# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_complex1 _database_code_depnum_ccdc_archive 'CCDC 912377' #TrackingRef 'web_deposit_cif_file_0_SandipMukherjee_1353748871.cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H13 Cu2 N15' _chemical_formula_sum 'C9 H13 Cu2 N15' _chemical_formula_weight 458.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.4645(11) _cell_length_b 20.057(3) _cell_length_c 12.863(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.475(2) _cell_angle_gamma 90.00 _cell_volume 1621.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3248 _cell_measurement_theta_min 1.92 _cell_measurement_theta_max 26.21 _exptl_crystal_description rectangular _exptl_crystal_colour black _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.877 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 2.655 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4429 _exptl_absorpt_correction_T_max 0.5245 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15956 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 26.21 _reflns_number_total 3248 _reflns_number_gt 2447 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0405P)^2^+1.9467P] 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 3248 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 -0.04684(9) 0.12053(3) 0.26224(4) 0.03074(17) Uani 1 1 d . . . Cu2 Cu 0.53256(8) 0.07191(3) 0.46027(4) 0.02885(16) Uani 1 1 d . . . N1 N -0.0856(5) 0.02901(18) 0.1943(3) 0.0300(8) Uani 1 1 d . . . N2 N -0.2024(5) 0.14455(18) 0.1181(3) 0.0299(8) Uani 1 1 d . . . N3 N -0.0572(6) 0.21973(18) 0.2879(3) 0.0324(9) Uani 1 1 d . . . H3 H -0.0911 0.2253 0.3521 0.039 Uiso 1 1 calc R . . N4 N 0.1456(6) 0.0959(2) 0.3957(3) 0.0349(9) Uani 1 1 d . . . N5 N 0.0876(7) 0.1013(3) 0.4746(4) 0.0529(13) Uani 1 1 d . . . N6 N 0.0389(10) 0.1080(4) 0.5548(5) 0.118(3) Uani 1 1 d . . . N7 N 0.6074(6) 0.10699(19) 0.3281(3) 0.0318(9) Uani 1 1 d . . . N8 N 0.4582(6) 0.11340(18) 0.2544(3) 0.0317(9) Uani 1 1 d . . . N9 N 0.3174(7) 0.1209(2) 0.1816(3) 0.0520(12) Uani 1 1 d . . . N10 N 0.5069(6) -0.02228(18) 0.4105(3) 0.0347(9) Uani 1 1 d . . . N11 N 0.4949(6) -0.04318(18) 0.3213(3) 0.0314(9) Uani 1 1 d . . . N12 N 0.4810(7) -0.0626(2) 0.2366(3) 0.0509(12) Uani 1 1 d . . . N13 N 0.5787(7) 0.1564(2) 0.5370(3) 0.0436(11) Uani 1 1 d . . . N14 N 0.6559(6) 0.2019(2) 0.5026(3) 0.0382(10) Uani 1 1 d . . . N15 N 0.7273(8) 0.2486(2) 0.4708(4) 0.0542(12) Uani 1 1 d . . . C1 C -0.0184(7) -0.0289(2) 0.2359(4) 0.0399(12) Uani 1 1 d . . . H1 H 0.0561 -0.0306 0.3070 0.048 Uiso 1 1 calc R . . C2 C -0.0541(8) -0.0880(3) 0.1779(5) 0.0457(13) Uani 1 1 d . . . H2 H -0.0061 -0.1284 0.2102 0.055 Uiso 1 1 calc R . . C3 C -0.1601(8) -0.0860(3) 0.0730(5) 0.0475(14) Uani 1 1 d . . . H3A H -0.1854 -0.1249 0.0325 0.057 Uiso 1 1 calc R . . C4 C -0.2292(8) -0.0249(3) 0.0282(4) 0.0428(12) Uani 1 1 d . . . H4 H -0.3005 -0.0220 -0.0434 0.051 Uiso 1 1 calc R . . C5 C -0.1916(7) 0.0314(2) 0.0903(4) 0.0322(11) Uani 1 1 d . . . C6 C -0.2562(7) 0.0988(2) 0.0519(4) 0.0350(11) Uani 1 1 d . . . H6 H -0.3327 0.1069 -0.0177 0.042 Uiso 1 1 calc R . . C7 C -0.2415(8) 0.2156(2) 0.0987(4) 0.0412(12) Uani 1 1 d . . . H7A H -0.3794 0.2226 0.0506 0.049 Uiso 1 1 calc R . . H7B H -0.1332 0.2348 0.0668 0.049 Uiso 1 1 calc R . . C8 C -0.2348(8) 0.2474(2) 0.2054(4) 0.0421(12) Uani 1 1 d . . . H8A H -0.2168 0.2952 0.2002 0.051 Uiso 1 1 calc R . . H8B H -0.3681 0.2394 0.2256 0.051 Uiso 1 1 calc R . . C9 C 0.1445(8) 0.2547(3) 0.2937(4) 0.0514(14) Uani 1 1 d . . . H9A H 0.2539 0.2349 0.3484 0.077 Uiso 1 1 calc R . . H9B H 0.1288 0.3008 0.3104 0.077 Uiso 1 1 calc R . . H9C H 0.1827 0.2514 0.2261 0.077 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 0.0320(3) 0.0288(3) 0.0279(3) 0.0015(2) -0.0003(2) 0.0002(2) Cu2 0.0351(3) 0.0270(3) 0.0261(3) 0.0009(2) 0.0105(2) 0.0011(2) N1 0.028(2) 0.032(2) 0.032(2) 0.0020(17) 0.0103(16) -0.0018(17) N2 0.0240(19) 0.035(2) 0.029(2) 0.0048(18) 0.0026(16) -0.0035(17) N3 0.035(2) 0.027(2) 0.035(2) 0.0021(17) 0.0083(17) -0.0027(17) N4 0.028(2) 0.051(3) 0.025(2) 0.0067(18) 0.0066(17) 0.0026(18) N5 0.033(2) 0.082(4) 0.046(3) 0.029(3) 0.013(2) 0.019(2) N6 0.091(5) 0.213(8) 0.063(4) 0.064(5) 0.042(4) 0.086(5) N7 0.029(2) 0.038(2) 0.028(2) 0.0021(17) 0.0069(17) -0.0035(18) N8 0.035(2) 0.031(2) 0.033(2) -0.0025(18) 0.0165(19) -0.0054(18) N9 0.041(3) 0.077(4) 0.035(2) 0.008(2) 0.003(2) -0.006(2) N10 0.051(2) 0.027(2) 0.027(2) -0.0004(18) 0.0133(18) 0.0037(19) N11 0.032(2) 0.030(2) 0.032(2) 0.0028(19) 0.0067(17) 0.0006(17) N12 0.057(3) 0.063(3) 0.034(3) -0.010(2) 0.013(2) -0.009(2) N13 0.057(3) 0.035(2) 0.044(3) -0.008(2) 0.023(2) -0.014(2) N14 0.037(2) 0.036(3) 0.044(3) -0.009(2) 0.014(2) 0.001(2) N15 0.073(3) 0.030(3) 0.067(3) -0.011(2) 0.032(3) -0.012(2) C1 0.032(3) 0.041(3) 0.048(3) 0.004(2) 0.011(2) 0.001(2) C2 0.041(3) 0.030(3) 0.069(4) 0.003(3) 0.020(3) 0.003(2) C3 0.047(3) 0.040(3) 0.063(4) -0.015(3) 0.027(3) -0.014(3) C4 0.041(3) 0.048(3) 0.041(3) -0.009(3) 0.013(2) -0.011(3) C5 0.024(2) 0.043(3) 0.032(3) -0.005(2) 0.0120(19) -0.006(2) C6 0.028(2) 0.047(3) 0.029(3) 0.006(2) 0.0032(19) -0.003(2) C7 0.037(3) 0.039(3) 0.044(3) 0.011(2) 0.001(2) 0.001(2) C8 0.039(3) 0.031(3) 0.057(3) 0.002(2) 0.012(2) 0.008(2) C9 0.050(3) 0.043(3) 0.058(4) 0.001(3) 0.005(3) -0.013(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N4 1.934(4) . ? Cu1 N2 1.952(4) . ? Cu1 N3 2.021(4) . ? Cu1 N1 2.023(4) . ? Cu2 N13 1.949(4) . ? Cu2 N10 1.989(4) . ? Cu2 N7 2.001(4) . ? Cu2 N10 2.004(4) 3_656 ? N1 C1 1.310(6) . ? N1 C5 1.355(5) . ? N2 C6 1.246(6) . ? N2 C7 1.459(6) . ? N3 C9 1.467(6) . ? N3 C8 1.478(6) . ? N4 N5 1.166(5) . ? N5 N6 1.154(7) . ? N7 N8 1.191(5) . ? N8 N9 1.153(5) . ? N10 N11 1.207(5) . ? N10 Cu2 2.004(4) 3_656 ? N11 N12 1.141(5) . ? N13 N14 1.175(5) . ? N14 N15 1.160(5) . ? C1 C2 1.390(7) . ? C2 C3 1.364(7) . ? C3 C4 1.384(7) . ? C4 C5 1.371(6) . ? C5 C6 1.467(6) . ? C7 C8 1.504(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N2 171.11(16) . . ? N4 Cu1 N3 98.38(16) . . ? N2 Cu1 N3 83.25(15) . . ? N4 Cu1 N1 98.10(16) . . ? N2 Cu1 N1 80.16(15) . . ? N3 Cu1 N1 163.40(14) . . ? N13 Cu2 N10 168.59(17) . . ? N13 Cu2 N7 94.93(16) . . ? N10 Cu2 N7 94.55(15) . . ? N13 Cu2 N10 92.64(16) . 3_656 ? N10 Cu2 N10 77.15(16) . 3_656 ? N7 Cu2 N10 169.17(15) . 3_656 ? C1 N1 C5 118.5(4) . . ? C1 N1 Cu1 129.2(3) . . ? C5 N1 Cu1 112.2(3) . . ? C6 N2 C7 126.4(4) . . ? C6 N2 Cu1 117.9(3) . . ? C7 N2 Cu1 115.7(3) . . ? C9 N3 C8 112.9(4) . . ? C9 N3 Cu1 114.6(3) . . ? C8 N3 Cu1 107.6(3) . . ? N5 N4 Cu1 118.6(3) . . ? N6 N5 N4 176.9(7) . . ? N8 N7 Cu2 113.8(3) . . ? N9 N8 N7 177.9(5) . . ? N11 N10 Cu2 128.1(3) . . ? N11 N10 Cu2 128.6(3) . 3_656 ? Cu2 N10 Cu2 102.85(16) . 3_656 ? N12 N11 N10 179.1(5) . . ? N14 N13 Cu2 120.8(3) . . ? N15 N14 N13 177.0(5) . . ? N1 C1 C2 122.6(5) . . ? C3 C2 C1 119.2(5) . . ? C2 C3 C4 118.5(5) . . ? C5 C4 C3 119.4(5) . . ? N1 C5 C4 121.8(4) . . ? N1 C5 C6 113.8(4) . . ? C4 C5 C6 124.4(4) . . ? N2 C6 C5 115.9(4) . . ? N2 C7 C8 106.9(4) . . ? N3 C8 C7 110.3(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.21 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.539 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.093 data_complex2 _database_code_depnum_ccdc_archive 'CCDC 912378' #TrackingRef 'web_deposit_cif_file_0_SandipMukherjee_1353748871.cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H46 Cu4 N22 O6' _chemical_formula_sum 'C28 H46 Cu4 N22 O6' _chemical_formula_weight 1041.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.4570(17) _cell_length_b 11.9376(7) _cell_length_c 13.4981(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.481(7) _cell_angle_gamma 90.00 _cell_volume 2144.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3650 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 29.2 _exptl_crystal_description rectangular _exptl_crystal_colour black _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 2.023 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.5136 _exptl_absorpt_correction_T_max 0.7121 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6572 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0709 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3650 _reflns_number_gt 2342 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0498P)^2^+2.6190P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3650 _refine_ls_number_parameters 279 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1009 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1397 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.27217(7) 0.77643(5) 0.08731(5) 0.0362(3) Uani 1 1 d . . . Cu2 Cu 0.47193(7) 0.92500(5) 0.08561(5) 0.0370(3) Uani 1 1 d . . . O1 O 0.4163(4) 0.7683(3) 0.0845(3) 0.0399(12) Uani 1 1 d . . . O2 O 0.6096(5) 0.8037(4) 0.0963(4) 0.0614(16) Uani 1 1 d . . . O1W O 0.2985(6) 0.8094(5) 0.2665(4) 0.0577(18) Uani 1 1 d . . . C1 C 0.4775(6) 0.6804(5) 0.1030(4) 0.0380(18) Uani 1 1 d . . . C2 C 0.5805(7) 0.6946(5) 0.1078(4) 0.046(2) Uani 1 1 d . . . C3 C 0.6471(7) 0.6063(6) 0.1249(4) 0.062(2) Uani 1 1 d . . . H3 H 0.7159 0.6178 0.1284 0.074 Uiso 1 1 calc R . . C4 C 0.6088(9) 0.4995(6) 0.1367(5) 0.064(3) Uani 1 1 d . . . H4 H 0.6525 0.4389 0.1474 0.077 Uiso 1 1 calc R . . C5 C 0.5106(8) 0.4830(5) 0.1330(5) 0.059(3) Uani 1 1 d . . . H5 H 0.4875 0.4108 0.1416 0.071 Uiso 1 1 calc R . . C6 C 0.4399(7) 0.5717(5) 0.1164(4) 0.047(2) Uani 1 1 d . . . C7 C 0.3370(8) 0.5466(5) 0.1128(4) 0.054(2) Uani 1 1 d . . . H7 H 0.3207 0.4719 0.1214 0.065 Uiso 1 1 calc R . . C8 C 0.1614(9) 0.5758(7) 0.0992(6) 0.077(3) Uani 1 1 d . . . H8A H 0.1490 0.5139 0.0524 0.092 Uiso 1 1 calc R . . H8B H 0.1559 0.5469 0.1654 0.092 Uiso 1 1 calc R . . C10 C 0.0776(11) 0.790(2) -0.0415(7) 0.276(14) Uani 1 1 d D . . H10A H 0.0514 0.7181 -0.0672 0.332 Uiso 1 1 calc R . . H10B H 0.0194 0.8366 -0.0377 0.332 Uiso 1 1 calc R . . C11 C 0.1218(13) 0.8346(8) -0.1161(8) 0.182(9) Uani 1 1 d D . . H11A H 0.0969 0.9092 -0.1300 0.273 Uiso 1 1 calc R . . H11B H 0.1066 0.7894 -0.1752 0.273 Uiso 1 1 calc R . . H11C H 0.1932 0.8370 -0.0960 0.273 Uiso 1 1 calc R . . C12 C 0.0698(9) 0.8393(8) 0.1224(6) 0.082(3) Uani 1 1 d . . . H12A H 0.0898 0.9160 0.1121 0.098 Uiso 1 1 calc R . . H12B H 0.0966 0.8196 0.1909 0.098 Uiso 1 1 calc R . . C13 C -0.0422(9) 0.8375(8) 0.1139(7) 0.086(3) Uani 1 1 d . . . H13A H -0.0632 0.8876 0.1624 0.129 Uiso 1 1 calc R . . H13B H -0.0643 0.7629 0.1258 0.129 Uiso 1 1 calc R . . H13C H -0.0711 0.8609 0.0478 0.129 Uiso 1 1 calc R . . C14 C 0.7104(9) 0.8278(8) 0.1069(7) 0.086(3) Uani 1 1 d . . . H14A H 0.7194 0.9065 0.0967 0.130 Uiso 1 1 calc R . . H14B H 0.7408 0.7862 0.0583 0.130 Uiso 1 1 calc R . . H14C H 0.7416 0.8075 0.1731 0.130 Uiso 1 1 calc R . . N1 N 0.2647(6) 0.6152(4) 0.0991(3) 0.0480(17) Uani 1 1 d . . . N2 N 0.1186(5) 0.7692(4) 0.0575(4) 0.0525(18) Uani 1 1 d . . . N3 N 0.2894(5) 0.9382(4) 0.0672(3) 0.0432(16) Uani 1 1 d . . . N4 N 0.2527(5) 1.0142(4) 0.1055(3) 0.0464(17) Uani 1 1 d . . . N5 N 0.2195(7) 1.0909(5) 0.1387(5) 0.087(3) Uani 1 1 d . . . N6 N 0.5348(5) 1.0707(4) 0.0646(3) 0.0466(17) Uani 1 1 d . . . N7 N 0.5624(7) 1.1432(4) 0.1187(4) 0.088(3) Uani 1 1 d . . . N8 N 0.5912(14) 1.2131(6) 0.1698(6) 0.242(10) Uani 1 1 d . . . N9 N 0.4783(6) 0.9324(5) 0.2327(3) 0.0537(19) Uani 1 1 d . . . N10 N 0.5470(6) 0.9738(4) 0.2840(4) 0.0478(19) Uani 1 1 d . . . N11 N 0.6097(7) 1.0131(6) 0.3378(5) 0.085(3) Uani 1 1 d . . . C9 C 0.0871(15) 0.6552(9) 0.0744(19) 0.271(14) Uani 1 1 d . . . H9A H 0.0460 0.6571 0.1277 0.325 Uiso 1 1 calc R . . H9B H 0.0445 0.6301 0.0143 0.325 Uiso 1 1 calc R . . H1W H 0.312(7) 0.750(6) 0.286(5) 0.07(3) Uiso 1 1 d . . . H2W H 0.354(7) 0.843(6) 0.274(5) 0.06(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0342(7) 0.0359(4) 0.0395(4) 0.0023(3) 0.0088(3) -0.0059(4) Cu2 0.0376(7) 0.0363(4) 0.0384(4) 0.0027(3) 0.0104(3) -0.0071(4) O1 0.040(4) 0.0255(18) 0.056(2) 0.0077(16) 0.0119(19) -0.002(2) O2 0.021(5) 0.064(3) 0.102(4) 0.017(2) 0.017(3) 0.003(3) O1W 0.063(6) 0.051(3) 0.059(3) 0.010(2) 0.010(3) -0.011(3) C1 0.042(6) 0.039(3) 0.032(3) 0.003(2) 0.005(3) 0.009(3) C2 0.044(7) 0.050(4) 0.046(3) 0.006(3) 0.014(3) 0.018(4) C3 0.059(8) 0.072(5) 0.056(4) 0.010(3) 0.011(3) 0.026(5) C4 0.083(10) 0.048(4) 0.061(4) 0.005(3) 0.008(4) 0.031(5) C5 0.078(10) 0.038(4) 0.062(4) 0.007(3) 0.008(4) 0.010(4) C6 0.068(8) 0.031(3) 0.041(3) 0.001(2) 0.009(3) 0.003(4) C7 0.082(9) 0.035(3) 0.043(3) 0.002(2) 0.001(3) -0.020(4) C8 0.077(10) 0.076(5) 0.073(5) 0.024(4) -0.004(4) -0.035(6) C10 0.064(13) 0.72(4) 0.046(6) -0.009(12) -0.004(5) -0.001(19) C11 0.33(3) 0.108(8) 0.085(7) 0.039(6) -0.063(10) -0.075(11) C12 0.041(10) 0.115(7) 0.092(6) -0.046(5) 0.019(5) -0.001(6) C13 0.035(11) 0.118(7) 0.108(7) -0.016(5) 0.024(5) 0.008(7) C14 0.032(10) 0.102(6) 0.126(8) 0.039(5) 0.013(5) 0.013(6) N1 0.051(6) 0.042(3) 0.051(3) 0.007(2) 0.008(3) -0.014(3) N2 0.050(6) 0.053(3) 0.054(3) -0.007(2) 0.003(3) -0.007(3) N3 0.046(6) 0.034(3) 0.052(3) 0.003(2) 0.014(2) -0.001(3) N4 0.051(6) 0.045(3) 0.044(3) 0.000(2) 0.007(2) -0.007(3) N5 0.106(11) 0.063(4) 0.097(5) -0.027(3) 0.030(5) 0.006(5) N6 0.058(6) 0.043(3) 0.040(3) -0.001(2) 0.013(2) -0.018(3) N7 0.184(11) 0.035(3) 0.047(3) 0.005(3) 0.023(4) -0.015(4) N8 0.58(3) 0.055(5) 0.077(6) -0.011(4) 0.005(9) -0.086(9) N9 0.054(6) 0.071(3) 0.038(3) 0.006(2) 0.014(3) -0.022(4) N10 0.041(6) 0.056(3) 0.045(3) 0.013(2) 0.003(3) -0.010(3) N11 0.076(9) 0.099(5) 0.073(5) 0.017(4) -0.010(4) -0.033(5) C9 0.02(3) 0.062(7) 0.74(5) -0.004(13) 0.08(2) -0.009(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.935(5) . ? Cu1 O1 1.948(5) . ? Cu1 N3 1.969(5) . ? Cu1 N2 2.048(7) . ? Cu1 O1W 2.425(5) . ? Cu2 N6 1.972(5) . ? Cu2 N9 1.976(5) . ? Cu2 O1 2.014(4) . ? Cu2 N6 2.017(4) 3_675 ? Cu2 O2 2.339(6) . ? Cu2 N3 2.438(7) . ? O1 C1 1.335(7) . ? O2 C14 1.373(11) . ? O2 C2 1.375(8) . ? O1W H1W 0.77(7) . ? O1W H2W 0.84(9) . ? C1 C2 1.388(10) . ? C1 C6 1.414(8) . ? C2 C3 1.382(9) . ? C3 C4 1.393(11) . ? C3 H3 0.9300 . ? C4 C5 1.329(12) . ? C4 H4 0.9300 . ? C5 C6 1.419(10) . ? C5 H5 0.9300 . ? C6 C7 1.410(11) . ? C7 N1 1.264(10) . ? C7 H7 0.9300 . ? C8 C9 1.383(19) . ? C8 N1 1.468(12) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C11 1.352(13) . ? C10 N2 1.390(12) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N2 1.439(10) . ? C12 C13 1.494(14) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? N2 C9 1.453(13) . ? N3 N4 1.187(7) . ? N4 N5 1.140(8) . ? N6 N7 1.158(7) . ? N6 Cu2 2.017(4) 3_675 ? N7 N8 1.115(9) . ? N9 N10 1.179(9) . ? N10 N11 1.131(9) . ? C9 H9A 0.9700 . ? C9 H9B 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 N1 Cu1 O1 90.9(3) . . ? N1 Cu1 N3 174.6(3) . . ? O1 Cu1 N3 84.8(2) . . ? N1 Cu1 N2 84.9(3) . . ? O1 Cu1 N2 166.58(18) . . ? N3 Cu1 N2 98.6(2) . . ? N1 Cu1 O1W 94.7(2) . . ? O1 Cu1 O1W 91.6(2) . . ? N3 Cu1 O1W 88.6(2) . . ? N2 Cu1 O1W 101.4(2) . . ? N6 Cu2 N9 98.6(2) . . ? N6 Cu2 O1 169.91(19) . . ? N9 Cu2 O1 90.58(19) . . ? N6 Cu2 N6 77.9(2) . 3_675 ? N9 Cu2 N6 176.0(2) . 3_675 ? O1 Cu2 N6 93.14(17) . 3_675 ? N6 Cu2 O2 101.7(2) . . ? N9 Cu2 O2 92.8(2) . . ? O1 Cu2 O2 73.5(2) . . ? N6 Cu2 O2 89.7(2) 3_675 . ? N6 Cu2 N3 112.0(2) . . ? N9 Cu2 N3 89.6(3) . . ? O1 Cu2 N3 72.04(18) . . ? N6 Cu2 N3 90.0(2) 3_675 . ? O2 Cu2 N3 145.44(18) . . ? C1 O1 Cu1 128.6(4) . . ? C1 O1 Cu2 120.7(5) . . ? Cu1 O1 Cu2 108.87(19) . . ? C14 O2 C2 118.7(7) . . ? C14 O2 Cu2 129.6(5) . . ? C2 O2 Cu2 110.9(5) . . ? Cu1 O1W H1W 100(5) . . ? Cu1 O1W H2W 102(5) . . ? H1W O1W H2W 104(9) . . ? O1 C1 C2 119.8(5) . . ? O1 C1 C6 121.5(7) . . ? C2 C1 C6 118.7(6) . . ? O2 C2 C3 123.6(8) . . ? O2 C2 C1 114.2(6) . . ? C3 C2 C1 122.2(7) . . ? C2 C3 C4 118.4(9) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 120.9(8) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 122.4(7) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C7 C6 C1 124.0(7) . . ? C7 C6 C5 118.6(7) . . ? C1 C6 C5 117.4(8) . . ? N1 C7 C6 126.7(6) . . ? N1 C7 H7 116.6 . . ? C6 C7 H7 116.6 . . ? C9 C8 N1 115.5(9) . . ? C9 C8 H8A 108.4 . . ? N1 C8 H8A 108.4 . . ? C9 C8 H8B 108.4 . . ? N1 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C11 C10 N2 129.0(13) . . ? C11 C10 H10A 105.0 . . ? N2 C10 H10A 105.0 . . ? C11 C10 H10B 105.0 . . ? N2 C10 H10B 105.0 . . ? H10A C10 H10B 105.9 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 C13 119.4(7) . . ? N2 C12 H12A 107.5 . . ? C13 C12 H12A 107.5 . . ? N2 C12 H12B 107.5 . . ? C13 C12 H12B 107.5 . . ? H12A C12 H12B 107.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 N1 C8 120.1(7) . . ? C7 N1 Cu1 127.5(6) . . ? C8 N1 Cu1 112.3(6) . . ? C10 N2 C12 109.3(11) . . ? C10 N2 C9 103.5(13) . . ? C12 N2 C9 106.1(10) . . ? C10 N2 Cu1 115.3(7) . . ? C12 N2 Cu1 113.2(5) . . ? C9 N2 Cu1 108.5(9) . . ? N4 N3 Cu1 128.7(5) . . ? N4 N3 Cu2 118.8(5) . . ? Cu1 N3 Cu2 93.4(2) . . ? N5 N4 N3 176.4(7) . . ? N7 N6 Cu2 132.4(4) . . ? N7 N6 Cu2 125.2(4) . 3_675 ? Cu2 N6 Cu2 102.1(2) . 3_675 ? N8 N7 N6 178.3(13) . . ? N10 N9 Cu2 121.6(6) . . ? N11 N10 N9 176.0(10) . . ? C8 C9 N2 117.6(15) . . ? C8 C9 H9A 107.9 . . ? N2 C9 H9A 107.9 . . ? C8 C9 H9B 107.9 . . ? N2 C9 H9B 107.9 . . ? H9A C9 H9B 107.2 . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.774 _refine_diff_density_min -0.828 _refine_diff_density_rms 0.081 data_complex3 _database_code_depnum_ccdc_archive 'CCDC 912379' #TrackingRef 'web_deposit_cif_file_0_SandipMukherjee_1353748871.cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H34 Cu4 N22 O4' _chemical_formula_sum 'C24 H34 Cu4 N22 O4' _chemical_formula_weight 948.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4131(6) _cell_length_b 21.4937(10) _cell_length_c 18.2110(17) _cell_angle_alpha 90.00 _cell_angle_beta 98.342(7) _cell_angle_gamma 90.00 _cell_volume 3645.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8311 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 28.94 _exptl_crystal_description rectangular _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 2.368 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.4510 _exptl_absorpt_correction_T_max 0.5890 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16659 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0996 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8311 _reflns_number_gt 4544 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0403P)^2^+0.8374P] 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 8311 _refine_ls_number_parameters 487 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1366 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.1397 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.05076(7) 0.73784(3) 0.79097(4) 0.0398(2) Uani 1 1 d . . . Cu2 Cu 0.17734(7) 0.66905(3) 0.70682(4) 0.0434(2) Uani 1 1 d . . . Cu3 Cu 0.45861(7) 0.60812(3) 0.78196(4) 0.0435(2) Uani 1 1 d . . . Cu4 Cu 0.66764(7) 0.53746(3) 0.68777(4) 0.0473(2) Uani 1 1 d . . . O1 O 0.0870(4) 0.75129(16) 0.7227(2) 0.0453(10) Uani 1 1 d . . . O2 O 0.2572(4) 0.7401(2) 0.6215(3) 0.0641(12) Uani 1 1 d . . . O3 O 0.5435(4) 0.52495(16) 0.7617(2) 0.0488(11) Uani 1 1 d . . . O4 O 0.3683(5) 0.53382(19) 0.8601(3) 0.0717(14) Uani 1 1 d . . . N1 N -0.0947(5) 0.8258(2) 0.7899(3) 0.0469(12) Uani 1 1 d . . . N2 N -0.1756(5) 0.7324(2) 0.8710(3) 0.0434(12) Uani 1 1 d . . . H2 H -0.2313 0.6979 0.8620 0.052 Uiso 1 1 calc R . . N3 N 0.0239(5) 0.6524(2) 0.8020(3) 0.0464(13) Uani 1 1 d . . . N4 N -0.0448(5) 0.6059(2) 0.7880(3) 0.0416(12) Uani 1 1 d . . . N5 N -0.1039(6) 0.5605(3) 0.7744(3) 0.0689(17) Uani 1 1 d . . . N6 N 0.0242(5) 0.6410(3) 0.6289(3) 0.0568(14) Uani 1 1 d . . . N7 N 0.0509(5) 0.6351(2) 0.5674(3) 0.0489(13) Uani 1 1 d . . . N8 N 0.0709(7) 0.6282(3) 0.5072(3) 0.0807(19) Uani 1 1 d . . . N9 N 0.3493(5) 0.6877(2) 0.7841(3) 0.0495(13) Uani 1 1 d . . . N10 N 0.3500(5) 0.7230(2) 0.8337(3) 0.0516(13) Uani 1 1 d . . . N11 N 0.3531(8) 0.7588(3) 0.8789(4) 0.099(2) Uani 1 1 d . . . N12 N 0.2897(5) 0.5923(2) 0.7038(3) 0.0598(15) Uani 1 1 d . . . N13 N 0.2639(6) 0.5470(3) 0.6689(3) 0.0681(17) Uani 1 1 d . . . N14 N 0.2381(10) 0.5031(3) 0.6370(5) 0.141(4) Uani 1 1 d . . . N15 N 0.6094(5) 0.6311(2) 0.8623(3) 0.0553(14) Uani 1 1 d . . . N16 N 0.6660(6) 0.5911(3) 0.9002(3) 0.0632(15) Uani 1 1 d . . . N17 N 0.7265(8) 0.5555(3) 0.9395(4) 0.109(3) Uani 1 1 d . . . N18 N 0.6050(5) 0.6248(2) 0.6881(3) 0.0497(13) Uani 1 1 d . . . N19 N 0.6780(5) 0.6700(2) 0.6911(3) 0.0433(12) Uani 1 1 d . . . N20 N 0.7428(6) 0.7140(3) 0.6922(3) 0.0642(16) Uani 1 1 d . . . N21 N 0.6973(5) 0.4486(2) 0.6803(3) 0.0540(14) Uani 1 1 d . . . N22 N 0.7835(5) 0.5439(3) 0.6044(3) 0.0621(15) Uani 1 1 d . . . H22 H 0.8552 0.5711 0.6207 0.075 Uiso 1 1 calc R . . C1 C 0.0994(6) 0.7999(3) 0.6795(3) 0.0408(14) Uani 1 1 d . . . C2 C 0.1870(6) 0.7962(3) 0.6236(3) 0.0489(16) Uani 1 1 d . . . C3 C 0.2032(7) 0.8457(3) 0.5783(4) 0.067(2) Uani 1 1 d . . . H3 H 0.2610 0.8419 0.5412 0.081 Uiso 1 1 calc R . . C4 C 0.1339(8) 0.9016(4) 0.5874(5) 0.086(3) Uani 1 1 d . . . H4 H 0.1453 0.9354 0.5568 0.103 Uiso 1 1 calc R . . C5 C 0.0495(8) 0.9065(3) 0.6413(4) 0.069(2) Uani 1 1 d . . . H5 H 0.0046 0.9442 0.6477 0.083 Uiso 1 1 calc R . . C6 C 0.0275(6) 0.8564(3) 0.6878(4) 0.0479(15) Uani 1 1 d . . . C7 C -0.0627(7) 0.8658(3) 0.7436(4) 0.0533(17) Uani 1 1 d . . . H7 H -0.1020 0.9053 0.7464 0.064 Uiso 1 1 calc R . . C8 C -0.1852(7) 0.8433(3) 0.8453(4) 0.0576(18) Uani 1 1 d . . . H8A H -0.2481 0.8774 0.8271 0.069 Uiso 1 1 calc R . . H8B H -0.1261 0.8566 0.8907 0.069 Uiso 1 1 calc R . . C9 C -0.2721(6) 0.7875(3) 0.8600(4) 0.0573(17) Uani 1 1 d . . . H9A H -0.3171 0.7943 0.9040 0.069 Uiso 1 1 calc R . . H9B H -0.3471 0.7804 0.8183 0.069 Uiso 1 1 calc R . . C10 C -0.0921(6) 0.7256(3) 0.9458(3) 0.0606(18) Uani 1 1 d . . . H10A H -0.0317 0.7621 0.9561 0.073 Uiso 1 1 calc R . . H10B H -0.0292 0.6899 0.9455 0.073 Uiso 1 1 calc R . . C11 C -0.1792(7) 0.7178(3) 1.0073(4) 0.074(2) Uani 1 1 d . . . H11A H -0.1165 0.7141 1.0536 0.111 Uiso 1 1 calc R . . H11B H -0.2368 0.6809 0.9989 0.111 Uiso 1 1 calc R . . H11C H -0.2406 0.7533 1.0090 0.111 Uiso 1 1 calc R . . C12 C 0.3466(7) 0.7298(3) 0.5662(4) 0.080(2) Uani 1 1 d . . . H12A H 0.3868 0.6887 0.5718 0.119 Uiso 1 1 calc R . . H12B H 0.4228 0.7599 0.5716 0.119 Uiso 1 1 calc R . . H12C H 0.2909 0.7338 0.5180 0.119 Uiso 1 1 calc R . . C13 C 0.4991(6) 0.4718(3) 0.7897(3) 0.0436(15) Uani 1 1 d . . . C14 C 0.4088(6) 0.4750(3) 0.8442(4) 0.0523(17) Uani 1 1 d . . . C15 C 0.3604(6) 0.4215(3) 0.8741(4) 0.0592(18) Uani 1 1 d . . . H15 H 0.2990 0.4240 0.9097 0.071 Uiso 1 1 calc R . . C16 C 0.4034(7) 0.3641(3) 0.8510(4) 0.070(2) Uani 1 1 d . . . H16 H 0.3695 0.3279 0.8703 0.084 Uiso 1 1 calc R . . C17 C 0.4941(7) 0.3607(3) 0.8005(4) 0.0620(19) Uani 1 1 d . . . H17 H 0.5245 0.3217 0.7868 0.074 Uiso 1 1 calc R . . C18 C 0.5445(6) 0.4141(3) 0.7677(4) 0.0480(16) Uani 1 1 d . . . C19 C 0.6414(7) 0.4060(3) 0.7157(4) 0.0575(18) Uani 1 1 d . . . H19 H 0.6670 0.3652 0.7064 0.069 Uiso 1 1 calc R . . C20 C 0.7973(9) 0.4342(4) 0.6292(4) 0.097(3) Uani 1 1 d . . . H20A H 0.8733 0.4082 0.6544 0.117 Uiso 1 1 calc R . . H20B H 0.7474 0.4104 0.5881 0.117 Uiso 1 1 calc R . . C21 C 0.8550(15) 0.4834(5) 0.6029(10) 0.229(10) Uani 1 1 d . . . H21A H 0.8651 0.4746 0.5516 0.275 Uiso 1 1 calc R . . H21B H 0.9511 0.4878 0.6299 0.275 Uiso 1 1 calc R . . C22 C 0.7290(10) 0.5644(11) 0.5341(6) 0.275(13) Uani 1 1 d D . . H22A H 0.8006 0.5931 0.5208 0.330 Uiso 1 1 calc R . . H22B H 0.7328 0.5284 0.5024 0.330 Uiso 1 1 calc R . . C23 C 0.6050(15) 0.5909(4) 0.5103(6) 0.173(6) Uani 1 1 d D . . H23A H 0.6029 0.6035 0.4596 0.260 Uiso 1 1 calc R . . H23B H 0.5929 0.6268 0.5402 0.260 Uiso 1 1 calc R . . H23C H 0.5287 0.5619 0.5137 0.260 Uiso 1 1 calc R . . C24 C 0.2836(8) 0.5445(3) 0.9148(4) 0.090(3) Uani 1 1 d . . . H24A H 0.2659 0.5883 0.9183 0.135 Uiso 1 1 calc R . . H24B H 0.3321 0.5296 0.9615 0.135 Uiso 1 1 calc R . . H24C H 0.1940 0.5229 0.9027 0.135 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 0.0475(4) 0.0324(4) 0.0403(4) -0.0011(3) 0.0090(3) 0.0041(3) Cu2 0.0439(4) 0.0398(4) 0.0478(5) -0.0072(4) 0.0105(3) 0.0010(3) Cu3 0.0450(4) 0.0345(4) 0.0522(5) -0.0084(4) 0.0109(3) -0.0006(3) Cu4 0.0481(4) 0.0476(4) 0.0479(5) -0.0100(4) 0.0131(4) 0.0018(3) O1 0.054(2) 0.034(2) 0.050(3) 0.004(2) 0.014(2) 0.0068(18) O2 0.069(3) 0.066(3) 0.063(3) 0.008(3) 0.030(2) 0.000(2) O3 0.054(2) 0.035(2) 0.061(3) -0.005(2) 0.022(2) 0.0002(19) O4 0.096(3) 0.044(3) 0.089(4) -0.006(3) 0.061(3) -0.007(2) N1 0.051(3) 0.037(3) 0.051(3) -0.007(3) 0.004(3) 0.006(2) N2 0.048(3) 0.037(3) 0.046(3) -0.007(3) 0.012(2) -0.002(2) N3 0.051(3) 0.037(3) 0.052(3) 0.000(3) 0.010(3) 0.006(2) N4 0.048(3) 0.035(3) 0.042(3) -0.001(3) 0.008(2) 0.006(3) N5 0.072(4) 0.047(3) 0.085(5) -0.007(4) 0.001(3) -0.003(3) N6 0.056(3) 0.071(4) 0.045(4) -0.004(3) 0.014(3) 0.001(3) N7 0.045(3) 0.044(3) 0.057(4) -0.009(3) 0.004(3) -0.002(2) N8 0.092(5) 0.100(5) 0.051(4) -0.008(4) 0.015(4) 0.004(4) N9 0.053(3) 0.039(3) 0.056(3) -0.015(3) 0.005(3) 0.004(2) N10 0.072(4) 0.035(3) 0.049(4) -0.003(3) 0.011(3) 0.004(3) N11 0.150(6) 0.078(5) 0.068(5) -0.033(4) 0.007(4) 0.022(4) N12 0.050(3) 0.045(3) 0.083(4) -0.023(3) 0.006(3) 0.003(3) N13 0.098(5) 0.037(3) 0.062(4) -0.013(3) -0.012(3) 0.006(3) N14 0.222(9) 0.049(4) 0.124(7) -0.033(5) -0.068(7) 0.012(5) N15 0.070(4) 0.039(3) 0.053(4) 0.003(3) -0.004(3) 0.001(3) N16 0.091(5) 0.051(4) 0.046(4) 0.002(3) 0.005(3) 0.002(3) N17 0.160(7) 0.082(5) 0.075(5) 0.022(5) -0.013(5) 0.018(5) N18 0.052(3) 0.044(3) 0.057(4) -0.001(3) 0.020(3) 0.003(3) N19 0.046(3) 0.044(3) 0.040(3) 0.004(3) 0.006(2) 0.007(3) N20 0.069(4) 0.051(3) 0.073(4) 0.005(3) 0.011(3) -0.008(3) N21 0.063(3) 0.057(4) 0.040(3) -0.017(3) 0.003(3) 0.016(3) N22 0.059(3) 0.071(4) 0.059(4) -0.025(3) 0.020(3) -0.015(3) C1 0.049(3) 0.038(3) 0.034(3) 0.009(3) 0.000(3) -0.008(3) C2 0.047(4) 0.053(4) 0.046(4) 0.004(3) 0.003(3) -0.012(3) C3 0.071(5) 0.076(5) 0.059(5) 0.019(4) 0.022(4) -0.010(4) C4 0.094(6) 0.070(5) 0.096(7) 0.041(5) 0.023(5) -0.006(5) C5 0.085(5) 0.041(4) 0.081(6) 0.024(4) 0.006(4) 0.003(4) C6 0.050(4) 0.036(3) 0.055(4) 0.003(3) -0.001(3) -0.001(3) C7 0.063(4) 0.034(3) 0.059(5) -0.008(3) -0.006(4) 0.003(3) C8 0.076(4) 0.043(4) 0.056(4) -0.013(3) 0.016(4) 0.012(3) C9 0.055(4) 0.065(4) 0.053(4) 0.001(4) 0.015(3) 0.019(3) C10 0.057(4) 0.077(5) 0.046(4) -0.002(4) 0.000(3) 0.004(4) C11 0.091(5) 0.088(5) 0.046(4) -0.012(4) 0.019(4) -0.010(4) C12 0.082(5) 0.087(6) 0.078(6) -0.015(5) 0.039(4) -0.011(4) C13 0.048(3) 0.031(3) 0.049(4) -0.005(3) 0.000(3) -0.003(3) C14 0.052(4) 0.040(4) 0.065(5) -0.005(3) 0.009(3) 0.000(3) C15 0.058(4) 0.046(4) 0.074(5) 0.015(4) 0.012(4) -0.009(3) C16 0.075(5) 0.039(4) 0.095(6) 0.021(4) 0.002(5) -0.011(4) C17 0.067(4) 0.037(4) 0.077(5) -0.009(4) -0.010(4) -0.001(3) C18 0.046(4) 0.036(3) 0.057(4) -0.006(3) -0.005(3) 0.002(3) C19 0.065(4) 0.043(4) 0.060(5) -0.015(4) -0.009(4) 0.021(3) C20 0.118(7) 0.122(8) 0.059(5) 0.009(5) 0.033(5) 0.073(6) C21 0.269(16) 0.082(7) 0.41(2) -0.095(11) 0.294(18) -0.063(9) C22 0.071(7) 0.72(4) 0.037(6) 0.011(13) 0.004(5) -0.043(13) C23 0.346(19) 0.098(8) 0.095(9) 0.036(7) 0.100(11) 0.095(10) C24 0.112(6) 0.067(5) 0.105(7) 0.013(5) 0.065(6) 0.014(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.935(5) . ? Cu1 O1 1.944(4) . ? Cu1 N3 1.965(4) . ? Cu1 N2 2.004(4) . ? Cu2 N6 1.965(5) . ? Cu2 N12 1.965(5) . ? Cu2 O1 2.000(3) . ? Cu2 N9 2.025(5) . ? Cu2 O2 2.377(4) . ? Cu2 N3 2.437(5) . ? Cu3 N15 1.949(5) . ? Cu3 N9 1.999(5) . ? Cu3 N12 2.004(5) . ? Cu3 O3 2.014(3) . ? Cu3 N18 2.373(5) . ? Cu3 O4 2.377(4) . ? Cu4 O3 1.926(4) . ? Cu4 N21 1.939(5) . ? Cu4 N18 1.968(5) . ? Cu4 N22 1.999(5) . ? O1 C1 1.323(6) . ? O2 C2 1.379(7) . ? O2 C12 1.421(7) . ? O3 C13 1.341(6) . ? O4 C14 1.364(7) . ? O4 C24 1.382(7) . ? N1 C7 1.269(7) . ? N1 C8 1.462(7) . ? N2 C10 1.478(7) . ? N2 C9 1.487(7) . ? N3 N4 1.198(6) . ? N4 N5 1.134(6) . ? N6 N7 1.189(7) . ? N7 N8 1.149(7) . ? N9 N10 1.179(6) . ? N10 N11 1.123(7) . ? N12 N13 1.168(6) . ? N13 N14 1.116(7) . ? N15 N16 1.180(7) . ? N16 N17 1.142(7) . ? N18 N19 1.187(6) . ? N19 N20 1.124(6) . ? N21 C19 1.276(8) . ? N21 C20 1.449(8) . ? N22 C22 1.379(12) . ? N22 C21 1.466(12) . ? C1 C2 1.401(8) . ? C1 C6 1.409(8) . ? C2 C3 1.368(8) . ? C3 C4 1.389(9) . ? C4 C5 1.353(9) . ? C5 C6 1.403(8) . ? C6 C7 1.430(8) . ? C8 C9 1.498(8) . ? C10 C11 1.492(8) . ? C13 C18 1.390(7) . ? C13 C14 1.399(8) . ? C14 C15 1.376(8) . ? C15 C16 1.383(9) . ? C16 C17 1.344(9) . ? C17 C18 1.408(8) . ? C18 C19 1.417(9) . ? C20 C21 1.311(11) . ? C22 C23 1.315(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 O1 90.55(18) . . ? N1 Cu1 N3 170.6(2) . . ? O1 Cu1 N3 86.68(17) . . ? N1 Cu1 N2 85.2(2) . . ? O1 Cu1 N2 171.84(18) . . ? N3 Cu1 N2 96.36(19) . . ? N6 Cu2 N12 93.7(2) . . ? N6 Cu2 O1 95.31(19) . . ? N12 Cu2 O1 171.0(2) . . ? N6 Cu2 N9 172.4(2) . . ? N12 Cu2 N9 78.8(2) . . ? O1 Cu2 N9 92.20(17) . . ? N6 Cu2 O2 89.61(19) . . ? N12 Cu2 O2 107.4(2) . . ? O1 Cu2 O2 73.02(15) . . ? N9 Cu2 O2 91.75(18) . . ? N6 Cu2 N3 91.17(19) . . ? N12 Cu2 N3 105.9(2) . . ? O1 Cu2 N3 73.67(15) . . ? N9 Cu2 N3 91.78(19) . . ? O2 Cu2 N3 146.60(15) . . ? N15 Cu3 N9 95.1(2) . . ? N15 Cu3 N12 173.3(2) . . ? N9 Cu3 N12 78.6(2) . . ? N15 Cu3 O3 95.58(19) . . ? N9 Cu3 O3 169.12(19) . . ? N12 Cu3 O3 90.81(19) . . ? N15 Cu3 N18 93.8(2) . . ? N9 Cu3 N18 103.85(19) . . ? N12 Cu3 N18 89.9(2) . . ? O3 Cu3 N18 73.45(16) . . ? N15 Cu3 O4 90.3(2) . . ? N9 Cu3 O4 109.45(18) . . ? N12 Cu3 O4 89.7(2) . . ? O3 Cu3 O4 72.47(15) . . ? N18 Cu3 O4 145.91(16) . . ? O3 Cu4 N21 91.1(2) . . ? O3 Cu4 N18 85.32(18) . . ? N21 Cu4 N18 170.6(2) . . ? O3 Cu4 N22 173.92(19) . . ? N21 Cu4 N22 85.1(2) . . ? N18 Cu4 N22 97.7(2) . . ? C1 O1 Cu1 128.4(3) . . ? C1 O1 Cu2 122.4(4) . . ? Cu1 O1 Cu2 107.33(17) . . ? C2 O2 C12 119.5(5) . . ? C2 O2 Cu2 110.2(3) . . ? C12 O2 Cu2 129.7(4) . . ? C13 O3 Cu4 129.7(4) . . ? C13 O3 Cu3 122.2(3) . . ? Cu4 O3 Cu3 107.52(18) . . ? C14 O4 C24 120.9(5) . . ? C14 O4 Cu3 111.2(4) . . ? C24 O4 Cu3 127.9(4) . . ? C7 N1 C8 120.2(5) . . ? C7 N1 Cu1 126.7(4) . . ? C8 N1 Cu1 112.9(4) . . ? C10 N2 C9 115.8(5) . . ? C10 N2 Cu1 112.7(3) . . ? C9 N2 Cu1 105.5(4) . . ? N4 N3 Cu1 125.7(4) . . ? N4 N3 Cu2 109.2(4) . . ? Cu1 N3 Cu2 91.77(18) . . ? N5 N4 N3 176.7(6) . . ? N7 N6 Cu2 118.7(4) . . ? N8 N7 N6 177.0(7) . . ? N10 N9 Cu3 128.4(4) . . ? N10 N9 Cu2 125.1(4) . . ? Cu3 N9 Cu2 100.3(2) . . ? N11 N10 N9 176.8(7) . . ? N13 N12 Cu2 130.1(5) . . ? N13 N12 Cu3 127.5(4) . . ? Cu2 N12 Cu3 102.2(2) . . ? N14 N13 N12 178.3(9) . . ? N16 N15 Cu3 118.2(4) . . ? N17 N16 N15 175.2(8) . . ? N19 N18 Cu4 127.6(4) . . ? N19 N18 Cu3 118.9(4) . . ? Cu4 N18 Cu3 93.65(19) . . ? N20 N19 N18 177.2(6) . . ? C19 N21 C20 121.7(6) . . ? C19 N21 Cu4 126.7(4) . . ? C20 N21 Cu4 111.6(5) . . ? C22 N22 C21 112.1(10) . . ? C22 N22 Cu4 123.8(6) . . ? C21 N22 Cu4 104.8(6) . . ? O1 C1 C2 119.9(5) . . ? O1 C1 C6 122.1(5) . . ? C2 C1 C6 118.0(6) . . ? C3 C2 O2 124.6(6) . . ? C3 C2 C1 121.5(6) . . ? O2 C2 C1 113.9(5) . . ? C2 C3 C4 120.3(7) . . ? C5 C4 C3 119.2(7) . . ? C4 C5 C6 122.2(7) . . ? C5 C6 C1 118.7(6) . . ? C5 C6 C7 118.5(6) . . ? C1 C6 C7 122.8(6) . . ? N1 C7 C6 126.8(6) . . ? N1 C8 C9 107.8(5) . . ? N2 C9 C8 108.8(5) . . ? N2 C10 C11 115.2(5) . . ? O3 C13 C18 121.6(6) . . ? O3 C13 C14 118.9(5) . . ? C18 C13 C14 119.4(6) . . ? O4 C14 C15 124.8(6) . . ? O4 C14 C13 114.3(5) . . ? C15 C14 C13 120.7(6) . . ? C14 C15 C16 119.7(7) . . ? C17 C16 C15 120.1(6) . . ? C16 C17 C18 122.1(6) . . ? C13 C18 C17 118.0(6) . . ? C13 C18 C19 123.9(6) . . ? C17 C18 C19 118.2(6) . . ? N21 C19 C18 127.0(6) . . ? C21 C20 N21 113.9(8) . . ? C20 C21 N22 119.5(8) . . ? C23 C22 N22 129.6(11) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.863 _refine_diff_density_min -0.704 _refine_diff_density_rms 0.093 #===END