Electronic Supplementary Information for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name 'S. Brooker' _publ_contact_author_address ; Chemistry Department University of Otago PO Box 56 Dunedin 9001 NEW ZEALAND ; _publ_section_title ; Dicopper(II) complexes of a new pyrazolate-containing Schiff-base macrocycle and related acyclic ligand ; _publ_contact_author_email SBROOKER@ALKALI.OTAGO.AC.NZ _publ_author_name S.Brooker data_czas _database_code_depnum_ccdc_archive 'CCDC 623298' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 B Cu2 F4 N9 O S2' _chemical_formula_weight 734.55 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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 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 14.032(7) _cell_length_b 25.477(12) _cell_length_c 8.293(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.152(7) _cell_angle_gamma 90.00 _cell_volume 2960(2) _cell_formula_units_Z 4 _cell_measurement_temperature 158(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Thin plate' _exptl_crystal_colour Green _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 1.640 _exptl_absorpt_correction_type Semi-empirical(SADABS) _exptl_absorpt_correction_T_min 0.32 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 158(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' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23232 _diffrn_reflns_av_R_equivalents 0.1371 _diffrn_reflns_av_sigmaI/netI 0.2681 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 3 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.42 _reflns_number_total 6044 _reflns_number_gt 2258 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0607P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6044 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1753 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 0.757 _refine_ls_restrained_S_all 0.757 _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 -0.08574(6) 0.65612(3) 0.24066(8) 0.0383(3) Uani 1 1 d . . . Cu2 Cu 0.16538(6) 0.56613(3) 0.06692(8) 0.0340(3) Uani 1 1 d . . . N1 N 0.0310(4) 0.6176(2) 0.3204(5) 0.0308(14) Uani 1 1 d . . . N2 N 0.1142(4) 0.6004(2) 0.2703(5) 0.0334(15) Uani 1 1 d . . . C3 C 0.1767(5) 0.5903(3) 0.3987(7) 0.0334(17) Uiso 1 1 d . . . C4 C 0.1298(5) 0.6037(2) 0.5379(7) 0.0350(17) Uiso 1 1 d . . . H4 H 0.1551 0.6017 0.6463 0.042 Uiso 1 1 calc R . . C5 C 0.0422(5) 0.6198(2) 0.4876(7) 0.0286(16) Uiso 1 1 d . . . C6 C -0.0411(5) 0.6386(3) 0.5608(8) 0.0331(17) Uiso 1 1 d . . . H6 H -0.0427 0.6395 0.6751 0.040 Uiso 1 1 calc R . . N3 N -0.1121(4) 0.6541(2) 0.4754(6) 0.0382(15) Uani 1 1 d . . . C8 C -0.1989(5) 0.6732(3) 0.5401(7) 0.043(2) Uani 1 1 d . . . H8A H -0.1835 0.6900 0.6460 0.051 Uiso 1 1 calc R . . H8B H -0.2419 0.6432 0.5578 0.051 Uiso 1 1 calc R . . C9 C -0.2504(5) 0.7126(3) 0.4288(8) 0.044(2) Uani 1 1 d . . . H9A H -0.2058 0.7413 0.4040 0.053 Uiso 1 1 calc R . . H9B H -0.3041 0.7282 0.4847 0.053 Uiso 1 1 calc R . . C10 C -0.2886(5) 0.6875(3) 0.2716(8) 0.0418(19) Uiso 1 1 d . . . C11 C -0.3835(6) 0.6884(3) 0.2280(9) 0.060(2) Uiso 1 1 d . . . H11 H -0.4266 0.7058 0.2944 0.072 Uiso 1 1 calc R . . C12 C -0.4174(6) 0.6639(3) 0.0870(9) 0.067(2) Uiso 1 1 d . . . H12 H -0.4836 0.6637 0.0560 0.080 Uiso 1 1 calc R . . C13 C -0.3516(6) 0.6400(3) -0.0070(9) 0.055(2) Uiso 1 1 d . . . H13 H -0.3722 0.6227 -0.1044 0.066 Uiso 1 1 calc R . . C14 C -0.2572(5) 0.6413(3) 0.0407(8) 0.0400(18) Uiso 1 1 d . . . H14 H -0.2133 0.6251 -0.0270 0.048 Uiso 1 1 calc R . . N4 N -0.2220(4) 0.6642(2) 0.1790(6) 0.0437(16) Uani 1 1 d . . . C15 C 0.2688(5) 0.5721(3) 0.3647(7) 0.0351(17) Uiso 1 1 d . . . H15 H 0.3189 0.5704 0.4463 0.042 Uiso 1 1 calc R . . N5 N 0.2819(4) 0.5577(2) 0.2156(6) 0.0355(15) Uani 1 1 d . . . C17 C 0.3731(5) 0.5388(3) 0.1688(7) 0.043(2) Uani 1 1 d . . . H17A H 0.3758 0.5001 0.1797 0.052 Uiso 1 1 calc R . . H17B H 0.4248 0.5540 0.2401 0.052 Uiso 1 1 calc R . . C18 C 0.3867(5) 0.5545(3) -0.0072(7) 0.0420(19) Uani 1 1 d . . . H18A H 0.3729 0.5924 -0.0206 0.050 Uiso 1 1 calc R . . H18B H 0.4541 0.5487 -0.0318 0.050 Uiso 1 1 calc R . . C19 C 0.3241(5) 0.5244(3) -0.1235(7) 0.0351(17) Uiso 1 1 d . . . C20 C 0.3656(6) 0.4963(3) -0.2500(8) 0.050(2) Uiso 1 1 d . . . H20 H 0.4325 0.4974 -0.2616 0.059 Uiso 1 1 calc R . . C21 C 0.3077(5) 0.4679(3) -0.3546(8) 0.046(2) Uiso 1 1 d . . . H21 H 0.3343 0.4492 -0.4405 0.055 Uiso 1 1 calc R . . C22 C 0.2115(5) 0.4660(3) -0.3364(8) 0.0424(19) Uiso 1 1 d . . . H22 H 0.1712 0.4463 -0.4097 0.051 Uiso 1 1 calc R . . C23 C 0.1727(5) 0.4934(3) -0.2083(7) 0.0358(17) Uiso 1 1 d . . . H23 H 0.1063 0.4912 -0.1920 0.043 Uiso 1 1 calc R . . N6 N 0.2307(4) 0.5232(2) -0.1072(6) 0.0325(14) Uani 1 1 d . . . N50 N -0.0480(4) 0.6747(2) 0.0252(6) 0.0395(16) Uani 1 1 d . . . C50 C -0.0261(5) 0.7040(3) -0.0680(7) 0.039(2) Uani 1 1 d . . . S50 S 0.00566(16) 0.74347(7) -0.21219(19) 0.0504(6) Uani 1 1 d . . . N60 N 0.0420(4) 0.5658(2) -0.0511(5) 0.0323(14) Uani 1 1 d . . . C60 C -0.0314(5) 0.5550(3) -0.1175(7) 0.0302(18) Uani 1 1 d . . . S60 S -0.13068(15) 0.54171(8) -0.2180(2) 0.0461(6) Uani 1 1 d . . . O70 O 0.2309(4) 0.6428(2) -0.0342(5) 0.0466(14) Uani 1 1 d . . . C70 C 0.2116(6) 0.6875(3) -0.0001(8) 0.043(2) Uani 1 1 d . . . H70 H 0.1535 0.6934 0.0506 0.051 Uiso 1 1 calc R . . N70 N 0.2655(5) 0.7293(3) -0.0281(7) 0.0501(18) Uani 1 1 d . . . C71 C 0.2299(6) 0.7828(3) 0.0037(9) 0.070(3) Uani 1 1 d . . . H71A H 0.2099 0.7997 -0.0988 0.084 Uiso 1 1 calc R . . H71B H 0.2808 0.8035 0.0587 0.084 Uiso 1 1 calc R . . H71C H 0.1753 0.7806 0.0723 0.084 Uiso 1 1 calc R . . C72 C 0.3545(6) 0.7261(3) -0.1060(9) 0.065(3) Uani 1 1 d . . . H72A H 0.3706 0.6892 -0.1236 0.078 Uiso 1 1 calc R . . H72B H 0.4051 0.7427 -0.0374 0.078 Uiso 1 1 calc R . . H72C H 0.3484 0.7444 -0.2101 0.078 Uiso 1 1 calc R . . B1 B 0.4956(9) 0.6278(6) -0.4179(12) 0.073(4) Uani 1 1 d . . . F11 F 0.4301(5) 0.6218(2) -0.3196(7) 0.129(2) Uani 1 1 d . . . F12 F 0.5414(6) 0.6747(3) -0.3875(6) 0.170(4) Uani 1 1 d . . . F13 F 0.4696(5) 0.6251(4) -0.5676(6) 0.190(4) Uani 1 1 d . . . F14 F 0.5666(7) 0.5961(4) -0.3786(10) 0.231(6) 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 0.0524(7) 0.0436(6) 0.0188(4) 0.0012(4) 0.0026(4) 0.0055(5) Cu2 0.0439(6) 0.0353(6) 0.0222(4) -0.0035(4) -0.0034(4) 0.0033(5) N1 0.037(4) 0.037(4) 0.018(2) -0.001(2) 0.001(3) 0.006(3) N2 0.038(4) 0.040(4) 0.021(3) 0.003(2) -0.007(3) -0.001(3) N3 0.046(4) 0.040(4) 0.029(3) -0.003(3) 0.005(3) -0.002(3) C8 0.059(6) 0.043(5) 0.026(3) -0.013(3) 0.005(4) -0.001(4) C9 0.053(6) 0.033(5) 0.048(4) -0.009(4) 0.013(4) 0.007(4) N4 0.069(5) 0.033(4) 0.029(3) 0.003(3) 0.009(3) -0.004(3) N5 0.035(4) 0.032(4) 0.039(3) -0.001(3) -0.002(3) 0.008(3) C17 0.039(5) 0.042(5) 0.047(4) -0.002(4) -0.012(4) 0.014(4) C18 0.030(5) 0.045(5) 0.051(4) -0.004(4) 0.001(4) 0.000(4) N6 0.037(4) 0.024(4) 0.037(3) 0.003(2) 0.000(3) 0.004(3) N50 0.057(4) 0.048(4) 0.014(3) 0.003(3) 0.005(3) 0.007(3) C50 0.055(6) 0.039(5) 0.023(3) -0.011(3) 0.004(3) 0.008(4) S50 0.0815(17) 0.0400(13) 0.0303(9) 0.0042(8) 0.0088(10) 0.0014(12) N60 0.031(4) 0.040(4) 0.026(3) 0.004(3) 0.001(3) -0.002(3) C60 0.040(5) 0.029(5) 0.022(3) 0.005(3) 0.007(3) 0.006(4) S60 0.0542(15) 0.0467(13) 0.0356(9) 0.0051(8) -0.0121(9) -0.0098(11) O70 0.075(4) 0.027(3) 0.038(3) 0.004(2) 0.007(3) -0.003(3) C70 0.056(6) 0.035(6) 0.036(4) 0.011(4) -0.010(4) -0.004(5) N70 0.073(6) 0.030(4) 0.047(3) -0.002(3) 0.004(4) 0.006(4) C71 0.092(8) 0.042(6) 0.074(6) -0.006(4) 0.000(5) 0.010(6) C72 0.075(7) 0.059(6) 0.061(5) 0.006(4) 0.014(5) -0.006(5) B1 0.076(10) 0.099(10) 0.046(6) -0.023(6) 0.030(6) -0.031(9) F11 0.172(6) 0.107(5) 0.119(4) 0.001(4) 0.099(5) -0.008(4) F12 0.226(9) 0.211(8) 0.069(4) 0.018(4) -0.018(4) -0.140(8) F13 0.189(7) 0.331(11) 0.050(3) -0.010(5) -0.006(4) -0.172(7) F14 0.210(10) 0.284(13) 0.194(8) -0.109(8) -0.017(7) 0.156(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 N50 1.950(5) . y Cu1 N4 1.963(6) . y Cu1 N1 1.991(5) . y Cu1 N3 2.002(5) . y Cu2 N60 1.942(6) . y Cu2 N5 2.004(5) . y Cu2 N2 2.063(5) . y Cu2 N6 2.066(5) . y Cu2 O70 2.335(5) . y N1 N2 1.335(7) . ? N1 C5 1.388(7) . ? N2 C3 1.365(7) . ? C3 C4 1.401(8) . ? C3 C15 1.416(8) . ? C4 C5 1.341(8) . ? C5 C6 1.430(8) . ? C6 N3 1.252(7) . ? N3 C8 1.444(8) . ? C8 C9 1.519(9) . ? C9 C10 1.523(9) . ? C10 C11 1.361(9) . ? C10 N4 1.375(8) . ? C11 C12 1.386(10) . ? C12 C13 1.383(10) . ? C13 C14 1.363(9) . ? C14 N4 1.356(8) . ? C15 N5 1.313(7) . ? N5 C17 1.441(8) . ? C17 C18 1.536(8) . ? C18 C19 1.483(9) . ? C19 N6 1.325(8) . ? C19 C20 1.419(9) . ? C20 C21 1.365(9) . ? C21 C22 1.367(9) . ? C22 C23 1.406(8) . ? C23 N6 1.366(7) . ? N50 C50 1.130(8) . ? C50 S50 1.642(7) . ? N60 C60 1.172(7) . ? C60 S60 1.620(8) . ? O70 C70 1.209(8) . ? C70 N70 1.333(9) . ? N70 C72 1.439(9) . ? N70 C71 1.481(9) . ? B1 F11 1.272(10) . ? B1 F13 1.277(11) . ? B1 F14 1.310(14) . ? B1 F12 1.373(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N50 Cu1 N4 92.6(2) . . y N50 Cu1 N1 99.5(2) . . y N4 Cu1 N1 155.5(2) . . y N50 Cu1 N3 166.3(2) . . y N4 Cu1 N3 91.5(2) . . y N1 Cu1 N3 81.8(2) . . y N60 Cu2 N5 169.8(2) . . y N60 Cu2 N2 94.2(2) . . y N5 Cu2 N2 81.4(2) . . y N60 Cu2 N6 93.6(2) . . y N5 Cu2 N6 89.7(2) . . y N2 Cu2 N6 169.5(2) . . y N60 Cu2 O70 100.4(2) . . y N5 Cu2 O70 89.2(2) . . y N2 Cu2 O70 95.84(19) . . y N6 Cu2 O70 89.63(19) . . y N2 N1 C5 105.7(5) . . ? N2 N1 Cu1 140.9(4) . . y C5 N1 Cu1 111.0(4) . . ? N1 N2 C3 110.7(5) . . ? N1 N2 Cu2 138.0(4) . . y C3 N2 Cu2 108.7(4) . . ? N2 C3 C4 106.7(6) . . ? N2 C3 C15 117.4(6) . . ? C4 C3 C15 135.9(6) . . ? C5 C4 C3 106.3(6) . . ? C4 C5 N1 110.5(6) . . ? C4 C5 C6 136.7(6) . . ? N1 C5 C6 112.8(6) . . ? N3 C6 C5 120.5(6) . . ? C6 N3 C8 123.8(5) . . ? C6 N3 Cu1 112.0(5) . . ? C8 N3 Cu1 123.9(4) . . ? N3 C8 C9 112.3(5) . . ? C8 C9 C10 112.1(6) . . ? C11 C10 N4 122.9(7) . . ? C11 C10 C9 120.9(7) . . ? N4 C10 C9 116.2(6) . . ? C10 C11 C12 120.2(8) . . ? C13 C12 C11 117.7(8) . . ? C14 C13 C12 119.6(7) . . ? N4 C14 C13 124.0(7) . . ? C14 N4 C10 115.6(6) . . ? C14 N4 Cu1 118.6(5) . . ? C10 N4 Cu1 125.6(5) . . ? N5 C15 C3 117.1(6) . . ? C15 N5 C17 121.3(6) . . ? C15 N5 Cu2 113.5(5) . . ? C17 N5 Cu2 125.2(4) . . ? N5 C17 C18 109.1(5) . . ? C19 C18 C17 112.5(6) . . ? N6 C19 C20 120.8(6) . . ? N6 C19 C18 120.0(6) . . ? C20 C19 C18 119.2(7) . . ? C21 C20 C19 118.9(7) . . ? C20 C21 C22 120.4(7) . . ? C21 C22 C23 119.4(7) . . ? N6 C23 C22 119.8(7) . . ? C19 N6 C23 120.6(6) . . ? C19 N6 Cu2 122.6(4) . . ? C23 N6 Cu2 116.8(4) . . ? C50 N50 Cu1 152.4(6) . . ? N50 C50 S50 176.2(6) . . ? C60 N60 Cu2 166.6(6) . . ? N60 C60 S60 176.8(6) . . ? C70 O70 Cu2 127.4(5) . . ? O70 C70 N70 125.1(8) . . ? C70 N70 C72 123.2(7) . . ? C70 N70 C71 120.2(7) . . ? C72 N70 C71 116.2(7) . . ? F11 B1 F13 116.0(11) . . ? F11 B1 F14 109.5(12) . . ? F13 B1 F14 112.4(11) . . ? F11 B1 F12 109.6(10) . . ? F13 B1 F12 109.5(10) . . ? F14 B1 F12 98.6(11) . . ? 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 N50 Cu1 N1 N2 -5.2(7) . . . . ? N4 Cu1 N1 N2 113.3(7) . . . . ? N3 Cu1 N1 N2 -171.4(7) . . . . ? N50 Cu1 N1 C5 153.7(4) . . . . ? N4 Cu1 N1 C5 -87.9(6) . . . . ? N3 Cu1 N1 C5 -12.5(4) . . . . ? C5 N1 N2 C3 1.5(7) . . . . ? Cu1 N1 N2 C3 161.1(5) . . . . ? C5 N1 N2 Cu2 160.5(5) . . . . ? Cu1 N1 N2 Cu2 -40.0(10) . . . . y N60 Cu2 N2 N1 0.3(6) . . . . ? N5 Cu2 N2 N1 -170.5(6) . . . . ? N6 Cu2 N2 N1 -137.7(11) . . . . ? O70 Cu2 N2 N1 101.2(6) . . . . ? N60 Cu2 N2 C3 159.6(4) . . . . ? N5 Cu2 N2 C3 -11.2(4) . . . . ? N6 Cu2 N2 C3 21.6(15) . . . . ? O70 Cu2 N2 C3 -99.5(4) . . . . ? N1 N2 C3 C4 -1.7(7) . . . . ? Cu2 N2 C3 C4 -167.1(4) . . . . ? N1 N2 C3 C15 -179.5(6) . . . . ? Cu2 N2 C3 C15 15.2(7) . . . . ? N2 C3 C4 C5 1.2(7) . . . . ? C15 C3 C4 C5 178.3(8) . . . . ? C3 C4 C5 N1 -0.3(8) . . . . ? C3 C4 C5 C6 -179.9(8) . . . . ? N2 N1 C5 C4 -0.7(7) . . . . ? Cu1 N1 C5 C4 -167.1(4) . . . . ? N2 N1 C5 C6 179.0(5) . . . . ? Cu1 N1 C5 C6 12.6(7) . . . . ? C4 C5 C6 N3 175.3(7) . . . . ? N1 C5 C6 N3 -4.2(9) . . . . ? C5 C6 N3 C8 179.5(6) . . . . ? C5 C6 N3 Cu1 -6.5(8) . . . . ? N50 Cu1 N3 C6 -85.7(12) . . . . ? N4 Cu1 N3 C6 166.9(5) . . . . ? N1 Cu1 N3 C6 10.5(5) . . . . ? N50 Cu1 N3 C8 88.3(11) . . . . ? N4 Cu1 N3 C8 -19.1(5) . . . . ? N1 Cu1 N3 C8 -175.5(6) . . . . ? C6 N3 C8 C9 151.5(7) . . . . ? Cu1 N3 C8 C9 -21.8(8) . . . . ? N3 C8 C9 C10 66.8(8) . . . . ? C8 C9 C10 C11 120.6(8) . . . . ? C8 C9 C10 N4 -59.2(8) . . . . ? N4 C10 C11 C12 1.8(12) . . . . ? C9 C10 C11 C12 -178.0(7) . . . . ? C10 C11 C12 C13 -1.2(12) . . . . ? C11 C12 C13 C14 -0.2(11) . . . . ? C12 C13 C14 N4 1.2(11) . . . . ? C13 C14 N4 C10 -0.6(10) . . . . ? C13 C14 N4 Cu1 173.7(5) . . . . ? C11 C10 N4 C14 -0.9(10) . . . . ? C9 C10 N4 C14 179.0(6) . . . . ? C11 C10 N4 Cu1 -174.7(6) . . . . ? C9 C10 N4 Cu1 5.1(9) . . . . ? N50 Cu1 N4 C14 48.0(5) . . . . ? N1 Cu1 N4 C14 -71.8(7) . . . . ? N3 Cu1 N4 C14 -145.1(5) . . . . ? N50 Cu1 N4 C10 -138.3(6) . . . . ? N1 Cu1 N4 C10 101.8(7) . . . . ? N3 Cu1 N4 C10 28.5(6) . . . . ? N2 C3 C15 N5 -11.4(9) . . . . ? C4 C3 C15 N5 171.7(7) . . . . ? C3 C15 N5 C17 179.9(6) . . . . ? C3 C15 N5 Cu2 0.8(8) . . . . ? N60 Cu2 N5 C15 -59.2(15) . . . . ? N2 Cu2 N5 C15 5.8(5) . . . . ? N6 Cu2 N5 C15 -168.5(5) . . . . ? O70 Cu2 N5 C15 101.9(5) . . . . ? N60 Cu2 N5 C17 121.8(12) . . . . ? N2 Cu2 N5 C17 -173.2(6) . . . . ? N6 Cu2 N5 C17 12.4(5) . . . . ? O70 Cu2 N5 C17 -77.2(5) . . . . ? C15 N5 C17 C18 -147.9(6) . . . . ? Cu2 N5 C17 C18 31.1(8) . . . . ? N5 C17 C18 C19 -71.3(7) . . . . ? C17 C18 C19 N6 54.1(9) . . . . ? C17 C18 C19 C20 -124.9(6) . . . . ? N6 C19 C20 C21 -0.3(10) . . . . ? C18 C19 C20 C21 178.7(6) . . . . ? C19 C20 C21 C22 -0.7(10) . . . . ? C20 C21 C22 C23 -0.4(11) . . . . ? C21 C22 C23 N6 2.5(10) . . . . ? C20 C19 N6 C23 2.4(9) . . . . ? C18 C19 N6 C23 -176.6(6) . . . . ? C20 C19 N6 Cu2 -176.7(5) . . . . ? C18 C19 N6 Cu2 4.3(8) . . . . ? C22 C23 N6 C19 -3.5(9) . . . . ? C22 C23 N6 Cu2 175.7(5) . . . . ? N60 Cu2 N6 C19 157.0(5) . . . . ? N5 Cu2 N6 C19 -32.6(5) . . . . ? N2 Cu2 N6 C19 -64.9(14) . . . . ? O70 Cu2 N6 C19 56.6(5) . . . . ? N60 Cu2 N6 C23 -22.2(5) . . . . ? N5 Cu2 N6 C23 148.2(4) . . . . ? N2 Cu2 N6 C23 115.9(12) . . . . ? O70 Cu2 N6 C23 -122.6(4) . . . . ? N4 Cu1 N50 C50 91.3(13) . . . . ? N1 Cu1 N50 C50 -110.0(13) . . . . ? N3 Cu1 N50 C50 -16(2) . . . . ? Cu1 N50 C50 S50 -175(10) . . . . ? N5 Cu2 N60 C60 -45(3) . . . . ? N2 Cu2 N60 C60 -109(2) . . . . ? N6 Cu2 N60 C60 64(2) . . . . ? O70 Cu2 N60 C60 154(2) . . . . ? Cu2 N60 C60 S60 -123(11) . . . . ? N60 Cu2 O70 C70 75.7(6) . . . . ? N5 Cu2 O70 C70 -100.9(6) . . . . ? N2 Cu2 O70 C70 -19.6(6) . . . . ? N6 Cu2 O70 C70 169.3(6) . . . . ? Cu2 O70 C70 N70 162.4(5) . . . . ? O70 C70 N70 C72 0.9(11) . . . . ? O70 C70 N70 C71 173.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.015 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.104 # Attachment 'CZCS.CIF' data_czcs _database_code_depnum_ccdc_archive 'CCDC 623299' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 Cu2 N11 O S2' _chemical_formula_weight 638.72 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 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 16.272(5) _cell_length_b 14.165(4) _cell_length_c 11.528(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.869(4) _cell_angle_gamma 90.00 _cell_volume 2643.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 165(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 1.805 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 165(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 'area detector' _diffrn_measurement_method 'Bruker SMART' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19966 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0759 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 26.36 _reflns_number_total 5368 _reflns_number_gt 3380 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0476P)^2^+7.0558P] 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 5368 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0965 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.99232(4) 0.18814(5) 0.48916(6) 0.02214(18) Uani 1 1 d . . . Cu2 Cu 0.74794(4) 0.17978(5) 0.40089(6) 0.02239(18) Uani 1 1 d . . . N1 N 0.9251(3) 0.1690(3) 0.3409(4) 0.0214(10) Uani 1 1 d . . . N2 N 0.8433(3) 0.1662(3) 0.3112(4) 0.0219(10) Uani 1 1 d . . . C3 C 0.8289(3) 0.1205(4) 0.2078(5) 0.0231(12) Uani 1 1 d . . . C4 C 0.9042(3) 0.0948(4) 0.1676(5) 0.0263(12) Uani 1 1 d . . . H4 H 0.9133 0.0638 0.0970 0.032 Uiso 1 1 calc R . . C5 C 0.9631(3) 0.1262(4) 0.2570(5) 0.0238(12) Uani 1 1 d . . . C6 C 1.0519(3) 0.1145(4) 0.2880(5) 0.0268(13) Uani 1 1 d . . . H6 H 1.0875 0.0923 0.2336 0.032 Uiso 1 1 calc R . . N3 N 1.0789(3) 0.1360(3) 0.3936(4) 0.0269(11) Uani 1 1 d . . . C8 C 1.1655(4) 0.1253(4) 0.4402(5) 0.0327(14) Uani 1 1 d . . . H8A H 1.1920 0.1883 0.4470 0.039 Uiso 1 1 calc R . . H8B H 1.1948 0.0871 0.3854 0.039 Uiso 1 1 calc R . . C9 C 1.1737(4) 0.0772(4) 0.5606(5) 0.0340(14) Uani 1 1 d . . . H9A H 1.1432 0.0167 0.5537 0.041 Uiso 1 1 calc R . . H9B H 1.2327 0.0622 0.5822 0.041 Uiso 1 1 calc R . . C10 C 1.1425(3) 0.1337(4) 0.6595(5) 0.0308(14) Uani 1 1 d . . . H10A H 1.1581 0.1012 0.7346 0.037 Uiso 1 1 calc R . . H10B H 1.1686 0.1970 0.6634 0.037 Uiso 1 1 calc R . . N4 N 1.0522(3) 0.1438(3) 0.6408(4) 0.0269(11) Uani 1 1 d . . . C12 C 1.0038(3) 0.1247(4) 0.7196(5) 0.0256(13) Uani 1 1 d . . . H12 H 1.0248 0.1046 0.7955 0.031 Uiso 1 1 calc R . . N5 N 0.8979(3) 0.1745(3) 0.5803(4) 0.0240(10) Uani 1 1 d . . . N6 N 0.8173(3) 0.1705(3) 0.5511(4) 0.0223(10) Uani 1 1 d . . . C13 C 0.9151(3) 0.1355(4) 0.6866(5) 0.0237(12) Uani 1 1 d . . . C14 C 0.8418(4) 0.1052(4) 0.7289(5) 0.0275(13) Uani 1 1 d . . . H14 H 0.8351 0.0759 0.8014 0.033 Uiso 1 1 calc R . . C15 C 0.7811(4) 0.1282(4) 0.6388(5) 0.0259(13) Uani 1 1 d . . . C16 C 0.6929(4) 0.1081(4) 0.6063(5) 0.0276(13) Uani 1 1 d . . . H16 H 0.6585 0.0834 0.6609 0.033 Uiso 1 1 calc R . . N7 N 0.6652(3) 0.1255(3) 0.5011(4) 0.0250(10) Uani 1 1 d . . . C18 C 0.5792(3) 0.1071(4) 0.4554(5) 0.0317(14) Uani 1 1 d . . . H18A H 0.5498 0.1680 0.4421 0.038 Uiso 1 1 calc R . . H18B H 0.5516 0.0711 0.5139 0.038 Uiso 1 1 calc R . . C19 C 0.5736(4) 0.0516(4) 0.3412(5) 0.0348(14) Uani 1 1 d . . . H19A H 0.5154 0.0324 0.3208 0.042 Uiso 1 1 calc R . . H19B H 0.6068 -0.0068 0.3541 0.042 Uiso 1 1 calc R . . C20 C 0.6033(4) 0.1049(4) 0.2366(5) 0.0316(14) Uani 1 1 d . . . H20A H 0.5897 0.0674 0.1647 0.038 Uiso 1 1 calc R . . H20B H 0.5737 0.1659 0.2267 0.038 Uiso 1 1 calc R . . N8 N 0.6924(3) 0.1223(3) 0.2529(4) 0.0278(11) Uani 1 1 d . . . C22 C 0.7407(4) 0.1013(4) 0.1760(5) 0.0273(13) Uani 1 1 d . . . H22 H 0.7208 0.0750 0.1027 0.033 Uiso 1 1 calc R . . N50 N 1.0467(3) 0.3267(3) 0.4971(4) 0.0284(11) Uani 1 1 d . . . C50 C 1.1107(4) 0.3610(4) 0.5166(5) 0.0283(13) Uani 1 1 d . . . S50 S 1.20329(10) 0.40976(11) 0.54617(15) 0.0377(4) Uani 1 1 d . . . N60 N 0.6951(3) 0.3140(3) 0.3881(4) 0.0347(12) Uani 1 1 d . . . C60 C 0.6502(4) 0.3765(4) 0.3903(5) 0.0251(13) Uani 1 1 d . . . S60 S 0.58774(11) 0.46745(12) 0.39481(16) 0.0449(4) Uani 1 1 d . . . O70 O 0.3704(3) 0.0994(4) 0.4424(6) 0.0658(15) Uani 1 1 d . . . C70 C 0.3629(4) 0.1649(5) 0.3696(7) 0.0480(18) Uani 1 1 d . . . H70 H 0.3419 0.1501 0.2918 0.058 Uiso 1 1 calc R . . N70 N 0.3827(3) 0.2537(4) 0.3949(5) 0.0423(14) Uani 1 1 d . . . C71 C 0.3682(5) 0.3301(6) 0.3095(8) 0.070(2) Uani 1 1 d . . . H71A H 0.3387 0.3052 0.2376 0.084 Uiso 1 1 calc R . . H71B H 0.4213 0.3566 0.2924 0.084 Uiso 1 1 calc R . . H71C H 0.3350 0.3797 0.3414 0.084 Uiso 1 1 calc R . . C72 C 0.4149(5) 0.2819(6) 0.5115(7) 0.064(2) Uani 1 1 d . . . H72A H 0.3707 0.3109 0.5510 0.077 Uiso 1 1 calc R . . H72B H 0.4597 0.3276 0.5069 0.077 Uiso 1 1 calc R . . H72C H 0.4362 0.2263 0.5554 0.077 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 0.0216(4) 0.0223(3) 0.0221(4) -0.0002(3) 0.0004(3) 0.0005(3) Cu2 0.0221(4) 0.0224(3) 0.0227(4) -0.0007(3) 0.0021(3) 0.0010(3) N1 0.022(3) 0.019(2) 0.024(2) 0.0010(19) 0.0027(19) 0.0005(18) N2 0.022(3) 0.017(2) 0.026(2) 0.0032(19) -0.0017(19) 0.0014(18) C3 0.031(3) 0.021(3) 0.017(3) 0.004(2) 0.002(2) 0.003(2) C4 0.033(3) 0.025(3) 0.022(3) 0.001(2) 0.005(2) 0.003(2) C5 0.032(3) 0.017(3) 0.024(3) 0.005(2) 0.006(2) -0.002(2) C6 0.026(3) 0.025(3) 0.032(3) 0.006(3) 0.014(3) -0.001(2) N3 0.025(3) 0.021(2) 0.035(3) -0.004(2) 0.005(2) 0.000(2) C8 0.026(3) 0.029(3) 0.042(4) -0.008(3) 0.000(3) 0.002(3) C9 0.020(3) 0.034(3) 0.046(4) 0.006(3) -0.003(3) 0.005(3) C10 0.023(3) 0.036(3) 0.031(3) 0.001(3) -0.006(3) 0.000(3) N4 0.024(3) 0.024(2) 0.032(3) 0.000(2) -0.004(2) 0.001(2) C12 0.031(3) 0.019(3) 0.025(3) -0.004(2) -0.008(3) 0.000(2) N5 0.027(3) 0.021(2) 0.024(2) -0.001(2) 0.000(2) 0.001(2) N6 0.026(3) 0.018(2) 0.023(2) -0.0009(19) 0.0027(19) 0.0008(19) C13 0.032(3) 0.019(3) 0.018(3) -0.007(2) -0.002(2) 0.001(2) C14 0.035(4) 0.025(3) 0.023(3) -0.004(2) 0.005(3) -0.002(3) C15 0.032(3) 0.019(3) 0.027(3) -0.005(2) 0.005(3) 0.001(2) C16 0.034(3) 0.021(3) 0.028(3) -0.001(2) 0.008(3) -0.002(2) N7 0.021(3) 0.024(2) 0.030(3) -0.002(2) 0.003(2) -0.0039(19) C18 0.019(3) 0.037(3) 0.039(4) -0.003(3) 0.003(3) -0.002(3) C19 0.024(3) 0.041(4) 0.038(4) -0.005(3) -0.001(3) -0.006(3) C20 0.027(3) 0.039(3) 0.027(3) -0.001(3) -0.004(3) 0.003(3) N8 0.028(3) 0.026(3) 0.029(3) -0.002(2) 0.000(2) 0.000(2) C22 0.040(4) 0.024(3) 0.017(3) 0.001(2) -0.002(2) 0.004(3) N50 0.026(3) 0.031(3) 0.028(3) -0.004(2) 0.001(2) -0.005(2) C50 0.038(4) 0.024(3) 0.023(3) -0.002(2) 0.005(3) 0.006(3) S50 0.0295(9) 0.0388(9) 0.0448(9) -0.0028(7) 0.0038(7) -0.0077(7) N60 0.040(3) 0.027(3) 0.038(3) 0.003(2) 0.008(2) 0.005(2) C60 0.030(3) 0.026(3) 0.019(3) 0.000(2) -0.002(2) 0.001(3) S60 0.0449(10) 0.0391(9) 0.0493(10) -0.0024(8) -0.0015(8) 0.0202(8) O70 0.050(3) 0.045(3) 0.102(5) 0.017(3) 0.003(3) -0.006(3) C70 0.032(4) 0.046(4) 0.066(5) 0.002(4) 0.005(3) -0.007(3) N70 0.040(3) 0.035(3) 0.053(4) 0.003(3) 0.010(3) 0.003(3) C71 0.076(6) 0.052(5) 0.082(6) 0.030(5) 0.012(5) 0.004(4) C72 0.074(6) 0.053(5) 0.065(6) -0.005(4) 0.017(5) 0.014(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 N1 1.952(4) . y Cu1 N5 1.957(5) . y Cu1 N4 2.012(5) . y Cu1 N3 2.015(5) . y Cu1 N50 2.151(5) . y Cu2 N2 1.961(5) . y Cu2 N6 1.972(4) . y Cu2 N7 2.014(5) . y Cu2 N8 2.019(5) . y Cu2 N60 2.085(5) . y N1 N2 1.340(6) . ? N1 C5 1.344(7) . ? N2 C3 1.356(7) . ? C3 C4 1.401(8) . ? C3 C22 1.470(8) . ? C4 C5 1.405(8) . ? C5 C6 1.462(8) . ? C6 N3 1.288(7) . ? N3 C8 1.464(7) . ? C8 C9 1.540(9) . ? C9 C10 1.522(8) . ? C10 N4 1.470(7) . ? N4 C12 1.291(7) . ? C12 C13 1.462(8) . ? N5 N6 1.323(6) . ? N5 C13 1.347(7) . ? N6 C15 1.360(7) . ? C13 C14 1.401(8) . ? C14 C15 1.397(8) . ? C15 C16 1.472(8) . ? C16 N7 1.274(7) . ? N7 C18 1.467(7) . ? C18 C19 1.529(8) . ? C19 C20 1.542(8) . ? C20 N8 1.465(7) . ? N8 C22 1.278(7) . ? N50 C50 1.150(7) . ? C50 S50 1.662(7) . ? N60 C60 1.150(7) . ? C60 S60 1.645(6) . ? O70 C70 1.249(8) . ? C70 N70 1.324(8) . ? N70 C72 1.448(10) . ? N70 C71 1.466(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N5 93.21(18) . . y N1 Cu1 N4 153.57(18) . . y N5 Cu1 N4 80.79(19) . . y N1 Cu1 N3 80.28(19) . . y N5 Cu1 N3 152.67(19) . . y N4 Cu1 N3 93.3(2) . . y N1 Cu1 N50 110.82(18) . . y N5 Cu1 N50 114.14(18) . . y N4 Cu1 N50 95.00(18) . . y N3 Cu1 N50 92.87(18) . . y N2 Cu2 N6 92.53(18) . . y N2 Cu2 N7 151.29(18) . . y N6 Cu2 N7 80.01(19) . . y N2 Cu2 N8 79.89(19) . . y N6 Cu2 N8 151.83(18) . . y N7 Cu2 N8 93.64(19) . . y N2 Cu2 N60 113.25(18) . . y N6 Cu2 N60 108.51(19) . . y N7 Cu2 N60 95.36(19) . . y N8 Cu2 N60 99.4(2) . . y N2 N1 C5 108.7(4) . . ? N2 N1 Cu1 132.9(3) . . y C5 N1 Cu1 115.8(4) . . ? N1 N2 C3 108.5(4) . . ? N1 N2 Cu2 132.9(3) . . y C3 N2 Cu2 115.8(4) . . ? N2 C3 C4 109.6(5) . . ? N2 C3 C22 112.6(5) . . ? C4 C3 C22 137.3(5) . . ? C3 C4 C5 103.2(5) . . ? N1 C5 C4 110.0(5) . . ? N1 C5 C6 113.0(5) . . ? C4 C5 C6 136.5(5) . . ? N3 C6 C5 115.9(5) . . ? C6 N3 C8 123.0(5) . . ? C6 N3 Cu1 114.4(4) . . ? C8 N3 Cu1 122.6(4) . . ? N3 C8 C9 111.6(5) . . ? C10 C9 C8 116.0(5) . . ? N4 C10 C9 110.2(5) . . ? C12 N4 C10 123.3(5) . . ? C12 N4 Cu1 113.6(4) . . ? C10 N4 Cu1 123.1(4) . . ? N4 C12 C13 116.9(5) . . ? N6 N5 C13 108.8(4) . . ? N6 N5 Cu1 132.9(3) . . ? C13 N5 Cu1 115.3(4) . . ? N5 N6 C15 108.9(4) . . ? N5 N6 Cu2 133.2(3) . . ? C15 N6 Cu2 115.5(4) . . ? N5 C13 C14 109.7(5) . . ? N5 C13 C12 112.8(5) . . ? C14 C13 C12 136.9(5) . . ? C15 C14 C13 103.5(5) . . ? N6 C15 C14 109.1(5) . . ? N6 C15 C16 112.4(5) . . ? C14 C15 C16 137.8(5) . . ? N7 C16 C15 116.5(5) . . ? C16 N7 C18 122.6(5) . . ? C16 N7 Cu2 115.3(4) . . ? C18 N7 Cu2 122.0(4) . . ? N7 C18 C19 111.8(5) . . ? C18 C19 C20 115.2(5) . . ? N8 C20 C19 111.6(5) . . ? C22 N8 C20 122.9(5) . . ? C22 N8 Cu2 115.2(4) . . ? C20 N8 Cu2 121.9(4) . . ? N8 C22 C3 116.0(5) . . ? C50 N50 Cu1 138.9(4) . . ? N50 C50 S50 179.4(6) . . ? C60 N60 Cu2 163.4(5) . . ? N60 C60 S60 178.6(6) . . ? O70 C70 N70 123.6(7) . . ? C70 N70 C72 121.6(6) . . ? C70 N70 C71 122.4(7) . . ? C72 N70 C71 116.0(6) . . ? 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 N2 11.4(5) . . . . ? N4 Cu1 N1 N2 87.1(6) . . . . ? N3 Cu1 N1 N2 164.6(5) . . . . ? N50 Cu1 N1 N2 -106.0(4) . . . . ? N5 Cu1 N1 C5 -147.9(4) . . . . ? N4 Cu1 N1 C5 -72.2(6) . . . . ? N3 Cu1 N1 C5 5.4(4) . . . . ? N50 Cu1 N1 C5 94.8(4) . . . . ? C5 N1 N2 C3 0.6(5) . . . . ? Cu1 N1 N2 C3 -159.7(4) . . . . ? C5 N1 N2 Cu2 160.2(4) . . . . ? Cu1 N1 N2 Cu2 -0.1(7) . . . . ? N6 Cu2 N2 N1 -11.7(4) . . . . ? N7 Cu2 N2 N1 -85.3(6) . . . . ? N8 Cu2 N2 N1 -164.3(5) . . . . ? N60 Cu2 N2 N1 99.7(4) . . . . ? N6 Cu2 N2 C3 146.8(4) . . . . ? N7 Cu2 N2 C3 73.1(5) . . . . ? N8 Cu2 N2 C3 -5.9(4) . . . . ? N60 Cu2 N2 C3 -101.8(4) . . . . ? N1 N2 C3 C4 -1.6(6) . . . . ? Cu2 N2 C3 C4 -165.1(3) . . . . ? N1 N2 C3 C22 171.5(4) . . . . ? Cu2 N2 C3 C22 8.0(5) . . . . ? N2 C3 C4 C5 1.9(6) . . . . ? C22 C3 C4 C5 -168.7(6) . . . . ? N2 N1 C5 C4 0.7(6) . . . . ? Cu1 N1 C5 C4 164.8(3) . . . . ? N2 N1 C5 C6 -172.5(4) . . . . ? Cu1 N1 C5 C6 -8.4(6) . . . . ? C3 C4 C5 N1 -1.6(6) . . . . ? C3 C4 C5 C6 169.3(6) . . . . ? N1 C5 C6 N3 7.6(7) . . . . ? C4 C5 C6 N3 -163.0(6) . . . . ? C5 C6 N3 C8 177.8(5) . . . . ? C5 C6 N3 Cu1 -3.2(6) . . . . ? N1 Cu1 N3 C6 -1.0(4) . . . . ? N5 Cu1 N3 C6 77.0(6) . . . . ? N4 Cu1 N3 C6 153.2(4) . . . . ? N50 Cu1 N3 C6 -111.6(4) . . . . ? N1 Cu1 N3 C8 178.0(4) . . . . ? N5 Cu1 N3 C8 -104.0(5) . . . . ? N4 Cu1 N3 C8 -27.8(4) . . . . ? N50 Cu1 N3 C8 67.3(4) . . . . ? C6 N3 C8 C9 -133.5(6) . . . . ? Cu1 N3 C8 C9 47.7(6) . . . . ? N3 C8 C9 C10 -67.3(6) . . . . ? C8 C9 C10 N4 67.7(6) . . . . ? C9 C10 N4 C12 129.8(6) . . . . ? C9 C10 N4 Cu1 -49.9(6) . . . . ? N1 Cu1 N4 C12 -75.9(6) . . . . ? N5 Cu1 N4 C12 2.6(4) . . . . ? N3 Cu1 N4 C12 -150.5(4) . . . . ? N50 Cu1 N4 C12 116.3(4) . . . . ? N1 Cu1 N4 C10 103.7(5) . . . . ? N5 Cu1 N4 C10 -177.7(4) . . . . ? N3 Cu1 N4 C10 29.1(4) . . . . ? N50 Cu1 N4 C10 -64.0(4) . . . . ? C10 N4 C12 C13 -178.2(5) . . . . ? Cu1 N4 C12 C13 1.5(6) . . . . ? N1 Cu1 N5 N6 -10.2(5) . . . . ? N4 Cu1 N5 N6 -164.3(5) . . . . ? N3 Cu1 N5 N6 -85.1(6) . . . . ? N50 Cu1 N5 N6 104.3(5) . . . . ? N1 Cu1 N5 C13 147.5(4) . . . . ? N4 Cu1 N5 C13 -6.6(4) . . . . ? N3 Cu1 N5 C13 72.6(6) . . . . ? N50 Cu1 N5 C13 -98.0(4) . . . . ? C13 N5 N6 C15 -0.2(5) . . . . ? Cu1 N5 N6 C15 158.6(4) . . . . ? C13 N5 N6 Cu2 -161.0(4) . . . . ? Cu1 N5 N6 Cu2 -2.3(7) . . . . ? N2 Cu2 N6 N5 12.9(5) . . . . ? N7 Cu2 N6 N5 165.0(5) . . . . ? N8 Cu2 N6 N5 86.0(6) . . . . ? N60 Cu2 N6 N5 -102.7(5) . . . . ? N2 Cu2 N6 C15 -147.0(4) . . . . ? N7 Cu2 N6 C15 5.1(4) . . . . ? N8 Cu2 N6 C15 -73.8(6) . . . . ? N60 Cu2 N6 C15 97.4(4) . . . . ? N6 N5 C13 C14 -0.4(6) . . . . ? Cu1 N5 C13 C14 -163.3(3) . . . . ? N6 N5 C13 C12 171.9(4) . . . . ? Cu1 N5 C13 C12 9.0(6) . . . . ? N4 C12 C13 N5 -6.9(7) . . . . ? N4 C12 C13 C14 162.5(6) . . . . ? N5 C13 C14 C15 0.8(6) . . . . ? C12 C13 C14 C15 -168.9(6) . . . . ? N5 N6 C15 C14 0.7(6) . . . . ? Cu2 N6 C15 C14 165.3(3) . . . . ? N5 N6 C15 C16 -171.5(4) . . . . ? Cu2 N6 C15 C16 -6.9(6) . . . . ? C13 C14 C15 N6 -0.9(6) . . . . ? C13 C14 C15 C16 168.4(6) . . . . ? N6 C15 C16 N7 5.3(7) . . . . ? C14 C15 C16 N7 -163.8(6) . . . . ? C15 C16 N7 C18 178.6(5) . . . . ? C15 C16 N7 Cu2 -1.1(6) . . . . ? N2 Cu2 N7 C16 74.7(6) . . . . ? N6 Cu2 N7 C16 -2.1(4) . . . . ? N8 Cu2 N7 C16 150.3(4) . . . . ? N60 Cu2 N7 C16 -110.0(4) . . . . ? N2 Cu2 N7 C18 -105.0(5) . . . . ? N6 Cu2 N7 C18 178.2(4) . . . . ? N8 Cu2 N7 C18 -29.4(4) . . . . ? N60 Cu2 N7 C18 70.3(4) . . . . ? C16 N7 C18 C19 -130.1(6) . . . . ? Cu2 N7 C18 C19 49.6(6) . . . . ? N7 C18 C19 C20 -67.1(7) . . . . ? C18 C19 C20 N8 67.3(7) . . . . ? C19 C20 N8 C22 129.1(6) . . . . ? C19 C20 N8 Cu2 -49.9(6) . . . . ? N2 Cu2 N8 C22 2.5(4) . . . . ? N6 Cu2 N8 C22 -73.8(6) . . . . ? N7 Cu2 N8 C22 -149.3(4) . . . . ? N60 Cu2 N8 C22 114.6(4) . . . . ? N2 Cu2 N8 C20 -178.4(4) . . . . ? N6 Cu2 N8 C20 105.3(5) . . . . ? N7 Cu2 N8 C20 29.8(4) . . . . ? N60 Cu2 N8 C20 -66.3(4) . . . . ? C20 N8 C22 C3 -178.0(5) . . . . ? Cu2 N8 C22 C3 1.1(6) . . . . ? N2 C3 C22 N8 -5.9(7) . . . . ? C4 C3 C22 N8 164.5(6) . . . . ? N1 Cu1 N50 C50 -127.9(6) . . . . ? N5 Cu1 N50 C50 128.4(6) . . . . ? N4 Cu1 N50 C50 46.3(7) . . . . ? N3 Cu1 N50 C50 -47.2(7) . . . . ? Cu1 N50 C50 S50 -46(59) . . . . ? N2 Cu2 N60 C60 161.1(17) . . . . ? N6 Cu2 N60 C60 -97.7(17) . . . . ? N7 Cu2 N60 C60 -16.4(17) . . . . ? N8 Cu2 N60 C60 78.2(17) . . . . ? Cu2 N60 C60 S60 138(22) . . . . ? O70 C70 N70 C72 -0.1(11) . . . . ? O70 C70 N70 C71 -176.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.072 _refine_diff_density_min -0.627 _refine_diff_density_rms 0.114 # Attachment 'an117.cif' data_an117 _database_code_depnum_ccdc_archive 'CCDC 623300' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H32 Cu2 N6 O8' _chemical_formula_weight 671.65 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7717(5) _cell_length_b 12.2099(8) _cell_length_c 14.7707(9) _cell_angle_alpha 103.909(3) _cell_angle_beta 102.286(3) _cell_angle_gamma 106.107(3) _cell_volume 1407.49(15) _cell_formula_units_Z 2 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.569 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8847 _exptl_absorpt_correction_T_max 0.9399 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36609 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.45 _reflns_number_total 5771 _reflns_number_gt 4770 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0237P)^2^+1.6969P] 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 5771 _refine_ls_number_parameters 389 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0704 _refine_ls_wR_factor_gt 0.0656 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.46800(3) 0.46826(2) 0.22513(2) 0.01308(8) Uani 1 1 d . . . Cu2 Cu 0.29993(3) 0.77201(3) 0.20618(2) 0.01399(8) Uani 1 1 d . . . N1 N 0.3711(2) 0.53389(17) 0.12360(14) 0.0134(4) Uani 1 1 d . . . N2 N 0.2956(2) 0.61441(17) 0.12002(13) 0.0130(4) Uani 1 1 d . . . N3 N 0.4856(2) 0.35978(17) 0.10499(14) 0.0129(4) Uani 1 1 d . . . N4 N 0.5517(2) 0.37859(18) 0.31117(14) 0.0148(4) Uani 1 1 d . . . N5 N 0.1184(2) 0.74662(17) 0.08623(14) 0.0132(4) Uani 1 1 d . . . N6 N 0.2695(2) 0.92360(17) 0.28051(14) 0.0135(4) Uani 1 1 d . . . O30 O 0.28048(19) 0.47163(14) 0.28907(11) 0.0154(3) Uani 1 1 d . . . O31 O 0.1439(2) 0.29042(15) 0.17732(12) 0.0213(4) Uani 1 1 d . . . C30 C 0.1553(3) 0.3718(2) 0.24923(17) 0.0152(5) Uani 1 1 d . . . C31 C 0.0184(3) 0.3586(2) 0.2981(2) 0.0263(6) Uani 1 1 d . . . H31A H -0.0671 0.2787 0.2656 0.032 Uiso 1 1 calc R . . H31B H -0.0315 0.4203 0.2931 0.032 Uiso 1 1 calc R . . H31C H 0.0654 0.3683 0.3672 0.032 Uiso 1 1 calc R . . O40 O 0.63568(19) 0.63655(14) 0.31741(11) 0.0151(3) Uani 1 1 d . . . O41 O 0.8419(2) 0.58982(15) 0.27070(12) 0.0200(4) Uani 1 1 d . . . C40 C 0.7877(3) 0.6630(2) 0.31551(17) 0.0154(5) Uani 1 1 d . . . C41 C 0.9021(3) 0.7915(2) 0.37050(19) 0.0240(6) Uani 1 1 d . . . H41A H 1.0119 0.7920 0.4034 0.029 Uiso 1 1 calc R . . H41B H 0.8556 0.8287 0.4192 0.029 Uiso 1 1 calc R . . H41C H 0.9128 0.8370 0.3244 0.029 Uiso 1 1 calc R . . O50 O 0.5192(2) 0.81510(16) 0.30304(12) 0.0160(4) Uani 1 1 d D . . H50 H 0.586(4) 0.852(3) 0.278(2) 0.052(11) Uiso 1 1 d D . . H51 H 0.543(4) 0.757(2) 0.311(3) 0.053(11) Uiso 1 1 d D . . O60 O 0.1800(2) 0.67244(16) 0.30290(13) 0.0182(4) Uani 1 1 d D . . H60 H 0.210(4) 0.614(2) 0.299(2) 0.033(9) Uiso 1 1 d D . . H61 H 0.079(2) 0.647(3) 0.294(2) 0.041(10) Uiso 1 1 d D . . C3 C 0.2055(3) 0.5881(2) 0.02571(16) 0.0120(5) Uani 1 1 d . . . C4 C 0.2253(3) 0.4892(2) -0.03404(16) 0.0133(5) Uani 1 1 d . . . H4 H 0.1782 0.4522 -0.1028 0.016 Uiso 1 1 calc R . . C5 C 0.3306(3) 0.4576(2) 0.03135(16) 0.0125(5) Uani 1 1 d . . . C6 C 0.4062(3) 0.3652(2) 0.02404(17) 0.0139(5) Uani 1 1 d . . . H6 H 0.3970 0.3121 -0.0372 0.017 Uiso 1 1 calc R . . C8 C 0.5701(3) 0.2734(2) 0.10972(17) 0.0163(5) Uani 1 1 d . . . H8A H 0.6916 0.3157 0.1386 0.020 Uiso 1 1 calc R . . H8B H 0.5485 0.2188 0.0433 0.020 Uiso 1 1 calc R . . C9 C 0.5034(3) 0.2018(2) 0.17302(17) 0.0188(5) Uani 1 1 d . . . H9A H 0.3804 0.1753 0.1513 0.023 Uiso 1 1 calc R . . H9B H 0.5346 0.1288 0.1620 0.023 Uiso 1 1 calc R . . C10 C 0.5646(3) 0.2690(2) 0.28057(17) 0.0162(5) Uani 1 1 d . . . C11 C 0.6294(3) 0.2175(2) 0.34703(18) 0.0199(5) Uani 1 1 d . . . H11 H 0.6413 0.1416 0.3242 0.024 Uiso 1 1 calc R . . C12 C 0.6762(3) 0.2770(2) 0.44620(19) 0.0226(6) Uani 1 1 d . . . H12 H 0.7199 0.2424 0.4922 0.027 Uiso 1 1 calc R . . C13 C 0.6582(3) 0.3880(2) 0.47744(18) 0.0220(6) Uani 1 1 d . . . H13 H 0.6874 0.4303 0.5452 0.026 Uiso 1 1 calc R . . C14 C 0.5972(3) 0.4354(2) 0.40809(18) 0.0196(5) Uani 1 1 d . . . H14 H 0.5867 0.5120 0.4296 0.023 Uiso 1 1 calc R . . C15 C 0.1077(3) 0.6644(2) 0.01054(17) 0.0136(5) Uani 1 1 d . . . H15 H 0.0394 0.6535 -0.0525 0.016 Uiso 1 1 calc R . . C17 C 0.0242(3) 0.8273(2) 0.07890(17) 0.0155(5) Uani 1 1 d . . . H17A H -0.0639 0.8103 0.1110 0.019 Uiso 1 1 calc R . . H17B H -0.0292 0.8151 0.0094 0.019 Uiso 1 1 calc R . . C18 C 0.1438(3) 0.9563(2) 0.12882(17) 0.0158(5) Uani 1 1 d . . . H18A H 0.2427 0.9666 0.1052 0.019 Uiso 1 1 calc R . . H18B H 0.0888 1.0113 0.1094 0.019 Uiso 1 1 calc R . . C19 C 0.2000(3) 0.9920(2) 0.23845(17) 0.0140(5) Uani 1 1 d . . . C20 C 0.1807(3) 1.0932(2) 0.29533(18) 0.0193(5) Uani 1 1 d . . . H20 H 0.1312 1.1403 0.2648 0.023 Uiso 1 1 calc R . . C21 C 0.2334(3) 1.1251(2) 0.39588(19) 0.0221(6) Uani 1 1 d . . . H21 H 0.2221 1.1946 0.4351 0.026 Uiso 1 1 calc R . . C22 C 0.3032(3) 1.0541(2) 0.43890(18) 0.0182(5) Uani 1 1 d . . . H22 H 0.3396 1.0736 0.5080 0.022 Uiso 1 1 calc R . . C23 C 0.3185(3) 0.9547(2) 0.37896(17) 0.0153(5) Uani 1 1 d . . . H23 H 0.3658 0.9057 0.4083 0.018 Uiso 1 1 calc R . . O70 O 0.4792(2) 0.89394(17) 0.12241(13) 0.0271(4) Uani 1 1 d . . . O71 O 0.7210(3) 0.9268(3) 0.2243(2) 0.0696(9) Uani 1 1 d . . . C70 C 0.6354(3) 0.9339(2) 0.15121(18) 0.0189(5) Uani 1 1 d . . . C71 C 0.7243(3) 0.9951(2) 0.08829(19) 0.0245(6) Uani 1 1 d . . . H71A H 0.8199 1.0663 0.1308 0.029 Uiso 1 1 calc R . . H71B H 0.6471 1.0196 0.0459 0.029 Uiso 1 1 calc R . . H71C H 0.7629 0.9388 0.0479 0.029 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 0.01684(15) 0.01278(16) 0.01151(14) 0.00402(12) 0.00378(11) 0.00821(12) Cu2 0.01612(15) 0.01345(16) 0.01206(15) 0.00223(12) 0.00108(11) 0.00856(12) N1 0.0150(10) 0.0122(10) 0.0144(10) 0.0036(8) 0.0047(8) 0.0069(8) N2 0.0158(10) 0.0121(10) 0.0122(10) 0.0045(8) 0.0036(8) 0.0064(8) N3 0.0141(10) 0.0112(10) 0.0150(10) 0.0049(8) 0.0065(8) 0.0048(8) N4 0.0157(10) 0.0166(11) 0.0159(10) 0.0070(8) 0.0065(8) 0.0084(8) N5 0.0106(9) 0.0125(10) 0.0165(10) 0.0062(8) 0.0028(8) 0.0034(8) N6 0.0112(9) 0.0143(10) 0.0165(10) 0.0053(8) 0.0049(8) 0.0057(8) O30 0.0149(8) 0.0156(9) 0.0181(9) 0.0063(7) 0.0059(7) 0.0073(7) O31 0.0245(10) 0.0183(9) 0.0184(9) 0.0049(8) 0.0039(7) 0.0064(8) C30 0.0149(12) 0.0168(13) 0.0167(12) 0.0098(10) 0.0015(10) 0.0084(10) C31 0.0195(13) 0.0253(15) 0.0347(16) 0.0103(12) 0.0117(12) 0.0056(12) O40 0.0123(8) 0.0156(9) 0.0179(8) 0.0047(7) 0.0045(7) 0.0062(7) O41 0.0181(9) 0.0213(10) 0.0199(9) 0.0025(7) 0.0063(7) 0.0090(8) C40 0.0166(12) 0.0173(13) 0.0133(12) 0.0062(10) 0.0041(10) 0.0066(10) C41 0.0163(13) 0.0238(14) 0.0276(14) 0.0021(11) 0.0060(11) 0.0063(11) O50 0.0163(9) 0.0151(9) 0.0163(9) 0.0041(7) 0.0031(7) 0.0070(8) O60 0.0180(10) 0.0175(10) 0.0243(10) 0.0091(8) 0.0087(8) 0.0099(8) C3 0.0101(11) 0.0114(12) 0.0134(11) 0.0055(9) 0.0026(9) 0.0017(9) C4 0.0131(11) 0.0138(12) 0.0118(11) 0.0044(9) 0.0048(9) 0.0021(9) C5 0.0125(11) 0.0123(12) 0.0121(11) 0.0036(9) 0.0053(9) 0.0026(9) C6 0.0139(11) 0.0120(12) 0.0144(12) 0.0023(9) 0.0070(9) 0.0019(9) C8 0.0202(12) 0.0149(12) 0.0176(12) 0.0046(10) 0.0090(10) 0.0097(10) C9 0.0242(13) 0.0120(12) 0.0214(13) 0.0050(10) 0.0083(11) 0.0074(10) C10 0.0150(12) 0.0166(13) 0.0213(13) 0.0089(10) 0.0093(10) 0.0063(10) C11 0.0225(13) 0.0186(13) 0.0266(14) 0.0129(11) 0.0110(11) 0.0114(11) C12 0.0210(13) 0.0282(15) 0.0251(14) 0.0165(12) 0.0081(11) 0.0105(12) C13 0.0252(14) 0.0261(15) 0.0158(12) 0.0081(11) 0.0048(11) 0.0102(12) C14 0.0233(13) 0.0184(13) 0.0191(13) 0.0066(11) 0.0059(11) 0.0102(11) C15 0.0116(11) 0.0170(12) 0.0129(11) 0.0079(10) 0.0036(9) 0.0037(10) C17 0.0123(11) 0.0165(13) 0.0184(12) 0.0065(10) 0.0023(10) 0.0073(10) C18 0.0176(12) 0.0142(12) 0.0191(12) 0.0083(10) 0.0049(10) 0.0088(10) C19 0.0111(11) 0.0131(12) 0.0186(12) 0.0064(10) 0.0049(9) 0.0037(9) C20 0.0210(13) 0.0145(13) 0.0244(13) 0.0071(11) 0.0062(11) 0.0088(11) C21 0.0241(14) 0.0168(13) 0.0262(14) 0.0022(11) 0.0101(11) 0.0105(11) C22 0.0174(12) 0.0204(13) 0.0153(12) 0.0030(10) 0.0062(10) 0.0057(10) C23 0.0143(12) 0.0154(12) 0.0163(12) 0.0056(10) 0.0045(10) 0.0051(10) O70 0.0174(9) 0.0377(12) 0.0275(10) 0.0124(9) 0.0079(8) 0.0090(8) O71 0.0205(11) 0.113(2) 0.0800(19) 0.0791(19) 0.0011(12) -0.0005(13) C70 0.0218(13) 0.0136(13) 0.0202(13) 0.0029(10) 0.0055(11) 0.0071(11) C71 0.0211(14) 0.0255(15) 0.0272(14) 0.0081(12) 0.0073(11) 0.0086(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.0067(19) . ? Cu1 N3 2.0068(19) . ? Cu1 N4 2.0176(19) . ? Cu1 O30 2.0686(15) . ? Cu1 O40 2.0897(16) . ? Cu2 O50 1.9821(17) . ? Cu2 N5 2.0082(19) . ? Cu2 N2 2.0214(19) . ? Cu2 N6 2.0307(19) . ? Cu2 O60 2.3216(17) . ? Cu2 O70 2.5759(18) . ? N1 N2 1.334(3) . ? N1 C5 1.360(3) . ? N2 C3 1.358(3) . ? N3 C6 1.276(3) . ? N3 C8 1.454(3) . ? N4 C14 1.347(3) . ? N4 C10 1.350(3) . ? N5 C15 1.277(3) . ? N5 C17 1.459(3) . ? N6 C23 1.350(3) . ? N6 C19 1.352(3) . ? O30 C30 1.294(3) . ? O31 C30 1.232(3) . ? C30 C31 1.519(3) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? O40 C40 1.290(3) . ? O41 C40 1.244(3) . ? C40 C41 1.515(3) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? O50 H50 0.840(19) . ? O50 H51 0.815(19) . ? O60 H60 0.819(19) . ? O60 H61 0.822(19) . ? C3 C4 1.392(3) . ? C3 C15 1.454(3) . ? C4 C5 1.390(3) . ? C4 H4 0.9500 . ? C5 C6 1.453(3) . ? C6 H6 0.9500 . ? C8 C9 1.524(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.500(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.393(3) . ? C11 C12 1.382(4) . ? C11 H11 0.9500 . ? C12 C13 1.387(4) . ? C12 H12 0.9500 . ? C13 C14 1.376(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C17 C18 1.524(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.502(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.392(3) . ? C20 C21 1.379(3) . ? C20 H20 0.9500 . ? C21 C22 1.386(4) . ? C21 H21 0.9500 . ? C22 C23 1.379(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? O70 C70 1.256(3) . ? O71 C70 1.214(3) . ? C70 C71 1.533(3) . ? C71 H71A 0.9800 . ? C71 H71B 0.9800 . ? C71 H71C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 79.77(8) . . ? N1 Cu1 N4 171.48(8) . . ? N3 Cu1 N4 92.85(8) . . ? N1 Cu1 O30 91.82(7) . . ? N3 Cu1 O30 134.79(7) . . ? N4 Cu1 O30 90.38(7) . . ? N1 Cu1 O40 94.04(7) . . ? N3 Cu1 O40 129.01(7) . . ? N4 Cu1 O40 93.93(7) . . ? O30 Cu1 O40 95.64(6) . . ? O50 Cu2 N5 163.81(7) . . ? O50 Cu2 N2 97.43(7) . . ? N5 Cu2 N2 80.10(8) . . ? O50 Cu2 N6 90.86(7) . . ? N5 Cu2 N6 92.22(8) . . ? N2 Cu2 N6 171.65(8) . . ? O50 Cu2 O60 88.05(7) . . ? N5 Cu2 O60 107.87(7) . . ? N2 Cu2 O60 89.97(7) . . ? N6 Cu2 O60 89.27(7) . . ? O50 Cu2 O70 82.28(6) . . ? N5 Cu2 O70 81.83(7) . . ? N2 Cu2 O70 92.15(7) . . ? N6 Cu2 O70 89.99(7) . . ? O60 Cu2 O70 170.29(6) . . ? N2 N1 C5 108.25(18) . . ? N2 N1 Cu1 136.84(15) . . ? C5 N1 Cu1 112.07(15) . . ? N1 N2 C3 107.96(18) . . ? N1 N2 Cu2 139.38(15) . . ? C3 N2 Cu2 111.95(15) . . ? C6 N3 C8 122.3(2) . . ? C6 N3 Cu1 115.23(16) . . ? C8 N3 Cu1 122.21(14) . . ? C14 N4 C10 118.3(2) . . ? C14 N4 Cu1 115.42(16) . . ? C10 N4 Cu1 126.24(16) . . ? C15 N5 C17 120.9(2) . . ? C15 N5 Cu2 114.50(16) . . ? C17 N5 Cu2 123.79(15) . . ? C23 N6 C19 118.6(2) . . ? C23 N6 Cu2 116.58(15) . . ? C19 N6 Cu2 124.76(15) . . ? C30 O30 Cu1 110.88(14) . . ? O31 C30 O30 124.2(2) . . ? O31 C30 C31 120.4(2) . . ? O30 C30 C31 115.4(2) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C40 O40 Cu1 117.02(14) . . ? O41 C40 O40 123.6(2) . . ? O41 C40 C41 119.8(2) . . ? O40 C40 C41 116.6(2) . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? Cu2 O50 H50 103(2) . . ? Cu2 O50 H51 114(3) . . ? H50 O50 H51 110(3) . . ? Cu2 O60 H60 106(2) . . ? Cu2 O60 H61 123(2) . . ? H60 O60 H61 106(3) . . ? N2 C3 C4 110.4(2) . . ? N2 C3 C15 114.6(2) . . ? C4 C3 C15 134.9(2) . . ? C5 C4 C3 103.1(2) . . ? C5 C4 H4 128.4 . . ? C3 C4 H4 128.4 . . ? N1 C5 C4 110.2(2) . . ? N1 C5 C6 114.3(2) . . ? C4 C5 C6 135.5(2) . . ? N3 C6 C5 115.8(2) . . ? N3 C6 H6 122.1 . . ? C5 C6 H6 122.1 . . ? N3 C8 C9 107.72(18) . . ? N3 C8 H8A 110.2 . . ? C9 C8 H8A 110.2 . . ? N3 C8 H8B 110.2 . . ? C9 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? C10 C9 C8 114.8(2) . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.5 . . ? N4 C10 C11 121.1(2) . . ? N4 C10 C9 118.5(2) . . ? C11 C10 C9 120.3(2) . . ? C12 C11 C10 119.9(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 118.8(2) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C14 C13 C12 118.5(2) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? N4 C14 C13 123.3(2) . . ? N4 C14 H14 118.3 . . ? C13 C14 H14 118.3 . . ? N5 C15 C3 116.6(2) . . ? N5 C15 H15 121.7 . . ? C3 C15 H15 121.7 . . ? N5 C17 C18 108.38(18) . . ? N5 C17 H17A 110.0 . . ? C18 C17 H17A 110.0 . . ? N5 C17 H17B 110.0 . . ? C18 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? C19 C18 C17 113.87(19) . . ? C19 C18 H18A 108.8 . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18B 108.8 . . ? C17 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? N6 C19 C20 120.8(2) . . ? N6 C19 C18 118.5(2) . . ? C20 C19 C18 120.7(2) . . ? C21 C20 C19 120.1(2) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 119.1(2) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C23 C22 C21 118.4(2) . . ? C23 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? N6 C23 C22 123.1(2) . . ? N6 C23 H23 118.5 . . ? C22 C23 H23 118.5 . . ? C70 O70 Cu2 123.53(16) . . ? O71 C70 O70 125.1(2) . . ? O71 C70 C71 117.7(2) . . ? O70 C70 C71 117.2(2) . . ? C70 C71 H71A 109.5 . . ? C70 C71 H71B 109.5 . . ? H71A C71 H71B 109.5 . . ? C70 C71 H71C 109.5 . . ? H71A C71 H71C 109.5 . . ? H71B C71 H71C 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 N3 Cu1 N1 N2 173.0(2) . . . . ? N4 Cu1 N1 N2 142.6(5) . . . . ? O30 Cu1 N1 N2 37.7(2) . . . . ? O40 Cu1 N1 N2 -58.1(2) . . . . ? N3 Cu1 N1 C5 15.14(15) . . . . ? N4 Cu1 N1 C5 -15.2(6) . . . . ? O30 Cu1 N1 C5 -120.13(15) . . . . ? O40 Cu1 N1 C5 144.08(15) . . . . ? C5 N1 N2 C3 0.8(2) . . . . ? Cu1 N1 N2 C3 -157.61(17) . . . . ? C5 N1 N2 Cu2 -168.16(17) . . . . ? Cu1 N1 N2 Cu2 33.4(3) . . . . ? O50 Cu2 N2 N1 17.5(2) . . . . ? N5 Cu2 N2 N1 -178.7(2) . . . . ? N6 Cu2 N2 N1 -155.2(4) . . . . ? O60 Cu2 N2 N1 -70.5(2) . . . . ? O70 Cu2 N2 N1 100.0(2) . . . . ? O50 Cu2 N2 C3 -151.17(15) . . . . ? N5 Cu2 N2 C3 12.65(14) . . . . ? N6 Cu2 N2 C3 36.1(6) . . . . ? O60 Cu2 N2 C3 120.80(15) . . . . ? O70 Cu2 N2 C3 -68.68(15) . . . . ? N1 Cu1 N3 C6 -11.92(16) . . . . ? N4 Cu1 N3 C6 163.78(17) . . . . ? O30 Cu1 N3 C6 70.40(19) . . . . ? O40 Cu1 N3 C6 -98.83(17) . . . . ? N1 Cu1 N3 C8 173.48(18) . . . . ? N4 Cu1 N3 C8 -10.82(17) . . . . ? O30 Cu1 N3 C8 -104.19(17) . . . . ? O40 Cu1 N3 C8 86.58(18) . . . . ? N1 Cu1 N4 C14 -164.1(5) . . . . ? N3 Cu1 N4 C14 166.03(17) . . . . ? O30 Cu1 N4 C14 -59.09(17) . . . . ? O40 Cu1 N4 C14 36.60(17) . . . . ? N1 Cu1 N4 C10 15.4(6) . . . . ? N3 Cu1 N4 C10 -14.46(19) . . . . ? O30 Cu1 N4 C10 120.43(19) . . . . ? O40 Cu1 N4 C10 -143.89(18) . . . . ? O50 Cu2 N5 C15 69.6(3) . . . . ? N2 Cu2 N5 C15 -12.87(16) . . . . ? N6 Cu2 N5 C15 170.44(16) . . . . ? O60 Cu2 N5 C15 -99.61(16) . . . . ? O70 Cu2 N5 C15 80.77(16) . . . . ? O50 Cu2 N5 C17 -99.9(3) . . . . ? N2 Cu2 N5 C17 177.60(18) . . . . ? N6 Cu2 N5 C17 0.91(17) . . . . ? O60 Cu2 N5 C17 90.86(17) . . . . ? O70 Cu2 N5 C17 -88.76(17) . . . . ? O50 Cu2 N6 C23 -40.50(17) . . . . ? N5 Cu2 N6 C23 155.40(16) . . . . ? N2 Cu2 N6 C23 132.3(5) . . . . ? O60 Cu2 N6 C23 47.54(16) . . . . ? O70 Cu2 N6 C23 -122.78(16) . . . . ? O50 Cu2 N6 C19 141.61(18) . . . . ? N5 Cu2 N6 C19 -22.49(18) . . . . ? N2 Cu2 N6 C19 -45.6(6) . . . . ? O60 Cu2 N6 C19 -130.34(18) . . . . ? O70 Cu2 N6 C19 59.34(18) . . . . ? N1 Cu1 O30 C30 88.99(15) . . . . ? N3 Cu1 O30 C30 11.63(19) . . . . ? N4 Cu1 O30 C30 -82.78(15) . . . . ? O40 Cu1 O30 C30 -176.76(14) . . . . ? Cu1 O30 C30 O31 -5.9(3) . . . . ? Cu1 O30 C30 C31 173.29(16) . . . . ? N1 Cu1 O40 C40 -100.70(16) . . . . ? N3 Cu1 O40 C40 -20.59(19) . . . . ? N4 Cu1 O40 C40 76.29(16) . . . . ? O30 Cu1 O40 C40 167.06(15) . . . . ? Cu1 O40 C40 O41 -8.2(3) . . . . ? Cu1 O40 C40 C41 170.91(16) . . . . ? N1 N2 C3 C4 -1.1(2) . . . . ? Cu2 N2 C3 C4 171.15(14) . . . . ? N1 N2 C3 C15 176.71(18) . . . . ? Cu2 N2 C3 C15 -11.0(2) . . . . ? N2 C3 C4 C5 1.0(2) . . . . ? C15 C3 C4 C5 -176.3(2) . . . . ? N2 N1 C5 C4 -0.2(2) . . . . ? Cu1 N1 C5 C4 164.04(14) . . . . ? N2 N1 C5 C6 179.39(18) . . . . ? Cu1 N1 C5 C6 -16.4(2) . . . . ? C3 C4 C5 N1 -0.4(2) . . . . ? C3 C4 C5 C6 -179.9(2) . . . . ? C8 N3 C6 C5 -179.04(19) . . . . ? Cu1 N3 C6 C5 6.4(3) . . . . ? N1 C5 C6 N3 6.9(3) . . . . ? C4 C5 C6 N3 -173.6(2) . . . . ? C6 N3 C8 C9 -124.5(2) . . . . ? Cu1 N3 C8 C9 49.7(2) . . . . ? N3 C8 C9 C10 -74.1(3) . . . . ? C14 N4 C10 C11 -2.6(3) . . . . ? Cu1 N4 C10 C11 177.95(17) . . . . ? C14 N4 C10 C9 175.9(2) . . . . ? Cu1 N4 C10 C9 -3.6(3) . . . . ? C8 C9 C10 N4 51.1(3) . . . . ? C8 C9 C10 C11 -130.4(2) . . . . ? N4 C10 C11 C12 2.3(4) . . . . ? C9 C10 C11 C12 -176.1(2) . . . . ? C10 C11 C12 C13 -0.4(4) . . . . ? C11 C12 C13 C14 -1.2(4) . . . . ? C10 N4 C14 C13 0.9(4) . . . . ? Cu1 N4 C14 C13 -179.5(2) . . . . ? C12 C13 C14 N4 1.0(4) . . . . ? C17 N5 C15 C3 -179.53(19) . . . . ? Cu2 N5 C15 C3 10.6(2) . . . . ? N2 C3 C15 N5 0.5(3) . . . . ? C4 C3 C15 N5 177.6(2) . . . . ? C15 N5 C17 C18 -128.7(2) . . . . ? Cu2 N5 C17 C18 40.2(2) . . . . ? N5 C17 C18 C19 -73.4(2) . . . . ? C23 N6 C19 C20 0.7(3) . . . . ? Cu2 N6 C19 C20 178.50(17) . . . . ? C23 N6 C19 C18 -179.3(2) . . . . ? Cu2 N6 C19 C18 -1.4(3) . . . . ? C17 C18 C19 N6 54.5(3) . . . . ? C17 C18 C19 C20 -125.4(2) . . . . ? N6 C19 C20 C21 0.3(4) . . . . ? C18 C19 C20 C21 -179.8(2) . . . . ? C19 C20 C21 C22 -0.9(4) . . . . ? C20 C21 C22 C23 0.6(4) . . . . ? C19 N6 C23 C22 -1.0(3) . . . . ? Cu2 N6 C23 C22 -178.99(18) . . . . ? C21 C22 C23 N6 0.3(4) . . . . ? O50 Cu2 O70 C70 6.60(19) . . . . ? N5 Cu2 O70 C70 -170.3(2) . . . . ? N2 Cu2 O70 C70 -90.6(2) . . . . ? N6 Cu2 O70 C70 97.5(2) . . . . ? O60 Cu2 O70 C70 11.9(5) . . . . ? Cu2 O70 C70 O71 -4.6(4) . . . . ? Cu2 O70 C70 C71 174.73(15) . . . . ? 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 O60 H60 O30 0.819(19) 1.986(19) 2.804(2) 179(3) . O60 H61 O41 0.822(19) 1.926(19) 2.748(2) 178(3) 1_455 O50 H50 O70 0.840(19) 2.52(3) 3.032(2) 121(3) . O50 H50 O71 0.840(19) 1.74(2) 2.577(3) 179(4) . O50 H51 O40 0.815(19) 1.88(2) 2.685(2) 167(4) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.634 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.071 # Attachment 'an118a.cif' data_an118a _database_code_depnum_ccdc_archive 'CCDC 623301' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H34 Cu2 N8 O7' _chemical_formula_weight 649.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 7.6521(5) _cell_length_b 29.525(2) _cell_length_c 12.4181(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.076(2) _cell_angle_gamma 90.00 _cell_volume 2789.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 1.580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SCALE (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(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 Kappa Apex II area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 52536 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.42 _reflns_number_total 5741 _reflns_number_gt 5422 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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. All non-H anis. All H calc and ride on attached atoms including OH's on water and methanol in lattice H51, H61, H70a and H70b. ; _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^)+(0.0263P)^2^+18.0043P] 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 5741 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 1.244 _refine_ls_restrained_S_all 1.244 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.87609(7) 0.134335(19) 0.98405(4) 0.01812(15) Uani 1 1 d . . . Cu2 Cu 1.03013(7) 0.264267(19) 1.00968(4) 0.01478(14) Uani 1 1 d . . . N1 N 1.0845(5) 0.16474(14) 1.0607(3) 0.0178(8) Uani 1 1 d . . . N2 N 1.1344(5) 0.20722(13) 1.0688(3) 0.0163(8) Uani 1 1 d . . . N3 N 0.9600(6) 0.08533(14) 1.0885(3) 0.0254(9) Uani 1 1 d . . . N4 N 0.6232(5) 0.11362(14) 0.9716(3) 0.0231(9) Uani 1 1 d . . . N5 N 0.7563(5) 0.19205(13) 0.9454(3) 0.0159(7) Uani 1 1 d . . . N6 N 0.8071(5) 0.23453(13) 0.9566(3) 0.0164(7) Uani 1 1 d . . . N7 N 0.8690(5) 0.31762(14) 1.0115(3) 0.0190(8) Uani 1 1 d . . . N8 N 1.2060(5) 0.28919(14) 1.1260(3) 0.0205(8) Uani 1 1 d . . . C30 C 0.9808(7) 0.07943(17) 0.8029(4) 0.0279(11) Uani 1 1 d . . . C31 C 1.0957(10) 0.0671(2) 0.7157(5) 0.0450(16) Uani 1 1 d . . . H31A H 1.0631 0.0370 0.6871 0.054 Uiso 1 1 calc R . . H31B H 1.2192 0.0669 0.7464 0.054 Uiso 1 1 calc R . . H31C H 1.0796 0.0894 0.6571 0.054 Uiso 1 1 calc R . . O30 O 1.0155(5) 0.11541(12) 0.8530(3) 0.0274(8) Uani 1 1 d . . . O31 O 0.8572(6) 0.05372(15) 0.8203(4) 0.0468(11) Uani 1 1 d . . . C40 C 1.2033(6) 0.30401(17) 0.8293(4) 0.0206(10) Uani 1 1 d . . . C41 C 1.2745(7) 0.30320(19) 0.7199(4) 0.0286(11) Uani 1 1 d . . . H41A H 1.2865 0.3343 0.6940 0.034 Uiso 1 1 calc R . . H41B H 1.1933 0.2864 0.6680 0.034 Uiso 1 1 calc R . . H41C H 1.3897 0.2883 0.7268 0.034 Uiso 1 1 calc R . . O40 O 1.1260(4) 0.26843(11) 0.8562(2) 0.0185(7) Uani 1 1 d . . . O41 O 1.2267(6) 0.33805(14) 0.8872(3) 0.0410(10) Uani 1 1 d . . . C3 C 1.2488(6) 0.21210(17) 1.1594(4) 0.0199(9) Uani 1 1 d . . . C4 C 1.2746(6) 0.17014(18) 1.2102(4) 0.0233(10) Uani 1 1 d . . . H4 H 1.3494 0.1631 1.2740 0.028 Uiso 1 1 calc R . . C5 C 1.1652(6) 0.14106(17) 1.1457(4) 0.0224(10) Uani 1 1 d . . . C6 C 1.0947(7) 0.09533(18) 1.1548(4) 0.0265(11) Uani 1 1 d . . . H6 H 1.1456 0.0742 1.2068 0.032 Uiso 1 1 calc R . . C8 C 0.8689(8) 0.04209(18) 1.0933(5) 0.0334(12) Uani 1 1 d . . . H8A H 0.9187 0.0251 1.1581 0.040 Uiso 1 1 calc R . . H8B H 0.8871 0.0239 1.0285 0.040 Uiso 1 1 calc R . . C9 C 0.6728(8) 0.04914(19) 1.0983(5) 0.0355(13) Uani 1 1 d . . . H9A H 0.6570 0.0708 1.1575 0.043 Uiso 1 1 calc R . . H9B H 0.6203 0.0199 1.1172 0.043 Uiso 1 1 calc R . . C10 C 0.5723(7) 0.06685(19) 0.9942(5) 0.0324(12) Uani 1 1 d . . . H10A H 0.5963 0.0471 0.9330 0.039 Uiso 1 1 calc R . . H10B H 0.4445 0.0657 1.0008 0.039 Uiso 1 1 calc R . . C12 C 0.5099(6) 0.14488(17) 0.9521(4) 0.0227(10) Uani 1 1 d . . . H12 H 0.3874 0.1387 0.9447 0.027 Uiso 1 1 calc R . . C13 C 0.5776(6) 0.19061(17) 0.9418(4) 0.0188(9) Uani 1 1 d . . . C14 C 0.5134(6) 0.23436(17) 0.9505(4) 0.0205(10) Uani 1 1 d . . . H14 H 0.3945 0.2438 0.9495 0.025 Uiso 1 1 calc R . . C15 C 0.6640(5) 0.26119(16) 0.9610(3) 0.0171(9) Uani 1 1 d . . . C16 C 0.7050(6) 0.30807(17) 0.9890(4) 0.0205(9) Uani 1 1 d . . . H16 H 0.6159 0.3304 0.9907 0.025 Uiso 1 1 calc R . . C18 C 0.9284(7) 0.36272(17) 1.0471(4) 0.0242(10) Uani 1 1 d . . . H18A H 0.8252 0.3820 1.0560 0.029 Uiso 1 1 calc R . . H18B H 0.9941 0.3767 0.9911 0.029 Uiso 1 1 calc R . . C19 C 1.0467(7) 0.36041(18) 1.1545(4) 0.0268(11) Uani 1 1 d . . . H19A H 0.9833 0.3438 1.2077 0.032 Uiso 1 1 calc R . . H19B H 1.0671 0.3916 1.1822 0.032 Uiso 1 1 calc R . . C20 C 1.2256(6) 0.33758(17) 1.1484(4) 0.0243(10) Uani 1 1 d . . . H20A H 1.2856 0.3521 1.0905 0.029 Uiso 1 1 calc R . . H20B H 1.2997 0.3420 1.2179 0.029 Uiso 1 1 calc R . . C22 C 1.2897(6) 0.25933(18) 1.1857(4) 0.0226(10) Uani 1 1 d . . . H22 H 1.3741 0.2675 1.2441 0.027 Uiso 1 1 calc R . . C50 C 0.5838(13) -0.0087(3) 0.6377(8) 0.080(3) Uani 1 1 d . . . H50A H 0.5085 0.0182 0.6367 0.096 Uiso 1 1 calc R . . H50B H 0.5122 -0.0352 0.6147 0.096 Uiso 1 1 calc R . . H50C H 0.6737 -0.0042 0.5881 0.096 Uiso 1 1 calc R . . O51 O 0.6638(8) -0.01555(17) 0.7410(5) 0.0687(17) Uani 1 1 d . . . H51 H 0.7252 0.0068 0.7646 0.082 Uiso 1 1 d . . . C60 C 1.4137(12) 0.4407(2) 0.9152(7) 0.061(2) Uani 1 1 d . . . H60A H 1.3476 0.4389 0.9784 0.073 Uiso 1 1 calc R . . H60B H 1.3348 0.4501 0.8517 0.073 Uiso 1 1 calc R . . H60C H 1.5084 0.4630 0.9289 0.073 Uiso 1 1 calc R . . O61 O 1.4843(6) 0.39923(16) 0.8962(5) 0.0549(13) Uani 1 1 d . . . H61 H 1.3922 0.3847 0.8751 0.066 Uiso 1 1 d . . . O70 O 1.1883(5) 0.18450(13) 0.7507(3) 0.0328(9) Uani 1 1 d . . . H70A H 1.1766 0.2096 0.7808 0.039 Uiso 1 1 d . . . H70B H 1.1499 0.1603 0.7744 0.039 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0165(3) 0.0226(3) 0.0158(3) -0.0003(2) 0.0038(2) 0.0005(2) Cu2 0.0100(2) 0.0238(3) 0.0106(2) -0.0007(2) 0.00143(18) 0.0002(2) N1 0.0142(17) 0.028(2) 0.0116(17) 0.0035(15) 0.0045(14) 0.0056(15) N2 0.0087(16) 0.028(2) 0.0131(17) 0.0008(15) 0.0033(13) 0.0017(15) N3 0.030(2) 0.023(2) 0.025(2) 0.0045(17) 0.0098(18) 0.0052(17) N4 0.022(2) 0.029(2) 0.019(2) -0.0041(17) 0.0051(16) -0.0033(17) N5 0.0122(17) 0.025(2) 0.0104(17) -0.0002(15) 0.0023(13) 0.0005(15) N6 0.0121(17) 0.025(2) 0.0123(17) 0.0011(15) 0.0025(14) 0.0005(15) N7 0.0193(19) 0.025(2) 0.0137(18) -0.0002(15) 0.0065(15) 0.0016(16) N8 0.0144(18) 0.035(2) 0.0128(18) -0.0026(16) 0.0026(14) -0.0038(16) C30 0.041(3) 0.023(3) 0.019(2) 0.005(2) 0.004(2) 0.009(2) C31 0.072(5) 0.033(3) 0.034(3) -0.008(3) 0.023(3) 0.004(3) O30 0.035(2) 0.0279(19) 0.0210(17) -0.0001(15) 0.0097(15) 0.0073(15) O31 0.055(3) 0.044(3) 0.043(3) -0.012(2) 0.010(2) -0.010(2) C40 0.014(2) 0.033(3) 0.015(2) 0.0038(19) 0.0021(17) 0.0016(19) C41 0.027(3) 0.040(3) 0.021(2) 0.002(2) 0.010(2) -0.007(2) O40 0.0105(14) 0.0318(18) 0.0136(15) 0.0008(13) 0.0028(11) 0.0004(13) O41 0.061(3) 0.035(2) 0.031(2) -0.0103(18) 0.023(2) -0.016(2) C3 0.0102(19) 0.037(3) 0.013(2) 0.0012(19) 0.0023(16) 0.0008(18) C4 0.015(2) 0.038(3) 0.018(2) 0.005(2) 0.0029(17) 0.0058(19) C5 0.020(2) 0.031(3) 0.017(2) 0.0065(19) 0.0043(18) 0.0081(19) C6 0.032(3) 0.028(3) 0.020(2) 0.005(2) 0.005(2) 0.011(2) C8 0.041(3) 0.025(3) 0.035(3) 0.004(2) 0.007(2) 0.000(2) C9 0.044(3) 0.026(3) 0.039(3) 0.003(2) 0.015(3) -0.009(2) C10 0.030(3) 0.030(3) 0.039(3) -0.005(2) 0.010(2) -0.008(2) C12 0.018(2) 0.035(3) 0.015(2) -0.0046(19) 0.0032(17) -0.006(2) C13 0.011(2) 0.033(3) 0.013(2) -0.0028(18) 0.0009(16) -0.0010(18) C14 0.011(2) 0.037(3) 0.013(2) 0.0004(19) 0.0006(16) 0.0027(19) C15 0.0115(19) 0.030(2) 0.0096(19) 0.0022(17) -0.0013(15) 0.0056(18) C16 0.018(2) 0.029(3) 0.015(2) 0.0020(18) 0.0035(17) 0.0060(19) C18 0.027(2) 0.024(2) 0.023(2) -0.0005(19) 0.007(2) 0.000(2) C19 0.030(3) 0.029(3) 0.023(2) -0.005(2) 0.007(2) -0.005(2) C20 0.023(2) 0.033(3) 0.017(2) -0.004(2) 0.0016(18) -0.009(2) C22 0.012(2) 0.038(3) 0.018(2) -0.002(2) 0.0036(17) -0.0036(19) C50 0.077(6) 0.078(6) 0.079(6) -0.005(5) -0.018(5) -0.011(5) O51 0.074(4) 0.042(3) 0.081(4) 0.006(3) -0.034(3) -0.007(3) C60 0.083(6) 0.033(4) 0.064(5) 0.002(3) -0.002(4) -0.001(4) O61 0.044(3) 0.043(3) 0.078(4) -0.004(2) 0.005(2) -0.006(2) O70 0.030(2) 0.035(2) 0.036(2) -0.0099(17) 0.0139(16) -0.0027(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 Cu1 N5 1.970(4) . ? Cu1 N1 1.983(4) . ? Cu1 N3 2.003(4) . ? Cu1 N4 2.020(4) . ? Cu1 O30 2.113(3) . ? Cu2 N6 1.970(4) . ? Cu2 N2 1.972(4) . ? Cu2 N7 2.002(4) . ? Cu2 N8 2.007(4) . ? Cu2 O40 2.117(3) . ? N1 N2 1.312(6) . ? N1 C5 1.359(6) . ? N2 C3 1.358(6) . ? N3 C6 1.284(7) . ? N3 C8 1.459(7) . ? N4 C12 1.272(7) . ? N4 C10 1.470(7) . ? N5 N6 1.316(5) . ? N5 C13 1.364(5) . ? N6 C15 1.355(6) . ? N7 C16 1.287(6) . ? N7 C18 1.460(6) . ? N8 C22 1.279(6) . ? N8 C20 1.460(6) . ? C30 O30 1.245(6) . ? C30 O31 1.249(7) . ? C30 C31 1.510(8) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C40 O41 1.238(6) . ? C40 O40 1.268(6) . ? C40 C41 1.517(6) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C3 C4 1.395(7) . ? C3 C22 1.459(7) . ? C4 C5 1.392(7) . ? C4 H4 0.9500 . ? C5 C6 1.463(7) . ? C6 H6 0.9500 . ? C8 C9 1.522(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.526(8) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C12 C13 1.457(7) . ? C12 H12 0.9500 . ? C13 C14 1.390(7) . ? C14 C15 1.393(6) . ? C14 H14 0.9500 . ? C15 C16 1.453(7) . ? C16 H16 0.9500 . ? C18 C19 1.533(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.535(7) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C22 H22 0.9500 . ? C50 O51 1.377(10) . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? O51 H51 0.8449 . ? C60 O61 1.370(8) . ? C60 H60A 0.9800 . ? C60 H60B 0.9800 . ? C60 H60C 0.9800 . ? O61 H61 0.8427 . ? O70 H70A 0.8390 . ? O70 H70B 0.8392 . ? 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 93.15(16) . . ? N5 Cu1 N3 153.07(16) . . ? N1 Cu1 N3 80.21(17) . . ? N5 Cu1 N4 79.98(16) . . ? N1 Cu1 N4 152.73(16) . . ? N3 Cu1 N4 93.98(18) . . ? N5 Cu1 O30 107.53(14) . . ? N1 Cu1 O30 92.49(15) . . ? N3 Cu1 O30 98.86(15) . . ? N4 Cu1 O30 114.76(16) . . ? N6 Cu2 N2 92.64(16) . . ? N6 Cu2 N7 80.90(16) . . ? N2 Cu2 N7 153.29(15) . . ? N6 Cu2 N8 153.59(15) . . ? N2 Cu2 N8 80.28(16) . . ? N7 Cu2 N8 94.02(17) . . ? N6 Cu2 O40 95.43(14) . . ? N2 Cu2 O40 102.68(14) . . ? N7 Cu2 O40 103.71(14) . . ? N8 Cu2 O40 110.92(14) . . ? N2 N1 C5 109.1(4) . . ? N2 N1 Cu1 133.0(3) . . ? C5 N1 Cu1 114.6(3) . . ? N1 N2 C3 108.8(4) . . ? N1 N2 Cu2 133.2(3) . . ? C3 N2 Cu2 114.7(3) . . ? C6 N3 C8 122.0(5) . . ? C6 N3 Cu1 115.5(4) . . ? C8 N3 Cu1 122.5(4) . . ? C12 N4 C10 121.9(4) . . ? C12 N4 Cu1 115.0(3) . . ? C10 N4 Cu1 122.8(3) . . ? N6 N5 C13 108.5(4) . . ? N6 N5 Cu1 132.4(3) . . ? C13 N5 Cu1 114.8(3) . . ? N5 N6 C15 109.1(4) . . ? N5 N6 Cu2 134.1(3) . . ? C15 N6 Cu2 113.8(3) . . ? C16 N7 C18 122.0(4) . . ? C16 N7 Cu2 114.3(3) . . ? C18 N7 Cu2 123.3(3) . . ? C22 N8 C20 122.0(4) . . ? C22 N8 Cu2 114.9(3) . . ? C20 N8 Cu2 122.9(3) . . ? O30 C30 O31 123.9(5) . . ? O30 C30 C31 117.0(5) . . ? O31 C30 C31 119.1(5) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 O30 Cu1 120.8(3) . . ? O41 C40 O40 124.2(4) . . ? O41 C40 C41 119.3(4) . . ? O40 C40 C41 116.4(4) . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C40 O40 Cu2 120.1(3) . . ? N2 C3 C4 109.2(4) . . ? N2 C3 C22 113.0(4) . . ? C4 C3 C22 137.0(4) . . ? C5 C4 C3 103.9(4) . . ? C5 C4 H4 128.1 . . ? C3 C4 H4 128.1 . . ? N1 C5 C4 109.0(4) . . ? N1 C5 C6 113.2(4) . . ? C4 C5 C6 136.8(4) . . ? N3 C6 C5 116.1(4) . . ? N3 C6 H6 121.9 . . ? C5 C6 H6 121.9 . . ? N3 C8 C9 111.1(4) . . ? N3 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? N3 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C10 115.0(5) . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? N4 C10 C9 111.3(4) . . ? N4 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? N4 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? N4 C12 C13 116.6(4) . . ? N4 C12 H12 121.7 . . ? C13 C12 H12 121.7 . . ? N5 C13 C14 109.2(4) . . ? N5 C13 C12 113.0(4) . . ? C14 C13 C12 136.3(4) . . ? C13 C14 C15 103.9(4) . . ? C13 C14 H14 128.1 . . ? C15 C14 H14 128.1 . . ? N6 C15 C14 109.3(4) . . ? N6 C15 C16 114.1(4) . . ? C14 C15 C16 136.0(4) . . ? N7 C16 C15 116.2(4) . . ? N7 C16 H16 121.9 . . ? C15 C16 H16 121.9 . . ? N7 C18 C19 111.0(4) . . ? N7 C18 H18A 109.4 . . ? C19 C18 H18A 109.4 . . ? N7 C18 H18B 109.4 . . ? C19 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C18 C19 C20 115.1(4) . . ? C18 C19 H19A 108.5 . . ? C20 C19 H19A 108.5 . . ? C18 C19 H19B 108.5 . . ? C20 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? N8 C20 C19 111.4(4) . . ? N8 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? N8 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? N8 C22 C3 116.6(4) . . ? N8 C22 H22 121.7 . . ? C3 C22 H22 121.7 . . ? O51 C50 H50A 109.5 . . ? O51 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? O51 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C50 O51 H51 112.6 . . ? O61 C60 H60A 109.5 . . ? O61 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? O61 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? C60 O61 H61 100.2 . . ? H70A O70 H70B 122.6 . . ? 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 N2 -8.6(4) . . . . ? N3 Cu1 N1 N2 -162.3(4) . . . . ? N4 Cu1 N1 N2 -82.8(5) . . . . ? O30 Cu1 N1 N2 99.1(4) . . . . ? N5 Cu1 N1 C5 148.3(3) . . . . ? N3 Cu1 N1 C5 -5.4(3) . . . . ? N4 Cu1 N1 C5 74.2(5) . . . . ? O30 Cu1 N1 C5 -104.0(3) . . . . ? C5 N1 N2 C3 0.0(5) . . . . ? Cu1 N1 N2 C3 157.8(3) . . . . ? C5 N1 N2 Cu2 -157.7(3) . . . . ? Cu1 N1 N2 Cu2 0.2(6) . . . . ? N6 Cu2 N2 N1 9.2(4) . . . . ? N7 Cu2 N2 N1 84.1(5) . . . . ? N8 Cu2 N2 N1 163.6(4) . . . . ? O40 Cu2 N2 N1 -86.9(4) . . . . ? N6 Cu2 N2 C3 -147.5(3) . . . . ? N7 Cu2 N2 C3 -72.6(5) . . . . ? N8 Cu2 N2 C3 6.9(3) . . . . ? O40 Cu2 N2 C3 116.4(3) . . . . ? N5 Cu1 N3 C6 -75.2(5) . . . . ? N1 Cu1 N3 C6 2.3(4) . . . . ? N4 Cu1 N3 C6 -150.8(4) . . . . ? O30 Cu1 N3 C6 93.3(4) . . . . ? N5 Cu1 N3 C8 101.5(5) . . . . ? N1 Cu1 N3 C8 179.0(4) . . . . ? N4 Cu1 N3 C8 25.8(4) . . . . ? O30 Cu1 N3 C8 -90.0(4) . . . . ? N5 Cu1 N4 C12 -3.5(3) . . . . ? N1 Cu1 N4 C12 73.8(5) . . . . ? N3 Cu1 N4 C12 150.1(4) . . . . ? O30 Cu1 N4 C12 -108.3(3) . . . . ? N5 Cu1 N4 C10 -177.5(4) . . . . ? N1 Cu1 N4 C10 -100.3(5) . . . . ? N3 Cu1 N4 C10 -24.0(4) . . . . ? O30 Cu1 N4 C10 77.7(4) . . . . ? N1 Cu1 N5 N6 6.7(4) . . . . ? N3 Cu1 N5 N6 81.2(5) . . . . ? N4 Cu1 N5 N6 160.1(4) . . . . ? O30 Cu1 N5 N6 -86.9(4) . . . . ? N1 Cu1 N5 C13 -146.9(3) . . . . ? N3 Cu1 N5 C13 -72.5(5) . . . . ? N4 Cu1 N5 C13 6.5(3) . . . . ? O30 Cu1 N5 C13 119.5(3) . . . . ? C13 N5 N6 C15 0.4(5) . . . . ? Cu1 N5 N6 C15 -154.5(3) . . . . ? C13 N5 N6 Cu2 158.6(3) . . . . ? Cu1 N5 N6 Cu2 3.8(6) . . . . ? N2 Cu2 N6 N5 -11.3(4) . . . . ? N7 Cu2 N6 N5 -165.2(4) . . . . ? N8 Cu2 N6 N5 -84.6(5) . . . . ? O40 Cu2 N6 N5 91.7(4) . . . . ? N2 Cu2 N6 C15 146.2(3) . . . . ? N7 Cu2 N6 C15 -7.7(3) . . . . ? N8 Cu2 N6 C15 72.9(5) . . . . ? O40 Cu2 N6 C15 -110.8(3) . . . . ? N6 Cu2 N7 C16 5.8(3) . . . . ? N2 Cu2 N7 C16 -71.8(5) . . . . ? N8 Cu2 N7 C16 -148.1(3) . . . . ? O40 Cu2 N7 C16 99.2(3) . . . . ? N6 Cu2 N7 C18 179.2(4) . . . . ? N2 Cu2 N7 C18 101.6(5) . . . . ? N8 Cu2 N7 C18 25.3(4) . . . . ? O40 Cu2 N7 C18 -87.4(3) . . . . ? N6 Cu2 N8 C22 71.6(5) . . . . ? N2 Cu2 N8 C22 -4.5(3) . . . . ? N7 Cu2 N8 C22 149.2(3) . . . . ? O40 Cu2 N8 C22 -104.5(3) . . . . ? N6 Cu2 N8 C20 -102.6(5) . . . . ? N2 Cu2 N8 C20 -178.7(4) . . . . ? N7 Cu2 N8 C20 -25.0(4) . . . . ? O40 Cu2 N8 C20 81.4(4) . . . . ? O31 C30 O30 Cu1 4.8(7) . . . . ? C31 C30 O30 Cu1 -175.8(4) . . . . ? N5 Cu1 O30 C30 -118.7(4) . . . . ? N1 Cu1 O30 C30 147.2(4) . . . . ? N3 Cu1 O30 C30 66.7(4) . . . . ? N4 Cu1 O30 C30 -31.8(4) . . . . ? O41 C40 O40 Cu2 -0.8(6) . . . . ? C41 C40 O40 Cu2 177.4(3) . . . . ? N6 Cu2 O40 C40 138.6(3) . . . . ? N2 Cu2 O40 C40 -127.5(3) . . . . ? N7 Cu2 O40 C40 56.6(3) . . . . ? N8 Cu2 O40 C40 -43.2(4) . . . . ? N1 N2 C3 C4 1.1(5) . . . . ? Cu2 N2 C3 C4 163.3(3) . . . . ? N1 N2 C3 C22 -170.4(4) . . . . ? Cu2 N2 C3 C22 -8.1(5) . . . . ? N2 C3 C4 C5 -1.6(5) . . . . ? C22 C3 C4 C5 166.8(5) . . . . ? N2 N1 C5 C4 -1.0(5) . . . . ? Cu1 N1 C5 C4 -163.4(3) . . . . ? N2 N1 C5 C6 169.7(4) . . . . ? Cu1 N1 C5 C6 7.3(5) . . . . ? C3 C4 C5 N1 1.6(5) . . . . ? C3 C4 C5 C6 -165.9(5) . . . . ? C8 N3 C6 C5 -175.7(4) . . . . ? Cu1 N3 C6 C5 1.0(6) . . . . ? N1 C5 C6 N3 -5.5(6) . . . . ? C4 C5 C6 N3 161.6(5) . . . . ? C6 N3 C8 C9 127.3(5) . . . . ? Cu1 N3 C8 C9 -49.2(6) . . . . ? N3 C8 C9 C10 70.2(6) . . . . ? C12 N4 C10 C9 -128.3(5) . . . . ? Cu1 N4 C10 C9 45.3(6) . . . . ? C8 C9 C10 N4 -68.1(6) . . . . ? C10 N4 C12 C13 174.1(4) . . . . ? Cu1 N4 C12 C13 -0.1(5) . . . . ? N6 N5 C13 C14 0.3(5) . . . . ? Cu1 N5 C13 C14 160.1(3) . . . . ? N6 N5 C13 C12 -168.0(4) . . . . ? Cu1 N5 C13 C12 -8.3(5) . . . . ? N4 C12 C13 N5 5.5(6) . . . . ? N4 C12 C13 C14 -158.5(5) . . . . ? N5 C13 C14 C15 -0.8(5) . . . . ? C12 C13 C14 C15 163.5(5) . . . . ? N5 N6 C15 C14 -0.9(5) . . . . ? Cu2 N6 C15 C14 -164.0(3) . . . . ? N5 N6 C15 C16 171.5(4) . . . . ? Cu2 N6 C15 C16 8.4(5) . . . . ? C13 C14 C15 N6 1.1(5) . . . . ? C13 C14 C15 C16 -168.9(5) . . . . ? C18 N7 C16 C15 -176.4(4) . . . . ? Cu2 N7 C16 C15 -2.9(5) . . . . ? N6 C15 C16 N7 -3.6(6) . . . . ? C14 C15 C16 N7 166.0(5) . . . . ? C16 N7 C18 C19 125.6(5) . . . . ? Cu2 N7 C18 C19 -47.3(5) . . . . ? N7 C18 C19 C20 68.0(5) . . . . ? C22 N8 C20 C19 -127.0(5) . . . . ? Cu2 N8 C20 C19 46.8(5) . . . . ? C18 C19 C20 N8 -68.0(5) . . . . ? C20 N8 C22 C3 175.6(4) . . . . ? Cu2 N8 C22 C3 1.4(5) . . . . ? N2 C3 C22 N8 4.4(6) . . . . ? C4 C3 C22 N8 -163.7(5) . . . . ? 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 O70 H70A O40 0.84 2.03 2.866(5) 174.8 . O70 H70B O30 0.84 1.99 2.807(5) 163.0 . O61 H61 O41 0.84 1.89 2.667(6) 153.2 . O51 H51 O31 0.84 1.81 2.652(7) 177.8 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.287 _refine_diff_density_min -1.151 _refine_diff_density_rms 0.119