# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1896 data_Liao _publ_requested_journal ' dalton' _publ_contact_author ; Dai-Zheng Liao Department of Chemistry, Nankai University, Tianjin 300071,China ; _publ_contact_author_email ' coord@sun.nankai.edu.cn ' _publ_section_title ; Crystal structure, redox and spectral properties of copper(II) complexes with macrocyclic ligands incorporating both oxamido and imine groups ; data_1 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H24 Cu N4 O6' _chemical_formula_weight 540.02 _chemical_melting_point ? _chemical_compound_source ? 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 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 24.859(3) _cell_length_b 13.2164(10) _cell_length_c 7.0968(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.19(2) _cell_angle_gamma 90.00 _cell_volume 2318.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 46 _cell_measurement_theta_min 4.95 _cell_measurement_theta_max 12.32 _exptl_crystal_description brick _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method ? _exptl_crystal_F_000 1116 _exptl_absorpt_coefficient_mu 0.993 _exptl_absorpt_correction_type empiral _exptl_absorpt_correction_T_min 0.6745 _exptl_absorpt_correction_T_max 0.7837 _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 'Siemens P4' _diffrn_measurement_method '/w scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2411 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0911 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2048 _reflns_number_observed 1369 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0684P)^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 ' using the model ' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2048 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_obs 0.0578 _refine_ls_wR_factor_all 0.1537 _refine_ls_wR_factor_obs 0.1331 _refine_ls_goodness_of_fit_all 1.066 _refine_ls_goodness_of_fit_obs 1.150 _refine_ls_restrained_S_all 1.066 _refine_ls_restrained_S_obs 1.150 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu Cu 0.0000 0.36492(7) 0.7500 0.0315(3) Uani 1 d S . O1 O 0.1301(2) 0.2031(3) 1.2518(5) 0.0495(11) Uani 1 d . . O2 O 0.1321(2) 0.1038(3) 0.9990(6) 0.0607(13) Uani 1 d . . O3 O 0.0448(2) 0.6439(3) 0.8765(6) 0.0526(11) Uani 1 d . . N1 N 0.0435(2) 0.2606(3) 0.8927(6) 0.0347(11) Uani 1 d . . N2 N 0.0508(2) 0.4701(3) 0.8298(6) 0.0287(10) Uani 1 d . . C3 C 0.1573(3) 0.1271(5) 1.3734(8) 0.065(2) Uani 1 d . . H3A H 0.1917(3) 0.1097(5) 1.3293(8) 0.078 Uiso 1 calc R . H3B H 0.1354(3) 0.0663(5) 1.3722(8) 0.078 Uiso 1 calc R . C1 C 0.0934(2) 0.2693(4) 0.9629(7) 0.0312(12) Uani 1 d . . C2 C 0.1211(2) 0.1821(4) 1.0711(8) 0.0380(14) Uani 1 d . . C4 C 0.1658(3) 0.1683(6) 1.5642(9) 0.088(3) Uani 1 d . . H4A H 0.1839(3) 0.1190(6) 1.6479(9) 0.133 Uiso 1 calc R . H4B H 0.1315(3) 0.1849(6) 1.6068(9) 0.133 Uiso 1 calc R . H4C H 0.1876(3) 0.2282(6) 1.5640(9) 0.133 Uiso 1 calc R . C5 C 0.0282(2) 0.5634(4) 0.8123(7) 0.0325(13) Uani 1 d . . C6 C 0.0116(2) 0.1702(4) 0.9297(8) 0.0419(15) Uani 1 d . . H6A H -0.0223(2) 0.1909(4) 0.9736(8) 0.050 Uiso 1 calc R . H6B H 0.0313(2) 0.1302(4) 1.0291(8) 0.050 Uiso 1 calc R . C7 C 0.0000 0.1048(6) 0.7500 0.052(2) Uani 1 d S . H7 H -0.0342(47) 0.0640(87) 0.7756(170) 0.062 Uiso 0.50 d P . C8 C 0.1057(2) 0.4574(4) 0.8921(7) 0.0291(12) Uani 1 d . . C9 C 0.1266(2) 0.3594(4) 0.9404(7) 0.0306(12) Uani 1 d . . C10 C 0.1833(2) 0.3473(4) 0.9824(8) 0.0400(14) Uani 1 d . . H10 H 0.1972(2) 0.2834(4) 1.0137(8) 0.048 Uiso 1 calc R . C11 C 0.2180(2) 0.4265(5) 0.9780(8) 0.047(2) Uani 1 d . . H12 H 0.2551(2) 0.4167(5) 1.0005(8) 0.056 Uiso 1 calc R . C12 C 0.1971(2) 0.5215(5) 0.9399(8) 0.045(2) Uani 1 d . . H13 H 0.2206(2) 0.5764(5) 0.9415(8) 0.054 Uiso 1 calc R . C13 C 0.1430(2) 0.5370(4) 0.8998(7) 0.0385(14) Uani 1 d . . H14 H 0.1303(2) 0.6026(4) 0.8767(7) 0.046 Uiso 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 Cu 0.0317(6) 0.0210(5) 0.0392(6) 0.000 -0.0075(4) 0.000 O1 0.069(3) 0.040(2) 0.037(2) 0.003(2) -0.008(2) 0.020(2) O2 0.086(4) 0.039(2) 0.053(3) -0.008(2) -0.009(2) 0.025(2) O3 0.043(2) 0.025(2) 0.089(3) -0.019(2) 0.001(2) -0.006(2) N1 0.036(3) 0.027(2) 0.040(3) 0.002(2) 0.000(2) 0.002(2) N2 0.026(2) 0.025(2) 0.033(2) 0.003(2) -0.004(2) -0.001(2) C3 0.093(5) 0.053(4) 0.047(4) 0.017(3) -0.009(4) 0.023(4) C1 0.034(3) 0.027(3) 0.032(3) -0.002(2) 0.002(2) 0.010(2) C2 0.039(3) 0.034(3) 0.039(3) 0.004(3) -0.004(3) 0.007(3) C4 0.108(7) 0.119(7) 0.036(4) 0.017(4) -0.002(4) 0.044(6) C5 0.034(3) 0.023(3) 0.041(3) -0.004(2) 0.008(2) -0.005(2) C6 0.039(3) 0.030(3) 0.054(4) 0.015(3) -0.008(3) -0.001(3) C7 0.065(6) 0.024(5) 0.062(6) 0.000 -0.011(5) 0.000 C8 0.035(3) 0.033(3) 0.019(3) -0.003(2) 0.000(2) 0.000(2) C9 0.032(3) 0.034(3) 0.025(3) -0.003(2) 0.000(2) 0.003(3) C10 0.034(3) 0.045(4) 0.041(3) 0.003(3) 0.001(3) 0.009(3) C11 0.028(3) 0.073(5) 0.038(3) -0.002(3) 0.000(3) -0.003(3) C12 0.034(3) 0.058(4) 0.043(3) 0.003(3) -0.004(3) -0.014(3) C13 0.037(3) 0.040(3) 0.036(3) 0.008(3) -0.004(3) -0.006(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 Cu N2 1.923(4) . ? Cu N2 1.923(4) 2_556 ? Cu N1 1.965(4) 2_556 ? Cu N1 1.965(4) . ? Cu O3 2.986(4) 6_565 ? Cu O3 2.986(4) 5_567 ? Cu Cu 5.0339(13) 5_567 ? Cu Cu 5.0339(13) 5_566 ? O1 C2 1.308(6) . ? O1 C3 1.444(6) . ? O2 C2 1.199(6) . ? O3 C5 1.211(6) . ? N1 C1 1.290(6) . ? N1 C6 1.474(6) . ? N2 C5 1.355(6) . ? N2 C8 1.397(6) . ? C3 C4 1.454(9) . ? C1 C9 1.467(7) . ? C1 C2 1.510(7) . ? C5 C5 1.575(10) 2_556 ? C6 C7 1.542(7) . ? C7 C6 1.542(7) 2_556 ? C8 C13 1.399(7) . ? C8 C9 1.424(7) . ? C9 C10 1.417(7) . ? C10 C11 1.358(8) . ? C11 C12 1.373(8) . ? C12 C13 1.362(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu N2 87.4(2) . 2_556 ? N2 Cu N1 165.3(2) . 2_556 ? N2 Cu N1 92.7(2) 2_556 2_556 ? N2 Cu N1 92.7(2) . . ? N2 Cu N1 165.3(2) 2_556 . ? N1 Cu N1 90.9(2) 2_556 . ? N2 Cu O3 89.63(15) . 6_565 ? N2 Cu O3 93.60(14) 2_556 6_565 ? N1 Cu O3 75.67(15) 2_556 6_565 ? N1 Cu O3 101.12(14) . 6_565 ? N2 Cu O3 93.60(14) . 5_567 ? N2 Cu O3 89.63(15) 2_556 5_567 ? N1 Cu O3 101.12(14) 2_556 5_567 ? N1 Cu O3 75.67(15) . 5_567 ? O3 Cu O3 175.54(14) 6_565 5_567 ? N2 Cu Cu 47.88(13) . 5_567 ? N2 Cu Cu 69.19(12) 2_556 5_567 ? N1 Cu Cu 144.99(13) 2_556 5_567 ? N1 Cu Cu 100.16(12) . 5_567 ? O3 Cu Cu 132.98(8) 6_565 5_567 ? O3 Cu Cu 51.21(7) 5_567 5_567 ? N2 Cu Cu 69.19(12) . 5_566 ? N2 Cu Cu 47.88(13) 2_556 5_566 ? N1 Cu Cu 100.16(12) 2_556 5_566 ? N1 Cu Cu 144.99(13) . 5_566 ? O3 Cu Cu 51.21(7) 6_565 5_566 ? O3 Cu Cu 132.98(8) 5_567 5_566 ? Cu Cu Cu 89.64(3) 5_567 5_566 ? C2 O1 C3 117.2(4) . . ? C1 N1 C6 121.1(4) . . ? C1 N1 Cu 126.1(4) . . ? C6 N1 Cu 112.6(3) . . ? C5 N2 C8 121.3(4) . . ? C5 N2 Cu 112.2(3) . . ? C8 N2 Cu 126.4(3) . . ? O1 C3 C4 107.9(5) . . ? N1 C1 C9 124.0(5) . . ? N1 C1 C2 119.7(5) . . ? C9 C1 C2 116.3(4) . . ? O2 C2 O1 125.4(5) . . ? O2 C2 C1 123.6(5) . . ? O1 C2 C1 110.9(5) . . ? O3 C5 N2 130.0(5) . . ? O3 C5 C5 117.2(3) . 2_556 ? N2 C5 C5 112.8(3) . 2_556 ? N1 C6 C7 111.3(5) . . ? C6 C7 C6 111.8(6) . 2_556 ? N2 C8 C13 122.7(5) . . ? N2 C8 C9 120.3(4) . . ? C13 C8 C9 116.8(5) . . ? C10 C9 C8 118.9(5) . . ? C10 C9 C1 116.4(5) . . ? C8 C9 C1 124.6(4) . . ? C11 C10 C9 121.8(5) . . ? C10 C11 C12 118.9(5) . . ? C13 C12 C11 121.5(6) . . ? C12 C13 C8 122.1(6) . . ? _refine_diff_density_max 0.366 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.112 #==END data_2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H22 Cu N4 O6' _chemical_formula_weight 526.00 _chemical_melting_point ? _chemical_compound_source ? 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 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 23.871(3) _cell_length_b 8.0074(12) _cell_length_c 25.775(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.663(8) _cell_angle_gamma 90.00 _cell_volume 4440.8(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 5.26 _cell_measurement_theta_max 11.01 _exptl_crystal_description PRISM _exptl_crystal_colour RED _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method ? _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 1.030 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8162 _exptl_absorpt_correction_T_max 0.8662 _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3906 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3094 _reflns_number_observed 1724 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0459P)^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 ' using the model ' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3093 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_obs 0.0492 _refine_ls_wR_factor_all 0.1062 _refine_ls_wR_factor_obs 0.0817 _refine_ls_goodness_of_fit_all 1.001 _refine_ls_goodness_of_fit_obs 1.107 _refine_ls_restrained_S_all 1.003 _refine_ls_restrained_S_obs 1.107 _refine_ls_shift/esd_max -0.108 _refine_ls_shift/esd_mean 0.016 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu Cu 0.57408(3) 0.28167(11) 0.48605(4) 0.0361(3) Uani 1 d . . O1 O 0.6493(2) 0.2872(8) 0.6688(2) 0.064(2) Uani 1 d . . O2 O 0.7243(2) 0.4005(8) 0.6298(2) 0.063(2) Uani 1 d . . O3 O 0.5825(2) 0.2271(8) 0.2812(2) 0.068(2) Uani 1 d . . O4 O 0.6308(2) 0.0065(7) 0.3424(2) 0.053(2) Uani 1 d . . O5 O 0.3786(2) 0.0422(7) 0.4349(3) 0.066(2) Uani 1 d . . O6 O 0.3688(2) 0.2720(7) 0.3761(2) 0.0476(14) Uani 1 d . . N1 N 0.5759(2) 0.3273(7) 0.5658(2) 0.038(2) Uani 1 d . . N2 N 0.4938(2) 0.2140(8) 0.4438(2) 0.0374(15) Uani 1 d . . N3 N 0.6526(2) 0.3558(8) 0.5256(3) 0.040(2) Uani 1 d . . N4 N 0.5750(2) 0.2037(8) 0.4091(2) 0.0362(15) Uani 1 d . . C1 C 0.6315(3) 0.3214(9) 0.6130(3) 0.041(2) Uani 1 d . . C2 C 0.6757(3) 0.3642(9) 0.5898(3) 0.039(2) Uani 1 d . . C3 C 0.4743(3) 0.1573(10) 0.3776(3) 0.047(2) Uani 1 d . . H3A H 0.4561(3) 0.2492(10) 0.3482(3) 0.056 Uiso 1 calc R . H3B H 0.4462(3) 0.0685(10) 0.3668(3) 0.056 Uiso 1 calc R . C4 C 0.5257(3) 0.0945(10) 0.3717(3) 0.044(2) Uani 1 d . . H4A H 0.5348(3) -0.0192(10) 0.3875(3) 0.053 Uiso 1 calc R . H4B H 0.5168(3) 0.0951(10) 0.3273(3) 0.053 Uiso 1 calc R . C5 C 0.4587(3) 0.2265(9) 0.4660(3) 0.034(2) Uani 1 d . . C6 C 0.6151(3) 0.2341(9) 0.3945(3) 0.036(2) Uani 1 d . . C7 C 0.5294(3) 0.3281(8) 0.5779(3) 0.035(2) Uani 1 d . . C8 C 0.5364(4) 0.3848(10) 0.6370(3) 0.055(2) Uani 1 d . . H8 H 0.5730(4) 0.4134(10) 0.6691(3) 0.066 Uiso 1 calc R . C9 C 0.4902(4) 0.3988(11) 0.6485(4) 0.062(3) Uani 1 d . . H9 H 0.4961(4) 0.4352(11) 0.6882(4) 0.075 Uiso 1 calc R . C10 C 0.4351(4) 0.3589(10) 0.6012(4) 0.055(2) Uani 1 d . . H10 H 0.4039(4) 0.3685(10) 0.6089(4) 0.066 Uiso 1 calc R . C11 C 0.4273(3) 0.3058(10) 0.5438(4) 0.048(2) Uani 1 d . . H11 H 0.3902(3) 0.2800(10) 0.5121(4) 0.057 Uiso 1 calc R . C12 C 0.4733(3) 0.2880(9) 0.5299(3) 0.037(2) Uani 1 d . . C13 C 0.6834(3) 0.3935(9) 0.4936(3) 0.038(2) Uani 1 d . . C14 C 0.7323(3) 0.4978(10) 0.5205(4) 0.050(2) Uani 1 d . . H14 H 0.7441(3) 0.5441(10) 0.5606(4) 0.060 Uiso 1 calc R . C15 C 0.7633(3) 0.5333(10) 0.4889(4) 0.055(2) Uani 1 d . . H15 H 0.7951(3) 0.6036(10) 0.5078(4) 0.066 Uiso 1 calc R . C16 C 0.7477(4) 0.4664(11) 0.4305(4) 0.057(2) Uani 1 d . . H16 H 0.7699(4) 0.4851(11) 0.4106(4) 0.068 Uiso 1 calc R . C17 C 0.6991(3) 0.3717(10) 0.4016(4) 0.047(2) Uani 1 d . . H17 H 0.6878(3) 0.3299(10) 0.3609(4) 0.056 Uiso 1 calc R . C18 C 0.6654(3) 0.3350(9) 0.4312(3) 0.038(2) Uani 1 d . . C19 C 0.3968(3) 0.1707(11) 0.4240(4) 0.046(2) Uani 1 d . . C20 C 0.3116(3) 0.2175(11) 0.3269(4) 0.063(3) Uani 1 d . . H20A H 0.2835(3) 0.2336(11) 0.3416(4) 0.075 Uiso 1 calc R . H20B H 0.3122(3) 0.1000(11) 0.3173(4) 0.075 Uiso 1 calc R . C21 C 0.2965(3) 0.3206(12) 0.2694(4) 0.078(3) Uani 1 d . . H21A H 0.2592(3) 0.2888(12) 0.2360(4) 0.117 Uiso 1 calc R . H21B H 0.3246(3) 0.3034(12) 0.2554(4) 0.117 Uiso 1 calc R . H21C H 0.2961(3) 0.4364(12) 0.2796(4) 0.117 Uiso 1 calc R . C22 C 0.6074(3) 0.1560(12) 0.3320(4) 0.048(2) Uani 1 d . . C23 C 0.6316(4) -0.0762(13) 0.2882(4) 0.080(3) Uani 1 d . . H23A H 0.5930(4) -0.0813(13) 0.2523(4) 0.096 Uiso 1 calc R . H23B H 0.6558(4) -0.0144(13) 0.2752(4) 0.096 Uiso 1 calc R . C24 C 0.6540(4) -0.2424(13) 0.3079(4) 0.095(4) Uani 1 d . . H24A H 0.6550(4) -0.2992(13) 0.2731(4) 0.143 Uiso 1 calc R . H24B H 0.6298(4) -0.3027(13) 0.3205(4) 0.143 Uiso 1 calc R . H24C H 0.6923(4) -0.2360(13) 0.3434(4) 0.143 Uiso 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 Cu 0.0342(5) 0.0454(6) 0.0302(5) 0.0007(6) 0.0166(4) 0.0007(5) O1 0.058(3) 0.105(5) 0.025(3) 0.011(4) 0.015(3) 0.019(4) O2 0.036(3) 0.105(5) 0.037(3) -0.016(3) 0.008(3) -0.005(3) O3 0.082(4) 0.088(5) 0.037(3) 0.009(4) 0.032(3) 0.019(4) O4 0.071(4) 0.054(4) 0.036(3) -0.001(3) 0.026(3) 0.019(3) O5 0.060(4) 0.054(4) 0.094(5) -0.004(4) 0.045(4) -0.014(3) O6 0.027(3) 0.059(4) 0.047(3) -0.001(3) 0.010(2) -0.003(3) N1 0.039(4) 0.051(5) 0.028(3) 0.005(3) 0.019(3) 0.006(3) N2 0.037(3) 0.048(4) 0.032(3) 0.002(3) 0.020(3) 0.001(3) N3 0.037(4) 0.053(4) 0.030(4) 0.004(3) 0.016(3) 0.005(3) N4 0.035(3) 0.045(4) 0.030(3) -0.003(3) 0.017(3) -0.003(3) C1 0.035(4) 0.050(6) 0.029(5) -0.002(4) 0.008(4) 0.008(4) C2 0.040(5) 0.039(5) 0.034(5) -0.004(4) 0.015(4) 0.012(4) C3 0.037(4) 0.065(6) 0.036(5) -0.006(4) 0.017(4) -0.005(4) C4 0.049(5) 0.053(6) 0.037(5) 0.000(4) 0.026(4) -0.005(4) C5 0.036(4) 0.025(4) 0.047(4) 0.012(4) 0.025(4) 0.002(4) C6 0.040(4) 0.042(5) 0.034(4) 0.013(4) 0.023(4) 0.016(4) C7 0.042(4) 0.033(5) 0.034(4) 0.005(4) 0.021(4) 0.007(4) C8 0.073(6) 0.061(6) 0.035(5) 0.004(5) 0.028(5) 0.017(5) C9 0.088(7) 0.066(7) 0.055(6) 0.005(5) 0.051(6) 0.017(6) C10 0.069(6) 0.055(6) 0.061(6) 0.024(5) 0.048(5) 0.027(5) C11 0.050(5) 0.052(6) 0.056(5) 0.008(5) 0.037(4) 0.009(5) C12 0.046(5) 0.034(5) 0.040(5) 0.010(4) 0.027(4) 0.005(4) C13 0.033(4) 0.041(5) 0.039(5) 0.004(4) 0.017(4) 0.007(4) C14 0.047(5) 0.047(6) 0.053(6) 0.000(5) 0.021(5) -0.008(4) C15 0.032(5) 0.054(6) 0.075(7) 0.012(6) 0.022(5) -0.008(4) C16 0.047(6) 0.067(7) 0.065(6) 0.017(6) 0.035(5) 0.008(5) C17 0.047(5) 0.048(6) 0.048(5) 0.000(5) 0.024(5) 0.005(5) C18 0.029(4) 0.044(6) 0.045(5) 0.015(4) 0.020(4) 0.000(4) C19 0.045(5) 0.044(6) 0.061(6) 0.000(5) 0.036(5) 0.002(5) C20 0.036(4) 0.078(7) 0.068(6) -0.011(6) 0.019(4) -0.014(5) C21 0.051(5) 0.105(9) 0.052(6) -0.015(6) 0.004(5) -0.008(6) C22 0.035(5) 0.083(8) 0.036(5) 0.005(5) 0.025(4) -0.002(5) C23 0.118(8) 0.096(9) 0.038(6) -0.011(6) 0.048(6) 0.021(7) C24 0.122(8) 0.107(10) 0.060(6) -0.004(7) 0.045(6) 0.034(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 1.915(5) . ? Cu N3 1.919(5) . ? Cu N2 1.943(5) . ? Cu N4 1.951(5) . ? O1 C1 1.212(7) . ? O2 C2 1.214(7) . ? O3 C22 1.210(9) . ? O4 C22 1.317(9) . ? O4 C23 1.462(8) . ? O5 C19 1.217(8) . ? O6 C19 1.305(8) . ? O6 C20 1.469(7) . ? N1 C1 1.360(8) . ? N1 C7 1.396(8) . ? N2 C5 1.275(7) . ? N2 C3 1.479(8) . ? N3 C2 1.353(8) . ? N3 C13 1.392(8) . ? N4 C6 1.288(8) . ? N4 C4 1.466(8) . ? C1 C2 1.553(9) . ? C3 C4 1.521(9) . ? C5 C12 1.468(9) . ? C5 C19 1.521(10) . ? C6 C18 1.441(9) . ? C6 C22 1.539(9) . ? C7 C12 1.410(9) . ? C7 C8 1.407(9) . ? C8 C9 1.381(10) . ? C9 C10 1.388(10) . ? C10 C11 1.354(10) . ? C11 C12 1.414(8) . ? C13 C18 1.411(9) . ? C13 C14 1.409(9) . ? C14 C15 1.384(10) . ? C15 C16 1.359(10) . ? C16 C17 1.361(10) . ? C17 C18 1.409(9) . ? C20 C21 1.484(10) . ? C23 C24 1.441(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu N3 87.0(2) . . ? N1 Cu N2 93.9(2) . . ? N3 Cu N2 177.8(3) . . ? N1 Cu N4 172.1(3) . . ? N3 Cu N4 93.5(2) . . ? N2 Cu N4 85.9(2) . . ? C22 O4 C23 116.9(6) . . ? C19 O6 C20 116.7(6) . . ? C1 N1 C7 122.7(6) . . ? C1 N1 Cu 108.6(4) . . ? C7 N1 Cu 127.1(5) . . ? C5 N2 C3 121.2(6) . . ? C5 N2 Cu 126.7(5) . . ? C3 N2 Cu 111.9(4) . . ? C2 N3 C13 123.0(6) . . ? C2 N3 Cu 111.5(5) . . ? C13 N3 Cu 125.4(5) . . ? C6 N4 C4 123.8(6) . . ? C6 N4 Cu 125.3(5) . . ? C4 N4 Cu 110.7(4) . . ? O1 C1 N1 127.9(7) . . ? O1 C1 C2 118.8(6) . . ? N1 C1 C2 113.4(6) . . ? O2 C2 N3 129.4(7) . . ? O2 C2 C1 117.9(6) . . ? N3 C2 C1 112.7(6) . . ? N2 C3 C4 109.4(5) . . ? N4 C4 C3 108.8(6) . . ? N2 C5 C12 125.3(6) . . ? N2 C5 C19 118.2(6) . . ? C12 C5 C19 116.5(6) . . ? N4 C6 C18 125.8(6) . . ? N4 C6 C22 116.3(6) . . ? C18 C6 C22 118.0(6) . . ? N1 C7 C12 121.4(6) . . ? N1 C7 C8 120.3(7) . . ? C12 C7 C8 118.0(7) . . ? C9 C8 C7 121.5(8) . . ? C8 C9 C10 120.4(8) . . ? C11 C10 C9 119.1(7) . . ? C10 C11 C12 122.6(8) . . ? C7 C12 C11 118.5(7) . . ? C7 C12 C5 124.8(6) . . ? C11 C12 C5 116.7(6) . . ? N3 C13 C18 121.2(6) . . ? N3 C13 C14 122.1(7) . . ? C18 C13 C14 116.6(7) . . ? C15 C14 C13 122.0(8) . . ? C16 C15 C14 120.6(8) . . ? C15 C16 C17 119.3(8) . . ? C16 C17 C18 122.2(8) . . ? C17 C18 C13 119.1(7) . . ? C17 C18 C6 115.9(7) . . ? C13 C18 C6 124.9(6) . . ? O5 C19 O6 126.7(8) . . ? O5 C19 C5 121.3(8) . . ? O6 C19 C5 111.9(7) . . ? O6 C20 C21 106.8(6) . . ? O3 C22 O4 126.6(8) . . ? O3 C22 C6 122.5(8) . . ? O4 C22 C6 110.9(7) . . ? C24 C23 O4 108.0(7) . . ? _refine_diff_density_max 0.306 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.078 #==END