# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_8691 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 Br2 Cu2 N2 S2' _chemical_formula_weight 637.38 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' 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' Br Br -0.2901 2.4595 '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 7.8242(10) _cell_length_b 8.0124(11) _cell_length_c 9.5144(12) _cell_angle_alpha 94.764(3) _cell_angle_beta 95.869(3) _cell_angle_gamma 110.659(2) _cell_volume 550.62(12) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1366 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description Block _exptl_crystal_colour Pink _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.922 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 5.758 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2770 _exptl_absorpt_correction_T_max 0.8024 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 3800 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2512 _reflns_number_gt 1917 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0808P)^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 2512 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1375 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.51494(10) 0.09625(9) 0.16914(7) 0.0796(3) Uani 1 1 d . . . Br1 Br 0.29962(6) -0.17652(6) 0.06419(5) 0.0587(2) Uani 1 1 d . . . S1 S 0.70354(18) 0.24215(16) 0.48821(13) 0.0615(3) Uani 1 1 d . . . N1 N 0.6459(4) 0.4543(4) 0.3288(3) 0.0441(7) Uani 1 1 d . . . C1 C 0.6208(6) 0.2807(6) 0.3238(4) 0.0520(10) Uani 1 1 d . . . C2 C 0.7317(5) 0.5650(5) 0.4583(4) 0.0420(8) Uani 1 1 d . . . C3 C 0.7687(6) 0.7476(6) 0.4891(4) 0.0522(10) Uani 1 1 d . . . H3 H 0.7377 0.8127 0.4209 0.063 Uiso 1 1 calc R . . C4 C 0.8535(7) 0.8297(7) 0.6251(5) 0.0616(12) Uani 1 1 d . . . H4 H 0.8809 0.9522 0.6487 0.074 Uiso 1 1 calc R . . C5 C 0.8981(6) 0.7304(8) 0.7269(5) 0.0671(13) Uani 1 1 d . . . H5 H 0.9560 0.7889 0.8170 0.081 Uiso 1 1 calc R . . C6 C 0.8595(6) 0.5497(7) 0.6981(4) 0.0631(13) Uani 1 1 d . . . H6 H 0.8894 0.4851 0.7672 0.076 Uiso 1 1 calc R . . C7 C 0.7731(5) 0.4653(6) 0.5611(4) 0.0460(9) Uani 1 1 d . . . C8 C 0.5947(5) 0.5308(6) 0.2015(4) 0.0503(10) Uani 1 1 d . . . H8A H 0.5309 0.6101 0.2283 0.060 Uiso 1 1 calc R . . H8B H 0.5112 0.4343 0.1312 0.060 Uiso 1 1 calc R . . C9 C 0.7611(6) 0.6331(6) 0.1380(4) 0.0520(10) Uani 1 1 d . . . H9 H 0.8361 0.5717 0.1111 0.062 Uiso 1 1 calc R . . C10 C 0.8098(7) 0.7995(7) 0.1170(5) 0.0619(11) Uani 1 1 d . . . H10A H 0.7386 0.8658 0.1423 0.074 Uiso 1 1 calc R . . H10B H 0.9161 0.8532 0.0766 0.074 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 0.0911(5) 0.0553(4) 0.0861(5) -0.0156(3) -0.0197(4) 0.0333(4) Br1 0.0625(3) 0.0447(3) 0.0627(3) 0.0090(2) 0.0122(2) 0.0106(2) S1 0.0693(7) 0.0509(7) 0.0665(7) 0.0216(5) 0.0097(5) 0.0214(6) N1 0.0456(17) 0.0422(19) 0.0401(16) 0.0073(13) 0.0034(13) 0.0108(14) C1 0.055(2) 0.050(3) 0.053(2) 0.0065(18) 0.0063(18) 0.021(2) C2 0.0378(19) 0.050(2) 0.0380(18) 0.0091(15) 0.0032(14) 0.0152(16) C3 0.058(2) 0.051(3) 0.045(2) 0.0068(18) 0.0056(18) 0.018(2) C4 0.067(3) 0.057(3) 0.054(2) 0.000(2) 0.006(2) 0.016(2) C5 0.064(3) 0.084(4) 0.041(2) 0.002(2) 0.002(2) 0.014(3) C6 0.055(3) 0.084(4) 0.045(2) 0.023(2) 0.0053(19) 0.015(2) C7 0.0393(19) 0.056(3) 0.046(2) 0.0191(17) 0.0098(15) 0.0174(18) C8 0.050(2) 0.056(3) 0.042(2) 0.0111(17) -0.0059(16) 0.0172(19) C9 0.062(3) 0.055(3) 0.040(2) 0.0094(17) 0.0076(17) 0.022(2) C10 0.065(3) 0.067(3) 0.058(3) 0.018(2) 0.010(2) 0.027(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 Cu1 C1 1.887(4) . ? Cu1 Br1 2.3037(8) . ? Cu1 Br1 2.7721(10) 2_655 ? Br1 Cu1 2.7720(10) 2_655 ? S1 C1 1.725(4) . ? S1 C7 1.733(4) . ? N1 C1 1.331(5) . ? N1 C2 1.408(5) . ? N1 C8 1.483(5) . ? C2 C3 1.387(6) . ? C2 C7 1.395(5) . ? C3 C4 1.386(6) . ? C4 C5 1.396(7) . ? C5 C6 1.367(7) . ? C6 C7 1.402(6) . ? C8 C9 1.490(6) . ? C9 C10 1.290(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 C1 Cu1 Br1 152.31(14) . . ? C1 Cu1 Br1 111.25(14) . 2_655 ? Br1 Cu1 Br1 96.44(3) . 2_655 ? Cu1 Br1 Cu1 83.56(3) . 2_655 ? C1 S1 C7 93.61(19) . . ? C1 N1 C2 117.3(3) . . ? C1 N1 C8 121.6(3) . . ? C2 N1 C8 121.0(3) . . ? N1 C1 S1 108.8(3) . . ? N1 C1 Cu1 128.7(3) . . ? S1 C1 Cu1 122.5(2) . . ? C3 C2 C7 121.5(3) . . ? C3 C2 N1 127.4(3) . . ? C7 C2 N1 111.0(4) . . ? C4 C3 C2 117.6(4) . . ? C3 C4 C5 120.7(5) . . ? C6 C5 C4 122.1(4) . . ? C5 C6 C7 117.7(4) . . ? C2 C7 C6 120.3(4) . . ? C2 C7 S1 109.3(3) . . ? C6 C7 S1 130.3(3) . . ? N1 C8 C9 111.1(3) . . ? C10 C9 C8 125.5(4) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.701 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.133 _database_code_depnum_ccdc_archive 'CCDC 952963' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9086 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H44 Br4 Cu4 N4 S4' _chemical_formula_weight 1282.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Br Br -0.2901 2.4595 '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 9.5728(7) _cell_length_b 10.8961(8) _cell_length_c 11.5350(8) _cell_angle_alpha 75.9430(10) _cell_angle_beta 89.9310(10) _cell_angle_gamma 74.7520(10) _cell_volume 1123.53(14) _cell_formula_units_Z 1 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 6015 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.46 _exptl_crystal_description Plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.896 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 5.644 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.0099 _exptl_absorpt_correction_T_max 0.4549 _exptl_absorpt_process_details 'Sadabs. (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 14572 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5150 _reflns_number_gt 4229 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.0199P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5150 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.12046(4) 1.21133(3) 0.09682(3) 0.04821(11) Uani 1 1 d . . . Cu2 Cu -0.01828(5) 0.95569(3) 0.14631(4) 0.05968(13) Uani 1 1 d . . . S1 S 0.18068(7) 1.49737(6) 0.02183(6) 0.04091(16) Uani 1 1 d . . . S2 S -0.05805(9) 0.66546(7) 0.21704(7) 0.05144(19) Uani 1 1 d . . . Br1 Br -0.08431(3) 1.16653(3) 0.20249(3) 0.04820(10) Uani 1 1 d . . . Br2 Br 0.20694(3) 1.01175(3) 0.02608(2) 0.04272(9) Uani 1 1 d . . . N1 N 0.3470(2) 1.31080(19) 0.17013(19) 0.0359(4) Uani 1 1 d . . . N2 N 0.1423(2) 0.7137(2) 0.31970(19) 0.0408(5) Uani 1 1 d . . . C1 C 0.2261(3) 1.3356(2) 0.1006(2) 0.0371(5) Uani 1 1 d . . . C2 C 0.4072(3) 1.4161(2) 0.1651(2) 0.0367(5) Uani 1 1 d . . . C3 C 0.5320(3) 1.4148(3) 0.2281(3) 0.0481(6) Uani 1 1 d . . . H3 H 0.5886 1.3378 0.2791 0.058 Uiso 1 1 calc R . . C4 C 0.5683(4) 1.5307(3) 0.2122(3) 0.0578(8) Uani 1 1 d . . . H4 H 0.6510 1.5322 0.2533 0.069 Uiso 1 1 calc R . . C5 C 0.4851(4) 1.6462(3) 0.1364(3) 0.0555(8) Uani 1 1 d . . . H5 H 0.5120 1.7237 0.1291 0.067 Uiso 1 1 calc R . . C6 C 0.3638(3) 1.6482(3) 0.0722(3) 0.0480(7) Uani 1 1 d . . . H6 H 0.3088 1.7251 0.0201 0.058 Uiso 1 1 calc R . . C7 C 0.3261(3) 1.5301(2) 0.0879(2) 0.0365(5) Uani 1 1 d . . . C8 C 0.4112(3) 1.1772(2) 0.2460(2) 0.0441(6) Uani 1 1 d . . . H8A H 0.3353 1.1330 0.2652 0.053 Uiso 1 1 calc R . . H8B H 0.4522 1.1834 0.3205 0.053 Uiso 1 1 calc R . . C9 C 0.5277(3) 1.0962(3) 0.1867(3) 0.0503(7) Uani 1 1 d . . . H9A H 0.6101 1.1330 0.1777 0.060 Uiso 1 1 calc R . . H9B H 0.4909 1.0992 0.1074 0.060 Uiso 1 1 calc R . . C10 C 0.5764(4) 0.9542(3) 0.2599(3) 0.0636(9) Uani 1 1 d . . . H10A H 0.5995 0.9518 0.3415 0.095 Uiso 1 1 calc R . . H10B H 0.6607 0.9080 0.2274 0.095 Uiso 1 1 calc R . . H10C H 0.4997 0.9130 0.2569 0.095 Uiso 1 1 calc R . . C11 C 0.0321(3) 0.7768(3) 0.2373(2) 0.0432(6) Uani 1 1 d . . . C12 C 0.1605(3) 0.5795(2) 0.3704(2) 0.0444(6) Uani 1 1 d . . . C13 C 0.2642(4) 0.4961(3) 0.4578(3) 0.0606(8) Uani 1 1 d . . . H13 H 0.3336 0.5263 0.4902 0.073 Uiso 1 1 calc R . . C14 C 0.2614(5) 0.3671(3) 0.4953(4) 0.0761(11) Uani 1 1 d . . . H14 H 0.3298 0.3094 0.5544 0.091 Uiso 1 1 calc R . . C15 C 0.1602(5) 0.3213(3) 0.4477(4) 0.0811(13) Uani 1 1 d . . . H15 H 0.1615 0.2333 0.4748 0.097 Uiso 1 1 calc R . . C16 C 0.0553(4) 0.4043(3) 0.3594(3) 0.0671(10) Uani 1 1 d . . . H16 H -0.0128 0.3727 0.3269 0.080 Uiso 1 1 calc R . . C17 C 0.0550(3) 0.5361(3) 0.3211(3) 0.0467(6) Uani 1 1 d . . . C18 C 0.2348(3) 0.7866(3) 0.3576(3) 0.0520(7) Uani 1 1 d . . . H18A H 0.2366 0.8615 0.2925 0.062 Uiso 1 1 calc R . . H18B H 0.3332 0.7303 0.3760 0.062 Uiso 1 1 calc R . . C19 C 0.1800(4) 0.8342(4) 0.4674(3) 0.0682(10) Uani 1 1 d . . . H19A H 0.0783 0.8824 0.4519 0.082 Uiso 1 1 calc R . . H19B H 0.1879 0.7589 0.5348 0.082 Uiso 1 1 calc R . . C20 C 0.2642(5) 0.9208(4) 0.4989(3) 0.0872(13) Uani 1 1 d . . . H20A H 0.3638 0.8717 0.5191 0.131 Uiso 1 1 calc R . . H20B H 0.2243 0.9520 0.5661 0.131 Uiso 1 1 calc R . . H20C H 0.2586 0.9943 0.4316 0.131 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 0.0506(2) 0.03852(19) 0.0574(2) -0.00626(16) -0.00409(17) -0.02057(16) Cu2 0.0752(3) 0.0370(2) 0.0588(3) 0.00040(17) -0.0056(2) -0.01294(18) S1 0.0373(3) 0.0317(3) 0.0508(4) -0.0069(3) -0.0016(3) -0.0075(3) S2 0.0598(4) 0.0470(4) 0.0528(4) -0.0162(3) 0.0021(4) -0.0202(3) Br1 0.04987(17) 0.04612(17) 0.05793(19) -0.02292(14) 0.01434(13) -0.01993(13) Br2 0.04547(16) 0.04014(16) 0.04467(16) -0.01426(12) 0.00281(12) -0.01191(12) N1 0.0370(11) 0.0274(10) 0.0416(12) -0.0051(9) 0.0047(9) -0.0089(8) N2 0.0509(13) 0.0344(11) 0.0364(12) -0.0057(9) 0.0016(10) -0.0137(10) C1 0.0355(13) 0.0343(13) 0.0423(14) -0.0100(11) 0.0075(11) -0.0104(10) C2 0.0408(13) 0.0354(13) 0.0368(13) -0.0117(10) 0.0071(11) -0.0128(10) C3 0.0471(15) 0.0508(16) 0.0446(16) -0.0077(13) -0.0023(12) -0.0142(13) C4 0.0593(18) 0.073(2) 0.0568(19) -0.0245(17) 0.0031(15) -0.0365(17) C5 0.0680(19) 0.0505(17) 0.063(2) -0.0234(15) 0.0103(16) -0.0333(16) C6 0.0591(17) 0.0355(14) 0.0537(17) -0.0141(12) 0.0096(14) -0.0175(13) C7 0.0380(13) 0.0320(12) 0.0417(14) -0.0121(11) 0.0068(11) -0.0106(10) C8 0.0506(15) 0.0344(13) 0.0424(15) -0.0009(11) 0.0023(12) -0.0113(12) C9 0.0450(15) 0.0387(15) 0.0600(18) -0.0035(13) 0.0058(13) -0.0072(12) C10 0.062(2) 0.0362(16) 0.082(2) -0.0044(15) 0.0054(17) -0.0056(14) C11 0.0547(16) 0.0374(14) 0.0372(14) -0.0083(11) 0.0052(12) -0.0128(12) C12 0.0573(16) 0.0334(13) 0.0396(15) -0.0097(11) 0.0129(13) -0.0070(12) C13 0.0631(19) 0.0542(18) 0.0478(18) -0.0004(14) 0.0044(15) 0.0013(15) C14 0.091(3) 0.0438(19) 0.068(2) 0.0064(16) 0.020(2) 0.0057(19) C15 0.116(3) 0.0307(16) 0.086(3) -0.0066(17) 0.045(3) -0.0094(19) C16 0.097(3) 0.0409(17) 0.073(2) -0.0217(16) 0.033(2) -0.0286(18) C17 0.0613(17) 0.0348(13) 0.0468(16) -0.0146(12) 0.0188(13) -0.0141(12) C18 0.0630(18) 0.0528(17) 0.0422(16) -0.0051(13) -0.0008(14) -0.0255(15) C19 0.092(3) 0.082(2) 0.0479(18) -0.0185(17) 0.0072(17) -0.050(2) C20 0.131(4) 0.096(3) 0.062(2) -0.025(2) 0.015(2) -0.073(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 C1 1.900(2) . ? Cu1 Br1 2.4030(5) . ? Cu1 Br2 2.4482(5) . ? Cu2 C11 1.910(3) . ? Cu2 Br1 2.4608(5) . ? Cu2 Br2 2.5828(5) 2_575 ? Cu2 Br2 2.6867(5) . ? S1 C1 1.715(3) . ? S1 C7 1.744(3) . ? S2 C11 1.720(3) . ? S2 C17 1.725(3) . ? Br2 Cu2 2.5827(5) 2_575 ? N1 C1 1.337(3) . ? N1 C2 1.402(3) . ? N1 C8 1.475(3) . ? N2 C11 1.339(3) . ? N2 C12 1.401(3) . ? N2 C18 1.465(3) . ? C2 C7 1.378(4) . ? C2 C3 1.394(4) . ? C3 C4 1.367(4) . ? C4 C5 1.386(4) . ? C5 C6 1.371(4) . ? C6 C7 1.396(4) . ? C8 C9 1.504(4) . ? C9 C10 1.520(4) . ? C12 C13 1.382(4) . ? C12 C17 1.397(4) . ? C13 C14 1.374(5) . ? C14 C15 1.370(6) . ? C15 C16 1.393(6) . ? C16 C17 1.396(4) . ? C18 C19 1.525(4) . ? C19 C20 1.497(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 C1 Cu1 Br1 131.45(8) . . ? C1 Cu1 Br2 125.78(7) . . ? Br1 Cu1 Br2 100.629(14) . . ? C11 Cu2 Br1 133.08(8) . . ? C11 Cu2 Br2 109.53(8) . 2_575 ? Br1 Cu2 Br2 103.985(17) . 2_575 ? C11 Cu2 Br2 110.78(9) . . ? Br1 Cu2 Br2 92.878(15) . . ? Br2 Cu2 Br2 101.850(17) 2_575 . ? C1 S1 C7 93.47(12) . . ? C11 S2 C17 93.78(13) . . ? Cu1 Br1 Cu2 86.072(16) . . ? Cu1 Br2 Cu2 103.219(16) . 2_575 ? Cu1 Br2 Cu2 80.407(14) . . ? Cu2 Br2 Cu2 78.150(17) 2_575 . ? C1 N1 C2 116.8(2) . . ? C1 N1 C8 119.8(2) . . ? C2 N1 C8 123.3(2) . . ? C11 N2 C12 117.8(2) . . ? C11 N2 C18 119.9(2) . . ? C12 N2 C18 122.3(2) . . ? N1 C1 S1 108.84(17) . . ? N1 C1 Cu1 124.56(18) . . ? S1 C1 Cu1 126.55(15) . . ? C7 C2 C3 120.6(2) . . ? C7 C2 N1 111.8(2) . . ? C3 C2 N1 127.6(2) . . ? C4 C3 C2 117.6(3) . . ? C3 C4 C5 121.9(3) . . ? C6 C5 C4 121.1(3) . . ? C5 C6 C7 117.4(3) . . ? C2 C7 C6 121.4(2) . . ? C2 C7 S1 109.03(18) . . ? C6 C7 S1 129.6(2) . . ? N1 C8 C9 112.7(2) . . ? C8 C9 C10 111.1(3) . . ? N2 C11 S2 108.26(18) . . ? N2 C11 Cu2 128.6(2) . . ? S2 C11 Cu2 123.08(16) . . ? C13 C12 C17 121.9(3) . . ? C13 C12 N2 127.6(3) . . ? C17 C12 N2 110.4(2) . . ? C14 C13 C12 117.8(4) . . ? C15 C14 C13 121.6(4) . . ? C14 C15 C16 121.2(3) . . ? C15 C16 C17 118.3(4) . . ? C16 C17 C12 119.2(3) . . ? C16 C17 S2 131.0(3) . . ? C12 C17 S2 109.78(19) . . ? N2 C18 C19 111.3(2) . . ? C20 C19 C18 111.7(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.403 _refine_diff_density_min -0.702 _refine_diff_density_rms 0.124 _database_code_depnum_ccdc_archive 'CCDC 952964' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9211 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H44 Br4 Cu4 N4 S4' _chemical_formula_weight 1330.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1913(8) _cell_length_b 15.8654(11) _cell_length_c 13.3763(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.003(2) _cell_angle_gamma 90.00 _cell_volume 2371.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2658 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 22.40 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Neasured' _exptl_crystal_density_diffrn 1.864 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 5.351 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2234 _exptl_absorpt_correction_T_max 0.6167 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 16738 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5430 _reflns_number_gt 3603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Three terminal C atoms of the two but-2-ene groups were disordered into two positions with occupancy ratio 85:15 and 83:17 respectively. Alert B "Large Non-Solvent C" is due to the disorder of the terminal carbons. ; _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^)+(0.0591P)^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 5430 _refine_ls_number_parameters 294 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.979 _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 0.24393(5) 0.93634(4) 0.39036(5) 0.05409(19) Uani 1 1 d . . . Cu2 Cu 0.50592(6) 0.89094(4) 0.49214(5) 0.0678(2) Uani 1 1 d . . . Br1 Br 0.30595(4) 0.85068(3) 0.53539(4) 0.05037(15) Uani 1 1 d . . . Br2 Br 0.43183(4) 1.00222(3) 0.35547(4) 0.04847(15) Uani 1 1 d . . . S1 S -0.02557(11) 0.99753(7) 0.36949(8) 0.0444(3) Uani 1 1 d . . . S2 S 0.78092(10) 0.85374(7) 0.53942(9) 0.0482(3) Uani 1 1 d . . . N1 N 0.0462(3) 0.8915(2) 0.2482(3) 0.0412(8) Uani 1 1 d . A . N2 N 0.6793(3) 0.7847(2) 0.3919(3) 0.0486(9) Uani 1 1 d . B . C1 C 0.0878(4) 0.9366(3) 0.3270(3) 0.0426(10) Uani 1 1 d . . . C2 C -0.0753(4) 0.9019(3) 0.2189(3) 0.0406(10) Uani 1 1 d . . . C3 C -0.1408(5) 0.8632(3) 0.1408(3) 0.0517(12) Uani 1 1 d . . . H3 H -0.1045 0.8248 0.0983 0.062 Uiso 1 1 calc R . . C4 C -0.2588(5) 0.8824(4) 0.1276(4) 0.0649(15) Uani 1 1 d . . . H4 H -0.3042 0.8568 0.0748 0.078 Uiso 1 1 calc R . . C5 C -0.3146(4) 0.9387(3) 0.1898(4) 0.0582(13) Uani 1 1 d . . . H5 H -0.3967 0.9498 0.1788 0.070 Uiso 1 1 calc R . . C6 C -0.2517(4) 0.9778(3) 0.2665(4) 0.0494(11) Uani 1 1 d . . . H6 H -0.2892 1.0155 0.3091 0.059 Uiso 1 1 calc R . . C7 C -0.1304(4) 0.9602(3) 0.2797(3) 0.0388(10) Uani 1 1 d . . . C12 C 0.6533(4) 0.8362(3) 0.4658(4) 0.0509(12) Uani 1 1 d . . . C13 C 0.7982(4) 0.7565(3) 0.3888(3) 0.0448(11) Uani 1 1 d . . . C14 C 0.8474(5) 0.7029(3) 0.3195(4) 0.0557(12) Uani 1 1 d . . . H14 H 0.7995 0.6798 0.2665 0.067 Uiso 1 1 calc R . . C15 C 0.9666(5) 0.6847(3) 0.3298(4) 0.0609(14) Uani 1 1 d . . . H15 H 1.0007 0.6480 0.2841 0.073 Uiso 1 1 calc R . . C16 C 1.0388(5) 0.7200(3) 0.4077(4) 0.0605(14) Uani 1 1 d . . . H16 H 1.1209 0.7074 0.4130 0.073 Uiso 1 1 calc R . . C17 C 0.9903(4) 0.7732(3) 0.4767(4) 0.0517(12) Uani 1 1 d . . . H17 H 1.0385 0.7972 0.5289 0.062 Uiso 1 1 calc R . . C18 C 0.8690(4) 0.7899(2) 0.4669(3) 0.0407(10) Uani 1 1 d . . . C8 C 0.1221(4) 0.8330(3) 0.1952(4) 0.0583(13) Uani 1 1 d D . . H8A H 0.0731 0.7865 0.1675 0.070 Uiso 0.833(10) 1 calc PR A 1 H8B H 0.1828 0.8091 0.2425 0.070 Uiso 0.833(10) 1 calc PR A 1 H8C H 0.0897 0.7756 0.1976 0.070 Uiso 0.167(10) 1 d PR A 2 H8D H 0.2034 0.8327 0.2262 0.070 Uiso 0.167(10) 1 d PR A 2 C19 C 0.5898(5) 0.7620(3) 0.3125(4) 0.0751(17) Uani 1 1 d D . . H19A H 0.6284 0.7596 0.2485 0.090 Uiso 0.851(12) 1 calc PR B 1 H19B H 0.5285 0.8062 0.3073 0.090 Uiso 0.851(12) 1 calc PR B 1 H19C H 0.6168 0.7717 0.2450 0.090 Uiso 0.149(12) 1 d PR B 2 H19D H 0.5117 0.7885 0.3205 0.090 Uiso 0.149(12) 1 d PR B 2 C9 C 0.1821(5) 0.8762(4) 0.1127(4) 0.0579(19) Uani 0.833(10) 1 d PD A 1 H9A H 0.1364 0.8923 0.0549 0.069 Uiso 0.833(10) 1 calc PR A 1 C10 C 0.3002(5) 0.8927(4) 0.1191(5) 0.066(2) Uani 0.833(10) 1 d PD A 1 H10A H 0.3456 0.8719 0.1749 0.079 Uiso 0.833(10) 1 calc PR A 1 C11 C 0.3623(6) 0.9414(4) 0.0438(5) 0.074(2) Uani 0.833(10) 1 d PD A 1 H11A H 0.3972 0.9916 0.0746 0.110 Uiso 0.833(10) 1 calc PR A 1 H11B H 0.3056 0.9575 -0.0102 0.110 Uiso 0.833(10) 1 calc PR A 1 H11C H 0.4251 0.9071 0.0172 0.110 Uiso 0.833(10) 1 calc PR A 1 C9A C 0.124(2) 0.863(2) 0.0891(10) 0.105(19) Uiso 0.167(10) 1 d PD A 2 H9AA H 0.0550 0.8537 0.0469 0.126 Uiso 0.167(10) 1 calc PR A 2 C10A C 0.217(3) 0.9010(19) 0.0511(15) 0.089(12) Uiso 0.167(10) 1 d PD A 2 H10B H 0.2112 0.9170 -0.0166 0.107 Uiso 0.167(10) 1 calc PR A 2 C11A C 0.331(3) 0.920(3) 0.110(3) 0.089(12) Uiso 0.167(10) 1 d PD A 2 H11D H 0.3983 0.9066 0.0701 0.134 Uiso 0.167(10) 1 calc PR A 2 H11E H 0.3350 0.8862 0.1705 0.134 Uiso 0.167(10) 1 calc PR A 2 H11F H 0.3330 0.9792 0.1275 0.134 Uiso 0.167(10) 1 calc PR A 2 C20 C 0.5311(5) 0.6798(4) 0.3305(5) 0.065(2) Uani 0.851(12) 1 d PD B 1 H20A H 0.5774 0.6305 0.3365 0.078 Uiso 0.851(12) 1 calc PR B 1 C21 C 0.4119(5) 0.6757(4) 0.3382(8) 0.081(3) Uani 0.851(12) 1 d PD B 1 H21A H 0.3671 0.7258 0.3338 0.097 Uiso 0.851(12) 1 calc PR B 1 C22 C 0.3491(6) 0.5956(4) 0.3533(5) 0.090(3) Uani 0.851(12) 1 d PD B 1 H22A H 0.3000 0.6006 0.4107 0.135 Uiso 0.851(12) 1 calc PR B 1 H22B H 0.4072 0.5509 0.3651 0.135 Uiso 0.851(12) 1 calc PR B 1 H22C H 0.2987 0.5826 0.2941 0.135 Uiso 0.851(12) 1 calc PR B 1 C20A C 0.594(3) 0.6712(11) 0.342(5) 0.16(2) Uiso 0.149(12) 1 d PD B 2 H20B H 0.6683 0.6442 0.3522 0.187 Uiso 0.149(12) 1 calc PR B 2 C21A C 0.493(5) 0.6274(19) 0.355(4) 0.16(2) Uiso 0.149(12) 1 d PD B 2 H21B H 0.4985 0.5712 0.3766 0.187 Uiso 0.149(12) 1 calc PR B 2 C22A C 0.373(4) 0.666(4) 0.334(8) 0.16(2) Uiso 0.149(12) 1 d PD B 2 H22D H 0.3158 0.6231 0.3136 0.234 Uiso 0.149(12) 1 calc PR B 2 H22E H 0.3775 0.7081 0.2817 0.234 Uiso 0.149(12) 1 calc PR B 2 H22F H 0.3474 0.6934 0.3948 0.234 Uiso 0.149(12) 1 calc PR B 2 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 0.0405(4) 0.0630(4) 0.0579(4) -0.0007(3) -0.0052(3) 0.0020(3) Cu2 0.0395(4) 0.0792(5) 0.0850(5) 0.0014(3) 0.0063(3) 0.0102(3) Br1 0.0405(3) 0.0584(3) 0.0521(3) 0.0105(2) 0.0005(2) -0.0054(2) Br2 0.0407(3) 0.0583(3) 0.0466(3) 0.0040(2) 0.0043(2) -0.0024(2) S1 0.0447(7) 0.0512(6) 0.0370(6) -0.0042(5) -0.0005(5) -0.0032(5) S2 0.0378(7) 0.0500(6) 0.0569(8) -0.0095(5) 0.0027(5) 0.0006(5) N1 0.037(2) 0.046(2) 0.041(2) 0.0029(16) 0.0054(17) -0.0001(15) N2 0.043(2) 0.056(2) 0.046(2) -0.0039(18) -0.0029(18) -0.0070(17) C1 0.040(3) 0.046(2) 0.041(3) 0.0058(19) -0.001(2) -0.0023(19) C2 0.043(3) 0.043(2) 0.037(2) -0.0001(18) 0.005(2) -0.0065(18) C3 0.057(3) 0.056(3) 0.043(3) -0.014(2) 0.007(2) -0.012(2) C4 0.055(4) 0.092(4) 0.046(3) -0.009(3) -0.004(3) -0.021(3) C5 0.035(3) 0.084(4) 0.055(3) -0.001(3) -0.002(2) -0.002(2) C6 0.043(3) 0.055(3) 0.050(3) 0.001(2) 0.006(2) 0.000(2) C7 0.041(3) 0.043(2) 0.033(2) 0.0025(18) 0.0027(19) -0.0064(18) C12 0.039(3) 0.046(3) 0.067(3) 0.005(2) -0.003(2) -0.0030(19) C13 0.047(3) 0.044(2) 0.044(3) 0.002(2) 0.010(2) -0.007(2) C14 0.063(4) 0.055(3) 0.050(3) -0.005(2) 0.013(3) -0.011(2) C15 0.070(4) 0.054(3) 0.061(3) 0.002(2) 0.029(3) 0.005(3) C16 0.050(3) 0.058(3) 0.075(4) 0.012(3) 0.018(3) 0.008(2) C17 0.042(3) 0.053(3) 0.060(3) 0.001(2) 0.004(2) -0.006(2) C18 0.037(2) 0.039(2) 0.047(3) 0.0006(19) 0.006(2) -0.0046(18) C8 0.052(3) 0.059(3) 0.065(3) -0.002(2) 0.014(3) 0.006(2) C19 0.051(4) 0.105(5) 0.068(4) -0.008(3) -0.011(3) -0.003(3) C9 0.061(5) 0.054(4) 0.062(4) 0.000(3) 0.034(4) 0.001(3) C10 0.066(5) 0.061(5) 0.072(5) -0.016(3) 0.022(4) 0.001(3) C11 0.073(5) 0.066(4) 0.085(5) -0.003(4) 0.034(4) 0.007(3) C20 0.050(4) 0.086(5) 0.060(4) -0.024(3) 0.005(3) -0.022(3) C21 0.083(6) 0.080(5) 0.080(6) -0.014(4) 0.005(5) -0.006(5) C22 0.102(7) 0.101(6) 0.071(5) -0.029(4) 0.036(4) -0.049(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 Cu1 C1 1.901(4) . ? Cu1 Br2 2.4155(8) . ? Cu1 Br1 2.4396(7) . ? Cu2 C12 1.913(5) . ? Cu2 Br1 2.4263(8) . ? Cu2 Br2 2.6435(8) . ? Cu2 Br2 2.7139(9) 3_676 ? Br2 Cu2 2.7139(9) 3_676 ? S1 C1 1.715(5) . ? S1 C7 1.738(4) . ? S2 C12 1.715(5) . ? S2 C18 1.743(4) . ? N1 C1 1.338(5) . ? N1 C2 1.405(5) . ? N1 C8 1.467(6) . ? N2 C12 1.328(6) . ? N2 C13 1.406(6) . ? N2 C19 1.466(6) . ? C2 C3 1.388(6) . ? C2 C7 1.396(6) . ? C3 C4 1.358(7) . ? C4 C5 1.390(7) . ? C5 C6 1.363(7) . ? C6 C7 1.387(6) . ? C13 C18 1.384(6) . ? C13 C14 1.392(6) . ? C14 C15 1.365(7) . ? C15 C16 1.401(8) . ? C16 C17 1.382(7) . ? C17 C18 1.383(6) . ? C8 C9 1.488(4) . ? C8 C9A 1.495(5) . ? C19 C20 1.486(4) . ? C19 C20A 1.496(5) . ? C9 C10 1.346(5) . ? C10 C11 1.474(4) . ? C9A C10A 1.336(5) . ? C10A C11A 1.489(5) . ? C20 C21 1.344(5) . ? C21 C22 1.471(4) . ? C20A C21A 1.340(5) . ? C21A C22A 1.493(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 C1 Cu1 Br2 134.57(13) . . ? C1 Cu1 Br1 124.90(13) . . ? Br2 Cu1 Br1 100.40(3) . . ? C12 Cu2 Br1 137.68(14) . . ? C12 Cu2 Br2 114.71(15) . . ? Br1 Cu2 Br2 94.64(3) . . ? C12 Cu2 Br2 103.41(15) . 3_676 ? Br1 Cu2 Br2 100.90(3) . 3_676 ? Br2 Cu2 Br2 99.28(3) . 3_676 ? Cu2 Br1 Cu1 83.75(3) . . ? Cu1 Br2 Cu2 79.75(2) . . ? Cu1 Br2 Cu2 108.48(3) . 3_676 ? Cu2 Br2 Cu2 80.72(3) . 3_676 ? C1 S1 C7 93.7(2) . . ? C12 S2 C18 93.7(2) . . ? C1 N1 C2 116.7(4) . . ? C1 N1 C8 122.2(4) . . ? C2 N1 C8 121.1(4) . . ? C12 N2 C13 117.6(4) . . ? C12 N2 C19 121.4(4) . . ? C13 N2 C19 120.9(4) . . ? N1 C1 S1 109.2(3) . . ? N1 C1 Cu1 128.6(3) . . ? S1 C1 Cu1 122.2(2) . . ? C3 C2 C7 120.0(4) . . ? C3 C2 N1 128.5(4) . . ? C7 C2 N1 111.5(4) . . ? C4 C3 C2 118.0(5) . . ? C3 C4 C5 122.0(5) . . ? C6 C5 C4 120.8(5) . . ? C5 C6 C7 117.9(5) . . ? C6 C7 C2 121.2(4) . . ? C6 C7 S1 129.8(4) . . ? C2 C7 S1 109.0(3) . . ? N2 C12 S2 108.6(3) . . ? N2 C12 Cu2 129.9(4) . . ? S2 C12 Cu2 121.4(3) . . ? C18 C13 C14 120.5(5) . . ? C18 C13 N2 111.1(4) . . ? C14 C13 N2 128.4(4) . . ? C15 C14 C13 118.7(5) . . ? C14 C15 C16 120.9(5) . . ? C17 C16 C15 120.6(5) . . ? C16 C17 C18 118.1(5) . . ? C17 C18 C13 121.2(4) . . ? C17 C18 S2 129.8(4) . . ? C13 C18 S2 109.0(3) . . ? N1 C8 C9 111.2(4) . . ? N1 C8 C9A 107.2(14) . . ? C9 C8 C9A 28.8(9) . . ? N2 C19 C20 112.9(5) . . ? N2 C19 C20A 92(2) . . ? C20 C19 C20A 28.1(15) . . ? C10 C9 C8 121.5(5) . . ? C9 C10 C11 123.8(5) . . ? C10A C9A C8 123.6(8) . . ? C9A C10A C11A 123.7(8) . . ? C21 C20 C19 120.2(5) . . ? C20 C21 C22 122.4(6) . . ? C21A C20A C19 121.2(7) . . ? C20A C21A C22A 121.2(7) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.027 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 952965' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9282 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cu2 I2 N2 S2' _chemical_formula_weight 679.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 8.5427(5) _cell_length_b 16.1539(9) _cell_length_c 14.0458(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.0100(10) _cell_angle_gamma 90.00 _cell_volume 1927.64(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7201 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 27.44 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 5.627 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2661 _exptl_absorpt_correction_T_max 0.5516 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13477 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.44 _reflns_number_total 4404 _reflns_number_gt 4130 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+4.1354P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4404 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0691 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 -0.08300(6) 0.08207(3) 0.60006(4) 0.02962(13) Uani 1 1 d . . . Cu2 Cu 0.08605(6) -0.04807(3) 0.63152(4) 0.02564(12) Uani 1 1 d . . . I1 I -0.04120(3) 0.021254(15) 0.774785(17) 0.02111(7) Uani 1 1 d . . . I2 I 0.16827(3) 0.079623(14) 0.504233(17) 0.01870(7) Uani 1 1 d . . . S1 S -0.42943(11) 0.15392(5) 0.56529(6) 0.01850(18) Uani 1 1 d . . . S2 S 0.19772(11) -0.23607(6) 0.65552(7) 0.02101(19) Uani 1 1 d . . . N1 N -0.2068(4) 0.2537(2) 0.5947(2) 0.0201(6) Uani 1 1 d . . . N2 N 0.4027(4) -0.12487(19) 0.6696(2) 0.0205(6) Uani 1 1 d . . . C1 C -0.2309(4) 0.1723(2) 0.5856(3) 0.0203(7) Uani 1 1 d . . . C2 C -0.3410(4) 0.3044(2) 0.5860(2) 0.0180(7) Uani 1 1 d . . . C3 C -0.3444(5) 0.3905(2) 0.5950(3) 0.0231(8) Uani 1 1 d . . . H3 H -0.2504 0.4219 0.6075 0.028 Uiso 1 1 calc R . . C4 C -0.4913(5) 0.4283(2) 0.5848(3) 0.0262(8) Uani 1 1 d . . . H4 H -0.4981 0.4867 0.5913 0.031 Uiso 1 1 calc R . . C5 C -0.6296(5) 0.3822(2) 0.5651(3) 0.0267(8) Uani 1 1 d . . . H5 H -0.7284 0.4098 0.5574 0.032 Uiso 1 1 calc R . . C6 C -0.6244(5) 0.2970(2) 0.5566(3) 0.0223(8) Uani 1 1 d . . . H6 H -0.7182 0.2657 0.5429 0.027 Uiso 1 1 calc R . . C7 C -0.4786(4) 0.2587(2) 0.5688(2) 0.0178(7) Uani 1 1 d . . . C8 C -0.0496(5) 0.2905(3) 0.6087(3) 0.0269(8) Uani 1 1 d . . . H8A H 0.0297 0.2465 0.6157 0.040 Uiso 1 1 calc R . . H8B H -0.0405 0.3247 0.6667 0.040 Uiso 1 1 calc R . . H8C H -0.0327 0.3250 0.5533 0.040 Uiso 1 1 calc R . . C9 C 0.2471(4) -0.1318(2) 0.6542(3) 0.0198(7) Uani 1 1 d . . . C10 C 0.4920(5) -0.1984(2) 0.6805(2) 0.0193(7) Uani 1 1 d . . . C11 C 0.6543(5) -0.2055(2) 0.6942(3) 0.0218(8) Uani 1 1 d . . . H11 H 0.7202 -0.1580 0.6983 0.026 Uiso 1 1 calc R . . C12 C 0.7170(5) -0.2845(2) 0.7018(3) 0.0225(8) Uani 1 1 d . . . H12 H 0.8280 -0.2915 0.7112 0.027 Uiso 1 1 calc R . . C13 C 0.6196(5) -0.3540(2) 0.6959(3) 0.0242(8) Uani 1 1 d . . . H13 H 0.6658 -0.4075 0.7011 0.029 Uiso 1 1 calc R . . C14 C 0.4576(5) -0.3469(2) 0.6828(3) 0.0224(8) Uani 1 1 d . . . H14 H 0.3919 -0.3945 0.6792 0.027 Uiso 1 1 calc R . . C15 C 0.3941(4) -0.2677(2) 0.6748(2) 0.0197(7) Uani 1 1 d . . . C16 C 0.4813(5) -0.0469(2) 0.6686(3) 0.0231(8) Uani 1 1 d . . . H16A H 0.4036 -0.0021 0.6662 0.035 Uiso 1 1 calc R . . H16B H 0.5397 -0.0438 0.6123 0.035 Uiso 1 1 calc R . . H16C H 0.5547 -0.0414 0.7268 0.035 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 0.0258(3) 0.0312(3) 0.0330(3) 0.0096(2) 0.0086(2) 0.0131(2) Cu2 0.0233(3) 0.0236(2) 0.0304(3) 0.0023(2) 0.0045(2) 0.00966(19) I1 0.02133(13) 0.02200(13) 0.02035(12) 0.00132(9) 0.00384(9) 0.00321(9) I2 0.01486(12) 0.01816(12) 0.02329(13) 0.00218(8) 0.00303(9) -0.00269(8) S1 0.0187(4) 0.0159(4) 0.0212(4) 0.0000(3) 0.0038(3) 0.0007(3) S2 0.0196(4) 0.0213(4) 0.0222(4) 0.0008(3) 0.0029(3) 0.0010(3) N1 0.0172(15) 0.0260(16) 0.0173(14) -0.0015(12) 0.0030(12) -0.0024(12) N2 0.0232(16) 0.0218(16) 0.0164(14) 0.0011(12) 0.0023(12) 0.0049(13) C1 0.0191(18) 0.0255(19) 0.0168(17) 0.0020(14) 0.0041(14) 0.0029(14) C2 0.0186(18) 0.0222(18) 0.0133(16) 0.0004(13) 0.0031(13) 0.0034(14) C3 0.028(2) 0.0229(18) 0.0184(17) -0.0015(14) 0.0018(15) -0.0053(15) C4 0.043(2) 0.0154(17) 0.0205(18) -0.0015(14) 0.0027(17) 0.0033(16) C5 0.031(2) 0.025(2) 0.0250(19) -0.0001(15) 0.0040(16) 0.0102(16) C6 0.0222(19) 0.0235(18) 0.0216(18) -0.0021(15) 0.0042(15) 0.0022(15) C7 0.0235(19) 0.0166(16) 0.0136(16) 0.0010(13) 0.0027(13) 0.0013(14) C8 0.023(2) 0.032(2) 0.026(2) -0.0015(16) 0.0017(16) -0.0066(16) C9 0.0199(18) 0.0222(18) 0.0173(17) -0.0005(14) 0.0026(14) 0.0059(14) C10 0.027(2) 0.0179(17) 0.0125(16) 0.0012(13) 0.0023(14) 0.0075(15) C11 0.027(2) 0.0213(18) 0.0172(17) 0.0006(14) 0.0030(15) 0.0021(15) C12 0.0196(18) 0.0260(19) 0.0219(18) 0.0012(15) 0.0016(14) 0.0052(15) C13 0.030(2) 0.0212(18) 0.0224(19) 0.0012(15) 0.0067(16) 0.0072(15) C14 0.025(2) 0.0212(18) 0.0211(18) 0.0020(14) 0.0031(15) -0.0002(15) C15 0.0206(18) 0.0243(18) 0.0143(16) 0.0006(14) 0.0019(13) 0.0039(14) C16 0.0201(19) 0.031(2) 0.0185(17) -0.0018(15) 0.0036(14) 0.0071(16) _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 C1 1.926(4) . ? Cu1 Cu2 2.5626(7) . ? Cu1 I1 2.6329(6) . ? Cu1 I2 2.6506(6) . ? Cu1 I2 3.0456(6) 3_556 ? Cu2 C9 1.932(4) . ? Cu2 I1 2.6350(5) . ? Cu2 I2 2.7835(6) 3_556 ? Cu2 I2 2.8649(5) . ? I2 Cu2 2.7835(6) 3_556 ? I2 Cu1 3.0456(6) 3_556 ? S1 C1 1.716(4) . ? S1 C7 1.746(4) . ? S2 C9 1.737(4) . ? S2 C15 1.747(4) . ? N1 C1 1.334(5) . ? N1 C2 1.404(5) . ? N1 C8 1.463(5) . ? N2 C9 1.328(5) . ? N2 C10 1.411(5) . ? N2 C16 1.428(5) . ? C2 C7 1.388(5) . ? C2 C3 1.398(5) . ? C3 C4 1.389(6) . ? C4 C5 1.400(6) . ? C5 C6 1.381(5) . ? C6 C7 1.386(5) . ? C10 C11 1.385(5) . ? C10 C15 1.395(5) . ? C11 C12 1.383(5) . ? C12 C13 1.394(6) . ? C13 C14 1.382(6) . ? C14 C15 1.390(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 C1 Cu1 Cu2 172.24(11) . . ? C1 Cu1 I1 113.84(11) . . ? Cu2 Cu1 I1 60.933(16) . . ? C1 Cu1 I2 120.98(11) . . ? Cu2 Cu1 I2 66.647(17) . . ? I1 Cu1 I2 115.45(2) . . ? C1 Cu1 I2 118.52(12) . 3_556 ? Cu2 Cu1 I2 58.763(17) . 3_556 ? I1 Cu1 I2 97.503(17) . 3_556 ? I2 Cu1 I2 84.754(16) . 3_556 ? C9 Cu2 Cu1 168.97(12) . . ? C9 Cu2 I1 121.01(11) . . ? Cu1 Cu2 I1 60.851(17) . . ? C9 Cu2 I2 118.44(11) . 3_556 ? Cu1 Cu2 I2 69.315(19) . 3_556 ? I1 Cu2 I2 104.251(18) . 3_556 ? C9 Cu2 I2 112.95(11) . . ? Cu1 Cu2 I2 58.147(16) . . ? I1 Cu2 I2 108.558(18) . . ? I2 Cu2 I2 85.936(15) 3_556 . ? Cu1 I1 Cu2 58.216(16) . . ? Cu1 I2 Cu2 74.638(17) . 3_556 ? Cu1 I2 Cu2 55.206(15) . . ? Cu2 I2 Cu2 94.063(15) 3_556 . ? Cu1 I2 Cu1 95.245(16) . 3_556 ? Cu2 I2 Cu1 51.921(14) 3_556 3_556 ? Cu2 I2 Cu1 67.711(15) . 3_556 ? C1 S1 C7 93.65(18) . . ? C9 S2 C15 93.13(18) . . ? C1 N1 C2 116.7(3) . . ? C1 N1 C8 122.9(3) . . ? C2 N1 C8 120.3(3) . . ? C9 N2 C10 117.9(3) . . ? C9 N2 C16 122.4(3) . . ? C10 N2 C16 119.5(3) . . ? N1 C1 S1 109.1(3) . . ? N1 C1 Cu1 130.0(3) . . ? S1 C1 Cu1 120.8(2) . . ? C7 C2 C3 121.3(3) . . ? C7 C2 N1 112.0(3) . . ? C3 C2 N1 126.7(4) . . ? C4 C3 C2 117.1(4) . . ? C3 C4 C5 121.4(4) . . ? C6 C5 C4 120.9(4) . . ? C5 C6 C7 118.1(4) . . ? C6 C7 C2 121.2(3) . . ? C6 C7 S1 130.2(3) . . ? C2 C7 S1 108.6(3) . . ? N2 C9 S2 108.7(3) . . ? N2 C9 Cu2 130.6(3) . . ? S2 C9 Cu2 120.7(2) . . ? C11 C10 C15 121.8(3) . . ? C11 C10 N2 127.4(3) . . ? C15 C10 N2 110.8(3) . . ? C12 C11 C10 117.5(4) . . ? C11 C12 C13 120.9(4) . . ? C14 C13 C12 121.7(4) . . ? C13 C14 C15 117.6(4) . . ? C14 C15 C10 120.5(4) . . ? C14 C15 S2 129.9(3) . . ? C10 C15 S2 109.6(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.359 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.135 _database_code_depnum_ccdc_archive 'CCDC 952966' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9095 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H31 Br Cu2 N2 O S2' _chemical_formula_weight 658.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 9.3023(6) _cell_length_b 21.4109(15) _cell_length_c 14.8244(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.819(2) _cell_angle_gamma 90.00 _cell_volume 2931.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2946 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 21.74 _exptl_crystal_description Block _exptl_crystal_colour 'Light Yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 2.976 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4688 _exptl_absorpt_correction_T_max 0.8416 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 20626 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6713 _reflns_number_gt 3539 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0921P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6713 _refine_ls_number_parameters 335 _refine_ls_number_restraints 71 _refine_ls_R_factor_all 0.1113 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1776 _refine_ls_wR_factor_gt 0.1549 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.011 _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 0.06098(7) 0.62561(3) 0.64958(4) 0.0818(2) Uani 1 1 d . . . Cu2 Cu 0.33803(7) 0.61656(4) 0.77456(5) 0.0912(3) Uani 1 1 d . . . Br1 Br 0.22009(6) 0.72366(3) 0.72798(4) 0.0839(2) Uani 1 1 d . . . S1 S -0.24496(14) 0.64578(7) 0.53573(9) 0.0810(4) Uani 1 1 d . . . S2 S 0.68018(16) 0.60054(8) 0.78983(10) 0.0906(5) Uani 1 1 d . A . N1 N -0.0212(4) 0.68072(19) 0.4731(3) 0.0673(10) Uani 1 1 d . . . N2 N 0.5649(4) 0.6478(2) 0.9162(3) 0.0753(11) Uani 1 1 d D . . O1 O 0.1638(3) 0.57253(17) 0.7347(2) 0.0770(9) Uani 1 1 d . B . C1 C -0.0593(5) 0.6539(2) 0.5478(3) 0.0726(13) Uani 1 1 d . . . C2 C -0.1324(5) 0.6958(2) 0.4038(3) 0.0655(12) Uani 1 1 d . . . C3 C -0.1180(6) 0.7239(2) 0.3224(4) 0.0758(13) Uani 1 1 d . . . H3 H -0.0272 0.7340 0.3063 0.091 Uiso 1 1 calc R . . C4 C -0.2421(7) 0.7366(3) 0.2650(4) 0.0878(16) Uani 1 1 d . . . H4 H -0.2355 0.7560 0.2095 0.105 Uiso 1 1 calc R . . C5 C -0.3774(7) 0.7208(3) 0.2895(4) 0.0906(17) Uani 1 1 d . . . H5 H -0.4600 0.7299 0.2499 0.109 Uiso 1 1 calc R . . C6 C -0.3916(6) 0.6923(3) 0.3699(4) 0.0804(15) Uani 1 1 d . . . H6 H -0.4824 0.6817 0.3856 0.096 Uiso 1 1 calc R . . C7 C -0.2664(5) 0.6794(2) 0.4283(3) 0.0676(12) Uani 1 1 d . . . C8 C 0.1337(5) 0.6943(3) 0.4641(4) 0.0829(15) Uani 1 1 d . . . H8A H 0.1391 0.7308 0.4260 0.099 Uiso 1 1 calc R . . H8B H 0.1840 0.7039 0.5236 0.099 Uiso 1 1 calc R . . C9 C 0.2045(6) 0.6432(3) 0.4259(5) 0.1028(19) Uani 1 1 d . . . H9 H 0.1780 0.6346 0.3647 0.123 Uiso 1 1 calc R . . C10 C 0.3050(9) 0.6071(4) 0.4705(8) 0.153(4) Uani 1 1 d . . . H10 H 0.3363 0.6160 0.5311 0.183 Uiso 1 1 calc R . . C11 C 0.3680(11) 0.5541(5) 0.4281(8) 0.207(5) Uani 1 1 d . . . H11A H 0.3078 0.5181 0.4321 0.311 Uiso 1 1 calc R . . H11B H 0.4629 0.5459 0.4588 0.311 Uiso 1 1 calc R . . H11C H 0.3749 0.5635 0.3654 0.311 Uiso 1 1 calc R . . C12 C 0.5250(5) 0.6241(3) 0.8321(4) 0.0768(14) Uani 1 1 d . A . C13 C 0.7120(5) 0.6482(2) 0.9494(3) 0.0699(13) Uani 1 1 d . A . C14 C 0.7761(6) 0.6701(3) 1.0317(4) 0.0834(15) Uani 1 1 d . . . H14 H 0.7201 0.6865 1.0740 0.100 Uiso 1 1 calc R A . C15 C 0.9227(6) 0.6674(3) 1.0502(4) 0.0934(17) Uani 1 1 d . A . H15 H 0.9677 0.6813 1.1060 0.112 Uiso 1 1 calc R . . C16 C 1.0025(6) 0.6446(3) 0.9877(5) 0.104(2) Uani 1 1 d . . . H16 H 1.1026 0.6439 1.0016 0.124 Uiso 1 1 calc R A . C17 C 0.9437(6) 0.6223(3) 0.9045(5) 0.0945(17) Uani 1 1 d . A . H17 H 1.0020 0.6070 0.8628 0.113 Uiso 1 1 calc R . . C18 C 0.7937(5) 0.6235(2) 0.8850(4) 0.0746(13) Uani 1 1 d . . . C19A C 0.4408(19) 0.6677(9) 0.9639(13) 0.082(6) Uani 0.50 1 d PDU A 1 H19A H 0.4650 0.7056 0.9983 0.098 Uiso 0.50 1 calc PR A 1 H19B H 0.3568 0.6760 0.9202 0.098 Uiso 0.50 1 calc PR A 1 C20A C 0.4103(19) 0.6174(9) 1.0242(10) 0.098(5) Uani 0.50 1 d PDU A 1 H20A H 0.4029 0.5762 1.0045 0.117 Uiso 0.50 1 calc PR A 1 C21A C 0.3933(15) 0.6330(8) 1.1095(9) 0.112(5) Uani 0.50 1 d PDU A 1 H21A H 0.4133 0.6743 1.1262 0.135 Uiso 0.50 1 calc PR A 1 C22A C 0.346(2) 0.5917(9) 1.1802(11) 0.134(6) Uani 0.50 1 d PDU A 1 H22A H 0.2424 0.5883 1.1719 0.201 Uiso 0.50 1 calc PR A 1 H22B H 0.3769 0.6089 1.2391 0.201 Uiso 0.50 1 calc PR A 1 H22C H 0.3880 0.5510 1.1755 0.201 Uiso 0.50 1 calc PR A 1 C19B C 0.469(2) 0.6850(8) 0.9710(14) 0.094(7) Uani 0.50 1 d PDU A 2 H19C H 0.5248 0.7204 0.9971 0.112 Uiso 0.50 1 calc PR A 2 H19D H 0.3897 0.7015 0.9298 0.112 Uiso 0.50 1 calc PR A 2 C20B C 0.4091(17) 0.6523(7) 1.0445(11) 0.098(5) Uani 0.50 1 d PDU A 2 H20B H 0.3635 0.6751 1.0864 0.117 Uiso 0.50 1 calc PR A 2 C21B C 0.418(2) 0.5897(8) 1.0527(17) 0.159(9) Uani 0.50 1 d PDU A 2 H21B H 0.4749 0.5678 1.0159 0.191 Uiso 0.50 1 calc PR A 2 C22B C 0.340(2) 0.5542(13) 1.1192(16) 0.195(10) Uani 0.50 1 d PDU A 2 H22D H 0.2851 0.5827 1.1515 0.293 Uiso 0.50 1 calc PR A 2 H22E H 0.4091 0.5327 1.1615 0.293 Uiso 0.50 1 calc PR A 2 H22F H 0.2759 0.5244 1.0871 0.293 Uiso 0.50 1 calc PR A 2 C23 C 0.1558(6) 0.5064(3) 0.7349(4) 0.1021(18) Uani 1 1 d D . . C24A C 0.0052(9) 0.4856(6) 0.7515(9) 0.151(3) Uiso 0.50 1 d PD B 1 H24A H -0.0645 0.5015 0.7041 0.226 Uiso 0.50 1 calc PR B 1 H24B H -0.0162 0.5014 0.8091 0.226 Uiso 0.50 1 calc PR B 1 H24C H 0.0009 0.4408 0.7518 0.226 Uiso 0.50 1 calc PR B 1 C25A C 0.2617(13) 0.4793(6) 0.8083(8) 0.151(3) Uiso 0.50 1 d PD B 1 H25A H 0.2390 0.4936 0.8664 0.226 Uiso 0.50 1 calc PR B 1 H25B H 0.3578 0.4925 0.7997 0.226 Uiso 0.50 1 calc PR B 1 H25C H 0.2562 0.4346 0.8060 0.226 Uiso 0.50 1 calc PR B 1 C26A C 0.1845(16) 0.4824(6) 0.6433(6) 0.151(3) Uiso 0.50 1 d PD B 1 H26A H 0.1159 0.5004 0.5971 0.226 Uiso 0.50 1 calc PR B 1 H26B H 0.1751 0.4378 0.6419 0.226 Uiso 0.50 1 calc PR B 1 H26C H 0.2808 0.4938 0.6325 0.226 Uiso 0.50 1 calc PR B 1 C24B C 0.0083(10) 0.4848(6) 0.6956(9) 0.151(3) Uiso 0.50 1 d PD B 2 H24D H -0.0628 0.5010 0.7314 0.226 Uiso 0.50 1 calc PR B 2 H24E H 0.0051 0.4400 0.6960 0.226 Uiso 0.50 1 calc PR B 2 H24F H -0.0119 0.4997 0.6343 0.226 Uiso 0.50 1 calc PR B 2 C25B C 0.1841(15) 0.4855(6) 0.8341(5) 0.151(3) Uiso 0.50 1 d PD B 2 H25D H 0.2794 0.4984 0.8591 0.226 Uiso 0.50 1 calc PR B 2 H25E H 0.1770 0.4409 0.8373 0.226 Uiso 0.50 1 calc PR B 2 H25F H 0.1137 0.5042 0.8681 0.226 Uiso 0.50 1 calc PR B 2 C26B C 0.2740(13) 0.4814(6) 0.6845(9) 0.151(3) Uiso 0.50 1 d PD B 2 H26D H 0.3661 0.4954 0.7136 0.226 Uiso 0.50 1 calc PR B 2 H26E H 0.2604 0.4963 0.6230 0.226 Uiso 0.50 1 calc PR B 2 H26F H 0.2711 0.4366 0.6847 0.226 Uiso 0.50 1 calc PR B 2 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 0.0609(4) 0.1040(6) 0.0770(4) 0.0067(3) -0.0058(3) 0.0100(3) Cu2 0.0549(4) 0.1235(7) 0.0906(5) 0.0035(4) -0.0110(3) -0.0119(4) Br1 0.0640(3) 0.0786(4) 0.1047(5) -0.0127(3) -0.0082(3) 0.0014(3) S1 0.0579(7) 0.1006(11) 0.0834(9) 0.0047(7) 0.0036(6) -0.0067(7) S2 0.0716(9) 0.0953(11) 0.1022(11) -0.0170(8) -0.0010(7) 0.0026(8) N1 0.050(2) 0.074(3) 0.077(3) -0.001(2) 0.0000(18) -0.0018(19) N2 0.046(2) 0.094(3) 0.085(3) 0.016(2) 0.0041(19) 0.004(2) O1 0.0565(18) 0.071(2) 0.098(2) 0.0074(17) -0.0131(16) -0.0052(16) C1 0.058(3) 0.079(3) 0.078(3) -0.002(3) -0.009(2) -0.002(2) C2 0.054(3) 0.068(3) 0.072(3) -0.006(2) -0.004(2) 0.004(2) C3 0.075(3) 0.074(3) 0.079(3) -0.004(3) 0.008(3) 0.008(3) C4 0.094(4) 0.087(4) 0.077(4) -0.002(3) -0.011(3) 0.013(3) C5 0.077(4) 0.098(4) 0.088(4) -0.018(3) -0.027(3) 0.015(3) C6 0.056(3) 0.088(4) 0.094(4) -0.017(3) -0.003(3) 0.001(3) C7 0.051(3) 0.077(3) 0.073(3) -0.013(2) 0.000(2) 0.000(2) C8 0.049(3) 0.101(4) 0.097(4) 0.006(3) 0.001(2) -0.004(3) C9 0.062(3) 0.115(5) 0.133(5) -0.003(4) 0.017(3) 0.006(4) C10 0.091(5) 0.127(7) 0.255(10) 0.055(7) 0.081(6) 0.028(5) C11 0.122(8) 0.162(9) 0.349(16) 0.054(10) 0.074(9) 0.048(7) C12 0.052(3) 0.085(4) 0.089(4) 0.004(3) -0.006(2) -0.001(3) C13 0.045(2) 0.082(3) 0.082(3) 0.016(3) 0.001(2) 0.002(2) C14 0.066(3) 0.103(4) 0.077(3) 0.007(3) -0.008(3) -0.002(3) C15 0.064(3) 0.116(5) 0.095(4) 0.015(3) -0.015(3) -0.006(3) C16 0.050(3) 0.124(5) 0.128(6) 0.026(4) -0.022(3) -0.006(3) C17 0.058(3) 0.098(4) 0.128(5) 0.006(4) 0.017(3) 0.006(3) C18 0.049(3) 0.076(3) 0.098(4) 0.003(3) 0.003(2) 0.002(2) C19A 0.046(8) 0.126(11) 0.074(9) -0.002(8) 0.010(7) -0.010(8) C20A 0.065(8) 0.083(10) 0.145(14) -0.019(10) 0.008(8) 0.018(9) C21A 0.074(8) 0.128(11) 0.132(11) 0.020(10) 0.002(8) -0.013(8) C22A 0.128(12) 0.163(15) 0.115(11) 0.023(11) 0.029(10) -0.013(11) C19B 0.040(7) 0.140(14) 0.097(11) 0.007(9) -0.008(6) -0.004(9) C20B 0.070(8) 0.135(13) 0.087(9) 0.000(9) 0.005(7) 0.001(10) C21B 0.112(12) 0.156(16) 0.206(17) 0.074(13) 0.008(11) 0.060(11) C22B 0.154(16) 0.24(2) 0.180(17) 0.071(17) -0.021(15) 0.009(17) C23 0.091(4) 0.086(5) 0.129(5) -0.007(3) 0.011(4) 0.007(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 C1 1.869(5) . ? Cu1 O1 1.874(3) . ? Cu1 Br1 2.7460(9) . ? Cu1 Cu2 2.9964(8) . ? Cu2 C12 1.852(5) . ? Cu2 O1 1.907(3) . ? Cu2 Br1 2.5998(10) . ? S1 C1 1.724(5) . ? S1 C7 1.737(5) . ? S2 C12 1.716(5) . ? S2 C18 1.731(5) . ? N1 C1 1.332(6) . ? N1 C2 1.407(5) . ? N1 C8 1.491(6) . ? N2 C12 1.356(7) . ? N2 C13 1.398(6) . ? N2 C19A 1.485(9) . ? N2 C19B 1.501(9) . ? O1 C23 1.418(7) . ? C2 C3 1.369(7) . ? C2 C7 1.385(6) . ? C3 C4 1.378(7) . ? C4 C5 1.393(8) . ? C5 C6 1.359(8) . ? C6 C7 1.394(6) . ? C8 C9 1.428(8) . ? C9 C10 1.328(10) . ? C10 C11 1.452(12) . ? C13 C14 1.375(7) . ? C13 C18 1.392(7) . ? C14 C15 1.360(7) . ? C15 C16 1.346(9) . ? C16 C17 1.374(9) . ? C17 C18 1.391(7) . ? C19A C20A 1.449(10) . ? C20A C21A 1.335(9) . ? C21A C22A 1.479(9) . ? C19B C20B 1.462(10) . ? C20B C21B 1.347(10) . ? C21B C22B 1.500(10) . ? C23 C25A 1.495(5) . ? C23 C24B 1.498(5) . ? C23 C26B 1.500(5) . ? C23 C26A 1.505(5) . ? C23 C24A 1.517(5) . ? C23 C25B 1.529(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 C1 Cu1 O1 161.5(2) . . ? C1 Cu1 Br1 109.57(16) . . ? O1 Cu1 Br1 88.41(11) . . ? C1 Cu1 Cu2 155.29(17) . . ? O1 Cu1 Cu2 37.97(10) . . ? Br1 Cu1 Cu2 53.62(2) . . ? C12 Cu2 O1 154.6(2) . . ? C12 Cu2 Br1 112.91(17) . . ? O1 Cu2 Br1 92.14(11) . . ? C12 Cu2 Cu1 166.28(17) . . ? O1 Cu2 Cu1 37.19(10) . . ? Br1 Cu2 Cu1 58.26(2) . . ? Cu2 Br1 Cu1 68.12(2) . . ? C1 S1 C7 93.3(2) . . ? C12 S2 C18 94.4(3) . . ? C1 N1 C2 117.5(4) . . ? C1 N1 C8 120.9(4) . . ? C2 N1 C8 121.6(4) . . ? C12 N2 C13 118.4(4) . . ? C12 N2 C19A 113.7(10) . . ? C13 N2 C19A 127.9(10) . . ? C12 N2 C19B 125.5(10) . . ? C13 N2 C19B 115.0(10) . . ? C19A N2 C19B 17.7(14) . . ? C23 O1 Cu1 125.8(3) . . ? C23 O1 Cu2 122.4(3) . . ? Cu1 O1 Cu2 104.84(17) . . ? N1 C1 S1 108.6(3) . . ? N1 C1 Cu1 128.2(4) . . ? S1 C1 Cu1 123.2(3) . . ? C3 C2 C7 121.9(5) . . ? C3 C2 N1 127.2(5) . . ? C7 C2 N1 110.9(4) . . ? C2 C3 C4 117.9(5) . . ? C3 C4 C5 120.5(6) . . ? C6 C5 C4 121.5(5) . . ? C5 C6 C7 118.2(5) . . ? C2 C7 C6 119.9(5) . . ? C2 C7 S1 109.7(3) . . ? C6 C7 S1 130.4(4) . . ? C9 C8 N1 112.5(5) . . ? C10 C9 C8 125.4(8) . . ? C9 C10 C11 122.4(11) . . ? N2 C12 S2 107.2(3) . . ? N2 C12 Cu2 126.6(4) . . ? S2 C12 Cu2 126.2(3) . . ? C14 C13 C18 121.5(5) . . ? C14 C13 N2 128.1(5) . . ? C18 C13 N2 110.4(4) . . ? C15 C14 C13 118.9(6) . . ? C16 C15 C14 119.9(6) . . ? C15 C16 C17 123.4(5) . . ? C16 C17 C18 117.5(6) . . ? C17 C18 C13 118.7(5) . . ? C17 C18 S2 131.6(5) . . ? C13 C18 S2 109.7(3) . . ? C20A C19A N2 107.5(12) . . ? C21A C20A C19A 116.9(16) . . ? C20A C21A C22A 126.9(17) . . ? C20B C19B N2 117.0(15) . . ? C21B C20B C19B 121(2) . . ? C20B C21B C22B 122(2) . . ? O1 C23 C25A 111.0(7) . . ? O1 C23 C24B 110.7(7) . . ? C25A C23 C24B 131.1(9) . . ? O1 C23 C26B 108.2(7) . . ? C25A C23 C26B 76.4(7) . . ? C24B C23 C26B 112.8(6) . . ? O1 C23 C26A 108.8(7) . . ? C25A C23 C26A 110.6(6) . . ? C24B C23 C26A 78.2(7) . . ? C26B C23 C26A 37.8(7) . . ? O1 C23 C24A 110.1(7) . . ? C25A C23 C24A 108.0(6) . . ? C24B C23 C24A 32.1(7) . . ? C26B C23 C24A 136.2(8) . . ? C26A C23 C24A 108.2(6) . . ? O1 C23 C25B 107.0(6) . . ? C25A C23 C25B 33.2(7) . . ? C24B C23 C25B 109.2(6) . . ? C26B C23 C25B 108.8(6) . . ? C26A C23 C25B 137.7(8) . . ? C24A C23 C25B 79.4(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.675 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 952967' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9269 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H27 Br2 Cu2 N3 S3' _chemical_formula_weight 812.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 8.9738(3) _cell_length_b 18.1681(7) _cell_length_c 18.9695(7) _cell_angle_alpha 95.1390(10) _cell_angle_beta 92.8190(10) _cell_angle_gamma 98.3760(10) _cell_volume 3041.36(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9642 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.44 _exptl_crystal_description Plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.775 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 4.258 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2246 _exptl_absorpt_correction_T_max 0.7842 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40380 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 27.49 _reflns_number_total 13959 _reflns_number_gt 11225 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+0.3205P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13959 _refine_ls_number_parameters 734 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 1.09500(4) 0.80505(2) 0.08901(2) 0.02532(10) Uani 1 1 d . . . Cu2 Cu 0.89296(4) 0.69479(2) 0.12101(2) 0.02427(10) Uani 1 1 d . . . Cu3 Cu 0.28203(4) 0.16460(2) 0.39485(2) 0.02445(10) Uani 1 1 d . . . Cu4 Cu 0.18852(4) 0.29689(2) 0.35086(2) 0.01932(9) Uani 1 1 d . . . Br1 Br 1.06109(4) 0.686525(18) 0.014997(17) 0.02316(8) Uani 1 1 d . . . Br2 Br 0.83479(3) 0.831500(18) 0.091885(17) 0.02291(8) Uani 1 1 d . . . Br3 Br 0.37384(3) 0.289942(17) 0.459651(16) 0.02120(8) Uani 1 1 d . . . Br4 Br 0.01927(3) 0.163194(17) 0.368424(17) 0.02213(8) Uani 1 1 d . . . S1 S 1.42677(9) 0.84029(5) 0.16214(5) 0.02658(19) Uani 1 1 d . . . S2 S 0.53404(9) 0.65674(4) 0.09902(4) 0.02220(17) Uani 1 1 d . . . S3 S 1.17935(9) 0.68250(5) 0.22857(4) 0.02171(17) Uani 1 1 d . . . S4 S 0.60943(9) 0.12019(4) 0.40637(4) 0.02080(17) Uani 1 1 d . . . S5 S -0.14091(8) 0.33471(4) 0.38289(4) 0.01871(16) Uani 1 1 d . . . S6 S 0.50207(9) 0.28211(5) 0.28001(4) 0.02354(18) Uani 1 1 d . . . N1 N 1.2954(3) 0.94628(15) 0.13227(13) 0.0200(6) Uani 1 1 d . . . N2 N 0.6848(3) 0.55191(15) 0.09958(13) 0.0200(6) Uani 1 1 d . A . N3 N 0.9633(3) 0.74262(14) 0.27155(13) 0.0192(5) Uani 1 1 d . . . N4 N 0.3882(3) 0.01824(14) 0.39624(13) 0.0188(5) Uani 1 1 d . . . N5 N 0.0766(3) 0.43855(14) 0.38887(13) 0.0163(5) Uani 1 1 d . . . N6 N 0.2617(3) 0.25864(14) 0.20401(13) 0.0172(5) Uani 1 1 d . . . C1 C 1.2702(4) 0.87164(18) 0.12569(17) 0.0224(7) Uani 1 1 d . . . C2 C 1.4337(3) 0.98177(17) 0.16611(16) 0.0187(6) Uani 1 1 d . . . C3 C 1.4825(4) 1.05797(18) 0.18008(17) 0.0250(7) Uani 1 1 d . . . H3 H 1.4228 1.0936 0.1652 0.030 Uiso 1 1 calc R . . C4 C 1.6214(4) 1.08004(19) 0.21643(18) 0.0271(7) Uani 1 1 d . . . H4 H 1.6573 1.1319 0.2270 0.032 Uiso 1 1 calc R . . C5 C 1.7094(4) 1.02859(19) 0.23778(18) 0.0266(7) Uani 1 1 d . . . H5 H 1.8042 1.0458 0.2627 0.032 Uiso 1 1 calc R . . C6 C 1.6622(4) 0.95300(19) 0.22356(18) 0.0255(7) Uani 1 1 d . . . H6 H 1.7231 0.9177 0.2379 0.031 Uiso 1 1 calc R . . C7 C 1.5218(3) 0.93014(17) 0.18732(16) 0.0193(6) Uani 1 1 d . . . C8 C 1.1834(4) 0.99082(19) 0.10594(17) 0.0245(7) Uani 1 1 d . . . H8A H 1.1799 1.0341 0.1412 0.029 Uiso 1 1 calc R . . H8B H 1.0826 0.9598 0.1017 0.029 Uiso 1 1 calc R . . C9 C 1.2165(4) 1.0189(2) 0.03561(18) 0.0278(8) Uani 1 1 d . . . H9 H 1.1651 1.0581 0.0219 0.033 Uiso 1 1 calc R . . C10 C 1.3096(4) 0.9944(2) -0.0087(2) 0.0354(9) Uani 1 1 d . . . H10A H 1.3635 0.9554 0.0028 0.042 Uiso 1 1 calc R . . H10B H 1.3234 1.0158 -0.0523 0.042 Uiso 1 1 calc R . . C11 C 0.7079(3) 0.62694(18) 0.10371(16) 0.0212(7) Uani 1 1 d . . . C12 C 0.5348(3) 0.51515(17) 0.09257(15) 0.0184(6) Uani 1 1 d . . . C13 C 0.4831(4) 0.43824(18) 0.08507(16) 0.0212(7) Uani 1 1 d . . . H13 H 0.5512 0.4029 0.0861 0.025 Uiso 1 1 calc R . . C14 C 0.3306(4) 0.41607(18) 0.07620(17) 0.0256(7) Uani 1 1 d . . . H14 H 0.2925 0.3641 0.0701 0.031 Uiso 1 1 calc R . . C15 C 0.2292(4) 0.4673(2) 0.07590(17) 0.0271(7) Uani 1 1 d . . . H15 H 0.1240 0.4497 0.0700 0.033 Uiso 1 1 calc R . . C16 C 0.2786(4) 0.54248(19) 0.08390(16) 0.0234(7) Uani 1 1 d . . . H16 H 0.2092 0.5773 0.0840 0.028 Uiso 1 1 calc R . . C17 C 0.4335(3) 0.56653(17) 0.09184(16) 0.0188(6) Uani 1 1 d . . . C18 C 0.8137(4) 0.5103(2) 0.10311(18) 0.0273(8) Uani 1 1 d D . . H18A H 0.9051 0.5414 0.0888 0.033 Uiso 0.724(9) 1 calc PR A 1 H18B H 0.7927 0.4643 0.0698 0.033 Uiso 0.724(9) 1 calc PR A 1 H18C H 0.9063 0.5459 0.0981 0.033 Uiso 0.276(9) 1 calc PR A 2 H18D H 0.8022 0.4728 0.0612 0.033 Uiso 0.276(9) 1 calc PR A 2 C19A C 0.8414(14) 0.4897(5) 0.1774(3) 0.033(2) Uani 0.724(9) 1 d PD A 1 H19A H 0.8361 0.5261 0.2161 0.039 Uiso 0.724(9) 1 calc PR A 1 C20A C 0.8721(6) 0.4248(3) 0.1907(3) 0.0379(16) Uani 0.724(9) 1 d PD A 1 H20A H 0.8779 0.3877 0.1527 0.045 Uiso 0.724(9) 1 calc PR A 1 H20B H 0.8887 0.4142 0.2383 0.045 Uiso 0.724(9) 1 calc PR A 1 C19B C 0.840(4) 0.4702(16) 0.1676(9) 0.033(2) Uani 0.276(9) 1 d PD A 2 H19B H 0.9151 0.4382 0.1665 0.039 Uiso 0.276(9) 1 calc PR A 2 C20B C 0.7672(15) 0.4767(9) 0.2244(7) 0.041(4) Uani 0.276(9) 1 d PD A 2 H20C H 0.6917 0.5083 0.2270 0.049 Uiso 0.276(9) 1 calc PR A 2 H20D H 0.7890 0.4499 0.2634 0.049 Uiso 0.276(9) 1 calc PR A 2 C21 C 1.0103(3) 0.71398(17) 0.21056(17) 0.0205(7) Uani 1 1 d . . . C22 C 1.0542(3) 0.74002(17) 0.33393(16) 0.0190(6) Uani 1 1 d . . . C23 C 1.0242(4) 0.76410(17) 0.40265(17) 0.0220(7) Uani 1 1 d . . . H23 H 0.9348 0.7845 0.4123 0.026 Uiso 1 1 calc R . . C24 C 1.1290(4) 0.75720(18) 0.45639(17) 0.0236(7) Uani 1 1 d . . . H24 H 1.1118 0.7735 0.5039 0.028 Uiso 1 1 calc R . . C25 C 1.2593(4) 0.72678(17) 0.44243(17) 0.0227(7) Uani 1 1 d . . . H25 H 1.3296 0.7229 0.4805 0.027 Uiso 1 1 calc R . . C26 C 1.2882(3) 0.70220(18) 0.37419(17) 0.0221(7) Uani 1 1 d . . . H26 H 1.3772 0.6815 0.3647 0.027 Uiso 1 1 calc R . . C27 C 1.1829(3) 0.70874(17) 0.31976(16) 0.0189(6) Uani 1 1 d . . . C28 C 0.8227(3) 0.77508(19) 0.27372(17) 0.0237(7) Uani 1 1 d . . . H28A H 0.8002 0.7924 0.2269 0.028 Uiso 1 1 calc R . . H28B H 0.8379 0.8193 0.3092 0.028 Uiso 1 1 calc R . . C29 C 0.6898(4) 0.7220(2) 0.29184(17) 0.0285(8) Uani 1 1 d . . . H29 H 0.5980 0.7415 0.2973 0.034 Uiso 1 1 calc R . . C30 C 0.6873(4) 0.6520(2) 0.30087(19) 0.0345(9) Uani 1 1 d . . . H30A H 0.7762 0.6297 0.2960 0.041 Uiso 1 1 calc R . . H30B H 0.5965 0.6229 0.3123 0.041 Uiso 1 1 calc R . . C31 C 0.4175(3) 0.09274(18) 0.39517(16) 0.0201(6) Uani 1 1 d . . . C32 C 0.5117(4) -0.01954(17) 0.40688(15) 0.0199(6) Uani 1 1 d . . . C33 C 0.5097(4) -0.09550(18) 0.41215(17) 0.0244(7) Uani 1 1 d . . . H33 H 0.4176 -0.1292 0.4063 0.029 Uiso 1 1 calc R . . C34 C 0.6452(4) -0.12067(18) 0.42612(17) 0.0259(7) Uani 1 1 d . . . H34 H 0.6461 -0.1722 0.4309 0.031 Uiso 1 1 calc R . . C35 C 0.7808(4) -0.07132(19) 0.43335(17) 0.0260(7) Uani 1 1 d . . . H35 H 0.8727 -0.0899 0.4426 0.031 Uiso 1 1 calc R . . C36 C 0.7840(4) 0.00397(19) 0.42729(16) 0.0224(7) Uani 1 1 d . . . H36 H 0.8766 0.0373 0.4319 0.027 Uiso 1 1 calc R . . C37 C 0.6475(3) 0.02961(17) 0.41416(16) 0.0188(6) Uani 1 1 d . . . C38 C 0.2324(3) -0.02266(18) 0.38754(17) 0.0222(7) Uani 1 1 d . . . H38A H 0.1608 0.0132 0.3969 0.027 Uiso 1 1 calc R . . H38B H 0.2197 -0.0594 0.4231 0.027 Uiso 1 1 calc R . . C39 C 0.1938(4) -0.06291(19) 0.31478(17) 0.0244(7) Uani 1 1 d . . . H39 H 0.2579 -0.0962 0.2964 0.029 Uiso 1 1 calc R . . C40 C 0.0746(4) -0.0536(2) 0.27602(18) 0.0304(8) Uani 1 1 d . . . H40A H 0.0093 -0.0205 0.2937 0.037 Uiso 1 1 calc R . . H40B H 0.0533 -0.0798 0.2302 0.037 Uiso 1 1 calc R . . C41 C 0.0496(3) 0.36381(17) 0.37609(15) 0.0173(6) Uani 1 1 d . . . C42 C -0.0462(3) 0.47544(17) 0.40511(15) 0.0171(6) Uani 1 1 d . . . C43 C -0.0453(4) 0.55169(17) 0.42187(16) 0.0213(7) Uani 1 1 d . . . H43 H 0.0451 0.5862 0.4218 0.026 Uiso 1 1 calc R . . C44 C -0.1795(4) 0.57576(18) 0.43865(17) 0.0240(7) Uani 1 1 d . . . H44 H -0.1811 0.6274 0.4512 0.029 Uiso 1 1 calc R . . C45 C -0.3134(4) 0.52490(19) 0.43734(17) 0.0253(7) Uani 1 1 d . . . H45 H -0.4046 0.5428 0.4486 0.030 Uiso 1 1 calc R . . C46 C -0.3151(3) 0.44950(19) 0.42008(16) 0.0223(7) Uani 1 1 d . . . H46 H -0.4060 0.4152 0.4193 0.027 Uiso 1 1 calc R . . C47 C -0.1794(3) 0.42495(17) 0.40383(16) 0.0185(6) Uani 1 1 d . . . C48 C 0.2291(3) 0.47968(18) 0.38315(16) 0.0199(6) Uani 1 1 d . . . H48A H 0.3051 0.4473 0.3943 0.024 Uiso 1 1 calc R . . H48B H 0.2462 0.5242 0.4183 0.024 Uiso 1 1 calc R . . C49 C 0.2494(4) 0.50377(18) 0.31059(18) 0.0245(7) Uani 1 1 d . . . H49 H 0.1783 0.5318 0.2915 0.029 Uiso 1 1 calc R . . C50 C 0.3597(4) 0.4885(2) 0.27175(19) 0.0319(8) Uani 1 1 d . . . H50A H 0.4326 0.4606 0.2894 0.038 Uiso 1 1 calc R . . H50B H 0.3669 0.5053 0.2259 0.038 Uiso 1 1 calc R . . C51 C 0.3082(3) 0.27669(17) 0.27200(16) 0.0182(6) Uani 1 1 d . . . C52 C 0.3718(3) 0.24605(17) 0.15556(16) 0.0191(6) Uani 1 1 d . . . C53 C 0.3494(4) 0.22378(18) 0.08346(17) 0.0227(7) Uani 1 1 d . . . H53 H 0.2512 0.2151 0.0604 0.027 Uiso 1 1 calc R . . C54 C 0.4754(4) 0.21468(19) 0.04643(18) 0.0265(7) Uani 1 1 d . . . H54 H 0.4632 0.1989 -0.0029 0.032 Uiso 1 1 calc R . . C55 C 0.6196(4) 0.2281(2) 0.07978(19) 0.0308(8) Uani 1 1 d . . . H55 H 0.7042 0.2218 0.0529 0.037 Uiso 1 1 calc R . . C56 C 0.6412(4) 0.2505(2) 0.15143(19) 0.0300(8) Uani 1 1 d . . . H56 H 0.7398 0.2601 0.1741 0.036 Uiso 1 1 calc R . . C57 C 0.5158(3) 0.25872(18) 0.18964(17) 0.0219(7) Uani 1 1 d . . . C58 C 0.1011(3) 0.25067(19) 0.18007(17) 0.0222(7) Uani 1 1 d . . . H58A H 0.0918 0.2728 0.1345 0.027 Uiso 1 1 calc R . . H58B H 0.0474 0.2786 0.2153 0.027 Uiso 1 1 calc R . . C59 C 0.0287(3) 0.1707(2) 0.17048(18) 0.0264(7) Uani 1 1 d . . . H59 H 0.0337 0.1418 0.2097 0.032 Uiso 1 1 calc R . . C60 C -0.0414(4) 0.1381(2) 0.11101(19) 0.0321(8) Uani 1 1 d . . . H60A H -0.0481 0.1656 0.0710 0.039 Uiso 1 1 calc R . . H60B H -0.0854 0.0870 0.1080 0.039 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 0.0234(2) 0.0221(2) 0.0282(2) 0.00087(17) -0.00142(17) -0.00215(17) Cu2 0.0246(2) 0.0281(2) 0.01727(19) 0.00336(17) -0.00090(16) -0.00547(17) Cu3 0.0256(2) 0.0236(2) 0.0256(2) 0.00045(17) 0.00287(17) 0.00940(17) Cu4 0.01916(19) 0.0207(2) 0.01922(19) 0.00128(15) 0.00233(15) 0.00684(15) Br1 0.02529(16) 0.02161(17) 0.02121(16) -0.00081(13) 0.00571(13) -0.00066(13) Br2 0.02230(16) 0.02632(17) 0.02145(16) 0.00636(13) 0.00025(12) 0.00601(13) Br3 0.02255(16) 0.01889(16) 0.02176(16) -0.00036(12) -0.00506(12) 0.00532(12) Br4 0.01883(15) 0.01770(16) 0.02897(17) 0.00121(13) 0.00333(13) -0.00012(12) S1 0.0232(4) 0.0164(4) 0.0399(5) 0.0011(4) -0.0013(4) 0.0040(3) S2 0.0262(4) 0.0164(4) 0.0234(4) 0.0004(3) 0.0014(3) 0.0019(3) S3 0.0225(4) 0.0236(4) 0.0196(4) 0.0023(3) 0.0046(3) 0.0043(3) S4 0.0207(4) 0.0148(4) 0.0261(4) 0.0006(3) 0.0005(3) 0.0011(3) S5 0.0176(4) 0.0156(4) 0.0232(4) 0.0030(3) 0.0017(3) 0.0027(3) S6 0.0151(4) 0.0296(5) 0.0250(4) 0.0003(3) -0.0009(3) 0.0024(3) N1 0.0206(13) 0.0210(14) 0.0185(13) 0.0015(11) 0.0005(10) 0.0042(11) N2 0.0194(13) 0.0213(14) 0.0201(13) 0.0062(11) 0.0024(10) 0.0032(11) N3 0.0210(13) 0.0191(14) 0.0177(13) 0.0031(11) -0.0004(10) 0.0029(11) N4 0.0183(13) 0.0191(14) 0.0177(13) -0.0021(11) 0.0034(10) 0.0007(10) N5 0.0140(12) 0.0190(13) 0.0155(12) 0.0022(10) 0.0003(10) 0.0010(10) N6 0.0147(12) 0.0181(13) 0.0196(13) 0.0032(11) 0.0029(10) 0.0034(10) C1 0.0212(16) 0.0216(17) 0.0236(16) -0.0013(13) 0.0027(13) 0.0020(13) C2 0.0193(15) 0.0213(16) 0.0151(14) 0.0015(12) 0.0030(12) 0.0012(13) C3 0.0283(17) 0.0203(17) 0.0260(17) 0.0025(14) -0.0007(14) 0.0030(14) C4 0.0332(19) 0.0174(17) 0.0277(18) -0.0008(14) -0.0037(15) -0.0023(14) C5 0.0246(17) 0.0289(19) 0.0250(17) 0.0029(15) -0.0033(14) 0.0009(14) C6 0.0236(16) 0.0266(18) 0.0271(17) 0.0035(14) -0.0016(14) 0.0072(14) C7 0.0202(15) 0.0168(16) 0.0200(15) 0.0000(13) 0.0046(12) -0.0006(12) C8 0.0235(17) 0.0231(17) 0.0274(18) 0.0031(14) -0.0012(14) 0.0055(14) C9 0.0288(18) 0.0265(19) 0.0270(18) 0.0052(15) -0.0041(14) 0.0009(15) C10 0.036(2) 0.038(2) 0.0289(19) 0.0076(17) -0.0042(16) -0.0057(17) C11 0.0220(16) 0.0275(18) 0.0143(15) 0.0036(13) 0.0025(12) 0.0032(13) C12 0.0205(15) 0.0209(16) 0.0137(14) 0.0002(12) 0.0024(12) 0.0036(13) C13 0.0276(17) 0.0179(16) 0.0189(15) 0.0021(13) 0.0025(13) 0.0058(13) C14 0.0339(19) 0.0171(16) 0.0239(17) 0.0015(13) 0.0019(14) -0.0026(14) C15 0.0205(16) 0.034(2) 0.0238(17) 0.0001(15) -0.0003(13) -0.0027(14) C16 0.0256(17) 0.0273(18) 0.0186(16) -0.0003(14) 0.0017(13) 0.0102(14) C17 0.0242(16) 0.0183(16) 0.0138(14) 0.0008(12) 0.0029(12) 0.0026(13) C18 0.0199(16) 0.035(2) 0.0304(18) 0.0120(16) 0.0037(14) 0.0089(15) C19A 0.034(2) 0.038(6) 0.029(3) 0.004(3) -0.001(3) 0.016(4) C20A 0.042(3) 0.041(3) 0.033(3) 0.012(2) 0.002(2) 0.011(3) C19B 0.034(2) 0.038(6) 0.029(3) 0.004(3) -0.001(3) 0.016(4) C20B 0.030(8) 0.054(10) 0.038(8) 0.016(7) -0.004(6) -0.004(7) C21 0.0207(15) 0.0168(16) 0.0231(16) 0.0032(13) 0.0020(13) -0.0013(12) C22 0.0210(15) 0.0173(15) 0.0181(15) 0.0042(12) -0.0008(12) 0.0004(12) C23 0.0239(16) 0.0182(16) 0.0247(17) 0.0017(13) 0.0007(13) 0.0063(13) C24 0.0311(18) 0.0216(17) 0.0162(15) 0.0018(13) -0.0013(13) -0.0012(14) C25 0.0241(16) 0.0200(16) 0.0222(16) 0.0063(13) -0.0068(13) -0.0023(13) C26 0.0184(15) 0.0197(16) 0.0279(17) 0.0065(14) -0.0021(13) 0.0004(13) C27 0.0227(16) 0.0160(15) 0.0177(15) 0.0041(12) 0.0028(12) 0.0002(12) C28 0.0239(16) 0.0270(18) 0.0216(16) 0.0036(14) -0.0014(13) 0.0089(14) C29 0.0225(17) 0.040(2) 0.0237(17) 0.0033(15) 0.0034(14) 0.0077(15) C30 0.0270(19) 0.042(2) 0.033(2) 0.0043(17) 0.0058(16) -0.0013(17) C31 0.0193(15) 0.0219(16) 0.0181(15) -0.0019(13) 0.0008(12) 0.0019(13) C32 0.0269(16) 0.0203(16) 0.0128(14) -0.0001(12) 0.0048(12) 0.0048(13) C33 0.0309(18) 0.0194(17) 0.0220(16) 0.0026(13) 0.0059(14) -0.0004(14) C34 0.039(2) 0.0162(16) 0.0253(17) 0.0056(14) 0.0094(15) 0.0086(14) C35 0.0299(18) 0.0276(19) 0.0237(17) 0.0047(14) 0.0052(14) 0.0126(15) C36 0.0224(16) 0.0270(18) 0.0186(16) 0.0034(13) 0.0047(13) 0.0051(14) C37 0.0225(15) 0.0165(15) 0.0179(15) 0.0032(12) 0.0051(12) 0.0025(12) C38 0.0179(15) 0.0245(17) 0.0227(16) -0.0006(14) 0.0030(13) -0.0007(13) C39 0.0204(16) 0.0248(18) 0.0265(17) -0.0003(14) 0.0056(13) -0.0015(13) C40 0.0259(18) 0.038(2) 0.0252(18) 0.0012(16) 0.0031(14) -0.0008(16) C41 0.0185(15) 0.0220(16) 0.0108(14) 0.0033(12) -0.0012(11) 0.0015(12) C42 0.0198(15) 0.0191(16) 0.0132(14) 0.0019(12) 0.0008(12) 0.0057(12) C43 0.0270(17) 0.0177(16) 0.0183(15) 0.0000(13) 0.0035(13) 0.0008(13) C44 0.0334(18) 0.0198(17) 0.0209(16) 0.0023(13) 0.0043(14) 0.0100(14) C45 0.0225(16) 0.0301(19) 0.0266(17) 0.0041(15) 0.0049(14) 0.0127(14) C46 0.0186(15) 0.0269(18) 0.0221(16) 0.0041(14) 0.0035(13) 0.0037(13) C47 0.0226(15) 0.0155(15) 0.0177(15) 0.0021(12) 0.0001(12) 0.0037(12) C48 0.0156(14) 0.0200(16) 0.0230(16) -0.0008(13) 0.0009(12) 0.0007(12) C49 0.0245(17) 0.0201(17) 0.0283(18) 0.0082(14) -0.0004(14) -0.0013(13) C50 0.035(2) 0.034(2) 0.0264(18) 0.0077(16) 0.0063(15) -0.0008(16) C51 0.0147(14) 0.0183(16) 0.0211(15) 0.0007(12) -0.0011(12) 0.0026(12) C52 0.0181(15) 0.0188(16) 0.0223(16) 0.0061(13) 0.0033(12) 0.0057(12) C53 0.0226(16) 0.0231(17) 0.0241(17) 0.0059(14) 0.0043(13) 0.0058(13) C54 0.0327(19) 0.0295(19) 0.0198(16) 0.0076(14) 0.0105(14) 0.0067(15) C55 0.0250(18) 0.035(2) 0.036(2) 0.0100(17) 0.0164(15) 0.0074(15) C56 0.0179(16) 0.036(2) 0.038(2) 0.0097(17) 0.0084(15) 0.0035(15) C57 0.0202(15) 0.0189(16) 0.0271(17) 0.0053(13) 0.0035(13) 0.0019(13) C58 0.0148(15) 0.0311(19) 0.0217(16) 0.0030(14) 0.0010(12) 0.0068(13) C59 0.0169(15) 0.035(2) 0.0268(18) 0.0045(15) 0.0016(13) 0.0018(14) C60 0.0231(17) 0.039(2) 0.033(2) -0.0004(17) -0.0020(15) 0.0049(16) _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 C1 1.899(3) . ? Cu1 Br1 2.4343(5) . ? Cu1 Br2 2.4538(5) . ? Cu1 Cu2 2.6338(6) . ? Cu2 C11 1.914(3) . ? Cu2 C21 1.931(3) . ? Cu2 Br1 2.5794(5) . ? Cu2 Br2 2.7097(5) . ? Cu3 C31 1.910(3) . ? Cu3 Br4 2.3823(5) . ? Cu3 Br3 2.4956(5) . ? Cu3 Cu4 2.8381(5) . ? Cu4 C41 1.913(3) . ? Cu4 C51 1.924(3) . ? Cu4 Br3 2.6096(5) . ? Cu4 Br4 2.7272(5) . ? S1 C1 1.728(3) . ? S1 C7 1.742(3) . ? S2 C11 1.725(3) . ? S2 C17 1.742(3) . ? S3 C21 1.727(3) . ? S3 C27 1.750(3) . ? S4 C31 1.719(3) . ? S4 C37 1.746(3) . ? S5 C41 1.729(3) . ? S5 C47 1.740(3) . ? S6 C51 1.727(3) . ? S6 C57 1.744(3) . ? N1 C1 1.335(4) . ? N1 C2 1.408(4) . ? N1 C8 1.474(4) . ? N2 C11 1.343(4) . ? N2 C12 1.407(4) . ? N2 C18 1.473(4) . ? N3 C21 1.338(4) . ? N3 C22 1.412(4) . ? N3 C28 1.469(4) . ? N4 C31 1.343(4) . ? N4 C32 1.402(4) . ? N4 C38 1.479(4) . ? N5 C41 1.342(4) . ? N5 C42 1.403(4) . ? N5 C48 1.475(4) . ? N6 C51 1.333(4) . ? N6 C52 1.411(4) . ? N6 C58 1.472(4) . ? C2 C7 1.385(4) . ? C2 C3 1.387(4) . ? C3 C4 1.382(5) . ? C4 C5 1.383(5) . ? C5 C6 1.375(5) . ? C6 C7 1.394(4) . ? C8 C9 1.498(5) . ? C9 C10 1.309(5) . ? C12 C17 1.396(4) . ? C12 C13 1.399(4) . ? C13 C14 1.367(5) . ? C14 C15 1.394(5) . ? C15 C16 1.365(5) . ? C16 C17 1.392(4) . ? C18 C19B 1.505(15) . ? C18 C19A 1.508(7) . ? C19A C20A 1.293(9) . ? C19B C20B 1.29(2) . ? C22 C27 1.387(4) . ? C22 C23 1.389(4) . ? C23 C24 1.379(4) . ? C24 C25 1.391(5) . ? C25 C26 1.381(5) . ? C26 C27 1.389(4) . ? C28 C29 1.496(5) . ? C29 C30 1.295(5) . ? C32 C33 1.390(4) . ? C32 C37 1.395(4) . ? C33 C34 1.382(5) . ? C34 C35 1.395(5) . ? C35 C36 1.379(5) . ? C36 C37 1.391(4) . ? C38 C39 1.503(4) . ? C39 C40 1.308(5) . ? C42 C43 1.392(4) . ? C42 C47 1.394(4) . ? C43 C44 1.382(4) . ? C44 C45 1.403(5) . ? C45 C46 1.377(5) . ? C46 C47 1.396(4) . ? C48 C49 1.493(4) . ? C49 C50 1.309(5) . ? C52 C53 1.387(4) . ? C52 C57 1.395(4) . ? C53 C54 1.382(4) . ? C54 C55 1.391(5) . ? C55 C56 1.379(5) . ? C56 C57 1.387(4) . ? C58 C59 1.494(5) . ? C59 C60 1.312(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 C1 Cu1 Br1 132.24(10) . . ? C1 Cu1 Br2 125.57(10) . . ? Br1 Cu1 Br2 101.604(18) . . ? C1 Cu1 Cu2 143.08(10) . . ? Br1 Cu1 Cu2 61.038(15) . . ? Br2 Cu1 Cu2 64.249(16) . . ? C11 Cu2 C21 124.81(13) . . ? C11 Cu2 Br1 111.29(9) . . ? C21 Cu2 Br1 112.05(9) . . ? C11 Cu2 Cu1 153.21(9) . . ? C21 Cu2 Cu1 81.27(9) . . ? Br1 Cu2 Cu1 55.662(14) . . ? C11 Cu2 Br2 107.37(10) . . ? C21 Cu2 Br2 103.99(9) . . ? Br1 Cu2 Br2 91.453(16) . . ? Cu1 Cu2 Br2 54.651(14) . . ? C31 Cu3 Br4 136.67(9) . . ? C31 Cu3 Br3 116.70(9) . . ? Br4 Cu3 Br3 105.252(18) . . ? C31 Cu3 Cu4 152.27(10) . . ? Br4 Cu3 Cu4 62.268(14) . . ? Br3 Cu3 Cu4 58.163(13) . . ? C41 Cu4 C51 137.12(13) . . ? C41 Cu4 Br3 109.78(9) . . ? C51 Cu4 Br3 102.45(9) . . ? C41 Cu4 Br4 100.47(9) . . ? C51 Cu4 Br4 105.29(9) . . ? Br3 Cu4 Br4 93.156(15) . . ? C41 Cu4 Cu3 139.23(9) . . ? C51 Cu4 Cu3 82.86(9) . . ? Br3 Cu4 Cu3 54.332(13) . . ? Br4 Cu4 Cu3 50.643(13) . . ? Cu1 Br1 Cu2 63.300(15) . . ? Cu1 Br2 Cu2 61.100(15) . . ? Cu3 Br3 Cu4 67.505(15) . . ? Cu3 Br4 Cu4 67.090(15) . . ? C1 S1 C7 93.75(15) . . ? C11 S2 C17 94.02(15) . . ? C21 S3 C27 93.96(15) . . ? C31 S4 C37 93.73(15) . . ? C41 S5 C47 93.65(15) . . ? C51 S6 C57 93.52(15) . . ? C1 N1 C2 117.5(3) . . ? C1 N1 C8 122.0(3) . . ? C2 N1 C8 120.5(3) . . ? C11 N2 C12 117.9(3) . . ? C11 N2 C18 120.4(3) . . ? C12 N2 C18 121.7(3) . . ? C21 N3 C22 117.2(3) . . ? C21 N3 C28 121.5(3) . . ? C22 N3 C28 121.3(3) . . ? C31 N4 C32 117.2(3) . . ? C31 N4 C38 121.8(3) . . ? C32 N4 C38 121.0(3) . . ? C41 N5 C42 117.5(2) . . ? C41 N5 C48 120.5(2) . . ? C42 N5 C48 121.9(2) . . ? C51 N6 C52 117.6(2) . . ? C51 N6 C58 121.6(3) . . ? C52 N6 C58 120.8(2) . . ? N1 C1 S1 108.2(2) . . ? N1 C1 Cu1 129.6(2) . . ? S1 C1 Cu1 122.09(18) . . ? C7 C2 C3 121.1(3) . . ? C7 C2 N1 111.4(3) . . ? C3 C2 N1 127.5(3) . . ? C4 C3 C2 117.3(3) . . ? C3 C4 C5 121.7(3) . . ? C6 C5 C4 121.3(3) . . ? C5 C6 C7 117.5(3) . . ? C2 C7 C6 121.1(3) . . ? C2 C7 S1 109.1(2) . . ? C6 C7 S1 129.7(3) . . ? N1 C8 C9 113.5(3) . . ? C10 C9 C8 125.9(3) . . ? N2 C11 S2 108.0(2) . . ? N2 C11 Cu2 129.2(2) . . ? S2 C11 Cu2 122.57(19) . . ? C17 C12 C13 120.7(3) . . ? C17 C12 N2 110.9(3) . . ? C13 C12 N2 128.3(3) . . ? C14 C13 C12 117.3(3) . . ? C13 C14 C15 122.0(3) . . ? C16 C15 C14 121.2(3) . . ? C15 C16 C17 118.0(3) . . ? C16 C17 C12 120.8(3) . . ? C16 C17 S2 130.0(3) . . ? C12 C17 S2 109.2(2) . . ? N2 C18 C19B 119.0(12) . . ? N2 C18 C19A 110.3(5) . . ? C19B C18 C19A 14.7(13) . . ? C20A C19A C18 122.8(6) . . ? C20B C19B C18 124(2) . . ? N3 C21 S3 108.4(2) . . ? N3 C21 Cu2 125.6(2) . . ? S3 C21 Cu2 125.18(18) . . ? C27 C22 C23 121.5(3) . . ? C27 C22 N3 111.9(3) . . ? C23 C22 N3 126.6(3) . . ? C24 C23 C22 117.5(3) . . ? C23 C24 C25 121.3(3) . . ? C26 C25 C24 121.1(3) . . ? C25 C26 C27 117.9(3) . . ? C22 C27 C26 120.7(3) . . ? C22 C27 S3 108.6(2) . . ? C26 C27 S3 130.7(2) . . ? N3 C28 C29 113.7(3) . . ? C30 C29 C28 126.5(3) . . ? N4 C31 S4 108.7(2) . . ? N4 C31 Cu3 129.7(2) . . ? S4 C31 Cu3 121.09(18) . . ? C33 C32 C37 120.7(3) . . ? C33 C32 N4 127.8(3) . . ? C37 C32 N4 111.5(3) . . ? C34 C33 C32 118.3(3) . . ? C33 C34 C35 120.8(3) . . ? C36 C35 C34 121.3(3) . . ? C35 C36 C37 118.0(3) . . ? C36 C37 C32 120.9(3) . . ? C36 C37 S4 130.2(2) . . ? C32 C37 S4 108.9(2) . . ? N4 C38 C39 113.0(3) . . ? C40 C39 C38 122.1(3) . . ? N5 C41 S5 108.3(2) . . ? N5 C41 Cu4 128.4(2) . . ? S5 C41 Cu4 123.26(17) . . ? C43 C42 C47 121.0(3) . . ? C43 C42 N5 127.8(3) . . ? C47 C42 N5 111.2(3) . . ? C44 C43 C42 118.1(3) . . ? C43 C44 C45 120.9(3) . . ? C46 C45 C44 121.2(3) . . ? C45 C46 C47 118.0(3) . . ? C42 C47 C46 120.8(3) . . ? C42 C47 S5 109.3(2) . . ? C46 C47 S5 129.8(2) . . ? N5 C48 C49 111.6(2) . . ? C50 C49 C48 123.7(3) . . ? N6 C51 S6 108.7(2) . . ? N6 C51 Cu4 128.1(2) . . ? S6 C51 Cu4 123.24(17) . . ? C53 C52 C57 121.4(3) . . ? C53 C52 N6 127.8(3) . . ? C57 C52 N6 110.8(3) . . ? C54 C53 C52 117.5(3) . . ? C53 C54 C55 121.5(3) . . ? C56 C55 C54 120.8(3) . . ? C55 C56 C57 118.5(3) . . ? C56 C57 C52 120.3(3) . . ? C56 C57 S6 130.4(3) . . ? C52 C57 S6 109.4(2) . . ? N6 C58 C59 111.9(3) . . ? C60 C59 C58 123.7(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.808 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.117 _database_code_depnum_ccdc_archive 'CCDC 952968' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9278 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H39 Br2 Cu2 N3 O S3' _chemical_formula_weight 912.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9571(4) _cell_length_b 25.9573(11) _cell_length_c 17.0010(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.6650(10) _cell_angle_gamma 90.00 _cell_volume 3884.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4112 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 22.82 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 3.345 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5543 _exptl_absorpt_correction_T_max 0.8245 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 27500 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8913 _reflns_number_gt 6052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^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 8913 _refine_ls_number_parameters 449 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 0.33349(6) 0.135060(18) 0.47541(3) 0.04685(14) Uani 1 1 d . . . Cu2 Cu 0.22079(5) 0.237331(18) 0.50328(3) 0.03842(13) Uani 1 1 d . . . S1 S 0.66913(11) 0.10822(4) 0.45276(7) 0.0471(3) Uani 1 1 d . . . S2 S -0.11028(10) 0.25279(4) 0.53958(6) 0.0428(2) Uani 1 1 d . A . S3 S 0.52609(10) 0.25684(4) 0.43489(6) 0.0450(3) Uani 1 1 d . . . N1 N 0.4656(3) 0.04219(12) 0.41547(19) 0.0378(7) Uani 1 1 d . . . N2 N 0.1071(3) 0.28856(11) 0.63728(18) 0.0356(7) Uani 1 1 d D . . N3 N 0.2779(3) 0.28423(11) 0.35389(18) 0.0353(7) Uani 1 1 d . . . Br1 Br 0.43717(4) 0.182174(15) 0.60013(2) 0.04128(11) Uani 1 1 d . . . Br2 Br 0.07198(4) 0.154273(16) 0.43305(3) 0.05010(13) Uani 1 1 d . . . C1 C 0.4814(4) 0.09067(14) 0.4424(2) 0.0397(9) Uani 1 1 d . . . C2 C 0.5983(4) 0.01655(14) 0.4035(2) 0.0381(9) Uani 1 1 d . . . C3 C 0.6116(4) -0.03461(15) 0.3816(3) 0.0450(10) Uani 1 1 d . . . H3 H 0.5259 -0.0561 0.3696 0.054 Uiso 1 1 calc R . . C4 C 0.7545(5) -0.05268(16) 0.3782(3) 0.0544(11) Uani 1 1 d . . . H4 H 0.7671 -0.0873 0.3644 0.065 Uiso 1 1 calc R . . C5 C 0.8806(5) -0.02064(16) 0.3949(3) 0.0588(12) Uani 1 1 d . . . H5 H 0.9769 -0.0338 0.3913 0.071 Uiso 1 1 calc R . . C6 C 0.8677(5) 0.02967(17) 0.4166(3) 0.0548(12) Uani 1 1 d . . . H6 H 0.9537 0.0510 0.4281 0.066 Uiso 1 1 calc R . . C7 C 0.7242(4) 0.04846(14) 0.4211(2) 0.0417(9) Uani 1 1 d . . . C8 C 0.3156(4) 0.01693(16) 0.3973(3) 0.0474(10) Uani 1 1 d . . . H8A H 0.3242 -0.0179 0.4199 0.057 Uiso 1 1 calc R . . H8B H 0.2440 0.0362 0.4231 0.057 Uiso 1 1 calc R . . C9 C 0.2548(5) 0.0136(2) 0.3108(3) 0.0669(14) Uani 1 1 d . . . H9 H 0.2478 0.0439 0.2801 0.080 Uiso 1 1 calc R . . C10 C 0.2082(5) -0.0315(2) 0.2735(3) 0.0773(16) Uani 1 1 d . . . H10 H 0.2237 -0.0614 0.3052 0.093 Uiso 1 1 calc R . . C11 C 0.1391(7) -0.0387(3) 0.1922(4) 0.115(2) Uani 1 1 d . . . H11A H 0.1377 -0.0062 0.1638 0.173 Uiso 1 1 calc R . . H11B H 0.0358 -0.0509 0.1892 0.173 Uiso 1 1 calc R . . H11C H 0.1964 -0.0639 0.1679 0.173 Uiso 1 1 calc R . . C12 C 0.0829(4) 0.26192(14) 0.5687(2) 0.0354(8) Uani 1 1 d . A . C13 C -0.0203(4) 0.30171(13) 0.6701(2) 0.0343(8) Uani 1 1 d . A . C14 C -0.0225(4) 0.32718(15) 0.7419(2) 0.0429(9) Uani 1 1 d . . . H14 H 0.0680 0.3384 0.7745 0.051 Uiso 1 1 calc R A . C15 C -0.1615(5) 0.33548(16) 0.7637(2) 0.0473(10) Uani 1 1 d . A . H15 H -0.1656 0.3526 0.8120 0.057 Uiso 1 1 calc R . . C16 C -0.2954(4) 0.31904(15) 0.7154(2) 0.0474(10) Uani 1 1 d . . . H16 H -0.3888 0.3252 0.7314 0.057 Uiso 1 1 calc R A . C17 C -0.2931(4) 0.29389(16) 0.6448(3) 0.0458(10) Uani 1 1 d . A . H17 H -0.3838 0.2828 0.6123 0.055 Uiso 1 1 calc R . . C18 C -0.1539(4) 0.28518(14) 0.6222(2) 0.0359(8) Uani 1 1 d . . . C23 C 0.3314(4) 0.26095(14) 0.4233(2) 0.0356(8) Uani 1 1 d . . . C24 C 0.3842(4) 0.30013(14) 0.3080(2) 0.0386(9) Uani 1 1 d . . . C25 C 0.3544(5) 0.32417(16) 0.2329(3) 0.0500(10) Uani 1 1 d . . . H25 H 0.2549 0.3321 0.2072 0.060 Uiso 1 1 calc R . . C26 C 0.4789(6) 0.33562(16) 0.1982(3) 0.0583(12) Uani 1 1 d . . . H26 H 0.4634 0.3519 0.1479 0.070 Uiso 1 1 calc R . . C27 C 0.6250(5) 0.32378(17) 0.2356(3) 0.0605(13) Uani 1 1 d . . . H27 H 0.7067 0.3322 0.2103 0.073 Uiso 1 1 calc R . . C28 C 0.6534(5) 0.30012(16) 0.3087(3) 0.0536(11) Uani 1 1 d . . . H28 H 0.7533 0.2919 0.3335 0.064 Uiso 1 1 calc R . . C29 C 0.5311(4) 0.28846(15) 0.3454(2) 0.0415(9) Uani 1 1 d . . . C30 C 0.1137(4) 0.29505(16) 0.3304(3) 0.0449(10) Uani 1 1 d . . . H30A H 0.0560 0.2685 0.3527 0.054 Uiso 1 1 calc R . . H30B H 0.0848 0.2937 0.2719 0.054 Uiso 1 1 calc R . . C31 C 0.0747(5) 0.34629(19) 0.3590(3) 0.0616(13) Uani 1 1 d . . . H31 H 0.1028 0.3532 0.4140 0.074 Uiso 1 1 calc R . . C32 C 0.0046(5) 0.3823(2) 0.3139(4) 0.0721(14) Uani 1 1 d . . . H32 H -0.0191 0.3755 0.2587 0.087 Uiso 1 1 calc R . . C33 C -0.0417(7) 0.4330(2) 0.3408(4) 0.105(2) Uani 1 1 d . . . H33A H 0.0058 0.4384 0.3962 0.157 Uiso 1 1 calc R . . H33B H -0.1513 0.4339 0.3360 0.157 Uiso 1 1 calc R . . H33C H -0.0100 0.4599 0.3078 0.157 Uiso 1 1 calc R . . O1S O 0.7385(8) 0.4912(3) 0.4948(4) 0.186(3) Uani 1 1 d . . . C1S C 0.7452(13) 0.4472(4) 0.5198(5) 0.141(3) Uani 1 1 d . . . C2S C 0.6069(13) 0.4151(4) 0.5045(7) 0.216(6) Uani 1 1 d . . . H2S1 H 0.5809 0.4046 0.5550 0.325 Uiso 1 1 calc R . . H2S2 H 0.6252 0.3848 0.4742 0.325 Uiso 1 1 calc R . . H2S3 H 0.5238 0.4348 0.4741 0.325 Uiso 1 1 calc R . . C3S C 0.8847(11) 0.4256(4) 0.5648(6) 0.191(5) Uani 1 1 d . . . H3S1 H 0.9690 0.4483 0.5606 0.286 Uiso 1 1 calc R . . H3S2 H 0.9025 0.3920 0.5433 0.286 Uiso 1 1 calc R . . H3S3 H 0.8760 0.4222 0.6206 0.286 Uiso 1 1 calc R . . C19B C 0.258(4) 0.3128(19) 0.662(3) 0.056(5) Uani 0.197(10) 1 d PD A 2 H19A H 0.3350 0.2861 0.6601 0.068 Uiso 0.197(10) 1 calc PR A 2 H19B H 0.2676 0.3235 0.7177 0.068 Uiso 0.197(10) 1 calc PR A 2 C20B C 0.299(3) 0.3585(8) 0.6152(17) 0.056(5) Uani 0.197(10) 1 d PD A 2 H20B H 0.3167 0.3531 0.5629 0.068 Uiso 0.197(10) 1 calc PR A 2 C21B C 0.312(3) 0.4054(9) 0.6444(13) 0.056(5) Uani 0.197(10) 1 d PD A 2 H21B H 0.3132 0.4320 0.6071 0.068 Uiso 0.197(10) 1 calc PR A 2 C22B C 0.324(4) 0.4216(13) 0.7294(13) 0.056(5) Uani 0.197(10) 1 d PD A 2 H22A H 0.2381 0.4430 0.7346 0.085 Uiso 0.197(10) 1 calc PR A 2 H22B H 0.4175 0.4410 0.7459 0.085 Uiso 0.197(10) 1 calc PR A 2 H22C H 0.3258 0.3914 0.7630 0.085 Uiso 0.197(10) 1 calc PR A 2 C19A C 0.2615(7) 0.3044(3) 0.6764(6) 0.0389(16) Uani 0.803(10) 1 d PD A 1 H19C H 0.3376 0.2840 0.6554 0.047 Uiso 0.803(10) 1 calc PR A 1 H19D H 0.2753 0.2986 0.7342 0.047 Uiso 0.803(10) 1 calc PR A 1 C20A C 0.2803(6) 0.3600(2) 0.6596(4) 0.0498(16) Uani 0.803(10) 1 d PD A 1 H20A H 0.2682 0.3704 0.6058 0.060 Uiso 0.803(10) 1 calc PR A 1 C21A C 0.3119(8) 0.3949(3) 0.7139(5) 0.069(3) Uani 0.803(10) 1 d PD A 1 H21A H 0.3282 0.3838 0.7674 0.082 Uiso 0.803(10) 1 calc PR A 1 C22A C 0.3254(10) 0.4519(3) 0.6997(6) 0.102(3) Uani 0.803(10) 1 d PD A 1 H22D H 0.3086 0.4586 0.6426 0.153 Uiso 0.803(10) 1 calc PR A 1 H22E H 0.4262 0.4636 0.7242 0.153 Uiso 0.803(10) 1 calc PR A 1 H22F H 0.2501 0.4703 0.7232 0.153 Uiso 0.803(10) 1 calc PR A 1 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 0.0521(3) 0.0427(3) 0.0489(3) -0.0036(2) 0.0175(2) 0.0050(2) Cu2 0.0349(2) 0.0437(3) 0.0401(3) -0.0011(2) 0.0158(2) -0.0006(2) S1 0.0444(5) 0.0344(5) 0.0619(7) -0.0052(5) 0.0083(5) -0.0027(4) S2 0.0314(5) 0.0591(6) 0.0388(6) -0.0119(5) 0.0090(4) -0.0036(4) S3 0.0284(4) 0.0643(7) 0.0428(6) 0.0009(5) 0.0075(4) -0.0019(5) N1 0.0335(16) 0.0399(18) 0.0409(19) -0.0067(14) 0.0097(14) -0.0027(14) N2 0.0288(15) 0.0390(17) 0.0392(18) -0.0068(14) 0.0070(13) -0.0014(13) N3 0.0300(15) 0.0417(17) 0.0349(18) 0.0028(14) 0.0080(13) -0.0030(13) Br1 0.0402(2) 0.0427(2) 0.0399(2) -0.00354(17) 0.00458(17) 0.00062(17) Br2 0.0404(2) 0.0439(2) 0.0658(3) -0.0126(2) 0.0095(2) -0.00755(18) C1 0.041(2) 0.038(2) 0.040(2) -0.0049(17) 0.0070(17) 0.0032(17) C2 0.043(2) 0.036(2) 0.036(2) 0.0004(17) 0.0098(17) -0.0002(17) C3 0.042(2) 0.035(2) 0.060(3) -0.0048(19) 0.015(2) -0.0025(18) C4 0.057(3) 0.037(2) 0.071(3) -0.003(2) 0.019(2) 0.003(2) C5 0.045(2) 0.049(3) 0.085(4) -0.005(2) 0.020(2) 0.006(2) C6 0.039(2) 0.048(3) 0.079(3) 0.002(2) 0.015(2) -0.003(2) C7 0.039(2) 0.033(2) 0.054(3) 0.0032(18) 0.0101(18) -0.0023(17) C8 0.038(2) 0.050(2) 0.056(3) -0.014(2) 0.0114(19) -0.0090(19) C9 0.047(3) 0.077(3) 0.074(4) -0.009(3) 0.003(2) -0.007(2) C10 0.050(3) 0.116(5) 0.064(4) -0.020(3) 0.005(2) 0.002(3) C11 0.085(4) 0.147(6) 0.105(6) -0.049(5) -0.003(4) 0.001(4) C12 0.0306(18) 0.041(2) 0.036(2) 0.0006(17) 0.0111(16) -0.0022(16) C13 0.0321(18) 0.0334(19) 0.038(2) -0.0013(16) 0.0071(16) 0.0010(16) C14 0.040(2) 0.045(2) 0.043(2) -0.0074(18) 0.0067(18) -0.0017(18) C15 0.052(2) 0.051(2) 0.040(2) -0.0071(19) 0.012(2) 0.007(2) C16 0.042(2) 0.055(3) 0.049(3) -0.003(2) 0.019(2) 0.005(2) C17 0.0321(19) 0.055(3) 0.051(3) -0.006(2) 0.0111(18) -0.0040(19) C18 0.0357(19) 0.041(2) 0.033(2) -0.0029(16) 0.0113(16) -0.0014(17) C23 0.0281(17) 0.040(2) 0.040(2) -0.0091(17) 0.0098(16) -0.0073(16) C24 0.040(2) 0.036(2) 0.043(2) -0.0027(17) 0.0174(18) -0.0078(17) C25 0.052(2) 0.050(3) 0.049(3) 0.005(2) 0.014(2) -0.010(2) C26 0.079(3) 0.049(3) 0.054(3) 0.004(2) 0.032(3) -0.013(2) C27 0.059(3) 0.061(3) 0.073(3) -0.002(3) 0.040(3) -0.018(2) C28 0.040(2) 0.057(3) 0.068(3) -0.001(2) 0.024(2) -0.011(2) C29 0.037(2) 0.046(2) 0.044(2) -0.0066(18) 0.0135(18) -0.0087(18) C30 0.0279(18) 0.054(2) 0.052(3) 0.009(2) 0.0064(18) -0.0010(18) C31 0.042(2) 0.078(3) 0.065(3) 0.009(3) 0.012(2) 0.012(2) C32 0.062(3) 0.075(3) 0.083(4) 0.000(3) 0.021(3) 0.004(3) C33 0.107(5) 0.091(4) 0.121(6) -0.003(4) 0.033(4) 0.040(4) O1S 0.257(8) 0.134(5) 0.171(6) 0.055(5) 0.052(5) 0.075(5) C1S 0.227(11) 0.107(7) 0.092(6) 0.028(5) 0.039(7) 0.055(7) C2S 0.244(13) 0.161(10) 0.211(13) 0.053(9) -0.045(10) -0.045(9) C3S 0.217(11) 0.160(9) 0.185(11) 0.081(8) 0.012(8) 0.057(8) C19B 0.054(8) 0.066(11) 0.046(10) -0.002(8) 0.003(6) 0.002(8) C20B 0.054(8) 0.066(11) 0.046(10) -0.002(8) 0.003(6) 0.002(8) C21B 0.054(8) 0.066(11) 0.046(10) -0.002(8) 0.003(6) 0.002(8) C22B 0.054(8) 0.066(11) 0.046(10) -0.002(8) 0.003(6) 0.002(8) C19A 0.022(2) 0.045(4) 0.048(5) -0.014(3) 0.003(2) 0.002(2) C20A 0.038(3) 0.048(4) 0.065(4) -0.007(3) 0.016(3) -0.015(2) C21A 0.055(4) 0.060(4) 0.089(7) -0.006(4) 0.010(4) -0.008(4) C22A 0.115(6) 0.057(5) 0.130(8) -0.002(5) 0.012(6) -0.031(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 Cu1 C1 1.917(4) . ? Cu1 Br2 2.3727(6) . ? Cu1 Br1 2.4749(6) . ? Cu1 Cu2 2.9099(7) . ? Cu2 C12 1.917(4) . ? Cu2 C23 1.925(4) . ? Cu2 Br2 2.6947(6) . ? Cu2 Br1 2.7085(6) . ? S1 C1 1.719(4) . ? S1 C7 1.743(4) . ? S2 C12 1.726(3) . ? S2 C18 1.743(4) . ? S3 C23 1.722(3) . ? S3 C29 1.736(4) . ? N1 C1 1.338(5) . ? N1 C2 1.410(4) . ? N1 C8 1.475(4) . ? N2 C12 1.339(5) . ? N2 C13 1.402(4) . ? N2 C19A 1.478(5) . ? N2 C19B 1.481(18) . ? N3 C23 1.334(5) . ? N3 C24 1.400(4) . ? N3 C30 1.477(4) . ? C2 C7 1.386(5) . ? C2 C3 1.390(5) . ? C3 C4 1.375(5) . ? C4 C5 1.389(6) . ? C5 C6 1.367(6) . ? C6 C7 1.390(5) . ? C8 C9 1.473(6) . ? C9 C10 1.360(7) . ? C10 C11 1.418(7) . ? C13 C18 1.385(5) . ? C13 C14 1.391(5) . ? C14 C15 1.381(5) . ? C15 C16 1.389(5) . ? C16 C17 1.371(5) . ? C17 C18 1.389(5) . ? C24 C29 1.385(5) . ? C24 C25 1.402(6) . ? C25 C26 1.387(6) . ? C26 C27 1.379(6) . ? C27 C28 1.367(6) . ? C28 C29 1.391(5) . ? C30 C31 1.481(6) . ? C31 C32 1.296(7) . ? C32 C33 1.476(7) . ? O1S C1S 1.218(9) . ? C1S C3S 1.451(11) . ? C1S C2S 1.474(12) . ? C19B C20B 1.508(19) . ? C20B C21B 1.313(18) . ? C21B C22B 1.488(18) . ? C19A C20A 1.488(8) . ? C20A C21A 1.286(8) . ? C21A C22A 1.507(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 C1 Cu1 Br2 137.27(11) . . ? C1 Cu1 Br1 112.21(11) . . ? Br2 Cu1 Br1 110.43(2) . . ? C1 Cu1 Cu2 151.10(12) . . ? Br2 Cu1 Cu2 60.327(17) . . ? Br1 Cu1 Cu2 59.748(17) . . ? C12 Cu2 C23 140.76(15) . . ? C12 Cu2 Br2 101.79(11) . . ? C23 Cu2 Br2 102.65(11) . . ? C12 Cu2 Br1 106.78(11) . . ? C23 Cu2 Br1 101.17(11) . . ? Br2 Cu2 Br1 94.939(19) . . ? C12 Cu2 Cu1 132.70(11) . . ? C23 Cu2 Cu1 86.34(11) . . ? Br2 Cu2 Cu1 49.911(16) . . ? Br1 Cu2 Cu1 52.121(15) . . ? C1 S1 C7 93.43(18) . . ? C12 S2 C18 93.75(17) . . ? C23 S3 C29 93.48(18) . . ? C1 N1 C2 117.1(3) . . ? C1 N1 C8 121.7(3) . . ? C2 N1 C8 121.3(3) . . ? C12 N2 C13 117.4(3) . . ? C12 N2 C19A 121.5(5) . . ? C13 N2 C19A 121.1(5) . . ? C12 N2 C19B 117(3) . . ? C13 N2 C19B 124(3) . . ? C19A N2 C19B 12.8(15) . . ? C23 N3 C24 117.2(3) . . ? C23 N3 C30 120.2(3) . . ? C24 N3 C30 122.6(3) . . ? Cu1 Br1 Cu2 68.131(18) . . ? Cu1 Br2 Cu2 69.762(18) . . ? N1 C1 S1 108.9(3) . . ? N1 C1 Cu1 129.1(3) . . ? S1 C1 Cu1 121.8(2) . . ? C7 C2 C3 121.5(3) . . ? C7 C2 N1 111.1(3) . . ? C3 C2 N1 127.3(3) . . ? C4 C3 C2 117.6(4) . . ? C3 C4 C5 121.0(4) . . ? C6 C5 C4 121.4(4) . . ? C5 C6 C7 118.4(4) . . ? C2 C7 C6 120.1(4) . . ? C2 C7 S1 109.5(3) . . ? C6 C7 S1 130.3(3) . . ? C9 C8 N1 113.0(4) . . ? C10 C9 C8 122.7(5) . . ? C9 C10 C11 127.5(6) . . ? N2 C12 S2 108.2(2) . . ? N2 C12 Cu2 131.3(3) . . ? S2 C12 Cu2 120.5(2) . . ? C18 C13 C14 120.8(3) . . ? C18 C13 N2 111.6(3) . . ? C14 C13 N2 127.5(3) . . ? C15 C14 C13 118.0(4) . . ? C14 C15 C16 121.1(4) . . ? C17 C16 C15 120.8(4) . . ? C16 C17 C18 118.7(4) . . ? C13 C18 C17 120.6(3) . . ? C13 C18 S2 109.0(3) . . ? C17 C18 S2 130.4(3) . . ? N3 C23 S3 108.6(3) . . ? N3 C23 Cu2 128.4(3) . . ? S3 C23 Cu2 122.9(2) . . ? C29 C24 N3 111.5(3) . . ? C29 C24 C25 121.4(4) . . ? N3 C24 C25 127.2(4) . . ? C26 C25 C24 116.8(4) . . ? C27 C26 C25 121.7(4) . . ? C28 C27 C26 121.3(4) . . ? C27 C28 C29 118.5(4) . . ? C24 C29 C28 120.4(4) . . ? C24 C29 S3 109.2(3) . . ? C28 C29 S3 130.3(3) . . ? N3 C30 C31 111.4(3) . . ? C32 C31 C30 124.9(5) . . ? C31 C32 C33 126.3(6) . . ? O1S C1S C3S 121.8(11) . . ? O1S C1S C2S 118.9(10) . . ? C3S C1S C2S 119.3(9) . . ? N2 C19B C20B 119(2) . . ? C21B C20B C19B 123(4) . . ? C20B C21B C22B 128(3) . . ? N2 C19A C20A 108.3(5) . . ? C21A C20A C19A 124.4(7) . . ? C20A C21A C22A 126.2(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.790 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 952969' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9345a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 Br Cu N2 S2' _chemical_formula_weight 521.99 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0408(19) _cell_length_b 20.945(3) _cell_length_c 8.6404(14) _cell_angle_alpha 90.00 _cell_angle_beta 99.034(3) _cell_angle_gamma 90.00 _cell_volume 2152.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4892 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.42 _exptl_crystal_description Needle _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 3.076 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3725 _exptl_absorpt_correction_T_max 0.8369 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15214 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4939 _reflns_number_gt 4273 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4939 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 0.17328(3) 0.468316(16) 0.05294(4) 0.01646(10) Uani 1 1 d . . . Br1 Br 0.24395(2) 0.561738(13) -0.08636(3) 0.01977(9) Uani 1 1 d . . . S1 S 0.22678(5) 0.45550(3) 0.42918(7) 0.01730(15) Uani 1 1 d . . . S2 S 0.03367(6) 0.45885(3) -0.29058(8) 0.01793(15) Uani 1 1 d . . . N1 N 0.37679(18) 0.43554(10) 0.2665(2) 0.0142(4) Uani 1 1 d . . . N2 N -0.00312(18) 0.37801(10) -0.0922(2) 0.0164(5) Uani 1 1 d . . . C1 C 0.2678(2) 0.45166(12) 0.2469(3) 0.0150(5) Uani 1 1 d . . . C2 C 0.4327(2) 0.42692(12) 0.4205(3) 0.0139(5) Uani 1 1 d . . . C3 C 0.5462(2) 0.41388(12) 0.4690(3) 0.0170(5) Uani 1 1 d . . . H3 H 0.5959 0.4071 0.3954 0.020 Uiso 1 1 calc R . . C4 C 0.5839(2) 0.41123(13) 0.6287(3) 0.0191(6) Uani 1 1 d . . . H4 H 0.6612 0.4030 0.6652 0.023 Uiso 1 1 calc R . . C5 C 0.5110(2) 0.42031(13) 0.7371(3) 0.0198(6) Uani 1 1 d . . . H5 H 0.5395 0.4181 0.8459 0.024 Uiso 1 1 calc R . . C6 C 0.3979(2) 0.43255(13) 0.6893(3) 0.0195(6) Uani 1 1 d . . . H6 H 0.3481 0.4383 0.7631 0.023 Uiso 1 1 calc R . . C7 C 0.3600(2) 0.43611(12) 0.5285(3) 0.0148(5) Uani 1 1 d . . . C8 C 0.4330(2) 0.42321(13) 0.1296(3) 0.0161(5) Uani 1 1 d . . . H8A H 0.5145 0.4321 0.1575 0.019 Uiso 1 1 calc R . . H8B H 0.4020 0.4521 0.0429 0.019 Uiso 1 1 calc R . . C9 C 0.4161(2) 0.35565(13) 0.0773(3) 0.0215(6) Uani 1 1 d . . . H9 H 0.3414 0.3400 0.0537 0.026 Uiso 1 1 calc R . . C10 C 0.5004(3) 0.31589(14) 0.0616(4) 0.0280(7) Uani 1 1 d . . . H10 H 0.5751 0.3313 0.0892 0.034 Uiso 1 1 calc R . . C11 C 0.4850(3) 0.24886(16) 0.0034(4) 0.0397(8) Uani 1 1 d . . . H11A H 0.4045 0.2390 -0.0197 0.060 Uiso 1 1 calc R . . H11B H 0.5217 0.2195 0.0839 0.060 Uiso 1 1 calc R . . H11C H 0.5187 0.2441 -0.0921 0.060 Uiso 1 1 calc R . . C12 C 0.0591(2) 0.43077(13) -0.1010(3) 0.0173(5) Uani 1 1 d . . . C13 C -0.0709(2) 0.35776(13) -0.2301(3) 0.0165(5) Uani 1 1 d . . . C14 C -0.1429(2) 0.30500(13) -0.2486(3) 0.0210(6) Uani 1 1 d . . . H14 H -0.1508 0.2779 -0.1628 0.025 Uiso 1 1 calc R . . C15 C -0.2024(2) 0.29369(14) -0.3969(3) 0.0233(6) Uani 1 1 d . . . H15 H -0.2514 0.2579 -0.4135 0.028 Uiso 1 1 calc R . . C16 C -0.1914(2) 0.33418(14) -0.5225(3) 0.0235(6) Uani 1 1 d . . . H16 H -0.2334 0.3254 -0.6228 0.028 Uiso 1 1 calc R . . C17 C -0.1214(2) 0.38624(13) -0.5041(3) 0.0199(6) Uani 1 1 d . . . H17 H -0.1144 0.4136 -0.5898 0.024 Uiso 1 1 calc R . . C18 C -0.0605(2) 0.39780(13) -0.3551(3) 0.0169(5) Uani 1 1 d . . . C19 C -0.0005(2) 0.34270(13) 0.0575(3) 0.0206(6) Uani 1 1 d . . . H19A H -0.0785 0.3332 0.0729 0.025 Uiso 1 1 calc R . . H19B H 0.0339 0.3702 0.1453 0.025 Uiso 1 1 calc R . . C20 C 0.0642(2) 0.28163(14) 0.0619(3) 0.0229(6) Uani 1 1 d . . . H20 H 0.0432 0.2513 -0.0191 0.028 Uiso 1 1 calc R . . C21 C 0.1492(2) 0.26789(15) 0.1731(4) 0.0276(6) Uani 1 1 d . . . H21 H 0.1730 0.3001 0.2485 0.033 Uiso 1 1 calc R . . C22 C 0.2107(3) 0.20589(16) 0.1896(4) 0.0340(7) Uani 1 1 d . . . H22A H 0.1941 0.1835 0.2830 0.051 Uiso 1 1 calc R . . H22B H 0.2917 0.2139 0.2002 0.051 Uiso 1 1 calc R . . H22C H 0.1867 0.1796 0.0967 0.051 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 0.01568(17) 0.01987(19) 0.01270(17) -0.00006(12) -0.00129(12) 0.00254(13) Br1 0.01745(15) 0.02127(16) 0.01943(15) 0.00418(10) -0.00075(10) -0.00012(10) S1 0.0150(3) 0.0235(3) 0.0135(3) 0.0006(2) 0.0026(2) 0.0026(3) S2 0.0218(3) 0.0178(3) 0.0131(3) 0.0020(2) -0.0006(3) -0.0015(3) N1 0.0165(10) 0.0145(11) 0.0114(10) -0.0006(8) 0.0014(8) 0.0002(8) N2 0.0175(10) 0.0190(11) 0.0123(10) 0.0033(9) 0.0007(8) 0.0010(9) C1 0.0163(12) 0.0134(12) 0.0152(12) 0.0002(10) 0.0024(10) 0.0005(10) C2 0.0189(12) 0.0112(12) 0.0104(12) 0.0003(9) -0.0014(10) -0.0003(10) C3 0.0193(13) 0.0147(13) 0.0169(13) 0.0010(10) 0.0031(10) 0.0023(10) C4 0.0190(13) 0.0154(13) 0.0211(14) 0.0024(10) -0.0025(11) 0.0018(11) C5 0.0295(15) 0.0180(13) 0.0104(12) 0.0004(10) -0.0015(11) -0.0018(11) C6 0.0258(14) 0.0201(14) 0.0127(13) 0.0014(10) 0.0032(11) -0.0011(11) C7 0.0162(12) 0.0135(13) 0.0141(12) 0.0000(9) 0.0005(10) 0.0006(10) C8 0.0181(12) 0.0187(13) 0.0114(12) 0.0011(10) 0.0019(10) 0.0039(10) C9 0.0301(15) 0.0196(14) 0.0156(13) -0.0018(11) 0.0062(11) -0.0013(12) C10 0.0365(17) 0.0234(15) 0.0242(15) 0.0026(12) 0.0055(13) 0.0009(13) C11 0.051(2) 0.0261(18) 0.043(2) -0.0064(15) 0.0121(17) 0.0054(16) C12 0.0167(12) 0.0211(14) 0.0138(12) 0.0025(10) 0.0014(10) 0.0039(11) C13 0.0167(12) 0.0176(13) 0.0148(12) -0.0004(10) 0.0007(10) 0.0050(10) C14 0.0183(13) 0.0195(14) 0.0243(15) 0.0025(11) 0.0008(11) 0.0017(11) C15 0.0216(13) 0.0172(14) 0.0299(16) -0.0046(11) -0.0001(12) -0.0002(11) C16 0.0233(14) 0.0220(15) 0.0220(14) -0.0068(11) -0.0059(11) 0.0080(12) C17 0.0248(14) 0.0173(13) 0.0159(13) 0.0001(10) -0.0020(11) 0.0070(11) C18 0.0178(12) 0.0148(13) 0.0176(13) -0.0004(10) 0.0010(10) 0.0020(10) C19 0.0221(13) 0.0245(14) 0.0144(13) 0.0052(11) 0.0008(11) -0.0034(11) C20 0.0241(14) 0.0195(14) 0.0250(15) 0.0056(11) 0.0032(12) -0.0008(12) C21 0.0235(14) 0.0296(16) 0.0301(16) 0.0061(13) 0.0049(12) 0.0007(13) C22 0.0315(17) 0.0319(18) 0.0383(18) 0.0100(14) 0.0042(14) 0.0089(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 Cu1 C1 1.904(3) . ? Cu1 C12 1.924(3) . ? Cu1 Br1 2.5146(5) . ? S1 C1 1.724(3) . ? S1 C7 1.745(3) . ? S2 C12 1.722(3) . ? S2 C18 1.741(3) . ? N1 C1 1.340(3) . ? N1 C2 1.405(3) . ? N1 C8 1.475(3) . ? N2 C12 1.344(3) . ? N2 C13 1.400(3) . ? N2 C19 1.486(3) . ? C2 C7 1.389(4) . ? C2 C3 1.392(4) . ? C3 C4 1.384(4) . ? C4 C5 1.394(4) . ? C5 C6 1.383(4) . ? C6 C7 1.395(4) . ? C8 C9 1.490(4) . ? C9 C10 1.336(4) . ? C10 C11 1.493(4) . ? C13 C18 1.389(4) . ? C13 C14 1.398(4) . ? C14 C15 1.386(4) . ? C15 C16 1.400(4) . ? C16 C17 1.373(4) . ? C17 C18 1.399(4) . ? C19 C20 1.495(4) . ? C20 C21 1.320(4) . ? C21 C22 1.491(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 C1 Cu1 C12 142.81(11) . . ? C1 Cu1 Br1 111.32(8) . . ? C12 Cu1 Br1 104.24(8) . . ? C1 S1 C7 93.76(13) . . ? C12 S2 C18 93.63(13) . . ? C1 N1 C2 117.8(2) . . ? C1 N1 C8 120.4(2) . . ? C2 N1 C8 121.7(2) . . ? C12 N2 C13 117.2(2) . . ? C12 N2 C19 121.5(2) . . ? C13 N2 C19 121.3(2) . . ? N1 C1 S1 108.15(18) . . ? N1 C1 Cu1 126.53(19) . . ? S1 C1 Cu1 125.32(15) . . ? C7 C2 C3 121.1(2) . . ? C7 C2 N1 111.1(2) . . ? C3 C2 N1 127.7(2) . . ? C4 C3 C2 117.4(2) . . ? C3 C4 C5 121.4(2) . . ? C6 C5 C4 121.3(2) . . ? C5 C6 C7 117.4(3) . . ? C2 C7 C6 121.3(2) . . ? C2 C7 S1 109.23(19) . . ? C6 C7 S1 129.4(2) . . ? N1 C8 C9 110.6(2) . . ? C10 C9 C8 123.6(3) . . ? C9 C10 C11 124.4(3) . . ? N2 C12 S2 108.50(19) . . ? N2 C12 Cu1 129.87(19) . . ? S2 C12 Cu1 121.26(15) . . ? C18 C13 C14 121.2(2) . . ? C18 C13 N2 111.5(2) . . ? C14 C13 N2 127.2(2) . . ? C15 C14 C13 117.5(3) . . ? C14 C15 C16 121.0(3) . . ? C17 C16 C15 121.5(3) . . ? C16 C17 C18 117.9(3) . . ? C13 C18 C17 120.9(2) . . ? C13 C18 S2 109.17(19) . . ? C17 C18 S2 130.0(2) . . ? N2 C19 C20 112.8(2) . . ? C21 C20 C19 123.1(3) . . ? C20 C21 C22 125.2(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.802 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.149 _database_code_depnum_ccdc_archive 'CCDC 952970' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9244 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H48 Cu2 I2 N4 O2 S4' _chemical_formula_weight 1198.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8912(8) _cell_length_b 9.9787(9) _cell_length_c 14.6609(13) _cell_angle_alpha 79.561(2) _cell_angle_beta 73.790(2) _cell_angle_gamma 75.256(2) _cell_volume 1199.39(19) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4586 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 27.56 _exptl_crystal_description PLATE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 2.389 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4801 _exptl_absorpt_correction_T_max 0.8699 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8437 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5463 _reflns_number_gt 4889 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.0620P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5463 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.1034 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.07424(5) 0.43028(4) 0.39187(3) 0.01740(11) Uani 1 1 d . . . I1 I 0.14894(2) 0.663306(19) 0.444744(14) 0.01618(9) Uani 1 1 d . . . S1 S 0.43974(10) 0.33612(8) 0.40497(6) 0.01724(17) Uani 1 1 d . . . S2 S -0.26204(10) 0.50494(9) 0.33642(6) 0.01995(18) Uani 1 1 d . . . N1 N 0.3056(3) 0.1570(3) 0.38222(19) 0.0143(5) Uani 1 1 d . . . N2 N -0.0407(3) 0.6133(3) 0.2297(2) 0.0168(6) Uani 1 1 d . . . C1 C 0.2705(4) 0.2934(3) 0.3931(2) 0.0154(6) Uani 1 1 d . . . C2 C 0.4630(4) 0.0827(3) 0.3808(2) 0.0142(6) Uani 1 1 d . . . C3 C 0.5274(4) -0.0586(3) 0.3714(2) 0.0184(7) Uani 1 1 d . . . H3 H 0.4645 -0.1175 0.3632 0.022 Uiso 1 1 calc R . . C4 C 0.6866(4) -0.1096(3) 0.3743(2) 0.0188(7) Uani 1 1 d . . . H4 H 0.7332 -0.2053 0.3677 0.023 Uiso 1 1 calc R . . C5 C 0.7802(4) -0.0248(4) 0.3869(2) 0.0204(7) Uani 1 1 d . . . H5 H 0.8887 -0.0634 0.3890 0.025 Uiso 1 1 calc R . . C6 C 0.7164(4) 0.1152(3) 0.3962(2) 0.0187(7) Uani 1 1 d . . . H6 H 0.7794 0.1736 0.4049 0.022 Uiso 1 1 calc R . . C7 C 0.5570(4) 0.1680(3) 0.3926(2) 0.0166(6) Uani 1 1 d . . . C8 C 0.1835(4) 0.0916(3) 0.3684(2) 0.0181(7) Uani 1 1 d . . . H8A H 0.0757 0.1392 0.4024 0.022 Uiso 1 1 calc R . . H8B H 0.2019 -0.0075 0.3964 0.022 Uiso 1 1 calc R . . C9 C 0.1892(4) 0.0998(4) 0.2646(3) 0.0223(7) Uani 1 1 d . . . H9 H 0.1830 0.1886 0.2274 0.027 Uiso 1 1 calc R . . C10 C 0.2024(5) -0.0089(4) 0.2223(3) 0.0284(8) Uani 1 1 d . . . H10A H 0.2089 -0.0989 0.2577 0.034 Uiso 1 1 calc R . . H10B H 0.2055 0.0023 0.1561 0.034 Uiso 1 1 calc R . . C11 C -0.0659(4) 0.5224(3) 0.3099(2) 0.0159(6) Uani 1 1 d . . . C12 C -0.3048(4) 0.6185(3) 0.2374(2) 0.0181(7) Uani 1 1 d . . . C13 C -0.4475(4) 0.6628(4) 0.2076(3) 0.0230(7) Uani 1 1 d . . . H13 H -0.5396 0.6268 0.2413 0.028 Uiso 1 1 calc R . . C14 C -0.4511(4) 0.7606(4) 0.1274(3) 0.0248(8) Uani 1 1 d . . . H14 H -0.5464 0.7915 0.1054 0.030 Uiso 1 1 calc R . . C15 C -0.3160(5) 0.8142(4) 0.0788(3) 0.0269(8) Uani 1 1 d . . . H15 H -0.3219 0.8822 0.0248 0.032 Uiso 1 1 calc R . . C16 C -0.1734(4) 0.7709(4) 0.1073(2) 0.0215(7) Uani 1 1 d . . . H16 H -0.0816 0.8073 0.0737 0.026 Uiso 1 1 calc R . . C17 C -0.1700(4) 0.6716(3) 0.1874(2) 0.0165(6) Uani 1 1 d . . . C18 C 0.1179(4) 0.6445(4) 0.1867(2) 0.0210(7) Uani 1 1 d . . . H18A H 0.1784 0.6256 0.2368 0.025 Uiso 1 1 calc R . . H18B H 0.1050 0.7450 0.1626 0.025 Uiso 1 1 calc R . . C19 C 0.2133(4) 0.5611(4) 0.1063(3) 0.0259(8) Uani 1 1 d . . . H19 H 0.3195 0.5739 0.0779 0.031 Uiso 1 1 calc R . . C20 C 0.1650(5) 0.4724(5) 0.0712(3) 0.0383(10) Uani 1 1 d . . . H20A H 0.0598 0.4559 0.0972 0.046 Uiso 1 1 calc R . . H20B H 0.2351 0.4244 0.0198 0.046 Uiso 1 1 calc R . . O1S O 0.7748(4) 0.1285(3) -0.0041(2) 0.0402(7) Uani 1 1 d . . . C1S C 0.7355(5) 0.1649(4) 0.0746(3) 0.0313(9) Uani 1 1 d . . . C2S C 0.8572(8) 0.1518(11) 0.1301(4) 0.099(3) Uani 1 1 d . . . H2S1 H 0.9628 0.1064 0.0940 0.149 Uiso 1 1 calc R . . H2S2 H 0.8276 0.0957 0.1918 0.149 Uiso 1 1 calc R . . H2S3 H 0.8611 0.2449 0.1409 0.149 Uiso 1 1 calc R . . C3S C 0.5657(7) 0.2156(9) 0.1243(4) 0.075(2) Uani 1 1 d . . . H3S1 H 0.4979 0.2305 0.0794 0.112 Uiso 1 1 calc R . . H3S2 H 0.5544 0.3037 0.1488 0.112 Uiso 1 1 calc R . . H3S3 H 0.5325 0.1460 0.1777 0.112 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 0.0130(2) 0.0157(2) 0.0231(2) -0.00057(15) -0.00748(16) -0.00039(15) I1 0.01746(13) 0.01241(12) 0.01831(13) -0.00137(8) -0.00382(8) -0.00353(8) S1 0.0122(4) 0.0128(4) 0.0276(4) -0.0027(3) -0.0067(3) -0.0021(3) S2 0.0150(4) 0.0205(4) 0.0254(4) 0.0040(3) -0.0082(3) -0.0067(3) N1 0.0123(13) 0.0129(12) 0.0180(13) -0.0005(10) -0.0050(10) -0.0027(10) N2 0.0137(13) 0.0162(13) 0.0217(14) -0.0018(10) -0.0063(11) -0.0038(10) C1 0.0131(15) 0.0151(15) 0.0182(16) 0.0003(11) -0.0048(12) -0.0040(12) C2 0.0125(15) 0.0153(15) 0.0128(15) -0.0013(11) -0.0011(11) -0.0017(12) C3 0.0209(17) 0.0162(15) 0.0178(16) -0.0037(12) -0.0044(13) -0.0028(13) C4 0.0206(17) 0.0119(14) 0.0192(16) -0.0029(12) -0.0037(13) 0.0041(12) C5 0.0136(16) 0.0251(17) 0.0190(16) -0.0015(13) -0.0027(13) 0.0000(13) C6 0.0151(16) 0.0180(15) 0.0220(17) -0.0011(12) -0.0052(13) -0.0020(12) C7 0.0177(16) 0.0142(14) 0.0188(16) -0.0012(12) -0.0051(13) -0.0052(12) C8 0.0144(16) 0.0165(15) 0.0254(18) -0.0045(13) -0.0062(13) -0.0039(12) C9 0.0199(17) 0.0221(17) 0.0268(19) 0.0002(14) -0.0103(14) -0.0050(13) C10 0.028(2) 0.034(2) 0.0268(19) -0.0066(16) -0.0078(16) -0.0095(16) C11 0.0124(15) 0.0132(14) 0.0231(17) -0.0026(12) -0.0060(12) -0.0023(11) C12 0.0172(16) 0.0160(15) 0.0199(16) 0.0017(12) -0.0071(13) -0.0015(12) C13 0.0161(17) 0.0281(18) 0.0248(18) -0.0040(14) -0.0094(14) 0.0007(13) C14 0.0222(18) 0.0259(18) 0.0270(19) -0.0048(14) -0.0142(15) 0.0039(14) C15 0.035(2) 0.0219(17) 0.0225(18) 0.0016(14) -0.0133(16) -0.0007(15) C16 0.0256(18) 0.0195(16) 0.0199(17) 0.0003(13) -0.0073(14) -0.0056(13) C17 0.0158(16) 0.0141(14) 0.0214(16) -0.0040(12) -0.0085(13) -0.0008(12) C18 0.0180(17) 0.0259(17) 0.0212(17) 0.0016(13) -0.0049(13) -0.0114(14) C19 0.0175(18) 0.0316(19) 0.0244(19) -0.0017(15) -0.0032(14) -0.0008(14) C20 0.029(2) 0.040(2) 0.044(3) -0.023(2) -0.0020(18) 0.0006(18) O1S 0.050(2) 0.0360(16) 0.0291(16) 0.0042(13) -0.0051(14) -0.0101(14) C1S 0.031(2) 0.036(2) 0.024(2) 0.0068(16) -0.0069(16) -0.0101(17) C2S 0.050(4) 0.223(10) 0.031(3) 0.008(4) -0.016(3) -0.051(5) C3S 0.039(3) 0.137(6) 0.036(3) -0.011(3) -0.010(2) 0.004(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 C11 1.923(3) . ? Cu1 C1 1.925(3) . ? Cu1 I1 2.8331(5) 2_566 ? Cu1 I1 2.8594(5) . ? I1 Cu1 2.8330(5) 2_566 ? S1 C1 1.724(3) . ? S1 C7 1.746(3) . ? S2 C11 1.724(3) . ? S2 C12 1.740(3) . ? N1 C1 1.346(4) . ? N1 C2 1.403(4) . ? N1 C8 1.476(4) . ? N2 C11 1.351(4) . ? N2 C17 1.404(4) . ? N2 C18 1.463(4) . ? C2 C3 1.396(4) . ? C2 C7 1.396(4) . ? C3 C4 1.388(5) . ? C4 C5 1.394(5) . ? C5 C6 1.384(5) . ? C6 C7 1.393(5) . ? C8 C9 1.497(5) . ? C9 C10 1.309(5) . ? C12 C17 1.395(5) . ? C12 C13 1.396(5) . ? C13 C14 1.388(5) . ? C14 C15 1.395(6) . ? C15 C16 1.385(5) . ? C16 C17 1.394(5) . ? C18 C19 1.497(5) . ? C19 C20 1.310(6) . ? O1S C1S 1.203(5) . ? C1S C3S 1.482(7) . ? C1S C2S 1.494(7) . ? 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 C11 Cu1 C1 141.65(14) . . ? C11 Cu1 I1 100.56(10) . 2_566 ? C1 Cu1 I1 103.87(10) . 2_566 ? C11 Cu1 I1 101.27(9) . . ? C1 Cu1 I1 100.49(10) . . ? I1 Cu1 I1 104.817(15) 2_566 . ? Cu1 I1 Cu1 75.183(15) 2_566 . ? C1 S1 C7 93.82(16) . . ? C11 S2 C12 93.93(16) . . ? C1 N1 C2 117.4(3) . . ? C1 N1 C8 120.5(3) . . ? C2 N1 C8 122.1(3) . . ? C11 N2 C17 117.6(3) . . ? C11 N2 C18 120.7(3) . . ? C17 N2 C18 121.6(3) . . ? N1 C1 S1 108.4(2) . . ? N1 C1 Cu1 129.4(2) . . ? S1 C1 Cu1 122.10(17) . . ? C3 C2 C7 120.5(3) . . ? C3 C2 N1 128.0(3) . . ? C7 C2 N1 111.5(3) . . ? C4 C3 C2 117.5(3) . . ? C3 C4 C5 122.0(3) . . ? C6 C5 C4 120.5(3) . . ? C5 C6 C7 118.0(3) . . ? C6 C7 C2 121.4(3) . . ? C6 C7 S1 129.6(3) . . ? C2 C7 S1 108.9(2) . . ? N1 C8 C9 111.3(3) . . ? C10 C9 C8 123.5(3) . . ? N2 C11 S2 108.0(2) . . ? N2 C11 Cu1 130.1(2) . . ? S2 C11 Cu1 121.76(18) . . ? C17 C12 C13 120.5(3) . . ? C17 C12 S2 109.4(2) . . ? C13 C12 S2 130.0(3) . . ? C14 C13 C12 118.2(3) . . ? C13 C14 C15 120.6(3) . . ? C16 C15 C14 121.8(3) . . ? C15 C16 C17 117.3(3) . . ? C16 C17 C12 121.5(3) . . ? C16 C17 N2 127.5(3) . . ? C12 C17 N2 111.0(3) . . ? N2 C18 C19 113.2(3) . . ? C20 C19 C18 126.5(4) . . ? O1S C1S C3S 122.7(4) . . ? O1S C1S C2S 120.8(5) . . ? C3S C1S C2S 116.3(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.844 _refine_diff_density_min -0.860 _refine_diff_density_rms 0.232 _database_code_depnum_ccdc_archive 'CCDC 952971'