Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Miguel Julve' _publ_contact_author_address ; Instituto di Ciencia Molecular Universitat di Valencia Valencia 46980 SPAIN ; _publ_contact_author_email MIGUEL.JULVE@UV.ES _publ_section_title ; Ligand effects on the structures and magnetic properties tricyanomethanide-containing copper(II) complexes ; loop_ _publ_author_name 'Miguel Julve' 'Donatella Armentano' 'Abdeslem Bentama' 'G.De Munno' 'F. Lloret' ; S.-E.Stiriba ; C.Yuste # Attachment 'DATA_1_CCDC 650797.CIF' data_cudppnt _database_code_depnum_ccdc_archive 'CCDC 650797' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H11 Cu2 N13 O' _chemical_formula_weight 648.58 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 P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 7.4872(14) _cell_length_b 23.624(5) _cell_length_c 7.7646(16) _cell_angle_alpha 90.00 _cell_angle_beta 105.152(4) _cell_angle_gamma 90.00 _cell_volume 1325.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7366 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 24.55 _exptl_crystal_description parallelepiped _exptl_crystal_colour Brown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 1.653 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7552 _exptl_absorpt_correction_T_max 0.8522 _exptl_absorpt_process_details sadabs _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 detedtor' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11644 _diffrn_reflns_av_R_equivalents 0.0943 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2281 _reflns_number_gt 2139 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius Saint' _computing_cell_refinement 'Bruker-Nonius Saint' _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^)+(0.1000P)^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 2281 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1366 _refine_ls_R_factor_gt 0.1304 _refine_ls_wR_factor_ref 0.4253 _refine_ls_wR_factor_gt 0.4242 _refine_ls_goodness_of_fit_ref 3.633 _refine_ls_restrained_S_all 3.633 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.19571(17) -0.17888(6) -0.67006(16) 0.0435(8) Uani 1 1 d . . . O1 O -0.1570(15) -0.2500 -0.7670(15) 0.052(3) Uani 1 2 d S . . N1 N -0.2291(13) -0.1162(5) -0.5113(13) 0.050(3) Uani 1 1 d . . . C1 C -0.213(2) -0.0614(6) -0.544(3) 0.077(5) Uani 1 1 d . . . C2 C -0.262(4) -0.0185(8) -0.437(4) 0.119(9) Uani 1 1 d . . . C3 C -0.330(4) -0.0357(10) -0.287(4) 0.137(11) Uani 1 1 d . . . C4 C -0.348(3) -0.0939(7) -0.260(3) 0.082(5) Uani 1 1 d . . . C5 C -0.2973(16) -0.1314(6) -0.3680(19) 0.052(3) Uani 1 1 d . . . C6 C -0.3096(14) -0.1932(6) -0.3505(14) 0.042(3) Uani 1 1 d . . . C7 C -0.3519(14) -0.2208(6) -0.2025(14) 0.045(3) Uani 1 1 d . . . N2 N -0.2737(12) -0.2224(4) -0.4809(11) 0.037(2) Uani 1 1 d . . . N3 N -0.4862(16) -0.1583(6) -0.8537(16) 0.069(3) Uani 1 1 d . . . C9 C -0.6263(15) -0.1372(6) -0.8921(16) 0.053(3) Uani 1 1 d . . . C8 C -0.7931(16) -0.1076(6) -0.9429(19) 0.065(4) Uani 1 1 d . . . C10 C -0.9399(16) -0.1229(5) -0.8698(17) 0.055(3) Uani 1 1 d . . . N4 N -1.0552(14) -0.1372(5) -0.8112(16) 0.058(3) Uani 1 1 d . . . C11 C -0.819(2) -0.0613(10) -1.065(3) 0.119(9) Uani 1 1 d . . . N5 N -0.831(3) -0.0260(14) -1.157(4) 0.204(17) Uani 1 1 d . . . C12 C 0.189(3) -0.2500 -1.292(3) 0.136(17) Uani 1 2 d S . . C13 C 0.215(3) -0.197(2) -1.374(4) 0.20(2) Uani 1 1 d . . . N6 N 0.251(5) -0.153(2) -1.425(5) 0.26(2) Uani 1 1 d . . . C14 C 0.137(3) -0.2500 -1.127(3) 0.085(8) Uani 1 2 d S . . N7 N 0.093(3) -0.2500 -1.000(3) 0.093(7) Uani 1 2 d S . . 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 0.0360(10) 0.0728(14) 0.0282(11) 0.0137(6) 0.0200(7) 0.0076(6) O1 0.033(5) 0.094(9) 0.037(6) 0.000 0.024(5) 0.000 N1 0.038(5) 0.084(7) 0.036(5) 0.023(5) 0.025(4) 0.020(5) C1 0.073(10) 0.065(8) 0.112(14) 0.018(9) 0.060(10) 0.016(7) C2 0.17(2) 0.082(11) 0.16(2) -0.005(13) 0.13(2) 0.004(13) C3 0.19(3) 0.100(15) 0.18(3) 0.005(16) 0.15(2) 0.030(15) C4 0.110(13) 0.070(9) 0.092(12) -0.011(9) 0.073(11) -0.005(9) C5 0.040(6) 0.075(9) 0.053(7) 0.018(6) 0.031(5) 0.018(5) C6 0.032(6) 0.077(8) 0.020(5) -0.007(5) 0.011(4) 0.000(5) C7 0.027(5) 0.089(8) 0.022(5) -0.002(5) 0.011(4) -0.001(5) N2 0.030(4) 0.073(5) 0.014(4) 0.006(4) 0.015(3) 0.009(4) N3 0.045(7) 0.119(9) 0.052(7) 0.018(7) 0.026(5) 0.014(7) C9 0.028(6) 0.099(10) 0.037(7) 0.022(6) 0.014(5) 0.013(6) C8 0.039(6) 0.099(10) 0.067(9) 0.048(8) 0.031(6) 0.017(7) C10 0.040(6) 0.074(8) 0.057(8) 0.046(7) 0.023(6) 0.023(6) N4 0.036(5) 0.083(8) 0.062(7) 0.033(6) 0.027(5) 0.019(5) C11 0.078(12) 0.144(17) 0.16(2) 0.106(17) 0.069(13) 0.028(11) N5 0.118(17) 0.27(3) 0.23(3) 0.19(3) 0.063(18) 0.025(17) C12 0.048(13) 0.32(6) 0.035(13) 0.000 0.010(10) 0.000 C13 0.048(11) 0.48(6) 0.086(17) 0.10(3) 0.027(11) 0.10(2) N6 0.21(4) 0.45(6) 0.15(3) 0.21(3) 0.09(2) 0.08(4) C14 0.042(10) 0.17(2) 0.048(12) 0.000 0.014(9) 0.000 N7 0.090(15) 0.108(15) 0.103(18) 0.000 0.064(14) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.894(5) . ? Cu1 N4 1.971(10) 1_655 ? Cu1 N1 1.984(11) . ? Cu1 N2 2.002(8) . ? Cu1 N3 2.319(12) . ? Cu1 Cu1 3.360(3) 4 ? O1 Cu1 1.894(5) 4 ? N1 C1 1.330(18) . ? N1 C5 1.387(16) . ? C1 C2 1.42(2) . ? C2 C3 1.44(3) . ? C3 C4 1.40(3) . ? C4 C5 1.34(2) . ? C5 C6 1.471(19) . ? C6 N2 1.311(15) . ? C6 C7 1.427(16) . ? C7 C7 1.38(3) 4 ? N2 N2 1.302(19) 4 ? N3 C9 1.130(16) . ? C9 C8 1.395(16) . ? C8 C10 1.411(16) . ? C8 C11 1.43(2) . ? C10 N4 1.127(15) . ? N4 Cu1 1.971(10) 1_455 ? C11 N5 1.08(2) . ? C12 C14 1.43(3) . ? C12 C13 1.45(4) 4 ? C12 C13 1.45(4) . ? C13 N6 1.16(6) . ? C14 N7 1.12(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N4 93.6(4) . 1_655 ? O1 Cu1 N1 165.1(4) . . ? N4 Cu1 N1 98.3(5) 1_655 . ? O1 Cu1 N2 86.6(4) . . ? N4 Cu1 N2 165.0(4) 1_655 . ? N1 Cu1 N2 79.6(4) . . ? O1 Cu1 N3 99.1(5) . . ? N4 Cu1 N3 96.0(4) 1_655 . ? N1 Cu1 N3 88.6(4) . . ? N2 Cu1 N3 98.8(4) . . ? O1 Cu1 Cu1 27.5(3) . 4 ? N4 Cu1 Cu1 120.0(3) 1_655 4 ? N1 Cu1 Cu1 138.3(3) . 4 ? N2 Cu1 Cu1 59.1(3) . 4 ? N3 Cu1 Cu1 102.1(4) . 4 ? Cu1 O1 Cu1 125.0(6) 4 . ? C1 N1 C5 118.4(11) . . ? C1 N1 Cu1 125.1(9) . . ? C5 N1 Cu1 115.9(9) . . ? N1 C1 C2 122.2(15) . . ? C1 C2 C3 118.0(17) . . ? C4 C3 C2 117.8(19) . . ? C5 C4 C3 119.9(17) . . ? C4 C5 N1 123.6(13) . . ? C4 C5 C6 124.3(13) . . ? N1 C5 C6 112.1(11) . . ? N2 C6 C7 120.9(13) . . ? N2 C6 C5 115.0(10) . . ? C7 C6 C5 124.1(12) . . ? C7 C7 C6 117.2(8) 4 . ? N2 N2 C6 121.9(7) 4 . ? N2 N2 Cu1 120.9(3) 4 . ? C6 N2 Cu1 117.0(8) . . ? C9 N3 Cu1 155.8(12) . . ? N3 C9 C8 175.8(15) . . ? C9 C8 C10 119.4(11) . . ? C9 C8 C11 121.8(12) . . ? C10 C8 C11 118.8(11) . . ? N4 C10 C8 177.5(14) . . ? C10 N4 Cu1 161.9(9) . 1_455 ? N5 C11 C8 177(2) . . ? C14 C12 C13 119.5(18) . 4 ? C14 C12 C13 119.5(18) . . ? C13 C12 C13 121(4) 4 . ? N6 C13 C12 173(3) . . ? N7 C14 C12 179(3) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.415 _refine_diff_density_min -2.115 _refine_diff_density_rms 0.220 # Attachment 'DATA_2_CCDC 650798.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 650798' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H10 Cu N10' _chemical_formula_weight 477.94 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9667(11) _cell_length_b 10.1084(11) _cell_length_c 11.2802(12) _cell_angle_alpha 92.895(4) _cell_angle_beta 111.856(4) _cell_angle_gamma 101.973(4) _cell_volume 1021.56(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3937 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 25.81 _exptl_crystal_description parallelepiped _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 482 _exptl_absorpt_coefficient_mu 1.103 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.812 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_process_details sadabs _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 13539 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.98 _reflns_number_total 3937 _reflns_number_gt 3334 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius SAINT' _computing_cell_refinement 'Bruker-Nonius SAINT' _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^)+(0.0597P)^2^+0.4439P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3937 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.39403(3) 0.79948(3) 0.19682(3) 0.02597(13) Uani 1 1 d . . . N1 N 0.3133(3) 0.6757(2) 0.2995(2) 0.0291(5) Uani 1 1 d . . . N2 N 0.4655(2) 0.9340(2) 0.37805(19) 0.0223(4) Uani 1 1 d . . . N3 N 0.1975(2) 0.8245(2) 0.0738(2) 0.0266(5) Uani 1 1 d . . . N4 N 0.4662(2) 0.9205(2) 0.0851(2) 0.0243(5) Uani 1 1 d . . . C1 C 0.2366(4) 0.5461(3) 0.2535(3) 0.0483(9) Uani 1 1 d . . . H1A H 0.2106 0.5143 0.1672 0.058 Uiso 1 1 calc R . . C2 C 0.1950(5) 0.4585(3) 0.3295(4) 0.0734(14) Uani 1 1 d . . . H2A H 0.1385 0.3699 0.2946 0.088 Uiso 1 1 calc R . . C3 C 0.2383(6) 0.5041(4) 0.4583(4) 0.0745(14) Uani 1 1 d . . . H3A H 0.2147 0.4453 0.5123 0.089 Uiso 1 1 calc R . . C4 C 0.3165(4) 0.6369(3) 0.5065(3) 0.0481(9) Uani 1 1 d . . . H4A H 0.3456 0.6694 0.5932 0.058 Uiso 1 1 calc R . . C5 C 0.3511(3) 0.7215(3) 0.4246(2) 0.0275(6) Uani 1 1 d . . . C6 C 0.4296(3) 0.8674(2) 0.4656(2) 0.0225(5) Uani 1 1 d . . . C7 C 0.5355(3) 1.0657(2) 0.4118(2) 0.0245(5) Uani 1 1 d . . . H7A H 0.5617 1.1140 0.3525 0.029 Uiso 1 1 calc R . . C8 C 0.0629(3) 0.7694(3) 0.0738(3) 0.0348(6) Uani 1 1 d . . . H8A H 0.0572 0.7184 0.1389 0.042 Uiso 1 1 calc R . . C9 C -0.0667(3) 0.7857(3) -0.0186(3) 0.0358(7) Uani 1 1 d . . . H9A H -0.1584 0.7450 -0.0167 0.043 Uiso 1 1 calc R . . C10 C -0.0596(3) 0.8623(3) -0.1136(3) 0.0333(6) Uani 1 1 d . . . H10A H -0.1464 0.8748 -0.1766 0.040 Uiso 1 1 calc R . . C11 C 0.0788(3) 0.9215(3) -0.1152(3) 0.0296(6) Uani 1 1 d . . . H11A H 0.0863 0.9743 -0.1786 0.036 Uiso 1 1 calc R . . C12 C 0.2038(3) 0.8999(2) -0.0207(2) 0.0249(5) Uani 1 1 d . . . C13 C 0.3577(3) 0.9539(3) -0.0122(2) 0.0245(5) Uani 1 1 d . . . C14 C 0.6072(3) 0.9652(3) 0.0980(3) 0.0265(6) Uani 1 1 d . . . H14A H 0.6831 0.9420 0.1650 0.032 Uiso 1 1 calc R . . N5 N 0.5380(3) 0.6843(3) 0.2079(3) 0.0416(6) Uani 1 1 d . . . N6 N 0.8195(4) 0.4715(3) 0.0721(4) 0.0708(10) Uani 1 1 d . . . N7 N 0.4416(3) 0.2427(3) 0.1504(3) 0.0529(7) Uani 1 1 d . . . C15 C 0.6135(3) 0.4713(3) 0.1557(3) 0.0352(6) Uani 1 1 d . . . C16 C 0.5747(3) 0.5903(3) 0.1832(3) 0.0337(6) Uani 1 1 d . . . C17 C 0.7294(4) 0.4733(3) 0.1113(3) 0.0447(8) Uani 1 1 d . . . C18 C 0.5186(3) 0.3448(3) 0.1526(3) 0.0369(7) Uani 1 1 d . . . N8 N 0.8955(4) 0.7982(4) 0.2634(3) 0.0667(9) Uani 1 1 d . . . N9 N 0.7640(4) 0.8957(5) 0.5806(3) 0.0829(12) Uani 1 1 d . . . N10 N 1.1925(4) 0.7991(4) 0.6767(3) 0.0749(11) Uani 1 1 d . . . C19 C 0.9501(3) 0.8222(3) 0.5042(3) 0.0392(7) Uani 1 1 d . . . C20 C 0.9230(4) 0.8081(3) 0.3724(4) 0.0455(8) Uani 1 1 d . . . C21 C 0.8463(4) 0.8624(4) 0.5447(3) 0.0491(8) Uani 1 1 d . . . C22 C 1.0846(4) 0.8098(4) 0.5975(3) 0.0468(8) 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 0.0307(2) 0.02446(19) 0.0269(2) 0.00517(13) 0.01740(15) 0.00339(13) N1 0.0373(13) 0.0218(11) 0.0275(12) -0.0006(9) 0.0166(10) -0.0009(10) N2 0.0241(11) 0.0217(11) 0.0230(10) 0.0021(8) 0.0125(9) 0.0036(9) N3 0.0268(12) 0.0259(11) 0.0303(12) 0.0032(9) 0.0172(10) 0.0021(9) N4 0.0275(12) 0.0228(11) 0.0255(11) 0.0041(9) 0.0149(9) 0.0035(9) C1 0.078(2) 0.0267(16) 0.0354(17) -0.0064(13) 0.0292(17) -0.0088(15) C2 0.128(4) 0.0278(18) 0.053(2) -0.0102(16) 0.050(3) -0.028(2) C3 0.140(4) 0.0320(18) 0.045(2) 0.0018(15) 0.052(3) -0.022(2) C4 0.080(3) 0.0297(16) 0.0318(16) -0.0010(12) 0.0308(17) -0.0071(16) C5 0.0342(15) 0.0220(13) 0.0279(14) 0.0013(11) 0.0163(12) 0.0027(11) C6 0.0224(13) 0.0204(12) 0.0254(13) 0.0042(10) 0.0113(11) 0.0029(10) C7 0.0286(14) 0.0213(13) 0.0280(13) 0.0052(10) 0.0169(11) 0.0036(10) C8 0.0346(16) 0.0343(15) 0.0394(16) 0.0070(13) 0.0223(13) 0.0012(12) C9 0.0265(15) 0.0381(16) 0.0433(17) -0.0012(13) 0.0199(13) -0.0016(12) C10 0.0251(14) 0.0370(16) 0.0352(15) -0.0042(12) 0.0115(12) 0.0049(12) C11 0.0308(14) 0.0330(15) 0.0288(14) 0.0040(11) 0.0164(12) 0.0069(12) C12 0.0282(14) 0.0213(13) 0.0291(13) -0.0003(10) 0.0182(11) 0.0022(10) C13 0.0286(14) 0.0229(13) 0.0255(13) 0.0009(10) 0.0153(11) 0.0056(11) C14 0.0260(13) 0.0268(14) 0.0281(13) 0.0052(11) 0.0123(11) 0.0059(11) N5 0.0467(16) 0.0312(14) 0.0612(17) 0.0125(12) 0.0348(14) 0.0123(12) N6 0.089(3) 0.058(2) 0.096(3) 0.0071(18) 0.069(2) 0.0191(18) N7 0.0504(18) 0.0414(17) 0.0630(19) 0.0058(14) 0.0189(15) 0.0095(14) C15 0.0389(16) 0.0342(16) 0.0377(16) 0.0055(12) 0.0190(13) 0.0125(13) C16 0.0350(16) 0.0329(15) 0.0356(16) 0.0093(12) 0.0162(13) 0.0074(13) C17 0.058(2) 0.0342(17) 0.0496(19) 0.0035(14) 0.0291(18) 0.0125(15) C18 0.0394(17) 0.0368(17) 0.0347(16) 0.0038(13) 0.0117(13) 0.0155(14) N8 0.074(2) 0.076(2) 0.055(2) 0.0118(17) 0.0348(18) 0.0115(18) N9 0.064(2) 0.151(4) 0.056(2) 0.027(2) 0.0274(18) 0.063(3) N10 0.047(2) 0.122(3) 0.058(2) -0.005(2) 0.0201(17) 0.030(2) C19 0.0388(17) 0.0402(17) 0.0435(18) 0.0091(14) 0.0215(14) 0.0090(14) C20 0.0471(19) 0.0399(18) 0.052(2) 0.0098(15) 0.0250(17) 0.0056(15) C21 0.0448(19) 0.065(2) 0.0414(18) 0.0161(16) 0.0150(16) 0.0222(17) C22 0.042(2) 0.053(2) 0.050(2) -0.0014(16) 0.0266(17) 0.0087(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 N1 1.994(2) . ? Cu1 N5 2.001(3) . ? Cu1 N3 2.011(2) . ? Cu1 N4 2.017(2) . ? Cu1 N2 2.184(2) . ? N1 C1 1.338(4) . ? N1 C5 1.346(3) . ? N2 C7 1.330(3) . ? N2 C6 1.337(3) . ? N3 C8 1.341(3) . ? N3 C12 1.354(3) . ? N4 C14 1.334(3) . ? N4 C13 1.339(3) . ? C1 C2 1.370(4) . ? C2 C3 1.376(5) . ? C3 C4 1.372(4) . ? C4 C5 1.378(4) . ? C5 C6 1.478(3) . ? C6 C7 1.393(4) 2_676 ? C7 C6 1.393(4) 2_676 ? C8 C9 1.373(4) . ? C9 C10 1.368(4) . ? C10 C11 1.392(4) . ? C11 C12 1.372(4) . ? C12 C13 1.482(4) . ? C13 C14 1.393(4) 2_675 ? C14 C13 1.393(4) 2_675 ? N5 C16 1.143(4) . ? N6 C17 1.141(4) . ? N7 C18 1.145(4) . ? C15 C16 1.392(4) . ? C15 C18 1.414(4) . ? C15 C17 1.417(4) . ? N8 C20 1.150(4) . ? N9 C21 1.139(4) . ? N10 C22 1.144(5) . ? C19 C21 1.397(5) . ? C19 C22 1.397(5) . ? C19 C20 1.403(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 N1 Cu1 N5 88.26(10) . . ? N1 Cu1 N3 96.98(9) . . ? N5 Cu1 N3 139.88(10) . . ? N1 Cu1 N4 177.11(9) . . ? N5 Cu1 N4 92.59(9) . . ? N3 Cu1 N4 80.59(8) . . ? N1 Cu1 N2 78.62(8) . . ? N5 Cu1 N2 110.80(10) . . ? N3 Cu1 N2 109.23(8) . . ? N4 Cu1 N2 103.62(8) . . ? C1 N1 C5 118.9(2) . . ? C1 N1 Cu1 123.05(19) . . ? C5 N1 Cu1 117.71(17) . . ? C7 N2 C6 117.9(2) . . ? C7 N2 Cu1 130.78(17) . . ? C6 N2 Cu1 111.32(16) . . ? C8 N3 C12 118.0(2) . . ? C8 N3 Cu1 126.35(19) . . ? C12 N3 Cu1 115.62(17) . . ? C14 N4 C13 119.1(2) . . ? C14 N4 Cu1 126.42(18) . . ? C13 N4 Cu1 114.45(17) . . ? N1 C1 C2 122.2(3) . . ? C1 C2 C3 118.8(3) . . ? C4 C3 C2 119.6(3) . . ? C3 C4 C5 119.0(3) . . ? N1 C5 C4 121.5(2) . . ? N1 C5 C6 115.3(2) . . ? C4 C5 C6 123.3(2) . . ? N2 C6 C7 120.8(2) . 2_676 ? N2 C6 C5 116.5(2) . . ? C7 C6 C5 122.7(2) 2_676 . ? N2 C7 C6 121.3(2) . 2_676 ? N3 C8 C9 122.4(3) . . ? C10 C9 C8 119.4(3) . . ? C9 C10 C11 119.3(3) . . ? C12 C11 C10 118.3(3) . . ? N3 C12 C11 122.6(2) . . ? N3 C12 C13 113.3(2) . . ? C11 C12 C13 124.1(2) . . ? N4 C13 C14 120.0(2) . 2_675 ? N4 C13 C12 116.0(2) . . ? C14 C13 C12 123.9(2) 2_675 . ? N4 C14 C13 120.8(2) . 2_675 ? C16 N5 Cu1 155.9(3) . . ? C16 C15 C18 117.9(3) . . ? C16 C15 C17 121.9(3) . . ? C18 C15 C17 119.4(3) . . ? N5 C16 C15 176.7(3) . . ? N6 C17 C15 177.7(4) . . ? N7 C18 C15 179.7(4) . . ? C21 C19 C22 118.8(3) . . ? C21 C19 C20 119.3(3) . . ? C22 C19 C20 121.6(3) . . ? N8 C20 C19 177.2(4) . . ? N9 C21 C19 178.4(4) . . ? N10 C22 C19 177.7(4) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.733 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.077 # Attachment 'DATA_3_CCDC 650799.CIF' data_cudpp _database_code_depnum_ccdc_archive 'CCDC 650799' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H22 Cu2 N20 O' _chemical_formula_weight 973.90 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)/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 9.7205(5) _cell_length_b 18.3381(12) _cell_length_c 24.4679(16) _cell_angle_alpha 90.00 _cell_angle_beta 96.964(3) _cell_angle_gamma 90.00 _cell_volume 4329.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8884 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 25.71 _exptl_crystal_description parallelepiped _exptl_crystal_colour maroon _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 1.044 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7049 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details sadabs _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 91048 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 27.62 _reflns_number_total 10050 _reflns_number_gt 7732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius SAINT' _computing_cell_refinement 'Bruker-Nonius SAINT' _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^)+(0.0578P)^2^+3.1348P] 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 10050 _refine_ls_number_parameters 603 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 1.158 _refine_ls_restrained_S_all 1.158 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 1.38018(3) 0.879784(16) 0.127833(12) 0.03499(10) Uani 1 1 d . . . Cu2 Cu 0.87456(4) 0.628439(17) 0.053363(13) 0.03893(10) Uani 1 1 d . . . N1 N 0.9341(3) 0.66603(13) -0.01644(9) 0.0430(5) Uani 1 1 d . . . N2 N 1.0331(2) 0.69601(11) 0.08512(9) 0.0359(5) Uani 1 1 d . . . N3 N 1.2196(2) 0.80368(11) 0.11648(8) 0.0347(5) Uani 1 1 d . . . N4 N 1.2846(2) 0.91145(11) 0.05414(9) 0.0360(5) Uani 1 1 d . . . N5 N 0.7054(2) 0.70633(12) 0.05909(9) 0.0393(5) Uani 1 1 d . . . N6 N 0.8090(2) 0.59868(12) 0.12521(9) 0.0385(5) Uani 1 1 d . . . N7 N 0.5388(2) 0.81394(12) 0.09221(9) 0.0391(5) Uani 1 1 d . . . N8 N 0.4746(2) 0.82881(12) 0.19416(9) 0.0370(5) Uani 1 1 d . . . C1 C 0.8928(4) 0.63842(19) -0.06649(13) 0.0584(9) Uani 1 1 d . . . H1A H 0.8181 0.6064 -0.0708 0.070 Uiso 1 1 calc R . . C2 C 0.9581(4) 0.65621(19) -0.11179(12) 0.0600(9) Uani 1 1 d . . . H2A H 0.9270 0.6370 -0.1462 0.072 Uiso 1 1 calc R . . C3 C 1.0688(4) 0.70244(18) -0.10525(12) 0.0556(8) Uani 1 1 d . . . H3A H 1.1161 0.7137 -0.1350 0.067 Uiso 1 1 calc R . . C4 C 1.1105(3) 0.73262(16) -0.05380(11) 0.0446(6) Uani 1 1 d . . . H4A H 1.1858 0.7642 -0.0487 0.054 Uiso 1 1 calc R . . C5 C 1.0384(3) 0.71506(13) -0.01048(10) 0.0349(5) Uani 1 1 d . . . C6 C 1.0765(3) 0.74073(13) 0.04675(10) 0.0315(5) Uani 1 1 d . . . C7 C 1.0840(3) 0.70347(14) 0.13771(11) 0.0411(6) Uani 1 1 d . . . H7B H 1.0503 0.6748 0.1645 0.049 Uiso 1 1 calc R . . C8 C 1.1877(3) 0.75431(14) 0.15251(11) 0.0398(6) Uani 1 1 d . . . H8B H 1.2351 0.7537 0.1879 0.048 Uiso 1 1 calc R . . C9 C 1.1575(3) 0.80165(13) 0.06413(10) 0.0316(5) Uani 1 1 d . . . C10 C 1.1774(3) 0.86912(13) 0.03237(10) 0.0339(5) Uani 1 1 d . . . C11 C 1.0885(3) 0.89175(15) -0.01274(12) 0.0449(6) Uani 1 1 d . . . H11A H 1.0121 0.8635 -0.0259 0.054 Uiso 1 1 calc R . . C12 C 1.1143(4) 0.95677(17) -0.03797(13) 0.0564(8) Uani 1 1 d . . . H12A H 1.0566 0.9723 -0.0689 0.068 Uiso 1 1 calc R . . C13 C 1.2263(4) 0.99854(17) -0.01700(13) 0.0561(8) Uani 1 1 d . . . H13A H 1.2462 1.0421 -0.0339 0.067 Uiso 1 1 calc R . . C14 C 1.3081(3) 0.97462(15) 0.02927(12) 0.0475(7) Uani 1 1 d . . . H14A H 1.3825 1.0033 0.0439 0.057 Uiso 1 1 calc R . . C15 C 0.5775(3) 0.78153(13) 0.18723(10) 0.0353(5) Uani 1 1 d . . . C16 C 0.6642(3) 0.75516(16) 0.23180(12) 0.0476(7) Uani 1 1 d . . . H16A H 0.7387 0.7253 0.2265 0.057 Uiso 1 1 calc R . . C17 C 0.6386(4) 0.77375(19) 0.28430(13) 0.0607(9) Uani 1 1 d . . . H17A H 0.6956 0.7563 0.3148 0.073 Uiso 1 1 calc R . . C18 C 0.5285(4) 0.81819(19) 0.29122(12) 0.0621(9) Uani 1 1 d . . . H18A H 0.5070 0.8293 0.3263 0.074 Uiso 1 1 calc R . . C19 C 0.4513(3) 0.84567(17) 0.24561(12) 0.0489(7) Uani 1 1 d . . . H19A H 0.3792 0.8775 0.2504 0.059 Uiso 1 1 calc R . . C20 C 0.5949(3) 0.76479(13) 0.12892(10) 0.0345(5) Uani 1 1 d . . . C21 C 0.5665(3) 0.81053(16) 0.04077(11) 0.0466(7) Uani 1 1 d . . . H21A H 0.5233 0.8429 0.0149 0.056 Uiso 1 1 calc R . . C22 C 0.6590(3) 0.75949(16) 0.02477(11) 0.0474(7) Uani 1 1 d . . . H22A H 0.6885 0.7624 -0.0099 0.057 Uiso 1 1 calc R . . C23 C 0.6673(3) 0.70529(13) 0.11019(10) 0.0333(5) Uani 1 1 d . . . C24 C 0.6989(3) 0.63502(13) 0.13941(10) 0.0347(5) Uani 1 1 d . . . C25 C 0.8408(4) 0.53360(16) 0.14831(13) 0.0532(8) Uani 1 1 d . . . H25A H 0.9197 0.5094 0.1400 0.064 Uiso 1 1 calc R . . C26 C 0.7589(4) 0.50136(17) 0.18431(14) 0.0610(9) Uani 1 1 d . . . H26A H 0.7828 0.4562 0.2000 0.073 Uiso 1 1 calc R . . C27 C 0.6424(4) 0.53697(17) 0.19632(13) 0.0561(8) Uani 1 1 d . . . H27A H 0.5842 0.5153 0.2191 0.067 Uiso 1 1 calc R . . C28 C 0.6120(3) 0.60523(15) 0.17434(11) 0.0436(6) Uani 1 1 d . . . H28A H 0.5347 0.6307 0.1828 0.052 Uiso 1 1 calc R . . N9 N 1.2255(5) 0.95655(17) 0.16991(13) 0.0837(11) Uani 1 1 d . . . N10 N 1.0379(4) 1.1465(2) 0.24535(16) 0.0882(11) Uani 1 1 d . . . N11 N 1.2117(4) 1.16748(19) 0.08722(13) 0.0773(9) Uani 1 1 d . . . C29 C 1.1515(3) 1.08944(17) 0.16694(12) 0.0491(7) Uani 1 1 d . . . C30 C 1.1909(4) 1.01589(18) 0.16917(13) 0.0549(8) Uani 1 1 d . . . C31 C 1.0869(4) 1.12066(19) 0.21018(15) 0.0573(8) Uani 1 1 d . . . C32 C 1.1856(3) 1.13276(17) 0.12326(13) 0.0508(7) Uani 1 1 d . . . N12 N 1.5102(4) 0.96740(16) 0.13956(13) 0.0735(9) Uani 1 1 d . . . N13 N 1.6173(5) 1.1757(3) 0.07749(17) 0.1105(16) Uani 1 1 d . . . N14 N 1.6515(4) 1.1458(2) 0.25844(14) 0.0811(10) Uani 1 1 d . . . C33 C 1.5994(4) 1.09580(18) 0.16079(13) 0.0526(7) Uani 1 1 d . . . C34 C 1.5519(4) 1.02452(18) 0.15069(13) 0.0540(8) Uani 1 1 d . . . C35 C 1.6096(4) 1.1408(2) 0.11527(15) 0.0658(10) Uani 1 1 d . . . C36 C 1.6296(4) 1.12278(17) 0.21494(14) 0.0540(8) Uani 1 1 d . . . N15 N 0.7797(6) 0.5402(2) 0.02167(16) 0.137(2) Uani 1 1 d . . . N16 N 0.4728(8) 0.4004(4) 0.0852(2) 0.179(3) Uani 1 1 d . . . N17 N 0.6407(4) 0.33958(19) -0.06850(18) 0.0817(10) Uani 1 1 d . . . C37 C 0.6336(5) 0.4256(2) 0.01235(16) 0.0742(11) Uani 1 1 d . . . C38 C 0.7139(6) 0.4883(2) 0.01646(16) 0.0918(16) Uani 1 1 d . . . C39 C 0.5447(7) 0.4114(3) 0.0531(2) 0.1082(19) Uani 1 1 d . . . C40 C 0.6372(4) 0.37849(17) -0.03250(17) 0.0580(9) Uani 1 1 d . . . N18 N 0.2555(6) 0.4580(3) 0.24056(19) 0.1137(15) Uani 1 1 d . . . N19 N -0.1199(4) 0.3316(2) 0.23222(13) 0.0756(9) Uani 1 1 d . . . N20 N 0.1199(4) 0.36519(18) 0.39572(13) 0.0697(8) Uani 1 1 d . . . C41 C 0.0884(4) 0.3864(2) 0.29202(14) 0.0583(8) Uani 1 1 d . . . C42 C 0.1803(5) 0.4267(2) 0.26506(17) 0.0739(10) Uani 1 1 d . . . C43 C -0.0261(4) 0.3559(2) 0.25977(14) 0.0586(8) Uani 1 1 d . . . C44 C 0.1069(4) 0.37542(19) 0.34959(15) 0.0559(8) Uani 1 1 d . . . O1 O 1.0462(6) 0.5386(4) 0.0556(3) 0.0880(17) Uiso 0.50 1 d P . . O2 O 0.2048(6) 0.5294(3) 0.1334(2) 0.0733(14) Uiso 0.50 1 d P . . 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 0.04436(19) 0.02710(16) 0.03207(17) 0.00168(11) -0.00125(13) -0.00212(12) Cu2 0.0538(2) 0.03136(17) 0.03429(18) -0.00600(12) 0.01626(14) -0.01102(13) N1 0.0579(14) 0.0405(12) 0.0327(11) -0.0096(9) 0.0143(10) -0.0167(11) N2 0.0478(12) 0.0300(10) 0.0312(10) -0.0020(8) 0.0100(9) -0.0055(9) N3 0.0457(12) 0.0256(10) 0.0319(11) 0.0010(8) 0.0016(9) 0.0006(9) N4 0.0447(12) 0.0280(10) 0.0342(11) 0.0038(8) 0.0006(9) -0.0033(9) N5 0.0519(13) 0.0360(11) 0.0313(11) 0.0022(9) 0.0098(10) -0.0060(10) N6 0.0530(13) 0.0289(10) 0.0356(11) 0.0022(9) 0.0130(10) -0.0006(9) N7 0.0488(13) 0.0330(11) 0.0336(11) 0.0035(9) -0.0025(10) -0.0016(9) N8 0.0443(12) 0.0348(11) 0.0312(11) -0.0002(9) 0.0021(9) 0.0011(9) C1 0.079(2) 0.0598(19) 0.0382(16) -0.0156(14) 0.0136(15) -0.0315(17) C2 0.088(2) 0.061(2) 0.0318(15) -0.0158(14) 0.0130(15) -0.0212(18) C3 0.081(2) 0.0555(18) 0.0343(15) -0.0056(13) 0.0221(15) -0.0127(16) C4 0.0581(17) 0.0434(15) 0.0347(14) -0.0033(11) 0.0157(12) -0.0109(13) C5 0.0444(14) 0.0290(12) 0.0320(12) -0.0032(10) 0.0081(10) -0.0035(10) C6 0.0400(13) 0.0265(11) 0.0290(12) -0.0020(9) 0.0081(10) -0.0022(9) C7 0.0574(17) 0.0359(13) 0.0312(13) 0.0029(10) 0.0100(12) -0.0053(12) C8 0.0555(16) 0.0336(13) 0.0298(12) 0.0014(10) 0.0027(11) 0.0006(12) C9 0.0386(13) 0.0265(11) 0.0294(12) -0.0001(9) 0.0033(10) 0.0000(9) C10 0.0430(14) 0.0275(12) 0.0310(12) 0.0002(9) 0.0035(10) -0.0014(10) C11 0.0526(17) 0.0382(14) 0.0403(15) 0.0044(11) -0.0087(12) -0.0058(12) C12 0.073(2) 0.0436(16) 0.0468(17) 0.0139(13) -0.0161(15) -0.0008(15) C13 0.076(2) 0.0388(15) 0.0506(18) 0.0178(13) -0.0058(16) -0.0097(15) C14 0.0594(18) 0.0336(14) 0.0470(16) 0.0084(12) -0.0038(13) -0.0116(12) C15 0.0439(14) 0.0290(12) 0.0321(12) -0.0007(10) 0.0013(10) -0.0032(10) C16 0.0602(18) 0.0405(15) 0.0390(15) -0.0016(12) -0.0065(13) 0.0082(13) C17 0.088(2) 0.0559(19) 0.0336(15) 0.0001(13) -0.0119(15) 0.0132(18) C18 0.096(3) 0.060(2) 0.0299(14) -0.0055(13) 0.0070(16) 0.0107(19) C19 0.0630(19) 0.0468(16) 0.0373(15) -0.0053(12) 0.0075(13) 0.0067(14) C20 0.0400(13) 0.0311(12) 0.0316(12) 0.0013(10) 0.0010(10) -0.0053(10) C21 0.0622(18) 0.0415(15) 0.0347(14) 0.0091(11) 0.0003(13) 0.0002(13) C22 0.0665(19) 0.0466(16) 0.0300(13) 0.0074(11) 0.0094(13) -0.0041(14) C23 0.0394(13) 0.0314(12) 0.0292(12) 0.0014(9) 0.0048(10) -0.0056(10) C24 0.0464(14) 0.0283(12) 0.0300(12) -0.0005(9) 0.0076(10) -0.0031(10) C25 0.071(2) 0.0352(15) 0.0562(18) 0.0060(13) 0.0211(16) 0.0102(14) C26 0.092(3) 0.0338(15) 0.061(2) 0.0155(14) 0.0242(18) 0.0073(16) C27 0.079(2) 0.0432(16) 0.0498(18) 0.0134(13) 0.0233(16) -0.0059(15) C28 0.0546(17) 0.0382(14) 0.0404(15) 0.0055(11) 0.0153(13) -0.0024(12) N9 0.148(3) 0.0434(17) 0.0585(19) -0.0057(14) 0.007(2) 0.0104(19) N10 0.091(3) 0.103(3) 0.074(2) -0.019(2) 0.025(2) 0.012(2) N11 0.096(2) 0.078(2) 0.0550(18) 0.0170(17) -0.0023(17) -0.0168(19) C29 0.0605(18) 0.0446(16) 0.0422(15) -0.0032(12) 0.0065(13) -0.0004(14) C30 0.080(2) 0.0466(18) 0.0383(15) -0.0047(13) 0.0071(15) -0.0060(16) C31 0.060(2) 0.059(2) 0.0535(19) -0.0084(15) 0.0097(16) 0.0008(15) C32 0.0580(19) 0.0495(17) 0.0419(16) -0.0026(13) -0.0058(14) -0.0032(14) N12 0.109(3) 0.0484(16) 0.0552(17) -0.0041(13) -0.0228(17) -0.0121(17) N13 0.115(3) 0.141(4) 0.073(2) 0.031(3) -0.001(2) -0.062(3) N14 0.102(3) 0.083(2) 0.062(2) -0.0319(18) 0.0254(18) -0.031(2) C33 0.0635(19) 0.0484(17) 0.0461(17) -0.0074(13) 0.0075(14) -0.0125(15) C34 0.067(2) 0.0479(17) 0.0440(16) -0.0046(13) -0.0079(15) -0.0036(15) C35 0.068(2) 0.076(2) 0.054(2) -0.0001(18) 0.0074(17) -0.0311(19) C36 0.062(2) 0.0477(17) 0.0544(19) -0.0113(14) 0.0164(15) -0.0160(14) N15 0.272(6) 0.084(3) 0.072(2) -0.044(2) 0.087(3) -0.112(4) N16 0.243(7) 0.212(7) 0.094(4) 0.035(4) 0.066(4) -0.083(6) N17 0.069(2) 0.060(2) 0.114(3) -0.033(2) 0.0036(19) -0.0060(16) C37 0.119(3) 0.0460(19) 0.058(2) -0.0012(16) 0.012(2) -0.032(2) C38 0.170(5) 0.062(2) 0.050(2) -0.0141(17) 0.036(2) -0.053(3) C39 0.173(5) 0.088(3) 0.066(3) 0.011(2) 0.025(3) -0.050(4) C40 0.0535(19) 0.0366(16) 0.081(2) -0.0041(16) -0.0042(17) -0.0085(13) N18 0.145(4) 0.106(3) 0.096(3) 0.005(3) 0.036(3) -0.037(3) N19 0.087(2) 0.095(3) 0.0456(16) -0.0037(16) 0.0081(16) -0.002(2) N20 0.075(2) 0.077(2) 0.0539(18) 0.0004(15) -0.0054(15) -0.0113(16) C41 0.061(2) 0.065(2) 0.0492(18) -0.0001(15) 0.0074(15) 0.0042(16) C42 0.093(3) 0.065(2) 0.063(2) 0.0021(19) 0.010(2) -0.005(2) C43 0.071(2) 0.066(2) 0.0389(16) 0.0013(15) 0.0093(16) 0.0096(18) C44 0.0548(19) 0.059(2) 0.053(2) -0.0027(15) 0.0003(15) 0.0019(15) _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 N8 1.997(2) 1_655 ? Cu1 N4 2.011(2) . ? Cu1 N12 2.043(3) . ? Cu1 N3 2.088(2) . ? Cu1 N7 2.218(2) 1_655 ? Cu1 N9 2.383(4) . ? Cu2 N15 1.973(3) . ? Cu2 N1 1.992(2) . ? Cu2 N6 2.017(2) . ? Cu2 N2 2.055(2) . ? Cu2 N5 2.195(2) . ? Cu2 O1 2.341(6) . ? N1 C1 1.341(4) . ? N1 C5 1.350(3) . ? N2 C7 1.328(3) . ? N2 C6 1.352(3) . ? N3 C8 1.326(3) . ? N3 C9 1.349(3) . ? N4 C14 1.341(3) . ? N4 C10 1.355(3) . ? N5 C22 1.329(4) . ? N5 C23 1.346(3) . ? N6 C25 1.340(4) . ? N6 C24 1.342(3) . ? N7 C21 1.320(4) . ? N7 C20 1.341(3) . ? N7 Cu1 2.218(2) 1_455 ? N8 C19 1.342(3) . ? N8 C15 1.350(3) . ? N8 Cu1 1.997(2) 1_455 ? C1 C2 1.381(4) . ? C2 C3 1.364(5) . ? C3 C4 1.390(4) . ? C4 C5 1.378(4) . ? C5 C6 1.481(3) . ? C6 C9 1.403(3) . ? C7 C8 1.389(4) . ? C9 C10 1.486(3) . ? C10 C11 1.381(4) . ? C11 C12 1.380(4) . ? C12 C13 1.378(4) . ? C13 C14 1.374(4) . ? C15 C16 1.382(4) . ? C15 C20 1.489(4) . ? C16 C17 1.380(4) . ? C17 C18 1.372(5) . ? C18 C19 1.364(4) . ? C20 C23 1.405(4) . ? C21 C22 1.387(4) . ? C23 C24 1.488(3) . ? C24 C28 1.385(4) . ? C25 C26 1.389(4) . ? C26 C27 1.369(5) . ? C27 C28 1.380(4) . ? N9 C30 1.138(4) . ? N10 C31 1.136(5) . ? N11 C32 1.141(4) . ? C29 C30 1.402(4) . ? C29 C32 1.403(4) . ? C29 C31 1.415(5) . ? N12 C34 1.144(4) . ? N13 C35 1.135(5) . ? N14 C36 1.141(4) . ? C33 C34 1.399(4) . ? C33 C35 1.399(5) . ? C33 C36 1.411(4) . ? N15 C38 1.145(5) . ? N16 C39 1.131(7) . ? N17 C40 1.137(5) . ? C37 C38 1.387(5) . ? C37 C40 1.401(5) . ? C37 C39 1.420(7) . ? N18 C42 1.152(6) . ? N19 C43 1.155(5) . ? N20 C44 1.136(5) . ? C41 C42 1.387(6) . ? C41 C43 1.400(5) . ? C41 C44 1.413(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 N8 Cu1 N4 168.64(9) 1_655 . ? N8 Cu1 N12 92.21(11) 1_655 . ? N4 Cu1 N12 96.29(10) . . ? N8 Cu1 N3 93.32(9) 1_655 . ? N4 Cu1 N3 79.45(8) . . ? N12 Cu1 N3 169.91(12) . . ? N8 Cu1 N7 77.98(8) 1_655 1_655 ? N4 Cu1 N7 94.16(8) . 1_655 ? N12 Cu1 N7 92.05(12) . 1_655 ? N3 Cu1 N7 97.36(8) . 1_655 ? N8 Cu1 N9 100.22(10) 1_655 . ? N4 Cu1 N9 88.26(10) . . ? N12 Cu1 N9 83.49(15) . . ? N3 Cu1 N9 87.22(11) . . ? N7 Cu1 N9 175.14(11) 1_655 . ? N15 Cu2 N1 96.73(12) . . ? N15 Cu2 N6 86.49(12) . . ? N1 Cu2 N6 175.33(9) . . ? N15 Cu2 N2 159.4(2) . . ? N1 Cu2 N2 80.39(9) . . ? N6 Cu2 N2 97.78(9) . . ? N15 Cu2 N5 103.9(2) . . ? N1 Cu2 N5 97.31(9) . . ? N6 Cu2 N5 78.58(8) . . ? N2 Cu2 N5 96.71(9) . . ? N15 Cu2 O1 74.3(3) . . ? N1 Cu2 O1 89.05(17) . . ? N6 Cu2 O1 95.10(17) . . ? N2 Cu2 O1 85.17(17) . . ? N5 Cu2 O1 173.59(17) . . ? C1 N1 C5 119.2(2) . . ? C1 N1 Cu2 124.5(2) . . ? C5 N1 Cu2 115.49(17) . . ? C7 N2 C6 120.0(2) . . ? C7 N2 Cu2 127.03(18) . . ? C6 N2 Cu2 112.68(16) . . ? C8 N3 C9 119.9(2) . . ? C8 N3 Cu1 126.79(18) . . ? C9 N3 Cu1 112.72(16) . . ? C14 N4 C10 118.8(2) . . ? C14 N4 Cu1 124.79(18) . . ? C10 N4 Cu1 115.88(16) . . ? C22 N5 C23 119.1(2) . . ? C22 N5 Cu2 129.52(19) . . ? C23 N5 Cu2 110.04(17) . . ? C25 N6 C24 118.9(2) . . ? C25 N6 Cu2 121.84(19) . . ? C24 N6 Cu2 115.95(17) . . ? C21 N7 C20 119.6(2) . . ? C21 N7 Cu1 129.21(19) . 1_455 ? C20 N7 Cu1 110.39(17) . 1_455 ? C19 N8 C15 118.6(2) . . ? C19 N8 Cu1 122.76(19) . 1_455 ? C15 N8 Cu1 118.22(17) . 1_455 ? N1 C1 C2 121.9(3) . . ? C3 C2 C1 119.0(3) . . ? C2 C3 C4 119.5(3) . . ? C5 C4 C3 119.0(3) . . ? N1 C5 C4 121.2(2) . . ? N1 C5 C6 114.4(2) . . ? C4 C5 C6 124.1(2) . . ? N2 C6 C9 118.9(2) . . ? N2 C6 C5 113.6(2) . . ? C9 C6 C5 127.3(2) . . ? N2 C7 C8 119.7(2) . . ? N3 C8 C7 120.4(2) . . ? N3 C9 C6 118.7(2) . . ? N3 C9 C10 113.7(2) . . ? C6 C9 C10 127.5(2) . . ? N4 C10 C11 121.3(2) . . ? N4 C10 C9 114.5(2) . . ? C11 C10 C9 124.0(2) . . ? C12 C11 C10 119.1(3) . . ? C13 C12 C11 119.5(3) . . ? C14 C13 C12 118.8(3) . . ? N4 C14 C13 122.4(3) . . ? N8 C15 C16 121.0(2) . . ? N8 C15 C20 115.1(2) . . ? C16 C15 C20 123.7(2) . . ? C17 C16 C15 119.1(3) . . ? C18 C17 C16 119.5(3) . . ? C19 C18 C17 118.6(3) . . ? N8 C19 C18 122.9(3) . . ? N7 C20 C23 118.9(2) . . ? N7 C20 C15 114.8(2) . . ? C23 C20 C15 126.3(2) . . ? N7 C21 C22 121.0(3) . . ? N5 C22 C21 119.9(3) . . ? N5 C23 C20 119.8(2) . . ? N5 C23 C24 113.2(2) . . ? C20 C23 C24 126.8(2) . . ? N6 C24 C28 121.9(2) . . ? N6 C24 C23 115.5(2) . . ? C28 C24 C23 122.2(2) . . ? N6 C25 C26 121.7(3) . . ? C27 C26 C25 119.0(3) . . ? C26 C27 C28 119.5(3) . . ? C27 C28 C24 118.7(3) . . ? C30 N9 Cu1 139.3(3) . . ? C30 C29 C32 119.0(3) . . ? C30 C29 C31 120.3(3) . . ? C32 C29 C31 120.5(3) . . ? N9 C30 C29 178.1(4) . . ? N10 C31 C29 178.4(4) . . ? N11 C32 C29 178.9(4) . . ? C34 N12 Cu1 161.6(4) . . ? C34 C33 C35 117.6(3) . . ? C34 C33 C36 121.3(3) . . ? C35 C33 C36 120.9(3) . . ? N12 C34 C33 176.2(4) . . ? N13 C35 C33 178.2(5) . . ? N14 C36 C33 178.4(5) . . ? C38 N15 Cu2 162.4(3) . . ? C38 C37 C40 120.1(4) . . ? C38 C37 C39 119.1(4) . . ? C40 C37 C39 120.8(4) . . ? N15 C38 C37 177.7(4) . . ? N16 C39 C37 179.3(8) . . ? N17 C40 C37 179.2(4) . . ? C42 C41 C43 117.3(3) . . ? C42 C41 C44 122.6(4) . . ? C43 C41 C44 120.1(3) . . ? N18 C42 C41 176.7(5) . . ? N19 C43 C41 178.6(4) . . ? N20 C44 C41 178.4(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C5 C6 N2 19.4(3) . . . . ? N3 C9 C10 N4 18.7(3) . . . . ? N6 C24 C23 N5 29.6(3) . . . . ? N7 C20 C15 N8 19.9(3) . . . . ? C5 C6 C9 C10 26.3(4) . . . . ? C15 C20 C23 C24 22.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.543 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.072 # Attachment 'DATA_4_CCDC 650800.CIF' data_4 _database_code_depnum_ccdc_archive 'CCDC 650800' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H12 Cu N10' _chemical_formula_weight 528.00 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' 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 29.974(3) _cell_length_b 7.4460(8) _cell_length_c 23.687(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.658(8) _cell_angle_gamma 90.00 _cell_volume 4639.0(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7249 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 29.20 _exptl_crystal_description parallelepiped _exptl_crystal_colour maroon _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2136 _exptl_absorpt_coefficient_mu 0.980 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.862 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details sadabs _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 51216 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 30.65 _reflns_number_total 7131 _reflns_number_gt 5965 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius SAINT' _computing_cell_refinement 'Bruker-Nonius SAINT' _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^)+(0.0464P)^2^+2.2097P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7131 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.003 _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 0.630005(6) 1.09657(2) 0.835436(7) 0.02929(6) Uani 1 1 d . . . N1 N 0.58968(4) 1.19819(15) 0.87404(5) 0.0315(2) Uani 1 1 d . . . N2 N 0.68074(4) 1.07394(15) 0.93149(5) 0.0284(2) Uani 1 1 d . . . C1 C 0.54816(6) 1.2994(2) 0.84327(8) 0.0402(3) Uani 1 1 d . . . H1A H 0.5368 1.3276 0.8003 0.048 Uiso 1 1 calc R . . C2 C 0.52132(6) 1.3639(2) 0.87284(9) 0.0452(4) Uani 1 1 d . . . H2A H 0.4922 1.4331 0.8502 0.054 Uiso 1 1 calc R . . C3 C 0.53860(6) 1.3234(2) 0.93643(9) 0.0454(4) Uani 1 1 d . . . H3A H 0.5214 1.3661 0.9576 0.055 Uiso 1 1 calc R . . C4 C 0.58186(6) 1.2185(2) 0.96921(8) 0.0403(3) Uani 1 1 d . . . H4A H 0.5939 1.1902 1.0124 0.048 Uiso 1 1 calc R . . C5 C 0.60679(5) 1.15645(19) 0.93656(6) 0.0313(3) Uani 1 1 d . . . C6 C 0.65689(5) 1.06411(18) 0.96650(6) 0.0293(3) Uani 1 1 d . . . C7 C 0.73118(5) 1.02999(18) 0.95906(6) 0.0285(2) Uani 1 1 d . . . C8 C 0.75870(5) 1.0505(2) 0.92493(7) 0.0340(3) Uani 1 1 d . . . H8A H 0.7426 1.0918 0.8827 0.041 Uiso 1 1 calc R . . C9 C 0.80943(5) 1.0089(2) 0.95480(7) 0.0376(3) Uani 1 1 d . . . H9A H 0.8276 1.0219 0.9325 0.045 Uiso 1 1 calc R . . C10 C 0.83447(5) 0.9466(2) 1.01881(7) 0.0376(3) Uani 1 1 d . . . H10A H 0.8688 0.9174 1.0379 0.045 Uiso 1 1 calc R . . C11 C 0.80894(5) 0.92857(19) 1.05298(7) 0.0342(3) Uani 1 1 d . . . H11A H 0.8259 0.8888 1.0954 0.041 Uiso 1 1 calc R . . C12 C 0.75639(5) 0.97071(18) 1.02371(6) 0.0293(2) Uani 1 1 d . . . N3 N 0.73058(4) 0.94392(16) 1.05696(5) 0.0326(2) Uani 1 1 d . . . C13 C 0.68182(5) 0.98460(19) 1.02904(6) 0.0313(3) Uani 1 1 d . . . C14 C 0.65447(6) 0.9268(2) 1.06449(7) 0.0346(3) Uani 1 1 d . . . C15 C 0.67736(7) 0.9434(3) 1.13057(8) 0.0472(4) Uani 1 1 d . . . H15A H 0.7086 1.0005 1.1534 0.057 Uiso 1 1 calc R . . C16 C 0.65240(8) 0.8723(3) 1.16185(9) 0.0599(5) Uani 1 1 d . . . H16A H 0.6667 0.8807 1.2063 0.072 Uiso 1 1 calc R . . C17 C 0.60656(8) 0.7897(3) 1.12637(10) 0.0642(5) Uani 1 1 d . . . H17A H 0.5892 0.7402 1.1464 0.077 Uiso 1 1 calc R . . C18 C 0.58636(8) 0.7809(3) 1.06054(10) 0.0609(5) Uani 1 1 d . . . H18A H 0.5551 0.7247 1.0368 0.073 Uiso 1 1 calc R . . N4 N 0.60936(5) 0.8489(2) 1.02904(7) 0.0464(3) Uani 1 1 d . . . N5 N 0.66241(5) 0.90278(16) 0.81100(6) 0.0369(3) Uani 1 1 d . . . N6 N 0.65916(6) 0.32503(18) 0.80741(7) 0.0452(3) Uani 1 1 d . . . N7 N 0.72370(10) 0.6185(3) 0.69847(11) 0.0861(7) Uani 1 1 d . . . C19 C 0.67993(6) 0.61472(19) 0.76785(7) 0.0369(3) Uani 1 1 d . . . C20 C 0.67049(5) 0.77447(19) 0.79084(6) 0.0321(3) Uani 1 1 d . . . C21 C 0.66865(6) 0.4537(2) 0.78885(7) 0.0351(3) Uani 1 1 d . . . C22 C 0.70389(8) 0.6159(2) 0.72899(9) 0.0501(4) Uani 1 1 d . . . N8 N 0.56827(5) 1.0746(2) 0.74790(6) 0.0442(3) Uani 1 1 d . . . N9 N 0.42786(7) 0.7571(3) 0.65388(10) 0.0718(5) Uani 1 1 d . . . N10 N 0.53827(9) 0.7296(3) 0.58057(11) 0.0889(7) Uani 1 1 d . . . C23 C 0.51159(6) 0.8579(2) 0.65983(8) 0.0449(4) Uani 1 1 d . . . C24 C 0.54303(6) 0.9742(2) 0.70832(7) 0.0390(3) Uani 1 1 d . . . C25 C 0.46538(7) 0.8018(2) 0.65620(9) 0.0499(4) Uani 1 1 d . . . C26 C 0.52653(8) 0.7900(3) 0.61573(9) 0.0562(5) 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 0.03340(9) 0.03111(9) 0.02405(9) -0.00136(6) 0.01434(7) 0.00046(6) N1 0.0320(5) 0.0329(6) 0.0297(5) -0.0026(4) 0.0148(5) -0.0001(4) N2 0.0306(5) 0.0320(5) 0.0249(5) 0.0001(4) 0.0152(4) -0.0011(4) C1 0.0367(7) 0.0420(8) 0.0378(8) 0.0008(6) 0.0146(6) 0.0034(6) C2 0.0353(7) 0.0434(8) 0.0577(10) -0.0014(7) 0.0229(7) 0.0046(6) C3 0.0420(8) 0.0478(9) 0.0589(10) -0.0040(8) 0.0342(8) 0.0014(7) C4 0.0413(7) 0.0475(8) 0.0411(8) -0.0017(6) 0.0270(7) -0.0001(6) C5 0.0322(6) 0.0331(6) 0.0315(6) -0.0031(5) 0.0175(5) -0.0034(5) C6 0.0321(6) 0.0327(6) 0.0262(6) -0.0030(5) 0.0166(5) -0.0031(5) C7 0.0296(6) 0.0306(6) 0.0274(6) -0.0015(5) 0.0152(5) -0.0019(5) C8 0.0348(7) 0.0406(7) 0.0300(6) 0.0016(5) 0.0183(6) -0.0013(6) C9 0.0345(7) 0.0448(8) 0.0390(8) -0.0005(6) 0.0220(6) -0.0022(6) C10 0.0289(6) 0.0410(7) 0.0395(8) -0.0028(6) 0.0138(6) -0.0008(5) C11 0.0333(6) 0.0376(7) 0.0271(6) -0.0012(5) 0.0109(5) 0.0000(5) C12 0.0324(6) 0.0300(6) 0.0261(6) -0.0021(5) 0.0146(5) -0.0034(5) N3 0.0365(6) 0.0372(6) 0.0257(5) -0.0007(4) 0.0161(5) -0.0029(5) C13 0.0372(6) 0.0342(7) 0.0262(6) -0.0024(5) 0.0182(5) -0.0036(5) C14 0.0409(7) 0.0396(7) 0.0304(7) 0.0018(5) 0.0228(6) 0.0004(6) C15 0.0539(9) 0.0616(10) 0.0319(7) -0.0016(7) 0.0253(7) -0.0050(8) C16 0.0751(13) 0.0795(13) 0.0392(9) 0.0050(9) 0.0390(10) -0.0008(10) C17 0.0738(13) 0.0802(14) 0.0629(12) 0.0097(11) 0.0523(11) -0.0068(11) C18 0.0566(10) 0.0797(14) 0.0599(11) -0.0022(10) 0.0387(9) -0.0189(10) N4 0.0472(7) 0.0599(8) 0.0404(7) -0.0031(6) 0.0276(6) -0.0116(6) N5 0.0466(7) 0.0342(6) 0.0372(6) -0.0010(5) 0.0259(6) -0.0003(5) N6 0.0664(9) 0.0351(7) 0.0458(7) -0.0035(6) 0.0362(7) -0.0050(6) N7 0.133(2) 0.0838(14) 0.0895(15) -0.0073(11) 0.0922(16) -0.0051(12) C19 0.0534(9) 0.0313(7) 0.0358(7) -0.0012(5) 0.0293(7) -0.0002(6) C20 0.0392(7) 0.0331(7) 0.0281(6) 0.0016(5) 0.0195(5) -0.0020(5) C21 0.0461(8) 0.0327(7) 0.0316(7) -0.0045(5) 0.0228(6) -0.0006(6) C22 0.0760(12) 0.0429(9) 0.0488(10) -0.0024(7) 0.0439(10) -0.0015(8) N8 0.0422(7) 0.0558(8) 0.0300(6) -0.0043(6) 0.0136(6) -0.0006(6) N9 0.0620(10) 0.0777(12) 0.0866(13) -0.0328(10) 0.0444(10) -0.0175(9) N10 0.0984(15) 0.1148(18) 0.0764(13) -0.0378(13) 0.0602(12) -0.0253(13) C23 0.0477(9) 0.0480(9) 0.0385(8) -0.0094(7) 0.0202(7) -0.0047(7) C24 0.0400(7) 0.0447(8) 0.0313(7) 0.0026(6) 0.0163(6) 0.0042(6) C25 0.0524(9) 0.0468(9) 0.0507(10) -0.0146(8) 0.0249(8) -0.0018(7) C26 0.0622(11) 0.0642(12) 0.0469(10) -0.0149(9) 0.0300(9) -0.0147(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 Cu1 N5 1.9748(12) . ? Cu1 N1 1.9823(11) . ? Cu1 N8 2.0174(14) . ? Cu1 N2 2.0491(12) . ? Cu1 N6 2.1575(14) 1_565 ? N1 C1 1.3333(18) . ? N1 C5 1.3506(17) . ? N2 C6 1.3313(16) . ? N2 C7 1.3685(17) . ? C1 C2 1.382(2) . ? C2 C3 1.371(3) . ? C3 C4 1.389(2) . ? C4 C5 1.3872(19) . ? C5 C6 1.4863(19) . ? C6 C13 1.4288(19) . ? C7 C8 1.4133(18) . ? C7 C12 1.4145(18) . ? C8 C9 1.370(2) . ? C9 C10 1.409(2) . ? C10 C11 1.361(2) . ? C11 C12 1.4187(19) . ? C12 N3 1.3576(17) . ? N3 C13 1.3184(18) . ? C13 C14 1.4908(18) . ? C14 N4 1.335(2) . ? C14 C15 1.381(2) . ? C15 C16 1.386(2) . ? C16 C17 1.366(3) . ? C17 C18 1.377(3) . ? C18 N4 1.335(2) . ? N5 C20 1.1446(18) . ? N6 C21 1.146(2) . ? N6 Cu1 2.1575(14) 1_545 ? N7 C22 1.135(2) . ? C19 C20 1.393(2) . ? C19 C21 1.400(2) . ? C19 C22 1.413(2) . ? N8 C24 1.153(2) . ? N9 C25 1.148(2) . ? N10 C26 1.140(3) . ? C23 C24 1.385(2) . ? C23 C25 1.409(3) . ? C23 C26 1.413(2) . ? 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 N5 Cu1 N1 155.30(5) . . ? N5 Cu1 N8 88.68(6) . . ? N1 Cu1 N8 92.49(5) . . ? N5 Cu1 N2 93.33(5) . . ? N1 Cu1 N2 79.12(5) . . ? N8 Cu1 N2 163.94(5) . . ? N5 Cu1 N6 99.04(5) . 1_565 ? N1 Cu1 N6 105.52(5) . 1_565 ? N8 Cu1 N6 93.15(6) . 1_565 ? N2 Cu1 N6 102.25(5) . 1_565 ? C1 N1 C5 119.57(12) . . ? C1 N1 Cu1 125.41(10) . . ? C5 N1 Cu1 115.02(9) . . ? C6 N2 C7 119.34(11) . . ? C6 N2 Cu1 111.22(9) . . ? C7 N2 Cu1 127.68(9) . . ? N1 C1 C2 122.50(15) . . ? C3 C2 C1 118.39(15) . . ? C2 C3 C4 119.83(14) . . ? C5 C4 C3 118.93(15) . . ? N1 C5 C4 120.78(13) . . ? N1 C5 C6 113.28(11) . . ? C4 C5 C6 125.39(13) . . ? N2 C6 C13 119.91(12) . . ? N2 C6 C5 113.49(12) . . ? C13 C6 C5 126.35(12) . . ? N2 C7 C8 121.04(12) . . ? N2 C7 C12 119.05(11) . . ? C8 C7 C12 119.86(12) . . ? C9 C8 C7 119.20(13) . . ? C8 C9 C10 121.11(13) . . ? C11 C10 C9 120.73(13) . . ? C10 C11 C12 119.79(13) . . ? N3 C12 C7 121.11(12) . . ? N3 C12 C11 119.48(12) . . ? C7 C12 C11 119.30(12) . . ? C13 N3 C12 118.57(12) . . ? N3 C13 C6 121.20(12) . . ? N3 C13 C14 115.33(12) . . ? C6 C13 C14 123.24(12) . . ? N4 C14 C15 123.70(14) . . ? N4 C14 C13 115.85(12) . . ? C15 C14 C13 120.28(14) . . ? C14 C15 C16 118.03(17) . . ? C17 C16 C15 119.01(17) . . ? C16 C17 C18 118.97(16) . . ? N4 C18 C17 123.40(18) . . ? C18 N4 C14 116.88(15) . . ? C20 N5 Cu1 164.65(13) . . ? C21 N6 Cu1 171.65(14) . 1_545 ? C20 C19 C21 117.62(13) . . ? C20 C19 C22 120.75(13) . . ? C21 C19 C22 121.43(13) . . ? N5 C20 C19 177.90(15) . . ? N6 C21 C19 177.82(15) . . ? N7 C22 C19 178.9(2) . . ? C24 N8 Cu1 144.02(13) . . ? C24 C23 C25 119.61(15) . . ? C24 C23 C26 120.38(16) . . ? C25 C23 C26 119.96(15) . . ? N8 C24 C23 178.2(2) . . ? N9 C25 C23 179.2(2) . . ? N10 C26 C23 177.7(2) . . ? 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 N5 Cu1 N1 C1 -123.43(15) . . . . ? N8 Cu1 N1 C1 -31.17(13) . . . . ? N2 Cu1 N1 C1 162.63(13) . . . . ? N6 Cu1 N1 C1 62.80(13) 1_565 . . . ? N5 Cu1 N1 C5 55.86(17) . . . . ? N8 Cu1 N1 C5 148.12(10) . . . . ? N2 Cu1 N1 C5 -18.08(10) . . . . ? N6 Cu1 N1 C5 -117.92(10) 1_565 . . . ? N5 Cu1 N2 C6 -130.78(10) . . . . ? N1 Cu1 N2 C6 25.50(9) . . . . ? N8 Cu1 N2 C6 -34.0(2) . . . . ? N6 Cu1 N2 C6 129.22(9) 1_565 . . . ? N5 Cu1 N2 C7 33.81(12) . . . . ? N1 Cu1 N2 C7 -169.91(12) . . . . ? N8 Cu1 N2 C7 130.62(19) . . . . ? N6 Cu1 N2 C7 -66.20(12) 1_565 . . . ? C5 N1 C1 C2 -0.3(2) . . . . ? Cu1 N1 C1 C2 179.01(12) . . . . ? N1 C1 C2 C3 0.7(3) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C1 N1 C5 C4 -0.4(2) . . . . ? Cu1 N1 C5 C4 -179.72(11) . . . . ? C1 N1 C5 C6 -172.33(12) . . . . ? Cu1 N1 C5 C6 8.34(15) . . . . ? C3 C4 C5 N1 0.5(2) . . . . ? C3 C4 C5 C6 171.43(14) . . . . ? C7 N2 C6 C13 -8.75(19) . . . . ? Cu1 N2 C6 C13 157.29(10) . . . . ? C7 N2 C6 C5 165.86(12) . . . . ? Cu1 N2 C6 C5 -28.11(14) . . . . ? N1 C5 C6 N2 13.79(17) . . . . ? C4 C5 C6 N2 -157.71(14) . . . . ? N1 C5 C6 C13 -172.01(13) . . . . ? C4 C5 C6 C13 16.5(2) . . . . ? C6 N2 C7 C8 -175.59(13) . . . . ? Cu1 N2 C7 C8 20.93(19) . . . . ? C6 N2 C7 C12 1.61(19) . . . . ? Cu1 N2 C7 C12 -161.88(10) . . . . ? N2 C7 C8 C9 178.50(14) . . . . ? C12 C7 C8 C9 1.3(2) . . . . ? C7 C8 C9 C10 -0.1(2) . . . . ? C8 C9 C10 C11 -0.9(2) . . . . ? C9 C10 C11 C12 0.8(2) . . . . ? N2 C7 C12 N3 5.0(2) . . . . ? C8 C7 C12 N3 -177.72(13) . . . . ? N2 C7 C12 C11 -178.68(12) . . . . ? C8 C7 C12 C11 -1.5(2) . . . . ? C10 C11 C12 N3 176.72(13) . . . . ? C10 C11 C12 C7 0.4(2) . . . . ? C7 C12 N3 C13 -4.0(2) . . . . ? C11 C12 N3 C13 179.72(13) . . . . ? C12 N3 C13 C6 -3.3(2) . . . . ? C12 N3 C13 C14 171.38(12) . . . . ? N2 C6 C13 N3 10.0(2) . . . . ? C5 C6 C13 N3 -163.90(13) . . . . ? N2 C6 C13 C14 -164.28(13) . . . . ? C5 C6 C13 C14 21.9(2) . . . . ? N3 C13 C14 N4 -134.89(15) . . . . ? C6 C13 C14 N4 39.7(2) . . . . ? N3 C13 C14 C15 40.6(2) . . . . ? C6 C13 C14 C15 -144.84(16) . . . . ? N4 C14 C15 C16 1.1(3) . . . . ? C13 C14 C15 C16 -174.01(16) . . . . ? C14 C15 C16 C17 -0.1(3) . . . . ? C15 C16 C17 C18 -0.5(3) . . . . ? C16 C17 C18 N4 0.2(4) . . . . ? C17 C18 N4 C14 0.8(3) . . . . ? C15 C14 N4 C18 -1.4(3) . . . . ? C13 C14 N4 C18 173.89(17) . . . . ? N1 Cu1 N5 C20 52.5(5) . . . . ? N8 Cu1 N5 C20 -40.6(4) . . . . ? N2 Cu1 N5 C20 123.5(4) . . . . ? N6 Cu1 N5 C20 -133.6(4) 1_565 . . . ? Cu1 N5 C20 C19 -65(5) . . . . ? C21 C19 C20 N5 8(5) . . . . ? C22 C19 C20 N5 -167(5) . . . . ? Cu1 N6 C21 C19 71(6) 1_545 . . . ? C20 C19 C21 N6 -9(5) . . . . ? C22 C19 C21 N6 166(5) . . . . ? C20 C19 C22 N7 51(14) . . . . ? C21 C19 C22 N7 -124(14) . . . . ? N5 Cu1 N8 C24 36.8(2) . . . . ? N1 Cu1 N8 C24 -118.5(2) . . . . ? N2 Cu1 N8 C24 -60.6(3) . . . . ? N6 Cu1 N8 C24 135.8(2) 1_565 . . . ? Cu1 N8 C24 C23 168(94) . . . . ? C25 C23 C24 N8 -70(6) . . . . ? C26 C23 C24 N8 113(6) . . . . ? C24 C23 C25 N9 -3(21) . . . . ? C26 C23 C25 N9 174(100) . . . . ? C24 C23 C26 N10 128(6) . . . . ? C25 C23 C26 N10 -49(6) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.65 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.358 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.051