Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global #=== _journal_coden_Cambridge 222 _publ_contact_author_name ; David Rorabacher ; _publ_contact_author_address ; Department of Chemistry Wayne State University Detroit, Michigan 48202 ; _publ_contact_author_email dbr@chem.wayne.edu _publ_requested_journal 'Dalton Trans' _publ_section_title ; Comparative Study of Donor Atom Effects on the Thermodynamic and Electron-Transfer Kinetic Properties of Copper(II/I) Complexes with Sexadentate Macrocyclic Ligands. CuII/I([18]aneS4N2) and CuII/I([18]aneS4O2) ; loop_ _publ_author_name _publ_author_address 'Gezahegn Chaka' ; Department of Chemistry Wayne State University Detroit, Michigan 48202 USA ; 'Ashoka Kandegedara' ; Department of Chemistry Wayne State University Detroit, Michigan 48202 USA ; 'Mary Jane Heeg' ; Department of Chemistry Wayne State University Detroit, Michigan 48202 USA ; 'D. B. Rorabacher' ; Department of Chemistry Wayne State University Detroit, Michigan 48202 USA ; #=== data_asho _database_code_depnum_ccdc_archive 'CCDC 619234' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H24 Cl2 Cu O10 S4' _chemical_formula_weight 590.99 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M P-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' _cell_length_a 10.4913(15) _cell_length_b 10.4913(15) _cell_length_c 5.4814(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 522.49(15) _cell_formula_units_Z 1 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 870 _cell_measurement_theta_min 4. _cell_measurement_theta_max 28. _exptl_crystal_description rod _exptl_crystal_colour dark _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.878 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 303 _exptl_absorpt_coefficient_mu 1.750 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5412 _exptl_absorpt_correction_T_max 0.7793 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method 'SMART CCD' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3634 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 14.45 _diffrn_reflns_theta_max 28.28 _reflns_number_total 682 _reflns_number_gt 592 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXL-93 _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^)+(0.0188P)^2^+0.3078P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 682 _refine_ls_number_parameters 46 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0703 _refine_ls_wR_factor_gt 0.0678 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 0.0000 0.0000 0.5000 0.0280(3) Uani 1 6 d S . . Cl1 Cl -0.3333 0.3333 0.87968(18) 0.0374(3) Uani 1 3 d S . . O1 O 0.1954(3) 0.5520(4) 1.0353(7) 0.0805(8) Uani 1 1 d . . . O2 O 0.3333 0.6667 1.3782(9) 0.100(2) Uani 1 3 d S . . S1 S 0.09183(9) 0.21665(8) 0.73207(13) 0.0376(3) Uani 0.67 1 d P A 1 O3 O 0.09183(9) 0.21665(8) 0.73207(13) 0.0376(3) Uani 0.33 1 d P A 2 C1 C -0.0074(4) 0.2968(4) 0.6328(7) 0.0560(8) Uani 1 1 d . . . H1A H -0.0929 0.2631 0.7373 0.067 Uiso 1 1 calc R A 1 H1B H 0.0528 0.4024 0.6549 0.067 Uiso 1 1 calc R A 1 C2 C 0.2681(4) 0.3274(3) 0.6280(7) 0.0559(7) Uani 1 1 d . . . H2A H 0.2925 0.4292 0.6464 0.067 Uiso 1 1 calc R A 1 H2B H 0.3344 0.3127 0.7318 0.067 Uiso 1 1 calc R 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 0.0262(3) 0.0262(3) 0.0315(4) 0.000 0.000 0.01310(17) Cl1 0.0340(4) 0.0340(4) 0.0441(5) 0.000 0.000 0.01698(19) O1 0.0474(13) 0.0613(16) 0.108(2) -0.0090(14) -0.0149(13) 0.0088(12) O2 0.127(3) 0.127(3) 0.047(2) 0.000 0.000 0.0634(17) S1 0.0365(4) 0.0376(4) 0.0389(4) -0.0095(3) -0.0033(3) 0.0185(3) O3 0.0365(4) 0.0376(4) 0.0389(4) -0.0095(3) -0.0033(3) 0.0185(3) C1 0.0565(17) 0.0448(15) 0.0747(19) -0.0150(13) -0.0049(14) 0.0312(14) C2 0.0456(15) 0.0396(14) 0.0728(19) -0.0162(13) -0.0115(13) 0.0142(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 2.3500(7) 4_556 ? Cu1 S1 2.3500(7) 4_556 ? Cu1 S1 2.3500(7) . ? Cu1 O3 2.3500(7) 3 ? Cu1 S1 2.3500(7) 5_556 ? Cu1 S1 2.3500(7) 3 ? Cu1 O3 2.3500(7) 5_556 ? Cu1 S1 2.3500(7) 2 ? Cu1 O3 2.3500(7) 2 ? Cu1 O3 2.3500(7) 6_556 ? Cu1 S1 2.3500(7) 6_556 ? Cl1 O2 1.414(5) 4_567 ? Cl1 O1 1.420(3) 6_557 ? Cl1 O1 1.420(3) 4_567 ? Cl1 O1 1.420(3) 5_457 ? O1 Cl1 1.420(3) 4_567 ? O2 Cl1 1.414(5) 4_567 ? S1 C2 1.716(4) . ? S1 C1 1.721(3) . ? C1 C2 1.506(5) 6_556 ? C2 C1 1.506(5) 5_556 ? 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 O3 Cu1 S1 0.00(4) 4_556 4_556 ? O3 Cu1 S1 180.00(4) 4_556 . ? S1 Cu1 S1 180.00(4) 4_556 . ? O3 Cu1 O3 86.53(3) 4_556 3 ? S1 Cu1 O3 86.53(3) 4_556 3 ? S1 Cu1 O3 93.47(3) . 3 ? O3 Cu1 S1 93.47(3) 4_556 5_556 ? S1 Cu1 S1 93.47(3) 4_556 5_556 ? S1 Cu1 S1 86.53(3) . 5_556 ? O3 Cu1 S1 86.53(3) 3 5_556 ? O3 Cu1 S1 86.53(3) 4_556 3 ? S1 Cu1 S1 86.53(3) 4_556 3 ? S1 Cu1 S1 93.47(3) . 3 ? O3 Cu1 S1 0.00(4) 3 3 ? S1 Cu1 S1 86.53(3) 5_556 3 ? O3 Cu1 O3 93.47(3) 4_556 5_556 ? S1 Cu1 O3 93.47(3) 4_556 5_556 ? S1 Cu1 O3 86.53(3) . 5_556 ? O3 Cu1 O3 86.53(3) 3 5_556 ? S1 Cu1 O3 0.00(4) 5_556 5_556 ? S1 Cu1 O3 86.53(3) 3 5_556 ? O3 Cu1 S1 86.53(3) 4_556 2 ? S1 Cu1 S1 86.53(3) 4_556 2 ? S1 Cu1 S1 93.47(3) . 2 ? O3 Cu1 S1 93.47(3) 3 2 ? S1 Cu1 S1 180.00(3) 5_556 2 ? S1 Cu1 S1 93.47(3) 3 2 ? O3 Cu1 S1 180.00(3) 5_556 2 ? O3 Cu1 O3 86.53(3) 4_556 2 ? S1 Cu1 O3 86.53(3) 4_556 2 ? S1 Cu1 O3 93.47(3) . 2 ? O3 Cu1 O3 93.47(3) 3 2 ? S1 Cu1 O3 180.00(3) 5_556 2 ? S1 Cu1 O3 93.47(3) 3 2 ? O3 Cu1 O3 180.00(3) 5_556 2 ? S1 Cu1 O3 0.00(6) 2 2 ? O3 Cu1 O3 93.47(3) 4_556 6_556 ? S1 Cu1 O3 93.47(3) 4_556 6_556 ? S1 Cu1 O3 86.53(3) . 6_556 ? O3 Cu1 O3 180.0 3 6_556 ? S1 Cu1 O3 93.47(3) 5_556 6_556 ? S1 Cu1 O3 180.0 3 6_556 ? O3 Cu1 O3 93.47(3) 5_556 6_556 ? S1 Cu1 O3 86.53(3) 2 6_556 ? O3 Cu1 O3 86.53(3) 2 6_556 ? O3 Cu1 S1 93.47(3) 4_556 6_556 ? S1 Cu1 S1 93.47(3) 4_556 6_556 ? S1 Cu1 S1 86.53(3) . 6_556 ? O3 Cu1 S1 180.0 3 6_556 ? S1 Cu1 S1 93.47(3) 5_556 6_556 ? S1 Cu1 S1 180.0 3 6_556 ? O3 Cu1 S1 93.47(3) 5_556 6_556 ? S1 Cu1 S1 86.53(3) 2 6_556 ? O3 Cu1 S1 86.53(3) 2 6_556 ? O3 Cu1 S1 0.00(3) 6_556 6_556 ? O2 Cl1 O1 109.16(17) 4_567 6_557 ? O2 Cl1 O1 109.16(17) 4_567 4_567 ? O1 Cl1 O1 109.78(17) 6_557 4_567 ? O2 Cl1 O1 109.16(17) 4_567 5_457 ? O1 Cl1 O1 109.78(17) 6_557 5_457 ? O1 Cl1 O1 109.78(17) 4_567 5_457 ? C2 S1 C1 105.90(19) . . ? C2 S1 Cu1 104.89(11) . . ? C1 S1 Cu1 104.23(11) . . ? C2 C1 S1 116.7(2) 6_556 . ? C1 C2 S1 116.2(2) 5_556 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Cu1 S1 C2 28(7) 4_556 . . . ? S1 Cu1 S1 C2 28(7) 4_556 . . . ? O3 Cu1 S1 C2 78.62(14) 3 . . . ? S1 Cu1 S1 C2 -7.69(13) 5_556 . . . ? S1 Cu1 S1 C2 78.62(14) 3 . . . ? O3 Cu1 S1 C2 -7.69(13) 5_556 . . . ? S1 Cu1 S1 C2 172.31(13) 2 . . . ? O3 Cu1 S1 C2 172.31(13) 2 . . . ? O3 Cu1 S1 C2 -101.38(14) 6_556 . . . ? S1 Cu1 S1 C2 -101.38(14) 6_556 . . . ? O3 Cu1 S1 C1 139(7) 4_556 . . . ? S1 Cu1 S1 C1 139(7) 4_556 . . . ? O3 Cu1 S1 C1 -170.29(13) 3 . . . ? S1 Cu1 S1 C1 103.40(14) 5_556 . . . ? S1 Cu1 S1 C1 -170.29(13) 3 . . . ? O3 Cu1 S1 C1 103.40(14) 5_556 . . . ? S1 Cu1 S1 C1 -76.60(14) 2 . . . ? O3 Cu1 S1 C1 -76.60(14) 2 . . . ? O3 Cu1 S1 C1 9.71(13) 6_556 . . . ? S1 Cu1 S1 C1 9.71(13) 6_556 . . . ? C2 S1 C1 C2 80.4(3) . . . 6_556 ? Cu1 S1 C1 C2 -30.0(3) . . . 6_556 ? C1 S1 C2 C1 -81.8(3) . . . 5_556 ? Cu1 S1 C2 C1 28.1(3) . . . 5_556 ? _diffrn_measured_fraction_theta_max 0.792 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.792 _refine_diff_density_max 0.256 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.041 #=== data_meza _database_code_depnum_ccdc_archive 'CCDC 619235' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H24 Cl Cu O6 S4' _chemical_formula_weight 491.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.5531(8) _cell_length_b 9.8811(4) _cell_length_c 24.7535(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3804.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6519 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 31.8 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 1.753 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7432 _exptl_absorpt_correction_T_max 0.8172 _exptl_absorpt_process_details ? _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 'Bruker APEX2 kappa' _diffrn_measurement_method 'Bruker APEX2' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31315 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 33.24 _reflns_number_total 6439 _reflns_number_gt 4874 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXL-97 _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^)+(0.0334P)^2^+1.9327P] 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 6439 _refine_ls_number_parameters 305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.383241(14) 0.81918(2) 0.870853(9) 0.01169(6) Uani 1 1 d . . . S1 S 0.47637(3) 0.97139(5) 0.831035(18) 0.01216(10) Uani 1 1 d . . . S2 S 0.37557(3) 0.68310(5) 0.794765(19) 0.01176(9) Uani 1 1 d . . . O1 O 0.18660(10) 0.84310(15) 0.80360(6) 0.0220(3) Uani 1 1 d . . . S3 S 0.26555(3) 0.92376(5) 0.909339(19) 0.01324(10) Uani 1 1 d . . . S4 S 0.41244(3) 0.69095(5) 0.947358(19) 0.01362(10) Uani 1 1 d . . . O2 O 0.55758(9) 0.94320(13) 0.94062(5) 0.0155(3) Uani 1 1 d . . . C1 C 0.46538(13) 0.9134(2) 0.76203(7) 0.0143(4) Uani 1 1 d . . . C2 C 0.46185(12) 0.7606(2) 0.75661(8) 0.0141(4) Uani 1 1 d . . . C3 C 0.28421(13) 0.7150(2) 0.75057(8) 0.0169(4) Uani 1 1 d . . . C4 C 0.20078(13) 0.7104(2) 0.78174(9) 0.0227(4) Uani 1 1 d . . . H4A H 0.1528 0.6847 0.7575 0.027 Uiso 1 1 calc R . . H4B H 0.2045 0.6429 0.8112 0.027 Uiso 1 1 calc R . . C5 C 0.12838(14) 0.8443(2) 0.84750(9) 0.0209(4) Uani 1 1 d . . . C6 C 0.17136(14) 0.8155(2) 0.90065(9) 0.0207(4) Uani 1 1 d . . . C7 C 0.29206(14) 0.8855(2) 0.97913(8) 0.0159(4) Uani 1 1 d . . . C8 C 0.31995(13) 0.7395(2) 0.98784(8) 0.0164(4) Uani 1 1 d . . . C9 C 0.49823(14) 0.7588(2) 0.99013(8) 0.0198(4) Uani 1 1 d . . . C10 C 0.57467(13) 0.8083(2) 0.95814(9) 0.0179(4) Uani 1 1 d . . . C11 C 0.61402(14) 0.9852(2) 0.89824(8) 0.0182(4) Uani 1 1 d . . . C12 C 0.58798(12) 0.9253(2) 0.84424(8) 0.0162(4) Uani 1 1 d . . . Cl1 Cl 0.62165(3) 0.47510(5) 0.873743(18) 0.01486(10) Uani 1 1 d . . . O3 O 0.65076(11) 0.51085(16) 0.92704(6) 0.0263(4) Uani 1 1 d . . . O4 O 0.55627(11) 0.56889(16) 0.85633(6) 0.0266(4) Uani 1 1 d . . . O5 O 0.69268(11) 0.48080(19) 0.83677(7) 0.0335(4) Uani 1 1 d . . . O6 O 0.58718(12) 0.34027(16) 0.87447(7) 0.0328(4) Uani 1 1 d . . . H1A H 0.4114(15) 0.956(2) 0.7495(9) 0.017(6) Uiso 1 1 d . . . H1B H 0.5136(18) 0.949(3) 0.7426(11) 0.032(7) Uiso 1 1 d . . . H2A H 0.5117(15) 0.719(2) 0.7707(9) 0.016(6) Uiso 1 1 d . . . H2B H 0.4563(14) 0.734(2) 0.7180(9) 0.015(6) Uiso 1 1 d . . . H3A H 0.2844(17) 0.651(3) 0.7255(11) 0.035(7) Uiso 1 1 d . . . H3B H 0.2925(16) 0.801(3) 0.7342(10) 0.026(7) Uiso 1 1 d . . . H5A H 0.0852(15) 0.779(2) 0.8411(9) 0.015(6) Uiso 1 1 d . . . H5B H 0.1079(16) 0.937(3) 0.8475(10) 0.029(7) Uiso 1 1 d . . . H6A H 0.1916(19) 0.710(3) 0.9013(11) 0.042(8) Uiso 1 1 d . . . H6B H 0.1318(18) 0.838(3) 0.9289(12) 0.039(8) Uiso 1 1 d . . . H7A H 0.2438(15) 0.905(2) 1.0002(9) 0.022(6) Uiso 1 1 d . . . H7B H 0.3386(14) 0.945(2) 0.9880(9) 0.013(5) Uiso 1 1 d . . . H8A H 0.3342(16) 0.723(3) 1.0246(10) 0.030(7) Uiso 1 1 d . . . H8B H 0.2770(16) 0.678(2) 0.9779(9) 0.020(6) Uiso 1 1 d . . . H9A H 0.4757(15) 0.830(2) 1.0107(10) 0.018(6) Uiso 1 1 d . . . H9B H 0.5161(17) 0.689(3) 1.0112(11) 0.030(7) Uiso 1 1 d . . . H10A H 0.5864(15) 0.748(2) 0.9283(9) 0.019(6) Uiso 1 1 d . . . H10B H 0.6279(15) 0.810(2) 0.9814(10) 0.020(6) Uiso 1 1 d . . . H11A H 0.6077(14) 1.084(2) 0.8954(9) 0.011(5) Uiso 1 1 d . . . H11B H 0.6713(17) 0.960(2) 0.9047(9) 0.024(6) Uiso 1 1 d . . . H12A H 0.5965(13) 0.834(2) 0.8426(9) 0.009(5) Uiso 1 1 d . . . H12B H 0.6222(17) 0.963(3) 0.8153(11) 0.032(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00968(11) 0.01547(13) 0.00992(11) 0.00024(8) 0.00125(8) -0.00043(9) S1 0.0124(2) 0.0117(2) 0.0124(2) -0.00034(16) 0.00069(17) -0.00147(16) S2 0.0106(2) 0.0113(2) 0.0133(2) -0.00061(16) -0.00111(16) 0.00013(16) O1 0.0205(7) 0.0223(8) 0.0231(8) 0.0000(6) 0.0035(6) 0.0008(6) S3 0.0119(2) 0.0130(2) 0.0147(2) 0.00001(17) 0.00289(17) -0.00009(17) S4 0.0140(2) 0.0145(2) 0.0123(2) 0.00135(17) -0.00160(17) -0.00038(17) O2 0.0152(7) 0.0157(7) 0.0155(7) -0.0013(5) 0.0010(5) 0.0002(5) C1 0.0167(9) 0.0168(10) 0.0094(8) 0.0008(7) 0.0014(7) -0.0025(8) C2 0.0125(9) 0.0167(9) 0.0130(9) -0.0032(7) 0.0025(7) -0.0009(7) C3 0.0131(9) 0.0225(11) 0.0151(9) -0.0028(8) -0.0028(7) 0.0011(8) C4 0.0126(9) 0.0260(11) 0.0296(11) 0.0004(9) -0.0040(9) -0.0030(8) C5 0.0154(10) 0.0244(11) 0.0228(11) 0.0067(9) -0.0007(8) -0.0026(9) C6 0.0151(9) 0.0272(12) 0.0199(10) 0.0023(8) 0.0018(8) -0.0062(8) C7 0.0181(9) 0.0176(10) 0.0121(9) -0.0020(7) 0.0040(7) -0.0011(8) C8 0.0162(9) 0.0207(10) 0.0123(9) 0.0026(8) 0.0026(7) -0.0016(8) C9 0.0181(10) 0.0251(12) 0.0161(10) 0.0034(9) -0.0052(8) -0.0046(9) C10 0.0149(9) 0.0184(10) 0.0204(10) 0.0023(8) -0.0030(8) 0.0004(8) C11 0.0163(10) 0.0197(11) 0.0185(10) -0.0009(8) -0.0012(8) -0.0054(8) C12 0.0100(8) 0.0215(11) 0.0171(9) -0.0014(8) 0.0018(7) -0.0013(8) Cl1 0.0170(2) 0.0141(2) 0.0135(2) -0.00103(16) -0.00402(17) 0.00055(17) O3 0.0373(9) 0.0257(8) 0.0159(7) -0.0034(6) -0.0125(7) 0.0037(7) O4 0.0302(9) 0.0249(8) 0.0246(8) -0.0047(6) -0.0127(7) 0.0122(7) O5 0.0220(8) 0.0494(11) 0.0292(9) -0.0056(8) 0.0066(7) -0.0038(8) O6 0.0432(10) 0.0191(8) 0.0362(10) 0.0039(7) -0.0115(8) -0.0111(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 S3 2.3078(5) . ? Cu1 S1 2.3090(5) . ? Cu1 S2 2.3172(5) . ? Cu1 S4 2.3234(5) . ? S1 C1 1.8097(19) . ? S1 C12 1.824(2) . ? S2 C2 1.8107(19) . ? S2 C3 1.821(2) . ? O1 C5 1.415(3) . ? O1 C4 1.436(3) . ? S3 C7 1.816(2) . ? S3 C6 1.827(2) . ? S4 C8 1.817(2) . ? S4 C9 1.830(2) . ? O2 C10 1.427(2) . ? O2 C11 1.429(2) . ? C1 C2 1.517(3) . ? C3 C4 1.510(3) . ? C5 C6 1.503(3) . ? C7 C8 1.523(3) . ? C9 C10 1.510(3) . ? C11 C12 1.517(3) . ? Cl1 O5 1.4357(17) . ? Cl1 O6 1.4362(17) . ? Cl1 O3 1.4388(15) . ? Cl1 O4 1.4417(15) . ? 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 S3 Cu1 S1 112.465(19) . . ? S3 Cu1 S2 123.678(19) . . ? S1 Cu1 S2 93.629(18) . . ? S3 Cu1 S4 93.598(19) . . ? S1 Cu1 S4 125.488(19) . . ? S2 Cu1 S4 110.862(19) . . ? C1 S1 C12 100.37(9) . . ? C1 S1 Cu1 97.90(7) . . ? C12 S1 Cu1 110.96(7) . . ? C2 S2 C3 101.06(10) . . ? C2 S2 Cu1 98.08(6) . . ? C3 S2 Cu1 115.35(7) . . ? C5 O1 C4 113.31(17) . . ? C7 S3 C6 99.92(10) . . ? C7 S3 Cu1 96.87(7) . . ? C6 S3 Cu1 108.97(8) . . ? C8 S4 C9 99.29(10) . . ? C8 S4 Cu1 98.68(7) . . ? C9 S4 Cu1 114.47(7) . . ? C10 O2 C11 112.32(16) . . ? C2 C1 S1 113.70(13) . . ? C1 C2 S2 113.66(13) . . ? C4 C3 S2 111.00(14) . . ? O1 C4 C3 107.29(17) . . ? O1 C5 C6 112.72(18) . . ? C5 C6 S3 110.40(15) . . ? C8 C7 S3 113.36(14) . . ? C7 C8 S4 113.42(14) . . ? C10 C9 S4 112.91(15) . . ? O2 C10 C9 108.39(17) . . ? O2 C11 C12 111.69(16) . . ? C11 C12 S1 108.33(14) . . ? O5 Cl1 O6 109.37(11) . . ? O5 Cl1 O3 109.43(10) . . ? O6 Cl1 O3 109.49(10) . . ? O5 Cl1 O4 109.09(11) . . ? O6 Cl1 O4 109.68(11) . . ? O3 Cl1 O4 109.77(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S3 Cu1 S1 C1 -116.18(7) . . . . ? S2 Cu1 S1 C1 12.68(7) . . . . ? S4 Cu1 S1 C1 131.59(7) . . . . ? S3 Cu1 S1 C12 139.47(7) . . . . ? S2 Cu1 S1 C12 -91.66(7) . . . . ? S4 Cu1 S1 C12 27.25(8) . . . . ? S3 Cu1 S2 C2 130.58(7) . . . . ? S1 Cu1 S2 C2 10.42(7) . . . . ? S4 Cu1 S2 C2 -119.87(7) . . . . ? S3 Cu1 S2 C3 24.22(9) . . . . ? S1 Cu1 S2 C3 -95.94(8) . . . . ? S4 Cu1 S2 C3 133.77(8) . . . . ? S1 Cu1 S3 C7 -112.66(7) . . . . ? S2 Cu1 S3 C7 136.37(7) . . . . ? S4 Cu1 S3 C7 18.29(7) . . . . ? S1 Cu1 S3 C6 144.34(8) . . . . ? S2 Cu1 S3 C6 33.38(8) . . . . ? S4 Cu1 S3 C6 -84.70(8) . . . . ? S3 Cu1 S4 C8 4.94(7) . . . . ? S1 Cu1 S4 C8 125.94(7) . . . . ? S2 Cu1 S4 C8 -123.27(7) . . . . ? S3 Cu1 S4 C9 -99.46(9) . . . . ? S1 Cu1 S4 C9 21.54(9) . . . . ? S2 Cu1 S4 C9 132.32(9) . . . . ? C12 S1 C1 C2 72.50(16) . . . . ? Cu1 S1 C1 C2 -40.61(14) . . . . ? S1 C1 C2 S2 57.56(18) . . . . ? C3 S2 C2 C1 79.24(16) . . . . ? Cu1 S2 C2 C1 -38.69(14) . . . . ? C2 S2 C3 C4 -157.61(15) . . . . ? Cu1 S2 C3 C4 -53.06(17) . . . . ? C5 O1 C4 C3 -160.11(17) . . . . ? S2 C3 C4 O1 86.46(18) . . . . ? C4 O1 C5 C6 85.6(2) . . . . ? O1 C5 C6 S3 50.3(2) . . . . ? C7 S3 C6 C5 171.53(16) . . . . ? Cu1 S3 C6 C5 -87.61(16) . . . . ? C6 S3 C7 C8 65.26(17) . . . . ? Cu1 S3 C7 C8 -45.44(15) . . . . ? S3 C7 C8 S4 57.90(18) . . . . ? C9 S4 C8 C7 82.27(16) . . . . ? Cu1 S4 C8 C7 -34.44(15) . . . . ? C8 S4 C9 C10 -147.20(16) . . . . ? Cu1 S4 C9 C10 -43.17(18) . . . . ? C11 O2 C10 C9 -163.73(16) . . . . ? S4 C9 C10 O2 83.95(19) . . . . ? C10 O2 C11 C12 77.4(2) . . . . ? O2 C11 C12 S1 55.7(2) . . . . ? C1 S1 C12 C11 171.64(15) . . . . ? Cu1 S1 C12 C11 -85.66(15) . . . . ? _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.225 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.110 #===end