# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Shi-Ping Yan' _publ_contact_author_email YANSP@NANKAI.EDU.CN _publ_section_title ; Synthesis, X-ray Crystal Structures, Magnetism, and DNA Cleavage Properties of Copper (II) Complexes with 1,4-tpbd ligand ; loop_ _publ_author_name 'Shi-Ping Yan.' 'Gong-Jun Chen.' 'Wen Gu.' 'Fu-Ping Huang.' 'Ying-Ying Kou.' ; Dongdong Li ; 'Xin Liu.' 'Jin-Lei Tian.' # Attachment '1.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 639516' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 Br2 Cu N6' _chemical_formula_sum 'C30 H28 Br2 Cu N6' _chemical_formula_weight 695.94 _chemical_absolute_configuration rmad 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.372(4) _cell_length_b 12.813(6) _cell_length_c 13.103(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.509(5) _cell_angle_gamma 90.00 _cell_volume 1354.4(12) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3003 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 27.9 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 698 _exptl_absorpt_coefficient_mu 3.789 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6190 _exptl_absorpt_correction_T_max 0.6592 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12782 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.1065 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.88 _reflns_number_total 6328 _reflns_number_gt 5127 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0417P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.045(12) _refine_ls_number_reflns 6328 _refine_ls_number_parameters 353 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.013 _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 0.59652(8) -0.02396(6) 0.57182(5) 0.01366(16) Uani 1 1 d U . . Br1 Br 0.40639(7) -0.03973(5) 0.38757(4) 0.01926(15) Uani 1 1 d . . . Br2 Br 0.70876(8) -0.19264(5) 0.64474(5) 0.02434(16) Uani 1 1 d U . . N1 N 0.4118(6) -0.0159(4) 0.6412(3) 0.0145(10) Uani 1 1 d . . . N2 N 0.7869(6) 0.0141(4) 0.5152(4) 0.0152(11) Uani 1 1 d . . . N3 N 0.6210(6) 0.1354(4) 0.6206(4) 0.0130(11) Uani 1 1 d . . . N4 N 1.0822(6) 0.1680(4) 1.0267(4) 0.0207(12) Uani 1 1 d . . . N5 N 1.3925(6) 0.3799(4) 1.0567(4) 0.0200(12) Uani 1 1 d . . . N6 N 0.8970(6) -0.0175(5) 1.1689(4) 0.0235(12) Uani 1 1 d . . . C1 C 0.3271(7) -0.0983(5) 0.6652(5) 0.0156(13) Uani 1 1 d . . . H1 H 0.3607 -0.1669 0.6528 0.019 Uiso 1 1 calc R . . C2 C 0.1934(8) -0.0855(5) 0.7069(5) 0.0207(15) Uani 1 1 d . . . H2 H 0.1333 -0.1441 0.7212 0.025 Uiso 1 1 calc R . . C3 C 0.1488(8) 0.0150(6) 0.7276(5) 0.0246(16) Uani 1 1 d . . . H3 H 0.0584 0.0256 0.7574 0.030 Uiso 1 1 calc R . . C4 C 0.2355(7) 0.0995(6) 0.7050(5) 0.0209(15) Uani 1 1 d . . . C5 C 0.3665(7) 0.0809(5) 0.6597(4) 0.0130(12) Uani 1 1 d . . . C6 C 0.4577(7) 0.1689(5) 0.6246(5) 0.0156(13) Uani 1 1 d . . . H6A H 0.3942 0.1932 0.5537 0.019 Uiso 1 1 calc R . . H6B H 0.4681 0.2281 0.6746 0.019 Uiso 1 1 calc R . . C7 C 0.8854(7) -0.0529(5) 0.4815(4) 0.0171(13) Uani 1 1 d . . . H7 H 0.8691 -0.1258 0.4867 0.021 Uiso 1 1 calc R . . C8 C 1.0092(7) -0.0174(5) 0.4395(4) 0.0200(14) Uani 1 1 d . . . H8 H 1.0776 -0.0659 0.4159 0.024 Uiso 1 1 calc R . . C9 C 1.0345(7) 0.0884(5) 0.4314(5) 0.0191(14) Uani 1 1 d . . . H9 H 1.1211 0.1139 0.4038 0.023 Uiso 1 1 calc R . . C10 C 0.9306(8) 0.1558(6) 0.4644(5) 0.0191(14) Uani 1 1 d . . . H10 H 0.9445 0.2291 0.4595 0.023 Uiso 1 1 calc R . . C11 C 0.8064(7) 0.1172(5) 0.5048(4) 0.0148(12) Uani 1 1 d . . . C12 C 0.6789(8) 0.1834(5) 0.5336(5) 0.0170(13) Uani 1 1 d . . . H12A H 0.7262 0.2531 0.5562 0.020 Uiso 1 1 calc R . . H12B H 0.5833 0.1927 0.4708 0.020 Uiso 1 1 calc R . . C13 C 0.7451(7) 0.1431(5) 0.7253(4) 0.0134(9) Uani 1 1 d U . . C14 C 0.7609(7) 0.0634(4) 0.7994(5) 0.0142(13) Uani 1 1 d . . . H14 H 0.6958 0.0021 0.7811 0.017 Uiso 1 1 calc R . . C15 C 0.8701(7) 0.0719(5) 0.8994(5) 0.0143(13) Uani 1 1 d . . . H15 H 0.8767 0.0170 0.9491 0.017 Uiso 1 1 calc R . . C16 C 0.9716(7) 0.1610(5) 0.9284(5) 0.0132(12) Uani 1 1 d . . . C17 C 0.9547(7) 0.2405(5) 0.8526(5) 0.0165(14) Uani 1 1 d . . . H17 H 1.0221 0.3011 0.8692 0.020 Uiso 1 1 calc R . . C18 C 0.8414(7) 0.2324(5) 0.7540(5) 0.0144(9) Uani 1 1 d U . . H18 H 0.8293 0.2887 0.7053 0.017 Uiso 1 1 calc R . . C19 C 1.1663(8) 0.2670(5) 1.0611(5) 0.0211(14) Uani 1 1 d . . . H19A H 1.1986 0.2687 1.1395 0.025 Uiso 1 1 calc R . . H19B H 1.0862 0.3244 1.0361 0.025 Uiso 1 1 calc R . . C20 C 1.3187(7) 0.2884(5) 1.0235(4) 0.0150(13) Uani 1 1 d . . . C21 C 1.3784(8) 0.2205(6) 0.9602(5) 0.0200(14) Uani 1 1 d . . . H21 H 1.3231 0.1563 0.9382 0.024 Uiso 1 1 calc R . . C22 C 1.5179(8) 0.2462(5) 0.9291(5) 0.0240(16) Uani 1 1 d . . . H22 H 1.5607 0.2000 0.8862 0.029 Uiso 1 1 calc R . . C23 C 1.5940(8) 0.3400(6) 0.9615(6) 0.0309(18) Uani 1 1 d . . . H23 H 1.6896 0.3612 0.9410 0.037 Uiso 1 1 calc R . . C24 C 1.5263(8) 0.4019(6) 1.0246(5) 0.0269(16) Uani 1 1 d . . . H24 H 1.5801 0.4664 1.0474 0.032 Uiso 1 1 calc R . . C25 C 1.0900(7) 0.0872(5) 1.1053(5) 0.0199(14) Uani 1 1 d . . . H25A H 1.1860 0.1011 1.1668 0.024 Uiso 1 1 calc R . . H25B H 1.1093 0.0192 1.0747 0.024 Uiso 1 1 calc R . . C26 C 0.9371(8) 0.0789(5) 1.1436(4) 0.0163(13) Uani 1 1 d . . . C27 C 0.8432(8) 0.1653(5) 1.1517(5) 0.0219(14) Uani 1 1 d . . . H27 H 0.8757 0.2327 1.1348 0.026 Uiso 1 1 calc R . . C28 C 0.6988(8) 0.1521(6) 1.1855(5) 0.0243(15) Uani 1 1 d . . . H28 H 0.6304 0.2100 1.1905 0.029 Uiso 1 1 calc R . . C29 C 0.6598(9) 0.0549(6) 1.2106(5) 0.0258(16) Uani 1 1 d . . . H29 H 0.5628 0.0433 1.2335 0.031 Uiso 1 1 calc R . . C30 C 0.7614(8) -0.0268(6) 1.2027(5) 0.0273(15) Uani 1 1 d . . . H30 H 0.7332 -0.0942 1.2226 0.033 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 0.0122(3) 0.0151(4) 0.0152(3) -0.0010(3) 0.0063(3) -0.0002(3) Br1 0.0154(3) 0.0262(4) 0.0165(3) -0.0003(3) 0.0047(2) -0.0034(3) Br2 0.0284(4) 0.0225(4) 0.0220(3) 0.0011(3) 0.0065(3) 0.0018(3) N1 0.012(2) 0.016(3) 0.015(2) -0.002(2) 0.0031(18) -0.002(2) N2 0.012(3) 0.020(3) 0.013(2) -0.002(2) 0.001(2) 0.000(2) N3 0.015(3) 0.016(3) 0.008(2) -0.003(2) 0.004(2) -0.004(2) N4 0.016(3) 0.027(3) 0.017(3) -0.006(2) 0.002(2) -0.005(2) N5 0.016(3) 0.019(3) 0.023(3) -0.002(2) 0.002(2) -0.005(2) N6 0.025(3) 0.026(3) 0.017(2) 0.000(2) 0.002(2) -0.007(3) C1 0.009(3) 0.025(4) 0.014(3) -0.004(3) 0.005(2) -0.004(3) C2 0.018(4) 0.023(4) 0.017(3) 0.000(3) -0.002(3) -0.004(3) C3 0.018(4) 0.040(4) 0.019(3) 0.006(3) 0.010(3) 0.002(3) C4 0.009(3) 0.040(4) 0.013(3) -0.003(3) 0.001(2) -0.004(3) C5 0.010(3) 0.018(3) 0.009(3) 0.000(2) -0.001(2) 0.000(2) C6 0.008(3) 0.020(3) 0.021(3) -0.001(3) 0.007(2) 0.003(2) C7 0.019(3) 0.016(3) 0.019(3) -0.003(3) 0.010(2) -0.002(3) C8 0.013(3) 0.027(4) 0.020(3) -0.002(3) 0.005(2) -0.004(3) C9 0.010(3) 0.031(4) 0.017(3) 0.002(3) 0.006(2) -0.004(3) C10 0.013(3) 0.029(4) 0.015(3) 0.006(3) 0.002(2) -0.002(3) C11 0.013(3) 0.017(3) 0.014(3) -0.002(2) 0.002(2) -0.001(2) C12 0.019(3) 0.011(3) 0.024(3) -0.001(3) 0.011(3) -0.001(2) C13 0.015(2) 0.016(2) 0.0089(19) -0.0029(17) 0.0024(16) 0.0012(17) C14 0.020(3) 0.008(3) 0.018(3) 0.000(2) 0.011(3) 0.005(2) C15 0.017(3) 0.010(3) 0.019(3) 0.001(2) 0.009(3) 0.000(2) C16 0.012(3) 0.013(3) 0.017(3) 0.000(2) 0.008(2) 0.005(2) C17 0.009(3) 0.020(4) 0.022(3) -0.002(3) 0.006(3) -0.001(2) C18 0.016(2) 0.016(2) 0.0104(19) -0.0020(17) 0.0019(17) 0.0007(18) C19 0.025(4) 0.023(4) 0.014(3) -0.006(3) 0.004(3) 0.001(3) C20 0.015(3) 0.018(3) 0.013(3) -0.005(2) 0.004(2) -0.007(3) C21 0.018(3) 0.022(3) 0.018(4) -0.005(3) 0.001(3) 0.000(3) C22 0.015(3) 0.031(4) 0.028(4) -0.001(3) 0.010(3) 0.008(3) C23 0.016(4) 0.040(5) 0.037(4) 0.010(3) 0.007(3) -0.003(3) C24 0.022(4) 0.026(4) 0.027(4) 0.000(3) -0.004(3) -0.012(3) C25 0.014(3) 0.029(4) 0.013(3) 0.002(3) -0.002(2) -0.002(3) C26 0.018(3) 0.019(3) 0.011(3) 0.003(2) 0.002(2) 0.000(3) C27 0.020(3) 0.027(4) 0.018(3) 0.000(3) 0.004(3) -0.001(3) C28 0.023(4) 0.034(4) 0.016(3) -0.006(3) 0.004(3) 0.005(3) C29 0.016(3) 0.040(5) 0.020(3) -0.006(3) 0.001(3) -0.009(3) C30 0.031(4) 0.028(4) 0.022(3) 0.001(3) 0.006(3) -0.011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.991(5) . ? Cu1 N1 1.995(5) . ? Cu1 N3 2.133(5) . ? Cu1 Br2 2.4468(14) . ? Cu1 Br1 2.5195(14) . ? N1 C5 1.338(7) . ? N1 C1 1.354(7) . ? N2 C11 1.342(8) . ? N2 C7 1.344(7) . ? N3 C6 1.447(7) . ? N3 C12 1.486(7) . ? N3 C13 1.486(7) . ? N4 C16 1.374(7) . ? N4 C25 1.450(8) . ? N4 C19 1.462(8) . ? N5 C24 1.327(8) . ? N5 C20 1.343(7) . ? N6 C30 1.330(8) . ? N6 C26 1.345(8) . ? C1 C2 1.381(8) . ? C1 H1 0.9500 . ? C2 C3 1.387(9) . ? C2 H2 0.9500 . ? C3 C4 1.379(10) . ? C3 H3 0.9500 . ? C4 C5 1.399(8) . ? C5 C6 1.501(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.375(8) . ? C7 H7 0.9500 . ? C8 C9 1.381(9) . ? C8 H8 0.9500 . ? C9 C10 1.375(9) . ? C9 H9 0.9500 . ? C10 C11 1.378(8) . ? C10 H10 0.9500 . ? C11 C12 1.489(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.390(8) . ? C13 C18 1.393(8) . ? C14 C15 1.387(8) . ? C14 H14 0.9500 . ? C15 C16 1.414(8) . ? C15 H15 0.9500 . ? C16 C17 1.402(8) . ? C17 C18 1.388(8) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.510(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.385(8) . ? C21 C22 1.375(9) . ? C21 H21 0.9500 . ? C22 C23 1.374(10) . ? C22 H22 0.9500 . ? C23 C24 1.372(10) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.498(8) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.377(9) . ? C27 C28 1.404(9) . ? C27 H27 0.9500 . ? C28 C29 1.350(10) . ? C28 H28 0.9500 . ? C29 C30 1.370(10) . ? C29 H29 0.9500 . ? C30 H30 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 N2 Cu1 N1 162.3(2) . . ? N2 Cu1 N3 81.65(19) . . ? N1 Cu1 N3 80.7(2) . . ? N2 Cu1 Br2 95.74(14) . . ? N1 Cu1 Br2 97.53(15) . . ? N3 Cu1 Br2 137.08(14) . . ? N2 Cu1 Br1 91.49(14) . . ? N1 Cu1 Br1 94.18(13) . . ? N3 Cu1 Br1 110.46(14) . . ? Br2 Cu1 Br1 112.43(4) . . ? C5 N1 C1 119.3(5) . . ? C5 N1 Cu1 115.0(4) . . ? C1 N1 Cu1 125.7(4) . . ? C11 N2 C7 119.6(5) . . ? C11 N2 Cu1 114.2(4) . . ? C7 N2 Cu1 126.0(4) . . ? C6 N3 C12 114.2(5) . . ? C6 N3 C13 112.4(4) . . ? C12 N3 C13 112.9(5) . . ? C6 N3 Cu1 106.2(4) . . ? C12 N3 Cu1 101.0(3) . . ? C13 N3 Cu1 109.1(4) . . ? C16 N4 C25 120.7(5) . . ? C16 N4 C19 119.6(5) . . ? C25 N4 C19 118.3(5) . . ? C24 N5 C20 115.9(6) . . ? C30 N6 C26 117.1(6) . . ? N1 C1 C2 121.9(6) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C1 C2 C3 118.5(6) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 120.1(6) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 118.4(6) . . ? N1 C5 C4 121.8(6) . . ? N1 C5 C6 116.7(5) . . ? C4 C5 C6 121.5(5) . . ? N3 C6 C5 110.6(5) . . ? N3 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N2 C7 C8 121.0(6) . . ? N2 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C7 C8 C9 120.2(6) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 118.0(6) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? C9 C10 C11 120.1(6) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? N2 C11 C10 121.1(6) . . ? N2 C11 C12 114.8(5) . . ? C10 C11 C12 124.0(6) . . ? N3 C12 C11 111.3(5) . . ? N3 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? N3 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C18 118.4(5) . . ? C14 C13 N3 120.6(5) . . ? C18 C13 N3 121.0(5) . . ? C15 C14 C13 121.2(5) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 120.9(5) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? N4 C16 C17 122.1(6) . . ? N4 C16 C15 120.7(5) . . ? C17 C16 C15 117.2(5) . . ? C18 C17 C16 121.3(6) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C13 121.0(6) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? N4 C19 C20 115.9(5) . . ? N4 C19 H19A 108.3 . . ? C20 C19 H19A 108.3 . . ? N4 C19 H19B 108.3 . . ? C20 C19 H19B 108.3 . . ? H19A C19 H19B 107.4 . . ? N5 C20 C21 122.3(6) . . ? N5 C20 C19 114.2(5) . . ? C21 C20 C19 123.6(6) . . ? C22 C21 C20 119.9(6) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C23 C22 C21 118.6(6) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C24 C23 C22 117.4(6) . . ? C24 C23 H23 121.3 . . ? C22 C23 H23 121.3 . . ? N5 C24 C23 126.0(6) . . ? N5 C24 H24 117.0 . . ? C23 C24 H24 117.0 . . ? N4 C25 C26 114.1(5) . . ? N4 C25 H25A 108.7 . . ? C26 C25 H25A 108.7 . . ? N4 C25 H25B 108.7 . . ? C26 C25 H25B 108.7 . . ? H25A C25 H25B 107.6 . . ? N6 C26 C27 122.3(6) . . ? N6 C26 C25 116.0(5) . . ? C27 C26 C25 121.7(6) . . ? C26 C27 C28 119.0(6) . . ? C26 C27 H27 120.5 . . ? C28 C27 H27 120.5 . . ? C29 C28 C27 118.2(7) . . ? C29 C28 H28 120.9 . . ? C27 C28 H28 120.9 . . ? C28 C29 C30 119.4(6) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? N6 C30 C29 124.0(7) . . ? N6 C30 H30 118.0 . . ? C29 C30 H30 118.0 . . ? 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 N2 Cu1 N1 C5 13.3(9) . . . . ? N3 Cu1 N1 C5 15.0(4) . . . . ? Br2 Cu1 N1 C5 151.6(4) . . . . ? Br1 Cu1 N1 C5 -95.1(4) . . . . ? N2 Cu1 N1 C1 -170.1(6) . . . . ? N3 Cu1 N1 C1 -168.4(5) . . . . ? Br2 Cu1 N1 C1 -31.7(5) . . . . ? Br1 Cu1 N1 C1 81.6(4) . . . . ? N1 Cu1 N2 C11 -16.6(9) . . . . ? N3 Cu1 N2 C11 -18.3(4) . . . . ? Br2 Cu1 N2 C11 -155.2(4) . . . . ? Br1 Cu1 N2 C11 92.1(4) . . . . ? N1 Cu1 N2 C7 168.0(5) . . . . ? N3 Cu1 N2 C7 166.3(5) . . . . ? Br2 Cu1 N2 C7 29.5(5) . . . . ? Br1 Cu1 N2 C7 -83.2(5) . . . . ? N2 Cu1 N3 C6 152.1(4) . . . . ? N1 Cu1 N3 C6 -27.4(4) . . . . ? Br2 Cu1 N3 C6 -118.5(3) . . . . ? Br1 Cu1 N3 C6 63.6(4) . . . . ? N2 Cu1 N3 C12 32.7(4) . . . . ? N1 Cu1 N3 C12 -146.8(4) . . . . ? Br2 Cu1 N3 C12 122.1(3) . . . . ? Br1 Cu1 N3 C12 -55.8(4) . . . . ? N2 Cu1 N3 C13 -86.6(4) . . . . ? N1 Cu1 N3 C13 94.0(4) . . . . ? Br2 Cu1 N3 C13 2.9(5) . . . . ? Br1 Cu1 N3 C13 -175.0(3) . . . . ? C5 N1 C1 C2 0.9(8) . . . . ? Cu1 N1 C1 C2 -175.6(4) . . . . ? N1 C1 C2 C3 -2.0(10) . . . . ? C1 C2 C3 C4 1.0(10) . . . . ? C2 C3 C4 C5 0.9(9) . . . . ? C1 N1 C5 C4 1.2(8) . . . . ? Cu1 N1 C5 C4 178.0(4) . . . . ? C1 N1 C5 C6 -175.9(5) . . . . ? Cu1 N1 C5 C6 0.9(6) . . . . ? C3 C4 C5 N1 -2.0(9) . . . . ? C3 C4 C5 C6 174.9(6) . . . . ? C12 N3 C6 C5 144.9(5) . . . . ? C13 N3 C6 C5 -84.7(6) . . . . ? Cu1 N3 C6 C5 34.5(5) . . . . ? N1 C5 C6 N3 -25.5(7) . . . . ? C4 C5 C6 N3 157.4(5) . . . . ? C11 N2 C7 C8 2.0(9) . . . . ? Cu1 N2 C7 C8 177.2(4) . . . . ? N2 C7 C8 C9 0.1(9) . . . . ? C7 C8 C9 C10 -1.3(9) . . . . ? C8 C9 C10 C11 0.4(9) . . . . ? C7 N2 C11 C10 -3.0(8) . . . . ? Cu1 N2 C11 C10 -178.6(4) . . . . ? C7 N2 C11 C12 173.5(5) . . . . ? Cu1 N2 C11 C12 -2.1(6) . . . . ? C9 C10 C11 N2 1.7(9) . . . . ? C9 C10 C11 C12 -174.4(6) . . . . ? C6 N3 C12 C11 -156.2(5) . . . . ? C13 N3 C12 C11 73.7(6) . . . . ? Cu1 N3 C12 C11 -42.7(5) . . . . ? N2 C11 C12 N3 32.9(7) . . . . ? C10 C11 C12 N3 -150.8(6) . . . . ? C6 N3 C13 C14 83.8(7) . . . . ? C12 N3 C13 C14 -145.2(5) . . . . ? Cu1 N3 C13 C14 -33.7(6) . . . . ? C6 N3 C13 C18 -92.5(6) . . . . ? C12 N3 C13 C18 38.5(7) . . . . ? Cu1 N3 C13 C18 150.0(5) . . . . ? C18 C13 C14 C15 -0.2(8) . . . . ? N3 C13 C14 C15 -176.6(5) . . . . ? C13 C14 C15 C16 -1.5(9) . . . . ? C25 N4 C16 C17 176.4(5) . . . . ? C19 N4 C16 C17 10.1(8) . . . . ? C25 N4 C16 C15 -3.9(8) . . . . ? C19 N4 C16 C15 -170.3(5) . . . . ? C14 C15 C16 N4 -178.5(5) . . . . ? C14 C15 C16 C17 1.1(8) . . . . ? N4 C16 C17 C18 -179.5(5) . . . . ? C15 C16 C17 C18 0.8(9) . . . . ? C16 C17 C18 C13 -2.5(9) . . . . ? C14 C13 C18 C17 2.2(8) . . . . ? N3 C13 C18 C17 178.6(5) . . . . ? C16 N4 C19 C20 -83.1(7) . . . . ? C25 N4 C19 C20 110.2(6) . . . . ? C24 N5 C20 C21 0.3(9) . . . . ? C24 N5 C20 C19 -179.5(6) . . . . ? N4 C19 C20 N5 180.0(5) . . . . ? N4 C19 C20 C21 0.1(9) . . . . ? N5 C20 C21 C22 -0.1(10) . . . . ? C19 C20 C21 C22 179.8(6) . . . . ? C20 C21 C22 C23 -0.6(9) . . . . ? C21 C22 C23 C24 0.9(10) . . . . ? C20 N5 C24 C23 0.1(10) . . . . ? C22 C23 C24 N5 -0.7(11) . . . . ? C16 N4 C25 C26 -65.9(7) . . . . ? C19 N4 C25 C26 100.7(6) . . . . ? C30 N6 C26 C27 -0.1(8) . . . . ? C30 N6 C26 C25 -179.7(5) . . . . ? N4 C25 C26 N6 146.7(5) . . . . ? N4 C25 C26 C27 -33.0(8) . . . . ? N6 C26 C27 C28 -1.3(9) . . . . ? C25 C26 C27 C28 178.3(5) . . . . ? C26 C27 C28 C29 1.2(9) . . . . ? C27 C28 C29 C30 0.2(9) . . . . ? C26 N6 C30 C29 1.6(9) . . . . ? C28 C29 C30 N6 -1.7(10) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.679 _refine_diff_density_min -0.792 _refine_diff_density_rms 0.145 # Attachment '2.cif' data_070709c _database_code_depnum_ccdc_archive 'CCDC 689792' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 Cl2 Cu N3 O10' _chemical_formula_weight 534.76 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 P2(1)/n 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 10.428(5) _cell_length_b 17.954(8) _cell_length_c 10.785(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.410(7) _cell_angle_gamma 90.00 _cell_volume 1926.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3381 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 26.11 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.844 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.475 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.696534 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 9520 _diffrn_reflns_av_R_equivalents 0.0963 _diffrn_reflns_av_sigmaI/netI 0.0844 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3389 _reflns_number_gt 2460 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+0.6928P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3389 _refine_ls_number_parameters 280 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _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 0.56521(5) 0.11800(3) 0.70459(4) 0.02279(17) Uani 1 1 d . . . O1 O 0.5242(3) 0.00056(17) 0.6433(3) 0.0548(9) Uani 1 1 d D . . H1A H 0.5796 -0.0288 0.6939 0.066 Uiso 1 1 d RD . . H1B H 0.4418 -0.0044 0.6372 0.066 Uiso 1 1 d RD . . O2 O 0.5776(3) 0.14441(17) 0.5289(2) 0.0380(8) Uani 1 1 d D . . H2A H 0.6555 0.1557 0.5259 0.046 Uiso 1 1 d RD . . H2B H 0.5114 0.1619 0.4694 0.046 Uiso 1 1 d RD . . N1 N 0.7562(3) 0.10131(17) 0.7834(3) 0.0250(8) Uani 1 1 d . . . N2 N 0.5652(3) 0.13470(16) 0.8931(3) 0.0172(7) Uani 1 1 d . . . N3 N 0.3769(3) 0.14436(17) 0.6661(3) 0.0231(8) Uani 1 1 d . . . C1 C 0.8413(4) 0.0680(2) 0.7293(4) 0.0320(10) Uani 1 1 d . . . H1 H 0.8090 0.0521 0.6435 0.038 Uiso 1 1 calc R . . C2 C 0.9728(5) 0.0567(3) 0.7947(4) 0.0427(12) Uani 1 1 d . . . H2 H 1.0293 0.0325 0.7554 0.051 Uiso 1 1 calc R . . C3 C 1.0204(5) 0.0819(3) 0.9200(4) 0.0419(12) Uani 1 1 d . . . H3 H 1.1108 0.0764 0.9658 0.050 Uiso 1 1 calc R . . C4 C 0.9360(4) 0.1147(2) 0.9772(4) 0.0350(11) Uani 1 1 d . . . H4 H 0.9672 0.1307 1.0631 0.042 Uiso 1 1 calc R . . C5 C 0.8037(4) 0.12404(19) 0.9069(3) 0.0212(9) Uani 1 1 d . . . C6 C 0.7037(4) 0.1597(2) 0.9619(3) 0.0241(9) Uani 1 1 d . . . H6A H 0.7250 0.1472 1.0534 0.029 Uiso 1 1 calc R . . H6B H 0.7090 0.2134 0.9548 0.029 Uiso 1 1 calc R . . C7 C 0.4650(4) 0.1950(2) 0.8778(3) 0.0233(9) Uani 1 1 d . . . H7A H 0.5043 0.2422 0.8645 0.028 Uiso 1 1 calc R . . H7B H 0.4375 0.1989 0.9559 0.028 Uiso 1 1 calc R . . C8 C 0.3453(4) 0.1782(2) 0.7636(3) 0.0224(9) Uani 1 1 d . . . C9 C 0.2167(4) 0.1973(2) 0.7564(4) 0.0304(10) Uani 1 1 d . . . H9 H 0.1973 0.2209 0.8255 0.037 Uiso 1 1 calc R . . C10 C 0.1163(4) 0.1806(2) 0.6437(4) 0.0366(11) Uani 1 1 d . . . H10 H 0.0278 0.1938 0.6349 0.044 Uiso 1 1 calc R . . C11 C 0.1471(4) 0.1447(2) 0.5457(4) 0.0371(11) Uani 1 1 d . . . H11 H 0.0796 0.1321 0.4702 0.045 Uiso 1 1 calc R . . C12 C 0.2775(4) 0.1272(2) 0.5584(4) 0.0302(11) Uani 1 1 d . . . H12 H 0.2980 0.1028 0.4908 0.036 Uiso 1 1 calc R . . C13 C 0.5305(4) 0.0661(2) 0.9478(3) 0.0183(8) Uani 1 1 d . . . C14 C 0.6137(4) 0.0070(2) 0.9674(4) 0.0410(12) Uani 1 1 d . . . H14 H 0.6932 0.0108 0.9455 0.049 Uiso 1 1 calc R . . C15 C 0.4154(4) 0.0590(2) 0.9811(4) 0.0401(12) Uani 1 1 d . . . H15 H 0.3559 0.0989 0.9692 0.048 Uiso 1 1 calc R . . Cl1 Cl 0.27332(12) 0.19076(6) 0.22185(9) 0.0358(3) Uani 1 1 d . . . Cl2 Cl 0.78046(12) 0.09917(6) 0.33784(9) 0.0378(3) Uani 1 1 d . . . O3 O 0.2689(4) 0.11147(18) 0.2243(4) 0.0692(12) Uani 1 1 d . . . O4 O 0.3804(4) 0.21638(19) 0.3294(3) 0.0635(11) Uani 1 1 d . . . O5 O 0.1509(3) 0.22024(19) 0.2333(3) 0.0535(9) Uani 1 1 d . . . O6 O 0.2915(4) 0.2158(2) 0.1050(3) 0.0751(12) Uani 1 1 d . . . O7 O 0.6485(4) 0.1136(3) 0.2579(3) 0.0852(15) Uani 1 1 d . . . O8 O 0.8720(4) 0.1123(2) 0.2681(3) 0.0677(12) Uani 1 1 d . . . O9 O 0.7932(7) 0.0281(2) 0.3883(5) 0.140(2) Uani 1 1 d . . . O10 O 0.8079(3) 0.1499(2) 0.4442(3) 0.0540(9) 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 0.0234(3) 0.0266(3) 0.0179(2) -0.00113(19) 0.0054(2) 0.0009(2) O1 0.047(2) 0.0414(19) 0.070(2) -0.0241(16) 0.0078(18) -0.0043(18) O2 0.0293(17) 0.060(2) 0.0240(13) 0.0096(14) 0.0074(13) -0.0010(17) N1 0.030(2) 0.0212(17) 0.0251(16) 0.0054(14) 0.0099(15) 0.0004(16) N2 0.0205(17) 0.0154(16) 0.0179(14) 0.0017(12) 0.0089(13) 0.0020(14) N3 0.0246(19) 0.0189(16) 0.0236(15) 0.0042(14) 0.0039(14) 0.0018(16) C1 0.035(3) 0.033(2) 0.034(2) 0.0016(19) 0.019(2) 0.004(2) C2 0.037(3) 0.041(3) 0.060(3) 0.009(2) 0.029(3) 0.010(2) C3 0.024(3) 0.044(3) 0.056(3) 0.013(2) 0.008(2) 0.005(2) C4 0.026(2) 0.039(3) 0.036(2) 0.006(2) 0.004(2) -0.002(2) C5 0.021(2) 0.018(2) 0.0260(19) 0.0059(16) 0.0079(17) -0.0055(17) C6 0.026(2) 0.020(2) 0.0236(18) -0.0040(16) 0.0039(17) -0.0080(19) C7 0.027(2) 0.019(2) 0.0246(18) 0.0029(16) 0.0079(17) 0.0037(19) C8 0.025(2) 0.0133(19) 0.030(2) 0.0051(16) 0.0104(18) 0.0008(18) C9 0.030(3) 0.024(2) 0.041(2) 0.0081(19) 0.017(2) 0.008(2) C10 0.022(2) 0.029(2) 0.058(3) 0.017(2) 0.009(2) 0.006(2) C11 0.028(3) 0.030(2) 0.044(2) 0.008(2) -0.003(2) -0.004(2) C12 0.032(3) 0.030(2) 0.0242(19) 0.0049(17) 0.0017(19) -0.004(2) C13 0.022(2) 0.018(2) 0.0148(16) 0.0030(15) 0.0056(16) -0.0026(17) C14 0.029(3) 0.031(3) 0.074(3) 0.022(2) 0.033(2) 0.006(2) C15 0.037(3) 0.019(2) 0.073(3) 0.021(2) 0.030(2) 0.012(2) Cl1 0.0444(7) 0.0337(6) 0.0305(5) 0.0016(5) 0.0128(5) 0.0082(5) Cl2 0.0439(7) 0.0389(7) 0.0332(5) -0.0022(5) 0.0152(5) -0.0058(6) O3 0.093(3) 0.033(2) 0.079(2) -0.0049(17) 0.022(2) 0.005(2) O4 0.058(2) 0.053(2) 0.062(2) -0.0028(18) -0.0081(19) 0.011(2) O5 0.048(2) 0.061(2) 0.0546(19) -0.0145(17) 0.0201(17) 0.0088(19) O6 0.099(3) 0.089(3) 0.055(2) 0.025(2) 0.050(2) 0.025(3) O7 0.037(2) 0.158(5) 0.053(2) -0.031(2) 0.0023(18) -0.016(2) O8 0.045(2) 0.119(4) 0.0454(19) 0.007(2) 0.0224(17) 0.002(2) O9 0.270(8) 0.038(3) 0.139(4) 0.023(3) 0.101(5) -0.001(4) O10 0.056(2) 0.064(2) 0.0395(17) -0.0194(16) 0.0112(16) -0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.941(3) . ? Cu1 N1 1.941(3) . ? Cu1 O2 1.995(3) . ? Cu1 N2 2.055(3) . ? Cu1 O1 2.213(3) . ? O1 H1A 0.8491 . ? O1 H1B 0.8468 . ? O2 H2A 0.8465 . ? O2 H2B 0.8491 . ? N1 C5 1.339(5) . ? N1 C1 1.340(5) . ? N2 C13 1.458(4) . ? N2 C7 1.480(5) . ? N2 C6 1.482(5) . ? N3 C8 1.339(5) . ? N3 C12 1.340(4) . ? C1 C2 1.357(6) . ? C1 H1 0.9300 . ? C2 C3 1.370(6) . ? C2 H2 0.9300 . ? C3 C4 1.352(6) . ? C3 H3 0.9300 . ? C4 C5 1.371(5) . ? C4 H4 0.9300 . ? C5 C6 1.489(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.499(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.364(6) . ? C9 C10 1.380(6) . ? C9 H9 0.9300 . ? C10 C11 1.356(6) . ? C10 H10 0.9300 . ? C11 C12 1.362(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.346(5) . ? C13 C15 1.358(6) . ? C14 C15 1.381(6) 3_657 ? C14 H14 0.9300 . ? C15 C14 1.381(6) 3_657 ? C15 H15 0.9300 . ? Cl1 O6 1.403(3) . ? Cl1 O5 1.421(4) . ? Cl1 O4 1.424(3) . ? Cl1 O3 1.425(3) . ? Cl2 O9 1.377(4) . ? Cl2 O8 1.401(4) . ? Cl2 O7 1.412(4) . ? Cl2 O10 1.425(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N1 166.36(13) . . ? N3 Cu1 O2 95.04(12) . . ? N1 Cu1 O2 95.91(13) . . ? N3 Cu1 N2 82.91(12) . . ? N1 Cu1 N2 83.87(13) . . ? O2 Cu1 N2 157.56(12) . . ? N3 Cu1 O1 94.35(13) . . ? N1 Cu1 O1 93.72(13) . . ? O2 Cu1 O1 90.25(13) . . ? N2 Cu1 O1 112.17(12) . . ? Cu1 O1 H1A 111.5 . . ? Cu1 O1 H1B 102.9 . . ? H1A O1 H1B 117.7 . . ? Cu1 O2 H2A 115.4 . . ? Cu1 O2 H2B 122.4 . . ? H2A O2 H2B 117.0 . . ? C5 N1 C1 118.3(4) . . ? C5 N1 Cu1 114.4(3) . . ? C1 N1 Cu1 127.2(3) . . ? C13 N2 C7 114.3(3) . . ? C13 N2 C6 112.1(3) . . ? C7 N2 C6 112.6(3) . . ? C13 N2 Cu1 110.5(2) . . ? C7 N2 Cu1 101.88(19) . . ? C6 N2 Cu1 104.5(2) . . ? C8 N3 C12 118.4(3) . . ? C8 N3 Cu1 114.4(2) . . ? C12 N3 Cu1 126.9(3) . . ? N1 C1 C2 122.5(4) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 118.4(4) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 120.1(4) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.0(4) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 121.6(4) . . ? N1 C5 C6 115.7(3) . . ? C4 C5 C6 122.7(3) . . ? N2 C6 C5 111.3(3) . . ? N2 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N2 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N2 C7 C8 109.3(3) . . ? N2 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N2 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? N3 C8 C9 122.6(3) . . ? N3 C8 C7 113.4(3) . . ? C9 C8 C7 124.0(4) . . ? C8 C9 C10 118.0(4) . . ? C8 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? C11 C10 C9 119.8(4) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 119.5(4) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? N3 C12 C11 121.7(4) . . ? N3 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C14 C13 C15 117.7(4) . . ? C14 C13 N2 120.2(3) . . ? C15 C13 N2 122.1(3) . . ? C13 C14 C15 122.1(4) . 3_657 ? C13 C14 H14 119.0 . . ? C15 C14 H14 119.0 3_657 . ? C13 C15 C14 120.3(4) . 3_657 ? C13 C15 H15 119.9 . . ? C14 C15 H15 119.9 3_657 . ? O6 Cl1 O5 109.0(2) . . ? O6 Cl1 O4 110.1(3) . . ? O5 Cl1 O4 108.4(2) . . ? O6 Cl1 O3 110.5(2) . . ? O5 Cl1 O3 109.6(3) . . ? O4 Cl1 O3 109.2(2) . . ? O9 Cl2 O8 111.6(3) . . ? O9 Cl2 O7 111.8(4) . . ? O8 Cl2 O7 109.7(2) . . ? O9 Cl2 O10 107.5(3) . . ? O8 Cl2 O10 108.7(2) . . ? O7 Cl2 O10 107.4(2) . . ? 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 N3 Cu1 N1 C5 -0.4(7) . . . . ? O2 Cu1 N1 C5 142.8(3) . . . . ? N2 Cu1 N1 C5 -14.7(3) . . . . ? O1 Cu1 N1 C5 -126.6(3) . . . . ? N3 Cu1 N1 C1 177.2(5) . . . . ? O2 Cu1 N1 C1 -39.7(3) . . . . ? N2 Cu1 N1 C1 162.9(3) . . . . ? O1 Cu1 N1 C1 51.0(3) . . . . ? N3 Cu1 N2 C13 88.7(2) . . . . ? N1 Cu1 N2 C13 -94.7(2) . . . . ? O2 Cu1 N2 C13 174.7(3) . . . . ? O1 Cu1 N2 C13 -3.2(3) . . . . ? N3 Cu1 N2 C7 -33.2(2) . . . . ? N1 Cu1 N2 C7 143.5(2) . . . . ? O2 Cu1 N2 C7 52.9(4) . . . . ? O1 Cu1 N2 C7 -125.0(2) . . . . ? N3 Cu1 N2 C6 -150.6(2) . . . . ? N1 Cu1 N2 C6 26.1(2) . . . . ? O2 Cu1 N2 C6 -64.5(4) . . . . ? O1 Cu1 N2 C6 117.6(2) . . . . ? N1 Cu1 N3 C8 2.4(7) . . . . ? O2 Cu1 N3 C8 -140.8(3) . . . . ? N2 Cu1 N3 C8 16.7(3) . . . . ? O1 Cu1 N3 C8 128.5(3) . . . . ? N1 Cu1 N3 C12 -172.2(5) . . . . ? O2 Cu1 N3 C12 44.6(3) . . . . ? N2 Cu1 N3 C12 -157.9(3) . . . . ? O1 Cu1 N3 C12 -46.1(3) . . . . ? C5 N1 C1 C2 -0.1(6) . . . . ? Cu1 N1 C1 C2 -177.6(3) . . . . ? N1 C1 C2 C3 -1.4(7) . . . . ? C1 C2 C3 C4 2.3(7) . . . . ? C2 C3 C4 C5 -1.7(7) . . . . ? C1 N1 C5 C4 0.7(5) . . . . ? Cu1 N1 C5 C4 178.5(3) . . . . ? C1 N1 C5 C6 -179.2(3) . . . . ? Cu1 N1 C5 C6 -1.4(4) . . . . ? C3 C4 C5 N1 0.2(6) . . . . ? C3 C4 C5 C6 -179.9(4) . . . . ? C13 N2 C6 C5 86.6(4) . . . . ? C7 N2 C6 C5 -142.9(3) . . . . ? Cu1 N2 C6 C5 -33.1(3) . . . . ? N1 C5 C6 N2 24.7(4) . . . . ? C4 C5 C6 N2 -155.2(3) . . . . ? C13 N2 C7 C8 -75.2(3) . . . . ? C6 N2 C7 C8 155.4(3) . . . . ? Cu1 N2 C7 C8 44.0(3) . . . . ? C12 N3 C8 C9 -1.4(5) . . . . ? Cu1 N3 C8 C9 -176.5(3) . . . . ? C12 N3 C8 C7 -179.5(3) . . . . ? Cu1 N3 C8 C7 5.4(4) . . . . ? N2 C7 C8 N3 -35.1(4) . . . . ? N2 C7 C8 C9 146.8(4) . . . . ? N3 C8 C9 C10 0.1(6) . . . . ? C7 C8 C9 C10 178.0(3) . . . . ? C8 C9 C10 C11 1.4(6) . . . . ? C9 C10 C11 C12 -1.6(6) . . . . ? C8 N3 C12 C11 1.3(6) . . . . ? Cu1 N3 C12 C11 175.7(3) . . . . ? C10 C11 C12 N3 0.2(6) . . . . ? C7 N2 C13 C14 -179.6(3) . . . . ? C6 N2 C13 C14 -50.0(5) . . . . ? Cu1 N2 C13 C14 66.2(4) . . . . ? C7 N2 C13 C15 0.1(5) . . . . ? C6 N2 C13 C15 129.8(4) . . . . ? Cu1 N2 C13 C15 -114.1(4) . . . . ? C15 C13 C14 C15 0.3(7) . . . 3_657 ? N2 C13 C14 C15 -180.0(4) . . . 3_657 ? C14 C13 C15 C14 -0.3(7) . . . 3_657 ? N2 C13 C15 C14 180.0(4) . . . 3_657 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.725 _refine_diff_density_min -0.616 _refine_diff_density_rms 0.088 # Attachment '3.cif' data_070831a _database_code_depnum_ccdc_archive 'CCDC 694617' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H29 Cl2 Cu N6 O9' _chemical_formula_weight 752.03 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.848(4) _cell_length_b 12.525(4) _cell_length_c 13.498(4) _cell_angle_alpha 95.499(5) _cell_angle_beta 101.124(6) _cell_angle_gamma 115.852(5) _cell_volume 1731.7(10) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2524 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 22.52 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.844 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.696461 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8897 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6049 _reflns_number_gt 3823 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1359P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6049 _refine_ls_number_parameters 472 _refine_ls_number_restraints 102 _refine_ls_R_factor_all 0.1086 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.2223 _refine_ls_wR_factor_gt 0.1843 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.140 _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 0.73016(7) 0.77713(6) 0.71929(5) 0.0487(3) Uani 1 1 d . . . O1 O 0.5348(4) 0.7111(4) 0.5913(3) 0.0754(13) Uani 1 1 d . . . N1 N 0.8105(5) 0.7093(4) 0.6223(3) 0.0517(11) Uani 1 1 d . . . N2 N 0.9349(4) 0.7993(4) 0.8363(3) 0.0516(11) Uani 1 1 d . . . N3 N 0.6637(5) 0.6213(4) 0.7765(3) 0.0514(11) Uani 1 1 d . . . N4 N 0.6747(4) 0.8653(4) 0.8254(4) 0.0520(11) Uani 1 1 d . . . N5 N 0.8180(5) 0.9495(4) 0.6915(3) 0.0545(12) Uani 1 1 d . . . N6 N 0.3917(7) 0.7567(7) 0.4926(6) 0.105(2) Uani 1 1 d . . . C1 C 0.7415(6) 0.6396(5) 0.5263(4) 0.0611(16) Uani 1 1 d . . . H1 H 0.6558 0.6241 0.5019 0.073 Uiso 1 1 calc R . . C2 C 0.7950(7) 0.5909(6) 0.4637(4) 0.0701(19) Uani 1 1 d . . . H2 H 0.7458 0.5451 0.3981 0.084 Uiso 1 1 calc R . . C3 C 0.9208(7) 0.6104(5) 0.4989(4) 0.0612(16) Uani 1 1 d . . . H3 H 0.9562 0.5754 0.4588 0.073 Uiso 1 1 calc R . . C4 C 0.9954(6) 0.6848(5) 0.5973(4) 0.0595(15) Uani 1 1 d . . . H4 H 1.0814 0.7015 0.6224 0.071 Uiso 1 1 calc R . . C5 C 0.9366(6) 0.7324(5) 0.6559(4) 0.0507(14) Uani 1 1 d . . . C6 C 1.0162(6) 0.8201(5) 0.7614(4) 0.0590(15) Uani 1 1 d . . . H6A H 1.0906 0.8078 0.7887 0.071 Uiso 1 1 calc R . . H6B H 1.0481 0.9031 0.7522 0.071 Uiso 1 1 calc R . . C7 C 0.8938(6) 0.6785(5) 0.8646(4) 0.0590(16) Uani 1 1 d . . . H7A H 0.9325 0.6907 0.9376 0.071 Uiso 1 1 calc R . . H7B H 0.9289 0.6354 0.8275 0.071 Uiso 1 1 calc R . . C8 C 0.7474(6) 0.5979(5) 0.8431(4) 0.0605(16) Uani 1 1 d . . . C9 C 0.7028(10) 0.4967(7) 0.8884(6) 0.104(3) Uani 1 1 d . . . H9 H 0.7606 0.4800 0.9329 0.124 Uiso 1 1 calc R . . C10 C 0.5659(11) 0.4194(8) 0.8645(8) 0.119(3) Uani 1 1 d . . . H10 H 0.5335 0.3532 0.8958 0.142 Uiso 1 1 calc R . . C11 C 0.4823(9) 0.4427(7) 0.7956(7) 0.102(3) Uani 1 1 d . . . H11 H 0.3933 0.3914 0.7775 0.122 Uiso 1 1 calc R . . C12 C 0.5338(7) 0.5438(5) 0.7542(5) 0.0714(18) Uani 1 1 d . . . H12 H 0.4771 0.5604 0.7083 0.086 Uiso 1 1 calc R . . C13 C 0.9713(5) 0.9018(5) 0.9198(4) 0.0461(13) Uani 1 1 d . . . C14 C 0.9136(5) 0.8822(5) 1.0034(4) 0.0490(13) Uani 1 1 d . . . H14 H 0.8564 0.8038 1.0067 0.059 Uiso 1 1 calc R . . C15 C 1.0587(5) 1.0213(5) 0.9191(4) 0.0484(13) Uani 1 1 d . . . H15 H 1.0990 1.0365 0.8657 0.058 Uiso 1 1 calc R . . C16 C 0.6059(6) 0.8216(6) 0.8936(5) 0.0655(17) Uani 1 1 d . . . H16 H 0.5636 0.7382 0.8889 0.079 Uiso 1 1 calc R . . C17 C 0.5951(7) 0.8961(7) 0.9713(5) 0.076(2) Uani 1 1 d . . . H17 H 0.5451 0.8617 1.0160 0.092 Uiso 1 1 calc R . . C18 C 0.6586(7) 1.0210(7) 0.9821(5) 0.0734(19) Uani 1 1 d . . . H18 H 0.6548 1.0713 1.0353 0.088 Uiso 1 1 calc R . . C19 C 0.7296(6) 1.0705(6) 0.9097(4) 0.0583(15) Uani 1 1 d . . . C20 C 0.8000(7) 1.2001(6) 0.9124(5) 0.0681(18) Uani 1 1 d . . . H20 H 0.7950 1.2546 0.9610 0.082 Uiso 1 1 calc R . . C21 C 0.8736(7) 1.2428(6) 0.8446(5) 0.0738(19) Uani 1 1 d . . . H21 H 0.9170 1.3258 0.8476 0.089 Uiso 1 1 calc R . . C22 C 0.8850(6) 1.1614(5) 0.7684(4) 0.0580(15) Uani 1 1 d . . . C23 C 0.9628(7) 1.2002(6) 0.6975(5) 0.0725(18) Uani 1 1 d . . . H23 H 1.0131 1.2823 0.7003 0.087 Uiso 1 1 calc R . . C24 C 0.9626(8) 1.1153(6) 0.6252(6) 0.082(2) Uani 1 1 d . . . H24 H 1.0110 1.1395 0.5775 0.099 Uiso 1 1 calc R . . C25 C 0.8876(8) 0.9898(6) 0.6237(5) 0.0745(19) Uani 1 1 d . . . H25 H 0.8872 0.9333 0.5734 0.089 Uiso 1 1 calc R . . C26 C 0.8138(5) 1.0342(5) 0.7622(4) 0.0504(14) Uani 1 1 d . . . C27 C 0.7375(5) 0.9875(5) 0.8346(4) 0.0481(13) Uani 1 1 d . . . C28 C 0.4765(10) 0.7680(9) 0.5719(7) 0.114(3) Uani 1 1 d . . . H28 H 0.4977 0.8322 0.6249 0.137 Uiso 1 1 calc R . . C29 C 0.3325(19) 0.8369(18) 0.4728(11) 0.275(12) Uani 1 1 d . . . H29A H 0.2620 0.8166 0.5047 0.412 Uiso 1 1 calc R . . H29B H 0.3003 0.8268 0.3998 0.412 Uiso 1 1 calc R . . H29C H 0.3965 0.9196 0.5011 0.412 Uiso 1 1 calc R . . C30 C 0.3568(11) 0.6653(10) 0.3983(8) 0.148(4) Uani 1 1 d . . . H30A H 0.3693 0.7046 0.3408 0.221 Uiso 1 1 calc R . . H30B H 0.2674 0.6058 0.3848 0.221 Uiso 1 1 calc R . . H30C H 0.4111 0.6264 0.4084 0.221 Uiso 1 1 calc R . . Cl1 Cl 0.6986(3) 0.9111(2) 0.3188(2) 0.1196(9) Uani 1 1 d D . . Cl2 Cl 0.1984(2) 0.58200(19) 0.81861(15) 0.0941(7) Uani 1 1 d D . . O2 O 0.6859(9) 0.8258(7) 0.3862(6) 0.203(4) Uani 1 1 d DU . . O3 O 0.8041(7) 1.0265(5) 0.3727(5) 0.155(3) Uani 1 1 d DU . . O4 O 0.7250(8) 0.8686(6) 0.2275(5) 0.168(3) Uani 1 1 d DU . . O5 O 0.5793(8) 0.9146(10) 0.2897(9) 0.251(5) Uani 1 1 d DU . . O6 O 0.0889(12) 0.5168(10) 0.7283(7) 0.129(5) Uani 0.488(11) 1 d PDU A 1 O7 O 0.1279(12) 0.5478(10) 0.9039(7) 0.122(5) Uani 0.488(11) 1 d PDU A 1 O8 O 0.2921(14) 0.5453(16) 0.8293(14) 0.219(11) Uani 0.488(11) 1 d PDU A 1 O9 O 0.2401(12) 0.7089(6) 0.8302(10) 0.125(5) Uani 0.488(11) 1 d PDU A 1 O6' O 0.2558(13) 0.6299(13) 0.7330(8) 0.163(7) Uani 0.512(11) 1 d PDU A 2 O7' O 0.2755(13) 0.6645(11) 0.9092(7) 0.161(7) Uani 0.512(11) 1 d PDU A 2 O8' O 0.2164(16) 0.4717(11) 0.8193(12) 0.170(7) Uani 0.512(11) 1 d PDU A 2 O9' O 0.0649(8) 0.5420(14) 0.7880(13) 0.175(8) Uani 0.512(11) 1 d PDU A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0529(5) 0.0449(4) 0.0457(4) 0.0002(3) 0.0067(3) 0.0247(3) O1 0.064(3) 0.089(3) 0.070(3) 0.014(2) -0.001(2) 0.041(3) N1 0.056(3) 0.048(3) 0.044(3) -0.005(2) 0.003(2) 0.025(2) N2 0.049(3) 0.053(3) 0.041(2) -0.009(2) 0.001(2) 0.021(2) N3 0.051(3) 0.044(2) 0.050(3) -0.002(2) 0.002(2) 0.021(2) N4 0.049(3) 0.054(3) 0.056(3) 0.005(2) 0.012(2) 0.029(2) N5 0.065(3) 0.054(3) 0.049(3) 0.006(2) 0.015(2) 0.032(2) N6 0.083(5) 0.150(7) 0.103(5) 0.033(5) 0.009(4) 0.078(5) C1 0.064(4) 0.064(4) 0.044(3) -0.008(3) -0.005(3) 0.032(3) C2 0.090(5) 0.065(4) 0.035(3) -0.017(3) -0.004(3) 0.031(4) C3 0.084(5) 0.065(4) 0.044(3) -0.001(3) 0.017(3) 0.045(4) C4 0.072(4) 0.070(4) 0.046(3) 0.001(3) 0.012(3) 0.044(3) C5 0.058(4) 0.049(3) 0.040(3) -0.002(2) 0.003(3) 0.027(3) C6 0.050(3) 0.070(4) 0.044(3) -0.015(3) 0.005(3) 0.025(3) C7 0.072(4) 0.065(4) 0.047(3) -0.002(3) 0.003(3) 0.045(3) C8 0.071(4) 0.052(3) 0.045(3) -0.005(3) -0.003(3) 0.028(3) C9 0.124(8) 0.074(5) 0.095(6) 0.036(4) -0.004(5) 0.040(5) C10 0.120(8) 0.078(6) 0.127(8) 0.052(6) 0.023(6) 0.018(6) C11 0.081(6) 0.070(5) 0.121(7) 0.029(5) 0.012(5) 0.010(4) C12 0.065(4) 0.055(4) 0.073(4) 0.008(3) -0.002(3) 0.017(3) C13 0.042(3) 0.051(3) 0.032(3) -0.010(2) -0.003(2) 0.020(3) C14 0.046(3) 0.048(3) 0.039(3) -0.004(2) 0.003(2) 0.016(3) C15 0.043(3) 0.059(3) 0.032(3) -0.002(2) 0.003(2) 0.019(3) C16 0.056(4) 0.080(4) 0.066(4) 0.014(3) 0.024(3) 0.034(3) C17 0.063(4) 0.103(6) 0.068(4) 0.013(4) 0.024(3) 0.042(4) C18 0.065(4) 0.093(5) 0.066(4) -0.008(4) 0.013(3) 0.047(4) C19 0.056(4) 0.070(4) 0.053(3) -0.001(3) 0.005(3) 0.040(3) C20 0.078(5) 0.059(4) 0.062(4) -0.011(3) 0.004(3) 0.038(4) C21 0.081(5) 0.056(4) 0.078(5) 0.002(3) 0.000(4) 0.036(4) C22 0.063(4) 0.050(3) 0.053(3) 0.007(3) 0.000(3) 0.027(3) C23 0.080(5) 0.059(4) 0.073(4) 0.016(3) 0.014(4) 0.030(4) C24 0.105(6) 0.074(5) 0.088(5) 0.037(4) 0.049(5) 0.044(4) C25 0.107(6) 0.068(4) 0.064(4) 0.016(3) 0.035(4) 0.048(4) C26 0.052(3) 0.057(3) 0.043(3) 0.002(3) 0.001(3) 0.033(3) C27 0.046(3) 0.054(3) 0.047(3) 0.000(2) 0.001(2) 0.032(3) C28 0.111(7) 0.121(7) 0.096(6) -0.005(5) -0.022(6) 0.067(6) C29 0.34(2) 0.40(3) 0.192(14) -0.006(16) -0.048(15) 0.32(2) C30 0.132(10) 0.161(10) 0.101(8) 0.024(7) 0.008(7) 0.036(8) Cl1 0.111(2) 0.1040(17) 0.1039(17) 0.0087(14) 0.0452(15) 0.0109(15) Cl2 0.1194(18) 0.0947(14) 0.0777(13) -0.0060(11) 0.0141(12) 0.0677(14) O2 0.222(8) 0.178(7) 0.147(6) 0.073(6) 0.060(6) 0.026(5) O3 0.159(6) 0.117(5) 0.130(5) -0.001(4) 0.052(5) 0.011(4) O4 0.181(7) 0.153(6) 0.119(5) -0.002(4) 0.073(5) 0.025(5) O5 0.217(9) 0.267(9) 0.294(10) 0.031(7) 0.035(7) 0.152(8) O6 0.175(10) 0.093(7) 0.085(7) 0.003(6) 0.005(7) 0.048(7) O7 0.134(9) 0.120(8) 0.103(8) 0.012(6) 0.042(7) 0.049(7) O8 0.217(14) 0.214(13) 0.265(15) 0.060(10) 0.067(10) 0.131(10) O9 0.146(9) 0.085(7) 0.139(9) 0.011(6) 0.023(7) 0.058(6) O6' 0.157(10) 0.197(11) 0.123(9) 0.028(8) 0.057(7) 0.065(8) O7' 0.183(11) 0.139(9) 0.114(9) 0.001(7) 0.036(8) 0.039(7) O8' 0.160(10) 0.154(10) 0.218(11) -0.011(7) 0.029(8) 0.112(9) O9' 0.153(10) 0.187(11) 0.220(13) 0.058(9) 0.079(9) 0.094(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 2.052(5) . ? Cu1 N5 2.057(5) . ? Cu1 N1 2.077(4) . ? Cu1 N4 2.096(4) . ? Cu1 O1 2.353(5) . ? O1 C28 1.204(9) . ? N1 C5 1.362(7) . ? N1 C1 1.365(7) . ? N2 C13 1.469(6) . ? N2 C7 1.487(7) . ? N2 C6 1.492(7) . ? N3 C8 1.355(7) . ? N3 C12 1.365(8) . ? N4 C16 1.346(7) . ? N4 C27 1.358(7) . ? N5 C25 1.337(8) . ? N5 C26 1.381(7) . ? N6 C28 1.268(10) . ? N6 C29 1.472(13) . ? N6 C30 1.485(12) . ? C1 C2 1.390(8) . ? C1 H1 0.9300 . ? C2 C3 1.376(9) . ? C2 H2 0.9300 . ? C3 C4 1.416(8) . ? C3 H3 0.9300 . ? C4 C5 1.396(7) . ? C4 H4 0.9300 . ? C5 C6 1.551(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.528(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.396(9) . ? C9 C10 1.428(13) . ? C9 H9 0.9300 . ? C10 C11 1.371(12) . ? C10 H10 0.9300 . ? C11 C12 1.372(10) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C15 1.403(8) . ? C13 C14 1.416(7) . ? C14 C15 1.393(7) 2_777 ? C14 H14 0.9300 . ? C15 C14 1.393(7) 2_777 ? C15 H15 0.9300 . ? C16 C17 1.398(9) . ? C16 H16 0.9300 . ? C17 C18 1.387(10) . ? C17 H17 0.9300 . ? C18 C19 1.423(9) . ? C18 H18 0.9300 . ? C19 C27 1.427(7) . ? C19 C20 1.458(9) . ? C20 C21 1.371(10) . ? C20 H20 0.9300 . ? C21 C22 1.445(9) . ? C21 H21 0.9300 . ? C22 C26 1.426(8) . ? C22 C23 1.428(9) . ? C23 C24 1.371(9) . ? C23 H23 0.9300 . ? C24 C25 1.425(9) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.451(8) . ? C28 H28 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? Cl1 O5 1.413(6) . ? Cl1 O3 1.433(5) . ? Cl1 O4 1.438(5) . ? Cl1 O2 1.447(6) . ? Cl2 O8 1.363(8) . ? Cl2 O7' 1.379(7) . ? Cl2 O9' 1.394(8) . ? Cl2 O9 1.426(7) . ? Cl2 O6 1.454(8) . ? Cl2 O8' 1.488(7) . ? Cl2 O6' 1.496(8) . ? Cl2 O7 1.536(7) . ? 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 N3 Cu1 N5 168.69(17) . . ? N3 Cu1 N1 91.41(18) . . ? N5 Cu1 N1 93.92(18) . . ? N3 Cu1 N4 92.83(18) . . ? N5 Cu1 N4 80.80(18) . . ? N1 Cu1 N4 172.16(18) . . ? N3 Cu1 O1 93.92(18) . . ? N5 Cu1 O1 95.75(18) . . ? N1 Cu1 O1 93.12(17) . . ? N4 Cu1 O1 93.17(17) . . ? C28 O1 Cu1 126.4(5) . . ? C5 N1 C1 117.9(5) . . ? C5 N1 Cu1 119.3(3) . . ? C1 N1 Cu1 122.8(4) . . ? C13 N2 C7 116.5(4) . . ? C13 N2 C6 117.3(4) . . ? C7 N2 C6 113.4(4) . . ? C8 N3 C12 118.7(5) . . ? C8 N3 Cu1 120.4(4) . . ? C12 N3 Cu1 120.7(4) . . ? C16 N4 C27 117.7(5) . . ? C16 N4 Cu1 129.8(4) . . ? C27 N4 Cu1 111.6(4) . . ? C25 N5 C26 117.9(5) . . ? C25 N5 Cu1 129.1(4) . . ? C26 N5 Cu1 112.6(4) . . ? C28 N6 C29 128.0(10) . . ? C28 N6 C30 120.2(8) . . ? C29 N6 C30 111.2(9) . . ? N1 C1 C2 122.2(6) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 120.0(5) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 118.9(5) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.4(6) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 122.6(5) . . ? N1 C5 C6 117.0(4) . . ? C4 C5 C6 120.4(5) . . ? N2 C6 C5 110.9(5) . . ? N2 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N2 C7 C8 116.0(5) . . ? N2 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? N2 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? N3 C8 C9 121.1(7) . . ? N3 C8 C7 120.0(5) . . ? C9 C8 C7 118.8(6) . . ? C8 C9 C10 118.3(8) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? C11 C10 C9 120.1(7) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 118.1(8) . . ? C10 C11 H11 120.9 . . ? C12 C11 H11 120.9 . . ? N3 C12 C11 123.6(7) . . ? N3 C12 H12 118.2 . . ? C11 C12 H12 118.2 . . ? C15 C13 C14 117.5(4) . . ? C15 C13 N2 122.7(5) . . ? C14 C13 N2 119.8(5) . . ? C15 C14 C13 121.0(5) 2_777 . ? C15 C14 H14 119.5 2_777 . ? C13 C14 H14 119.5 . . ? C14 C15 C13 121.5(5) 2_777 . ? C14 C15 H15 119.2 2_777 . ? C13 C15 H15 119.2 . . ? N4 C16 C17 122.9(6) . . ? N4 C16 H16 118.6 . . ? C17 C16 H16 118.6 . . ? C18 C17 C16 120.3(7) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 118.5(6) . . ? C17 C18 H18 120.8 . . ? C19 C18 H18 120.8 . . ? C18 C19 C27 117.1(6) . . ? C18 C19 C20 123.7(6) . . ? C27 C19 C20 119.1(6) . . ? C21 C20 C19 121.0(6) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 121.3(6) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C26 C22 C23 117.3(5) . . ? C26 C22 C21 118.6(6) . . ? C23 C22 C21 124.1(6) . . ? C24 C23 C22 119.5(6) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C25 119.6(6) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? N5 C25 C24 123.0(6) . . ? N5 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? N5 C26 C22 122.7(5) . . ? N5 C26 C27 116.5(5) . . ? C22 C26 C27 120.7(5) . . ? N4 C27 C19 123.5(5) . . ? N4 C27 C26 117.4(4) . . ? C19 C27 C26 119.1(5) . . ? O1 C28 N6 131.9(9) . . ? O1 C28 H28 114.1 . . ? N6 C28 H28 114.1 . . ? N6 C29 H29A 109.5 . . ? N6 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N6 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N6 C30 H30A 109.5 . . ? N6 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N6 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O5 Cl1 O3 112.6(5) . . ? O5 Cl1 O4 108.5(5) . . ? O3 Cl1 O4 110.5(4) . . ? O5 Cl1 O2 108.7(5) . . ? O3 Cl1 O2 108.1(5) . . ? O4 Cl1 O2 108.5(5) . . ? O8 Cl2 O7' 85.4(10) . . ? O8 Cl2 O9' 144.1(10) . . ? O7' Cl2 O9' 121.7(7) . . ? O8 Cl2 O9 117.3(8) . . ? O7' Cl2 O9 56.6(7) . . ? O9' Cl2 O9 98.1(8) . . ? O8 Cl2 O6 115.4(7) . . ? O7' Cl2 O6 159.1(8) . . ? O9' Cl2 O6 39.9(7) . . ? O9 Cl2 O6 109.7(6) . . ? O8 Cl2 O8' 38.1(9) . . ? O7' Cl2 O8' 108.7(7) . . ? O9' Cl2 O8' 106.6(7) . . ? O9 Cl2 O8' 155.4(8) . . ? O6 Cl2 O8' 89.3(8) . . ? O8 Cl2 O6' 80.8(9) . . ? O7' Cl2 O6' 107.8(7) . . ? O9' Cl2 O6' 108.6(7) . . ? O9 Cl2 O6' 69.0(7) . . ? O6 Cl2 O6' 77.5(7) . . ? O8' Cl2 O6' 101.7(6) . . ? O8 Cl2 O7 109.3(7) . . ? O7' Cl2 O7 71.3(7) . . ? O9' Cl2 O7 65.0(7) . . ? O9 Cl2 O7 103.1(6) . . ? O6 Cl2 O7 99.7(6) . . ? O8' Cl2 O7 88.3(8) . . ? O6' Cl2 O7 169.6(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 N3 Cu1 O1 C28 132.2(8) . . . . ? N5 Cu1 O1 C28 -41.9(8) . . . . ? N1 Cu1 O1 C28 -136.2(8) . . . . ? N4 Cu1 O1 C28 39.1(8) . . . . ? N3 Cu1 N1 C5 -91.9(4) . . . . ? N5 Cu1 N1 C5 78.2(4) . . . . ? N4 Cu1 N1 C5 30.8(15) . . . . ? O1 Cu1 N1 C5 174.1(4) . . . . ? N3 Cu1 N1 C1 86.7(5) . . . . ? N5 Cu1 N1 C1 -103.3(5) . . . . ? N4 Cu1 N1 C1 -150.6(11) . . . . ? O1 Cu1 N1 C1 -7.3(5) . . . . ? N5 Cu1 N3 C8 -44.0(11) . . . . ? N1 Cu1 N3 C8 74.1(4) . . . . ? N4 Cu1 N3 C8 -99.3(4) . . . . ? O1 Cu1 N3 C8 167.4(4) . . . . ? N5 Cu1 N3 C12 131.3(9) . . . . ? N1 Cu1 N3 C12 -110.6(5) . . . . ? N4 Cu1 N3 C12 76.0(5) . . . . ? O1 Cu1 N3 C12 -17.4(5) . . . . ? N3 Cu1 N4 C16 -7.3(5) . . . . ? N5 Cu1 N4 C16 -177.9(5) . . . . ? N1 Cu1 N4 C16 -129.9(12) . . . . ? O1 Cu1 N4 C16 86.8(5) . . . . ? N3 Cu1 N4 C27 161.1(4) . . . . ? N5 Cu1 N4 C27 -9.5(4) . . . . ? N1 Cu1 N4 C27 38.5(14) . . . . ? O1 Cu1 N4 C27 -104.8(4) . . . . ? N3 Cu1 N5 C25 124.6(9) . . . . ? N1 Cu1 N5 C25 6.7(6) . . . . ? N4 Cu1 N5 C25 -179.1(6) . . . . ? O1 Cu1 N5 C25 -86.8(6) . . . . ? N3 Cu1 N5 C26 -47.5(11) . . . . ? N1 Cu1 N5 C26 -165.4(4) . . . . ? N4 Cu1 N5 C26 8.8(4) . . . . ? O1 Cu1 N5 C26 101.1(4) . . . . ? C5 N1 C1 C2 1.1(9) . . . . ? Cu1 N1 C1 C2 -177.5(5) . . . . ? N1 C1 C2 C3 1.3(10) . . . . ? C1 C2 C3 C4 -2.7(10) . . . . ? C2 C3 C4 C5 1.8(9) . . . . ? C1 N1 C5 C4 -2.0(8) . . . . ? Cu1 N1 C5 C4 176.6(4) . . . . ? C1 N1 C5 C6 175.3(5) . . . . ? Cu1 N1 C5 C6 -6.1(7) . . . . ? C3 C4 C5 N1 0.6(9) . . . . ? C3 C4 C5 C6 -176.6(5) . . . . ? C13 N2 C6 C5 -153.9(4) . . . . ? C7 N2 C6 C5 65.6(6) . . . . ? N1 C5 C6 N2 38.9(7) . . . . ? C4 C5 C6 N2 -143.8(5) . . . . ? C13 N2 C7 C8 97.2(6) . . . . ? C6 N2 C7 C8 -122.0(5) . . . . ? C12 N3 C8 C9 0.0(9) . . . . ? Cu1 N3 C8 C9 175.4(5) . . . . ? C12 N3 C8 C7 176.3(5) . . . . ? Cu1 N3 C8 C7 -8.3(7) . . . . ? N2 C7 C8 N3 18.1(7) . . . . ? N2 C7 C8 C9 -165.5(6) . . . . ? N3 C8 C9 C10 -1.3(12) . . . . ? C7 C8 C9 C10 -177.6(8) . . . . ? C8 C9 C10 C11 2.5(15) . . . . ? C9 C10 C11 C12 -2.4(15) . . . . ? C8 N3 C12 C11 0.1(10) . . . . ? Cu1 N3 C12 C11 -175.2(6) . . . . ? C10 C11 C12 N3 1.1(13) . . . . ? C7 N2 C13 C15 153.2(5) . . . . ? C6 N2 C13 C15 14.0(7) . . . . ? C7 N2 C13 C14 -29.2(7) . . . . ? C6 N2 C13 C14 -168.4(5) . . . . ? C15 C13 C14 C15 1.1(9) . . . 2_777 ? N2 C13 C14 C15 -176.7(5) . . . 2_777 ? C14 C13 C15 C14 -1.1(9) . . . 2_777 ? N2 C13 C15 C14 176.6(5) . . . 2_777 ? C27 N4 C16 C17 1.0(9) . . . . ? Cu1 N4 C16 C17 168.9(5) . . . . ? N4 C16 C17 C18 -1.2(10) . . . . ? C16 C17 C18 C19 2.7(10) . . . . ? C17 C18 C19 C27 -4.0(9) . . . . ? C17 C18 C19 C20 179.8(6) . . . . ? C18 C19 C20 C21 175.8(6) . . . . ? C27 C19 C20 C21 -0.3(9) . . . . ? C19 C20 C21 C22 -0.5(10) . . . . ? C20 C21 C22 C26 2.4(9) . . . . ? C20 C21 C22 C23 -178.2(6) . . . . ? C26 C22 C23 C24 2.2(9) . . . . ? C21 C22 C23 C24 -177.2(7) . . . . ? C22 C23 C24 C25 -1.7(11) . . . . ? C26 N5 C25 C24 3.5(10) . . . . ? Cu1 N5 C25 C24 -168.3(5) . . . . ? C23 C24 C25 N5 -1.2(12) . . . . ? C25 N5 C26 C22 -2.9(8) . . . . ? Cu1 N5 C26 C22 170.2(4) . . . . ? C25 N5 C26 C27 -180.0(5) . . . . ? Cu1 N5 C26 C27 -6.9(6) . . . . ? C23 C22 C26 N5 0.1(8) . . . . ? C21 C22 C26 N5 179.6(5) . . . . ? C23 C22 C26 C27 177.0(5) . . . . ? C21 C22 C26 C27 -3.5(8) . . . . ? C16 N4 C27 C19 -2.6(8) . . . . ? Cu1 N4 C27 C19 -172.6(4) . . . . ? C16 N4 C27 C26 178.7(5) . . . . ? Cu1 N4 C27 C26 8.7(6) . . . . ? C18 C19 C27 N4 4.1(8) . . . . ? C20 C19 C27 N4 -179.5(5) . . . . ? C18 C19 C27 C26 -177.2(5) . . . . ? C20 C19 C27 C26 -0.8(8) . . . . ? N5 C26 C27 N4 -1.4(7) . . . . ? C22 C26 C27 N4 -178.5(5) . . . . ? N5 C26 C27 C19 179.9(5) . . . . ? C22 C26 C27 C19 2.8(8) . . . . ? Cu1 O1 C28 N6 160.3(9) . . . . ? C29 N6 C28 O1 -175.0(15) . . . . ? C30 N6 C28 O1 -5.5(19) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.678 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.083 # Attachment '4.cif' data_r80110a _database_code_depnum_ccdc_archive 'CCDC 694618' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H52 Cl4 Cu2 N10 O20' _chemical_formula_weight 1381.90 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.014(2) _cell_length_b 12.259(3) _cell_length_c 12.887(3) _cell_angle_alpha 64.99(3) _cell_angle_beta 78.94(3) _cell_angle_gamma 77.72(3) _cell_volume 1391.5(5) _cell_formula_units_Z 1 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3787 _cell_measurement_theta_min 1.755 _cell_measurement_theta_max 27.857 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 1.044 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8850 _exptl_absorpt_correction_T_max 0.9594 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _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 8553 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4871 _reflns_number_gt 4375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0869P)^2^+1.0182P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4871 _refine_ls_number_parameters 416 _refine_ls_number_restraints 92 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1364 _refine_ls_wR_factor_gt 0.1318 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.135 _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 0.73513(4) 0.82508(3) 0.34828(3) 0.01593(16) Uani 1 1 d . . . N1 N 0.8194(3) 0.8630(3) 0.1847(2) 0.0213(6) Uani 1 1 d . . . N2 N 0.9770(3) 0.7570(2) 0.3745(2) 0.0159(6) Uani 1 1 d . . . N3 N 0.7972(3) 0.9760(2) 0.3392(2) 0.0174(6) Uani 1 1 d . . . N4 N 0.6890(3) 0.6643(2) 0.3692(2) 0.0194(6) Uani 1 1 d . . . N5 N 0.6722(3) 0.7610(2) 0.5178(2) 0.0172(6) Uani 1 1 d . . . C1 C 0.7381(4) 0.9041(3) 0.0986(3) 0.0299(8) Uani 1 1 d . . . H1 H 0.6444 0.9280 0.1137 0.036 Uiso 1 1 calc R . . C2 C 0.7911(5) 0.9113(4) -0.0103(3) 0.0393(10) Uani 1 1 d . . . H2 H 0.7344 0.9404 -0.0686 0.047 Uiso 1 1 calc R . . C3 C 0.9298(5) 0.8747(4) -0.0315(3) 0.0407(10) Uani 1 1 d . . . H3 H 0.9675 0.8762 -0.1039 0.049 Uiso 1 1 calc R . . C4 C 1.0121(4) 0.8358(4) 0.0552(3) 0.0321(9) Uani 1 1 d . . . H4 H 1.1062 0.8124 0.0412 0.039 Uiso 1 1 calc R . . C5 C 0.9549(4) 0.8316(3) 0.1628(3) 0.0219(7) Uani 1 1 d . . . C6 C 1.0475(4) 0.7992(3) 0.2559(3) 0.0206(7) Uani 1 1 d . . . H6A H 1.1218 0.7359 0.2503 0.025 Uiso 1 1 calc R . . H6B H 1.0882 0.8702 0.2410 0.025 Uiso 1 1 calc R . . C7 C 0.9898(3) 0.8333(3) 0.4347(3) 0.0180(7) Uani 1 1 d . . . H7A H 1.0863 0.8329 0.4366 0.022 Uiso 1 1 calc R . . H7B H 0.9469 0.7998 0.5136 0.022 Uiso 1 1 calc R . . C8 C 0.9214(3) 0.9626(3) 0.3737(3) 0.0173(7) Uani 1 1 d . . . C9 C 0.9790(3) 1.0628(3) 0.3562(3) 0.0189(7) Uani 1 1 d . . . H9 H 1.0645 1.0521 0.3802 0.023 Uiso 1 1 calc R . . C10 C 0.9103(4) 1.1787(3) 0.3033(3) 0.0225(7) Uani 1 1 d . . . H10 H 0.9480 1.2466 0.2918 0.027 Uiso 1 1 calc R . . C11 C 0.7835(4) 1.1916(3) 0.2676(3) 0.0246(8) Uani 1 1 d . . . H11 H 0.7348 1.2686 0.2316 0.029 Uiso 1 1 calc R . . C12 C 0.7308(4) 1.0893(3) 0.2863(3) 0.0215(7) Uani 1 1 d . . . H12 H 0.6462 1.0985 0.2615 0.026 Uiso 1 1 calc R . . C13 C 0.9933(3) 0.6277(3) 0.4392(3) 0.0148(6) Uani 1 1 d . . . C14 C 1.0081(3) 0.5510(3) 0.3815(3) 0.0167(7) Uani 1 1 d . . . H14 H 1.0142 0.5844 0.3015 0.020 Uiso 1 1 calc R . . C15 C 0.9861(3) 0.5739(3) 0.5592(3) 0.0159(6) Uani 1 1 d . . . H15 H 0.9773 0.6226 0.6000 0.019 Uiso 1 1 calc R . . C16 C 0.6947(4) 0.6218(3) 0.2877(3) 0.0247(8) Uani 1 1 d . . . H16 H 0.7042 0.6754 0.2107 0.030 Uiso 1 1 calc R . . C17 C 0.6871(4) 0.5024(3) 0.3135(3) 0.0275(8) Uani 1 1 d . . . H17 H 0.6901 0.4764 0.2548 0.033 Uiso 1 1 calc R . . C18 C 0.6748(4) 0.4215(3) 0.4271(3) 0.0264(8) Uani 1 1 d . . . H18 H 0.6725 0.3397 0.4461 0.032 Uiso 1 1 calc R . . C19 C 0.6658(3) 0.4644(3) 0.5127(3) 0.0223(7) Uani 1 1 d . . . H19 H 0.6558 0.4121 0.5901 0.027 Uiso 1 1 calc R . . C20 C 0.6720(3) 0.5865(3) 0.4806(3) 0.0193(7) Uani 1 1 d . . . C21 C 0.6569(3) 0.6427(3) 0.5645(3) 0.0186(7) Uani 1 1 d . . . C22 C 0.6254(4) 0.5806(3) 0.6821(3) 0.0249(8) Uani 1 1 d . . . H22 H 0.6143 0.4990 0.7126 0.030 Uiso 1 1 calc R . . C23 C 0.6107(4) 0.6425(3) 0.7538(3) 0.0281(8) Uani 1 1 d . . . H23 H 0.5911 0.6023 0.8332 0.034 Uiso 1 1 calc R . . C24 C 0.6256(4) 0.7644(3) 0.7056(3) 0.0271(8) Uani 1 1 d . . . H24 H 0.6155 0.8076 0.7517 0.032 Uiso 1 1 calc R . . C25 C 0.6558(3) 0.8204(3) 0.5877(3) 0.0216(7) Uani 1 1 d . . . H25 H 0.6651 0.9025 0.5551 0.026 Uiso 1 1 calc R . . Cl1 Cl 0.37863(8) 0.90559(7) 0.33781(7) 0.0192(2) Uani 1 1 d . . . O1 O 0.5150(2) 0.9410(2) 0.3010(2) 0.0294(6) Uani 1 1 d . . . O2 O 0.3786(3) 0.7966(2) 0.3231(2) 0.0375(7) Uani 1 1 d . . . O3 O 0.2834(3) 1.0022(3) 0.2695(2) 0.0339(6) Uani 1 1 d . . . O4 O 0.3407(3) 0.8858(3) 0.4573(2) 0.0356(7) Uani 1 1 d . . . Cl2 Cl 0.43945(10) 0.71846(9) 0.03136(7) 0.0316(2) Uani 1 1 d D . . O5 O 0.3506(5) 0.7092(4) 0.1329(3) 0.0845(14) Uani 1 1 d DU A . O6 O 0.3666(8) 0.7202(9) -0.0528(5) 0.085(3) Uani 0.653(12) 1 d PDU A 1 O7 O 0.5018(11) 0.8265(7) -0.0164(8) 0.127(4) Uani 0.653(12) 1 d PDU A 1 O8 O 0.5419(7) 0.6125(7) 0.0631(6) 0.092(3) Uani 0.653(12) 1 d PDU A 1 O6' O 0.4241(17) 0.8406(8) -0.0528(9) 0.099(5) Uani 0.347(12) 1 d PDU A 2 O7' O 0.5785(7) 0.6775(14) 0.0540(11) 0.073(4) Uani 0.347(12) 1 d PDU A 2 O8' O 0.4043(14) 0.6423(14) -0.0189(12) 0.083(4) Uani 0.347(12) 1 d PDU A 2 O9 O 0.7757(5) 0.4861(4) 0.0227(4) 0.0811(13) Uani 1 1 d D . . H9A H 0.7155 0.5513 0.0108 0.122 Uiso 1 1 d RD . . H9B H 0.7468 0.4263 0.0205 0.122 Uiso 1 1 d RD . . O10 O 1.0019(4) 0.4577(4) 0.1620(3) 0.0704(11) Uani 1 1 d D . . H10A H 0.9383 0.5167 0.1642 0.106 Uiso 1 1 d RD . . H10B H 0.9703 0.4435 0.1092 0.106 Uiso 1 1 d RD . . 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 0.0183(2) 0.0131(2) 0.0166(2) -0.00498(18) -0.00339(16) -0.00361(17) N1 0.0255(15) 0.0192(15) 0.0192(14) -0.0045(12) -0.0073(12) -0.0054(12) N2 0.0172(14) 0.0142(13) 0.0171(14) -0.0071(11) -0.0041(11) -0.0003(11) N3 0.0168(13) 0.0159(14) 0.0194(14) -0.0074(11) -0.0017(11) -0.0019(11) N4 0.0173(14) 0.0188(14) 0.0237(15) -0.0087(12) -0.0073(11) -0.0007(11) N5 0.0149(13) 0.0154(13) 0.0210(14) -0.0063(12) -0.0035(11) -0.0025(11) C1 0.036(2) 0.0277(19) 0.0222(19) -0.0032(16) -0.0119(16) -0.0031(16) C2 0.056(3) 0.042(2) 0.0185(19) -0.0067(18) -0.0138(18) -0.009(2) C3 0.057(3) 0.045(3) 0.020(2) -0.0128(18) -0.0007(18) -0.009(2) C4 0.041(2) 0.032(2) 0.0191(18) -0.0093(16) 0.0008(16) -0.0016(17) C5 0.0290(19) 0.0162(16) 0.0185(17) -0.0046(14) -0.0040(14) -0.0031(14) C6 0.0235(17) 0.0192(17) 0.0186(17) -0.0073(14) 0.0003(13) -0.0051(14) C7 0.0225(16) 0.0151(16) 0.0191(16) -0.0080(14) -0.0058(13) -0.0027(13) C8 0.0207(16) 0.0175(16) 0.0148(15) -0.0085(13) -0.0007(13) -0.0016(13) C9 0.0201(16) 0.0209(17) 0.0181(16) -0.0096(14) 0.0010(13) -0.0070(13) C10 0.0316(19) 0.0180(17) 0.0213(17) -0.0089(14) -0.0001(14) -0.0112(14) C11 0.0329(19) 0.0140(16) 0.0235(18) -0.0058(14) -0.0039(15) 0.0003(14) C12 0.0222(17) 0.0178(17) 0.0222(17) -0.0058(14) -0.0045(14) -0.0012(14) C13 0.0104(14) 0.0152(15) 0.0182(16) -0.0062(13) -0.0030(12) -0.0003(12) C14 0.0162(15) 0.0181(16) 0.0146(15) -0.0060(13) -0.0045(12) 0.0012(13) C15 0.0149(15) 0.0152(16) 0.0188(16) -0.0089(13) -0.0038(12) 0.0013(12) C16 0.0246(18) 0.0255(18) 0.0279(19) -0.0117(16) -0.0095(15) -0.0038(15) C17 0.0252(18) 0.0275(19) 0.040(2) -0.0221(18) -0.0082(16) -0.0023(15) C18 0.0188(17) 0.0176(17) 0.045(2) -0.0129(17) -0.0060(16) -0.0036(14) C19 0.0155(17) 0.0162(17) 0.033(2) -0.0068(15) -0.0052(14) -0.0030(13) C20 0.0119(15) 0.0195(17) 0.0265(18) -0.0091(15) -0.0049(13) -0.0003(13) C21 0.0129(15) 0.0172(16) 0.0256(17) -0.0078(14) -0.0046(13) -0.0016(13) C22 0.0243(18) 0.0205(17) 0.0249(18) -0.0030(15) -0.0031(14) -0.0057(14) C23 0.0281(19) 0.030(2) 0.0209(18) -0.0050(16) -0.0028(15) -0.0040(16) C24 0.0266(18) 0.033(2) 0.0241(18) -0.0142(16) -0.0013(15) -0.0040(16) C25 0.0207(17) 0.0207(17) 0.0248(18) -0.0109(15) -0.0027(14) -0.0017(14) Cl1 0.0193(4) 0.0193(4) 0.0193(4) -0.0062(3) -0.0027(3) -0.0059(3) O1 0.0160(12) 0.0223(13) 0.0419(15) -0.0029(12) -0.0074(11) -0.0039(10) O2 0.0522(18) 0.0307(15) 0.0386(16) -0.0192(13) 0.0019(13) -0.0194(13) O3 0.0225(13) 0.0363(15) 0.0348(15) -0.0062(12) -0.0108(11) 0.0018(12) O4 0.0537(18) 0.0332(15) 0.0195(13) -0.0103(12) 0.0018(12) -0.0113(13) Cl2 0.0352(5) 0.0312(5) 0.0214(5) -0.0058(4) -0.0040(4) -0.0004(4) O5 0.101(3) 0.086(3) 0.040(2) -0.021(2) 0.022(2) 0.004(2) O6 0.108(5) 0.108(6) 0.046(3) -0.026(4) -0.035(3) -0.014(4) O7 0.139(7) 0.095(5) 0.125(6) 0.010(5) -0.028(6) -0.075(5) O8 0.056(4) 0.081(5) 0.079(4) 0.009(4) -0.004(3) 0.020(4) O6' 0.121(8) 0.070(7) 0.075(7) 0.004(5) -0.023(6) -0.012(6) O7' 0.053(6) 0.084(8) 0.106(7) -0.055(6) -0.047(5) 0.012(5) O8' 0.100(8) 0.099(8) 0.085(8) -0.057(6) -0.024(6) -0.028(6) O9 0.074(3) 0.091(3) 0.064(3) -0.020(2) -0.016(2) 0.003(2) O10 0.088(3) 0.066(3) 0.058(2) -0.027(2) -0.006(2) -0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N5 2.004(3) . ? Cu1 N1 2.007(3) . ? Cu1 N4 2.015(3) . ? Cu1 N3 2.025(3) . ? Cu1 O1 2.388(2) . ? Cu1 N2 2.427(3) . ? N1 C5 1.338(5) . ? N1 C1 1.360(5) . ? N2 C13 1.435(4) . ? N2 C6 1.475(4) . ? N2 C7 1.482(4) . ? N3 C12 1.347(4) . ? N3 C8 1.355(4) . ? N4 C16 1.343(4) . ? N4 C20 1.348(4) . ? N5 C21 1.345(4) . ? N5 C25 1.348(4) . ? C1 C2 1.373(5) . ? C1 H1 0.9300 . ? C2 C3 1.378(6) . ? C2 H2 0.9300 . ? C3 C4 1.375(6) . ? C3 H3 0.9300 . ? C4 C5 1.379(5) . ? C4 H4 0.9300 . ? C5 C6 1.524(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.514(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.382(5) . ? C9 C10 1.379(5) . ? C9 H9 0.9300 . ? C10 C11 1.388(5) . ? C10 H10 0.9300 . ? C11 C12 1.374(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C15 1.395(4) . ? C13 C14 1.396(4) . ? C14 C15 1.386(5) 2_766 ? C14 H14 0.9300 . ? C15 C14 1.386(5) 2_766 ? C15 H15 0.9300 . ? C16 C17 1.373(5) . ? C16 H16 0.9300 . ? C17 C18 1.377(6) . ? C17 H17 0.9300 . ? C18 C19 1.391(5) . ? C18 H18 0.9300 . ? C19 C20 1.387(5) . ? C19 H19 0.9300 . ? C20 C21 1.480(5) . ? C21 C22 1.384(5) . ? C22 C23 1.395(5) . ? C22 H22 0.9300 . ? C23 C24 1.384(5) . ? C23 H23 0.9300 . ? C24 C25 1.379(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? Cl1 O2 1.427(3) . ? Cl1 O3 1.431(3) . ? Cl1 O4 1.440(3) . ? Cl1 O1 1.451(3) . ? Cl2 O6 1.410(5) . ? Cl2 O5 1.410(3) . ? Cl2 O7' 1.418(6) . ? Cl2 O6' 1.426(7) . ? Cl2 O7 1.427(5) . ? Cl2 O8 1.432(5) . ? Cl2 O8' 1.468(6) . ? O9 H9A 0.8683 . ? O9 H9B 0.8560 . ? O10 H10A 0.8629 . ? O10 H10B 0.8943 . ? 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 N5 Cu1 N1 170.46(11) . . ? N5 Cu1 N4 80.98(11) . . ? N1 Cu1 N4 93.30(12) . . ? N5 Cu1 N3 96.10(11) . . ? N1 Cu1 N3 88.83(12) . . ? N4 Cu1 N3 173.74(10) . . ? N5 Cu1 O1 92.59(10) . . ? N1 Cu1 O1 95.66(11) . . ? N4 Cu1 O1 96.61(10) . . ? N3 Cu1 O1 89.03(10) . . ? N5 Cu1 N2 93.93(10) . . ? N1 Cu1 N2 79.12(11) . . ? N4 Cu1 N2 96.99(10) . . ? N3 Cu1 N2 77.62(10) . . ? O1 Cu1 N2 165.69(9) . . ? C5 N1 C1 119.6(3) . . ? C5 N1 Cu1 119.4(2) . . ? C1 N1 Cu1 120.4(2) . . ? C13 N2 C6 116.0(2) . . ? C13 N2 C7 117.1(2) . . ? C6 N2 C7 112.2(3) . . ? C13 N2 Cu1 107.25(19) . . ? C6 N2 Cu1 103.75(18) . . ? C7 N2 Cu1 97.64(17) . . ? C12 N3 C8 118.8(3) . . ? C12 N3 Cu1 123.1(2) . . ? C8 N3 Cu1 117.5(2) . . ? C16 N4 C20 118.2(3) . . ? C16 N4 Cu1 127.7(2) . . ? C20 N4 Cu1 113.2(2) . . ? C21 N5 C25 118.8(3) . . ? C21 N5 Cu1 114.0(2) . . ? C25 N5 Cu1 127.0(2) . . ? N1 C1 C2 121.5(4) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C1 C2 C3 118.8(4) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 119.4(4) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 119.8(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 120.8(3) . . ? N1 C5 C6 119.2(3) . . ? C4 C5 C6 119.9(3) . . ? N2 C6 C5 114.5(3) . . ? N2 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? N2 C6 H6B 108.6 . . ? C5 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? N2 C7 C8 110.3(2) . . ? N2 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N2 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N3 C8 C9 120.9(3) . . ? N3 C8 C7 116.4(3) . . ? C9 C8 C7 122.6(3) . . ? C10 C9 C8 120.3(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 118.4(3) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C12 C11 C10 119.2(3) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? N3 C12 C11 122.4(3) . . ? N3 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C15 C13 C14 117.5(3) . . ? C15 C13 N2 123.0(3) . . ? C14 C13 N2 119.3(3) . . ? C15 C14 C13 121.5(3) 2_766 . ? C15 C14 H14 119.2 2_766 . ? C13 C14 H14 119.2 . . ? C14 C15 C13 120.9(3) 2_766 . ? C14 C15 H15 119.5 2_766 . ? C13 C15 H15 119.5 . . ? N4 C16 C17 122.7(3) . . ? N4 C16 H16 118.7 . . ? C17 C16 H16 118.7 . . ? C16 C17 C18 119.4(3) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 118.7(3) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 118.9(3) . . ? C20 C19 H19 120.6 . . ? C18 C19 H19 120.6 . . ? N4 C20 C19 122.1(3) . . ? N4 C20 C21 114.7(3) . . ? C19 C20 C21 123.2(3) . . ? N5 C21 C22 121.9(3) . . ? N5 C21 C20 114.8(3) . . ? C22 C21 C20 123.3(3) . . ? C21 C22 C23 118.9(3) . . ? C21 C22 H22 120.6 . . ? C23 C22 H22 120.6 . . ? C24 C23 C22 119.2(3) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C25 C24 C23 118.6(3) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? N5 C25 C24 122.6(3) . . ? N5 C25 H25 118.7 . . ? C24 C25 H25 118.7 . . ? O2 Cl1 O3 110.26(18) . . ? O2 Cl1 O4 109.84(17) . . ? O3 Cl1 O4 109.38(17) . . ? O2 Cl1 O1 109.61(17) . . ? O3 Cl1 O1 108.45(16) . . ? O4 Cl1 O1 109.27(17) . . ? Cl1 O1 Cu1 130.50(15) . . ? O6 Cl2 O5 110.4(4) . . ? O6 Cl2 O7' 132.7(5) . . ? O5 Cl2 O7' 111.4(5) . . ? O6 Cl2 O6' 73.4(6) . . ? O5 Cl2 O6' 110.5(5) . . ? O7' Cl2 O6' 110.4(6) . . ? O6 Cl2 O7 107.9(4) . . ? O5 Cl2 O7 112.0(4) . . ? O7' Cl2 O7 75.3(6) . . ? O6' Cl2 O7 38.1(6) . . ? O6 Cl2 O8 109.8(4) . . ? O5 Cl2 O8 106.1(3) . . ? O7' Cl2 O8 36.8(5) . . ? O6' Cl2 O8 139.2(6) . . ? O7 Cl2 O8 110.6(5) . . ? O6 Cl2 O8' 36.2(5) . . ? O5 Cl2 O8' 109.9(5) . . ? O7' Cl2 O8' 107.3(6) . . ? O6' Cl2 O8' 107.0(6) . . ? O7 Cl2 O8' 133.3(6) . . ? O8 Cl2 O8' 75.7(6) . . ? H9A O9 H9B 114.8 . . ? H10A O10 H10B 97.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 Cu1 N1 C5 -39.9(8) . . . . ? N4 Cu1 N1 C5 -92.7(3) . . . . ? N3 Cu1 N1 C5 81.4(3) . . . . ? O1 Cu1 N1 C5 170.3(3) . . . . ? N2 Cu1 N1 C5 3.8(2) . . . . ? N5 Cu1 N1 C1 130.7(6) . . . . ? N4 Cu1 N1 C1 78.0(3) . . . . ? N3 Cu1 N1 C1 -107.9(3) . . . . ? O1 Cu1 N1 C1 -19.0(3) . . . . ? N2 Cu1 N1 C1 174.4(3) . . . . ? N5 Cu1 N2 C13 58.4(2) . . . . ? N1 Cu1 N2 C13 -115.0(2) . . . . ? N4 Cu1 N2 C13 -23.0(2) . . . . ? N3 Cu1 N2 C13 153.8(2) . . . . ? O1 Cu1 N2 C13 175.3(3) . . . . ? N5 Cu1 N2 C6 -178.30(19) . . . . ? N1 Cu1 N2 C6 8.29(19) . . . . ? N4 Cu1 N2 C6 100.3(2) . . . . ? N3 Cu1 N2 C6 -82.9(2) . . . . ? O1 Cu1 N2 C6 -61.4(4) . . . . ? N5 Cu1 N2 C7 -63.16(19) . . . . ? N1 Cu1 N2 C7 123.4(2) . . . . ? N4 Cu1 N2 C7 -144.54(19) . . . . ? N3 Cu1 N2 C7 32.23(19) . . . . ? O1 Cu1 N2 C7 53.7(4) . . . . ? N5 Cu1 N3 C12 -109.9(3) . . . . ? N1 Cu1 N3 C12 78.3(3) . . . . ? N4 Cu1 N3 C12 -171.8(9) . . . . ? O1 Cu1 N3 C12 -17.4(3) . . . . ? N2 Cu1 N3 C12 157.4(3) . . . . ? N5 Cu1 N3 C8 79.6(2) . . . . ? N1 Cu1 N3 C8 -92.2(2) . . . . ? N4 Cu1 N3 C8 17.7(11) . . . . ? O1 Cu1 N3 C8 172.1(2) . . . . ? N2 Cu1 N3 C8 -13.1(2) . . . . ? N5 Cu1 N4 C16 177.0(3) . . . . ? N1 Cu1 N4 C16 -10.7(3) . . . . ? N3 Cu1 N4 C16 -120.4(9) . . . . ? O1 Cu1 N4 C16 85.4(3) . . . . ? N2 Cu1 N4 C16 -90.1(3) . . . . ? N5 Cu1 N4 C20 -14.1(2) . . . . ? N1 Cu1 N4 C20 158.3(2) . . . . ? N3 Cu1 N4 C20 48.5(11) . . . . ? O1 Cu1 N4 C20 -105.6(2) . . . . ? N2 Cu1 N4 C20 78.8(2) . . . . ? N1 Cu1 N5 C21 -42.1(7) . . . . ? N4 Cu1 N5 C21 11.5(2) . . . . ? N3 Cu1 N5 C21 -162.9(2) . . . . ? O1 Cu1 N5 C21 107.8(2) . . . . ? N2 Cu1 N5 C21 -84.9(2) . . . . ? N1 Cu1 N5 C25 132.2(6) . . . . ? N4 Cu1 N5 C25 -174.2(3) . . . . ? N3 Cu1 N5 C25 11.4(3) . . . . ? O1 Cu1 N5 C25 -77.9(3) . . . . ? N2 Cu1 N5 C25 89.3(3) . . . . ? C5 N1 C1 C2 1.8(6) . . . . ? Cu1 N1 C1 C2 -168.9(3) . . . . ? N1 C1 C2 C3 0.6(6) . . . . ? C1 C2 C3 C4 -2.1(7) . . . . ? C2 C3 C4 C5 1.3(7) . . . . ? C1 N1 C5 C4 -2.6(5) . . . . ? Cu1 N1 C5 C4 168.1(3) . . . . ? C1 N1 C5 C6 173.2(3) . . . . ? Cu1 N1 C5 C6 -16.1(4) . . . . ? C3 C4 C5 N1 1.1(6) . . . . ? C3 C4 C5 C6 -174.7(4) . . . . ? C13 N2 C6 C5 99.6(3) . . . . ? C7 N2 C6 C5 -122.0(3) . . . . ? Cu1 N2 C6 C5 -17.7(3) . . . . ? N1 C5 C6 N2 24.0(4) . . . . ? C4 C5 C6 N2 -160.1(3) . . . . ? C13 N2 C7 C8 -159.6(3) . . . . ? C6 N2 C7 C8 62.6(3) . . . . ? Cu1 N2 C7 C8 -45.7(3) . . . . ? C12 N3 C8 C9 0.6(4) . . . . ? Cu1 N3 C8 C9 171.5(2) . . . . ? C12 N3 C8 C7 178.8(3) . . . . ? Cu1 N3 C8 C7 -10.3(3) . . . . ? N2 C7 C8 N3 43.6(4) . . . . ? N2 C7 C8 C9 -138.2(3) . . . . ? N3 C8 C9 C10 0.2(5) . . . . ? C7 C8 C9 C10 -177.9(3) . . . . ? C8 C9 C10 C11 -0.5(5) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C8 N3 C12 C11 -1.0(5) . . . . ? Cu1 N3 C12 C11 -171.3(3) . . . . ? C10 C11 C12 N3 0.6(5) . . . . ? C6 N2 C13 C15 152.6(3) . . . . ? C7 N2 C13 C15 16.4(4) . . . . ? Cu1 N2 C13 C15 -92.1(3) . . . . ? C6 N2 C13 C14 -31.8(4) . . . . ? C7 N2 C13 C14 -168.0(3) . . . . ? Cu1 N2 C13 C14 83.6(3) . . . . ? C15 C13 C14 C15 0.7(5) . . . 2_766 ? N2 C13 C14 C15 -175.1(3) . . . 2_766 ? C14 C13 C15 C14 -0.7(5) . . . 2_766 ? N2 C13 C15 C14 175.0(3) . . . 2_766 ? C20 N4 C16 C17 -1.5(5) . . . . ? Cu1 N4 C16 C17 167.0(3) . . . . ? N4 C16 C17 C18 -0.8(5) . . . . ? C16 C17 C18 C19 2.1(5) . . . . ? C17 C18 C19 C20 -1.2(5) . . . . ? C16 N4 C20 C19 2.5(5) . . . . ? Cu1 N4 C20 C19 -167.6(2) . . . . ? C16 N4 C20 C21 -175.8(3) . . . . ? Cu1 N4 C20 C21 14.1(3) . . . . ? C18 C19 C20 N4 -1.2(5) . . . . ? C18 C19 C20 C21 177.0(3) . . . . ? C25 N5 C21 C22 -0.3(5) . . . . ? Cu1 N5 C21 C22 174.5(2) . . . . ? C25 N5 C21 C20 177.9(3) . . . . ? Cu1 N5 C21 C20 -7.3(3) . . . . ? N4 C20 C21 N5 -4.6(4) . . . . ? C19 C20 C21 N5 177.0(3) . . . . ? N4 C20 C21 C22 173.6(3) . . . . ? C19 C20 C21 C22 -4.7(5) . . . . ? N5 C21 C22 C23 -0.7(5) . . . . ? C20 C21 C22 C23 -178.8(3) . . . . ? C21 C22 C23 C24 1.1(5) . . . . ? C22 C23 C24 C25 -0.5(5) . . . . ? C21 N5 C25 C24 0.9(5) . . . . ? Cu1 N5 C25 C24 -173.1(3) . . . . ? C23 C24 C25 N5 -0.5(5) . . . . ? O2 Cl1 O1 Cu1 -49.4(3) . . . . ? O3 Cl1 O1 Cu1 -169.80(19) . . . . ? O4 Cl1 O1 Cu1 71.0(2) . . . . ? N5 Cu1 O1 Cl1 -50.0(2) . . . . ? N1 Cu1 O1 Cl1 125.2(2) . . . . ? N4 Cu1 O1 Cl1 31.2(2) . . . . ? N3 Cu1 O1 Cl1 -146.1(2) . . . . ? N2 Cu1 O1 Cl1 -167.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.837 _refine_diff_density_min -0.623 _refine_diff_density_rms 0.089