# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Berta Covelo' _publ_contact_author_email BCOVELO@UVIGO.ES _publ_section_title ; From copper(II) carboxylate to copper(II) 4-pyridylsulfonate coordination polymers as a consequence of the copper(II)-assisted oxidative cleavage of the 4,4'-dipyridyldisulfide ligand ; loop_ _publ_author_name 'Berta Covelo' 'Rosa Carballo' 'Nuria Fernandez-Hermida' 'Ana B Lago' ; E.M.Vazquez-Lopez ; # Attachment 'B816721D.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 706584' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Cl2 Cu2 N2 O7 S2' _chemical_formula_weight 584.37 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4405(6) _cell_length_b 11.4677(8) _cell_length_c 11.7069(8) _cell_angle_alpha 108.7040(10) _cell_angle_beta 95.0000(10) _cell_angle_gamma 95.8130(10) _cell_volume 1059.14(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour blue _exptl_crystal_size_max .53 _exptl_crystal_size_mid .32 _exptl_crystal_size_min .20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.832 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 2.496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6803 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 6597 _diffrn_reflns_av_R_equivalents 0.0159 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.02 _reflns_number_total 4601 _reflns_number_gt 3731 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4601 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.14452(5) 0.93803(3) 0.01230(3) 0.03418(13) Uani 1 1 d . . . Cu2 Cu -0.11221(6) 0.79121(3) -0.21772(3) 0.04252(14) Uani 1 1 d . . . O1 O -0.0053(3) 0.95729(19) -0.1159(2) 0.0301(5) Uani 1 1 d . . . O11 O -0.0813(5) 0.7482(3) -0.0262(6) 0.132(2) Uani 1 1 d . . . O12 O -0.2822(5) 0.8292(4) -0.0651(4) 0.1203(19) Uani 1 1 d . . . O21 O 0.2957(3) 0.8667(2) -0.0947(2) 0.0462(6) Uani 1 1 d . . . O22 O 0.1293(4) 0.7170(2) -0.2409(2) 0.0567(7) Uani 1 1 d . . . O31 O -0.1065(3) 0.8272(2) -0.3711(2) 0.0500(6) Uani 1 1 d . . . O32 O 0.0841(3) 0.9922(2) -0.3158(2) 0.0486(6) Uani 1 1 d . . . C11 C -0.2062(5) 0.7828(3) -0.0029(3) 0.0464(9) Uani 1 1 d . . . H11 H -0.2469 0.7739 0.0656 0.056 Uiso 1 1 calc R . . C21 C 0.2617(5) 0.7736(4) -0.1897(3) 0.0506(9) Uani 1 1 d . . . H21 H 0.3491 0.7430 -0.2266 0.061 Uiso 1 1 calc R . . C31 C -0.0100(5) 0.9072(3) -0.3911(3) 0.0459(8) Uani 1 1 d . . . H31 H -0.0093 0.9019 -0.4720 0.055 Uiso 1 1 calc R . . N1 N 0.2743(3) 0.9105(2) 0.1479(2) 0.0328(6) Uani 1 1 d . . . N2 N 0.2324(4) 0.3771(2) 0.3150(2) 0.0395(6) Uani 1 1 d . . . S1 S 0.59778(10) 0.83705(8) 0.44128(8) 0.0400(2) Uani 1 1 d . . . S2 S 0.45214(12) 0.77185(7) 0.54307(7) 0.0438(2) Uani 1 1 d . . . C1 C 0.4336(4) 0.9417(3) 0.1653(3) 0.0401(7) Uani 1 1 d . . . H1 H 0.4806 0.9790 0.1144 0.048 Uiso 1 1 calc R . . C2 C 0.5311(4) 0.9210(3) 0.2556(3) 0.0393(7) Uani 1 1 d . . . H2 H 0.6415 0.9443 0.2652 0.047 Uiso 1 1 calc R . . C3 C 0.4633(4) 0.8652(3) 0.3315(3) 0.0321(6) Uani 1 1 d . . . C4 C 0.2970(4) 0.8332(3) 0.3142(3) 0.0392(7) Uani 1 1 d . . . H4 H 0.2468 0.7962 0.3640 0.047 Uiso 1 1 calc R . . C5 C 0.2090(4) 0.8574(3) 0.2223(3) 0.0387(7) Uani 1 1 d . . . H5 H 0.0981 0.8358 0.2112 0.046 Uiso 1 1 calc R . . C6 C 0.3759(4) 0.6165(3) 0.4517(3) 0.0362(7) Uani 1 1 d . . . C7 C 0.2557(5) 0.5565(3) 0.4930(3) 0.0442(8) Uani 1 1 d . . . H7 H 0.2207 0.5960 0.5671 0.053 Uiso 1 1 calc R . . C8 C 0.1876(5) 0.4374(3) 0.4237(3) 0.0467(9) Uani 1 1 d . . . H8 H 0.1077 0.3973 0.4532 0.056 Uiso 1 1 calc R . . C9 C 0.3510(5) 0.4348(3) 0.2771(3) 0.0452(9) Uani 1 1 d . . . H9 H 0.3852 0.3931 0.2034 0.054 Uiso 1 1 calc R . . C10 C 0.4265(5) 0.5545(3) 0.3421(3) 0.0438(8) Uani 1 1 d . . . H10 H 0.5090 0.5917 0.3124 0.053 Uiso 1 1 calc R . . H100 H 0.028(4) 0.972(3) -0.161(3) 0.033(11) Uiso 1 1 d . . . Cl2 Cl 0.1167(3) 0.37347(17) 0.71900(18) 0.1200(7) Uani 1 1 d . . . Cl1 Cl 0.2867(3) 0.5336(2) 0.9492(2) 0.1485(8) Uani 1 1 d . . . C100 C 0.1035(8) 0.4770(5) 0.8615(6) 0.0946(19) Uani 1 1 d . . . H10A H 0.0529 0.5462 0.8520 0.114 Uiso 1 1 calc R . . H10B H 0.0352 0.4358 0.9036 0.114 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 0.0348(2) 0.0394(2) 0.0277(2) 0.00831(16) 0.00254(15) 0.01257(17) Cu2 0.0612(3) 0.0302(2) 0.0286(2) 0.00306(16) 0.00876(19) -0.00877(19) O1 0.0333(12) 0.0286(10) 0.0274(11) 0.0073(9) 0.0047(9) 0.0050(9) O11 0.078(3) 0.0487(18) 0.271(6) 0.037(3) 0.085(4) 0.0132(19) O12 0.082(3) 0.130(3) 0.167(4) 0.113(3) -0.058(3) -0.057(2) O21 0.0394(13) 0.0594(15) 0.0353(12) 0.0072(11) 0.0065(10) 0.0131(12) O22 0.071(2) 0.0439(14) 0.0465(15) 0.0005(12) 0.0078(14) 0.0144(14) O31 0.0646(17) 0.0448(13) 0.0347(13) 0.0153(11) -0.0073(12) -0.0146(12) O32 0.0441(14) 0.0538(14) 0.0457(14) 0.0182(12) 0.0039(11) -0.0073(12) C11 0.055(2) 0.0380(17) 0.0398(19) 0.0055(15) 0.0136(17) -0.0053(17) C21 0.062(3) 0.057(2) 0.0385(19) 0.0144(17) 0.0175(18) 0.027(2) C31 0.056(2) 0.0490(19) 0.0322(17) 0.0149(15) 0.0033(16) 0.0004(18) N1 0.0294(13) 0.0356(13) 0.0350(14) 0.0138(11) 0.0020(11) 0.0067(11) N2 0.0497(17) 0.0309(13) 0.0326(14) 0.0042(11) 0.0088(12) -0.0010(12) S1 0.0391(5) 0.0364(4) 0.0402(5) 0.0125(3) -0.0093(3) -0.0018(3) S2 0.0621(6) 0.0328(4) 0.0292(4) 0.0053(3) -0.0027(4) -0.0032(4) C1 0.0363(18) 0.0493(19) 0.0372(17) 0.0198(15) 0.0043(14) 0.0002(15) C2 0.0271(16) 0.0463(18) 0.0408(18) 0.0128(15) 0.0000(13) -0.0024(14) C3 0.0314(16) 0.0280(14) 0.0331(16) 0.0065(12) -0.0010(12) 0.0040(13) C4 0.0326(17) 0.0453(18) 0.0442(19) 0.0230(15) 0.0037(14) 0.0006(15) C5 0.0269(16) 0.0450(18) 0.049(2) 0.0223(16) 0.0046(14) 0.0058(14) C6 0.0448(19) 0.0286(14) 0.0321(16) 0.0087(12) -0.0037(14) 0.0026(14) C7 0.056(2) 0.0398(17) 0.0294(16) 0.0027(13) 0.0112(15) -0.0005(16) C8 0.058(2) 0.0404(17) 0.0368(18) 0.0072(15) 0.0163(17) -0.0041(17) C9 0.053(2) 0.0344(16) 0.0418(19) 0.0029(14) 0.0167(17) 0.0012(16) C10 0.050(2) 0.0360(16) 0.0423(19) 0.0091(14) 0.0119(16) -0.0030(16) Cl2 0.1379(16) 0.1029(11) 0.1167(13) 0.0254(10) 0.0587(12) 0.0059(11) Cl1 0.174(2) 0.1243(15) 0.1460(18) 0.0624(14) -0.0240(16) -0.0057(15) C100 0.105(5) 0.080(3) 0.116(5) 0.044(3) 0.048(4) 0.025(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 O21 1.923(2) . ? Cu1 O1 1.960(2) . ? Cu1 O1 1.973(2) 2_575 ? Cu1 N1 1.977(3) . ? Cu1 O11 2.637(4) . ? Cu1 O12 2.655(4) 2_575 ? Cu1 Cu1 2.9829(8) 2_575 ? Cu1 Cu2 3.1808(6) . ? Cu2 O1 1.967(2) . ? Cu2 O31 1.971(2) . ? Cu2 N2 2.011(3) 2_565 ? Cu2 O22 2.292(3) . ? Cu2 O12 2.348(5) . ? Cu2 O11 2.443(6) . ? O1 Cu1 1.973(2) 2_575 ? O1 H100 0.68(3) . ? O11 C11 1.187(5) . ? O12 C11 1.209(5) . ? O21 C21 1.257(4) . ? O22 C21 1.231(5) . ? O31 C31 1.256(4) . ? O32 C31 1.236(4) . ? C11 H11 0.9300 . ? C21 H21 0.9300 . ? C31 H31 0.9300 . ? N1 C1 1.336(4) . ? N1 C5 1.337(4) . ? N2 C9 1.330(4) . ? N2 C8 1.347(4) . ? N2 Cu2 2.011(3) 2_565 ? S1 C3 1.769(3) . ? S1 S2 2.0325(13) . ? S2 C6 1.777(3) . ? C1 C2 1.379(5) . ? C1 H1 0.9300 . ? C2 C3 1.381(4) . ? C2 H2 0.9300 . ? C3 C4 1.394(4) . ? C4 C5 1.371(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.376(5) . ? C6 C10 1.381(5) . ? C7 C8 1.379(5) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.391(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? Cl2 C100 1.730(6) . ? Cl1 C100 1.721(7) . ? C100 H10A 0.9700 . ? C100 H10B 0.9700 . ? 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 O21 Cu1 O1 94.95(10) . . ? O21 Cu1 O1 168.29(10) . 2_575 ? O1 Cu1 O1 81.34(10) . 2_575 ? O21 Cu1 N1 89.50(10) . . ? O1 Cu1 N1 173.52(10) . . ? O1 Cu1 N1 95.20(10) 2_575 . ? O21 Cu1 O11 102.68(12) . . ? O1 Cu1 O11 78.21(15) . . ? O1 Cu1 O11 87.50(10) 2_575 . ? N1 Cu1 O11 96.24(15) . . ? O21 Cu1 O12 94.85(14) . 2_575 ? O1 Cu1 O12 90.35(10) . 2_575 ? O1 Cu1 O12 74.16(14) 2_575 2_575 ? N1 Cu1 O12 93.98(11) . 2_575 ? O11 Cu1 O12 159.74(13) . 2_575 ? O21 Cu1 Cu1 134.78(8) . 2_575 ? O1 Cu1 Cu1 40.84(6) . 2_575 ? O1 Cu1 Cu1 40.50(7) 2_575 2_575 ? N1 Cu1 Cu1 135.45(8) . 2_575 ? O11 Cu1 Cu1 80.61(9) . 2_575 ? O12 Cu1 Cu1 79.83(10) 2_575 2_575 ? O21 Cu1 Cu2 83.41(7) . . ? O1 Cu1 Cu2 35.99(6) . . ? O1 Cu1 Cu2 99.48(7) 2_575 . ? N1 Cu1 Cu2 140.58(8) . . ? O11 Cu1 Cu2 48.56(14) . . ? O12 Cu1 Cu2 125.19(8) 2_575 . ? Cu1 Cu1 Cu2 65.000(16) 2_575 . ? O1 Cu2 O31 94.16(10) . . ? O1 Cu2 N2 176.41(10) . 2_565 ? O31 Cu2 N2 88.01(10) . 2_565 ? O1 Cu2 O22 91.52(9) . . ? O31 Cu2 O22 89.76(11) . . ? N2 Cu2 O22 91.34(11) 2_565 . ? O1 Cu2 O12 81.89(11) . . ? O31 Cu2 O12 134.73(13) . . ? N2 Cu2 O12 94.55(12) 2_565 . ? O22 Cu2 O12 135.21(12) . . ? O1 Cu2 O11 83.09(11) . . ? O31 Cu2 O11 172.53(12) . . ? N2 Cu2 O11 95.09(12) 2_565 . ? O22 Cu2 O11 83.38(12) . . ? O12 Cu2 O11 51.89(13) . . ? O1 Cu2 Cu1 35.82(7) . . ? O31 Cu2 Cu1 120.62(7) . . ? N2 Cu2 Cu1 144.16(9) 2_565 . ? O22 Cu2 Cu1 69.54(7) . . ? O12 Cu2 Cu1 80.43(9) . . ? O11 Cu2 Cu1 54.02(9) . . ? Cu1 O1 Cu2 108.19(10) . . ? Cu1 O1 Cu1 98.66(10) . 2_575 ? Cu2 O1 Cu1 114.61(11) . 2_575 ? Cu1 O1 H100 117(3) . . ? Cu2 O1 H100 97(3) . . ? Cu1 O1 H100 122(3) 2_575 . ? C11 O11 Cu2 90.7(4) . . ? C11 O11 Cu1 110.9(3) . . ? Cu2 O11 Cu1 77.42(12) . . ? C11 O12 Cu2 94.8(3) . . ? C21 O21 Cu1 125.0(3) . . ? C21 O22 Cu2 126.2(2) . . ? C31 O31 Cu2 126.9(2) . . ? O11 C11 O12 122.2(5) . . ? O11 C11 H11 118.9 . . ? O12 C11 H11 118.9 . . ? O22 C21 O21 129.3(4) . . ? O22 C21 H21 115.3 . . ? O21 C21 H21 115.3 . . ? O32 C31 O31 127.6(3) . . ? O32 C31 H31 116.2 . . ? O31 C31 H31 116.2 . . ? C1 N1 C5 117.8(3) . . ? C1 N1 Cu1 119.9(2) . . ? C5 N1 Cu1 122.3(2) . . ? C9 N2 C8 117.5(3) . . ? C9 N2 Cu2 124.0(2) . 2_565 ? C8 N2 Cu2 118.4(2) . 2_565 ? C3 S1 S2 104.07(11) . . ? C6 S2 S1 105.32(12) . . ? N1 C1 C2 122.7(3) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 119.4(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 118.1(3) . . ? C2 C3 S1 116.4(2) . . ? C4 C3 S1 125.5(2) . . ? C5 C4 C3 118.7(3) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 123.4(3) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C7 C6 C10 118.7(3) . . ? C7 C6 S2 116.9(2) . . ? C10 C6 S2 124.4(3) . . ? C6 C7 C8 119.5(3) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? N2 C8 C7 122.5(3) . . ? N2 C8 H8 118.8 . . ? C7 C8 H8 118.8 . . ? N2 C9 C10 123.4(3) . . ? N2 C9 H9 118.3 . . ? C10 C9 H9 118.3 . . ? C6 C10 C9 118.3(3) . . ? C6 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? Cl1 C100 Cl2 113.4(3) . . ? Cl1 C100 H10A 108.9 . . ? Cl2 C100 H10A 108.9 . . ? Cl1 C100 H10B 108.9 . . ? Cl2 C100 H10B 108.9 . . ? H10A C100 H10B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 S1 S2 C6 75.28(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H100 O32 0.68(3) 1.99(4) 2.655(3) 168(4) . C1 H1 O21 0.93 2.53 3.348(4) 146.6 2_675 C2 H2 O32 0.93 2.32 3.246(4) 172.7 2_675 C7 H7 O22 0.93 2.47 3.396(4) 175.1 1_556 C8 H8 O31 0.93 2.44 2.893(4) 109.9 2_565 C9 H9 O12 0.93 2.56 3.199(6) 126.7 2_565 C100 H10A O22 0.97 2.58 3.332(6) 134.1 1_556 _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.936 _refine_diff_density_min -0.762 _refine_diff_density_rms 0.089 # Attachment 'b816721d_3.cif' data_bc1a _database_code_depnum_ccdc_archive 'CCDC 706585' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 Cu N6 O10 S6' _chemical_formula_weight 892.52 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.9365(13) _cell_length_b 10.7022(7) _cell_length_c 20.3222(14) _cell_angle_alpha 90.00 _cell_angle_beta 114.9010(10) _cell_angle_gamma 90.00 _cell_volume 3735.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1836 _exptl_absorpt_coefficient_mu 0.983 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8520 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11065 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 28.04 _reflns_number_total 4303 _reflns_number_gt 2781 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0247P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4303 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0697 _refine_ls_wR_factor_gt 0.0635 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.883 _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 Cu Cu 0.0000 0.18283(3) 0.2500 0.02771(11) Uani 1 2 d S . . S1 S 0.08605(4) 0.62335(5) 0.49837(3) 0.03909(17) Uani 1 1 d . . . S2 S -0.00580(4) 0.74077(5) 0.47291(4) 0.04013(18) Uani 1 1 d . . . N1 N 0.01887(11) 0.31789(16) 0.32652(10) 0.0282(4) Uani 1 1 d . . . N2 N 0.01003(10) 1.04825(15) 0.32486(10) 0.0266(4) Uani 1 1 d . . . O1 O 0.13697(11) 0.1804(2) 0.28471(13) 0.0458(5) Uani 1 1 d . . . C1 C -0.02851(13) 0.4172(2) 0.31567(13) 0.0318(6) Uani 1 1 d . . . H1 H -0.0739 0.4211 0.2730 0.038 Uiso 1 1 calc R . . C2 C -0.01258(13) 0.5130(2) 0.36502(13) 0.0313(6) Uani 1 1 d . . . H2 H -0.0466 0.5803 0.3555 0.038 Uiso 1 1 calc R . . C3 C 0.05456(13) 0.50840(19) 0.42911(12) 0.0280(5) Uani 1 1 d . . . C4 C 0.10356(13) 0.40527(19) 0.44154(13) 0.0290(5) Uani 1 1 d . . . H4 H 0.1488 0.3986 0.4842 0.035 Uiso 1 1 calc R . . C5 C 0.08368(13) 0.3141(2) 0.38951(13) 0.0302(5) Uani 1 1 d . . . H5 H 0.1167 0.2457 0.3981 0.036 Uiso 1 1 calc R . . C6 C 0.00551(13) 0.85603(19) 0.41562(12) 0.0273(5) Uani 1 1 d . . . C7 C -0.03607(13) 0.9664(2) 0.40873(12) 0.0304(6) Uani 1 1 d . . . H7 H -0.0660 0.9775 0.4347 0.036 Uiso 1 1 calc R . . C8 C -0.03245(13) 1.0582(2) 0.36335(12) 0.0290(5) Uani 1 1 d . . . H8 H -0.0608 1.1311 0.3590 0.035 Uiso 1 1 calc R . . C9 C 0.05120(13) 0.94232(19) 0.33313(13) 0.0293(5) Uani 1 1 d . . . H9 H 0.0818 0.9342 0.3077 0.035 Uiso 1 1 calc R . . C10 C 0.05035(13) 0.84528(19) 0.37740(13) 0.0306(6) Uani 1 1 d . . . H10 H 0.0796 0.7736 0.3814 0.037 Uiso 1 1 calc R . . H1A H 0.1680(17) 0.128(3) 0.3094(17) 0.066(12) Uiso 1 1 d . . . H1B H 0.1535(14) 0.204(2) 0.2595(14) 0.033(9) Uiso 1 1 d . . . S11 S 0.27351(4) 0.80720(7) 0.69609(4) 0.0498(2) Uani 1 1 d . . . O11 O 0.19992(11) 0.75206(16) 0.68817(10) 0.0547(5) Uani 1 1 d . . . O12 O 0.31676(12) 0.8639(2) 0.76670(12) 0.0746(6) Uani 1 1 d . . . O13 O 0.31677(14) 0.7223(2) 0.67322(15) 0.0988(9) Uani 1 1 d . . . N11 N 0.19685(16) 1.1236(3) 0.5305(2) 0.0841(10) Uani 1 1 d . . . C11 C 0.21442(18) 1.1431(3) 0.5992(2) 0.0743(11) Uani 1 1 d . . . H11 H 0.2095 1.2241 0.6134 0.089 Uiso 1 1 calc R . . C12 C 0.23966(16) 1.0519(3) 0.65224(18) 0.0557(8) Uani 1 1 d . . . H12 H 0.2518 1.0715 0.7004 0.067 Uiso 1 1 calc R . . C13 C 0.24636(14) 0.9311(2) 0.63189(15) 0.0408(7) Uani 1 1 d . . . C14 C 0.22893(17) 0.9078(3) 0.56022(18) 0.0616(9) Uani 1 1 d . . . H14 H 0.2329 0.8276 0.5445 0.074 Uiso 1 1 calc R . . C15 C 0.20504(19) 1.0078(4) 0.51163(19) 0.0831(12) Uani 1 1 d . . . H15 H 0.1943 0.9922 0.4633 0.100 Uiso 1 1 calc R . . O1W O 0.2606(2) 0.0239(3) 0.36541(17) 0.0811(9) Uani 1 1 d . . . H1WA H 0.2854(17) 0.038(3) 0.3419(18) 0.055(12) Uiso 1 1 d . . . H1WB H 0.249(2) -0.037(3) 0.353(2) 0.082(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0374(3) 0.0209(2) 0.0264(2) 0.000 0.0150(2) 0.000 S1 0.0567(4) 0.0251(3) 0.0291(4) -0.0020(3) 0.0118(3) 0.0008(3) S2 0.0665(5) 0.0252(3) 0.0436(4) 0.0031(3) 0.0378(4) 0.0026(3) N1 0.0341(11) 0.0214(10) 0.0293(11) 0.0004(9) 0.0136(10) 0.0008(9) N2 0.0316(11) 0.0227(10) 0.0281(11) -0.0006(8) 0.0152(10) 0.0017(8) O1 0.0349(12) 0.0606(14) 0.0449(13) 0.0036(11) 0.0197(11) 0.0004(11) C1 0.0305(14) 0.0303(13) 0.0290(14) -0.0010(11) 0.0070(12) 0.0035(11) C2 0.0362(15) 0.0217(12) 0.0338(15) -0.0003(11) 0.0125(12) 0.0058(11) C3 0.0382(14) 0.0205(12) 0.0287(14) 0.0008(10) 0.0174(12) -0.0028(11) C4 0.0320(14) 0.0258(13) 0.0245(14) 0.0023(10) 0.0072(11) -0.0023(10) C5 0.0349(14) 0.0220(12) 0.0341(15) 0.0049(11) 0.0149(12) 0.0054(11) C6 0.0360(14) 0.0214(12) 0.0256(13) -0.0018(9) 0.0141(11) -0.0034(10) C7 0.0362(14) 0.0296(13) 0.0313(15) -0.0008(11) 0.0199(12) 0.0012(11) C8 0.0358(14) 0.0250(12) 0.0287(14) -0.0019(10) 0.0160(12) 0.0052(11) C9 0.0315(14) 0.0293(13) 0.0322(15) 0.0016(11) 0.0185(12) 0.0028(11) C10 0.0372(14) 0.0235(13) 0.0348(15) 0.0034(10) 0.0189(12) 0.0072(10) S11 0.0497(5) 0.0463(4) 0.0642(5) 0.0083(4) 0.0346(4) 0.0115(4) O11 0.0609(13) 0.0503(11) 0.0645(14) -0.0011(10) 0.0379(11) -0.0101(10) O12 0.0559(14) 0.0896(16) 0.0577(15) 0.0092(13) 0.0039(12) -0.0110(12) O13 0.116(2) 0.0758(16) 0.157(3) 0.0348(16) 0.110(2) 0.0498(14) N11 0.0532(18) 0.083(2) 0.088(3) 0.035(2) 0.0020(18) -0.0209(17) C11 0.052(2) 0.046(2) 0.100(3) 0.007(2) 0.007(2) -0.0046(16) C12 0.0492(19) 0.0439(18) 0.062(2) -0.0021(16) 0.0118(16) -0.0019(14) C13 0.0336(15) 0.0396(16) 0.0492(19) 0.0004(13) 0.0173(14) -0.0064(12) C14 0.065(2) 0.064(2) 0.056(2) -0.0117(17) 0.0262(18) -0.0221(17) C15 0.063(2) 0.126(3) 0.045(2) 0.007(2) 0.0079(19) -0.038(3) O1W 0.099(2) 0.064(2) 0.073(2) 0.0078(16) 0.0297(18) 0.0159(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 2.0414(18) . ? Cu N1 2.0414(18) 2 ? Cu N2 2.0449(18) 2_545 ? Cu N2 2.0449(18) 1_545 ? Cu O1 2.3843(19) 2 ? Cu O1 2.3843(19) . ? S1 C3 1.773(2) . ? S1 S2 2.0283(9) . ? S2 C6 1.770(2) . ? N1 C1 1.348(3) . ? N1 C5 1.350(3) . ? N2 C8 1.342(3) . ? N2 C9 1.346(2) . ? N2 Cu 2.0449(18) 1_565 ? O1 H1A 0.81(3) . ? O1 H1B 0.75(2) . ? C1 C2 1.376(3) . ? C1 H1 0.9300 . ? C2 C3 1.386(3) . ? C2 H2 0.9300 . ? C3 C4 1.395(3) . ? C4 C5 1.370(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C10 1.376(3) . ? C6 C7 1.393(3) . ? C7 C8 1.369(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.379(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? S11 O13 1.4261(19) . ? S11 O12 1.452(2) . ? S11 O11 1.4585(18) . ? S11 C13 1.778(3) . ? N11 C11 1.310(5) . ? N11 C15 1.326(4) . ? C11 C12 1.381(4) . ? C11 H11 0.9300 . ? C12 C13 1.380(3) . ? C12 H12 0.9300 . ? C13 C14 1.374(4) . ? C14 C15 1.396(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O1W H1WA 0.81(3) . ? O1W H1WB 0.70(3) . ? 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 Cu N1 89.84(10) . 2 ? N1 Cu N2 175.62(7) . 2_545 ? N1 Cu N2 90.02(7) 2 2_545 ? N1 Cu N2 90.02(7) . 1_545 ? N1 Cu N2 175.62(7) 2 1_545 ? N2 Cu N2 90.45(10) 2_545 1_545 ? N1 Cu O1 93.03(8) . 2 ? N1 Cu O1 87.86(7) 2 2 ? N2 Cu O1 91.35(8) 2_545 2 ? N2 Cu O1 87.77(7) 1_545 2 ? N1 Cu O1 87.86(7) . . ? N1 Cu O1 93.03(8) 2 . ? N2 Cu O1 87.77(7) 2_545 . ? N2 Cu O1 91.35(8) 1_545 . ? O1 Cu O1 178.75(12) 2 . ? C3 S1 S2 105.17(8) . . ? C6 S2 S1 105.74(8) . . ? C1 N1 C5 117.09(19) . . ? C1 N1 Cu 122.88(16) . . ? C5 N1 Cu 119.90(15) . . ? C8 N2 C9 116.89(19) . . ? C8 N2 Cu 119.14(14) . 1_565 ? C9 N2 Cu 123.62(15) . 1_565 ? Cu O1 H1A 127(2) . . ? Cu O1 H1B 120.6(19) . . ? H1A O1 H1B 105(3) . . ? N1 C1 C2 122.8(2) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 119.4(2) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 118.4(2) . . ? C2 C3 S1 126.18(17) . . ? C4 C3 S1 115.43(18) . . ? C5 C4 C3 118.6(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 123.7(2) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C10 C6 C7 118.1(2) . . ? C10 C6 S2 125.97(17) . . ? C7 C6 S2 115.91(17) . . ? C8 C7 C6 119.3(2) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? N2 C8 C7 123.2(2) . . ? N2 C8 H8 118.4 . . ? C7 C8 H8 118.4 . . ? N2 C9 C10 123.4(2) . . ? N2 C9 H9 118.3 . . ? C10 C9 H9 118.3 . . ? C6 C10 C9 119.0(2) . . ? C6 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? O13 S11 O12 115.22(16) . . ? O13 S11 O11 111.07(13) . . ? O12 S11 O11 113.17(13) . . ? O13 S11 C13 105.33(13) . . ? O12 S11 C13 106.37(13) . . ? O11 S11 C13 104.66(11) . . ? C11 N11 C15 116.7(3) . . ? N11 C11 C12 124.7(3) . . ? N11 C11 H11 117.7 . . ? C12 C11 H11 117.7 . . ? C13 C12 C11 118.3(3) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? C14 C13 C12 118.5(3) . . ? C14 C13 S11 120.6(2) . . ? C12 C13 S11 120.9(2) . . ? C13 C14 C15 118.2(3) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? N11 C15 C14 123.7(3) . . ? N11 C15 H15 118.1 . . ? C14 C15 H15 118.1 . . ? H1WA O1W H1WB 97(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 S1 S2 C6 -89.00(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WB O13 0.70(3) 2.28(3) 2.956(5) 162(4) 7_556 O1W H1WA O12 0.81(3) 2.14(3) 2.897(5) 156(3) 6_565 O1 H1B O11 0.75(2) 2.04(2) 2.786(3) 173(3) 6_565 O1 H1A O1W 0.81(3) 1.98(3) 2.783(4) 167(3) . C2 H2 O12 0.93 2.53 3.276(3) 138.0 8_465 C9 H9 O13 0.93 2.45 3.105(3) 127.3 7_566 _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.332 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.084 # Attachment 'b816721d_4.cif' data_126a _database_code_depnum_ccdc_archive 'CCDC 706586' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 Cu N6 O8 S6' _chemical_formula_weight 856.48 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 20.144(2) _cell_length_b 16.6614(17) _cell_length_c 10.5603(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3544.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1756 _exptl_absorpt_coefficient_mu 1.028 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8381 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10189 _diffrn_reflns_av_R_equivalents 0.0868 _diffrn_reflns_av_sigmaI/netI 0.1761 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.03 _reflns_number_total 3997 _reflns_number_gt 1907 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0162P)^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 0.47(2) _refine_ls_number_reflns 3997 _refine_ls_number_parameters 232 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1314 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 0.774 _refine_ls_restrained_S_all 0.773 _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 Cu Cu 0.5000 0.0000 0.27981(8) 0.0433(3) Uani 1 2 d S . . S1 S 0.72774(6) 0.00663(10) -0.16210(11) 0.0469(4) Uani 1 1 d . . . S2 S 0.71291(7) 0.10157(8) -0.27830(12) 0.0478(4) Uani 1 1 d . . . S3 S 0.44080(7) 0.21869(9) 0.24506(14) 0.0538(4) Uani 1 1 d . . . N1 N 0.5699(2) 0.0143(3) 0.1465(4) 0.0355(12) Uani 1 1 d . . . N2 N 0.5679(2) 0.0267(3) -0.5854(4) 0.0404(12) Uani 1 1 d . . . C1 C 0.5631(3) 0.0586(3) 0.0411(5) 0.0409(15) Uani 1 1 d . . . H1 H 0.5249 0.0896 0.0331 0.049 Uiso 1 1 calc R . . C2 C 0.6087(3) 0.0615(3) -0.0562(5) 0.0423(16) Uani 1 1 d . . . H2 H 0.6020 0.0936 -0.1271 0.051 Uiso 1 1 calc R . . C3 C 0.6646(3) 0.0148(3) -0.0437(5) 0.0338(15) Uani 1 1 d . . . C4 C 0.6738(2) -0.0296(3) 0.0626(4) 0.0383(15) Uani 1 1 d . . . H4 H 0.7123 -0.0598 0.0726 0.046 Uiso 1 1 calc R . . C5 C 0.6258(2) -0.0296(3) 0.1554(5) 0.0397(14) Uani 1 1 d . . . H5 H 0.6323 -0.0611 0.2270 0.048 Uiso 1 1 calc R . . C6 C 0.6560(2) 0.0666(3) -0.3933(4) 0.0355(14) Uani 1 1 d . . . C7 C 0.6238(3) -0.0067(3) -0.3933(5) 0.0413(16) Uani 1 1 d . . . H7 H 0.6320 -0.0441 -0.3298 0.050 Uiso 1 1 calc R . . C8 C 0.5800(3) -0.0233(3) -0.4878(5) 0.0411(15) Uani 1 1 d . . . H8 H 0.5571 -0.0718 -0.4848 0.049 Uiso 1 1 calc R . . C9 C 0.5994(3) 0.0967(3) -0.5866(5) 0.0432(15) Uani 1 1 d . . . H9 H 0.5912 0.1319 -0.6531 0.052 Uiso 1 1 calc R . . C10 C 0.6435(2) 0.1195(3) -0.4942(5) 0.0405(14) Uani 1 1 d . . . H10 H 0.6647 0.1690 -0.4983 0.049 Uiso 1 1 calc R . . O2 O 0.47677(17) 0.2932(2) 0.2597(5) 0.0801(13) Uani 1 1 d . . . O1 O 0.47906(15) 0.14723(19) 0.2726(4) 0.0596(10) Uani 1 1 d . . . O3 O 0.4060(2) 0.2139(3) 0.1262(4) 0.0893(16) Uani 1 1 d . . . C11 C 0.3793(3) 0.2180(3) 0.3634(5) 0.0447(15) Uani 1 1 d . . . C12 C 0.3127(3) 0.2062(3) 0.3349(5) 0.0526(17) Uani 1 1 d . . . H12 H 0.2997 0.1996 0.2510 0.063 Uiso 1 1 calc R . . C13 C 0.2658(3) 0.2042(4) 0.4291(8) 0.069(2) Uani 1 1 d . . . H13 H 0.2216 0.1955 0.4072 0.083 Uiso 1 1 calc R . . N14 N 0.2809(3) 0.2142(4) 0.5495(7) 0.087(2) Uani 1 1 d . . . C15 C 0.3445(4) 0.2265(4) 0.5783(7) 0.082(2) Uani 1 1 d . . . H15 H 0.3556 0.2335 0.6631 0.098 Uiso 1 1 calc R . . C16 C 0.3956(3) 0.2296(4) 0.4886(6) 0.0578(19) Uani 1 1 d . . . H16 H 0.4392 0.2391 0.5129 0.069 Uiso 1 1 calc R . . O1W O 0.4050(2) 0.1648(3) 0.8704(5) 0.1196(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0377(5) 0.0631(6) 0.0293(5) 0.000 0.000 0.0041(5) S1 0.0341(8) 0.0709(12) 0.0357(8) -0.0010(8) 0.0020(6) 0.0032(8) S2 0.0490(8) 0.0563(10) 0.0382(8) -0.0055(8) 0.0006(7) -0.0136(7) S3 0.0522(10) 0.0556(11) 0.0536(11) -0.0016(9) 0.0043(8) 0.0021(8) N1 0.035(3) 0.041(3) 0.030(3) 0.002(2) -0.006(2) 0.007(2) N2 0.036(3) 0.049(3) 0.036(3) 0.001(3) -0.001(2) 0.003(3) C1 0.048(4) 0.040(4) 0.035(3) 0.001(3) -0.003(3) 0.011(3) C2 0.046(4) 0.052(4) 0.030(3) 0.001(3) 0.003(3) 0.011(3) C3 0.035(3) 0.037(4) 0.029(3) -0.005(3) -0.003(3) -0.006(3) C4 0.028(3) 0.052(4) 0.035(3) -0.001(3) 0.000(3) 0.009(3) C5 0.045(4) 0.039(4) 0.035(3) 0.003(3) -0.004(3) 0.005(3) C6 0.033(3) 0.040(4) 0.034(3) -0.005(3) 0.011(3) 0.001(3) C7 0.047(4) 0.038(4) 0.039(3) 0.005(3) 0.000(3) -0.003(3) C8 0.046(4) 0.043(4) 0.035(3) 0.000(3) -0.007(3) -0.004(3) C9 0.040(4) 0.050(4) 0.040(3) 0.001(3) -0.005(3) -0.003(3) C10 0.040(4) 0.030(4) 0.051(4) 0.005(3) 0.016(3) -0.002(3) O2 0.074(3) 0.067(3) 0.098(3) -0.013(3) 0.010(3) -0.020(2) O1 0.050(2) 0.060(2) 0.069(3) -0.003(3) 0.001(2) 0.0253(18) O3 0.094(4) 0.120(5) 0.054(3) 0.019(3) -0.001(3) 0.008(3) C11 0.056(4) 0.026(3) 0.051(4) -0.006(3) -0.001(3) 0.002(3) C12 0.058(4) 0.043(4) 0.057(4) 0.001(3) -0.009(4) 0.001(3) C13 0.053(5) 0.064(5) 0.091(6) -0.001(5) 0.020(5) 0.000(4) N14 0.095(6) 0.084(5) 0.083(5) -0.010(4) 0.039(5) 0.003(4) C15 0.101(7) 0.065(5) 0.080(6) -0.006(4) -0.004(6) 0.004(5) C16 0.061(5) 0.047(5) 0.066(5) -0.007(4) -0.005(4) 0.001(4) O1W 0.092(4) 0.175(6) 0.091(4) -0.003(3) 0.007(3) -0.034(4) _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 Cu N1 2.005(4) 2_655 ? Cu N1 2.005(4) . ? Cu N2 2.023(4) 2_656 ? Cu N2 2.023(4) 1_556 ? Cu O1 2.490(3) . ? S1 C3 1.789(5) . ? S1 S2 2.024(2) . ? S2 C6 1.769(5) . ? S3 O3 1.440(4) . ? S3 O2 1.446(4) . ? S3 O1 1.448(3) . ? S3 C11 1.760(6) . ? N1 C1 1.344(6) . ? N1 C5 1.346(6) . ? N2 C9 1.328(6) . ? N2 C8 1.348(7) . ? N2 Cu 2.023(4) 1_554 ? C1 C2 1.379(6) . ? C2 C3 1.375(7) . ? C3 C4 1.356(6) . ? C4 C5 1.376(6) . ? C6 C7 1.383(7) . ? C6 C10 1.405(7) . ? C7 C8 1.360(7) . ? C9 C10 1.373(7) . ? C11 C16 1.376(7) . ? C11 C12 1.389(7) . ? C12 C13 1.373(8) . ? C13 N14 1.317(7) . ? N14 C15 1.334(8) . ? C15 C16 1.399(8) . ? 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 Cu N1 90.8(2) 2_655 . ? N1 Cu N2 89.61(14) 2_655 2_656 ? N1 Cu N2 174.0(2) . 2_656 ? N1 Cu N2 174.0(2) 2_655 1_556 ? N1 Cu N2 89.61(14) . 1_556 ? N2 Cu N2 90.6(3) 2_656 1_556 ? N1 Cu O1 88.64(15) 2_655 . ? N1 Cu O1 88.89(15) . . ? N2 Cu O1 97.10(16) 2_656 . ? N2 Cu O1 85.39(16) 1_556 . ? C3 S1 S2 105.04(19) . . ? C6 S2 S1 104.8(2) . . ? O3 S3 O2 112.6(3) . . ? O3 S3 O1 112.9(3) . . ? O2 S3 O1 114.7(2) . . ? O3 S3 C11 106.0(3) . . ? O2 S3 C11 106.4(3) . . ? O1 S3 C11 103.1(3) . . ? C1 N1 C5 116.2(5) . . ? C1 N1 Cu 125.1(4) . . ? C5 N1 Cu 118.4(4) . . ? C9 N2 C8 117.6(5) . . ? C9 N2 Cu 120.6(4) . 1_554 ? C8 N2 Cu 121.6(4) . 1_554 ? N1 C1 C2 124.7(5) . . ? C3 C2 C1 117.0(5) . . ? C4 C3 C2 120.0(5) . . ? C4 C3 S1 116.1(4) . . ? C2 C3 S1 123.9(4) . . ? C3 C4 C5 119.5(5) . . ? N1 C5 C4 122.6(5) . . ? C7 C6 C10 118.0(5) . . ? C7 C6 S2 126.5(4) . . ? C10 C6 S2 115.5(4) . . ? C8 C7 C6 118.9(5) . . ? N2 C8 C7 123.5(5) . . ? N2 C9 C10 123.1(5) . . ? C9 C10 C6 118.8(5) . . ? S3 O1 Cu 155.0(2) . . ? C16 C11 C12 117.3(6) . . ? C16 C11 S3 120.9(5) . . ? C12 C11 S3 121.8(5) . . ? C13 C12 C11 120.8(6) . . ? N14 C13 C12 122.5(7) . . ? C13 N14 C15 117.5(7) . . ? N14 C15 C16 123.9(7) . . ? C11 C16 C15 118.0(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C12 H12 N14 0.93 2.69 3.557(8) 155.9 8_544 C13 H13 O1W 0.93 2.63 3.557(8) 173.7 8_544 C15 H15 O1W 0.93 2.66 3.473(9) 145.8 . _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.819 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.058 # Attachment 'b816721d_5.cif' data_121 _database_code_depnum_ccdc_archive 'CCDC 706587' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 Cu N2 O10 S4' _chemical_formula_weight 572.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6637(14) _cell_length_b 7.8319(14) _cell_length_c 10.2543(18) _cell_angle_alpha 71.048(3) _cell_angle_beta 83.663(3) _cell_angle_gamma 77.074(3) _cell_volume 566.89(18) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1442 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 27.55 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 295 _exptl_absorpt_coefficient_mu 1.384 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8692 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3699 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2581 _reflns_number_gt 1996 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+0.2530P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2581 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0951 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 Cu Cu 0.5000 1.0000 0.5000 0.03146(15) Uani 1 2 d S . . N1 N 0.4063(3) 0.8256(3) 0.4312(2) 0.0302(5) Uani 1 1 d . . . O1 O 0.2921(3) 0.2506(3) 0.3504(2) 0.0571(7) Uani 1 1 d . . . O2 O 0.0078(3) 0.4600(3) 0.2985(2) 0.0550(6) Uani 1 1 d . . . O3 O 0.2514(3) 0.4798(3) 0.1265(2) 0.0513(6) Uani 1 1 d . . . O4 O 0.3083(3) 0.9863(3) 0.65023(19) 0.0361(4) Uani 1 1 d . . . S1 S 0.19912(10) 0.43089(9) 0.27194(7) 0.03586(19) Uani 1 1 d . . . S2 S 0.30678(11) 0.82541(9) 0.78372(7) 0.0383(2) Uani 1 1 d . . . C1 C 0.2323(4) 0.8175(4) 0.4449(3) 0.0387(7) Uani 1 1 d . . . H1 H 0.1548 0.8938 0.4885 0.046 Uiso 1 1 calc R . . C2 C 0.1623(4) 0.7021(4) 0.3980(3) 0.0387(7) Uani 1 1 d . . . H2 H 0.0405 0.7008 0.4096 0.046 Uiso 1 1 calc R . . C3 C 0.2766(4) 0.5883(3) 0.3333(3) 0.0305(6) Uani 1 1 d . . . C4 C 0.4563(4) 0.5967(4) 0.3169(3) 0.0355(6) Uani 1 1 d . . . H4 H 0.5359 0.5236 0.2720 0.043 Uiso 1 1 calc R . . C5 C 0.5159(4) 0.7147(4) 0.3680(3) 0.0337(6) Uani 1 1 d . . . H5 H 0.6374 0.7177 0.3582 0.040 Uiso 1 1 calc R . . C6 C 0.4137(5) 0.8785(5) 0.9065(3) 0.0551(9) Uani 1 1 d . . . H6A H 0.5356 0.8852 0.8758 0.083 Uiso 1 1 calc R . . H6B H 0.4115 0.7841 0.9939 0.083 Uiso 1 1 calc R . . H6C H 0.3517 0.9949 0.9162 0.083 Uiso 1 1 calc R . . C7 C 0.0831(5) 0.8676(6) 0.8484(4) 0.0630(10) Uani 1 1 d . . . H7A H 0.0520 0.9906 0.8545 0.094 Uiso 1 1 calc R . . H7B H 0.0715 0.7810 0.9384 0.094 Uiso 1 1 calc R . . H7C H 0.0043 0.8541 0.7875 0.094 Uiso 1 1 calc R . . O1W O 0.2172(4) 0.3134(4) 0.9183(3) 0.0627(7) Uani 1 1 d . . . H11 H 0.223(5) 0.373(6) 0.979(5) 0.084(14) Uiso 1 1 d . . . H12 H 0.138(7) 0.394(7) 0.857(5) 0.101(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0463(3) 0.0278(3) 0.0263(3) -0.01173(19) 0.0020(2) -0.0163(2) N1 0.0403(13) 0.0254(11) 0.0270(11) -0.0098(9) -0.0015(9) -0.0083(9) O1 0.0863(18) 0.0265(11) 0.0607(15) -0.0044(10) -0.0311(13) -0.0155(11) O2 0.0523(14) 0.0673(16) 0.0591(15) -0.0289(13) -0.0028(11) -0.0258(12) O3 0.0774(17) 0.0537(14) 0.0316(11) -0.0171(10) -0.0023(11) -0.0251(12) O4 0.0508(12) 0.0323(10) 0.0273(10) -0.0091(8) 0.0052(8) -0.0160(9) S1 0.0508(5) 0.0294(4) 0.0319(4) -0.0089(3) -0.0089(3) -0.0147(3) S2 0.0570(5) 0.0275(4) 0.0325(4) -0.0095(3) 0.0034(3) -0.0147(3) C1 0.0422(17) 0.0389(16) 0.0400(16) -0.0205(13) -0.0017(13) -0.0056(13) C2 0.0383(16) 0.0406(16) 0.0427(17) -0.0178(13) -0.0038(13) -0.0100(12) C3 0.0432(16) 0.0256(13) 0.0244(13) -0.0059(10) -0.0047(11) -0.0115(11) C4 0.0475(17) 0.0291(14) 0.0327(15) -0.0135(12) 0.0054(12) -0.0110(12) C5 0.0407(16) 0.0279(14) 0.0353(15) -0.0112(12) 0.0020(12) -0.0120(12) C6 0.077(2) 0.053(2) 0.0360(18) -0.0129(15) -0.0125(16) -0.0115(18) C7 0.061(2) 0.071(3) 0.055(2) -0.0122(19) 0.0151(18) -0.0279(19) O1W 0.0581(17) 0.0734(19) 0.0607(17) -0.0309(16) -0.0053(14) -0.0048(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O4 2.0014(19) 2_676 ? Cu O4 2.0014(19) . ? Cu N1 2.014(2) . ? Cu N1 2.014(2) 2_676 ? Cu O1 2.434(2) 1_565 ? Cu O1 2.434(2) 2_666 ? Cu Cu 7.8319(14) 1_565 ? N1 C1 1.339(4) . ? N1 C5 1.341(3) . ? O1 S1 1.445(2) . ? O1 Cu 2.434(2) 1_545 ? O2 S1 1.441(2) . ? O3 S1 1.448(2) . ? O4 S2 1.5310(19) . ? S1 C3 1.784(3) . ? S2 C7 1.768(4) . ? S2 C6 1.774(3) . ? C1 C2 1.376(4) . ? C2 C3 1.382(4) . ? C3 C4 1.383(4) . ? C4 C5 1.375(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu O4 180.000(1) 2_676 . ? O4 Cu N1 88.78(8) 2_676 . ? O4 Cu N1 91.22(8) . . ? O4 Cu N1 91.22(8) 2_676 2_676 ? O4 Cu N1 88.78(8) . 2_676 ? N1 Cu N1 180.000(1) . 2_676 ? O4 Cu O1 92.03(9) 2_676 1_565 ? O4 Cu O1 87.97(9) . 1_565 ? N1 Cu O1 87.74(8) . 1_565 ? N1 Cu O1 92.26(8) 2_676 1_565 ? O4 Cu O1 87.97(9) 2_676 2_666 ? O4 Cu O1 92.03(9) . 2_666 ? N1 Cu O1 92.26(8) . 2_666 ? N1 Cu O1 87.74(8) 2_676 2_666 ? O1 Cu O1 180.0 1_565 2_666 ? O4 Cu Cu 91.84(5) 2_676 1_565 ? O4 Cu Cu 88.16(5) . 1_565 ? N1 Cu Cu 150.67(6) . 1_565 ? N1 Cu Cu 29.33(6) 2_676 1_565 ? O1 Cu Cu 62.93(5) 1_565 1_565 ? O1 Cu Cu 117.07(5) 2_666 1_565 ? C1 N1 C5 117.4(2) . . ? C1 N1 Cu 121.44(18) . . ? C5 N1 Cu 121.13(19) . . ? S1 O1 Cu 163.37(13) . 1_545 ? S2 O4 Cu 125.37(12) . . ? O2 S1 O1 113.25(15) . . ? O2 S1 O3 113.55(14) . . ? O1 S1 O3 113.03(14) . . ? O2 S1 C3 106.29(13) . . ? O1 S1 C3 104.98(12) . . ? O3 S1 C3 104.71(12) . . ? O4 S2 C7 103.03(16) . . ? O4 S2 C6 106.01(14) . . ? C7 S2 C6 98.87(18) . . ? N1 C1 C2 123.4(3) . . ? C1 C2 C3 118.6(3) . . ? C2 C3 C4 118.6(2) . . ? C2 C3 S1 121.9(2) . . ? C4 C3 S1 119.4(2) . . ? C5 C4 C3 119.1(2) . . ? N1 C5 C4 122.8(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H11 O3 0.91(5) 2.00(5) 2.899(4) 174(4) 1_556 O1W H12 O2 0.91(5) 1.93(5) 2.825(4) 169(4) 2_566 O1W H12 S1 0.91(5) 2.88(5) 3.738(3) 159(4) 2_566 C1 H1 O4 0.93 2.50 2.990(3) 113.1 . C2 H2 O2 0.93 2.57 2.927(4) 103.5 . C5 H5 O4 0.93 2.42 2.900(3) 112.1 2_676 C6 H6C O1W 0.96 2.48 3.438(5) 172.9 1_565 _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.293 _refine_diff_density_min -0.557 _refine_diff_density_rms 0.077