# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_Cu-benzene _database_code_depnum_ccdc_archive 'CCDC 900653' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H27 Cu3 N8 O0' _chemical_formula_weight 642.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4287(18) _cell_length_b 11.7031(18) _cell_length_c 12.918(2) _cell_angle_alpha 64.005(3) _cell_angle_beta 89.783(3) _cell_angle_gamma 71.129(3) _cell_volume 1450.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1131 _cell_measurement_theta_min 2.260 _cell_measurement_theta_max 21.190 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 2.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7329 _exptl_absorpt_correction_T_max 0.9169 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8472 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5028 _reflns_number_gt 3740 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1106P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5028 _refine_ls_number_parameters 338 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1868 _refine_ls_wR_factor_gt 0.1575 _refine_ls_goodness_of_fit_ref 1.025 _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 -0.1077(8) 0.4972(11) -0.1271(7) 0.111(4) Uani 1 1 d . . . H1A H -0.0905 0.5208 -0.0678 0.167 Uiso 1 1 calc R . . H1B H -0.0327 0.4325 -0.1308 0.167 Uiso 1 1 calc R . . H1C H -0.1716 0.4580 -0.1086 0.167 Uiso 1 1 calc R . . Cu1 Cu 0.37501(7) 1.16842(8) 0.08005(7) 0.0491(3) Uani 1 1 d . . . N1 N -0.2843(4) 0.7807(5) -0.4059(4) 0.0451(12) Uani 1 1 d . . . C2 C -0.1508(6) 0.6205(7) -0.2407(6) 0.0533(16) Uani 1 1 d . . . Cu2 Cu 0.54559(7) 0.86861(9) 0.49800(7) 0.0524(3) Uani 1 1 d . . . N2 N -0.2642(5) 0.6651(6) -0.3013(4) 0.0530(14) Uani 1 1 d . . . H2 H -0.3185 0.6264 -0.2780 0.064 Uiso 1 1 calc R . . C3 C -0.0922(6) 0.7089(8) -0.3103(6) 0.0565(18) Uani 1 1 d . . . Cu3 Cu 0.31549(7) 0.63807(8) 0.79610(7) 0.0455(3) Uani 1 1 d . . . N3 N 0.1598(4) 0.7650(5) -0.1754(4) 0.0400(11) Uani 1 1 d . . . C4 C -0.1773(6) 0.8033(7) -0.4094(6) 0.0507(16) Uani 1 1 d . . . N4 N 0.3792(4) 0.8948(5) 0.1418(5) 0.0508(13) Uani 1 1 d . . . H4 H 0.4024 0.8752 0.2127 0.061 Uiso 1 1 calc R . . C5 C -0.1656(7) 0.9248(8) -0.5131(8) 0.085(3) Uani 1 1 d . . . H5A H -0.2111 0.9390 -0.5827 0.128 Uiso 1 1 calc R . . H5B H -0.0789 0.9083 -0.5208 0.128 Uiso 1 1 calc R . . H5C H -0.1995 1.0042 -0.5018 0.128 Uiso 1 1 calc R . . N5 N 0.3515(4) 1.0213(5) 0.0503(5) 0.0462(12) Uani 1 1 d . . . C6 C 0.0372(6) 0.7043(9) -0.2781(7) 0.065(2) Uani 1 1 d . . . H6A H 0.0921 0.6096 -0.2362 0.079 Uiso 1 1 calc R . . H6B H 0.0690 0.7461 -0.3496 0.079 Uiso 1 1 calc R . . N6 N 0.4372(6) 1.0595(6) 0.2455(5) 0.0585(15) Uani 1 1 d . . . C7 C 0.0447(5) 0.7720(6) -0.2063(6) 0.0477(15) Uani 1 1 d . . . N7 N 0.4641(5) 0.7551(6) 0.6139(5) 0.0615(15) Uani 1 1 d . . . C8 C -0.0590(6) 0.8388(9) -0.1708(8) 0.076(2) Uani 1 1 d . . . H8 H -0.1389 0.8447 -0.1929 0.091 Uiso 1 1 calc R . . N8 N 0.3281(5) 0.4603(6) 0.9074(6) 0.0657(16) Uani 1 1 d . . . C9 C -0.0403(7) 0.8959(10) -0.1026(9) 0.098(3) Uani 1 1 d . . . H9 H -0.1076 0.9385 -0.0755 0.117 Uiso 1 1 calc R . . C10 C 0.0778(6) 0.8901(10) -0.0742(9) 0.090(3) Uani 1 1 d . . . H10 H 0.0904 0.9309 -0.0297 0.108 Uiso 1 1 calc R . . C11 C 0.1762(5) 0.8246(7) -0.1115(6) 0.0534(17) Uani 1 1 d . . . C12 C 0.3091(6) 0.8130(9) -0.0866(8) 0.073(2) Uani 1 1 d . . . H12A H 0.3364 0.8571 -0.1602 0.087 Uiso 1 1 calc R . . H12B H 0.3618 0.7174 -0.0496 0.087 Uiso 1 1 calc R . . C13 C 0.3907(8) 0.6587(8) 0.1959(8) 0.083(3) Uani 1 1 d . . . H13A H 0.4513 0.6318 0.2612 0.125 Uiso 1 1 calc R . . H13B H 0.4223 0.6015 0.1592 0.125 Uiso 1 1 calc R . . H13C H 0.3141 0.6496 0.2224 0.125 Uiso 1 1 calc R . . C14 C 0.3664(6) 0.8036(6) 0.1099(7) 0.0499(16) Uani 1 1 d . . . C15 C 0.3302(6) 0.8744(7) -0.0090(7) 0.0550(18) Uani 1 1 d . . . C16 C 0.3224(5) 1.0081(7) -0.0422(6) 0.0491(16) Uani 1 1 d . . . C17 C 0.2840(7) 1.1282(8) -0.1595(6) 0.073(2) Uani 1 1 d . . . H17A H 0.2597 1.2099 -0.1512 0.110 Uiso 1 1 calc R . . H17B H 0.2145 1.1282 -0.2010 0.110 Uiso 1 1 calc R . . H17C H 0.3530 1.1241 -0.2020 0.110 Uiso 1 1 calc R . . C18 C 0.4793(6) 0.9898(7) 0.3415(6) 0.0499(16) Uani 1 1 d . . . C19 C 0.4100(6) 0.7059(6) 0.6840(6) 0.0476(15) Uani 1 1 d . . . C20 C 0.3429(6) 0.3477(7) 0.9764(6) 0.0547(17) Uani 1 1 d . . . C21 C 0.7086(18) 0.415(2) 0.4941(15) 0.200(9) Uani 1 1 d D . . H21 H 0.6329 0.4380 0.4502 0.240 Uiso 1 1 calc R . . C22 C 0.773(2) 0.282(2) 0.5607(18) 0.177(8) Uani 1 1 d D . . H22 H 0.7463 0.2160 0.5585 0.213 Uiso 1 1 calc R . . C23 C 0.880(2) 0.248(2) 0.632(2) 0.221(11) Uani 1 1 d D . . H23 H 0.9270 0.1565 0.6810 0.265 Uiso 1 1 calc R . . C24 C 0.9189(16) 0.347(3) 0.6316(17) 0.157(6) Uani 1 1 d D . . H24 H 0.9891 0.3245 0.6830 0.189 Uiso 1 1 calc R . . C25 C 0.852(2) 0.483(2) 0.554(2) 0.177(8) Uani 1 1 d D . . H25 H 0.8838 0.5486 0.5491 0.212 Uiso 1 1 calc R . . C26 C 0.742(2) 0.5230(15) 0.4835(18) 0.226(12) Uani 1 1 d D . . H26 H 0.6948 0.6136 0.4337 0.271 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.077(6) 0.158(10) 0.059(6) -0.027(6) -0.011(5) -0.026(6) Cu1 0.0518(5) 0.0388(5) 0.0501(5) -0.0140(4) 0.0046(4) -0.0175(4) N1 0.041(3) 0.038(3) 0.049(3) -0.012(3) 0.002(2) -0.016(2) C2 0.056(4) 0.048(4) 0.045(4) -0.014(3) -0.007(3) -0.015(3) Cu2 0.0477(5) 0.0562(5) 0.0443(5) -0.0132(4) 0.0035(4) -0.0220(4) N2 0.048(3) 0.062(4) 0.050(3) -0.019(3) 0.002(3) -0.031(3) C3 0.046(4) 0.077(5) 0.063(4) -0.044(4) 0.005(3) -0.024(4) Cu3 0.0405(4) 0.0429(5) 0.0547(5) -0.0219(4) 0.0150(3) -0.0175(3) N3 0.034(2) 0.037(3) 0.050(3) -0.020(2) 0.009(2) -0.015(2) C4 0.043(4) 0.049(4) 0.062(4) -0.025(4) 0.012(3) -0.019(3) N4 0.046(3) 0.049(3) 0.057(4) -0.026(3) 0.005(3) -0.015(3) C5 0.069(5) 0.068(5) 0.103(7) -0.017(5) 0.020(5) -0.037(4) N5 0.044(3) 0.043(3) 0.050(3) -0.020(3) 0.004(2) -0.017(2) C6 0.040(4) 0.095(6) 0.089(6) -0.068(5) 0.008(3) -0.022(4) N6 0.070(4) 0.059(4) 0.046(3) -0.024(3) -0.003(3) -0.022(3) C7 0.033(3) 0.050(4) 0.064(4) -0.028(3) 0.007(3) -0.016(3) N7 0.051(3) 0.080(4) 0.058(4) -0.027(3) 0.010(3) -0.036(3) C8 0.033(3) 0.107(7) 0.126(7) -0.086(6) 0.015(4) -0.026(4) N8 0.064(4) 0.034(3) 0.084(4) -0.016(3) 0.022(3) -0.014(3) C9 0.038(4) 0.153(9) 0.173(10) -0.136(9) 0.038(5) -0.034(5) C10 0.046(4) 0.137(8) 0.157(9) -0.122(8) 0.037(5) -0.039(5) C11 0.040(3) 0.062(4) 0.079(5) -0.048(4) 0.012(3) -0.021(3) C12 0.038(4) 0.102(6) 0.125(7) -0.089(6) 0.022(4) -0.029(4) C13 0.089(6) 0.053(5) 0.121(8) -0.048(5) 0.036(5) -0.030(4) C14 0.041(3) 0.033(3) 0.073(5) -0.024(4) 0.010(3) -0.011(3) C15 0.036(3) 0.068(5) 0.085(5) -0.053(4) 0.016(3) -0.024(3) C16 0.033(3) 0.054(4) 0.062(4) -0.032(4) 0.006(3) -0.011(3) C17 0.065(5) 0.079(6) 0.061(5) -0.029(5) -0.002(4) -0.012(4) C18 0.044(3) 0.055(4) 0.059(4) -0.028(4) 0.007(3) -0.024(3) C19 0.047(3) 0.043(4) 0.051(4) -0.016(3) 0.009(3) -0.021(3) C20 0.051(4) 0.045(4) 0.065(5) -0.024(4) 0.014(3) -0.015(3) C21 0.204(18) 0.24(2) 0.182(18) -0.15(2) -0.022(15) -0.030(19) C22 0.22(2) 0.18(2) 0.21(2) -0.16(2) 0.082(17) -0.078(17) C23 0.18(2) 0.23(3) 0.24(3) -0.15(2) 0.07(2) -0.01(2) C24 0.122(12) 0.167(16) 0.179(17) -0.089(16) 0.002(11) -0.033(13) C25 0.196(19) 0.22(3) 0.18(2) -0.14(2) 0.064(15) -0.085(18) C26 0.41(4) 0.073(9) 0.175(18) -0.048(11) 0.01(2) -0.074(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 C1 C2 1.472(10) . ? Cu1 C20 1.837(7) 1_564 ? Cu1 N6 1.933(6) . ? Cu1 N5 2.017(5) . ? N1 C4 1.329(7) . ? N1 N2 1.382(7) . ? N1 Cu2 1.996(5) 1_454 ? C2 N2 1.334(8) . ? C2 C3 1.398(9) . ? Cu2 C18 1.865(7) . ? Cu2 N7 1.980(6) . ? Cu2 N1 1.996(5) 1_656 ? Cu2 Cu2 2.9346(18) 2_676 ? C3 C4 1.371(9) . ? C3 C6 1.515(8) . ? Cu3 C19 1.852(6) . ? Cu3 N8 1.898(6) . ? Cu3 N3 2.067(4) 1_556 ? N3 C11 1.339(7) . ? N3 C7 1.343(7) . ? N3 Cu3 2.067(4) 1_554 ? C4 C5 1.512(10) . ? N4 C14 1.348(8) . ? N4 N5 1.362(7) . ? N5 C16 1.326(8) . ? C6 C7 1.479(9) . ? N6 C18 1.139(8) . ? C7 C8 1.391(9) . ? N7 C19 1.141(8) . ? C8 C9 1.370(10) . ? N8 C20 1.177(8) . ? C9 C10 1.372(10) . ? C10 C11 1.359(9) . ? C11 C12 1.504(8) . ? C12 C15 1.524(9) . ? C13 C14 1.494(10) . ? C14 C15 1.374(10) . ? C15 C16 1.400(9) . ? C16 C17 1.484(9) . ? C20 Cu1 1.837(7) 1_546 ? C21 C22 1.343(9) . ? C21 C26 1.383(9) . ? C22 C23 1.370(9) . ? C23 C24 1.373(10) . ? C24 C25 1.389(9) . ? C25 C26 1.371(9) . ? 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 C20 Cu1 N6 133.8(3) 1_564 . ? C20 Cu1 N5 128.7(3) 1_564 . ? N6 Cu1 N5 97.5(2) . . ? C4 N1 N2 104.6(5) . . ? C4 N1 Cu2 138.3(5) . 1_454 ? N2 N1 Cu2 117.0(3) . 1_454 ? N2 C2 C3 105.7(6) . . ? N2 C2 C1 121.6(7) . . ? C3 C2 C1 132.6(7) . . ? C18 Cu2 N7 126.5(2) . . ? C18 Cu2 N1 135.0(2) . 1_656 ? N7 Cu2 N1 97.3(2) . 1_656 ? C18 Cu2 Cu2 78.1(2) . 2_676 ? N7 Cu2 Cu2 105.32(19) . 2_676 ? N1 Cu2 Cu2 101.81(15) 1_656 2_676 ? C2 N2 N1 111.9(5) . . ? C4 C3 C2 106.4(6) . . ? C4 C3 C6 127.4(7) . . ? C2 C3 C6 126.1(7) . . ? C19 Cu3 N8 134.0(3) . . ? C19 Cu3 N3 121.8(2) . 1_556 ? N8 Cu3 N3 104.2(2) . 1_556 ? C11 N3 C7 120.3(5) . . ? C11 N3 Cu3 119.0(4) . 1_554 ? C7 N3 Cu3 120.1(4) . 1_554 ? N1 C4 C3 111.3(6) . . ? N1 C4 C5 119.3(6) . . ? C3 C4 C5 129.4(6) . . ? C14 N4 N5 113.1(5) . . ? C16 N5 N4 104.5(5) . . ? C16 N5 Cu1 136.6(5) . . ? N4 N5 Cu1 118.6(4) . . ? C7 C6 C3 115.8(5) . . ? C18 N6 Cu1 175.8(6) . . ? N3 C7 C8 120.7(6) . . ? N3 C7 C6 115.8(5) . . ? C8 C7 C6 123.5(5) . . ? C19 N7 Cu2 169.7(6) . . ? C9 C8 C7 118.3(6) . . ? C20 N8 Cu3 176.3(6) . . ? C8 C9 C10 119.9(6) . . ? C11 C10 C9 119.7(7) . . ? N3 C11 C10 121.0(6) . . ? N3 C11 C12 114.8(5) . . ? C10 C11 C12 124.3(6) . . ? C11 C12 C15 115.4(5) . . ? N4 C14 C15 105.1(6) . . ? N4 C14 C13 122.5(7) . . ? C15 C14 C13 132.4(7) . . ? C14 C15 C16 106.6(6) . . ? C14 C15 C12 124.9(7) . . ? C16 C15 C12 128.4(7) . . ? N5 C16 C15 110.6(6) . . ? N5 C16 C17 119.8(6) . . ? C15 C16 C17 129.5(6) . . ? N6 C18 Cu2 177.0(6) . . ? N7 C19 Cu3 176.0(6) . . ? N8 C20 Cu1 176.3(6) . 1_546 ? C22 C21 C26 127.2(18) . . ? C21 C22 C23 117.0(19) . . ? C22 C23 C24 120(2) . . ? C23 C24 C25 119.5(19) . . ? C26 C25 C24 122.6(18) . . ? C25 C26 C21 113.3(17) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.748 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.131 data_Cu-MeCN-RT _database_code_depnum_ccdc_archive 'CCDC 900655' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 Cu3 N8 O0' _chemical_formula_weight 564.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 '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 11.4262(5) _cell_length_b 11.4509(5) _cell_length_c 12.5243(7) _cell_angle_alpha 66.620(5) _cell_angle_beta 89.182(4) _cell_angle_gamma 69.908(4) _cell_volume 1398.38(12) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3497 _cell_measurement_theta_min 3.8811 _cell_measurement_theta_max 72.9678 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 2.804 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6784 _exptl_absorpt_correction_T_max 0.8725 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9078 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 73.12 _reflns_number_total 5390 _reflns_number_gt 3987 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.074 0.500 0.500 334 48 ' ' _platon_squeeze_details ; ; _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^)+(0.1422P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5390 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.2170 _refine_ls_wR_factor_gt 0.1940 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.12706(7) 0.81901(7) -0.08289(6) 0.0602(2) Uani 1 1 d . . . N1 N 0.7803(4) 1.2307(5) 0.4171(4) 0.0625(10) Uani 1 1 d . . . C1 C 0.6025(9) 1.5043(11) 0.1402(8) 0.121(3) Uani 1 1 d . . . H1A H 0.5471 1.5822 0.1512 0.181 Uiso 1 1 calc R . . H1B H 0.5587 1.4864 0.0872 0.181 Uiso 1 1 calc R . . H1C H 0.6743 1.5227 0.1080 0.181 Uiso 1 1 calc R . . N2 N 0.7584(4) 1.3410(5) 0.3150(4) 0.0681(11) Uani 1 1 d . . . H2 H 0.8118 1.3801 0.2910 0.082 Uiso 1 1 calc R . . C2 C 0.6446(6) 1.3842(7) 0.2540(6) 0.0745(15) Uani 1 1 d . . . Cu2 Cu -0.04699(7) 1.13210(9) -0.49394(7) 0.0663(3) Uani 1 1 d . . . N3 N 0.3415(4) 1.2249(4) 0.1934(4) 0.0566(9) Uani 1 1 d . . . C3 C 0.5887(5) 1.2972(7) 0.3199(6) 0.0723(15) Uani 1 1 d . . . Cu3 Cu 0.18414(7) 1.36329(7) -0.78168(7) 0.0583(2) Uani 1 1 d . . . C4 C 0.6755(5) 1.2027(6) 0.4218(6) 0.0658(12) Uani 1 1 d . . . N4 N 0.1281(4) 1.0932(5) -0.1372(5) 0.0664(11) Uani 1 1 d . . . H4 H 0.1070 1.1135 -0.2099 0.080 Uiso 1 1 calc R . . N5 N 0.1518(4) 0.9673(4) -0.0480(4) 0.0580(9) Uani 1 1 d . . . C5 C 0.6652(8) 1.0828(9) 0.5264(8) 0.105(3) Uani 1 1 d . . . H5A H 0.7012 1.0009 0.5139 0.158 Uiso 1 1 calc R . . H5B H 0.5782 1.0993 0.5354 0.158 Uiso 1 1 calc R . . H5C H 0.7097 1.0722 0.5961 0.158 Uiso 1 1 calc R . . C6 C 0.4596(6) 1.3003(9) 0.2914(8) 0.088(2) Uani 1 1 d . . . H6A H 0.4053 1.3943 0.2439 0.106 Uiso 1 1 calc R . . H6B H 0.4251 1.2689 0.3641 0.106 Uiso 1 1 calc R . . N6 N 0.0652(5) 0.9245(5) -0.2483(4) 0.0685(11) Uani 1 1 d . . . C7 C 0.4573(5) 1.2135(6) 0.2266(6) 0.0698(14) Uani 1 1 d . . . N7 N 0.0325(5) 1.2584(6) -0.5978(5) 0.0769(13) Uani 1 1 d . . . C8 C 0.5643(6) 1.1272(10) 0.2049(9) 0.104(3) Uani 1 1 d . . . H8 H 0.6437 1.1216 0.2280 0.125 Uiso 1 1 calc R . . N8 N 0.1698(5) 1.5374(5) -0.9032(5) 0.0772(13) Uani 1 1 d . . . C9 C 0.5510(6) 1.0497(11) 0.1485(11) 0.125(4) Uani 1 1 d . . . H9 H 0.6217 0.9896 0.1347 0.150 Uiso 1 1 calc R . . C10 C 0.4324(6) 1.0621(10) 0.1129(10) 0.112(3) Uani 1 1 d . . . H10 H 0.4217 1.0125 0.0728 0.135 Uiso 1 1 calc R . . C11 C 0.3276(5) 1.1510(7) 0.1381(7) 0.0749(16) Uani 1 1 d . . . C12 C 0.1926(5) 1.1697(9) 0.1075(8) 0.094(2) Uani 1 1 d . . . H12A H 0.1613 1.1267 0.1793 0.112 Uiso 1 1 calc R . . H12B H 0.1419 1.2668 0.0739 0.112 Uiso 1 1 calc R . . C13 C 0.1229(9) 1.3253(8) -0.1807(10) 0.116(3) Uani 1 1 d . . . H13A H 0.1949 1.3257 -0.2209 0.174 Uiso 1 1 calc R . . H13B H 0.1122 1.3807 -0.1378 0.174 Uiso 1 1 calc R . . H13C H 0.0492 1.3615 -0.2369 0.174 Uiso 1 1 calc R . . C14 C 0.1420(5) 1.1817(6) -0.0971(7) 0.0774(17) Uani 1 1 d . . . C15 C 0.1746(5) 1.1115(7) 0.0224(7) 0.0715(15) Uani 1 1 d . . . C16 C 0.1800(4) 0.9785(6) 0.0492(5) 0.0613(12) Uani 1 1 d . . . C17 C 0.2145(7) 0.8592(8) 0.1648(6) 0.0854(18) Uani 1 1 d . . . H17A H 0.2270 0.7778 0.1535 0.128 Uiso 1 1 calc R . . H17B H 0.1481 0.8726 0.2116 0.128 Uiso 1 1 calc R . . H17C H 0.2908 0.8497 0.2043 0.128 Uiso 1 1 calc R . . C18 C 0.0229(5) 0.9979(6) -0.3431(5) 0.0621(12) Uani 1 1 d . . . C19 C 0.0901(5) 1.3019(5) -0.6644(5) 0.0601(11) Uani 1 1 d . . . C20 C 0.1572(6) 1.6412(6) -0.9727(5) 0.0670(13) 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 0.0618(4) 0.0520(4) 0.0607(4) -0.0157(3) 0.0031(3) -0.0230(3) N1 0.050(2) 0.067(2) 0.068(2) -0.024(2) 0.0027(18) -0.0240(19) C1 0.091(6) 0.126(7) 0.096(6) -0.012(5) -0.025(4) -0.023(5) N2 0.057(2) 0.075(3) 0.068(3) -0.020(2) -0.0021(19) -0.030(2) C2 0.062(3) 0.085(4) 0.071(3) -0.031(3) -0.002(3) -0.024(3) Cu2 0.0558(4) 0.0716(5) 0.0596(4) -0.0128(4) 0.0033(3) -0.0267(4) N3 0.0413(18) 0.058(2) 0.078(3) -0.035(2) 0.0086(17) -0.0185(16) C3 0.051(3) 0.088(4) 0.092(4) -0.054(3) 0.002(3) -0.022(3) Cu3 0.0484(4) 0.0506(4) 0.0743(5) -0.0223(3) 0.0128(3) -0.0210(3) C4 0.050(3) 0.071(3) 0.086(4) -0.039(3) 0.012(2) -0.026(2) N4 0.052(2) 0.056(2) 0.081(3) -0.020(2) 0.0019(19) -0.0195(18) N5 0.052(2) 0.053(2) 0.065(2) -0.0195(18) -0.0047(17) -0.0193(17) C5 0.080(5) 0.110(6) 0.126(6) -0.029(5) 0.021(4) -0.057(5) C6 0.048(3) 0.114(5) 0.132(6) -0.084(5) 0.006(3) -0.024(3) N6 0.078(3) 0.069(3) 0.058(2) -0.022(2) 0.001(2) -0.032(2) C7 0.044(2) 0.079(3) 0.102(4) -0.054(3) 0.009(2) -0.022(2) N7 0.063(3) 0.083(3) 0.077(3) -0.016(2) 0.006(2) -0.038(3) C8 0.043(3) 0.143(7) 0.174(8) -0.116(7) 0.015(4) -0.029(4) N8 0.072(3) 0.058(3) 0.088(3) -0.018(2) 0.022(2) -0.023(2) C9 0.045(3) 0.167(9) 0.224(11) -0.151(9) 0.027(5) -0.028(4) C10 0.052(3) 0.153(7) 0.196(9) -0.140(8) 0.023(4) -0.032(4) C11 0.042(2) 0.087(4) 0.122(5) -0.068(4) 0.018(3) -0.025(2) C12 0.045(3) 0.119(6) 0.163(7) -0.102(6) 0.020(3) -0.032(3) C13 0.101(6) 0.060(4) 0.175(9) -0.036(5) 0.042(6) -0.030(4) C14 0.049(3) 0.057(3) 0.134(6) -0.045(3) 0.023(3) -0.023(2) C15 0.042(2) 0.077(3) 0.114(5) -0.057(4) 0.010(3) -0.022(2) C16 0.044(2) 0.070(3) 0.077(3) -0.037(3) 0.005(2) -0.021(2) C17 0.079(4) 0.091(4) 0.072(4) -0.032(3) -0.008(3) -0.017(3) C18 0.059(3) 0.067(3) 0.058(3) -0.019(2) 0.008(2) -0.029(2) C19 0.048(2) 0.053(2) 0.074(3) -0.019(2) 0.008(2) -0.020(2) C20 0.067(3) 0.050(3) 0.076(3) -0.018(2) 0.010(2) -0.022(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C20 1.863(5) 1_546 ? Cu1 N6 1.928(5) . ? Cu1 N5 2.019(4) . ? N1 C4 1.337(7) . ? N1 N2 1.343(7) . ? N1 Cu2 1.986(4) 1_656 ? C1 C2 1.471(11) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? N2 C2 1.343(7) . ? N2 H2 0.8600 . ? C2 C3 1.361(10) . ? Cu2 C18 1.861(5) . ? Cu2 N1 1.986(4) 1_454 ? Cu2 N7 1.997(5) . ? Cu2 Cu2 2.9080(18) 2_574 ? N3 C11 1.334(7) . ? N3 C7 1.340(7) . ? N3 Cu3 2.064(4) 1_556 ? C3 C4 1.409(9) . ? C3 C6 1.508(8) . ? Cu3 C19 1.860(5) . ? Cu3 N8 1.921(5) . ? Cu3 N3 2.064(4) 1_554 ? C4 C5 1.514(10) . ? N4 C14 1.350(8) . ? N4 N5 1.365(6) . ? N4 H4 0.8600 . ? N5 C16 1.328(7) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.519(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N6 C18 1.139(7) . ? C7 C8 1.386(9) . ? N7 C19 1.121(8) . ? C8 C9 1.379(10) . ? C8 H8 0.9300 . ? N8 C20 1.121(8) . ? C9 C10 1.375(10) . ? C9 H9 0.9300 . ? C10 C11 1.407(9) . ? C10 H10 0.9300 . ? C11 C12 1.516(7) . ? C12 C15 1.512(9) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.497(10) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.371(10) . ? C15 C16 1.403(8) . ? C16 C17 1.482(9) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C20 Cu1 1.863(5) 1_564 ? 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 C20 Cu1 N6 136.7(2) 1_546 . ? C20 Cu1 N5 125.2(2) 1_546 . ? N6 Cu1 N5 98.10(19) . . ? C4 N1 N2 104.8(4) . . ? C4 N1 Cu2 134.9(4) . 1_656 ? N2 N1 Cu2 119.2(3) . 1_656 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 N2 C2 113.3(5) . . ? N1 N2 H2 123.4 . . ? C2 N2 H2 123.4 . . ? N2 C2 C3 105.8(5) . . ? N2 C2 C1 121.5(7) . . ? C3 C2 C1 132.6(6) . . ? C18 Cu2 N1 134.8(2) . 1_454 ? C18 Cu2 N7 125.3(2) . . ? N1 Cu2 N7 97.8(2) 1_454 . ? C18 Cu2 Cu2 71.97(18) . 2_574 ? N1 Cu2 Cu2 106.52(14) 1_454 2_574 ? N7 Cu2 Cu2 111.86(19) . 2_574 ? C11 N3 C7 119.6(4) . . ? C11 N3 Cu3 119.6(3) . 1_556 ? C7 N3 Cu3 120.7(3) . 1_556 ? C2 C3 C4 106.3(5) . . ? C2 C3 C6 127.5(7) . . ? C4 C3 C6 126.2(7) . . ? C19 Cu3 N8 135.5(2) . . ? C19 Cu3 N3 120.0(2) . 1_554 ? N8 Cu3 N3 104.4(2) . 1_554 ? N1 C4 C3 109.8(5) . . ? N1 C4 C5 120.1(6) . . ? C3 C4 C5 130.1(6) . . ? C14 N4 N5 111.4(5) . . ? C14 N4 H4 124.3 . . ? N5 N4 H4 124.3 . . ? C16 N5 N4 105.6(4) . . ? C16 N5 Cu1 134.8(4) . . ? N4 N5 Cu1 119.4(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 C7 114.3(5) . . ? C3 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C3 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C18 N6 Cu1 173.0(5) . . ? N3 C7 C8 121.9(5) . . ? N3 C7 C6 114.1(5) . . ? C8 C7 C6 123.9(5) . . ? C19 N7 Cu2 161.8(6) . . ? C9 C8 C7 118.9(6) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C20 N8 Cu3 177.4(6) . . ? C10 C9 C8 119.5(6) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 118.8(6) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? N3 C11 C10 121.3(5) . . ? N3 C11 C12 114.9(5) . . ? C10 C11 C12 123.8(5) . . ? C15 C12 C11 114.7(5) . . ? C15 C12 H12A 108.6 . . ? C11 C12 H12A 108.6 . . ? C15 C12 H12B 108.6 . . ? C11 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C14 C15 106.6(5) . . ? N4 C14 C13 120.4(8) . . ? C15 C14 C13 132.9(7) . . ? C14 C15 C16 106.0(5) . . ? C14 C15 C12 126.4(7) . . ? C16 C15 C12 127.5(7) . . ? N5 C16 C15 110.4(5) . . ? N5 C16 C17 120.8(5) . . ? C15 C16 C17 128.8(6) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N6 C18 Cu2 174.2(5) . . ? N7 C19 Cu3 174.4(5) . . ? N8 C20 Cu1 175.8(6) . 1_564 ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 73.12 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.448 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.142 data_Cu-Ethanol-RT _database_code_depnum_ccdc_archive 'CCDC 918401' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 Cu3 N8 O2' _chemical_formula_weight 625.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4964(6) _cell_length_b 11.3571(6) _cell_length_c 12.9352(7) _cell_angle_alpha 115.386(5) _cell_angle_beta 91.133(4) _cell_angle_gamma 69.305(5) _cell_volume 1409.93(13) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4572 _cell_measurement_theta_min 2.7952 _cell_measurement_theta_max 29.4409 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 634 _exptl_absorpt_coefficient_mu 2.274 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5894 _exptl_absorpt_correction_T_max 0.8045 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9916 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4981 _reflns_number_gt 3991 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4981 _refine_ls_number_parameters 321 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.896 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.001 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 Cu2 Cu 0.94121(2) 0.13681(2) 0.006150(19) 0.05174(7) Uani 1 1 d . . . Cu1 Cu 1.12206(2) -0.17028(2) -0.405769(18) 0.04577(6) Uani 1 1 d . . . N1 N 1.77134(13) 0.23323(15) -0.89940(13) 0.0494(5) Uani 1 1 d . . . N3 N 1.34221(12) 0.21218(13) -0.69227(12) 0.0399(4) Uani 1 1 d . . . N4 N 1.13214(13) 0.10228(13) -0.36806(13) 0.0467(4) Uani 1 1 d . . . H4 H 1.1119 0.1329 -0.2949 0.056 Uiso 1 1 calc R . . N5 N 1.15212(13) -0.03115(14) -0.44813(13) 0.0458(4) Uani 1 1 d . . . N7 N 1.02308(14) 0.26293(16) 0.11123(14) 0.0547(5) Uani 1 1 d . . . N2 N 1.74915(14) 0.34773(16) -0.79807(13) 0.0538(5) Uani 1 1 d . . . H2 H 1.8020 0.3880 -0.7746 0.065 Uiso 1 1 calc R . . N6 N 1.05697(16) -0.05615(15) -0.24261(13) 0.0538(5) Uani 1 1 d . . . C16 C 1.17898(16) -0.03416(18) -0.54964(15) 0.0473(5) Uani 1 1 d . . . C18 C 1.01185(17) 0.01223(18) -0.14773(16) 0.0501(5) Uani 1 1 d . . . C4 C 1.66986(17) 0.20258(18) -0.90420(18) 0.0538(6) Uani 1 1 d . . . C19 C 1.08326(16) 0.30210(16) 0.17761(15) 0.0422(5) Uani 1 1 d . . . C15 C 1.17793(16) 0.09634(17) -0.53277(17) 0.0501(5) Uani 1 1 d . . . C2 C 1.63572(18) 0.3933(2) -0.73677(17) 0.0575(6) Uani 1 1 d . . . C14 C 1.14730(16) 0.18048(17) -0.41519(18) 0.0520(6) Uani 1 1 d . . . C12 C 1.19981(17) 0.14064(19) -0.62260(18) 0.0628(5) Uani 1 1 d . . . H12A H 1.1790 0.0824 -0.6948 0.075 Uiso 1 1 calc R . . H12B H 1.1422 0.2373 -0.5982 0.075 Uiso 1 1 calc R . . C3 C 1.58138(17) 0.30073(18) -0.80344(17) 0.0557(5) Uani 1 1 d . . . C11 C 1.33104(16) 0.13112(18) -0.64534(16) 0.0505(5) Uani 1 1 d . . . C17 C 1.2096(2) -0.1660(2) -0.66035(18) 0.0670(7) Uani 1 1 d . . . H17A H 1.2980 -0.2218 -0.6747 0.100 Uiso 1 1 calc R . . H17B H 1.1876 -0.1422 -0.7229 0.100 Uiso 1 1 calc R . . H17C H 1.1628 -0.2188 -0.6547 0.100 Uiso 1 1 calc R . . C7 C 1.45566(16) 0.20777(18) -0.71918(17) 0.0521(5) Uani 1 1 d . . . C6 C 1.45521(18) 0.3028(2) -0.77256(19) 0.0680(6) Uani 1 1 d . . . H6A H 1.4170 0.2765 -0.8423 0.082 Uiso 1 1 calc R . . H6B H 1.4020 0.3987 -0.7189 0.082 Uiso 1 1 calc R . . C8 C 1.56286(19) 0.1224(2) -0.6987(2) 0.0859(7) Uani 1 1 d . . . H8 H 1.6415 0.1199 -0.7179 0.103 Uiso 1 1 calc R . . C10 C 1.43558(19) 0.0441(2) -0.6223(2) 0.0821(6) Uani 1 1 d . . . H10 H 1.4275 -0.0113 -0.5891 0.099 Uiso 1 1 calc R . . C5 C 1.6613(2) 0.0786(3) -1.0055(3) 0.0931(11) Uani 1 1 d . . . H5A H 1.5909 0.1098 -1.0415 0.140 Uiso 1 1 calc R . . H5B H 1.6501 0.0149 -0.9798 0.140 Uiso 1 1 calc R . . H5C H 1.7373 0.0311 -1.0603 0.140 Uiso 1 1 calc R . . C13 C 1.1321(2) 0.3332(2) -0.3426(2) 0.0773(8) Uani 1 1 d . . . H13A H 1.0474 0.3880 -0.3020 0.116 Uiso 1 1 calc R . . H13B H 1.1494 0.3701 -0.3922 0.116 Uiso 1 1 calc R . . H13C H 1.1898 0.3379 -0.2877 0.116 Uiso 1 1 calc R . . C1 C 1.5898(3) 0.5204(3) -0.6215(2) 0.0979(11) Uani 1 1 d . . . H1A H 1.6586 0.5477 -0.5931 0.147 Uiso 1 1 calc R . . H1B H 1.5555 0.4987 -0.5680 0.147 Uiso 1 1 calc R . . H1C H 1.5257 0.5964 -0.6294 0.147 Uiso 1 1 calc R . . C9 C 1.5510(2) 0.0413(3) -0.6493(2) 0.1047(8) Uani 1 1 d . . . H9 H 1.6223 -0.0163 -0.6340 0.126 Uiso 1 1 calc R . . O1 O 0.8722(4) 0.7486(3) 0.1170(2) 0.2132(12) Uani 1 1 d . . . O2 O 0.8435(4) 0.5039(5) 0.0065(7) 0.404(5) Uani 1 1 d DU . . C22 C 0.7231(5) 0.6068(7) 0.0135(8) 0.649(12) Uani 1 1 d DU . . H22A H 0.7187 0.6113 -0.0598 0.779 Uiso 1 1 calc R . . H22B H 0.7167 0.6985 0.0728 0.779 Uiso 1 1 calc R . . C21 C 0.6079(5) 0.5769(10) 0.0418(11) 0.726(16) Uani 1 1 d DU . . H21A H 0.5989 0.5955 0.1215 1.089 Uiso 1 1 calc R . . H21B H 0.6212 0.4800 -0.0069 1.089 Uiso 1 1 calc R . . H21C H 0.5328 0.6368 0.0281 1.089 Uiso 1 1 calc R . . Cu3 Cu 1.180766(18) 0.35734(2) 0.293108(18) 0.04275(6) Uani 1 1 d . . . N8 N 1.16461(16) 0.53290(17) 0.42002(15) 0.0600(6) Uani 1 1 d . . . C20 C 1.15191(18) 0.64370(18) 0.48951(17) 0.0501(6) 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 Cu2 0.04459(10) 0.05853(11) 0.04020(11) 0.00901(9) 0.00000(9) -0.02302(9) Cu1 0.05352(11) 0.03968(8) 0.04014(10) 0.01253(7) -0.00194(9) -0.02006(8) N1 0.0412(7) 0.0533(7) 0.0500(8) 0.0170(6) -0.0020(6) -0.0216(6) N3 0.0279(6) 0.0445(5) 0.0496(7) 0.0230(5) -0.0042(5) -0.0138(5) N4 0.0415(7) 0.0424(6) 0.0495(8) 0.0159(5) 0.0007(6) -0.0144(6) N5 0.0441(7) 0.0430(6) 0.0483(7) 0.0184(5) 0.0016(6) -0.0167(5) N7 0.0503(7) 0.0630(7) 0.0471(8) 0.0152(6) -0.0094(7) -0.0296(6) N2 0.0432(7) 0.0622(7) 0.0469(8) 0.0128(6) 0.0022(6) -0.0247(6) N6 0.0716(9) 0.0514(6) 0.0362(7) 0.0139(5) 0.0010(7) -0.0279(6) C16 0.0354(8) 0.0610(8) 0.0513(9) 0.0316(6) -0.0028(7) -0.0166(6) C18 0.0516(9) 0.0575(8) 0.0431(9) 0.0180(7) -0.0086(7) -0.0288(7) C4 0.0417(8) 0.0564(8) 0.0731(11) 0.0330(7) -0.0122(8) -0.0247(7) C19 0.0410(8) 0.0367(7) 0.0430(8) 0.0127(6) -0.0048(7) -0.0148(6) C15 0.0327(7) 0.0625(7) 0.0729(9) 0.0441(6) -0.0107(7) -0.0207(6) C2 0.0455(9) 0.0761(9) 0.0533(10) 0.0305(7) 0.0009(8) -0.0236(8) C14 0.0378(8) 0.0471(7) 0.0794(11) 0.0351(7) -0.0163(8) -0.0175(6) C12 0.0399(8) 0.0904(8) 0.0956(10) 0.0707(7) -0.0180(8) -0.0303(7) C3 0.0373(8) 0.0700(8) 0.0744(10) 0.0469(7) -0.0027(8) -0.0182(7) C11 0.0373(8) 0.0624(7) 0.0663(9) 0.0402(6) -0.0106(7) -0.0207(6) C17 0.0703(12) 0.0699(10) 0.0532(11) 0.0240(8) 0.0038(10) -0.0227(9) C7 0.0337(8) 0.0658(8) 0.0698(9) 0.0435(6) -0.0068(7) -0.0171(7) C6 0.0372(9) 0.0880(9) 0.1057(12) 0.0684(8) -0.0058(9) -0.0220(8) C8 0.0345(9) 0.1298(11) 0.1380(13) 0.1048(9) -0.0100(9) -0.0238(9) C10 0.0381(9) 0.1175(9) 0.1375(12) 0.1035(8) -0.0145(9) -0.0230(8) C5 0.0667(12) 0.0771(13) 0.114(2) 0.0144(13) -0.0144(13) -0.0399(10) C13 0.0714(12) 0.0571(9) 0.1142(16) 0.0433(9) -0.0315(12) -0.0314(8) C1 0.0736(15) 0.1097(18) 0.0672(16) 0.0071(14) 0.0183(13) -0.0274(14) C9 0.0373(11) 0.1509(12) 0.1807(16) 0.1353(10) -0.0171(11) -0.0197(10) O1 0.412(3) 0.2318(15) 0.0882(14) 0.0642(12) -0.0337(19) -0.2327(16) O2 0.426(10) 0.228(4) 0.492(8) 0.171(5) 0.013(8) -0.037(6) C22 0.46(2) 0.940(16) 0.499(9) 0.550(9) 0.032(13) 0.074(17) C21 0.99(4) 0.734(14) 0.726(12) 0.599(9) -0.39(2) -0.303(19) Cu3 0.03838(10) 0.04086(9) 0.04791(11) 0.01743(7) -0.01027(8) -0.01736(7) N8 0.0553(9) 0.0456(7) 0.0622(10) 0.0122(7) -0.0153(8) -0.0164(6) C20 0.0522(9) 0.0453(8) 0.0474(9) 0.0161(7) -0.0080(8) -0.0186(7) _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 Cu2 C18 1.8603(17) . ? Cu2 N1 1.9853(14) 1_456 ? Cu2 N7 2.0044(17) . ? Cu2 Cu2 2.8504(5) 2_755 ? Cu1 C20 1.8623(17) 1_544 ? Cu1 N6 1.9302(14) . ? Cu1 N5 2.0131(17) . ? N1 C4 1.324(3) . ? N1 N2 1.3384(19) . ? N1 Cu2 1.9853(14) 1_654 ? N3 C7 1.335(2) . ? N3 C11 1.341(3) . ? N3 Cu3 2.0711(13) 1_554 ? N4 C14 1.330(3) . ? N4 N5 1.3562(18) . ? N4 H4 0.8600 . ? N5 C16 1.338(3) . ? N7 C19 1.132(2) . ? N2 C2 1.345(3) . ? N2 H2 0.8600 . ? N6 C18 1.141(2) . ? C16 C15 1.398(3) . ? C16 C17 1.492(2) . ? C4 C3 1.408(2) . ? C4 C5 1.490(3) . ? C19 Cu3 1.8733(18) . ? C15 C14 1.374(3) . ? C15 C12 1.506(3) . ? C2 C3 1.380(3) . ? C2 C1 1.494(3) . ? C14 C13 1.522(3) . ? C12 C11 1.500(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C3 C6 1.502(3) . ? C11 C10 1.381(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C7 C8 1.375(3) . ? C7 C6 1.508(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C9 1.368(4) . ? C8 H8 0.9300 . ? C10 C9 1.364(4) . ? C10 H10 0.9300 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C9 H9 0.9300 . ? O2 C22 1.435(6) . ? C22 C21 1.565(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? Cu3 N8 1.9101(16) . ? Cu3 N3 2.0711(13) 1_556 ? N8 C20 1.148(2) . ? C20 Cu1 1.8623(17) 1_566 ? 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 C18 Cu2 N1 136.91(8) . 1_456 ? C18 Cu2 N7 121.81(8) . . ? N1 Cu2 N7 98.55(6) 1_456 . ? C18 Cu2 Cu2 72.99(7) . 2_755 ? N1 Cu2 Cu2 109.68(5) 1_456 2_755 ? N7 Cu2 Cu2 109.10(5) . 2_755 ? C20 Cu1 N6 134.25(9) 1_544 . ? C20 Cu1 N5 124.24(8) 1_544 . ? N6 Cu1 N5 101.49(7) . . ? C4 N1 N2 105.76(14) . . ? C4 N1 Cu2 134.68(11) . 1_654 ? N2 N1 Cu2 118.98(12) . 1_654 ? C7 N3 C11 120.02(15) . . ? C7 N3 Cu3 120.68(13) . 1_554 ? C11 N3 Cu3 119.01(11) . 1_554 ? C14 N4 N5 112.53(15) . . ? C14 N4 H4 123.7 . . ? N5 N4 H4 123.7 . . ? C16 N5 N4 104.63(16) . . ? C16 N5 Cu1 132.91(12) . . ? N4 N5 Cu1 122.06(12) . . ? C19 N7 Cu2 160.10(17) . . ? N1 N2 C2 113.02(17) . . ? N1 N2 H2 123.5 . . ? C2 N2 H2 123.5 . . ? C18 N6 Cu1 176.14(18) . . ? N5 C16 C15 110.55(15) . . ? N5 C16 C17 120.96(19) . . ? C15 C16 C17 128.4(2) . . ? N6 C18 Cu2 174.8(2) . . ? N1 C4 C3 109.97(16) . . ? N1 C4 C5 121.01(18) . . ? C3 C4 C5 129.0(2) . . ? N7 C19 Cu3 175.0(2) . . ? C14 C15 C16 105.40(19) . . ? C14 C15 C12 126.14(17) . . ? C16 C15 C12 128.41(16) . . ? N2 C2 C3 105.40(15) . . ? N2 C2 C1 122.6(2) . . ? C3 C2 C1 132.0(2) . . ? N4 C14 C15 106.88(16) . . ? N4 C14 C13 122.2(2) . . ? C15 C14 C13 130.9(2) . . ? C11 C12 C15 115.46(17) . . ? C11 C12 H12A 108.4 . . ? C15 C12 H12A 108.4 . . ? C11 C12 H12B 108.4 . . ? C15 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C2 C3 C4 105.85(17) . . ? C2 C3 C6 126.74(16) . . ? C4 C3 C6 127.39(18) . . ? N3 C11 C10 120.88(19) . . ? N3 C11 C12 115.49(16) . . ? C10 C11 C12 123.6(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C7 C8 121.4(2) . . ? N3 C7 C6 114.68(16) . . ? C8 C7 C6 123.87(19) . . ? C3 C6 C7 116.03(17) . . ? C3 C6 H6A 108.3 . . ? C7 C6 H6A 108.3 . . ? C3 C6 H6B 108.3 . . ? C7 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C9 C8 C7 118.4(2) . . ? C9 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? C9 C10 C11 118.6(2) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C10 C9 C8 120.6(2) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? O2 C22 C21 114.5(6) . . ? O2 C22 H22A 108.7 . . ? C21 C22 H22A 108.7 . . ? O2 C22 H22B 108.6 . . ? C21 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 Cu3 N8 134.20(7) . . ? C19 Cu3 N3 121.60(6) . 1_556 ? N8 Cu3 N3 104.14(6) . 1_556 ? C20 N8 Cu3 173.8(2) . . ? N8 C20 Cu1 174.9(2) . 1_566 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.499 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.062 data_Cu-Ethanol-100K _database_code_depnum_ccdc_archive 'CCDC 918402' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 Cu3 N8 O2' _chemical_formula_weight 625.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.5152(3) _cell_length_b 11.3120(4) _cell_length_c 12.6953(4) _cell_angle_alpha 114.171(3) _cell_angle_beta 91.497(3) _cell_angle_gamma 68.347(3) _cell_volume 1386.93(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6653 _cell_measurement_theta_min 3.2223 _cell_measurement_theta_max 29.2907 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 634 _exptl_absorpt_coefficient_mu 2.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5957 _exptl_absorpt_correction_T_max 0.7532 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9785 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4889 _reflns_number_gt 4406 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4889 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1364 _refine_ls_wR_factor_gt 0.1306 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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 1.11949(2) -0.17140(2) -0.40603(2) 0.02137(7) Uani 1 1 d . . . N1 N 1.77149(16) 0.23978(18) -0.89787(15) 0.0237(4) Uani 1 1 d . . . O1 O 1.1154(3) 0.2545(3) -0.1212(2) 0.1423(9) Uani 1 1 d . . . C1 C 1.5916(2) 0.5339(3) -0.6224(2) 0.0461(8) Uani 1 1 d . . . H1A H 1.6535 0.5239 -0.5689 0.069 Uiso 1 1 calc R . . H1B H 1.5103 0.5467 -0.5878 0.069 Uiso 1 1 calc R . . H1C H 1.5814 0.6160 -0.6363 0.069 Uiso 1 1 calc R . . Cu2 Cu 0.94181(2) 0.13464(3) 0.00869(2) 0.02270(7) Uani 1 1 d . . . N2 N 1.74984(16) 0.35833(19) -0.79804(16) 0.0256(5) Uani 1 1 d . . . H2 H 1.8035 0.3997 -0.7771 0.031 Uiso 1 1 calc R . . O2 O 0.8383(3) 0.5151(4) 0.0301(3) 0.1310(15) Uani 1 1 d . . . C2 C 1.6363(2) 0.4055(2) -0.7345(2) 0.0297(6) Uani 1 1 d . . . Cu3 Cu 1.18194(2) 0.36024(2) 0.28921(2) 0.02006(7) Uani 1 1 d . . . N3 N 1.34428(15) 0.21531(17) -0.69300(15) 0.0216(4) Uani 1 1 d . . . C3 C 1.58182(19) 0.3120(2) -0.7978(2) 0.0292(6) Uani 1 1 d . . . N4 N 1.12964(15) 0.10101(17) -0.37094(16) 0.0244(5) Uani 1 1 d . . . H4 H 1.1078 0.1328 -0.2955 0.029 Uiso 1 1 calc R . . C4 C 1.6688(2) 0.2116(2) -0.8984(2) 0.0273(5) Uani 1 1 d . . . N5 N 1.15039(16) -0.03312(18) -0.45053(16) 0.0257(5) Uani 1 1 d . . . C5 C 1.6599(2) 0.0861(3) -0.9950(3) 0.0442(8) Uani 1 1 d . . . H5A H 1.7356 0.0375 -1.0536 0.066 Uiso 1 1 calc R . . H5B H 1.5849 0.1160 -1.0311 0.066 Uiso 1 1 calc R . . H5C H 1.6533 0.0221 -0.9640 0.066 Uiso 1 1 calc R . . N6 N 1.05413(17) -0.05960(18) -0.24308(15) 0.0252(5) Uani 1 1 d . . . C6 C 1.4553(2) 0.3168(2) -0.7642(2) 0.0366(6) Uani 1 1 d . . . H6A H 1.4120 0.2982 -0.8340 0.044 Uiso 1 1 calc R . . H6B H 1.4039 0.4136 -0.7055 0.044 Uiso 1 1 calc R . . N7 N 1.02602(16) 0.25937(19) 0.10563(16) 0.0277(5) Uani 1 1 d . . . C7 C 1.45813(19) 0.2148(2) -0.7151(2) 0.0282(6) Uani 1 1 d . . . N8 N 1.16389(16) 0.5339(2) 0.41813(17) 0.0299(5) Uani 1 1 d . . . C8 C 1.5658(2) 0.1271(3) -0.6927(3) 0.0502(7) Uani 1 1 d . . . H8 H 1.6459 0.1263 -0.7101 0.060 Uiso 1 1 calc R . . C9 C 1.5564(2) 0.0412(3) -0.6454(3) 0.0628(8) Uani 1 1 d . . . H9 H 1.6292 -0.0171 -0.6268 0.075 Uiso 1 1 calc R . . C10 C 1.4385(2) 0.0408(3) -0.6249(3) 0.0524(7) Uani 1 1 d . . . H10 H 1.4301 -0.0198 -0.5941 0.063 Uiso 1 1 calc R . . C11 C 1.3347(2) 0.1287(2) -0.6497(2) 0.0317(6) Uani 1 1 d . . . C12 C 1.2022(2) 0.1358(3) -0.6313(2) 0.0406(6) Uani 1 1 d . . . H12A H 1.1415 0.2336 -0.6099 0.049 Uiso 1 1 calc R . . H12B H 1.1846 0.0746 -0.7062 0.049 Uiso 1 1 calc R . . C13 C 1.1320(2) 0.3294(2) -0.3499(3) 0.0433(7) Uani 1 1 d . . . H13A H 1.0528 0.3820 -0.2954 0.065 Uiso 1 1 calc R . . H13B H 1.1309 0.3729 -0.4028 0.065 Uiso 1 1 calc R . . H13C H 1.2032 0.3308 -0.3061 0.065 Uiso 1 1 calc R . . C14 C 1.14619(19) 0.1779(2) -0.4203(2) 0.0297(6) Uani 1 1 d . . . C15 C 1.1785(2) 0.0924(2) -0.5392(2) 0.0327(6) Uani 1 1 d . . . C16 C 1.18092(19) -0.0377(2) -0.55325(19) 0.0280(5) Uani 1 1 d . . . C17 C 1.2103(2) -0.1688(3) -0.6636(2) 0.0388(7) Uani 1 1 d . . . H17A H 1.3000 -0.2079 -0.6949 0.058 Uiso 1 1 calc R . . H17B H 1.1588 -0.1466 -0.7209 0.058 Uiso 1 1 calc R . . H17C H 1.1914 -0.2380 -0.6476 0.058 Uiso 1 1 calc R . . C18 C 1.01102(19) 0.0070(2) -0.14624(19) 0.0223(5) Uani 1 1 d . . . C19 C 1.08652(19) 0.3021(2) 0.17254(18) 0.0217(5) Uani 1 1 d . . . C20 C 1.14982(19) 0.6436(2) 0.48843(19) 0.0246(5) Uani 1 1 d . . . C21 C 0.6094(6) 0.6266(9) 0.0573(9) 0.215(5) Uani 1 1 d . . . H21A H 0.5732 0.5923 0.1021 0.323 Uiso 1 1 calc R . . H21B H 0.5461 0.6650 0.0142 0.323 Uiso 1 1 calc R . . H21C H 0.6354 0.7007 0.1108 0.323 Uiso 1 1 calc R . . C22 C 0.7344(8) 0.4942(6) -0.0361(5) 0.213(3) Uani 1 1 d . . . H22A H 0.7317 0.4018 -0.0529 0.255 Uiso 1 1 calc R . . H22B H 0.7414 0.5022 -0.1103 0.255 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02751(12) 0.02040(10) 0.01648(12) 0.00558(9) -0.00094(9) -0.01223(10) N1 0.0224(8) 0.0268(7) 0.0239(8) 0.0112(6) -0.0008(7) -0.0114(7) O1 0.328(2) 0.1692(13) 0.0423(12) 0.0514(10) -0.0568(15) -0.2107(14) C1 0.0319(12) 0.0481(14) 0.0396(15) 0.0077(12) 0.0073(11) -0.0082(11) Cu2 0.02124(11) 0.02613(11) 0.01747(12) 0.00321(9) 0.00023(9) -0.01269(10) N2 0.0205(8) 0.0282(8) 0.0255(9) 0.0065(7) 0.0004(7) -0.0122(7) O2 0.137(3) 0.111(2) 0.143(3) 0.045(2) -0.034(2) -0.059(2) C2 0.0226(10) 0.0353(10) 0.0305(11) 0.0187(8) 0.0020(8) -0.0053(9) Cu3 0.01888(11) 0.02045(11) 0.01997(12) 0.00592(9) -0.00278(9) -0.00995(9) N3 0.0201(7) 0.0241(7) 0.0216(8) 0.0103(6) -0.0009(6) -0.0090(6) C3 0.0183(9) 0.0318(9) 0.0441(11) 0.0262(8) -0.0001(8) -0.0054(8) N4 0.0251(8) 0.0221(7) 0.0282(9) 0.0098(7) -0.0023(7) -0.0124(7) C4 0.0223(9) 0.0286(9) 0.0380(11) 0.0184(8) -0.0045(8) -0.0128(8) N5 0.0276(8) 0.0249(7) 0.0278(9) 0.0128(6) 0.0000(7) -0.0118(7) C5 0.0312(11) 0.0383(12) 0.0606(17) 0.0110(11) -0.0071(11) -0.0227(10) N6 0.0344(9) 0.0234(7) 0.0193(8) 0.0070(6) -0.0011(7) -0.0151(7) C6 0.0166(10) 0.0397(10) 0.0634(13) 0.0357(9) 0.0010(9) -0.0056(9) N7 0.0305(8) 0.0343(8) 0.0178(9) 0.0028(7) 0.0015(7) -0.0215(7) C7 0.0175(9) 0.0352(9) 0.0357(11) 0.0196(8) 0.0014(8) -0.0090(8) N8 0.0226(8) 0.0280(9) 0.0318(10) 0.0078(7) -0.0066(7) -0.0083(7) C8 0.0208(11) 0.0712(12) 0.0815(15) 0.0598(11) -0.0027(11) -0.0115(11) C9 0.0211(11) 0.0886(14) 0.1129(18) 0.0836(12) -0.0065(12) -0.0117(12) C10 0.0275(11) 0.0784(12) 0.0836(15) 0.0671(11) -0.0071(11) -0.0179(11) C11 0.0256(10) 0.0455(10) 0.0380(11) 0.0274(8) -0.0062(9) -0.0180(9) C12 0.0296(10) 0.0692(11) 0.0604(12) 0.0532(9) -0.0186(9) -0.0305(9) C13 0.0393(12) 0.0386(10) 0.0742(16) 0.0373(10) -0.0247(11) -0.0249(9) C14 0.0204(9) 0.0312(9) 0.0498(12) 0.0250(8) -0.0115(9) -0.0148(8) C15 0.0201(9) 0.0512(10) 0.0456(11) 0.0345(9) -0.0098(8) -0.0186(8) C16 0.0204(9) 0.0429(10) 0.0297(10) 0.0225(8) -0.0020(8) -0.0139(8) C17 0.0381(12) 0.0493(12) 0.0308(12) 0.0210(9) 0.0012(10) -0.0143(11) C18 0.0218(9) 0.0275(8) 0.0224(10) 0.0110(7) -0.0055(8) -0.0146(8) C19 0.0260(9) 0.0205(8) 0.0194(10) 0.0075(7) -0.0004(8) -0.0111(8) C20 0.0225(9) 0.0258(9) 0.0239(10) 0.0084(8) -0.0034(8) -0.0104(8) C21 0.099(5) 0.200(7) 0.335(11) 0.135(7) -0.027(6) -0.022(5) C22 0.470(7) 0.147(3) 0.136(3) 0.111(2) -0.204(4) -0.196(4) _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 C20 1.867(2) 1_544 ? Cu1 N6 1.9188(17) . ? Cu1 N5 2.009(2) . ? N1 C4 1.333(3) . ? N1 N2 1.358(2) . ? N1 Cu2 1.9781(16) 1_654 ? C1 C2 1.481(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? Cu2 C18 1.870(2) . ? Cu2 N1 1.9781(16) 1_456 ? Cu2 N7 1.9928(19) . ? Cu2 Cu2 2.7524(5) 2_755 ? N2 C2 1.354(3) . ? N2 H2 0.8800 . ? O2 C22 1.480(8) . ? C2 C3 1.388(3) . ? Cu3 C19 1.867(2) . ? Cu3 N8 1.9138(19) . ? Cu3 N3 2.0622(17) 1_556 ? N3 C11 1.341(3) . ? N3 C7 1.345(3) . ? N3 Cu3 2.0622(17) 1_554 ? C3 C4 1.401(3) . ? C3 C6 1.504(3) . ? N4 C14 1.327(3) . ? N4 N5 1.367(2) . ? N4 H4 0.8800 . ? C4 C5 1.484(3) . ? N5 C16 1.335(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? N6 C18 1.150(3) . ? C6 C7 1.511(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N7 C19 1.150(3) . ? C7 C8 1.381(3) . ? N8 C20 1.147(3) . ? C8 C9 1.370(4) . ? C8 H8 0.9500 . ? C9 C10 1.391(4) . ? C9 H9 0.9500 . ? C10 C11 1.370(4) . ? C10 H10 0.9500 . ? C11 C12 1.517(3) . ? C12 C15 1.506(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.519(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.385(3) . ? C15 C16 1.398(4) . ? C16 C17 1.493(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C20 Cu1 1.867(2) 1_566 ? C21 C22 1.663(9) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 C20 Cu1 N6 134.61(10) 1_544 . ? C20 Cu1 N5 123.56(9) 1_544 . ? N6 Cu1 N5 101.82(8) . . ? C4 N1 N2 105.66(16) . . ? C4 N1 Cu2 134.22(14) . 1_654 ? N2 N1 Cu2 119.22(14) . 1_654 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C18 Cu2 N1 136.55(8) . 1_456 ? C18 Cu2 N7 120.64(9) . . ? N1 Cu2 N7 98.92(7) 1_456 . ? C18 Cu2 Cu2 69.75(7) . 2_755 ? N1 Cu2 Cu2 113.68(6) 1_456 2_755 ? N7 Cu2 Cu2 111.80(6) . 2_755 ? C2 N2 N1 112.28(19) . . ? C2 N2 H2 123.9 . . ? N1 N2 H2 123.9 . . ? N2 C2 C3 105.58(18) . . ? N2 C2 C1 122.0(2) . . ? C3 C2 C1 132.4(2) . . ? C19 Cu3 N8 135.82(8) . . ? C19 Cu3 N3 120.51(8) . 1_556 ? N8 Cu3 N3 103.48(8) . 1_556 ? C11 N3 C7 119.86(19) . . ? C11 N3 Cu3 119.17(14) . 1_554 ? C7 N3 Cu3 120.75(16) . 1_554 ? C2 C3 C4 106.3(2) . . ? C2 C3 C6 126.70(19) . . ? C4 C3 C6 127.0(2) . . ? C14 N4 N5 112.40(18) . . ? C14 N4 H4 123.8 . . ? N5 N4 H4 123.8 . . ? N1 C4 C3 110.2(2) . . ? N1 C4 C5 120.74(19) . . ? C3 C4 C5 129.0(2) . . ? C16 N5 N4 104.76(19) . . ? C16 N5 Cu1 132.64(16) . . ? N4 N5 Cu1 122.34(15) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C18 N6 Cu1 177.62(19) . . ? C3 C6 C7 115.77(19) . . ? C3 C6 H6A 108.3 . . ? C7 C6 H6A 108.3 . . ? C3 C6 H6B 108.3 . . ? C7 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C19 N7 Cu2 160.6(2) . . ? N3 C7 C8 120.9(2) . . ? N3 C7 C6 114.30(19) . . ? C8 C7 C6 124.8(2) . . ? C20 N8 Cu3 173.7(2) . . ? C9 C8 C7 119.6(2) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 118.9(3) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 119.2(3) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? N3 C11 C10 121.4(2) . . ? N3 C11 C12 115.2(2) . . ? C10 C11 C12 123.4(2) . . ? C15 C12 C11 115.3(2) . . ? C15 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C15 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C14 C15 106.7(2) . . ? N4 C14 C13 122.4(2) . . ? C15 C14 C13 130.8(2) . . ? C14 C15 C16 105.4(2) . . ? C14 C15 C12 125.9(2) . . ? C16 C15 C12 128.7(2) . . ? N5 C16 C15 110.7(2) . . ? N5 C16 C17 121.0(2) . . ? C15 C16 C17 128.3(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N6 C18 Cu2 172.7(2) . . ? N7 C19 Cu3 173.7(2) . . ? N8 C20 Cu1 175.0(2) . 1_566 ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 C22 C21 101.0(5) . . ? O2 C22 H22A 111.6 . . ? C21 C22 H22A 111.6 . . ? O2 C22 H22B 111.6 . . ? C21 C22 H22B 111.6 . . ? H22A C22 H22B 109.4 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.101 _refine_diff_density_min -0.913 _refine_diff_density_rms 0.090 data_Cu-THF _database_code_depnum_ccdc_archive 'CCDC 918403' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H29 Cu3 N8 O2' _chemical_formula_weight 652.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4723(7) _cell_length_b 11.4569(7) _cell_length_c 13.1199(8) _cell_angle_alpha 64.295(6) _cell_angle_beta 89.824(5) _cell_angle_gamma 110.147(6) _cell_volume 1434.82(15) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4541 _cell_measurement_theta_min 2.8191 _cell_measurement_theta_max 29.4730 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 2.238 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5438 _exptl_absorpt_correction_T_max 0.8072 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10456 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5056 _reflns_number_gt 4055 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0658P)^2^+0.1426P] 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 5056 _refine_ls_number_parameters 338 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.042 _refine_ls_shift/su_mean 0.002 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 1.1509(5) -0.2237(5) 0.8757(3) 0.352(3) Uani 1 1 d . . . N1 N 0.78041(15) 0.76990(15) 0.10310(12) 0.0541(5) Uani 1 1 d . . . C1 C 0.5973(3) 0.4840(3) 0.3816(2) 0.1022(12) Uani 1 1 d . . . H1A H 0.6607 0.4449 0.4010 0.153 Uiso 1 1 calc R . . H1B H 0.5215 0.4154 0.3796 0.153 Uiso 1 1 calc R . . H1C H 0.5799 0.5103 0.4384 0.153 Uiso 1 1 calc R . . Cu1 Cu 0.12028(2) 1.17083(2) 0.591077(17) 0.04936(7) Uani 1 1 d . . . O2 O 1.2498(4) -0.3475(4) 0.9624(4) 0.573(6) Uani 1 1 d D . . N2 N 0.75726(16) 0.65518(16) 0.20503(12) 0.0586(5) Uani 1 1 d . . . H2 H 0.8099 0.6151 0.2281 0.070 Uiso 1 1 calc R . . C2 C 0.6435(2) 0.6106(2) 0.26627(16) 0.0616(6) Uani 1 1 d . . . Cu2 Cu -0.04955(2) 0.86103(2) 1.004737(18) 0.05659(8) Uani 1 1 d . . . N3 N 0.34412(14) 0.78515(13) 0.31273(11) 0.0443(4) Uani 1 1 d . . . C3 C 0.58778(19) 0.69935(19) 0.20138(15) 0.0582(6) Uani 1 1 d . . . Cu3 Cu 0.18393(2) 0.64504(2) 1.295807(17) 0.04615(7) Uani 1 1 d . . . N4 N 0.12711(15) 0.90003(14) 0.63048(13) 0.0537(5) Uani 1 1 d . . . H4 H 0.1051 0.8710 0.7027 0.064 Uiso 1 1 calc R . . C4 C 0.6767(2) 0.79754(19) 0.10029(17) 0.0582(6) Uani 1 1 d . . . N5 N 0.15077(15) 1.03225(14) 0.54874(12) 0.0484(4) Uani 1 1 d . . . C5 C 0.6676(3) 0.9214(2) -0.0011(2) 0.0958(11) Uani 1 1 d . . . H5A H 0.7141 1.0056 0.0040 0.144 Uiso 1 1 calc R . . H5B H 0.5807 0.9100 -0.0011 0.144 Uiso 1 1 calc R . . H5C H 0.7022 0.9278 -0.0709 0.144 Uiso 1 1 calc R . . C6 C 0.4608(2) 0.6967(2) 0.23284(18) 0.0709(7) Uani 1 1 d . . . H6A H 0.4067 0.6008 0.2860 0.085 Uiso 1 1 calc R . . H6B H 0.4240 0.7243 0.1639 0.085 Uiso 1 1 calc R . . N6 N 0.05570(18) 1.05242(16) 0.75345(12) 0.0614(5) Uani 1 1 d . . . C7 C 0.45985(18) 0.78941(18) 0.28651(15) 0.0532(6) Uani 1 1 d . . . N7 N 0.03235(16) 0.74494(16) 1.11408(13) 0.0590(5) Uani 1 1 d . . . C8 C 0.5648(2) 0.8695(2) 0.3096(2) 0.0841(8) Uani 1 1 d . . . H8 H 0.6437 0.8708 0.2913 0.101 Uiso 1 1 calc R . . N8 N 0.16642(18) 0.46710(16) 1.41946(14) 0.0651(6) Uani 1 1 d . . . C9 C 0.5518(2) 0.9487(2) 0.3604(2) 0.0989(8) Uani 1 1 d . . . H9 H 0.6221 1.0034 0.3772 0.119 Uiso 1 1 calc R . . C10 C 0.4350(2) 0.9461(2) 0.3859(2) 0.0845(7) Uani 1 1 d . . . H10 H 0.4254 0.9999 0.4192 0.101 Uiso 1 1 calc R . . C11 C 0.33179(19) 0.86310(18) 0.36168(16) 0.0566(6) Uani 1 1 d . . . C12 C 0.1995(2) 0.8548(2) 0.38385(18) 0.0743(6) Uani 1 1 d . . . H12A H 0.1802 0.9123 0.3116 0.089 Uiso 1 1 calc R . . H12B H 0.1415 0.7587 0.4098 0.089 Uiso 1 1 calc R . . C13 C 0.1235(3) 0.6676(2) 0.6613(2) 0.0937(10) Uani 1 1 d . . . H13A H 0.1658 0.6602 0.7255 0.141 Uiso 1 1 calc R . . H13B H 0.1579 0.6351 0.6169 0.141 Uiso 1 1 calc R . . H13C H 0.0350 0.6113 0.6889 0.141 Uiso 1 1 calc R . . C14 C 0.1418(2) 0.81948(19) 0.58654(18) 0.0602(6) Uani 1 1 d . . . C15 C 0.17551(18) 0.90046(18) 0.47059(17) 0.0572(6) Uani 1 1 d . . . C16 C 0.18030(18) 1.03329(18) 0.44991(15) 0.0504(5) Uani 1 1 d . . . C17 C 0.2139(2) 1.1638(2) 0.33917(16) 0.0749(8) Uani 1 1 d . . . H17A H 0.1932 1.2318 0.3511 0.112 Uiso 1 1 calc R . . H17B H 0.1676 1.1430 0.2843 0.112 Uiso 1 1 calc R . . H17C H 0.3028 1.2008 0.3106 0.112 Uiso 1 1 calc R . . C18 C 0.0145(2) 0.98338(19) 0.84877(15) 0.0556(6) Uani 1 1 d . . . C19 C 0.09003(18) 0.70382(17) 1.18121(14) 0.0467(5) Uani 1 1 d . . . C20 C 0.1515(2) 0.35645(18) 1.48797(15) 0.0536(6) Uani 1 1 d . . . C21 C 1.1990(4) -0.5028(5) 1.0364(6) 0.401(7) Uani 1 1 d D . . H21A H 1.1516 -0.5299 1.1098 0.482 Uiso 1 1 calc R . . H21B H 1.1459 -0.5518 0.9986 0.482 Uiso 1 1 calc R . . C22 C 1.3157(4) -0.5293(5) 1.0502(4) 0.406(9) Uani 1 1 d D . . H22A H 1.3017 -0.6217 1.0585 0.488 Uiso 1 1 calc R . . H22B H 1.3457 -0.5238 1.1177 0.488 Uiso 1 1 calc R . . C23 C 1.4079(4) -0.4200(6) 0.9455(5) 0.471(10) Uani 1 1 d D . . H23A H 1.4807 -0.3641 0.9645 0.565 Uiso 1 1 calc R . . H23B H 1.4362 -0.4618 0.9051 0.565 Uiso 1 1 calc R . . C24 C 1.3431(5) -0.3344(5) 0.8756(3) 0.384(7) Uani 1 1 d D . . H24A H 1.3016 -0.3698 0.8247 0.461 Uiso 1 1 calc R . . H24B H 1.4008 -0.2377 0.8301 0.461 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.485(6) 0.452(5) 0.163(3) -0.084(3) -0.029(4) 0.305(4) N1 0.0442(8) 0.0600(7) 0.0549(7) -0.0187(5) -0.0031(6) 0.0270(6) C1 0.0756(18) 0.1190(19) 0.0665(13) -0.0127(12) 0.0183(13) 0.0265(15) Cu1 0.05328(13) 0.04326(9) 0.04509(9) -0.01346(7) -0.00381(9) 0.02055(9) O2 0.919(14) 0.444(6) 0.380(7) -0.135(5) 0.089(9) 0.363(8) N2 0.0422(8) 0.0724(8) 0.0514(7) -0.0160(6) 0.0027(7) 0.0278(7) C2 0.0455(11) 0.0806(10) 0.0578(9) -0.0325(7) 0.0009(8) 0.0226(9) Cu2 0.04592(13) 0.06487(12) 0.04149(10) -0.00960(8) -0.00290(9) 0.02152(10) N3 0.0286(7) 0.0481(6) 0.0585(6) -0.0265(5) -0.0065(6) 0.0148(5) C3 0.0380(10) 0.0726(8) 0.0765(9) -0.0464(7) -0.0051(8) 0.0196(8) Cu3 0.03923(12) 0.04349(9) 0.05411(10) -0.01941(7) -0.01281(9) 0.01819(8) N4 0.0463(9) 0.0410(6) 0.0617(8) -0.0171(5) 0.0018(7) 0.0121(6) C4 0.0420(11) 0.0623(8) 0.0774(10) -0.0354(7) -0.0152(9) 0.0240(8) N5 0.0430(8) 0.0440(6) 0.0531(7) -0.0190(5) 0.0005(6) 0.0156(6) C5 0.0661(15) 0.0752(13) 0.1203(19) -0.0167(13) -0.0207(14) 0.0361(11) C6 0.0352(11) 0.0898(9) 0.1107(11) -0.0699(8) -0.0070(9) 0.0190(9) N6 0.0708(11) 0.0615(7) 0.0433(7) -0.0159(5) -0.0017(7) 0.0269(7) C7 0.0300(9) 0.0626(8) 0.0759(9) -0.0406(6) -0.0090(8) 0.0165(7) N7 0.0492(9) 0.0699(8) 0.0515(7) -0.0168(6) -0.0096(7) 0.0306(7) C8 0.0292(11) 0.1208(12) 0.1308(13) -0.0874(9) -0.0090(10) 0.0221(10) N8 0.0613(11) 0.0476(7) 0.0702(9) -0.0152(6) -0.0209(8) 0.0188(7) C9 0.0363(13) 0.1432(12) 0.1696(13) -0.1272(9) -0.0250(11) 0.0212(11) C10 0.0417(12) 0.1183(10) 0.1421(11) -0.1042(8) -0.0205(10) 0.0275(10) C11 0.0334(10) 0.0686(8) 0.0855(9) -0.0508(7) -0.0125(8) 0.0196(7) C12 0.0438(11) 0.0995(9) 0.1219(11) -0.0830(7) -0.0224(9) 0.0328(9) C13 0.0850(17) 0.0600(10) 0.1457(18) -0.0506(11) -0.0408(15) 0.0346(11) C14 0.0369(10) 0.0503(8) 0.0958(11) -0.0362(8) -0.0170(9) 0.0164(8) C15 0.0315(10) 0.0690(8) 0.0907(9) -0.0524(6) -0.0126(8) 0.0207(7) C16 0.0362(10) 0.0582(8) 0.0597(8) -0.0304(6) -0.0031(7) 0.0174(7) C17 0.0764(16) 0.0810(11) 0.0597(10) -0.0306(8) 0.0013(10) 0.0243(11) C18 0.0505(11) 0.0611(9) 0.0496(8) -0.0171(7) -0.0066(8) 0.0264(8) C19 0.0385(10) 0.0423(7) 0.0523(8) -0.0161(6) -0.0052(7) 0.0152(7) C20 0.0551(12) 0.0471(8) 0.0531(8) -0.0182(6) -0.0109(8) 0.0202(8) C21 0.308(10) 0.259(7) 0.610(15) -0.168(8) -0.023(11) 0.124(7) C22 0.528(19) 0.300(10) 0.164(5) -0.038(6) -0.032(8) -0.003(12) C23 0.459(17) 0.381(14) 0.252(9) 0.016(9) -0.094(10) 0.015(13) C24 0.668(18) 0.318(7) 0.173(5) -0.108(5) -0.041(8) 0.203(10) _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 N1 C4 1.329(3) . ? N1 N2 1.3488(19) . ? N1 Cu2 1.9933(15) 1_654 ? C1 C2 1.495(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? Cu1 C20 1.8596(17) 1_564 ? Cu1 N6 1.9283(14) . ? Cu1 N5 2.0244(18) . ? O2 C24 1.483(6) . ? O2 C21 1.494(5) . ? N2 C2 1.337(3) . ? N2 H2 0.8600 . ? C2 C3 1.367(3) . ? Cu2 C18 1.8668(17) . ? Cu2 N7 1.9808(17) . ? Cu2 N1 1.9933(16) 1_456 ? Cu2 Cu2 2.9342(6) 2_577 ? N3 C11 1.347(3) . ? N3 C7 1.350(3) . ? N3 Cu3 2.0694(15) 1_554 ? C3 C4 1.404(2) . ? C3 C6 1.500(3) . ? Cu3 C19 1.872(2) . ? Cu3 N8 1.9171(15) . ? Cu3 N3 2.0694(15) 1_556 ? N4 C14 1.334(3) . ? N4 N5 1.3506(18) . ? N4 H4 0.8600 . ? C4 C5 1.503(3) . ? N5 C16 1.333(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.511(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N6 C18 1.138(2) . ? C7 C8 1.366(3) . ? N7 C19 1.138(3) . ? C8 C9 1.380(4) . ? C8 H8 0.9300 . ? N8 C20 1.142(2) . ? C9 C10 1.368(4) . ? C9 H9 0.9300 . ? C10 C11 1.377(3) . ? C10 H10 0.9300 . ? C11 C12 1.507(3) . ? C12 C15 1.503(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.517(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.360(3) . ? C15 C16 1.406(3) . ? C16 C17 1.486(2) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C20 Cu1 1.8596(17) 1_546 ? C21 C22 1.467(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.470(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.443(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 N2 104.84(14) . . ? C4 N1 Cu2 136.35(11) . 1_654 ? N2 N1 Cu2 118.60(14) . 1_654 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C20 Cu1 N6 135.46(9) 1_564 . ? C20 Cu1 N5 124.70(8) 1_564 . ? N6 Cu1 N5 99.84(7) . . ? C24 O2 C21 99.4(4) . . ? C2 N2 N1 112.66(18) . . ? C2 N2 H2 123.7 . . ? N1 N2 H2 123.7 . . ? N2 C2 C3 106.53(15) . . ? N2 C2 C1 121.9(2) . . ? C3 C2 C1 131.6(2) . . ? C18 Cu2 N7 126.07(9) . . ? C18 Cu2 N1 134.42(8) . 1_456 ? N7 Cu2 N1 97.97(6) . 1_456 ? C18 Cu2 Cu2 76.39(7) . 2_577 ? N7 Cu2 Cu2 108.01(6) . 2_577 ? N1 Cu2 Cu2 102.95(5) 1_456 2_577 ? C11 N3 C7 119.24(17) . . ? C11 N3 Cu3 119.34(13) . 1_554 ? C7 N3 Cu3 121.07(14) . 1_554 ? C2 C3 C4 105.44(19) . . ? C2 C3 C6 127.54(16) . . ? C4 C3 C6 126.98(19) . . ? C19 Cu3 N8 134.29(8) . . ? C19 Cu3 N3 122.02(6) . 1_556 ? N8 Cu3 N3 103.67(7) . 1_556 ? C14 N4 N5 112.38(15) . . ? C14 N4 H4 123.8 . . ? N5 N4 H4 123.8 . . ? N1 C4 C3 110.52(17) . . ? N1 C4 C5 120.54(18) . . ? C3 C4 C5 128.9(2) . . ? C16 N5 N4 104.90(16) . . ? C16 N5 Cu1 134.50(12) . . ? N4 N5 Cu1 120.23(12) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 C7 115.75(18) . . ? C3 C6 H6A 108.3 . . ? C7 C6 H6A 108.3 . . ? C3 C6 H6B 108.3 . . ? C7 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C18 N6 Cu1 178.0(2) . . ? N3 C7 C8 121.7(2) . . ? N3 C7 C6 114.05(17) . . ? C8 C7 C6 124.3(2) . . ? C19 N7 Cu2 164.53(18) . . ? C7 C8 C9 119.0(2) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C20 N8 Cu3 174.66(19) . . ? C10 C9 C8 119.6(2) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 119.4(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? N3 C11 C10 121.1(2) . . ? N3 C11 C12 115.13(18) . . ? C10 C11 C12 123.8(2) . . ? C15 C12 C11 115.56(19) . . ? C15 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C15 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C14 C15 106.99(17) . . ? N4 C14 C13 122.3(2) . . ? C15 C14 C13 130.7(2) . . ? C14 C15 C16 105.53(19) . . ? C14 C15 C12 126.61(19) . . ? C16 C15 C12 127.85(16) . . ? N5 C16 C15 110.19(15) . . ? N5 C16 C17 120.48(19) . . ? C15 C16 C17 129.3(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N6 C18 Cu2 176.1(2) . . ? N7 C19 Cu3 175.8(2) . . ? N8 C20 Cu1 175.1(2) . 1_546 ? C22 C21 O2 101.3(3) . . ? C22 C21 H21A 111.5 . . ? O2 C21 H21A 111.5 . . ? C22 C21 H21B 111.5 . . ? O2 C21 H21B 111.5 . . ? H21A C21 H21B 109.3 . . ? C21 C22 C23 106.0(4) . . ? C21 C22 H22A 110.5 . . ? C23 C22 H22A 110.5 . . ? C21 C22 H22B 110.5 . . ? C23 C22 H22B 110.5 . . ? H22A C22 H22B 108.7 . . ? C24 C23 C22 106.0(4) . . ? C24 C23 H23A 110.5 . . ? C22 C23 H23A 110.5 . . ? C24 C23 H23B 110.5 . . ? C22 C23 H23B 110.5 . . ? H23A C23 H23B 108.7 . . ? C23 C24 O2 102.7(4) . . ? C23 C24 H24A 111.2 . . ? O2 C24 H24A 111.2 . . ? C23 C24 H24B 111.2 . . ? O2 C24 H24B 111.2 . . ? H24A C24 H24B 109.1 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.699 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.067 data_Cu-Cyclohexane _database_code_depnum_ccdc_archive 'CCDC 918404' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H33 Cu3 N8' _chemical_formula_weight 648.22 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 11.4507(6) _cell_length_b 11.6026(5) _cell_length_c 13.2025(7) _cell_angle_alpha 65.360(5) _cell_angle_beta 71.368(5) _cell_angle_gamma 71.461(4) _cell_volume 1475.61(12) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3097 _cell_measurement_theta_min 2.8521 _cell_measurement_theta_max 29.4261 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 2.171 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6129 _exptl_absorpt_correction_T_max 0.8808 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10464 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5185 _reflns_number_gt 3603 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0605P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5185 _refine_ls_number_parameters 338 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1263 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.034 _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 N1 N 0.2938(3) 0.1167(4) -0.3911(4) 0.0499(10) Uani 1 1 d . . . C1 C 0.1089(6) 0.1230(8) -0.1103(6) 0.098(2) Uani 1 1 d . . . H1A H 0.1507 0.0478 -0.0571 0.146 Uiso 1 1 calc R . . H1B H 0.0196 0.1278 -0.0870 0.146 Uiso 1 1 calc R . . H1C H 0.1263 0.1996 -0.1120 0.146 Uiso 1 1 calc R . . Cu1 Cu -0.38203(5) -0.75598(6) 0.08878(5) 0.0484(2) Uani 1 1 d . . . N2 N 0.2707(3) 0.1279(4) -0.2878(4) 0.0563(11) Uani 1 1 d . . . H2 H 0.3248 0.1427 -0.2647 0.068 Uiso 1 1 calc R . . C2 C 0.1559(4) 0.1136(5) -0.2263(5) 0.0552(14) Uani 1 1 d . . . Cu2 Cu -0.53619(5) -0.86368(6) 0.50565(5) 0.0513(2) Uani 1 1 d . . . N3 N -0.1517(3) -0.1027(3) -0.1774(3) 0.0390(9) Uani 1 1 d . . . C3 C 0.0989(4) 0.0910(5) -0.2913(5) 0.0526(13) Uani 1 1 d . . . Cu3 Cu -0.30981(5) -0.95167(5) 0.80240(5) 0.04526(19) Uani 1 1 d . . . N4 N -0.3855(3) -0.5261(4) 0.1307(4) 0.0504(11) Uani 1 1 d . . . H4 H -0.4120 -0.5685 0.2016 0.060 Uiso 1 1 calc R . . C4 C 0.1878(4) 0.0951(5) -0.3939(5) 0.0513(13) Uani 1 1 d . . . N5 N -0.3542(3) -0.5757(4) 0.0461(4) 0.0456(10) Uani 1 1 d . . . C5 C 0.1783(5) 0.0744(7) -0.4933(6) 0.090(2) Uani 1 1 d . . . H5A H 0.2004 0.1454 -0.5614 0.135 Uiso 1 1 calc R . . H5B H 0.0934 0.0693 -0.4846 0.135 Uiso 1 1 calc R . . H5C H 0.2349 -0.0051 -0.4987 0.135 Uiso 1 1 calc R . . C6 C -0.0307(4) 0.0626(5) -0.2570(5) 0.0648(17) Uani 1 1 d . . . H6A H -0.0845 0.1073 -0.2051 0.078 Uiso 1 1 calc R . . H6B H -0.0656 0.0986 -0.3245 0.078 Uiso 1 1 calc R . . N6 N -0.4451(4) -0.7927(4) 0.2510(4) 0.0601(12) Uani 1 1 d . . . C7 C -0.0360(4) -0.0775(4) -0.2012(4) 0.0482(13) Uani 1 1 d . . . N7 N -0.4538(4) -0.8773(4) 0.6214(4) 0.0579(12) Uani 1 1 d . . . C8 C 0.0662(4) -0.1775(5) -0.1741(5) 0.0683(18) Uani 1 1 d . . . H8 H 0.1455 -0.1599 -0.1910 0.082 Uiso 1 1 calc R . . N8 N -0.3319(4) -0.8900(5) 0.9231(4) 0.0624(12) Uani 1 1 d . . . C9 C 0.0504(4) -0.3023(5) -0.1224(6) 0.077(2) Uani 1 1 d . . . H9 H 0.1188 -0.3703 -0.1039 0.093 Uiso 1 1 calc R . . C10 C -0.0668(4) -0.3272(5) -0.0979(6) 0.0690(18) Uani 1 1 d . . . H10 H -0.0786 -0.4120 -0.0626 0.083 Uiso 1 1 calc R . . C11 C -0.1668(4) -0.2249(5) -0.1264(5) 0.0505(13) Uani 1 1 d . . . C12 C -0.2983(4) -0.2414(5) -0.1083(6) 0.0720(19) Uani 1 1 d . . . H12A H -0.3124 -0.2278 -0.1814 0.086 Uiso 1 1 calc R . . H12B H -0.3581 -0.1742 -0.0813 0.086 Uiso 1 1 calc R . . C13 C -0.3987(6) -0.3281(6) 0.1676(7) 0.085(2) Uani 1 1 d . . . H13A H -0.4764 -0.3421 0.2223 0.128 Uiso 1 1 calc R . . H13B H -0.4065 -0.2373 0.1229 0.128 Uiso 1 1 calc R . . H13C H -0.3315 -0.3566 0.2070 0.128 Uiso 1 1 calc R . . C14 C -0.3701(4) -0.4037(5) 0.0908(6) 0.0551(14) Uani 1 1 d . . . C15 C -0.3258(4) -0.3713(5) -0.0254(5) 0.0541(14) Uani 1 1 d . . . C16 C -0.3187(4) -0.4808(5) -0.0487(5) 0.0501(13) Uani 1 1 d . . . C17 C -0.2754(5) -0.4985(6) -0.1611(5) 0.0719(17) Uani 1 1 d . . . H17A H -0.1865 -0.5009 -0.1880 0.108 Uiso 1 1 calc R . . H17B H -0.3201 -0.4276 -0.2149 0.108 Uiso 1 1 calc R . . H17C H -0.2915 -0.5786 -0.1529 0.108 Uiso 1 1 calc R . . C18 C -0.4808(4) -0.8203(5) 0.3478(5) 0.0509(12) Uani 1 1 d . . . C19 C -0.3994(4) -0.9033(4) 0.6902(4) 0.0442(11) Uani 1 1 d . . . C20 C -0.3487(4) -0.8426(5) 0.9891(5) 0.0512(13) Uani 1 1 d . . . C21 C 1.1051(15) -0.417(2) -0.3607(15) 0.358(16) Uani 1 1 d D . . H21A H 1.1296 -0.4845 -0.2922 0.430 Uiso 1 1 calc R . . H21B H 1.0252 -0.3630 -0.3375 0.430 Uiso 1 1 calc R . . C22 C 1.0870(15) -0.479(2) -0.431(2) 0.369(16) Uani 1 1 d D . . H22A H 1.0071 -0.4342 -0.4542 0.443 Uiso 1 1 calc R . . H22B H 1.0809 -0.5679 -0.3841 0.443 Uiso 1 1 calc R . . C23 C 1.190(2) -0.480(2) -0.5383(18) 0.394(18) Uani 1 1 d D . . H23A H 1.1891 -0.5484 -0.5616 0.473 Uiso 1 1 calc R . . H23B H 1.1730 -0.3978 -0.5997 0.473 Uiso 1 1 calc R . . C24 C 1.3189(14) -0.5003(17) -0.5189(17) 0.300(12) Uani 1 1 d D . . H24A H 1.3797 -0.4921 -0.5908 0.360 Uiso 1 1 calc R . . H24B H 1.3412 -0.5882 -0.4667 0.360 Uiso 1 1 calc R . . C25 C 1.3291(14) -0.4072(18) -0.471(2) 0.348(15) Uani 1 1 d D . . H25A H 1.3770 -0.4555 -0.4119 0.417 Uiso 1 1 calc R . . H25B H 1.3762 -0.3449 -0.5315 0.417 Uiso 1 1 calc R . . C26 C 1.205(2) -0.3342(15) -0.4222(17) 0.321(14) Uani 1 1 d D . . H26A H 1.1739 -0.2586 -0.4834 0.385 Uiso 1 1 calc R . . H26B H 1.2174 -0.3041 -0.3690 0.385 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.041(2) 0.062(3) 0.052(3) -0.022(2) -0.0069(18) -0.0179(17) C1 0.073(4) 0.148(7) 0.057(5) -0.031(5) 0.002(3) -0.028(4) Cu1 0.0545(4) 0.0549(4) 0.0438(4) -0.0243(3) -0.0072(3) -0.0162(3) N2 0.043(2) 0.085(3) 0.045(3) -0.019(2) -0.0043(19) -0.030(2) C2 0.049(3) 0.064(4) 0.044(4) -0.014(3) 0.000(2) -0.018(2) Cu2 0.0461(3) 0.0706(4) 0.0375(4) -0.0186(3) -0.0050(3) -0.0174(3) N3 0.0321(19) 0.046(2) 0.041(3) -0.0165(19) -0.0070(16) -0.0093(15) C3 0.044(3) 0.050(3) 0.061(4) -0.014(3) -0.008(2) -0.018(2) Cu3 0.0429(3) 0.0507(4) 0.0497(4) -0.0229(3) -0.0153(3) -0.0074(2) N4 0.052(2) 0.054(3) 0.050(3) -0.023(2) -0.0069(19) -0.0146(18) C4 0.041(3) 0.059(3) 0.059(4) -0.025(3) -0.013(2) -0.009(2) N5 0.045(2) 0.052(3) 0.044(3) -0.021(2) -0.0025(18) -0.0160(17) C5 0.061(4) 0.136(6) 0.110(6) -0.084(5) -0.025(3) -0.008(3) C6 0.038(3) 0.055(3) 0.091(5) -0.015(3) -0.008(3) -0.018(2) N6 0.084(3) 0.061(3) 0.040(3) -0.017(2) -0.005(2) -0.031(2) C7 0.034(2) 0.049(3) 0.057(4) -0.014(3) -0.008(2) -0.011(2) N7 0.051(2) 0.087(3) 0.046(3) -0.025(3) -0.008(2) -0.028(2) C8 0.033(3) 0.058(4) 0.099(5) -0.010(3) -0.014(3) -0.014(2) N8 0.060(3) 0.075(3) 0.066(3) -0.041(3) -0.024(2) 0.000(2) C9 0.038(3) 0.052(4) 0.113(6) -0.005(3) -0.020(3) -0.004(2) C10 0.050(3) 0.044(3) 0.101(5) -0.005(3) -0.026(3) -0.012(2) C11 0.038(3) 0.043(3) 0.065(4) -0.010(3) -0.014(2) -0.012(2) C12 0.048(3) 0.057(3) 0.105(6) -0.009(3) -0.026(3) -0.021(2) C13 0.087(4) 0.072(4) 0.122(7) -0.056(4) -0.042(4) -0.001(3) C14 0.045(3) 0.048(3) 0.084(5) -0.031(3) -0.020(3) -0.006(2) C15 0.037(3) 0.049(3) 0.076(5) -0.018(3) -0.013(3) -0.014(2) C16 0.040(3) 0.054(3) 0.052(4) -0.013(3) -0.006(2) -0.017(2) C17 0.071(4) 0.076(4) 0.063(5) -0.021(3) -0.001(3) -0.027(3) C18 0.056(3) 0.058(3) 0.043(4) -0.016(3) -0.011(2) -0.021(2) C19 0.039(2) 0.050(3) 0.047(3) -0.023(3) -0.008(2) -0.0076(19) C20 0.052(3) 0.057(3) 0.049(4) -0.025(3) -0.011(2) -0.008(2) C21 0.208(18) 0.62(5) 0.33(3) -0.30(4) 0.056(18) -0.13(2) C22 0.32(3) 0.63(5) 0.33(3) -0.29(3) 0.00(2) -0.22(3) C23 0.27(2) 0.65(5) 0.35(3) -0.38(4) -0.05(2) 0.07(3) C24 0.168(14) 0.33(3) 0.43(3) -0.23(2) 0.047(16) -0.056(14) C25 0.37(3) 0.190(18) 0.47(4) -0.09(2) -0.03(3) -0.15(2) C26 0.37(3) 0.27(2) 0.34(3) -0.23(2) 0.13(2) -0.13(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C4 1.329(5) . ? N1 N2 1.357(5) . ? N1 Cu2 2.008(4) 1_664 ? C1 C2 1.491(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? Cu1 C20 1.851(6) 1_554 ? Cu1 N6 1.933(5) . ? Cu1 N5 2.030(4) . ? N2 C2 1.326(6) . ? N2 H2 0.8600 . ? C2 C3 1.373(7) . ? Cu2 C18 1.867(6) . ? Cu2 N7 1.969(4) . ? Cu2 N1 2.008(4) 1_446 ? Cu2 Cu2 3.0599(13) 2_436 ? N3 C11 1.333(5) . ? N3 C7 1.358(5) . ? N3 Cu3 2.079(3) 1_564 ? C3 C4 1.403(7) . ? C3 C6 1.508(6) . ? Cu3 C19 1.864(5) . ? Cu3 N8 1.921(5) . ? Cu3 N3 2.079(3) 1_546 ? N4 C14 1.343(6) . ? N4 N5 1.363(5) . ? N4 H4 0.8600 . ? C4 C5 1.471(8) . ? N5 C16 1.324(6) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.491(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N6 C18 1.145(6) . ? C7 C8 1.379(6) . ? N7 C19 1.148(6) . ? C8 C9 1.364(7) . ? C8 H8 0.9300 . ? N8 C20 1.152(6) . ? C9 C10 1.371(7) . ? C9 H9 0.9300 . ? C10 C11 1.379(6) . ? C10 H10 0.9300 . ? C11 C12 1.508(6) . ? C12 C15 1.509(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.501(8) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.376(8) . ? C15 C16 1.400(7) . ? C16 C17 1.486(8) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C20 Cu1 1.851(6) 1_556 ? C21 C22 1.482(9) . ? C21 C26 1.531(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.527(9) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.503(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.507(9) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.505(9) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 N2 104.8(4) . . ? C4 N1 Cu2 137.5(4) . 1_664 ? N2 N1 Cu2 117.6(3) . 1_664 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C20 Cu1 N6 136.3(2) 1_554 . ? C20 Cu1 N5 125.9(2) 1_554 . ? N6 Cu1 N5 97.85(17) . . ? C2 N2 N1 112.9(4) . . ? C2 N2 H2 123.6 . . ? N1 N2 H2 123.6 . . ? N2 C2 C3 106.3(5) . . ? N2 C2 C1 122.5(5) . . ? C3 C2 C1 131.2(5) . . ? C18 Cu2 N7 130.96(18) . . ? C18 Cu2 N1 131.70(19) . 1_446 ? N7 Cu2 N1 96.71(17) . 1_446 ? C18 Cu2 Cu2 81.18(15) . 2_436 ? N7 Cu2 Cu2 105.24(14) . 2_436 ? N1 Cu2 Cu2 94.92(12) 1_446 2_436 ? C11 N3 C7 119.8(3) . . ? C11 N3 Cu3 119.3(3) . 1_564 ? C7 N3 Cu3 120.3(3) . 1_564 ? C2 C3 C4 105.8(4) . . ? C2 C3 C6 126.8(5) . . ? C4 C3 C6 127.4(5) . . ? C19 Cu3 N8 133.14(18) . . ? C19 Cu3 N3 123.55(17) . 1_546 ? N8 Cu3 N3 103.29(16) . 1_546 ? C14 N4 N5 112.3(4) . . ? C14 N4 H4 123.9 . . ? N5 N4 H4 123.9 . . ? N1 C4 C3 110.2(5) . . ? N1 C4 C5 120.5(5) . . ? C3 C4 C5 129.3(4) . . ? C16 N5 N4 104.8(4) . . ? C16 N5 Cu1 137.1(4) . . ? N4 N5 Cu1 117.9(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C3 115.4(4) . . ? C7 C6 H6A 108.4 . . ? C3 C6 H6A 108.4 . . ? C7 C6 H6B 108.4 . . ? C3 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C18 N6 Cu1 176.8(5) . . ? N3 C7 C8 120.4(4) . . ? N3 C7 C6 115.0(4) . . ? C8 C7 C6 124.5(4) . . ? C19 N7 Cu2 170.3(4) . . ? C9 C8 C7 119.6(4) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C20 N8 Cu3 174.2(5) . . ? C8 C9 C10 119.8(4) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C9 C10 C11 119.1(5) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? N3 C11 C10 121.4(4) . . ? N3 C11 C12 115.0(4) . . ? C10 C11 C12 123.6(4) . . ? C11 C12 C15 115.5(4) . . ? C11 C12 H12A 108.4 . . ? C15 C12 H12A 108.4 . . ? C11 C12 H12B 108.4 . . ? C15 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C14 C15 106.3(5) . . ? N4 C14 C13 122.2(6) . . ? C15 C14 C13 131.4(5) . . ? C14 C15 C16 105.5(4) . . ? C14 C15 C12 125.9(5) . . ? C16 C15 C12 128.5(6) . . ? N5 C16 C15 111.1(5) . . ? N5 C16 C17 121.0(5) . . ? C15 C16 C17 127.9(5) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N6 C18 Cu2 178.7(5) . . ? N7 C19 Cu3 178.0(4) . . ? N8 C20 Cu1 175.9(5) . 1_556 ? C22 C21 C26 113.6(8) . . ? C22 C21 H21A 108.8 . . ? C26 C21 H21A 108.8 . . ? C22 C21 H21B 108.8 . . ? C26 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C23 115.6(7) . . ? C21 C22 H22A 108.4 . . ? C23 C22 H22A 108.4 . . ? C21 C22 H22B 108.4 . . ? C23 C22 H22B 108.4 . . ? H22A C22 H22B 107.4 . . ? C24 C23 C22 112.0(9) . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C23 C24 C25 114.3(8) . . ? C23 C24 H24A 108.7 . . ? C25 C24 H24A 108.7 . . ? C23 C24 H24B 108.7 . . ? C25 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? C26 C25 C24 114.7(7) . . ? C26 C25 H25A 108.6 . . ? C24 C25 H25A 108.6 . . ? C26 C25 H25B 108.6 . . ? C24 C25 H25B 108.6 . . ? H25A C25 H25B 107.6 . . ? C25 C26 C21 112.6(9) . . ? C25 C26 H26A 109.1 . . ? C21 C26 H26A 109.1 . . ? C25 C26 H26B 109.1 . . ? C21 C26 H26B 109.1 . . ? H26A C26 H26B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.524 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.076 data_Cu-MeCN-100K _database_code_depnum_ccdc_archive 'CCDC 918405' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 Cu3 N9 O' _chemical_formula_weight 621.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3700(4) _cell_length_b 11.4274(5) _cell_length_c 12.1912(6) _cell_angle_alpha 67.952(4) _cell_angle_beta 87.743(3) _cell_angle_gamma 69.803(3) _cell_volume 1370.45(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5347 _cell_measurement_theta_min 2.7674 _cell_measurement_theta_max 29.3873 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 2.337 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6521 _exptl_absorpt_correction_T_max 0.8535 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9451 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4837 _reflns_number_gt 4031 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1614P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4837 _refine_ls_number_parameters 321 _refine_ls_number_restraints 360 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.2077 _refine_ls_wR_factor_gt 0.1890 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.097 _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 Cu3 Cu 0.68489(4) 0.36753(4) -0.27502(4) 0.02769(12) Uani 1 1 d . . . N1 N 1.2778(3) 0.2265(3) 0.9275(3) 0.0338(9) Uani 1 1 d . . . C1 C 1.1074(6) 0.5040(5) 0.6507(5) 0.0723(18) Uani 1 1 d U . . H1A H 1.0858 0.5855 0.6683 0.108 Uiso 1 1 calc R . . H1B H 1.0338 0.5070 0.6090 0.108 Uiso 1 1 calc R . . H1C H 1.1769 0.4996 0.6004 0.108 Uiso 1 1 calc R . . Cu1 Cu 0.62899(4) -0.18390(4) 0.41948(4) 0.02520(11) Uani 1 1 d . . . N2 N 1.2612(3) 0.3385(3) 0.8269(3) 0.0411(10) Uani 1 1 d . . . H2 H 1.3170 0.3781 0.8047 0.049 Uiso 1 1 calc R . . C2 C 1.1468(4) 0.3816(4) 0.7647(4) 0.0517(11) Uani 1 1 d U . . O1 O 0.7020(7) 0.1664(8) 0.1318(7) 0.158(3) Uani 1 1 d . . . Cu2 Cu 0.45180(4) 0.12349(4) 0.01006(4) 0.02824(12) Uani 1 1 d . . . N3 N 0.8408(3) 0.2273(3) 0.6964(3) 0.0343(8) Uani 1 1 d . . . C3 C 1.0866(4) 0.2943(4) 0.8307(4) 0.0476(11) Uani 1 1 d U . . C4 C 1.1735(4) 0.1994(4) 0.9312(4) 0.0410(10) Uani 1 1 d U . . N4 N 0.6304(3) 0.0901(3) 0.3590(4) 0.0517(11) Uani 1 1 d . . . H4 H 0.6092 0.1094 0.2839 0.062 Uiso 1 1 calc R . . N5 N 0.6537(3) -0.0318(3) 0.4494(3) 0.0316(8) Uani 1 1 d . . . C5 C 1.1573(4) 0.0843(5) 1.0289(4) 0.0501(13) Uani 1 1 d U . . H5A H 1.2310 0.0395 1.0882 0.075 Uiso 1 1 calc R . . H5B H 1.1486 0.0200 0.9975 0.075 Uiso 1 1 calc R . . H5C H 1.0816 0.1165 1.0661 0.075 Uiso 1 1 calc R . . N6 N 0.5650(3) -0.0870(3) 0.2528(3) 0.0279(8) Uani 1 1 d . . . C6 C 0.9603(4) 0.2992(5) 0.7978(5) 0.0539(11) Uani 1 1 d U . . H6A H 0.9094 0.3940 0.7475 0.065 Uiso 1 1 calc R . . H6B H 0.9189 0.2732 0.8715 0.065 Uiso 1 1 calc R . . N7 N 0.5313(3) 0.2547(3) -0.0843(3) 0.0386(9) Uani 1 1 d . . . C7 C 0.9573(4) 0.2122(4) 0.7335(4) 0.0459(10) Uani 1 1 d U . . N8 N 0.6735(3) 0.5380(3) -0.3937(3) 0.0364(9) Uani 1 1 d . . . C8 C 1.0649(4) 0.1204(4) 0.7141(5) 0.0513(10) Uani 1 1 d U . . H8 H 1.1465 0.1119 0.7393 0.062 Uiso 1 1 calc R . . C9 C 1.0493(5) 0.0426(5) 0.6574(5) 0.0627(12) Uani 1 1 d U . . H9 H 1.1209 -0.0221 0.6438 0.075 Uiso 1 1 calc R . . N9 N 0.0873(13) 0.6576(10) -0.1209(10) 0.218(6) Uani 1 1 d . . . C10 C 0.9317(4) 0.0577(5) 0.6206(6) 0.0664(11) Uani 1 1 d U . . H10 H 0.9209 0.0040 0.5810 0.080 Uiso 1 1 calc R . . C11 C 0.8279(4) 0.1516(4) 0.6412(5) 0.0583(10) Uani 1 1 d U . . C12 C 0.6914(4) 0.1780(5) 0.6043(6) 0.0686(11) Uani 1 1 d U . . H12A H 0.6512 0.1432 0.6769 0.082 Uiso 1 1 calc R . . H12B H 0.6463 0.2769 0.5667 0.082 Uiso 1 1 calc R . . C13 C 0.6294(6) 0.3201(5) 0.3175(7) 0.103(2) Uani 1 1 d U . . H13A H 0.7092 0.3207 0.2842 0.155 Uiso 1 1 calc R . . H13B H 0.6049 0.3818 0.3595 0.155 Uiso 1 1 calc R . . H13C H 0.5638 0.3496 0.2531 0.155 Uiso 1 1 calc R . . C14 C 0.6454(4) 0.1787(4) 0.4036(5) 0.0642(11) Uani 1 1 d U . . C15 C 0.6743(4) 0.1164(5) 0.5207(5) 0.0637(11) Uani 1 1 d U . . C16 C 0.6794(4) -0.0164(4) 0.5469(5) 0.0523(9) Uani 1 1 d U . . C17 C 0.7120(4) -0.1297(5) 0.6638(5) 0.0622(13) Uani 1 1 d U . . H17A H 0.6935 -0.2050 0.6580 0.093 Uiso 1 1 calc R . . H17B H 0.6623 -0.1004 0.7224 0.093 Uiso 1 1 calc R . . H17C H 0.8019 -0.1592 0.6887 0.093 Uiso 1 1 calc R . . C18 C 0.5227(3) -0.0144(3) 0.1585(3) 0.0228(8) Uani 1 1 d . . . C19 C 0.5890(4) 0.3052(3) -0.1544(4) 0.0359(11) Uani 1 1 d . . . C20 C 0.6596(3) 0.6416(4) -0.4671(4) 0.0310(10) Uani 1 1 d . . . C21 C 0.215(3) 0.4552(10) 0.0665(10) 0.371(7) Uani 1 1 d U . . H21A H 0.3054 0.4366 0.0782 0.557 Uiso 1 1 calc R . . H21B H 0.2024 0.3784 0.0576 0.557 Uiso 1 1 calc R . . H21C H 0.1749 0.4689 0.1356 0.557 Uiso 1 1 calc R . . C22 C 0.158(3) 0.5771(10) -0.0408(10) 0.350(8) Uani 1 1 d U . . 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 Cu3 0.0374(2) 0.02020(17) 0.0289(2) -0.01038(15) 0.00940(18) -0.01384(16) N1 0.0353(15) 0.0318(14) 0.0249(15) -0.0098(12) -0.0060(13) -0.0011(13) C1 0.074(3) 0.055(3) 0.058(3) -0.018(2) -0.025(3) 0.012(3) Cu1 0.0332(2) 0.02182(17) 0.0218(2) -0.00593(15) 0.00108(17) -0.01379(16) N2 0.0497(19) 0.0314(15) 0.0329(18) -0.0124(13) -0.0091(15) -0.0023(15) C2 0.0483(19) 0.0492(17) 0.0529(19) -0.0350(15) -0.0058(17) 0.0062(17) O1 0.165(5) 0.193(5) 0.138(6) -0.050(4) 0.024(4) -0.106(4) Cu2 0.0315(2) 0.02670(19) 0.0233(2) -0.00678(16) 0.00298(18) -0.00983(17) N3 0.0415(15) 0.0315(12) 0.0442(17) -0.0233(12) 0.0195(14) -0.0218(12) C3 0.0414(18) 0.0518(16) 0.0528(18) -0.0402(14) -0.0055(16) 0.0027(16) C4 0.0333(16) 0.0476(15) 0.0498(18) -0.0354(14) 0.0073(15) -0.0056(14) N4 0.069(2) 0.0291(13) 0.067(2) -0.0253(14) 0.0464(18) -0.0270(14) N5 0.0373(14) 0.0316(12) 0.0413(17) -0.0224(12) 0.0182(13) -0.0228(11) C5 0.0366(19) 0.065(2) 0.053(3) -0.029(2) 0.0069(18) -0.0167(18) N6 0.0330(14) 0.0280(13) 0.0249(15) -0.0100(11) 0.0030(12) -0.0137(11) C6 0.0409(17) 0.0611(16) 0.0696(19) -0.0499(14) -0.0011(16) -0.0020(15) N7 0.0502(17) 0.0303(14) 0.0356(18) -0.0089(13) 0.0124(15) -0.0199(13) C7 0.0396(16) 0.0511(14) 0.0676(18) -0.0441(13) 0.0181(15) -0.0183(13) N8 0.0389(15) 0.0280(14) 0.0384(19) -0.0060(13) 0.0029(14) -0.0148(12) C8 0.0419(17) 0.0568(15) 0.0752(19) -0.0466(14) 0.0202(16) -0.0191(15) C9 0.0474(19) 0.0725(18) 0.105(2) -0.0681(17) 0.0312(18) -0.0291(16) N9 0.298(12) 0.137(7) 0.151(7) -0.058(6) 0.105(8) -0.002(8) C10 0.0502(17) 0.0804(17) 0.114(2) -0.0756(15) 0.0400(17) -0.0375(15) C11 0.0442(15) 0.0719(15) 0.1034(19) -0.0677(14) 0.0373(15) -0.0386(13) C12 0.0507(18) 0.0866(17) 0.121(2) -0.0816(16) 0.0369(18) -0.0435(15) C13 0.101(3) 0.045(2) 0.184(5) -0.056(3) 0.097(3) -0.046(2) C14 0.0534(17) 0.0625(16) 0.123(2) -0.0694(16) 0.0632(17) -0.0439(14) C15 0.0454(17) 0.0814(17) 0.117(2) -0.0772(16) 0.0486(18) -0.0456(15) C16 0.0358(15) 0.0802(15) 0.095(2) -0.0756(14) 0.0373(15) -0.0419(13) C17 0.039(2) 0.105(2) 0.077(2) -0.069(2) 0.0163(19) -0.031(2) C18 0.0225(14) 0.0264(13) 0.0247(17) -0.0102(12) 0.0029(13) -0.0147(12) C19 0.050(2) 0.0179(15) 0.032(2) -0.0060(14) 0.0113(18) -0.0083(15) C20 0.0322(16) 0.0317(16) 0.0308(19) -0.0099(14) -0.0016(15) -0.0155(14) C21 0.749(17) 0.135(5) 0.125(5) -0.113(4) -0.028(10) 0.042(10) C22 0.730(18) 0.099(5) 0.089(5) -0.068(4) 0.026(10) 0.043(10) _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 Cu3 C19 1.866(4) . ? Cu3 N8 1.905(3) . ? Cu3 N3 2.059(3) 1_554 ? N1 C4 1.320(6) . ? N1 N2 1.360(4) . ? N1 Cu2 1.993(3) 1_656 ? C1 C2 1.499(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? Cu1 C20 1.871(4) 1_546 ? Cu1 N6 1.938(3) . ? Cu1 N5 2.014(3) . ? N2 C2 1.365(6) . ? N2 H2 0.8800 . ? C2 C3 1.392(7) . ? Cu2 C18 1.872(3) . ? Cu2 N7 1.986(4) . ? Cu2 N1 1.993(3) 1_454 ? Cu2 Cu2 2.7550(9) 2_655 ? N3 C11 1.325(7) . ? N3 C7 1.349(6) . ? N3 Cu3 2.059(3) 1_556 ? C3 C4 1.418(6) . ? C3 C6 1.482(7) . ? C4 C5 1.468(6) . ? N4 N5 1.357(4) . ? N4 C14 1.374(7) . ? N4 H4 0.8800 . ? N5 C16 1.322(6) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? N6 C18 1.137(4) . ? C6 C7 1.489(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N7 C19 1.158(6) . ? C7 C8 1.389(6) . ? N8 C20 1.146(5) . ? C8 C9 1.372(8) . ? C8 H8 0.9500 . ? C9 C10 1.359(7) . ? C9 H9 0.9500 . ? N9 C22 1.15(2) . ? C10 C11 1.382(7) . ? C10 H10 0.9500 . ? C11 C12 1.527(7) . ? C12 C15 1.489(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.512(7) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.329(8) . ? C15 C16 1.409(7) . ? C16 C17 1.474(7) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C20 Cu1 1.871(4) 1_564 ? C21 C22 1.465(15) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C19 Cu3 N8 136.02(15) . . ? C19 Cu3 N3 118.10(14) . 1_554 ? N8 Cu3 N3 105.80(14) . 1_554 ? C4 N1 N2 106.5(3) . . ? C4 N1 Cu2 134.5(3) . 1_656 ? N2 N1 Cu2 117.2(3) . 1_656 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C20 Cu1 N6 136.02(17) 1_546 . ? C20 Cu1 N5 125.74(16) 1_546 . ? N6 Cu1 N5 98.21(13) . . ? N1 N2 C2 111.3(4) . . ? N1 N2 H2 124.3 . . ? C2 N2 H2 124.3 . . ? N2 C2 C3 106.3(4) . . ? N2 C2 C1 120.9(5) . . ? C3 C2 C1 132.8(5) . . ? C18 Cu2 N7 123.70(15) . . ? C18 Cu2 N1 135.16(15) . 1_454 ? N7 Cu2 N1 97.87(14) . 1_454 ? C18 Cu2 Cu2 69.54(12) . 2_655 ? N7 Cu2 Cu2 114.26(11) . 2_655 ? N1 Cu2 Cu2 110.65(11) 1_454 2_655 ? C11 N3 C7 119.4(4) . . ? C11 N3 Cu3 120.6(3) . 1_556 ? C7 N3 Cu3 120.1(3) . 1_556 ? C2 C3 C4 105.2(4) . . ? C2 C3 C6 126.2(4) . . ? C4 C3 C6 128.6(4) . . ? N1 C4 C3 110.6(4) . . ? N1 C4 C5 121.8(4) . . ? C3 C4 C5 127.6(4) . . ? N5 N4 C14 109.0(4) . . ? N5 N4 H4 125.5 . . ? C14 N4 H4 125.5 . . ? C16 N5 N4 106.0(3) . . ? C16 N5 Cu1 133.5(3) . . ? N4 N5 Cu1 120.2(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C18 N6 Cu1 170.4(3) . . ? C3 C6 C7 116.3(4) . . ? C3 C6 H6A 108.2 . . ? C7 C6 H6A 108.2 . . ? C3 C6 H6B 108.2 . . ? C7 C6 H6B 108.2 . . ? H6A C6 H6B 107.4 . . ? C19 N7 Cu2 160.7(4) . . ? N3 C7 C8 121.8(5) . . ? N3 C7 C6 114.8(4) . . ? C8 C7 C6 123.4(4) . . ? C20 N8 Cu3 176.0(4) . . ? C9 C8 C7 117.8(5) . . ? C9 C8 H8 121.1 . . ? C7 C8 H8 121.1 . . ? C10 C9 C8 120.2(5) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.6(5) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? N3 C11 C10 121.2(4) . . ? N3 C11 C12 114.2(4) . . ? C10 C11 C12 124.6(5) . . ? C15 C12 C11 115.3(4) . . ? C15 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C15 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 N4 109.2(4) . . ? C15 C14 C13 132.4(6) . . ? N4 C14 C13 118.4(6) . . ? C14 C15 C16 104.7(5) . . ? C14 C15 C12 126.6(5) . . ? C16 C15 C12 128.7(5) . . ? N5 C16 C15 111.1(4) . . ? N5 C16 C17 121.4(4) . . ? C15 C16 C17 127.4(5) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N6 C18 Cu2 172.4(3) . . ? N7 C19 Cu3 172.0(4) . . ? N8 C20 Cu1 176.0(4) . 1_564 ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N9 C22 C21 160(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.269 _refine_diff_density_min -1.093 _refine_diff_density_rms 0.128 #End of Crystallographic Information File