# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Ke Wen' _publ_contact_author_email KWEN@BRAIN.ECNU.EDU.CN _publ_section_title ; Coordination-Driven Self-Assembly of Discrete and Polymeric Copper(II) and Dicopper(II) Supramolecular Structures Based on Oxacalix[2]benzene[2]pyrazines ; loop_ _publ_author_name 'Ke Wen' 'Xiao-Yan Li' 'Ming-Liang Ma' 'Xiao-Li Zhao' # Attachment 'Cif-3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 737910' #TrackingRef 'Cif-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H18 Cu N7 O10' _chemical_formula_weight 640.00 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2199(2) _cell_length_b 10.8679(2) _cell_length_c 13.2317(3) _cell_angle_alpha 85.3510(10) _cell_angle_beta 88.1270(10) _cell_angle_gamma 83.6900(10) _cell_volume 1313.08(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.446 _exptl_crystal_size_mid 0.248 _exptl_crystal_size_min 0.165 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.905 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.851885 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 15230 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4553 _reflns_number_gt 4193 _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^)+(0.0368P)^2^+0.9987P] 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 4553 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.20489(2) 0.66702(2) 0.533598(17) 0.01865(8) Uani 1 1 d . . . O1 O -0.47807(14) 0.72678(12) 0.26253(11) 0.0221(3) Uani 1 1 d . . . O2 O -0.27024(14) 0.85326(13) 0.34390(10) 0.0212(3) Uani 1 1 d . . . O3 O 0.14177(14) 0.78637(14) 0.13860(10) 0.0236(3) Uani 1 1 d . . . O4 O -0.02063(15) 0.58575(13) 0.13811(11) 0.0237(3) Uani 1 1 d . . . O5 O 0.1341(2) 0.45465(17) 0.44411(14) 0.0468(5) Uani 1 1 d . . . O6 O 0.3064(2) 0.42818(18) 0.32974(14) 0.0543(5) Uani 1 1 d . . . O7 O 0.32372(15) 0.55659(13) 0.44434(11) 0.0236(3) Uani 1 1 d . . . O8 O -0.04185(18) 0.94357(14) 0.65315(11) 0.0325(4) Uani 1 1 d . . . O9 O 0.07495(16) 0.76696(12) 0.62178(11) 0.0257(3) Uani 1 1 d . . . O10 O 0.14638(17) 0.93906(14) 0.55050(12) 0.0320(4) Uani 1 1 d . . . N1 N -0.25530(17) 0.65406(15) 0.19288(12) 0.0187(3) Uani 1 1 d . . . N2 N -0.23245(17) 0.46225(15) 0.34424(12) 0.0196(3) Uani 1 1 d . . . N3 N 0.09590(16) 0.74455(14) 0.40800(12) 0.0175(3) Uani 1 1 d . . . N4 N -0.06453(17) 0.83126(15) 0.23838(12) 0.0182(3) Uani 1 1 d . . . N5 N 0.2520(2) 0.47567(17) 0.40482(14) 0.0295(4) Uani 1 1 d . . . N6 N 0.05978(19) 0.88791(15) 0.60738(13) 0.0228(4) Uani 1 1 d . . . N7 N 0.4122(2) 0.75393(18) 0.54915(16) 0.0341(4) Uani 1 1 d . . . C1 C -0.4570(2) 0.84705(18) 0.22408(15) 0.0194(4) Uani 1 1 d . . . C2 C -0.5524(2) 0.9058(2) 0.15284(16) 0.0264(5) Uani 1 1 d . . . H2A H -0.6250 0.8623 0.1267 0.032 Uiso 1 1 calc R . . C3 C -0.5414(2) 1.0289(2) 0.11967(17) 0.0302(5) Uani 1 1 d . . . H3A H -0.6080 1.0704 0.0716 0.036 Uiso 1 1 calc R . . C4 C -0.4342(2) 1.0915(2) 0.15618(17) 0.0305(5) Uani 1 1 d . . . H4A H -0.4258 1.1752 0.1319 0.037 Uiso 1 1 calc R . . C5 C -0.3385(2) 1.03266(19) 0.22821(16) 0.0258(5) Uani 1 1 d . . . H5A H -0.2647 1.0757 0.2534 0.031 Uiso 1 1 calc R . . C6 C -0.3517(2) 0.91129(18) 0.26275(15) 0.0195(4) Uani 1 1 d . . . C7 C -0.0313(2) 0.67694(18) 0.05666(15) 0.0209(4) Uani 1 1 d . . . C8 C -0.1121(2) 0.6631(2) -0.02696(16) 0.0288(5) Uani 1 1 d . . . H8A H -0.1710 0.5966 -0.0271 0.035 Uiso 1 1 calc R . . C9 C -0.1058(3) 0.7479(2) -0.11094(17) 0.0350(5) Uani 1 1 d . . . H9A H -0.1616 0.7400 -0.1687 0.042 Uiso 1 1 calc R . . C10 C -0.0192(3) 0.8435(2) -0.11113(17) 0.0342(5) Uani 1 1 d . . . H10A H -0.0147 0.9004 -0.1693 0.041 Uiso 1 1 calc R . . C11 C 0.0610(2) 0.8571(2) -0.02732(16) 0.0266(5) Uani 1 1 d . . . H11A H 0.1212 0.9227 -0.0278 0.032 Uiso 1 1 calc R . . C12 C 0.0532(2) 0.77485(18) 0.05705(14) 0.0193(4) Uani 1 1 d . . . C13 C -0.12404(19) 0.82282(17) 0.33041(15) 0.0170(4) Uani 1 1 d . . . C14 C -0.0469(2) 0.77819(17) 0.41616(14) 0.0173(4) Uani 1 1 d . . . H14A H -0.0956 0.7716 0.4804 0.021 Uiso 1 1 calc R . . C15 C 0.1604(2) 0.75149(18) 0.31545(15) 0.0194(4) Uani 1 1 d . . . H15A H 0.2625 0.7295 0.3073 0.023 Uiso 1 1 calc R . . C16 C 0.0761(2) 0.79102(17) 0.23266(14) 0.0183(4) Uani 1 1 d . . . C17 C -0.3583(2) 0.64007(18) 0.26333(15) 0.0190(4) Uani 1 1 d . . . C18 C -0.3515(2) 0.54490(18) 0.33908(15) 0.0203(4) Uani 1 1 d . . . H18A H -0.4300 0.5380 0.3868 0.024 Uiso 1 1 calc R . . C19 C -0.1242(2) 0.47455(18) 0.27557(15) 0.0208(4) Uani 1 1 d . . . H19A H -0.0387 0.4171 0.2776 0.025 Uiso 1 1 calc R . . C20 C -0.1386(2) 0.57246(17) 0.20137(15) 0.0189(4) Uani 1 1 d . . . C21 C 0.5067(2) 0.8058(2) 0.56810(17) 0.0295(5) Uani 1 1 d . . . C22 C 0.6273(3) 0.8735(3) 0.5930(2) 0.0386(6) Uani 1 1 d . . . C23 C 0.5142(3) 0.4488(2) 0.0987(2) 0.0434(6) Uani 1 1 d . . . H23A H 0.5241 0.4132 0.1664 0.052 Uiso 1 1 calc R . . C24 C 0.6158(3) 0.4125(2) 0.0245(2) 0.0464(7) Uani 1 1 d . . . H24A H 0.6957 0.3524 0.0415 0.056 Uiso 1 1 calc R . . C25 C 0.6014(3) 0.4633(2) -0.0741(2) 0.0445(7) Uani 1 1 d . . . H25A H 0.6709 0.4379 -0.1249 0.053 Uiso 1 1 calc R . . H22A H 0.669(3) 0.912(3) 0.535(2) 0.048(8) Uiso 1 1 d . . . H22B H 0.594(4) 0.933(3) 0.634(3) 0.065(10) Uiso 1 1 d . . . H22C H 0.695(4) 0.822(3) 0.622(3) 0.067(11) 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 0.02102(13) 0.01742(14) 0.01679(14) 0.00154(9) -0.00037(9) -0.00098(9) O1 0.0162(6) 0.0202(7) 0.0286(8) 0.0046(6) 0.0016(6) -0.0013(5) O2 0.0162(6) 0.0304(8) 0.0159(7) -0.0010(6) 0.0002(5) 0.0015(5) O3 0.0185(7) 0.0347(8) 0.0173(7) -0.0002(6) 0.0031(5) -0.0040(6) O4 0.0236(7) 0.0201(7) 0.0248(8) 0.0052(6) 0.0087(6) 0.0010(6) O5 0.0513(11) 0.0485(11) 0.0448(11) -0.0014(9) 0.0004(9) -0.0266(9) O6 0.0701(13) 0.0523(12) 0.0395(11) -0.0238(9) -0.0004(9) 0.0128(10) O7 0.0224(7) 0.0245(8) 0.0226(8) 0.0003(6) 0.0017(6) 0.0005(6) O8 0.0465(9) 0.0261(8) 0.0229(8) -0.0044(6) 0.0026(7) 0.0060(7) O9 0.0392(8) 0.0162(7) 0.0201(7) 0.0009(6) 0.0022(6) 0.0011(6) O10 0.0367(9) 0.0241(8) 0.0358(9) 0.0017(7) -0.0002(7) -0.0091(7) N1 0.0197(8) 0.0178(8) 0.0188(8) -0.0003(7) 0.0001(6) -0.0037(6) N2 0.0216(8) 0.0192(8) 0.0178(8) 0.0013(7) 0.0006(6) -0.0034(6) N3 0.0193(8) 0.0152(8) 0.0179(8) -0.0010(6) -0.0002(6) -0.0022(6) N4 0.0183(8) 0.0193(8) 0.0174(8) -0.0020(7) 0.0002(6) -0.0031(6) N5 0.0390(11) 0.0226(9) 0.0256(10) 0.0004(8) -0.0043(8) 0.0024(8) N6 0.0319(9) 0.0202(9) 0.0166(9) -0.0020(7) -0.0087(7) -0.0016(7) N7 0.0286(10) 0.0315(11) 0.0427(12) -0.0011(9) -0.0019(8) -0.0071(8) C1 0.0176(9) 0.0193(10) 0.0202(10) 0.0006(8) 0.0042(7) -0.0001(7) C2 0.0198(10) 0.0340(12) 0.0247(11) 0.0035(9) -0.0027(8) -0.0028(9) C3 0.0264(11) 0.0325(12) 0.0282(12) 0.0090(10) -0.0010(9) 0.0047(9) C4 0.0343(12) 0.0210(11) 0.0340(13) 0.0055(9) 0.0049(9) 0.0004(9) C5 0.0239(10) 0.0237(11) 0.0301(12) -0.0053(9) 0.0024(9) -0.0029(8) C6 0.0170(9) 0.0237(10) 0.0165(10) -0.0014(8) 0.0018(7) 0.0030(8) C7 0.0237(10) 0.0187(10) 0.0183(10) -0.0007(8) 0.0068(8) 0.0031(8) C8 0.0311(11) 0.0314(12) 0.0250(12) -0.0099(9) 0.0034(9) -0.0045(9) C9 0.0381(12) 0.0475(14) 0.0187(11) -0.0062(10) -0.0028(9) 0.0027(11) C10 0.0410(13) 0.0391(13) 0.0184(11) 0.0080(10) 0.0042(9) 0.0049(10) C11 0.0316(11) 0.0230(11) 0.0235(11) 0.0015(9) 0.0084(9) 0.0001(9) C12 0.0186(9) 0.0221(10) 0.0162(10) -0.0014(8) 0.0044(7) 0.0019(8) C13 0.0165(9) 0.0147(9) 0.0206(10) -0.0045(8) 0.0014(7) -0.0030(7) C14 0.0201(9) 0.0164(9) 0.0159(9) -0.0027(7) 0.0016(7) -0.0031(7) C15 0.0171(9) 0.0195(10) 0.0214(10) 0.0007(8) 0.0021(7) -0.0031(7) C16 0.0205(9) 0.0175(10) 0.0174(10) -0.0010(8) 0.0038(7) -0.0059(7) C17 0.0169(9) 0.0191(10) 0.0215(10) -0.0023(8) -0.0019(7) -0.0035(7) C18 0.0183(9) 0.0222(10) 0.0202(10) 0.0006(8) 0.0001(8) -0.0032(8) C19 0.0227(10) 0.0175(10) 0.0219(10) -0.0004(8) 0.0016(8) -0.0024(8) C20 0.0213(9) 0.0171(10) 0.0191(10) -0.0034(8) 0.0021(8) -0.0046(7) C21 0.0265(11) 0.0310(12) 0.0308(12) -0.0038(10) 0.0042(9) -0.0027(9) C22 0.0323(13) 0.0480(16) 0.0397(15) -0.0165(13) 0.0096(12) -0.0171(12) C23 0.0519(15) 0.0325(14) 0.0487(16) -0.0093(12) 0.0031(12) -0.0141(12) C24 0.0397(14) 0.0297(13) 0.069(2) -0.0080(13) 0.0061(13) -0.0010(11) C25 0.0463(15) 0.0288(13) 0.0604(18) -0.0172(12) 0.0190(13) -0.0095(11) _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 O9 1.9506(14) . ? Cu1 O7 1.9727(14) . ? Cu1 N3 2.0439(16) . ? Cu1 N2 2.0571(16) 2_566 ? Cu1 N7 2.2456(19) . ? O1 C17 1.370(2) . ? O1 C1 1.395(2) . ? O2 C13 1.362(2) . ? O2 C6 1.398(2) . ? O3 C16 1.368(2) . ? O3 C12 1.396(2) . ? O4 C20 1.364(2) . ? O4 C7 1.402(2) . ? O5 N5 1.225(3) . ? O6 N5 1.224(2) . ? O7 N5 1.307(2) . ? O8 N6 1.228(2) . ? O9 N6 1.305(2) . ? O10 N6 1.226(2) . ? N1 C20 1.319(2) . ? N1 C17 1.321(3) . ? N2 C19 1.338(3) . ? N2 C18 1.340(2) . ? N2 Cu1 2.0571(16) 2_566 ? N3 C14 1.330(2) . ? N3 C15 1.344(2) . ? N4 C13 1.320(2) . ? N4 C16 1.324(2) . ? N7 C21 1.133(3) . ? C1 C2 1.380(3) . ? C1 C6 1.389(3) . ? C2 C3 1.388(3) . ? C2 H2A 0.9500 . ? C3 C4 1.380(3) . ? C3 H3A 0.9500 . ? C4 C5 1.388(3) . ? C4 H4A 0.9500 . ? C5 C6 1.378(3) . ? C5 H5A 0.9500 . ? C7 C8 1.381(3) . ? C7 C12 1.386(3) . ? C8 C9 1.389(3) . ? C8 H8A 0.9500 . ? C9 C10 1.378(4) . ? C9 H9A 0.9500 . ? C10 C11 1.379(3) . ? C10 H10A 0.9500 . ? C11 C12 1.377(3) . ? C11 H11A 0.9500 . ? C13 C14 1.384(3) . ? C14 H14A 0.9500 . ? C15 C16 1.376(3) . ? C15 H15A 0.9500 . ? C17 C18 1.378(3) . ? C18 H18A 0.9500 . ? C19 C20 1.386(3) . ? C19 H19A 0.9500 . ? C21 C22 1.460(3) . ? C22 H22A 0.93(3) . ? C22 H22B 0.90(4) . ? C22 H22C 0.87(4) . ? C23 C25 1.379(4) 2_665 ? C23 C24 1.385(4) . ? C23 H23A 0.9500 . ? C24 C25 1.379(4) . ? C24 H24A 0.9500 . ? C25 C23 1.379(4) 2_665 ? C25 H25A 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 O9 Cu1 O7 175.28(6) . . ? O9 Cu1 N3 91.31(6) . . ? O7 Cu1 N3 87.94(6) . . ? O9 Cu1 N2 86.76(6) . 2_566 ? O7 Cu1 N2 91.72(6) . 2_566 ? N3 Cu1 N2 152.05(6) . 2_566 ? O9 Cu1 N7 99.83(7) . . ? O7 Cu1 N7 84.79(7) . . ? N3 Cu1 N7 110.64(7) . . ? N2 Cu1 N7 97.14(7) 2_566 . ? C17 O1 C1 116.80(14) . . ? C13 O2 C6 119.33(15) . . ? C16 O3 C12 117.42(14) . . ? C20 O4 C7 119.45(15) . . ? N5 O7 Cu1 114.56(12) . . ? N6 O9 Cu1 120.51(12) . . ? C20 N1 C17 115.38(17) . . ? C19 N2 C18 118.96(17) . . ? C19 N2 Cu1 120.26(13) . 2_566 ? C18 N2 Cu1 120.28(13) . 2_566 ? C14 N3 C15 118.58(16) . . ? C14 N3 Cu1 118.93(13) . . ? C15 N3 Cu1 122.16(12) . . ? C13 N4 C16 115.05(16) . . ? O6 N5 O5 124.7(2) . . ? O6 N5 O7 117.38(19) . . ? O5 N5 O7 117.89(18) . . ? O10 N6 O8 124.03(17) . . ? O10 N6 O9 119.12(17) . . ? O8 N6 O9 116.85(17) . . ? C21 N7 Cu1 170.23(19) . . ? C2 C1 C6 120.10(19) . . ? C2 C1 O1 118.30(18) . . ? C6 C1 O1 121.34(17) . . ? C1 C2 C3 119.4(2) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C6 C5 C4 119.3(2) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? C5 C6 C1 120.52(18) . . ? C5 C6 O2 121.27(18) . . ? C1 C6 O2 117.93(17) . . ? C8 C7 C12 120.44(19) . . ? C8 C7 O4 120.77(18) . . ? C12 C7 O4 118.45(18) . . ? C7 C8 C9 118.9(2) . . ? C7 C8 H8A 120.6 . . ? C9 C8 H8A 120.6 . . ? C10 C9 C8 120.5(2) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C12 C11 C10 119.6(2) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? C11 C12 C7 120.25(19) . . ? C11 C12 O3 118.35(18) . . ? C7 C12 O3 121.17(18) . . ? N4 C13 O2 119.86(16) . . ? N4 C13 C14 123.54(17) . . ? O2 C13 C14 116.53(16) . . ? N3 C14 C13 119.60(17) . . ? N3 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? N3 C15 C16 118.89(17) . . ? N3 C15 H15A 120.6 . . ? C16 C15 H15A 120.6 . . ? N4 C16 O3 118.17(17) . . ? N4 C16 C15 124.14(17) . . ? O3 C16 C15 117.68(16) . . ? N1 C17 O1 118.13(17) . . ? N1 C17 C18 124.07(17) . . ? O1 C17 C18 117.79(17) . . ? N2 C18 C17 118.88(17) . . ? N2 C18 H18A 120.6 . . ? C17 C18 H18A 120.6 . . ? N2 C19 C20 119.00(17) . . ? N2 C19 H19A 120.5 . . ? C20 C19 H19A 120.5 . . ? N1 C20 O4 119.85(17) . . ? N1 C20 C19 123.65(18) . . ? O4 C20 C19 116.42(16) . . ? N7 C21 C22 179.4(3) . . ? C21 C22 H22A 111.7(18) . . ? C21 C22 H22B 110(2) . . ? H22A C22 H22B 108(3) . . ? C21 C22 H22C 109(2) . . ? H22A C22 H22C 108(3) . . ? H22B C22 H22C 111(3) . . ? C25 C23 C24 119.9(3) 2_665 . ? C25 C23 H23A 120.1 2_665 . ? C24 C23 H23A 120.1 . . ? C25 C24 C23 120.3(3) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? C24 C25 C23 119.9(2) . 2_665 ? C24 C25 H25A 120.1 . . ? C23 C25 H25A 120.1 2_665 . ? 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 O9 Cu1 O7 N5 13.2(8) . . . . ? N3 Cu1 O7 N5 -67.64(13) . . . . ? N2 Cu1 O7 N5 84.40(13) 2_566 . . . ? N7 Cu1 O7 N5 -178.58(13) . . . . ? O7 Cu1 O9 N6 -137.5(7) . . . . ? N3 Cu1 O9 N6 -56.71(14) . . . . ? N2 Cu1 O9 N6 151.19(14) 2_566 . . . ? N7 Cu1 O9 N6 54.50(14) . . . . ? O9 Cu1 N3 C14 -32.57(14) . . . . ? O7 Cu1 N3 C14 142.76(14) . . . . ? N2 Cu1 N3 C14 53.0(2) 2_566 . . . ? N7 Cu1 N3 C14 -133.59(14) . . . . ? O9 Cu1 N3 C15 154.14(15) . . . . ? O7 Cu1 N3 C15 -30.52(15) . . . . ? N2 Cu1 N3 C15 -120.31(17) 2_566 . . . ? N7 Cu1 N3 C15 53.13(16) . . . . ? Cu1 O7 N5 O6 160.94(15) . . . . ? Cu1 O7 N5 O5 -17.6(2) . . . . ? Cu1 O9 N6 O10 -13.1(2) . . . . ? Cu1 O9 N6 O8 167.33(13) . . . . ? O9 Cu1 N7 C21 12.0(11) . . . . ? O7 Cu1 N7 C21 -167.0(11) . . . . ? N3 Cu1 N7 C21 107.1(11) . . . . ? N2 Cu1 N7 C21 -76.0(11) 2_566 . . . ? C17 O1 C1 C2 130.88(19) . . . . ? C17 O1 C1 C6 -55.1(2) . . . . ? C6 C1 C2 C3 0.6(3) . . . . ? O1 C1 C2 C3 174.64(18) . . . . ? C1 C2 C3 C4 1.2(3) . . . . ? C2 C3 C4 C5 -1.5(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C4 C5 C6 C1 1.8(3) . . . . ? C4 C5 C6 O2 -171.99(18) . . . . ? C2 C1 C6 C5 -2.1(3) . . . . ? O1 C1 C6 C5 -175.95(17) . . . . ? C2 C1 C6 O2 171.88(17) . . . . ? O1 C1 C6 O2 -2.0(3) . . . . ? C13 O2 C6 C5 -71.2(2) . . . . ? C13 O2 C6 C1 114.87(19) . . . . ? C20 O4 C7 C8 -72.2(2) . . . . ? C20 O4 C7 C12 114.48(19) . . . . ? C12 C7 C8 C9 0.8(3) . . . . ? O4 C7 C8 C9 -172.41(18) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C10 C11 C12 C7 1.9(3) . . . . ? C10 C11 C12 O3 176.39(18) . . . . ? C8 C7 C12 C11 -2.1(3) . . . . ? O4 C7 C12 C11 171.28(16) . . . . ? C8 C7 C12 O3 -176.42(17) . . . . ? O4 C7 C12 O3 -3.1(3) . . . . ? C16 O3 C12 C11 128.88(18) . . . . ? C16 O3 C12 C7 -56.7(2) . . . . ? C16 N4 C13 O2 -175.30(16) . . . . ? C16 N4 C13 C14 1.4(3) . . . . ? C6 O2 C13 N4 -9.9(3) . . . . ? C6 O2 C13 C14 173.12(16) . . . . ? C15 N3 C14 C13 -2.0(3) . . . . ? Cu1 N3 C14 C13 -175.53(13) . . . . ? N4 C13 C14 N3 1.9(3) . . . . ? O2 C13 C14 N3 178.76(16) . . . . ? C14 N3 C15 C16 -1.1(3) . . . . ? Cu1 N3 C15 C16 172.21(13) . . . . ? C13 N4 C16 O3 174.12(16) . . . . ? C13 N4 C16 C15 -4.8(3) . . . . ? C12 O3 C16 N4 -25.3(2) . . . . ? C12 O3 C16 C15 153.71(17) . . . . ? N3 C15 C16 N4 4.8(3) . . . . ? N3 C15 C16 O3 -174.11(16) . . . . ? C20 N1 C17 O1 175.79(16) . . . . ? C20 N1 C17 C18 -2.8(3) . . . . ? C1 O1 C17 N1 -29.5(2) . . . . ? C1 O1 C17 C18 149.19(17) . . . . ? C19 N2 C18 C17 -0.2(3) . . . . ? Cu1 N2 C18 C17 171.75(14) 2_566 . . . ? N1 C17 C18 N2 1.7(3) . . . . ? O1 C17 C18 N2 -176.95(16) . . . . ? C18 N2 C19 C20 0.1(3) . . . . ? Cu1 N2 C19 C20 -171.87(13) 2_566 . . . ? C17 N1 C20 O4 -173.92(17) . . . . ? C17 N1 C20 C19 2.7(3) . . . . ? C7 O4 C20 N1 -7.9(3) . . . . ? C7 O4 C20 C19 175.25(17) . . . . ? N2 C19 C20 N1 -1.4(3) . . . . ? N2 C19 C20 O4 175.31(17) . . . . ? Cu1 N7 C21 C22 -22(30) . . . . ? C25 C23 C24 C25 -0.4(4) 2_665 . . . ? C23 C24 C25 C23 0.4(4) . . . 2_665 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.376 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.053 # Attachment 'Cif-4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 737911' #TrackingRef 'Cif-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 Cu N4 O8' _chemical_formula_weight 553.96 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.40610(10) _cell_length_b 11.65250(10) _cell_length_c 13.5896(2) _cell_angle_alpha 111.5010(10) _cell_angle_beta 96.2460(10) _cell_angle_gamma 103.6780(10) _cell_volume 1174.91(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Rectangular _exptl_crystal_colour blue _exptl_crystal_size_max 0.386 _exptl_crystal_size_mid 0.286 _exptl_crystal_size_min 0.203 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 566 _exptl_absorpt_coefficient_mu 0.988 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.856106 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 13703 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4113 _reflns_number_gt 3825 _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^)+(0.0384P)^2^+0.5598P] 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 SHELXL _refine_ls_extinction_coef 0.0061(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4113 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 -0.40694(3) 0.610474(19) 0.074663(16) 0.03318(10) Uani 1 1 d . . . N1 N -0.23393(19) 0.79715(14) 0.19567(12) 0.0318(3) Uani 1 1 d . . . N2 N 0.01565(18) 1.01873(13) 0.33012(12) 0.0302(3) Uani 1 1 d . . . N3 N 0.2557(2) 1.12977(16) 0.22937(12) 0.0389(4) Uani 1 1 d . . . N4 N 0.2476(3) 1.0215(2) 0.01098(15) 0.0651(6) Uani 1 1 d . . . O1 O -0.12822(17) 1.13963(12) 0.27859(11) 0.0403(3) Uani 1 1 d . . . O2 O 0.1191(2) 1.26845(15) 0.20297(12) 0.0516(4) Uani 1 1 d . . . O3 O 0.3757(2) 0.98053(15) 0.25295(11) 0.0509(4) Uani 1 1 d . . . O4 O 0.16503(16) 0.89519(12) 0.37288(12) 0.0423(3) Uani 1 1 d . . . O5 O -0.33955(19) 0.50594(13) 0.14854(11) 0.0463(3) Uani 1 1 d . . . O6 O -0.49709(19) 0.31721(13) 0.01952(12) 0.0473(4) Uani 1 1 d . . . O7 O -0.60261(19) 0.60867(15) 0.13979(12) 0.0521(4) Uani 1 1 d . . . O8 O -0.76418(17) 0.42092(14) 0.01151(12) 0.0472(4) Uani 1 1 d . . . C1 C -0.0996(2) 0.79074(17) 0.25225(15) 0.0347(4) Uani 1 1 d . . . H1A H -0.0899 0.7112 0.2476 0.042 Uiso 1 1 calc R . . C2 C 0.0257(2) 0.90341(16) 0.31810(14) 0.0306(4) Uani 1 1 d . . . C3 C -0.1172(2) 1.02233(16) 0.27193(13) 0.0292(4) Uani 1 1 d . . . C4 C -0.2450(2) 0.91213(17) 0.20344(14) 0.0316(4) Uani 1 1 d . . . H4A H -0.3372 0.9185 0.1635 0.038 Uiso 1 1 calc R . . C5 C 0.0057(3) 1.2915(2) 0.46156(17) 0.0462(5) Uani 1 1 d . . . H5A H -0.0762 1.2483 0.4872 0.055 Uiso 1 1 calc R . . C6 C 0.1324(3) 1.3997(2) 0.53301(19) 0.0586(6) Uani 1 1 d . . . H6A H 0.1367 1.4291 0.6071 0.070 Uiso 1 1 calc R . . C7 C 0.2520(3) 1.4638(2) 0.4945(2) 0.0624(7) Uani 1 1 d . . . H7A H 0.3365 1.5371 0.5428 0.075 Uiso 1 1 calc R . . C8 C 0.2476(3) 1.4205(2) 0.3855(2) 0.0547(6) Uani 1 1 d . . . H8A H 0.3289 1.4644 0.3600 0.066 Uiso 1 1 calc R . . C9 C 0.1222(3) 1.31166(18) 0.31362(17) 0.0413(4) Uani 1 1 d . . . C10 C 0.0014(2) 1.24815(17) 0.35233(16) 0.0367(4) Uani 1 1 d . . . C11 C 0.2985(2) 1.01057(16) 0.42337(15) 0.0322(4) Uani 1 1 d . . . C12 C 0.4024(2) 1.05299(18) 0.36427(15) 0.0351(4) Uani 1 1 d . . . C13 C 0.5372(2) 1.1627(2) 0.41620(17) 0.0417(5) Uani 1 1 d . . . H13A H 0.6082 1.1916 0.3767 0.050 Uiso 1 1 calc R . . C14 C 0.5665(3) 1.22940(19) 0.52674(17) 0.0440(5) Uani 1 1 d . . . H14A H 0.6577 1.3034 0.5617 0.053 Uiso 1 1 calc R . . C15 C 0.4626(3) 1.18784(19) 0.58557(16) 0.0433(5) Uani 1 1 d . . . H15A H 0.4827 1.2336 0.6602 0.052 Uiso 1 1 calc R . . C16 C 0.3276(2) 1.07747(19) 0.53346(16) 0.0383(4) Uani 1 1 d . . . H16A H 0.2566 1.0486 0.5730 0.046 Uiso 1 1 calc R . . C17 C 0.3132(3) 1.0311(2) 0.18683(15) 0.0414(4) Uani 1 1 d . . . C18 C 0.3101(3) 0.9752(2) 0.07712(18) 0.0571(6) Uani 1 1 d . . . H18A H 0.3518 0.9054 0.0499 0.069 Uiso 1 1 calc R . . C19 C 0.1857(3) 1.1191(3) 0.05223(18) 0.0561(6) Uani 1 1 d . . . H19A H 0.1406 1.1529 0.0075 0.067 Uiso 1 1 calc R . . C20 C 0.1882(3) 1.1708(2) 0.16200(16) 0.0414(5) Uani 1 1 d . . . C21 C -0.3958(2) 0.38512(18) 0.10887(15) 0.0376(4) Uani 1 1 d . . . C22 C -0.3379(3) 0.3158(2) 0.17297(19) 0.0563(6) Uani 1 1 d . . . H22A H -0.3894 0.2244 0.1340 0.084 Uiso 1 1 calc R . . H22B H -0.3690 0.3442 0.2419 0.084 Uiso 1 1 calc R . . H22C H -0.2182 0.3347 0.1840 0.084 Uiso 1 1 calc R . . C23 C -0.7388(3) 0.5207(2) 0.09666(16) 0.0405(4) Uani 1 1 d . . . C24 C -0.8838(3) 0.5359(3) 0.1506(2) 0.0601(6) Uani 1 1 d . . . H24A H -0.8489 0.6156 0.2141 0.090 Uiso 1 1 calc R . . H24B H -0.9214 0.4650 0.1709 0.090 Uiso 1 1 calc R . . H24C H -0.9739 0.5370 0.1013 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02987(14) 0.02726(14) 0.02847(14) 0.00167(9) -0.00121(9) 0.00271(9) N1 0.0290(8) 0.0280(7) 0.0280(7) 0.0048(6) 0.0010(6) 0.0030(6) N2 0.0266(7) 0.0263(7) 0.0322(7) 0.0093(6) 0.0022(6) 0.0039(6) N3 0.0437(9) 0.0418(9) 0.0314(8) 0.0156(7) 0.0109(7) 0.0104(7) N4 0.0806(15) 0.0757(15) 0.0323(10) 0.0171(10) 0.0143(10) 0.0186(12) O1 0.0393(7) 0.0278(6) 0.0469(8) 0.0138(6) -0.0056(6) 0.0066(6) O2 0.0657(10) 0.0528(9) 0.0467(8) 0.0296(7) 0.0119(7) 0.0214(8) O3 0.0700(10) 0.0495(9) 0.0339(7) 0.0094(6) 0.0118(7) 0.0309(8) O4 0.0292(7) 0.0278(6) 0.0585(9) 0.0143(6) -0.0100(6) 0.0022(5) O5 0.0511(9) 0.0326(7) 0.0409(8) 0.0098(6) -0.0067(6) 0.0027(6) O6 0.0492(8) 0.0333(7) 0.0443(8) 0.0091(6) -0.0098(7) 0.0051(6) O7 0.0410(8) 0.0546(9) 0.0401(8) -0.0013(7) 0.0102(6) 0.0099(7) O8 0.0350(7) 0.0489(8) 0.0444(8) 0.0076(7) 0.0100(6) 0.0063(6) C1 0.0327(10) 0.0250(8) 0.0378(10) 0.0072(7) 0.0008(8) 0.0057(7) C2 0.0258(9) 0.0284(9) 0.0328(9) 0.0097(7) 0.0021(7) 0.0055(7) C3 0.0313(9) 0.0276(8) 0.0274(8) 0.0107(7) 0.0063(7) 0.0072(7) C4 0.0291(9) 0.0347(9) 0.0258(8) 0.0097(7) 0.0007(7) 0.0066(7) C5 0.0496(12) 0.0373(11) 0.0482(12) 0.0131(9) 0.0137(10) 0.0124(9) C6 0.0729(16) 0.0412(12) 0.0436(12) 0.0027(10) 0.0071(11) 0.0106(11) C7 0.0673(16) 0.0321(11) 0.0618(15) 0.0054(10) -0.0024(12) -0.0025(11) C8 0.0526(13) 0.0360(11) 0.0699(15) 0.0236(11) 0.0093(11) 0.0015(10) C9 0.0484(12) 0.0319(10) 0.0459(11) 0.0182(9) 0.0079(9) 0.0131(9) C10 0.0378(10) 0.0238(8) 0.0439(11) 0.0107(8) 0.0020(8) 0.0089(8) C11 0.0238(8) 0.0269(9) 0.0407(10) 0.0115(8) -0.0016(7) 0.0057(7) C12 0.0361(10) 0.0360(10) 0.0325(9) 0.0106(8) 0.0046(8) 0.0157(8) C13 0.0344(10) 0.0419(11) 0.0533(12) 0.0246(9) 0.0132(9) 0.0093(8) C14 0.0359(11) 0.0312(10) 0.0526(12) 0.0133(9) -0.0046(9) 0.0007(8) C15 0.0461(12) 0.0399(11) 0.0328(10) 0.0071(8) -0.0019(8) 0.0102(9) C16 0.0354(10) 0.0433(11) 0.0381(10) 0.0193(9) 0.0085(8) 0.0105(8) C17 0.0433(11) 0.0440(11) 0.0322(10) 0.0120(8) 0.0101(8) 0.0098(9) C18 0.0683(16) 0.0609(14) 0.0356(11) 0.0100(10) 0.0160(11) 0.0210(12) C19 0.0619(15) 0.0678(15) 0.0375(11) 0.0276(11) 0.0075(10) 0.0088(12) C20 0.0413(11) 0.0430(11) 0.0376(10) 0.0201(9) 0.0087(8) 0.0024(9) C21 0.0340(10) 0.0369(10) 0.0363(10) 0.0112(8) 0.0046(8) 0.0079(8) C22 0.0655(15) 0.0453(12) 0.0486(12) 0.0185(10) -0.0057(11) 0.0088(11) C23 0.0381(11) 0.0513(12) 0.0354(10) 0.0173(9) 0.0093(8) 0.0189(9) C24 0.0509(14) 0.0805(17) 0.0596(14) 0.0292(13) 0.0250(12) 0.0315(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O7 1.9502(15) . ? Cu1 O8 1.9687(14) 2_465 ? Cu1 O6 1.9714(14) 2_465 ? Cu1 O5 1.9777(14) . ? Cu1 N1 2.2164(14) . ? Cu1 Cu1 2.6017(4) 2_465 ? N1 C1 1.328(2) . ? N1 C4 1.331(2) . ? N2 C3 1.315(2) . ? N2 C2 1.317(2) . ? N3 C20 1.314(3) . ? N3 C17 1.314(3) . ? N4 C19 1.325(3) . ? N4 C18 1.327(3) . ? O1 C3 1.362(2) . ? O1 C10 1.404(2) . ? O2 C20 1.363(3) . ? O2 C9 1.395(3) . ? O3 C17 1.364(3) . ? O3 C12 1.397(2) . ? O4 C2 1.360(2) . ? O4 C11 1.407(2) . ? O5 C21 1.253(2) . ? O6 C21 1.256(2) . ? O6 Cu1 1.9714(14) 2_465 ? O7 C23 1.251(3) . ? O8 C23 1.257(2) . ? O8 Cu1 1.9687(14) 2_465 ? C1 C2 1.383(2) . ? C1 H1A 0.9300 . ? C3 C4 1.387(2) . ? C4 H4A 0.9300 . ? C5 C10 1.375(3) . ? C5 C6 1.382(3) . ? C5 H5A 0.9300 . ? C6 C7 1.374(4) . ? C6 H6A 0.9300 . ? C7 C8 1.373(4) . ? C7 H7A 0.9300 . ? C8 C9 1.382(3) . ? C8 H8A 0.9300 . ? C9 C10 1.379(3) . ? C11 C16 1.372(3) . ? C11 C12 1.376(3) . ? C12 C13 1.377(3) . ? C13 C14 1.376(3) . ? C13 H13A 0.9300 . ? C14 C15 1.368(3) . ? C14 H14A 0.9300 . ? C15 C16 1.382(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C18 1.385(3) . ? C18 H18A 0.9300 . ? C19 C20 1.385(3) . ? C19 H19A 0.9300 . ? C21 C22 1.502(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.502(3) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Cu1 O8 168.97(6) . 2_465 ? O7 Cu1 O6 89.02(7) . 2_465 ? O8 Cu1 O6 90.57(7) 2_465 2_465 ? O7 Cu1 O5 89.42(7) . . ? O8 Cu1 O5 88.90(7) 2_465 . ? O6 Cu1 O5 169.06(5) 2_465 . ? O7 Cu1 N1 98.89(6) . . ? O8 Cu1 N1 92.12(6) 2_465 . ? O6 Cu1 N1 96.05(6) 2_465 . ? O5 Cu1 N1 94.89(6) . . ? O7 Cu1 Cu1 85.15(4) . 2_465 ? O8 Cu1 Cu1 83.84(4) 2_465 2_465 ? O6 Cu1 Cu1 84.03(4) 2_465 2_465 ? O5 Cu1 Cu1 85.05(4) . 2_465 ? N1 Cu1 Cu1 175.96(4) . 2_465 ? C1 N1 C4 119.23(15) . . ? C1 N1 Cu1 116.15(12) . . ? C4 N1 Cu1 123.94(12) . . ? C3 N2 C2 116.65(15) . . ? C20 N3 C17 116.72(17) . . ? C19 N4 C18 118.37(19) . . ? C3 O1 C10 116.35(14) . . ? C20 O2 C9 115.57(15) . . ? C17 O3 C12 116.36(15) . . ? C2 O4 C11 115.63(14) . . ? C21 O5 Cu1 122.20(13) . . ? C21 O6 Cu1 123.63(13) . 2_465 ? C23 O7 Cu1 122.63(13) . . ? C23 O8 Cu1 123.08(13) . 2_465 ? N1 C1 C2 119.47(17) . . ? N1 C1 H1A 120.3 . . ? C2 C1 H1A 120.3 . . ? N2 C2 O4 118.49(15) . . ? N2 C2 C1 122.64(16) . . ? O4 C2 C1 118.86(16) . . ? N2 C3 O1 118.29(15) . . ? N2 C3 C4 122.89(16) . . ? O1 C3 C4 118.81(16) . . ? N1 C4 C3 119.05(16) . . ? N1 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C10 C5 C6 119.5(2) . . ? C10 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C7 C6 C5 119.9(2) . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C8 C7 C6 120.5(2) . . ? C8 C7 H7A 119.8 . . ? C6 C7 H7A 119.8 . . ? C7 C8 C9 119.9(2) . . ? C7 C8 H8A 120.0 . . ? C9 C8 H8A 120.0 . . ? C10 C9 C8 119.5(2) . . ? C10 C9 O2 121.08(18) . . ? C8 C9 O2 119.40(19) . . ? C5 C10 C9 120.61(19) . . ? C5 C10 O1 120.19(18) . . ? C9 C10 O1 119.19(18) . . ? C16 C11 C12 120.39(17) . . ? C16 C11 O4 118.83(17) . . ? C12 C11 O4 120.72(17) . . ? C11 C12 C13 119.72(17) . . ? C11 C12 O3 119.69(17) . . ? C13 C12 O3 120.50(18) . . ? C14 C13 C12 119.78(18) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C15 C14 C13 120.60(18) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C14 C15 C16 119.62(18) . . ? C14 C15 H15A 120.2 . . ? C16 C15 H15A 120.2 . . ? C11 C16 C15 119.91(18) . . ? C11 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? N3 C17 O3 118.71(17) . . ? N3 C17 C18 122.4(2) . . ? O3 C17 C18 118.9(2) . . ? N4 C18 C17 120.0(2) . . ? N4 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? N4 C19 C20 120.0(2) . . ? N4 C19 H19A 120.0 . . ? C20 C19 H19A 120.0 . . ? N3 C20 O2 118.07(17) . . ? N3 C20 C19 122.4(2) . . ? O2 C20 C19 119.5(2) . . ? O5 C21 O6 125.06(19) . . ? O5 C21 C22 117.60(17) . . ? O6 C21 C22 117.34(18) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O7 C23 O8 125.19(18) . . ? O7 C23 C24 117.37(19) . . ? O8 C23 C24 117.4(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 O7 Cu1 N1 C1 114.78(14) . . . . ? O8 Cu1 N1 C1 -64.46(14) 2_465 . . . ? O6 Cu1 N1 C1 -155.26(14) 2_465 . . . ? O5 Cu1 N1 C1 24.61(14) . . . . ? Cu1 Cu1 N1 C1 -64.3(6) 2_465 . . . ? O7 Cu1 N1 C4 -74.81(15) . . . . ? O8 Cu1 N1 C4 105.94(14) 2_465 . . . ? O6 Cu1 N1 C4 15.15(15) 2_465 . . . ? O5 Cu1 N1 C4 -164.98(14) . . . . ? Cu1 Cu1 N1 C4 106.1(6) 2_465 . . . ? O7 Cu1 O5 C21 85.32(16) . . . . ? O8 Cu1 O5 C21 -83.77(16) 2_465 . . . ? O6 Cu1 O5 C21 3.5(4) 2_465 . . . ? N1 Cu1 O5 C21 -175.80(16) . . . . ? Cu1 Cu1 O5 C21 0.15(15) 2_465 . . . ? O8 Cu1 O7 C23 -6.5(5) 2_465 . . . ? O6 Cu1 O7 C23 81.45(17) 2_465 . . . ? O5 Cu1 O7 C23 -87.72(17) . . . . ? N1 Cu1 O7 C23 177.42(17) . . . . ? Cu1 Cu1 O7 C23 -2.64(17) 2_465 . . . ? C4 N1 C1 C2 0.1(3) . . . . ? Cu1 N1 C1 C2 170.97(13) . . . . ? C3 N2 C2 O4 176.88(16) . . . . ? C3 N2 C2 C1 -3.2(3) . . . . ? C11 O4 C2 N2 -10.4(2) . . . . ? C11 O4 C2 C1 169.72(17) . . . . ? N1 C1 C2 N2 2.2(3) . . . . ? N1 C1 C2 O4 -177.90(16) . . . . ? C2 N2 C3 O1 -177.11(15) . . . . ? C2 N2 C3 C4 2.1(3) . . . . ? C10 O1 C3 N2 -3.1(2) . . . . ? C10 O1 C3 C4 177.58(16) . . . . ? C1 N1 C4 C3 -1.1(3) . . . . ? Cu1 N1 C4 C3 -171.23(12) . . . . ? N2 C3 C4 N1 0.0(3) . . . . ? O1 C3 C4 N1 179.22(15) . . . . ? C10 C5 C6 C7 0.6(4) . . . . ? C5 C6 C7 C8 -0.6(4) . . . . ? C6 C7 C8 C9 0.0(4) . . . . ? C7 C8 C9 C10 0.6(3) . . . . ? C7 C8 C9 O2 -179.9(2) . . . . ? C20 O2 C9 C10 -82.9(2) . . . . ? C20 O2 C9 C8 97.7(2) . . . . ? C6 C5 C10 C9 0.0(3) . . . . ? C6 C5 C10 O1 -178.92(19) . . . . ? C8 C9 C10 C5 -0.6(3) . . . . ? O2 C9 C10 C5 179.97(18) . . . . ? C8 C9 C10 O1 178.29(18) . . . . ? O2 C9 C10 O1 -1.2(3) . . . . ? C3 O1 C10 C5 -76.3(2) . . . . ? C3 O1 C10 C9 104.8(2) . . . . ? C2 O4 C11 C16 104.0(2) . . . . ? C2 O4 C11 C12 -78.7(2) . . . . ? C16 C11 C12 C13 0.5(3) . . . . ? O4 C11 C12 C13 -176.75(16) . . . . ? C16 C11 C12 O3 177.03(17) . . . . ? O4 C11 C12 O3 -0.3(3) . . . . ? C17 O3 C12 C11 108.2(2) . . . . ? C17 O3 C12 C13 -75.3(2) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? O3 C12 C13 C14 -176.78(17) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? C12 C11 C16 C15 -0.3(3) . . . . ? O4 C11 C16 C15 177.02(16) . . . . ? C14 C15 C16 C11 -0.1(3) . . . . ? C20 N3 C17 O3 -176.32(17) . . . . ? C20 N3 C17 C18 2.6(3) . . . . ? C12 O3 C17 N3 -11.6(3) . . . . ? C12 O3 C17 C18 169.5(2) . . . . ? C19 N4 C18 C17 -1.6(4) . . . . ? N3 C17 C18 N4 0.1(4) . . . . ? O3 C17 C18 N4 179.0(2) . . . . ? C18 N4 C19 C20 0.4(4) . . . . ? C17 N3 C20 O2 176.47(18) . . . . ? C17 N3 C20 C19 -3.8(3) . . . . ? C9 O2 C20 N3 -2.3(3) . . . . ? C9 O2 C20 C19 177.92(19) . . . . ? N4 C19 C20 N3 2.4(3) . . . . ? N4 C19 C20 O2 -177.8(2) . . . . ? Cu1 O5 C21 O6 0.9(3) . . . . ? Cu1 O5 C21 C22 -179.07(15) . . . . ? Cu1 O6 C21 O5 -1.8(3) 2_465 . . . ? Cu1 O6 C21 C22 178.16(15) 2_465 . . . ? Cu1 O7 C23 O8 4.3(3) . . . . ? Cu1 O7 C23 C24 -175.32(15) . . . . ? Cu1 O8 C23 O7 -3.3(3) 2_465 . . . ? Cu1 O8 C23 C24 176.34(15) 2_465 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.281 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.043 # Attachment 'complex_5.cif' data_z _database_code_depnum_ccdc_archive 'CCDC 737912' #TrackingRef 'complex_5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 Cu0.50 N3 O6' _chemical_formula_weight 295.95 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 Hexagonal _symmetry_space_group_name_H-M P6(3)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 13.0752(3) _cell_length_b 13.0752(3) _cell_length_c 25.2402(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3736.97(18) _cell_formula_units_Z 12 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9923 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 27.89 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.549 _exptl_crystal_size_mid 0.390 _exptl_crystal_size_min 0.146 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1794 _exptl_absorpt_coefficient_mu 0.951 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.765436 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 41248 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0092 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2159 _reflns_number_gt 1816 _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^)+(0.1612P)^2^+9.8080P] 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 2159 _refine_ls_number_parameters 204 _refine_ls_number_restraints 96 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.2658 _refine_ls_wR_factor_gt 0.2433 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.205 _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 -1.0000 -0.5000 0.5000 0.0615(6) Uani 1 2 d S . . O1 O -1.1289(5) -0.3304(8) 0.6557(3) 0.123(3) Uani 1 1 d U . . O2 O -0.7370(3) -0.2334(4) 0.65459(14) 0.0457(10) Uani 1 1 d . . . N1 N -0.9701(5) -0.4055(5) 0.56717(19) 0.0518(14) Uani 1 1 d . . . N2 N -0.9318(4) -0.2781(4) 0.65985(17) 0.0374(10) Uani 1 1 d . . . C1 C -0.8646(5) -0.3520(6) 0.5895(2) 0.0441(13) Uani 1 1 d . . . H1A H -0.8010 -0.3573 0.5741 0.053 Uiso 1 1 calc R . . C2 C -0.8479(4) -0.2873(4) 0.63608(18) 0.0316(10) Uani 1 1 d . . . C3 C -1.0356(6) -0.3340(8) 0.6360(3) 0.066(2) Uani 1 1 d . . . C4 C -1.0562(6) -0.3967(8) 0.5894(3) 0.073(2) Uani 1 1 d . . . H4A H -1.1322 -0.4333 0.5735 0.088 Uiso 1 1 calc R . . C5 C -0.7526(5) -0.2346(6) 0.7500 0.0273(13) Uani 1 2 d S . . H5A H -0.8143 -0.3147 0.7500 0.033 Uiso 1 2 calc SR . . C6 C -0.7063(4) -0.1744(4) 0.70356(18) 0.0291(10) Uani 1 1 d . . . C7 C -0.6171(4) -0.0572(5) 0.7027(2) 0.0362(12) Uani 1 1 d . . . H7A H -0.5867 -0.0173 0.6701 0.043 Uiso 1 1 calc R . . C8 C -0.5737(6) 0.0000(6) 0.7500 0.0375(16) Uani 1 2 d S . . H8A H -0.5128 0.0804 0.7500 0.045 Uiso 1 2 calc SR . . C9 C -1.1653(6) -0.1461(6) 0.7500 0.0396(17) Uani 1 2 d S . . H9A H -1.1838 -0.0845 0.7500 0.048 Uiso 1 2 calc SR . . C10 C -1.1522(4) -0.1898(6) 0.7035(2) 0.0469(14) Uani 1 1 d . . . H10A H -1.1615 -0.1591 0.6708 0.056 Uiso 1 1 calc R . . C11 C -1.1258(5) -0.2775(6) 0.7038(2) 0.0511(16) Uani 1 1 d . . . C12 C -1.1133(6) -0.3261(7) 0.7500 0.051(2) Uani 1 2 d S . . H12A H -1.0971 -0.3893 0.7500 0.061 Uiso 1 2 calc SR . . N3 N -0.9823(14) -0.6560(11) 0.5530(5) 0.099(3) Uani 0.67 1 d PU . . O3 O -1.0920(14) -0.6663(11) 0.5497(5) 0.127(4) Uani 0.67 1 d PU . . O4 O -0.8994(8) -0.5650(6) 0.5281(3) 0.0646(18) Uani 0.67 1 d PU . . O5 O -0.9384(15) -0.7242(12) 0.5714(6) 0.140(5) Uani 0.67 1 d PU . . O9 O -0.814(2) -0.462(2) 0.5056(8) 0.107(5) Uani 0.33 1 d PU . . N4 N -0.6667 -0.3333 0.4793(16) 0.196(7) Uani 1 3 d SU . . O6 O -0.7766(19) -0.3427(15) 0.4622(7) 0.221(6) Uani 1 1 d U . . O7 O -1.0000 -1.0000 0.4280(17) 0.245(11) Uani 1 3 d SU . . O8 O -0.3333 0.3333 0.7500 0.213(11) Uani 1 6 d SU . . O10 O -0.6667 -0.3333 0.318(3) 0.224(12) Uani 0.50 3 d SPU . . 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 0.0887(10) 0.0907(10) 0.0347(8) -0.0339(5) -0.0251(5) 0.0671(8) O1 0.062(3) 0.224(7) 0.103(4) -0.118(5) -0.042(3) 0.086(4) O2 0.0380(19) 0.074(3) 0.0260(19) -0.0125(17) -0.0003(14) 0.0286(19) N1 0.067(3) 0.079(4) 0.031(2) -0.026(2) -0.019(2) 0.053(3) N2 0.041(2) 0.051(3) 0.029(2) -0.0119(18) -0.0071(17) 0.029(2) C1 0.057(3) 0.065(3) 0.027(3) -0.013(2) -0.006(2) 0.042(3) C2 0.039(2) 0.040(2) 0.023(2) -0.0009(19) -0.0014(19) 0.024(2) C3 0.046(3) 0.112(6) 0.053(4) -0.050(4) -0.019(3) 0.049(4) C4 0.058(4) 0.120(7) 0.049(4) -0.053(4) -0.024(3) 0.050(4) C5 0.027(3) 0.031(3) 0.029(3) 0.000 0.000 0.019(3) C6 0.026(2) 0.041(3) 0.026(2) -0.0035(18) -0.0005(17) 0.0208(19) C7 0.032(2) 0.043(3) 0.041(3) 0.014(2) 0.009(2) 0.025(2) C8 0.030(3) 0.027(3) 0.056(5) 0.000 0.000 0.014(3) C9 0.025(3) 0.028(3) 0.065(5) 0.000 0.000 0.013(3) C10 0.025(2) 0.069(4) 0.045(3) 0.020(3) 0.001(2) 0.022(2) C11 0.028(2) 0.078(4) 0.049(4) -0.036(3) -0.015(2) 0.028(3) C12 0.028(4) 0.034(4) 0.094(7) 0.000 0.000 0.017(3) N3 0.129(6) 0.079(5) 0.063(5) -0.005(4) -0.021(5) 0.032(5) O3 0.135(7) 0.098(6) 0.095(6) -0.013(5) 0.011(6) 0.019(5) O4 0.103(5) 0.057(3) 0.036(3) -0.015(3) -0.023(3) 0.042(3) O5 0.165(9) 0.104(7) 0.120(8) 0.028(6) -0.039(7) 0.043(6) O9 0.116(8) 0.101(8) 0.084(8) -0.018(7) 0.001(7) 0.039(6) N4 0.189(7) 0.189(7) 0.209(10) 0.000 0.000 0.095(4) O6 0.220(9) 0.197(8) 0.226(9) -0.008(7) 0.001(7) 0.089(7) O7 0.249(11) 0.249(11) 0.237(15) 0.000 0.000 0.125(5) O8 0.208(11) 0.208(11) 0.225(15) 0.000 0.000 0.104(5) O10 0.220(12) 0.220(12) 0.232(17) 0.000 0.000 0.110(6) _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 2.017(4) 7_346 ? Cu1 N1 2.017(4) . ? Cu1 O4 2.018(8) . ? Cu1 O4 2.018(8) 7_346 ? Cu1 O9 2.23(3) . ? Cu1 O9 2.23(3) 7_346 ? Cu1 O3 2.266(13) 7_346 ? Cu1 O3 2.266(13) . ? O1 C3 1.339(8) . ? O1 C11 1.387(7) . ? O2 C2 1.340(6) . ? O2 C6 1.405(6) . ? N1 C4 1.313(9) . ? N1 C1 1.321(8) . ? N2 C2 1.307(6) . ? N2 C3 1.321(7) . ? C1 C2 1.401(7) . ? C1 H1A 0.9500 . ? C3 C4 1.383(8) . ? C4 H4A 0.9500 . ? C5 C6 1.372(6) 10_557 ? C5 C6 1.372(6) . ? C5 H5A 0.9500 . ? C6 C7 1.386(7) . ? C7 C8 1.371(7) . ? C7 H7A 0.9500 . ? C8 C7 1.371(7) 10_557 ? C8 H8A 0.9500 . ? C9 C10 1.354(7) . ? C9 C10 1.354(7) 10_557 ? C9 H9A 0.9500 . ? C10 C11 1.352(9) . ? C10 H10A 0.9500 . ? C11 C12 1.377(8) . ? C12 C11 1.377(8) 10_557 ? C12 H12A 0.9500 . ? N3 O4 1.302(15) . ? N3 O5 1.36(2) . ? N3 O3 1.38(2) . ? O3 O6 1.81(3) 7_346 ? O4 O9 1.37(3) . ? O9 O6 1.76(3) . ? N4 O6 1.45(2) . ? N4 O6 1.45(2) 3_445 ? N4 O6 1.45(2) 2_455 ? O6 O3 1.81(3) 7_346 ? O8 O10 1.73(7) 7_456 ? O8 O10 1.73(7) 4_455 ? O10 O8 1.73(7) 7_456 ? 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 N1 180.000(1) 7_346 . ? N1 Cu1 O4 90.3(2) 7_346 . ? N1 Cu1 O4 89.7(2) . . ? N1 Cu1 O4 89.7(2) 7_346 7_346 ? N1 Cu1 O4 90.3(2) . 7_346 ? O4 Cu1 O4 180.0(4) . 7_346 ? N1 Cu1 O9 92.6(6) 7_346 . ? N1 Cu1 O9 87.4(6) . . ? O4 Cu1 O9 37.2(7) . . ? O4 Cu1 O9 142.8(7) 7_346 . ? N1 Cu1 O9 87.4(6) 7_346 7_346 ? N1 Cu1 O9 92.6(6) . 7_346 ? O4 Cu1 O9 142.8(7) . 7_346 ? O4 Cu1 O9 37.2(7) 7_346 7_346 ? O9 Cu1 O9 180.0(11) . 7_346 ? N1 Cu1 O3 88.3(3) 7_346 7_346 ? N1 Cu1 O3 91.7(3) . 7_346 ? O4 Cu1 O3 117.0(5) . 7_346 ? O4 Cu1 O3 63.0(5) 7_346 7_346 ? O9 Cu1 O3 79.9(8) . 7_346 ? O9 Cu1 O3 100.1(8) 7_346 7_346 ? N1 Cu1 O3 91.7(3) 7_346 . ? N1 Cu1 O3 88.3(3) . . ? O4 Cu1 O3 63.0(5) . . ? O4 Cu1 O3 117.0(5) 7_346 . ? O9 Cu1 O3 100.1(8) . . ? O9 Cu1 O3 79.9(8) 7_346 . ? O3 Cu1 O3 180.0(5) 7_346 . ? C3 O1 C11 122.8(5) . . ? C2 O2 C6 122.2(4) . . ? C4 N1 C1 119.1(5) . . ? C4 N1 Cu1 120.0(4) . . ? C1 N1 Cu1 120.9(4) . . ? C2 N2 C3 114.7(5) . . ? N1 C1 C2 118.9(5) . . ? N1 C1 H1A 120.5 . . ? C2 C1 H1A 120.5 . . ? N2 C2 O2 121.9(4) . . ? N2 C2 C1 123.8(5) . . ? O2 C2 C1 114.3(4) . . ? N2 C3 O1 120.9(5) . . ? N2 C3 C4 123.8(6) . . ? O1 C3 C4 115.2(6) . . ? N1 C4 C3 119.7(6) . . ? N1 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C6 C5 C6 117.3(6) 10_557 . ? C6 C5 H5A 121.3 10_557 . ? C6 C5 H5A 121.3 . . ? C5 C6 C7 122.2(5) . . ? C5 C6 O2 120.9(4) . . ? C7 C6 O2 116.4(4) . . ? C8 C7 C6 118.7(5) . . ? C8 C7 H7A 120.7 . . ? C6 C7 H7A 120.7 . . ? C7 C8 C7 120.9(7) . 10_557 ? C7 C8 H8A 119.5 . . ? C7 C8 H8A 119.5 10_557 . ? C10 C9 C10 120.3(7) . 10_557 ? C10 C9 H9A 119.8 . . ? C10 C9 H9A 119.8 10_557 . ? C11 C10 C9 119.5(5) . . ? C11 C10 H10A 120.2 . . ? C9 C10 H10A 120.2 . . ? C10 C11 C12 122.4(5) . . ? C10 C11 O1 117.5(7) . . ? C12 C11 O1 119.4(7) . . ? C11 C12 C11 115.9(7) . 10_557 ? C11 C12 H12A 122.1 . . ? C11 C12 H12A 122.1 10_557 . ? O4 N3 O5 109.5(15) . . ? O4 N3 O3 114.3(12) . . ? O5 N3 O3 135.8(14) . . ? N3 O3 O6 169.8(13) . 7_346 ? N3 O3 Cu1 85.0(8) . . ? O6 O3 Cu1 84.9(9) 7_346 . ? N3 O4 O9 174.0(14) . . ? N3 O4 Cu1 97.8(9) . . ? O9 O4 Cu1 79.7(13) . . ? O4 O9 O6 149(2) . . ? O4 O9 Cu1 63.1(11) . . ? O6 O9 Cu1 87.0(14) . . ? O6 N4 O6 111.5(17) . 3_445 ? O6 N4 O6 111.5(17) . 2_455 ? O6 N4 O6 111.5(17) 3_445 2_455 ? N4 O6 O9 73.4(15) . . ? N4 O6 O3 169.1(19) . 7_346 ? O9 O6 O3 107.9(15) . 7_346 ? O10 O8 O10 180.00(4) 7_456 4_455 ? 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 N1 Cu1 N1 C4 11(29) 7_346 . . . ? O4 Cu1 N1 C4 -139.4(7) . . . . ? O4 Cu1 N1 C4 40.6(7) 7_346 . . . ? O9 Cu1 N1 C4 -176.5(10) . . . . ? O9 Cu1 N1 C4 3.5(10) 7_346 . . . ? O3 Cu1 N1 C4 103.7(8) 7_346 . . . ? O3 Cu1 N1 C4 -76.3(8) . . . . ? N1 Cu1 N1 C1 -169(17) 7_346 . . . ? O4 Cu1 N1 C1 40.5(6) . . . . ? O4 Cu1 N1 C1 -139.5(6) 7_346 . . . ? O9 Cu1 N1 C1 3.4(8) . . . . ? O9 Cu1 N1 C1 -176.6(8) 7_346 . . . ? O3 Cu1 N1 C1 -76.5(7) 7_346 . . . ? O3 Cu1 N1 C1 103.5(7) . . . . ? C4 N1 C1 C2 -0.1(10) . . . . ? Cu1 N1 C1 C2 180.0(4) . . . . ? C3 N2 C2 O2 178.4(6) . . . . ? C3 N2 C2 C1 -0.9(9) . . . . ? C6 O2 C2 N2 7.1(8) . . . . ? C6 O2 C2 C1 -173.6(5) . . . . ? N1 C1 C2 N2 1.3(9) . . . . ? N1 C1 C2 O2 -178.0(5) . . . . ? C2 N2 C3 O1 -179.0(8) . . . . ? C2 N2 C3 C4 -0.7(12) . . . . ? C11 O1 C3 N2 -5.5(16) . . . . ? C11 O1 C3 C4 176.0(9) . . . . ? C1 N1 C4 C3 -1.3(13) . . . . ? Cu1 N1 C4 C3 178.6(7) . . . . ? N2 C3 C4 N1 1.8(15) . . . . ? O1 C3 C4 N1 -179.8(9) . . . . ? C6 C5 C6 C7 -0.6(8) 10_557 . . . ? C6 C5 C6 O2 171.2(3) 10_557 . . . ? C2 O2 C6 C5 63.1(7) . . . . ? C2 O2 C6 C7 -124.6(5) . . . . ? C5 C6 C7 C8 0.2(7) . . . . ? O2 C6 C7 C8 -172.0(5) . . . . ? C6 C7 C8 C7 0.2(9) . . . 10_557 ? C10 C9 C10 C11 -0.1(11) 10_557 . . . ? C9 C10 C11 C12 1.1(9) . . . . ? C9 C10 C11 O1 171.5(6) . . . . ? C3 O1 C11 C10 122.5(10) . . . . ? C3 O1 C11 C12 -66.8(13) . . . . ? C10 C11 C12 C11 -1.9(11) . . . 10_557 ? O1 C11 C12 C11 -172.2(5) . . . 10_557 ? O4 N3 O3 O6 3(7) . . . 7_346 ? O5 N3 O3 O6 -168(6) . . . 7_346 ? O4 N3 O3 Cu1 0.4(10) . . . . ? O5 N3 O3 Cu1 -171.2(17) . . . . ? N1 Cu1 O3 N3 89.2(7) 7_346 . . . ? N1 Cu1 O3 N3 -90.8(7) . . . . ? O4 Cu1 O3 N3 -0.2(6) . . . . ? O4 Cu1 O3 N3 179.8(6) 7_346 . . . ? O9 Cu1 O3 N3 -3.8(9) . . . . ? O9 Cu1 O3 N3 176.2(9) 7_346 . . . ? O3 Cu1 O3 N3 -174(100) 7_346 . . . ? N1 Cu1 O3 O6 -90.2(7) 7_346 . . 7_346 ? N1 Cu1 O3 O6 89.8(7) . . . 7_346 ? O4 Cu1 O3 O6 -179.7(8) . . . 7_346 ? O4 Cu1 O3 O6 0.3(8) 7_346 . . 7_346 ? O9 Cu1 O3 O6 176.8(9) . . . 7_346 ? O9 Cu1 O3 O6 -3.2(9) 7_346 . . 7_346 ? O3 Cu1 O3 O6 6(100) 7_346 . . 7_346 ? O5 N3 O4 O9 -122(15) . . . . ? O3 N3 O4 O9 65(15) . . . . ? O5 N3 O4 Cu1 173.4(10) . . . . ? O3 N3 O4 Cu1 -0.4(11) . . . . ? N1 Cu1 O4 N3 -91.5(6) 7_346 . . . ? N1 Cu1 O4 N3 88.5(6) . . . . ? O4 Cu1 O4 N3 12(100) 7_346 . . . ? O9 Cu1 O4 N3 174.5(12) . . . . ? O9 Cu1 O4 N3 -5.5(12) 7_346 . . . ? O3 Cu1 O4 N3 -179.8(7) 7_346 . . . ? O3 Cu1 O4 N3 0.2(7) . . . . ? N1 Cu1 O4 O9 94.0(9) 7_346 . . . ? N1 Cu1 O4 O9 -86.0(9) . . . . ? O4 Cu1 O4 O9 -163(100) 7_346 . . . ? O9 Cu1 O4 O9 180.000(3) 7_346 . . . ? O3 Cu1 O4 O9 5.8(10) 7_346 . . . ? O3 Cu1 O4 O9 -174.2(10) . . . . ? N3 O4 O9 O6 -82(14) . . . . ? Cu1 O4 O9 O6 -17(3) . . . . ? N3 O4 O9 Cu1 -66(15) . . . . ? N1 Cu1 O9 O4 -87.0(8) 7_346 . . . ? N1 Cu1 O9 O4 93.0(8) . . . . ? O4 Cu1 O9 O4 180.000(4) 7_346 . . . ? O9 Cu1 O9 O4 108(100) 7_346 . . . ? O3 Cu1 O9 O4 -174.8(9) 7_346 . . . ? O3 Cu1 O9 O4 5.2(9) . . . . ? N1 Cu1 O9 O6 84.5(9) 7_346 . . . ? N1 Cu1 O9 O6 -95.5(9) . . . . ? O4 Cu1 O9 O6 171.5(15) . . . . ? O4 Cu1 O9 O6 -8.5(15) 7_346 . . . ? O9 Cu1 O9 O6 -81(100) 7_346 . . . ? O3 Cu1 O9 O6 -3.3(9) 7_346 . . . ? O3 Cu1 O9 O6 176.7(9) . . . . ? O6 N4 O6 O9 -171(3) 3_445 . . . ? O6 N4 O6 O9 63(2) 2_455 . . . ? O6 N4 O6 O3 -73(13) 3_445 . . 7_346 ? O6 N4 O6 O3 162(9) 2_455 . . 7_346 ? O4 O9 O6 N4 -172(4) . . . . ? Cu1 O9 O6 N4 173.0(17) . . . . ? O4 O9 O6 O3 19(4) . . . 7_346 ? Cu1 O9 O6 O3 4.3(12) . . . 7_346 ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 1.069 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.123 # Attachment 'Cif-6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 737913' #TrackingRef 'Cif-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H27 Cu2 N5 O12' _chemical_formula_weight 776.65 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.2875(6) _cell_length_b 13.1823(9) _cell_length_c 31.559(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3447.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 1.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5285 _exptl_absorpt_correction_T_max 0.7683 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 38874 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6063 _reflns_number_gt 5245 _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^)+(0.0641P)^2^+4.1717P] 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 0.011(17) _refine_ls_number_reflns 6063 _refine_ls_number_parameters 443 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1260 _refine_ls_wR_factor_gt 0.1153 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.120 _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 0.52716(7) 0.52586(5) -0.156690(17) 0.02863(16) Uani 1 1 d . . . Cu2 Cu 0.62690(7) 0.47797(5) -0.232935(17) 0.02787(16) Uani 1 1 d . . . N1 N 0.4670(5) 0.5633(3) -0.09050(12) 0.0270(9) Uani 1 1 d . . . N2 N 0.4132(5) 0.6117(3) -0.00625(12) 0.0257(9) Uani 1 1 d . . . N3 N 0.5901(5) 0.5967(3) 0.13270(12) 0.0273(9) Uani 1 1 d . . . N4 N 0.7736(5) 0.5523(3) 0.20376(13) 0.0283(10) Uani 1 1 d . . . N5 N 0.7169(9) 0.4287(9) 0.0056(5) 0.163(6) Uani 1 1 d . . . O1 O 0.8219(5) 0.4216(3) -0.20797(12) 0.0447(10) Uani 1 1 d . . . O2 O 0.7401(5) 0.4595(3) -0.14242(11) 0.0390(9) Uani 1 1 d . . . O3 O 0.7268(4) 0.6163(3) -0.22889(11) 0.0345(9) Uani 1 1 d . . . O4 O 0.6326(5) 0.6556(3) -0.16541(10) 0.0365(9) Uani 1 1 d . . . O5 O 0.5165(5) 0.3494(3) -0.21929(11) 0.0392(9) Uani 1 1 d . . . O6 O 0.4306(5) 0.3904(3) -0.15412(12) 0.0379(9) Uani 1 1 d . . . O7 O 0.4267(4) 0.5366(3) -0.25336(11) 0.0371(9) Uani 1 1 d . . . O8 O 0.3387(5) 0.5770(3) -0.18876(12) 0.0435(10) Uani 1 1 d . . . O9 O 0.5458(5) 0.7629(3) -0.01846(10) 0.0329(9) Uani 1 1 d . . . O10 O 0.2732(6) 0.4595(3) 0.00041(11) 0.0491(11) Uani 1 1 d . . . O11 O 0.7486(5) 0.7393(3) 0.12337(12) 0.0393(10) Uani 1 1 d . . . O12 O 0.4468(5) 0.4480(3) 0.14570(12) 0.0462(11) Uani 1 1 d . . . C1 C 0.8392(7) 0.4223(5) -0.16841(19) 0.0388(14) Uani 1 1 d . . . C2 C 0.9907(8) 0.3746(6) -0.1510(2) 0.063(2) Uani 1 1 d . . . H2A H 0.9902 0.3793 -0.1200 0.094 Uiso 1 1 calc R . . H2B H 1.0852 0.4103 -0.1622 0.094 Uiso 1 1 calc R . . H2C H 0.9952 0.3031 -0.1595 0.094 Uiso 1 1 calc R . . C3 C 0.7111(6) 0.6754(4) -0.19852(16) 0.0282(11) Uani 1 1 d . . . C4 C 0.7864(7) 0.7784(4) -0.20209(18) 0.0394(13) Uani 1 1 d . . . H4A H 0.8425 0.7841 -0.2293 0.059 Uiso 1 1 calc R . . H4B H 0.8636 0.7881 -0.1789 0.059 Uiso 1 1 calc R . . H4C H 0.7021 0.8304 -0.2004 0.059 Uiso 1 1 calc R . . C5 C 0.4487(7) 0.3292(4) -0.18422(17) 0.0336(12) Uani 1 1 d . . . C6 C 0.3882(9) 0.2245(5) -0.1780(2) 0.0494(16) Uani 1 1 d . . . H6A H 0.3390 0.2187 -0.1499 0.074 Uiso 1 1 calc R . . H6B H 0.4781 0.1765 -0.1803 0.074 Uiso 1 1 calc R . . H6C H 0.3074 0.2089 -0.1997 0.074 Uiso 1 1 calc R . . C7 C 0.3261(7) 0.5757(4) -0.22842(17) 0.0355(13) Uani 1 1 d . . . C8 C 0.1809(8) 0.6250(6) -0.2474(2) 0.059(2) Uani 1 1 d . . . H8A H 0.1852 0.6186 -0.2783 0.088 Uiso 1 1 calc R . . H8B H 0.1792 0.6970 -0.2397 0.088 Uiso 1 1 calc R . . H8C H 0.0832 0.5919 -0.2368 0.088 Uiso 1 1 calc R . . C9 C 0.3822(7) 0.5021(4) -0.06566(15) 0.0325(13) Uani 1 1 d . . . H9A H 0.3375 0.4413 -0.0768 0.039 Uiso 1 1 calc R . . C10 C 0.3591(6) 0.5271(4) -0.02333(14) 0.0295(10) Uani 1 1 d . . . C11 C 0.4933(6) 0.6724(4) -0.03178(14) 0.0234(10) Uani 1 1 d . . . C12 C 0.5235(6) 0.6491(4) -0.07470(14) 0.0258(10) Uani 1 1 d . . . H12A H 0.5835 0.6945 -0.0920 0.031 Uiso 1 1 calc R . . C13 C 0.5650(6) 0.5147(4) 0.15581(15) 0.0271(10) Uani 1 1 d . . . C14 C 0.6552(6) 0.4902(4) 0.19127(15) 0.0310(12) Uani 1 1 d . . . H14A H 0.6332 0.4298 0.2066 0.037 Uiso 1 1 calc R . . C15 C 0.8040(6) 0.6345(4) 0.18105(16) 0.0295(12) Uani 1 1 d . . . H15A H 0.8887 0.6791 0.1891 0.035 Uiso 1 1 calc R . . C16 C 0.7111(6) 0.6551(4) 0.14546(15) 0.0275(11) Uani 1 1 d . . . C17 C 0.5368(6) 0.7867(4) 0.02459(14) 0.0237(10) Uani 1 1 d . . . C18 C 0.4312(6) 0.8630(4) 0.03648(16) 0.0296(11) Uani 1 1 d . . . H18A H 0.3598 0.8922 0.0163 0.036 Uiso 1 1 calc R . . C19 C 0.4309(7) 0.8960(4) 0.07800(17) 0.0354(13) Uani 1 1 d . . . H19A H 0.3591 0.9485 0.0864 0.042 Uiso 1 1 calc R . . C20 C 0.5336(7) 0.8537(4) 0.10720(16) 0.0348(12) Uani 1 1 d . . . H20A H 0.5349 0.8769 0.1357 0.042 Uiso 1 1 calc R . . C21 C 0.6351(6) 0.7765(4) 0.09420(15) 0.0288(11) Uani 1 1 d . . . C22 C 0.6368(7) 0.7407(4) 0.05340(15) 0.0283(11) Uani 1 1 d . . . H22A H 0.7048 0.6859 0.0454 0.034 Uiso 1 1 calc R . . C23 C 0.2466(7) 0.4795(5) 0.04353(15) 0.0349(12) Uani 1 1 d . . . C24 C 0.0929(7) 0.4965(4) 0.05621(19) 0.0438(16) Uani 1 1 d . . . H24A H 0.0095 0.5039 0.0358 0.053 Uiso 1 1 calc R . . C25 C 0.0580(8) 0.5030(5) 0.09867(19) 0.0493(17) Uani 1 1 d . . . H25A H -0.0495 0.5162 0.1076 0.059 Uiso 1 1 calc R . . C26 C 0.1779(7) 0.4906(5) 0.12818(17) 0.0381(14) Uani 1 1 d . . . H26A H 0.1544 0.4946 0.1576 0.046 Uiso 1 1 calc R . . C27 C 0.3308(6) 0.4724(4) 0.11465(15) 0.0317(11) Uani 1 1 d . . . C28 C 0.3714(6) 0.4671(4) 0.07230(15) 0.0345(12) Uani 1 1 d . . . H28A H 0.4793 0.4555 0.0633 0.041 Uiso 1 1 calc R . . C29 C 0.651(2) 0.3391(18) -0.0206(4) 0.224(12) Uani 1 1 d D . . C30 C 0.612(2) 0.2837(9) -0.0603(4) 0.166(7) Uani 1 1 d D . . H30A H 0.6650 0.3170 -0.0843 0.249 Uiso 1 1 calc R . . H30B H 0.4947 0.2842 -0.0648 0.249 Uiso 1 1 calc R . . H30C H 0.6496 0.2135 -0.0581 0.249 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 0.0303(3) 0.0382(3) 0.0173(3) -0.0069(3) 0.0001(2) -0.0017(3) Cu2 0.0263(3) 0.0376(3) 0.0198(3) -0.0061(3) 0.0033(2) 0.0006(3) N1 0.035(2) 0.032(2) 0.0136(19) -0.0029(17) -0.0042(18) 0.0033(19) N2 0.032(2) 0.031(2) 0.014(2) 0.0007(17) 0.0001(17) 0.0005(18) N3 0.031(2) 0.034(2) 0.017(2) 0.0010(17) -0.0044(17) -0.0051(18) N4 0.026(2) 0.037(3) 0.021(2) 0.0012(18) -0.0004(17) 0.0027(18) N5 0.032(4) 0.171(10) 0.285(16) 0.147(11) 0.026(7) -0.008(5) O1 0.040(2) 0.063(3) 0.032(2) -0.0021(19) -0.0008(17) 0.015(2) O2 0.036(2) 0.048(2) 0.032(2) -0.0062(18) -0.0141(17) 0.0049(19) O3 0.038(2) 0.037(2) 0.029(2) -0.0113(17) 0.0103(17) -0.0052(17) O4 0.049(2) 0.040(2) 0.0212(18) -0.0062(15) 0.0095(18) -0.0054(19) O5 0.051(2) 0.041(2) 0.0264(19) -0.0075(16) 0.0091(18) -0.0079(19) O6 0.044(2) 0.040(2) 0.030(2) -0.0073(18) 0.0046(18) -0.0124(18) O7 0.0284(18) 0.060(3) 0.0224(17) -0.0045(18) 0.0004(15) 0.0046(19) O8 0.036(2) 0.067(3) 0.027(2) -0.0118(19) -0.0024(17) 0.0112(19) O9 0.056(2) 0.0297(19) 0.0131(16) -0.0009(14) 0.0067(16) -0.0067(17) O10 0.074(3) 0.055(3) 0.0185(17) -0.0023(18) -0.0002(19) -0.034(2) O11 0.039(2) 0.046(2) 0.033(2) 0.0194(17) -0.0165(17) -0.0189(18) O12 0.056(3) 0.051(2) 0.032(2) 0.0201(17) -0.0256(19) -0.025(2) C1 0.030(3) 0.043(3) 0.044(4) -0.003(3) -0.008(3) 0.005(3) C2 0.056(4) 0.064(4) 0.069(5) -0.007(4) -0.024(4) 0.024(4) C3 0.022(2) 0.035(3) 0.028(3) -0.004(2) -0.005(2) 0.003(2) C4 0.040(3) 0.040(3) 0.038(3) -0.007(3) 0.000(3) -0.003(3) C5 0.033(3) 0.035(3) 0.032(3) -0.003(2) -0.005(2) -0.005(2) C6 0.064(4) 0.044(4) 0.040(3) -0.003(3) 0.010(3) -0.008(3) C7 0.034(3) 0.045(3) 0.028(3) -0.009(2) -0.002(2) -0.001(2) C8 0.040(4) 0.096(6) 0.040(4) -0.018(4) -0.015(3) 0.021(4) C9 0.043(3) 0.035(3) 0.020(2) -0.002(2) -0.007(2) -0.008(2) C10 0.034(3) 0.035(3) 0.020(2) 0.000(2) -0.004(2) 0.000(3) C11 0.029(3) 0.027(2) 0.014(2) -0.0020(19) -0.0016(19) 0.005(2) C12 0.025(2) 0.034(3) 0.018(2) 0.001(2) 0.002(2) 0.002(2) C13 0.026(2) 0.031(3) 0.024(2) 0.004(2) -0.0020(19) -0.004(2) C14 0.031(3) 0.037(3) 0.024(2) 0.004(2) -0.006(2) -0.002(2) C15 0.026(3) 0.037(3) 0.025(3) 0.005(2) -0.008(2) -0.005(2) C16 0.026(3) 0.037(3) 0.019(2) 0.000(2) -0.001(2) -0.006(2) C17 0.036(3) 0.021(2) 0.014(2) -0.0013(19) 0.003(2) -0.006(2) C18 0.031(3) 0.034(3) 0.024(3) 0.001(2) -0.004(2) 0.002(2) C19 0.039(3) 0.039(3) 0.029(3) -0.012(2) 0.006(2) 0.005(2) C20 0.045(3) 0.044(3) 0.015(2) -0.003(2) 0.001(2) -0.008(3) C21 0.031(3) 0.035(3) 0.021(2) 0.005(2) -0.006(2) -0.011(2) C22 0.029(3) 0.031(3) 0.026(3) 0.001(2) 0.004(2) -0.002(2) C23 0.050(3) 0.037(3) 0.018(2) 0.004(2) -0.006(2) -0.018(3) C24 0.042(3) 0.049(4) 0.041(3) 0.008(3) -0.015(3) -0.001(3) C25 0.041(3) 0.065(5) 0.042(3) -0.007(3) 0.004(3) 0.009(3) C26 0.047(3) 0.044(4) 0.023(3) -0.004(2) 0.006(2) -0.007(3) C27 0.043(3) 0.027(3) 0.025(3) 0.005(2) -0.014(2) -0.011(3) C28 0.032(3) 0.042(3) 0.030(3) -0.001(2) -0.004(2) -0.012(3) C29 0.178(14) 0.41(3) 0.082(8) -0.073(13) -0.060(9) 0.227(18) C30 0.231(17) 0.088(8) 0.179(14) 0.024(9) -0.023(14) 0.080(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.940(4) . ? Cu1 O6 1.958(4) . ? Cu1 O8 1.979(4) . ? Cu1 O2 2.021(4) . ? Cu1 N1 2.204(4) . ? Cu1 Cu2 2.6214(8) . ? Cu2 O7 1.940(4) . ? Cu2 O1 1.946(4) . ? Cu2 O5 1.974(4) . ? Cu2 O3 2.006(4) . ? Cu2 N4 2.198(4) 2_664 ? N1 C12 1.322(6) . ? N1 C9 1.327(6) . ? N2 C11 1.315(6) . ? N2 C10 1.317(7) . ? N3 C13 1.321(6) . ? N3 C16 1.327(6) . ? N4 C15 1.324(6) . ? N4 C14 1.337(7) . ? N4 Cu2 2.198(4) 2_665 ? N5 C29 1.54(2) . ? O1 C1 1.256(7) . ? O2 C1 1.260(7) . ? O3 C3 1.242(6) . ? O4 C3 1.258(6) . ? O5 C5 1.269(7) . ? O6 C5 1.255(6) . ? O7 C7 1.257(6) . ? O8 C7 1.256(7) . ? O9 C11 1.338(6) . ? O9 C17 1.396(5) . ? O10 C10 1.365(6) . ? O10 C23 1.403(6) . ? O11 C16 1.346(6) . ? O11 C21 1.405(6) . ? O12 C13 1.355(6) . ? O12 C27 1.410(6) . ? C1 C2 1.508(8) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.499(7) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.482(8) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.493(8) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.389(7) . ? C9 H9A 0.9500 . ? C11 C12 1.411(6) . ? C12 H12A 0.9500 . ? C13 C14 1.384(7) . ? C14 H14A 0.9500 . ? C15 C16 1.388(7) . ? C15 H15A 0.9500 . ? C17 C22 1.372(7) . ? C17 C18 1.384(7) . ? C18 C19 1.381(7) . ? C18 H18A 0.9500 . ? C19 C20 1.373(8) . ? C19 H19A 0.9500 . ? C20 C21 1.383(8) . ? C20 H20A 0.9500 . ? C21 C22 1.371(7) . ? C22 H22A 0.9500 . ? C23 C24 1.354(9) . ? C23 C28 1.386(7) . ? C24 C25 1.373(9) . ? C24 H24A 0.9500 . ? C25 C26 1.372(8) . ? C25 H25A 0.9500 . ? C26 C27 1.358(8) . ? C26 H26A 0.9500 . ? C27 C28 1.380(7) . ? C28 H28A 0.9500 . ? C29 C30 1.487(9) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 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 O4 Cu1 O6 173.53(15) . . ? O4 Cu1 O8 88.99(18) . . ? O6 Cu1 O8 90.56(18) . . ? O4 Cu1 O2 91.14(17) . . ? O6 Cu1 O2 87.29(17) . . ? O8 Cu1 O2 161.91(15) . . ? O4 Cu1 N1 92.22(15) . . ? O6 Cu1 N1 94.17(15) . . ? O8 Cu1 N1 103.28(16) . . ? O2 Cu1 N1 94.79(16) . . ? O4 Cu1 Cu2 86.57(10) . . ? O6 Cu1 Cu2 86.97(11) . . ? O8 Cu1 Cu2 82.04(11) . . ? O2 Cu1 Cu2 79.91(11) . . ? N1 Cu1 Cu2 174.53(12) . . ? O7 Cu2 O1 175.51(16) . . ? O7 Cu2 O5 91.04(17) . . ? O1 Cu2 O5 88.21(19) . . ? O7 Cu2 O3 90.68(17) . . ? O1 Cu2 O3 88.78(18) . . ? O5 Cu2 O3 163.29(14) . . ? O7 Cu2 N4 95.24(15) . 2_664 ? O1 Cu2 N4 89.25(16) . 2_664 ? O5 Cu2 N4 102.50(15) . 2_664 ? O3 Cu2 N4 93.90(15) . 2_664 ? O7 Cu2 Cu1 86.52(10) . . ? O1 Cu2 Cu1 88.98(12) . . ? O5 Cu2 Cu1 81.97(10) . . ? O3 Cu2 Cu1 81.54(10) . . ? N4 Cu2 Cu1 175.14(12) 2_664 . ? C12 N1 C9 119.0(4) . . ? C12 N1 Cu1 118.0(3) . . ? C9 N1 Cu1 122.9(3) . . ? C11 N2 C10 115.9(4) . . ? C13 N3 C16 115.2(4) . . ? C15 N4 C14 118.8(4) . . ? C15 N4 Cu2 124.7(3) . 2_665 ? C14 N4 Cu2 115.6(3) . 2_665 ? C1 O1 Cu2 119.6(4) . . ? C1 O2 Cu1 126.3(3) . . ? C3 O3 Cu2 125.2(3) . . ? C3 O4 Cu1 122.2(3) . . ? C5 O5 Cu2 125.2(3) . . ? C5 O6 Cu1 120.4(3) . . ? C7 O7 Cu2 121.5(3) . . ? C7 O8 Cu1 124.8(4) . . ? C11 O9 C17 119.2(4) . . ? C10 O10 C23 119.5(4) . . ? C16 O11 C21 118.2(4) . . ? C13 O12 C27 120.6(4) . . ? O1 C1 O2 125.1(5) . . ? O1 C1 C2 117.0(6) . . ? O2 C1 C2 117.9(5) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O3 C3 O4 124.4(5) . . ? O3 C3 C4 117.8(5) . . ? O4 C3 C4 117.7(5) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O6 C5 O5 125.3(5) . . ? O6 C5 C6 117.3(5) . . ? O5 C5 C6 117.5(5) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O8 C7 O7 125.0(5) . . ? O8 C7 C8 117.5(5) . . ? O7 C7 C8 117.5(5) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C10 119.8(5) . . ? N1 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? N2 C10 O10 120.4(4) . . ? N2 C10 C9 123.2(5) . . ? O10 C10 C9 116.4(5) . . ? N2 C11 O9 121.0(4) . . ? N2 C11 C12 123.0(4) . . ? O9 C11 C12 116.0(4) . . ? N1 C12 C11 119.0(5) . . ? N1 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? N3 C13 O12 121.0(4) . . ? N3 C13 C14 123.5(5) . . ? O12 C13 C14 115.5(4) . . ? N4 C14 C13 119.5(5) . . ? N4 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? N4 C15 C16 119.5(5) . . ? N4 C15 H15A 120.2 . . ? C16 C15 H15A 120.2 . . ? N3 C16 O11 119.7(4) . . ? N3 C16 C15 123.4(5) . . ? O11 C16 C15 116.9(4) . . ? C22 C17 C18 121.6(4) . . ? C22 C17 O9 120.9(5) . . ? C18 C17 O9 117.4(4) . . ? C19 C18 C17 119.2(5) . . ? C19 C18 H18A 120.4 . . ? C17 C18 H18A 120.4 . . ? C20 C19 C18 120.5(5) . . ? C20 C19 H19A 119.8 . . ? C18 C19 H19A 119.8 . . ? C19 C20 C21 118.5(5) . . ? C19 C20 H20A 120.7 . . ? C21 C20 H20A 120.7 . . ? C22 C21 C20 122.6(5) . . ? C22 C21 O11 119.2(5) . . ? C20 C21 O11 118.0(4) . . ? C21 C22 C17 117.6(5) . . ? C21 C22 H22A 121.2 . . ? C17 C22 H22A 121.2 . . ? C24 C23 C28 121.9(5) . . ? C24 C23 O10 117.7(5) . . ? C28 C23 O10 119.7(5) . . ? C23 C24 C25 119.8(5) . . ? C23 C24 H24A 120.1 . . ? C25 C24 H24A 120.1 . . ? C26 C25 C24 120.1(6) . . ? C26 C25 H25A 119.9 . . ? C24 C25 H25A 119.9 . . ? C27 C26 C25 118.9(5) . . ? C27 C26 H26A 120.5 . . ? C25 C26 H26A 120.5 . . ? C26 C27 C28 122.8(5) . . ? C26 C27 O12 117.2(5) . . ? C28 C27 O12 119.7(5) . . ? C27 C28 C23 116.5(5) . . ? C27 C28 H28A 121.8 . . ? C23 C28 H28A 121.8 . . ? C30 C29 N5 155(2) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 O4 Cu1 Cu2 O7 -89.03(18) . . . . ? O6 Cu1 Cu2 O7 91.41(18) . . . . ? O8 Cu1 Cu2 O7 0.42(18) . . . . ? O2 Cu1 Cu2 O7 179.20(18) . . . . ? N1 Cu1 Cu2 O7 -166.3(12) . . . . ? O4 Cu1 Cu2 O1 91.09(18) . . . . ? O6 Cu1 Cu2 O1 -88.47(18) . . . . ? O8 Cu1 Cu2 O1 -179.45(19) . . . . ? O2 Cu1 Cu2 O1 -0.68(18) . . . . ? N1 Cu1 Cu2 O1 13.8(12) . . . . ? O4 Cu1 Cu2 O5 179.43(18) . . . . ? O6 Cu1 Cu2 O5 -0.13(17) . . . . ? O8 Cu1 Cu2 O5 -91.12(18) . . . . ? O2 Cu1 Cu2 O5 87.66(17) . . . . ? N1 Cu1 Cu2 O5 102.1(12) . . . . ? O4 Cu1 Cu2 O3 2.17(17) . . . . ? O6 Cu1 Cu2 O3 -177.38(17) . . . . ? O8 Cu1 Cu2 O3 91.63(18) . . . . ? O2 Cu1 Cu2 O3 -89.60(17) . . . . ? N1 Cu1 Cu2 O3 -75.1(12) . . . . ? O4 Cu1 Cu2 N4 22.3(13) . . . 2_664 ? O6 Cu1 Cu2 N4 -157.2(13) . . . 2_664 ? O8 Cu1 Cu2 N4 111.8(13) . . . 2_664 ? O2 Cu1 Cu2 N4 -69.4(13) . . . 2_664 ? N1 Cu1 Cu2 N4 -55.0(18) . . . 2_664 ? O4 Cu1 N1 C12 -5.4(4) . . . . ? O6 Cu1 N1 C12 173.6(4) . . . . ? O8 Cu1 N1 C12 -94.9(4) . . . . ? O2 Cu1 N1 C12 85.9(4) . . . . ? Cu2 Cu1 N1 C12 71.7(13) . . . . ? O4 Cu1 N1 C9 177.2(4) . . . . ? O6 Cu1 N1 C9 -3.9(4) . . . . ? O8 Cu1 N1 C9 87.7(4) . . . . ? O2 Cu1 N1 C9 -91.5(4) . . . . ? Cu2 Cu1 N1 C9 -105.8(12) . . . . ? O7 Cu2 O1 C1 0(3) . . . . ? O5 Cu2 O1 C1 -80.6(5) . . . . ? O3 Cu2 O1 C1 83.0(5) . . . . ? N4 Cu2 O1 C1 176.9(5) 2_664 . . . ? Cu1 Cu2 O1 C1 1.4(5) . . . . ? O4 Cu1 O2 C1 -86.2(5) . . . . ? O6 Cu1 O2 C1 87.6(5) . . . . ? O8 Cu1 O2 C1 4.1(9) . . . . ? N1 Cu1 O2 C1 -178.5(5) . . . . ? Cu2 Cu1 O2 C1 0.2(5) . . . . ? O7 Cu2 O3 C3 83.7(4) . . . . ? O1 Cu2 O3 C3 -91.8(4) . . . . ? O5 Cu2 O3 C3 -12.2(9) . . . . ? N4 Cu2 O3 C3 179.0(4) 2_664 . . . ? Cu1 Cu2 O3 C3 -2.7(4) . . . . ? O6 Cu1 O4 C3 1.3(18) . . . . ? O8 Cu1 O4 C3 -84.7(4) . . . . ? O2 Cu1 O4 C3 77.2(4) . . . . ? N1 Cu1 O4 C3 172.0(4) . . . . ? Cu2 Cu1 O4 C3 -2.6(4) . . . . ? O7 Cu2 O5 C5 -88.9(5) . . . . ? O1 Cu2 O5 C5 86.7(5) . . . . ? O3 Cu2 O5 C5 6.9(9) . . . . ? N4 Cu2 O5 C5 175.5(4) 2_664 . . . ? Cu1 Cu2 O5 C5 -2.6(4) . . . . ? O4 Cu1 O6 C5 -1.1(18) . . . . ? O8 Cu1 O6 C5 84.8(4) . . . . ? O2 Cu1 O6 C5 -77.3(4) . . . . ? N1 Cu1 O6 C5 -171.9(4) . . . . ? Cu2 Cu1 O6 C5 2.8(4) . . . . ? O1 Cu2 O7 C7 3(3) . . . . ? O5 Cu2 O7 C7 83.1(4) . . . . ? O3 Cu2 O7 C7 -80.2(4) . . . . ? N4 Cu2 O7 C7 -174.2(4) 2_664 . . . ? Cu1 Cu2 O7 C7 1.2(4) . . . . ? O4 Cu1 O8 C7 84.3(5) . . . . ? O6 Cu1 O8 C7 -89.2(5) . . . . ? O2 Cu1 O8 C7 -6.2(9) . . . . ? N1 Cu1 O8 C7 176.4(5) . . . . ? Cu2 Cu1 O8 C7 -2.3(5) . . . . ? Cu2 O1 C1 O2 -1.8(9) . . . . ? Cu2 O1 C1 C2 178.2(4) . . . . ? Cu1 O2 C1 O1 1.0(9) . . . . ? Cu1 O2 C1 C2 -179.0(4) . . . . ? Cu2 O3 C3 O4 1.6(7) . . . . ? Cu2 O3 C3 C4 -176.4(4) . . . . ? Cu1 O4 C3 O3 1.4(7) . . . . ? Cu1 O4 C3 C4 179.4(4) . . . . ? Cu1 O6 C5 O5 -5.7(8) . . . . ? Cu1 O6 C5 C6 173.3(4) . . . . ? Cu2 O5 C5 O6 5.8(8) . . . . ? Cu2 O5 C5 C6 -173.2(4) . . . . ? Cu1 O8 C7 O7 4.2(9) . . . . ? Cu1 O8 C7 C8 -175.2(5) . . . . ? Cu2 O7 C7 O8 -3.5(8) . . . . ? Cu2 O7 C7 C8 176.0(5) . . . . ? C12 N1 C9 C10 -2.2(8) . . . . ? Cu1 N1 C9 C10 175.2(4) . . . . ? C11 N2 C10 O10 -179.4(5) . . . . ? C11 N2 C10 C9 -0.5(7) . . . . ? C23 O10 C10 N2 -1.7(8) . . . . ? C23 O10 C10 C9 179.3(5) . . . . ? N1 C9 C10 N2 2.3(8) . . . . ? N1 C9 C10 O10 -178.8(5) . . . . ? C10 N2 C11 O9 176.2(4) . . . . ? C10 N2 C11 C12 -1.2(7) . . . . ? C17 O9 C11 N2 9.7(7) . . . . ? C17 O9 C11 C12 -172.8(4) . . . . ? C9 N1 C12 C11 0.7(7) . . . . ? Cu1 N1 C12 C11 -176.9(3) . . . . ? N2 C11 C12 N1 1.1(7) . . . . ? O9 C11 C12 N1 -176.3(4) . . . . ? C16 N3 C13 O12 -178.9(5) . . . . ? C16 N3 C13 C14 0.9(7) . . . . ? C27 O12 C13 N3 -10.5(8) . . . . ? C27 O12 C13 C14 169.7(5) . . . . ? C15 N4 C14 C13 -1.7(7) . . . . ? Cu2 N4 C14 C13 167.8(4) 2_665 . . . ? N3 C13 C14 N4 0.8(8) . . . . ? O12 C13 C14 N4 -179.4(5) . . . . ? C14 N4 C15 C16 1.1(7) . . . . ? Cu2 N4 C15 C16 -167.5(4) 2_665 . . . ? C13 N3 C16 O11 178.5(5) . . . . ? C13 N3 C16 C15 -1.6(7) . . . . ? C21 O11 C16 N3 15.8(7) . . . . ? C21 O11 C16 C15 -164.1(5) . . . . ? N4 C15 C16 N3 0.7(8) . . . . ? N4 C15 C16 O11 -179.4(5) . . . . ? C11 O9 C17 C22 71.3(6) . . . . ? C11 O9 C17 C18 -113.0(5) . . . . ? C22 C17 C18 C19 2.5(8) . . . . ? O9 C17 C18 C19 -173.3(5) . . . . ? C17 C18 C19 C20 -0.2(8) . . . . ? C18 C19 C20 C21 -0.9(8) . . . . ? C19 C20 C21 C22 -0.1(8) . . . . ? C19 C20 C21 O11 175.0(5) . . . . ? C16 O11 C21 C22 -88.1(6) . . . . ? C16 O11 C21 C20 96.7(6) . . . . ? C20 C21 C22 C17 2.2(8) . . . . ? O11 C21 C22 C17 -172.8(4) . . . . ? C18 C17 C22 C21 -3.4(8) . . . . ? O9 C17 C22 C21 172.2(4) . . . . ? C10 O10 C23 C24 114.2(6) . . . . ? C10 O10 C23 C28 -74.9(7) . . . . ? C28 C23 C24 C25 0.7(9) . . . . ? O10 C23 C24 C25 171.4(5) . . . . ? C23 C24 C25 C26 -1.1(10) . . . . ? C24 C25 C26 C27 0.4(10) . . . . ? C25 C26 C27 C28 0.8(10) . . . . ? C25 C26 C27 O12 -172.6(5) . . . . ? C13 O12 C27 C26 -109.3(6) . . . . ? C13 O12 C27 C28 77.1(7) . . . . ? C26 C27 C28 C23 -1.2(9) . . . . ? O12 C27 C28 C23 172.1(5) . . . . ? C24 C23 C28 C27 0.4(8) . . . . ? O10 C23 C28 C27 -170.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.440 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.101