Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Xigeng Zhou.' 'Zhen-Xia Chen.' 'Chuan-Feng Wang.' 'Zheng-Xing Zhang.' 'Zhen-Yu Zhu.' _publ_contact_author_name 'Prof Xigeng Zhou' _publ_contact_author_address ; Chemistry Fudan University Shanghai 200433 CHINA ; _publ_contact_author_email XGZHOU@FUDAN.EDU.CN _publ_section_title ; Crystal Engineering of Zinc(II) and Copper(II) Complexes Containing 3,5-Dimethylisoxazole-4-carboxylate Ligand via O-H...N, C-H...A (A = N, O and Pi) and Bifurcated C-H...N/O Interactions ; data_f50926c _database_code_depnum_ccdc_archive 'CCDC 624328' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H48 N6 O20 Zn3' _chemical_formula_weight 1128.95 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 11.500(5) _cell_length_b 17.654(8) _cell_length_c 12.048(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.909(10) _cell_angle_gamma 90.00 _cell_volume 2432.9(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 1.549 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7470 _exptl_absorpt_correction_T_max 0.8605 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_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 5370 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.1185 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3572 _reflns_number_gt 1722 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.1179P)^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 3572 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1273 _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.2013 _refine_ls_wR_factor_gt 0.1876 _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_restrained_S_all 0.842 _refine_ls_shift/su_max 0.005 _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 Zn1 Zn 0.0000 0.0000 1.0000 0.0358(4) Uani 1 2 d S . . Zn2 Zn 0.21267(11) 0.00789(5) 0.80488(8) 0.0433(4) Uani 1 1 d . . . O1 O 0.0743(7) 0.0979(3) 0.9344(6) 0.072(3) Uani 1 1 d . . . O2 O 0.1925(6) 0.1162(3) 0.8049(6) 0.061(2) Uani 1 1 d . . . O3 O 0.0366(6) 0.3331(3) 0.9207(5) 0.061(2) Uani 1 1 d . . . O4 O 0.1577(7) -0.0488(4) 1.0449(6) 0.070(2) Uani 1 1 d . . . O5 O 0.2944(7) -0.0455(4) 0.9281(5) 0.064(2) Uani 1 1 d . . . O6 O 0.4884(8) -0.1686(5) 1.1808(9) 0.103(3) Uani 1 1 d . . . O7 O -0.0257(7) -0.0551(4) 0.8494(6) 0.074(3) Uani 1 1 d . . . O8 O 0.0906(7) -0.0487(4) 0.7165(6) 0.069(2) Uani 1 1 d . . . O9 O -0.2299(8) -0.1897(5) 0.6239(7) 0.093(3) Uani 1 1 d . . . O10 O 0.3442(7) -0.0038(3) 0.7075(5) 0.061(2) Uani 1 1 d . . . N1 N 0.1145(8) 0.3463(4) 0.8384(7) 0.062(3) Uani 1 1 d . . . N2 N 0.4020(10) -0.1666(6) 1.2561(8) 0.077(3) Uani 1 1 d . . . N3 N -0.1547(10) -0.1887(6) 0.5398(8) 0.082(3) Uani 1 1 d . . . C1 C 0.1219(8) 0.1392(5) 0.8718(7) 0.041(2) Uani 1 1 d . . . C2 C 0.1049(9) 0.2220(5) 0.8764(7) 0.041(2) Uani 1 1 d . . . C3 C 0.1516(10) 0.2795(5) 0.8122(7) 0.047(3) Uani 1 1 d . . . C4 C 0.0329(9) 0.2593(5) 0.9416(8) 0.046(3) Uani 1 1 d . . . C5 C 0.2414(10) 0.2733(6) 0.7287(8) 0.064(3) Uani 1 1 d . . . H5A H 0.2586 0.3229 0.7020 0.096 Uiso 1 1 calc R . . H5B H 0.2108 0.2423 0.6671 0.096 Uiso 1 1 calc R . . H5C H 0.3116 0.2508 0.7642 0.096 Uiso 1 1 calc R . . C6 C -0.0435(9) 0.2355(5) 1.0273(8) 0.054(3) Uani 1 1 d . . . H6A H 0.0039 0.2205 1.0939 0.081 Uiso 1 1 calc R . . H6B H -0.0912 0.1936 0.9995 0.081 Uiso 1 1 calc R . . H6C H -0.0928 0.2770 1.0439 0.081 Uiso 1 1 calc R . . C7 C 0.2542(10) -0.0629(5) 1.0187(7) 0.044(3) Uani 1 1 d . . . C8 C 0.3349(10) -0.1046(5) 1.1000(8) 0.047(3) Uani 1 1 d . . . C9 C 0.3115(11) -0.1313(7) 1.2054(9) 0.065(3) Uani 1 1 d . . . C10 C 0.4458(12) -0.1317(7) 1.0902(10) 0.066(3) Uani 1 1 d . . . C11 C 0.2067(12) -0.1222(8) 1.2665(10) 0.105(5) Uani 1 1 d . . . H11A H 0.2220 -0.1434 1.3400 0.158 Uiso 1 1 calc R . . H11B H 0.1416 -0.1480 1.2269 0.158 Uiso 1 1 calc R . . H11C H 0.1886 -0.0694 1.2723 0.158 Uiso 1 1 calc R . . C12 C 0.5244(10) -0.1264(8) 0.9970(10) 0.089(4) Uani 1 1 d . . . H12A H 0.5989 -0.1487 1.0210 0.133 Uiso 1 1 calc R . . H12B H 0.5352 -0.0741 0.9784 0.133 Uiso 1 1 calc R . . H12C H 0.4891 -0.1529 0.9326 0.133 Uiso 1 1 calc R . . C13 C 0.0000(10) -0.0702(5) 0.7569(7) 0.045(3) Uani 1 1 d . . . C14 C -0.0778(10) -0.1173(6) 0.6843(8) 0.052(3) Uani 1 1 d . . . C15 C -0.0667(12) -0.1461(7) 0.5773(9) 0.070(4) Uani 1 1 d . . . C16 C -0.1813(11) -0.1470(6) 0.7092(8) 0.060(3) Uani 1 1 d . . . C17 C 0.0282(12) -0.1345(9) 0.5017(10) 0.106(5) Uani 1 1 d . . . H17A H 0.0961 -0.1632 0.5293 0.158 Uiso 1 1 calc R . . H17B H 0.0480 -0.0817 0.4998 0.158 Uiso 1 1 calc R . . H17C H 0.0011 -0.1513 0.4277 0.158 Uiso 1 1 calc R . . C18 C -0.2514(11) -0.1403(8) 0.8054(10) 0.096(5) Uani 1 1 d . . . H18A H -0.3293 -0.1585 0.7843 0.143 Uiso 1 1 calc R . . H18B H -0.2545 -0.0883 0.8278 0.143 Uiso 1 1 calc R . . H18C H -0.2159 -0.1701 0.8665 0.143 Uiso 1 1 calc R . . C19 C 0.3698(12) 0.0454(6) 0.6169(10) 0.084(4) Uani 1 1 d . . . H19A H 0.3414 0.0960 0.6302 0.101 Uiso 1 1 calc R . . H19B H 0.4539 0.0484 0.6153 0.101 Uiso 1 1 calc R . . C20 C 0.318(2) 0.0192(9) 0.5114(14) 0.188(12) Uani 1 1 d . . . H20A H 0.3546 -0.0272 0.4925 0.282 Uiso 1 1 calc R . . H20B H 0.3277 0.0567 0.4554 0.282 Uiso 1 1 calc R . . H20C H 0.2359 0.0105 0.5152 0.282 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 Zn1 0.0411(11) 0.0287(8) 0.0403(7) 0.0000(6) 0.0166(7) 0.0012(7) Zn2 0.0519(9) 0.0305(6) 0.0513(6) -0.0008(5) 0.0238(6) 0.0010(6) O1 0.103(7) 0.030(4) 0.093(5) 0.004(3) 0.057(5) -0.009(4) O2 0.075(6) 0.028(3) 0.089(5) -0.001(3) 0.048(5) 0.006(3) O3 0.078(6) 0.025(3) 0.088(5) -0.002(3) 0.046(4) 0.002(3) O4 0.047(6) 0.084(6) 0.084(5) 0.019(4) 0.028(5) 0.030(4) O5 0.062(6) 0.070(5) 0.065(4) 0.015(4) 0.024(4) 0.015(4) O6 0.072(9) 0.110(8) 0.119(7) 0.014(6) -0.025(6) 0.034(6) O7 0.090(7) 0.076(5) 0.059(4) -0.030(4) 0.026(5) -0.025(5) O8 0.064(6) 0.076(5) 0.069(5) -0.018(4) 0.022(4) -0.017(4) O9 0.081(8) 0.098(7) 0.096(6) -0.013(5) -0.006(6) -0.027(6) O10 0.076(6) 0.037(4) 0.079(4) 0.005(3) 0.052(4) 0.001(4) N1 0.080(8) 0.033(4) 0.081(6) -0.003(4) 0.051(6) -0.004(5) N2 0.065(10) 0.098(8) 0.065(6) 0.016(6) -0.007(6) -0.003(7) N3 0.084(10) 0.092(8) 0.070(6) -0.035(6) 0.007(6) -0.009(7) C1 0.039(7) 0.038(5) 0.046(5) -0.003(4) 0.011(5) -0.004(5) C2 0.043(7) 0.031(5) 0.049(5) 0.002(4) 0.009(5) 0.000(5) C3 0.057(8) 0.031(5) 0.055(5) 0.005(4) 0.018(5) 0.001(5) C4 0.053(8) 0.026(5) 0.062(6) -0.008(4) 0.018(6) 0.004(5) C5 0.076(10) 0.053(7) 0.071(7) 0.005(5) 0.039(7) -0.007(6) C6 0.058(8) 0.040(6) 0.069(6) 0.004(5) 0.028(6) -0.002(5) C7 0.049(9) 0.034(5) 0.049(6) 0.002(4) 0.003(6) -0.003(5) C8 0.035(8) 0.047(6) 0.060(6) 0.002(5) 0.008(6) 0.004(5) C9 0.052(10) 0.083(9) 0.057(7) 0.007(6) -0.014(7) 0.007(7) C10 0.059(11) 0.061(8) 0.077(8) 0.000(6) -0.005(7) 0.002(7) C11 0.105(13) 0.144(14) 0.073(8) 0.027(8) 0.042(9) 0.003(11) C12 0.044(10) 0.106(11) 0.120(10) -0.002(8) 0.032(9) 0.008(7) C13 0.054(8) 0.034(5) 0.049(6) -0.001(4) 0.014(6) -0.002(5) C14 0.057(9) 0.054(6) 0.046(5) -0.005(5) 0.003(6) -0.008(6) C15 0.073(11) 0.080(8) 0.057(7) -0.020(6) 0.007(7) -0.011(8) C16 0.065(10) 0.063(7) 0.051(6) -0.009(5) -0.006(6) -0.012(7) C17 0.107(13) 0.141(13) 0.078(8) -0.048(8) 0.048(9) -0.024(10) C18 0.073(11) 0.131(12) 0.087(9) -0.020(8) 0.031(8) -0.036(9) C19 0.103(12) 0.059(8) 0.101(9) 0.007(7) 0.058(9) -0.001(8) C20 0.35(4) 0.086(12) 0.115(14) 0.008(10) -0.033(17) 0.057(17) _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 Zn1 O4 2.030(8) . ? Zn1 O4 2.030(8) 3_557 ? Zn1 O7 2.054(6) . ? Zn1 O7 2.054(6) 3_557 ? Zn1 O1 2.117(6) 3_557 ? Zn1 O1 2.117(6) . ? Zn2 O5 1.920(7) . ? Zn2 O2 1.926(6) . ? Zn2 O8 1.948(8) . ? Zn2 O10 2.018(6) . ? O1 C1 1.218(10) . ? O2 C1 1.269(9) . ? O3 C4 1.329(10) . ? O3 N1 1.422(9) . ? O4 C7 1.210(11) . ? O5 C7 1.266(10) . ? O6 C10 1.321(13) . ? O6 N2 1.412(12) . ? O7 C13 1.211(9) . ? O8 C13 1.254(11) . ? O9 C16 1.349(12) . ? O9 N3 1.399(12) . ? O10 C19 1.448(11) . ? N1 C3 1.305(11) . ? N2 C9 1.309(14) . ? N3 C15 1.304(14) . ? C1 C2 1.476(12) . ? C2 C4 1.367(11) . ? C2 C3 1.416(12) . ? C3 C5 1.518(11) . ? C4 C6 1.483(12) . ? C7 C8 1.476(14) . ? C8 C10 1.378(15) . ? C8 C9 1.406(13) . ? C9 C11 1.484(15) . ? C10 C12 1.516(14) . ? C13 C14 1.448(14) . ? C14 C16 1.362(14) . ? C14 C15 1.403(13) . ? C15 C17 1.506(14) . ? C16 C18 1.483(13) . ? C19 C20 1.425(18) . ? 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 Zn1 O4 180.000(1) . 3_557 ? O4 Zn1 O7 94.5(3) . . ? O4 Zn1 O7 85.5(3) 3_557 . ? O4 Zn1 O7 85.5(3) . 3_557 ? O4 Zn1 O7 94.5(3) 3_557 3_557 ? O7 Zn1 O7 180.000(1) . 3_557 ? O4 Zn1 O1 86.5(3) . 3_557 ? O4 Zn1 O1 93.5(3) 3_557 3_557 ? O7 Zn1 O1 85.2(3) . 3_557 ? O7 Zn1 O1 94.8(3) 3_557 3_557 ? O4 Zn1 O1 93.5(3) . . ? O4 Zn1 O1 86.5(3) 3_557 . ? O7 Zn1 O1 94.8(3) . . ? O7 Zn1 O1 85.2(3) 3_557 . ? O1 Zn1 O1 180.00(19) 3_557 . ? O5 Zn2 O2 122.4(3) . . ? O5 Zn2 O8 116.0(3) . . ? O2 Zn2 O8 115.4(3) . . ? O5 Zn2 O10 93.6(3) . . ? O2 Zn2 O10 101.5(2) . . ? O8 Zn2 O10 99.8(3) . . ? C1 O1 Zn1 160.8(6) . . ? C1 O2 Zn2 113.8(6) . . ? C4 O3 N1 109.2(6) . . ? C7 O4 Zn1 146.7(7) . . ? C7 O5 Zn2 126.3(7) . . ? C10 O6 N2 107.0(10) . . ? C13 O7 Zn1 152.9(7) . . ? C13 O8 Zn2 121.6(7) . . ? C16 O9 N3 107.8(9) . . ? C19 O10 Zn2 126.9(6) . . ? C3 N1 O3 105.4(6) . . ? C9 N2 O6 106.9(9) . . ? C15 N3 O9 105.8(8) . . ? O1 C1 O2 124.0(8) . . ? O1 C1 C2 120.0(8) . . ? O2 C1 C2 115.9(8) . . ? C4 C2 C3 104.8(8) . . ? C4 C2 C1 126.1(8) . . ? C3 C2 C1 129.1(8) . . ? N1 C3 C2 111.4(8) . . ? N1 C3 C5 119.2(8) . . ? C2 C3 C5 129.3(8) . . ? O3 C4 C2 109.3(8) . . ? O3 C4 C6 116.3(8) . . ? C2 C4 C6 134.5(8) . . ? O4 C7 O5 126.9(10) . . ? O4 C7 C8 117.4(9) . . ? O5 C7 C8 115.6(9) . . ? C10 C8 C9 103.1(10) . . ? C10 C8 C7 129.8(9) . . ? C9 C8 C7 126.9(10) . . ? N2 C9 C8 111.3(11) . . ? N2 C9 C11 117.9(11) . . ? C8 C9 C11 130.8(12) . . ? O6 C10 C8 111.6(11) . . ? O6 C10 C12 116.4(12) . . ? C8 C10 C12 132.1(11) . . ? O7 C13 O8 125.6(10) . . ? O7 C13 C14 119.2(9) . . ? O8 C13 C14 115.2(8) . . ? C16 C14 C15 103.1(10) . . ? C16 C14 C13 125.9(9) . . ? C15 C14 C13 130.9(10) . . ? N3 C15 C14 112.8(10) . . ? N3 C15 C17 116.9(10) . . ? C14 C15 C17 130.3(12) . . ? O9 C16 C14 110.5(9) . . ? O9 C16 C18 115.1(11) . . ? C14 C16 C18 134.4(10) . . ? C20 C19 O10 112.2(12) . . ? _diffrn_measured_fraction_theta_max 0.832 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.832 _refine_diff_density_max 2.567 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.150 # Attachment 'F51021B-data1.CIF' data_f51021b _database_code_depnum_ccdc_archive 'CCDC 624329' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H40 N6 O20 Zn3' _chemical_formula_weight 1072.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.122(7) _cell_length_b 10.124(7) _cell_length_c 11.446(8) _cell_angle_alpha 88.961(9) _cell_angle_beta 69.655(9) _cell_angle_gamma 89.692(9) _cell_volume 1099.5(14) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 1.709 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8477 _exptl_absorpt_correction_T_max 0.9194 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 4591 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3790 _reflns_number_gt 3369 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0639P)^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 SHELXL _refine_ls_extinction_coef 0.0006(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3790 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Zn1 Zn 0.0000 0.0000 0.0000 0.02654(12) Uani 1 2 d S . . Zn2 Zn 0.12593(2) 0.20104(2) 0.18624(2) 0.02962(12) Uani 1 1 d . . . N1 N -0.5263(2) 0.3017(2) 0.2804(2) 0.0507(6) Uani 1 1 d . . . N2 N 0.0980(2) -0.4195(2) 0.3183(2) 0.0457(5) Uani 1 1 d . . . N3 N 0.4991(2) 0.2395(3) -0.3935(2) 0.0540(6) Uani 1 1 d . . . O1 O -0.13552(16) 0.10905(16) 0.14661(15) 0.0389(4) Uani 1 1 d . . . O2 O -0.05613(16) 0.28339(16) 0.21665(16) 0.0381(4) Uani 1 1 d . . . O3 O -0.47820(17) 0.39874(19) 0.34270(18) 0.0508(5) Uani 1 1 d . . . O4 O 0.11969(17) -0.07748(16) 0.09904(15) 0.0378(4) Uani 1 1 d . . . O5 O 0.12753(18) 0.02946(15) 0.26428(15) 0.0402(4) Uani 1 1 d . . . O6 O 0.11177(19) -0.35019(17) 0.41898(17) 0.0466(4) Uani 1 1 d . . . O7 O 0.13851(16) 0.15406(16) -0.08044(16) 0.0404(4) Uani 1 1 d . . . O8 O 0.26784(17) 0.23245(18) 0.02445(15) 0.0456(4) Uani 1 1 d . . . O9 O 0.5678(2) 0.3086(2) -0.3238(2) 0.0703(6) Uani 1 1 d . . . O10 O 0.1886(2) 0.31436(19) 0.29837(18) 0.0428(4) Uani 1 1 d . . . C1 C -0.1522(2) 0.2184(2) 0.1976(2) 0.0303(5) Uani 1 1 d . . . C2 C -0.2953(2) 0.2740(2) 0.2440(2) 0.0324(5) Uani 1 1 d . . . C3 C -0.4175(2) 0.2289(2) 0.2232(2) 0.0398(6) Uani 1 1 d . . . C4 C -0.3404(2) 0.3805(2) 0.3189(2) 0.0371(5) Uani 1 1 d . . . C5 C -0.4363(3) 0.1151(3) 0.1493(3) 0.0571(8) Uani 1 1 d . . . H5A H -0.4261 0.0338 0.1899 0.086 Uiso 1 1 calc R . . H5B H -0.3664 0.1194 0.0673 0.086 Uiso 1 1 calc R . . H5C H -0.5285 0.1188 0.1433 0.086 Uiso 1 1 calc R . . C6 C -0.2727(3) 0.4735(3) 0.3779(3) 0.0497(7) Uani 1 1 d . . . H6A H -0.2223 0.5394 0.3178 0.075 Uiso 1 1 calc R . . H6B H -0.2083 0.4265 0.4083 0.075 Uiso 1 1 calc R . . H6C H -0.3434 0.5155 0.4461 0.075 Uiso 1 1 calc R . . C7 C 0.1209(2) -0.0754(2) 0.2066(2) 0.0302(5) Uani 1 1 d . . . C8 C 0.1165(2) -0.2017(2) 0.2739(2) 0.0334(5) Uani 1 1 d . . . C9 C 0.1007(3) -0.3320(2) 0.2334(2) 0.0381(5) Uani 1 1 d . . . C10 C 0.1238(2) -0.2211(2) 0.3892(2) 0.0371(5) Uani 1 1 d . . . C11 C 0.0924(3) -0.3759(3) 0.1130(3) 0.0559(7) Uani 1 1 d . . . H11A H 0.0817 -0.4702 0.1152 0.084 Uiso 1 1 calc R . . H11B H 0.1772 -0.3511 0.0464 0.084 Uiso 1 1 calc R . . H11C H 0.0129 -0.3349 0.0997 0.084 Uiso 1 1 calc R . . C12 C 0.1458(3) -0.1333(3) 0.4825(2) 0.0518(7) Uani 1 1 d . . . H12A H 0.0565 -0.1127 0.5446 0.078 Uiso 1 1 calc R . . H12B H 0.1907 -0.0531 0.4421 0.078 Uiso 1 1 calc R . . H12C H 0.2046 -0.1768 0.5214 0.078 Uiso 1 1 calc R . . C13 C 0.2470(2) 0.2049(2) -0.0751(2) 0.0340(5) Uani 1 1 d . . . C14 C 0.3626(2) 0.2370(2) -0.1925(2) 0.0380(5) Uani 1 1 d . . . C15 C 0.3778(3) 0.1989(3) -0.3136(2) 0.0482(6) Uani 1 1 d . . . C16 C 0.4841(3) 0.3065(3) -0.2059(3) 0.0481(6) Uani 1 1 d . . . C17 C 0.2847(4) 0.1268(4) -0.3639(3) 0.0754(10) Uani 1 1 d . . . H17A H 0.3368 0.1009 -0.4476 0.113 Uiso 1 1 calc R . . H17B H 0.2078 0.1828 -0.3638 0.113 Uiso 1 1 calc R . . H17C H 0.2485 0.0496 -0.3131 0.113 Uiso 1 1 calc R . . C18 C 0.5310(4) 0.3768(4) -0.1159(3) 0.0754(10) Uani 1 1 d . . . H18A H 0.5706 0.3147 -0.0728 0.113 Uiso 1 1 calc R . . H18B H 0.4520 0.4203 -0.0568 0.113 Uiso 1 1 calc R . . H18C H 0.6010 0.4412 -0.1592 0.113 Uiso 1 1 calc R . . H10A H 0.277(4) 0.319(3) 0.301(3) 0.077(11) Uiso 1 1 d . . . H10B H 0.171(3) 0.396(3) 0.301(3) 0.052(9) 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 Zn1 0.0257(2) 0.0263(2) 0.0280(2) -0.00290(14) -0.00973(15) -0.00011(14) Zn2 0.02682(17) 0.02801(17) 0.03409(18) -0.00276(11) -0.01055(12) 0.00010(11) N1 0.0315(11) 0.0524(14) 0.0707(16) -0.0137(11) -0.0204(11) 0.0088(10) N2 0.0493(13) 0.0316(11) 0.0575(14) 0.0036(10) -0.0206(11) -0.0022(9) N3 0.0491(14) 0.0654(15) 0.0340(12) 0.0030(11) 0.0023(10) 0.0007(11) O1 0.0333(9) 0.0384(9) 0.0410(9) -0.0131(7) -0.0071(7) 0.0065(7) O2 0.0271(8) 0.0386(9) 0.0507(10) -0.0080(7) -0.0159(7) 0.0043(7) O3 0.0343(10) 0.0538(11) 0.0640(12) -0.0210(9) -0.0159(8) 0.0164(8) O4 0.0451(9) 0.0379(9) 0.0353(9) -0.0011(7) -0.0201(7) 0.0056(7) O5 0.0562(11) 0.0278(8) 0.0386(9) -0.0034(7) -0.0188(8) 0.0041(7) O6 0.0544(11) 0.0380(10) 0.0447(10) 0.0109(8) -0.0143(8) 0.0033(8) O7 0.0351(9) 0.0390(9) 0.0443(10) 0.0054(7) -0.0106(7) -0.0099(7) O8 0.0371(9) 0.0586(11) 0.0357(10) -0.0013(8) -0.0057(7) -0.0122(8) O9 0.0449(12) 0.0827(16) 0.0653(14) 0.0104(12) 0.0031(10) -0.0079(10) O10 0.0388(10) 0.0350(10) 0.0627(12) -0.0173(8) -0.0272(9) 0.0072(8) C1 0.0280(11) 0.0326(12) 0.0291(11) 0.0011(9) -0.0085(9) 0.0044(9) C2 0.0301(12) 0.0340(12) 0.0328(12) -0.0025(9) -0.0107(9) 0.0048(9) C3 0.0297(12) 0.0440(14) 0.0460(14) -0.0042(11) -0.0135(10) 0.0043(10) C4 0.0300(12) 0.0401(13) 0.0404(13) -0.0034(10) -0.0111(10) 0.0077(10) C5 0.0446(16) 0.0555(17) 0.080(2) -0.0219(15) -0.0321(15) 0.0065(13) C6 0.0475(15) 0.0453(15) 0.0578(17) -0.0165(12) -0.0196(13) 0.0096(12) C7 0.0255(11) 0.0293(11) 0.0348(12) -0.0023(9) -0.0090(9) 0.0035(9) C8 0.0328(12) 0.0309(12) 0.0358(12) 0.0004(9) -0.0110(10) 0.0035(9) C9 0.0383(13) 0.0286(12) 0.0506(15) 0.0007(10) -0.0195(11) 0.0010(10) C10 0.0359(13) 0.0365(13) 0.0359(13) -0.0006(10) -0.0088(10) 0.0074(10) C11 0.077(2) 0.0365(14) 0.071(2) -0.0090(13) -0.0464(17) 0.0038(13) C12 0.0693(19) 0.0509(16) 0.0351(14) -0.0079(12) -0.0179(13) 0.0183(14) C13 0.0320(12) 0.0295(11) 0.0363(13) 0.0015(9) -0.0067(10) 0.0005(9) C14 0.0323(12) 0.0351(13) 0.0402(14) 0.0030(10) -0.0045(10) -0.0005(9) C15 0.0526(16) 0.0463(15) 0.0383(15) 0.0037(11) -0.0067(12) 0.0023(12) C16 0.0328(13) 0.0501(15) 0.0518(16) 0.0055(12) -0.0028(12) -0.0040(11) C17 0.088(3) 0.088(3) 0.0486(18) 0.0005(17) -0.0218(17) -0.023(2) C18 0.054(2) 0.092(3) 0.073(2) -0.0003(19) -0.0128(17) -0.0337(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 2.0690(18) 2 ? Zn1 O4 2.0690(18) . ? Zn1 O7 2.0784(18) 2 ? Zn1 O7 2.0784(18) . ? Zn1 O1 2.0896(18) . ? Zn1 O1 2.0896(18) 2 ? Zn2 O8 1.9307(19) . ? Zn2 O2 1.9391(19) . ? Zn2 O5 1.9415(19) . ? Zn2 O10 1.9980(19) . ? N1 C3 1.301(3) . ? N1 O3 1.408(3) . ? N2 C9 1.296(3) . ? N2 O6 1.407(3) . ? N3 C15 1.313(3) . ? N3 O9 1.421(3) . ? O1 C1 1.244(3) . ? O2 C1 1.259(3) . ? O3 C4 1.338(3) . ? O4 C7 1.236(3) . ? O5 C7 1.274(3) . ? O6 C10 1.340(3) . ? O7 C13 1.236(3) . ? O8 C13 1.265(3) . ? O9 C16 1.320(3) . ? C1 C2 1.471(3) . ? C2 C4 1.365(3) . ? C2 C3 1.418(3) . ? C3 C5 1.493(4) . ? C4 C6 1.470(4) . ? C7 C8 1.473(3) . ? C8 C10 1.358(3) . ? C8 C9 1.434(3) . ? C9 C11 1.486(4) . ? C10 C12 1.478(4) . ? C13 C14 1.475(3) . ? C14 C16 1.380(4) . ? C14 C15 1.401(4) . ? C15 C17 1.467(4) . ? C16 C18 1.471(5) . ? 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 Zn1 O4 180.00(10) 2 . ? O4 Zn1 O7 94.73(8) 2 2 ? O4 Zn1 O7 85.27(8) . 2 ? O4 Zn1 O7 85.27(8) 2 . ? O4 Zn1 O7 94.73(8) . . ? O7 Zn1 O7 180.00(11) 2 . ? O4 Zn1 O1 84.06(8) 2 . ? O4 Zn1 O1 95.94(8) . . ? O7 Zn1 O1 83.88(8) 2 . ? O7 Zn1 O1 96.12(8) . . ? O4 Zn1 O1 95.94(8) 2 2 ? O4 Zn1 O1 84.06(8) . 2 ? O7 Zn1 O1 96.12(8) 2 2 ? O7 Zn1 O1 83.88(8) . 2 ? O1 Zn1 O1 180.0 . 2 ? O8 Zn2 O2 116.82(8) . . ? O8 Zn2 O5 116.93(8) . . ? O2 Zn2 O5 117.15(7) . . ? O8 Zn2 O10 103.33(9) . . ? O2 Zn2 O10 97.30(8) . . ? O5 Zn2 O10 99.79(9) . . ? C3 N1 O3 106.21(19) . . ? C9 N2 O6 106.7(2) . . ? C15 N3 O9 106.6(2) . . ? C1 O1 Zn1 143.61(15) . . ? C1 O2 Zn2 119.00(15) . . ? C4 O3 N1 108.69(18) . . ? C7 O4 Zn1 138.01(15) . . ? C7 O5 Zn2 119.88(15) . . ? C10 O6 N2 108.48(18) . . ? C13 O7 Zn1 140.09(16) . . ? C13 O8 Zn2 121.74(15) . . ? C16 O9 N3 107.9(2) . . ? O1 C1 O2 124.8(2) . . ? O1 C1 C2 118.02(19) . . ? O2 C1 C2 117.2(2) . . ? C4 C2 C3 104.4(2) . . ? C4 C2 C1 127.3(2) . . ? C3 C2 C1 128.3(2) . . ? N1 C3 C2 111.2(2) . . ? N1 C3 C5 118.7(2) . . ? C2 C3 C5 130.1(2) . . ? O3 C4 C2 109.5(2) . . ? O3 C4 C6 115.9(2) . . ? C2 C4 C6 134.6(2) . . ? O4 C7 O5 124.5(2) . . ? O4 C7 C8 118.7(2) . . ? O5 C7 C8 116.8(2) . . ? C10 C8 C9 104.2(2) . . ? C10 C8 C7 127.9(2) . . ? C9 C8 C7 127.8(2) . . ? N2 C9 C8 110.8(2) . . ? N2 C9 C11 119.3(2) . . ? C8 C9 C11 129.9(2) . . ? O6 C10 C8 109.8(2) . . ? O6 C10 C12 115.9(2) . . ? C8 C10 C12 134.2(2) . . ? O7 C13 O8 125.0(2) . . ? O7 C13 C14 118.7(2) . . ? O8 C13 C14 116.3(2) . . ? C16 C14 C15 104.7(2) . . ? C16 C14 C13 127.0(2) . . ? C15 C14 C13 128.3(2) . . ? N3 C15 C14 110.7(3) . . ? N3 C15 C17 117.1(3) . . ? C14 C15 C17 132.2(3) . . ? O9 C16 C14 110.1(3) . . ? O9 C16 C18 117.8(2) . . ? C14 C16 C18 132.0(3) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.279 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.066 # Attachment 'F51124B-data3.CIF' data_f51124b _database_code_depnum_ccdc_archive 'CCDC 624330' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H44 N8 O18 Zn3' _chemical_formula_weight 1193.00 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' 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' Zn Zn 0.2839 1.4301 '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 11.377(7) _cell_length_b 20.360(12) _cell_length_c 11.665(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.981(8) _cell_angle_gamma 90.00 _cell_volume 2622(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1220 _exptl_absorpt_coefficient_mu 1.440 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8694 _exptl_absorpt_correction_T_max 0.8694 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_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 10796 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4603 _reflns_number_gt 2690 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0824P)^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 4603 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1454 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.904 _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 Zn2 Zn 0.20792(6) 1.01448(3) 0.31714(6) 0.0561(2) Uani 1 1 d . . . Zn1 Zn 0.0000 1.0000 0.5000 0.0435(2) Uani 1 2 d S . . N1 N 0.1106(5) 1.3046(2) 0.3618(5) 0.0770(16) Uani 1 1 d . . . N2 N -0.1500(7) 0.8261(4) 0.0173(5) 0.111(2) Uani 1 1 d . . . N3 N 0.4755(6) 0.8199(4) 0.6794(8) 0.115(2) Uani 1 1 d . . . N4 N 0.3236(4) 1.01478(18) 0.2077(4) 0.0631(13) Uani 1 1 d . . . O1 O 0.0441(4) 1.08916(17) 0.4277(4) 0.0733(12) Uani 1 1 d . . . O2 O 0.1883(3) 1.10684(16) 0.3354(3) 0.0678(12) Uani 1 1 d . . . O3 O 0.0282(4) 1.29408(17) 0.4356(4) 0.0921(15) Uani 1 1 d . . . O5 O 0.0778(4) 0.9656(2) 0.2175(3) 0.0825(13) Uani 1 1 d . . . O4 O -0.0285(4) 0.9489(2) 0.3474(3) 0.0805(13) Uani 1 1 d . . . O6 O -0.2227(6) 0.8190(3) 0.0963(5) 0.130(2) Uani 1 1 d . . . O7 O 0.1778(4) 0.9692(2) 0.5589(4) 0.0817(13) Uani 1 1 d . . . O8 O 0.2982(4) 0.9588(2) 0.4391(4) 0.0780(12) Uani 1 1 d . . . O9 O 0.4004(6) 0.8276(3) 0.7583(6) 0.140(2) Uani 1 1 d . . . C1 C 0.1087(5) 1.1260(2) 0.3866(4) 0.0487(13) Uani 1 1 d . . . C2 C 0.0921(4) 1.1976(2) 0.3913(4) 0.0489(13) Uani 1 1 d . . . C3 C 0.1465(5) 1.2469(2) 0.3384(5) 0.0579(14) Uani 1 1 d . . . C4 C 0.2336(5) 1.2448(3) 0.2625(5) 0.0725(18) Uani 1 1 d . . . H4A H 0.2516 1.2887 0.2423 0.109 Uiso 1 1 calc R . . H4B H 0.1990 1.2206 0.1918 0.109 Uiso 1 1 calc R . . H4C H 0.3069 1.2236 0.3044 0.109 Uiso 1 1 calc R . . C5 C 0.0201(5) 1.2295(2) 0.4518(5) 0.0592(15) Uani 1 1 d . . . C6 C -0.0604(6) 1.2088(3) 0.5272(6) 0.0735(18) Uani 1 1 d . . . H6A H -0.0960 1.2468 0.5538 0.110 Uiso 1 1 calc R . . H6B H -0.0143 1.1850 0.5942 0.110 Uiso 1 1 calc R . . H6C H -0.1232 1.1810 0.4826 0.110 Uiso 1 1 calc R . . C7 C -0.0065(5) 0.9397(2) 0.2511(5) 0.0557(14) Uani 1 1 d . . . C8 C -0.0833(6) 0.8914(3) 0.1711(5) 0.0641(15) Uani 1 1 d . . . C9 C -0.0665(8) 0.8674(4) 0.0634(6) 0.090(2) Uani 1 1 d . . . C10 C 0.0253(8) 0.8840(5) -0.0032(6) 0.146(4) Uani 1 1 d . . . H10A H 0.0105 0.8587 -0.0747 0.219 Uiso 1 1 calc R . . H10B H 0.1047 0.8742 0.0444 0.219 Uiso 1 1 calc R . . H10C H 0.0202 0.9299 -0.0223 0.219 Uiso 1 1 calc R . . C11 C -0.1815(6) 0.8599(3) 0.1877(6) 0.082(2) Uani 1 1 d . . . C12 C -0.2478(7) 0.8604(5) 0.2825(7) 0.133(4) Uani 1 1 d . . . H12A H -0.3153 0.8308 0.2623 0.199 Uiso 1 1 calc R . . H12B H -0.2767 0.9040 0.2911 0.199 Uiso 1 1 calc R . . H12C H -0.1944 0.8468 0.3555 0.199 Uiso 1 1 calc R . . C13 C 0.2656(5) 0.9449(3) 0.5311(5) 0.0547(14) Uani 1 1 d . . . C14 C 0.3385(5) 0.8963(3) 0.6105(5) 0.0660(16) Uani 1 1 d . . . C15 C 0.3193(7) 0.8732(4) 0.7168(7) 0.097(2) Uani 1 1 d . . . C16 C 0.2307(7) 0.8907(6) 0.7836(6) 0.153(5) Uani 1 1 d . . . H16A H 0.2437 0.8643 0.8537 0.229 Uiso 1 1 calc R . . H16B H 0.1505 0.8831 0.7358 0.229 Uiso 1 1 calc R . . H16C H 0.2397 0.9363 0.8052 0.229 Uiso 1 1 calc R . . C17 C 0.4360(7) 0.8607(4) 0.5934(7) 0.096(2) Uani 1 1 d . . . C18 C 0.5003(7) 0.8619(6) 0.4969(7) 0.148(4) Uani 1 1 d . . . H18A H 0.5643 0.8300 0.5127 0.221 Uiso 1 1 calc R . . H18B H 0.5338 0.9048 0.4923 0.221 Uiso 1 1 calc R . . H18C H 0.4444 0.8517 0.4233 0.221 Uiso 1 1 calc R . . C19 C 0.3687(8) 0.9591(3) 0.1837(7) 0.127(4) Uani 1 1 d . . . H19A H 0.3525 0.9218 0.2234 0.153 Uiso 1 1 calc R . . C20 C 0.4376(7) 0.9519(3) 0.1047(7) 0.122(3) Uani 1 1 d . . . H20A H 0.4682 0.9108 0.0929 0.146 Uiso 1 1 calc R . . C21 C 0.4620(5) 1.0033(2) 0.0439(5) 0.0515(13) Uani 1 1 d . . . C22 C 0.4168(5) 1.0624(2) 0.0678(5) 0.0662(17) Uani 1 1 d . . . H22A H 0.4328 1.1001 0.0292 0.079 Uiso 1 1 calc R . . C23 C 0.3478(5) 1.0659(3) 0.1487(5) 0.0673(17) Uani 1 1 d . . . H23A H 0.3165 1.1065 0.1626 0.081 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 Zn2 0.0754(5) 0.0397(3) 0.0724(5) -0.0020(3) 0.0552(4) 0.0016(3) Zn1 0.0519(5) 0.0385(4) 0.0507(5) -0.0047(4) 0.0327(4) -0.0003(3) N1 0.106(4) 0.032(2) 0.117(4) 0.002(3) 0.076(4) 0.004(2) N2 0.152(7) 0.105(5) 0.068(4) -0.029(4) 0.010(5) -0.005(5) N3 0.088(5) 0.112(5) 0.129(6) 0.010(5) -0.003(5) 0.034(4) N4 0.088(3) 0.034(2) 0.093(3) -0.004(2) 0.072(3) -0.002(2) O1 0.106(3) 0.0373(19) 0.099(3) 0.001(2) 0.067(3) -0.001(2) O2 0.089(3) 0.0395(19) 0.096(3) -0.0043(19) 0.063(3) 0.0051(18) O3 0.128(4) 0.037(2) 0.138(4) 0.001(2) 0.085(3) 0.011(2) O5 0.094(3) 0.100(3) 0.071(3) -0.015(2) 0.053(3) -0.019(3) O4 0.096(3) 0.093(3) 0.067(3) -0.030(2) 0.049(2) -0.035(2) O6 0.156(6) 0.114(4) 0.100(4) -0.015(4) -0.010(4) -0.050(4) O7 0.061(3) 0.121(4) 0.073(3) 0.022(3) 0.035(2) 0.025(3) O8 0.092(3) 0.076(3) 0.082(3) 0.018(2) 0.052(3) 0.016(2) O9 0.119(5) 0.135(5) 0.140(6) 0.056(5) -0.021(4) -0.002(4) C1 0.065(4) 0.035(3) 0.052(3) -0.003(2) 0.025(3) 0.005(2) C2 0.059(3) 0.040(3) 0.055(3) -0.004(2) 0.028(3) 0.001(2) C3 0.066(4) 0.044(3) 0.073(4) -0.002(3) 0.035(3) 0.001(3) C4 0.091(5) 0.058(4) 0.083(4) 0.003(3) 0.050(4) -0.003(3) C5 0.077(4) 0.035(3) 0.073(4) -0.002(3) 0.035(3) 0.009(3) C6 0.092(5) 0.051(3) 0.099(5) -0.001(3) 0.066(4) 0.006(3) C7 0.069(4) 0.050(3) 0.054(3) 0.000(3) 0.026(3) 0.007(3) C8 0.082(4) 0.061(3) 0.049(4) -0.007(3) 0.015(3) -0.007(3) C9 0.123(7) 0.086(5) 0.058(4) -0.016(4) 0.018(5) 0.010(5) C10 0.184(10) 0.192(11) 0.076(5) -0.038(6) 0.058(6) 0.020(8) C11 0.084(5) 0.088(5) 0.065(4) -0.012(4) 0.001(4) -0.027(4) C12 0.103(7) 0.199(10) 0.100(7) -0.025(6) 0.030(5) -0.060(6) C13 0.051(3) 0.055(3) 0.062(4) 0.001(3) 0.022(3) -0.003(3) C14 0.050(4) 0.071(4) 0.075(4) 0.008(3) 0.012(3) -0.002(3) C15 0.064(5) 0.116(6) 0.099(6) 0.040(5) -0.005(5) -0.010(4) C16 0.092(6) 0.286(14) 0.089(6) 0.071(8) 0.037(5) 0.009(7) C17 0.071(5) 0.100(6) 0.102(6) 0.003(5) -0.009(5) 0.015(4) C18 0.104(7) 0.222(12) 0.117(7) -0.021(7) 0.028(6) 0.074(7) C19 0.215(9) 0.044(3) 0.191(8) 0.024(4) 0.181(7) 0.029(5) C20 0.203(8) 0.030(3) 0.198(8) 0.015(4) 0.178(7) 0.020(4) C21 0.070(4) 0.033(3) 0.067(3) -0.002(2) 0.045(3) -0.002(2) C22 0.098(4) 0.041(3) 0.082(4) 0.012(3) 0.063(4) 0.012(3) C23 0.095(5) 0.044(3) 0.086(4) 0.004(3) 0.067(4) 0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn2 O2 1.912(3) . ? Zn2 O8 1.912(4) . ? Zn2 O5 1.925(4) . ? Zn2 N4 2.043(4) . ? Zn1 O4 2.019(4) 3_576 ? Zn1 O4 2.019(4) . ? Zn1 O7 2.071(4) 3_576 ? Zn1 O7 2.071(4) . ? Zn1 O1 2.113(4) 3_576 ? Zn1 O1 2.113(4) . ? N1 C3 1.295(6) . ? N1 O3 1.433(6) . ? N2 C9 1.284(9) . ? N2 O6 1.387(8) . ? N3 C17 1.297(9) . ? N3 O9 1.408(9) . ? N4 C19 1.303(7) . ? N4 C23 1.314(6) . ? O1 C1 1.226(6) . ? O2 C1 1.262(5) . ? O3 C5 1.334(6) . ? O5 C7 1.237(6) . ? O4 C7 1.223(6) . ? O6 C11 1.345(8) . ? O7 C13 1.226(6) . ? O8 C13 1.249(6) . ? O9 C15 1.317(9) . ? C1 C2 1.472(7) . ? C2 C5 1.368(6) . ? C2 C3 1.399(6) . ? C3 C4 1.480(7) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.477(7) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.487(7) . ? C8 C11 1.342(8) . ? C8 C9 1.403(8) . ? C9 C10 1.483(10) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.482(10) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.468(8) . ? C14 C17 1.379(9) . ? C14 C15 1.392(9) . ? C15 C16 1.458(10) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.483(9) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.354(7) . ? C19 H19A 0.9300 . ? C20 C21 1.330(7) . ? C20 H20A 0.9300 . ? C21 C22 1.363(7) . ? C21 C21 1.498(9) 3_675 ? C22 C23 1.367(7) . ? C22 H22A 0.9300 . ? C23 H23A 0.9300 . ? 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 O2 Zn2 O8 123.78(18) . . ? O2 Zn2 O5 118.89(19) . . ? O8 Zn2 O5 109.8(2) . . ? O2 Zn2 N4 100.19(14) . . ? O8 Zn2 N4 98.96(18) . . ? O5 Zn2 N4 98.15(18) . . ? O4 Zn1 O4 180.000(1) 3_576 . ? O4 Zn1 O7 94.17(18) 3_576 3_576 ? O4 Zn1 O7 85.83(18) . 3_576 ? O4 Zn1 O7 85.83(18) 3_576 . ? O4 Zn1 O7 94.17(18) . . ? O7 Zn1 O7 180.000(1) 3_576 . ? O4 Zn1 O1 95.37(16) 3_576 3_576 ? O4 Zn1 O1 84.63(16) . 3_576 ? O7 Zn1 O1 94.93(17) 3_576 3_576 ? O7 Zn1 O1 85.07(17) . 3_576 ? O4 Zn1 O1 84.63(16) 3_576 . ? O4 Zn1 O1 95.37(16) . . ? O7 Zn1 O1 85.07(17) 3_576 . ? O7 Zn1 O1 94.93(17) . . ? O1 Zn1 O1 180.0(2) 3_576 . ? C3 N1 O3 106.0(4) . . ? C9 N2 O6 106.9(6) . . ? C17 N3 O9 106.4(7) . . ? C19 N4 C23 115.7(5) . . ? C19 N4 Zn2 118.6(4) . . ? C23 N4 Zn2 125.3(3) . . ? C1 O1 Zn1 154.8(4) . . ? C1 O2 Zn2 118.3(3) . . ? C5 O3 N1 108.0(4) . . ? C7 O5 Zn2 124.8(4) . . ? C7 O4 Zn1 149.7(4) . . ? C11 O6 N2 108.2(6) . . ? C13 O7 Zn1 145.8(4) . . ? C13 O8 Zn2 123.8(4) . . ? C15 O9 N3 108.7(6) . . ? O1 C1 O2 124.3(4) . . ? O1 C1 C2 119.8(4) . . ? O2 C1 C2 115.9(4) . . ? C5 C2 C3 105.6(4) . . ? C5 C2 C1 126.0(5) . . ? C3 C2 C1 128.3(4) . . ? N1 C3 C2 111.3(4) . . ? N1 C3 C4 116.3(5) . . ? C2 C3 C4 132.4(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 . . ? O3 C5 C2 109.0(5) . . ? O3 C5 C6 116.1(4) . . ? C2 C5 C6 134.9(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 . . ? O4 C7 O5 125.0(5) . . ? O4 C7 C8 117.3(5) . . ? O5 C7 C8 117.7(5) . . ? C11 C8 C9 105.1(6) . . ? C11 C8 C7 127.5(6) . . ? C9 C8 C7 127.4(6) . . ? N2 C9 C8 110.8(7) . . ? N2 C9 C10 118.3(7) . . ? C8 C9 C10 130.8(8) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 O6 108.9(7) . . ? C8 C11 C12 134.1(6) . . ? O6 C11 C12 116.9(7) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O7 C13 O8 124.4(5) . . ? O7 C13 C14 118.5(5) . . ? O8 C13 C14 117.1(5) . . ? C17 C14 C15 104.9(7) . . ? C17 C14 C13 127.9(6) . . ? C15 C14 C13 127.1(6) . . ? O9 C15 C14 108.6(7) . . ? O9 C15 C16 119.3(8) . . ? C14 C15 C16 132.1(7) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N3 C17 C14 111.4(8) . . ? N3 C17 C18 117.1(8) . . ? C14 C17 C18 131.5(8) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N4 C19 C20 124.2(5) . . ? N4 C19 H19A 117.9 . . ? C20 C19 H19A 117.9 . . ? C21 C20 C19 120.5(5) . . ? C21 C20 H20A 119.7 . . ? C19 C20 H20A 119.7 . . ? C20 C21 C22 116.6(5) . . ? C20 C21 C21 121.6(5) . 3_675 ? C22 C21 C21 121.8(5) . 3_675 ? C21 C22 C23 119.7(5) . . ? C21 C22 H22A 120.2 . . ? C23 C22 H22A 120.2 . . ? N4 C23 C22 123.2(5) . . ? N4 C23 H23A 118.4 . . ? C22 C23 H23A 118.4 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.739 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.082 # Attachment 'F60303A-data4.CIF' data_f60303a _database_code_depnum_ccdc_archive 'CCDC 624331' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Cu0.50 N2 O3' _chemical_formula_weight 249.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.738(3) _cell_length_b 9.471(5) _cell_length_c 10.852(7) _cell_angle_alpha 64.246(7) _cell_angle_beta 80.464(12) _cell_angle_gamma 89.857(9) _cell_volume 522.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 257 _exptl_absorpt_coefficient_mu 1.095 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9473 _exptl_absorpt_correction_T_max 0.9575 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 2213 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.1600 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1819 _reflns_number_gt 1003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0294P)^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 1819 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.0932 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 0.777 _refine_ls_restrained_S_all 0.777 _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 1.0000 0.0000 0.0363(3) Uani 1 2 d S . . O1 O 1.0898(6) 0.9616(4) 0.1719(3) 0.0410(9) Uani 1 1 d . . . O2 O 0.7945(6) 0.7793(5) 0.2530(4) 0.0711(13) Uani 1 1 d . . . N2 N 1.1880(9) 0.8117(7) 0.5720(5) 0.0761(17) Uani 1 1 d . . . N1 N 0.7964(6) 1.1687(4) 0.0121(4) 0.0351(10) Uani 1 1 d . . . O3 O 1.0019(10) 0.6878(7) 0.6348(5) 0.1144(18) Uani 1 1 d . . . C1 C 0.9545(10) 0.8471(7) 0.2706(6) 0.0426(14) Uani 1 1 d . . . C2 C 1.0099(9) 0.8067(6) 0.4084(5) 0.0444(14) Uani 1 1 d . . . C3 C 1.1865(11) 0.8765(8) 0.4398(6) 0.0651(18) Uani 1 1 d . . . C4 C 0.9005(11) 0.6900(8) 0.5343(7) 0.0689(18) Uani 1 1 d . . . C5 C 1.3672(10) 1.0063(8) 0.3539(6) 0.087(2) Uani 1 1 d . . . H5A H 1.4381 1.0386 0.4126 0.130 Uiso 1 1 calc R . . H5B H 1.2950 1.0932 0.2906 0.130 Uiso 1 1 calc R . . H5C H 1.4870 0.9722 0.3021 0.130 Uiso 1 1 calc R . . C6 C 0.7036(12) 0.5763(8) 0.5660(6) 0.107(2) Uani 1 1 d . . . H6A H 0.7288 0.4777 0.6397 0.161 Uiso 1 1 calc R . . H6B H 0.6930 0.5621 0.4846 0.161 Uiso 1 1 calc R . . H6C H 0.5589 0.6139 0.5946 0.161 Uiso 1 1 calc R . . C7 C 0.8506(7) 1.2476(6) 0.0817(4) 0.0390(13) Uani 1 1 d . . . H7 H 0.9702 1.2138 0.1340 0.047 Uiso 1 1 calc R . . C8 C 0.7378(8) 1.3753(6) 0.0791(5) 0.0427(13) Uani 1 1 d . . . H8 H 0.7830 1.4265 0.1286 0.051 Uiso 1 1 calc R . . C9 C 0.5594(7) 1.4297(5) 0.0051(5) 0.0322(12) Uani 1 1 d . . . C10 C 0.4982(7) 1.3440(6) -0.0632(5) 0.0405(13) Uani 1 1 d . . . H10 H 0.3741 1.3719 -0.1124 0.049 Uiso 1 1 calc R . . C11 C 0.6229(7) 1.2182(6) -0.0571(4) 0.0377(13) Uani 1 1 d . . . H11 H 0.5815 1.1643 -0.1053 0.045 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 0.0481(6) 0.0350(7) 0.0358(6) -0.0208(5) -0.0191(5) 0.0143(5) O1 0.061(2) 0.042(2) 0.032(2) -0.022(2) -0.0237(18) 0.020(2) O2 0.068(3) 0.087(3) 0.073(3) -0.044(3) -0.025(2) -0.008(2) N2 0.077(4) 0.115(5) 0.035(3) -0.028(3) -0.022(3) -0.014(3) N1 0.040(3) 0.039(3) 0.036(3) -0.022(2) -0.014(2) 0.012(2) O3 0.154(5) 0.134(5) 0.052(3) -0.032(4) -0.036(3) 0.036(4) C1 0.059(4) 0.040(4) 0.038(4) -0.023(3) -0.018(3) 0.019(3) C2 0.052(4) 0.048(4) 0.038(4) -0.021(3) -0.017(3) 0.015(3) C3 0.078(5) 0.090(5) 0.048(4) -0.042(4) -0.030(4) 0.025(4) C4 0.079(5) 0.075(5) 0.043(4) -0.020(4) -0.004(4) 0.004(4) C5 0.080(5) 0.122(7) 0.067(5) -0.046(5) -0.023(4) -0.020(5) C6 0.128(6) 0.090(6) 0.073(5) -0.017(5) 0.008(4) -0.022(5) C7 0.047(3) 0.040(4) 0.039(3) -0.021(3) -0.021(3) 0.016(3) C8 0.055(3) 0.041(4) 0.049(3) -0.032(3) -0.022(3) 0.015(3) C9 0.031(3) 0.034(3) 0.035(3) -0.017(3) -0.010(2) 0.006(2) C10 0.043(3) 0.042(4) 0.049(3) -0.026(3) -0.024(3) 0.016(3) C11 0.044(3) 0.042(4) 0.040(3) -0.025(3) -0.018(3) 0.012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.898(3) . ? Cu1 O1 1.898(3) 2_775 ? Cu1 N1 2.014(3) . ? Cu1 N1 2.014(3) 2_775 ? O1 C1 1.283(6) . ? O2 C1 1.208(5) . ? N2 C3 1.294(6) . ? N2 O3 1.432(6) . ? N1 C11 1.309(5) . ? N1 C7 1.340(5) . ? O3 C4 1.312(7) . ? C1 C2 1.464(7) . ? C2 C4 1.375(7) . ? C2 C3 1.376(7) . ? C3 C5 1.465(7) . ? C4 C6 1.452(8) . ? C7 C8 1.362(5) . ? C8 C9 1.367(5) . ? C9 C10 1.393(5) . ? C9 C9 1.464(8) 2_685 ? C10 C11 1.371(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 180.000(1) . 2_775 ? O1 Cu1 N1 90.16(13) . . ? O1 Cu1 N1 89.84(13) 2_775 . ? O1 Cu1 N1 89.84(13) . 2_775 ? O1 Cu1 N1 90.16(13) 2_775 2_775 ? N1 Cu1 N1 180.0 . 2_775 ? C1 O1 Cu1 109.1(3) . . ? C3 N2 O3 106.4(5) . . ? C11 N1 C7 116.5(4) . . ? C11 N1 Cu1 123.0(3) . . ? C7 N1 Cu1 120.2(3) . . ? C4 O3 N2 106.9(5) . . ? O2 C1 O1 123.8(5) . . ? O2 C1 C2 122.6(6) . . ? O1 C1 C2 113.6(5) . . ? C4 C2 C3 104.8(5) . . ? C4 C2 C1 127.9(6) . . ? C3 C2 C1 127.3(6) . . ? N2 C3 C2 111.5(6) . . ? N2 C3 C5 115.8(6) . . ? C2 C3 C5 132.7(6) . . ? O3 C4 C2 110.4(6) . . ? O3 C4 C6 119.8(7) . . ? C2 C4 C6 129.8(6) . . ? N1 C7 C8 122.7(4) . . ? C7 C8 C9 121.3(4) . . ? C8 C9 C10 115.8(4) . . ? C8 C9 C9 123.0(5) . 2_685 ? C10 C9 C9 121.3(5) . 2_685 ? C11 C10 C9 119.3(4) . . ? N1 C11 C10 124.4(4) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.385 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.070 # Attachment 'F60331B-data5.CIF' data_f60331b _database_code_depnum_ccdc_archive 'CCDC 624332' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cu N2 O6' _chemical_formula_weight 343.78 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 10.028(4) _cell_length_b 12.693(5) _cell_length_c 11.881(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.236(6) _cell_angle_gamma 90.00 _cell_volume 1500.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(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 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 1.482 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8906 _exptl_absorpt_correction_T_max 0.9296 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_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 5993 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.1667 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2630 _reflns_number_gt 1264 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0444P)^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 2630 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1022 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 0.642 _refine_ls_restrained_S_all 0.642 _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 0.94378(5) 0.06365(4) 0.91668(5) 0.02861(19) Uani 1 1 d . . . N1 N 0.4585(4) 0.0561(4) 1.1924(4) 0.0455(11) Uani 1 1 d . . . N2 N 0.8319(4) 0.1553(3) 0.7784(3) 0.0361(11) Uani 1 1 d . . . O1 O 0.7948(3) 0.0674(3) 1.0127(3) 0.0437(9) Uani 1 1 d . . . O2 O 0.8858(3) -0.0443(3) 1.1495(3) 0.0460(10) Uani 1 1 d . . . O3 O 0.6230(3) 0.4270(2) 0.6477(2) 0.0388(8) Uani 1 1 d . . . O4 O 0.5329(3) 0.3189(2) 0.5059(3) 0.0439(10) Uani 1 1 d . . . C1 C 0.7907(5) 0.0124(4) 1.1009(4) 0.0374(13) Uani 1 1 d . . . C2 C 0.6627(5) 0.0127(4) 1.1545(4) 0.0397(13) Uani 1 1 d . . . C3 C 0.6259(6) -0.0565(5) 1.2366(5) 0.0527(15) Uani 1 1 d . . . C4 C 0.6977(6) -0.1484(5) 1.2949(5) 0.082(2) Uani 1 1 d . . . H4A H 0.6433 -0.1787 1.3474 0.123 Uiso 1 1 calc R . . H4B H 0.7816 -0.1253 1.3351 0.123 Uiso 1 1 calc R . . H4C H 0.7144 -0.2003 1.2395 0.123 Uiso 1 1 calc R . . O5 O 0.5027(5) -0.0308(4) 1.2612(4) 0.1072(17) Uani 1 1 d . . . C5 C 0.5555(6) 0.0799(5) 1.1298(5) 0.0513(15) Uani 1 1 d . . . C6 C 0.5268(5) 0.1702(4) 1.0505(5) 0.0733(19) Uani 1 1 d . . . H6A H 0.4390 0.1978 1.0573 0.110 Uiso 1 1 calc R . . H6B H 0.5301 0.1468 0.9741 0.110 Uiso 1 1 calc R . . H6C H 0.5928 0.2244 1.0690 0.110 Uiso 1 1 calc R . . C7 C 0.6079(4) 0.3389(4) 0.5975(4) 0.0314(12) Uani 1 1 d . . . C8 C 0.6906(5) 0.2492(4) 0.6515(4) 0.0287(11) Uani 1 1 d . . . C9 C 0.7202(5) 0.1574(4) 0.6010(4) 0.0354(13) Uani 1 1 d . . . C10 C 0.6812(6) 0.1089(4) 0.4867(4) 0.0651(18) Uani 1 1 d . . . H10A H 0.7250 0.0419 0.4834 0.098 Uiso 1 1 calc R . . H10B H 0.7080 0.1544 0.4291 0.098 Uiso 1 1 calc R . . H10C H 0.5855 0.0991 0.4744 0.098 Uiso 1 1 calc R . . O6 O 0.8061(3) 0.0991(2) 0.6735(3) 0.0408(9) Uani 1 1 d . . . C11 C 0.7634(4) 0.2436(4) 0.7634(4) 0.0302(12) Uani 1 1 d . . . C12 C 0.7666(5) 0.3209(4) 0.8598(4) 0.0416(14) Uani 1 1 d . . . H12A H 0.8247 0.2947 0.9241 0.062 Uiso 1 1 calc R . . H12B H 0.6775 0.3297 0.8798 0.062 Uiso 1 1 calc R . . H12C H 0.7997 0.3875 0.8369 0.062 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 0.0313(3) 0.0194(3) 0.0325(3) -0.0007(3) -0.0065(2) 0.0003(3) N1 0.030(3) 0.054(3) 0.055(3) 0.010(3) 0.016(2) 0.007(3) N2 0.045(3) 0.023(2) 0.037(3) -0.002(2) -0.010(2) 0.005(2) O1 0.047(2) 0.044(2) 0.041(2) 0.0094(19) 0.0108(17) 0.011(2) O2 0.039(2) 0.048(2) 0.051(2) 0.0099(19) 0.0066(17) 0.0099(18) O3 0.048(2) 0.0253(18) 0.0373(19) 0.0015(18) -0.0165(16) 0.0036(19) O4 0.054(2) 0.028(2) 0.041(2) -0.0014(17) -0.0264(19) 0.0004(17) C1 0.041(4) 0.029(3) 0.041(4) -0.013(3) -0.001(3) -0.009(3) C2 0.041(4) 0.041(3) 0.038(3) -0.003(3) 0.008(3) -0.003(3) C3 0.042(4) 0.066(4) 0.052(4) -0.007(4) 0.015(3) 0.000(4) C4 0.081(5) 0.090(5) 0.077(5) 0.028(4) 0.015(4) 0.003(4) O5 0.091(4) 0.138(5) 0.100(4) -0.018(4) 0.040(3) -0.030(4) C5 0.045(4) 0.049(4) 0.060(4) -0.012(3) 0.006(3) -0.003(3) C6 0.053(4) 0.075(5) 0.092(5) 0.001(4) 0.008(3) 0.017(3) C7 0.030(3) 0.031(3) 0.033(3) 0.004(3) 0.002(2) -0.006(2) C8 0.034(3) 0.023(2) 0.027(3) 0.003(2) -0.005(2) -0.002(2) C9 0.045(3) 0.027(3) 0.030(3) 0.005(2) -0.010(2) 0.004(2) C10 0.097(5) 0.044(3) 0.047(4) -0.007(3) -0.024(3) 0.017(3) O6 0.054(2) 0.0258(19) 0.039(2) -0.0015(16) -0.0101(18) 0.0115(16) C11 0.032(3) 0.026(3) 0.032(3) 0.002(2) 0.000(2) 0.000(2) C12 0.052(4) 0.033(3) 0.037(3) 0.005(3) -0.004(3) 0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.976(3) 4_666 ? Cu1 O3 1.978(3) 2_646 ? Cu1 O2 1.985(3) 3_757 ? Cu1 O1 1.992(3) . ? Cu1 N2 2.202(4) . ? Cu1 Cu1 2.6907(13) 3_757 ? N1 C5 1.332(6) . ? N1 O5 1.410(6) . ? N2 C11 1.316(5) . ? N2 O6 1.431(4) . ? O1 C1 1.264(6) . ? O2 C1 1.273(5) . ? O2 Cu1 1.985(3) 3_757 ? O3 C7 1.267(5) . ? O3 Cu1 1.978(3) 2_656 ? O4 C7 1.268(5) . ? O4 Cu1 1.976(3) 4_565 ? C1 C2 1.503(7) . ? C2 C5 1.375(6) . ? C2 C3 1.397(7) . ? C3 O5 1.346(6) . ? C3 C4 1.494(7) . ? C5 C6 1.489(7) . ? C7 C8 1.505(6) . ? C8 C9 1.360(6) . ? C8 C11 1.435(5) . ? C9 O6 1.359(5) . ? C9 C10 1.497(6) . ? C11 C12 1.505(6) . ? 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 O3 167.69(11) 4_666 2_646 ? O4 Cu1 O2 87.25(14) 4_666 3_757 ? O3 Cu1 O2 90.25(13) 2_646 3_757 ? O4 Cu1 O1 89.78(14) 4_666 . ? O3 Cu1 O1 90.04(14) 2_646 . ? O2 Cu1 O1 167.36(12) 3_757 . ? O4 Cu1 N2 98.93(13) 4_666 . ? O3 Cu1 N2 93.37(13) 2_646 . ? O2 Cu1 N2 98.79(14) 3_757 . ? O1 Cu1 N2 93.80(14) . . ? O4 Cu1 Cu1 86.52(9) 4_666 3_757 ? O3 Cu1 Cu1 81.26(9) 2_646 3_757 ? O2 Cu1 Cu1 85.14(10) 3_757 3_757 ? O1 Cu1 Cu1 82.41(10) . 3_757 ? N2 Cu1 Cu1 173.39(10) . 3_757 ? C5 N1 O5 107.6(4) . . ? C11 N2 O6 105.9(3) . . ? C11 N2 Cu1 139.4(3) . . ? O6 N2 Cu1 113.9(2) . . ? C1 O1 Cu1 124.5(3) . . ? C1 O2 Cu1 121.5(3) . 3_757 ? C7 O3 Cu1 125.2(3) . 2_656 ? C7 O4 Cu1 119.2(3) . 4_565 ? O1 C1 O2 126.0(5) . . ? O1 C1 C2 117.9(5) . . ? O2 C1 C2 116.1(5) . . ? C5 C2 C3 105.7(5) . . ? C5 C2 C1 126.7(5) . . ? C3 C2 C1 127.5(5) . . ? O5 C3 C2 109.2(5) . . ? O5 C3 C4 119.4(6) . . ? C2 C3 C4 131.3(5) . . ? C3 O5 N1 107.1(5) . . ? N1 C5 C2 110.3(5) . . ? N1 C5 C6 115.6(5) . . ? C2 C5 C6 134.1(5) . . ? O4 C7 O3 127.2(4) . . ? O4 C7 C8 116.7(4) . . ? O3 C7 C8 116.1(4) . . ? C9 C8 C11 104.7(4) . . ? C9 C8 C7 126.8(4) . . ? C11 C8 C7 128.4(4) . . ? O6 C9 C8 110.1(4) . . ? O6 C9 C10 115.0(4) . . ? C8 C9 C10 134.9(4) . . ? C9 O6 N2 108.1(3) . . ? N2 C11 C8 111.3(4) . . ? N2 C11 C12 119.4(4) . . ? C8 C11 C12 129.3(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.462 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.071