Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Chen, Yun-Ti' 'Leng, Xue-Bing' 'Lin, Hua-Kuan' 'Su, Xun-cheng' 'Zhu, Shou-Rong' _publ_contact_author_name 'Prof Shou-Rong Zhu' _publ_contact_author_address ; Department of Chemistry Nankai University Tianjin 300071 CHINA ; _publ_contact_author_email 'SZHU@NANKAI.EDU.CN' _publ_section_title ; Engineering of Noninterpenetrating 3-D and 2-D Network and Guest Adsorption Based on 4,4'-Di(3-methyl)pyridyl Sulfide Copper(II) complexes ; data_000605b _database_code_CSD 168662 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24.50 H26 Cl Cu N4 O4.50 S3' _chemical_formula_weight 643.66 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' 'Cl' 'Cl' 0.1484 0.1585 '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 18.698(2) _cell_length_b 14.3969(18) _cell_length_c 12.9711(16) _cell_angle_alpha 90.00 _cell_angle_beta 121.106(2) _cell_angle_gamma 90.00 _cell_volume 2989.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1324 _exptl_absorpt_coefficient_mu 1.067 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6117 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2637 _reflns_number_gt 2279 _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^)+(0.0807P)^2^+3.7342P] 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 2637 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.0000 0.0000 0.0330(2) Uani 1 2 d S . . S1 S 0.0000 0.14667(8) 0.2500 0.0438(3) Uani 1 2 d S . . O1 O 0.00797(14) 0.08864(18) 0.16480(19) 0.0464(6) Uani 1 1 d . . . O2 O 0.0760(3) 0.2017(3) 0.3163(4) 0.136(2) Uani 1 1 d . . . S2 S 0.37658(5) 0.13400(7) 0.14214(9) 0.0504(3) Uani 1 1 d . . . N1 N 0.12059(14) 0.03856(18) 0.0594(2) 0.0330(5) Uani 1 1 d . . . N2 N 0.45637(14) 0.38360(17) 0.3924(2) 0.0333(5) Uani 1 1 d . . . C1 C 0.15882(18) 0.1093(2) 0.1364(3) 0.0373(7) Uani 1 1 d . . . H1A H 0.1314 0.1381 0.1705 0.045 Uiso 1 1 calc R . . C2 C 0.23708(19) 0.1412(2) 0.1670(3) 0.0395(7) Uani 1 1 d . . . H2A H 0.2616 0.1904 0.2205 0.047 Uiso 1 1 calc R . . C3 C 0.27855(17) 0.0986(2) 0.1168(3) 0.0337(6) Uani 1 1 d . . . C4 C 0.24032(19) 0.0235(2) 0.0379(3) 0.0364(7) Uani 1 1 d . . . C5 C 0.1624(2) -0.0033(2) 0.0140(3) 0.0362(7) Uani 1 1 d . . . H5A H 0.1371 -0.0537 -0.0371 0.043 Uiso 1 1 calc R . . C6 C 0.2806(3) -0.0254(3) -0.0221(4) 0.0600(11) Uani 1 1 d . . . H6A H 0.2447 -0.0744 -0.0724 0.090 Uiso 1 1 calc R . . H6B H 0.3333 -0.0511 0.0382 0.090 Uiso 1 1 calc R . . H6C H 0.2896 0.0181 -0.0704 0.090 Uiso 1 1 calc R . . C7 C 0.40309(17) 0.2294(2) 0.2428(3) 0.0369(7) Uani 1 1 d . . . C8 C 0.43987(19) 0.2166(2) 0.3666(3) 0.0396(7) Uani 1 1 d . . . C9 C 0.46525(19) 0.2977(2) 0.4362(3) 0.0385(7) Uani 1 1 d . . . H9A H 0.4901 0.2912 0.5191 0.046 Uiso 1 1 calc R . . C10 C 0.41922(19) 0.3935(2) 0.2731(3) 0.0415(7) Uani 1 1 d . . . H10A H 0.4113 0.4529 0.2408 0.050 Uiso 1 1 calc R . . C11 C 0.3923(2) 0.3181(2) 0.1967(3) 0.0426(7) Uani 1 1 d . . . H11A H 0.3669 0.3270 0.1141 0.051 Uiso 1 1 calc R . . C12 C 0.4522(3) 0.1242(3) 0.4252(4) 0.0613(10) Uani 1 1 d . . . H12A H 0.4789 0.1322 0.5107 0.092 Uiso 1 1 calc R . . H12B H 0.4867 0.0862 0.4075 0.092 Uiso 1 1 calc R . . H12C H 0.3990 0.0946 0.3951 0.092 Uiso 1 1 calc R . . Cl2 Cl 0.2876(8) 0.2652(6) 0.4292(10) 0.147(3) Uani 0.25 1 d P . . O3 O 0.5000 -0.0938(9) 0.2500 0.223(12) Uani 0.50 2 d SP . . Cl1 Cl 0.1531(11) 0.3534(10) 0.2326(11) 0.228(7) Uani 0.25 1 d P . . C13 C 0.2031(17) 0.284(2) 0.332(3) 0.143(15) Uani 0.25 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 Cu1 0.0225(3) 0.0359(3) 0.0360(3) 0.0092(2) 0.0120(2) -0.00183(18) S1 0.0668(8) 0.0334(6) 0.0461(6) 0.000 0.0398(6) 0.000 O1 0.0468(13) 0.0630(15) 0.0377(11) -0.0068(10) 0.0278(10) -0.0010(11) O2 0.196(5) 0.132(4) 0.124(3) -0.074(3) 0.114(3) -0.125(4) S2 0.0390(4) 0.0591(6) 0.0679(6) -0.0329(4) 0.0381(4) -0.0208(4) N1 0.0274(12) 0.0364(13) 0.0344(12) 0.0025(10) 0.0155(10) -0.0033(10) N2 0.0263(12) 0.0375(14) 0.0351(13) -0.0044(10) 0.0151(10) -0.0004(10) C1 0.0287(14) 0.0459(17) 0.0409(16) -0.0064(14) 0.0205(13) -0.0034(13) C2 0.0323(15) 0.0452(18) 0.0436(16) -0.0159(14) 0.0214(13) -0.0093(13) C3 0.0267(13) 0.0398(16) 0.0367(15) -0.0055(12) 0.0177(12) -0.0049(12) C4 0.0337(15) 0.0373(16) 0.0421(16) -0.0077(13) 0.0222(14) -0.0038(13) C5 0.0331(16) 0.0337(16) 0.0388(16) -0.0055(12) 0.0164(14) -0.0066(11) C6 0.054(2) 0.064(2) 0.077(3) -0.036(2) 0.044(2) -0.0157(19) C7 0.0255(14) 0.0458(18) 0.0446(16) -0.0151(14) 0.0218(13) -0.0116(12) C8 0.0360(16) 0.0428(17) 0.0487(17) -0.0051(14) 0.0280(14) -0.0079(13) C9 0.0382(16) 0.0447(18) 0.0363(16) -0.0048(13) 0.0218(14) -0.0034(14) C10 0.0392(16) 0.0407(17) 0.0364(15) -0.0003(13) 0.0137(13) 0.0008(14) C11 0.0381(16) 0.0508(19) 0.0334(15) -0.0062(14) 0.0147(13) -0.0046(14) C12 0.079(3) 0.045(2) 0.071(3) 0.0018(18) 0.047(2) -0.0102(19) Cl2 0.211(10) 0.107(5) 0.199(9) -0.040(6) 0.160(9) -0.027(6) O3 0.37(3) 0.050(7) 0.098(9) 0.000 0.011(13) 0.000 Cl1 0.285(17) 0.173(11) 0.148(9) -0.057(8) 0.056(10) 0.002(11) C13 0.083(16) 0.16(3) 0.21(3) -0.15(3) 0.09(2) -0.055(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.047(2) . ? Cu1 N1 2.047(2) 5 ? Cu1 N2 2.061(2) 4_545 ? Cu1 N2 2.061(2) 8_455 ? Cu1 O1 2.427(2) . ? Cu1 O1 2.427(2) 5 ? S1 O1 1.453(2) . ? S1 O1 1.453(2) 2 ? S1 O2 1.458(4) . ? S1 O2 1.458(4) 2 ? S2 C3 1.762(3) . ? S2 C7 1.780(3) . ? N1 C5 1.340(4) . ? N1 C1 1.345(4) . ? N2 C9 1.335(4) . ? N2 C10 1.336(4) . ? N2 Cu1 2.061(2) 4 ? C1 C2 1.381(4) . ? C2 C3 1.387(4) . ? C3 C4 1.404(4) . ? C4 C5 1.379(4) . ? C4 C6 1.510(4) . ? C7 C11 1.379(5) . ? C7 C8 1.395(4) . ? C8 C9 1.400(4) . ? C8 C12 1.490(5) . ? C10 C11 1.378(5) . ? Cl2 C13 1.45(4) . ? Cl1 C13 1.52(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.00(18) . 5 ? N1 Cu1 N2 89.54(9) . 4_545 ? N1 Cu1 N2 90.46(9) 5 4_545 ? N1 Cu1 N2 90.46(9) . 8_455 ? N1 Cu1 N2 89.54(9) 5 8_455 ? N2 Cu1 N2 180.00(8) 4_545 8_455 ? N1 Cu1 O1 88.35(9) . . ? N1 Cu1 O1 91.65(9) 5 . ? N2 Cu1 O1 90.47(9) 4_545 . ? N2 Cu1 O1 89.53(9) 8_455 . ? N1 Cu1 O1 91.65(9) . 5 ? N1 Cu1 O1 88.35(9) 5 5 ? N2 Cu1 O1 89.53(9) 4_545 5 ? N2 Cu1 O1 90.47(9) 8_455 5 ? O1 Cu1 O1 180.00(9) . 5 ? O1 S1 O1 109.8(2) . 2 ? O1 S1 O2 108.0(2) . . ? O1 S1 O2 108.4(2) 2 . ? O1 S1 O2 108.4(2) . 2 ? O1 S1 O2 108.0(2) 2 2 ? O2 S1 O2 114.2(5) . 2 ? S1 O1 Cu1 171.23(15) . . ? C3 S2 C7 103.24(13) . . ? C5 N1 C1 117.4(2) . . ? C5 N1 Cu1 119.4(2) . . ? C1 N1 Cu1 123.0(2) . . ? C9 N2 C10 117.9(3) . . ? C9 N2 Cu1 123.1(2) . 4 ? C10 N2 Cu1 119.0(2) . 4 ? N1 C1 C2 122.9(3) . . ? C1 C2 C3 119.0(3) . . ? C2 C3 C4 119.0(3) . . ? C2 C3 S2 124.4(2) . . ? C4 C3 S2 116.6(2) . . ? C5 C4 C3 117.4(3) . . ? C5 C4 C6 120.3(3) . . ? C3 C4 C6 122.2(3) . . ? N1 C5 C4 124.3(3) . . ? C11 C7 C8 119.7(3) . . ? C11 C7 S2 118.3(2) . . ? C8 C7 S2 121.8(3) . . ? C7 C8 C9 115.7(3) . . ? C7 C8 C12 124.0(3) . . ? C9 C8 C12 120.3(3) . . ? N2 C9 C8 124.8(3) . . ? N2 C10 C11 121.8(3) . . ? C10 C11 C7 120.0(3) . . ? Cl2 C13 Cl1 141(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.605 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.083 data_001110c _database_code_CSD 168663 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H27 Cl9 Cu N6 O0 S4' _chemical_formula_weight 970.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.588(3) _cell_length_b 18.717(5) _cell_length_c 18.227(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.980(5) _cell_angle_gamma 90.00 _cell_volume 4288.6(19) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1956 _exptl_absorpt_coefficient_mu 1.294 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6601 _exptl_absorpt_correction_T_max 0.7818 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16805 _diffrn_reflns_av_R_equivalents 0.0841 _diffrn_reflns_av_sigmaI/netI 0.1371 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.03 _reflns_number_total 7252 _reflns_number_gt 2710 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7252 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1906 _refine_ls_R_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.1767 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.032 _refine_ls_shift/su_mean 0.003 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 0.20901(6) 0.25196(5) -0.10232(4) 0.0497(3) Uani 1 1 d . . . N1 N 0.1286(4) 0.3265(3) -0.0106(3) 0.0555(15) Uani 1 1 d . . . N2 N -0.2084(5) 0.3216(3) 0.3019(3) 0.0594(16) Uani 1 1 d . . . N3 N 0.2874(4) 0.1891(3) -0.0234(3) 0.0495(14) Uani 1 1 d . . . N4 N 0.6295(4) 0.1860(3) 0.3173(3) 0.0479(14) Uani 1 1 d . . . N5 N 0.3317(5) 0.3173(3) -0.1033(3) 0.0610(17) Uani 1 1 d . . . N6 N 0.0864(5) 0.1865(3) -0.1037(3) 0.0632(17) Uani 1 1 d . . . S1 S -0.03291(17) 0.47000(10) 0.15055(12) 0.0731(6) Uani 1 1 d . . . S2 S 0.46333(17) 0.04520(10) 0.14345(11) 0.0697(6) Uani 1 1 d . . . S3 S 0.4804(2) 0.41592(15) -0.05215(19) 0.1266(11) Uani 1 1 d . . . S4 S -0.0571(3) 0.0811(2) -0.0758(2) 0.1854(18) Uani 1 1 d . . . C1 C 0.0518(6) 0.3001(4) 0.0292(4) 0.068(2) Uani 1 1 d . . . H1A H 0.0306 0.2529 0.0218 0.081 Uiso 1 1 calc R . . C2 C 0.0018(6) 0.3411(4) 0.0821(4) 0.063(2) Uani 1 1 d . . . H2A H -0.0499 0.3210 0.1103 0.076 Uiso 1 1 calc R . . C3 C 0.0306(5) 0.4111(4) 0.0912(4) 0.0521(18) Uani 1 1 d . . . C4 C 0.1108(5) 0.4394(4) 0.0496(4) 0.0518(18) Uani 1 1 d . . . C5 C 0.1562(5) 0.3946(4) 0.0012(4) 0.0544(19) Uani 1 1 d . . . H5A H 0.2106 0.4130 -0.0258 0.065 Uiso 1 1 calc R . . C6 C 0.1502(6) 0.5148(4) 0.0587(4) 0.075(2) Uani 1 1 d . . . H6A H 0.1097 0.5389 0.0944 0.113 Uiso 1 1 calc R . . H6B H 0.1421 0.5393 0.0124 0.113 Uiso 1 1 calc R . . H6C H 0.2239 0.5143 0.0750 0.113 Uiso 1 1 calc R . . C7 C -0.1044(6) 0.4105(4) 0.2075(4) 0.0576(19) Uani 1 1 d . . . C8 C -0.2116(6) 0.4124(4) 0.2071(4) 0.064(2) Uani 1 1 d . . . C9 C -0.2594(6) 0.3657(4) 0.2571(4) 0.068(2) Uani 1 1 d . . . H9A H -0.3332 0.3666 0.2580 0.082 Uiso 1 1 calc R . . C10 C -0.1055(7) 0.3200(4) 0.2999(4) 0.077(2) Uani 1 1 d . . . H10A H -0.0686 0.2867 0.3293 0.093 Uiso 1 1 calc R . . C11 C -0.0461(6) 0.3657(5) 0.2559(4) 0.077(2) Uani 1 1 d . . . H11A H 0.0279 0.3660 0.2591 0.093 Uiso 1 1 calc R . . C12 C -0.2806(6) 0.4588(5) 0.1580(5) 0.101(3) Uani 1 1 d . . . H12A H -0.2369 0.4870 0.1275 0.151 Uiso 1 1 calc R . . H12B H -0.3220 0.4898 0.1873 0.151 Uiso 1 1 calc R . . H12C H -0.3274 0.4294 0.1276 0.151 Uiso 1 1 calc R . . C13 C 0.2861(5) 0.1167(4) -0.0267(4) 0.0526(18) Uani 1 1 d . . . H13A H 0.2484 0.0962 -0.0666 0.063 Uiso 1 1 calc R . . C14 C 0.3341(5) 0.0719(4) 0.0218(4) 0.0506(17) Uani 1 1 d . . . C15 C 0.3944(5) 0.1037(4) 0.0810(3) 0.0504(17) Uani 1 1 d . . . C16 C 0.3992(5) 0.1771(4) 0.0876(3) 0.0491(17) Uani 1 1 d . . . H16A H 0.4380 0.1988 0.1262 0.059 Uiso 1 1 calc R . . C17 C 0.3431(5) 0.2177(4) 0.0334(3) 0.0535(18) Uani 1 1 d . . . H17A H 0.3449 0.2672 0.0375 0.064 Uiso 1 1 calc R . . C18 C 0.3277(5) -0.0068(4) 0.0139(4) 0.064(2) Uani 1 1 d . . . H18A H 0.2827 -0.0185 -0.0286 0.096 Uiso 1 1 calc R . . H18B H 0.2985 -0.0270 0.0569 0.096 Uiso 1 1 calc R . . H18C H 0.3976 -0.0258 0.0082 0.096 Uiso 1 1 calc R . . C19 C 0.5243(6) 0.1036(3) 0.2088(4) 0.0514(18) Uani 1 1 d . . . C20 C 0.4660(5) 0.1368(4) 0.2616(4) 0.0529(18) Uani 1 1 d . . . C21 C 0.5255(6) 0.1780(4) 0.3152(4) 0.0573(19) Uani 1 1 d . . . H21A H 0.4883 0.2008 0.3512 0.069 Uiso 1 1 calc R . . C22 C 0.6815(5) 0.1545(4) 0.2654(4) 0.0542(18) Uani 1 1 d . . . H22A H 0.7546 0.1613 0.2647 0.065 Uiso 1 1 calc R . . C23 C 0.6325(6) 0.1117(4) 0.2118(4) 0.060(2) Uani 1 1 d . . . H23A H 0.6730 0.0884 0.1779 0.072 Uiso 1 1 calc R . . C24 C 0.3974(6) 0.3584(5) -0.0833(4) 0.070(2) Uani 1 1 d . . . C25 C 0.0286(6) 0.1430(5) -0.0930(4) 0.070(2) Uani 1 1 d . . . C26 C 0.3504(5) 0.1299(4) 0.2663(4) 0.077(2) Uani 1 1 d . . . H26A H 0.3224 0.1004 0.2268 0.116 Uiso 1 1 calc R . . H26B H 0.3181 0.1763 0.2627 0.116 Uiso 1 1 calc R . . H26C H 0.3350 0.1084 0.3124 0.116 Uiso 1 1 calc R . . C100 C 0.3502(10) 0.3731(16) 0.2343(7) 0.324(17) Uani 1 1 d . . . H10B H 0.3966 0.3611 0.2773 0.389 Uiso 1 1 calc R . . C101 C 0.6648(9) 0.2658(6) 0.9809(7) 0.139(4) Uani 1 1 d . . . H10C H 0.6145 0.3039 0.9667 0.166 Uiso 1 1 calc R . . C102 C 0.4988(12) 0.4026(8) 0.6507(7) 0.185(6) Uani 1 1 d . . . H10D H 0.4843 0.4451 0.6204 0.222 Uiso 1 1 calc R . . Cl1 Cl 0.2531(5) 0.3065(3) 0.2111(4) 0.277(3) Uani 1 1 d . . . Cl2 Cl 0.2439(3) 0.4418(2) 0.2536(2) 0.1817(16) Uani 1 1 d . . . Cl3 Cl 0.4112(4) 0.3906(5) 0.1649(4) 0.408(6) Uani 1 1 d . . . Cl4 Cl 0.6084(3) 0.1926(2) 0.9538(3) 0.1947(18) Uani 1 1 d . . . Cl5 Cl 0.6717(3) 0.2644(3) 1.0806(2) 0.230(2) Uani 1 1 d . . . Cl6 Cl 0.7818(3) 0.2953(3) 0.9610(2) 0.220(2) Uani 1 1 d . . . Cl7 Cl 0.4790(7) 0.4293(6) 0.7335(5) 0.615(4) Uani 1 1 d . . . Cl8 Cl 0.6158(2) 0.3768(2) 0.6278(2) 0.1749(16) Uani 1 1 d . . . Cl9 Cl 0.3945(3) 0.3438(2) 0.6247(3) 0.1964(19) 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 0.0523(5) 0.0569(5) 0.0394(4) 0.0040(4) -0.0031(3) -0.0066(4) N1 0.073(4) 0.050(4) 0.045(4) 0.009(3) 0.012(3) -0.008(3) N2 0.045(4) 0.076(5) 0.057(4) 0.013(3) 0.005(3) 0.007(3) N3 0.054(4) 0.056(4) 0.039(3) -0.005(3) 0.005(3) -0.007(3) N4 0.052(4) 0.052(4) 0.039(3) 0.006(3) -0.005(3) -0.004(3) N5 0.057(4) 0.074(5) 0.051(4) -0.001(3) -0.004(3) 0.002(4) N6 0.074(5) 0.066(5) 0.050(4) -0.002(3) 0.003(3) -0.009(4) S1 0.0971(15) 0.0535(12) 0.0717(13) -0.0005(12) 0.0338(11) -0.0046(12) S2 0.0982(14) 0.0527(12) 0.0556(12) -0.0005(11) -0.0200(10) 0.0029(12) S3 0.112(2) 0.0811(18) 0.181(3) -0.001(2) -0.0484(19) -0.0269(17) S4 0.184(3) 0.182(4) 0.189(4) 0.030(3) -0.003(3) -0.119(3) C1 0.093(6) 0.051(5) 0.059(5) -0.002(4) 0.009(4) -0.015(5) C2 0.077(5) 0.059(5) 0.055(5) -0.009(4) 0.021(4) -0.017(4) C3 0.053(4) 0.059(5) 0.044(4) 0.004(4) -0.003(3) -0.004(4) C4 0.057(4) 0.053(5) 0.046(4) 0.001(4) 0.002(3) 0.000(4) C5 0.055(4) 0.068(6) 0.042(4) 0.013(4) 0.008(3) -0.009(4) C6 0.110(6) 0.064(5) 0.055(5) 0.000(4) 0.028(4) -0.005(5) C7 0.064(5) 0.065(5) 0.045(4) -0.013(4) 0.018(4) -0.011(4) C8 0.068(5) 0.085(6) 0.039(4) -0.003(4) 0.001(4) -0.003(5) C9 0.058(5) 0.088(6) 0.059(5) -0.010(5) 0.009(4) 0.008(5) C10 0.081(6) 0.084(6) 0.068(5) 0.030(5) 0.007(5) -0.001(5) C11 0.051(5) 0.109(7) 0.072(5) 0.030(5) 0.007(4) -0.005(5) C12 0.076(6) 0.102(8) 0.123(8) 0.032(6) 0.004(5) 0.013(5) C13 0.054(4) 0.065(6) 0.039(4) 0.001(4) -0.002(3) -0.004(4) C14 0.050(4) 0.053(5) 0.049(4) -0.002(4) 0.003(3) -0.007(4) C15 0.059(4) 0.057(5) 0.035(4) 0.001(3) 0.004(3) -0.011(4) C16 0.066(5) 0.042(4) 0.039(4) -0.003(3) -0.005(3) -0.007(4) C17 0.082(5) 0.036(4) 0.042(4) 0.001(3) -0.005(4) -0.011(4) C18 0.074(5) 0.049(5) 0.067(5) -0.012(4) -0.010(4) -0.002(4) C19 0.066(5) 0.044(4) 0.044(4) 0.002(3) -0.003(4) 0.000(4) C20 0.056(5) 0.049(4) 0.052(4) 0.015(4) -0.004(4) -0.011(4) C21 0.055(5) 0.071(5) 0.047(4) 0.015(4) 0.003(4) 0.003(4) C22 0.057(4) 0.061(5) 0.045(4) -0.002(4) 0.006(4) 0.000(4) C23 0.071(5) 0.072(5) 0.037(4) -0.006(4) 0.009(4) -0.005(4) C24 0.056(5) 0.072(6) 0.080(6) 0.018(5) -0.005(4) -0.008(5) C25 0.056(5) 0.083(6) 0.071(6) -0.007(5) -0.002(4) -0.017(5) C26 0.066(5) 0.081(6) 0.084(6) -0.003(5) 0.005(4) -0.018(5) C100 0.098(10) 0.78(5) 0.089(10) -0.051(18) -0.009(8) -0.062(19) C101 0.115(8) 0.122(10) 0.176(12) 0.016(9) -0.027(7) -0.029(7) C102 0.243(16) 0.178(13) 0.144(11) -0.029(10) 0.117(11) -0.055(12) Cl1 0.289(6) 0.195(5) 0.356(8) -0.081(5) 0.102(6) -0.026(5) Cl2 0.168(3) 0.150(3) 0.225(4) -0.004(3) -0.007(3) 0.062(3) Cl3 0.221(5) 0.612(15) 0.404(9) -0.281(10) 0.150(6) -0.214(7) Cl4 0.180(3) 0.119(3) 0.284(6) -0.024(3) -0.001(3) -0.019(3) Cl5 0.188(4) 0.342(7) 0.159(4) 0.053(4) 0.006(3) 0.009(4) Cl6 0.169(3) 0.282(5) 0.209(4) 0.077(4) 0.007(3) -0.097(4) Cl7 0.605(9) 0.714(10) 0.573(11) -0.512(8) 0.478(8) -0.507 Cl8 0.097(2) 0.248(5) 0.180(3) -0.021(3) 0.012(2) -0.005(2) Cl9 0.134(3) 0.192(4) 0.269(5) -0.068(4) 0.068(3) -0.041(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 Cu1 N6 1.969(7) . ? Cu1 N5 1.971(7) . ? Cu1 N3 2.070(5) . ? Cu1 N4 2.084(5) 4_565 ? Cu1 N1 2.438(6) . ? N1 C5 1.336(8) . ? N1 C1 1.333(8) . ? N2 C10 1.298(8) . ? N2 C9 1.307(9) . ? N3 C17 1.332(7) . ? N3 C13 1.355(8) . ? N4 C22 1.318(7) . ? N4 C21 1.316(7) . ? N4 Cu1 2.084(5) 4_666 ? N5 C24 1.173(8) . ? N6 C25 1.116(8) . ? S1 C3 1.764(7) . ? S1 C7 1.795(7) . ? S2 C19 1.763(7) . ? S2 C15 1.773(7) . ? S3 C24 1.585(9) . ? S4 C25 1.625(9) . ? C1 C2 1.406(9) . ? C2 C3 1.368(9) . ? C3 C4 1.398(9) . ? C4 C5 1.363(9) . ? C4 C6 1.502(9) . ? C7 C8 1.350(9) . ? C7 C11 1.398(10) . ? C8 C9 1.419(10) . ? C8 C12 1.492(10) . ? C10 C11 1.413(10) . ? C13 C14 1.340(9) . ? C14 C15 1.417(9) . ? C14 C18 1.481(9) . ? C15 C16 1.380(8) . ? C16 C17 1.406(9) . ? C19 C23 1.368(9) . ? C19 C20 1.388(9) . ? C20 C21 1.426(9) . ? C20 C26 1.467(9) . ? C22 C23 1.382(9) . ? C100 Cl3 1.549(15) . ? C100 Cl1 1.78(2) . ? C100 Cl2 1.90(2) . ? C101 Cl4 1.608(11) . ? C101 Cl6 1.632(11) . ? C101 Cl5 1.815(13) . ? C102 Cl7 1.621(13) . ? C102 Cl8 1.624(13) . ? C102 Cl9 1.760(14) . ? 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 N6 Cu1 N5 178.7(2) . . ? N6 Cu1 N3 90.0(2) . . ? N5 Cu1 N3 90.8(2) . . ? N6 Cu1 N4 89.4(2) . 4_565 ? N5 Cu1 N4 89.8(2) . 4_565 ? N3 Cu1 N4 179.2(2) . 4_565 ? N6 Cu1 N1 90.7(2) . . ? N5 Cu1 N1 90.3(2) . . ? N3 Cu1 N1 92.8(2) . . ? N4 Cu1 N1 87.82(19) 4_565 . ? C5 N1 C1 117.1(6) . . ? C5 N1 Cu1 122.9(5) . . ? C1 N1 Cu1 120.0(5) . . ? C10 N2 C9 117.1(6) . . ? C17 N3 C13 116.2(6) . . ? C17 N3 Cu1 121.6(5) . . ? C13 N3 Cu1 122.2(4) . . ? C22 N4 C21 117.2(6) . . ? C22 N4 Cu1 121.1(5) . 4_666 ? C21 N4 Cu1 121.7(5) . 4_666 ? C24 N5 Cu1 160.7(6) . . ? C25 N6 Cu1 165.8(7) . . ? C3 S1 C7 102.9(3) . . ? C19 S2 C15 103.4(3) . . ? N1 C1 C2 122.3(7) . . ? C3 C2 C1 118.8(7) . . ? C2 C3 C4 119.4(7) . . ? C2 C3 S1 123.2(5) . . ? C4 C3 S1 117.4(6) . . ? C5 C4 C3 117.2(6) . . ? C5 C4 C6 120.1(6) . . ? C3 C4 C6 122.6(7) . . ? N1 C5 C4 125.2(6) . . ? C8 C7 C11 120.7(7) . . ? C8 C7 S1 120.8(6) . . ? C11 C7 S1 118.3(6) . . ? C7 C8 C9 115.9(7) . . ? C7 C8 C12 124.7(8) . . ? C9 C8 C12 119.4(7) . . ? N2 C9 C8 125.5(7) . . ? N2 C10 C11 124.1(7) . . ? C7 C11 C10 116.5(7) . . ? C14 C13 N3 126.3(6) . . ? C13 C14 C15 116.4(6) . . ? C13 C14 C18 122.5(6) . . ? C15 C14 C18 121.1(6) . . ? C16 C15 C14 120.2(6) . . ? C16 C15 S2 122.8(5) . . ? C14 C15 S2 117.0(5) . . ? C15 C16 C17 117.3(6) . . ? N3 C17 C16 123.6(6) . . ? C23 C19 C20 119.0(6) . . ? C23 C19 S2 119.5(6) . . ? C20 C19 S2 121.2(6) . . ? C19 C20 C21 116.0(6) . . ? C19 C20 C26 124.2(7) . . ? C21 C20 C26 119.7(7) . . ? N4 C21 C20 124.7(7) . . ? N4 C22 C23 123.1(6) . . ? C19 C23 C22 119.9(6) . . ? N5 C24 S3 175.9(8) . . ? N6 C25 S4 178.5(8) . . ? Cl3 C100 Cl1 108.5(10) . . ? Cl3 C100 Cl2 113.1(16) . . ? Cl1 C100 Cl2 92.1(6) . . ? Cl4 C101 Cl6 127.6(9) . . ? Cl4 C101 Cl5 107.0(7) . . ? Cl6 C101 Cl5 103.4(6) . . ? Cl7 C102 Cl8 121.1(11) . . ? Cl7 C102 Cl9 107.2(6) . . ? Cl8 C102 Cl9 114.7(8) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.434 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.077