Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Timothy Patten' 'Marcin Brynda' 'Pin-Chieh Chiang' 'Jocelyn M Goodwin' 'Marylin Olmstead' 'Katerina Penkina' _publ_contact_author_name 'Timothy Patten' _publ_contact_author_address ; Department of Chemistry University of California One Shields Avenue Davis CA 95616 UNITED STATES OF AMERICA ; _publ_contact_author_email PATTEN@CHEM.UCDAVIS.EDU _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Asymmetric Dinuclear Copper(I) Complexes of bis-(2-(2-pyridyl)ethyl)-2-(N-toluenesulfonylamino)ethylamine with Short Copper-Copper Distances. ; data_mn1530 _database_code_depnum_ccdc_archive 'CCDC 644442' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cu(PETAEA)CuCl, Compound 1' _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 Cl Cu2 N4 O2 S' _chemical_formula_sum 'C23 H27 Cl Cu2 N4 O2 S' _chemical_formula_weight 586.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' _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 9.1111(6) _cell_length_b 10.8627(7) _cell_length_c 13.4127(9) _cell_angle_alpha 68.776(3) _cell_angle_beta 84.102(3) _cell_angle_gamma 87.524(3) _cell_volume 1230.86(14) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 870 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 20.0 _exptl_crystal_description needle _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 1.949 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.557 _exptl_absorpt_correction_T_max 0.892 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13798 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5612 _reflns_number_gt 4922 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART 5.054 (Bruker, 2002)' _computing_cell_refinement 'SMART 5.054' _computing_data_reduction 'SAINT 6.36A (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _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^)+(0.0289P)^2^+0.8878P] 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 5612 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0646 _refine_ls_wR_factor_gt 0.0599 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.38196(2) 0.44554(2) 0.314772(17) 0.01310(6) Uani 1 1 d . . . Cu2 Cu 0.64892(2) 0.43856(2) 0.210555(17) 0.01446(6) Uani 1 1 d . . . Cl1 Cl 0.79783(5) 0.28374(4) 0.21358(4) 0.02130(10) Uani 1 1 d . . . S1 S 0.58122(5) 0.70150(4) 0.22396(3) 0.01385(9) Uani 1 1 d . . . O1 O 0.46571(14) 0.79175(13) 0.23637(11) 0.0199(3) Uani 1 1 d . . . O2 O 0.66779(14) 0.63780(13) 0.31352(10) 0.0182(3) Uani 1 1 d . . . N1 N 0.37824(16) 0.25539(14) 0.40354(12) 0.0151(3) Uani 1 1 d . . . N2 N 0.25641(16) 0.44765(14) 0.18541(12) 0.0142(3) Uani 1 1 d . . . N3 N 0.23660(16) 0.54475(14) 0.38659(12) 0.0149(3) Uani 1 1 d . . . N4 N 0.51813(16) 0.58518(14) 0.19235(12) 0.0131(3) Uani 1 1 d . . . C1 C 0.3713(2) 0.21654(18) 0.51160(15) 0.0190(4) Uani 1 1 d . . . H1 H 0.3948 0.2789 0.5420 0.023 Uiso 1 1 calc R . . C2 C 0.3317(2) 0.0909(2) 0.57999(16) 0.0266(4) Uani 1 1 d . . . H2 H 0.3287 0.0674 0.6556 0.032 Uiso 1 1 calc R . . C3 C 0.2965(3) -0.0002(2) 0.53602(18) 0.0350(5) Uani 1 1 d . . . H3 H 0.2679 -0.0873 0.5810 0.042 Uiso 1 1 calc R . . C4 C 0.3038(3) 0.0381(2) 0.42545(17) 0.0297(5) Uani 1 1 d . . . H4 H 0.2805 -0.0232 0.3939 0.036 Uiso 1 1 calc R . . C5 C 0.3451(2) 0.16636(18) 0.36008(15) 0.0184(4) Uani 1 1 d . . . C6 C 0.3510(2) 0.21212(18) 0.23951(15) 0.0181(4) Uani 1 1 d . . . H6A H 0.3436 0.1342 0.2186 0.022 Uiso 1 1 calc R . . H6B H 0.4479 0.2536 0.2083 0.022 Uiso 1 1 calc R . . C7 C 0.2284(2) 0.31122(18) 0.19114(15) 0.0181(4) Uani 1 1 d . . . H7A H 0.2179 0.3132 0.1178 0.022 Uiso 1 1 calc R . . H7B H 0.1338 0.2802 0.2351 0.022 Uiso 1 1 calc R . . C8 C 0.11514(19) 0.52010(18) 0.18461(14) 0.0166(4) Uani 1 1 d . . . H8A H 0.0486 0.4953 0.1411 0.020 Uiso 1 1 calc R . . H8B H 0.1337 0.6161 0.1503 0.020 Uiso 1 1 calc R . . C9 C 0.0391(2) 0.49056(19) 0.29817(14) 0.0173(4) Uani 1 1 d . . . H9A H -0.0678 0.5089 0.2929 0.021 Uiso 1 1 calc R . . H9B H 0.0508 0.3952 0.3400 0.021 Uiso 1 1 calc R . . C10 C 0.09616(19) 0.56823(17) 0.35935(14) 0.0151(3) Uani 1 1 d . . . C11 C 0.0057(2) 0.65855(18) 0.38868(15) 0.0189(4) Uani 1 1 d . . . H11 H -0.0913 0.6760 0.3667 0.023 Uiso 1 1 calc R . . C12 C 0.0583(2) 0.72285(18) 0.45016(15) 0.0212(4) Uani 1 1 d . . . H12 H -0.0015 0.7859 0.4696 0.025 Uiso 1 1 calc R . . C13 C 0.1990(2) 0.69388(18) 0.48273(15) 0.0201(4) Uani 1 1 d . . . H13 H 0.2359 0.7333 0.5278 0.024 Uiso 1 1 calc R . . C14 C 0.2846(2) 0.60617(18) 0.44810(14) 0.0173(4) Uani 1 1 d . . . H14 H 0.3822 0.5883 0.4688 0.021 Uiso 1 1 calc R . . C15 C 0.3545(2) 0.51719(17) 0.08790(14) 0.0153(3) Uani 1 1 d . . . H15A H 0.2961 0.5490 0.0250 0.018 Uiso 1 1 calc R . . H15B H 0.4304 0.4548 0.0757 0.018 Uiso 1 1 calc R . . C16 C 0.42971(19) 0.63365(17) 0.09824(14) 0.0150(3) Uani 1 1 d . . . H16A H 0.4948 0.6785 0.0321 0.018 Uiso 1 1 calc R . . H16B H 0.3546 0.6981 0.1078 0.018 Uiso 1 1 calc R . . C17 C 0.70284(19) 0.79421(17) 0.11173(14) 0.0146(3) Uani 1 1 d . . . C18 C 0.6672(2) 0.92351(19) 0.05089(16) 0.0218(4) Uani 1 1 d . . . H18 H 0.5813 0.9646 0.0716 0.026 Uiso 1 1 calc R . . C19 C 0.7587(2) 0.99253(19) -0.04084(17) 0.0247(4) Uani 1 1 d . . . H19 H 0.7332 1.0803 -0.0832 0.030 Uiso 1 1 calc R . . C20 C 0.8867(2) 0.93536(18) -0.07158(15) 0.0184(4) Uani 1 1 d . . . C21 C 0.9222(2) 0.80639(18) -0.00759(15) 0.0168(4) Uani 1 1 d . . . H21 H 1.0104 0.7665 -0.0262 0.020 Uiso 1 1 calc R . . C22 C 0.8305(2) 0.73538(17) 0.08297(14) 0.0158(3) Uani 1 1 d . . . H22 H 0.8550 0.6471 0.1249 0.019 Uiso 1 1 calc R . . C23 C 0.9835(2) 1.0098(2) -0.17201(16) 0.0253(4) Uani 1 1 d . . . H23A H 0.9234 1.0739 -0.2237 0.038 Uiso 1 1 calc R . . H23B H 1.0294 0.9475 -0.2037 0.038 Uiso 1 1 calc R . . H23C H 1.0604 1.0563 -0.1539 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01378(11) 0.01360(11) 0.01222(11) -0.00483(8) -0.00129(8) -0.00159(8) Cu2 0.01347(11) 0.01393(11) 0.01578(12) -0.00518(8) -0.00132(8) 0.00055(8) Cl1 0.0192(2) 0.0181(2) 0.0252(2) -0.00694(18) -0.00065(18) 0.00423(16) S1 0.0134(2) 0.0145(2) 0.0145(2) -0.00633(16) -0.00003(16) -0.00146(15) O1 0.0182(7) 0.0182(6) 0.0245(7) -0.0102(5) 0.0028(5) 0.0001(5) O2 0.0191(7) 0.0217(6) 0.0146(6) -0.0071(5) -0.0027(5) -0.0017(5) N1 0.0153(7) 0.0151(7) 0.0154(7) -0.0060(6) -0.0012(6) -0.0002(6) N2 0.0138(7) 0.0159(7) 0.0128(7) -0.0055(6) 0.0005(6) -0.0021(6) N3 0.0150(7) 0.0159(7) 0.0131(7) -0.0049(6) 0.0008(6) -0.0013(6) N4 0.0131(7) 0.0132(7) 0.0130(7) -0.0046(6) -0.0018(6) -0.0003(5) C1 0.0226(10) 0.0188(9) 0.0169(9) -0.0076(7) -0.0029(7) -0.0006(7) C2 0.0400(12) 0.0222(10) 0.0151(9) -0.0038(8) -0.0015(8) -0.0034(9) C3 0.0606(16) 0.0179(10) 0.0225(11) -0.0016(8) -0.0019(10) -0.0115(10) C4 0.0497(14) 0.0174(9) 0.0230(11) -0.0078(8) -0.0023(9) -0.0079(9) C5 0.0214(9) 0.0169(9) 0.0177(9) -0.0071(7) -0.0015(7) -0.0002(7) C6 0.0234(10) 0.0162(8) 0.0164(9) -0.0082(7) -0.0001(7) -0.0029(7) C7 0.0204(9) 0.0200(9) 0.0161(9) -0.0084(7) -0.0017(7) -0.0050(7) C8 0.0138(8) 0.0228(9) 0.0135(8) -0.0068(7) -0.0021(7) -0.0006(7) C9 0.0136(8) 0.0233(9) 0.0151(9) -0.0072(7) 0.0001(7) -0.0023(7) C10 0.0157(8) 0.0163(8) 0.0105(8) -0.0021(7) 0.0022(6) -0.0021(7) C11 0.0175(9) 0.0186(9) 0.0158(9) -0.0016(7) 0.0017(7) 0.0013(7) C12 0.0281(10) 0.0150(8) 0.0182(9) -0.0053(7) 0.0057(8) 0.0007(7) C13 0.0279(10) 0.0171(9) 0.0159(9) -0.0075(7) 0.0035(7) -0.0049(7) C14 0.0183(9) 0.0193(9) 0.0136(8) -0.0054(7) 0.0007(7) -0.0043(7) C15 0.0155(8) 0.0191(8) 0.0116(8) -0.0058(7) 0.0000(6) -0.0030(7) C16 0.0140(8) 0.0164(8) 0.0133(8) -0.0035(7) -0.0018(7) -0.0007(6) C17 0.0144(8) 0.0150(8) 0.0149(8) -0.0056(7) -0.0018(7) -0.0028(6) C18 0.0186(9) 0.0172(9) 0.0275(10) -0.0067(8) 0.0007(8) 0.0021(7) C19 0.0267(11) 0.0147(9) 0.0264(11) -0.0002(8) -0.0016(8) 0.0008(8) C20 0.0218(9) 0.0175(9) 0.0165(9) -0.0059(7) -0.0022(7) -0.0070(7) C21 0.0142(8) 0.0193(9) 0.0179(9) -0.0081(7) -0.0001(7) -0.0011(7) C22 0.0159(9) 0.0135(8) 0.0174(9) -0.0047(7) -0.0017(7) -0.0006(7) C23 0.0305(11) 0.0220(10) 0.0195(10) -0.0031(8) 0.0027(8) -0.0077(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 N1 1.9755(15) . ? Cu1 N3 2.0517(15) . ? Cu1 N4 2.1158(14) . ? Cu1 N2 2.1671(15) . ? Cu1 Cu2 2.6903(3) . ? Cu2 N4 1.9054(15) . ? Cu2 Cl1 2.1060(5) . ? S1 O2 1.4456(13) . ? S1 O1 1.4454(13) . ? S1 N4 1.6148(14) . ? S1 C17 1.7788(18) . ? N1 C1 1.350(2) . ? N1 C5 1.355(2) . ? N2 C15 1.477(2) . ? N2 C8 1.478(2) . ? N2 C7 1.488(2) . ? N3 C14 1.347(2) . ? N3 C10 1.355(2) . ? N4 C16 1.487(2) . ? C1 C2 1.379(3) . ? C1 H1 0.9500 . ? C2 C3 1.386(3) . ? C2 H2 0.9500 . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.395(3) . ? C4 H4 0.9500 . ? C5 C6 1.506(3) . ? C6 C7 1.539(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.534(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.511(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.393(3) . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.383(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.520(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.389(3) . ? C17 C22 1.390(3) . ? C18 C19 1.395(3) . ? C18 H18 0.9500 . ? C19 C20 1.393(3) . ? C19 H19 0.9500 . ? C20 C21 1.397(3) . ? C20 C23 1.508(3) . ? C21 C22 1.392(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 109.29(6) . . ? N1 Cu1 N4 140.05(6) . . ? N3 Cu1 N4 108.60(6) . . ? N1 Cu1 N2 100.75(6) . . ? N3 Cu1 N2 99.48(6) . . ? N4 Cu1 N2 85.04(5) . . ? N1 Cu1 Cu2 95.31(4) . . ? N3 Cu1 Cu2 147.84(4) . . ? N4 Cu1 Cu2 44.76(4) . . ? N2 Cu1 Cu2 95.77(4) . . ? N4 Cu2 Cl1 174.18(5) . . ? N4 Cu2 Cu1 51.43(4) . . ? Cl1 Cu2 Cu1 132.872(16) . . ? O2 S1 O1 117.83(8) . . ? O2 S1 N4 106.49(8) . . ? O1 S1 N4 111.67(8) . . ? O2 S1 C17 108.12(8) . . ? O1 S1 C17 106.27(8) . . ? N4 S1 C17 105.80(8) . . ? C1 N1 C5 118.36(15) . . ? C1 N1 Cu1 119.84(12) . . ? C5 N1 Cu1 119.71(12) . . ? C15 N2 C8 110.27(14) . . ? C15 N2 C7 109.95(14) . . ? C8 N2 C7 109.85(14) . . ? C15 N2 Cu1 103.30(10) . . ? C8 N2 Cu1 112.10(11) . . ? C7 N2 Cu1 111.20(11) . . ? C14 N3 C10 118.10(16) . . ? C14 N3 Cu1 120.49(12) . . ? C10 N3 Cu1 120.54(12) . . ? C16 N4 S1 113.83(11) . . ? C16 N4 Cu2 120.19(11) . . ? S1 N4 Cu2 114.28(8) . . ? C16 N4 Cu1 105.04(10) . . ? S1 N4 Cu1 115.63(8) . . ? Cu2 N4 Cu1 83.81(5) . . ? N1 C1 C2 123.32(17) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 118.58(19) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 118.72(19) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 120.25(19) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 120.77(17) . . ? N1 C5 C6 117.61(16) . . ? C4 C5 C6 121.60(17) . . ? C5 C6 C7 113.89(16) . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? N2 C7 C6 113.53(14) . . ? N2 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? N2 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? N2 C8 C9 112.07(14) . . ? N2 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? N2 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 114.99(15) . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? N3 C10 C11 121.41(17) . . ? N3 C10 C9 117.79(16) . . ? C11 C10 C9 120.78(16) . . ? C12 C11 C10 119.51(18) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 119.11(18) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 118.37(18) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? N3 C14 C13 123.36(18) . . ? N3 C14 H14 118.3 . . ? C13 C14 H14 118.3 . . ? N2 C15 C16 111.35(14) . . ? N2 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? N2 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N4 C16 C15 109.15(14) . . ? N4 C16 H16A 109.9 . . ? C15 C16 H16A 109.9 . . ? N4 C16 H16B 109.9 . . ? C15 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? C18 C17 C22 120.26(17) . . ? C18 C17 S1 119.87(14) . . ? C22 C17 S1 119.83(13) . . ? C17 C18 C19 119.37(18) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C20 C19 C18 121.37(18) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C21 118.19(17) . . ? C19 C20 C23 121.01(17) . . ? C21 C20 C23 120.80(18) . . ? C22 C21 C20 121.10(17) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C17 C22 C21 119.68(16) . . ? C17 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.503 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.067 #===END data_mn1588 _database_code_depnum_ccdc_archive 'CCDC 644443' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cu(PEMAEA)CuCl Compound 2' _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 Cl Cu2 N4 O3 S' _chemical_formula_sum 'C23 H27 Cl Cu2 N4 O3 S' _chemical_formula_weight 602.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 9.5617(12) _cell_length_b 9.9875(10) _cell_length_c 13.4720(12) _cell_angle_alpha 92.187(8) _cell_angle_beta 91.981(9) _cell_angle_gamma 108.049(8) _cell_volume 1220.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 5.6 _cell_measurement_theta_max 30.0 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 4.233 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2003 _exptl_absorpt_correction_T_max 0.7282 _exptl_absorpt_process_details ;XABS2, Parkin, S., Moezzi, B. and Hope, H. J. Appl. Crystallogr. 28 (1995) 53-56. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Siemens rotating anode' _diffrn_radiation_monochromator 'nickel filter' _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.2 _diffrn_reflns_number 4351 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 56.09 _reflns_number_total 3203 _reflns_number_gt 3044 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens P3/Pc' _computing_cell_refinement 'Siemens P3/Pc' _computing_data_reduction 'Siemens XDISK' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL97 _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^)+(0.1298P)^2^+1.3756P] 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 SHELXL _refine_ls_extinction_coef 0.0086(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3203 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1700 _refine_ls_wR_factor_gt 0.1676 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 0.39240(6) 0.24561(6) 0.22083(4) 0.0184(3) Uani 1 1 d . . . Cu2 Cu 0.28362(6) 0.36280(6) 0.36721(4) 0.0197(3) Uani 1 1 d . . . Cl1 Cl 0.25844(13) 0.32165(11) 0.51806(8) 0.0297(4) Uani 1 1 d . . . S1 S 0.12631(11) 0.37786(11) 0.18139(8) 0.0191(4) Uani 1 1 d . . . O1 O 0.1243(3) 0.3636(3) 0.0750(2) 0.0283(8) Uani 1 1 d . . . O2 O 0.0272(3) 0.2648(3) 0.2318(2) 0.0263(7) Uani 1 1 d . . . O3 O -0.0018(4) 0.9136(3) 0.2627(3) 0.0333(8) Uani 1 1 d . . . N1 N 0.4649(4) 0.1275(4) 0.3126(3) 0.0204(8) Uani 1 1 d . . . N2 N 0.5925(4) 0.4158(4) 0.2046(3) 0.0209(8) Uani 1 1 d . . . N3 N 0.3632(4) 0.1559(4) 0.0791(3) 0.0235(9) Uani 1 1 d . . . N4 N 0.2882(4) 0.4050(4) 0.2308(3) 0.0194(8) Uani 1 1 d . . . C1 C 0.4038(5) -0.0143(5) 0.3076(3) 0.0240(10) Uani 1 1 d . . . H1 H 0.3128 -0.0543 0.2708 0.029 Uiso 1 1 calc R . . C2 C 0.4674(5) -0.1035(5) 0.3534(4) 0.0290(11) Uani 1 1 d . . . H2 H 0.4190 -0.2023 0.3505 0.035 Uiso 1 1 calc R . . C3 C 0.6013(6) -0.0475(5) 0.4029(4) 0.0319(12) Uani 1 1 d . . . H3 H 0.6487 -0.1070 0.4337 0.038 Uiso 1 1 calc R . . C4 C 0.6664(5) 0.0968(5) 0.4075(4) 0.0296(11) Uani 1 1 d . . . H4 H 0.7601 0.1372 0.4409 0.036 Uiso 1 1 calc R . . C5 C 0.5954(5) 0.1835(5) 0.3633(3) 0.0210(10) Uani 1 1 d . . . C6 C 0.6609(5) 0.3404(5) 0.3703(3) 0.0262(11) Uani 1 1 d . . . H6A H 0.7450 0.3660 0.4199 0.031 Uiso 1 1 calc R . . H6B H 0.5863 0.3816 0.3954 0.031 Uiso 1 1 calc R . . C7 C 0.7143(5) 0.4065(5) 0.2734(4) 0.0262(11) Uani 1 1 d . . . H7A H 0.7833 0.5026 0.2885 0.031 Uiso 1 1 calc R . . H7B H 0.7692 0.3502 0.2396 0.031 Uiso 1 1 calc R . . C8 C 0.6359(5) 0.4184(5) 0.1006(3) 0.0240(10) Uani 1 1 d . . . H8A H 0.7386 0.4807 0.0975 0.029 Uiso 1 1 calc R . . H8B H 0.5720 0.4588 0.0601 0.029 Uiso 1 1 calc R . . C9 C 0.6246(5) 0.2722(5) 0.0556(4) 0.0297(11) Uani 1 1 d . . . H9A H 0.6929 0.2841 0.0006 0.036 Uiso 1 1 calc R . . H9B H 0.6588 0.2197 0.1070 0.036 Uiso 1 1 calc R . . C10 C 0.4735(5) 0.1836(5) 0.0160(3) 0.0246(10) Uani 1 1 d . . . C11 C 0.4494(6) 0.1314(5) -0.0815(4) 0.0329(12) Uani 1 1 d . . . H11 H 0.5286 0.1528 -0.1250 0.039 Uiso 1 1 calc R . . C12 C 0.3121(7) 0.0489(5) -0.1160(4) 0.0398(13) Uani 1 1 d . . . H12 H 0.2944 0.0141 -0.1834 0.048 Uiso 1 1 calc R . . C13 C 0.2002(6) 0.0178(5) -0.0506(4) 0.0360(13) Uani 1 1 d . . . H13 H 0.1042 -0.0410 -0.0717 0.043 Uiso 1 1 calc R . . C14 C 0.2294(5) 0.0729(5) 0.0453(4) 0.0272(11) Uani 1 1 d . . . H14 H 0.1515 0.0515 0.0899 0.033 Uiso 1 1 calc R . . C15 C 0.5524(5) 0.5430(4) 0.2320(3) 0.0205(10) Uani 1 1 d . . . H15A H 0.6238 0.6263 0.2049 0.025 Uiso 1 1 calc R . . H15B H 0.5576 0.5572 0.3053 0.025 Uiso 1 1 calc R . . C16 C 0.3980(5) 0.5304(5) 0.1919(3) 0.0211(10) Uani 1 1 d . . . H16A H 0.3737 0.6166 0.2120 0.025 Uiso 1 1 calc R . . H16B H 0.3940 0.5216 0.1184 0.025 Uiso 1 1 calc R . . C17 C 0.0850(4) 0.5372(4) 0.2101(3) 0.0188(10) Uani 1 1 d . . . C18 C 0.0499(5) 0.6120(5) 0.1327(3) 0.0214(10) Uani 1 1 d . . . H18 H 0.0473 0.5775 0.0658 0.026 Uiso 1 1 calc R . . C19 C 0.0191(5) 0.7354(5) 0.1532(3) 0.0227(10) Uani 1 1 d . . . H19 H -0.0053 0.7859 0.1005 0.027 Uiso 1 1 calc R . . C20 C 0.0236(5) 0.7864(5) 0.2512(4) 0.0232(10) Uani 1 1 d . . . C21 C 0.0565(5) 0.7118(5) 0.3293(3) 0.0228(10) Uani 1 1 d . . . H21 H 0.0593 0.7462 0.3963 0.027 Uiso 1 1 calc R . . C22 C 0.0854(4) 0.5853(4) 0.3072(3) 0.0194(10) Uani 1 1 d . . . H22 H 0.1056 0.5321 0.3597 0.023 Uiso 1 1 calc R . . C23 C 0.0146(6) 0.9788(5) 0.3611(4) 0.0322(11) Uani 1 1 d . . . H23A H -0.0040 1.0697 0.3584 0.048 Uiso 1 1 calc R . . H23B H 0.1149 0.9936 0.3883 0.048 Uiso 1 1 calc R . . H23C H -0.0561 0.9174 0.4038 0.048 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 0.0157(4) 0.0201(5) 0.0180(5) 0.0005(3) 0.0010(3) 0.0038(3) Cu2 0.0210(5) 0.0224(5) 0.0155(5) 0.0022(3) 0.0017(3) 0.0062(3) Cl1 0.0464(8) 0.0266(7) 0.0171(6) 0.0037(5) 0.0053(5) 0.0120(5) S1 0.0170(6) 0.0207(6) 0.0190(7) -0.0024(4) -0.0031(4) 0.0059(4) O1 0.0325(18) 0.0329(18) 0.0220(18) -0.0076(14) -0.0071(14) 0.0160(15) O2 0.0165(16) 0.0225(17) 0.0360(19) 0.0010(13) -0.0029(13) 0.0008(13) O3 0.047(2) 0.0240(17) 0.0320(19) -0.0046(14) -0.0046(15) 0.0165(15) N1 0.0215(19) 0.025(2) 0.0146(19) -0.0016(15) 0.0004(15) 0.0074(16) N2 0.0122(18) 0.0224(19) 0.027(2) 0.0007(16) 0.0030(15) 0.0040(15) N3 0.030(2) 0.024(2) 0.019(2) 0.0003(15) 0.0035(16) 0.0115(16) N4 0.0181(19) 0.0222(19) 0.019(2) 0.0018(15) -0.0014(15) 0.0077(15) C1 0.025(2) 0.026(3) 0.019(2) -0.0041(19) 0.0065(19) 0.004(2) C2 0.037(3) 0.023(2) 0.028(3) 0.002(2) 0.009(2) 0.010(2) C3 0.045(3) 0.033(3) 0.026(3) 0.006(2) 0.004(2) 0.023(2) C4 0.029(3) 0.039(3) 0.023(3) 0.003(2) 0.000(2) 0.013(2) C5 0.019(2) 0.029(2) 0.016(2) 0.0024(18) 0.0018(18) 0.0087(19) C6 0.023(2) 0.026(2) 0.028(3) -0.003(2) -0.0086(19) 0.0075(19) C7 0.014(2) 0.026(2) 0.038(3) 0.001(2) -0.0007(19) 0.0064(18) C8 0.018(2) 0.025(2) 0.026(3) 0.0063(19) 0.0085(18) 0.0017(18) C9 0.029(3) 0.033(3) 0.030(3) 0.001(2) 0.011(2) 0.013(2) C10 0.033(3) 0.023(2) 0.023(3) 0.0021(19) 0.008(2) 0.016(2) C11 0.051(3) 0.026(3) 0.025(3) 0.005(2) 0.015(2) 0.016(2) C12 0.069(4) 0.031(3) 0.023(3) -0.003(2) -0.002(3) 0.022(3) C13 0.044(3) 0.033(3) 0.036(3) -0.006(2) -0.012(2) 0.021(2) C14 0.025(2) 0.026(2) 0.029(3) -0.010(2) -0.005(2) 0.006(2) C15 0.019(2) 0.017(2) 0.023(2) 0.0030(17) 0.0025(18) 0.0018(17) C16 0.024(2) 0.020(2) 0.022(2) 0.0033(18) 0.0045(18) 0.0098(18) C17 0.011(2) 0.021(2) 0.021(2) -0.0029(18) 0.0003(17) 0.0008(17) C18 0.016(2) 0.022(2) 0.023(2) -0.0008(18) -0.0017(18) 0.0012(18) C19 0.019(2) 0.024(2) 0.023(2) 0.0048(18) -0.0057(18) 0.0028(18) C20 0.013(2) 0.018(2) 0.035(3) 0.0016(19) -0.0001(18) 0.0008(17) C21 0.015(2) 0.026(2) 0.024(2) -0.0023(19) 0.0025(18) 0.0026(18) C22 0.014(2) 0.023(2) 0.022(2) 0.0045(18) 0.0024(17) 0.0056(17) C23 0.035(3) 0.024(3) 0.038(3) -0.002(2) 0.010(2) 0.009(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 N1 1.990(4) . ? Cu1 N3 2.050(4) . ? Cu1 N4 2.126(3) . ? Cu1 N2 2.154(3) . ? Cu1 Cu2 2.6572(8) . ? Cu2 N4 1.900(3) . ? Cu2 Cl1 2.0960(12) . ? S1 O1 1.434(3) . ? S1 O2 1.440(3) . ? S1 N4 1.602(3) . ? S1 C17 1.786(4) . ? O3 C20 1.370(6) . ? O3 C23 1.436(6) . ? N1 C5 1.348(6) . ? N1 C1 1.353(6) . ? N2 C15 1.474(6) . ? N2 C8 1.475(6) . ? N2 C7 1.491(6) . ? N3 C10 1.345(6) . ? N3 C14 1.344(6) . ? N4 C16 1.489(6) . ? C1 C2 1.376(7) . ? C1 H1 0.9500 . ? C2 C3 1.366(7) . ? C2 H2 0.9500 . ? C3 C4 1.379(8) . ? C3 H3 0.9500 . ? C4 C5 1.393(7) . ? C4 H4 0.9500 . ? C5 C6 1.495(7) . ? C6 C7 1.518(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.530(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.508(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.380(7) . ? C11 C12 1.370(8) . ? C11 H11 0.9500 . ? C12 C13 1.377(8) . ? C12 H12 0.9500 . ? C13 C14 1.370(7) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.519(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.376(6) . ? C17 C18 1.396(6) . ? C18 C19 1.373(7) . ? C18 H18 0.9500 . ? C19 C20 1.391(7) . ? C19 H19 0.9500 . ? C20 C21 1.393(7) . ? C21 C22 1.398(6) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 109.96(14) . . ? N1 Cu1 N4 137.90(14) . . ? N3 Cu1 N4 109.94(14) . . ? N1 Cu1 N2 100.50(14) . . ? N3 Cu1 N2 99.39(15) . . ? N4 Cu1 N2 85.75(13) . . ? N1 Cu1 Cu2 92.87(10) . . ? N3 Cu1 Cu2 147.76(11) . . ? N4 Cu1 Cu2 45.14(9) . . ? N2 Cu1 Cu2 98.38(10) . . ? N4 Cu2 Cl1 174.12(11) . . ? N4 Cu2 Cu1 52.46(10) . . ? Cl1 Cu2 Cu1 132.48(4) . . ? O1 S1 O2 117.30(19) . . ? O1 S1 N4 111.89(19) . . ? O2 S1 N4 107.48(18) . . ? O1 S1 C17 106.12(19) . . ? O2 S1 C17 108.90(19) . . ? N4 S1 C17 104.35(19) . . ? C20 O3 C23 118.0(4) . . ? C5 N1 C1 118.2(4) . . ? C5 N1 Cu1 119.5(3) . . ? C1 N1 Cu1 120.5(3) . . ? C15 N2 C8 110.4(3) . . ? C15 N2 C7 109.6(3) . . ? C8 N2 C7 110.8(3) . . ? C15 N2 Cu1 103.7(2) . . ? C8 N2 Cu1 110.2(3) . . ? C7 N2 Cu1 111.9(3) . . ? C10 N3 C14 118.2(4) . . ? C10 N3 Cu1 121.7(3) . . ? C14 N3 Cu1 120.0(3) . . ? C16 N4 S1 112.3(3) . . ? C16 N4 Cu2 123.1(3) . . ? S1 N4 Cu2 112.00(19) . . ? C16 N4 Cu1 103.7(2) . . ? S1 N4 Cu1 120.5(2) . . ? Cu2 N4 Cu1 82.39(13) . . ? N1 C1 C2 123.1(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 118.9(4) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 118.8(4) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C3 C4 C5 120.3(5) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N1 C5 C4 120.6(4) . . ? N1 C5 C6 118.0(4) . . ? C4 C5 C6 121.4(4) . . ? C5 C6 C7 115.0(4) . . ? C5 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? C5 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? N2 C7 C6 113.2(4) . . ? N2 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? N2 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? N2 C8 C9 113.0(4) . . ? N2 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? N2 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 115.8(4) . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9B 108.3 . . ? C8 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? N3 C10 C11 121.1(4) . . ? N3 C10 C9 117.9(4) . . ? C11 C10 C9 121.0(4) . . ? C12 C11 C10 120.4(5) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 118.4(5) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C14 C13 C12 119.0(5) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? N3 C14 C13 122.9(5) . . ? N3 C14 H14 118.5 . . ? C13 C14 H14 118.5 . . ? N2 C15 C16 111.3(4) . . ? N2 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? N2 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N4 C16 C15 110.6(3) . . ? N4 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? N4 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? C22 C17 C18 120.0(4) . . ? C22 C17 S1 120.7(3) . . ? C18 C17 S1 119.2(3) . . ? C19 C18 C17 120.1(4) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.0(4) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? O3 C20 C19 115.0(4) . . ? O3 C20 C21 124.5(4) . . ? C19 C20 C21 120.5(4) . . ? C20 C21 C22 118.8(4) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? C17 C22 C21 120.5(4) . . ? C17 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 56.09 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.642 _refine_diff_density_min -1.446 _refine_diff_density_rms 0.181 #===END data_mn1643 _database_code_depnum_ccdc_archive 'CCDC 644444' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cu(PENAEA)CuCl Compound 3' _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 Cl Cu2 N5 O4 S' _chemical_formula_sum 'C22 H24 Cl Cu2 N5 O4 S' _chemical_formula_weight 617.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9933(9) _cell_length_b 10.8437(11) _cell_length_c 26.491(3) _cell_angle_alpha 94.085(3) _cell_angle_beta 98.630(4) _cell_angle_gamma 92.039(3) _cell_volume 2544.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 972 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 20.0 _exptl_crystal_description needle _exptl_crystal_colour red-brown _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 1.897 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.377 _exptl_absorpt_correction_T_max 0.895 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28321 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.48 _reflns_number_total 11643 _reflns_number_gt 9820 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART 5.054 (Bruker, 2003)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT 6.45A (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL97 _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^)+(0.0336P)^2^+1.5338P] 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 11643 _refine_ls_number_parameters 631 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.22197(3) 0.58101(2) 0.099963(9) 0.01375(6) Uani 1 1 d . . . Cu2 Cu -0.01058(3) 0.60905(2) 0.151174(9) 0.01437(6) Uani 1 1 d . . . Cl1 Cl -0.14007(6) 0.76555(5) 0.15875(2) 0.02255(11) Uani 1 1 d . . . S1 S 0.02224(6) 0.34704(4) 0.115245(18) 0.01411(10) Uani 1 1 d . . . O1 O 0.12629(17) 0.25602(13) 0.10241(6) 0.0212(3) Uani 1 1 d . . . O2 O -0.08019(16) 0.39175(13) 0.07387(5) 0.0183(3) Uani 1 1 d . . . O3 O -0.40225(19) -0.01336(14) 0.23666(6) 0.0267(4) Uani 1 1 d . . . O4 O -0.53588(18) 0.14881(16) 0.22756(6) 0.0271(4) Uani 1 1 d . . . N1 N 0.20213(18) 0.75398(15) 0.08144(6) 0.0144(3) Uani 1 1 d . . . N2 N 0.38942(18) 0.60293(15) 0.16717(6) 0.0137(3) Uani 1 1 d . . . N3 N 0.31898(19) 0.46621(16) 0.05205(6) 0.0154(3) Uani 1 1 d . . . N4 N 0.10518(18) 0.46634(15) 0.14836(6) 0.0131(3) Uani 1 1 d . . . N5 N -0.4213(2) 0.09250(17) 0.22419(6) 0.0205(4) Uani 1 1 d . . . C1 C 0.1562(2) 0.7778(2) 0.03231(8) 0.0188(4) Uani 1 1 d . . . H1B H 0.1219 0.7104 0.0080 0.023 Uiso 1 1 calc R . . C2 C 0.1568(3) 0.8961(2) 0.01580(8) 0.0239(5) Uani 1 1 d . . . H2B H 0.1236 0.9094 -0.0191 0.029 Uiso 1 1 calc R . . C3 C 0.2066(3) 0.9947(2) 0.05113(9) 0.0253(5) Uani 1 1 d . . . H3A H 0.2073 1.0770 0.0410 0.030 Uiso 1 1 calc R . . C4 C 0.2555(3) 0.9713(2) 0.10148(8) 0.0208(4) Uani 1 1 d . . . H4A H 0.2912 1.0377 0.1262 0.025 Uiso 1 1 calc R . . C5 C 0.2523(2) 0.85030(18) 0.11585(7) 0.0151(4) Uani 1 1 d . . . C6 C 0.3026(2) 0.82226(18) 0.17060(7) 0.0156(4) Uani 1 1 d . . . H6A H 0.2159 0.7842 0.1838 0.019 Uiso 1 1 calc R . . H6B H 0.3319 0.9013 0.1913 0.019 Uiso 1 1 calc R . . C7 C 0.4347(2) 0.73598(18) 0.17867(7) 0.0161(4) Uani 1 1 d . . . H7A H 0.5092 0.7588 0.1566 0.019 Uiso 1 1 calc R . . H7B H 0.4846 0.7491 0.2147 0.019 Uiso 1 1 calc R . . C8 C 0.5213(2) 0.53057(19) 0.15845(7) 0.0168(4) Uani 1 1 d . . . H8A H 0.5005 0.4431 0.1647 0.020 Uiso 1 1 calc R . . H8B H 0.6096 0.5625 0.1835 0.020 Uiso 1 1 calc R . . C9 C 0.5601(2) 0.5360(2) 0.10421(7) 0.0179(4) Uani 1 1 d . . . H9A H 0.5470 0.6213 0.0938 0.021 Uiso 1 1 calc R . . H9B H 0.6677 0.5183 0.1051 0.021 Uiso 1 1 calc R . . C10 C 0.4678(2) 0.44777(19) 0.06396(7) 0.0165(4) Uani 1 1 d . . . C11 C 0.5350(3) 0.3520(2) 0.03918(8) 0.0213(4) Uani 1 1 d . . . H11A H 0.6391 0.3390 0.0486 0.026 Uiso 1 1 calc R . . C12 C 0.4486(3) 0.2756(2) 0.00074(8) 0.0231(5) Uani 1 1 d . . . H12A H 0.4925 0.2091 -0.0161 0.028 Uiso 1 1 calc R . . C13 C 0.2976(3) 0.2976(2) -0.01287(8) 0.0205(4) Uani 1 1 d . . . H13A H 0.2369 0.2484 -0.0399 0.025 Uiso 1 1 calc R . . C14 C 0.2376(2) 0.39255(19) 0.01379(7) 0.0181(4) Uani 1 1 d . . . H14A H 0.1337 0.4069 0.0048 0.022 Uiso 1 1 calc R . . C15 C 0.3198(2) 0.55438(19) 0.20947(7) 0.0152(4) Uani 1 1 d . . . H15A H 0.2580 0.6185 0.2233 0.018 Uiso 1 1 calc R . . H15B H 0.3999 0.5355 0.2374 0.018 Uiso 1 1 calc R . . C16 C 0.2213(2) 0.43806(19) 0.19150(7) 0.0163(4) Uani 1 1 d . . . H16A H 0.2836 0.3711 0.1802 0.020 Uiso 1 1 calc R . . H16B H 0.1723 0.4099 0.2200 0.020 Uiso 1 1 calc R . . C17 C -0.0947(2) 0.27205(18) 0.15406(7) 0.0150(4) Uani 1 1 d . . . C18 C -0.1026(3) 0.14314(19) 0.15235(8) 0.0205(4) Uani 1 1 d . . . H18A H -0.0367 0.0965 0.1345 0.025 Uiso 1 1 calc R . . C19 C -0.2073(3) 0.0833(2) 0.17692(8) 0.0224(5) Uani 1 1 d . . . H19A H -0.2146 -0.0045 0.1761 0.027 Uiso 1 1 calc R . . C20 C -0.3003(2) 0.15494(19) 0.20248(7) 0.0165(4) Uani 1 1 d . . . C21 C -0.2901(2) 0.28264(19) 0.20685(8) 0.0186(4) Uani 1 1 d . . . H21A H -0.3525 0.3289 0.2263 0.022 Uiso 1 1 calc R . . C22 C -0.1855(2) 0.34144(19) 0.18183(8) 0.0180(4) Uani 1 1 d . . . H22A H -0.1763 0.4293 0.1838 0.022 Uiso 1 1 calc R . . Cu3 Cu 0.29004(3) 1.04989(2) 0.397454(9) 0.01293(6) Uani 1 1 d . . . Cu4 Cu 0.53052(3) 1.06155(2) 0.351513(9) 0.01348(6) Uani 1 1 d . . . Cl2 Cl 0.67522(6) 1.21564(5) 0.345650(19) 0.02024(11) Uani 1 1 d . . . S2 S 0.47303(5) 0.81188(4) 0.386278(18) 0.01298(10) Uani 1 1 d . . . O5 O 0.35989(17) 0.72330(13) 0.39639(6) 0.0187(3) Uani 1 1 d . . . O6 O 0.57237(16) 0.87262(13) 0.42974(5) 0.0175(3) Uani 1 1 d . . . O7 O 1.02396(19) 0.59941(16) 0.27023(7) 0.0311(4) Uani 1 1 d . . . O8 O 0.94646(19) 0.42633(15) 0.29585(7) 0.0299(4) Uani 1 1 d . . . N6 N 0.31592(19) 1.22966(15) 0.41599(6) 0.0142(3) Uani 1 1 d . . . N7 N 0.12766(18) 1.04341(15) 0.32887(6) 0.0131(3) Uani 1 1 d . . . N8 N 0.18251(19) 0.95326(15) 0.44486(6) 0.0146(3) Uani 1 1 d . . . N9 N 0.40327(18) 0.91784(15) 0.35217(6) 0.0122(3) Uani 1 1 d . . . N10 N 0.9353(2) 0.53707(17) 0.29003(7) 0.0212(4) Uani 1 1 d . . . C23 C 0.3505(2) 1.27279(19) 0.46576(8) 0.0186(4) Uani 1 1 d . . . H23A H 0.3833 1.2161 0.4904 0.022 Uiso 1 1 calc R . . C24 C 0.3403(3) 1.3949(2) 0.48245(8) 0.0234(5) Uani 1 1 d . . . H24A H 0.3651 1.4213 0.5178 0.028 Uiso 1 1 calc R . . C25 C 0.2932(3) 1.4788(2) 0.44679(8) 0.0230(5) Uani 1 1 d . . . H25A H 0.2860 1.5638 0.4572 0.028 Uiso 1 1 calc R . . C26 C 0.2571(2) 1.43595(19) 0.39568(8) 0.0197(4) Uani 1 1 d . . . H26A H 0.2241 1.4916 0.3707 0.024 Uiso 1 1 calc R . . C27 C 0.2692(2) 1.31136(19) 0.38107(7) 0.0151(4) Uani 1 1 d . . . C28 C 0.2297(2) 1.26170(18) 0.32581(7) 0.0152(4) Uani 1 1 d . . . H28A H 0.3174 1.2196 0.3154 0.018 Uiso 1 1 calc R . . H28B H 0.2103 1.3322 0.3043 0.018 Uiso 1 1 calc R . . C29 C 0.0916(2) 1.17052(18) 0.31515(7) 0.0156(4) Uani 1 1 d . . . H29A H 0.0135 1.2012 0.3349 0.019 Uiso 1 1 calc R . . H29B H 0.0494 1.1676 0.2783 0.019 Uiso 1 1 calc R . . C30 C -0.0101(2) 0.97345(19) 0.33713(7) 0.0153(4) Uani 1 1 d . . . H30A H 0.0051 0.8838 0.3318 0.018 Uiso 1 1 calc R . . H30B H -0.0951 0.9939 0.3113 0.018 Uiso 1 1 calc R . . C31 C -0.0518(2) 1.0009(2) 0.39064(7) 0.0174(4) Uani 1 1 d . . . H31A H -0.0331 1.0906 0.4004 0.021 Uiso 1 1 calc R . . H31B H -0.1611 0.9821 0.3889 0.021 Uiso 1 1 calc R . . C32 C 0.0318(2) 0.93029(19) 0.43233(7) 0.0154(4) Uani 1 1 d . . . C33 C -0.0450(2) 0.8466(2) 0.45809(8) 0.0211(4) Uani 1 1 d . . . H33A H -0.1503 0.8304 0.4485 0.025 Uiso 1 1 calc R . . C34 C 0.0338(3) 0.7874(2) 0.49781(8) 0.0226(5) Uani 1 1 d . . . H34A H -0.0167 0.7292 0.5153 0.027 Uiso 1 1 calc R . . C35 C 0.1872(2) 0.81426(19) 0.51163(8) 0.0184(4) Uani 1 1 d . . . H35A H 0.2433 0.7770 0.5394 0.022 Uiso 1 1 calc R . . C36 C 0.2561(2) 0.89639(19) 0.48410(7) 0.0168(4) Uani 1 1 d . . . H36A H 0.3613 0.9139 0.4933 0.020 Uiso 1 1 calc R . . C37 C 0.1976(2) 0.97821(19) 0.28788(7) 0.0154(4) Uani 1 1 d . . . H37A H 0.2647 1.0373 0.2741 0.018 Uiso 1 1 calc R . . H37B H 0.1179 0.9462 0.2596 0.018 Uiso 1 1 calc R . . C38 C 0.2880(2) 0.87129(18) 0.30808(7) 0.0151(4) Uani 1 1 d . . . H38A H 0.2199 0.8082 0.3190 0.018 Uiso 1 1 calc R . . H38B H 0.3379 0.8320 0.2806 0.018 Uiso 1 1 calc R . . C39 C 0.5933(2) 0.72497(18) 0.35071(7) 0.0139(4) Uani 1 1 d . . . C40 C 0.6184(2) 0.60303(19) 0.36208(8) 0.0180(4) Uani 1 1 d . . . H40A H 0.5604 0.5638 0.3840 0.022 Uiso 1 1 calc R . . C41 C 0.7286(3) 0.53942(19) 0.34119(8) 0.0205(4) Uani 1 1 d . . . H41A H 0.7485 0.4569 0.3489 0.025 Uiso 1 1 calc R . . C42 C 0.8086(2) 0.59957(19) 0.30870(7) 0.0165(4) Uani 1 1 d . . . C43 C 0.7780(2) 0.71679(19) 0.29370(7) 0.0162(4) Uani 1 1 d . . . H43A H 0.8297 0.7527 0.2692 0.019 Uiso 1 1 calc R . . C44 C 0.6694(2) 0.78034(18) 0.31563(7) 0.0144(4) Uani 1 1 d . . . H44A H 0.6470 0.8617 0.3067 0.017 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 0.01358(12) 0.01359(12) 0.01351(11) -0.00033(9) 0.00118(9) -0.00070(9) Cu2 0.01347(12) 0.01226(12) 0.01743(12) -0.00027(9) 0.00308(9) 0.00108(9) Cl1 0.0209(3) 0.0169(2) 0.0298(3) -0.0016(2) 0.0043(2) 0.0060(2) S1 0.0159(2) 0.0118(2) 0.0153(2) -0.00110(17) 0.00593(18) -0.00089(18) O1 0.0215(8) 0.0153(7) 0.0292(8) -0.0021(6) 0.0134(6) 0.0008(6) O2 0.0205(8) 0.0187(7) 0.0148(7) -0.0008(5) 0.0018(6) -0.0031(6) O3 0.0380(10) 0.0190(8) 0.0228(8) 0.0066(6) 0.0040(7) -0.0093(7) O4 0.0180(8) 0.0374(10) 0.0270(8) 0.0078(7) 0.0052(6) -0.0037(7) N1 0.0123(8) 0.0159(8) 0.0151(8) -0.0004(6) 0.0032(6) 0.0003(7) N2 0.0115(8) 0.0166(8) 0.0133(8) 0.0003(6) 0.0035(6) 0.0002(7) N3 0.0165(9) 0.0173(9) 0.0128(8) 0.0007(6) 0.0042(6) -0.0014(7) N4 0.0127(8) 0.0123(8) 0.0142(8) 0.0005(6) 0.0018(6) 0.0005(6) N5 0.0218(10) 0.0245(10) 0.0140(8) 0.0036(7) -0.0002(7) -0.0079(8) C1 0.0176(10) 0.0213(11) 0.0168(10) -0.0020(8) 0.0015(8) 0.0013(8) C2 0.0305(13) 0.0237(11) 0.0179(10) 0.0057(9) 0.0019(9) 0.0069(10) C3 0.0323(13) 0.0183(11) 0.0268(11) 0.0060(9) 0.0063(10) 0.0062(9) C4 0.0239(11) 0.0156(10) 0.0229(10) -0.0011(8) 0.0045(9) 0.0011(9) C5 0.0127(10) 0.0152(10) 0.0176(9) -0.0017(7) 0.0039(7) 0.0005(8) C6 0.0169(10) 0.0146(10) 0.0144(9) -0.0038(7) 0.0026(7) -0.0013(8) C7 0.0151(10) 0.0173(10) 0.0149(9) -0.0012(7) 0.0012(7) -0.0020(8) C8 0.0125(10) 0.0204(10) 0.0169(9) -0.0008(8) 0.0011(7) 0.0023(8) C9 0.0131(10) 0.0232(11) 0.0178(10) -0.0010(8) 0.0055(8) -0.0007(8) C10 0.0171(10) 0.0190(10) 0.0145(9) 0.0024(8) 0.0061(8) -0.0015(8) C11 0.0202(11) 0.0262(12) 0.0183(10) 0.0017(8) 0.0054(8) 0.0040(9) C12 0.0311(13) 0.0201(11) 0.0194(10) -0.0032(8) 0.0101(9) 0.0021(9) C13 0.0256(11) 0.0209(11) 0.0141(9) -0.0035(8) 0.0045(8) -0.0067(9) C14 0.0175(10) 0.0207(10) 0.0162(9) 0.0014(8) 0.0045(8) -0.0044(8) C15 0.0143(10) 0.0197(10) 0.0116(9) 0.0010(7) 0.0027(7) 0.0008(8) C16 0.0166(10) 0.0170(10) 0.0158(9) 0.0043(8) 0.0028(8) 0.0011(8) C17 0.0124(9) 0.0153(10) 0.0175(9) 0.0015(7) 0.0032(7) -0.0024(8) C18 0.0242(11) 0.0138(10) 0.0248(11) -0.0010(8) 0.0085(9) 0.0012(9) C19 0.0289(12) 0.0131(10) 0.0260(11) 0.0034(8) 0.0066(9) -0.0013(9) C20 0.0163(10) 0.0166(10) 0.0162(9) 0.0046(8) 0.0006(8) -0.0044(8) C21 0.0192(11) 0.0180(10) 0.0204(10) 0.0044(8) 0.0071(8) 0.0023(8) C22 0.0214(11) 0.0111(9) 0.0232(10) 0.0019(8) 0.0081(8) 0.0006(8) Cu3 0.01287(12) 0.01280(12) 0.01293(11) 0.00130(9) 0.00106(9) 0.00144(9) Cu4 0.01305(12) 0.01186(12) 0.01571(12) 0.00213(9) 0.00232(9) 0.00025(9) Cl2 0.0189(2) 0.0164(2) 0.0250(2) 0.00503(19) 0.00171(19) -0.00346(19) S2 0.0140(2) 0.0118(2) 0.0142(2) 0.00257(17) 0.00440(17) 0.00258(18) O5 0.0194(8) 0.0146(7) 0.0247(7) 0.0042(6) 0.0101(6) 0.0021(6) O6 0.0199(8) 0.0184(7) 0.0141(7) 0.0015(5) 0.0011(6) 0.0045(6) O7 0.0254(9) 0.0341(10) 0.0381(10) 0.0020(8) 0.0174(7) 0.0071(8) O8 0.0302(9) 0.0213(9) 0.0392(10) -0.0008(7) 0.0077(7) 0.0118(7) N6 0.0132(8) 0.0145(8) 0.0151(8) 0.0022(6) 0.0026(6) 0.0001(7) N7 0.0122(8) 0.0138(8) 0.0134(8) 0.0000(6) 0.0028(6) 0.0020(6) N8 0.0153(8) 0.0150(8) 0.0139(8) 0.0001(6) 0.0031(6) 0.0024(7) N9 0.0121(8) 0.0118(8) 0.0125(7) 0.0018(6) 0.0012(6) 0.0003(6) N10 0.0179(9) 0.0245(10) 0.0202(9) -0.0041(7) 0.0017(7) 0.0047(8) C23 0.0191(11) 0.0193(10) 0.0166(10) 0.0026(8) 0.0005(8) -0.0034(8) C24 0.0304(13) 0.0214(11) 0.0171(10) -0.0027(8) 0.0035(9) -0.0071(9) C25 0.0290(12) 0.0140(10) 0.0259(11) -0.0020(8) 0.0057(9) -0.0022(9) C26 0.0228(11) 0.0157(10) 0.0207(10) 0.0038(8) 0.0029(8) -0.0001(8) C27 0.0122(9) 0.0161(10) 0.0170(9) 0.0030(8) 0.0025(7) -0.0004(8) C28 0.0169(10) 0.0147(10) 0.0146(9) 0.0030(7) 0.0030(7) 0.0030(8) C29 0.0148(10) 0.0159(10) 0.0157(9) 0.0010(7) 0.0005(7) 0.0047(8) C30 0.0128(10) 0.0178(10) 0.0148(9) 0.0016(8) 0.0009(7) 0.0000(8) C31 0.0134(10) 0.0222(11) 0.0173(10) 0.0021(8) 0.0039(8) 0.0029(8) C32 0.0155(10) 0.0177(10) 0.0130(9) -0.0019(7) 0.0039(7) 0.0018(8) C33 0.0175(11) 0.0251(11) 0.0210(10) 0.0011(9) 0.0051(8) -0.0018(9) C34 0.0266(12) 0.0216(11) 0.0216(10) 0.0041(8) 0.0092(9) -0.0019(9) C35 0.0233(11) 0.0185(10) 0.0148(9) 0.0031(8) 0.0052(8) 0.0050(9) C36 0.0164(10) 0.0197(10) 0.0144(9) -0.0017(8) 0.0035(8) 0.0034(8) C37 0.0146(10) 0.0185(10) 0.0129(9) -0.0008(7) 0.0026(7) 0.0020(8) C38 0.0145(10) 0.0140(9) 0.0161(9) -0.0020(7) 0.0014(7) 0.0019(8) C39 0.0129(9) 0.0139(9) 0.0146(9) -0.0005(7) 0.0019(7) 0.0015(8) C40 0.0204(11) 0.0149(10) 0.0200(10) 0.0032(8) 0.0065(8) 0.0004(8) C41 0.0242(11) 0.0130(10) 0.0252(11) 0.0025(8) 0.0051(9) 0.0041(8) C42 0.0143(10) 0.0177(10) 0.0169(9) -0.0043(8) 0.0015(8) 0.0042(8) C43 0.0154(10) 0.0169(10) 0.0163(9) -0.0004(8) 0.0040(8) -0.0001(8) C44 0.0160(10) 0.0106(9) 0.0168(9) 0.0015(7) 0.0024(7) 0.0013(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 N1 1.9797(17) . ? Cu1 N3 2.0264(17) . ? Cu1 N2 2.1456(16) . ? Cu1 N4 2.1980(16) . ? Cu1 Cu2 2.6730(4) . ? Cu2 N4 1.8988(17) . ? Cu2 Cl1 2.1068(6) . ? S1 O1 1.4417(15) . ? S1 O2 1.4456(15) . ? S1 N4 1.6039(17) . ? S1 C17 1.791(2) . ? O3 N5 1.228(2) . ? O4 N5 1.228(2) . ? N1 C1 1.351(3) . ? N1 C5 1.354(3) . ? N2 C15 1.482(2) . ? N2 C8 1.482(3) . ? N2 C7 1.483(3) . ? N3 C14 1.350(3) . ? N3 C10 1.354(3) . ? N4 C16 1.485(2) . ? N5 C20 1.471(3) . ? C1 C2 1.384(3) . ? C1 H1B 0.9500 . ? C2 C3 1.385(3) . ? C2 H2B 0.9500 . ? C3 C4 1.384(3) . ? C3 H3A 0.9500 . ? C4 C5 1.392(3) . ? C4 H4A 0.9500 . ? C5 C6 1.509(3) . ? C6 C7 1.537(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.533(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.508(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.393(3) . ? C11 C12 1.386(3) . ? C11 H11A 0.9500 . ? C12 C13 1.386(3) . ? C12 H12A 0.9500 . ? C13 C14 1.379(3) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.520(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.385(3) . ? C17 C18 1.394(3) . ? C18 C19 1.390(3) . ? C18 H18A 0.9500 . ? C19 C20 1.380(3) . ? C19 H19A 0.9500 . ? C20 C21 1.380(3) . ? C21 C22 1.391(3) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? Cu3 N6 1.9730(17) . ? Cu3 N8 2.0223(16) . ? Cu3 N7 2.1485(16) . ? Cu3 N9 2.1800(16) . ? Cu3 Cu4 2.6395(4) . ? Cu4 N9 1.9030(16) . ? Cu4 Cl2 2.1100(6) . ? S2 O5 1.4418(15) . ? S2 O6 1.4488(15) . ? S2 N9 1.5998(16) . ? S2 C39 1.788(2) . ? O7 N10 1.227(2) . ? O8 N10 1.227(2) . ? N6 C23 1.354(3) . ? N6 C27 1.358(2) . ? N7 C30 1.482(2) . ? N7 C37 1.484(2) . ? N7 C29 1.485(2) . ? N8 C36 1.346(3) . ? N8 C32 1.356(3) . ? N9 C38 1.486(2) . ? N10 C42 1.476(3) . ? C23 C24 1.376(3) . ? C23 H23A 0.9500 . ? C24 C25 1.390(3) . ? C24 H24A 0.9500 . ? C25 C26 1.386(3) . ? C25 H25A 0.9500 . ? C26 C27 1.391(3) . ? C26 H26A 0.9500 . ? C27 C28 1.509(3) . ? C28 C29 1.539(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.532(3) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.512(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.397(3) . ? C33 C34 1.388(3) . ? C33 H33A 0.9500 . ? C34 C35 1.389(3) . ? C34 H34A 0.9500 . ? C35 C36 1.377(3) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? C37 C38 1.522(3) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C44 1.391(3) . ? C39 C40 1.396(3) . ? C40 C41 1.386(3) . ? C40 H40A 0.9500 . ? C41 C42 1.385(3) . ? C41 H41A 0.9500 . ? C42 C43 1.383(3) . ? C43 C44 1.389(3) . ? C43 H43A 0.9500 . ? C44 H44A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 116.30(7) . . ? N1 Cu1 N2 101.77(7) . . ? N3 Cu1 N2 102.61(7) . . ? N1 Cu1 N4 133.03(6) . . ? N3 Cu1 N4 107.91(6) . . ? N2 Cu1 N4 82.60(6) . . ? N1 Cu1 Cu2 88.58(5) . . ? N3 Cu1 Cu2 145.34(5) . . ? N2 Cu1 Cu2 94.70(4) . . ? N4 Cu1 Cu2 44.57(4) . . ? N4 Cu2 Cl1 176.67(5) . . ? N4 Cu2 Cu1 54.33(5) . . ? Cl1 Cu2 Cu1 128.351(19) . . ? O1 S1 O2 117.88(9) . . ? O1 S1 N4 112.53(9) . . ? O2 S1 N4 106.98(9) . . ? O1 S1 C17 105.42(9) . . ? O2 S1 C17 105.47(9) . . ? N4 S1 C17 107.95(9) . . ? C1 N1 C5 118.27(17) . . ? C1 N1 Cu1 120.18(14) . . ? C5 N1 Cu1 120.99(13) . . ? C15 N2 C8 109.99(15) . . ? C15 N2 C7 110.70(15) . . ? C8 N2 C7 110.47(15) . . ? C15 N2 Cu1 106.85(12) . . ? C8 N2 Cu1 109.45(11) . . ? C7 N2 Cu1 109.31(12) . . ? C14 N3 C10 118.27(18) . . ? C14 N3 Cu1 122.40(14) . . ? C10 N3 Cu1 118.41(13) . . ? C16 N4 S1 114.64(13) . . ? C16 N4 Cu2 122.20(13) . . ? S1 N4 Cu2 115.74(9) . . ? C16 N4 Cu1 105.88(12) . . ? S1 N4 Cu1 110.45(8) . . ? Cu2 N4 Cu1 81.10(6) . . ? O3 N5 O4 124.41(18) . . ? O3 N5 C20 117.83(18) . . ? O4 N5 C20 117.74(17) . . ? N1 C1 C2 123.00(19) . . ? N1 C1 H1B 118.5 . . ? C2 C1 H1B 118.5 . . ? C1 C2 C3 118.7(2) . . ? C1 C2 H2B 120.7 . . ? C3 C2 H2B 120.7 . . ? C4 C3 C2 118.8(2) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C3 C4 C5 119.9(2) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? N1 C5 C4 121.29(18) . . ? N1 C5 C6 117.67(17) . . ? C4 C5 C6 121.04(18) . . ? C5 C6 C7 115.22(16) . . ? C5 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? C5 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? N2 C7 C6 113.75(16) . . ? N2 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? N2 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N2 C8 C9 113.20(16) . . ? N2 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N2 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 115.19(17) . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? N3 C10 C11 121.31(19) . . ? N3 C10 C9 117.95(18) . . ? C11 C10 C9 120.73(19) . . ? C12 C11 C10 119.5(2) . . ? C12 C11 H11A 120.3 . . ? C10 C11 H11A 120.3 . . ? C13 C12 C11 119.2(2) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C14 C13 C12 118.3(2) . . ? C14 C13 H13A 120.8 . . ? C12 C13 H13A 120.8 . . ? N3 C14 C13 123.3(2) . . ? N3 C14 H14A 118.3 . . ? C13 C14 H14A 118.3 . . ? N2 C15 C16 111.55(15) . . ? N2 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? N2 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? N4 C16 C15 108.76(15) . . ? N4 C16 H16A 109.9 . . ? C15 C16 H16A 109.9 . . ? N4 C16 H16B 109.9 . . ? C15 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? C22 C17 C18 120.78(18) . . ? C22 C17 S1 119.92(15) . . ? C18 C17 S1 119.07(15) . . ? C19 C18 C17 119.7(2) . . ? C19 C18 H18A 120.2 . . ? C17 C18 H18A 120.2 . . ? C20 C19 C18 118.09(19) . . ? C20 C19 H19A 121.0 . . ? C18 C19 H19A 121.0 . . ? C19 C20 C21 123.42(19) . . ? C19 C20 N5 118.44(18) . . ? C21 C20 N5 118.08(19) . . ? C20 C21 C22 117.86(19) . . ? C20 C21 H21A 121.1 . . ? C22 C21 H21A 121.1 . . ? C17 C22 C21 120.06(19) . . ? C17 C22 H22A 120.0 . . ? C21 C22 H22A 120.0 . . ? N6 Cu3 N8 114.99(7) . . ? N6 Cu3 N7 101.45(6) . . ? N8 Cu3 N7 102.90(7) . . ? N6 Cu3 N9 134.58(7) . . ? N8 Cu3 N9 107.56(6) . . ? N7 Cu3 N9 83.32(6) . . ? N6 Cu3 Cu4 89.46(5) . . ? N8 Cu3 Cu4 144.65(5) . . ? N7 Cu3 Cu4 96.19(4) . . ? N9 Cu3 Cu4 45.28(4) . . ? N9 Cu4 Cl2 175.86(5) . . ? N9 Cu4 Cu3 54.48(5) . . ? Cl2 Cu4 Cu3 129.130(19) . . ? O5 S2 O6 117.75(9) . . ? O5 S2 N9 112.53(9) . . ? O6 S2 N9 107.28(8) . . ? O5 S2 C39 105.26(9) . . ? O6 S2 C39 105.08(9) . . ? N9 S2 C39 108.35(9) . . ? C23 N6 C27 118.06(18) . . ? C23 N6 Cu3 120.06(13) . . ? C27 N6 Cu3 120.44(13) . . ? C30 N7 C37 110.36(15) . . ? C30 N7 C29 110.47(15) . . ? C37 N7 C29 109.98(15) . . ? C30 N7 Cu3 108.98(11) . . ? C37 N7 Cu3 106.50(12) . . ? C29 N7 Cu3 110.48(12) . . ? C36 N8 C32 118.25(17) . . ? C36 N8 Cu3 122.78(14) . . ? C32 N8 Cu3 118.31(13) . . ? C38 N9 S2 114.06(13) . . ? C38 N9 Cu4 123.18(12) . . ? S2 N9 Cu4 115.94(9) . . ? C38 N9 Cu3 105.46(11) . . ? S2 N9 Cu3 110.87(8) . . ? Cu4 N9 Cu3 80.24(6) . . ? O7 N10 O8 124.10(19) . . ? O7 N10 C42 117.94(18) . . ? O8 N10 C42 117.95(18) . . ? N6 C23 C24 123.16(19) . . ? N6 C23 H23A 118.4 . . ? C24 C23 H23A 118.4 . . ? C23 C24 C25 118.9(2) . . ? C23 C24 H24A 120.5 . . ? C25 C24 H24A 120.5 . . ? C26 C25 C24 118.6(2) . . ? C26 C25 H25A 120.7 . . ? C24 C25 H25A 120.7 . . ? C25 C26 C27 119.97(19) . . ? C25 C26 H26A 120.0 . . ? C27 C26 H26A 120.0 . . ? N6 C27 C26 121.32(18) . . ? N6 C27 C28 117.45(18) . . ? C26 C27 C28 121.23(17) . . ? C27 C28 C29 114.12(16) . . ? C27 C28 H28A 108.7 . . ? C29 C28 H28A 108.7 . . ? C27 C28 H28B 108.7 . . ? C29 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? N7 C29 C28 112.85(16) . . ? N7 C29 H29A 109.0 . . ? C28 C29 H29A 109.0 . . ? N7 C29 H29B 109.0 . . ? C28 C29 H29B 109.0 . . ? H29A C29 H29B 107.8 . . ? N7 C30 C31 113.37(16) . . ? N7 C30 H30A 108.9 . . ? C31 C30 H30A 108.9 . . ? N7 C30 H30B 108.9 . . ? C31 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? C32 C31 C30 115.37(17) . . ? C32 C31 H31A 108.4 . . ? C30 C31 H31A 108.4 . . ? C32 C31 H31B 108.4 . . ? C30 C31 H31B 108.4 . . ? H31A C31 H31B 107.5 . . ? N8 C32 C33 121.19(18) . . ? N8 C32 C31 118.01(17) . . ? C33 C32 C31 120.77(19) . . ? C34 C33 C32 119.5(2) . . ? C34 C33 H33A 120.2 . . ? C32 C33 H33A 120.2 . . ? C33 C34 C35 119.09(19) . . ? C33 C34 H34A 120.5 . . ? C35 C34 H34A 120.5 . . ? C36 C35 C34 118.29(19) . . ? C36 C35 H35A 120.9 . . ? C34 C35 H35A 120.9 . . ? N8 C36 C35 123.63(19) . . ? N8 C36 H36A 118.2 . . ? C35 C36 H36A 118.2 . . ? N7 C37 C38 111.18(15) . . ? N7 C37 H37A 109.4 . . ? C38 C37 H37A 109.4 . . ? N7 C37 H37B 109.4 . . ? C38 C37 H37B 109.4 . . ? H37A C37 H37B 108.0 . . ? N9 C38 C37 109.69(16) . . ? N9 C38 H38A 109.7 . . ? C37 C38 H38A 109.7 . . ? N9 C38 H38B 109.7 . . ? C37 C38 H38B 109.7 . . ? H38A C38 H38B 108.2 . . ? C44 C39 C40 120.71(18) . . ? C44 C39 S2 120.86(15) . . ? C40 C39 S2 118.23(15) . . ? C41 C40 C39 119.70(19) . . ? C41 C40 H40A 120.1 . . ? C39 C40 H40A 120.1 . . ? C42 C41 C40 118.14(19) . . ? C42 C41 H41A 120.9 . . ? C40 C41 H41A 120.9 . . ? C43 C42 C41 123.27(19) . . ? C43 C42 N10 118.16(18) . . ? C41 C42 N10 118.55(18) . . ? C42 C43 C44 117.85(18) . . ? C42 C43 H43A 121.1 . . ? C44 C43 H43A 121.1 . . ? C43 C44 C39 120.02(18) . . ? C43 C44 H44A 120.0 . . ? C39 C44 H44A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.510 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.070 #===END