 0.0360(7) 0.0170(6) -0.0048(5) -0.0056(5) -0.0007(6) F21 0.0271(7) 0.0351(8) 0.0268(7) 0.0038(6) 0.0052(5) -0.0051(6) F13 0.0493(9) 0.0340(8) 0.0454(9) 0.0073(7) -0.0258(7) -0.0204(7) F12 0.0245(7) 0.0362(8) 0.0295(7) -0.0065(6) -0.0058(5) 0.0054(6) F23 0.0458(9) 0.0330(8) 0.0301(7) -0.0110(6) 0.0017(6) -0.0148(6) N11 0.0161(8) 0.0221(8) 0.0165(8) -0.0021(6) -0.0030(6) -0.0010(6) O11 0.0327(9) 0.0212(8) 0.0269(8) -0.0053(6) -0.0057(7) 0.0024(6) O22 0.0169(7) 0.0295(8) 0.0279(8) -0.0049(6) 0.0054(6) -0.0035(6) C16 0.0224(10) 0.0282(11) 0.0171(9) -0.0072(8) 0.0038(8) -0.0024(8) C15 0.0156(9) 0.0263(10) 0.0173(9) -0.0005(8) -0.0016(7) 0.0015(8) F22 0.0233(7) 0.0255(7) 0.0626(10) -0.0026(7) -0.0029(7) 0.0044(6) C26 0.0320(13) 0.0508(15) 0.0153(10) -0.0118(10) -0.0027(9) 0.0097(11) N22 0.0192(9) 0.0297(10) 0.0156(8) -0.0065(7) -0.0024(6) 0.0042(7) C21 0.0223(11) 0.0242(11) 0.0269(11) 0.0012(9) -0.0044(9) -0.0050(8) N21 0.0187(8) 0.0223(8) 0.0169(8) -0.0010(7) -0.0026(6) -0.0029(7) C24 0.0358(13) 0.0409(14) 0.0178(10) -0.0042(9) -0.0051(9) -0.0076(10) C11 0.0189(10) 0.0237(10) 0.0243(10) 0.0027(8) -0.0095(8) -0.0024(8) N12 0.0202(9) 0.0235(9) 0.0151(8) -0.0062(7) 0.0020(6) -0.0033(7) C27 0.0195(10) 0.0250(10) 0.0247(10) -0.0031(8) 0.0023(8) -0.0023(8) C25 0.0249(11) 0.0269(11) 0.0175(10) -0.0028(8) -0.0037(8) -0.0039(8) C17 0.0252(11) 0.0248(10) 0.0200(10) -0.0027(8) -0.0055(8) -0.0046(8) C22 0.0248(12) 0.0321(12) 0.0348(13) 0.0050(10) -0.0126(10) -0.0025(9) C111 0.0253(11) 0.0228(10) 0.0295(11) -0.0047(9) -0.0086(9) -0.0030(8) C12 0.0240(11) 0.0296(12) 0.0310(12) 0.0065(9) -0.0105(9) -0.0083(9) C14 0.0205(11) 0.0369(12) 0.0169(10) 0.0016(9) -0.0004(8) -0.0005(9) C23 0.0396(14) 0.0393(14) 0.0238(11) 0.0053(10) -0.0149(10) -0.0108(11) C211 0.0225(12) 0.0396(14) 0.0327(13) -0.0029(10) -0.0020(9) 0.0107(10) C13 0.0207(11) 0.0415(14) 0.0252(11) 0.0111(10) -0.0036(9) -0.0073(10) _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 N12 1.9412(17) . ? Ni1 N22 1.9464(17) . ? Ni1 N11 2.0210(18) . ? Ni1 N21 2.0276(17) . ? S20 O22 1.4366(16) . ? S20 O21 1.4368(16) . ? S20 N22 1.5670(18) . ? S20 C27 1.842(2) . ? S10 O12 1.4378(16) . ? S10 O11 1.4410(16) . ? S10 N12 1.5660(18) . ? S10 C17 1.846(2) . ? F11 C17 1.341(3) . ? F21 C27 1.333(2) . ? F13 C17 1.330(3) . ? F12 C17 1.327(3) . ? F23 C27 1.335(3) . ? N11 C15 1.358(3) . ? N11 C11 1.359(3) . ? C16 N12 1.476(3) . ? C16 C15 1.505(3) . ? C15 C14 1.390(3) . ? F22 C27 1.338(3) . ? C26 N22 1.469(3) . ? C26 C25 1.506(3) . ? C21 N21 1.360(3) . ? C21 C22 1.392(3) . ? C21 C211 1.493(3) . ? N21 C25 1.351(3) . ? C24 C23 1.381(4) . ? C24 C25 1.393(3) . ? C11 C12 1.391(3) . ? C11 C111 1.502(3) . ? C22 C23 1.385(4) . ? C12 C13 1.387(4) . ? C14 C13 1.384(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 N12 Ni1 N22 137.32(8) . . ? N12 Ni1 N11 82.13(7) . . ? N22 Ni1 N11 124.26(8) . . ? N12 Ni1 N21 124.25(7) . . ? N22 Ni1 N21 82.23(7) . . ? N11 Ni1 N21 108.20(7) . . ? O22 S20 O21 120.16(10) . . ? O22 S20 N22 113.76(10) . . ? O21 S20 N22 110.02(9) . . ? O22 S20 C27 102.99(10) . . ? O21 S20 C27 102.96(10) . . ? N22 S20 C27 104.87(10) . . ? O12 S10 O11 119.84(10) . . ? O12 S10 N12 109.47(9) . . ? O11 S10 N12 113.92(10) . . ? O12 S10 C17 103.73(10) . . ? O11 S10 C17 102.99(10) . . ? N12 S10 C17 105.01(10) . . ? C15 N11 C11 119.40(19) . . ? C15 N11 Ni1 114.49(14) . . ? C11 N11 Ni1 126.04(14) . . ? N12 C16 C15 108.49(16) . . ? N11 C15 C14 121.8(2) . . ? N11 C15 C16 116.51(18) . . ? C14 C15 C16 121.63(19) . . ? N22 C26 C25 108.84(17) . . ? C26 N22 S20 118.09(15) . . ? C26 N22 Ni1 117.13(14) . . ? S20 N22 Ni1 124.44(10) . . ? N21 C21 C22 120.1(2) . . ? N21 C21 C211 117.4(2) . . ? C22 C21 C211 122.5(2) . . ? C25 N21 C21 119.67(18) . . ? C25 N21 Ni1 114.15(14) . . ? C21 N21 Ni1 126.18(15) . . ? C23 C24 C25 119.0(2) . . ? N11 C11 C12 120.6(2) . . ? N11 C11 C111 117.31(19) . . ? C12 C11 C111 122.1(2) . . ? C16 N12 S10 118.30(14) . . ? C16 N12 Ni1 116.29(13) . . ? S10 N12 Ni1 123.65(10) . . ? F21 C27 F23 107.97(18) . . ? F21 C27 F22 107.57(18) . . ? F23 C27 F22 108.11(18) . . ? F21 C27 S20 110.80(15) . . ? F23 C27 S20 111.07(15) . . ? F22 C27 S20 111.17(15) . . ? N21 C25 C24 121.8(2) . . ? N21 C25 C26 117.60(18) . . ? C24 C25 C26 120.6(2) . . ? F12 C17 F13 108.32(19) . . ? F12 C17 F11 107.52(17) . . ? F13 C17 F11 108.09(18) . . ? F12 C17 S10 111.84(15) . . ? F13 C17 S10 110.69(15) . . ? F11 C17 S10 110.24(15) . . ? C23 C22 C21 120.4(2) . . ? C13 C12 C11 120.0(2) . . ? C13 C14 C15 118.9(2) . . ? C24 C23 C22 119.0(2) . . ? C14 C13 C12 119.2(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.688 _refine_diff_density_min -0.597 _refine_diff_density_rms 0.079 data_NiL4 _database_code_CSD 186308 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H30 N4 Ni O4 S2' _chemical_formula_weight 609.39 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 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 32.016(11) _cell_length_b 11.932(4) _cell_length_c 16.782(8) _cell_angle_alpha 90 _cell_angle_beta 118.86(2) _cell_angle_gamma 90 _cell_volume 5615(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7235 _cell_measurement_theta_min 2.4356 _cell_measurement_theta_max 28.5423 _exptl_crystal_description block _exptl_crystal_colour clear_light_purple _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2544 _exptl_absorpt_coefficient_mu 0.881 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 0.932 _exptl_absorpt_correction_T_min 0.796 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15s exposure) covering 0.3\% in \w. Crystal to detector distance cm. ; _diffrn_ambient_temperature 120(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 'Bruker SMART CCD 6K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 38824 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 30.09 _reflns_number_total 8059 _reflns_number_gt 6051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0707P)^2^+4.7403P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 8059 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Ni Ni 0.172309(9) 0.75635(2) 0.205877(17) 0.01964(8) Uani 1 1 d . . . S21 S 0.15154(2) 0.51756(4) 0.24735(3) 0.02395(12) Uani 1 1 d . . . S11 S 0.10919(2) 0.94171(5) 0.22194(4) 0.02689(13) Uani 1 1 d . . . O11 O 0.11628(6) 1.06134(15) 0.22646(13) 0.0386(4) Uani 1 1 d . . . O12 O 0.07999(6) 0.89301(17) 0.13348(11) 0.0384(4) Uani 1 1 d . . . O21 O 0.18524(6) 0.42758(14) 0.26658(11) 0.0327(4) Uani 1 1 d . . . O22 O 0.15677(6) 0.58264(14) 0.32437(10) 0.0326(4) Uani 1 1 d . . . N21 N 0.17428(6) 0.74664(13) 0.08794(12) 0.0204(3) Uani 1 1 d . . . N22 N 0.15088(7) 0.60356(15) 0.17468(12) 0.0252(4) Uani 1 1 d . . . N12 N 0.15827(6) 0.87519(15) 0.26501(12) 0.0237(4) Uani 1 1 d . . . N11 N 0.23920(6) 0.77843(14) 0.31268(12) 0.0198(3) Uani 1 1 d . . . C165 C 0.05415(11) 0.7766(3) 0.3585(2) 0.0474(7) Uani 1 1 d . . . H16A H 0.0442 0.7022 0.3604 0.057 Uiso 1 1 calc R . . C17 C 0.03543(11) 0.8261(4) 0.4845(2) 0.0616(10) Uani 1 1 d . . . H17A H 0.0282 0.7458 0.4798 0.092 Uiso 1 1 calc R . . H17B H 0.0067 0.8691 0.4712 0.092 Uiso 1 1 calc R . . H17C H 0.0606 0.8435 0.5462 0.092 Uiso 1 1 calc R . . C262 C 0.05410(9) 0.5191(2) 0.15294(18) 0.0340(5) Uani 1 1 d . . . H26A H 0.0568 0.5970 0.1447 0.041 Uiso 1 1 calc R . . C264 C 0.00472(9) 0.3558(2) 0.13164(18) 0.0357(5) Uani 1 1 d . . . C22 C 0.19194(9) 0.8119(2) -0.02660(16) 0.0323(5) Uani 1 1 d . . . H22A H 0.2012 0.8714 -0.0524 0.039 Uiso 1 1 calc R . . C164 C 0.05210(9) 0.8569(3) 0.41673(18) 0.0427(7) Uani 1 1 d . . . C12 C 0.32055(8) 0.73284(19) 0.41141(17) 0.0291(5) Uani 1 1 d . . . H12B H 0.3491 0.6972 0.4209 0.035 Uiso 1 1 calc R . . C21 C 0.18678(8) 0.83119(17) 0.04963(14) 0.0245(4) Uani 1 1 d . . . C162 C 0.08242(10) 0.9931(2) 0.35104(19) 0.0404(6) Uani 1 1 d . . . H16B H 0.0921 1.0677 0.3486 0.049 Uiso 1 1 calc R . . C13 C 0.31952(9) 0.7927(2) 0.48160(16) 0.0316(5) Uani 1 1 d . . . H13A H 0.3469 0.7954 0.5401 0.038 Uiso 1 1 calc R . . C163 C 0.06631(11) 0.9645(3) 0.4121(2) 0.0479(7) Uani 1 1 d . . . H16C H 0.0651 1.0203 0.4513 0.057 Uiso 1 1 calc R . . C23 C 0.18372(9) 0.7065(2) -0.06529(15) 0.0304(5) Uani 1 1 d . . . H23A H 0.1876 0.6927 -0.1171 0.036 Uiso 1 1 calc R . . C266 C 0.09049(8) 0.33955(18) 0.20829(15) 0.0274(5) Uani 1 1 d . . . H26B H 0.1183 0.2942 0.2373 0.033 Uiso 1 1 calc R . . C161 C 0.08418(8) 0.9113(2) 0.29374(16) 0.0281(5) Uani 1 1 d . . . C25 C 0.16573(8) 0.64443(17) 0.04977(14) 0.0219(4) Uani 1 1 d . . . C11 C 0.27978(8) 0.72535(17) 0.32762(15) 0.0238(4) Uani 1 1 d . . . C265 C 0.04565(9) 0.2922(2) 0.17584(16) 0.0310(5) Uani 1 1 d . . . H26C H 0.0430 0.2142 0.1842 0.037 Uiso 1 1 calc R . . C166 C 0.07043(10) 0.8030(2) 0.29761(19) 0.0415(6) Uani 1 1 d . . . H16D H 0.0721 0.7470 0.2590 0.050 Uiso 1 1 calc R . . C26 C 0.15216(9) 0.55443(18) 0.09630(15) 0.0280(5) Uani 1 1 d . . . H26D H 0.1205 0.5233 0.0534 0.034 Uiso 1 1 calc R . . H26E H 0.1758 0.4928 0.1164 0.034 Uiso 1 1 calc R . . C24 C 0.16980(8) 0.62157(18) -0.02740(14) 0.0263(4) Uani 1 1 d . . . H24A H 0.1631 0.5488 -0.0536 0.032 Uiso 1 1 calc R . . C14 C 0.27841(8) 0.84781(18) 0.46539(15) 0.0271(4) Uani 1 1 d . . . H14A H 0.2770 0.8894 0.5123 0.033 Uiso 1 1 calc R . . C261 C 0.09439(8) 0.45381(18) 0.19800(14) 0.0233(4) Uani 1 1 d . . . C15 C 0.23911(7) 0.84148(17) 0.37929(14) 0.0216(4) Uani 1 1 d . . . C211 C 0.19518(10) 0.94323(19) 0.09396(17) 0.0328(5) Uani 1 1 d . . . H21B H 0.1892 0.9391 0.1459 0.049 Uiso 1 1 calc R . . H21C H 0.1736 0.9982 0.0500 0.049 Uiso 1 1 calc R . . H21D H 0.2283 0.9661 0.1151 0.049 Uiso 1 1 calc R . . C16 C 0.19454(8) 0.90645(18) 0.35536(14) 0.0243(4) Uani 1 1 d . . . H16E H 0.1833 0.8901 0.3998 0.029 Uiso 1 1 calc R . . H16F H 0.2011 0.9878 0.3575 0.029 Uiso 1 1 calc R . . C263 C 0.00955(9) 0.4699(2) 0.1198(2) 0.0418(6) Uani 1 1 d . . . H26F H -0.0182 0.5148 0.0883 0.050 Uiso 1 1 calc R . . C27 C -0.04353(10) 0.3016(3) 0.0944(2) 0.0539(8) Uani 1 1 d . . . H27A H -0.0396 0.2208 0.1063 0.081 Uiso 1 1 calc R . . H27B H -0.0618 0.3147 0.0287 0.081 Uiso 1 1 calc R . . H27C H -0.0606 0.3340 0.1241 0.081 Uiso 1 1 calc R . . C111 C 0.27889(8) 0.6609(2) 0.25047(16) 0.0293(5) Uani 1 1 d . . . H11B H 0.2472 0.6673 0.1970 0.044 Uiso 1 1 calc R . . H11C H 0.2859 0.5819 0.2677 0.044 Uiso 1 1 calc R . . H11D H 0.3029 0.6914 0.2361 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.02260(14) 0.01917(14) 0.01710(14) -0.00307(9) 0.00953(11) -0.00167(10) S21 0.0281(3) 0.0231(2) 0.0196(2) 0.00207(19) 0.0106(2) -0.0045(2) S11 0.0245(3) 0.0290(3) 0.0291(3) 0.0021(2) 0.0145(2) 0.0036(2) O11 0.0398(10) 0.0287(9) 0.0568(12) 0.0103(8) 0.0309(9) 0.0090(7) O12 0.0275(9) 0.0580(12) 0.0254(8) 0.0004(8) 0.0095(7) 0.0026(8) O21 0.0275(8) 0.0332(9) 0.0347(9) 0.0096(7) 0.0129(7) 0.0015(7) O22 0.0444(10) 0.0341(9) 0.0200(7) -0.0034(7) 0.0162(7) -0.0127(8) N21 0.0235(8) 0.0181(8) 0.0183(8) -0.0001(6) 0.0091(7) -0.0006(6) N22 0.0352(10) 0.0217(8) 0.0206(8) -0.0017(7) 0.0151(8) -0.0058(7) N12 0.0234(9) 0.0245(9) 0.0229(8) -0.0040(7) 0.0109(7) 0.0013(7) N11 0.0221(8) 0.0188(8) 0.0196(8) 0.0009(6) 0.0109(7) -0.0007(6) C165 0.0431(16) 0.0557(17) 0.0444(16) 0.0039(13) 0.0218(13) -0.0158(13) C17 0.0378(16) 0.110(3) 0.0432(17) 0.0220(18) 0.0242(14) 0.0051(18) C262 0.0338(13) 0.0224(11) 0.0413(14) 0.0000(10) 0.0145(11) 0.0012(9) C264 0.0326(13) 0.0395(13) 0.0375(13) -0.0047(11) 0.0189(11) -0.0065(10) C22 0.0451(14) 0.0271(11) 0.0299(12) 0.0041(9) 0.0222(11) -0.0031(10) C164 0.0201(11) 0.075(2) 0.0325(13) 0.0123(13) 0.0119(10) 0.0025(12) C12 0.0233(10) 0.0257(11) 0.0332(12) 0.0080(9) 0.0097(9) 0.0008(8) C21 0.0302(11) 0.0200(9) 0.0233(10) 0.0015(8) 0.0130(9) -0.0009(8) C162 0.0460(16) 0.0381(14) 0.0482(16) -0.0010(12) 0.0316(14) 0.0053(12) C13 0.0292(11) 0.0298(11) 0.0243(11) 0.0054(9) 0.0037(9) -0.0071(9) C163 0.0477(16) 0.0619(19) 0.0470(16) -0.0035(14) 0.0332(14) 0.0095(14) C23 0.0404(13) 0.0336(12) 0.0207(10) -0.0009(9) 0.0175(10) -0.0003(10) C266 0.0302(11) 0.0227(10) 0.0276(11) 0.0036(8) 0.0126(9) -0.0001(9) C161 0.0227(10) 0.0333(12) 0.0289(11) 0.0004(9) 0.0129(9) 0.0019(9) C25 0.0269(10) 0.0187(9) 0.0184(9) 0.0002(7) 0.0096(8) -0.0001(8) C11 0.0246(10) 0.0202(9) 0.0270(11) 0.0051(8) 0.0127(9) 0.0013(8) C265 0.0342(12) 0.0274(11) 0.0308(12) 0.0007(9) 0.0153(10) -0.0064(9) C166 0.0457(15) 0.0423(15) 0.0398(14) -0.0082(12) 0.0234(12) -0.0158(12) C26 0.0435(13) 0.0191(10) 0.0270(11) -0.0042(8) 0.0214(10) -0.0062(9) C24 0.0357(12) 0.0227(10) 0.0205(10) -0.0024(8) 0.0134(9) 0.0004(9) C14 0.0310(11) 0.0251(10) 0.0227(10) -0.0010(8) 0.0110(9) -0.0070(9) C261 0.0278(11) 0.0215(10) 0.0215(10) -0.0007(8) 0.0127(9) -0.0018(8) C15 0.0256(10) 0.0204(9) 0.0215(9) -0.0004(8) 0.0136(8) -0.0053(8) C211 0.0472(14) 0.0204(10) 0.0360(12) 0.0008(9) 0.0242(11) -0.0056(10) C16 0.0289(11) 0.0229(10) 0.0230(10) -0.0044(8) 0.0141(9) -0.0020(8) C263 0.0296(13) 0.0365(13) 0.0536(17) 0.0003(12) 0.0156(12) 0.0055(11) C27 0.0345(15) 0.0586(19) 0.069(2) -0.0024(16) 0.0249(15) -0.0111(14) C111 0.0300(11) 0.0298(11) 0.0316(11) 0.0040(9) 0.0177(10) 0.0079(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 Ni N12 1.9047(18) . ? Ni N22 1.9291(19) . ? Ni N21 2.014(2) . ? Ni N11 2.040(2) . ? S21 O21 1.4440(18) . ? S21 O22 1.4467(17) . ? S21 N22 1.5861(19) . ? S21 C261 1.775(2) . ? S11 O12 1.4408(19) . ? S11 O11 1.4416(19) . ? S11 N12 1.5891(19) . ? S11 C161 1.777(2) . ? N21 C25 1.343(3) . ? N21 C21 1.356(3) . ? N22 C26 1.459(3) . ? N12 C16 1.445(3) . ? N11 C15 1.349(3) . ? N11 C11 1.355(3) . ? C165 C166 1.389(4) . ? C165 C164 1.392(4) . ? C17 C164 1.516(4) . ? C262 C261 1.379(3) . ? C262 C263 1.386(4) . ? C264 C265 1.381(4) . ? C264 C263 1.395(4) . ? C264 C27 1.504(4) . ? C22 C23 1.381(3) . ? C22 C21 1.386(3) . ? C164 C163 1.376(4) . ? C12 C11 1.385(3) . ? C12 C13 1.391(4) . ? C21 C211 1.490(3) . ? C162 C161 1.390(3) . ? C162 C163 1.394(4) . ? C13 C14 1.376(3) . ? C23 C24 1.380(3) . ? C266 C265 1.387(3) . ? C266 C261 1.387(3) . ? C161 C166 1.376(4) . ? C25 C24 1.390(3) . ? C25 C26 1.510(3) . ? C11 C111 1.494(3) . ? C14 C15 1.386(3) . ? C15 C16 1.499(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 N12 Ni N22 134.63(8) . . ? N12 Ni N21 133.00(8) . . ? N22 Ni N21 81.64(7) . . ? N12 Ni N11 81.82(8) . . ? N22 Ni N11 116.45(8) . . ? N21 Ni N11 110.69(8) . . ? O21 S21 O22 116.59(11) . . ? O21 S21 N22 112.58(10) . . ? O22 S21 N22 107.02(10) . . ? O21 S21 C261 106.05(10) . . ? O22 S21 C261 107.20(10) . . ? N22 S21 C261 106.88(10) . . ? O12 S11 O11 117.44(12) . . ? O12 S11 N12 105.95(11) . . ? O11 S11 N12 112.00(10) . . ? O12 S11 C161 109.61(11) . . ? O11 S11 C161 106.11(11) . . ? N12 S11 C161 105.07(11) . . ? C25 N21 C21 119.22(18) . . ? C25 N21 Ni 115.17(14) . . ? C21 N21 Ni 125.42(14) . . ? C26 N22 S21 115.95(15) . . ? C26 N22 Ni 117.61(13) . . ? S21 N22 Ni 122.12(10) . . ? C16 N12 S11 117.76(15) . . ? C16 N12 Ni 117.83(14) . . ? S11 N12 Ni 124.40(11) . . ? C15 N11 C11 119.51(18) . . ? C15 N11 Ni 112.26(14) . . ? C11 N11 Ni 127.45(15) . . ? C166 C165 C164 121.5(3) . . ? C261 C262 C263 119.3(2) . . ? C265 C264 C263 118.2(2) . . ? C265 C264 C27 120.3(2) . . ? C263 C264 C27 121.5(3) . . ? C23 C22 C21 120.3(2) . . ? C163 C164 C165 118.2(2) . . ? C163 C164 C17 120.9(3) . . ? C165 C164 C17 120.8(3) . . ? C11 C12 C13 119.8(2) . . ? N21 C21 C22 120.5(2) . . ? N21 C21 C211 117.01(19) . . ? C22 C21 C211 122.5(2) . . ? C161 C162 C163 119.3(3) . . ? C14 C13 C12 119.3(2) . . ? C164 C163 C162 121.3(3) . . ? C24 C23 C22 118.9(2) . . ? C265 C266 C261 119.4(2) . . ? C166 C161 C162 120.4(2) . . ? C166 C161 S11 118.86(19) . . ? C162 C161 S11 120.51(19) . . ? N21 C25 C24 122.25(19) . . ? N21 C25 C26 116.26(18) . . ? C24 C25 C26 121.48(19) . . ? N11 C11 C12 120.5(2) . . ? N11 C11 C111 117.67(19) . . ? C12 C11 C111 121.8(2) . . ? C264 C265 C266 121.4(2) . . ? C161 C166 C165 119.3(3) . . ? N22 C26 C25 108.72(17) . . ? C23 C24 C25 118.8(2) . . ? C13 C14 C15 118.7(2) . . ? C262 C261 C266 120.5(2) . . ? C262 C261 S21 119.63(17) . . ? C266 C261 S21 119.85(17) . . ? N11 C15 C14 122.0(2) . . ? N11 C15 C16 116.69(18) . . ? C14 C15 C16 121.27(19) . . ? N12 C16 C15 109.07(17) . . ? C262 C263 C264 121.3(2) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 30.09 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.729 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.084 data_CoL1 _database_code_CSD 186309 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 Co N4 O4 S2,0.16(H2 O)' _chemical_formula_sum 'C26 H26.26 Co N4 O4.16 S2' _chemical_formula_weight 583.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Co' 'Co' 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 29.967(6) _cell_length_b 7.9772(15) _cell_length_c 26.183(5) _cell_angle_alpha 90 _cell_angle_beta 121.349(5) _cell_angle_gamma 90 _cell_volume 5345.2(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 738 _cell_measurement_theta_min 12.06558 _cell_measurement_theta_max 23.22 _exptl_crystal_description block _exptl_crystal_colour clear_dark_purple _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.45 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2417 _exptl_absorpt_coefficient_mu 0.838 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84095 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (20s exposure) covering 0.3\% in \w. Crystal to detector distance cm. ; _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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 27490 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6115 _reflns_number_gt 4482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^+8.5320P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens diffmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 6115 _refine_ls_number_parameters 447 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 Co1 Co 0.124691(14) 0.80529(5) 0.017961(16) 0.01281(11) Uani 1 1 d . . . S10 S 0.15044(3) 1.19265(8) 0.03827(3) 0.01307(15) Uani 1 1 d . . . S20 S 0.05766(3) 0.70995(8) -0.11783(3) 0.01413(15) Uani 1 1 d . . . N22 N 0.11017(9) 0.6933(3) -0.05478(10) 0.0150(5) Uani 1 1 d . . . N21 N 0.19595(9) 0.6958(3) 0.05115(10) 0.0154(5) Uani 1 1 d . . . O22 O 0.01776(8) 0.7636(2) -0.10584(9) 0.0190(4) Uani 1 1 d . . . O21 O 0.04687(8) 0.5621(2) -0.15469(9) 0.0210(5) Uani 1 1 d . . . N11 N 0.07878(9) 0.7571(3) 0.05215(10) 0.0128(5) Uani 1 1 d . . . C14 C 0.02747(11) 0.8838(4) 0.08755(12) 0.0157(6) Uani 1 1 d . . . N12 N 0.12081(9) 1.0339(3) 0.04288(10) 0.0140(5) Uani 1 1 d . . . O12 O 0.17654(8) 1.1395(3) 0.00770(9) 0.0181(4) Uani 1 1 d . . . C213 C 0.06579(11) 0.9972(4) -0.24098(13) 0.0182(6) Uani 1 1 d . . . C116 C 0.24962(11) 1.1760(4) 0.13708(14) 0.0207(6) Uani 1 1 d . . . C211 C 0.06586(10) 0.8794(3) -0.15629(12) 0.0136(5) Uani 1 1 d . . . C212 C 0.06320(11) 0.8567(4) -0.21036(13) 0.0174(6) Uani 1 1 d . . . O11 O 0.11657(8) 1.3379(2) 0.01521(9) 0.0175(4) Uani 1 1 d . . . C115 C 0.28811(12) 1.2169(4) 0.19486(14) 0.0246(7) Uani 1 1 d . . . C215 C 0.07493(11) 1.1764(3) -0.16231(13) 0.0150(6) Uani 1 1 d . . . C214 C 0.07059(11) 1.1585(3) -0.21776(13) 0.0163(6) Uani 1 1 d . . . C13 C 0.00914(11) 0.7281(4) 0.09108(13) 0.0185(6) Uani 1 1 d . . . C111 C 0.20007(11) 1.2452(3) 0.11251(12) 0.0146(5) Uani 1 1 d . . . C112 C 0.18958(12) 1.3536(4) 0.14695(13) 0.0194(6) Uani 1 1 d . . . C15 C 0.06282(10) 0.8942(3) 0.06841(11) 0.0119(5) Uani 1 1 d . . . C25 C 0.19991(11) 0.6050(3) 0.01015(13) 0.0151(6) Uani 1 1 d . . . C26 C 0.15304(11) 0.5985(4) -0.05222(13) 0.0157(6) Uani 1 1 d . . . C16 C 0.08553(11) 1.0611(3) 0.06498(13) 0.0133(5) Uani 1 1 d . . . C21 C 0.23769(11) 0.7037(4) 0.10754(13) 0.0201(6) Uani 1 1 d . . . C113 C 0.22854(13) 1.3905(4) 0.20505(14) 0.0236(7) Uani 1 1 d . . . C12 C 0.02622(12) 0.5862(4) 0.07542(13) 0.0192(6) Uani 1 1 d . . . C22 C 0.28413(12) 0.6237(4) 0.12476(15) 0.0252(7) Uani 1 1 d . . . C11 C 0.06041(11) 0.6052(3) 0.05559(13) 0.0158(6) Uani 1 1 d . . . C216 C 0.07268(11) 1.0392(3) -0.13164(12) 0.0146(5) Uani 1 1 d . . . C114 C 0.27835(12) 1.3250(4) 0.22975(13) 0.0237(7) Uani 1 1 d . . . C23 C 0.28817(12) 0.5298(4) 0.08234(15) 0.0253(7) Uani 1 1 d . . . C24 C 0.24598(12) 0.5216(4) 0.02520(16) 0.0208(7) Uani 1 1 d . . . C117 C 0.32134(16) 1.3713(6) 0.29235(17) 0.0382(9) Uani 1 1 d . . . C217 C 0.06883(13) 1.3127(4) -0.25234(15) 0.0236(7) Uani 1 1 d . . . H11B H 0.3327(19) 1.272(7) 0.318(2) 0.070(16) Uiso 1 1 d . . . H115 H 0.3173(14) 1.170(4) 0.2095(15) 0.021(9) Uiso 1 1 d . . . H212 H 0.0589(14) 0.747(5) -0.2279(16) 0.032(10) Uiso 1 1 d . . . H11A H 0.3488(16) 1.412(5) 0.2941(16) 0.036(11) Uiso 1 1 d . . . H215 H 0.0807(13) 1.278(5) -0.1430(15) 0.027(9) Uiso 1 1 d . . . H213 H 0.0628(11) 0.984(4) -0.2799(14) 0.016(8) Uiso 1 1 d . . . H113 H 0.2222(14) 1.463(5) 0.2303(16) 0.031(10) Uiso 1 1 d . . . H22 H 0.3118(12) 0.643(4) 0.1647(14) 0.014(8) Uiso 1 1 d . . . H21 H 0.2338(14) 0.773(5) 0.1385(16) 0.034(10) Uiso 1 1 d . . . H11 H 0.0738(12) 0.516(4) 0.0445(14) 0.017(8) Uiso 1 1 d . . . H13 H -0.0131(14) 0.719(4) 0.1032(15) 0.026(9) Uiso 1 1 d . . . H11C H 0.3075(14) 1.449(5) 0.3115(16) 0.033(10) Uiso 1 1 d . . . H116 H 0.2571(12) 1.104(4) 0.1139(14) 0.017(8) Uiso 1 1 d . . . H16A H 0.1056(11) 1.112(4) 0.1093(13) 0.010(7) Uiso 1 1 d . . . H14 H 0.0171(12) 0.989(4) 0.0976(14) 0.021(8) Uiso 1 1 d . . . H21A H 0.0821(13) 1.286(4) -0.2792(15) 0.028(9) Uiso 1 1 d . . . H26A H 0.1624(12) 0.646(4) -0.0798(14) 0.019(8) Uiso 1 1 d . . . H112 H 0.1592(13) 1.406(4) 0.1318(14) 0.022(9) Uiso 1 1 d . . . H21B H 0.0362(16) 1.353(5) -0.2742(17) 0.037(11) Uiso 1 1 d . . . H21C H 0.0898(16) 1.405(5) -0.2252(18) 0.042(11) Uiso 1 1 d . . . H26B H 0.1455(12) 0.481(4) -0.0609(13) 0.015(8) Uiso 1 1 d . . . H216 H 0.0780(11) 1.053(4) -0.0929(14) 0.012(7) Uiso 1 1 d . . . H23 H 0.3183(14) 0.473(5) 0.0936(15) 0.030(9) Uiso 1 1 d . . . H12 H 0.0146(12) 0.482(4) 0.0758(13) 0.014(8) Uiso 1 1 d . . . H16B H 0.0558(12) 1.138(4) 0.0381(13) 0.014(8) Uiso 1 1 d . . . H24 H 0.2468(13) 0.473(4) 0.0012(14) 0.016(9) Uiso 1 1 d . . . O1W O 0.0947(8) 0.307(3) 0.1869(9) 0.050(5) Uani 0.13 1 d P . . 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 0.01367(19) 0.01054(18) 0.01546(19) -0.00076(15) 0.00846(16) 0.00173(15) S10 0.0134(3) 0.0117(3) 0.0145(3) -0.0007(3) 0.0075(3) -0.0005(3) S20 0.0156(3) 0.0082(3) 0.0174(3) -0.0010(3) 0.0078(3) -0.0001(3) N22 0.0170(11) 0.0130(11) 0.0160(11) 0.0023(10) 0.0092(10) 0.0063(10) N21 0.0159(11) 0.0125(11) 0.0195(12) 0.0015(10) 0.0102(10) 0.0004(10) O22 0.0170(10) 0.0137(10) 0.0284(11) 0.0018(9) 0.0132(9) 0.0005(8) O21 0.0271(11) 0.0095(10) 0.0208(11) -0.0048(8) 0.0086(9) -0.0015(8) N11 0.0117(11) 0.0123(11) 0.0127(11) -0.0013(9) 0.0051(9) 0.0000(9) C14 0.0153(13) 0.0159(14) 0.0156(13) -0.0007(12) 0.0079(12) 0.0028(12) N12 0.0148(11) 0.0116(11) 0.0179(12) -0.0022(9) 0.0103(10) -0.0014(9) O12 0.0187(10) 0.0183(10) 0.0210(10) -0.0048(8) 0.0128(9) -0.0027(8) C213 0.0153(14) 0.0233(15) 0.0163(14) 0.0024(12) 0.0085(12) 0.0040(12) C116 0.0169(14) 0.0228(16) 0.0226(15) -0.0008(13) 0.0103(13) -0.0007(12) C211 0.0111(12) 0.0103(13) 0.0157(13) 0.0001(11) 0.0044(11) 0.0013(10) C212 0.0183(14) 0.0151(14) 0.0176(14) -0.0025(12) 0.0086(12) 0.0020(11) O11 0.0191(10) 0.0126(10) 0.0201(10) 0.0029(8) 0.0096(9) 0.0027(8) C115 0.0140(15) 0.0314(18) 0.0235(16) 0.0001(14) 0.0063(13) -0.0002(14) C215 0.0130(13) 0.0087(13) 0.0194(14) -0.0011(11) 0.0056(11) -0.0009(10) C214 0.0115(13) 0.0158(14) 0.0195(14) 0.0036(11) 0.0065(12) 0.0013(11) C13 0.0163(14) 0.0226(16) 0.0204(15) 0.0007(12) 0.0122(13) 0.0010(12) C111 0.0146(13) 0.0125(12) 0.0168(14) -0.0005(11) 0.0083(12) -0.0027(11) C112 0.0193(15) 0.0157(14) 0.0200(15) -0.0027(12) 0.0081(13) 0.0006(12) C15 0.0108(12) 0.0120(13) 0.0085(12) 0.0012(10) 0.0019(10) 0.0018(10) C25 0.0166(14) 0.0098(13) 0.0215(14) 0.0036(11) 0.0118(12) 0.0009(11) C26 0.0223(15) 0.0103(13) 0.0203(15) 0.0016(11) 0.0150(13) 0.0044(11) C16 0.0138(13) 0.0112(13) 0.0157(13) -0.0005(11) 0.0082(12) 0.0017(11) C21 0.0181(14) 0.0172(14) 0.0222(15) 0.0000(13) 0.0085(12) -0.0029(12) C113 0.0280(17) 0.0214(16) 0.0205(15) -0.0060(13) 0.0119(14) -0.0057(13) C12 0.0204(15) 0.0160(15) 0.0206(15) 0.0003(12) 0.0103(13) -0.0038(12) C22 0.0168(15) 0.0244(16) 0.0283(17) 0.0048(14) 0.0074(14) -0.0014(13) C11 0.0169(14) 0.0109(13) 0.0195(14) -0.0012(11) 0.0093(12) 0.0005(11) C216 0.0150(13) 0.0121(13) 0.0139(14) 0.0004(11) 0.0056(12) 0.0024(11) C114 0.0207(15) 0.0271(17) 0.0186(15) -0.0010(13) 0.0071(13) -0.0087(13) C23 0.0156(15) 0.0215(16) 0.0382(19) 0.0072(14) 0.0135(15) 0.0053(13) C24 0.0209(16) 0.0162(15) 0.0332(18) 0.0023(14) 0.0195(15) 0.0036(12) C117 0.029(2) 0.054(3) 0.0232(18) -0.0104(18) 0.0077(16) -0.0133(19) C217 0.0209(16) 0.0203(16) 0.0275(17) 0.0090(14) 0.0110(14) 0.0017(14) O1W 0.030(10) 0.068(15) 0.040(11) 0.006(11) 0.011(9) -0.010(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 Co1 N22 1.937(2) . ? Co1 N12 1.960(2) . ? Co1 N11 2.031(2) . ? Co1 N21 2.037(2) . ? S10 O12 1.443(2) . ? S10 O11 1.449(2) . ? S10 N12 1.587(2) . ? S10 C111 1.777(3) . ? S20 O21 1.450(2) . ? S20 O22 1.450(2) . ? S20 N22 1.586(2) . ? S20 C211 1.777(3) . ? N22 C26 1.462(3) . ? N21 C25 1.350(4) . ? N21 C21 1.352(4) . ? N11 C15 1.348(3) . ? N11 C11 1.353(4) . ? C14 C13 1.380(4) . ? C14 C15 1.390(4) . ? N12 C16 1.461(3) . ? C213 C214 1.398(4) . ? C213 C212 1.404(4) . ? C116 C115 1.382(4) . ? C116 C111 1.389(4) . ? C211 C212 1.388(4) . ? C211 C216 1.395(4) . ? C115 C114 1.394(5) . ? C215 C216 1.380(4) . ? C215 C214 1.396(4) . ? C214 C217 1.512(4) . ? C13 C12 1.389(4) . ? C111 C112 1.398(4) . ? C112 C113 1.384(4) . ? C15 C16 1.519(4) . ? C25 C24 1.392(4) . ? C25 C26 1.502(4) . ? C21 C22 1.376(4) . ? C113 C114 1.384(5) . ? C12 C11 1.377(4) . ? C22 C23 1.396(5) . ? C114 C117 1.512(5) . ? C23 C24 1.368(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 N22 Co1 N12 137.24(10) . . ? N22 Co1 N11 119.28(10) . . ? N12 Co1 N11 81.85(9) . . ? N22 Co1 N21 82.59(9) . . ? N12 Co1 N21 119.19(10) . . ? N11 Co1 N21 122.08(9) . . ? O12 S10 O11 117.90(12) . . ? O12 S10 N12 107.08(12) . . ? O11 S10 N12 111.81(12) . . ? O12 S10 C111 106.81(13) . . ? O11 S10 C111 105.86(12) . . ? N12 S10 C111 106.75(13) . . ? O21 S20 O22 117.45(12) . . ? O21 S20 N22 112.44(12) . . ? O22 S20 N22 106.41(12) . . ? O21 S20 C211 106.88(13) . . ? O22 S20 C211 105.70(12) . . ? N22 S20 C211 107.37(13) . . ? C26 N22 S20 117.60(19) . . ? C26 N22 Co1 116.80(18) . . ? S20 N22 Co1 125.35(13) . . ? C25 N21 C21 118.7(2) . . ? C25 N21 Co1 113.40(19) . . ? C21 N21 Co1 127.9(2) . . ? C15 N11 C11 118.8(2) . . ? C15 N11 Co1 114.75(18) . . ? C11 N11 Co1 126.25(18) . . ? C13 C14 C15 118.8(3) . . ? C16 N12 S10 117.39(18) . . ? C16 N12 Co1 116.77(17) . . ? S10 N12 Co1 125.78(13) . . ? C214 C213 C212 120.7(3) . . ? C115 C116 C111 119.7(3) . . ? C212 C211 C216 120.5(3) . . ? C212 C211 S20 121.8(2) . . ? C216 C211 S20 117.6(2) . . ? C211 C212 C213 119.2(3) . . ? C116 C115 C114 121.5(3) . . ? C216 C215 C214 121.2(3) . . ? C215 C214 C213 118.7(3) . . ? C215 C214 C217 119.6(3) . . ? C213 C214 C217 121.6(3) . . ? C14 C13 C12 119.5(3) . . ? C116 C111 C112 119.5(3) . . ? C116 C111 S10 119.8(2) . . ? C112 C111 S10 120.7(2) . . ? C113 C112 C111 119.8(3) . . ? N11 C15 C14 121.8(2) . . ? N11 C15 C16 116.7(2) . . ? C14 C15 C16 121.5(2) . . ? N21 C25 C24 121.0(3) . . ? N21 C25 C26 117.6(2) . . ? C24 C25 C26 121.3(3) . . ? N22 C26 C25 109.5(2) . . ? N12 C16 C15 109.4(2) . . ? N21 C21 C22 122.6(3) . . ? C114 C113 C112 121.4(3) . . ? C11 C12 C13 118.8(3) . . ? C21 C22 C23 118.7(3) . . ? N11 C11 C12 122.2(3) . . ? C215 C216 C211 119.7(3) . . ? C113 C114 C115 118.1(3) . . ? C113 C114 C117 121.2(3) . . ? C115 C114 C117 120.7(3) . . ? C24 C23 C22 118.8(3) . . ? C23 C24 C25 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.517 _refine_diff_density_min -0.726 _refine_diff_density_rms 0.156 data_CoL2 _database_code_CSD 186310 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Co F6 N4 O4 S2' _chemical_formula_weight 537.33 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 8.2696(3) _cell_length_b 9.8013(3) _cell_length_c 13.0497(4) _cell_angle_alpha 93.0150(10) _cell_angle_beta 95.5990(10) _cell_angle_gamma 108.4180(10) _cell_volume 994.84(6) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 6846 _cell_measurement_theta_min 2.1985 _cell_measurement_theta_max 27.477 _exptl_crystal_description irregular _exptl_crystal_colour clear_light_purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.794 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 538 _exptl_absorpt_coefficient_mu 1.158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 0.841 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (20s exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 110(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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 11046 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4537 _reflns_number_gt 3872 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0476P)^2^+0.9273P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4537 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Co Co 0.18133(4) 0.23487(3) 0.28162(2) 0.01633(10) Uani 1 1 d . . . S11 S 0.17061(7) 0.52323(6) 0.19715(4) 0.01607(13) Uani 1 1 d . . . S21 S 0.53453(7) 0.18073(7) 0.27292(4) 0.01775(14) Uani 1 1 d . . . F11 F 0.2660(2) 0.51259(18) 0.01120(12) 0.0319(4) Uani 1 1 d . . . F12 F 0.3857(2) 0.71762(19) 0.10071(15) 0.0412(5) Uani 1 1 d . . . F13 F 0.4675(2) 0.5346(2) 0.13504(14) 0.0399(4) Uani 1 1 d . . . F21 F 0.6092(3) 0.0183(2) 0.41236(14) 0.0441(5) Uani 1 1 d . . . F22 F 0.6261(2) -0.0524(2) 0.25549(14) 0.0373(4) Uani 1 1 d . . . F23 F 0.3796(3) -0.0889(2) 0.3085(2) 0.0562(6) Uani 1 1 d . . . N11 N 0.0080(2) 0.0730(2) 0.18690(15) 0.0153(4) Uani 1 1 d . . . N12 N 0.1035(2) 0.3549(2) 0.18540(15) 0.0168(4) Uani 1 1 d . . . N21 N 0.1663(3) 0.2793(2) 0.43348(15) 0.0191(4) Uani 1 1 d . . . N22 N 0.4054(2) 0.2228(2) 0.33818(15) 0.0174(4) Uani 1 1 d . . . O11 O 0.0456(2) 0.58950(19) 0.16109(15) 0.0238(4) Uani 1 1 d . . . O12 O 0.2709(2) 0.57356(19) 0.29638(13) 0.0223(4) Uani 1 1 d . . . O21 O 0.7107(2) 0.2697(2) 0.29891(14) 0.0250(4) Uani 1 1 d . . . O22 O 0.4631(3) 0.1498(2) 0.16672(14) 0.0314(5) Uani 1 1 d . . . C11 C -0.0206(3) -0.0708(3) 0.18976(18) 0.0187(5) Uani 1 1 d . . . H11B H 0.0432 -0.1026 0.2424 0.022 Uiso 1 1 calc R . . C12 C -0.1381(3) -0.1726(3) 0.11978(19) 0.0191(5) Uani 1 1 d . . . H12B H -0.1552 -0.2726 0.1241 0.023 Uiso 1 1 calc R . . C13 C -0.2317(3) -0.1260(3) 0.04230(18) 0.0189(5) Uani 1 1 d . . . H13A H -0.3138 -0.1940 -0.0070 0.023 Uiso 1 1 calc R . . C14 C -0.2037(3) 0.0201(3) 0.03817(18) 0.0183(5) Uani 1 1 d . . . H14A H -0.2670 0.0538 -0.0136 0.022 Uiso 1 1 calc R . . C15 C -0.0811(3) 0.1177(3) 0.11100(17) 0.0152(4) Uani 1 1 d . . . C16 C -0.0437(3) 0.2788(2) 0.10768(18) 0.0164(5) Uani 1 1 d . . . H16A H -0.0168 0.3070 0.0380 0.020 Uiso 1 1 calc R . . H16B H -0.1456 0.3053 0.1227 0.020 Uiso 1 1 calc R . . C17 C 0.3316(3) 0.5750(3) 0.1060(2) 0.0241(5) Uani 1 1 d . . . C21 C 0.0312(3) 0.3017(3) 0.4733(2) 0.0272(6) Uani 1 1 d . . . H21B H -0.0719 0.2871 0.4287 0.033 Uiso 1 1 calc R . . C22 C 0.0374(4) 0.3453(3) 0.5765(2) 0.0290(6) Uani 1 1 d . . . H22B H -0.0599 0.3594 0.6028 0.035 Uiso 1 1 calc R . . C23 C 0.1899(3) 0.3681(3) 0.6412(2) 0.0246(5) Uani 1 1 d . . . H23A H 0.1987 0.3997 0.7122 0.030 Uiso 1 1 calc R . . C24 C 0.3280(3) 0.3443(3) 0.60092(19) 0.0215(5) Uani 1 1 d . . . H24A H 0.4319 0.3575 0.6443 0.026 Uiso 1 1 calc R . . C25 C 0.3137(3) 0.3007(3) 0.49603(18) 0.0171(5) Uani 1 1 d . . . C26 C 0.4620(3) 0.2772(3) 0.44782(18) 0.0182(5) Uani 1 1 d . . . H26A H 0.5582 0.3692 0.4529 0.022 Uiso 1 1 calc R . . H26B H 0.5027 0.2064 0.4850 0.022 Uiso 1 1 calc R . . C27 C 0.5364(4) 0.0044(3) 0.3138(2) 0.0283(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 Co 0.01792(17) 0.01842(18) 0.01233(17) 0.00109(12) -0.00245(12) 0.00673(12) S11 0.0169(3) 0.0160(3) 0.0152(3) 0.0001(2) 0.0003(2) 0.0059(2) S21 0.0178(3) 0.0229(3) 0.0131(3) 0.0029(2) 0.0007(2) 0.0076(2) F11 0.0345(9) 0.0362(9) 0.0186(8) 0.0003(7) 0.0064(7) 0.0020(7) F12 0.0454(10) 0.0232(9) 0.0445(11) 0.0057(8) 0.0128(8) -0.0063(7) F13 0.0214(8) 0.0634(13) 0.0372(10) 0.0045(9) 0.0066(7) 0.0158(8) F21 0.0745(14) 0.0467(11) 0.0293(9) 0.0195(8) 0.0166(9) 0.0396(10) F22 0.0482(11) 0.0364(10) 0.0394(10) 0.0038(8) 0.0189(8) 0.0267(8) F23 0.0412(11) 0.0222(9) 0.1056(19) 0.0053(10) 0.0311(12) 0.0042(8) N11 0.0173(9) 0.0170(10) 0.0124(9) 0.0026(7) 0.0004(7) 0.0068(8) N12 0.0173(9) 0.0160(10) 0.0153(10) 0.0018(8) -0.0033(7) 0.0044(8) N21 0.0203(10) 0.0237(11) 0.0132(10) 0.0011(8) -0.0024(8) 0.0083(8) N22 0.0176(9) 0.0221(10) 0.0137(9) 0.0006(8) 0.0001(7) 0.0088(8) O11 0.0243(9) 0.0200(9) 0.0289(10) 0.0026(7) -0.0020(7) 0.0112(7) O12 0.0234(9) 0.0241(9) 0.0166(9) -0.0027(7) -0.0028(7) 0.0059(7) O21 0.0217(9) 0.0288(10) 0.0219(9) 0.0042(8) 0.0030(7) 0.0041(7) O22 0.0303(10) 0.0516(13) 0.0143(9) -0.0032(8) -0.0042(8) 0.0192(9) C11 0.0216(11) 0.0203(12) 0.0155(11) 0.0040(9) 0.0014(9) 0.0086(9) C12 0.0229(12) 0.0163(11) 0.0180(12) 0.0028(9) 0.0038(9) 0.0055(9) C13 0.0189(11) 0.0196(12) 0.0154(11) 0.0004(9) 0.0007(9) 0.0031(9) C14 0.0196(11) 0.0208(12) 0.0147(11) 0.0032(9) 0.0007(9) 0.0068(9) C15 0.0159(10) 0.0164(11) 0.0140(11) 0.0032(8) 0.0039(8) 0.0053(8) C16 0.0157(10) 0.0164(11) 0.0155(11) 0.0032(9) -0.0029(8) 0.0040(9) C17 0.0227(12) 0.0240(13) 0.0228(13) 0.0005(10) 0.0039(10) 0.0033(10) C21 0.0228(12) 0.0389(16) 0.0223(13) 0.0006(11) -0.0004(10) 0.0146(11) C22 0.0283(14) 0.0394(16) 0.0226(13) -0.0004(12) 0.0051(11) 0.0157(12) C23 0.0312(13) 0.0280(14) 0.0146(12) 0.0022(10) 0.0008(10) 0.0101(11) C24 0.0244(12) 0.0243(13) 0.0144(11) 0.0026(9) -0.0034(9) 0.0075(10) C25 0.0207(11) 0.0149(11) 0.0156(11) 0.0037(9) -0.0001(9) 0.0062(9) C26 0.0181(11) 0.0218(12) 0.0139(11) 0.0008(9) -0.0029(9) 0.0070(9) C27 0.0301(14) 0.0229(13) 0.0369(16) 0.0042(11) 0.0144(12) 0.0122(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 Co N12 1.962(2) . ? Co N22 1.968(2) . ? Co N11 2.028(2) . ? Co N21 2.031(2) . ? S11 O11 1.4397(18) . ? S11 O12 1.4397(18) . ? S11 N12 1.560(2) . ? S11 C17 1.841(3) . ? S21 O22 1.4298(19) . ? S21 O21 1.4380(18) . ? S21 N22 1.567(2) . ? S21 C27 1.840(3) . ? F11 C17 1.334(3) . ? F12 C17 1.334(3) . ? F13 C17 1.333(3) . ? F21 C27 1.347(4) . ? F22 C27 1.329(3) . ? F23 C27 1.322(3) . ? N11 C15 1.350(3) . ? N11 C11 1.357(3) . ? N12 C16 1.474(3) . ? N21 C25 1.350(3) . ? N21 C21 1.350(3) . ? N22 C26 1.477(3) . ? C11 C12 1.375(3) . ? C12 C13 1.397(3) . ? C13 C14 1.381(3) . ? C14 C15 1.396(3) . ? C15 C16 1.514(3) . ? C21 C22 1.383(4) . ? C22 C23 1.396(4) . ? C23 C24 1.381(4) . ? C24 C25 1.395(3) . ? C25 C26 1.506(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 N12 Co N22 135.44(8) . . ? N12 Co N11 82.25(8) . . ? N22 Co N11 122.17(8) . . ? N12 Co N21 116.01(9) . . ? N22 Co N21 81.83(8) . . ? N11 Co N21 125.16(8) . . ? O11 S11 O12 119.43(11) . . ? O11 S11 N12 114.41(11) . . ? O12 S11 N12 109.64(11) . . ? O11 S11 C17 103.09(12) . . ? O12 S11 C17 103.11(11) . . ? N12 S11 C17 105.22(12) . . ? O22 S21 O21 119.35(12) . . ? O22 S21 N22 109.58(11) . . ? O21 S21 N22 114.52(11) . . ? O22 S21 C27 103.88(14) . . ? O21 S21 C27 102.72(12) . . ? N22 S21 C27 104.87(12) . . ? C15 N11 C11 118.4(2) . . ? C15 N11 Co 114.44(16) . . ? C11 N11 Co 127.14(16) . . ? C16 N12 S11 119.38(16) . . ? C16 N12 Co 116.31(15) . . ? S11 N12 Co 123.70(11) . . ? C25 N21 C21 119.2(2) . . ? C25 N21 Co 114.40(16) . . ? C21 N21 Co 126.05(17) . . ? C26 N22 S21 118.72(16) . . ? C26 N22 Co 115.73(15) . . ? S21 N22 Co 124.99(12) . . ? N11 C11 C12 122.8(2) . . ? C11 C12 C13 118.6(2) . . ? C14 C13 C12 119.2(2) . . ? C13 C14 C15 119.2(2) . . ? N11 C15 C14 121.8(2) . . ? N11 C15 C16 117.4(2) . . ? C14 C15 C16 120.8(2) . . ? N12 C16 C15 108.85(18) . . ? F13 C17 F11 107.9(2) . . ? F13 C17 F12 108.2(2) . . ? F11 C17 F12 107.9(2) . . ? F13 C17 S11 110.96(19) . . ? F11 C17 S11 110.88(17) . . ? F12 C17 S11 110.93(19) . . ? N21 C21 C22 122.4(2) . . ? C21 C22 C23 118.4(3) . . ? C24 C23 C22 119.3(2) . . ? C23 C24 C25 119.5(2) . . ? N21 C25 C24 121.1(2) . . ? N21 C25 C26 117.4(2) . . ? C24 C25 C26 121.5(2) . . ? N22 C26 C25 109.11(19) . . ? F23 C27 F22 108.0(2) . . ? F23 C27 F21 107.5(2) . . ? F22 C27 F21 107.6(2) . . ? F23 C27 S21 111.9(2) . . ? F22 C27 S21 111.22(19) . . ? F21 C27 S21 110.48(19) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.743 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.082 data_CoL3 _database_code_CSD 186311 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Co F6 N4 O4 S2' _chemical_formula_weight 565.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 7.9999(2) _cell_length_b 9.3718(3) _cell_length_c 14.7362(5) _cell_angle_alpha 82.6250(10) _cell_angle_beta 81.5270(10) _cell_angle_gamma 81.7260(10) _cell_volume 1074.89(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6279 _cell_measurement_theta_min 4.419 _cell_measurement_theta_max 54.899 _exptl_crystal_description cube _exptl_crystal_colour clear_pale_purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 570 _exptl_absorpt_coefficient_mu 1.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.683 _exptl_absorpt_correction_T_max 0.764 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (10s exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _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 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\w-scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 11963 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4897 _reflns_number_gt 4121 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0438P)^2^+1.3994P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4897 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.09891(4) 0.20545(3) 0.24464(2) 0.01555(10) Uani 1 1 d . . . N12 N 0.0014(3) 0.2683(2) 0.12327(14) 0.0177(4) Uani 1 1 d . . . N13 N 0.2907(3) 0.1121(2) 0.16350(14) 0.0208(4) Uani 1 1 d . . . C15 C 0.1041(3) 0.2218(3) 0.04891(17) 0.0219(5) Uani 1 1 d . . . N21 N -0.0598(3) 0.1075(2) 0.34687(14) 0.0177(4) Uani 1 1 d . . . C21 C -0.1249(3) -0.0180(3) 0.34445(18) 0.0216(5) Uani 1 1 d . . . C14 C 0.0587(4) 0.2524(3) -0.03939(18) 0.0296(6) Uani 1 1 d . . . H14A H 0.1308 0.2179 -0.0895 0.036 Uiso 1 1 calc R . . C24 C -0.2039(3) 0.1253(3) 0.50023(18) 0.0246(5) Uani 1 1 d . . . H24A H -0.2294 0.1754 0.5521 0.029 Uiso 1 1 calc R . . C12 C -0.2010(4) 0.3837(3) 0.0245(2) 0.0299(6) Uani 1 1 d . . . H12A H -0.3050 0.4395 0.0172 0.036 Uiso 1 1 calc R . . N22 N 0.1018(3) 0.3347(2) 0.33926(14) 0.0183(4) Uani 1 1 d . . . C25 C -0.0993(3) 0.1777(3) 0.42320(17) 0.0197(5) Uani 1 1 d . . . C11 C -0.1512(3) 0.3488(3) 0.11165(18) 0.0227(5) Uani 1 1 d . . . C22 C -0.2296(3) -0.0747(3) 0.41965(19) 0.0277(6) Uani 1 1 d . . . H22A H -0.2732 -0.1608 0.4175 0.033 Uiso 1 1 calc R . . S20 S 0.19322(8) 0.47442(6) 0.32335(4) 0.01825(14) Uani 1 1 d . . . S10 S 0.46585(7) 0.03683(6) 0.19104(4) 0.01755(13) Uani 1 1 d . . . O21 O 0.2830(2) 0.4877(2) 0.23127(12) 0.0234(4) Uani 1 1 d . . . F21 F 0.3000(2) 0.41646(18) 0.48616(10) 0.0304(4) Uani 1 1 d . . . F22 F 0.4696(2) 0.31718(18) 0.37810(11) 0.0307(4) Uani 1 1 d . . . O22 O 0.0907(2) 0.59918(19) 0.35915(13) 0.0256(4) Uani 1 1 d . . . C211 C -0.0795(3) -0.0874(3) 0.25600(19) 0.0248(5) Uani 1 1 d . . . H21B H -0.0061 -0.0306 0.2131 0.037 Uiso 1 1 calc R . . H21C H -0.1815 -0.0922 0.2300 0.037 Uiso 1 1 calc R . . H21D H -0.0219 -0.1836 0.2684 0.037 Uiso 1 1 calc R . . C111 C -0.2602(4) 0.3942(3) 0.1973(2) 0.0335(7) Uani 1 1 d . . . H11A H -0.2023 0.3590 0.2500 0.050 Uiso 1 1 calc R . . H11B H -0.3662 0.3547 0.2042 0.050 Uiso 1 1 calc R . . H11C H -0.2821 0.4982 0.1927 0.050 Uiso 1 1 calc R . . C23 C -0.2697(3) -0.0030(3) 0.49841(19) 0.0288(6) Uani 1 1 d . . . H23A H -0.3398 -0.0406 0.5492 0.035 Uiso 1 1 calc R . . C27 C 0.3650(3) 0.4361(3) 0.39719(18) 0.0226(5) Uani 1 1 d . . . F12 F 0.3292(2) -0.19335(18) 0.26976(12) 0.0323(4) Uani 1 1 d . . . F23 F 0.4575(2) 0.54589(19) 0.38628(13) 0.0403(4) Uani 1 1 d . . . F13 F 0.5964(2) -0.23720(18) 0.22089(14) 0.0396(4) Uani 1 1 d . . . O11 O 0.6067(2) 0.0538(2) 0.11926(13) 0.0238(4) Uani 1 1 d . . . F11 F 0.4124(2) -0.19769(19) 0.12417(12) 0.0394(4) Uani 1 1 d . . . O12 O 0.4812(2) 0.0606(2) 0.28346(12) 0.0256(4) Uani 1 1 d . . . C17 C 0.4502(3) -0.1584(3) 0.20236(19) 0.0244(5) Uani 1 1 d . . . C26 C -0.0281(3) 0.3183(3) 0.42096(17) 0.0223(5) Uani 1 1 d . . . H26A H -0.1189 0.3988 0.4180 0.027 Uiso 1 1 calc R . . H26B H 0.0227 0.3189 0.4767 0.027 Uiso 1 1 calc R . . C13 C -0.0956(4) 0.3352(3) -0.0517(2) 0.0314(6) Uani 1 1 d . . . H13A H -0.1282 0.3581 -0.1104 0.038 Uiso 1 1 calc R . . C16 C 0.2720(4) 0.1327(4) 0.06441(18) 0.0356(7) Uani 1 1 d . . . H16A H 0.2777 0.0389 0.0420 0.043 Uiso 1 1 calc R . . H16B H 0.3647 0.1814 0.0301 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.01566(17) 0.01878(17) 0.01144(16) -0.00472(12) -0.00037(11) 0.00172(12) N12 0.0177(10) 0.0199(10) 0.0153(10) -0.0029(8) -0.0031(8) 0.0000(8) N13 0.0187(10) 0.0288(11) 0.0129(10) -0.0066(8) -0.0009(8) 0.0069(8) C15 0.0225(13) 0.0269(13) 0.0160(12) -0.0041(10) -0.0031(10) -0.0004(10) N21 0.0165(10) 0.0201(10) 0.0158(10) -0.0018(8) -0.0030(8) 0.0009(8) C21 0.0173(12) 0.0240(13) 0.0239(13) 0.0010(10) -0.0094(10) -0.0005(10) C14 0.0336(15) 0.0393(16) 0.0156(12) -0.0043(11) -0.0031(11) -0.0026(12) C24 0.0206(13) 0.0349(15) 0.0155(12) -0.0006(10) -0.0011(10) 0.0022(11) C12 0.0258(14) 0.0294(14) 0.0344(15) 0.0033(12) -0.0138(12) 0.0004(11) N22 0.0200(10) 0.0213(10) 0.0135(9) -0.0058(8) 0.0008(8) -0.0016(8) C25 0.0165(12) 0.0251(13) 0.0167(11) -0.0033(10) -0.0028(9) 0.0021(9) C11 0.0202(13) 0.0218(12) 0.0256(13) 0.0001(10) -0.0043(10) -0.0020(10) C22 0.0234(14) 0.0308(14) 0.0298(14) 0.0064(11) -0.0103(11) -0.0082(11) S20 0.0212(3) 0.0181(3) 0.0155(3) -0.0033(2) -0.0040(2) 0.0004(2) S10 0.0157(3) 0.0201(3) 0.0163(3) -0.0057(2) -0.0013(2) 0.0019(2) O21 0.0256(10) 0.0266(10) 0.0173(9) -0.0005(7) -0.0025(7) -0.0034(8) F21 0.0364(9) 0.0364(9) 0.0182(8) -0.0068(7) -0.0080(7) 0.0038(7) F22 0.0263(9) 0.0340(9) 0.0306(9) -0.0085(7) -0.0066(7) 0.0078(7) O22 0.0308(10) 0.0186(9) 0.0264(10) -0.0047(7) -0.0050(8) 0.0036(8) C211 0.0246(13) 0.0225(13) 0.0297(14) -0.0054(11) -0.0095(11) -0.0023(10) C111 0.0230(14) 0.0398(16) 0.0327(16) -0.0061(13) -0.0027(12) 0.0138(12) C23 0.0194(13) 0.0413(16) 0.0230(13) 0.0090(12) -0.0026(10) -0.0060(11) C27 0.0264(13) 0.0219(12) 0.0204(12) -0.0026(10) -0.0062(10) -0.0024(10) F12 0.0253(8) 0.0306(9) 0.0359(9) 0.0039(7) 0.0060(7) -0.0040(7) F23 0.0471(11) 0.0350(10) 0.0462(11) 0.0050(8) -0.0255(9) -0.0189(8) F13 0.0213(9) 0.0235(8) 0.0699(13) -0.0038(8) -0.0014(8) 0.0058(7) O11 0.0180(9) 0.0266(10) 0.0252(9) -0.0042(7) 0.0011(7) -0.0003(7) F11 0.0505(11) 0.0356(10) 0.0368(10) -0.0170(8) 0.0012(8) -0.0163(8) O12 0.0265(10) 0.0306(10) 0.0195(9) -0.0086(8) -0.0072(7) 0.0061(8) C17 0.0191(13) 0.0242(13) 0.0282(13) -0.0049(11) 0.0013(10) 0.0000(10) C26 0.0228(13) 0.0256(13) 0.0172(12) -0.0085(10) 0.0041(10) -0.0001(10) C13 0.0362(16) 0.0377(16) 0.0220(13) 0.0051(12) -0.0138(12) -0.0077(13) C16 0.0305(16) 0.059(2) 0.0127(12) -0.0097(12) -0.0037(11) 0.0164(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 Co1 N22 1.965(2) . ? Co1 N13 1.972(2) . ? Co1 N21 2.035(2) . ? Co1 N12 2.040(2) . ? N12 C15 1.349(3) . ? N12 C11 1.361(3) . ? N13 C16 1.475(3) . ? N13 S10 1.561(2) . ? C15 C14 1.386(4) . ? C15 C16 1.508(4) . ? N21 C25 1.351(3) . ? N21 C21 1.360(3) . ? C21 C22 1.384(4) . ? C21 C211 1.504(4) . ? C14 C13 1.383(4) . ? C24 C23 1.384(4) . ? C24 C25 1.388(4) . ? C12 C11 1.385(4) . ? C12 C13 1.386(4) . ? N22 C26 1.478(3) . ? N22 S20 1.565(2) . ? C25 C26 1.504(4) . ? C11 C111 1.498(4) . ? C22 C23 1.389(4) . ? S20 O21 1.4379(18) . ? S20 O22 1.4396(18) . ? S20 C27 1.844(3) . ? S10 O12 1.4333(18) . ? S10 O11 1.4390(18) . ? S10 C17 1.836(3) . ? F21 C27 1.337(3) . ? F22 C27 1.328(3) . ? C27 F23 1.331(3) . ? F12 C17 1.325(3) . ? F13 C17 1.335(3) . ? F11 C17 1.341(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 N22 Co1 N13 129.35(9) . . ? N22 Co1 N21 82.12(8) . . ? N13 Co1 N21 127.66(9) . . ? N22 Co1 N12 124.51(8) . . ? N13 Co1 N12 82.88(8) . . ? N21 Co1 N12 115.13(8) . . ? C15 N12 C11 119.3(2) . . ? C15 N12 Co1 113.73(16) . . ? C11 N12 Co1 126.97(17) . . ? C16 N13 S10 117.17(17) . . ? C16 N13 Co1 115.25(16) . . ? S10 N13 Co1 127.11(12) . . ? N12 C15 C14 122.1(2) . . ? N12 C15 C16 117.8(2) . . ? C14 C15 C16 120.1(2) . . ? C25 N21 C21 119.5(2) . . ? C25 N21 Co1 114.20(17) . . ? C21 N21 Co1 126.34(17) . . ? N21 C21 C22 120.6(2) . . ? N21 C21 C211 116.3(2) . . ? C22 C21 C211 123.1(2) . . ? C13 C14 C15 118.9(3) . . ? C23 C24 C25 118.8(2) . . ? C11 C12 C13 119.9(3) . . ? C26 N22 S20 117.90(16) . . ? C26 N22 Co1 115.21(16) . . ? S20 N22 Co1 124.79(12) . . ? N21 C25 C24 122.0(2) . . ? N21 C25 C26 117.2(2) . . ? C24 C25 C26 120.8(2) . . ? N12 C11 C12 120.7(2) . . ? N12 C11 C111 116.5(2) . . ? C12 C11 C111 122.9(3) . . ? C21 C22 C23 120.0(3) . . ? O21 S20 O22 119.78(11) . . ? O21 S20 N22 109.53(11) . . ? O22 S20 N22 113.96(11) . . ? O21 S20 C27 103.66(12) . . ? O22 S20 C27 102.71(12) . . ? N22 S20 C27 105.36(12) . . ? O12 S10 O11 119.75(12) . . ? O12 S10 N13 110.32(11) . . ? O11 S10 N13 113.86(11) . . ? O12 S10 C17 102.48(12) . . ? O11 S10 C17 103.32(11) . . ? N13 S10 C17 105.03(12) . . ? C24 C23 C22 119.1(2) . . ? F22 C27 F23 107.8(2) . . ? F22 C27 F21 107.5(2) . . ? F23 C27 F21 108.0(2) . . ? F22 C27 S20 111.92(17) . . ? F23 C27 S20 110.89(18) . . ? F21 C27 S20 110.50(18) . . ? F12 C17 F13 107.9(2) . . ? F12 C17 F11 107.8(2) . . ? F13 C17 F11 107.6(2) . . ? F12 C17 S10 110.82(18) . . ? F13 C17 S10 111.52(18) . . ? F11 C17 S10 110.99(19) . . ? N22 C26 C25 109.26(19) . . ? C14 C13 C12 119.2(3) . . ? N13 C16 C15 110.3(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.633 _refine_diff_density_min -0.597 _refine_diff_density_rms 0.081 data_CoL4 _database_code_CSD 186312 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H30 Co N4 O4 S2' _chemical_formula_weight 609.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Co' 'Co' 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 32.4490(9) _cell_length_b 12.0653(4) _cell_length_c 16.7380(5) _cell_angle_alpha 90.00 _cell_angle_beta 119.7210(10) _cell_angle_gamma 90.00 _cell_volume 5691.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5766 _cell_measurement_theta_min 2.5175 _cell_measurement_theta_max 27.47 _exptl_crystal_description irregular _exptl_crystal_colour lustrous_intense_red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2536 _exptl_absorpt_coefficient_mu 0.790 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 30866 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6536 _reflns_number_gt 5091 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+0.1928P] 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 6536 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.122 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_shift/su_max 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 Co Co 0.173236(10) 0.75450(2) 0.200686(19) 0.01600(10) Uani 1 1 d . . . S21 S 0.15167(2) 0.51620(5) 0.23910(4) 0.02062(14) Uani 1 1 d . . . S11 S 0.10935(2) 0.94517(5) 0.21113(4) 0.02313(15) Uani 1 1 d . . . O11 O 0.11691(6) 1.06408(15) 0.21835(13) 0.0345(4) Uani 1 1 d . . . O12 O 0.07989(6) 0.89969(17) 0.12013(11) 0.0337(4) Uani 1 1 d . . . O21 O 0.18519(6) 0.42788(14) 0.25521(12) 0.0280(4) Uani 1 1 d . . . O22 O 0.15893(7) 0.58020(15) 0.31850(11) 0.0298(4) Uani 1 1 d . . . N21 N 0.17218(7) 0.74782(14) 0.07720(13) 0.0185(4) Uani 1 1 d . . . N22 N 0.14850(7) 0.60351(16) 0.16537(12) 0.0221(4) Uani 1 1 d . . . N12 N 0.15808(7) 0.87814(16) 0.25509(12) 0.0194(4) Uani 1 1 d . . . N11 N 0.23966(6) 0.77755(15) 0.31325(12) 0.0165(4) Uani 1 1 d . . . C165 C 0.05650(10) 0.7754(3) 0.3472(2) 0.0385(7) Uani 1 1 d . . . H16A H 0.0479 0.7007 0.3498 0.046 Uiso 1 1 calc R . . C17 C 0.03567(11) 0.8223(3) 0.4702(2) 0.0528(9) Uani 1 1 d . . . H17A H 0.0287 0.7427 0.4647 0.079 Uiso 1 1 calc R . . H17B H 0.0069 0.8641 0.4559 0.079 Uiso 1 1 calc R . . H17C H 0.0606 0.8391 0.5331 0.079 Uiso 1 1 calc R . . C262 C 0.05443(10) 0.5150(2) 0.1545(2) 0.0421(7) Uani 1 1 d . . . H26A H 0.0564 0.5928 0.1484 0.050 Uiso 1 1 calc R . . C264 C 0.00700(10) 0.3497(2) 0.1335(2) 0.0365(6) Uani 1 1 d . . . C22 C 0.19118(10) 0.8083(2) -0.03609(17) 0.0319(6) Uani 1 1 d . . . H22A H 0.2009 0.8658 -0.0619 0.038 Uiso 1 1 calc R . . C164 C 0.05239(9) 0.8544(3) 0.40358(18) 0.0354(7) Uani 1 1 d . . . C12 C 0.32043(9) 0.7324(2) 0.41897(17) 0.0260(5) Uani 1 1 d . . . H12B H 0.3490 0.6957 0.4318 0.031 Uiso 1 1 calc R . . C21 C 0.18603(9) 0.82973(19) 0.03973(16) 0.0232(5) Uani 1 1 d . . . C162 C 0.08067(10) 0.9935(2) 0.3377(2) 0.0377(7) Uani 1 1 d . . . H16B H 0.0890 1.0683 0.3348 0.045 Uiso 1 1 calc R . . C13 C 0.31843(9) 0.7958(2) 0.48706(17) 0.0276(5) Uani 1 1 d . . . H13A H 0.3452 0.8003 0.5471 0.033 Uiso 1 1 calc R . . C163 C 0.06453(11) 0.9625(3) 0.3975(2) 0.0441(7) Uani 1 1 d . . . H16C H 0.0618 1.0174 0.4353 0.053 Uiso 1 1 calc R . . C23 C 0.18216(10) 0.7033(2) -0.07443(17) 0.0306(6) Uani 1 1 d . . . H23A H 0.1865 0.6878 -0.1254 0.037 Uiso 1 1 calc R . . C266 C 0.09195(9) 0.3364(2) 0.19764(16) 0.0243(5) Uani 1 1 d . . . H26B H 0.1197 0.2920 0.2203 0.029 Uiso 1 1 calc R . . C161 C 0.08442(8) 0.9129(2) 0.28192(16) 0.0243(5) Uani 1 1 d . . . C25 C 0.16244(8) 0.64614(19) 0.03883(15) 0.0201(5) Uani 1 1 d . . . C11 C 0.28045(8) 0.72367(19) 0.33267(16) 0.0205(5) Uani 1 1 d . . . C265 C 0.04820(9) 0.2873(2) 0.16896(18) 0.0281(5) Uani 1 1 d . . . H26C H 0.0464 0.2092 0.1737 0.034 Uiso 1 1 calc R . . C166 C 0.07292(10) 0.8033(2) 0.28726(19) 0.0339(6) Uani 1 1 d . . . H16D H 0.0762 0.7481 0.2504 0.041 Uiso 1 1 calc R . . C26 C 0.14740(10) 0.5586(2) 0.08334(16) 0.0267(5) Uani 1 1 d . . . H26D H 0.1149 0.5331 0.0393 0.032 Uiso 1 1 calc R . . H26E H 0.1690 0.4941 0.1004 0.032 Uiso 1 1 calc R . . C24 C 0.16679(9) 0.62135(19) -0.03785(16) 0.0249(5) Uani 1 1 d . . . H24A H 0.1593 0.5495 -0.0645 0.030 Uiso 1 1 calc R . . C14 C 0.27717(8) 0.8516(2) 0.46624(16) 0.0241(5) Uani 1 1 d . . . H14A H 0.2752 0.8953 0.5114 0.029 Uiso 1 1 calc R . . C261 C 0.09509(8) 0.45087(19) 0.19308(16) 0.0218(5) Uani 1 1 d . . . C15 C 0.23853(8) 0.84247(18) 0.37764(14) 0.0175(4) Uani 1 1 d . . . C211 C 0.19559(10) 0.9414(2) 0.08521(17) 0.0295(6) Uani 1 1 d . . . H21B H 0.1897 0.9382 0.1372 0.044 Uiso 1 1 calc R . . H21C H 0.1746 0.9966 0.0407 0.044 Uiso 1 1 calc R . . H21D H 0.2287 0.9621 0.1074 0.044 Uiso 1 1 calc R . . C16 C 0.19339(8) 0.90630(19) 0.34924(15) 0.0202(5) Uani 1 1 d . . . H16E H 0.1810 0.8882 0.3911 0.024 Uiso 1 1 calc R . . H16F H 0.2000 0.9868 0.3538 0.024 Uiso 1 1 calc R . . C263 C 0.01086(11) 0.4650(3) 0.1249(3) 0.0502(9) Uani 1 1 d . . . H26F H -0.0170 0.5092 0.0982 0.060 Uiso 1 1 calc R . . C27 C -0.04036(11) 0.2949(3) 0.1014(3) 0.0567(9) Uani 1 1 d . . . H27A H -0.0357 0.2151 0.1137 0.085 Uiso 1 1 calc R . . H27B H -0.0607 0.3071 0.0352 0.085 Uiso 1 1 calc R . . H27C H -0.0554 0.3267 0.1344 0.085 Uiso 1 1 calc R . . C111 C 0.27967(9) 0.6570(2) 0.25634(17) 0.0276(5) Uani 1 1 d . . . H11B H 0.2482 0.6620 0.2016 0.041 Uiso 1 1 calc R . . H11C H 0.2869 0.5793 0.2755 0.041 Uiso 1 1 calc R . . H11D H 0.3035 0.6860 0.2421 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co 0.02102(17) 0.01341(16) 0.01373(16) -0.00197(11) 0.00874(13) -0.00145(11) S21 0.0265(3) 0.0178(3) 0.0168(3) 0.0017(2) 0.0102(2) -0.0044(2) S11 0.0206(3) 0.0239(3) 0.0269(3) 0.0032(2) 0.0133(2) 0.0036(2) O11 0.0351(10) 0.0223(9) 0.0555(12) 0.0096(9) 0.0295(10) 0.0085(8) O12 0.0224(9) 0.0528(12) 0.0212(9) 0.0031(8) 0.0073(7) 0.0021(8) O21 0.0266(9) 0.0261(9) 0.0299(9) 0.0064(7) 0.0130(8) 0.0005(7) O22 0.0433(11) 0.0283(9) 0.0190(8) -0.0037(7) 0.0163(8) -0.0132(8) N21 0.0261(10) 0.0140(9) 0.0163(9) 0.0012(7) 0.0112(8) 0.0003(7) N22 0.0343(11) 0.0159(9) 0.0167(9) -0.0015(8) 0.0131(9) -0.0070(8) N12 0.0203(9) 0.0196(10) 0.0182(9) -0.0043(8) 0.0096(8) 0.0013(8) N11 0.0196(9) 0.0136(9) 0.0176(9) 0.0022(7) 0.0103(8) -0.0009(7) C165 0.0352(15) 0.0405(16) 0.0401(16) 0.0013(13) 0.0190(13) -0.0121(13) C17 0.0342(16) 0.091(3) 0.0380(16) 0.0182(18) 0.0216(14) 0.0044(17) C262 0.0370(16) 0.0190(13) 0.059(2) -0.0002(13) 0.0157(15) 0.0026(11) C264 0.0311(15) 0.0298(14) 0.0481(17) -0.0070(13) 0.0192(13) -0.0059(11) C22 0.0525(17) 0.0245(13) 0.0283(13) 0.0025(11) 0.0273(13) -0.0044(12) C164 0.0174(12) 0.0597(19) 0.0282(13) 0.0062(13) 0.0106(11) 0.0032(12) C12 0.0199(12) 0.0216(12) 0.0330(14) 0.0077(10) 0.0105(11) 0.0016(9) C21 0.0308(13) 0.0169(11) 0.0224(12) 0.0013(9) 0.0135(10) -0.0016(10) C162 0.0460(17) 0.0305(15) 0.0507(17) 0.0020(13) 0.0347(15) 0.0093(13) C13 0.0253(13) 0.0272(13) 0.0212(12) 0.0041(10) 0.0047(10) -0.0068(10) C163 0.0495(18) 0.0495(19) 0.0472(18) -0.0027(15) 0.0345(16) 0.0115(15) C23 0.0479(16) 0.0295(14) 0.0220(12) -0.0020(11) 0.0230(12) -0.0004(12) C266 0.0263(12) 0.0183(11) 0.0287(12) 0.0009(10) 0.0139(10) 0.0013(10) C161 0.0175(11) 0.0294(13) 0.0274(12) -0.0006(10) 0.0123(10) 0.0022(10) C25 0.0253(12) 0.0165(11) 0.0167(10) 0.0000(9) 0.0091(9) 0.0001(9) C11 0.0228(12) 0.0147(10) 0.0261(12) 0.0054(9) 0.0136(10) 0.0015(9) C265 0.0355(14) 0.0175(11) 0.0329(14) 0.0002(10) 0.0182(12) -0.0042(10) C166 0.0346(14) 0.0349(15) 0.0345(14) -0.0080(12) 0.0189(12) -0.0113(12) C26 0.0446(15) 0.0167(11) 0.0226(12) -0.0044(10) 0.0195(11) -0.0070(11) C24 0.0386(14) 0.0170(11) 0.0193(11) -0.0036(9) 0.0144(11) -0.0010(10) C14 0.0277(13) 0.0226(12) 0.0175(11) -0.0022(9) 0.0077(10) -0.0064(10) C261 0.0249(12) 0.0170(11) 0.0231(11) -0.0002(9) 0.0115(10) -0.0030(9) C15 0.0213(11) 0.0150(10) 0.0179(10) 0.0003(8) 0.0109(9) -0.0039(9) C211 0.0490(16) 0.0166(12) 0.0294(13) -0.0006(10) 0.0244(12) -0.0049(11) C16 0.0229(12) 0.0193(11) 0.0188(11) -0.0044(9) 0.0105(9) -0.0008(9) C263 0.0284(15) 0.0315(16) 0.080(2) -0.0083(16) 0.0184(16) 0.0042(12) C27 0.0337(17) 0.049(2) 0.085(3) -0.0064(19) 0.0274(18) -0.0093(15) C111 0.0295(13) 0.0255(13) 0.0310(13) 0.0040(11) 0.0175(11) 0.0090(10) _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 Co N12 1.9339(18) . ? Co N22 1.9601(19) . ? Co N21 2.0517(19) . ? Co N11 2.0607(18) . ? S21 O21 1.4493(18) . ? S21 O22 1.4517(17) . ? S21 N22 1.5866(19) . ? S21 C261 1.784(2) . ? S11 O12 1.4461(18) . ? S11 O11 1.4504(19) . ? S11 N12 1.595(2) . ? S11 C161 1.778(2) . ? N21 C25 1.348(3) . ? N21 C21 1.361(3) . ? N22 C26 1.460(3) . ? N12 C16 1.457(3) . ? N11 C15 1.348(3) . ? N11 C11 1.361(3) . ? C165 C166 1.391(4) . ? C165 C164 1.394(4) . ? C17 C164 1.512(4) . ? C262 C261 1.383(4) . ? C262 C263 1.383(4) . ? C264 C265 1.385(4) . ? C264 C263 1.410(4) . ? C264 C27 1.507(4) . ? C22 C21 1.384(3) . ? C22 C23 1.384(4) . ? C164 C163 1.381(4) . ? C12 C11 1.386(3) . ? C12 C13 1.400(4) . ? C21 C211 1.502(3) . ? C162 C163 1.392(4) . ? C162 C161 1.394(4) . ? C13 C14 1.380(4) . ? C23 C24 1.380(3) . ? C266 C265 1.386(3) . ? C266 C261 1.390(3) . ? C161 C166 1.388(4) . ? C25 C24 1.392(3) . ? C25 C26 1.506(3) . ? C11 C111 1.499(3) . ? C14 C15 1.393(3) . ? C15 C16 1.508(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 N12 Co N22 134.20(8) . . ? N12 Co N21 128.57(8) . . ? N22 Co N21 81.94(7) . . ? N12 Co N11 81.97(8) . . ? N22 Co N11 119.17(8) . . ? N21 Co N11 114.45(8) . . ? O21 S21 O22 117.03(11) . . ? O21 S21 N22 112.71(11) . . ? O22 S21 N22 106.11(10) . . ? O21 S21 C261 105.80(11) . . ? O22 S21 C261 107.19(11) . . ? N22 S21 C261 107.55(11) . . ? O12 S11 O11 117.34(12) . . ? O12 S11 N12 106.25(10) . . ? O11 S11 N12 112.03(11) . . ? O12 S11 C161 109.72(11) . . ? O11 S11 C161 105.99(11) . . ? N12 S11 C161 104.84(11) . . ? C25 N21 C21 119.64(19) . . ? C25 N21 Co 113.50(14) . . ? C21 N21 Co 126.25(15) . . ? C26 N22 S21 116.55(16) . . ? C26 N22 Co 116.36(14) . . ? S21 N22 Co 121.57(11) . . ? C16 N12 S11 116.69(15) . . ? C16 N12 Co 116.24(14) . . ? S11 N12 Co 126.83(11) . . ? C15 N11 C11 119.70(19) . . ? C15 N11 Co 112.25(14) . . ? C11 N11 Co 127.32(16) . . ? C166 C165 C164 121.5(3) . . ? C261 C262 C263 119.5(3) . . ? C265 C264 C263 117.6(2) . . ? C265 C264 C27 120.7(3) . . ? C263 C264 C27 121.6(3) . . ? C21 C22 C23 120.1(2) . . ? C163 C164 C165 118.0(3) . . ? C163 C164 C17 121.1(3) . . ? C165 C164 C17 120.9(3) . . ? C11 C12 C13 119.5(2) . . ? N21 C21 C22 120.3(2) . . ? N21 C21 C211 116.8(2) . . ? C22 C21 C211 122.9(2) . . ? C163 C162 C161 118.9(3) . . ? C14 C13 C12 119.4(2) . . ? C164 C163 C162 122.0(3) . . ? C24 C23 C22 119.3(2) . . ? C265 C266 C261 119.7(2) . . ? C166 C161 C162 120.4(2) . . ? C166 C161 S11 118.51(19) . . ? C162 C161 S11 120.8(2) . . ? N21 C25 C24 121.9(2) . . ? N21 C25 C26 117.36(19) . . ? C24 C25 C26 120.7(2) . . ? N11 C11 C12 120.6(2) . . ? N11 C11 C111 116.7(2) . . ? C12 C11 C111 122.7(2) . . ? C264 C265 C266 121.4(2) . . ? C161 C166 C165 119.3(3) . . ? N22 C26 C25 109.99(18) . . ? C23 C24 C25 118.7(2) . . ? C13 C14 C15 118.6(2) . . ? C262 C261 C266 120.2(2) . . ? C262 C261 S21 119.60(19) . . ? C266 C261 S21 120.21(18) . . ? N11 C15 C14 122.0(2) . . ? N11 C15 C16 116.88(18) . . ? C14 C15 C16 121.1(2) . . ? N12 C16 C15 110.00(17) . . ? C262 C263 C264 121.4(3) . . ? _refine_diff_density_max 0.623 _refine_diff_density_min -0.736