# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Rong Cao' _publ_contact_author_address ; State Key Laboratory of Structural Chemistry Fujiao Institute of Research on the Structure of Matter Fuzhou Yangqiao West Road 155# Fuzhou Fujian 350002 CHINA ; _publ_contact_author_email RCAO@FJIRSM.AC.CN loop_ _publ_author_name 'Rong Cao.' 'Guoliang Li.' 'Xinfa Li.' 'Jian Lu.' 'Bo Xu.' 'Hongxun Yang.' # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 764594' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H20 Cd2 N4 O12' _chemical_formula_weight 613.10 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' Cd Cd -0.8075 1.2024 '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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.197(6) _cell_length_b 9.590(4) _cell_length_c 14.161(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.895(7) _cell_angle_gamma 90.00 _cell_volume 1770.7(13) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2481 _cell_measurement_theta_min 2.6362 _cell_measurement_theta_max 27.4816 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 2.475 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6120 _exptl_absorpt_correction_T_max 0.6643 _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 'mini mercury' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 2149 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7517 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2031 _reflns_number_gt 1696 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0953P)^2^+2.6803P] 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 2031 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1665 _refine_ls_wR_factor_gt 0.1371 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.003 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 Cd1 Cd 0.86869(4) 0.08199(5) 0.66979(4) 0.0334(2) Uani 1 1 d . . . N1 N 0.8597(4) 0.2194(5) 0.5271(4) 0.0260(11) Uani 1 1 d . . . C1 C 0.9231(5) 0.2277(7) 0.8390(5) 0.0316(15) Uani 1 1 d . . . O1 O 0.8672(4) 0.2876(5) 0.7686(4) 0.0390(12) Uani 1 1 d . . . O2 O 1.0483(4) 0.1022(5) 0.6696(4) 0.0355(11) Uani 1 1 d . . . C2 C 0.9563(5) 0.3071(8) 0.9275(5) 0.0350(15) Uani 1 1 d . . . H2A H 0.8968 0.3265 0.9578 0.042 Uiso 1 1 calc R . . H2B H 0.9843 0.3957 0.9109 0.042 Uiso 1 1 calc R . . N2 N 0.8544(5) -0.2116(8) 0.6432(6) 0.0499(18) Uani 1 1 d . . . O3 O 0.8375(6) -0.1189(6) 0.5749(5) 0.0584(17) Uani 1 1 d . . . C3 C 0.9634(5) 0.2327(7) 0.5005(5) 0.0359(15) Uani 1 1 d . . . H3A H 0.9574 0.2823 0.4402 0.043 Uiso 1 1 calc R . . H3B H 0.9886 0.1398 0.4900 0.043 Uiso 1 1 calc R . . O4 O 0.8799(5) -0.1656(8) 0.7236(5) 0.0668(18) Uani 1 1 d . . . C4 C 0.8160(5) 0.3609(6) 0.5389(5) 0.0267(13) Uani 1 1 d . . . H4A H 0.8203 0.4166 0.4825 0.032 Uiso 1 1 calc R . . H4B H 0.8556 0.4071 0.5934 0.032 Uiso 1 1 calc R . . O5 O 0.8417(7) -0.3298(7) 0.6251(6) 0.083(2) Uani 1 1 d . . . C5 C 0.7936(5) 0.1506(7) 0.4464(5) 0.0308(14) Uani 1 1 d . . . H5A H 0.8201 0.0578 0.4378 0.037 Uiso 1 1 calc R . . H5B H 0.7968 0.2030 0.3883 0.037 Uiso 1 1 calc R . . O6W O 0.7051(4) 0.0477(5) 0.7029(4) 0.0448(14) Uani 1 1 d . . . H6WA H 0.6979 0.0931 0.7539 0.067 Uiso 1 1 d R . . H6WB H 0.6959 -0.0398 0.7116 0.067 Uiso 1 1 d 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 Cd1 0.0358(4) 0.0296(3) 0.0339(4) -0.0004(2) 0.0024(2) -0.00390(19) N1 0.029(3) 0.021(3) 0.026(3) -0.004(2) -0.002(2) 0.000(2) C1 0.028(3) 0.027(3) 0.040(4) -0.003(3) 0.008(3) -0.003(3) O1 0.042(3) 0.037(3) 0.035(3) -0.010(2) -0.006(2) 0.009(2) O2 0.034(3) 0.030(2) 0.041(3) 0.007(2) 0.001(2) -0.001(2) C2 0.037(3) 0.034(4) 0.034(4) 0.001(3) 0.005(3) 0.001(3) N2 0.060(4) 0.041(4) 0.056(5) -0.016(3) 0.034(4) -0.013(3) O3 0.101(5) 0.033(3) 0.047(4) 0.000(3) 0.030(3) -0.005(3) C3 0.034(3) 0.039(4) 0.034(4) 0.005(3) 0.003(3) -0.001(3) O4 0.076(4) 0.061(4) 0.063(5) 0.012(4) 0.011(4) -0.005(4) C4 0.040(3) 0.016(3) 0.022(3) -0.001(2) 0.000(3) 0.002(2) O5 0.150(7) 0.029(3) 0.080(5) -0.002(3) 0.048(5) -0.023(4) C5 0.039(4) 0.019(3) 0.032(4) -0.002(3) -0.003(3) 0.000(3) O6W 0.054(3) 0.036(3) 0.049(4) -0.010(2) 0.024(3) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O6W 2.303(5) . ? Cd1 O3 2.349(6) . ? Cd1 O2 2.376(6) 2_756 ? Cd1 O2 2.378(5) . ? Cd1 N1 2.401(6) . ? Cd1 O1 2.419(5) . ? Cd1 O4 2.491(7) . ? N1 C3 1.480(8) . ? N1 C5 1.481(8) . ? N1 C4 1.493(7) . ? C1 O2 1.273(8) 2_756 ? C1 O1 1.281(9) . ? C1 C2 1.475(10) . ? O2 C1 1.273(8) 2_756 ? O2 Cd1 2.376(6) 2_756 ? C2 C3 1.528(9) 2_756 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N2 O5 1.169(9) . ? N2 O4 1.219(10) . ? N2 O3 1.307(10) . ? C3 C2 1.528(9) 2_756 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.497(9) 7_656 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C4 1.497(9) 7_656 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? O6W H6WA 0.8600 . ? O6W H6WB 0.8599 . ? 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 O6W Cd1 O3 85.0(2) . . ? O6W Cd1 O2 97.2(2) . 2_756 ? O3 Cd1 O2 129.0(2) . 2_756 ? O6W Cd1 O2 167.9(2) . . ? O3 Cd1 O2 98.8(2) . . ? O2 Cd1 O2 71.5(2) 2_756 . ? O6W Cd1 N1 108.90(19) . . ? O3 Cd1 N1 89.26(19) . . ? O2 Cd1 N1 135.81(17) 2_756 . ? O2 Cd1 N1 82.75(18) . . ? O6W Cd1 O1 84.65(18) . . ? O3 Cd1 O1 169.4(2) . . ? O2 Cd1 O1 54.81(16) 2_756 . ? O2 Cd1 O1 91.81(18) . . ? N1 Cd1 O1 92.03(17) . . ? O6W Cd1 O4 79.3(2) . . ? O3 Cd1 O4 52.4(2) . . ? O2 Cd1 O4 77.8(2) 2_756 . ? O2 Cd1 O4 93.8(2) . . ? N1 Cd1 O4 140.7(2) . . ? O1 Cd1 O4 127.3(2) . . ? C3 N1 C5 107.5(5) . . ? C3 N1 C4 109.8(5) . . ? C5 N1 C4 107.5(5) . . ? C3 N1 Cd1 109.5(4) . . ? C5 N1 Cd1 110.6(4) . . ? C4 N1 Cd1 112.0(4) . . ? O2 C1 O1 119.6(7) 2_756 . ? O2 C1 C2 121.0(7) 2_756 . ? O1 C1 C2 119.3(6) . . ? C1 O1 Cd1 91.7(4) . . ? C1 O2 Cd1 93.9(4) 2_756 2_756 ? C1 O2 Cd1 112.8(4) 2_756 . ? Cd1 O2 Cd1 107.7(2) 2_756 . ? C1 C2 C3 114.2(6) . 2_756 ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 2_756 . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 2_756 . ? H2A C2 H2B 107.6 . . ? O5 N2 O4 124.5(9) . . ? O5 N2 O3 119.7(8) . . ? O4 N2 O3 115.8(7) . . ? N2 O3 Cd1 98.0(5) . . ? N1 C3 C2 116.4(6) . 2_756 ? N1 C3 H3A 108.2 . . ? C2 C3 H3A 108.2 2_756 . ? N1 C3 H3B 108.2 . . ? C2 C3 H3B 108.2 2_756 . ? H3A C3 H3B 107.3 . . ? N2 O4 Cd1 93.7(5) . . ? N1 C4 C5 110.3(5) . 7_656 ? N1 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 7_656 . ? N1 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 7_656 . ? H4A C4 H4B 108.1 . . ? N1 C5 C4 113.1(6) . 7_656 ? N1 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 7_656 . ? N1 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 7_656 . ? H5A C5 H5B 107.8 . . ? Cd1 O6W H6WA 109.1 . . ? Cd1 O6W H6WB 109.0 . . ? H6WA O6W H6WB 109.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6W H6WA O5 0.86 2.01 2.857(9) 168.2 4_656 O6W H6WB O1 0.86 1.89 2.723(7) 161.8 4_646 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.955 _refine_diff_density_min -1.390 _refine_diff_density_rms 0.323 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 764595' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 N2 O6 Zn2' _chemical_formula_weight 393.00 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.705(7) _cell_length_b 13.169(10) _cell_length_c 6.581(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.864(12) _cell_angle_gamma 90.00 _cell_volume 631.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 653 _cell_measurement_theta_min 3.0936 _cell_measurement_theta_max 27.4565 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.066 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 3.824 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3934 _exptl_absorpt_correction_T_max 0.5978 _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 'mini mercury' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number 1506 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4835 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1436 _reflns_number_gt 1157 _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^)+(0.0624P)^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 1436 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.003 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 0.56298(6) 0.78493(3) 0.09299(7) 0.01632(19) Uani 1 1 d . . . O2 O 0.8004(4) 0.7161(2) 0.2037(5) 0.0230(7) Uani 1 1 d . . . O3 O 0.4446(4) 0.7367(2) -0.1941(5) 0.0213(6) Uani 1 1 d . . . N1 N 0.6542(4) 0.9358(2) 0.1246(5) 0.0156(7) Uani 1 1 d . . . C1 C 0.9570(6) 0.7525(3) 0.2169(7) 0.0195(8) Uani 1 1 d . . . C3 C 0.8469(6) 0.9331(3) 0.2788(7) 0.0231(9) Uani 1 1 d . . . H3A H 0.8426 0.9093 0.4166 0.028 Uiso 1 1 calc R . . H3B H 0.8940 1.0020 0.2989 0.028 Uiso 1 1 calc R . . C4 C 0.5426(6) 0.9977(3) 0.2261(6) 0.0207(8) Uani 1 1 d . . . H4A H 0.5996 1.0637 0.2650 0.025 Uiso 1 1 calc R . . H4B H 0.5400 0.9645 0.3566 0.025 Uiso 1 1 calc R . . C5 C 0.6512(6) 0.9883(3) -0.0771(6) 0.0203(8) Uani 1 1 d . . . H5A H 0.7202 0.9488 -0.1490 0.024 Uiso 1 1 calc R . . H5B H 0.7098 1.0542 -0.0422 0.024 Uiso 1 1 calc R . . C2 C 0.9815(5) 0.8673(3) 0.2137(7) 0.0230(9) Uani 1 1 d . . . H2A H 1.1039 0.8834 0.3079 0.028 Uiso 1 1 calc R . . H2B H 0.9757 0.8866 0.0695 0.028 Uiso 1 1 calc R . . O1 O 1.0908(4) 0.6980(2) 0.2323(6) 0.0315(8) Uani 1 1 d . . . H1 H 0.340(8) 0.770(3) -0.239(8) 0.021(12) 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 0.0169(3) 0.0160(3) 0.0164(3) -0.00002(17) 0.00581(19) -0.00002(17) O2 0.0186(14) 0.0204(15) 0.0298(17) 0.0043(12) 0.0078(13) 0.0006(12) O3 0.0150(14) 0.0301(17) 0.0187(15) -0.0050(12) 0.0056(13) -0.0010(12) N1 0.0160(16) 0.0137(16) 0.0198(17) -0.0007(13) 0.0096(14) 0.0004(13) C1 0.0198(19) 0.021(2) 0.019(2) -0.0017(16) 0.0073(17) -0.0009(17) C3 0.023(2) 0.019(2) 0.023(2) -0.0019(17) 0.0014(17) -0.0014(17) C4 0.030(2) 0.0164(19) 0.019(2) -0.0021(15) 0.0117(18) 0.0009(17) C5 0.023(2) 0.021(2) 0.020(2) 0.0044(16) 0.0118(18) 0.0023(17) C2 0.0184(19) 0.023(2) 0.027(2) 0.0036(17) 0.0056(18) 0.0006(17) O1 0.0195(15) 0.0266(17) 0.048(2) 0.0014(15) 0.0106(15) 0.0058(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 Zn1 O3 1.921(3) . ? Zn1 O3 1.924(3) 4_576 ? Zn1 O2 1.959(3) . ? Zn1 N1 2.095(4) . ? O2 C1 1.274(5) . ? O3 Zn1 1.924(3) 4_575 ? O3 H1 0.88(5) . ? N1 C5 1.490(5) . ? N1 C4 1.490(5) . ? N1 C3 1.504(5) . ? C1 O1 1.233(5) . ? C1 C2 1.525(6) . ? C3 C2 1.515(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.510(6) 3_675 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C4 1.510(6) 3_675 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? 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 O3 Zn1 O3 118.75(15) . 4_576 ? O3 Zn1 O2 107.59(14) . . ? O3 Zn1 O2 105.45(14) 4_576 . ? O3 Zn1 N1 116.63(13) . . ? O3 Zn1 N1 106.92(13) 4_576 . ? O2 Zn1 N1 99.13(13) . . ? C1 O2 Zn1 127.0(3) . . ? Zn1 O3 Zn1 125.38(17) . 4_575 ? Zn1 O3 H1 105(3) . . ? Zn1 O3 H1 115(4) 4_575 . ? C5 N1 C4 107.5(3) . . ? C5 N1 C3 109.9(3) . . ? C4 N1 C3 107.3(3) . . ? C5 N1 Zn1 116.3(2) . . ? C4 N1 Zn1 109.8(2) . . ? C3 N1 Zn1 105.7(2) . . ? O1 C1 O2 122.3(4) . . ? O1 C1 C2 118.3(4) . . ? O2 C1 C2 119.4(4) . . ? N1 C3 C2 116.1(3) . . ? N1 C3 H3A 108.3 . . ? C2 C3 H3A 108.3 . . ? N1 C3 H3B 108.3 . . ? C2 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? N1 C4 C5 111.6(3) . 3_675 ? N1 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 3_675 . ? N1 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 3_675 . ? H4A C4 H4B 108.0 . . ? N1 C5 C4 111.3(3) . 3_675 ? N1 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 3_675 . ? N1 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 3_675 . ? H5A C5 H5B 108.0 . . ? C3 C2 C1 117.6(3) . . ? C3 C2 H2A 107.9 . . ? C1 C2 H2A 107.9 . . ? C3 C2 H2B 107.9 . . ? C1 C2 H2B 107.9 . . ? H2A C2 H2B 107.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H1 O1 0.88(5) 1.91(6) 2.748(5) 157(5) 4_475 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.607 _refine_diff_density_min -0.706 _refine_diff_density_rms 0.200 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 764596' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H22 Cu N2 O7' _chemical_formula_weight 345.84 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 monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.955(8) _cell_length_b 7.032(5) _cell_length_c 10.184(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.489(11) _cell_angle_gamma 90.00 _cell_volume 705.1(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2252 _cell_measurement_theta_min 3.5569 _cell_measurement_theta_max 27.4680 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 1.581 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6075 _exptl_absorpt_correction_T_max 0.7973 _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 'mini mercury' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number 1729 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5382 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3016 _reflns_number_gt 2799 _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^)+(0.0135P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.027(13) _refine_ls_number_reflns 3016 _refine_ls_number_parameters 199 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0672 _refine_ls_wR_factor_gt 0.0659 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.020 _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 Cu1 Cu 0.60919(3) 0.66002(6) 0.30111(3) 0.02284(10) Uani 1 1 d . . . N1 N 0.7733(2) 0.7832(4) 0.4089(2) 0.0241(6) Uani 1 1 d . . . N2 N 0.7704(2) 0.5706(4) 0.2207(2) 0.0209(5) Uani 1 1 d . . . C1 C 0.4940(3) 0.8417(5) 0.5119(3) 0.0313(8) Uani 1 1 d . . . C2 C 0.6346(3) 0.8287(6) 0.5916(3) 0.0359(9) Uani 1 1 d . . . H2A H 0.6545 0.6964 0.6134 0.043 Uiso 1 1 calc R . . H2B H 0.6352 0.8973 0.6743 0.043 Uiso 1 1 calc R . . C3 C 0.7469(3) 0.9081(6) 0.5199(3) 0.0353(9) Uani 1 1 d . . . H3A H 0.7208 1.0335 0.4854 0.042 Uiso 1 1 calc R . . H3B H 0.8296 0.9213 0.5827 0.042 Uiso 1 1 calc R . . C4 C 0.8668(3) 0.6219(5) 0.4513(3) 0.0275(8) Uani 1 1 d . . . H4A H 0.8407 0.5603 0.5289 0.033 Uiso 1 1 calc R . . H4B H 0.9592 0.6677 0.4735 0.033 Uiso 1 1 calc R . . C5 C 0.8568(3) 0.4810(5) 0.3350(3) 0.0294(8) Uani 1 1 d . . . H5A H 0.9464 0.4543 0.3129 0.035 Uiso 1 1 calc R . . H5B H 0.8166 0.3624 0.3585 0.035 Uiso 1 1 calc R . . C6 C 0.8298(3) 0.8872(5) 0.3034(3) 0.0326(9) Uani 1 1 d . . . H6A H 0.9189 0.9374 0.3376 0.039 Uiso 1 1 calc R . . H6B H 0.7710 0.9925 0.2715 0.039 Uiso 1 1 calc R . . C7 C 0.8401(3) 0.7469(5) 0.1908(3) 0.0272(7) Uani 1 1 d . . . H7A H 0.7974 0.7997 0.1069 0.033 Uiso 1 1 calc R . . H7B H 0.9346 0.7208 0.1845 0.033 Uiso 1 1 calc R . . C8 C 0.7386(3) 0.4411(5) 0.1070(3) 0.0288(7) Uani 1 1 d . . . H8A H 0.7118 0.3188 0.1388 0.035 Uiso 1 1 calc R . . H8B H 0.8199 0.4218 0.0666 0.035 Uiso 1 1 calc R . . C9 C 0.6258(3) 0.5143(5) 0.0019(3) 0.0308(8) Uani 1 1 d . . . H9A H 0.6525 0.6385 -0.0268 0.037 Uiso 1 1 calc R . . H9B H 0.6194 0.4301 -0.0742 0.037 Uiso 1 1 calc R . . C10 C 0.4863(3) 0.5321(4) 0.0416(3) 0.0262(7) Uani 1 1 d . . . O1 O 0.3974(2) 0.8980(4) 0.5659(2) 0.0390(6) Uani 1 1 d . . . O2 O 0.4764(2) 0.7936(3) 0.38889(19) 0.0351(6) Uani 1 1 d . . . O3 O 0.47206(19) 0.5778(3) 0.16037(18) 0.0287(5) Uani 1 1 d . . . O4 O 0.3853(2) 0.5058(4) -0.0446(2) 0.0395(6) Uani 1 1 d . . . O5W O 0.9422(3) 0.6604(5) 0.8569(2) 0.0580(6) Uani 1 1 d D . . H5WB H 0.977(4) 0.612(5) 0.929(2) 0.087 Uiso 1 1 d D . . H5WA H 0.882(3) 0.584(5) 0.822(3) 0.087 Uiso 1 1 d D . . O6W O 0.8054(2) 0.3328(4) 0.7281(2) 0.0501(7) Uani 1 1 d D . . H6WB H 0.828(3) 0.249(4) 0.786(3) 0.075 Uiso 1 1 d D . . H6WA H 0.7213(14) 0.319(6) 0.701(3) 0.075 Uiso 1 1 d D . . O7W O 0.8539(3) 0.0398(4) 0.9245(3) 0.0443(6) Uani 1 1 d D . . H7WB H 0.877(3) -0.062(3) 0.892(4) 0.067 Uiso 1 1 d D . . H7WA H 0.780(2) 0.017(5) 0.954(4) 0.067 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01641(16) 0.0260(2) 0.02516(16) -0.00350(19) -0.00005(11) 0.00119(19) N1 0.0217(13) 0.0262(15) 0.0227(11) -0.0038(11) -0.0019(10) 0.0012(11) N2 0.0194(13) 0.0191(13) 0.0239(12) -0.0002(11) 0.0019(10) 0.0001(11) C1 0.0274(16) 0.033(2) 0.0333(16) -0.0092(17) 0.0036(13) -0.0003(17) C2 0.0288(17) 0.049(2) 0.0275(16) -0.0094(16) -0.0024(13) 0.0107(17) C3 0.0231(17) 0.043(2) 0.0374(18) -0.0156(17) -0.0045(14) 0.0034(16) C4 0.0186(13) 0.037(2) 0.0258(13) 0.0058(15) -0.0020(10) 0.0063(14) C5 0.0233(17) 0.030(2) 0.0331(18) 0.0083(16) 0.0002(13) 0.0109(15) C6 0.0322(19) 0.033(2) 0.0315(18) -0.0011(16) 0.0002(14) -0.0087(16) C7 0.0280(17) 0.0256(18) 0.0273(15) 0.0053(14) 0.0018(12) -0.0048(15) C8 0.0277(17) 0.0252(18) 0.0331(17) -0.0081(14) 0.0034(13) 0.0031(14) C9 0.0341(18) 0.032(2) 0.0248(15) -0.0089(15) 0.0004(13) -0.0016(16) C10 0.0296(17) 0.0151(17) 0.0319(16) -0.0005(14) -0.0026(13) -0.0017(14) O1 0.0252(12) 0.0484(17) 0.0443(13) -0.0188(12) 0.0082(10) 0.0020(11) O2 0.0229(11) 0.0509(16) 0.0306(11) -0.0107(12) 0.0007(9) 0.0075(11) O3 0.0187(11) 0.0399(14) 0.0269(11) -0.0023(10) 0.0013(8) -0.0030(9) O4 0.0304(13) 0.0476(17) 0.0360(12) -0.0081(12) -0.0100(10) -0.0029(12) O5W 0.0559(17) 0.0550(17) 0.0608(16) -0.002(2) 0.0004(12) -0.005(2) O6W 0.0359(15) 0.058(2) 0.0524(16) 0.0147(14) -0.0067(12) -0.0099(14) O7W 0.0408(16) 0.0408(16) 0.0533(16) 0.0084(14) 0.0134(12) 0.0035(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 O3 1.917(2) . ? Cu1 O2 1.943(2) . ? Cu1 N2 2.007(3) . ? Cu1 N1 2.023(3) . ? Cu1 O1 2.293(3) 2_646 ? N1 C6 1.478(4) . ? N1 C3 1.485(4) . ? N1 C4 1.490(4) . ? N2 C8 1.471(4) . ? N2 C7 1.474(4) . ? N2 C5 1.482(4) . ? C1 O1 1.241(4) . ? C1 O2 1.285(4) . ? C1 C2 1.513(4) . ? C2 C3 1.528(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.536(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.527(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.522(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.508(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O4 1.247(3) . ? C10 O3 1.279(3) . ? O1 Cu1 2.293(3) 2_656 ? O5W H5WB 0.836(10) . ? O5W H5WA 0.845(10) . ? O6W H6WB 0.839(10) . ? O6W H6WA 0.849(10) . ? O7W H7WB 0.837(10) . ? O7W H7WA 0.846(10) . ? 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 O3 Cu1 O2 91.83(10) . . ? O3 Cu1 N2 97.16(11) . . ? O2 Cu1 N2 167.95(10) . . ? O3 Cu1 N1 164.48(9) . . ? O2 Cu1 N1 95.34(11) . . ? N2 Cu1 N1 74.05(11) . . ? O3 Cu1 O1 96.90(10) . 2_646 ? O2 Cu1 O1 92.04(10) . 2_646 ? N2 Cu1 O1 94.80(10) . 2_646 ? N1 Cu1 O1 96.58(10) . 2_646 ? C6 N1 C3 112.9(3) . . ? C6 N1 C4 107.4(2) . . ? C3 N1 C4 113.7(2) . . ? C6 N1 Cu1 100.44(18) . . ? C3 N1 Cu1 116.53(19) . . ? C4 N1 Cu1 104.55(19) . . ? C8 N2 C7 114.3(2) . . ? C8 N2 C5 112.8(2) . . ? C7 N2 C5 106.5(2) . . ? C8 N2 Cu1 115.01(19) . . ? C7 N2 Cu1 104.46(18) . . ? C5 N2 Cu1 102.65(18) . . ? O1 C1 O2 120.8(3) . . ? O1 C1 C2 119.9(3) . . ? O2 C1 C2 119.3(3) . . ? C1 C2 C3 113.9(3) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? N1 C3 C2 111.8(3) . . ? N1 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? N1 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? N1 C4 C5 107.5(2) . . ? N1 C4 H4A 110.2 . . ? C5 C4 H4A 110.2 . . ? N1 C4 H4B 110.2 . . ? C5 C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? N2 C5 C4 107.2(3) . . ? N2 C5 H5A 110.3 . . ? C4 C5 H5A 110.3 . . ? N2 C5 H5B 110.3 . . ? C4 C5 H5B 110.3 . . ? H5A C5 H5B 108.5 . . ? N1 C6 C7 107.5(3) . . ? N1 C6 H6A 110.2 . . ? C7 C6 H6A 110.2 . . ? N1 C6 H6B 110.2 . . ? C7 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? N2 C7 C6 107.6(2) . . ? N2 C7 H7A 110.2 . . ? C6 C7 H7A 110.2 . . ? N2 C7 H7B 110.2 . . ? C6 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? N2 C8 C9 113.3(3) . . ? N2 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N2 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C10 C9 C8 116.9(3) . . ? C10 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? C10 C9 H9B 108.1 . . ? C8 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? O4 C10 O3 120.8(3) . . ? O4 C10 C9 118.5(3) . . ? O3 C10 C9 120.6(3) . . ? C1 O1 Cu1 127.6(2) . 2_656 ? C1 O2 Cu1 124.9(2) . . ? C10 O3 Cu1 128.06(19) . . ? H5WB O5W H5WA 106.7(17) . . ? H6WB O6W H6WA 107.1(16) . . ? H7WB O7W H7WA 106.8(16) . . ? 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 O3 Cu1 N1 C6 0.7(5) . . . . ? O2 Cu1 N1 C6 -116.45(19) . . . . ? N2 Cu1 N1 C6 57.73(19) . . . . ? O1 Cu1 N1 C6 150.86(19) 2_646 . . . ? O3 Cu1 N1 C3 123.1(4) . . . . ? O2 Cu1 N1 C3 5.9(2) . . . . ? N2 Cu1 N1 C3 -179.9(2) . . . . ? O1 Cu1 N1 C3 -86.8(2) 2_646 . . . ? O3 Cu1 N1 C4 -110.5(4) . . . . ? O2 Cu1 N1 C4 132.35(17) . . . . ? N2 Cu1 N1 C4 -53.47(17) . . . . ? O1 Cu1 N1 C4 39.67(18) 2_646 . . . ? O3 Cu1 N2 C8 -13.3(2) . . . . ? O2 Cu1 N2 C8 -151.2(4) . . . . ? N1 Cu1 N2 C8 179.8(2) . . . . ? O1 Cu1 N2 C8 84.3(2) 2_646 . . . ? O3 Cu1 N2 C7 112.84(18) . . . . ? O2 Cu1 N2 C7 -25.2(5) . . . . ? N1 Cu1 N2 C7 -54.09(18) . . . . ? O1 Cu1 N2 C7 -149.58(18) 2_646 . . . ? O3 Cu1 N2 C5 -136.16(19) . . . . ? O2 Cu1 N2 C5 85.8(5) . . . . ? N1 Cu1 N2 C5 56.91(19) . . . . ? O1 Cu1 N2 C5 -38.58(19) 2_646 . . . ? O1 C1 C2 C3 -135.2(3) . . . . ? O2 C1 C2 C3 45.0(4) . . . . ? C6 N1 C3 C2 153.8(3) . . . . ? C4 N1 C3 C2 -83.5(3) . . . . ? Cu1 N1 C3 C2 38.3(3) . . . . ? C1 C2 C3 N1 -71.5(4) . . . . ? C6 N1 C4 C5 -67.9(3) . . . . ? C3 N1 C4 C5 166.4(3) . . . . ? Cu1 N1 C4 C5 38.2(3) . . . . ? C8 N2 C5 C4 -173.0(3) . . . . ? C7 N2 C5 C4 60.9(3) . . . . ? Cu1 N2 C5 C4 -48.6(3) . . . . ? N1 C4 C5 N2 6.4(3) . . . . ? C3 N1 C6 C7 -175.0(2) . . . . ? C4 N1 C6 C7 58.8(3) . . . . ? Cu1 N1 C6 C7 -50.2(3) . . . . ? C8 N2 C7 C6 164.3(2) . . . . ? C5 N2 C7 C6 -70.5(3) . . . . ? Cu1 N2 C7 C6 37.7(3) . . . . ? N1 C6 C7 N2 8.7(3) . . . . ? C7 N2 C8 C9 -71.1(3) . . . . ? C5 N2 C8 C9 167.1(3) . . . . ? Cu1 N2 C8 C9 49.8(3) . . . . ? N2 C8 C9 C10 -65.4(4) . . . . ? C8 C9 C10 O4 -147.8(3) . . . . ? C8 C9 C10 O3 33.9(4) . . . . ? O2 C1 O1 Cu1 -132.9(3) . . . 2_656 ? C2 C1 O1 Cu1 47.2(4) . . . 2_656 ? O1 C1 O2 Cu1 -168.0(2) . . . . ? C2 C1 O2 Cu1 11.9(4) . . . . ? O3 Cu1 O2 C1 159.9(3) . . . . ? N2 Cu1 O2 C1 -61.8(6) . . . . ? N1 Cu1 O2 C1 -33.9(3) . . . . ? O1 Cu1 O2 C1 62.9(3) 2_646 . . . ? O4 C10 O3 Cu1 -170.3(2) . . . . ? C9 C10 O3 Cu1 8.0(4) . . . . ? O2 Cu1 O3 C10 155.2(3) . . . . ? N2 Cu1 O3 C10 -16.8(3) . . . . ? N1 Cu1 O3 C10 37.6(5) . . . . ? O1 Cu1 O3 C10 -112.5(3) 2_646 . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.497 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.063