# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_[Cl2iPr2Cu]2(u-S(CH2)3S) _database_code_depnum_ccdc_archive 'CCDC 909176' #TrackingRef '15147_web_deposit_cif_file_0_TimothyH.Warren_1352065596.cmpd_3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cl2iPr2Cu]2(u-S(CH2)3S)' _chemical_melting_point ? _chemical_formula_moiety 'C57 H74 N4 S2 Cl4 Cu2' _chemical_formula_sum 'C57 H74 Cl4 Cu2 N4 S2' _chemical_formula_weight 1148.20 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' 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 C2221 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, -z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 14.073(3) _cell_length_b 21.020(4) _cell_length_c 19.083(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5644.9(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12162 _cell_measurement_theta_min 5.500 _cell_measurement_theta_max 36.647 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2408 _exptl_absorpt_coefficient_mu 1.057 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6300 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details "SADABS based on Blessing's method; Blessing, Acta Cryst. (1995) A51 33-38" _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22035 _diffrn_reflns_av_R_equivalents 0.1101 _diffrn_reflns_av_sigmaI/netI 0.1089 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5502 _reflns_number_gt 3859 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker APEXII' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows; Ferrugia L J (1997), J. Appl. Cryst. 30, 565' _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^)+(0.0574P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 5502 _refine_ls_number_parameters 327 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1098 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.1342 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.034 _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 0.92856(6) 0.73729(3) 0.80251(4) 0.0268(2) Uani 1 1 d . . . Cl1 Cl 0.73337(12) 0.74117(8) 1.05872(8) 0.0379(4) Uani 1 1 d . . . Cl2 Cl 0.79394(13) 0.58479(8) 1.02692(9) 0.0377(5) Uani 1 1 d . . . S1 S 1.08848(12) 0.77076(8) 0.81001(9) 0.0390(4) Uani 1 1 d D . . N1 N 0.8191(3) 0.7457(2) 0.9308(2) 0.0203(11) Uani 1 1 d . . . N2 N 0.8523(4) 0.6470(2) 0.9098(2) 0.0220(12) Uani 1 1 d . . . C1 C 0.8603(4) 0.7068(3) 0.8807(3) 0.0221(14) Uani 1 1 d . . . C2 C 0.7879(4) 0.7106(3) 0.9889(3) 0.0221(14) Uani 1 1 d . . . C3 C 0.8105(4) 0.6498(3) 0.9747(3) 0.0227(14) Uani 1 1 d . . . C4 C 0.8061(4) 0.8134(3) 0.9197(3) 0.0195(13) Uani 1 1 d . . . C5 C 0.7335(5) 0.8316(3) 0.8728(3) 0.0254(15) Uani 1 1 d . . . C6 C 0.7264(5) 0.8964(3) 0.8583(3) 0.0302(16) Uani 1 1 d . . . H6 H 0.6804 0.9104 0.8254 0.036 Uiso 1 1 calc R . . C7 C 0.7830(5) 0.9400(3) 0.8897(3) 0.0312(16) Uani 1 1 d U . . H7 H 0.7766 0.9838 0.8785 0.037 Uiso 1 1 calc R . . C8 C 0.8499(5) 0.9205(3) 0.9382(4) 0.0391(18) Uani 1 1 d . . . H8 H 0.8884 0.9517 0.9604 0.047 Uiso 1 1 calc R . . C9 C 0.8632(4) 0.8560(3) 0.9558(3) 0.0229(14) Uani 1 1 d . . . C10 C 0.8751(4) 0.5885(3) 0.8748(3) 0.0213(14) Uani 1 1 d U . . C11 C 0.9704(4) 0.5676(3) 0.8727(3) 0.0246(15) Uani 1 1 d . . . C12 C 0.9877(5) 0.5083(3) 0.8448(3) 0.0283(16) Uani 1 1 d . . . H12 H 1.0509 0.4925 0.8432 0.034 Uiso 1 1 calc R . . C13 C 0.9146(5) 0.4716(3) 0.8193(3) 0.0299(16) Uani 1 1 d . . . H13 H 0.9282 0.4304 0.8017 0.036 Uiso 1 1 calc R . . C14 C 0.8222(4) 0.4930(3) 0.8187(3) 0.0249(15) Uani 1 1 d . . . H14 H 0.7738 0.4674 0.7984 0.030 Uiso 1 1 calc R . . C15 C 0.7988(5) 0.5526(3) 0.8478(3) 0.0231(14) Uani 1 1 d . . . C16 C 0.6641(5) 0.7846(3) 0.8409(4) 0.0329(17) Uani 1 1 d . . . H16 H 0.6882 0.7407 0.8505 0.040 Uiso 1 1 calc R . . C17 C 0.9343(5) 0.8372(3) 1.0099(3) 0.0293(15) Uani 1 1 d . . . H17 H 0.9330 0.7897 1.0137 0.035 Uiso 1 1 calc R . . C18 C 1.0512(5) 0.6087(3) 0.8998(4) 0.0342(18) Uani 1 1 d . . . H18 H 1.0266 0.6529 0.9069 0.041 Uiso 1 1 calc R . . C19 C 0.6977(4) 0.5765(3) 0.8456(3) 0.0273(15) Uani 1 1 d . . . H19 H 0.6934 0.6123 0.8799 0.033 Uiso 1 1 calc R . . C20 C 0.6535(6) 0.7920(4) 0.7619(4) 0.049(2) Uani 1 1 d . . . H20A H 0.6252 0.8336 0.7514 0.073 Uiso 1 1 calc R . . H20B H 0.6123 0.7582 0.7437 0.073 Uiso 1 1 calc R . . H20C H 0.7161 0.7891 0.7397 0.073 Uiso 1 1 calc R . . C21 C 0.5688(6) 0.7917(4) 0.8770(4) 0.063(2) Uani 1 1 d . . . H21A H 0.5771 0.7871 0.9278 0.094 Uiso 1 1 calc R . . H21B H 0.5252 0.7588 0.8600 0.094 Uiso 1 1 calc R . . H21C H 0.5424 0.8338 0.8667 0.094 Uiso 1 1 calc R . . C22 C 1.0351(5) 0.8565(4) 0.9886(4) 0.047(2) Uani 1 1 d . . . H22A H 1.0505 0.8376 0.9431 0.071 Uiso 1 1 calc R . . H22B H 1.0803 0.8414 1.0239 0.071 Uiso 1 1 calc R . . H22C H 1.0389 0.9030 0.9852 0.071 Uiso 1 1 calc R . . C23 C 0.9097(5) 0.8641(3) 1.0818(4) 0.0439(19) Uani 1 1 d . . . H23A H 0.9176 0.9104 1.0812 0.066 Uiso 1 1 calc R . . H23B H 0.9520 0.8456 1.1171 0.066 Uiso 1 1 calc R . . H23C H 0.8436 0.8536 1.0932 0.066 Uiso 1 1 calc R . . C24 C 1.1322(5) 0.6111(4) 0.8447(4) 0.048(2) Uani 1 1 d . . . H24A H 1.1564 0.5681 0.8366 0.072 Uiso 1 1 calc R . . H24B H 1.1837 0.6382 0.8621 0.072 Uiso 1 1 calc R . . H24C H 1.1076 0.6286 0.8007 0.072 Uiso 1 1 calc R . . C25 C 1.0885(6) 0.5845(4) 0.9692(4) 0.064(3) Uani 1 1 d . . . H25A H 1.0391 0.5888 1.0051 0.096 Uiso 1 1 calc R . . H25B H 1.1445 0.6093 0.9829 0.096 Uiso 1 1 calc R . . H25C H 1.1061 0.5395 0.9645 0.096 Uiso 1 1 calc R . . C26 C 0.6715(5) 0.6036(4) 0.7746(4) 0.048(2) Uani 1 1 d . . . H26A H 0.7184 0.6357 0.7610 0.072 Uiso 1 1 calc R . . H26B H 0.6084 0.6232 0.7772 0.072 Uiso 1 1 calc R . . H26C H 0.6707 0.5694 0.7398 0.072 Uiso 1 1 calc R . . C27 C 0.6271(5) 0.5258(3) 0.8697(4) 0.051(2) Uani 1 1 d . . . H27A H 0.6254 0.4912 0.8354 0.076 Uiso 1 1 calc R . . H27B H 0.5637 0.5448 0.8738 0.076 Uiso 1 1 calc R . . H27C H 0.6469 0.5091 0.9153 0.076 Uiso 1 1 calc R . . C28 C 1.057(3) 0.8572(7) 0.791(3) 0.053(8) Uani 0.50 1 d PD . . H28A H 1.0144 0.8712 0.8293 0.064 Uiso 0.50 1 calc PR . . H28B H 1.1170 0.8819 0.7967 0.064 Uiso 0.50 1 calc PR . . C29 C 1.0126(11) 0.8786(7) 0.7232(7) 0.037(4) Uani 0.50 1 d PDU . . H29A H 1.0132 0.9257 0.7227 0.045 Uiso 0.50 1 calc PR . . H29B H 1.0544 0.8643 0.6845 0.045 Uiso 0.50 1 calc PR . . C30 C 0.913(3) 0.8575(7) 0.706(3) 0.053(8) Uani 0.50 1 d PD . . H30A H 0.8900 0.8803 0.6642 0.064 Uiso 0.50 1 calc PR . . H30B H 0.8704 0.8678 0.7458 0.064 Uiso 0.50 1 calc PR . . 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 0.0360(4) 0.0172(3) 0.0273(4) 0.0021(4) 0.0058(4) 0.0008(4) Cl1 0.0453(10) 0.0359(9) 0.0324(9) -0.0045(8) 0.0076(8) 0.0001(9) Cl2 0.0619(12) 0.0228(8) 0.0285(9) 0.0092(7) 0.0066(9) -0.0003(9) S1 0.0406(11) 0.0428(10) 0.0335(9) -0.0114(9) 0.0067(9) -0.0102(9) N1 0.021(3) 0.016(3) 0.024(3) -0.003(2) -0.002(2) -0.003(2) N2 0.027(3) 0.021(3) 0.018(3) -0.002(2) -0.002(2) -0.002(2) C1 0.020(3) 0.019(3) 0.027(4) 0.000(3) -0.009(3) 0.006(3) C2 0.023(3) 0.028(3) 0.015(3) -0.001(3) -0.003(3) 0.000(3) C3 0.025(4) 0.023(3) 0.020(3) 0.007(3) 0.002(3) -0.003(3) C4 0.014(3) 0.015(3) 0.029(3) 0.004(3) 0.004(3) 0.005(3) C5 0.026(4) 0.024(3) 0.026(4) 0.006(3) 0.003(3) 0.006(3) C6 0.032(4) 0.024(3) 0.035(4) 0.004(3) 0.002(3) 0.010(3) C7 0.036(3) 0.019(3) 0.039(3) 0.005(2) 0.005(3) 0.010(2) C8 0.045(5) 0.023(3) 0.050(5) -0.011(3) 0.006(4) -0.011(3) C9 0.027(4) 0.014(3) 0.028(4) -0.004(3) 0.007(3) 0.003(3) C10 0.030(3) 0.013(2) 0.021(3) 0.002(2) 0.000(2) -0.003(2) C11 0.027(4) 0.018(3) 0.029(4) 0.004(3) -0.003(3) 0.003(3) C12 0.031(4) 0.020(3) 0.035(4) -0.004(3) -0.001(3) 0.008(3) C13 0.041(4) 0.018(3) 0.030(4) -0.001(3) 0.005(3) 0.001(3) C14 0.029(4) 0.019(3) 0.027(4) -0.003(3) 0.007(3) -0.006(3) C15 0.032(4) 0.013(3) 0.024(3) 0.005(3) 0.003(3) -0.006(3) C16 0.031(4) 0.025(3) 0.042(4) 0.005(3) -0.013(3) 0.001(3) C17 0.028(4) 0.026(3) 0.033(4) -0.010(3) -0.004(3) -0.002(3) C18 0.036(5) 0.022(3) 0.045(4) 0.006(3) -0.010(3) 0.005(3) C19 0.030(4) 0.020(3) 0.032(4) -0.004(3) 0.000(3) 0.001(3) C20 0.051(5) 0.058(5) 0.038(5) 0.000(4) -0.010(4) 0.015(4) C21 0.054(6) 0.086(6) 0.048(5) 0.007(4) -0.016(5) -0.027(5) C22 0.045(5) 0.052(5) 0.044(5) -0.013(4) -0.004(4) -0.001(4) C23 0.039(5) 0.052(5) 0.041(4) -0.009(4) 0.001(4) -0.004(4) C24 0.036(5) 0.044(5) 0.064(5) -0.015(4) 0.003(4) -0.006(4) C25 0.084(7) 0.051(5) 0.057(5) 0.007(4) -0.023(5) -0.028(5) C26 0.041(5) 0.058(5) 0.044(5) -0.002(4) -0.001(4) 0.014(4) C27 0.028(4) 0.030(4) 0.095(7) -0.005(4) 0.006(4) -0.002(3) C28 0.07(3) 0.035(4) 0.054(6) -0.003(13) 0.017(11) -0.008(8) C29 0.041(5) 0.033(5) 0.039(5) -0.002(3) 0.006(4) 0.001(4) C30 0.07(3) 0.035(4) 0.054(6) -0.003(13) 0.017(11) -0.008(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C1 1.887(6) . ? Cu1 S1 2.2721(18) 4_756 ? Cu1 S1 2.362(2) . ? Cu1 Cu1 2.8387(15) 4_756 ? Cl1 C2 1.667(6) . ? Cl2 C3 1.708(6) . ? S1 C28 1.902(13) . ? S1 Cu1 2.2721(18) 4_756 ? N1 C1 1.385(7) . ? N1 C2 1.403(7) . ? N1 C4 1.449(7) . ? N2 C3 1.372(7) . ? N2 C1 1.378(7) . ? N2 C10 1.436(7) . ? C2 C3 1.343(8) . ? C4 C9 1.387(8) . ? C4 C5 1.410(8) . ? C5 C6 1.394(8) . ? C5 C16 1.516(9) . ? C6 C7 1.353(9) . ? C6 H6 0.9500 . ? C7 C8 1.382(9) . ? C7 H7 0.9500 . ? C8 C9 1.409(8) . ? C8 H8 0.9500 . ? C9 C17 1.492(8) . ? C10 C11 1.411(9) . ? C10 C15 1.411(8) . ? C11 C12 1.378(8) . ? C11 C18 1.519(9) . ? C12 C13 1.375(9) . ? C12 H12 0.9500 . ? C13 C14 1.375(9) . ? C13 H13 0.9500 . ? C14 C15 1.410(8) . ? C14 H14 0.9500 . ? C15 C19 1.509(9) . ? C16 C21 1.515(10) . ? C16 C20 1.525(9) . ? C16 H16 1.0000 . ? C17 C23 1.523(9) . ? C17 C22 1.530(9) . ? C17 H17 1.0000 . ? C18 C25 1.513(9) . ? C18 C24 1.551(10) . ? C18 H18 1.0000 . ? C19 C26 1.513(9) . ? C19 C27 1.527(9) . ? C19 H19 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.51(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.50(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 S1 1.849(13) 4_756 ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? 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 S1 143.02(18) . 4_756 ? C1 Cu1 S1 122.56(18) . . ? S1 Cu1 S1 93.76(7) 4_756 . ? C1 Cu1 Cu1 156.77(17) . 4_756 ? S1 Cu1 Cu1 53.68(5) 4_756 4_756 ? S1 Cu1 Cu1 50.80(5) . 4_756 ? C28 S1 Cu1 95.4(14) . 4_756 ? C28 S1 Cu1 93.1(12) . . ? Cu1 S1 Cu1 75.52(6) 4_756 . ? C1 N1 C2 111.4(5) . . ? C1 N1 C4 122.1(5) . . ? C2 N1 C4 126.3(5) . . ? C3 N2 C1 111.0(5) . . ? C3 N2 C10 123.6(5) . . ? C1 N2 C10 125.1(5) . . ? N2 C1 N1 103.1(5) . . ? N2 C1 Cu1 132.0(4) . . ? N1 C1 Cu1 123.9(4) . . ? C3 C2 N1 105.5(5) . . ? C3 C2 Cl1 129.5(5) . . ? N1 C2 Cl1 125.0(4) . . ? C2 C3 N2 108.9(5) . . ? C2 C3 Cl2 127.7(5) . . ? N2 C3 Cl2 123.4(4) . . ? C9 C4 C5 124.0(5) . . ? C9 C4 N1 119.3(5) . . ? C5 C4 N1 116.7(5) . . ? C6 C5 C4 116.3(6) . . ? C6 C5 C16 120.7(6) . . ? C4 C5 C16 123.0(5) . . ? C7 C6 C5 122.2(6) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C6 C7 C8 119.7(6) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C9 122.4(6) . . ? C7 C8 H8 118.8 . . ? C9 C8 H8 118.8 . . ? C4 C9 C8 115.3(6) . . ? C4 C9 C17 124.1(5) . . ? C8 C9 C17 120.6(6) . . ? C11 C10 C15 123.2(5) . . ? C11 C10 N2 119.5(5) . . ? C15 C10 N2 117.2(6) . . ? C12 C11 C10 117.4(6) . . ? C12 C11 C18 121.0(6) . . ? C10 C11 C18 121.6(5) . . ? C13 C12 C11 120.8(6) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 121.8(6) . . ? C12 C13 H13 119.1 . . ? C14 C13 H13 119.1 . . ? C13 C14 C15 120.6(6) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 116.2(6) . . ? C14 C15 C19 120.3(6) . . ? C10 C15 C19 123.4(5) . . ? C5 C16 C21 108.9(6) . . ? C5 C16 C20 113.2(6) . . ? C21 C16 C20 110.7(6) . . ? C5 C16 H16 108.0 . . ? C21 C16 H16 108.0 . . ? C20 C16 H16 108.0 . . ? C9 C17 C23 111.8(5) . . ? C9 C17 C22 111.6(6) . . ? C23 C17 C22 110.6(6) . . ? C9 C17 H17 107.6 . . ? C23 C17 H17 107.6 . . ? C22 C17 H17 107.6 . . ? C25 C18 C11 111.5(6) . . ? C25 C18 C24 110.4(6) . . ? C11 C18 C24 109.7(5) . . ? C25 C18 H18 108.4 . . ? C11 C18 H18 108.4 . . ? C24 C18 H18 108.4 . . ? C15 C19 C26 112.3(6) . . ? C15 C19 C27 111.9(5) . . ? C26 C19 C27 111.9(6) . . ? C15 C19 H19 106.7 . . ? C26 C19 H19 106.7 . . ? C27 C19 H19 106.7 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C23 H23A 109.5 . . ? C17 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C17 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C18 C24 H24A 109.5 . . ? C18 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C18 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C18 C25 H25A 109.5 . . ? C18 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C18 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C19 C26 H26A 109.5 . . ? C19 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C19 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C19 C27 H27A 109.5 . . ? C19 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C19 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 S1 123(2) . . ? C29 C28 H28A 106.6 . . ? S1 C28 H28A 106.6 . . ? C29 C28 H28B 106.6 . . ? S1 C28 H28B 106.6 . . ? H28A C28 H28B 106.6 . . ? C30 C29 C28 119(4) . . ? C30 C29 H29A 107.6 . . ? C28 C29 H29A 107.6 . . ? C30 C29 H29B 107.6 . . ? C28 C29 H29B 107.6 . . ? H29A C29 H29B 107.0 . . ? C29 C30 S1 109.8(19) . 4_756 ? C29 C30 H30A 109.7 . . ? S1 C30 H30A 109.7 4_756 . ? C29 C30 H30B 109.7 . . ? S1 C30 H30B 109.7 4_756 . ? H30A C30 H30B 108.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.618 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.092 data_[Cl2iPr2Cu]2(u-S(CH2)4S) _database_code_depnum_ccdc_archive 'CCDC 909177' #TrackingRef '15148_web_deposit_cif_file_1_TimothyH.Warren_1352065596.cmpd_4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cl2iPr2Cu]2(u-S(CH2)4S)' _chemical_melting_point ? _chemical_formula_moiety 'C58 H76 N4 Cl4 S2 Cu2' _chemical_formula_sum 'C58 H76 Cl4 Cu2 N4 S2' _chemical_formula_weight 1162.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 52.089(10) _cell_length_b 8.9421(17) _cell_length_c 35.545(7) _cell_angle_alpha 90.00 _cell_angle_beta 129.297(2) _cell_angle_gamma 90.00 _cell_volume 12813(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11260 _cell_measurement_theta_min 4.646 _cell_measurement_theta_max 46.321 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4880 _exptl_absorpt_coefficient_mu 0.932 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6175 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details "SADABS based on Blessing's method; Blessing, Acta Cryst. (1995) A51 33-38" _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53680 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -66 _diffrn_reflns_limit_h_max 66 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 27.00 _reflns_number_total 13951 _reflns_number_gt 9042 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker APEXII' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows; Ferrugia L J (1997), J. Appl. Cryst. 30, 565' _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. A badly disordered molecule of fluorobenzene was identified and the SQUEEZE subroutine of Platon was used to remove this from the reflection data allowing final refinement in the absence of the disordered solvent. Thus, the refined structure has "solvent accessible voids". The SQUEEZE subroutine identified 367 e / cell which corresponds to 0.92 molecules of fluorobenzene / dinuclear compound 4. Disorder in the C4 linker was also identified and modeled with a 73/27 ratio of C55A - C58A / C55B - C58B occupancies. S2 (connected to C58) was also modeled with these occupancies as S2A and S2B over two clearly separate positions. Some of the minor occupancy C atoms have more oblique thermal ellipsoids than their major occupancy counterparts. ; _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^)+(0.0602P)^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 13951 _refine_ls_number_parameters 693 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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 0.165489(10) 0.89771(5) 0.394903(14) 0.02260(11) Uani 1 1 d . . . Cu2 Cu 0.093583(10) 1.01662(5) 0.533144(15) 0.02857(12) Uani 1 1 d . . . Cl2 Cl 0.09772(2) 0.47057(9) 0.24669(3) 0.02767(19) Uani 1 1 d . . . Cl4 Cl 0.18530(2) 1.39497(10) 0.69341(3) 0.0328(2) Uani 1 1 d . . . S1 S 0.17088(2) 1.09864(10) 0.43146(3) 0.0272(2) Uani 1 1 d . . . Cl1 Cl 0.18188(2) 0.46496(9) 0.29584(3) 0.02818(19) Uani 1 1 d . . . Cl3 Cl 0.12444(2) 1.26878(10) 0.70071(3) 0.0298(2) Uani 1 1 d . . . S2A S 0.06044(7) 0.8807(3) 0.46966(10) 0.0393(6) Uani 0.73 1 d P A 1 N4 N 0.14576(7) 1.2128(3) 0.61555(10) 0.0221(6) Uani 1 1 d . . . N3 N 0.10878(6) 1.1354(3) 0.62012(9) 0.0208(6) Uani 1 1 d . . . N1 N 0.17927(6) 0.6721(3) 0.34903(9) 0.0196(6) Uani 1 1 d . . . C2 C 0.16271(8) 0.5678(3) 0.31188(12) 0.0211(7) Uani 1 1 d . . . C29 C 0.12976(8) 1.2287(4) 0.65930(11) 0.0212(7) Uani 1 1 d . A . C15 C 0.09022(8) 0.6131(4) 0.33605(11) 0.0214(7) Uani 1 1 d . . . C19 C 0.11056(8) 0.4746(4) 0.36507(12) 0.0238(7) Uani 1 1 d . . . H19 H 0.1225 0.4420 0.3529 0.029 Uiso 1 1 calc R . . N2 N 0.12851(6) 0.6706(3) 0.32034(9) 0.0192(6) Uani 1 1 d . . . C5 C 0.23435(8) 0.6089(4) 0.42265(12) 0.0228(7) Uani 1 1 d . . . C11 C 0.08061(8) 0.8317(4) 0.28674(12) 0.0247(7) Uani 1 1 d . . . C3 C 0.13083(8) 0.5677(3) 0.29337(12) 0.0206(7) Uani 1 1 d . . . C31 C 0.07965(8) 1.0622(4) 0.60819(12) 0.0223(7) Uani 1 1 d . A . C12 C 0.05303(8) 0.8679(4) 0.28340(12) 0.0273(8) Uani 1 1 d . . . H12 H 0.0400 0.9532 0.2654 0.033 Uiso 1 1 calc R . . C6 C 0.26872(8) 0.6337(4) 0.45327(13) 0.0269(8) Uani 1 1 d . . . H6 H 0.2830 0.5768 0.4822 0.032 Uiso 1 1 calc R . . C44 C 0.04916(9) 1.3096(4) 0.57097(13) 0.0316(8) Uani 1 1 d . A . H44 H 0.0724 1.3471 0.5898 0.038 Uiso 1 1 calc R . . C28 C 0.11832(8) 1.1256(4) 0.59218(12) 0.0224(7) Uani 1 1 d . A . C4 C 0.21474(8) 0.6963(4) 0.38098(11) 0.0208(7) Uani 1 1 d . . . C14 C 0.06261(8) 0.6528(4) 0.33162(12) 0.0275(8) Uani 1 1 d . . . H14 H 0.0560 0.5923 0.3461 0.033 Uiso 1 1 calc R . . C17 C 0.20514(9) 0.8996(4) 0.32280(12) 0.0285(8) Uani 1 1 d . . . H17 H 0.1828 0.8511 0.3013 0.034 Uiso 1 1 calc R . . C25 C 0.06194(10) 0.9024(5) 0.20469(13) 0.0397(10) Uani 1 1 d . . . H25A H 0.0595 0.7956 0.1969 0.060 Uiso 1 1 calc R . . H25B H 0.0683 0.9558 0.1876 0.060 Uiso 1 1 calc R . . H25C H 0.0408 0.9421 0.1944 0.060 Uiso 1 1 calc R . . C21 C 0.23445(9) 0.3383(4) 0.43985(13) 0.0327(8) Uani 1 1 d . . . H21A H 0.2310 0.3176 0.4099 0.049 Uiso 1 1 calc R . . H21B H 0.2230 0.2625 0.4443 0.049 Uiso 1 1 calc R . . H21C H 0.2582 0.3359 0.4676 0.049 Uiso 1 1 calc R . . C1 C 0.15823(8) 0.7369(4) 0.35475(11) 0.0205(7) Uani 1 1 d . . . C30 C 0.15276(8) 1.2767(4) 0.65646(12) 0.0231(7) Uani 1 1 d . A . C37 C 0.16553(8) 1.2351(4) 0.60005(12) 0.0238(7) Uani 1 1 d . A . C9 C 0.22744(8) 0.8046(4) 0.36815(12) 0.0238(7) Uani 1 1 d . . . C16 C 0.22066(8) 0.4918(4) 0.43645(12) 0.0255(8) Uani 1 1 d . . . H16 H 0.1961 0.4882 0.4101 0.031 Uiso 1 1 calc R . . C8 C 0.26171(8) 0.8248(4) 0.39999(13) 0.0280(8) Uani 1 1 d . . . H8 H 0.2713 0.8980 0.3928 0.034 Uiso 1 1 calc R . . C36 C 0.05075(8) 1.1479(4) 0.58529(11) 0.0250(8) Uani 1 1 d . . . C34 C 0.02467(10) 0.9284(5) 0.58650(15) 0.0397(10) Uani 1 1 d . . . H34 H 0.0056 0.8822 0.5792 0.048 Uiso 1 1 calc R A . C7 C 0.28198(9) 0.7405(4) 0.44164(13) 0.0295(8) Uani 1 1 d . . . H7 H 0.3053 0.7556 0.4626 0.035 Uiso 1 1 calc R . . C10 C 0.09871(8) 0.7055(4) 0.31374(11) 0.0206(7) Uani 1 1 d . . . C35 C 0.02328(9) 1.0759(4) 0.57458(13) 0.0331(9) Uani 1 1 d . A . H35 H 0.0031 1.1296 0.5587 0.040 Uiso 1 1 calc R . . C20 C 0.22758(9) 0.5334(4) 0.48393(13) 0.0332(9) Uani 1 1 d . . . H20A H 0.2168 0.4608 0.4905 0.050 Uiso 1 1 calc R . . H20B H 0.2188 0.6336 0.4809 0.050 Uiso 1 1 calc R . . H20C H 0.2516 0.5324 0.5107 0.050 Uiso 1 1 calc R . . C23 C 0.21793(11) 0.9116(5) 0.29415(15) 0.0464(11) Uani 1 1 d . . . H23A H 0.2390 0.9661 0.3135 0.070 Uiso 1 1 calc R . . H23B H 0.2016 0.9651 0.2636 0.070 Uiso 1 1 calc R . . H23C H 0.2213 0.8110 0.2870 0.070 Uiso 1 1 calc R . . C49 C 0.03237(11) 1.3210(5) 0.51721(14) 0.0490(11) Uani 1 1 d . . . H49A H 0.0096 1.2829 0.4980 0.073 Uiso 1 1 calc R A . H49B H 0.0448 1.2616 0.5103 0.073 Uiso 1 1 calc R . . H49C H 0.0319 1.4258 0.5087 0.073 Uiso 1 1 calc R . . C13 C 0.04475(8) 0.7803(4) 0.30615(12) 0.0295(8) Uani 1 1 d . . . H13 H 0.0264 0.8079 0.3043 0.035 Uiso 1 1 calc R . . C26 C 0.13681(9) 0.5137(4) 0.41897(13) 0.0326(8) Uani 1 1 d . . . H26A H 0.1510 0.5943 0.4226 0.049 Uiso 1 1 calc R . . H26B H 0.1504 0.4252 0.4368 0.049 Uiso 1 1 calc R . . H26C H 0.1258 0.5465 0.4320 0.049 Uiso 1 1 calc R . . C38 C 0.15488(9) 1.3439(4) 0.56479(13) 0.0302(8) Uani 1 1 d . . . C39 C 0.17388(10) 1.3594(4) 0.54981(14) 0.0384(10) Uani 1 1 d . A . H39 H 0.1675 1.4312 0.5256 0.046 Uiso 1 1 calc R . . C42 C 0.19388(9) 1.1485(4) 0.62172(13) 0.0327(9) Uani 1 1 d . . . C33 C 0.05342(10) 0.8463(4) 0.60893(14) 0.0352(9) Uani 1 1 d . A . H33 H 0.0539 0.7443 0.6168 0.042 Uiso 1 1 calc R . . C43 C 0.11356(9) 0.8216(4) 0.64446(14) 0.0350(9) Uani 1 1 d . A . H43 H 0.1264 0.8690 0.6354 0.042 Uiso 1 1 calc R . . C58A C 0.07967(13) 0.8629(7) 0.44111(19) 0.0331(12) Uani 0.73 1 d P A 1 H58A H 0.0881 0.7595 0.4460 0.040 Uiso 0.73 1 calc PR A 1 H58B H 0.0625 0.8791 0.4057 0.040 Uiso 0.73 1 calc PR A 1 C41 C 0.21164(9) 1.1714(5) 0.60483(15) 0.0412(10) Uani 1 1 d . A . H41 H 0.2312 1.1149 0.6184 0.049 Uiso 1 1 calc R . . C50 C 0.03158(10) 1.4076(4) 0.58373(15) 0.0438(10) Uani 1 1 d . . . H50A H 0.0314 1.5115 0.5748 0.066 Uiso 1 1 calc R A . H50B H 0.0434 1.4015 0.6187 0.066 Uiso 1 1 calc R . . H50C H 0.0087 1.3725 0.5658 0.066 Uiso 1 1 calc R . . C22 C 0.20095(11) 1.0550(4) 0.33575(16) 0.0445(10) Uani 1 1 d . . . H22A H 0.1933 1.0461 0.3548 0.067 Uiso 1 1 calc R . . H22B H 0.1845 1.1111 0.3059 0.067 Uiso 1 1 calc R . . H22C H 0.2223 1.1077 0.3549 0.067 Uiso 1 1 calc R . . C40 C 0.20130(10) 1.2743(5) 0.56907(15) 0.0441(11) Uani 1 1 d . . . H40 H 0.2134 1.2861 0.5576 0.053 Uiso 1 1 calc R A . C18 C 0.08880(9) 0.9238(4) 0.25956(13) 0.0283(8) Uani 1 1 d . . . H18 H 0.1101 0.8848 0.2688 0.034 Uiso 1 1 calc R A . C46 C 0.20436(10) 1.0358(5) 0.66088(15) 0.0424(10) Uani 1 1 d . A . H46 H 0.1935 1.0652 0.6751 0.051 Uiso 1 1 calc R . . C32 C 0.08185(9) 0.9119(4) 0.62010(12) 0.0267(8) Uani 1 1 d . . . C51 C 0.09716(11) 1.4153(5) 0.49063(15) 0.0527(12) Uani 1 1 d . . . H51A H 0.1055 1.4238 0.4725 0.079 Uiso 1 1 calc R A . H51B H 0.0795 1.4890 0.4783 0.079 Uiso 1 1 calc R . . H51C H 0.0883 1.3145 0.4865 0.079 Uiso 1 1 calc R . . C24 C 0.09385(10) 1.0883(4) 0.27346(15) 0.0410(10) Uani 1 1 d . . . H24A H 0.0730 1.1311 0.2632 0.061 Uiso 1 1 calc R . . H24B H 0.1009 1.1417 0.2573 0.061 Uiso 1 1 calc R . . H24C H 0.1109 1.0982 0.3088 0.061 Uiso 1 1 calc R . . C56A C 0.1231(3) 0.9660(11) 0.4355(5) 0.033(2) Uani 0.73 1 d P A 1 H56A H 0.1310 0.8632 0.4374 0.040 Uiso 0.73 1 calc PR A 1 H56B H 0.1060 0.9918 0.4007 0.040 Uiso 0.73 1 calc PR A 1 C53 C 0.19141(14) 0.8801(5) 0.6384(2) 0.0673(15) Uani 1 1 d . . . H53A H 0.1673 0.8844 0.6124 0.101 Uiso 1 1 calc R A . H53B H 0.1966 0.8097 0.6635 0.101 Uiso 1 1 calc R . . H53C H 0.2021 0.8465 0.6250 0.101 Uiso 1 1 calc R . . C47 C 0.10712(12) 0.6594(5) 0.62730(19) 0.0625(14) Uani 1 1 d . . . H47A H 0.1282 0.6105 0.6408 0.094 Uiso 1 1 calc R A . H47B H 0.0926 0.6568 0.5917 0.094 Uiso 1 1 calc R . . H47C H 0.0964 0.6068 0.6383 0.094 Uiso 1 1 calc R . . C27 C 0.08933(9) 0.3430(4) 0.35865(14) 0.0340(9) Uani 1 1 d . . . H27A H 0.1031 0.2529 0.3731 0.051 Uiso 1 1 calc R . . H27B H 0.0713 0.3261 0.3239 0.051 Uiso 1 1 calc R . . H27C H 0.0800 0.3656 0.3748 0.051 Uiso 1 1 calc R . . C48 C 0.13484(11) 0.8296(5) 0.69889(16) 0.0577(13) Uani 1 1 d . . . H48A H 0.1386 0.9346 0.7091 0.087 Uiso 1 1 calc R A . H48B H 0.1562 0.7809 0.7138 0.087 Uiso 1 1 calc R . . H48C H 0.1236 0.7786 0.7093 0.087 Uiso 1 1 calc R . . C45 C 0.12529(10) 1.4439(4) 0.54417(14) 0.0363(9) Uani 1 1 d . A . H45 H 0.1168 1.4216 0.5621 0.044 Uiso 1 1 calc R . . C55A C 0.1512(2) 1.0709(12) 0.4580(3) 0.0186(16) Uani 0.73 1 d P A 1 H55A H 0.1686 1.0377 0.4919 0.022 Uiso 0.73 1 calc PR A 1 H55B H 0.1434 1.1698 0.4595 0.022 Uiso 0.73 1 calc PR A 1 C52 C 0.13565(14) 1.6085(5) 0.5531(2) 0.0733(16) Uani 1 1 d . . . H52A H 0.1530 1.6255 0.5880 0.110 Uiso 1 1 calc R A . H52B H 0.1164 1.6715 0.5411 0.110 Uiso 1 1 calc R . . H52C H 0.1441 1.6340 0.5359 0.110 Uiso 1 1 calc R . . C54 C 0.24153(12) 1.0345(7) 0.7020(2) 0.095(2) Uani 1 1 d . . . H54A H 0.2528 0.9957 0.6901 0.142 Uiso 1 1 calc R A . H54B H 0.2466 0.9705 0.7284 0.142 Uiso 1 1 calc R . . H54C H 0.2492 1.1366 0.7142 0.142 Uiso 1 1 calc R . . C57A C 0.10772(14) 0.9701(7) 0.4604(2) 0.0308(12) Uani 0.73 1 d P A 1 H57A H 0.1254 0.9494 0.4954 0.037 Uiso 0.73 1 calc PR A 1 H57B H 0.0995 1.0728 0.4575 0.037 Uiso 0.73 1 calc PR A 1 C58B C 0.0807(4) 0.9753(19) 0.4339(5) 0.033(3) Uani 0.27 1 d P A 2 H58C H 0.0646 0.9561 0.3985 0.040 Uiso 0.27 1 calc PR A 2 H58D H 0.0872 1.0819 0.4386 0.040 Uiso 0.27 1 calc PR A 2 C56B C 0.1283(6) 0.914(3) 0.4364(10) 0.025(5) Uani 0.27 1 d P A 2 H56C H 0.1123 0.9360 0.4012 0.030 Uiso 0.27 1 calc PR A 2 H56D H 0.1416 0.8262 0.4414 0.030 Uiso 0.27 1 calc PR A 2 C57B C 0.1101(4) 0.883(2) 0.4552(7) 0.046(4) Uani 0.27 1 d P A 2 H57C H 0.1033 0.7763 0.4489 0.056 Uiso 0.27 1 calc PR A 2 H57D H 0.1255 0.8976 0.4909 0.056 Uiso 0.27 1 calc PR A 2 C55B C 0.1519(12) 1.054(5) 0.4645(17) 0.092(15) Uani 0.27 1 d P A 2 H55C H 0.1698 1.0299 0.4992 0.110 Uiso 0.27 1 calc PR A 2 H55D H 0.1392 1.1408 0.4623 0.110 Uiso 0.27 1 calc PR A 2 S2B S 0.0601(2) 0.9413(9) 0.4600(3) 0.0451(17) Uani 0.27 1 d P A 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 0.0218(2) 0.0273(2) 0.0219(2) -0.00170(18) 0.01534(19) 0.00155(18) Cu2 0.0255(2) 0.0385(3) 0.0266(2) -0.0085(2) 0.0188(2) -0.0035(2) Cl2 0.0263(4) 0.0279(4) 0.0293(5) -0.0051(4) 0.0178(4) -0.0047(4) Cl4 0.0285(5) 0.0392(5) 0.0298(5) -0.0102(4) 0.0180(4) -0.0098(4) S1 0.0270(5) 0.0291(5) 0.0291(5) -0.0040(4) 0.0195(4) -0.0006(4) Cl1 0.0280(4) 0.0302(5) 0.0321(5) -0.0041(4) 0.0218(4) 0.0033(4) Cl3 0.0321(5) 0.0394(5) 0.0244(4) -0.0057(4) 0.0209(4) -0.0033(4) S2A 0.0292(9) 0.0617(17) 0.0371(13) -0.0229(11) 0.0257(10) -0.0164(12) N4 0.0246(15) 0.0233(15) 0.0227(15) -0.0003(12) 0.0169(13) 0.0009(12) N3 0.0177(14) 0.0244(15) 0.0206(14) -0.0012(11) 0.0123(13) -0.0009(11) N1 0.0194(14) 0.0208(14) 0.0204(14) -0.0010(11) 0.0134(13) -0.0004(12) C2 0.0258(18) 0.0184(17) 0.0245(18) 0.0022(13) 0.0185(16) 0.0037(14) C29 0.0217(17) 0.0243(17) 0.0190(17) -0.0019(14) 0.0135(15) -0.0007(14) C15 0.0190(17) 0.0276(18) 0.0190(17) 0.0013(14) 0.0128(15) 0.0012(14) C19 0.0256(18) 0.0233(18) 0.0286(19) 0.0037(15) 0.0200(17) 0.0021(15) N2 0.0183(14) 0.0196(14) 0.0219(14) 0.0032(11) 0.0138(13) 0.0024(11) C5 0.0211(17) 0.0282(19) 0.0209(17) -0.0029(14) 0.0141(15) 0.0009(15) C11 0.0257(18) 0.0289(19) 0.0220(18) 0.0037(15) 0.0162(16) 0.0059(15) C3 0.0260(18) 0.0179(17) 0.0212(17) 0.0030(13) 0.0165(16) 0.0025(14) C31 0.0227(18) 0.0228(18) 0.0224(18) -0.0047(14) 0.0147(16) -0.0021(14) C12 0.0239(18) 0.034(2) 0.0244(18) 0.0037(15) 0.0154(16) 0.0091(15) C6 0.0220(18) 0.030(2) 0.0293(19) 0.0008(15) 0.0164(16) 0.0038(15) C44 0.0262(19) 0.034(2) 0.028(2) 0.0009(16) 0.0141(17) 0.0062(16) C28 0.0216(17) 0.0236(18) 0.0236(18) -0.0003(14) 0.0150(16) 0.0022(14) C4 0.0178(16) 0.0228(18) 0.0230(17) -0.0057(14) 0.0135(15) -0.0009(14) C14 0.0245(18) 0.035(2) 0.0280(19) 0.0021(16) 0.0190(17) 0.0000(16) C17 0.0290(19) 0.0282(19) 0.0252(19) 0.0005(15) 0.0156(17) -0.0053(16) C25 0.048(2) 0.047(2) 0.032(2) 0.0078(19) 0.029(2) 0.008(2) C21 0.035(2) 0.035(2) 0.033(2) 0.0026(17) 0.0241(19) -0.0025(17) C1 0.0229(17) 0.0231(17) 0.0203(17) 0.0065(14) 0.0159(15) 0.0059(14) C30 0.0235(18) 0.0228(18) 0.0222(18) -0.0001(14) 0.0141(16) 0.0004(14) C37 0.0242(18) 0.0279(19) 0.0265(18) -0.0074(15) 0.0195(16) -0.0067(15) C9 0.0284(19) 0.0227(18) 0.0257(18) -0.0029(14) 0.0197(16) -0.0003(15) C16 0.0196(17) 0.034(2) 0.0215(17) 0.0039(15) 0.0125(15) 0.0007(15) C8 0.0294(19) 0.030(2) 0.032(2) -0.0037(16) 0.0228(18) -0.0063(16) C36 0.0221(18) 0.033(2) 0.0165(17) -0.0045(14) 0.0107(15) 0.0006(15) C34 0.033(2) 0.051(3) 0.045(2) -0.020(2) 0.029(2) -0.0175(19) C7 0.0216(18) 0.037(2) 0.030(2) -0.0059(16) 0.0167(17) -0.0043(16) C10 0.0199(16) 0.0257(18) 0.0209(17) -0.0014(14) 0.0151(15) 0.0015(14) C35 0.0230(19) 0.044(2) 0.030(2) -0.0102(17) 0.0158(17) -0.0021(17) C20 0.036(2) 0.042(2) 0.032(2) 0.0007(17) 0.0262(19) 0.0014(18) C23 0.060(3) 0.053(3) 0.036(2) 0.009(2) 0.035(2) 0.010(2) C49 0.057(3) 0.047(3) 0.036(2) 0.011(2) 0.027(2) 0.019(2) C13 0.0227(18) 0.040(2) 0.0279(19) 0.0013(16) 0.0169(17) 0.0081(16) C26 0.032(2) 0.030(2) 0.028(2) 0.0029(16) 0.0158(18) 0.0006(17) C38 0.037(2) 0.029(2) 0.029(2) -0.0094(16) 0.0231(18) -0.0093(17) C39 0.047(2) 0.043(2) 0.037(2) -0.0094(18) 0.032(2) -0.017(2) C42 0.029(2) 0.039(2) 0.034(2) -0.0048(17) 0.0218(18) -0.0024(17) C33 0.046(2) 0.0263(19) 0.050(2) -0.0115(18) 0.038(2) -0.0129(18) C43 0.039(2) 0.027(2) 0.048(2) 0.0079(18) 0.032(2) 0.0047(17) C58A 0.039(3) 0.040(3) 0.029(3) -0.010(2) 0.026(3) -0.009(3) C41 0.026(2) 0.055(3) 0.049(3) -0.014(2) 0.027(2) -0.0069(19) C50 0.044(2) 0.038(2) 0.043(2) -0.0030(19) 0.025(2) 0.007(2) C22 0.056(3) 0.035(2) 0.047(3) 0.0060(19) 0.035(2) 0.010(2) C40 0.041(2) 0.065(3) 0.040(2) -0.016(2) 0.032(2) -0.018(2) C18 0.031(2) 0.030(2) 0.031(2) 0.0092(16) 0.0228(18) 0.0090(16) C46 0.036(2) 0.046(2) 0.048(3) 0.005(2) 0.027(2) 0.012(2) C32 0.031(2) 0.0262(19) 0.0297(19) -0.0051(15) 0.0228(18) -0.0028(16) C51 0.043(3) 0.066(3) 0.046(3) -0.001(2) 0.027(2) 0.001(2) C24 0.052(3) 0.034(2) 0.040(2) 0.0109(18) 0.031(2) 0.0054(19) C56A 0.042(5) 0.026(6) 0.042(4) 0.006(4) 0.032(4) 0.010(4) C53 0.097(4) 0.044(3) 0.090(4) 0.002(3) 0.073(4) 0.008(3) C47 0.066(3) 0.038(3) 0.074(3) -0.005(2) 0.040(3) 0.014(2) C27 0.028(2) 0.035(2) 0.035(2) 0.0075(17) 0.0182(18) 0.0001(17) C48 0.049(3) 0.057(3) 0.054(3) 0.010(2) 0.026(2) 0.021(2) C45 0.047(2) 0.033(2) 0.038(2) 0.0072(17) 0.032(2) 0.0016(18) C55A 0.020(3) 0.024(4) 0.011(2) -0.001(2) 0.010(3) 0.001(3) C52 0.075(4) 0.036(3) 0.088(4) 0.007(3) 0.041(3) 0.005(3) C54 0.042(3) 0.126(5) 0.077(4) 0.051(4) 0.019(3) 0.020(3) C57A 0.029(3) 0.034(3) 0.031(3) -0.009(3) 0.020(3) -0.003(3) C58B 0.026(8) 0.050(10) 0.022(7) 0.010(7) 0.014(7) 0.003(7) C56B 0.015(10) 0.030(14) 0.023(8) -0.007(10) 0.009(8) -0.012(9) C57B 0.052(11) 0.044(11) 0.057(11) -0.010(9) 0.041(10) 0.004(9) C55B 0.14(3) 0.08(2) 0.15(3) 0.05(2) 0.14(3) 0.05(2) S2B 0.029(2) 0.074(5) 0.036(3) -0.010(3) 0.022(2) -0.010(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 1.888(3) . ? Cu1 S1 2.1293(10) . ? Cu2 C28 1.894(3) . ? Cu2 S2B 2.124(8) . ? Cu2 S2A 2.148(3) . ? Cl2 C3 1.691(3) . ? Cl4 C30 1.702(3) . ? S1 C55A 1.793(11) . ? S1 C55B 1.99(4) . ? Cl1 C2 1.699(3) . ? Cl3 C29 1.699(3) . ? S2A C58A 1.829(5) . ? N4 C28 1.355(4) . ? N4 C30 1.379(4) . ? N4 C37 1.457(4) . ? N3 C28 1.367(4) . ? N3 C29 1.379(4) . ? N3 C31 1.447(4) . ? N1 C1 1.364(4) . ? N1 C2 1.384(4) . ? N1 C4 1.447(4) . ? C2 C3 1.344(4) . ? C29 C30 1.336(4) . ? C15 C14 1.390(4) . ? C15 C10 1.397(4) . ? C15 C19 1.529(4) . ? C19 C27 1.530(5) . ? C19 C26 1.531(5) . ? N2 C1 1.358(4) . ? N2 C3 1.388(4) . ? N2 C10 1.450(4) . ? C5 C4 1.390(4) . ? C5 C6 1.404(5) . ? C5 C16 1.513(4) . ? C11 C10 1.392(4) . ? C11 C12 1.402(4) . ? C11 C18 1.521(5) . ? C31 C32 1.392(5) . ? C31 C36 1.401(4) . ? C12 C13 1.377(5) . ? C6 C7 1.386(5) . ? C44 C36 1.518(5) . ? C44 C49 1.520(5) . ? C44 C50 1.529(5) . ? C4 C9 1.402(4) . ? C14 C13 1.384(5) . ? C17 C9 1.516(5) . ? C17 C22 1.522(5) . ? C17 C23 1.534(5) . ? C25 C18 1.530(5) . ? C21 C16 1.518(5) . ? C37 C42 1.390(5) . ? C37 C38 1.394(5) . ? C9 C8 1.393(5) . ? C16 C20 1.532(4) . ? C8 C7 1.377(5) . ? C36 C35 1.384(5) . ? C34 C35 1.374(5) . ? C34 C33 1.381(5) . ? C38 C39 1.396(5) . ? C38 C45 1.511(5) . ? C39 C40 1.360(6) . ? C42 C41 1.401(5) . ? C42 C46 1.513(5) . ? C33 C32 1.397(5) . ? C43 C48 1.503(6) . ? C43 C32 1.523(5) . ? C43 C47 1.526(5) . ? C58A C57A 1.502(7) . ? C41 C40 1.373(6) . ? C18 C24 1.521(5) . ? C46 C54 1.517(6) . ? C46 C53 1.533(6) . ? C51 C45 1.517(6) . ? C56A C55A 1.476(18) . ? C56A C57A 1.527(13) . ? C45 C52 1.530(6) . ? C58B C57B 1.46(2) . ? C58B S2B 1.832(15) . ? C56B C57B 1.49(4) . ? C56B C55B 1.59(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 S1 171.89(10) . . ? C28 Cu2 S2B 167.0(2) . . ? C28 Cu2 S2A 170.06(12) . . ? S2B Cu2 S2A 17.10(16) . . ? C55A S1 C55B 4.9(15) . . ? C55A S1 Cu1 107.8(3) . . ? C55B S1 Cu1 105.5(14) . . ? C58A S2A Cu2 105.9(2) . . ? C28 N4 C30 110.9(3) . . ? C28 N4 C37 124.8(3) . . ? C30 N4 C37 124.3(3) . . ? C28 N3 C29 110.6(3) . . ? C28 N3 C31 123.7(3) . . ? C29 N3 C31 125.6(3) . . ? C1 N1 C2 110.8(3) . . ? C1 N1 C4 124.5(3) . . ? C2 N1 C4 124.4(3) . . ? C3 C2 N1 107.3(3) . . ? C3 C2 Cl1 129.9(3) . . ? N1 C2 Cl1 122.8(2) . . ? C30 C29 N3 107.1(3) . . ? C30 C29 Cl3 130.1(3) . . ? N3 C29 Cl3 122.9(2) . . ? C14 C15 C10 117.5(3) . . ? C14 C15 C19 120.6(3) . . ? C10 C15 C19 121.9(3) . . ? C15 C19 C27 113.3(3) . . ? C15 C19 C26 110.4(3) . . ? C27 C19 C26 110.5(3) . . ? C1 N2 C3 111.3(3) . . ? C1 N2 C10 123.0(3) . . ? C3 N2 C10 125.7(3) . . ? C4 C5 C6 117.0(3) . . ? C4 C5 C16 123.7(3) . . ? C6 C5 C16 119.3(3) . . ? C10 C11 C12 117.1(3) . . ? C10 C11 C18 122.5(3) . . ? C12 C11 C18 120.4(3) . . ? C2 C3 N2 106.4(3) . . ? C2 C3 Cl2 131.1(3) . . ? N2 C3 Cl2 122.5(2) . . ? C32 C31 C36 123.8(3) . . ? C32 C31 N3 118.6(3) . . ? C36 C31 N3 117.7(3) . . ? C13 C12 C11 120.3(3) . . ? C7 C6 C5 120.6(3) . . ? C36 C44 C49 110.5(3) . . ? C36 C44 C50 111.2(3) . . ? C49 C44 C50 111.0(3) . . ? N4 C28 N3 104.2(3) . . ? N4 C28 Cu2 133.5(2) . . ? N3 C28 Cu2 122.2(2) . . ? C5 C4 C9 123.7(3) . . ? C5 C4 N1 117.6(3) . . ? C9 C4 N1 118.6(3) . . ? C13 C14 C15 120.2(3) . . ? C9 C17 C22 110.5(3) . . ? C9 C17 C23 112.5(3) . . ? C22 C17 C23 110.1(3) . . ? N2 C1 N1 104.2(3) . . ? N2 C1 Cu1 125.6(2) . . ? N1 C1 Cu1 129.9(2) . . ? C29 C30 N4 107.2(3) . . ? C29 C30 Cl4 130.1(3) . . ? N4 C30 Cl4 122.7(2) . . ? C42 C37 C38 124.4(3) . . ? C42 C37 N4 118.1(3) . . ? C38 C37 N4 117.5(3) . . ? C8 C9 C4 116.8(3) . . ? C8 C9 C17 121.1(3) . . ? C4 C9 C17 122.1(3) . . ? C5 C16 C21 110.8(3) . . ? C5 C16 C20 111.0(3) . . ? C21 C16 C20 111.2(3) . . ? C7 C8 C9 121.2(3) . . ? C35 C36 C31 116.7(3) . . ? C35 C36 C44 121.5(3) . . ? C31 C36 C44 121.7(3) . . ? C35 C34 C33 121.0(3) . . ? C8 C7 C6 120.7(3) . . ? C11 C10 C15 123.5(3) . . ? C11 C10 N2 118.3(3) . . ? C15 C10 N2 118.2(3) . . ? C34 C35 C36 121.2(3) . . ? C12 C13 C14 121.4(3) . . ? C37 C38 C39 115.9(3) . . ? C37 C38 C45 123.5(3) . . ? C39 C38 C45 120.5(3) . . ? C40 C39 C38 121.6(4) . . ? C37 C42 C41 116.1(4) . . ? C37 C42 C46 121.2(3) . . ? C41 C42 C46 122.7(3) . . ? C34 C33 C32 120.5(4) . . ? C48 C43 C32 110.9(3) . . ? C48 C43 C47 110.8(4) . . ? C32 C43 C47 113.1(3) . . ? C57A C58A S2A 114.1(4) . . ? C40 C41 C42 121.1(4) . . ? C39 C40 C41 120.8(4) . . ? C24 C18 C11 112.2(3) . . ? C24 C18 C25 111.4(3) . . ? C11 C18 C25 110.1(3) . . ? C42 C46 C54 112.9(4) . . ? C42 C46 C53 110.1(4) . . ? C54 C46 C53 111.6(4) . . ? C31 C32 C33 116.8(3) . . ? C31 C32 C43 122.4(3) . . ? C33 C32 C43 120.8(3) . . ? C55A C56A C57A 112.1(8) . . ? C38 C45 C51 112.7(3) . . ? C38 C45 C52 110.6(3) . . ? C51 C45 C52 110.9(4) . . ? C56A C55A S1 120.2(6) . . ? C58A C57A C56A 116.0(6) . . ? C57B C58B S2B 113.7(11) . . ? C57B C56B C55B 109(2) . . ? C58B C57B C56B 114.5(17) . . ? C56B C55B S1 105(2) . . ? C58B S2B Cu2 106.1(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.528 _refine_diff_density_min -0.685 _refine_diff_density_rms 0.082 data_[Cl2iPrCu]SCH2CH2Ph _database_code_depnum_ccdc_archive 'CCDC 909178' #TrackingRef '15149_web_deposit_cif_file_2_TimothyH.Warren_1352065596.cmpd_5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cl2iPrCu]SCH2CH2Ph' _chemical_melting_point ? _chemical_formula_moiety 'C35 H43 N2 S1 Cl2 Cu1' _chemical_formula_sum 'C35 H43 Cl2 Cu N2 S' _chemical_formula_weight 658.21 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' 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 Monoclinic _symmetry_space_group_name_H-M P21/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 9.260(12) _cell_length_b 24.43(3) _cell_length_c 15.506(19) _cell_angle_alpha 90.00 _cell_angle_beta 100.133(17) _cell_angle_gamma 90.00 _cell_volume 3452(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12412 _cell_measurement_theta_min 4.751 _cell_measurement_theta_max 41.842 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.873 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6154 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details "SADABS based on Blessing's method; Blessing, Acta Cryst. (1995) A51 33-38" _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28877 _diffrn_reflns_av_R_equivalents 0.0812 _diffrn_reflns_av_sigmaI/netI 0.0877 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7503 _reflns_number_gt 4523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker APEXII' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows; Ferrugia L J (1997), J. Appl. Cryst. 30, 565' _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^)+(0.0843P)^2^+4.3878P] 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 7503 _refine_ls_number_parameters 378 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1335 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.1908 _refine_ls_wR_factor_gt 0.1684 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.102 _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 0.04536(6) 0.37246(2) 0.30918(4) 0.02700(18) Uani 1 1 d . . . Cl1 Cl -0.38128(15) 0.52789(6) 0.16462(9) 0.0410(3) Uani 1 1 d . . . S1 S 0.21036(18) 0.33054(7) 0.39795(9) 0.0473(4) Uani 1 1 d . . . Cl2 Cl -0.3473(2) 0.42784(7) 0.00398(9) 0.0660(5) Uani 1 1 d . . . N1 N -0.1744(4) 0.45780(15) 0.2440(2) 0.0225(8) Uani 1 1 d . . . C4 C -0.1584(5) 0.4886(2) 0.3252(3) 0.0318(12) Uani 1 1 d . . . N2 N -0.1514(5) 0.39750(16) 0.1470(2) 0.0289(9) Uani 1 1 d . . . C1 C -0.0995(5) 0.41134(18) 0.2318(3) 0.0230(10) Uani 1 1 d . . . C2 C -0.2720(5) 0.4718(2) 0.1695(3) 0.0272(11) Uani 1 1 d . . . C3 C -0.2574(6) 0.4340(2) 0.1085(3) 0.0339(12) Uani 1 1 d . . . C28 C 0.3082(7) 0.2855(2) 0.3307(4) 0.0478(15) Uani 1 1 d . . . H28A H 0.3056 0.3022 0.2737 0.057 Uiso 1 1 calc R . . H28B H 0.4102 0.2825 0.3587 0.057 Uiso 1 1 calc R . . C9 C -0.2426(6) 0.4720(2) 0.3869(3) 0.0424(15) Uani 1 1 d . . . C10 C -0.1013(7) 0.3499(2) 0.1048(3) 0.0454(15) Uani 1 1 d . . . C32 C 0.3869(7) 0.1474(3) 0.1429(6) 0.069(2) Uani 1 1 d . . . H32 H 0.3601 0.1396 0.0835 0.083 Uiso 1 1 calc R . . C33 C 0.5097(7) 0.1240(2) 0.1900(5) 0.0497(15) Uani 1 1 d . . . H33 H 0.5665 0.1006 0.1624 0.060 Uiso 1 1 calc R . . C20 C 0.1684(7) 0.5210(3) 0.2773(6) 0.071(2) Uani 1 1 d . . . H20A H 0.2253 0.5316 0.3326 0.107 Uiso 1 1 calc R . . H20B H 0.2198 0.5310 0.2310 0.107 Uiso 1 1 calc R . . H20C H 0.1534 0.4821 0.2766 0.107 Uiso 1 1 calc R . . C18 C -0.3178(8) 0.2979(3) 0.1455(5) 0.065(2) Uani 1 1 d . . . H18 H -0.3449 0.3352 0.1601 0.078 Uiso 1 1 calc R . . C8 C -0.2307(7) 0.5036(3) 0.4633(4) 0.0593(17) Uani 1 1 d U . . H8 H -0.2837 0.4942 0.5069 0.071 Uiso 1 1 calc R . . C5 C -0.0669(7) 0.5348(2) 0.3332(4) 0.0530(18) Uani 1 1 d . . . C11 C -0.1834(8) 0.3020(2) 0.1029(4) 0.0535(17) Uani 1 1 d . . . C6 C -0.0633(8) 0.5639(3) 0.4150(5) 0.0664(18) Uani 1 1 d U . . H6 H -0.0043 0.5948 0.4269 0.080 Uiso 1 1 calc R . . C15 C 0.0266(9) 0.3556(3) 0.0708(4) 0.069(2) Uani 1 1 d . . . C34 C 0.5495(8) 0.1346(2) 0.2770(5) 0.0554(17) Uani 1 1 d . . . H34 H 0.6331 0.1186 0.3092 0.066 Uiso 1 1 calc R . . C23 C -0.5065(8) 0.4436(5) 0.3704(7) 0.116(4) Uani 1 1 d . . . H23A H -0.5167 0.4585 0.4263 0.174 Uiso 1 1 calc R . . H23B H -0.5721 0.4131 0.3567 0.174 Uiso 1 1 calc R . . H23C H -0.5299 0.4712 0.3261 0.174 Uiso 1 1 calc R . . C17 C -0.3476(6) 0.4242(3) 0.3735(4) 0.0470(15) Uani 1 1 d . . . H17 H -0.3423 0.4085 0.3160 0.056 Uiso 1 1 calc R . . C13 C -0.0149(11) 0.2605(4) 0.0251(6) 0.096(3) Uani 1 1 d U . . H13 H 0.0146 0.2301 -0.0037 0.115 Uiso 1 1 calc R . . C12 C -0.1368(9) 0.2563(4) 0.0600(5) 0.080(2) Uani 1 1 d U . . H12 H -0.1897 0.2237 0.0560 0.096 Uiso 1 1 calc R . . C14 C 0.0686(10) 0.3068(4) 0.0292(6) 0.089(3) Uani 1 1 d U . . H14 H 0.1535 0.3069 0.0049 0.107 Uiso 1 1 calc R . . C21 C 0.0392(9) 0.6127(3) 0.2554(9) 0.131(5) Uani 1 1 d . . . H21A H -0.0538 0.6306 0.2527 0.196 Uiso 1 1 calc R . . H21B H 0.0771 0.6203 0.2029 0.196 Uiso 1 1 calc R . . H21C H 0.1066 0.6259 0.3052 0.196 Uiso 1 1 calc R . . C22 C -0.3037(8) 0.3790(3) 0.4410(5) 0.075(2) Uani 1 1 d . . . H22A H -0.2069 0.3663 0.4375 0.113 Uiso 1 1 calc R . . H22B H -0.3719 0.3492 0.4294 0.113 Uiso 1 1 calc R . . H22C H -0.3049 0.3932 0.4987 0.113 Uiso 1 1 calc R . . C26 C 0.2716(10) 0.4012(4) 0.1197(8) 0.124(4) Uani 1 1 d . . . H26A H 0.2727 0.3917 0.1799 0.185 Uiso 1 1 calc R . . H26B H 0.3226 0.4352 0.1167 0.185 Uiso 1 1 calc R . . H26C H 0.3190 0.3729 0.0921 0.185 Uiso 1 1 calc R . . C16 C 0.0192(7) 0.5502(2) 0.2639(5) 0.066(2) Uani 1 1 d . . . H16 H -0.0366 0.5374 0.2080 0.080 Uiso 1 1 calc R . . C29 C 0.2462(10) 0.2317(3) 0.3189(8) 0.113(4) Uani 1 1 d . . . H29A H 0.1479 0.2342 0.2850 0.136 Uiso 1 1 calc R . . H29B H 0.2387 0.2164 0.3757 0.136 Uiso 1 1 calc R . . C30 C 0.3381(8) 0.1931(3) 0.2721(7) 0.081(3) Uani 1 1 d . . . C35 C 0.4638(9) 0.1695(3) 0.3169(5) 0.069(2) Uani 1 1 d . . . H35 H 0.4922 0.1772 0.3762 0.083 Uiso 1 1 calc R . . C19 C 0.1121(9) 0.4073(3) 0.0724(5) 0.087(3) Uani 1 1 d . . . H19 H 0.0654 0.4338 0.1061 0.104 Uiso 1 1 calc R . . C31 C 0.3032(7) 0.1822(3) 0.1824(7) 0.088(3) Uani 1 1 d . . . H31 H 0.2217 0.1988 0.1491 0.105 Uiso 1 1 calc R . . C7 C -0.1423(9) 0.5473(3) 0.4729(5) 0.076(2) Uani 1 1 d U . . H7 H -0.1361 0.5675 0.5243 0.091 Uiso 1 1 calc R . . C27 C 0.1046(14) 0.4318(4) -0.0199(7) 0.144(5) Uani 1 1 d . . . H27A H 0.1431 0.4059 -0.0566 0.217 Uiso 1 1 calc R . . H27B H 0.1616 0.4648 -0.0161 0.217 Uiso 1 1 calc R . . H27C H 0.0044 0.4399 -0.0447 0.217 Uiso 1 1 calc R . . C24 C -0.2796(9) 0.2663(3) 0.2305(5) 0.074(2) Uani 1 1 d . . . H24A H -0.2517 0.2296 0.2182 0.112 Uiso 1 1 calc R . . H24B H -0.3633 0.2652 0.2592 0.112 Uiso 1 1 calc R . . H24C H -0.1995 0.2840 0.2679 0.112 Uiso 1 1 calc R . . C25 C -0.4514(11) 0.2724(4) 0.0853(7) 0.123(4) Uani 1 1 d . . . H25A H -0.4742 0.2935 0.0324 0.185 Uiso 1 1 calc R . . H25B H -0.5342 0.2725 0.1149 0.185 Uiso 1 1 calc R . . H25C H -0.4289 0.2355 0.0713 0.185 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 0.0307(3) 0.0258(3) 0.0256(3) 0.0048(3) 0.0083(2) 0.0072(3) Cl1 0.0416(7) 0.0396(7) 0.0371(7) -0.0006(6) -0.0065(6) 0.0171(6) S1 0.0630(10) 0.0526(9) 0.0274(7) 0.0095(6) 0.0112(7) 0.0326(8) Cl2 0.1114(15) 0.0542(10) 0.0223(7) -0.0044(6) -0.0164(8) 0.0290(10) N1 0.0216(19) 0.024(2) 0.0203(19) -0.0006(16) -0.0003(15) 0.0023(16) C4 0.034(3) 0.027(3) 0.028(3) -0.007(2) -0.010(2) 0.015(2) N2 0.045(2) 0.024(2) 0.019(2) 0.0024(16) 0.0085(18) 0.0060(19) C1 0.026(2) 0.019(2) 0.025(2) 0.0046(18) 0.0070(19) 0.0023(19) C2 0.027(2) 0.029(3) 0.024(2) 0.005(2) 0.001(2) 0.008(2) C3 0.048(3) 0.032(3) 0.021(2) 0.000(2) 0.002(2) 0.004(2) C28 0.049(3) 0.042(3) 0.054(4) 0.010(3) 0.013(3) 0.011(3) C9 0.044(3) 0.055(4) 0.023(3) -0.009(2) -0.006(2) 0.031(3) C10 0.085(5) 0.031(3) 0.023(3) 0.006(2) 0.016(3) 0.025(3) C32 0.046(4) 0.049(4) 0.105(6) -0.038(4) -0.004(4) 0.000(3) C33 0.049(3) 0.029(3) 0.074(5) -0.008(3) 0.019(3) 0.002(3) C20 0.043(4) 0.039(4) 0.119(7) 0.024(4) -0.020(4) -0.011(3) C18 0.077(5) 0.028(3) 0.083(5) -0.009(3) -0.006(4) -0.006(3) C8 0.061(2) 0.063(2) 0.053(2) -0.0037(18) 0.0075(18) 0.0162(18) C5 0.052(4) 0.022(3) 0.068(4) -0.001(3) -0.037(3) 0.007(3) C11 0.095(5) 0.029(3) 0.035(3) -0.007(2) 0.005(3) 0.016(3) C6 0.065(2) 0.054(2) 0.069(2) -0.0053(18) -0.0191(18) 0.0037(18) C15 0.126(6) 0.051(4) 0.045(4) 0.020(3) 0.058(4) 0.040(4) C34 0.070(4) 0.029(3) 0.072(5) 0.008(3) 0.027(4) -0.001(3) C23 0.041(4) 0.186(11) 0.128(8) 0.020(8) 0.031(5) 0.040(6) C17 0.031(3) 0.081(5) 0.029(3) 0.012(3) 0.007(2) 0.009(3) C13 0.102(3) 0.093(3) 0.093(3) -0.004(2) 0.018(2) 0.008(2) C12 0.087(3) 0.074(3) 0.078(3) -0.0025(19) 0.0114(19) 0.0051(19) C14 0.093(3) 0.093(3) 0.086(3) 0.001(2) 0.028(2) 0.008(2) C21 0.067(5) 0.027(4) 0.275(14) 0.053(6) -0.034(7) -0.009(4) C22 0.071(5) 0.104(6) 0.047(4) 0.027(4) -0.002(4) -0.002(5) C26 0.099(7) 0.110(8) 0.182(11) 0.072(8) 0.081(8) 0.042(6) C16 0.046(4) 0.031(3) 0.105(6) 0.027(4) -0.032(4) -0.018(3) C29 0.086(6) 0.059(5) 0.222(12) -0.033(6) 0.099(7) -0.025(5) C30 0.048(4) 0.044(4) 0.163(9) -0.027(5) 0.056(5) -0.010(3) C35 0.094(6) 0.043(4) 0.080(5) -0.002(4) 0.043(5) -0.007(4) C19 0.113(7) 0.073(5) 0.101(6) 0.046(5) 0.090(6) 0.042(5) C31 0.038(4) 0.061(5) 0.156(9) -0.060(5) -0.007(5) 0.004(3) C7 0.081(3) 0.072(3) 0.071(3) -0.0074(19) 0.0010(19) 0.0168(19) C27 0.200(12) 0.129(9) 0.136(9) 0.089(8) 0.120(9) 0.053(8) C24 0.077(5) 0.063(5) 0.087(6) 0.001(4) 0.026(4) -0.024(4) C25 0.109(8) 0.072(6) 0.161(10) -0.016(6) -0.051(7) -0.017(6) _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 1.891(5) . ? Cu1 S1 2.130(2) . ? Cl1 C2 1.697(5) . ? S1 C28 1.858(6) . ? Cl2 C3 1.693(5) . ? N1 C1 1.361(6) . ? N1 C2 1.379(6) . ? N1 C4 1.452(6) . ? C4 C9 1.396(8) . ? C4 C5 1.403(8) . ? N2 C1 1.361(6) . ? N2 C3 1.382(6) . ? N2 C10 1.449(6) . ? C2 C3 1.346(7) . ? C28 C29 1.433(9) . ? C9 C8 1.402(8) . ? C9 C17 1.510(9) . ? C10 C15 1.386(9) . ? C10 C11 1.393(9) . ? C32 C33 1.365(9) . ? C32 C31 1.366(10) . ? C33 C34 1.359(9) . ? C20 C16 1.537(9) . ? C18 C11 1.511(10) . ? C18 C24 1.514(10) . ? C18 C25 1.544(10) . ? C8 C7 1.339(10) . ? C5 C6 1.449(9) . ? C5 C16 1.494(10) . ? C11 C12 1.407(10) . ? C6 C7 1.317(10) . ? C15 C14 1.440(10) . ? C15 C19 1.488(11) . ? C34 C35 1.384(9) . ? C23 C17 1.538(9) . ? C17 C22 1.526(9) . ? C13 C12 1.340(12) . ? C13 C14 1.366(12) . ? C21 C16 1.544(8) . ? C26 C19 1.536(13) . ? C29 C30 1.535(10) . ? C30 C35 1.373(11) . ? C30 C31 1.397(12) . ? C19 C27 1.542(11) . ? 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 S1 178.56(15) . . ? C28 S1 Cu1 106.7(2) . . ? C1 N1 C2 111.4(4) . . ? C1 N1 C4 125.2(4) . . ? C2 N1 C4 123.4(4) . . ? C9 C4 C5 125.1(5) . . ? C9 C4 N1 117.3(5) . . ? C5 C4 N1 117.5(5) . . ? C1 N2 C3 111.1(4) . . ? C1 N2 C10 123.3(4) . . ? C3 N2 C10 125.5(4) . . ? N2 C1 N1 103.9(4) . . ? N2 C1 Cu1 125.4(3) . . ? N1 C1 Cu1 130.8(3) . . ? C3 C2 N1 106.7(4) . . ? C3 C2 Cl1 130.9(4) . . ? N1 C2 Cl1 122.4(4) . . ? C2 C3 N2 106.9(4) . . ? C2 C3 Cl2 129.9(4) . . ? N2 C3 Cl2 123.3(4) . . ? C29 C28 S1 113.0(5) . . ? C4 C9 C8 116.6(6) . . ? C4 C9 C17 123.7(5) . . ? C8 C9 C17 119.6(6) . . ? C15 C10 C11 125.1(6) . . ? C15 C10 N2 117.1(6) . . ? C11 C10 N2 117.8(5) . . ? C33 C32 C31 120.4(8) . . ? C34 C33 C32 120.4(6) . . ? C11 C18 C24 109.2(6) . . ? C11 C18 C25 113.3(7) . . ? C24 C18 C25 111.1(7) . . ? C7 C8 C9 119.3(7) . . ? C4 C5 C6 113.1(7) . . ? C4 C5 C16 122.0(6) . . ? C6 C5 C16 124.9(6) . . ? C10 C11 C12 117.8(7) . . ? C10 C11 C18 122.3(5) . . ? C12 C11 C18 119.9(7) . . ? C7 C6 C5 121.0(7) . . ? C10 C15 C14 113.8(7) . . ? C10 C15 C19 124.4(6) . . ? C14 C15 C19 121.7(7) . . ? C33 C34 C35 119.0(7) . . ? C9 C17 C22 112.2(5) . . ? C9 C17 C23 110.8(7) . . ? C22 C17 C23 112.5(6) . . ? C12 C13 C14 123.7(9) . . ? C13 C12 C11 118.7(9) . . ? C13 C14 C15 120.8(8) . . ? C5 C16 C20 111.5(5) . . ? C5 C16 C21 113.5(8) . . ? C20 C16 C21 110.6(6) . . ? C28 C29 C30 112.4(6) . . ? C35 C30 C31 116.8(7) . . ? C35 C30 C29 120.6(10) . . ? C31 C30 C29 122.5(9) . . ? C30 C35 C34 122.3(8) . . ? C15 C19 C26 112.9(7) . . ? C15 C19 C27 112.1(9) . . ? C26 C19 C27 111.3(7) . . ? C32 C31 C30 121.0(8) . . ? C6 C7 C8 124.9(8) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.610 _refine_diff_density_min -0.768 _refine_diff_density_rms 0.103