# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dan Li' _publ_contact_author_address ; Department of Chemistry Shantou University Guangdong 515063 P. R. China ; _publ_contact_author_email dli@stu.edu.cn _publ_section_title ; pH-induced formation of metalloligand: increasing structure dimensionality by tuning number of ligand functional sites ; loop_ _publ_author_name 'Dan Li' 'Wen-Xiu Ni' 'Mian Li' 'Xiao-Ping Zhou' 'Zhen Li' ; Xiao-Chun Huang ; #====================================== data_4-Hpcih _database_code_depnum_ccdc_archive 'CCDC 643873' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N4 O' _chemical_formula_weight 226.24 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7099(11) _cell_length_b 14.665(2) _cell_length_c 10.2423(15) _cell_angle_alpha 90.00 _cell_angle_beta 109.166(3) _cell_angle_gamma 90.00 _cell_volume 1093.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 28.34 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7486 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 28.34 _reflns_number_total 2684 _reflns_number_gt 1865 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+0.0737P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2684 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1282 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C1 C 0.5092(2) 0.87818(11) 1.19291(15) 0.0446(4) Uani 1 1 d . . . H1 H 0.5887 0.9265 1.1964 0.053 Uiso 1 1 calc R . . C2 C 0.5702(2) 0.80130(11) 1.27210(17) 0.0481(4) Uani 1 1 d . . . H2 H 0.6927 0.7992 1.3280 0.058 Uiso 1 1 calc R . . C3 C 0.2901(2) 0.73559(11) 1.19301(17) 0.0465(4) Uani 1 1 d . . . H3 H 0.2132 0.6868 1.1933 0.056 Uiso 1 1 calc R . . C4 C 0.2159(2) 0.80909(10) 1.10928(15) 0.0417(4) Uani 1 1 d . . . H4 H 0.0927 0.8094 1.0547 0.050 Uiso 1 1 calc R . . C5 C 0.3282(2) 0.88227(9) 1.10815(14) 0.0363(4) Uani 1 1 d . . . C6 C 0.2628(2) 0.96683(10) 1.02350(16) 0.0414(4) Uani 1 1 d . . . C7 C -0.0515(2) 1.00225(11) 0.69615(16) 0.0476(4) Uani 1 1 d . . . H7 H -0.0819 0.9412 0.6772 0.057 Uiso 1 1 calc R . . C8 C -0.1377(2) 1.07050(11) 0.59118(15) 0.0402(4) Uani 1 1 d . . . C9 C -0.2704(2) 1.04322(11) 0.46950(17) 0.0518(5) Uani 1 1 d . . . H9 H -0.3033 0.9821 0.4549 0.062 Uiso 1 1 calc R . . C10 C -0.3529(2) 1.10719(13) 0.37071(17) 0.0554(5) Uani 1 1 d . . . H10 H -0.4397 1.0872 0.2891 0.066 Uiso 1 1 calc R . . C11 C -0.1886(3) 1.22150(12) 0.50220(18) 0.0525(5) Uani 1 1 d . . . H11 H -0.1606 1.2833 0.5144 0.063 Uiso 1 1 calc R . . C12 C -0.0960(2) 1.16256(11) 0.60627(15) 0.0425(4) Uani 1 1 d . . . H12 H -0.0068 1.1842 0.6855 0.051 Uiso 1 1 calc R . . N1 N 0.46470(18) 0.73002(9) 1.27341(14) 0.0456(4) Uani 1 1 d . . . N2 N 0.13230(18) 0.95131(8) 0.89958(13) 0.0444(4) Uani 1 1 d . . . H5 H 0.0929 0.8969 0.8759 0.053 Uiso 1 1 calc R . . N3 N 0.06338(18) 1.02354(8) 0.81208(13) 0.0418(3) Uani 1 1 d . . . N4 N -0.3163(2) 1.19551(11) 0.38461(14) 0.0564(4) Uani 1 1 d . . . O1 O 0.32471(18) 1.04147(8) 1.06409(12) 0.0645(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0448(9) 0.0392(9) 0.0397(8) 0.0039(7) 0.0003(7) -0.0054(7) C2 0.0399(9) 0.0492(10) 0.0435(9) 0.0057(8) -0.0022(7) 0.0026(8) C3 0.0496(10) 0.0361(8) 0.0473(9) 0.0045(7) 0.0069(8) -0.0044(7) C4 0.0392(8) 0.0386(8) 0.0379(8) 0.0011(7) -0.0002(7) -0.0009(7) C5 0.0446(9) 0.0314(8) 0.0267(7) -0.0003(6) 0.0032(6) 0.0011(6) C6 0.0473(9) 0.0336(8) 0.0344(8) 0.0008(6) 0.0012(7) -0.0012(7) C7 0.0562(10) 0.0339(8) 0.0392(8) 0.0021(7) -0.0028(7) -0.0006(7) C8 0.0416(9) 0.0388(8) 0.0329(7) 0.0006(6) 0.0023(7) 0.0026(7) C9 0.0559(11) 0.0415(9) 0.0423(9) -0.0025(7) -0.0050(8) 0.0000(8) C10 0.0536(11) 0.0578(11) 0.0385(9) -0.0028(8) -0.0070(8) 0.0088(9) C11 0.0647(11) 0.0377(9) 0.0483(10) 0.0050(8) 0.0091(9) 0.0014(8) C12 0.0448(9) 0.0406(8) 0.0356(8) 0.0005(7) 0.0045(7) -0.0016(7) N1 0.0494(8) 0.0381(7) 0.0420(7) 0.0073(6) 0.0053(6) 0.0041(6) N2 0.0546(9) 0.0303(7) 0.0349(7) 0.0034(5) -0.0034(6) 0.0003(6) N3 0.0464(8) 0.0352(7) 0.0346(7) 0.0056(5) 0.0009(6) 0.0029(6) N4 0.0632(10) 0.0508(9) 0.0438(8) 0.0077(7) 0.0022(7) 0.0124(7) O1 0.0820(10) 0.0346(7) 0.0507(7) 0.0022(5) -0.0139(6) -0.0098(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.378(2) . ? C1 C5 1.382(2) . ? C2 N1 1.327(2) . ? C3 N1 1.330(2) . ? C3 C4 1.379(2) . ? C4 C5 1.381(2) . ? C5 C6 1.502(2) . ? C6 O1 1.2117(18) . ? C6 N2 1.355(2) . ? C7 N3 1.265(2) . ? C7 C8 1.460(2) . ? C8 C12 1.385(2) . ? C8 C9 1.387(2) . ? C9 C10 1.373(2) . ? C10 N4 1.323(2) . ? C11 N4 1.337(2) . ? C11 C12 1.376(2) . ? N2 N3 1.3765(17) . ? 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 C2 C1 C5 118.96(15) . . ? N1 C2 C1 123.94(15) . . ? N1 C3 C4 124.20(15) . . ? C3 C4 C5 118.61(14) . . ? C4 C5 C1 117.88(13) . . ? C4 C5 C6 123.63(14) . . ? C1 C5 C6 118.46(14) . . ? O1 C6 N2 124.11(14) . . ? O1 C6 C5 121.87(14) . . ? N2 C6 C5 114.02(13) . . ? N3 C7 C8 122.10(15) . . ? C12 C8 C9 117.22(14) . . ? C12 C8 C7 123.59(14) . . ? C9 C8 C7 119.18(15) . . ? C10 C9 C8 119.45(16) . . ? N4 C10 C9 123.96(16) . . ? N4 C11 C12 124.08(16) . . ? C11 C12 C8 118.91(15) . . ? C2 N1 C3 116.39(13) . . ? C6 N2 N3 119.32(12) . . ? C7 N3 N2 115.00(13) . . ? C10 N4 C11 116.36(15) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.215 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.050 #====================================== data_Complex1 _database_code_depnum_ccdc_archive 'CCDC 646863' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H20 Cu4 N12 O2' _chemical_formula_weight 810.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.4337(6) _cell_length_b 32.490(2) _cell_length_c 10.2061(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.3930(10) _cell_angle_gamma 90.00 _cell_volume 3015.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3950 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.39 _exptl_crystal_description column _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 2.832 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19172 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 28.28 _reflns_number_total 6977 _reflns_number_gt 5077 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+1.7782P] 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 6977 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1392 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.187 _refine_ls_shift/su_max 0.002 _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 0.22905(6) 1.096449(16) 0.90494(6) 0.04239(16) Uani 1 1 d . . 2 Cu2 Cu 0.72976(6) 1.138448(16) 0.91027(6) 0.04256(16) Uani 1 1 d . . 2 Cu3 Cu 1.17392(6) 0.596812(17) 0.88916(7) 0.05146(18) Uani 1 1 d . . 2 Cu4 Cu 0.68130(6) 0.634724(16) 0.91329(6) 0.04643(17) Uani 1 1 d . . 2 O1 O -0.2180(3) 0.91911(10) 0.7809(4) 0.0621(10) Uani 1 1 d . . 2 O2 O 0.2585(3) 0.88481(9) 0.6982(3) 0.0524(8) Uani 1 1 d . A 2 C1 C -0.0079(5) 1.03352(12) 0.8022(4) 0.0405(10) Uani 1 1 d . . 2 H1 H -0.0603 1.0575 0.7727 0.049 Uiso 1 1 calc R . 2 C2 C -0.0804(4) 0.99650(12) 0.7747(4) 0.0393(9) Uani 1 1 d . . 2 H2 H -0.1800 0.9958 0.7295 0.047 Uiso 1 1 calc R . 2 C3 C -0.0041(4) 0.96032(11) 0.8150(4) 0.0333(9) Uani 1 1 d . . 2 C4 C 0.1420(5) 0.96322(11) 0.8847(4) 0.0377(9) Uani 1 1 d . . 2 H4 H 0.1970 0.9396 0.9145 0.045 Uiso 1 1 calc R . 2 C5 C 0.2058(5) 1.00185(13) 0.9098(4) 0.0392(10) Uani 1 1 d . . 2 H5 H 0.3043 1.0034 0.9579 0.047 Uiso 1 1 calc R . 2 C6 C -0.0882(5) 0.92028(12) 0.7817(4) 0.0385(9) Uani 1 1 d . . 2 C7 C 0.0101(5) 0.82175(12) 0.7104(5) 0.0459(11) Uani 1 1 d . . 2 H7A H 0.1094 0.8271 0.7216 0.055 Uiso 1 1 calc R . 2 C8 C -0.0472(5) 0.77996(12) 0.6770(4) 0.0414(10) Uani 1 1 d . . 2 C9 C -0.1939(5) 0.77244(13) 0.6140(5) 0.0475(11) Uani 1 1 d . . 2 H9 H -0.2597 0.7942 0.5886 0.057 Uiso 1 1 calc R . 2 C10 C -0.2409(5) 0.73247(13) 0.5895(5) 0.0469(11) Uani 1 1 d . . 2 H10 H -0.3398 0.7278 0.5475 0.056 Uiso 1 1 calc R . 2 C11 C -0.0100(5) 0.70782(13) 0.6818(5) 0.0529(12) Uani 1 1 d . . 2 H11 H 0.0545 0.6858 0.7054 0.063 Uiso 1 1 calc R . 2 C12 C 0.0461(5) 0.74679(13) 0.7097(5) 0.0512(12) Uani 1 1 d . . 2 H12 H 0.1458 0.7507 0.7501 0.061 Uiso 1 1 calc R . 2 C13 C 0.4789(5) 1.01529(14) 0.7078(6) 0.0614(14) Uani 1 1 d . A 2 H13 H 0.5585 1.0324 0.7451 0.074 Uiso 1 1 calc R A 2 C14 C 0.4947(5) 0.97330(12) 0.7340(5) 0.0533(13) Uani 1 1 d . A 2 H14 H 0.5825 0.9627 0.7880 0.064 Uiso 1 1 calc R A 2 C15 C 0.3779(4) 0.94767(12) 0.6786(4) 0.0368(9) Uani 1 1 d . A 2 C16 C 0.2508(5) 0.96510(13) 0.5981(4) 0.0421(10) Uani 1 1 d . A 2 H16 H 0.1705 0.9487 0.5571 0.051 Uiso 1 1 calc R A 2 C17 C 0.2446(5) 1.00718(13) 0.5793(4) 0.0441(10) Uani 1 1 d . A 2 H17 H 0.1577 1.0185 0.5265 0.053 Uiso 1 1 calc R A 2 C18 C 0.3762(4) 0.90251(12) 0.7089(4) 0.0350(9) Uani 1 1 d . A 2 C19 C 0.6291(4) 0.82661(12) 0.8375(4) 0.0391(9) Uani 1 1 d . . 2 H19 H 0.7128 0.8430 0.8608 0.047 Uiso 1 1 calc R . 2 C20 C 0.6371(4) 0.78274(12) 0.8698(4) 0.0365(9) Uani 1 1 d . . 2 C21 C 0.5160(5) 0.75714(12) 0.8273(5) 0.0458(11) Uani 1 1 d . . 2 H21 H 0.4251 0.7680 0.7815 0.055 Uiso 1 1 calc R . 2 C22 C 0.5314(5) 0.71581(13) 0.8532(5) 0.0519(12) Uani 1 1 d . . 2 H22 H 0.4489 0.6991 0.8242 0.062 Uiso 1 1 calc R . 2 C23 C 0.7751(5) 0.72333(13) 0.9620(5) 0.0507(12) Uani 1 1 d . . 2 H23 H 0.8646 0.7120 1.0094 0.061 Uiso 1 1 calc R . 2 C24 C 0.7678(5) 0.76514(13) 0.9404(5) 0.0459(11) Uani 1 1 d . . 2 H24 H 0.8507 0.7814 0.9732 0.055 Uiso 1 1 calc R . 2 C25 C 0.4319(5) 1.10448(12) 0.9233(4) 0.0375(9) Uani 1 1 d . . . C26 C 0.9317(5) 1.13150(11) 0.9215(4) 0.0365(9) Uani 1 1 d . . . C27 C 0.8680(5) 0.62089(13) 0.9027(4) 0.0413(10) Uani 1 1 d . . . C28 C 1.3692(5) 0.60951(12) 0.9041(4) 0.0416(10) Uani 1 1 d . . . N1 N 0.1341(4) 1.03672(10) 0.8690(3) 0.0364(8) Uani 1 1 d . . . N2 N -0.0101(4) 0.88879(9) 0.7547(3) 0.0375(8) Uani 1 1 d . . . H2A H 0.0808 0.8921 0.7564 0.045 Uiso 1 1 calc R . 2 N3 N -0.0765(4) 0.85077(10) 0.7240(3) 0.0417(9) Uani 1 1 d . . . N4 N -0.1513(4) 0.69952(11) 0.6229(4) 0.0476(9) Uani 1 1 d . . . N5 N 0.3564(4) 1.03241(10) 0.6325(4) 0.0477(9) Uani 1 1 d . . . N6 N 0.5053(4) 0.88331(9) 0.7466(3) 0.0362(8) Uani 1 1 d . . . H6 H 0.5863 0.8962 0.7523 0.043 Uiso 1 1 calc R A 2 N7 N 0.5040(4) 0.84194(9) 0.7762(3) 0.0375(8) Uani 1 1 d . . . N8 N 0.6592(4) 0.69802(11) 0.9182(4) 0.0482(9) Uani 1 1 d . . . N9 N 0.5522(4) 1.11185(10) 0.9292(4) 0.0418(8) Uani 1 1 d . . . N10 N 1.0517(4) 1.12473(11) 0.9224(4) 0.0409(8) Uani 1 1 d . . . N11 N 0.9873(4) 0.61456(12) 0.9016(4) 0.0526(10) Uani 1 1 d . . . N12 N 1.4904(4) 0.61590(11) 0.9136(4) 0.0445(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0270(3) 0.0377(3) 0.0640(4) -0.0061(2) 0.0147(2) -0.0054(2) Cu2 0.0275(3) 0.0352(3) 0.0665(4) 0.0058(2) 0.0151(2) 0.0035(2) Cu3 0.0320(3) 0.0393(3) 0.0874(5) -0.0031(3) 0.0233(3) 0.0007(2) Cu4 0.0305(3) 0.0362(3) 0.0744(4) 0.0040(3) 0.0173(3) 0.0049(2) O1 0.0326(18) 0.0351(17) 0.121(3) -0.0030(17) 0.0254(19) -0.0063(13) O2 0.0312(16) 0.0387(17) 0.087(2) -0.0003(16) 0.0161(16) -0.0050(13) C1 0.040(2) 0.026(2) 0.057(3) 0.0010(18) 0.014(2) -0.0012(17) C2 0.031(2) 0.031(2) 0.056(3) -0.0004(18) 0.0113(19) -0.0017(16) C3 0.031(2) 0.031(2) 0.040(2) -0.0013(16) 0.0136(17) -0.0064(16) C4 0.039(2) 0.0250(19) 0.049(2) 0.0015(17) 0.0110(19) 0.0029(16) C5 0.033(2) 0.038(2) 0.045(2) -0.0048(18) 0.0086(18) -0.0020(17) C6 0.033(2) 0.030(2) 0.053(3) 0.0041(18) 0.0126(19) -0.0050(17) C7 0.047(3) 0.032(2) 0.064(3) -0.004(2) 0.025(2) -0.0090(19) C8 0.046(3) 0.030(2) 0.054(3) -0.0053(18) 0.024(2) -0.0123(18) C9 0.055(3) 0.027(2) 0.062(3) -0.0051(19) 0.018(2) 0.0016(19) C10 0.036(2) 0.037(2) 0.066(3) -0.010(2) 0.011(2) -0.0066(19) C11 0.037(3) 0.032(2) 0.092(4) -0.006(2) 0.021(2) -0.0024(19) C12 0.036(2) 0.033(2) 0.085(3) -0.008(2) 0.018(2) -0.0062(18) C13 0.033(3) 0.035(2) 0.113(4) -0.008(3) 0.016(3) -0.0043(19) C14 0.028(2) 0.030(2) 0.097(4) -0.006(2) 0.007(2) 0.0013(17) C15 0.031(2) 0.033(2) 0.050(2) -0.0070(17) 0.0164(18) -0.0003(16) C16 0.036(2) 0.038(2) 0.050(3) -0.0046(19) 0.0053(19) -0.0038(18) C17 0.038(2) 0.038(2) 0.055(3) 0.0017(19) 0.011(2) 0.0050(19) C18 0.028(2) 0.032(2) 0.046(2) -0.0072(17) 0.0126(17) -0.0057(16) C19 0.032(2) 0.029(2) 0.057(3) -0.0049(18) 0.0136(19) -0.0049(16) C20 0.035(2) 0.030(2) 0.047(2) -0.0005(17) 0.0148(18) -0.0017(16) C21 0.029(2) 0.034(2) 0.070(3) 0.004(2) 0.007(2) 0.0037(17) C22 0.029(2) 0.037(2) 0.090(4) 0.002(2) 0.017(2) -0.0011(18) C23 0.034(2) 0.041(2) 0.073(3) 0.007(2) 0.007(2) 0.0061(19) C24 0.032(2) 0.039(2) 0.062(3) -0.002(2) 0.006(2) -0.0045(18) C25 0.036(2) 0.028(2) 0.050(2) -0.0016(17) 0.0143(19) -0.0015(17) C26 0.036(2) 0.028(2) 0.046(2) 0.0007(17) 0.0119(18) -0.0015(17) C27 0.033(2) 0.041(2) 0.053(3) 0.0028(19) 0.0177(19) 0.0054(18) C28 0.035(2) 0.032(2) 0.061(3) -0.0076(19) 0.018(2) 0.0002(18) N1 0.0326(19) 0.0285(17) 0.050(2) -0.0034(14) 0.0146(16) -0.0051(14) N2 0.0336(19) 0.0236(16) 0.059(2) -0.0023(15) 0.0193(16) -0.0060(14) N3 0.053(2) 0.0261(17) 0.050(2) -0.0050(15) 0.0196(17) -0.0114(16) N4 0.038(2) 0.036(2) 0.072(3) -0.0090(18) 0.0200(19) -0.0071(16) N5 0.035(2) 0.0281(17) 0.083(3) -0.0010(18) 0.0208(19) 0.0001(15) N6 0.0282(18) 0.0269(17) 0.055(2) 0.0010(14) 0.0127(15) -0.0048(13) N7 0.0334(19) 0.0273(17) 0.053(2) -0.0013(15) 0.0131(16) -0.0026(14) N8 0.035(2) 0.0345(19) 0.077(3) 0.0059(18) 0.0179(19) 0.0014(15) N9 0.031(2) 0.040(2) 0.057(2) 0.0018(16) 0.0148(16) -0.0001(15) N10 0.031(2) 0.0379(19) 0.055(2) -0.0043(16) 0.0124(16) -0.0006(15) N11 0.045(2) 0.046(2) 0.071(3) 0.0020(19) 0.023(2) 0.0083(18) N12 0.039(2) 0.037(2) 0.058(2) 0.0008(16) 0.0142(18) -0.0006(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C25 1.891(4) . ? Cu1 N10 1.958(4) 1_455 ? Cu1 N1 2.128(3) . ? Cu2 C26 1.892(4) . ? Cu2 N9 1.939(4) . ? Cu2 N4 2.113(3) 2_556 ? Cu3 C28 1.854(4) . ? Cu3 N11 1.889(4) . ? Cu3 N5 2.116(3) 2_646 ? Cu4 C27 1.849(4) . ? Cu4 N12 1.902(4) 1_455 ? Cu4 N8 2.069(3) . ? O1 C6 1.223(5) . ? O2 C18 1.229(5) . ? C1 N1 1.336(5) . ? C1 C2 1.375(5) . ? C2 C3 1.383(5) . ? C3 C4 1.376(5) . ? C3 C6 1.515(5) . ? C4 C5 1.386(5) . ? C5 N1 1.328(5) . ? C6 N2 1.331(5) . ? C7 N3 1.279(5) . ? C7 C8 1.467(5) . ? C8 C12 1.375(6) . ? C8 C9 1.384(6) . ? C9 C10 1.374(6) . ? C10 N4 1.350(5) . ? C11 N4 1.336(6) . ? C11 C12 1.373(6) . ? C13 N5 1.328(6) . ? C13 C14 1.391(6) . ? C14 C15 1.377(6) . ? C15 C16 1.382(5) . ? C15 C18 1.500(5) . ? C16 C17 1.379(6) . ? C17 N5 1.332(5) . ? C18 N6 1.331(5) . ? C19 N7 1.280(5) . ? C19 C20 1.461(5) . ? C20 C24 1.377(6) . ? C20 C21 1.386(5) . ? C21 C22 1.369(6) . ? C22 N8 1.343(5) . ? C23 N8 1.346(5) . ? C23 C24 1.375(6) . ? C25 N9 1.146(5) . ? C26 N10 1.151(5) . ? C27 N11 1.146(5) . ? C28 N12 1.141(5) . ? N2 N3 1.383(4) . ? N4 Cu2 2.113(3) 2_546 ? N5 Cu3 2.116(3) 2_656 ? N6 N7 1.378(4) . ? N10 Cu1 1.958(4) 1_655 ? N12 Cu4 1.902(4) 1_655 ? 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 C25 Cu1 N10 142.48(16) . 1_455 ? C25 Cu1 N1 120.76(15) . . ? N10 Cu1 N1 96.49(14) 1_455 . ? C26 Cu2 N9 145.43(15) . . ? C26 Cu2 N4 115.22(15) . 2_556 ? N9 Cu2 N4 99.16(15) . 2_556 ? C28 Cu3 N11 148.22(18) . . ? C28 Cu3 N5 109.42(16) . 2_646 ? N11 Cu3 N5 101.92(16) . 2_646 ? C27 Cu4 N12 147.01(18) . 1_455 ? C27 Cu4 N8 110.28(17) . . ? N12 Cu4 N8 102.61(15) 1_455 . ? N1 C1 C2 123.3(4) . . ? C1 C2 C3 119.4(4) . . ? C4 C3 C2 117.8(3) . . ? C4 C3 C6 124.6(4) . . ? C2 C3 C6 117.6(3) . . ? C3 C4 C5 118.9(4) . . ? N1 C5 C4 123.7(4) . . ? O1 C6 N2 125.6(4) . . ? O1 C6 C3 119.5(4) . . ? N2 C6 C3 114.9(4) . . ? N3 C7 C8 120.1(4) . . ? C12 C8 C9 118.1(4) . . ? C12 C8 C7 119.8(4) . . ? C9 C8 C7 122.1(4) . . ? C10 C9 C8 119.1(4) . . ? N4 C10 C9 123.6(4) . . ? N4 C11 C12 124.3(4) . . ? C11 C12 C8 119.0(4) . . ? N5 C13 C14 123.7(4) . . ? C15 C14 C13 118.7(4) . . ? C14 C15 C16 118.0(4) . . ? C14 C15 C18 123.9(4) . . ? C16 C15 C18 117.9(4) . . ? C17 C16 C15 119.1(4) . . ? N5 C17 C16 123.6(4) . . ? O2 C18 N6 122.8(4) . . ? O2 C18 C15 119.9(4) . . ? N6 C18 C15 117.3(3) . . ? N7 C19 C20 118.4(4) . . ? C24 C20 C21 117.6(4) . . ? C24 C20 C19 120.6(4) . . ? C21 C20 C19 121.7(4) . . ? C22 C21 C20 119.4(4) . . ? N8 C22 C21 123.6(4) . . ? N8 C23 C24 123.3(4) . . ? C23 C24 C20 119.6(4) . . ? N9 C25 Cu1 175.1(4) . . ? N10 C26 Cu2 174.9(4) . . ? N11 C27 Cu4 175.3(4) . . ? N12 C28 Cu3 177.6(4) . . ? C5 N1 C1 116.8(3) . . ? C5 N1 Cu1 124.6(3) . . ? C1 N1 Cu1 118.6(3) . . ? C6 N2 N3 119.4(3) . . ? C7 N3 N2 114.8(4) . . ? C11 N4 C10 115.9(4) . . ? C11 N4 Cu2 121.8(3) . 2_546 ? C10 N4 Cu2 122.3(3) . 2_546 ? C13 N5 C17 116.8(4) . . ? C13 N5 Cu3 123.2(3) . 2_656 ? C17 N5 Cu3 119.7(3) . 2_656 ? C18 N6 N7 117.4(3) . . ? C19 N7 N6 115.2(3) . . ? C22 N8 C23 116.4(4) . . ? C22 N8 Cu4 119.9(3) . . ? C23 N8 Cu4 122.5(3) . . ? C25 N9 Cu2 163.3(3) . . ? C26 N10 Cu1 162.1(3) . 1_655 ? C27 N11 Cu3 171.9(4) . . ? C28 N12 Cu4 170.5(4) . 1_655 ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 1.310 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.094 #====================================== data_Complex2 _database_code_depnum_ccdc_archive 'CCDC 646864' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H23 Cu4 N11 O4.50' _chemical_formula_weight 827.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pcca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 21.9969(15) _cell_length_b 7.3578(5) _cell_length_c 20.3447(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3292.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 28.30 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 2.600 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20812 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4066 _reflns_number_gt 3016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+2.0231P] 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 4066 _refine_ls_number_parameters 228 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1353 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.088 _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 O1 O 0.48745(12) 0.2958(3) 0.44312(12) 0.0474(6) Uani 1 1 d . . . Cu1 Cu 0.5000 0.5000 0.5000 0.03892(17) Uani 1 2 d S . . Cu2 Cu 0.2500 0.0000 0.82000(3) 0.04666(19) Uani 1 2 d S . . Cu3 Cu 0.41262(2) -0.42888(7) 0.82581(3) 0.05188(17) Uani 1 1 d . . . N1 N 0.41700(13) -0.3163(4) 0.36789(16) 0.0440(7) Uani 1 1 d . . . N2 N 0.42211(13) 0.2056(4) 0.52535(14) 0.0399(6) Uani 1 1 d . . . N3 N 0.43935(13) 0.3705(4) 0.55296(14) 0.0411(6) Uani 1 1 d . . . N4 N 0.30568(13) 0.1387(4) 0.74660(14) 0.0442(7) Uani 1 1 d . . . N5 N 0.34329(17) -0.2885(5) 0.84681(19) 0.0622(9) Uani 1 1 d . . . N6 N 0.47978(16) -0.4039(4) 0.76815(18) 0.0507(8) Uani 0.50 1 d P . 1 C14 C 0.47978(16) -0.4039(4) 0.76815(18) 0.0507(8) Uani 0.50 1 d P . 2 C1 C 0.45081(18) -0.1849(5) 0.34194(19) 0.0489(9) Uani 1 1 d . . . H1 H 0.4682 -0.2049 0.3009 0.059 Uiso 1 1 calc R . . C2 C 0.46150(16) -0.0205(4) 0.37245(19) 0.0441(8) Uani 1 1 d . . . H2 H 0.4848 0.0682 0.3519 0.053 Uiso 1 1 calc R . . C3 C 0.43718(15) 0.0105(4) 0.43367(16) 0.0358(7) Uani 1 1 d . . . C4 C 0.40125(17) -0.1249(5) 0.4608(2) 0.0486(9) Uani 1 1 d . . . H4 H 0.3833 -0.1082 0.5017 0.058 Uiso 1 1 calc R . . C5 C 0.39241(17) -0.2836(5) 0.4268(2) 0.0499(9) Uani 1 1 d . . . H5 H 0.3681 -0.3729 0.4456 0.060 Uiso 1 1 calc R . . C6 C 0.44967(15) 0.1845(4) 0.46908(16) 0.0376(7) Uani 1 1 d . . . C7 C 0.41884(17) 0.4154(5) 0.60893(18) 0.0452(8) Uani 1 1 d . . . H7 H 0.4310 0.5291 0.6240 0.054 Uiso 1 1 calc R . . C8 C 0.37831(16) 0.3129(5) 0.65392(17) 0.0403(7) Uani 1 1 d . . . C9 C 0.34599(18) 0.4086(5) 0.70046(19) 0.0466(8) Uani 1 1 d . . . H9 H 0.3485 0.5347 0.7019 0.056 Uiso 1 1 calc R . . C10 C 0.31041(17) 0.3184(5) 0.74434(18) 0.0466(8) Uani 1 1 d . . . H10 H 0.2882 0.3864 0.7744 0.056 Uiso 1 1 calc R . . C11 C 0.3376(2) 0.0456(5) 0.7034(2) 0.0583(11) Uani 1 1 d . . . H11 H 0.3357 -0.0806 0.7052 0.070 Uiso 1 1 calc R . . C12 C 0.3740(2) 0.1246(5) 0.6553(2) 0.0573(11) Uani 1 1 d . . . H12 H 0.3948 0.0535 0.6250 0.069 Uiso 1 1 calc R . . C13 C 0.30365(15) -0.1871(5) 0.84710(17) 0.0395(7) Uani 1 1 d . . . O1W O 0.3043(5) 0.7048(15) 0.5843(5) 0.122(3) Uani 0.50 1 d PU A 1 H1WA H 0.3133 0.8117 0.5968 0.147 Uiso 0.50 1 d PR A 1 H1WB H 0.2659 0.6998 0.5794 0.147 Uiso 0.50 1 d PR A 1 O2W O 0.2264(6) 0.806(2) 0.5003(6) 0.189(5) Uani 0.50 1 d PU B 2 H2WA H 0.2116 0.9021 0.5169 0.227 Uiso 0.50 1 d PR B 2 H2WB H 0.2213 0.7185 0.5271 0.227 Uiso 0.50 1 d PR B 2 O3W O 0.2755(11) 0.716(4) 0.5470(11) 0.134(8) Uani 0.25 1 d PU C 3 H3WA H 0.2545 0.8044 0.5616 0.160 Uiso 0.25 1 d PR C 3 H3WB H 0.2534 0.6510 0.5222 0.160 Uiso 0.25 1 d PR C 3 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 O1 0.0589(15) 0.0439(13) 0.0394(13) -0.0015(11) 0.0102(11) -0.0207(11) Cu1 0.0475(3) 0.0367(3) 0.0326(3) 0.0001(2) 0.0051(2) -0.0179(2) Cu2 0.0432(3) 0.0528(4) 0.0439(4) 0.000 0.000 -0.0012(3) Cu3 0.0566(3) 0.0419(3) 0.0572(3) 0.0052(2) 0.0050(2) 0.0081(2) N1 0.0455(16) 0.0339(15) 0.0527(18) -0.0026(13) 0.0062(14) -0.0078(12) N2 0.0462(15) 0.0373(14) 0.0363(15) -0.0028(12) 0.0060(12) -0.0145(12) N3 0.0494(16) 0.0374(14) 0.0366(15) -0.0017(12) 0.0054(13) -0.0136(13) N4 0.0463(16) 0.0402(15) 0.0460(17) -0.0015(13) 0.0142(13) -0.0052(13) N5 0.064(2) 0.057(2) 0.065(2) -0.0060(18) 0.0030(18) -0.0087(18) N6 0.057(2) 0.0419(18) 0.053(2) 0.0031(15) 0.0060(15) 0.0052(14) C14 0.057(2) 0.0419(18) 0.053(2) 0.0031(15) 0.0060(15) 0.0052(14) C1 0.061(2) 0.0409(19) 0.044(2) -0.0021(16) 0.0144(18) -0.0044(17) C2 0.0476(19) 0.0341(17) 0.051(2) 0.0055(15) 0.0066(16) -0.0099(14) C3 0.0392(17) 0.0316(16) 0.0366(17) 0.0022(13) -0.0003(13) -0.0048(13) C4 0.053(2) 0.0455(19) 0.047(2) -0.0041(17) 0.0119(16) -0.0168(16) C5 0.053(2) 0.0382(18) 0.059(2) -0.0013(17) 0.0090(18) -0.0140(16) C6 0.0400(16) 0.0395(18) 0.0333(17) 0.0045(14) 0.0014(13) -0.0075(13) C7 0.054(2) 0.0387(18) 0.043(2) -0.0009(15) 0.0026(16) -0.0138(15) C8 0.0439(18) 0.0416(18) 0.0356(17) 0.0017(14) 0.0061(14) -0.0095(14) C9 0.060(2) 0.0327(17) 0.048(2) -0.0022(15) 0.0054(17) -0.0093(15) C10 0.051(2) 0.043(2) 0.046(2) -0.0026(16) 0.0104(16) 0.0007(16) C11 0.081(3) 0.0348(18) 0.059(2) -0.0014(17) 0.031(2) -0.0101(18) C12 0.072(3) 0.043(2) 0.057(2) -0.0023(18) 0.031(2) -0.0012(19) C13 0.0374(17) 0.0390(17) 0.0421(18) -0.0036(15) -0.0028(14) 0.0048(14) O1W 0.121(6) 0.135(7) 0.112(6) 0.033(6) -0.008(6) -0.009(5) O2W 0.168(8) 0.260(10) 0.140(8) 0.035(7) -0.011(7) 0.026(8) O3W 0.120(10) 0.160(11) 0.121(11) 0.008(9) 0.006(8) 0.006(9) _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 O1 C6 1.281(4) . ? O1 Cu1 1.916(2) . ? Cu1 O1 1.916(2) 5_666 ? Cu1 N3 1.962(3) 5_666 ? Cu1 N3 1.962(3) . ? Cu2 C13 1.895(3) . ? Cu2 C13 1.895(3) 2 ? Cu2 N4 2.185(3) 2 ? Cu2 N4 2.184(3) . ? Cu3 N5 1.891(4) . ? Cu3 N6 1.895(3) . ? Cu3 N1 2.063(3) 7_546 ? N1 C1 1.329(4) . ? N1 C5 1.336(5) . ? N1 Cu3 2.063(3) 7_545 ? N2 C6 1.305(4) . ? N2 N3 1.390(4) . ? N3 C7 1.269(4) . ? N4 C11 1.316(5) . ? N4 C10 1.327(5) . ? N5 C13 1.147(5) . ? N6 N6 1.156(7) 3_656 ? C1 C2 1.380(5) . ? C2 C3 1.375(5) . ? C3 C4 1.386(5) . ? C3 C6 1.495(5) . ? C4 C5 1.371(5) . ? C7 C8 1.484(5) . ? C8 C9 1.377(5) . ? C8 C12 1.389(5) . ? C9 C10 1.360(5) . ? C11 C12 1.393(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 C6 O1 Cu1 110.2(2) . . ? O1 Cu1 O1 180.0 5_666 . ? O1 Cu1 N3 81.54(11) 5_666 5_666 ? O1 Cu1 N3 98.46(11) . 5_666 ? O1 Cu1 N3 98.46(11) 5_666 . ? O1 Cu1 N3 81.54(11) . . ? N3 Cu1 N3 180.00(12) 5_666 . ? C13 Cu2 C13 146.2(2) . 2 ? C13 Cu2 N4 102.04(13) . 2 ? C13 Cu2 N4 100.90(14) 2 2 ? C13 Cu2 N4 100.90(14) . . ? C13 Cu2 N4 102.04(13) 2 . ? N4 Cu2 N4 93.74(16) 2 . ? N5 Cu3 N6 135.67(16) . . ? N5 Cu3 N1 116.13(14) . 7_546 ? N6 Cu3 N1 107.98(13) . 7_546 ? C1 N1 C5 116.8(3) . . ? C1 N1 Cu3 121.5(2) . 7_545 ? C5 N1 Cu3 121.1(2) . 7_545 ? C6 N2 N3 109.4(3) . . ? C7 N3 N2 119.5(3) . . ? C7 N3 Cu1 127.5(2) . . ? N2 N3 Cu1 112.8(2) . . ? C11 N4 C10 117.0(3) . . ? C11 N4 Cu2 120.8(2) . . ? C10 N4 Cu2 122.2(2) . . ? C13 N5 Cu3 165.7(4) . . ? N6 N6 Cu3 174.29(15) 3_656 . ? N1 C1 C2 123.7(3) . . ? C3 C2 C1 119.1(3) . . ? C2 C3 C4 117.6(3) . . ? C2 C3 C6 120.5(3) . . ? C4 C3 C6 121.9(3) . . ? C5 C4 C3 119.5(3) . . ? N1 C5 C4 123.3(3) . . ? O1 C6 N2 126.0(3) . . ? O1 C6 C3 117.9(3) . . ? N2 C6 C3 116.1(3) . . ? N3 C7 C8 129.4(3) . . ? C9 C8 C12 117.4(3) . . ? C9 C8 C7 118.3(3) . . ? C12 C8 C7 124.1(3) . . ? C10 C9 C8 119.9(3) . . ? N4 C10 C9 123.6(3) . . ? N4 C11 C12 123.9(4) . . ? C8 C12 C11 118.0(4) . . ? N5 C13 Cu2 160.7(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.789 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.109