Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Prof Leonard Lindoy' _publ_contact_author_address ; School of Chemistry F11 University of Sydney Sydney NSW 2006. AUSTRALIA ; _publ_contact_author_email LINDOY@CHEM.USYD.EDU.AU _publ_contact_author_fax '+61 2 9351 3329' _publ_contact_author_phone '+61 2 9351 4400' _publ_section_title ; Towards a system for the systematic structural study of intermolecular interactions in crystals of transition metal complexes ; loop_ _publ_author_name 'Leonard Lindoy' 'Michael M. Bishop' 'Andrew Parkin' 'Peter Turner' data_3a _database_code_depnum_ccdc_archive 'CCDC 265654' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H40 Cl2 Cu N8 O14' _chemical_formula_weight 943.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.982(2) _cell_length_b 13.361(3) _cell_length_c 14.624(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.488(3) _cell_angle_gamma 90.00 _cell_volume 2068.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1019 _cell_measurement_theta_min 3.099 _cell_measurement_theta_max 27.472 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.330 _exptl_crystal_size_min 0.070 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 974 _exptl_absorpt_coefficient_mu 0.734 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.802 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _exptl_special_details ; ? ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 289 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 18913 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0136 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.03 _reflns_number_total 4653 _reflns_number_gt 4230 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _computing_publication_material ? _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^)+(0.03P)^2^+0.5P] 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 4653 _refine_ls_number_parameters 292 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.367 _refine_ls_restrained_S_all 1.370 _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 1.0000 0.0000 0.5000 0.01663(8) Uani 1 2 d S . . O1 O 0.69370(9) 0.08878(8) 0.46769(7) 0.0228(2) Uani 1 1 d . . . O2 O 1.17706(9) 0.06474(8) 0.28739(7) 0.0236(2) Uani 1 1 d . . . N1 N 0.86831(11) 0.08296(9) 0.40560(8) 0.0176(2) Uani 1 1 d . . . N2 N 0.78923(11) 0.17806(9) 0.27516(9) 0.0194(2) Uani 1 1 d D . . H2N H 0.7816(16) 0.1898(14) 0.2198(12) 0.027(5) Uiso 1 1 d D . . N3 N 0.98837(11) 0.11188(9) 0.29363(8) 0.0187(2) Uani 1 1 d D . . H3N H 0.9945(17) 0.1468(13) 0.2509(12) 0.027(5) Uiso 1 1 d D . . N4 N 1.10003(12) 0.00002(9) 0.40916(9) 0.0197(2) Uani 1 1 d . . . H4N H 1.1666(19) -0.0263(14) 0.4309(13) 0.027(5) Uiso 1 1 d . . . C1 C 0.74485(13) 0.10754(10) 0.40569(10) 0.0182(3) Uani 1 1 d . . . C2 C 0.67992(13) 0.16520(10) 0.31386(10) 0.0181(3) Uani 1 1 d . . . C3 C 0.88509(13) 0.12322(10) 0.32517(9) 0.0175(3) Uani 1 1 d . . . C4 C 1.09183(13) 0.05422(10) 0.33610(10) 0.0188(3) Uani 1 1 d . . . C5 C 1.29526(15) 0.01118(13) 0.32070(13) 0.0310(4) Uani 1 1 d . . . H5A H 1.3355 0.0299 0.3867 0.046 Uiso 1 1 calc R . . H5B H 1.3514 0.0285 0.2810 0.046 Uiso 1 1 calc R . . H5C H 1.2789 -0.0610 0.3169 0.046 Uiso 1 1 calc R . . C6 C 0.62772(14) 0.26421(10) 0.33918(10) 0.0202(3) Uani 1 1 d . . . C7 C 0.69742(15) 0.35182(12) 0.34560(11) 0.0273(3) Uani 1 1 d . . . H7 H 0.7771 0.3509 0.3317 0.033 Uiso 1 1 calc R . . C8 C 0.65115(18) 0.44096(12) 0.37226(12) 0.0351(4) Uani 1 1 d . . . H8 H 0.6995 0.5006 0.3768 0.042 Uiso 1 1 calc R . . C9 C 0.5351(2) 0.44297(13) 0.39215(12) 0.0381(4) Uani 1 1 d . . . H9 H 0.5033 0.5041 0.4097 0.046 Uiso 1 1 calc R . . C10 C 0.46508(18) 0.35569(14) 0.38656(13) 0.0379(4) Uani 1 1 d . . . H10 H 0.3854 0.3570 0.4005 0.045 Uiso 1 1 calc R . . C11 C 0.51143(16) 0.26613(12) 0.36057(12) 0.0287(3) Uani 1 1 d . . . H11 H 0.4638 0.2063 0.3574 0.034 Uiso 1 1 calc R . . C12 C 0.58254(13) 0.10051(11) 0.24429(10) 0.0199(3) Uani 1 1 d . . . C13 C 0.57801(14) -0.00297(11) 0.25456(12) 0.0242(3) Uani 1 1 d . . . H13 H 0.6301 -0.0345 0.3093 0.029 Uiso 1 1 calc R . . C14 C 0.49673(15) -0.06021(12) 0.18416(12) 0.0301(3) Uani 1 1 d . . . H14 H 0.4930 -0.1307 0.1915 0.036 Uiso 1 1 calc R . . C15 C 0.42160(16) -0.01482(13) 0.10375(13) 0.0332(4) Uani 1 1 d . . . H15 H 0.3673 -0.0541 0.0556 0.040 Uiso 1 1 calc R . . C16 C 0.42578(16) 0.08839(14) 0.09373(12) 0.0335(4) Uani 1 1 d . . . H16 H 0.3738 0.1197 0.0387 0.040 Uiso 1 1 calc R . . C17 C 0.50532(14) 0.14593(12) 0.16355(11) 0.0268(3) Uani 1 1 d . . . H17 H 0.5073 0.2165 0.1564 0.032 Uiso 1 1 calc R . . O7 O 1.03928(13) 0.23371(12) 0.15565(10) 0.0485(4) Uani 1 1 d . . . H7O H 0.9823 0.2562 0.1099 0.073 Uiso 1 1 calc R . . C18 C 1.15304(18) 0.22384(15) 0.12818(14) 0.0401(4) Uani 1 1 d . . . H18A H 1.1568 0.2759 0.0818 0.060 Uiso 1 1 calc R . . H18B H 1.1557 0.1578 0.0997 0.060 Uiso 1 1 calc R . . H18C H 1.2253 0.2310 0.1841 0.060 Uiso 1 1 calc R . . Cl1 Cl 1.22122(4) 0.21983(3) 0.52737(2) 0.02683(10) Uani 1 1 d . . . O3 O 1.33119(14) 0.16728(11) 0.51789(13) 0.0595(4) Uani 1 1 d . . . O4 O 1.1405(2) 0.24102(11) 0.43725(11) 0.0765(6) Uani 1 1 d . . . O5 O 1.26178(12) 0.31343(8) 0.57746(8) 0.0317(3) Uani 1 1 d . . . O6 O 1.15970(15) 0.15935(10) 0.58195(10) 0.0494(4) 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 Cu1 0.01669(12) 0.01979(13) 0.01452(12) 0.00177(9) 0.00608(9) 0.00199(9) O1 0.0218(5) 0.0270(5) 0.0225(5) 0.0052(4) 0.0107(4) 0.0044(4) O2 0.0197(5) 0.0322(6) 0.0217(5) 0.0050(4) 0.0106(4) 0.0032(4) N1 0.0173(6) 0.0201(6) 0.0162(5) 0.0003(4) 0.0059(4) 0.0000(4) N2 0.0183(6) 0.0246(6) 0.0154(6) 0.0036(5) 0.0045(5) 0.0005(5) N3 0.0185(6) 0.0235(6) 0.0146(6) 0.0031(5) 0.0053(5) -0.0002(5) N4 0.0173(6) 0.0238(6) 0.0190(6) 0.0030(5) 0.0067(5) 0.0043(5) C1 0.0191(7) 0.0162(6) 0.0190(7) -0.0014(5) 0.0043(5) -0.0005(5) C2 0.0168(6) 0.0192(7) 0.0188(6) 0.0016(5) 0.0054(5) 0.0001(5) C3 0.0188(6) 0.0170(6) 0.0160(6) -0.0028(5) 0.0035(5) -0.0033(5) C4 0.0176(6) 0.0216(7) 0.0178(6) -0.0028(5) 0.0059(5) -0.0016(5) C5 0.0230(8) 0.0409(9) 0.0336(9) 0.0067(7) 0.0155(7) 0.0086(7) C6 0.0234(7) 0.0198(7) 0.0156(6) 0.0013(5) 0.0022(5) 0.0031(5) C7 0.0309(8) 0.0234(7) 0.0256(8) 0.0018(6) 0.0038(6) -0.0012(6) C8 0.0531(11) 0.0197(8) 0.0277(8) 0.0010(6) 0.0025(8) 0.0003(7) C9 0.0625(12) 0.0260(8) 0.0257(8) 0.0014(7) 0.0117(8) 0.0176(8) C10 0.0446(10) 0.0369(9) 0.0370(9) 0.0036(8) 0.0194(8) 0.0161(8) C11 0.0300(8) 0.0260(8) 0.0330(8) 0.0005(6) 0.0133(7) 0.0031(6) C12 0.0160(6) 0.0243(7) 0.0206(7) -0.0027(5) 0.0069(5) 0.0005(5) C13 0.0194(7) 0.0241(7) 0.0294(8) -0.0030(6) 0.0069(6) 0.0018(5) C14 0.0261(8) 0.0255(8) 0.0403(9) -0.0108(7) 0.0117(7) -0.0017(6) C15 0.0268(8) 0.0399(9) 0.0320(9) -0.0156(7) 0.0064(7) -0.0063(7) C16 0.0284(8) 0.0447(10) 0.0238(8) -0.0017(7) 0.0004(6) -0.0016(7) C17 0.0254(8) 0.0286(8) 0.0245(8) 0.0006(6) 0.0036(6) -0.0006(6) O7 0.0399(7) 0.0677(10) 0.0424(8) 0.0311(7) 0.0191(6) 0.0179(7) C18 0.0403(10) 0.0423(10) 0.0416(10) 0.0098(8) 0.0177(8) -0.0066(8) Cl1 0.0390(2) 0.02070(17) 0.01921(17) -0.00207(13) 0.00513(15) -0.00375(14) O3 0.0527(9) 0.0454(8) 0.0886(12) -0.0314(8) 0.0333(9) -0.0079(7) O4 0.1276(16) 0.0306(7) 0.0373(8) 0.0017(6) -0.0372(9) -0.0108(9) O5 0.0466(7) 0.0238(6) 0.0222(5) -0.0055(4) 0.0051(5) -0.0052(5) O6 0.0735(10) 0.0327(7) 0.0546(9) -0.0054(6) 0.0389(8) -0.0130(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.9367(13) 3_756 ? Cu1 N4 1.9367(13) . ? Cu1 N1 2.0396(12) 3_756 ? Cu1 N1 2.0396(12) . ? O1 C1 1.2135(17) . ? O2 C4 1.3265(17) . ? O2 C5 1.4480(18) . ? N1 C3 1.3499(18) . ? N1 C1 1.3955(18) . ? N2 C3 1.3300(18) . ? N2 C2 1.4676(18) . ? N2 H2N 0.806(16) . ? N3 C3 1.3424(18) . ? N3 C4 1.3760(18) . ? N3 H3N 0.797(16) . ? N4 C4 1.2738(19) . ? N4 H4N 0.80(2) . ? C1 C2 1.5472(19) . ? C2 C6 1.5263(19) . ? C2 C12 1.5313(19) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.388(2) . ? C6 C11 1.394(2) . ? C7 C8 1.391(2) . ? C7 H7 0.9500 . ? C8 C9 1.381(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.392(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.393(2) . ? C12 C17 1.395(2) . ? C13 C14 1.397(2) . ? C13 H13 0.9500 . ? C14 C15 1.383(3) . ? C14 H14 0.9500 . ? C15 C16 1.389(3) . ? C15 H15 0.9500 . ? C16 C17 1.386(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? O7 C18 1.417(2) . ? O7 H7O 0.8400 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? Cl1 O4 1.4070(14) . ? Cl1 O6 1.4264(13) . ? Cl1 O3 1.4353(15) . ? Cl1 O5 1.4576(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N4 180.0 3_756 . ? N4 Cu1 N1 88.01(5) 3_756 3_756 ? N4 Cu1 N1 91.99(5) . 3_756 ? N4 Cu1 N1 91.99(5) 3_756 . ? N4 Cu1 N1 88.01(5) . . ? N1 Cu1 N1 180.00(6) 3_756 . ? C4 O2 C5 117.69(12) . . ? C3 N1 C1 105.41(11) . . ? C3 N1 Cu1 124.70(9) . . ? C1 N1 Cu1 129.85(9) . . ? C3 N2 C2 109.41(11) . . ? C3 N2 H2N 120.9(13) . . ? C2 N2 H2N 122.3(13) . . ? C3 N3 C4 125.43(12) . . ? C3 N3 H3N 117.4(13) . . ? C4 N3 H3N 116.7(13) . . ? C4 N4 Cu1 130.49(11) . . ? C4 N4 H4N 115.9(14) . . ? Cu1 N4 H4N 110.8(14) . . ? O1 C1 N1 126.58(13) . . ? O1 C1 C2 123.60(12) . . ? N1 C1 C2 109.82(11) . . ? N2 C2 C6 113.02(11) . . ? N2 C2 C12 107.93(11) . . ? C6 C2 C12 114.17(11) . . ? N2 C2 C1 99.10(11) . . ? C6 C2 C1 109.69(11) . . ? C12 C2 C1 111.95(11) . . ? N2 C3 N3 119.38(13) . . ? N2 C3 N1 115.25(12) . . ? N3 C3 N1 125.37(13) . . ? N4 C4 O2 127.49(13) . . ? N4 C4 N3 124.19(13) . . ? O2 C4 N3 108.32(12) . . ? O2 C5 H5A 109.5 . . ? O2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C11 119.41(14) . . ? C7 C6 C2 120.75(13) . . ? C11 C6 C2 119.77(13) . . ? C6 C7 C8 120.33(16) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.16(16) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 119.98(16) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 120.07(17) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C6 120.05(16) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? C13 C12 C17 119.45(14) . . ? C13 C12 C2 121.83(13) . . ? C17 C12 C2 118.40(13) . . ? C12 C13 C14 119.88(15) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 120.34(15) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.74(15) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 120.34(16) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C12 120.22(15) . . ? C16 C17 H17 119.9 . . ? C12 C17 H17 119.9 . . ? C18 O7 H7O 109.5 . . ? O7 C18 H18A 109.5 . . ? O7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O4 Cl1 O6 111.34(11) . . ? O4 Cl1 O3 110.14(12) . . ? O6 Cl1 O3 108.27(10) . . ? O4 Cl1 O5 109.25(8) . . ? O6 Cl1 O5 109.37(8) . . ? O3 Cl1 O5 108.43(8) . . ? 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 N4 Cu1 N1 C3 171.30(11) 3_756 . . . ? N4 Cu1 N1 C3 -8.70(11) . . . . ? N1 Cu1 N1 C3 -61(100) 3_756 . . . ? N4 Cu1 N1 C1 -11.37(12) 3_756 . . . ? N4 Cu1 N1 C1 168.63(12) . . . . ? N1 Cu1 N1 C1 117(100) 3_756 . . . ? N4 Cu1 N4 C4 134(100) 3_756 . . . ? N1 Cu1 N4 C4 -164.57(14) 3_756 . . . ? N1 Cu1 N4 C4 15.43(14) . . . . ? C3 N1 C1 O1 -176.91(14) . . . . ? Cu1 N1 C1 O1 5.4(2) . . . . ? C3 N1 C1 C2 2.26(14) . . . . ? Cu1 N1 C1 C2 -175.46(9) . . . . ? C3 N2 C2 C6 125.79(12) . . . . ? C3 N2 C2 C12 -106.97(13) . . . . ? C3 N2 C2 C1 9.76(14) . . . . ? O1 C1 C2 N2 171.96(13) . . . . ? N1 C1 C2 N2 -7.24(14) . . . . ? O1 C1 C2 C6 53.41(18) . . . . ? N1 C1 C2 C6 -125.79(12) . . . . ? O1 C1 C2 C12 -74.41(17) . . . . ? N1 C1 C2 C12 106.39(13) . . . . ? C2 N2 C3 N3 170.09(12) . . . . ? C2 N2 C3 N1 -9.91(16) . . . . ? C4 N3 C3 N2 -177.27(13) . . . . ? C4 N3 C3 N1 2.7(2) . . . . ? C1 N1 C3 N2 4.64(16) . . . . ? Cu1 N1 C3 N2 -177.49(9) . . . . ? C1 N1 C3 N3 -175.36(13) . . . . ? Cu1 N1 C3 N3 2.51(19) . . . . ? Cu1 N4 C4 O2 165.43(11) . . . . ? Cu1 N4 C4 N3 -15.5(2) . . . . ? C5 O2 C4 N4 -1.6(2) . . . . ? C5 O2 C4 N3 179.18(12) . . . . ? C3 N3 C4 N4 3.5(2) . . . . ? C3 N3 C4 O2 -177.27(12) . . . . ? N2 C2 C6 C7 -14.52(18) . . . . ? C12 C2 C6 C7 -138.40(14) . . . . ? C1 C2 C6 C7 95.03(15) . . . . ? N2 C2 C6 C11 168.57(13) . . . . ? C12 C2 C6 C11 44.68(18) . . . . ? C1 C2 C6 C11 -81.89(16) . . . . ? C11 C6 C7 C8 -0.6(2) . . . . ? C2 C6 C7 C8 -177.54(14) . . . . ? C6 C7 C8 C9 -0.3(2) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C9 C10 C11 C6 -0.7(3) . . . . ? C7 C6 C11 C10 1.1(2) . . . . ? C2 C6 C11 C10 178.03(14) . . . . ? N2 C2 C12 C13 93.67(15) . . . . ? C6 C2 C12 C13 -139.75(14) . . . . ? C1 C2 C12 C13 -14.37(18) . . . . ? N2 C2 C12 C17 -79.76(15) . . . . ? C6 C2 C12 C17 46.82(17) . . . . ? C1 C2 C12 C17 172.20(13) . . . . ? C17 C12 C13 C14 0.1(2) . . . . ? C2 C12 C13 C14 -173.24(13) . . . . ? C12 C13 C14 C15 0.7(2) . . . . ? C13 C14 C15 C16 -0.9(3) . . . . ? C14 C15 C16 C17 0.4(3) . . . . ? C15 C16 C17 C12 0.4(3) . . . . ? C13 C12 C17 C16 -0.7(2) . . . . ? C2 C12 C17 C16 172.92(14) . . . . ? 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 O7 H7O O3 0.84 2.10 2.928(2) 167.6 4_565 O7 H7O O5 0.84 2.52 3.022(2) 119.5 4_565 N2 H2N O5 0.806(16) 2.035(17) 2.8278(18) 167.5(18) 4_565 N3 H3N O7 0.797(16) 1.974(17) 2.7633(18) 170.7(18) . N4 H4N O1 0.80(2) 2.01(2) 2.7576(17) 156.3(19) 3_756 _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.410 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.050 #===END data_3c _database_code_depnum_ccdc_archive 'CCDC 265655' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H36 Cu N8 O5 S' _chemical_formula_weight 756.33 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 'P 21/c ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.366(3) _cell_length_b 14.299(3) _cell_length_c 19.892(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.054(3) _cell_angle_gamma 90.00 _cell_volume 3396.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 967 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.62 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.263 _exptl_crystal_size_mid 0.119 _exptl_crystal_size_min 0.102 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1572 _exptl_absorpt_coefficient_mu 0.762 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.818 _exptl_absorpt_correction_T_max 0.932 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 125 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.11 _diffrn_reflns_number 30324 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.13 _reflns_number_total 7647 _reflns_number_gt 5101 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _computing_publication_material ? _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^)+(0.02P)^2^+0.5P] 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 7647 _refine_ls_number_parameters 480 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.122 _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 0.79407(2) 0.286477(19) 0.185015(14) 0.01692(8) Uani 1 1 d . . . O1 O 1.07264(12) 0.30353(11) 0.18127(8) 0.0239(4) Uani 1 1 d . . . O2 O 0.55680(13) 0.28041(13) -0.00712(8) 0.0331(4) Uani 1 1 d . . . O3 O 0.51445(13) 0.31456(11) 0.18906(8) 0.0260(4) Uani 1 1 d . . . O4 O 1.02914(13) 0.26627(11) 0.37685(8) 0.0238(4) Uani 1 1 d . . . N1 N 0.88894(15) 0.29299(12) 0.11476(9) 0.0156(4) Uani 1 1 d . . . N2 N 0.92349(16) 0.26560(14) 0.01056(11) 0.0184(5) Uani 1 1 d . . . H2N H 0.9120(18) 0.2563(15) -0.0262(11) 0.010(7) Uiso 1 1 d . . . N3 N 0.73784(15) 0.26939(12) 0.00914(9) 0.0178(4) Uani 1 1 d . . . N4 N 0.66413(17) 0.29484(14) 0.10658(10) 0.0210(5) Uani 1 1 d . . . H4N H 0.6063(18) 0.3019(15) 0.1174(11) 0.014(6) Uiso 1 1 d . . . N5 N 0.69691(15) 0.28798(13) 0.25425(9) 0.0174(4) Uani 1 1 d . . . N6 N 0.66137(16) 0.26095(14) 0.35812(10) 0.0195(5) Uani 1 1 d D . . H6N H 0.677(2) 0.2541(18) 0.3994(9) 0.042(9) Uiso 1 1 d D . . N7 N 0.84689(15) 0.26048(12) 0.35908(9) 0.0168(4) Uani 1 1 d . . . N8 N 0.92308(17) 0.29753(14) 0.26428(10) 0.0209(5) Uani 1 1 d . . . H8N H 0.9807(19) 0.3036(15) 0.2547(12) 0.017(7) Uiso 1 1 d . . . C1 C 1.00235(19) 0.29017(15) 0.12592(11) 0.0175(5) Uani 1 1 d . . . C2 C 1.03411(18) 0.26602(15) 0.05730(11) 0.0166(5) Uani 1 1 d . . . C3 C 0.84372(19) 0.27557(14) 0.04461(11) 0.0162(5) Uani 1 1 d . . . C4 C 0.65542(18) 0.28153(15) 0.04183(11) 0.0182(5) Uani 1 1 d . . . C5 C 0.4574(2) 0.3004(2) 0.01446(14) 0.0490(9) Uani 1 1 d . . . H5A H 0.4437 0.2498 0.0444 0.073 Uiso 1 1 calc R . . H5B H 0.3936 0.3056 -0.0266 0.073 Uiso 1 1 calc R . . H5C H 0.4670 0.3595 0.0403 0.073 Uiso 1 1 calc R . . C6 C 1.08401(19) 0.16681(16) 0.06277(11) 0.0183(5) Uani 1 1 d . . . C7 C 1.0294(2) 0.09544(17) 0.08808(12) 0.0288(6) Uani 1 1 d . . . H7 H 0.9646 0.1094 0.1034 0.035 Uiso 1 1 calc R . . C8 C 1.0678(2) 0.00488(18) 0.09128(14) 0.0368(7) Uani 1 1 d . . . H8 H 1.0293 -0.0431 0.1087 0.044 Uiso 1 1 calc R . . C9 C 1.1615(2) -0.01664(18) 0.06941(13) 0.0364(7) Uani 1 1 d . . . H9 H 1.1882 -0.0792 0.0719 0.044 Uiso 1 1 calc R . . C10 C 1.2160(2) 0.05292(18) 0.04402(14) 0.0371(7) Uani 1 1 d . . . H10 H 1.2806 0.0383 0.0286 0.045 Uiso 1 1 calc R . . C11 C 1.1780(2) 0.14450(17) 0.04055(12) 0.0280(6) Uani 1 1 d . . . H11 H 1.2167 0.1921 0.0229 0.034 Uiso 1 1 calc R . . C12 C 1.11003(18) 0.34256(15) 0.04123(11) 0.0169(5) Uani 1 1 d . . . C13 C 1.0753(2) 0.40195(15) -0.01532(12) 0.0237(5) Uani 1 1 d . . . H13 H 1.0030 0.3946 -0.0462 0.028 Uiso 1 1 calc R . . C14 C 1.1461(2) 0.47238(17) -0.02700(14) 0.0332(6) Uani 1 1 d . . . H14 H 1.1226 0.5118 -0.0666 0.040 Uiso 1 1 calc R . . C15 C 1.2496(2) 0.48525(17) 0.01816(14) 0.0331(7) Uani 1 1 d . . . H15 H 1.2969 0.5341 0.0104 0.040 Uiso 1 1 calc R . . C16 C 1.2844(2) 0.42718(17) 0.07475(13) 0.0298(6) Uani 1 1 d . . . H16 H 1.3558 0.4363 0.1063 0.036 Uiso 1 1 calc R . . C17 C 1.21594(19) 0.35543(16) 0.08589(12) 0.0235(6) Uani 1 1 d . . . H17 H 1.2415 0.3146 0.1244 0.028 Uiso 1 1 calc R . . C18 C 0.58369(19) 0.29697(15) 0.24394(12) 0.0195(5) Uani 1 1 d . . . C19 C 0.55145(18) 0.28243(16) 0.31368(11) 0.0190(5) Uani 1 1 d . . . C20 C 0.74097(19) 0.26954(14) 0.32401(11) 0.0165(5) Uani 1 1 d . . . C21 C 0.93062(18) 0.27638(15) 0.32804(11) 0.0171(5) Uani 1 1 d . . . C22 C 1.13164(19) 0.27264(19) 0.35610(13) 0.0319(6) Uani 1 1 d . . . H22A H 1.1283 0.2305 0.3168 0.048 Uiso 1 1 calc R . . H22B H 1.1945 0.2548 0.3952 0.048 Uiso 1 1 calc R . . H22C H 1.1422 0.3370 0.3422 0.048 Uiso 1 1 calc R . . C23 C 0.46831(19) 0.20140(16) 0.30682(11) 0.0213(5) Uani 1 1 d . . . C24 C 0.4955(2) 0.11916(16) 0.34454(12) 0.0266(6) Uani 1 1 d . . . H24 H 0.5685 0.1110 0.3743 0.032 Uiso 1 1 calc R . . C25 C 0.4167(2) 0.04915(18) 0.33888(14) 0.0349(7) Uani 1 1 d . . . H25 H 0.4353 -0.0059 0.3661 0.042 Uiso 1 1 calc R . . C26 C 0.3113(2) 0.05808(18) 0.29422(14) 0.0349(7) Uani 1 1 d . . . H26 H 0.2577 0.0095 0.2904 0.042 Uiso 1 1 calc R . . C27 C 0.2848(2) 0.13907(19) 0.25493(14) 0.0338(7) Uani 1 1 d . . . H27 H 0.2132 0.1454 0.2230 0.041 Uiso 1 1 calc R . . C28 C 0.3616(2) 0.20997(18) 0.26198(12) 0.0277(6) Uani 1 1 d . . . H28 H 0.3417 0.2659 0.2359 0.033 Uiso 1 1 calc R . . C29 C 0.50719(19) 0.37349(17) 0.33770(11) 0.0225(5) Uani 1 1 d . . . C30 C 0.5506(2) 0.45857(18) 0.32546(13) 0.0357(7) Uani 1 1 d . . . H30 H 0.6054 0.4610 0.2997 0.043 Uiso 1 1 calc R . . C31 C 0.5154(2) 0.54114(19) 0.35023(15) 0.0432(7) Uani 1 1 d . . . H31 H 0.5454 0.5993 0.3407 0.052 Uiso 1 1 calc R . . C32 C 0.4383(2) 0.5389(2) 0.38812(15) 0.0442(8) Uani 1 1 d . . . H32 H 0.4152 0.5952 0.4058 0.053 Uiso 1 1 calc R . . C33 C 0.3946(3) 0.4554(2) 0.40041(15) 0.0480(8) Uani 1 1 d . . . H33 H 0.3406 0.4537 0.4268 0.058 Uiso 1 1 calc R . . C34 C 0.4273(2) 0.37274(19) 0.37529(13) 0.0361(7) Uani 1 1 d . . . H34 H 0.3948 0.3152 0.3838 0.043 Uiso 1 1 calc R . . S1 S 0.84963(6) 0.02860(4) 0.21435(4) 0.03169(17) Uani 1 1 d . . . O5 O 0.81949(14) 0.12048(11) 0.17909(9) 0.0339(4) Uani 1 1 d . . . C35 C 0.7742(2) 0.0165(2) 0.27800(15) 0.0509(8) Uani 1 1 d . . . H35A H 0.7894 0.0704 0.3095 0.076 Uiso 1 1 calc R . . H35B H 0.7976 -0.0409 0.3046 0.076 Uiso 1 1 calc R . . H35C H 0.6939 0.0134 0.2552 0.076 Uiso 1 1 calc R . . C36 C 0.9856(2) 0.04039(19) 0.27261(15) 0.0443(8) Uani 1 1 d . . . H36A H 1.0399 0.0556 0.2461 0.066 Uiso 1 1 calc R . . H36B H 1.0069 -0.0185 0.2977 0.066 Uiso 1 1 calc R . . H36C H 0.9846 0.0906 0.3060 0.066 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 0.01626(15) 0.02448(15) 0.01066(14) 0.00057(13) 0.00464(11) -0.00001(13) O1 0.0181(9) 0.0409(11) 0.0129(8) -0.0040(7) 0.0043(7) -0.0040(8) O2 0.0164(9) 0.0671(13) 0.0150(9) -0.0051(9) 0.0031(7) 0.0061(9) O3 0.0193(9) 0.0454(11) 0.0129(9) 0.0051(7) 0.0037(7) 0.0066(8) O4 0.0155(9) 0.0396(10) 0.0164(9) 0.0040(7) 0.0047(7) 0.0005(8) N1 0.0172(10) 0.0200(10) 0.0098(9) -0.0004(8) 0.0039(8) -0.0020(8) N2 0.0189(11) 0.0292(12) 0.0078(10) -0.0025(9) 0.0051(9) -0.0012(9) N3 0.0177(11) 0.0252(11) 0.0104(9) -0.0020(8) 0.0034(8) -0.0009(9) N4 0.0154(11) 0.0350(12) 0.0149(10) 0.0016(9) 0.0078(9) 0.0029(10) N5 0.0159(10) 0.0251(10) 0.0114(9) 0.0017(8) 0.0041(8) 0.0036(9) N6 0.0158(11) 0.0328(12) 0.0099(11) 0.0029(9) 0.0032(9) 0.0041(9) N7 0.0162(10) 0.0243(11) 0.0109(10) 0.0025(8) 0.0053(8) 0.0018(8) N8 0.0146(11) 0.0348(13) 0.0150(11) 0.0010(9) 0.0067(9) -0.0021(10) C1 0.0213(13) 0.0182(12) 0.0142(12) 0.0029(10) 0.0066(10) -0.0025(10) C2 0.0149(12) 0.0226(13) 0.0125(11) -0.0005(9) 0.0037(9) -0.0009(10) C3 0.0209(13) 0.0133(11) 0.0154(12) 0.0020(9) 0.0065(10) -0.0001(10) C4 0.0165(12) 0.0221(12) 0.0162(12) -0.0015(10) 0.0044(10) 0.0000(10) C5 0.0150(14) 0.104(3) 0.0256(15) -0.0100(16) 0.0015(12) 0.0110(16) C6 0.0184(13) 0.0232(13) 0.0120(12) -0.0004(10) 0.0016(10) -0.0004(10) C7 0.0291(15) 0.0283(14) 0.0317(15) 0.0037(12) 0.0124(12) -0.0009(12) C8 0.0438(18) 0.0247(15) 0.0421(18) 0.0053(12) 0.0117(14) -0.0043(13) C9 0.0472(18) 0.0236(15) 0.0367(17) 0.0054(12) 0.0075(14) 0.0099(13) C10 0.0374(17) 0.0393(17) 0.0398(17) 0.0042(13) 0.0190(14) 0.0134(14) C11 0.0296(15) 0.0284(14) 0.0289(15) 0.0045(11) 0.0127(12) 0.0049(12) C12 0.0208(13) 0.0165(12) 0.0168(12) -0.0044(9) 0.0109(10) -0.0015(10) C13 0.0228(13) 0.0227(13) 0.0271(14) 0.0012(11) 0.0092(11) 0.0024(11) C14 0.0419(17) 0.0235(14) 0.0387(16) 0.0097(12) 0.0184(14) 0.0013(13) C15 0.0355(17) 0.0237(14) 0.0475(18) -0.0036(13) 0.0241(14) -0.0083(12) C16 0.0249(14) 0.0328(15) 0.0344(16) -0.0104(12) 0.0127(12) -0.0084(12) C17 0.0233(14) 0.0288(14) 0.0207(13) 0.0002(11) 0.0099(11) -0.0010(11) C18 0.0206(13) 0.0214(13) 0.0176(12) 0.0009(10) 0.0071(10) 0.0014(11) C19 0.0158(12) 0.0288(13) 0.0130(12) 0.0025(10) 0.0046(10) 0.0033(11) C20 0.0204(13) 0.0163(12) 0.0130(12) -0.0005(9) 0.0049(10) 0.0017(9) C21 0.0180(13) 0.0161(12) 0.0167(12) -0.0013(10) 0.0034(10) 0.0023(10) C22 0.0172(14) 0.0531(18) 0.0254(14) 0.0052(13) 0.0052(11) 0.0000(12) C23 0.0188(13) 0.0309(14) 0.0170(12) -0.0013(11) 0.0095(10) 0.0025(11) C24 0.0241(14) 0.0296(14) 0.0257(14) 0.0001(11) 0.0056(11) 0.0034(12) C25 0.0328(16) 0.0265(15) 0.0445(18) 0.0059(13) 0.0086(14) 0.0031(12) C26 0.0259(15) 0.0330(16) 0.0472(18) -0.0072(13) 0.0122(13) -0.0034(12) C27 0.0196(14) 0.0464(18) 0.0335(16) -0.0026(13) 0.0033(12) 0.0011(13) C28 0.0218(14) 0.0362(15) 0.0244(13) 0.0061(12) 0.0048(11) 0.0022(12) C29 0.0203(13) 0.0305(14) 0.0163(13) 0.0042(10) 0.0041(10) 0.0052(11) C30 0.0368(17) 0.0386(17) 0.0363(16) 0.0014(13) 0.0181(13) 0.0011(13) C31 0.051(2) 0.0300(16) 0.0482(19) -0.0036(14) 0.0126(16) -0.0017(15) C32 0.0401(18) 0.0436(19) 0.050(2) -0.0157(15) 0.0139(15) 0.0079(15) C33 0.056(2) 0.052(2) 0.048(2) -0.0012(16) 0.0355(17) 0.0144(17) C34 0.0400(17) 0.0381(16) 0.0368(17) 0.0038(13) 0.0222(14) 0.0039(14) S1 0.0361(4) 0.0244(3) 0.0356(4) 0.0015(3) 0.0112(3) -0.0030(3) O5 0.0420(12) 0.0260(9) 0.0345(11) 0.0069(8) 0.0113(9) -0.0029(8) C35 0.057(2) 0.053(2) 0.049(2) 0.0146(16) 0.0247(17) 0.0005(17) C36 0.0393(18) 0.0380(17) 0.0510(19) -0.0002(14) 0.0035(15) -0.0004(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 N4 1.931(2) . ? Cu1 N8 1.936(2) . ? Cu1 N1 2.0468(17) . ? Cu1 N5 2.0495(18) . ? Cu1 O5 2.4013(17) . ? O1 C1 1.228(2) . ? O2 C4 1.349(3) . ? O2 C5 1.432(3) . ? O3 C18 1.226(3) . ? O4 C21 1.354(3) . ? O4 C22 1.434(3) . ? N1 C1 1.362(3) . ? N1 C3 1.385(3) . ? N2 C3 1.341(3) . ? N2 C2 1.440(3) . ? N2 H2N 0.72(2) . ? N3 C3 1.319(3) . ? N3 C4 1.355(3) . ? N4 C4 1.279(3) . ? N4 H4N 0.80(2) . ? N5 C18 1.367(3) . ? N5 C20 1.378(3) . ? N6 C20 1.338(3) . ? N6 C19 1.449(3) . ? N6 H6N 0.799(16) . ? N7 C20 1.321(3) . ? N7 C21 1.355(3) . ? N8 C21 1.284(3) . ? N8 H8N 0.79(2) . ? C1 C2 1.554(3) . ? C2 C12 1.529(3) . ? C2 C6 1.540(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C11 1.384(3) . ? C6 C7 1.388(3) . ? C7 C8 1.375(3) . ? C7 H7 0.9500 . ? C8 C9 1.375(4) . ? C8 H8 0.9500 . ? C9 C10 1.369(3) . ? C9 H9 0.9500 . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.386(3) . ? C12 C17 1.391(3) . ? C13 C14 1.394(3) . ? C13 H13 0.9500 . ? C14 C15 1.371(4) . ? C14 H14 0.9500 . ? C15 C16 1.375(3) . ? C15 H15 0.9500 . ? C16 C17 1.384(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.554(3) . ? C19 C23 1.531(3) . ? C19 C29 1.536(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.388(3) . ? C23 C28 1.393(3) . ? C24 C25 1.381(3) . ? C24 H24 0.9500 . ? C25 C26 1.379(4) . ? C25 H25 0.9500 . ? C26 C27 1.388(3) . ? C26 H26 0.9500 . ? C27 C28 1.371(3) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.377(3) . ? C29 C34 1.386(3) . ? C30 C31 1.392(3) . ? C30 H30 0.9500 . ? C31 C32 1.361(4) . ? C31 H31 0.9500 . ? C32 C33 1.359(4) . ? C32 H32 0.9500 . ? C33 C34 1.383(4) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? S1 O5 1.4902(17) . ? S1 C35 1.765(3) . ? S1 C36 1.785(3) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N8 171.74(8) . . ? N4 Cu1 N1 87.12(8) . . ? N8 Cu1 N1 93.16(8) . . ? N4 Cu1 N5 91.85(8) . . ? N8 Cu1 N5 87.41(8) . . ? N1 Cu1 N5 176.69(7) . . ? N4 Cu1 O5 96.52(7) . . ? N8 Cu1 O5 91.72(7) . . ? N1 Cu1 O5 84.60(6) . . ? N5 Cu1 O5 98.65(7) . . ? C4 O2 C5 117.82(18) . . ? C21 O4 C22 119.00(17) . . ? C1 N1 C3 106.74(17) . . ? C1 N1 Cu1 129.48(14) . . ? C3 N1 Cu1 121.80(14) . . ? C3 N2 C2 111.92(19) . . ? C3 N2 H2N 123.7(18) . . ? C2 N2 H2N 124.1(18) . . ? C3 N3 C4 120.04(19) . . ? C4 N4 Cu1 129.75(17) . . ? C4 N4 H4N 116.1(16) . . ? Cu1 N4 H4N 113.7(16) . . ? C18 N5 C20 106.90(17) . . ? C18 N5 Cu1 131.02(15) . . ? C20 N5 Cu1 121.82(14) . . ? C20 N6 C19 111.60(18) . . ? C20 N6 H6N 122(2) . . ? C19 N6 H6N 126(2) . . ? C20 N7 C21 120.87(18) . . ? C21 N8 Cu1 128.21(17) . . ? C21 N8 H8N 115.2(17) . . ? Cu1 N8 H8N 114.7(17) . . ? O1 C1 N1 126.9(2) . . ? O1 C1 C2 122.7(2) . . ? N1 C1 C2 110.36(18) . . ? N2 C2 C12 113.57(18) . . ? N2 C2 C6 109.74(18) . . ? C12 C2 C6 114.70(18) . . ? N2 C2 C1 98.83(17) . . ? C12 C2 C1 109.49(17) . . ? C6 C2 C1 109.31(17) . . ? N3 C3 N2 118.7(2) . . ? N3 C3 N1 129.5(2) . . ? N2 C3 N1 111.8(2) . . ? N4 C4 O2 123.6(2) . . ? N4 C4 N3 128.7(2) . . ? O2 C4 N3 107.69(18) . . ? O2 C5 H5A 109.5 . . ? O2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 118.3(2) . . ? C11 C6 C2 123.0(2) . . ? C7 C6 C2 118.6(2) . . ? C8 C7 C6 121.0(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C9 C8 C7 120.4(3) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 119.4(2) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 120.8(2) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C6 C11 C10 120.2(2) . . ? C6 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C17 118.7(2) . . ? C13 C12 C2 122.0(2) . . ? C17 C12 C2 119.3(2) . . ? C12 C13 C14 120.1(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 120.5(2) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.7(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 120.3(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 120.6(2) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? O3 C18 N5 127.2(2) . . ? O3 C18 C19 122.7(2) . . ? N5 C18 C19 110.10(18) . . ? N6 C19 C23 113.31(18) . . ? N6 C19 C29 110.09(18) . . ? C23 C19 C29 112.57(18) . . ? N6 C19 C18 98.94(17) . . ? C23 C19 C18 110.10(18) . . ? C29 C19 C18 111.05(18) . . ? N7 C20 N6 118.83(19) . . ? N7 C20 N5 128.98(19) . . ? N6 C20 N5 112.2(2) . . ? N8 C21 O4 123.7(2) . . ? N8 C21 N7 128.4(2) . . ? O4 C21 N7 107.88(18) . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 118.5(2) . . ? C24 C23 C19 122.0(2) . . ? C28 C23 C19 119.5(2) . . ? C25 C24 C23 120.2(2) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C26 C25 C24 120.9(2) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C27 119.0(2) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C28 C27 C26 120.2(2) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C28 C23 121.1(2) . . ? C27 C28 H28 119.5 . . ? C23 C28 H28 119.5 . . ? C30 C29 C34 117.9(2) . . ? C30 C29 C19 120.5(2) . . ? C34 C29 C19 121.5(2) . . ? C29 C30 C31 121.0(2) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C32 C31 C30 120.3(3) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C33 C32 C31 119.2(3) . . ? C33 C32 H32 120.4 . . ? C31 C32 H32 120.4 . . ? C32 C33 C34 121.3(3) . . ? C32 C33 H33 119.4 . . ? C34 C33 H33 119.4 . . ? C33 C34 C29 120.3(3) . . ? C33 C34 H34 119.8 . . ? C29 C34 H34 119.8 . . ? O5 S1 C35 108.04(12) . . ? O5 S1 C36 107.49(12) . . ? C35 S1 C36 97.32(14) . . ? S1 O5 Cu1 150.24(11) . . ? S1 C35 H35A 109.5 . . ? S1 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? S1 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? S1 C36 H36A 109.5 . . ? S1 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? S1 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? 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 N4 Cu1 N1 C1 -179.1(2) . . . . ? N8 Cu1 N1 C1 9.2(2) . . . . ? N5 Cu1 N1 C1 108.9(13) . . . . ? O5 Cu1 N1 C1 -82.24(19) . . . . ? N4 Cu1 N1 C3 -17.31(16) . . . . ? N8 Cu1 N1 C3 170.95(16) . . . . ? N5 Cu1 N1 C3 -89.3(13) . . . . ? O5 Cu1 N1 C3 79.52(16) . . . . ? N8 Cu1 N4 C4 108.8(6) . . . . ? N1 Cu1 N4 C4 16.6(2) . . . . ? N5 Cu1 N4 C4 -166.5(2) . . . . ? O5 Cu1 N4 C4 -67.6(2) . . . . ? N4 Cu1 N5 C18 -3.1(2) . . . . ? N8 Cu1 N5 C18 168.7(2) . . . . ? N1 Cu1 N5 C18 68.8(13) . . . . ? O5 Cu1 N5 C18 -99.9(2) . . . . ? N4 Cu1 N5 C20 170.18(17) . . . . ? N8 Cu1 N5 C20 -18.05(17) . . . . ? N1 Cu1 N5 C20 -118.0(13) . . . . ? O5 Cu1 N5 C20 73.29(16) . . . . ? N4 Cu1 N8 C21 106.8(6) . . . . ? N1 Cu1 N8 C21 -161.5(2) . . . . ? N5 Cu1 N8 C21 21.8(2) . . . . ? O5 Cu1 N8 C21 -76.8(2) . . . . ? C3 N1 C1 O1 178.8(2) . . . . ? Cu1 N1 C1 O1 -17.3(4) . . . . ? C3 N1 C1 C2 -1.7(2) . . . . ? Cu1 N1 C1 C2 162.15(14) . . . . ? C3 N2 C2 C12 -122.1(2) . . . . ? C3 N2 C2 C6 108.0(2) . . . . ? C3 N2 C2 C1 -6.3(2) . . . . ? O1 C1 C2 N2 -175.7(2) . . . . ? N1 C1 C2 N2 4.8(2) . . . . ? O1 C1 C2 C12 -56.8(3) . . . . ? N1 C1 C2 C12 123.7(2) . . . . ? O1 C1 C2 C6 69.6(3) . . . . ? N1 C1 C2 C6 -109.8(2) . . . . ? C4 N3 C3 N2 -178.3(2) . . . . ? C4 N3 C3 N1 0.5(3) . . . . ? C2 N2 C3 N3 -174.94(19) . . . . ? C2 N2 C3 N1 6.0(3) . . . . ? C1 N1 C3 N3 178.6(2) . . . . ? Cu1 N1 C3 N3 13.2(3) . . . . ? C1 N1 C3 N2 -2.5(2) . . . . ? Cu1 N1 C3 N2 -167.86(14) . . . . ? Cu1 N4 C4 O2 172.98(17) . . . . ? Cu1 N4 C4 N3 -9.3(4) . . . . ? C5 O2 C4 N4 3.6(4) . . . . ? C5 O2 C4 N3 -174.5(2) . . . . ? C3 N3 C4 N4 -3.7(4) . . . . ? C3 N3 C4 O2 174.29(19) . . . . ? N2 C2 C6 C11 115.9(2) . . . . ? C12 C2 C6 C11 -13.4(3) . . . . ? C1 C2 C6 C11 -136.7(2) . . . . ? N2 C2 C6 C7 -61.0(3) . . . . ? C12 C2 C6 C7 169.8(2) . . . . ? C1 C2 C6 C7 46.4(3) . . . . ? C11 C6 C7 C8 0.2(4) . . . . ? C2 C6 C7 C8 177.2(2) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 -0.4(4) . . . . ? C8 C9 C10 C11 0.4(4) . . . . ? C7 C6 C11 C10 -0.2(4) . . . . ? C2 C6 C11 C10 -177.1(2) . . . . ? C9 C10 C11 C6 -0.1(4) . . . . ? N2 C2 C12 C13 -3.0(3) . . . . ? C6 C2 C12 C13 124.4(2) . . . . ? C1 C2 C12 C13 -112.4(2) . . . . ? N2 C2 C12 C17 174.78(19) . . . . ? C6 C2 C12 C17 -57.9(3) . . . . ? C1 C2 C12 C17 65.4(3) . . . . ? C17 C12 C13 C14 0.5(3) . . . . ? C2 C12 C13 C14 178.3(2) . . . . ? C12 C13 C14 C15 -1.7(4) . . . . ? C13 C14 C15 C16 1.1(4) . . . . ? C14 C15 C16 C17 0.6(4) . . . . ? C15 C16 C17 C12 -1.7(4) . . . . ? C13 C12 C17 C16 1.1(3) . . . . ? C2 C12 C17 C16 -176.7(2) . . . . ? C20 N5 C18 O3 179.1(2) . . . . ? Cu1 N5 C18 O3 -6.9(4) . . . . ? C20 N5 C18 C19 -0.3(2) . . . . ? Cu1 N5 C18 C19 173.68(14) . . . . ? C20 N6 C19 C23 121.3(2) . . . . ? C20 N6 C19 C29 -111.6(2) . . . . ? C20 N6 C19 C18 4.8(2) . . . . ? O3 C18 C19 N6 177.9(2) . . . . ? N5 C18 C19 N6 -2.6(2) . . . . ? O3 C18 C19 C23 58.9(3) . . . . ? N5 C18 C19 C23 -121.6(2) . . . . ? O3 C18 C19 C29 -66.4(3) . . . . ? N5 C18 C19 C29 113.1(2) . . . . ? C21 N7 C20 N6 -174.39(19) . . . . ? C21 N7 C20 N5 5.1(3) . . . . ? C19 N6 C20 N7 174.00(19) . . . . ? C19 N6 C20 N5 -5.6(3) . . . . ? C18 N5 C20 N7 -176.0(2) . . . . ? Cu1 N5 C20 N7 9.3(3) . . . . ? C18 N5 C20 N6 3.6(3) . . . . ? Cu1 N5 C20 N6 -171.10(14) . . . . ? Cu1 N8 C21 O4 164.37(16) . . . . ? Cu1 N8 C21 N7 -15.7(4) . . . . ? C22 O4 C21 N8 -4.7(3) . . . . ? C22 O4 C21 N7 175.39(19) . . . . ? C20 N7 C21 N8 -2.8(4) . . . . ? C20 N7 C21 O4 177.14(18) . . . . ? N6 C19 C23 C24 4.8(3) . . . . ? C29 C19 C23 C24 -120.9(2) . . . . ? C18 C19 C23 C24 114.6(2) . . . . ? N6 C19 C23 C28 -175.7(2) . . . . ? C29 C19 C23 C28 58.5(3) . . . . ? C18 C19 C23 C28 -66.0(3) . . . . ? C28 C23 C24 C25 -2.0(3) . . . . ? C19 C23 C24 C25 177.5(2) . . . . ? C23 C24 C25 C26 2.2(4) . . . . ? C24 C25 C26 C27 -0.4(4) . . . . ? C25 C26 C27 C28 -1.7(4) . . . . ? C26 C27 C28 C23 1.9(4) . . . . ? C24 C23 C28 C27 -0.1(4) . . . . ? C19 C23 C28 C27 -179.6(2) . . . . ? N6 C19 C29 C30 73.8(3) . . . . ? C23 C19 C29 C30 -158.8(2) . . . . ? C18 C19 C29 C30 -34.8(3) . . . . ? N6 C19 C29 C34 -102.8(3) . . . . ? C23 C19 C29 C34 24.7(3) . . . . ? C18 C19 C29 C34 148.7(2) . . . . ? C34 C29 C30 C31 0.1(4) . . . . ? C19 C29 C30 C31 -176.5(2) . . . . ? C29 C30 C31 C32 1.0(4) . . . . ? C30 C31 C32 C33 -1.1(4) . . . . ? C31 C32 C33 C34 0.1(5) . . . . ? C32 C33 C34 C29 1.0(4) . . . . ? C30 C29 C34 C33 -1.1(4) . . . . ? C19 C29 C34 C33 175.5(2) . . . . ? C35 S1 O5 Cu1 49.3(2) . . . . ? C36 S1 O5 Cu1 -54.8(2) . . . . ? N4 Cu1 O5 S1 -142.3(2) . . . . ? N8 Cu1 O5 S1 38.2(2) . . . . ? N1 Cu1 O5 S1 131.2(2) . . . . ? N5 Cu1 O5 S1 -49.4(2) . . . . ? 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 N2 H2N N7 0.72(2) 2.23(2) 2.938(3) 170(2) 4_565 N4 H4N O3 0.80(2) 2.05(2) 2.788(2) 153(2) . N8 H8N O1 0.79(2) 2.07(2) 2.782(3) 150(2) . N6 H6N N3 0.799(16) 2.144(17) 2.938(3) 173(3) 4_566 _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 28.13 _diffrn_measured_fraction_theta_full 0.920 _refine_diff_density_max 0.510 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.067 #===END data_4a _database_code_depnum_ccdc_archive 'CCDC 265656' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H48 Cu N10 O4 S2' _chemical_formula_weight 860.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.992(3) _cell_length_b 10.823(3) _cell_length_c 11.164(3) _cell_angle_alpha 74.218(4) _cell_angle_beta 71.368(4) _cell_angle_gamma 66.793(4) _cell_volume 1036.6(5) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1002 _cell_measurement_theta_min 3.344 _cell_measurement_theta_max 27.997 _exptl_crystal_description blade _exptl_crystal_colour purple _exptl_crystal_size_max 0.278 _exptl_crystal_size_mid 0.216 _exptl_crystal_size_min 0.069 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 451 _exptl_absorpt_coefficient_mu 0.681 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.812 _exptl_absorpt_correction_T_max 0.961 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 110 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.2 _diffrn_reflns_number 9526 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.18 _reflns_number_total 4521 _reflns_number_gt 3899 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _computing_publication_material ? _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^)+(0.03P)^2^+0.5P] 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 4527 _refine_ls_number_parameters 271 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.197 _refine_ls_restrained_S_all 1.198 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.5000 0.5000 0.01757(10) Uani 1 2 d S . . O1 O 0.04930(16) 0.20107(14) 0.72666(14) 0.0267(3) Uani 1 1 d . . . N1 N 0.12200(18) 0.39206(16) 0.63413(14) 0.0177(3) Uani 1 1 d . . . N2 N 0.28828(19) 0.34929(17) 0.75100(16) 0.0203(4) Uani 1 1 d D . . N3 N 0.25927(18) 0.54626(16) 0.60516(15) 0.0185(3) Uani 1 1 d . . . N4 N 0.0798(2) 0.64023(17) 0.47781(17) 0.0236(4) Uani 1 1 d D . . N5 N 0.23303(19) 0.75465(17) 0.47931(15) 0.0224(4) Uani 1 1 d . . . C1 C 0.1242(2) 0.2719(2) 0.71556(18) 0.0198(4) Uani 1 1 d . . . C2 C 0.2371(2) 0.23325(19) 0.79906(18) 0.0186(4) Uani 1 1 d . . . C3 C 0.2227(2) 0.43679(19) 0.65774(17) 0.0174(4) Uani 1 1 d . . . C4 C 0.1868(2) 0.64460(19) 0.51886(17) 0.0180(4) Uani 1 1 d . . . C5 C 0.3612(3) 0.7555(2) 0.5146(2) 0.0321(5) Uani 1 1 d . . . H5A H 0.3295 0.7766 0.6015 0.048 Uiso 1 1 calc R . . H5B H 0.4005 0.8249 0.4542 0.048 Uiso 1 1 calc R . . H5C H 0.4396 0.6658 0.5119 0.048 Uiso 1 1 calc R . . C6 C 0.1566(2) 0.8758(2) 0.39913(19) 0.0246(4) Uani 1 1 d . . . H6A H 0.1847 0.8585 0.3112 0.037 Uiso 1 1 calc R . . H6B H 0.1856 0.9522 0.3996 0.037 Uiso 1 1 calc R . . H6C H 0.0478 0.8984 0.4325 0.037 Uiso 1 1 calc R . . C7 C 0.3683(2) 0.10087(19) 0.77417(17) 0.0190(4) Uani 1 1 d . . . C8 C 0.3849(2) 0.0230(2) 0.6873(2) 0.0279(5) Uani 1 1 d . . . H8 H 0.3091 0.0475 0.6427 0.033 Uiso 1 1 calc R . . C9 C 0.5126(3) -0.0916(2) 0.6650(2) 0.0333(5) Uani 1 1 d . . . H9 H 0.5236 -0.1439 0.6044 0.040 Uiso 1 1 calc R . . C10 C 0.6233(2) -0.1299(2) 0.7299(2) 0.0280(5) Uani 1 1 d . . . H10 H 0.7099 -0.2081 0.7144 0.034 Uiso 1 1 calc R . . C11 C 0.6063(2) -0.0526(2) 0.81795(19) 0.0250(4) Uani 1 1 d . . . H11 H 0.6812 -0.0784 0.8638 0.030 Uiso 1 1 calc R . . C12 C 0.4805(2) 0.0618(2) 0.83920(18) 0.0224(4) Uani 1 1 d . . . H12 H 0.4705 0.1146 0.8990 0.027 Uiso 1 1 calc R . . C13 C 0.1524(2) 0.22405(19) 0.94056(18) 0.0187(4) Uani 1 1 d . . . C14 C 0.1065(2) 0.1114(2) 1.00045(19) 0.0221(4) Uani 1 1 d . . . H14 H 0.1304 0.0409 0.9539 0.027 Uiso 1 1 calc R . . C15 C 0.0258(2) 0.1014(2) 1.1278(2) 0.0266(5) Uani 1 1 d . . . H15 H -0.0056 0.0246 1.1679 0.032 Uiso 1 1 calc R . . C16 C -0.0085(2) 0.2036(2) 1.1959(2) 0.0304(5) Uani 1 1 d . . . H16 H -0.0639 0.1973 1.2828 0.036 Uiso 1 1 calc R . . C17 C 0.0378(3) 0.3149(2) 1.1376(2) 0.0320(5) Uani 1 1 d . . . H17 H 0.0146 0.3847 1.1849 0.038 Uiso 1 1 calc R . . C18 C 0.1184(2) 0.3257(2) 1.0101(2) 0.0255(4) Uani 1 1 d . . . H18 H 0.1500 0.4024 0.9707 0.031 Uiso 1 1 calc R . . S1 S 0.62829(7) 0.34845(6) 0.84864(6) 0.03627(15) Uani 1 1 d . . . O2 O 0.46016(18) 0.39856(17) 0.88941(16) 0.0357(4) Uani 1 1 d . . . C19 C 0.6927(3) 0.2815(3) 0.9920(3) 0.0550(8) Uani 1 1 d . . . H19A H 0.6534 0.3530 1.0448 0.082 Uiso 1 1 calc R . . H19B H 0.8026 0.2497 0.9705 0.082 Uiso 1 1 calc R . . H19C H 0.6576 0.2051 1.0397 0.082 Uiso 1 1 calc R . . C20 C 0.6852(3) 0.4952(3) 0.8029(3) 0.0510(7) Uani 1 1 d . . . H20A H 0.6489 0.5529 0.7276 0.077 Uiso 1 1 calc R . . H20B H 0.7950 0.4663 0.7822 0.077 Uiso 1 1 calc R . . H20C H 0.6431 0.5469 0.8739 0.077 Uiso 1 1 calc R . . H2N H 0.342(2) 0.365(2) 0.781(2) 0.025(6) Uiso 1 1 d D . . H4N H 0.053(2) 0.701(2) 0.4257(19) 0.017(6) Uiso 1 1 d 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 0.02066(18) 0.01675(18) 0.01807(17) 0.00223(12) -0.00929(13) -0.00888(14) O1 0.0311(8) 0.0251(8) 0.0316(8) 0.0115(6) -0.0202(6) -0.0182(7) N1 0.0200(8) 0.0179(8) 0.0182(8) 0.0038(6) -0.0094(6) -0.0101(7) N2 0.0236(9) 0.0223(9) 0.0206(8) 0.0046(7) -0.0130(7) -0.0128(7) N3 0.0215(8) 0.0200(8) 0.0172(8) 0.0028(6) -0.0081(6) -0.0113(7) N4 0.0323(10) 0.0168(9) 0.0272(9) 0.0094(7) -0.0191(8) -0.0130(8) N5 0.0307(10) 0.0222(9) 0.0210(8) 0.0053(7) -0.0123(7) -0.0170(8) C1 0.0194(10) 0.0204(10) 0.0203(9) 0.0022(8) -0.0093(8) -0.0077(8) C2 0.0207(10) 0.0180(9) 0.0194(9) 0.0050(7) -0.0106(8) -0.0097(8) C3 0.0170(9) 0.0200(9) 0.0157(9) -0.0013(7) -0.0047(7) -0.0071(8) C4 0.0213(10) 0.0190(9) 0.0146(9) -0.0002(7) -0.0042(7) -0.0098(8) C5 0.0343(13) 0.0369(13) 0.0360(12) 0.0049(10) -0.0150(10) -0.0254(11) C6 0.0318(12) 0.0183(10) 0.0254(10) 0.0010(8) -0.0083(9) -0.0121(9) C7 0.0192(10) 0.0204(10) 0.0172(9) 0.0040(7) -0.0061(7) -0.0099(8) C8 0.0283(11) 0.0307(12) 0.0318(11) -0.0054(9) -0.0155(9) -0.0106(9) C9 0.0354(13) 0.0326(12) 0.0408(13) -0.0148(10) -0.0133(10) -0.0115(10) C10 0.0252(11) 0.0230(11) 0.0340(12) -0.0035(9) -0.0083(9) -0.0064(9) C11 0.0211(10) 0.0294(11) 0.0234(10) 0.0016(8) -0.0102(8) -0.0077(9) C12 0.0231(10) 0.0269(11) 0.0190(9) -0.0023(8) -0.0091(8) -0.0083(8) C13 0.0148(9) 0.0188(9) 0.0202(9) 0.0040(7) -0.0100(7) -0.0033(7) C14 0.0224(10) 0.0229(10) 0.0222(10) 0.0033(8) -0.0117(8) -0.0086(8) C15 0.0233(11) 0.0295(11) 0.0259(11) 0.0078(9) -0.0110(9) -0.0121(9) C16 0.0224(11) 0.0354(12) 0.0231(10) 0.0007(9) -0.0029(8) -0.0049(9) C17 0.0319(12) 0.0243(11) 0.0300(11) -0.0061(9) -0.0057(9) 0.0004(9) C18 0.0253(11) 0.0171(10) 0.0277(11) 0.0025(8) -0.0081(9) -0.0035(8) S1 0.0311(3) 0.0362(3) 0.0453(4) -0.0194(3) -0.0038(3) -0.0111(3) O2 0.0296(9) 0.0437(10) 0.0414(9) -0.0122(8) -0.0135(7) -0.0131(7) C19 0.0345(15) 0.0490(17) 0.074(2) 0.0007(15) -0.0272(14) -0.0026(13) C20 0.0447(16) 0.0499(17) 0.0582(17) -0.0146(14) 0.0046(13) -0.0253(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 N4 1.9034(17) 2_566 ? Cu1 N4 1.9034(17) . ? Cu1 N1 2.0459(15) 2_566 ? Cu1 N1 2.0459(15) . ? O1 C1 1.227(2) . ? N1 C1 1.366(2) . ? N1 C3 1.393(2) . ? N2 C3 1.349(2) . ? N2 C2 1.446(2) . ? N2 H2N 0.806(19) . ? N3 C3 1.307(2) . ? N3 C4 1.366(2) . ? N4 C4 1.312(2) . ? N4 H4N 0.773(18) . ? N5 C4 1.358(2) . ? N5 C6 1.454(2) . ? N5 C5 1.459(3) . ? C1 C2 1.550(3) . ? C2 C13 1.532(3) . ? C2 C7 1.534(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.383(3) . ? C7 C12 1.394(3) . ? C8 C9 1.395(3) . ? C8 H8 0.9500 . ? C9 C10 1.381(3) . ? C9 H9 0.9500 . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.389(3) . ? C13 C14 1.395(3) . ? C14 C15 1.391(3) . ? C14 H14 0.9500 . ? C15 C16 1.382(3) . ? C15 H15 0.9500 . ? C16 C17 1.382(3) . ? C16 H16 0.9500 . ? C17 C18 1.393(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? S1 O2 1.5004(17) . ? S1 C19 1.778(3) . ? S1 C20 1.787(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N4 180.00(11) 2_566 . ? N4 Cu1 N1 87.48(7) 2_566 2_566 ? N4 Cu1 N1 92.52(7) . 2_566 ? N4 Cu1 N1 92.52(7) 2_566 . ? N4 Cu1 N1 87.48(7) . . ? N1 Cu1 N1 180.0 2_566 . ? C1 N1 C3 107.07(15) . . ? C1 N1 Cu1 130.62(12) . . ? C3 N1 Cu1 122.30(12) . . ? C3 N2 C2 111.91(16) . . ? C3 N2 H2N 123.2(16) . . ? C2 N2 H2N 124.6(16) . . ? C3 N3 C4 121.03(16) . . ? C4 N4 Cu1 132.38(14) . . ? C4 N4 H4N 113.6(16) . . ? Cu1 N4 H4N 113.1(16) . . ? C4 N5 C6 120.85(16) . . ? C4 N5 C5 121.52(17) . . ? C6 N5 C5 117.63(16) . . ? O1 C1 N1 127.49(17) . . ? O1 C1 C2 122.16(16) . . ? N1 C1 C2 110.34(15) . . ? N2 C2 C13 113.60(16) . . ? N2 C2 C7 110.46(16) . . ? C13 C2 C7 111.22(15) . . ? N2 C2 C1 99.34(14) . . ? C13 C2 C1 108.85(15) . . ? C7 C2 C1 112.89(16) . . ? N3 C3 N2 118.42(17) . . ? N3 C3 N1 130.24(17) . . ? N2 C3 N1 111.33(16) . . ? N4 C4 N5 121.02(17) . . ? N4 C4 N3 125.70(17) . . ? N5 C4 N3 113.25(16) . . ? N5 C5 H5A 109.5 . . ? N5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N5 C6 H6A 109.5 . . ? N5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 118.73(19) . . ? C8 C7 C2 124.01(17) . . ? C12 C7 C2 117.18(17) . . ? C7 C8 C9 120.17(19) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.8(2) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.1(2) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 120.14(19) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C7 121.00(19) . . ? C11 C12 H12 119.5 . . ? C7 C12 H12 119.5 . . ? C18 C13 C14 119.20(18) . . ? C18 C13 C2 121.79(17) . . ? C14 C13 C2 118.99(17) . . ? C15 C14 C13 120.57(19) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 119.8(2) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 120.0(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.5(2) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C18 C17 119.93(19) . . ? C13 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? O2 S1 C19 106.27(12) . . ? O2 S1 C20 106.89(12) . . ? C19 S1 C20 96.92(15) . . ? S1 C19 H19A 109.5 . . ? S1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? S1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? S1 C20 H20A 109.5 . . ? S1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? S1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 N4 Cu1 N1 C1 -6.59(18) 2_566 . . . ? N4 Cu1 N1 C1 173.41(18) . . . . ? N1 Cu1 N1 C1 48(100) 2_566 . . . ? N4 Cu1 N1 C3 174.21(15) 2_566 . . . ? N4 Cu1 N1 C3 -5.79(15) . . . . ? N1 Cu1 N1 C3 -131(100) 2_566 . . . ? N4 Cu1 N4 C4 176(100) 2_566 . . . ? N1 Cu1 N4 C4 -169.8(2) 2_566 . . . ? N1 Cu1 N4 C4 10.2(2) . . . . ? C3 N1 C1 O1 178.5(2) . . . . ? Cu1 N1 C1 O1 -0.8(3) . . . . ? C3 N1 C1 C2 -0.6(2) . . . . ? Cu1 N1 C1 C2 -179.91(13) . . . . ? C3 N2 C2 C13 -116.34(18) . . . . ? C3 N2 C2 C7 117.89(17) . . . . ? C3 N2 C2 C1 -0.9(2) . . . . ? O1 C1 C2 N2 -178.26(19) . . . . ? N1 C1 C2 N2 0.9(2) . . . . ? O1 C1 C2 C13 -59.3(2) . . . . ? N1 C1 C2 C13 119.93(17) . . . . ? O1 C1 C2 C7 64.7(2) . . . . ? N1 C1 C2 C7 -116.06(18) . . . . ? C4 N3 C3 N2 -173.92(17) . . . . ? C4 N3 C3 N1 5.6(3) . . . . ? C2 N2 C3 N3 -179.72(17) . . . . ? C2 N2 C3 N1 0.7(2) . . . . ? C1 N1 C3 N3 -179.6(2) . . . . ? Cu1 N1 C3 N3 -0.2(3) . . . . ? C1 N1 C3 N2 0.0(2) . . . . ? Cu1 N1 C3 N2 179.37(12) . . . . ? Cu1 N4 C4 N5 173.66(15) . . . . ? Cu1 N4 C4 N3 -8.3(3) . . . . ? C6 N5 C4 N4 5.4(3) . . . . ? C5 N5 C4 N4 -174.14(19) . . . . ? C6 N5 C4 N3 -172.85(17) . . . . ? C5 N5 C4 N3 7.6(3) . . . . ? C3 N3 C4 N4 -1.7(3) . . . . ? C3 N3 C4 N5 176.48(17) . . . . ? N2 C2 C7 C8 -110.6(2) . . . . ? C13 C2 C7 C8 122.3(2) . . . . ? C1 C2 C7 C8 -0.4(3) . . . . ? N2 C2 C7 C12 66.1(2) . . . . ? C13 C2 C7 C12 -61.0(2) . . . . ? C1 C2 C7 C12 176.31(16) . . . . ? C12 C7 C8 C9 -0.6(3) . . . . ? C2 C7 C8 C9 176.05(19) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? C10 C11 C12 C7 0.7(3) . . . . ? C8 C7 C12 C11 -0.1(3) . . . . ? C2 C7 C12 C11 -176.96(18) . . . . ? N2 C2 C13 C18 5.4(3) . . . . ? C7 C2 C13 C18 130.72(19) . . . . ? C1 C2 C13 C18 -104.3(2) . . . . ? N2 C2 C13 C14 -175.60(16) . . . . ? C7 C2 C13 C14 -50.2(2) . . . . ? C1 C2 C13 C14 74.8(2) . . . . ? C18 C13 C14 C15 0.8(3) . . . . ? C2 C13 C14 C15 -178.25(17) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 -0.3(3) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C14 C13 C18 C17 -0.7(3) . . . . ? C2 C13 C18 C17 178.35(18) . . . . ? C16 C17 C18 C13 0.1(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 N2 H2N O2 0.806(19) 2.115(19) 2.913(2) 171(2) . N4 H4N O1 0.773(18) 2.084(19) 2.798(2) 154(2) 2_566 _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 28.18 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 0.410 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.060 #===END data_4b _database_code_depnum_ccdc_archive 'CCDC 265657' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H48 N10 Ni O4 S2' _chemical_formula_weight 855.71 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' Ni Ni 0.3393 1.1124 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.927(2) _cell_length_b 10.814(2) _cell_length_c 11.116(3) _cell_angle_alpha 73.819(4) _cell_angle_beta 71.650(3) _cell_angle_gamma 66.708(3) _cell_volume 1024.0(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 966 _cell_measurement_theta_min 2.526 _cell_measurement_theta_max 27.964 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.502 _exptl_crystal_size_mid 0.286 _exptl_crystal_size_min 0.114 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 450 _exptl_absorpt_coefficient_mu 0.630 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.792 _exptl_absorpt_correction_T_max 0.937 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 110 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.2 _diffrn_reflns_number 9445 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.03 _reflns_number_total 4507 _reflns_number_gt 4041 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _computing_publication_material ? _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^)+(0.0200P)^2^+1.0000P] 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 4507 _refine_ls_number_parameters 271 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0998 _refine_ls_goodness_of_fit_ref 1.394 _refine_ls_restrained_S_all 1.394 _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 Ni1 Ni 0.0000 0.5000 0.5000 0.01905(11) Uani 1 2 d S . . O1 O 0.04285(19) 0.20605(17) 0.72818(16) 0.0252(4) Uani 1 1 d . . . N1 N 0.1170(2) 0.39699(18) 0.63142(17) 0.0167(4) Uani 1 1 d . . . N2 N 0.2857(2) 0.35163(19) 0.74935(18) 0.0193(4) Uani 1 1 d D . . H2N H 0.342(2) 0.368(3) 0.782(2) 0.021(7) Uiso 1 1 d D . . N3 N 0.2572(2) 0.54860(19) 0.60306(18) 0.0184(4) Uani 1 1 d . . . N4 N 0.0740(2) 0.64097(19) 0.47805(19) 0.0210(4) Uani 1 1 d D . . H4N H 0.044(3) 0.7072(19) 0.4210(19) 0.024(7) Uiso 1 1 d D . . N5 N 0.2253(2) 0.7591(2) 0.47737(18) 0.0216(4) Uani 1 1 d . . . C1 C 0.1188(2) 0.2768(2) 0.7148(2) 0.0186(4) Uani 1 1 d . . . C2 C 0.2334(2) 0.2366(2) 0.7980(2) 0.0179(4) Uani 1 1 d . . . C3 C 0.2200(2) 0.4399(2) 0.6556(2) 0.0165(4) Uani 1 1 d . . . C4 C 0.1818(2) 0.6469(2) 0.5176(2) 0.0176(4) Uani 1 1 d . . . C5 C 0.3559(3) 0.7601(3) 0.5091(3) 0.0313(6) Uani 1 1 d . . . H5A H 0.3304 0.7697 0.5995 0.047 Uiso 1 1 calc R . . H5B H 0.3864 0.8371 0.4537 0.047 Uiso 1 1 calc R . . H5C H 0.4391 0.6742 0.4957 0.047 Uiso 1 1 calc R . . C6 C 0.1480(3) 0.8788(2) 0.3948(2) 0.0233(5) Uani 1 1 d . . . H6A H 0.1783 0.8607 0.3068 0.035 Uiso 1 1 calc R . . H6B H 0.1746 0.9568 0.3951 0.035 Uiso 1 1 calc R . . H6C H 0.0388 0.8997 0.4267 0.035 Uiso 1 1 calc R . . C7 C 0.3642(2) 0.1037(2) 0.7734(2) 0.0181(4) Uani 1 1 d . . . C8 C 0.3793(3) 0.0260(3) 0.6872(2) 0.0273(5) Uani 1 1 d . . . H8 H 0.3023 0.0510 0.6427 0.033 Uiso 1 1 calc R . . C9 C 0.5070(3) -0.0887(3) 0.6652(3) 0.0326(6) Uani 1 1 d . . . H9 H 0.5169 -0.1411 0.6051 0.039 Uiso 1 1 calc R . . C10 C 0.6190(3) -0.1272(2) 0.7295(2) 0.0271(5) Uani 1 1 d . . . H10 H 0.7059 -0.2057 0.7140 0.032 Uiso 1 1 calc R . . C11 C 0.6039(3) -0.0505(2) 0.8171(2) 0.0238(5) Uani 1 1 d . . . H11 H 0.6803 -0.0766 0.8625 0.029 Uiso 1 1 calc R . . C12 C 0.4779(3) 0.0638(2) 0.8383(2) 0.0216(5) Uani 1 1 d . . . H12 H 0.4687 0.1162 0.8982 0.026 Uiso 1 1 calc R . . C13 C 0.1500(2) 0.2266(2) 0.9398(2) 0.0182(4) Uani 1 1 d . . . C14 C 0.1025(3) 0.1145(2) 1.0004(2) 0.0213(5) Uani 1 1 d . . . H14 H 0.1253 0.0442 0.9540 0.026 Uiso 1 1 calc R . . C15 C 0.0223(3) 0.1046(3) 1.1278(2) 0.0255(5) Uani 1 1 d . . . H15 H -0.0105 0.0283 1.1680 0.031 Uiso 1 1 calc R . . C16 C -0.0099(3) 0.2058(3) 1.1960(2) 0.0290(5) Uani 1 1 d . . . H16 H -0.0654 0.1995 1.2831 0.035 Uiso 1 1 calc R . . C17 C 0.0387(3) 0.3160(3) 1.1374(2) 0.0305(6) Uani 1 1 d . . . H17 H 0.0176 0.3849 1.1848 0.037 Uiso 1 1 calc R . . C18 C 0.1184(3) 0.3269(2) 1.0094(2) 0.0245(5) Uani 1 1 d . . . H18 H 0.1511 0.4034 0.9696 0.029 Uiso 1 1 calc R . . S1 S 0.62375(8) 0.35364(7) 0.84272(7) 0.03355(17) Uani 1 1 d . . . O2 O 0.4552(2) 0.4008(2) 0.88832(19) 0.0339(4) Uani 1 1 d . . . C19 C 0.6957(4) 0.2839(4) 0.9840(4) 0.0542(9) Uani 1 1 d . . . H19A H 0.6590 0.3543 1.0373 0.081 Uiso 1 1 calc R . . H19B H 0.8061 0.2521 0.9597 0.081 Uiso 1 1 calc R . . H19C H 0.6615 0.2067 1.0329 0.081 Uiso 1 1 calc R . . C20 C 0.6770(4) 0.5020(3) 0.7963(3) 0.0505(8) Uani 1 1 d . . . H20A H 0.6344 0.5620 0.7235 0.076 Uiso 1 1 calc R . . H20B H 0.7871 0.4751 0.7709 0.076 Uiso 1 1 calc R . . H20C H 0.6387 0.5508 0.8690 0.076 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 Ni1 0.0211(2) 0.0193(2) 0.0192(2) 0.00151(16) -0.00903(16) -0.00933(17) O1 0.0295(9) 0.0248(9) 0.0283(9) 0.0121(7) -0.0195(7) -0.0178(7) N1 0.0175(9) 0.0177(9) 0.0169(9) 0.0026(7) -0.0078(7) -0.0089(7) N2 0.0213(10) 0.0205(9) 0.0209(10) 0.0042(7) -0.0116(8) -0.0121(8) N3 0.0204(9) 0.0204(9) 0.0176(9) 0.0028(7) -0.0083(7) -0.0111(8) N4 0.0258(10) 0.0159(9) 0.0249(10) 0.0072(8) -0.0150(8) -0.0110(8) N5 0.0300(11) 0.0220(10) 0.0201(10) 0.0057(8) -0.0130(8) -0.0170(9) C1 0.0188(11) 0.0199(11) 0.0178(10) 0.0026(8) -0.0083(9) -0.0079(9) C2 0.0191(11) 0.0189(10) 0.0181(11) 0.0036(8) -0.0097(9) -0.0095(9) C3 0.0145(10) 0.0200(10) 0.0147(10) -0.0020(8) -0.0035(8) -0.0062(8) C4 0.0207(11) 0.0184(10) 0.0144(10) -0.0004(8) -0.0033(8) -0.0097(9) C5 0.0356(14) 0.0368(14) 0.0328(14) 0.0054(11) -0.0146(11) -0.0264(12) C6 0.0302(13) 0.0178(11) 0.0239(12) 0.0013(9) -0.0083(10) -0.0120(10) C7 0.0193(11) 0.0192(11) 0.0162(10) 0.0034(8) -0.0056(8) -0.0103(9) C8 0.0265(13) 0.0307(13) 0.0317(13) -0.0059(10) -0.0153(11) -0.0101(11) C9 0.0333(14) 0.0320(14) 0.0407(15) -0.0152(12) -0.0130(12) -0.0100(11) C10 0.0232(12) 0.0221(12) 0.0336(14) -0.0043(10) -0.0066(10) -0.0057(10) C11 0.0204(11) 0.0278(12) 0.0220(12) 0.0013(9) -0.0092(9) -0.0074(10) C12 0.0221(11) 0.0261(12) 0.0181(11) -0.0015(9) -0.0084(9) -0.0087(10) C13 0.0139(10) 0.0195(11) 0.0184(11) 0.0033(8) -0.0089(8) -0.0032(8) C14 0.0207(11) 0.0230(11) 0.0215(11) 0.0024(9) -0.0110(9) -0.0081(9) C15 0.0212(12) 0.0291(13) 0.0243(12) 0.0073(10) -0.0102(10) -0.0110(10) C16 0.0209(12) 0.0335(14) 0.0212(12) 0.0001(10) -0.0022(10) -0.0028(10) C17 0.0298(13) 0.0237(12) 0.0277(13) -0.0064(10) -0.0046(11) 0.0013(10) C18 0.0239(12) 0.0169(11) 0.0263(12) 0.0008(9) -0.0066(10) -0.0029(9) S1 0.0298(3) 0.0343(4) 0.0401(4) -0.0166(3) -0.0042(3) -0.0107(3) O2 0.0277(10) 0.0416(11) 0.0391(11) -0.0109(9) -0.0132(8) -0.0119(8) C19 0.0319(16) 0.057(2) 0.065(2) -0.0007(17) -0.0242(16) -0.0018(15) C20 0.0449(18) 0.0469(19) 0.059(2) -0.0146(16) 0.0067(16) -0.0254(16) _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 Ni1 N4 1.8679(19) . ? Ni1 N4 1.8679(19) 2_566 ? Ni1 N1 1.9652(18) . ? Ni1 N1 1.9652(18) 2_566 ? O1 C1 1.224(3) . ? N1 C1 1.367(3) . ? N1 C3 1.396(3) . ? N2 C3 1.343(3) . ? N2 C2 1.438(3) . ? N2 H2N 0.840(10) . ? N3 C3 1.298(3) . ? N3 C4 1.359(3) . ? N4 C4 1.307(3) . ? N4 H4N 0.837(10) . ? N5 C4 1.360(3) . ? N5 C6 1.450(3) . ? N5 C5 1.452(3) . ? C1 C2 1.545(3) . ? C2 C13 1.528(3) . ? C2 C7 1.532(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.380(3) . ? C7 C12 1.391(3) . ? C8 C9 1.392(4) . ? C8 H8 0.9500 . ? C9 C10 1.374(4) . ? C9 H9 0.9500 . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.379(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.385(3) . ? C13 C14 1.394(3) . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 C16 1.382(4) . ? C15 H15 0.9500 . ? C16 C17 1.378(4) . ? C16 H16 0.9500 . ? C17 C18 1.392(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? S1 O2 1.500(2) . ? S1 C20 1.777(3) . ? S1 C19 1.779(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ni1 N4 180.0 . 2_566 ? N4 Ni1 N1 88.12(8) . . ? N4 Ni1 N1 91.88(8) 2_566 . ? N4 Ni1 N1 91.88(8) . 2_566 ? N4 Ni1 N1 88.12(8) 2_566 2_566 ? N1 Ni1 N1 180.000(1) . 2_566 ? C1 N1 C3 106.29(17) . . ? C1 N1 Ni1 130.58(14) . . ? C3 N1 Ni1 123.14(14) . . ? C3 N2 C2 111.95(18) . . ? C3 N2 H2N 123.4(18) . . ? C2 N2 H2N 124.2(18) . . ? C3 N3 C4 119.84(19) . . ? C4 N4 Ni1 132.27(16) . . ? C4 N4 H4N 113.4(19) . . ? Ni1 N4 H4N 113.1(19) . . ? C4 N5 C6 120.93(19) . . ? C4 N5 C5 121.20(19) . . ? C6 N5 C5 117.77(19) . . ? O1 C1 N1 128.0(2) . . ? O1 C1 C2 121.33(19) . . ? N1 C1 C2 110.64(18) . . ? N2 C2 C13 113.73(19) . . ? N2 C2 C7 110.33(18) . . ? C13 C2 C7 111.10(17) . . ? N2 C2 C1 99.43(16) . . ? C13 C2 C1 108.85(17) . . ? C7 C2 C1 112.94(18) . . ? N3 C3 N2 118.33(19) . . ? N3 C3 N1 130.0(2) . . ? N2 C3 N1 111.67(18) . . ? N4 C4 N3 125.43(19) . . ? N4 C4 N5 121.1(2) . . ? N3 C4 N5 113.47(19) . . ? N5 C5 H5A 109.5 . . ? N5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N5 C6 H6A 109.5 . . ? N5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 118.6(2) . . ? C8 C7 C2 124.3(2) . . ? C12 C7 C2 117.0(2) . . ? C7 C8 C9 120.2(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.8(2) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.3(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C7 121.0(2) . . ? C11 C12 H12 119.5 . . ? C7 C12 H12 119.5 . . ? C18 C13 C14 119.0(2) . . ? C18 C13 C2 121.8(2) . . ? C14 C13 C2 119.1(2) . . ? C15 C14 C13 120.6(2) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 120.0(2) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.5(2) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C18 C17 120.1(2) . . ? C13 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? O2 S1 C20 106.82(14) . . ? O2 S1 C19 106.02(14) . . ? C20 S1 C19 97.12(18) . . ? S1 C19 H19A 109.5 . . ? S1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? S1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? S1 C20 H20A 109.5 . . ? S1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? S1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 N4 Ni1 N1 C1 172.2(2) . . . . ? N4 Ni1 N1 C1 -7.8(2) 2_566 . . . ? N1 Ni1 N1 C1 -19(100) 2_566 . . . ? N4 Ni1 N1 C3 -7.76(18) . . . . ? N4 Ni1 N1 C3 172.24(18) 2_566 . . . ? N1 Ni1 N1 C3 161(100) 2_566 . . . ? N4 Ni1 N4 C4 -101(100) 2_566 . . . ? N1 Ni1 N4 C4 12.1(2) . . . . ? N1 Ni1 N4 C4 -167.9(2) 2_566 . . . ? C3 N1 C1 O1 178.2(2) . . . . ? Ni1 N1 C1 O1 -1.8(4) . . . . ? C3 N1 C1 C2 -1.1(2) . . . . ? Ni1 N1 C1 C2 178.94(15) . . . . ? C3 N2 C2 C13 -116.7(2) . . . . ? C3 N2 C2 C7 117.7(2) . . . . ? C3 N2 C2 C1 -1.2(2) . . . . ? O1 C1 C2 N2 -177.9(2) . . . . ? N1 C1 C2 N2 1.4(2) . . . . ? O1 C1 C2 C13 -58.7(3) . . . . ? N1 C1 C2 C13 120.6(2) . . . . ? O1 C1 C2 C7 65.2(3) . . . . ? N1 C1 C2 C7 -115.5(2) . . . . ? C4 N3 C3 N2 -173.2(2) . . . . ? C4 N3 C3 N1 6.0(4) . . . . ? C2 N2 C3 N3 180.0(2) . . . . ? C2 N2 C3 N1 0.7(3) . . . . ? C1 N1 C3 N3 -178.9(2) . . . . ? Ni1 N1 C3 N3 1.1(3) . . . . ? C1 N1 C3 N2 0.3(3) . . . . ? Ni1 N1 C3 N2 -179.73(15) . . . . ? Ni1 N4 C4 N3 -9.1(4) . . . . ? Ni1 N4 C4 N5 173.08(17) . . . . ? C3 N3 C4 N4 -2.4(4) . . . . ? C3 N3 C4 N5 175.6(2) . . . . ? C6 N5 C4 N4 3.4(3) . . . . ? C5 N5 C4 N4 -172.9(2) . . . . ? C6 N5 C4 N3 -174.6(2) . . . . ? C5 N5 C4 N3 9.1(3) . . . . ? N2 C2 C7 C8 -110.8(2) . . . . ? C13 C2 C7 C8 122.1(2) . . . . ? C1 C2 C7 C8 -0.5(3) . . . . ? N2 C2 C7 C12 65.9(2) . . . . ? C13 C2 C7 C12 -61.2(2) . . . . ? C1 C2 C7 C12 176.14(19) . . . . ? C12 C7 C8 C9 -0.7(4) . . . . ? C2 C7 C8 C9 175.9(2) . . . . ? C7 C8 C9 C10 0.6(4) . . . . ? C8 C9 C10 C11 0.0(4) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? C10 C11 C12 C7 0.3(4) . . . . ? C8 C7 C12 C11 0.3(3) . . . . ? C2 C7 C12 C11 -176.6(2) . . . . ? N2 C2 C13 C18 5.1(3) . . . . ? C7 C2 C13 C18 130.4(2) . . . . ? C1 C2 C13 C18 -104.7(2) . . . . ? N2 C2 C13 C14 -175.80(19) . . . . ? C7 C2 C13 C14 -50.6(3) . . . . ? C1 C2 C13 C14 74.4(2) . . . . ? C18 C13 C14 C15 1.2(3) . . . . ? C2 C13 C14 C15 -177.9(2) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? C14 C15 C16 C17 -0.4(4) . . . . ? C15 C16 C17 C18 0.8(4) . . . . ? C14 C13 C18 C17 -0.8(3) . . . . ? C2 C13 C18 C17 178.3(2) . . . . ? C16 C17 C18 C13 -0.2(4) . . . . ? 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 N2 H2N O2 0.840(10) 2.050(11) 2.882(3) 171(3) . N4 H4N O1 0.837(10) 1.941(15) 2.717(2) 154(3) 2_566 _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.909 _refine_diff_density_max 0.578 _refine_diff_density_min -1.003 _refine_diff_density_rms 0.073 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 265658' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H20 Cl2 Cu N6 O9 S' _chemical_formula_weight 546.83 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6940(13) _cell_length_b 7.3720(8) _cell_length_c 23.655(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.630(2) _cell_angle_gamma 90.00 _cell_volume 2032.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 925 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 27.86 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.357 _exptl_crystal_size_mid 0.179 _exptl_crystal_size_min 0.070 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.787 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116 _exptl_absorpt_coefficient_mu 1.499 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.622 _exptl_absorpt_correction_T_max 0.925 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 207 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.02 _diffrn_reflns_number 19465 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4859 _reflns_number_gt 4052 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _computing_publication_material ? _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^)+(0.03P)^2^+0.2P] 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 4859 _refine_ls_number_parameters 289 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 1.296 _refine_ls_restrained_S_all 1.300 _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 0.265692(17) 0.20208(3) 0.089836(9) 0.02702(8) Uani 1 1 d . . . S1 S 0.13697(4) 0.15010(7) 0.00995(2) 0.03358(12) Uani 1 1 d . . . O1 O 0.40664(11) 0.2992(2) 0.25431(6) 0.0392(3) Uani 1 1 d . . . N1 N 0.37024(13) 0.2346(2) 0.15796(6) 0.0280(3) Uani 1 1 d D . . H1N H 0.4403(14) 0.237(3) 0.1584(10) 0.039(6) Uiso 1 1 d D . . N2 N 0.22983(14) 0.2430(3) 0.22264(7) 0.0347(4) Uani 1 1 d . . . H2N H 0.2229(17) 0.270(3) 0.2535(10) 0.027(6) Uiso 1 1 d . . . N3 N 0.03643(15) 0.1917(3) 0.21590(8) 0.0404(4) Uani 1 1 d D . . H3N H -0.0223(16) 0.173(3) 0.1966(9) 0.041(7) Uiso 1 1 d D . . N4 N 0.13078(12) 0.2230(2) 0.13298(7) 0.0294(3) Uani 1 1 d . . . N5 N 0.37596(13) 0.2327(2) 0.03187(7) 0.0309(3) Uani 1 1 d . . . N6 N 0.51801(16) 0.2677(3) -0.02092(8) 0.0422(4) Uani 1 1 d D . . H6N H 0.5810(15) 0.262(4) -0.0303(11) 0.055(8) Uiso 1 1 d D . . C1 C 0.52762(17) 0.3301(3) 0.25039(9) 0.0413(5) Uani 1 1 d . . . H1A H 0.5644 0.2165 0.2402 0.062 Uiso 1 1 calc R . . H1B H 0.5624 0.3729 0.2871 0.062 Uiso 1 1 calc R . . H1C H 0.5382 0.4217 0.2213 0.062 Uiso 1 1 calc R . . C2 C 0.34027(15) 0.2595(3) 0.20782(8) 0.0275(4) Uani 1 1 d . . . C3 C 0.13039(15) 0.2173(3) 0.18785(8) 0.0299(4) Uani 1 1 d . . . C4 C 0.0313(2) 0.1736(4) 0.27682(10) 0.0505(6) Uani 1 1 d . . . H4A H 0.0862 0.0811 0.2914 0.076 Uiso 1 1 calc R . . H4B H -0.0463 0.1374 0.2850 0.076 Uiso 1 1 calc R . . H4C H 0.0505 0.2900 0.2952 0.076 Uiso 1 1 calc R . . C5 C 0.01849(15) 0.2102(3) 0.10071(8) 0.0339(4) Uani 1 1 d . . . H5A H -0.0386 0.2824 0.1198 0.041 Uiso 1 1 calc R . . H5B H -0.0073 0.0823 0.0994 0.041 Uiso 1 1 calc R . . C6 C 0.02642(16) 0.2803(3) 0.04084(8) 0.0355(4) Uani 1 1 d . . . H6A H 0.0465 0.4108 0.0416 0.043 Uiso 1 1 calc R . . H6B H -0.0480 0.2649 0.0183 0.043 Uiso 1 1 calc R . . C7 C 0.20729(17) 0.3109(3) -0.03487(8) 0.0393(5) Uani 1 1 d . . . H7A H 0.1854 0.2859 -0.0754 0.047 Uiso 1 1 calc R . . H7B H 0.1845 0.4367 -0.0263 0.047 Uiso 1 1 calc R . . C8 C 0.33302(16) 0.2868(3) -0.02212(8) 0.0308(4) Uani 1 1 d . . . C9 C 0.42145(17) 0.3093(3) -0.05523(8) 0.0355(4) Uani 1 1 d . . . C10 C 0.4259(2) 0.3671(4) -0.11535(9) 0.0510(6) Uani 1 1 d . . . H10A H 0.4357 0.2603 -0.1391 0.076 Uiso 1 1 calc R . . H10B H 0.4907 0.4500 -0.1183 0.076 Uiso 1 1 calc R . . H10C H 0.3543 0.4290 -0.1281 0.076 Uiso 1 1 calc R . . C11 C 0.48768(17) 0.2223(3) 0.03020(9) 0.0391(5) Uani 1 1 d . . . H11 H 0.5397 0.1872 0.0612 0.047 Uiso 1 1 calc R . . Cl1 Cl 0.22316(4) -0.28698(7) 0.10997(2) 0.03684(12) Uani 1 1 d . . . O2 O 0.25520(16) -0.4215(3) 0.07019(8) 0.0681(5) Uani 1 1 d . . . O3 O 0.10594(15) -0.2401(3) 0.09829(9) 0.0699(5) Uani 1 1 d . . . O4 O 0.29698(15) -0.1332(2) 0.10366(10) 0.0692(5) Uani 1 1 d . . . O5 O 0.24211(17) -0.3602(3) 0.16568(8) 0.0710(5) Uani 1 1 d . . . Cl2 Cl 0.73318(4) 0.12226(9) 0.14277(2) 0.04738(15) Uani 1 1 d . . . O6 O 0.61362(11) 0.0925(2) 0.14923(6) 0.0484(4) Uani 1 1 d . . . O7 O 0.77340(19) 0.2706(4) 0.17649(11) 0.1029(9) Uani 1 1 d . . . O8 O 0.79703(16) -0.0340(4) 0.16116(10) 0.0957(8) Uani 1 1 d . . . O9 O 0.74911(14) 0.1546(4) 0.08486(7) 0.0761(7) 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 Cu1 0.02216(12) 0.03795(14) 0.02094(12) -0.00014(9) 0.00156(8) 0.00111(9) S1 0.0293(2) 0.0424(3) 0.0286(2) -0.0044(2) -0.00031(18) -0.0015(2) O1 0.0286(7) 0.0644(10) 0.0241(7) -0.0041(6) -0.0009(5) -0.0036(6) N1 0.0211(7) 0.0374(9) 0.0254(8) -0.0014(6) 0.0011(6) 0.0003(6) N2 0.0277(8) 0.0557(11) 0.0210(9) -0.0006(8) 0.0040(6) -0.0023(7) N3 0.0266(9) 0.0642(12) 0.0310(9) 0.0004(8) 0.0062(7) -0.0067(8) N4 0.0225(7) 0.0385(9) 0.0273(8) -0.0002(7) 0.0018(6) -0.0001(6) N5 0.0285(8) 0.0394(9) 0.0250(8) 0.0005(7) 0.0027(6) 0.0011(7) N6 0.0307(9) 0.0624(12) 0.0347(10) -0.0002(8) 0.0094(8) -0.0010(8) C1 0.0309(10) 0.0581(14) 0.0340(11) -0.0052(10) -0.0025(8) -0.0102(9) C2 0.0272(9) 0.0301(9) 0.0250(9) 0.0021(7) 0.0012(7) 0.0006(7) C3 0.0263(9) 0.0349(10) 0.0287(10) 0.0003(8) 0.0042(7) -0.0004(7) C4 0.0440(12) 0.0720(17) 0.0378(12) -0.0020(11) 0.0170(10) -0.0160(11) C5 0.0214(8) 0.0483(12) 0.0317(10) -0.0016(9) 0.0009(7) 0.0001(8) C6 0.0256(9) 0.0474(12) 0.0327(10) -0.0010(9) -0.0029(8) 0.0042(8) C7 0.0354(10) 0.0558(13) 0.0265(10) 0.0087(9) 0.0017(8) 0.0043(9) C8 0.0340(10) 0.0360(10) 0.0223(9) -0.0005(8) 0.0010(7) 0.0001(8) C9 0.0408(11) 0.0398(11) 0.0262(10) -0.0016(8) 0.0058(8) -0.0036(8) C10 0.0583(14) 0.0674(16) 0.0286(11) 0.0073(11) 0.0120(10) -0.0059(12) C11 0.0288(10) 0.0584(13) 0.0303(10) 0.0010(9) 0.0035(8) 0.0019(9) Cl1 0.0376(3) 0.0350(3) 0.0386(3) -0.0006(2) 0.0070(2) -0.00039(19) O2 0.0832(13) 0.0601(11) 0.0646(12) -0.0221(9) 0.0268(10) -0.0044(10) O3 0.0400(10) 0.0880(14) 0.0812(14) 0.0080(11) 0.0029(9) 0.0095(9) O4 0.0555(10) 0.0349(9) 0.1177(17) 0.0073(10) 0.0093(10) -0.0058(8) O5 0.0832(14) 0.0842(14) 0.0457(10) 0.0136(10) 0.0068(9) 0.0029(11) Cl2 0.0231(2) 0.0785(4) 0.0404(3) 0.0059(3) 0.00157(19) 0.0060(2) O6 0.0242(7) 0.0727(11) 0.0490(9) 0.0074(8) 0.0073(6) 0.0040(7) O7 0.0646(14) 0.138(2) 0.106(2) -0.0501(17) 0.0103(13) -0.0294(14) O8 0.0542(11) 0.134(2) 0.1006(17) 0.0525(15) 0.0179(11) 0.0493(13) O9 0.0388(9) 0.144(2) 0.0463(10) 0.0221(11) 0.0083(8) -0.0004(10) _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 N4 1.9530(15) . ? Cu1 N1 1.9573(15) . ? Cu1 N5 1.9697(16) . ? Cu1 S1 2.3504(5) . ? S1 C6 1.811(2) . ? S1 C7 1.829(2) . ? O1 C2 1.327(2) . ? O1 C1 1.443(2) . ? N1 C2 1.270(2) . ? N1 H1N 0.819(15) . ? N2 C2 1.371(2) . ? N2 C3 1.382(2) . ? N2 H2N 0.77(2) . ? N3 C3 1.342(2) . ? N3 C4 1.454(3) . ? N3 H3N 0.806(15) . ? N4 C3 1.299(2) . ? N4 C5 1.468(2) . ? N5 C11 1.312(2) . ? N5 C8 1.392(2) . ? N6 C11 1.330(3) . ? N6 C9 1.371(3) . ? N6 H6N 0.788(16) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.518(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.487(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.357(3) . ? C9 C10 1.489(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11 0.9500 . ? Cl1 O3 1.4191(18) . ? Cl1 O5 1.4248(18) . ? Cl1 O2 1.4372(18) . ? Cl1 O4 1.4398(17) . ? Cl2 O7 1.411(2) . ? Cl2 O9 1.4176(17) . ? Cl2 O8 1.422(2) . ? Cl2 O6 1.4356(14) . ? 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 N4 Cu1 N1 92.14(7) . . ? N4 Cu1 N5 163.05(7) . . ? N1 Cu1 N5 99.13(6) . . ? N4 Cu1 S1 86.62(5) . . ? N1 Cu1 S1 177.23(5) . . ? N5 Cu1 S1 82.63(5) . . ? C6 S1 C7 105.03(10) . . ? C6 S1 Cu1 91.20(6) . . ? C7 S1 Cu1 94.11(7) . . ? C2 O1 C1 119.50(15) . . ? C2 N1 Cu1 125.53(13) . . ? C2 N1 H1N 109.6(16) . . ? Cu1 N1 H1N 124.8(16) . . ? C2 N2 C3 128.65(17) . . ? C2 N2 H2N 113.2(16) . . ? C3 N2 H2N 117.0(16) . . ? C3 N3 C4 127.17(18) . . ? C3 N3 H3N 116.0(17) . . ? C4 N3 H3N 116.5(17) . . ? C3 N4 C5 116.26(15) . . ? C3 N4 Cu1 126.00(12) . . ? C5 N4 Cu1 116.72(12) . . ? C11 N5 C8 105.99(16) . . ? C11 N5 Cu1 136.34(14) . . ? C8 N5 Cu1 117.61(12) . . ? C11 N6 C9 109.09(17) . . ? C11 N6 H6N 125(2) . . ? C9 N6 H6N 126(2) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 O1 127.93(17) . . ? N1 C2 N2 124.11(17) . . ? O1 C2 N2 107.92(16) . . ? N4 C3 N3 124.58(17) . . ? N4 C3 N2 121.32(16) . . ? N3 C3 N2 114.08(17) . . ? N3 C4 H4A 109.5 . . ? N3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N4 C5 C6 110.11(15) . . ? N4 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? N4 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.2 . . ? C5 C6 S1 107.18(13) . . ? C5 C6 H6A 110.3 . . ? S1 C6 H6A 110.3 . . ? C5 C6 H6B 110.3 . . ? S1 C6 H6B 110.3 . . ? H6A C6 H6B 108.5 . . ? C8 C7 S1 106.77(14) . . ? C8 C7 H7A 110.4 . . ? S1 C7 H7A 110.4 . . ? C8 C7 H7B 110.4 . . ? S1 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? C9 C8 N5 109.22(17) . . ? C9 C8 C7 130.94(18) . . ? N5 C8 C7 119.84(16) . . ? C8 C9 N6 105.10(17) . . ? C8 C9 C10 132.30(19) . . ? N6 C9 C10 122.59(18) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N5 C11 N6 110.59(18) . . ? N5 C11 H11 124.7 . . ? N6 C11 H11 124.7 . . ? O3 Cl1 O5 110.36(12) . . ? O3 Cl1 O2 109.82(12) . . ? O5 Cl1 O2 108.36(13) . . ? O3 Cl1 O4 111.47(12) . . ? O5 Cl1 O4 110.14(13) . . ? O2 Cl1 O4 106.56(12) . . ? O7 Cl2 O9 110.61(16) . . ? O7 Cl2 O8 108.18(17) . . ? O9 Cl2 O8 108.99(13) . . ? O7 Cl2 O6 109.95(12) . . ? O9 Cl2 O6 109.49(9) . . ? O8 Cl2 O6 109.60(12) . . ? 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 N4 Cu1 S1 C6 27.58(8) . . . . ? N1 Cu1 S1 C6 91.1(10) . . . . ? N5 Cu1 S1 C6 -139.29(8) . . . . ? N4 Cu1 S1 C7 132.74(8) . . . . ? N1 Cu1 S1 C7 -163.8(10) . . . . ? N5 Cu1 S1 C7 -34.12(8) . . . . ? N4 Cu1 N1 C2 -0.38(17) . . . . ? N5 Cu1 N1 C2 166.91(16) . . . . ? S1 Cu1 N1 C2 -63.7(11) . . . . ? N1 Cu1 N4 C3 -12.84(17) . . . . ? N5 Cu1 N4 C3 -144.7(2) . . . . ? S1 Cu1 N4 C3 164.68(16) . . . . ? N1 Cu1 N4 C5 179.24(14) . . . . ? N5 Cu1 N4 C5 47.4(3) . . . . ? S1 Cu1 N4 C5 -3.24(13) . . . . ? N4 Cu1 N5 C11 151.2(2) . . . . ? N1 Cu1 N5 C11 20.2(2) . . . . ? S1 Cu1 N5 C11 -157.7(2) . . . . ? N4 Cu1 N5 C8 -25.4(3) . . . . ? N1 Cu1 N5 C8 -156.40(14) . . . . ? S1 Cu1 N5 C8 25.76(13) . . . . ? Cu1 N1 C2 O1 -172.99(15) . . . . ? Cu1 N1 C2 N2 9.2(3) . . . . ? C1 O1 C2 N1 3.9(3) . . . . ? C1 O1 C2 N2 -177.98(17) . . . . ? C3 N2 C2 N1 -7.6(3) . . . . ? C3 N2 C2 O1 174.22(19) . . . . ? C5 N4 C3 N3 3.5(3) . . . . ? Cu1 N4 C3 N3 -164.48(16) . . . . ? C5 N4 C3 N2 -174.69(17) . . . . ? Cu1 N4 C3 N2 17.3(3) . . . . ? C4 N3 C3 N4 176.1(2) . . . . ? C4 N3 C3 N2 -5.6(3) . . . . ? C2 N2 C3 N4 -6.8(3) . . . . ? C2 N2 C3 N3 174.9(2) . . . . ? C3 N4 C5 C6 161.13(17) . . . . ? Cu1 N4 C5 C6 -29.8(2) . . . . ? N4 C5 C6 S1 56.49(19) . . . . ? C7 S1 C6 C5 -144.30(14) . . . . ? Cu1 S1 C6 C5 -49.72(13) . . . . ? C6 S1 C7 C8 133.17(14) . . . . ? Cu1 S1 C7 C8 40.82(14) . . . . ? C11 N5 C8 C9 -0.5(2) . . . . ? Cu1 N5 C8 C9 177.03(13) . . . . ? C11 N5 C8 C7 179.65(19) . . . . ? Cu1 N5 C8 C7 -2.8(2) . . . . ? S1 C7 C8 C9 149.6(2) . . . . ? S1 C7 C8 N5 -30.6(2) . . . . ? N5 C8 C9 N6 0.2(2) . . . . ? C7 C8 C9 N6 -179.9(2) . . . . ? N5 C8 C9 C10 -179.1(2) . . . . ? C7 C8 C9 C10 0.7(4) . . . . ? C11 N6 C9 C8 0.1(2) . . . . ? C11 N6 C9 C10 179.5(2) . . . . ? C8 N5 C11 N6 0.6(2) . . . . ? Cu1 N5 C11 N6 -176.24(16) . . . . ? C9 N6 C11 N5 -0.5(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 N2 H2N O8 0.77(2) 2.51(2) 3.240(3) 160(2) 2_655 N1 H1N O6 0.819(15) 2.314(18) 3.055(2) 151(2) . N3 H3N O7 0.806(15) 2.502(19) 3.194(3) 145(2) 1_455 N6 H6N O2 0.788(16) 2.50(2) 3.190(3) 148(2) 3_655 N6 H6N O4 0.788(16) 2.52(2) 3.190(3) 144(2) 3_655 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.484 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.060 #===END data_3b _database_code_depnum_ccdc_archive 'CCDC 265659' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'Cu (C17H15N4O2)2.MeOH' _chemical_formula_sum 'C35 H34 Cu N8 O5' _chemical_formula_weight 710.24 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6598(3) _cell_length_b 9.8301(4) _cell_length_c 10.0256(4) _cell_angle_alpha 102.016(2) _cell_angle_beta 98.708(2) _cell_angle_gamma 100.635(2) _cell_volume 804.25(5) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3147 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 28.4 _exptl_crystal_description plate _exptl_crystal_colour 'pale pink' _exptl_crystal_size_max 1.30 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 369 _exptl_absorpt_coefficient_mu 0.736 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1996) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7009 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.79 _reflns_number_total 3653 _reflns_number_gt 3129 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0396P)^2^+0.5808P] 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 3653 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 O3M O -0.4351(4) 0.0580(4) 0.0399(5) 0.0965(12) Uani 0.50 1 d P . -1 H3MO H -0.4680 0.1482 0.0402 0.145 Uiso 0.50 1 d PR . -1 C3M C -0.5649(4) -0.0580(4) -0.0399(5) 0.0965(12) Uani 0.50 1 d P A -2 H3M1 H -0.6655 -0.0450 -0.0110 0.145 Uiso 0.50 1 d PR A -2 H3M2 H -0.5424 -0.1479 -0.0236 0.145 Uiso 0.50 1 d PR A -2 H3M3 H -0.5746 -0.0605 -0.1391 0.145 Uiso 0.50 1 d PR A -2 Cu1 Cu 0.0000 0.0000 0.0000 0.01531(10) Uani 1 2 d S . . O1 O 0.31464(18) 0.27965(16) 0.00819(15) 0.0277(4) Uani 1 1 d . . . O2 O -0.29028(16) -0.20568(15) -0.38924(14) 0.0204(3) Uani 1 1 d . . . N1 N 0.10078(19) 0.10337(17) -0.13206(16) 0.0166(3) Uani 1 1 d . . . N2 N 0.1350(2) 0.14616(18) -0.33967(18) 0.0181(3) Uani 1 1 d . . . N3 N -0.06847(19) -0.04323(17) -0.35084(16) 0.0157(3) Uani 1 1 d . . . N4 N -0.1585(2) -0.11485(19) -0.15857(17) 0.0201(4) Uani 1 1 d . . . C1 C 0.2288(2) 0.2175(2) -0.1049(2) 0.0184(4) Uani 1 1 d . . . C2 C 0.2537(2) 0.2618(2) -0.24108(19) 0.0170(4) Uani 1 1 d . . . C3 C 0.0499(2) 0.06230(19) -0.27435(19) 0.0152(4) Uani 1 1 d . . . C4 C -0.1691(2) -0.1195(2) -0.28896(19) 0.0159(4) Uani 1 1 d . . . C5 C -0.4254(3) -0.2853(3) -0.3503(2) 0.0322(5) Uani 1 1 d . . . H5A H -0.3906 -0.3546 -0.3019 0.048 Uiso 1 1 calc R . . H5B H -0.5062 -0.3358 -0.4340 0.048 Uiso 1 1 calc R . . H5C H -0.4716 -0.2199 -0.2887 0.048 Uiso 1 1 calc R . . C6 C 0.2095(2) 0.4060(2) -0.2430(2) 0.0191(4) Uani 1 1 d . . . C7 C 0.1747(3) 0.4923(3) -0.1287(3) 0.0360(6) Uani 1 1 d . . . H7 H 0.1774 0.4623 -0.0444 0.043 Uiso 1 1 calc R . . C8 C 0.1360(4) 0.6217(3) -0.1356(3) 0.0474(7) Uani 1 1 d . . . H8 H 0.1111 0.6789 -0.0565 0.057 Uiso 1 1 calc R . . C9 C 0.1335(3) 0.6675(3) -0.2562(3) 0.0370(6) Uani 1 1 d . . . H9 H 0.1097 0.7573 -0.2602 0.044 Uiso 1 1 calc R . . C10 C 0.1658(3) 0.5818(3) -0.3714(3) 0.0338(5) Uani 1 1 d . . . H10 H 0.1625 0.6121 -0.4556 0.041 Uiso 1 1 calc R . . C11 C 0.2031(3) 0.4523(2) -0.3651(2) 0.0284(5) Uani 1 1 d . . . H11 H 0.2245 0.3940 -0.4454 0.034 Uiso 1 1 calc R . . C12 C 0.4247(2) 0.2617(2) -0.26170(19) 0.0173(4) Uani 1 1 d . . . C13 C 0.5441(2) 0.3859(2) -0.2157(2) 0.0229(4) Uani 1 1 d . . . H13 H 0.5196 0.4718 -0.1700 0.027 Uiso 1 1 calc R . . C14 C 0.6995(3) 0.3856(3) -0.2361(2) 0.0295(5) Uani 1 1 d . . . H14 H 0.7801 0.4714 -0.2053 0.035 Uiso 1 1 calc R . . C15 C 0.7367(3) 0.2605(3) -0.3013(2) 0.0299(5) Uani 1 1 d . . . H15 H 0.8424 0.2605 -0.3164 0.036 Uiso 1 1 calc R . . C16 C 0.6193(3) 0.1356(3) -0.3443(2) 0.0299(5) Uani 1 1 d . . . H16 H 0.6450 0.0492 -0.3873 0.036 Uiso 1 1 calc R . . C17 C 0.4642(3) 0.1361(2) -0.3247(2) 0.0244(4) Uani 1 1 d . . . H17 H 0.3843 0.0498 -0.3545 0.029 Uiso 1 1 calc R . . H4N H -0.229(3) -0.171(3) -0.139(3) 0.027(7) Uiso 1 1 d . . . H2N H 0.123(3) 0.125(3) -0.427(3) 0.034(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3M 0.080(3) 0.085(3) 0.136(4) 0.036(2) 0.026(2) 0.0348(19) C3M 0.080(3) 0.085(3) 0.136(4) 0.036(2) 0.026(2) 0.0348(19) Cu1 0.01647(18) 0.01686(17) 0.01059(17) 0.00289(12) 0.00185(12) -0.00014(12) O1 0.0318(8) 0.0277(8) 0.0136(7) 0.0044(6) -0.0011(6) -0.0129(6) O2 0.0194(7) 0.0222(7) 0.0135(7) 0.0027(5) -0.0001(5) -0.0061(5) N1 0.0181(8) 0.0176(8) 0.0109(8) 0.0017(6) 0.0013(6) -0.0009(6) N2 0.0196(8) 0.0201(8) 0.0109(8) 0.0033(6) 0.0019(6) -0.0034(6) N3 0.0169(8) 0.0174(8) 0.0109(7) 0.0031(6) 0.0024(6) -0.0003(6) N4 0.0192(8) 0.0237(9) 0.0138(8) 0.0054(7) 0.0027(6) -0.0042(7) C1 0.0207(10) 0.0186(9) 0.0140(9) 0.0039(7) 0.0036(7) 0.0000(7) C2 0.0187(9) 0.0176(9) 0.0115(9) 0.0023(7) 0.0016(7) -0.0016(7) C3 0.0166(9) 0.0155(9) 0.0140(9) 0.0044(7) 0.0034(7) 0.0039(7) C4 0.0164(9) 0.0159(9) 0.0144(9) 0.0022(7) 0.0024(7) 0.0028(7) C5 0.0259(11) 0.0381(13) 0.0224(11) 0.0057(10) 0.0017(9) -0.0137(10) C6 0.0137(9) 0.0212(10) 0.0204(10) 0.0044(8) 0.0032(7) -0.0002(7) C7 0.0525(16) 0.0330(13) 0.0274(12) 0.0075(10) 0.0156(11) 0.0156(11) C8 0.0655(19) 0.0345(14) 0.0486(17) 0.0041(12) 0.0254(15) 0.0225(13) C9 0.0327(13) 0.0263(12) 0.0566(17) 0.0118(11) 0.0110(11) 0.0143(10) C10 0.0335(13) 0.0325(12) 0.0387(14) 0.0177(11) 0.0041(10) 0.0079(10) C11 0.0367(12) 0.0274(11) 0.0242(11) 0.0087(9) 0.0083(9) 0.0103(9) C12 0.0196(9) 0.0203(9) 0.0126(9) 0.0065(7) 0.0023(7) 0.0036(7) C13 0.0223(10) 0.0218(10) 0.0221(10) 0.0033(8) 0.0036(8) 0.0019(8) C14 0.0195(10) 0.0343(12) 0.0306(12) 0.0063(10) 0.0025(9) -0.0004(9) C15 0.0199(10) 0.0436(13) 0.0284(12) 0.0107(10) 0.0036(9) 0.0116(10) C16 0.0313(12) 0.0316(12) 0.0278(12) 0.0038(9) 0.0033(9) 0.0156(10) C17 0.0264(11) 0.0201(10) 0.0249(11) 0.0044(8) 0.0017(8) 0.0047(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3M C3M 1.442(7) . ? O3M H3MO 0.9800 . ? C3M H3M1 0.9800 . ? C3M H3M2 0.9800 . ? C3M H3M3 0.9800 . ? Cu1 N4 1.9251(16) . ? Cu1 N4 1.9251(16) 2 ? Cu1 N1 2.0322(16) . ? Cu1 N1 2.0322(16) 2 ? O1 C1 1.225(2) . ? O2 C4 1.352(2) . ? O2 C5 1.435(2) . ? N1 C1 1.373(2) . ? N1 C3 1.377(2) . ? N2 C3 1.341(2) . ? N2 C2 1.455(2) . ? N2 H2N 0.84(3) . ? N3 C3 1.324(2) . ? N3 C4 1.350(2) . ? N4 C4 1.287(3) . ? N4 H4N 0.83(3) . ? C1 C2 1.550(3) . ? C2 C12 1.526(3) . ? C2 C6 1.538(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.385(3) . ? C6 C11 1.389(3) . ? C7 C8 1.387(4) . ? C7 H7 0.9500 . ? C8 C9 1.374(4) . ? C8 H8 0.9500 . ? C9 C10 1.379(4) . ? C9 H9 0.9500 . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.389(3) . ? C12 C17 1.392(3) . ? C13 C14 1.391(3) . ? C13 H13 0.9500 . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 C16 1.383(3) . ? C15 H15 0.9500 . ? C16 C17 1.387(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3M O3M H3MO 108.7 . . ? O3M C3M H3M1 109.9 . . ? O3M C3M H3M2 108.9 . . ? H3M1 C3M H3M2 109.5 . . ? O3M C3M H3M3 109.7 . . ? H3M1 C3M H3M3 109.5 . . ? H3M2 C3M H3M3 109.5 . . ? N4 Cu1 N4 180.0 . 2 ? N4 Cu1 N1 87.67(7) . . ? N4 Cu1 N1 92.33(7) 2 . ? N4 Cu1 N1 92.33(7) . 2 ? N4 Cu1 N1 87.67(7) 2 2 ? N1 Cu1 N1 180.00(8) . 2 ? C4 O2 C5 119.41(15) . . ? C1 N1 C3 106.69(15) . . ? C1 N1 Cu1 130.08(13) . . ? C3 N1 Cu1 123.19(12) . . ? C3 N2 C2 111.44(16) . . ? C3 N2 H2N 120.8(19) . . ? C2 N2 H2N 127.4(19) . . ? C3 N3 C4 120.08(16) . . ? C4 N4 Cu1 130.50(14) . . ? C4 N4 H4N 115.7(18) . . ? Cu1 N4 H4N 113.7(18) . . ? O1 C1 N1 127.33(18) . . ? O1 C1 C2 122.43(17) . . ? N1 C1 C2 110.24(15) . . ? N2 C2 C12 112.90(16) . . ? N2 C2 C6 110.52(16) . . ? C12 C2 C6 112.50(15) . . ? N2 C2 C1 98.85(14) . . ? C12 C2 C1 110.10(15) . . ? C6 C2 C1 111.20(16) . . ? N3 C3 N2 118.14(17) . . ? N3 C3 N1 129.46(17) . . ? N2 C3 N1 112.39(16) . . ? N4 C4 N3 128.37(18) . . ? N4 C4 O2 123.67(17) . . ? N3 C4 O2 107.96(16) . . ? O2 C5 H5A 109.5 . . ? O2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C11 118.1(2) . . ? C7 C6 C2 123.14(19) . . ? C11 C6 C2 118.79(18) . . ? C6 C7 C8 121.0(2) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 120.3(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.3(2) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C9 C10 C11 120.4(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C6 120.9(2) . . ? C10 C11 H11 119.6 . . ? C6 C11 H11 119.6 . . ? C13 C12 C17 118.83(19) . . ? C13 C12 C2 120.72(17) . . ? C17 C12 C2 120.44(17) . . ? C12 C13 C14 120.5(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 120.1(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 119.7(2) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.2(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 120.6(2) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? 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 N4 Cu1 N1 C1 176.58(18) . . . . ? N4 Cu1 N1 C1 -3.42(18) 2 . . . ? N1 Cu1 N1 C1 -66(100) 2 . . . ? N4 Cu1 N1 C3 -6.09(15) . . . . ? N4 Cu1 N1 C3 173.91(15) 2 . . . ? N1 Cu1 N1 C3 112(100) 2 . . . ? N4 Cu1 N4 C4 176(100) 2 . . . ? N1 Cu1 N4 C4 5.61(19) . . . . ? N1 Cu1 N4 C4 -174.39(19) 2 . . . ? C3 N1 C1 O1 -175.0(2) . . . . ? Cu1 N1 C1 O1 2.6(3) . . . . ? C3 N1 C1 C2 5.2(2) . . . . ? Cu1 N1 C1 C2 -177.18(13) . . . . ? C3 N2 C2 C12 121.44(17) . . . . ? C3 N2 C2 C6 -111.57(18) . . . . ? C3 N2 C2 C1 5.1(2) . . . . ? O1 C1 C2 N2 173.9(2) . . . . ? N1 C1 C2 N2 -6.2(2) . . . . ? O1 C1 C2 C12 55.5(3) . . . . ? N1 C1 C2 C12 -124.68(17) . . . . ? O1 C1 C2 C6 -69.9(2) . . . . ? N1 C1 C2 C6 109.94(18) . . . . ? C4 N3 C3 N2 -172.16(17) . . . . ? C4 N3 C3 N1 6.7(3) . . . . ? C2 N2 C3 N3 176.49(16) . . . . ? C2 N2 C3 N1 -2.6(2) . . . . ? C1 N1 C3 N3 179.29(19) . . . . ? Cu1 N1 C3 N3 1.4(3) . . . . ? C1 N1 C3 N2 -1.8(2) . . . . ? Cu1 N1 C3 N2 -179.65(12) . . . . ? Cu1 N4 C4 N3 0.3(3) . . . . ? Cu1 N4 C4 O2 -179.11(14) . . . . ? C3 N3 C4 N4 -8.0(3) . . . . ? C3 N3 C4 O2 171.54(16) . . . . ? C5 O2 C4 N4 7.5(3) . . . . ? C5 O2 C4 N3 -172.00(18) . . . . ? N2 C2 C6 C7 117.3(2) . . . . ? C12 C2 C6 C7 -115.5(2) . . . . ? C1 C2 C6 C7 8.5(3) . . . . ? N2 C2 C6 C11 -62.3(2) . . . . ? C12 C2 C6 C11 64.9(2) . . . . ? C1 C2 C6 C11 -171.05(18) . . . . ? C11 C6 C7 C8 -0.6(4) . . . . ? C2 C6 C7 C8 179.8(2) . . . . ? C6 C7 C8 C9 -0.8(4) . . . . ? C7 C8 C9 C10 1.6(4) . . . . ? C8 C9 C10 C11 -1.1(4) . . . . ? C9 C10 C11 C6 -0.3(4) . . . . ? C7 C6 C11 C10 1.2(3) . . . . ? C2 C6 C11 C10 -179.2(2) . . . . ? N2 C2 C12 C13 156.62(18) . . . . ? C6 C2 C12 C13 30.7(2) . . . . ? C1 C2 C12 C13 -94.0(2) . . . . ? N2 C2 C12 C17 -24.6(2) . . . . ? C6 C2 C12 C17 -150.56(18) . . . . ? C1 C2 C12 C17 84.8(2) . . . . ? C17 C12 C13 C14 1.9(3) . . . . ? C2 C12 C13 C14 -179.28(19) . . . . ? C12 C13 C14 C15 -0.7(3) . . . . ? C13 C14 C15 C16 -0.9(3) . . . . ? C14 C15 C16 C17 1.2(3) . . . . ? C15 C16 C17 C12 0.0(3) . . . . ? C13 C12 C17 C16 -1.6(3) . . . . ? C2 C12 C17 C16 179.66(19) . . . . ? 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 N4 H4N O1 0.83(3) 1.99(3) 2.748(2) 152(2) 2 N2 H2N N3 0.84(3) 2.15(3) 2.987(2) 172(3) 2_554 _diffrn_measured_fraction_theta_max 0.870 _diffrn_reflns_theta_full 28.79 _diffrn_measured_fraction_theta_full 0.870 _refine_diff_density_max 0.523 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.065 #===END data_3d _database_code_depnum_ccdc_archive 'CCDC 265660' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'Cu (C17H15N4O2)2 .2dmso' _chemical_formula_sum 'C38 H42 Cu N8 O6 S2' _chemical_formula_weight 834.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.8052(9) _cell_length_b 16.1700(10) _cell_length_c 16.6035(10) _cell_angle_alpha 90.00 _cell_angle_beta 111.955(3) _cell_angle_gamma 90.00 _cell_volume 3935.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4161 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.6 _exptl_crystal_description plate _exptl_crystal_colour pink _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1740 _exptl_absorpt_coefficient_mu 0.717 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.905 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1996) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25450 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0792 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 29.00 _reflns_number_total 9455 _reflns_number_gt 6124 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _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^)+(0.0453P)^2^+0.5136P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9455 _refine_ls_number_parameters 502 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0924 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.25336(2) 0.124218(19) 0.221630(19) 0.01772(9) Uani 1 1 d . . . O1 O 0.03383(12) 0.19589(11) 0.10472(11) 0.0247(4) Uani 1 1 d . . . O2 O 0.30169(12) -0.00567(12) 0.44584(11) 0.0269(4) Uani 1 1 d . . . O3 O 0.46970(12) 0.04415(12) 0.33621(11) 0.0254(4) Uani 1 1 d . . . O4 O 0.20508(12) 0.24559(12) -0.00717(11) 0.0277(4) Uani 1 1 d . . . N1 N 0.12617(13) 0.12008(13) 0.22509(13) 0.0186(4) Uani 1 1 d . . . N2 N 0.01558(14) 0.07546(13) 0.27007(14) 0.0236(5) Uani 1 1 d . . . H2N H -0.0107 0.0445 0.2977 0.028 Uiso 1 1 calc R . . N3 N 0.16011(14) 0.03662(13) 0.35635(13) 0.0203(5) Uani 1 1 d . . . N4 N 0.29397(15) 0.06472(14) 0.32777(13) 0.0249(5) Uani 1 1 d . . . H4N H 0.3532 0.0562 0.3504 0.030 Uiso 1 1 calc R . . N5 N 0.37801(13) 0.11693(13) 0.21274(13) 0.0184(5) Uani 1 1 d . . . N6 N 0.48499(14) 0.13975(13) 0.15521(13) 0.0208(5) Uani 1 1 d . . . H6N H 0.5091 0.1580 0.1187 0.025 Uiso 1 1 calc R . . N7 N 0.34460(14) 0.19625(13) 0.07926(13) 0.0199(5) Uani 1 1 d . . . N8 N 0.21551(15) 0.19140(14) 0.11982(14) 0.0237(5) Uani 1 1 d . . . H8N H 0.1612 0.2140 0.1059 0.028 Uiso 1 1 calc R . . C1 C 0.04530(17) 0.15403(15) 0.16923(17) 0.0200(6) Uani 1 1 d . . . C2 C -0.03237(17) 0.13295(16) 0.20102(16) 0.0210(5) Uani 1 1 d . . . C3 C 0.10491(17) 0.07577(15) 0.28615(16) 0.0196(5) Uani 1 1 d . . . C4 C 0.24948(18) 0.03437(16) 0.37288(16) 0.0215(6) Uani 1 1 d . . . C5 C 0.2581(2) -0.04238(19) 0.49910(17) 0.0315(7) Uani 1 1 d . . . H5A H 0.2277 0.0008 0.5199 0.047 Uiso 1 1 calc R . . H5B H 0.3040 -0.0700 0.5489 0.047 Uiso 1 1 calc R . . H5C H 0.2129 -0.0829 0.4649 0.047 Uiso 1 1 calc R . . C6 C -0.05559(17) 0.21277(16) 0.23854(17) 0.0212(6) Uani 1 1 d . . . C7 C -0.01363(18) 0.23159(18) 0.32575(18) 0.0282(6) Uani 1 1 d . . . H7 H 0.0285 0.1935 0.3634 0.034 Uiso 1 1 calc R . . C8 C -0.0318(2) 0.3049(2) 0.3594(2) 0.0361(7) Uani 1 1 d . . . H8 H -0.0019 0.3168 0.4194 0.043 Uiso 1 1 calc R . . C9 C -0.0932(2) 0.36034(19) 0.3059(2) 0.0413(8) Uani 1 1 d . . . H9 H -0.1066 0.4103 0.3288 0.050 Uiso 1 1 calc R . . C10 C -0.1351(2) 0.34273(19) 0.2184(2) 0.0384(8) Uani 1 1 d . . . H10 H -0.1775 0.3810 0.1813 0.046 Uiso 1 1 calc R . . C11 C -0.1164(2) 0.27027(17) 0.18430(19) 0.0295(6) Uani 1 1 d . . . H11 H -0.1448 0.2595 0.1238 0.035 Uiso 1 1 calc R . . C12 C -0.11239(18) 0.09068(16) 0.12989(18) 0.0245(6) Uani 1 1 d . . . C13 C -0.20145(19) 0.09800(19) 0.12512(19) 0.0332(7) Uani 1 1 d . . . H13 H -0.2144 0.1320 0.1657 0.040 Uiso 1 1 calc R . . C14 C -0.2718(2) 0.0564(2) 0.0620(2) 0.0479(9) Uani 1 1 d . . . H14 H -0.3325 0.0619 0.0599 0.057 Uiso 1 1 calc R . . C15 C -0.2546(2) 0.0077(2) 0.0027(3) 0.0567(10) Uani 1 1 d . . . H15 H -0.3031 -0.0201 -0.0411 0.068 Uiso 1 1 calc R . . C16 C -0.1664(3) -0.0008(3) 0.0069(3) 0.0700(13) Uani 1 1 d . . . H16 H -0.1539 -0.0350 -0.0339 0.084 Uiso 1 1 calc R . . C17 C -0.0958(2) 0.0402(2) 0.0703(2) 0.0505(10) Uani 1 1 d . . . H17 H -0.0351 0.0335 0.0729 0.061 Uiso 1 1 calc R . . C18 C 0.45727(17) 0.08043(16) 0.26811(16) 0.0194(5) Uani 1 1 d . . . C19 C 0.53391(17) 0.09140(16) 0.23237(16) 0.0198(5) Uani 1 1 d . . . C20 C 0.39823(17) 0.15296(15) 0.14680(16) 0.0181(5) Uani 1 1 d . . . C21 C 0.25691(17) 0.20888(15) 0.06834(16) 0.0203(6) Uani 1 1 d . . . C22 C 0.2438(2) 0.2555(2) -0.07206(19) 0.0399(8) Uani 1 1 d . . . H22A H 0.2945 0.2950 -0.0515 0.060 Uiso 1 1 calc R . . H22B H 0.1971 0.2763 -0.1257 0.060 Uiso 1 1 calc R . . H22C H 0.2664 0.2021 -0.0834 0.060 Uiso 1 1 calc R . . C23 C 0.55984(17) 0.00509(16) 0.21091(17) 0.0213(6) Uani 1 1 d . . . C24 C 0.5333(2) -0.02298(18) 0.12656(19) 0.0310(7) Uani 1 1 d . . . H24 H 0.5007 0.0127 0.0798 0.037 Uiso 1 1 calc R . . C25 C 0.5540(2) -0.1031(2) 0.1094(2) 0.0406(8) Uani 1 1 d . . . H25 H 0.5347 -0.1218 0.0511 0.049 Uiso 1 1 calc R . . C26 C 0.6019(2) -0.15528(18) 0.1759(2) 0.0355(7) Uani 1 1 d . . . H26 H 0.6166 -0.2097 0.1640 0.043 Uiso 1 1 calc R . . C27 C 0.6286(2) -0.12768(18) 0.2609(2) 0.0366(7) Uani 1 1 d . . . H27 H 0.6615 -0.1635 0.3075 0.044 Uiso 1 1 calc R . . C28 C 0.6074(2) -0.04828(18) 0.27821(19) 0.0309(7) Uani 1 1 d . . . H28 H 0.6255 -0.0301 0.3367 0.037 Uiso 1 1 calc R . . C29 C 0.61332(17) 0.14208(15) 0.29533(16) 0.0191(5) Uani 1 1 d . . . C30 C 0.70248(17) 0.13081(16) 0.30111(16) 0.0221(6) Uani 1 1 d . . . H30 H 0.7158 0.0889 0.2675 0.026 Uiso 1 1 calc R . . C31 C 0.77235(19) 0.18026(17) 0.35559(18) 0.0276(6) Uani 1 1 d . . . H31 H 0.8331 0.1721 0.3591 0.033 Uiso 1 1 calc R . . C32 C 0.7535(2) 0.24133(18) 0.40472(18) 0.0299(7) Uani 1 1 d . . . H32 H 0.8013 0.2752 0.4419 0.036 Uiso 1 1 calc R . . C33 C 0.6651(2) 0.25323(18) 0.39985(18) 0.0305(7) Uani 1 1 d . . . H33 H 0.6520 0.2952 0.4335 0.037 Uiso 1 1 calc R . . C34 C 0.59544(18) 0.20352(17) 0.34545(17) 0.0243(6) Uani 1 1 d . . . H34 H 0.5348 0.2116 0.3424 0.029 Uiso 1 1 calc R . . S1 S 0.60446(5) 0.31312(5) 0.08136(5) 0.03096(18) Uani 1 1 d . . . O5 O 0.58237(14) 0.22213(12) 0.07200(13) 0.0335(5) Uani 1 1 d . . . C35 C 0.4990(2) 0.3659(2) 0.0299(2) 0.0468(9) Uani 1 1 d . . . H35A H 0.4787 0.3591 -0.0332 0.070 Uiso 1 1 calc R . . H35B H 0.5073 0.4249 0.0445 0.070 Uiso 1 1 calc R . . H35C H 0.4531 0.3429 0.0500 0.070 Uiso 1 1 calc R . . C36 C 0.6203(2) 0.3409(2) 0.19041(19) 0.0397(8) Uani 1 1 d . . . H36A H 0.5655 0.3265 0.2016 0.060 Uiso 1 1 calc R . . H36B H 0.6314 0.4005 0.1984 0.060 Uiso 1 1 calc R . . H36C H 0.6728 0.3108 0.2310 0.060 Uiso 1 1 calc R . . S2 S -0.11066(5) -0.06686(5) 0.37305(5) 0.03405(19) Uani 1 1 d . . . O6 O -0.09069(14) 0.02196(12) 0.36052(13) 0.0324(5) Uani 1 1 d . . . C37 C -0.1242(2) -0.1184(2) 0.2744(2) 0.0434(8) Uani 1 1 d . . . H37A H -0.1768 -0.0952 0.2271 0.065 Uiso 1 1 calc R . . H37B H -0.1341 -0.1775 0.2804 0.065 Uiso 1 1 calc R . . H37C H -0.0691 -0.1108 0.2615 0.065 Uiso 1 1 calc R . . C38 C -0.0027(3) -0.1100(2) 0.4390(2) 0.0601(11) Uani 1 1 d . . . H38A H 0.0430 -0.0952 0.4145 0.090 Uiso 1 1 calc R . . H38B H -0.0079 -0.1703 0.4404 0.090 Uiso 1 1 calc R . . H38C H 0.0161 -0.0880 0.4981 0.090 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 0.01688(16) 0.01883(16) 0.01767(16) 0.00218(13) 0.00670(12) 0.00100(13) O1 0.0196(10) 0.0296(11) 0.0238(10) 0.0091(8) 0.0067(8) 0.0045(8) O2 0.0235(10) 0.0351(12) 0.0215(10) 0.0113(8) 0.0076(8) 0.0035(8) O3 0.0211(10) 0.0328(11) 0.0221(10) 0.0089(8) 0.0079(8) 0.0038(8) O4 0.0225(10) 0.0373(12) 0.0232(10) 0.0133(8) 0.0086(8) 0.0084(8) N1 0.0180(11) 0.0174(11) 0.0196(11) 0.0029(9) 0.0061(9) 0.0011(9) N2 0.0185(11) 0.0237(13) 0.0302(13) 0.0100(10) 0.0108(10) -0.0015(9) N3 0.0200(12) 0.0199(12) 0.0212(12) 0.0037(9) 0.0078(9) 0.0012(9) N4 0.0177(12) 0.0357(14) 0.0222(12) 0.0084(10) 0.0084(10) 0.0053(10) N5 0.0159(11) 0.0192(12) 0.0187(11) 0.0038(9) 0.0048(9) 0.0004(9) N6 0.0181(11) 0.0266(13) 0.0182(11) 0.0077(9) 0.0074(9) 0.0023(9) N7 0.0184(11) 0.0209(12) 0.0194(11) 0.0041(9) 0.0057(9) 0.0014(9) N8 0.0185(12) 0.0290(13) 0.0250(12) 0.0071(10) 0.0096(10) 0.0059(10) C1 0.0204(14) 0.0167(13) 0.0235(14) -0.0027(11) 0.0088(11) -0.0014(10) C2 0.0179(13) 0.0201(14) 0.0245(14) 0.0056(11) 0.0072(11) -0.0002(11) C3 0.0235(14) 0.0152(13) 0.0213(14) -0.0017(10) 0.0096(11) -0.0026(11) C4 0.0261(15) 0.0205(14) 0.0177(14) 0.0000(10) 0.0080(12) 0.0013(11) C5 0.0346(17) 0.0402(18) 0.0211(15) 0.0104(13) 0.0120(13) 0.0054(14) C6 0.0181(13) 0.0216(14) 0.0274(15) 0.0020(11) 0.0125(12) -0.0037(11) C7 0.0213(15) 0.0324(16) 0.0291(16) 0.0010(12) 0.0073(12) -0.0018(12) C8 0.0325(17) 0.043(2) 0.0343(17) -0.0099(14) 0.0137(14) -0.0091(14) C9 0.045(2) 0.0273(18) 0.055(2) -0.0099(15) 0.0234(17) -0.0037(15) C10 0.0441(19) 0.0268(17) 0.045(2) 0.0068(14) 0.0174(16) 0.0056(14) C11 0.0345(17) 0.0250(16) 0.0302(16) 0.0039(12) 0.0133(13) 0.0008(13) C12 0.0194(14) 0.0192(14) 0.0308(16) 0.0034(11) 0.0047(12) 0.0001(11) C13 0.0254(16) 0.0386(18) 0.0359(18) -0.0020(13) 0.0118(14) -0.0082(13) C14 0.0241(17) 0.051(2) 0.062(2) -0.0081(18) 0.0094(17) -0.0126(15) C15 0.037(2) 0.048(2) 0.070(3) -0.0248(19) 0.0025(19) -0.0129(17) C16 0.053(3) 0.063(3) 0.088(3) -0.053(2) 0.019(2) -0.012(2) C17 0.0291(18) 0.048(2) 0.071(3) -0.0310(19) 0.0144(18) -0.0041(16) C18 0.0186(13) 0.0182(14) 0.0210(14) 0.0015(10) 0.0069(11) -0.0006(10) C19 0.0169(13) 0.0244(14) 0.0180(14) 0.0045(10) 0.0061(11) 0.0014(11) C20 0.0194(13) 0.0156(13) 0.0193(13) -0.0007(10) 0.0074(11) -0.0012(10) C21 0.0222(14) 0.0163(13) 0.0217(14) 0.0006(10) 0.0076(11) 0.0004(10) C22 0.0306(17) 0.063(2) 0.0252(17) 0.0218(15) 0.0095(13) 0.0101(15) C23 0.0174(13) 0.0223(14) 0.0246(14) 0.0002(11) 0.0082(11) -0.0018(11) C24 0.0377(17) 0.0278(16) 0.0272(16) -0.0002(12) 0.0118(14) -0.0001(13) C25 0.052(2) 0.0344(19) 0.0396(19) -0.0118(14) 0.0221(16) -0.0043(15) C26 0.0379(18) 0.0183(15) 0.057(2) -0.0053(14) 0.0250(17) -0.0028(13) C27 0.0335(17) 0.0247(16) 0.051(2) 0.0083(15) 0.0153(15) 0.0054(14) C28 0.0330(17) 0.0272(16) 0.0297(16) 0.0025(12) 0.0086(13) 0.0034(13) C29 0.0197(13) 0.0200(14) 0.0173(13) 0.0053(10) 0.0065(11) -0.0003(10) C30 0.0222(14) 0.0241(14) 0.0222(14) 0.0026(11) 0.0109(11) 0.0004(11) C31 0.0216(14) 0.0319(16) 0.0301(16) 0.0044(12) 0.0105(13) -0.0026(12) C32 0.0291(16) 0.0338(17) 0.0241(15) 0.0014(12) 0.0066(13) -0.0097(13) C33 0.0392(18) 0.0273(16) 0.0275(16) -0.0049(12) 0.0151(14) -0.0045(13) C34 0.0214(14) 0.0274(16) 0.0264(15) -0.0004(11) 0.0114(12) -0.0013(11) S1 0.0371(4) 0.0286(4) 0.0317(4) 0.0030(3) 0.0180(3) -0.0054(3) O5 0.0424(13) 0.0264(11) 0.0416(12) -0.0002(9) 0.0269(10) -0.0040(9) C35 0.054(2) 0.040(2) 0.0357(19) 0.0098(15) 0.0049(16) 0.0074(17) C36 0.052(2) 0.0331(18) 0.0295(17) 0.0015(13) 0.0101(15) 0.0012(15) S2 0.0419(5) 0.0277(4) 0.0393(5) -0.0012(3) 0.0230(4) -0.0060(3) O6 0.0400(12) 0.0238(11) 0.0404(12) 0.0036(9) 0.0230(10) 0.0022(9) C37 0.048(2) 0.0352(19) 0.0402(19) -0.0063(15) 0.0083(16) 0.0023(16) C38 0.078(3) 0.029(2) 0.047(2) -0.0066(15) -0.007(2) 0.0080(18) _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 N4 1.897(2) . ? Cu1 N8 1.908(2) . ? Cu1 N5 2.033(2) . ? Cu1 N1 2.034(2) . ? O1 C1 1.222(3) . ? O2 C4 1.349(3) . ? O2 C5 1.436(3) . ? O3 C18 1.223(3) . ? O4 C21 1.352(3) . ? O4 C22 1.434(3) . ? N1 C3 1.382(3) . ? N1 C1 1.382(3) . ? N2 C3 1.335(3) . ? N2 C2 1.450(3) . ? N2 H2N 0.8800 . ? N3 C3 1.327(3) . ? N3 C4 1.335(3) . ? N4 C4 1.300(3) . ? N4 H4N 0.8800 . ? N5 C18 1.379(3) . ? N5 C20 1.379(3) . ? N6 C20 1.343(3) . ? N6 C19 1.452(3) . ? N6 H6N 0.8800 . ? N7 C20 1.325(3) . ? N7 C21 1.344(3) . ? N8 C21 1.287(3) . ? N8 H8N 0.8800 . ? C1 C2 1.545(3) . ? C2 C12 1.531(4) . ? C2 C6 1.536(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.382(4) . ? C6 C11 1.397(4) . ? C7 C8 1.385(4) . ? C7 H7 0.9500 . ? C8 C9 1.375(4) . ? C8 H8 0.9500 . ? C9 C10 1.381(4) . ? C9 H9 0.9500 . ? C10 C11 1.381(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C17 1.381(4) . ? C12 C13 1.385(4) . ? C13 C14 1.384(4) . ? C13 H13 0.9500 . ? C14 C15 1.366(5) . ? C14 H14 0.9500 . ? C15 C16 1.376(5) . ? C15 H15 0.9500 . ? C16 C17 1.384(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.545(3) . ? C19 C23 1.533(4) . ? C19 C29 1.536(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.380(4) . ? C23 C28 1.389(4) . ? C24 C25 1.391(4) . ? C24 H24 0.9500 . ? C25 C26 1.371(4) . ? C25 H25 0.9500 . ? C26 C27 1.387(4) . ? C26 H26 0.9500 . ? C27 C28 1.384(4) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.388(3) . ? C29 C34 1.391(4) . ? C30 C31 1.389(4) . ? C30 H30 0.9500 . ? C31 C32 1.383(4) . ? C31 H31 0.9500 . ? C32 C33 1.382(4) . ? C32 H32 0.9500 . ? C33 C34 1.389(4) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? S1 O5 1.507(2) . ? S1 C35 1.781(3) . ? S1 C36 1.790(3) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? S2 O6 1.502(2) . ? S2 C37 1.777(3) . ? S2 C38 1.789(3) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N8 175.74(10) . . ? N4 Cu1 N5 92.15(8) . . ? N8 Cu1 N5 87.71(8) . . ? N4 Cu1 N1 87.24(9) . . ? N8 Cu1 N1 93.32(9) . . ? N5 Cu1 N1 174.28(8) . . ? C4 O2 C5 118.6(2) . . ? C21 O4 C22 117.7(2) . . ? C3 N1 C1 106.3(2) . . ? C3 N1 Cu1 123.50(17) . . ? C1 N1 Cu1 130.10(16) . . ? C3 N2 C2 110.9(2) . . ? C3 N2 H2N 124.6 . . ? C2 N2 H2N 124.6 . . ? C3 N3 C4 119.4(2) . . ? C4 N4 Cu1 131.20(19) . . ? C4 N4 H4N 114.4 . . ? Cu1 N4 H4N 114.4 . . ? C18 N5 C20 106.7(2) . . ? C18 N5 Cu1 129.78(16) . . ? C20 N5 Cu1 123.47(16) . . ? C20 N6 C19 111.3(2) . . ? C20 N6 H6N 124.3 . . ? C19 N6 H6N 124.3 . . ? C20 N7 C21 119.7(2) . . ? C21 N8 Cu1 130.13(19) . . ? C21 N8 H8N 114.9 . . ? Cu1 N8 H8N 114.9 . . ? O1 C1 N1 127.3(2) . . ? O1 C1 C2 123.0(2) . . ? N1 C1 C2 109.7(2) . . ? N2 C2 C12 111.1(2) . . ? N2 C2 C6 110.6(2) . . ? C12 C2 C6 115.7(2) . . ? N2 C2 C1 99.47(19) . . ? C12 C2 C1 111.6(2) . . ? C6 C2 C1 107.1(2) . . ? N3 C3 N2 118.2(2) . . ? N3 C3 N1 129.2(2) . . ? N2 C3 N1 112.6(2) . . ? N4 C4 N3 129.0(2) . . ? N4 C4 O2 114.7(2) . . ? N3 C4 O2 116.3(2) . . ? O2 C5 H5A 109.5 . . ? O2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C11 118.3(3) . . ? C7 C6 C2 121.1(2) . . ? C11 C6 C2 120.6(2) . . ? C6 C7 C8 121.3(3) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 119.3(3) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C6 120.1(3) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? C17 C12 C13 118.1(3) . . ? C17 C12 C2 119.5(2) . . ? C13 C12 C2 122.3(2) . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.6(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 120.2(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 120.9(3) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? O3 C18 N5 127.9(2) . . ? O3 C18 C19 122.2(2) . . ? N5 C18 C19 110.0(2) . . ? N6 C19 C23 112.7(2) . . ? N6 C19 C29 110.1(2) . . ? C23 C19 C29 115.0(2) . . ? N6 C19 C18 99.51(19) . . ? C23 C19 C18 107.5(2) . . ? C29 C19 C18 111.0(2) . . ? N7 C20 N6 118.5(2) . . ? N7 C20 N5 129.1(2) . . ? N6 C20 N5 112.4(2) . . ? N8 C21 N7 129.2(2) . . ? N8 C21 O4 115.5(2) . . ? N7 C21 O4 115.4(2) . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 118.7(3) . . ? C24 C23 C19 121.9(2) . . ? C28 C23 C19 119.3(2) . . ? C23 C24 C25 120.6(3) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C26 C25 C24 120.6(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C27 119.2(3) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C28 C27 C26 120.3(3) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C28 C23 120.6(3) . . ? C27 C28 H28 119.7 . . ? C23 C28 H28 119.7 . . ? C30 C29 C34 118.7(2) . . ? C30 C29 C19 121.8(2) . . ? C34 C29 C19 119.4(2) . . ? C29 C30 C31 120.6(2) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C32 C31 C30 120.1(3) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C33 C32 C31 120.1(3) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 119.7(3) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? C33 C34 C29 120.9(3) . . ? C33 C34 H34 119.6 . . ? C29 C34 H34 119.6 . . ? O5 S1 C35 106.24(15) . . ? O5 S1 C36 106.77(13) . . ? C35 S1 C36 96.74(15) . . ? S1 C35 H35A 109.5 . . ? S1 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? S1 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? S1 C36 H36A 109.5 . . ? S1 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? S1 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O6 S2 C37 106.25(14) . . ? O6 S2 C38 104.80(15) . . ? C37 S2 C38 98.02(16) . . ? S2 C37 H37A 109.5 . . ? S2 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? S2 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? S2 C38 H38A 109.5 . . ? S2 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? S2 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? 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 N4 Cu1 N1 C3 -6.5(2) . . . . ? N8 Cu1 N1 C3 177.8(2) . . . . ? N5 Cu1 N1 C3 77.5(9) . . . . ? N4 Cu1 N1 C1 177.2(2) . . . . ? N8 Cu1 N1 C1 1.5(2) . . . . ? N5 Cu1 N1 C1 -98.8(8) . . . . ? N8 Cu1 N4 C4 100.9(12) . . . . ? N5 Cu1 N4 C4 -171.0(3) . . . . ? N1 Cu1 N4 C4 3.3(3) . . . . ? N4 Cu1 N5 C18 -0.1(2) . . . . ? N8 Cu1 N5 C18 175.7(2) . . . . ? N1 Cu1 N5 C18 -83.8(8) . . . . ? N4 Cu1 N5 C20 -177.6(2) . . . . ? N8 Cu1 N5 C20 -1.9(2) . . . . ? N1 Cu1 N5 C20 98.6(8) . . . . ? N4 Cu1 N8 C21 96.1(12) . . . . ? N5 Cu1 N8 C21 7.9(2) . . . . ? N1 Cu1 N8 C21 -166.4(2) . . . . ? C3 N1 C1 O1 -177.9(3) . . . . ? Cu1 N1 C1 O1 -1.1(4) . . . . ? C3 N1 C1 C2 3.3(3) . . . . ? Cu1 N1 C1 C2 -179.93(16) . . . . ? C3 N2 C2 C12 127.8(2) . . . . ? C3 N2 C2 C6 -102.3(2) . . . . ? C3 N2 C2 C1 10.1(3) . . . . ? O1 C1 C2 N2 173.1(2) . . . . ? N1 C1 C2 N2 -8.0(3) . . . . ? O1 C1 C2 C12 55.8(3) . . . . ? N1 C1 C2 C12 -125.3(2) . . . . ? O1 C1 C2 C6 -71.8(3) . . . . ? N1 C1 C2 C6 107.0(2) . . . . ? C4 N3 C3 N2 178.5(2) . . . . ? C4 N3 C3 N1 -2.9(4) . . . . ? C2 N2 C3 N3 169.5(2) . . . . ? C2 N2 C3 N1 -9.4(3) . . . . ? C1 N1 C3 N3 -175.2(2) . . . . ? Cu1 N1 C3 N3 7.8(4) . . . . ? C1 N1 C3 N2 3.5(3) . . . . ? Cu1 N1 C3 N2 -173.53(16) . . . . ? Cu1 N4 C4 N3 0.2(4) . . . . ? Cu1 N4 C4 O2 179.27(17) . . . . ? C3 N3 C4 N4 -1.6(4) . . . . ? C3 N3 C4 O2 179.3(2) . . . . ? C5 O2 C4 N4 -179.0(2) . . . . ? C5 O2 C4 N3 0.2(3) . . . . ? N2 C2 C6 C7 15.6(3) . . . . ? C12 C2 C6 C7 143.0(2) . . . . ? C1 C2 C6 C7 -91.8(3) . . . . ? N2 C2 C6 C11 -167.7(2) . . . . ? C12 C2 C6 C11 -40.3(3) . . . . ? C1 C2 C6 C11 84.8(3) . . . . ? C11 C6 C7 C8 0.9(4) . . . . ? C2 C6 C7 C8 177.6(2) . . . . ? C6 C7 C8 C9 0.5(4) . . . . ? C7 C8 C9 C10 -1.0(5) . . . . ? C8 C9 C10 C11 0.1(5) . . . . ? C9 C10 C11 C6 1.3(5) . . . . ? C7 C6 C11 C10 -1.7(4) . . . . ? C2 C6 C11 C10 -178.5(3) . . . . ? N2 C2 C12 C17 -77.7(3) . . . . ? C6 C2 C12 C17 155.1(3) . . . . ? C1 C2 C12 C17 32.3(4) . . . . ? N2 C2 C12 C13 99.3(3) . . . . ? C6 C2 C12 C13 -27.9(4) . . . . ? C1 C2 C12 C13 -150.7(3) . . . . ? C17 C12 C13 C14 -0.5(5) . . . . ? C2 C12 C13 C14 -177.5(3) . . . . ? C12 C13 C14 C15 -0.4(5) . . . . ? C13 C14 C15 C16 0.9(6) . . . . ? C14 C15 C16 C17 -0.5(7) . . . . ? C13 C12 C17 C16 1.0(5) . . . . ? C2 C12 C17 C16 178.0(3) . . . . ? C15 C16 C17 C12 -0.5(7) . . . . ? C20 N5 C18 O3 177.5(3) . . . . ? Cu1 N5 C18 O3 -0.4(4) . . . . ? C20 N5 C18 C19 -2.3(3) . . . . ? Cu1 N5 C18 C19 179.81(16) . . . . ? C20 N6 C19 C23 112.7(2) . . . . ? C20 N6 C19 C29 -117.5(2) . . . . ? C20 N6 C19 C18 -0.9(3) . . . . ? O3 C18 C19 N6 -177.8(2) . . . . ? N5 C18 C19 N6 2.0(3) . . . . ? O3 C18 C19 C23 64.6(3) . . . . ? N5 C18 C19 C23 -115.6(2) . . . . ? O3 C18 C19 C29 -61.9(3) . . . . ? N5 C18 C19 C29 117.9(2) . . . . ? C21 N7 C20 N6 178.6(2) . . . . ? C21 N7 C20 N5 -0.8(4) . . . . ? C19 N6 C20 N7 -179.9(2) . . . . ? C19 N6 C20 N5 -0.5(3) . . . . ? C18 N5 C20 N7 -178.8(3) . . . . ? Cu1 N5 C20 N7 -0.8(4) . . . . ? C18 N5 C20 N6 1.8(3) . . . . ? Cu1 N5 C20 N6 179.82(16) . . . . ? Cu1 N8 C21 N7 -12.4(4) . . . . ? Cu1 N8 C21 O4 168.03(18) . . . . ? C20 N7 C21 N8 7.5(4) . . . . ? C20 N7 C21 O4 -172.9(2) . . . . ? C22 O4 C21 N8 -171.2(3) . . . . ? C22 O4 C21 N7 9.2(3) . . . . ? N6 C19 C23 C24 -3.7(3) . . . . ? C29 C19 C23 C24 -130.9(3) . . . . ? C18 C19 C23 C24 104.9(3) . . . . ? N6 C19 C23 C28 179.7(2) . . . . ? C29 C19 C23 C28 52.5(3) . . . . ? C18 C19 C23 C28 -71.7(3) . . . . ? C28 C23 C24 C25 -0.1(4) . . . . ? C19 C23 C24 C25 -176.7(3) . . . . ? C23 C24 C25 C26 -0.7(5) . . . . ? C24 C25 C26 C27 0.9(5) . . . . ? C25 C26 C27 C28 -0.3(5) . . . . ? C26 C27 C28 C23 -0.5(4) . . . . ? C24 C23 C28 C27 0.7(4) . . . . ? C19 C23 C28 C27 177.4(3) . . . . ? N6 C19 C29 C30 -100.3(3) . . . . ? C23 C19 C29 C30 28.2(3) . . . . ? C18 C19 C29 C30 150.5(2) . . . . ? N6 C19 C29 C34 76.9(3) . . . . ? C23 C19 C29 C34 -154.6(2) . . . . ? C18 C19 C29 C34 -32.3(3) . . . . ? C34 C29 C30 C31 -0.3(4) . . . . ? C19 C29 C30 C31 176.9(2) . . . . ? C29 C30 C31 C32 0.0(4) . . . . ? C30 C31 C32 C33 0.1(4) . . . . ? C31 C32 C33 C34 0.1(4) . . . . ? C32 C33 C34 C29 -0.4(4) . . . . ? C30 C29 C34 C33 0.5(4) . . . . ? C19 C29 C34 C33 -176.8(2) . . . . ? 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 N8 H8N O1 0.88 2.03 2.788(3) 144.0 . N4 H4N O3 0.88 1.95 2.748(3) 150.0 . N2 H2N O6 0.88 1.95 2.777(3) 155.6 . N6 H6N O5 0.88 1.92 2.764(3) 160.4 . _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.903 _refine_diff_density_max 0.413 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.074