Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Gaynor, Declan' 'Haase, Wolfgang' 'Nolan, Kevin B.' 'Starikova, Zoya' _publ_contact_author_name 'Prof Kevin B Nolan' _publ_contact_author_address ; Prof Kevin B Nolan Department of Chemistry Royal College of Surgeons in Ireland 123 St. Stephen's Green Dublin 2 REPUBLIC OF IRELAND ; data_121e _database_code_CSD 154909 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H46 Cu3 N8 O21 S' _chemical_formula_weight 1053.41 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 Pna2(1) 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' _cell_length_a 15.2049(12) _cell_length_b 14.2017(11) _cell_length_c 18.5719(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4010.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2164 _exptl_absorpt_coefficient_mu 1.722 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 33960 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0712 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 30.03 _reflns_number_total 10045 _reflns_number_gt 7521 _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^)+(0.0466P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.126(11) _refine_ls_number_reflns 10045 _refine_ls_number_parameters 548 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.11662(3) -0.00115(4) 0.00198(3) 0.01834(9) Uani 1 1 d . . . Cu2 Cu -0.18392(3) 0.44835(3) 0.08029(2) 0.01563(10) Uani 1 1 d . . . Cu3 Cu -0.08587(3) 0.95297(3) -0.07624(2) 0.01580(10) Uani 1 1 d . . . S S -0.18187(6) 0.37720(7) 0.24362(5) 0.01774(19) Uani 1 1 d . . . O1 O 0.13457(17) -0.12413(19) 0.04638(15) 0.0194(6) Uani 1 1 d . . . O2 O 0.08295(17) -0.07234(17) -0.08194(17) 0.0214(6) Uani 1 1 d . . . O3 O 0.10228(17) 0.1219(2) -0.04207(16) 0.0209(6) Uani 1 1 d . . . O4 O 0.14157(18) 0.06890(18) 0.08813(17) 0.0239(6) Uani 1 1 d . . . O5 O -0.21113(17) 0.51061(18) -0.01113(15) 0.0196(6) Uani 1 1 d . . . O6 O -0.17209(17) 0.33581(19) 0.01806(15) 0.0193(6) Uani 1 1 d . . . O7 O -0.05650(17) 1.01231(18) 0.01573(14) 0.0186(6) Uani 1 1 d . . . O8 O -0.10225(17) 0.84005(19) -0.01572(15) 0.0190(6) Uani 1 1 d . . . O1S O -0.10125(18) 0.4145(2) 0.27759(16) 0.0278(7) Uani 1 1 d . . . O2S O -0.20252(18) 0.28447(19) 0.27304(16) 0.0235(6) Uani 1 1 d . . . O3S O -0.25455(17) 0.44329(19) 0.25772(15) 0.0224(6) Uani 1 1 d . . . O4S O -0.16740(19) 0.3682(2) 0.16540(16) 0.0233(6) Uani 1 1 d . . . O1W O -0.10287(18) 0.8798(2) -0.16588(16) 0.0235(6) Uani 1 1 d . . . N1 N 0.10215(19) -0.1651(2) -0.0674(2) 0.0200(7) Uani 1 1 d . . . H1N H 0.0965 -0.2083 -0.1009 0.024 Uiso 1 1 calc R . . N2 N 0.2600(2) -0.4909(2) -0.0763(2) 0.0203(7) Uani 1 1 d . . . H2NA H 0.2363 -0.4794 -0.1211 0.024 Uiso 1 1 calc R . . H2NB H 0.2522 -0.5537 -0.0658 0.024 Uiso 1 1 calc R . . N3 N 0.1237(2) 0.1625(2) 0.0735(2) 0.0205(7) Uani 1 1 d . . . H3N H 0.1261 0.2053 0.1078 0.025 Uiso 1 1 calc R . . N4 N -0.0304(2) 0.4892(2) 0.0739(2) 0.0209(7) Uani 1 1 d . . . H4NA H -0.0247 0.5516 0.0616 0.025 Uiso 1 1 calc R . . H4NB H -0.0047 0.4805 0.1183 0.025 Uiso 1 1 calc R . . N5 N -0.1982(2) 0.4457(2) -0.06563(19) 0.0165(7) Uani 1 1 d . . . H5N H -0.2013 0.4625 -0.1111 0.020 Uiso 1 1 calc R . . N6 N -0.0449(2) 0.0662(2) -0.13617(17) 0.0162(7) Uani 1 1 d . . . H6NA H 0.0051 0.0894 -0.1146 0.019 Uiso 1 1 calc R . . H6NB H -0.0284 0.0436 -0.1806 0.019 Uiso 1 1 calc R . . N7 N -0.0653(2) 0.9456(2) 0.06869(18) 0.0163(7) Uani 1 1 d . . . H7N H -0.0570 0.9606 0.1142 0.020 Uiso 1 1 calc R . . N8 N -0.2203(2) 0.5653(2) 0.13607(18) 0.0158(7) Uani 1 1 d . . . H8NA H -0.2679 0.5913 0.1129 0.019 Uiso 1 1 calc R . . H8NB H -0.2394 0.5461 0.1807 0.019 Uiso 1 1 calc R . . C1 C 0.1287(2) -0.1876(3) -0.0033(2) 0.0177(8) Uani 1 1 d . . . C2 C 0.1536(2) -0.2867(3) 0.0123(2) 0.0171(8) Uani 1 1 d . . . C3 C 0.1891(2) -0.3435(3) -0.0412(2) 0.0185(8) Uani 1 1 d . . . H3A H 0.1942 -0.3208 -0.0891 0.022 Uiso 1 1 calc R . . C4 C 0.2171(2) -0.4345(3) -0.0237(2) 0.0192(8) Uani 1 1 d . . . C5 C 0.2096(3) -0.4674(3) 0.0465(2) 0.0222(9) Uani 1 1 d . . . H5A H 0.2283 -0.5293 0.0583 0.027 Uiso 1 1 calc R . . C6 C 0.1745(3) -0.4090(3) 0.0997(2) 0.0236(9) Uani 1 1 d . . . H6A H 0.1702 -0.4312 0.1478 0.028 Uiso 1 1 calc R . . C7 C 0.1460(2) -0.3195(3) 0.0831(2) 0.0215(8) Uani 1 1 d . . . H7A H 0.1213 -0.2805 0.1194 0.026 Uiso 1 1 calc R . . C8 C 0.1032(2) 0.1859(3) 0.0073(3) 0.0200(8) Uani 1 1 d . . . C9 C 0.0784(2) 0.2839(3) -0.0101(2) 0.0183(8) Uani 1 1 d . . . C10 C 0.0393(2) 0.3415(3) 0.0414(2) 0.0167(8) Uani 1 1 d . . . H10A H 0.0307 0.3192 0.0891 0.020 Uiso 1 1 calc R . . C11 C 0.0126(2) 0.4327(3) 0.0223(2) 0.0187(8) Uani 1 1 d . . . C12 C 0.0251(3) 0.4636(3) -0.0479(2) 0.0195(8) Uani 1 1 d . . . H12A H 0.0069 0.5252 -0.0610 0.023 Uiso 1 1 calc R . . C13 C 0.0635(3) 0.4065(3) -0.0986(2) 0.0241(9) Uani 1 1 d . . . H13A H 0.0715 0.4288 -0.1464 0.029 Uiso 1 1 calc R . . C14 C 0.0906(2) 0.3158(3) -0.0802(2) 0.0190(8) Uani 1 1 d . . . H14A H 0.1171 0.2762 -0.1153 0.023 Uiso 1 1 calc R . . C15 C -0.1813(2) 0.3579(3) -0.0475(2) 0.0155(8) Uani 1 1 d . . . C16 C -0.1708(2) 0.2872(3) -0.1066(2) 0.0185(8) Uani 1 1 d . . . C17 C -0.1156(2) 0.2110(3) -0.0944(2) 0.0166(8) Uani 1 1 d . . . H17A H -0.0869 0.2040 -0.0492 0.020 Uiso 1 1 calc R . . C18 C -0.1026(2) 0.1451(3) -0.1486(2) 0.0166(8) Uani 1 1 d . . . C19 C -0.1464(2) 0.1533(3) -0.2136(2) 0.0195(8) Uani 1 1 d . . . H19A H -0.1393 0.1067 -0.2498 0.023 Uiso 1 1 calc R . . C20 C -0.2013(2) 0.2309(3) -0.2257(2) 0.0200(8) Uani 1 1 d . . . H20A H -0.2297 0.2382 -0.2709 0.024 Uiso 1 1 calc R . . C21 C -0.2142(3) 0.2972(3) -0.1719(2) 0.0208(8) Uani 1 1 d . . . H21A H -0.2524 0.3491 -0.1797 0.025 Uiso 1 1 calc R . . C22 C -0.0863(2) 0.8591(3) 0.0506(2) 0.0161(8) Uani 1 1 d . . . C23 C -0.0913(2) 0.7846(3) 0.1070(2) 0.0148(8) Uani 1 1 d . . . C24 C -0.1509(2) 0.7118(3) 0.0971(2) 0.0153(8) Uani 1 1 d . . . H24A H -0.1881 0.7119 0.0560 0.018 Uiso 1 1 calc R . . C25 C -0.1566(2) 0.6386(3) 0.1466(2) 0.0156(8) Uani 1 1 d . . . C26 C -0.1002(2) 0.6380(3) 0.2056(2) 0.0192(8) Uani 1 1 d . . . H26A H -0.1015 0.5869 0.2386 0.023 Uiso 1 1 calc R . . C27 C -0.0421(3) 0.7120(3) 0.2159(2) 0.0202(8) Uani 1 1 d . . . H27A H -0.0052 0.7121 0.2572 0.024 Uiso 1 1 calc R . . C28 C -0.0369(2) 0.7853(3) 0.1679(2) 0.0174(8) Uani 1 1 d . . . H28A H 0.0031 0.8356 0.1757 0.021 Uiso 1 1 calc R . . O2W O -0.00407(18) 0.2779(2) 0.34295(16) 0.0270(7) Uani 1 1 d . . . O3W O 0.1390(2) 0.3359(2) 0.4179(2) 0.0469(9) Uani 1 1 d . . . O4W O 0.0608(2) 0.4391(2) 0.21271(17) 0.0329(7) Uani 1 1 d . . . O5W O 0.0158(2) 1.0120(2) 0.19628(18) 0.0387(8) Uani 1 1 d . . . O6W O -0.1633(2) 0.1519(2) 0.0810(2) 0.0381(8) Uani 1 1 d . . . O7W O 0.1350(2) 0.2569(3) 0.2007(2) 0.0203(8) Uiso 0.70 1 d P . . O8W O -0.2922(3) 0.0477(3) 0.3059(3) 0.0328(10) Uiso 0.70 1 d P . . O9W O -0.1370(4) 0.1164(4) 0.2276(3) 0.0519(14) Uiso 0.70 1 d P . . O7W' O 0.1866(9) 0.2967(10) 0.1745(8) 0.056(3) Uiso 0.30 1 d P . . O8W' O -0.1478(8) -0.0014(8) 0.2922(6) 0.044(3) Uiso 0.30 1 d P . . O9W' O -0.0913(9) 0.1488(10) 0.2101(8) 0.052(3) Uiso 0.30 1 d P . . H1WA H -0.0752 0.8388 -0.1822 0.070 Uiso 1 1 d . . . H1WB H -0.1349 0.8703 -0.2023 0.070 Uiso 1 1 d . . . H2WA H 0.0454 0.3023 0.3713 0.070 Uiso 1 1 d . . . H2WB H -0.0504 0.3227 0.3378 0.070 Uiso 1 1 d . . . H3WA H 0.1646 0.3803 0.4524 0.070 Uiso 1 1 d . . . H3WB H 0.0983 0.3312 0.4540 0.070 Uiso 1 1 d . . . H4WA H 0.0122 0.4226 0.2332 0.070 Uiso 1 1 d . . . H4WB H 0.1014 0.4568 0.2413 0.070 Uiso 1 1 d . . . H5WA H 0.0427 1.0193 0.1703 0.070 Uiso 1 1 d . . . H5WB H -0.0036 1.0762 0.2077 0.070 Uiso 1 1 d . . . H6WA H -0.1114 0.1290 0.0533 0.070 Uiso 1 1 d . . . H6WB H -0.1668 0.2067 0.0643 0.070 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02012(19) 0.01423(19) 0.0207(2) -0.00215(17) -0.00345(18) 0.00022(16) Cu2 0.0196(2) 0.0136(2) 0.0136(2) -0.0005(2) 0.00013(18) 0.00098(18) Cu3 0.0204(2) 0.0135(2) 0.0135(2) 0.0002(2) -0.00153(19) -0.00109(18) S 0.0214(5) 0.0167(4) 0.0151(5) 0.0012(4) 0.0010(4) 0.0006(4) O1 0.0208(14) 0.0164(14) 0.0210(15) -0.0004(12) -0.0053(11) -0.0012(11) O2 0.0259(13) 0.0150(13) 0.0235(16) -0.0049(12) -0.0057(13) 0.0020(11) O3 0.0214(14) 0.0195(15) 0.0218(16) -0.0019(12) 0.0004(11) 0.0007(11) O4 0.0299(15) 0.0152(14) 0.0266(17) -0.0030(12) -0.0112(14) 0.0054(11) O5 0.0270(14) 0.0138(14) 0.0180(17) -0.0038(11) -0.0017(11) 0.0040(11) O6 0.0227(14) 0.0167(14) 0.0184(16) -0.0020(11) 0.0004(11) 0.0035(11) O7 0.0272(14) 0.0155(13) 0.0131(16) 0.0030(11) -0.0023(11) -0.0010(11) O8 0.0248(14) 0.0156(14) 0.0167(16) -0.0005(11) -0.0016(11) 0.0007(11) O1S 0.0312(16) 0.0250(15) 0.0270(17) 0.0025(13) -0.0035(13) -0.0014(12) O2S 0.0308(15) 0.0170(14) 0.0226(16) -0.0004(11) 0.0018(12) 0.0004(12) O3S 0.0247(14) 0.0203(15) 0.0222(15) 0.0045(11) 0.0037(11) 0.0027(11) O4S 0.0316(16) 0.0210(15) 0.0173(15) 0.0042(12) -0.0005(12) 0.0050(12) O1W 0.0306(16) 0.0222(15) 0.0178(15) -0.0060(12) -0.0070(12) 0.0029(12) N1 0.0202(17) 0.0179(17) 0.022(2) -0.0044(15) 0.0001(15) 0.0039(13) N2 0.0220(16) 0.0151(15) 0.0238(18) -0.0013(15) -0.0020(15) -0.0014(12) N3 0.0204(17) 0.0157(16) 0.025(2) -0.0041(14) -0.0052(15) 0.0028(13) N4 0.0220(17) 0.0196(17) 0.0211(19) 0.0014(15) 0.0014(14) 0.0014(13) N5 0.0219(15) 0.0153(17) 0.0122(17) -0.0004(13) 0.0031(13) -0.0009(13) N6 0.0192(16) 0.0145(16) 0.0148(17) 0.0004(12) 0.0000(13) 0.0008(13) N7 0.0250(16) 0.0127(16) 0.0112(18) 0.0010(12) -0.0025(13) -0.0033(13) N8 0.0171(15) 0.0149(16) 0.0153(17) 0.0006(12) 0.0009(13) 0.0016(12) C1 0.0162(18) 0.0174(19) 0.020(2) -0.0030(17) 0.0018(16) -0.0011(14) C2 0.0141(17) 0.0169(19) 0.020(2) -0.0023(16) -0.0032(16) -0.0022(14) C3 0.0170(19) 0.0138(18) 0.025(2) 0.0012(16) -0.0008(16) -0.0012(14) C4 0.0107(17) 0.020(2) 0.027(2) 0.0023(16) 0.0001(15) -0.0009(15) C5 0.0176(19) 0.022(2) 0.027(2) 0.0045(17) -0.0004(16) -0.0029(15) C6 0.024(2) 0.024(2) 0.023(2) 0.0086(17) 0.0008(17) -0.0010(17) C7 0.0185(18) 0.023(2) 0.023(2) -0.0054(18) 0.0038(18) -0.0013(16) C8 0.0173(19) 0.019(2) 0.023(2) -0.0017(18) 0.0033(17) 0.0005(15) C9 0.0143(17) 0.0163(19) 0.024(2) -0.0046(16) -0.0034(16) -0.0004(14) C10 0.0158(18) 0.0162(18) 0.018(2) 0.0002(15) 0.0005(15) -0.0022(14) C11 0.0125(17) 0.021(2) 0.023(2) -0.0036(15) -0.0004(15) -0.0013(15) C12 0.021(2) 0.015(2) 0.023(2) 0.0011(16) -0.0041(16) 0.0007(15) C13 0.025(2) 0.032(2) 0.015(2) 0.0031(17) 0.0013(15) -0.0016(18) C14 0.0155(17) 0.0205(19) 0.021(2) -0.0013(17) 0.0053(17) -0.0009(15) C15 0.0105(17) 0.018(2) 0.018(2) -0.0037(15) -0.0001(14) 0.0004(14) C16 0.0176(19) 0.020(2) 0.018(2) -0.0011(16) 0.0026(15) -0.0048(15) C17 0.0172(19) 0.020(2) 0.013(2) 0.0024(15) -0.0027(14) -0.0046(15) C18 0.0166(18) 0.0145(19) 0.019(2) 0.0010(14) 0.0074(15) -0.0033(14) C19 0.0193(18) 0.022(2) 0.017(2) -0.0052(16) 0.0025(16) -0.0045(16) C20 0.0209(19) 0.024(2) 0.015(2) 0.0010(15) -0.0026(15) -0.0033(16) C21 0.0169(19) 0.017(2) 0.028(2) -0.0032(16) -0.0028(16) 0.0007(15) C22 0.0120(18) 0.0168(19) 0.020(2) 0.0050(16) 0.0009(14) 0.0020(14) C23 0.0155(18) 0.0136(19) 0.015(2) 0.0025(14) 0.0007(15) 0.0023(14) C24 0.0142(17) 0.0174(19) 0.014(2) -0.0021(14) 0.0015(14) 0.0022(14) C25 0.0183(18) 0.0138(18) 0.015(2) -0.0031(14) 0.0003(15) 0.0021(14) C26 0.025(2) 0.021(2) 0.0125(19) 0.0020(15) 0.0017(15) 0.0002(15) C27 0.024(2) 0.021(2) 0.016(2) 0.0014(15) -0.0029(16) 0.0013(16) C28 0.0172(18) 0.0159(18) 0.019(2) -0.0006(15) -0.0006(15) -0.0014(15) O2W 0.0275(15) 0.0281(17) 0.0254(17) 0.0074(13) -0.0044(12) -0.0005(12) O3W 0.069(2) 0.0327(19) 0.039(2) 0.0093(17) -0.022(2) -0.0203(17) O4W 0.0353(17) 0.036(2) 0.0276(18) 0.0018(13) 0.0007(13) 0.0021(14) O5W 0.066(2) 0.0212(16) 0.0287(19) -0.0020(14) -0.0172(16) 0.0031(15) O6W 0.054(2) 0.0216(16) 0.0392(19) 0.0056(15) 0.0128(18) 0.0084(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.922(3) . ? Cu1 O2 1.927(3) . ? Cu1 O3 1.942(3) . ? Cu1 O1 1.951(3) . ? Cu2 O5 1.958(3) . ? Cu2 O4S 1.964(3) . ? Cu2 O6 1.981(3) . ? Cu2 N8 2.034(3) . ? Cu2 N4 2.408(3) . ? Cu3 O7 1.956(3) . ? Cu3 O8 1.974(3) . ? Cu3 O1W 1.980(3) . ? Cu3 N6 2.053(3) 1_565 ? Cu3 N2 2.405(3) 3_455 ? S O2S 1.460(3) . ? S O3S 1.473(3) . ? S O4S 1.475(3) . ? S O1S 1.477(3) . ? O1 C1 1.293(5) . ? O2 N1 1.376(4) . ? O3 C8 1.290(5) . ? O4 N3 1.384(4) . ? O5 N5 1.383(4) . ? O6 C15 1.265(5) . ? O7 N7 1.372(4) . ? O8 C22 1.284(5) . ? O1W H1WA 0.7796 . ? O1W H1WB 0.8443 . ? N1 C1 1.297(6) . ? N1 H1N 0.8800 . ? N2 C4 1.421(5) . ? N2 Cu3 2.405(3) 3 ? N2 H2NA 0.9200 . ? N2 H2NB 0.9200 . ? N3 C8 1.311(6) . ? N3 H3N 0.8800 . ? N4 C11 1.412(5) . ? N4 H4NA 0.9200 . ? N4 H4NB 0.9200 . ? N5 C15 1.317(5) . ? N5 H5N 0.8800 . ? N6 C18 1.441(5) . ? N6 Cu3 2.053(3) 1_545 ? N6 H6NA 0.9200 . ? N6 H6NB 0.9200 . ? N7 C22 1.314(5) . ? N7 H7N 0.8800 . ? N8 C25 1.437(5) . ? N8 H8NA 0.9200 . ? N8 H8NB 0.9200 . ? C1 C2 1.486(5) . ? C2 C3 1.388(5) . ? C2 C7 1.400(6) . ? C3 C4 1.399(6) . ? C3 H3A 0.9500 . ? C4 C5 1.390(6) . ? C5 C6 1.395(6) . ? C5 H5A 0.9500 . ? C6 C7 1.377(6) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 C9 1.479(5) . ? C9 C14 1.391(6) . ? C9 C10 1.392(5) . ? C10 C11 1.403(5) . ? C10 H10A 0.9500 . ? C11 C12 1.388(6) . ? C12 C13 1.373(6) . ? C12 H12A 0.9500 . ? C13 C14 1.394(6) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.495(6) . ? C16 C21 1.388(6) . ? C16 C17 1.389(6) . ? C17 C18 1.389(5) . ? C17 H17A 0.9500 . ? C18 C19 1.385(6) . ? C19 C20 1.400(6) . ? C19 H19A 0.9500 . ? C20 C21 1.386(6) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.490(5) . ? C23 C24 1.387(5) . ? C23 C28 1.402(5) . ? C24 C25 1.391(5) . ? C24 H24A 0.9500 . ? C25 C26 1.390(5) . ? C26 C27 1.386(6) . ? C26 H26A 0.9500 . ? C27 C28 1.374(5) . ? C27 H27A 0.9500 . ? C28 H28A 0.9500 . ? O2W H2WA 0.9809 . ? O2W H2WB 0.9537 . ? O3W H3WA 0.9797 . ? O3W H3WB 0.9158 . ? O4W H4WA 0.8639 . ? O4W H4WB 0.8517 . ? O5W H5WA 0.6411 . ? O5W H5WB 0.9817 . ? O6W H6WA 0.9970 . ? O6W H6WB 0.8388 . ? O7W O7W' 1.083(14) . ? O9W O9W' 0.894(13) . ? 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 Cu1 O2 175.83(14) . . ? O4 Cu1 O3 84.66(12) . . ? O2 Cu1 O3 95.84(12) . . ? O4 Cu1 O1 94.81(12) . . ? O2 Cu1 O1 84.80(12) . . ? O3 Cu1 O1 178.40(12) . . ? O5 Cu2 O4S 170.53(12) . . ? O5 Cu2 O6 82.97(11) . . ? O4S Cu2 O6 89.43(12) . . ? O5 Cu2 N8 90.89(12) . . ? O4S Cu2 N8 95.64(13) . . ? O6 Cu2 N8 168.74(12) . . ? O5 Cu2 N4 93.06(12) . . ? O4S Cu2 N4 93.16(12) . . ? O6 Cu2 N4 94.46(11) . . ? N8 Cu2 N4 95.30(12) . . ? O7 Cu3 O8 83.20(11) . . ? O7 Cu3 O1W 172.00(11) . . ? O8 Cu3 O1W 92.05(12) . . ? O7 Cu3 N6 93.82(12) . 1_565 ? O8 Cu3 N6 169.58(12) . 1_565 ? O1W Cu3 N6 89.71(13) . 1_565 ? O7 Cu3 N2 97.27(12) . 3_455 ? O8 Cu3 N2 93.41(11) . 3_455 ? O1W Cu3 N2 89.41(12) . 3_455 ? N6 Cu3 N2 96.88(12) 1_565 3_455 ? O2S S O3S 110.29(16) . . ? O2S S O4S 108.80(17) . . ? O3S S O4S 110.03(16) . . ? O2S S O1S 110.02(17) . . ? O3S S O1S 108.53(17) . . ? O4S S O1S 109.16(17) . . ? C1 O1 Cu1 108.3(3) . . ? N1 O2 Cu1 106.7(2) . . ? C8 O3 Cu1 109.4(3) . . ? N3 O4 Cu1 107.2(2) . . ? N5 O5 Cu2 107.7(2) . . ? C15 O6 Cu2 110.6(3) . . ? N7 O7 Cu3 107.8(2) . . ? C22 O8 Cu3 110.6(2) . . ? S O4S Cu2 136.31(18) . . ? Cu3 O1W H1WA 130.4 . . ? Cu3 O1W H1WB 146.4 . . ? H1WA O1W H1WB 83.1 . . ? C1 N1 O2 118.9(3) . . ? C1 N1 H1N 120.6 . . ? O2 N1 H1N 120.6 . . ? C4 N2 Cu3 108.7(2) . 3 ? C4 N2 H2NA 110.0 . . ? Cu3 N2 H2NA 110.0 3 . ? C4 N2 H2NB 110.0 . . ? Cu3 N2 H2NB 110.0 3 . ? H2NA N2 H2NB 108.3 . . ? C8 N3 O4 118.2(3) . . ? C8 N3 H3N 120.9 . . ? O4 N3 H3N 120.9 . . ? C11 N4 Cu2 110.2(2) . . ? C11 N4 H4NA 109.6 . . ? Cu2 N4 H4NA 109.6 . . ? C11 N4 H4NB 109.6 . . ? Cu2 N4 H4NB 109.6 . . ? H4NA N4 H4NB 108.1 . . ? C15 N5 O5 118.2(3) . . ? C15 N5 H5N 120.9 . . ? O5 N5 H5N 120.9 . . ? C18 N6 Cu3 120.7(2) . 1_545 ? C18 N6 H6NA 107.1 . . ? Cu3 N6 H6NA 107.1 1_545 . ? C18 N6 H6NB 107.1 . . ? Cu3 N6 H6NB 107.1 1_545 . ? H6NA N6 H6NB 106.8 . . ? C22 N7 O7 119.1(3) . . ? C22 N7 H7N 120.5 . . ? O7 N7 H7N 120.5 . . ? C25 N8 Cu2 118.5(2) . . ? C25 N8 H8NA 107.7 . . ? Cu2 N8 H8NA 107.7 . . ? C25 N8 H8NB 107.7 . . ? Cu2 N8 H8NB 107.7 . . ? H8NA N8 H8NB 107.1 . . ? O1 C1 N1 120.2(4) . . ? O1 C1 C2 120.3(4) . . ? N1 C1 C2 119.5(4) . . ? C3 C2 C7 120.7(4) . . ? C3 C2 C1 120.7(4) . . ? C7 C2 C1 118.5(4) . . ? C2 C3 C4 119.3(4) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 C4 C3 120.2(4) . . ? C5 C4 N2 119.6(4) . . ? C3 C4 N2 120.1(4) . . ? C4 C5 C6 119.7(4) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C7 C6 C5 120.7(4) . . ? C7 C6 H6A 119.6 . . ? C5 C6 H6A 119.6 . . ? C6 C7 C2 119.4(4) . . ? C6 C7 H7A 120.3 . . ? C2 C7 H7A 120.3 . . ? O3 C8 N3 119.4(4) . . ? O3 C8 C9 120.3(4) . . ? N3 C8 C9 120.2(4) . . ? C14 C9 C10 120.6(4) . . ? C14 C9 C8 118.5(4) . . ? C10 C9 C8 120.8(4) . . ? C9 C10 C11 119.4(4) . . ? C9 C10 H10A 120.3 . . ? C11 C10 H10A 120.3 . . ? C12 C11 C10 119.4(4) . . ? C12 C11 N4 121.4(4) . . ? C10 C11 N4 119.1(4) . . ? C13 C12 C11 121.0(4) . . ? C13 C12 H12A 119.5 . . ? C11 C12 H12A 119.5 . . ? C12 C13 C14 120.2(4) . . ? C12 C13 H13A 119.9 . . ? C14 C13 H13A 119.9 . . ? C9 C14 C13 119.4(4) . . ? C9 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? O6 C15 N5 120.1(4) . . ? O6 C15 C16 121.9(4) . . ? N5 C15 C16 117.9(4) . . ? C21 C16 C17 120.6(4) . . ? C21 C16 C15 121.5(4) . . ? C17 C16 C15 117.8(4) . . ? C18 C17 C16 119.5(4) . . ? C18 C17 H17A 120.2 . . ? C16 C17 H17A 120.2 . . ? C19 C18 C17 120.5(4) . . ? C19 C18 N6 119.9(3) . . ? C17 C18 N6 119.6(4) . . ? C18 C19 C20 119.5(4) . . ? C18 C19 H19A 120.3 . . ? C20 C19 H19A 120.3 . . ? C21 C20 C19 120.3(4) . . ? C21 C20 H20A 119.9 . . ? C19 C20 H20A 119.9 . . ? C20 C21 C16 119.5(4) . . ? C20 C21 H21A 120.2 . . ? C16 C21 H21A 120.2 . . ? O8 C22 N7 119.2(4) . . ? O8 C22 C23 121.0(3) . . ? N7 C22 C23 119.8(4) . . ? C24 C23 C28 119.8(3) . . ? C24 C23 C22 118.0(3) . . ? C28 C23 C22 122.2(3) . . ? C23 C24 C25 120.7(4) . . ? C23 C24 H24A 119.6 . . ? C25 C24 H24A 119.6 . . ? C26 C25 C24 119.2(3) . . ? C26 C25 N8 121.3(3) . . ? C24 C25 N8 119.6(3) . . ? C27 C26 C25 119.8(4) . . ? C27 C26 H26A 120.1 . . ? C25 C26 H26A 120.1 . . ? C28 C27 C26 121.4(4) . . ? C28 C27 H27A 119.3 . . ? C26 C27 H27A 119.3 . . ? C27 C28 C23 119.0(4) . . ? C27 C28 H28A 120.5 . . ? C23 C28 H28A 120.5 . . ? H2WA O2W H2WB 112.7 . . ? H3WA O3W H3WB 80.5 . . ? H4WA O4W H4WB 115.2 . . ? H5WA O5W H5WB 101.7 . . ? H6WA O6W H6WB 99.3 . . ? 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 O4 Cu1 O1 C1 -174.6(2) . . . . ? O2 Cu1 O1 C1 9.5(2) . . . . ? O3 Cu1 O1 C1 -104(5) . . . . ? O4 Cu1 O2 N1 -93.2(18) . . . . ? O3 Cu1 O2 N1 170.2(2) . . . . ? O1 Cu1 O2 N1 -8.4(2) . . . . ? O4 Cu1 O3 C8 -9.1(2) . . . . ? O2 Cu1 O3 C8 166.7(2) . . . . ? O1 Cu1 O3 C8 -80(5) . . . . ? O2 Cu1 O4 N3 -89.0(18) . . . . ? O3 Cu1 O4 N3 8.1(2) . . . . ? O1 Cu1 O4 N3 -173.5(2) . . . . ? O4S Cu2 O5 N5 -42.8(8) . . . . ? O6 Cu2 O5 N5 -5.9(2) . . . . ? N8 Cu2 O5 N5 -176.4(2) . . . . ? N4 Cu2 O5 N5 88.3(2) . . . . ? O5 Cu2 O6 C15 4.2(2) . . . . ? O4S Cu2 O6 C15 178.6(3) . . . . ? N8 Cu2 O6 C15 61.6(7) . . . . ? N4 Cu2 O6 C15 -88.3(3) . . . . ? O8 Cu3 O7 N7 -1.3(2) . . . . ? O1W Cu3 O7 N7 -55.2(9) . . . . ? N6 Cu3 O7 N7 -171.3(2) 1_565 . . . ? N2 Cu3 O7 N7 91.3(2) 3_455 . . . ? O7 Cu3 O8 C22 -0.2(2) . . . . ? O1W Cu3 O8 C22 173.3(3) . . . . ? N6 Cu3 O8 C22 73.7(8) 1_565 . . . ? N2 Cu3 O8 C22 -97.2(3) 3_455 . . . ? O2S S O4S Cu2 149.5(2) . . . . ? O3S S O4S Cu2 28.6(3) . . . . ? O1S S O4S Cu2 -90.4(3) . . . . ? O5 Cu2 O4S S -127.9(6) . . . . ? O6 Cu2 O4S S -164.5(3) . . . . ? N8 Cu2 O4S S 5.4(3) . . . . ? N4 Cu2 O4S S 101.0(3) . . . . ? Cu1 O2 N1 C1 6.3(4) . . . . ? Cu1 O4 N3 C8 -6.2(4) . . . . ? O5 Cu2 N4 C11 -74.3(3) . . . . ? O4S Cu2 N4 C11 98.5(3) . . . . ? O6 Cu2 N4 C11 8.8(3) . . . . ? N8 Cu2 N4 C11 -165.5(3) . . . . ? Cu2 O5 N5 C15 7.1(4) . . . . ? Cu3 O7 N7 C22 2.8(4) . . . . ? O5 Cu2 N8 C25 -85.2(3) . . . . ? O4S Cu2 N8 C25 101.7(3) . . . . ? O6 Cu2 N8 C25 -141.9(6) . . . . ? N4 Cu2 N8 C25 8.0(3) . . . . ? Cu1 O1 C1 N1 -8.9(4) . . . . ? Cu1 O1 C1 C2 170.2(3) . . . . ? O2 N1 C1 O1 1.9(5) . . . . ? O2 N1 C1 C2 -177.2(3) . . . . ? O1 C1 C2 C3 -148.3(4) . . . . ? N1 C1 C2 C3 30.8(5) . . . . ? O1 C1 C2 C7 27.6(5) . . . . ? N1 C1 C2 C7 -153.3(4) . . . . ? C7 C2 C3 C4 0.1(6) . . . . ? C1 C2 C3 C4 175.9(3) . . . . ? C2 C3 C4 C5 -0.1(6) . . . . ? C2 C3 C4 N2 -175.0(3) . . . . ? Cu3 N2 C4 C5 -89.8(4) 3 . . . ? Cu3 N2 C4 C3 85.1(4) 3 . . . ? C3 C4 C5 C6 -0.4(6) . . . . ? N2 C4 C5 C6 174.5(4) . . . . ? C4 C5 C6 C7 1.0(6) . . . . ? C5 C6 C7 C2 -0.9(6) . . . . ? C3 C2 C7 C6 0.4(6) . . . . ? C1 C2 C7 C6 -175.5(3) . . . . ? Cu1 O3 C8 N3 8.4(4) . . . . ? Cu1 O3 C8 C9 -169.4(3) . . . . ? O4 N3 C8 O3 -1.5(5) . . . . ? O4 N3 C8 C9 176.3(3) . . . . ? O3 C8 C9 C14 -27.2(5) . . . . ? N3 C8 C9 C14 155.0(4) . . . . ? O3 C8 C9 C10 149.4(4) . . . . ? N3 C8 C9 C10 -28.4(5) . . . . ? C14 C9 C10 C11 -0.5(5) . . . . ? C8 C9 C10 C11 -176.9(3) . . . . ? C9 C10 C11 C12 0.5(5) . . . . ? C9 C10 C11 N4 177.3(3) . . . . ? Cu2 N4 C11 C12 95.4(4) . . . . ? Cu2 N4 C11 C10 -81.4(4) . . . . ? C10 C11 C12 C13 -0.2(6) . . . . ? N4 C11 C12 C13 -177.0(4) . . . . ? C11 C12 C13 C14 0.0(6) . . . . ? C10 C9 C14 C13 0.2(6) . . . . ? C8 C9 C14 C13 176.8(3) . . . . ? C12 C13 C14 C9 0.0(6) . . . . ? Cu2 O6 C15 N5 -1.4(4) . . . . ? Cu2 O6 C15 C16 176.8(3) . . . . ? O5 N5 C15 O6 -4.1(5) . . . . ? O5 N5 C15 C16 177.7(3) . . . . ? O6 C15 C16 C21 152.6(4) . . . . ? N5 C15 C16 C21 -29.1(5) . . . . ? O6 C15 C16 C17 -27.8(5) . . . . ? N5 C15 C16 C17 150.4(4) . . . . ? C21 C16 C17 C18 1.1(6) . . . . ? C15 C16 C17 C18 -178.5(3) . . . . ? C16 C17 C18 C19 -2.0(6) . . . . ? C16 C17 C18 N6 179.6(3) . . . . ? Cu3 N6 C18 C19 -100.8(4) 1_545 . . . ? Cu3 N6 C18 C17 77.6(4) 1_545 . . . ? C17 C18 C19 C20 2.7(6) . . . . ? N6 C18 C19 C20 -179.0(3) . . . . ? C18 C19 C20 C21 -2.4(6) . . . . ? C19 C20 C21 C16 1.4(6) . . . . ? C17 C16 C21 C20 -0.8(6) . . . . ? C15 C16 C21 C20 178.8(4) . . . . ? Cu3 O8 C22 N7 1.9(4) . . . . ? Cu3 O8 C22 C23 -178.1(3) . . . . ? O7 N7 C22 O8 -3.3(5) . . . . ? O7 N7 C22 C23 176.7(3) . . . . ? O8 C22 C23 C24 -31.0(5) . . . . ? N7 C22 C23 C24 149.1(4) . . . . ? O8 C22 C23 C28 147.6(4) . . . . ? N7 C22 C23 C28 -32.4(5) . . . . ? C28 C23 C24 C25 -0.7(5) . . . . ? C22 C23 C24 C25 177.9(3) . . . . ? C23 C24 C25 C26 -1.6(6) . . . . ? C23 C24 C25 N8 178.4(3) . . . . ? Cu2 N8 C25 C26 -88.5(4) . . . . ? Cu2 N8 C25 C24 91.5(4) . . . . ? C24 C25 C26 C27 2.9(6) . . . . ? N8 C25 C26 C27 -177.1(3) . . . . ? C25 C26 C27 C28 -2.1(6) . . . . ? C26 C27 C28 C23 -0.2(6) . . . . ? C24 C23 C28 C27 1.6(6) . . . . ? C22 C23 C28 C27 -176.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.036 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.107 data_120e _database_code_CSD 154910 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 'Exp 1.20(e)' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H34 Cu5 N8 O19 S' _chemical_formula_weight 1136.39 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 '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' _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 13.9633(11) _cell_length_b 27.574(2) _cell_length_c 19.966(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.795(2) _cell_angle_gamma 90.00 _cell_volume 7648.3(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.974 _exptl_crystal_density_method ? _exptl_crystal_F_000 4568 _exptl_absorpt_coefficient_mu 2.882 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 Smart 1K CCD _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36014 _diffrn_reflns_av_R_equivalents 0.1909 _diffrn_reflns_av_sigmaI/netI 0.4073 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 30.03 _reflns_number_total 11017 _reflns_number_observed 2865 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0128P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11015 _refine_ls_number_parameters 567 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.2395 _refine_ls_R_factor_obs 0.0520 _refine_ls_wR_factor_all 0.1025 _refine_ls_wR_factor_obs 0.0754 _refine_ls_goodness_of_fit_all 0.673 _refine_ls_goodness_of_fit_obs 1.088 _refine_ls_restrained_S_all 0.711 _refine_ls_restrained_S_obs 1.118 _refine_ls_shift/esd_max 3.206 _refine_ls_shift/esd_mean 0.019 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 1.09010(6) 0.31774(3) 0.62624(6) 0.0369(3) Uani 1 d . . Cu2 Cu 0.92313(6) 0.18103(3) 0.68211(5) 0.0283(3) Uani 1 d . . Cu3 Cu 0.64078(6) 0.24506(3) 0.58246(6) 0.0400(3) Uani 1 d . . Cu4 Cu 0.81261(6) 0.37044(3) 0.50412(5) 0.0299(3) Uani 1 d . . Cu5 Cu 0.86034(6) 0.28527(3) 0.61223(6) 0.0402(3) Uani 1 d . . S1 S 0.77974(13) 0.39065(7) 0.67701(13) 0.0367(6) Uani 1 d D . N1 N 1.0520(4) 0.2559(2) 0.6639(3) 0.032(2) Uani 1 d . . N2 N 1.2185(4) 0.3083(2) 0.6798(3) 0.042(2) Uani 1 d . . H2A H 1.2593(4) 0.3308(2) 0.6667(3) 0.050 Uiso 1 calc R . H2B H 1.2114(4) 0.3139(2) 0.7234(3) 0.050 Uiso 1 calc R . N3 N 0.7859(4) 0.1956(2) 0.6604(3) 0.028(2) Uani 1 d . . N4 N 0.8925(4) 0.1119(2) 0.6646(3) 0.028(2) Uani 1 d . . H4A H 0.8830(4) 0.1075(2) 0.6198(3) 0.033 Uiso 1 calc R . H4B H 0.9442(4) 0.0942(2) 0.6799(3) 0.033 Uiso 1 calc R . N5 N 0.6796(4) 0.2991(2) 0.5316(3) 0.037(2) Uani 1 d . . N6 N 0.5128(4) 0.2483(2) 0.5308(4) 0.046(2) Uani 1 d . . H6A H 0.5163(4) 0.2321(2) 0.4920(4) 0.055 Uiso 1 calc R . H6B H 0.4713(4) 0.2320(2) 0.5542(4) 0.055 Uiso 1 calc R . N7 N 0.9490(4) 0.3588(2) 0.5347(3) 0.034(2) Uani 1 d . . N8 N 0.8463(3) 0.4370(2) 0.4811(3) 0.024(2) Uani 1 d . . H8A H 0.7999(3) 0.4477(2) 0.4501(3) 0.029 Uiso 1 calc R . H8B H 0.8429(3) 0.4552(2) 0.5182(3) 0.029 Uiso 1 calc R . O1 O 0.9521(3) 0.24777(15) 0.6702(3) 0.0317(14) Uani 1 d . . O2 O 1.0637(3) 0.17653(15) 0.6959(2) 0.0242(12) Uani 1 d . . O3 O 0.7628(3) 0.24226(15) 0.6356(3) 0.041(2) Uani 1 d . . O4 O 0.6299(3) 0.1806(2) 0.6205(3) 0.044(2) Uani 1 d . . O5 O 0.7823(3) 0.30571(15) 0.5304(3) 0.0307(13) Uani 1 d . . O6 O 0.6752(3) 0.37202(15) 0.4754(3) 0.0272(13) Uani 1 d . . O7 O 0.9658(3) 0.3180(2) 0.5776(3) 0.055(2) Uani 1 d . . O8 O 1.1102(3) 0.36614(15) 0.5540(2) 0.0256(13) Uani 1 d . . O9 O 0.8124(5) 0.3419(2) 0.6834(3) 0.074(2) Uani 1 d . . O10 O 0.7667(3) 0.4084(2) 0.6084(3) 0.0379(14) Uani 1 d . . O11 O 0.8785(6) 0.4152(3) 0.7077(4) 0.016(2) Uiso 0.50 d PD 1 O11' O 0.8103(7) 0.4234(3) 0.7217(5) 0.033(3) Uiso 0.50 d PD 2 O12 O 0.7142(5) 0.4109(3) 0.7295(4) 0.015(2) Uiso 0.50 d PD 1 O12' O 0.6753(6) 0.3746(3) 0.6798(5) 0.031(3) Uiso 0.50 d PD 2 O1S O 1.0400(6) -0.0475(3) 0.7387(5) 0.033(3) Uani 0.50 d P . O2S O 0.5853(7) 0.3794(3) 0.8017(7) 0.091(5) Uani 0.50 d P . O3S O 0.8215(4) 0.0027(2) 0.5681(2) 0.0302(14) Uani 1 d . . H3SB H 0.8032(4) -0.0292(2) 0.5942(2) 0.112(37) Uiso 1 d R . H3SA H 0.8645(4) 0.0060(2) 0.5860(2) 0.005(22) Uiso 1 d R . O4S O 0.8513(3) 0.0105(2) 0.4314(3) 0.0384(15) Uani 1 d . . H4SB H 0.8541(3) 0.0077(2) 0.4816(3) 0.150(50) Uiso 1 d R . H4SA H 0.8539(3) 0.0388(2) 0.4215(3) 0.053(30) Uiso 1 d R . O5S O 0.7475(4) 0.4219(2) 0.8665(3) 0.051(2) Uani 1 d . . H5SB H 0.7868(4) 0.4076(2) 0.8830(3) 0.004(19) Uiso 1 d R . H5SA H 0.7454(4) 0.4150(2) 0.8163(3) 0.271(87) Uiso 1 d R . O6S O 1.0010(3) 0.0180(2) 0.6411(4) 0.0388(15) Uani 1 d . . H6SA H 1.0025(3) -0.0010(2) 0.6711(4) 0.103(51) Uiso 1 d R . H6SB H 1.0120(3) 0.0082(2) 0.6044(4) 0.105(51) Uiso 1 d R . O7S O 1.0451(4) 0.3797(2) 0.6809(3) 0.051(2) Uani 1 d . . H7SA H 1.0673(4) 0.3881(2) 0.7136(3) 0.000(21) Uiso 1 d R . H7SB H 0.9871(4) 0.3781(2) 0.6882(3) 2.000(785) Uiso 1 d R . O8S O 0.5851(3) 0.2973(2) 0.6685(3) 0.066(2) Uani 1 d . . C1 C 1.1015(5) 0.2171(2) 0.6796(4) 0.029(2) Uani 1 d . . C2 C 1.2090(5) 0.2183(2) 0.6741(4) 0.028(2) Uani 1 d . . C3 C 1.2544(5) 0.1743(2) 0.6695(4) 0.030(2) Uani 1 d . . H3 H 1.2186(5) 0.1459(2) 0.6684(4) 0.036 Uiso 1 calc R . C4 C 1.3537(5) 0.1720(2) 0.6664(4) 0.032(2) Uani 1 d . . H4 H 1.3839(5) 0.1422(2) 0.6626(4) 0.039 Uiso 1 calc R . C5 C 1.4059(5) 0.2140(2) 0.6691(4) 0.033(2) Uani 1 d . . H5A H 1.4722(5) 0.2126(2) 0.6678(4) 0.040 Uiso 1 calc R . C6 C 1.3616(4) 0.2580(2) 0.6737(4) 0.029(2) Uani 1 d . . H6 H 1.3981(4) 0.2862(2) 0.6763(4) 0.035 Uiso 1 calc R . C7 C 1.2630(5) 0.2607(2) 0.6745(4) 0.033(2) Uani 1 d . . C8 C 0.7126(5) 0.1666(2) 0.6505(4) 0.029(2) Uani 1 d . . C9 C 0.7214(5) 0.1174(2) 0.6814(4) 0.024(2) Uani 1 d . . C10 C 0.6397(5) 0.0967(2) 0.7047(4) 0.028(2) Uani 1 d . . H10 H 0.5802(5) 0.1119(2) 0.6959(4) 0.033 Uiso 1 calc R . C11 C 0.6466(5) 0.0540(2) 0.7405(4) 0.029(2) Uani 1 d . . H11C H 0.5921(5) 0.0400(2) 0.7554(4) 0.034 Uiso 1 calc R . C12 C 0.7359(6) 0.0323(2) 0.7540(4) 0.027(2) Uani 1 d . . H12C H 0.7413(6) 0.0044(2) 0.7802(4) 0.033 Uiso 1 calc R . C13 C 0.8157(5) 0.0508(2) 0.7299(4) 0.027(2) Uani 1 d . . H13 H 0.8742(5) 0.0347(2) 0.7381(4) 0.032 Uiso 1 calc R . C14 C 0.8107(5) 0.0930(2) 0.6936(4) 0.021(2) Uani 1 d . . C15 C 0.6350(5) 0.3347(2) 0.5018(4) 0.027(2) Uani 1 d . . C16 C 0.5267(5) 0.3350(2) 0.4992(4) 0.024(2) Uani 1 d . . C17 C 0.4709(5) 0.2955(2) 0.5141(4) 0.030(2) Uani 1 d . . C18 C 0.3698(5) 0.3004(2) 0.5122(4) 0.040(2) Uani 1 d . . H18 H 0.3328(5) 0.2736(2) 0.5213(4) 0.048 Uiso 1 calc R . C19 C 0.3257(5) 0.3438(2) 0.4973(4) 0.037(2) Uani 1 d . . H19 H 0.2594(5) 0.3468(2) 0.4973(4) 0.044 Uiso 1 calc R . C20 C 0.3808(5) 0.3829(2) 0.4820(4) 0.034(2) Uani 1 d . . H20 H 0.3511(5) 0.4124(2) 0.4712(4) 0.041 Uiso 1 calc R . C21 C 0.4797(5) 0.3788(2) 0.4827(4) 0.034(2) Uani 1 d . . H21 H 0.5155(5) 0.4057(2) 0.4720(4) 0.041 Uiso 1 calc R . C22 C 1.0274(5) 0.3811(2) 0.5260(4) 0.024(2) Uani 1 d . . C23 C 1.0228(4) 0.4221(2) 0.4772(4) 0.018(2) Uani 1 d . . C24 C 1.1094(5) 0.4368(2) 0.4520(4) 0.024(2) Uani 1 d . . H24 H 1.1662(5) 0.4207(2) 0.4669(4) 0.029 Uiso 1 calc R . C25 C 1.1127(5) 0.4735(2) 0.4065(4) 0.022(2) Uani 1 d . . H25 H 1.1704(5) 0.4819(2) 0.3899(4) 0.026 Uiso 1 calc R . C26 C 1.0277(5) 0.4983(2) 0.3853(4) 0.024(2) Uani 1 d . . H26A H 1.0285(5) 0.5236(2) 0.3546(4) 0.029 Uiso 1 calc R . C27 C 0.9425(4) 0.4853(2) 0.4102(3) 0.018(2) Uani 1 d . . H27 H 0.8864(4) 0.5021(2) 0.3962(3) 0.022 Uiso 1 calc R . C28 C 0.9393(4) 0.4477(2) 0.4555(4) 0.019(2) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0157(5) 0.0176(5) 0.0727(9) 0.0109(6) -0.0178(5) -0.0032(4) Cu2 0.0175(5) 0.0152(4) 0.0485(8) 0.0039(5) -0.0155(5) -0.0011(4) Cu3 0.0153(5) 0.0220(5) 0.0778(9) 0.0201(6) -0.0195(5) -0.0055(4) Cu4 0.0157(5) 0.0168(5) 0.0538(8) 0.0069(5) -0.0133(5) -0.0022(4) Cu5 0.0190(5) 0.0189(5) 0.0771(9) 0.0157(6) -0.0233(5) -0.0058(4) S1 0.0217(10) 0.0270(11) 0.064(2) 0.0225(13) 0.0171(12) 0.0114(9) N1 0.011(3) 0.031(4) 0.049(5) -0.002(4) -0.013(3) 0.003(3) N2 0.015(3) 0.022(4) 0.082(6) 0.001(4) -0.028(3) 0.000(3) N3 0.020(3) 0.016(3) 0.045(5) -0.002(3) -0.007(3) -0.002(2) N4 0.018(3) 0.024(3) 0.037(4) 0.008(3) -0.012(3) 0.002(3) N5 0.015(3) 0.020(3) 0.070(6) 0.015(4) -0.016(4) 0.001(3) N6 0.015(3) 0.022(3) 0.094(6) 0.023(4) -0.022(4) -0.003(3) N7 0.022(3) 0.009(3) 0.066(6) 0.013(3) -0.014(3) -0.001(2) N8 0.018(3) 0.021(3) 0.031(4) -0.008(3) -0.006(3) 0.002(2) O1 0.012(2) 0.017(3) 0.062(4) 0.008(3) -0.015(3) 0.001(2) O2 0.025(3) 0.015(2) 0.030(4) -0.004(3) -0.008(2) -0.001(2) O3 0.022(3) 0.009(3) 0.087(5) 0.020(3) -0.023(3) -0.002(2) O4 0.017(3) 0.027(3) 0.082(5) 0.025(3) -0.026(3) -0.003(2) O5 0.013(2) 0.021(3) 0.053(4) 0.013(3) -0.017(3) 0.001(2) O6 0.010(2) 0.017(3) 0.052(4) 0.002(3) -0.004(2) 0.005(2) O7 0.016(3) 0.025(3) 0.119(6) 0.030(4) -0.024(3) -0.015(2) O8 0.008(2) 0.025(3) 0.042(4) 0.002(3) -0.006(2) 0.000(2) O9 0.150(6) 0.018(3) 0.041(5) -0.003(3) -0.055(4) 0.015(3) O10 0.045(3) 0.024(3) 0.039(4) 0.010(3) -0.024(3) 0.005(2) O1S 0.025(6) 0.041(6) 0.031(8) 0.012(6) -0.002(6) -0.001(4) O2S 0.049(7) 0.024(6) 0.181(15) -0.037(8) -0.087(8) 0.011(5) O3S 0.021(3) 0.037(3) 0.031(4) 0.005(3) -0.006(3) 0.001(2) O4S 0.047(4) 0.033(4) 0.034(5) 0.010(3) 0.001(3) 0.017(3) O5S 0.044(4) 0.043(3) 0.059(5) -0.014(3) -0.025(3) 0.026(3) O6S 0.034(3) 0.033(3) 0.047(4) -0.013(4) -0.009(3) 0.009(2) O7S 0.057(4) 0.077(5) 0.019(4) 0.008(4) 0.000(3) 0.035(3) O8S 0.016(3) 0.108(5) 0.073(5) 0.063(4) 0.002(3) 0.007(3) C1 0.024(4) 0.021(4) 0.038(6) -0.003(4) -0.011(4) -0.005(3) C2 0.021(4) 0.013(4) 0.047(6) 0.011(4) -0.007(4) 0.000(3) C3 0.028(4) 0.022(4) 0.038(6) 0.008(4) -0.006(4) -0.008(3) C4 0.035(4) 0.029(5) 0.032(6) 0.015(4) -0.004(4) 0.005(3) C5 0.022(4) 0.021(4) 0.054(6) 0.012(5) -0.013(4) 0.000(3) C6 0.013(4) 0.015(4) 0.057(6) 0.016(4) -0.013(4) -0.002(3) C7 0.026(4) 0.008(4) 0.061(7) 0.006(4) -0.022(4) -0.005(3) C8 0.019(4) 0.024(4) 0.040(6) -0.005(4) -0.010(4) -0.004(3) C9 0.036(4) 0.013(4) 0.020(5) -0.007(4) -0.007(4) -0.009(3) C10 0.031(4) 0.023(4) 0.026(5) -0.007(4) -0.011(4) -0.003(3) C11 0.044(5) 0.014(4) 0.025(5) -0.003(4) -0.007(4) -0.013(3) C12 0.059(6) 0.013(4) 0.010(5) 0.000(4) 0.000(4) 0.009(4) C13 0.041(5) 0.014(4) 0.024(6) 0.003(4) -0.003(4) 0.013(3) C14 0.029(4) 0.011(4) 0.021(5) -0.015(4) -0.006(4) -0.007(3) C15 0.019(4) 0.015(4) 0.044(6) 0.000(4) -0.012(4) -0.007(3) C16 0.025(4) 0.004(3) 0.039(6) 0.003(4) -0.011(4) -0.004(3) C17 0.025(4) 0.014(4) 0.046(6) 0.006(4) -0.021(4) -0.002(3) C18 0.018(4) 0.024(4) 0.074(7) 0.011(5) -0.015(4) -0.013(3) C19 0.022(4) 0.028(4) 0.056(7) 0.017(5) -0.015(4) 0.003(3) C20 0.019(4) 0.026(4) 0.056(7) 0.013(4) -0.004(4) 0.002(3) C21 0.025(4) 0.028(4) 0.047(6) 0.003(4) -0.008(4) -0.004(3) C22 0.019(4) 0.012(4) 0.041(6) -0.002(4) -0.003(4) -0.002(3) C23 0.012(3) 0.017(4) 0.024(5) -0.011(4) -0.006(3) 0.000(3) C24 0.021(4) 0.022(4) 0.029(6) -0.013(4) -0.001(4) 0.008(3) C25 0.027(4) 0.025(4) 0.013(5) -0.003(4) 0.002(4) 0.003(3) C26 0.031(4) 0.030(4) 0.011(5) -0.008(4) -0.001(4) 0.004(3) C27 0.016(4) 0.019(4) 0.017(5) -0.007(4) -0.009(3) 0.005(3) C28 0.016(4) 0.013(4) 0.026(5) -0.009(4) -0.004(4) 0.006(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 O7 1.901(5) . ? Cu1 N1 1.959(6) . ? Cu1 O8 2.006(5) . ? Cu1 N2 2.009(5) . ? Cu1 O7S 2.154(5) . ? Cu2 O1 1.904(4) . ? Cu2 O2 1.959(4) . ? Cu2 N3 1.963(5) . ? Cu2 N4 1.977(5) . ? Cu2 O2 2.428(5) 2_756 ? Cu3 O3 1.915(5) . ? Cu3 N5 1.913(6) . ? Cu3 O4 1.945(5) . ? Cu3 N6 1.973(5) . ? Cu3 O8S 2.430(6) . ? Cu4 O5 1.919(4) . ? Cu4 O6 1.947(4) . ? Cu4 N7 1.967(5) . ? Cu4 N8 1.960(5) . ? Cu5 O3 1.900(4) . ? Cu5 O7 1.915(5) . ? Cu5 O1 1.937(4) . ? Cu5 O5 1.953(5) . ? Cu5 O9 2.258(6) . ? S1 O11' 1.311(9) . ? S1 O9 1.422(5) . ? S1 O10 1.450(5) . ? S1 O12' 1.531(8) . ? S1 O12 1.563(7) . ? S1 O11 1.602(8) . ? N1 C1 1.294(8) . ? N1 O1 1.432(6) . ? N2 C7 1.461(7) . ? N3 C8 1.297(7) . ? N3 O3 1.405(6) . ? N4 C14 1.429(8) . ? N5 C15 1.276(8) . ? N5 O5 1.447(6) . ? N6 C17 1.452(7) . ? N7 C22 1.282(7) . ? N7 O7 1.419(7) . ? N8 C28 1.473(7) . ? O2 C1 1.292(7) . ? O2 Cu2 2.428(5) 2_756 ? O4 C8 1.305(7) . ? O6 C15 1.308(7) . ? O8 C22 1.299(7) . ? O1S O1S 1.247(15) 2_756 ? C1 C2 1.517(9) . ? C2 C3 1.375(8) . ? C2 C7 1.391(8) . ? C3 C4 1.395(8) . ? C4 C5 1.366(8) . ? C5 C6 1.369(8) . ? C6 C7 1.380(8) . ? C8 C9 1.489(9) . ? C9 C10 1.397(8) . ? C9 C14 1.416(9) . ? C10 C11 1.376(8) . ? C11 C12 1.386(9) . ? C12 C13 1.356(9) . ? C13 C14 1.370(8) . ? C15 C16 1.509(8) . ? C16 C17 1.388(8) . ? C16 C21 1.399(8) . ? C17 C18 1.415(8) . ? C18 C19 1.363(8) . ? C19 C20 1.377(8) . ? C20 C21 1.385(8) . ? C22 C23 1.490(9) . ? C23 C28 1.394(8) . ? C23 C24 1.415(8) . ? C24 C25 1.364(8) . ? C25 C26 1.398(8) . ? C26 C27 1.382(8) . ? C27 C28 1.378(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 O7 Cu1 N1 86.0(2) . . ? O7 Cu1 O8 79.4(2) . . ? N1 Cu1 O8 156.7(2) . . ? O7 Cu1 N2 172.6(2) . . ? N1 Cu1 N2 86.8(2) . . ? O8 Cu1 N2 106.7(2) . . ? O7 Cu1 O7S 87.6(2) . . ? N1 Cu1 O7S 113.0(2) . . ? O8 Cu1 O7S 84.6(2) . . ? N2 Cu1 O7S 97.1(2) . . ? O1 Cu2 O2 81.8(2) . . ? O1 Cu2 N3 89.4(2) . . ? O2 Cu2 N3 170.5(2) . . ? O1 Cu2 N4 162.7(2) . . ? O2 Cu2 N4 99.2(2) . . ? N3 Cu2 N4 88.2(2) . . ? O1 Cu2 O2 100.3(2) . 2_756 ? O2 Cu2 O2 83.3(2) . 2_756 ? N3 Cu2 O2 101.8(2) . 2_756 ? N4 Cu2 O2 96.9(2) . 2_756 ? O3 Cu3 N5 92.4(2) . . ? O3 Cu3 O4 81.2(2) . . ? N5 Cu3 O4 163.2(2) . . ? O3 Cu3 N6 177.8(3) . . ? N5 Cu3 N6 88.7(2) . . ? O4 Cu3 N6 98.2(2) . . ? O3 Cu3 O8S 87.8(2) . . ? N5 Cu3 O8S 92.4(2) . . ? O4 Cu3 O8S 102.9(2) . . ? N6 Cu3 O8S 90.3(2) . . ? O5 Cu4 O6 82.2(2) . . ? O5 Cu4 N7 89.8(2) . . ? O6 Cu4 N7 171.8(2) . . ? O5 Cu4 N8 177.6(2) . . ? O6 Cu4 N8 99.4(2) . . ? N7 Cu4 N8 88.7(2) . . ? O3 Cu5 O7 168.4(2) . . ? O3 Cu5 O1 88.1(2) . . ? O7 Cu5 O1 88.9(2) . . ? O3 Cu5 O5 91.9(2) . . ? O7 Cu5 O5 86.9(2) . . ? O1 Cu5 O5 159.0(2) . . ? O3 Cu5 O9 90.6(2) . . ? O7 Cu5 O9 100.9(2) . . ? O1 Cu5 O9 102.3(2) . . ? O5 Cu5 O9 98.7(2) . . ? O11' S1 O9 120.8(5) . . ? O11' S1 O10 114.3(5) . . ? O9 S1 O10 114.4(4) . . ? O11' S1 O12' 114.9(6) . . ? O9 S1 O12' 91.2(4) . . ? O10 S1 O12' 95.9(4) . . ? O9 S1 O12 118.8(4) . . ? O10 S1 O12 119.2(4) . . ? O9 S1 O11 96.3(4) . . ? O10 S1 O11 103.8(4) . . ? O12 S1 O11 97.6(4) . . ? C1 N1 O1 110.5(5) . . ? C1 N1 Cu1 130.8(5) . . ? O1 N1 Cu1 118.4(4) . . ? C7 N2 Cu1 116.2(4) . . ? C8 N3 O3 111.2(5) . . ? C8 N3 Cu2 130.2(5) . . ? O3 N3 Cu2 116.7(4) . . ? C14 N4 Cu2 116.6(4) . . ? C15 N5 O5 109.5(5) . . ? C15 N5 Cu3 134.0(5) . . ? O5 N5 Cu3 116.2(4) . . ? C17 N6 Cu3 118.9(4) . . ? C22 N7 O7 111.7(5) . . ? C22 N7 Cu4 133.9(5) . . ? O7 N7 Cu4 114.4(4) . . ? C28 N8 Cu4 120.7(4) . . ? N1 O1 Cu2 112.6(3) . . ? N1 O1 Cu5 117.1(4) . . ? Cu2 O1 Cu5 117.1(2) . . ? C1 O2 Cu2 109.8(4) . . ? C1 O2 Cu2 102.5(4) . 2_756 ? Cu2 O2 Cu2 96.4(2) . 2_756 ? N3 O3 Cu5 120.9(3) . . ? N3 O3 Cu3 113.1(3) . . ? Cu5 O3 Cu3 117.3(3) . . ? C8 O4 Cu3 110.5(4) . . ? N5 O5 Cu4 111.5(3) . . ? N5 O5 Cu5 114.8(4) . . ? Cu4 O5 Cu5 112.1(2) . . ? C15 O6 Cu4 108.3(4) . . ? N7 O7 Cu1 113.5(3) . . ? N7 O7 Cu5 120.3(3) . . ? Cu1 O7 Cu5 120.6(3) . . ? C22 O8 Cu1 109.7(4) . . ? S1 O9 Cu5 135.3(4) . . ? N1 C1 O2 123.7(6) . . ? N1 C1 C2 118.2(6) . . ? O2 C1 C2 117.9(6) . . ? C3 C2 C7 119.2(6) . . ? C3 C2 C1 117.0(6) . . ? C7 C2 C1 123.9(6) . . ? C2 C3 C4 120.7(6) . . ? C5 C4 C3 119.2(7) . . ? C4 C5 C6 120.7(6) . . ? C7 C6 C5 120.4(6) . . ? C6 C7 C2 119.7(6) . . ? C6 C7 N2 118.7(6) . . ? C2 C7 N2 121.4(6) . . ? N3 C8 O4 122.3(6) . . ? N3 C8 C9 117.8(6) . . ? O4 C8 C9 119.5(6) . . ? C10 C9 C14 118.9(6) . . ? C10 C9 C8 118.3(6) . . ? C14 C9 C8 122.6(6) . . ? C11 C10 C9 120.4(7) . . ? C10 C11 C12 119.1(7) . . ? C13 C12 C11 121.6(7) . . ? C12 C13 C14 120.5(7) . . ? C13 C14 C9 119.5(6) . . ? C13 C14 N4 121.6(6) . . ? C9 C14 N4 118.8(6) . . ? N5 C15 O6 125.7(6) . . ? N5 C15 C16 117.4(6) . . ? O6 C15 C16 116.8(6) . . ? C17 C16 C21 118.0(6) . . ? C17 C16 C15 124.8(6) . . ? C21 C16 C15 117.2(6) . . ? C16 C17 C18 119.9(6) . . ? C16 C17 N6 122.1(6) . . ? C18 C17 N6 118.0(6) . . ? C19 C18 C17 121.2(6) . . ? C18 C19 C20 119.0(7) . . ? C21 C20 C19 120.9(7) . . ? C20 C21 C16 121.0(7) . . ? N7 C22 O8 121.7(6) . . ? N7 C22 C23 118.1(6) . . ? O8 C22 C23 120.0(6) . . ? C28 C23 C24 117.5(6) . . ? C28 C23 C22 124.6(6) . . ? C24 C23 C22 117.9(6) . . ? C25 C24 C23 122.5(6) . . ? C24 C25 C26 118.7(6) . . ? C27 C26 C25 119.9(7) . . ? C28 C27 C26 121.2(6) . . ? C23 C28 C27 120.3(6) . . ? C23 C28 N8 121.9(6) . . ? C27 C28 N8 117.8(5) . . ? _refine_diff_density_max 0.903 _refine_diff_density_min -0.719 _refine_diff_density_rms 0.131 data_122a _database_code_CSD 154911 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cu1 N4 O4, H2 O' _chemical_formula_sum 'C14 H16 Cu1 N4 O5' _chemical_formula_weight 383.85 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' _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 17.7195(9) _cell_length_b 5.6014(3) _cell_length_c 15.5028(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.6520(10) _cell_angle_gamma 90.00 _cell_volume 1449.09(13) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 126 _cell_measurement_theta_min 6 _cell_measurement_theta_max 20 _exptl_crystal_description plate _exptl_crystal_colour black-water _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 1.544 _exptl_absorpt_correction_type 'psi-correction' _exptl_absorpt_correction_T_min 0.541 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'Sadabs program' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 6547 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 29.99 _reflns_number_total 2093 _reflns_number_gt 1786 _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^)+(0.0546P)^2^+0.6804P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment iso _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2093 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.5000 0.5000 0.0000 0.01550(10) Uani 1 2 d S . . O1 O 0.50657(6) 0.3333(2) -0.10565(7) 0.0194(2) Uani 1 1 d . . . O2 O 0.42066(7) 0.2641(2) -0.00128(7) 0.0187(2) Uani 1 1 d . . . O1W O 0.0000 0.1534(3) -0.2500 0.0313(4) Uani 1 2 d S . . N1 N 0.44509(7) 0.1671(2) -0.12976(9) 0.0177(3) Uani 1 1 d . . . N2 N 0.12910(9) -0.4612(3) -0.17431(10) 0.0197(3) Uani 1 1 d . . . C1 C 0.40382(9) 0.1370(3) -0.07445(10) 0.0160(3) Uani 1 1 d . . . C2 C 0.33592(9) -0.0309(3) -0.09957(10) 0.0154(3) Uani 1 1 d . . . C3 C 0.26787(10) 0.0374(3) -0.07955(11) 0.0174(3) Uani 1 1 d . . . C4 C 0.20011(9) -0.1039(3) -0.10315(10) 0.0181(3) Uani 1 1 d . . . C5 C 0.19933(9) -0.3230(3) -0.14699(10) 0.0165(3) Uani 1 1 d . . . C6 C 0.26762(9) -0.3940(3) -0.16679(10) 0.0169(3) Uani 1 1 d . . . C7 C 0.33558(9) -0.2489(3) -0.14323(10) 0.0162(3) Uani 1 1 d . . . H1N H 0.4308(13) 0.121(4) -0.1850(16) 0.027(5) Uiso 1 1 d . . . H2NA H 0.0983(15) -0.435(5) -0.1527(17) 0.026(6) Uiso 1 1 d . . . H2NB H 0.1344(14) -0.597(5) -0.1767(16) 0.027(6) Uiso 1 1 d . . . H1W H 0.0079(18) 0.046(5) -0.2059(19) 0.039(7) Uiso 1 1 d . . . H3 H 0.2686(13) 0.189(4) -0.0500(15) 0.024(5) Uiso 1 1 d . . . H4 H 0.1573(16) -0.055(5) -0.0884(18) 0.029(6) Uiso 1 1 d . . . H6 H 0.2684(16) -0.545(4) -0.1951(18) 0.033(7) Uiso 1 1 d . . . H7 H 0.3819(13) -0.298(4) -0.1554(14) 0.020(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01527(15) 0.01649(15) 0.01348(14) -0.00216(8) 0.00316(10) -0.00375(8) O1 0.0171(5) 0.0218(6) 0.0195(5) -0.0053(4) 0.0064(4) -0.0082(4) O2 0.0207(5) 0.0194(5) 0.0156(5) -0.0038(4) 0.0057(4) -0.0053(4) O1W 0.0436(11) 0.0207(9) 0.0293(9) 0.000 0.0121(8) 0.000 N1 0.0163(6) 0.0192(6) 0.0161(6) -0.0042(5) 0.0035(5) -0.0054(5) N2 0.0186(6) 0.0213(7) 0.0190(6) -0.0001(5) 0.0063(5) -0.0054(5) C1 0.0161(6) 0.0148(6) 0.0154(6) 0.0001(5) 0.0030(5) -0.0006(5) C2 0.0147(7) 0.0173(7) 0.0135(6) 0.0001(5) 0.0038(5) -0.0017(5) C3 0.0188(7) 0.0183(7) 0.0162(7) -0.0026(5) 0.0072(5) -0.0018(5) C4 0.0181(7) 0.0197(7) 0.0177(6) 0.0007(5) 0.0077(5) -0.0008(6) C5 0.0178(6) 0.0161(7) 0.0137(6) 0.0027(5) 0.0029(5) -0.0029(5) C6 0.0199(7) 0.0132(6) 0.0151(6) -0.0002(5) 0.0027(5) -0.0001(5) C7 0.0156(6) 0.0160(7) 0.0161(6) 0.0012(5) 0.0041(5) 0.0020(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9225(11) . ? Cu1 O1 1.9225(11) 5_665 ? Cu1 O2 1.9246(11) 5_665 ? Cu1 O2 1.9246(11) . ? O1 N1 1.3854(16) . ? O2 C1 1.2864(17) . ? N1 C1 1.3116(19) . ? N2 C5 1.4046(19) . ? C1 C2 1.473(2) . ? C2 C7 1.395(2) . ? C2 C3 1.396(2) . ? C3 C4 1.381(2) . ? C4 C5 1.400(2) . ? C5 C6 1.402(2) . ? C6 C7 1.396(2) . ? 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 O1 Cu1 O1 180.00(6) . 5_665 ? O1 Cu1 O2 95.10(4) . 5_665 ? O1 Cu1 O2 84.90(4) 5_665 5_665 ? O1 Cu1 O2 84.90(4) . . ? O1 Cu1 O2 95.10(4) 5_665 . ? O2 Cu1 O2 180.00(6) 5_665 . ? N1 O1 Cu1 106.79(8) . . ? C1 O2 Cu1 109.94(9) . . ? C1 N1 O1 118.07(12) . . ? O2 C1 N1 119.37(13) . . ? O2 C1 C2 120.88(13) . . ? N1 C1 C2 119.65(13) . . ? C7 C2 C3 119.01(14) . . ? C7 C2 C1 123.86(14) . . ? C3 C2 C1 117.12(13) . . ? C4 C3 C2 121.52(14) . . ? C3 C4 C5 119.78(14) . . ? C4 C5 C6 119.10(13) . . ? C4 C5 N2 119.50(14) . . ? C6 C5 N2 121.32(14) . . ? C7 C6 C5 120.63(14) . . ? C2 C7 C6 119.95(14) . . ? 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 O1 Cu1 O1 N1 36(84) 5_665 . . . ? O2 Cu1 O1 N1 -171.81(9) 5_665 . . . ? O2 Cu1 O1 N1 8.19(9) . . . . ? O1 Cu1 O2 C1 -8.05(10) . . . . ? O1 Cu1 O2 C1 171.95(10) 5_665 . . . ? O2 Cu1 O2 C1 -164(100) 5_665 . . . ? Cu1 O1 N1 C1 -7.56(16) . . . . ? Cu1 O2 C1 N1 6.07(17) . . . . ? Cu1 O2 C1 C2 -170.27(11) . . . . ? O1 N1 C1 O2 1.1(2) . . . . ? O1 N1 C1 C2 177.52(12) . . . . ? O2 C1 C2 C7 -145.60(15) . . . . ? N1 C1 C2 C7 38.1(2) . . . . ? O2 C1 C2 C3 35.7(2) . . . . ? N1 C1 C2 C3 -140.62(15) . . . . ? C7 C2 C3 C4 -0.9(2) . . . . ? C1 C2 C3 C4 177.81(14) . . . . ? C2 C3 C4 C5 1.0(2) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? C3 C4 C5 N2 -177.30(14) . . . . ? C4 C5 C6 C7 0.0(2) . . . . ? N2 C5 C6 C7 176.77(14) . . . . ? C3 C2 C7 C6 0.5(2) . . . . ? C1 C2 C7 C6 -178.20(14) . . . . ? C5 C6 C7 C2 0.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.736 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.086