# 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_1 _database_code_depnum_ccdc_archive 'CCDC 752341' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H22 Cu2 N8, C2 H3 N, Cl O4' _chemical_formula_sum 'C29 H25 Cl Cu2 N9 O4' _chemical_formula_weight 726.11 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 25.897(3) _cell_length_b 10.5743(10) _cell_length_c 11.8334(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3240.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1135 _cell_measurement_theta_min 2.332 _cell_measurement_theta_max 15.710 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1476 _exptl_absorpt_coefficient_mu 1.443 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8459 _exptl_absorpt_correction_T_max 0.8691 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15830 _diffrn_reflns_av_R_equivalents 0.1216 _diffrn_reflns_av_sigmaI/netI 0.1862 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 24.98 _reflns_number_total 5537 _reflns_number_gt 2120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0059P)^2^] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.010(18) _refine_ls_number_reflns 5537 _refine_ls_number_parameters 395 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1537 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0555 _refine_ls_goodness_of_fit_ref 0.771 _refine_ls_restrained_S_all 0.771 _refine_ls_shift/su_max 0.002 _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 Cu1 Cu 0.19876(4) 0.63836(8) 0.13502(10) 0.0620(3) Uani 1 1 d . . . Cu2 Cu 0.25791(4) 0.67779(8) 0.53422(10) 0.0643(3) Uani 1 1 d . . . C1 C 0.1168(4) 0.7732(8) 0.0025(8) 0.073(3) Uani 1 1 d . . . H1 H 0.0943 0.7407 0.0563 0.088 Uiso 1 1 calc R . . C2 C 0.0955(4) 0.8431(10) -0.0823(11) 0.088(4) Uani 1 1 d . . . H2 H 0.0602 0.8588 -0.0858 0.105 Uiso 1 1 calc R . . C3 C 0.1286(6) 0.8886(10) -0.1611(10) 0.096(4) Uani 1 1 d . . . H3 H 0.1160 0.9353 -0.2217 0.116 Uiso 1 1 calc R . . C4 C 0.1810(5) 0.8664(8) -0.1523(8) 0.079(3) Uani 1 1 d . . . H4 H 0.2041 0.8985 -0.2052 0.095 Uiso 1 1 calc R . . C5 C 0.1979(4) 0.7943(7) -0.0617(8) 0.056(2) Uani 1 1 d . . . C6 C 0.2527(4) 0.7699(7) -0.0402(8) 0.053(2) Uani 1 1 d . . . C7 C 0.2931(4) 0.8055(7) -0.1092(8) 0.072(3) Uani 1 1 d . . . H7 H 0.2864 0.8493 -0.1757 0.086 Uiso 1 1 calc R . . C8 C 0.3424(5) 0.7774(9) -0.0809(11) 0.095(4) Uani 1 1 d . . . H8 H 0.3697 0.8013 -0.1273 0.114 Uiso 1 1 calc R . . C9 C 0.3515(4) 0.7110(9) 0.0203(11) 0.097(4) Uani 1 1 d . . . H9 H 0.3848 0.6895 0.0422 0.117 Uiso 1 1 calc R . . C10 C 0.3100(4) 0.6793(8) 0.0852(8) 0.081(2) Uani 1 1 d . . . H10 H 0.3160 0.6354 0.1521 0.097 Uiso 1 1 calc R . . C11 C 0.1064(4) 0.4867(8) 0.1339(10) 0.080(3) Uani 1 1 d . . . H11 H 0.1175 0.4716 0.0604 0.096 Uiso 1 1 calc R . . C12 C 0.0651(4) 0.4185(9) 0.1718(9) 0.090(4) Uani 1 1 d U . . H12 H 0.0494 0.3579 0.1262 0.108 Uiso 1 1 calc R . . C13 C 0.0470(4) 0.4423(10) 0.2804(11) 0.081(2) Uani 1 1 d U . . C14 C 0.0710(4) 0.5343(9) 0.3428(7) 0.076(3) Uani 1 1 d . . . H14 H 0.0593 0.5545 0.4149 0.091 Uiso 1 1 calc R . . C15 C 0.1131(4) 0.5970(8) 0.2966(9) 0.070(3) Uani 1 1 d . . . H15 H 0.1290 0.6593 0.3400 0.084 Uiso 1 1 calc R . . C16 C 0.2448(4) 0.6453(7) 0.3795(7) 0.057(2) Uani 1 1 d . . . C17 C 0.1515(4) 0.6014(7) 0.6355(9) 0.070(2) Uani 1 1 d . . . H17 H 0.1375 0.6529 0.5797 0.084 Uiso 1 1 calc R . . C18 C 0.1178(5) 0.5418(10) 0.7054(8) 0.097(3) Uani 1 1 d . . . H18 H 0.0823 0.5525 0.6988 0.117 Uiso 1 1 calc R . . C19 C 0.1386(5) 0.4668(11) 0.7845(9) 0.097(3) Uani 1 1 d . . . H19 H 0.1168 0.4246 0.8344 0.117 Uiso 1 1 calc R . . C20 C 0.1911(4) 0.4501(8) 0.7945(8) 0.075(3) Uani 1 1 d . . . H20 H 0.2047 0.3959 0.8487 0.090 Uiso 1 1 calc R . . C21 C 0.2234(4) 0.5172(8) 0.7206(7) 0.059(3) Uani 1 1 d . . . C22 C 0.2802(4) 0.5107(7) 0.7243(8) 0.048(2) Uani 1 1 d . . . C23 C 0.3076(5) 0.4542(8) 0.8111(8) 0.073(3) Uani 1 1 d . . . H23 H 0.2901 0.4136 0.8692 0.088 Uiso 1 1 calc R . . C24 C 0.3595(5) 0.4576(10) 0.8119(11) 0.093(4) Uani 1 1 d . . . H24 H 0.3778 0.4208 0.8710 0.112 Uiso 1 1 calc R . . C25 C 0.3851(4) 0.5149(9) 0.7263(11) 0.084(3) Uani 1 1 d . . . H25 H 0.4210 0.5186 0.7254 0.101 Uiso 1 1 calc R . . C26 C 0.3562(4) 0.5675(7) 0.6403(9) 0.063(2) Uani 1 1 d . . . H26 H 0.3738 0.6061 0.5812 0.075 Uiso 1 1 calc R . . C29 C 0.4757(5) 0.7019(9) 0.2645(9) 0.139(5) Uani 1 1 d . . . H29A H 0.5037 0.7232 0.3140 0.209 Uiso 1 1 calc R . . H29B H 0.4763 0.6128 0.2490 0.209 Uiso 1 1 calc R . . H29C H 0.4436 0.7238 0.2999 0.209 Uiso 1 1 calc R . . C28 C 0.4807(5) 0.7685(14) 0.1640(10) 0.109(5) Uani 1 1 d . . . Cl1 Cl 0.02792(14) 0.8799(3) 0.5696(3) 0.0915(9) Uani 1 1 d . . . N1 N 0.1656(3) 0.7473(6) 0.0158(7) 0.057(2) Uani 1 1 d . . . N2 N 0.2613(3) 0.7078(6) 0.0580(6) 0.060(2) Uani 1 1 d . . . N3 N 0.1323(3) 0.5739(7) 0.1945(7) 0.070(2) Uani 1 1 d . . . N4 N 0.0072(3) 0.3738(8) 0.3246(7) 0.113(3) Uani 1 1 d . . . H4A H -0.0031 0.3882 0.3925 0.136 Uiso 1 1 calc R . . H4B H -0.0076 0.3164 0.2847 0.136 Uiso 1 1 calc R . . N6 N 0.2303(3) 0.6429(6) 0.2875(6) 0.064(2) Uani 1 1 d . . . N7 N 0.2034(3) 0.5925(5) 0.6398(7) 0.0568(18) Uani 1 1 d . . . N8 N 0.3043(3) 0.5671(5) 0.6358(8) 0.0563(18) Uani 1 1 d . . . N9 N 0.4884(4) 0.8244(11) 0.0816(8) 0.120(4) Uani 1 1 d . . . N5 N 0.2203(3) 0.4566(7) 0.0867(6) 0.082(3) Uani 1 1 d . . . C27 C 0.2698(4) 0.8493(8) 0.5712(7) 0.073(3) Uani 1 1 d . . . O3 O 0.0626(6) 0.9696(10) 0.5620(11) 0.304(10) Uani 1 1 d . . . O4 O 0.0486(4) 0.7764(8) 0.5239(9) 0.212(5) Uani 1 1 d . . . O1 O -0.0154(5) 0.9107(12) 0.5199(11) 0.274(8) Uani 1 1 d . . . O2 O 0.0190(4) 0.8671(9) 0.6842(6) 0.162(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0642(7) 0.0655(6) 0.0564(6) 0.0047(7) -0.0047(8) -0.0050(7) Cu2 0.0795(9) 0.0612(6) 0.0523(6) 0.0042(7) -0.0046(8) -0.0007(6) C1 0.087(9) 0.061(6) 0.071(8) -0.003(6) -0.026(7) -0.010(6) C2 0.048(8) 0.105(9) 0.110(10) 0.007(8) -0.013(8) -0.012(7) C3 0.096(10) 0.084(8) 0.109(11) 0.003(7) -0.037(9) 0.014(9) C4 0.110(11) 0.075(7) 0.053(6) 0.018(5) -0.002(7) -0.004(8) C5 0.063(8) 0.038(5) 0.068(7) -0.003(5) -0.009(7) 0.000(6) C6 0.057(7) 0.045(6) 0.058(6) -0.005(4) -0.008(6) -0.013(6) C7 0.078(9) 0.057(6) 0.081(7) 0.023(6) 0.009(7) -0.008(7) C8 0.061(9) 0.104(9) 0.119(11) 0.002(8) 0.034(8) -0.024(8) C9 0.083(9) 0.088(7) 0.122(11) 0.017(9) 0.024(10) -0.005(7) C10 0.055(5) 0.089(5) 0.099(6) 0.025(5) 0.004(5) -0.012(5) C11 0.087(9) 0.092(7) 0.062(6) 0.022(7) -0.017(8) -0.010(6) C12 0.092(9) 0.101(8) 0.078(8) 0.008(6) 0.021(7) -0.006(7) C13 0.055(5) 0.089(5) 0.099(6) 0.025(5) 0.004(5) -0.012(5) C14 0.076(8) 0.089(7) 0.062(7) 0.000(6) 0.013(7) 0.000(7) C15 0.074(8) 0.063(7) 0.073(8) -0.008(6) 0.001(6) 0.000(6) C16 0.061(6) 0.053(6) 0.058(6) -0.003(5) -0.003(6) -0.009(6) C17 0.075(7) 0.086(6) 0.049(5) -0.006(7) -0.005(8) 0.008(6) C18 0.085(7) 0.141(9) 0.065(7) 0.003(5) 0.014(6) -0.021(6) C19 0.085(7) 0.141(9) 0.065(7) 0.003(5) 0.014(6) -0.021(6) C20 0.099(9) 0.068(6) 0.059(6) 0.016(5) 0.002(8) -0.019(7) C21 0.079(8) 0.070(6) 0.027(5) -0.001(5) -0.012(6) -0.006(7) C22 0.067(8) 0.040(5) 0.038(6) -0.008(4) 0.000(6) -0.002(6) C23 0.086(9) 0.074(7) 0.061(7) 0.009(5) -0.009(8) -0.012(7) C24 0.095(11) 0.072(8) 0.113(11) 0.010(7) -0.022(10) -0.010(8) C25 0.053(8) 0.073(8) 0.126(11) -0.001(7) -0.018(8) 0.007(7) C26 0.068(7) 0.067(5) 0.053(6) 0.002(6) 0.004(7) 0.005(6) C29 0.219(15) 0.123(10) 0.076(9) 0.015(8) 0.016(10) 0.015(10) C28 0.065(9) 0.170(15) 0.091(11) -0.035(10) 0.001(9) 0.008(9) Cl1 0.091(3) 0.104(2) 0.079(2) 0.0025(18) 0.004(2) 0.010(2) N1 0.047(5) 0.059(4) 0.066(6) 0.005(5) 0.000(5) 0.006(4) N2 0.060(6) 0.072(5) 0.048(6) 0.018(4) -0.014(5) -0.011(5) N3 0.058(6) 0.078(6) 0.075(6) -0.017(5) 0.010(5) -0.012(5) N4 0.079(7) 0.139(7) 0.121(8) 0.021(6) -0.002(6) -0.036(6) N6 0.068(6) 0.063(5) 0.062(5) -0.018(5) -0.018(5) -0.004(4) N7 0.055(5) 0.080(5) 0.035(4) 0.008(5) -0.011(5) 0.004(4) N8 0.051(5) 0.054(4) 0.064(5) 0.013(5) 0.007(6) 0.002(4) N9 0.089(8) 0.193(11) 0.078(8) -0.017(8) 0.012(7) -0.024(7) N5 0.082(7) 0.073(5) 0.090(7) 0.002(4) 0.001(5) -0.004(5) C27 0.084(8) 0.065(6) 0.069(7) -0.005(5) -0.004(5) 0.013(6) O3 0.39(2) 0.245(11) 0.278(18) -0.049(11) 0.164(16) -0.196(13) O4 0.275(12) 0.184(8) 0.177(9) -0.051(8) 0.001(11) 0.139(9) O1 0.206(12) 0.44(2) 0.174(11) -0.005(13) -0.070(11) 0.180(14) O2 0.159(9) 0.266(11) 0.062(6) 0.005(6) -0.022(6) -0.041(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.979(8) . ? Cu1 N6 1.981(7) . ? Cu1 N2 1.999(7) . ? Cu1 N1 2.014(7) . ? Cu1 N5 2.082(8) . ? Cu2 C27 1.891(9) . ? Cu2 C16 1.893(9) . ? Cu2 N8 2.064(7) . ? Cu2 N7 2.090(7) . ? C1 N1 1.301(10) . ? C1 C2 1.364(12) . ? C1 H1 0.9300 . ? C2 C3 1.355(13) . ? C2 H2 0.9300 . ? C3 C4 1.381(14) . ? C3 H3 0.9300 . ? C4 C5 1.387(10) . ? C4 H4 0.9300 . ? C5 N1 1.337(10) . ? C5 C6 1.464(12) . ? C6 N2 1.354(10) . ? C6 C7 1.379(12) . ? C7 C8 1.354(12) . ? C7 H7 0.9300 . ? C8 C9 1.407(13) . ? C8 H8 0.9300 . ? C9 C10 1.362(11) . ? C9 H9 0.9300 . ? C10 N2 1.336(10) . ? C10 H10 0.9300 . ? C11 N3 1.348(9) . ? C11 C12 1.366(11) . ? C11 H11 0.9300 . ? C12 C13 1.391(13) . ? C12 H12 0.9300 . ? C13 N4 1.364(11) . ? C13 C14 1.372(12) . ? C14 C15 1.389(12) . ? C14 H14 0.9300 . ? C15 N3 1.330(10) . ? C15 H15 0.9300 . ? C16 N6 1.152(8) . ? C17 N7 1.350(9) . ? C17 C18 1.356(12) . ? C17 H17 0.9300 . ? C18 C19 1.340(13) . ? C18 H18 0.9300 . ? C19 C20 1.376(13) . ? C19 H19 0.9300 . ? C20 C21 1.403(11) . ? C20 H20 0.9300 . ? C21 N7 1.347(10) . ? C21 C22 1.472(11) . ? C22 N8 1.358(11) . ? C22 C23 1.384(11) . ? C23 C24 1.344(14) . ? C23 H23 0.9300 . ? C24 C25 1.353(13) . ? C24 H24 0.9300 . ? C25 C26 1.381(12) . ? C25 H25 0.9300 . ? C26 N8 1.343(9) . ? C26 H26 0.9300 . ? C29 C28 1.388(13) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C28 N9 1.157(14) . ? Cl1 O1 1.308(10) . ? Cl1 O3 1.309(10) . ? Cl1 O4 1.334(7) . ? Cl1 O2 1.383(7) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N5 C27 1.177(7) 4_544 ? C27 N5 1.177(7) 4 ? 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 N3 Cu1 N6 92.5(3) . . ? N3 Cu1 N2 173.2(3) . . ? N6 Cu1 N2 94.1(3) . . ? N3 Cu1 N1 94.3(3) . . ? N6 Cu1 N1 143.2(3) . . ? N2 Cu1 N1 79.4(3) . . ? N3 Cu1 N5 90.7(3) . . ? N6 Cu1 N5 99.3(3) . . ? N2 Cu1 N5 89.8(3) . . ? N1 Cu1 N5 116.8(3) . . ? C27 Cu2 C16 115.3(3) . . ? C27 Cu2 N8 108.3(3) . . ? C16 Cu2 N8 124.4(3) . . ? C27 Cu2 N7 112.7(3) . . ? C16 Cu2 N7 112.3(4) . . ? N8 Cu2 N7 78.5(3) . . ? N1 C1 C2 126.6(11) . . ? N1 C1 H1 116.7 . . ? C2 C1 H1 116.7 . . ? C3 C2 C1 116.3(11) . . ? C3 C2 H2 121.9 . . ? C1 C2 H2 121.9 . . ? C2 C3 C4 120.7(11) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 117.5(10) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? N1 C5 C4 122.5(10) . . ? N1 C5 C6 115.0(9) . . ? C4 C5 C6 122.4(11) . . ? N2 C6 C7 121.0(9) . . ? N2 C6 C5 113.2(9) . . ? C7 C6 C5 125.8(10) . . ? C8 C7 C6 120.6(10) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 118.5(11) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C10 C9 C8 118.2(11) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? N2 C10 C9 123.5(10) . . ? N2 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? N3 C11 C12 125.3(11) . . ? N3 C11 H11 117.4 . . ? C12 C11 H11 117.4 . . ? C11 C12 C13 118.2(11) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? N4 C13 C14 120.9(12) . . ? N4 C13 C12 120.9(12) . . ? C14 C13 C12 118.2(10) . . ? C13 C14 C15 118.9(10) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? N3 C15 C14 124.3(9) . . ? N3 C15 H15 117.8 . . ? C14 C15 H15 117.8 . . ? N6 C16 Cu2 167.6(8) . . ? N7 C17 C18 125.8(11) . . ? N7 C17 H17 117.1 . . ? C18 C17 H17 117.1 . . ? C19 C18 C17 116.4(12) . . ? C19 C18 H18 121.8 . . ? C17 C18 H18 121.8 . . ? C18 C19 C20 122.1(12) . . ? C18 C19 H19 118.9 . . ? C20 C19 H19 118.9 . . ? C19 C20 C21 118.2(10) . . ? C19 C20 H20 120.9 . . ? C21 C20 H20 120.9 . . ? N7 C21 C20 120.7(10) . . ? N7 C21 C22 115.6(9) . . ? C20 C21 C22 123.6(9) . . ? N8 C22 C23 121.7(10) . . ? N8 C22 C21 114.6(9) . . ? C23 C22 C21 123.7(10) . . ? C24 C23 C22 120.4(11) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 119.8(12) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C24 C25 C26 117.8(11) . . ? C24 C25 H25 121.1 . . ? C26 C25 H25 121.1 . . ? N8 C26 C25 124.8(10) . . ? N8 C26 H26 117.6 . . ? C25 C26 H26 117.6 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N9 C28 C29 175.5(16) . . ? O1 Cl1 O3 112.2(8) . . ? O1 Cl1 O4 111.6(8) . . ? O3 Cl1 O4 106.9(7) . . ? O1 Cl1 O2 108.7(8) . . ? O3 Cl1 O2 104.7(7) . . ? O4 Cl1 O2 112.6(6) . . ? C1 N1 C5 116.6(9) . . ? C1 N1 Cu1 128.2(8) . . ? C5 N1 Cu1 115.2(7) . . ? C10 N2 C6 118.2(8) . . ? C10 N2 Cu1 124.9(6) . . ? C6 N2 Cu1 115.8(7) . . ? C15 N3 C11 115.0(9) . . ? C15 N3 Cu1 125.8(7) . . ? C11 N3 Cu1 118.7(8) . . ? C13 N4 H4A 120.0 . . ? C13 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C16 N6 Cu1 174.6(7) . . ? C21 N7 C17 116.8(9) . . ? C21 N7 Cu2 114.8(7) . . ? C17 N7 Cu2 128.3(7) . . ? C26 N8 C22 115.6(9) . . ? C26 N8 Cu2 127.1(7) . . ? C22 N8 Cu2 115.5(7) . . ? C27 N5 Cu1 172.2(7) 4_544 . ? N5 C27 Cu2 174.7(8) 4 . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.317 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.062 data_2 _database_code_depnum_ccdc_archive 'CCDC 869858' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H22 Cu2 N8, (C2 H3 N), (B F4)' _chemical_formula_sum 'C29 H25 B Cu2 F4 N9' _chemical_formula_weight 713.47 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 25.707(6) _cell_length_b 10.625(3) _cell_length_c 11.749(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3209.1(14) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1379 _cell_measurement_theta_min 2.349 _cell_measurement_theta_max 16.123 _exptl_crystal_description lamella _exptl_crystal_colour brown _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1444 _exptl_absorpt_coefficient_mu 1.383 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8741 _exptl_absorpt_correction_T_max 0.8741 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15623 _diffrn_reflns_av_R_equivalents 0.1209 _diffrn_reflns_av_sigmaI/netI 0.1682 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5581 _reflns_number_gt 2257 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0123P)^2^] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.007(16) _refine_ls_number_reflns 5581 _refine_ls_number_parameters 407 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1432 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.0781 _refine_ls_wR_factor_gt 0.0652 _refine_ls_goodness_of_fit_ref 0.707 _refine_ls_restrained_S_all 0.707 _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 0.19783(3) 0.13692(7) 0.43737(8) 0.0654(3) Uani 1 1 d . . . Cu2 Cu 0.25906(3) 0.17896(7) 0.03658(8) 0.0671(3) Uani 1 1 d . . . N1 N 0.2612(3) 0.2032(6) 0.5172(6) 0.074(2) Uani 1 1 d . . . N2 N 0.1655(3) 0.2490(5) 0.5564(5) 0.0555(16) Uani 1 1 d . . . N3 N 0.1307(2) 0.0743(6) 0.3761(6) 0.0714(19) Uani 1 1 d . . . N4 N 0.0054(3) -0.1283(7) 0.2430(6) 0.122(3) Uani 1 1 d . . . H4A H -0.0092 -0.1867 0.2824 0.146 Uiso 1 1 d R . . H4B H -0.0045 -0.1144 0.1742 0.146 Uiso 1 1 d R . . N5 N 0.2296(2) 0.1419(5) 0.2829(5) 0.0680(18) Uani 1 1 d . . . N6 N 0.3060(3) 0.0691(4) -0.0634(6) 0.0605(14) Uani 1 1 d . . . N7 N 0.2055(3) 0.0939(5) -0.0707(6) 0.0636(16) Uani 1 1 d . . . N8 N 0.2177(2) -0.0426(7) 0.4830(5) 0.080(2) Uani 1 1 d . . . C1 C 0.3105(4) 0.1725(7) 0.4895(6) 0.087(3) Uani 1 1 d . . . H1 H 0.3163 0.1263 0.4235 0.104 Uiso 1 1 calc R . . C2 C 0.3528(4) 0.2071(8) 0.5551(10) 0.101(3) Uani 1 1 d . . . H2 H 0.3866 0.1850 0.5349 0.121 Uiso 1 1 calc R . . C3 C 0.3424(4) 0.2765(9) 0.6529(10) 0.102(3) Uani 1 1 d . . . H3 H 0.3700 0.3028 0.6983 0.122 Uiso 1 1 calc R . . C4 C 0.2945(4) 0.3061(7) 0.6832(7) 0.081(3) Uani 1 1 d . . . H4 H 0.2880 0.3508 0.7497 0.097 Uiso 1 1 calc R . . C5 C 0.2533(3) 0.2679(7) 0.6113(7) 0.061(2) Uani 1 1 d . . . C6 C 0.1979(4) 0.2964(6) 0.6355(7) 0.063(2) Uani 1 1 d . . . C7 C 0.1805(4) 0.3655(7) 0.7248(7) 0.078(2) Uani 1 1 d . . . H7 H 0.2038 0.3952 0.7792 0.094 Uiso 1 1 calc R . . C8 C 0.1284(5) 0.3912(9) 0.7345(9) 0.110(3) Uani 1 1 d . . . H8 H 0.1162 0.4404 0.7943 0.131 Uiso 1 1 calc R . . C9 C 0.0943(4) 0.3440(8) 0.6552(9) 0.092(3) Uani 1 1 d . . . H9 H 0.0587 0.3583 0.6600 0.110 Uiso 1 1 calc R . . C10 C 0.1153(4) 0.2757(7) 0.5702(7) 0.080(3) Uani 1 1 d . . . H10 H 0.0925 0.2442 0.5158 0.096 Uiso 1 1 calc R . . C11 C 0.1123(3) 0.0971(7) 0.2747(8) 0.076(2) Uani 1 1 d . . . H11 H 0.1284 0.1595 0.2318 0.091 Uiso 1 1 calc R . . C12 C 0.0703(4) 0.0348(9) 0.2268(7) 0.088(3) Uani 1 1 d . . . H12 H 0.0588 0.0550 0.1540 0.105 Uiso 1 1 calc R . . C13 C 0.0460(3) -0.0580(9) 0.2894(9) 0.077(2) Uani 1 1 d . . . C14 C 0.0627(4) -0.0802(8) 0.3980(8) 0.094(3) Uani 1 1 d . . . H14 H 0.0464 -0.1385 0.4450 0.112 Uiso 1 1 calc R . . C15 C 0.1039(3) -0.0131(8) 0.4330(8) 0.082(2) Uani 1 1 d . . . H15 H 0.1154 -0.0296 0.5066 0.099 Uiso 1 1 calc R . . C16 C 0.2448(3) 0.1454(7) 0.1890(7) 0.070(2) Uani 1 1 d . . . C17 C 0.3586(3) 0.0714(6) -0.0690(9) 0.075(2) Uani 1 1 d . . . H17 H 0.3762 0.1138 -0.0113 0.090 Uiso 1 1 calc R . . C18 C 0.3879(3) 0.0170(8) -0.1518(8) 0.079(3) Uani 1 1 d . . . H18 H 0.4240 0.0207 -0.1489 0.095 Uiso 1 1 calc R . . C19 C 0.3636(4) -0.0424(8) -0.2384(8) 0.091(3) Uani 1 1 d . . . H19 H 0.3823 -0.0798 -0.2971 0.110 Uiso 1 1 calc R . . C20 C 0.3091(4) -0.0453(7) -0.2362(7) 0.077(2) Uani 1 1 d . . . H20 H 0.2915 -0.0861 -0.2946 0.092 Uiso 1 1 calc R . . C21 C 0.2815(3) 0.0093(6) -0.1518(7) 0.059(2) Uani 1 1 d . . . C22 C 0.2253(3) 0.0147(7) -0.1481(7) 0.057(2) Uani 1 1 d . . . C23 C 0.1930(4) -0.0549(7) -0.2203(7) 0.083(3) Uani 1 1 d . . . H23 H 0.2069 -0.1108 -0.2730 0.099 Uiso 1 1 calc R . . C24 C 0.1398(4) -0.0383(9) -0.2112(8) 0.103(3) Uani 1 1 d . . . H24 H 0.1176 -0.0822 -0.2595 0.124 Uiso 1 1 calc R . . C25 C 0.1199(4) 0.0404(9) -0.1335(8) 0.093(3) Uani 1 1 d . . . H25 H 0.0842 0.0513 -0.1273 0.111 Uiso 1 1 calc R . . C26 C 0.1526(4) 0.1035(7) -0.0645(9) 0.083(2) Uani 1 1 d . . . H26 H 0.1383 0.1564 -0.0097 0.100 Uiso 1 1 calc R . . C27 C 0.2276(3) -0.1519(8) 0.4986(5) 0.068(2) Uani 1 1 d . . . N9 N 0.4884(4) 0.3149(12) 0.4842(8) 0.153(5) Uani 1 1 d . . . C28 C 0.4807(5) 0.2613(13) 0.4049(11) 0.123(4) Uani 1 1 d . . . C29 C 0.4751(4) 0.1914(10) 0.3025(10) 0.167(5) Uani 1 1 d . . . H29A H 0.5076 0.1911 0.2619 0.250 Uiso 1 1 calc R . . H29B H 0.4487 0.2294 0.2560 0.250 Uiso 1 1 calc R . . H29C H 0.4653 0.1064 0.3203 0.250 Uiso 1 1 calc R . . F1 F 0.4495(3) 0.7812(7) 0.5422(8) 0.242(4) Uani 1 1 d . . . F2 F 0.5117(3) 0.9002(11) 0.5459(7) 0.293(7) Uani 1 1 d . . . F3 F 0.4798(2) 0.8588(7) 0.3885(5) 0.178(3) Uani 1 1 d . . . F4 F 0.4385(4) 0.9648(9) 0.5015(8) 0.320(8) Uani 1 1 d . . . B1 B 0.4731(8) 0.8718(19) 0.4940(14) 0.136(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 Cu1 0.0675(6) 0.0731(5) 0.0557(5) -0.0078(6) 0.0036(6) -0.0065(5) Cu2 0.0811(7) 0.0681(5) 0.0522(5) -0.0047(6) 0.0060(7) -0.0004(5) N1 0.074(5) 0.077(5) 0.070(6) -0.032(4) 0.009(4) -0.019(4) N2 0.061(4) 0.057(4) 0.049(4) -0.003(4) 0.004(4) -0.004(3) N3 0.074(5) 0.089(5) 0.052(4) 0.002(4) 0.008(4) -0.016(4) N4 0.084(6) 0.154(6) 0.126(7) -0.035(6) 0.009(5) -0.035(5) N5 0.083(5) 0.069(4) 0.052(4) -0.003(4) -0.005(4) -0.004(3) N6 0.074(5) 0.054(3) 0.053(4) -0.015(4) -0.001(4) -0.006(3) N7 0.068(5) 0.069(4) 0.054(4) -0.013(5) 0.005(4) 0.005(3) N8 0.090(5) 0.083(5) 0.068(5) -0.009(4) -0.013(3) -0.030(4) C1 0.052(6) 0.120(7) 0.089(7) -0.024(5) 0.014(5) -0.008(6) C2 0.066(7) 0.112(8) 0.124(9) 0.001(8) 0.003(8) -0.012(6) C3 0.080(9) 0.101(8) 0.125(10) 0.004(7) -0.019(7) -0.034(7) C4 0.078(7) 0.086(7) 0.078(6) -0.027(5) -0.004(6) -0.024(6) C5 0.062(6) 0.052(5) 0.069(6) 0.000(4) -0.002(5) -0.016(5) C6 0.085(7) 0.052(5) 0.053(5) 0.001(4) 0.009(5) -0.016(5) C7 0.088(7) 0.076(6) 0.071(6) -0.025(5) 0.004(5) -0.007(6) C8 0.109(10) 0.095(8) 0.125(10) -0.014(7) 0.051(8) -0.001(7) C9 0.059(7) 0.094(8) 0.123(9) -0.013(7) 0.018(7) -0.004(6) C10 0.095(8) 0.070(6) 0.074(7) -0.005(5) 0.010(6) -0.007(5) C11 0.082(7) 0.074(6) 0.071(6) -0.008(5) -0.003(5) -0.007(5) C12 0.085(7) 0.095(7) 0.082(7) -0.005(6) -0.023(6) -0.009(6) C13 0.049(6) 0.083(7) 0.098(8) -0.027(6) -0.007(6) -0.011(5) C14 0.070(7) 0.124(8) 0.087(9) -0.015(6) -0.002(6) -0.017(6) C15 0.074(6) 0.118(7) 0.055(5) -0.012(7) 0.013(6) 0.004(5) C16 0.069(6) 0.080(6) 0.060(5) 0.013(5) -0.005(4) -0.009(5) C17 0.070(6) 0.074(5) 0.081(6) -0.009(6) -0.008(7) 0.002(5) C18 0.068(7) 0.082(7) 0.089(7) -0.009(6) 0.019(6) 0.003(5) C19 0.105(9) 0.083(7) 0.086(8) -0.011(6) 0.046(7) 0.006(6) C20 0.102(8) 0.074(6) 0.055(6) -0.016(4) -0.005(6) -0.013(6) C21 0.083(7) 0.050(5) 0.043(5) 0.004(4) 0.012(5) 0.006(5) C22 0.060(6) 0.059(6) 0.053(5) 0.004(4) -0.007(5) 0.002(5) C23 0.100(8) 0.088(6) 0.060(6) -0.010(5) -0.002(6) -0.011(6) C24 0.088(8) 0.133(10) 0.088(8) -0.003(7) -0.041(7) -0.037(7) C25 0.067(8) 0.117(9) 0.093(8) -0.016(6) 0.006(6) 0.005(6) C26 0.080(7) 0.100(7) 0.069(5) 0.001(7) -0.001(7) 0.002(5) C27 0.069(5) 0.083(6) 0.051(5) -0.002(4) 0.006(4) -0.017(5) N9 0.102(7) 0.216(12) 0.141(12) -0.038(8) -0.001(7) -0.025(7) C28 0.079(8) 0.163(14) 0.126(13) 0.009(9) 0.017(9) -0.002(8) C29 0.192(13) 0.180(13) 0.128(10) -0.028(9) 0.025(10) 0.017(9) F1 0.261(9) 0.213(8) 0.251(9) 0.040(8) -0.008(9) -0.134(7) F2 0.238(10) 0.501(17) 0.139(6) 0.010(9) -0.057(7) -0.203(11) F3 0.129(6) 0.294(9) 0.112(5) -0.040(6) -0.007(4) 0.022(5) F4 0.376(15) 0.279(10) 0.305(16) -0.003(9) 0.112(11) 0.183(11) B1 0.147(17) 0.180(17) 0.081(10) -0.072(10) 0.008(11) -0.051(14) _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 N3 1.984(6) . ? Cu1 N5 1.990(6) . ? Cu1 N1 2.008(7) . ? Cu1 N2 2.016(6) . ? Cu1 N8 2.046(7) . ? Cu2 C16 1.862(8) . ? Cu2 C27 1.883(9) 3_554 ? Cu2 N6 2.049(6) . ? Cu2 N7 2.074(6) . ? N1 C5 1.318(9) . ? N1 C1 1.349(8) . ? N2 C10 1.331(9) . ? N2 C6 1.346(8) . ? N3 C11 1.305(8) . ? N3 C15 1.335(8) . ? N4 C13 1.393(9) . ? N4 H4A 0.8601 . ? N4 H4B 0.8598 . ? N5 C16 1.172(7) . ? N6 C17 1.355(7) . ? N6 C21 1.370(9) . ? N7 C22 1.339(9) . ? N7 C26 1.367(8) . ? N8 C27 1.203(7) . ? C1 C2 1.383(10) . ? C1 H1 0.9300 . ? C2 C3 1.392(11) . ? C2 H2 0.9300 . ? C3 C4 1.320(10) . ? C3 H3 0.9300 . ? C4 C5 1.414(10) . ? C4 H4 0.9300 . ? C5 C6 1.483(10) . ? C6 C7 1.357(9) . ? C7 C8 1.373(12) . ? C7 H7 0.9300 . ? C8 C9 1.373(11) . ? C8 H8 0.9300 . ? C9 C10 1.347(10) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.386(10) . ? C11 H11 0.9300 . ? C12 C13 1.380(10) . ? C12 H12 0.9300 . ? C13 C14 1.367(10) . ? C14 C15 1.342(9) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.359(9) . ? C17 H17 0.9300 . ? C18 C19 1.351(10) . ? C18 H18 0.9300 . ? C19 C20 1.401(11) . ? C19 H19 0.9300 . ? C20 C21 1.351(9) . ? C20 H20 0.9300 . ? C21 C22 1.446(9) . ? C22 C23 1.399(9) . ? C23 C24 1.384(11) . ? C23 H23 0.9300 . ? C24 C25 1.339(11) . ? C24 H24 0.9300 . ? C25 C26 1.345(10) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 Cu2 1.883(9) 3_545 ? N9 C28 1.110(13) . ? C28 C29 1.421(12) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? F1 B1 1.271(18) . ? F2 B1 1.204(17) . ? F3 B1 1.259(13) . ? F4 B1 1.33(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N5 92.0(3) . . ? N3 Cu1 N1 173.1(3) . . ? N5 Cu1 N1 94.8(3) . . ? N3 Cu1 N2 95.2(3) . . ? N5 Cu1 N2 141.8(2) . . ? N1 Cu1 N2 78.7(3) . . ? N3 Cu1 N8 89.9(2) . . ? N5 Cu1 N8 99.3(2) . . ? N1 Cu1 N8 90.1(2) . . ? N2 Cu1 N8 118.1(2) . . ? C16 Cu2 C27 116.5(3) . 3_554 ? C16 Cu2 N6 123.9(3) . . ? C27 Cu2 N6 107.5(2) 3_554 . ? C16 Cu2 N7 111.7(3) . . ? C27 Cu2 N7 113.1(3) 3_554 . ? N6 Cu2 N7 78.1(3) . . ? C5 N1 C1 118.3(7) . . ? C5 N1 Cu1 116.7(6) . . ? C1 N1 Cu1 124.4(6) . . ? C10 N2 C6 115.9(7) . . ? C10 N2 Cu1 127.6(6) . . ? C6 N2 Cu1 116.4(6) . . ? C11 N3 C15 113.5(8) . . ? C11 N3 Cu1 125.8(6) . . ? C15 N3 Cu1 120.0(6) . . ? C13 N4 H4A 120.2 . . ? C13 N4 H4B 119.8 . . ? H4A N4 H4B 120.0 . . ? C16 N5 Cu1 175.3(6) . . ? C17 N6 C21 115.5(7) . . ? C17 N6 Cu2 127.2(6) . . ? C21 N6 Cu2 115.3(5) . . ? C22 N7 C26 117.6(7) . . ? C22 N7 Cu2 115.7(6) . . ? C26 N7 Cu2 126.6(7) . . ? C27 N8 Cu1 173.1(5) . . ? N1 C1 C2 122.7(8) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 116.7(9) . . ? C1 C2 H2 121.6 . . ? C3 C2 H2 121.6 . . ? C4 C3 C2 121.9(10) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 118.0(9) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? N1 C5 C4 122.4(8) . . ? N1 C5 C6 114.5(8) . . ? C4 C5 C6 123.1(8) . . ? N2 C6 C7 122.2(8) . . ? N2 C6 C5 112.7(7) . . ? C7 C6 C5 125.1(8) . . ? C6 C7 C8 119.6(9) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 119.5(9) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 116.4(9) . . ? C10 C9 H9 121.8 . . ? C8 C9 H9 121.8 . . ? N2 C10 C9 126.4(9) . . ? N2 C10 H10 116.8 . . ? C9 C10 H10 116.8 . . ? N3 C11 C12 124.4(8) . . ? N3 C11 H11 117.8 . . ? C12 C11 H11 117.8 . . ? C13 C12 C11 118.5(8) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C14 C13 C12 118.6(8) . . ? C14 C13 N4 120.6(10) . . ? C12 C13 N4 120.9(10) . . ? C15 C14 C13 116.3(9) . . ? C15 C14 H14 121.9 . . ? C13 C14 H14 121.9 . . ? N3 C15 C14 128.6(9) . . ? N3 C15 H15 115.7 . . ? C14 C15 H15 115.7 . . ? N5 C16 Cu2 167.8(7) . . ? N6 C17 C18 125.4(9) . . ? N6 C17 H17 117.3 . . ? C18 C17 H17 117.3 . . ? C19 C18 C17 118.8(9) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C18 C19 C20 117.3(9) . . ? C18 C19 H19 121.3 . . ? C20 C19 H19 121.3 . . ? C21 C20 C19 122.0(8) . . ? C21 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? C20 C21 N6 120.9(8) . . ? C20 C21 C22 124.4(9) . . ? N6 C21 C22 114.7(8) . . ? N7 C22 C23 121.1(8) . . ? N7 C22 C21 115.2(8) . . ? C23 C22 C21 123.6(9) . . ? C24 C23 C22 118.3(9) . . ? C24 C23 H23 120.9 . . ? C22 C23 H23 120.9 . . ? C25 C24 C23 120.6(9) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 119.0(10) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? C25 C26 N7 123.5(9) . . ? C25 C26 H26 118.3 . . ? N7 C26 H26 118.3 . . ? N8 C27 Cu2 174.8(6) . 3_545 ? N9 C28 C29 175.6(15) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? F2 B1 F3 114.4(18) . . ? F2 B1 F1 111.0(18) . . ? F3 B1 F1 114.9(13) . . ? F2 B1 F4 109.3(14) . . ? F3 B1 F4 103.8(18) . . ? F1 B1 F4 102.4(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 N1 C5 -19(3) . . . . ? N5 Cu1 N1 C5 150.8(6) . . . . ? N2 Cu1 N1 C5 8.8(6) . . . . ? N8 Cu1 N1 C5 -109.9(6) . . . . ? N3 Cu1 N1 C1 152(2) . . . . ? N5 Cu1 N1 C1 -38.1(7) . . . . ? N2 Cu1 N1 C1 180.0(7) . . . . ? N8 Cu1 N1 C1 61.2(7) . . . . ? N3 Cu1 N2 C10 -7.2(6) . . . . ? N5 Cu1 N2 C10 92.7(7) . . . . ? N1 Cu1 N2 C10 176.1(6) . . . . ? N8 Cu1 N2 C10 -100.0(6) . . . . ? N3 Cu1 N2 C6 168.3(5) . . . . ? N5 Cu1 N2 C6 -91.7(6) . . . . ? N1 Cu1 N2 C6 -8.4(5) . . . . ? N8 Cu1 N2 C6 75.6(5) . . . . ? N5 Cu1 N3 C11 -29.1(7) . . . . ? N1 Cu1 N3 C11 141(2) . . . . ? N2 Cu1 N3 C11 113.3(7) . . . . ? N8 Cu1 N3 C11 -128.4(7) . . . . ? N5 Cu1 N3 C15 140.6(6) . . . . ? N1 Cu1 N3 C15 -49(3) . . . . ? N2 Cu1 N3 C15 -76.9(6) . . . . ? N8 Cu1 N3 C15 41.3(6) . . . . ? N3 Cu1 N5 C16 23(7) . . . . ? N1 Cu1 N5 C16 -156(7) . . . . ? N2 Cu1 N5 C16 -78(7) . . . . ? N8 Cu1 N5 C16 113(7) . . . . ? C16 Cu2 N6 C17 -82.1(7) . . . . ? C27 Cu2 N6 C17 58.9(7) 3_554 . . . ? N7 Cu2 N6 C17 169.6(7) . . . . ? C16 Cu2 N6 C21 114.5(6) . . . . ? C27 Cu2 N6 C21 -104.6(5) 3_554 . . . ? N7 Cu2 N6 C21 6.1(5) . . . . ? C16 Cu2 N7 C22 -122.3(6) . . . . ? C27 Cu2 N7 C22 103.9(5) 3_554 . . . ? N6 Cu2 N7 C22 -0.3(5) . . . . ? C16 Cu2 N7 C26 52.5(7) . . . . ? C27 Cu2 N7 C26 -81.3(7) 3_554 . . . ? N6 Cu2 N7 C26 174.5(7) . . . . ? N3 Cu1 N8 C27 47(5) . . . . ? N5 Cu1 N8 C27 -45(5) . . . . ? N1 Cu1 N8 C27 -140(5) . . . . ? N2 Cu1 N8 C27 142(5) . . . . ? C5 N1 C1 C2 -0.5(12) . . . . ? Cu1 N1 C1 C2 -171.5(6) . . . . ? N1 C1 C2 C3 -0.2(13) . . . . ? C1 C2 C3 C4 1.3(14) . . . . ? C2 C3 C4 C5 -1.6(14) . . . . ? C1 N1 C5 C4 0.2(11) . . . . ? Cu1 N1 C5 C4 171.9(5) . . . . ? C1 N1 C5 C6 -179.5(6) . . . . ? Cu1 N1 C5 C6 -7.9(8) . . . . ? C3 C4 C5 N1 0.8(12) . . . . ? C3 C4 C5 C6 -179.4(7) . . . . ? C10 N2 C6 C7 1.0(10) . . . . ? Cu1 N2 C6 C7 -175.1(5) . . . . ? C10 N2 C6 C5 -177.2(6) . . . . ? Cu1 N2 C6 C5 6.7(7) . . . . ? N1 C5 C6 N2 0.7(9) . . . . ? C4 C5 C6 N2 -179.0(7) . . . . ? N1 C5 C6 C7 -177.4(7) . . . . ? C4 C5 C6 C7 2.8(11) . . . . ? N2 C6 C7 C8 -1.6(12) . . . . ? C5 C6 C7 C8 176.4(8) . . . . ? C6 C7 C8 C9 1.7(14) . . . . ? C7 C8 C9 C10 -1.2(15) . . . . ? C6 N2 C10 C9 -0.5(12) . . . . ? Cu1 N2 C10 C9 175.0(6) . . . . ? C8 C9 C10 N2 0.7(14) . . . . ? C15 N3 C11 C12 -2.5(12) . . . . ? Cu1 N3 C11 C12 167.9(6) . . . . ? N3 C11 C12 C13 0.0(13) . . . . ? C11 C12 C13 C14 3.2(13) . . . . ? C11 C12 C13 N4 -176.5(8) . . . . ? C12 C13 C14 C15 -3.5(13) . . . . ? N4 C13 C14 C15 176.2(7) . . . . ? C11 N3 C15 C14 2.1(13) . . . . ? Cu1 N3 C15 C14 -168.9(7) . . . . ? C13 C14 C15 N3 0.9(14) . . . . ? Cu1 N5 C16 Cu2 47(10) . . . . ? C27 Cu2 C16 N5 49(3) 3_554 . . . ? N6 Cu2 C16 N5 -173(3) . . . . ? N7 Cu2 C16 N5 -83(3) . . . . ? C21 N6 C17 C18 -2.0(11) . . . . ? Cu2 N6 C17 C18 -165.5(6) . . . . ? N6 C17 C18 C19 1.7(13) . . . . ? C17 C18 C19 C20 -0.8(13) . . . . ? C18 C19 C20 C21 0.4(13) . . . . ? C19 C20 C21 N6 -0.8(11) . . . . ? C19 C20 C21 C22 176.7(8) . . . . ? C17 N6 C21 C20 1.5(10) . . . . ? Cu2 N6 C21 C20 167.0(5) . . . . ? C17 N6 C21 C22 -176.2(6) . . . . ? Cu2 N6 C21 C22 -10.8(8) . . . . ? C26 N7 C22 C23 0.4(11) . . . . ? Cu2 N7 C22 C23 175.7(5) . . . . ? C26 N7 C22 C21 179.4(7) . . . . ? Cu2 N7 C22 C21 -5.3(8) . . . . ? C20 C21 C22 N7 -167.1(7) . . . . ? N6 C21 C22 N7 10.6(9) . . . . ? C20 C21 C22 C23 11.9(11) . . . . ? N6 C21 C22 C23 -170.5(6) . . . . ? N7 C22 C23 C24 1.1(11) . . . . ? C21 C22 C23 C24 -177.8(7) . . . . ? C22 C23 C24 C25 -1.4(14) . . . . ? C23 C24 C25 C26 0.2(15) . . . . ? C24 C25 C26 N7 1.4(15) . . . . ? C22 N7 C26 C25 -1.7(12) . . . . ? Cu2 N7 C26 C25 -176.4(6) . . . . ? Cu1 N8 C27 Cu2 -141(5) . . . 3_545 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.252 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.050 data_3 _database_code_depnum_ccdc_archive 'CCDC 869860' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C21 H16 Cu N5), 2(B F4), (H2 O)' _chemical_formula_sum 'C42 H34 B2 Cu2 F8 N10 O' _chemical_formula_weight 995.49 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M '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 8.8668(7) _cell_length_b 19.0323(15) _cell_length_c 25.6999(19) _cell_angle_alpha 90.00 _cell_angle_beta 102.594(2) _cell_angle_gamma 90.00 _cell_volume 4232.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2824 _cell_measurement_theta_min 2.289 _cell_measurement_theta_max 20.234 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 1.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8805 _exptl_absorpt_correction_T_max 0.8989 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21213 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0898 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7440 _reflns_number_gt 3372 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0918P)^2^] 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 7440 _refine_ls_number_parameters 586 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1243 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1762 _refine_ls_wR_factor_gt 0.1563 _refine_ls_goodness_of_fit_ref 0.850 _refine_ls_restrained_S_all 0.867 _refine_ls_shift/su_max 0.004 _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 0.49122(8) 0.80045(4) 0.83018(3) 0.0689(3) Uani 1 1 d . . . N1 N 0.6311(5) 0.8736(2) 0.87171(17) 0.0649(12) Uani 1 1 d . . . N2 N 0.6920(5) 0.7395(2) 0.86407(18) 0.0635(12) Uani 1 1 d . . . N3 N 0.5357(5) 0.8241(3) 0.75541(19) 0.0666(13) Uani 1 1 d . . . N4 N 0.3807(5) 0.7218(3) 0.7856(2) 0.0712(13) Uani 1 1 d . . . N5 N 0.2307(8) 0.8470(3) 0.8852(3) 0.115(2) Uani 1 1 d . . . C1 C 0.5882(7) 0.9414(3) 0.8749(3) 0.0752(17) Uani 1 1 d . . . H1 H 0.4913 0.9555 0.8559 0.090 Uiso 1 1 calc R . . C2 C 0.6819(8) 0.9894(3) 0.9048(3) 0.0785(18) Uani 1 1 d . . . H2 H 0.6517 1.0362 0.9052 0.094 Uiso 1 1 calc R . . C3 C 0.8229(8) 0.9677(4) 0.9347(3) 0.0803(18) Uani 1 1 d . . . H3 H 0.8874 0.9995 0.9564 0.096 Uiso 1 1 calc R . . C4 C 0.8667(6) 0.8998(3) 0.9323(2) 0.0731(17) Uani 1 1 d . . . H4 H 0.9617 0.8848 0.9523 0.088 Uiso 1 1 calc R . . C5 C 0.7693(6) 0.8530(3) 0.9000(2) 0.0583(14) Uani 1 1 d . . . C6 C 0.8059(6) 0.7784(3) 0.8930(2) 0.0585(14) Uani 1 1 d . . . C7 C 0.9493(7) 0.7492(3) 0.9150(2) 0.0744(17) Uani 1 1 d . . . H7 H 1.0268 0.7763 0.9358 0.089 Uiso 1 1 calc R . . C8 C 0.9749(8) 0.6797(4) 0.9055(3) 0.089(2) Uani 1 1 d . . . H8 H 1.0705 0.6593 0.9195 0.106 Uiso 1 1 calc R . . C9 C 0.8582(8) 0.6406(3) 0.8751(3) 0.0839(19) Uani 1 1 d . . . H9 H 0.8731 0.5934 0.8682 0.101 Uiso 1 1 calc R . . C10 C 0.7203(7) 0.6722(3) 0.8554(2) 0.0736(17) Uani 1 1 d . . . H10 H 0.6416 0.6456 0.8347 0.088 Uiso 1 1 calc R . . C11 C 0.6129(7) 0.8785(4) 0.7424(3) 0.0813(18) Uani 1 1 d . . . H11 H 0.6498 0.9122 0.7683 0.098 Uiso 1 1 calc R . . C12 C 0.6410(8) 0.8873(4) 0.6916(3) 0.096(2) Uani 1 1 d . . . H12 H 0.6932 0.9267 0.6833 0.116 Uiso 1 1 calc R . . C13 C 0.5907(9) 0.8371(5) 0.6543(3) 0.096(2) Uani 1 1 d . . . H13 H 0.6105 0.8408 0.6203 0.115 Uiso 1 1 calc R . . C14 C 0.5096(8) 0.7807(4) 0.6678(3) 0.086(2) Uani 1 1 d . . . H14 H 0.4725 0.7464 0.6425 0.103 Uiso 1 1 calc R . . C15 C 0.4837(6) 0.7749(3) 0.7178(3) 0.0664(16) Uani 1 1 d . . . C16 C 0.3985(6) 0.7179(3) 0.7353(3) 0.0678(16) Uani 1 1 d . . . C17 C 0.3354(8) 0.6616(4) 0.7042(3) 0.090(2) Uani 1 1 d . . . H17 H 0.3474 0.6577 0.6693 0.108 Uiso 1 1 calc R . . C18 C 0.2544(8) 0.6111(4) 0.7255(4) 0.103(3) Uani 1 1 d . . . H18 H 0.2128 0.5730 0.7046 0.124 Uiso 1 1 calc R . . C19 C 0.2345(8) 0.6160(4) 0.7758(3) 0.095(2) Uani 1 1 d . . . H19 H 0.1789 0.5825 0.7902 0.114 Uiso 1 1 calc R . . C20 C 0.3001(8) 0.6726(4) 0.8048(3) 0.0869(19) Uani 1 1 d . . . H20 H 0.2881 0.6771 0.8397 0.104 Uiso 1 1 calc R . . C21 C 0.3238(8) 0.8265(4) 0.8649(3) 0.0790(19) Uani 1 1 d . . . Cu2 Cu 0.98974(8) 0.73787(4) 0.58062(3) 0.0701(3) Uani 1 1 d . . . N6 N 1.1081(5) 0.8275(2) 0.5938(2) 0.0679(13) Uani 1 1 d . . . N7 N 0.9707(5) 0.7593(3) 0.65867(19) 0.0656(12) Uani 1 1 d . . . N8 N 0.8539(5) 0.6529(2) 0.5711(2) 0.0744(14) Uani 1 1 d . . . N9 N 0.7842(5) 0.7782(2) 0.53329(18) 0.0633(12) Uani 1 1 d . . . N10 N 1.2424(7) 0.6543(3) 0.5406(3) 0.105(2) Uani 1 1 d . . . C22 C 1.1758(7) 0.8583(3) 0.5585(3) 0.0861(19) Uani 1 1 d . . . H22 H 1.1656 0.8381 0.5250 0.103 Uiso 1 1 calc R . . C23 C 1.2614(7) 0.9195(4) 0.5702(3) 0.094(2) Uani 1 1 d . . . H23 H 1.3069 0.9403 0.5447 0.113 Uiso 1 1 calc R . . C24 C 1.2777(8) 0.9484(3) 0.6188(3) 0.088(2) Uani 1 1 d . . . H24 H 1.3364 0.9889 0.6275 0.106 Uiso 1 1 calc R . . C25 C 1.2081(7) 0.9179(3) 0.6550(3) 0.0808(18) Uani 1 1 d . . . H25 H 1.2173 0.9381 0.6885 0.097 Uiso 1 1 calc R . . C26 C 1.1234(6) 0.8571(3) 0.6423(2) 0.0585(14) Uani 1 1 d . . . C27 C 1.0468(6) 0.8178(3) 0.6791(2) 0.0625(15) Uani 1 1 d . . . C28 C 1.0538(7) 0.8385(4) 0.7312(3) 0.0863(19) Uani 1 1 d . . . H28 H 1.1046 0.8794 0.7449 0.104 Uiso 1 1 calc R . . C29 C 0.9827(9) 0.7960(5) 0.7615(3) 0.109(3) Uani 1 1 d . . . H29 H 0.9887 0.8074 0.7971 0.131 Uiso 1 1 calc R . . C30 C 0.9041(8) 0.7379(5) 0.7411(4) 0.097(2) Uani 1 1 d . . . H30 H 0.8529 0.7104 0.7617 0.116 Uiso 1 1 calc R . . C31 C 0.9021(7) 0.7208(3) 0.6896(3) 0.0797(18) Uani 1 1 d . . . H31 H 0.8503 0.6803 0.6755 0.096 Uiso 1 1 calc R . . C32 C 0.8995(7) 0.5893(4) 0.5915(3) 0.092(2) Uani 1 1 d . . . H32 H 0.9990 0.5845 0.6122 0.110 Uiso 1 1 calc R . . C33 C 0.8045(10) 0.5307(4) 0.5830(4) 0.107(2) Uani 1 1 d . . . H33 H 0.8392 0.4873 0.5974 0.128 Uiso 1 1 calc R . . C34 C 0.6604(10) 0.5386(4) 0.5532(3) 0.105(2) Uani 1 1 d . . . H34 H 0.5951 0.4999 0.5462 0.126 Uiso 1 1 calc R . . C35 C 0.6088(7) 0.6036(4) 0.5330(3) 0.092(2) Uani 1 1 d . . . H35 H 0.5080 0.6094 0.5136 0.110 Uiso 1 1 calc R . . C36 C 0.7102(7) 0.6602(3) 0.5423(2) 0.0675(16) Uani 1 1 d . . . C37 C 0.6703(7) 0.7309(3) 0.5218(2) 0.0665(15) Uani 1 1 d . . . C38 C 0.5235(7) 0.7494(4) 0.4919(3) 0.088(2) Uani 1 1 d . . . H38 H 0.4445 0.7163 0.4847 0.105 Uiso 1 1 calc R . . C39 C 0.4990(9) 0.8161(5) 0.4737(3) 0.104(2) Uani 1 1 d . . . H39 H 0.4030 0.8288 0.4532 0.125 Uiso 1 1 calc R . . C40 C 0.6156(8) 0.8650(4) 0.4855(3) 0.090(2) Uani 1 1 d . . . H40 H 0.5998 0.9113 0.4739 0.108 Uiso 1 1 calc R . . C41 C 0.7563(7) 0.8432(3) 0.5151(2) 0.0760(17) Uani 1 1 d . . . H41 H 0.8362 0.8758 0.5227 0.091 Uiso 1 1 calc R . . C42 C 1.1539(7) 0.6873(3) 0.5556(2) 0.0680(16) Uani 1 1 d . . . F5 F 0.2455(8) 0.5773(3) 0.9026(4) 0.237(3) Uani 1 1 d U . . F6 F 0.1577(7) 0.4817(4) 0.8758(3) 0.241(4) Uani 1 1 d U . . F7 F 0.1925(12) 0.5196(5) 0.9542(3) 0.276(4) Uani 1 1 d U . . F8 F 0.3757(7) 0.4849(4) 0.9222(3) 0.245(4) Uani 1 1 d U . . B2 B 0.261(2) 0.5168(6) 0.9085(5) 0.206(7) Uani 1 1 d U . . F1 F 0.8566(8) 0.5608(4) 0.7377(4) 0.288(5) Uani 1 1 d . . . F2 F 0.6484(9) 0.5580(4) 0.7645(3) 0.250(4) Uani 1 1 d . . . F3 F 0.6363(5) 0.5817(2) 0.67991(18) 0.1312(15) Uani 1 1 d . . . F4 F 0.7096(7) 0.4786(3) 0.7159(2) 0.176(2) Uani 1 1 d . . . B1 B 0.7116(13) 0.5471(5) 0.7245(4) 0.101(3) Uani 1 1 d . . . O1 O 0.9547(10) 0.9593(6) 0.8139(4) 0.291(5) Uani 1 1 d . . . H1A H 1.0223 0.9315 0.8314 0.437 Uiso 1 1 d R . . H1B H 0.9990 0.9957 0.8053 0.437 Uiso 1 1 d 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 0.0575(5) 0.0757(5) 0.0717(5) -0.0028(4) 0.0099(3) -0.0071(3) N1 0.054(3) 0.067(3) 0.070(3) 0.001(2) 0.006(2) 0.004(2) N2 0.061(3) 0.067(3) 0.063(3) -0.001(2) 0.014(2) -0.005(2) N3 0.055(3) 0.070(3) 0.072(3) 0.015(3) 0.006(2) 0.003(2) N4 0.062(3) 0.073(3) 0.075(4) -0.001(3) 0.008(3) -0.008(3) N5 0.122(6) 0.105(5) 0.130(6) -0.004(4) 0.053(4) -0.032(4) C1 0.065(4) 0.069(4) 0.089(5) 0.003(4) 0.011(3) 0.006(3) C2 0.086(5) 0.061(4) 0.093(5) -0.004(4) 0.028(4) -0.011(4) C3 0.082(5) 0.077(5) 0.081(5) -0.013(4) 0.017(4) -0.023(4) C4 0.056(4) 0.076(4) 0.085(5) 0.003(4) 0.010(3) -0.002(3) C5 0.050(3) 0.065(4) 0.062(4) 0.004(3) 0.016(3) -0.004(3) C6 0.056(4) 0.068(4) 0.054(3) 0.005(3) 0.017(3) 0.000(3) C7 0.057(4) 0.092(5) 0.071(4) 0.009(3) 0.008(3) 0.005(3) C8 0.083(5) 0.095(5) 0.086(5) 0.012(4) 0.017(4) 0.030(4) C9 0.094(5) 0.069(4) 0.089(5) 0.000(4) 0.020(4) 0.013(4) C10 0.078(5) 0.066(4) 0.077(4) 0.000(3) 0.017(3) 0.003(3) C11 0.076(4) 0.086(5) 0.081(5) 0.014(4) 0.017(3) 0.007(4) C12 0.091(5) 0.112(6) 0.093(6) 0.043(5) 0.035(4) 0.014(4) C13 0.092(5) 0.127(7) 0.073(5) 0.009(5) 0.027(4) 0.030(5) C14 0.080(5) 0.107(6) 0.071(5) 0.010(4) 0.016(4) 0.028(4) C15 0.057(4) 0.080(4) 0.061(4) 0.002(4) 0.009(3) 0.019(3) C16 0.058(4) 0.074(4) 0.063(4) -0.002(3) -0.005(3) 0.010(3) C17 0.094(5) 0.095(5) 0.070(5) -0.008(4) -0.008(4) 0.018(4) C18 0.087(5) 0.072(5) 0.134(8) -0.004(5) -0.014(5) -0.002(4) C19 0.090(5) 0.091(5) 0.097(6) 0.004(5) 0.006(4) -0.021(4) C20 0.086(5) 0.083(5) 0.090(5) -0.006(4) 0.013(4) -0.014(4) C21 0.079(5) 0.085(5) 0.074(5) -0.008(4) 0.018(4) -0.018(4) Cu2 0.0549(5) 0.0681(5) 0.0882(6) -0.0094(4) 0.0178(4) -0.0091(3) N6 0.063(3) 0.071(3) 0.072(4) 0.000(3) 0.020(3) -0.010(2) N7 0.050(3) 0.068(3) 0.078(3) 0.008(3) 0.015(2) 0.003(2) N8 0.056(3) 0.059(3) 0.107(4) -0.010(3) 0.015(3) -0.002(2) N9 0.054(3) 0.060(3) 0.076(3) -0.010(3) 0.012(2) -0.002(2) N10 0.091(5) 0.099(5) 0.137(6) 0.030(4) 0.051(4) 0.015(4) C22 0.092(5) 0.091(5) 0.077(5) -0.006(4) 0.020(4) -0.026(4) C23 0.079(5) 0.091(5) 0.116(7) 0.012(5) 0.029(4) -0.020(4) C24 0.087(5) 0.066(4) 0.111(6) -0.004(4) 0.022(4) -0.010(3) C25 0.073(4) 0.077(4) 0.092(5) -0.020(4) 0.017(4) -0.006(4) C26 0.049(3) 0.062(4) 0.064(4) -0.003(3) 0.012(3) 0.007(3) C27 0.048(3) 0.072(4) 0.066(4) 0.002(3) 0.009(3) 0.016(3) C28 0.067(4) 0.121(6) 0.070(5) -0.007(4) 0.013(3) -0.003(4) C29 0.085(6) 0.175(9) 0.068(5) 0.011(6) 0.016(4) 0.019(6) C30 0.077(5) 0.122(7) 0.096(7) 0.033(5) 0.030(4) 0.012(5) C31 0.073(4) 0.082(4) 0.090(5) 0.025(4) 0.028(4) 0.003(3) C32 0.072(5) 0.079(5) 0.126(6) -0.009(4) 0.025(4) -0.002(4) C33 0.098(6) 0.067(5) 0.170(8) -0.010(5) 0.060(6) -0.015(4) C34 0.089(6) 0.093(6) 0.144(7) -0.032(5) 0.050(5) -0.032(5) C35 0.063(4) 0.093(5) 0.127(6) -0.030(5) 0.037(4) -0.015(4) C36 0.057(4) 0.070(4) 0.082(4) -0.021(3) 0.030(3) -0.011(3) C37 0.057(4) 0.082(4) 0.066(4) -0.017(3) 0.023(3) 0.000(3) C38 0.058(4) 0.125(6) 0.079(5) -0.007(4) 0.011(3) -0.003(4) C39 0.074(5) 0.136(7) 0.093(6) 0.005(5) 0.001(4) 0.020(5) C40 0.082(5) 0.100(5) 0.085(5) 0.007(4) 0.011(4) 0.018(4) C41 0.074(5) 0.075(5) 0.079(5) -0.013(4) 0.017(3) -0.006(3) C42 0.061(4) 0.067(4) 0.074(4) 0.003(3) 0.009(3) -0.004(3) F5 0.223(7) 0.121(5) 0.371(11) 0.047(6) 0.073(7) 0.039(5) F6 0.154(5) 0.352(10) 0.241(7) -0.175(7) 0.093(5) -0.100(6) F7 0.439(12) 0.259(9) 0.152(6) -0.029(6) 0.113(7) 0.100(8) F8 0.162(6) 0.220(7) 0.325(10) -0.037(7) -0.008(6) 0.090(5) B2 0.299(13) 0.108(7) 0.132(9) -0.085(7) -0.127(9) 0.144(8) F1 0.137(6) 0.293(9) 0.376(12) 0.118(8) -0.068(7) -0.076(6) F2 0.293(9) 0.338(10) 0.126(5) 0.022(6) 0.064(5) 0.179(8) F3 0.140(4) 0.127(3) 0.120(4) 0.037(3) 0.015(3) 0.022(3) F4 0.239(6) 0.112(4) 0.135(4) -0.001(3) -0.050(4) 0.027(4) B1 0.117(8) 0.085(7) 0.091(8) 0.008(6) 0.006(6) -0.001(6) O1 0.212(9) 0.306(13) 0.357(14) -0.066(10) 0.063(9) 0.003(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C21 1.955(8) . ? Cu1 N4 2.006(5) . ? Cu1 N1 2.010(4) . ? Cu1 N3 2.093(5) . ? Cu1 N2 2.144(5) . ? N1 C5 1.340(6) . ? N1 C1 1.352(7) . ? N2 C10 1.334(7) . ? N2 C6 1.339(6) . ? N3 C11 1.324(7) . ? N3 C15 1.352(7) . ? N4 C20 1.335(7) . ? N4 C16 1.338(7) . ? N5 C21 1.138(8) . ? C1 C2 1.357(8) . ? C1 H1 0.9300 . ? C2 C3 1.380(8) . ? C2 H2 0.9300 . ? C3 C4 1.354(8) . ? C3 H3 0.9300 . ? C4 C5 1.384(7) . ? C4 H4 0.9300 . ? C5 C6 1.478(7) . ? C6 C7 1.389(7) . ? C7 C8 1.373(8) . ? C7 H7 0.9300 . ? C8 C9 1.372(8) . ? C8 H8 0.9300 . ? C9 C10 1.358(8) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.393(8) . ? C11 H11 0.9300 . ? C12 C13 1.356(9) . ? C12 H12 0.9300 . ? C13 C14 1.378(9) . ? C13 H13 0.9300 . ? C14 C15 1.359(8) . ? C14 H14 0.9300 . ? C15 C16 1.450(8) . ? C16 C17 1.380(8) . ? C17 C18 1.381(10) . ? C17 H17 0.9300 . ? C18 C19 1.347(10) . ? C18 H18 0.9300 . ? C19 C20 1.364(9) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? Cu2 C42 1.967(7) . ? Cu2 N6 1.993(5) . ? Cu2 N8 2.000(5) . ? Cu2 N7 2.089(5) . ? Cu2 N9 2.103(4) . ? N6 C22 1.327(7) . ? N6 C26 1.348(6) . ? N7 C31 1.322(7) . ? N7 C27 1.348(7) . ? N8 C36 1.334(7) . ? N8 C32 1.345(8) . ? N9 C41 1.327(7) . ? N9 C37 1.338(7) . ? N10 C42 1.134(7) . ? C22 C23 1.387(8) . ? C22 H22 0.9300 . ? C23 C24 1.343(9) . ? C23 H23 0.9300 . ? C24 C25 1.354(8) . ? C24 H24 0.9300 . ? C25 C26 1.379(8) . ? C25 H25 0.9300 . ? C26 C27 1.482(7) . ? C27 C28 1.382(8) . ? C28 C29 1.369(10) . ? C28 H28 0.9300 . ? C29 C30 1.351(10) . ? C29 H29 0.9300 . ? C30 C31 1.359(9) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 C33 1.387(9) . ? C32 H32 0.9300 . ? C33 C34 1.347(10) . ? C33 H33 0.9300 . ? C34 C35 1.380(10) . ? C34 H34 0.9300 . ? C35 C36 1.390(8) . ? C35 H35 0.9300 . ? C36 C37 1.460(8) . ? C37 C38 1.404(8) . ? C38 C39 1.354(9) . ? C38 H38 0.9300 . ? C39 C40 1.376(9) . ? C39 H39 0.9300 . ? C40 C41 1.376(8) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? F5 B2 1.166(12) . ? F6 B2 1.288(13) . ? F7 B2 1.44(2) . ? F8 B2 1.168(11) . ? F1 B1 1.283(11) . ? F2 B1 1.290(11) . ? F3 B1 1.364(9) . ? F4 B1 1.322(10) . ? O1 H1A 0.8502 . ? O1 H1B 0.8498 . ? 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 C21 Cu1 N4 97.2(2) . . ? C21 Cu1 N1 91.4(2) . . ? N4 Cu1 N1 171.3(2) . . ? C21 Cu1 N3 132.7(2) . . ? N4 Cu1 N3 78.6(2) . . ? N1 Cu1 N3 96.93(19) . . ? C21 Cu1 N2 126.7(2) . . ? N4 Cu1 N2 95.01(19) . . ? N1 Cu1 N2 78.30(18) . . ? N3 Cu1 N2 100.56(17) . . ? C5 N1 C1 118.8(5) . . ? C5 N1 Cu1 118.1(4) . . ? C1 N1 Cu1 122.9(4) . . ? C10 N2 C6 118.5(5) . . ? C10 N2 Cu1 128.4(4) . . ? C6 N2 Cu1 112.7(4) . . ? C11 N3 C15 118.4(6) . . ? C11 N3 Cu1 127.6(5) . . ? C15 N3 Cu1 113.9(4) . . ? C20 N4 C16 120.1(5) . . ? C20 N4 Cu1 123.2(5) . . ? C16 N4 Cu1 116.6(4) . . ? N1 C1 C2 122.1(6) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C1 C2 C3 118.8(6) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 119.7(6) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.5(6) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 121.0(5) . . ? N1 C5 C6 114.5(5) . . ? C4 C5 C6 124.5(5) . . ? N2 C6 C7 121.1(5) . . ? N2 C6 C5 116.1(5) . . ? C7 C6 C5 122.8(5) . . ? C8 C7 C6 119.1(6) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C9 C8 C7 119.3(6) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C10 C9 C8 118.6(6) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? N2 C10 C9 123.3(6) . . ? N2 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? N3 C11 C12 122.6(7) . . ? N3 C11 H11 118.7 . . ? C12 C11 H11 118.7 . . ? C13 C12 C11 118.7(7) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C14 118.7(7) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 120.4(7) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? N3 C15 C14 121.3(7) . . ? N3 C15 C16 114.5(6) . . ? C14 C15 C16 124.2(7) . . ? N4 C16 C17 119.0(6) . . ? N4 C16 C15 116.0(6) . . ? C17 C16 C15 125.0(7) . . ? C16 C17 C18 119.4(7) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 121.3(7) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 116.7(7) . . ? C18 C19 H19 121.7 . . ? C20 C19 H19 121.7 . . ? N4 C20 C19 123.5(7) . . ? N4 C20 H20 118.3 . . ? C19 C20 H20 118.3 . . ? N5 C21 Cu1 174.6(7) . . ? C42 Cu2 N6 94.3(2) . . ? C42 Cu2 N8 91.9(2) . . ? N6 Cu2 N8 173.8(2) . . ? C42 Cu2 N7 129.1(2) . . ? N6 Cu2 N7 79.6(2) . . ? N8 Cu2 N7 95.9(2) . . ? C42 Cu2 N9 126.8(2) . . ? N6 Cu2 N9 98.23(18) . . ? N8 Cu2 N9 78.6(2) . . ? N7 Cu2 N9 104.06(17) . . ? C22 N6 C26 118.6(5) . . ? C22 N6 Cu2 124.2(4) . . ? C26 N6 Cu2 117.2(4) . . ? C31 N7 C27 118.6(6) . . ? C31 N7 Cu2 127.8(5) . . ? C27 N7 Cu2 113.4(4) . . ? C36 N8 C32 118.7(5) . . ? C36 N8 Cu2 117.4(4) . . ? C32 N8 Cu2 123.9(4) . . ? C41 N9 C37 118.4(5) . . ? C41 N9 Cu2 128.0(4) . . ? C37 N9 Cu2 113.5(4) . . ? N6 C22 C23 122.0(6) . . ? N6 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? C24 C23 C22 119.2(7) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 C25 119.4(7) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C24 C25 C26 120.2(6) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? N6 C26 C25 120.6(6) . . ? N6 C26 C27 114.3(5) . . ? C25 C26 C27 125.1(6) . . ? N7 C27 C28 121.7(6) . . ? N7 C27 C26 115.4(5) . . ? C28 C27 C26 122.9(6) . . ? C29 C28 C27 117.0(7) . . ? C29 C28 H28 121.5 . . ? C27 C28 H28 121.5 . . ? C30 C29 C28 121.6(8) . . ? C30 C29 H29 119.2 . . ? C28 C29 H29 119.2 . . ? C29 C30 C31 118.1(7) . . ? C29 C30 H30 121.0 . . ? C31 C30 H30 121.0 . . ? N7 C31 C30 122.9(7) . . ? N7 C31 H31 118.6 . . ? C30 C31 H31 118.6 . . ? N8 C32 C33 122.8(6) . . ? N8 C32 H32 118.6 . . ? C33 C32 H32 118.6 . . ? C34 C33 C32 117.9(7) . . ? C34 C33 H33 121.1 . . ? C32 C33 H33 121.1 . . ? C33 C34 C35 120.6(7) . . ? C33 C34 H34 119.7 . . ? C35 C34 H34 119.7 . . ? C34 C35 C36 118.8(7) . . ? C34 C35 H35 120.6 . . ? C36 C35 H35 120.6 . . ? N8 C36 C35 121.2(6) . . ? N8 C36 C37 115.0(5) . . ? C35 C36 C37 123.8(6) . . ? N9 C37 C38 121.1(6) . . ? N9 C37 C36 115.4(5) . . ? C38 C37 C36 123.4(6) . . ? C39 C38 C37 118.9(7) . . ? C39 C38 H38 120.5 . . ? C37 C38 H38 120.5 . . ? C38 C39 C40 120.2(7) . . ? C38 C39 H39 119.9 . . ? C40 C39 H39 119.9 . . ? C41 C40 C39 117.7(7) . . ? C41 C40 H40 121.2 . . ? C39 C40 H40 121.2 . . ? N9 C41 C40 123.6(6) . . ? N9 C41 H41 118.2 . . ? C40 C41 H41 118.2 . . ? N10 C42 Cu2 175.5(6) . . ? F5 B2 F8 128.7(19) . . ? F5 B2 F6 112.2(9) . . ? F8 B2 F6 112.1(9) . . ? F5 B2 F7 90.5(10) . . ? F8 B2 F7 105.6(11) . . ? F6 B2 F7 100.5(18) . . ? F1 B1 F2 110.0(10) . . ? F1 B1 F4 102.7(9) . . ? F2 B1 F4 107.5(9) . . ? F1 B1 F3 113.8(9) . . ? F2 B1 F3 112.0(9) . . ? F4 B1 F3 110.4(8) . . ? H1A O1 H1B 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 Cu1 N1 C5 125.4(4) . . . . ? N4 Cu1 N1 C5 -42.5(15) . . . . ? N3 Cu1 N1 C5 -101.3(4) . . . . ? N2 Cu1 N1 C5 -1.9(4) . . . . ? C21 Cu1 N1 C1 -50.4(5) . . . . ? N4 Cu1 N1 C1 141.8(12) . . . . ? N3 Cu1 N1 C1 82.9(5) . . . . ? N2 Cu1 N1 C1 -177.7(5) . . . . ? C21 Cu1 N2 C10 102.7(5) . . . . ? N4 Cu1 N2 C10 -0.1(5) . . . . ? N1 Cu1 N2 C10 -174.4(5) . . . . ? N3 Cu1 N2 C10 -79.4(5) . . . . ? C21 Cu1 N2 C6 -84.7(4) . . . . ? N4 Cu1 N2 C6 172.5(4) . . . . ? N1 Cu1 N2 C6 -1.8(4) . . . . ? N3 Cu1 N2 C6 93.2(4) . . . . ? C21 Cu1 N3 C11 88.8(5) . . . . ? N4 Cu1 N3 C11 178.1(5) . . . . ? N1 Cu1 N3 C11 -9.5(5) . . . . ? N2 Cu1 N3 C11 -88.8(5) . . . . ? C21 Cu1 N3 C15 -94.5(4) . . . . ? N4 Cu1 N3 C15 -5.2(4) . . . . ? N1 Cu1 N3 C15 167.2(4) . . . . ? N2 Cu1 N3 C15 87.8(4) . . . . ? C21 Cu1 N4 C20 -45.8(5) . . . . ? N1 Cu1 N4 C20 121.9(13) . . . . ? N3 Cu1 N4 C20 -178.0(5) . . . . ? N2 Cu1 N4 C20 82.2(5) . . . . ? C21 Cu1 N4 C16 138.0(4) . . . . ? N1 Cu1 N4 C16 -54.2(15) . . . . ? N3 Cu1 N4 C16 5.9(4) . . . . ? N2 Cu1 N4 C16 -93.9(4) . . . . ? C5 N1 C1 C2 1.6(9) . . . . ? Cu1 N1 C1 C2 177.3(5) . . . . ? N1 C1 C2 C3 -2.7(10) . . . . ? C1 C2 C3 C4 2.0(10) . . . . ? C2 C3 C4 C5 -0.2(9) . . . . ? C1 N1 C5 C4 0.3(8) . . . . ? Cu1 N1 C5 C4 -175.6(4) . . . . ? C1 N1 C5 C6 -179.0(5) . . . . ? Cu1 N1 C5 C6 5.1(6) . . . . ? C3 C4 C5 N1 -1.0(9) . . . . ? C3 C4 C5 C6 178.3(6) . . . . ? C10 N2 C6 C7 -1.9(8) . . . . ? Cu1 N2 C6 C7 -175.3(4) . . . . ? C10 N2 C6 C5 178.3(5) . . . . ? Cu1 N2 C6 C5 4.9(6) . . . . ? N1 C5 C6 N2 -6.6(7) . . . . ? C4 C5 C6 N2 174.1(5) . . . . ? N1 C5 C6 C7 173.6(5) . . . . ? C4 C5 C6 C7 -5.7(9) . . . . ? N2 C6 C7 C8 1.7(9) . . . . ? C5 C6 C7 C8 -178.5(6) . . . . ? C6 C7 C8 C9 -0.7(10) . . . . ? C7 C8 C9 C10 0.0(10) . . . . ? C6 N2 C10 C9 1.2(9) . . . . ? Cu1 N2 C10 C9 173.4(5) . . . . ? C8 C9 C10 N2 -0.2(10) . . . . ? C15 N3 C11 C12 0.6(8) . . . . ? Cu1 N3 C11 C12 177.2(4) . . . . ? N3 C11 C12 C13 -1.8(9) . . . . ? C11 C12 C13 C14 2.0(10) . . . . ? C12 C13 C14 C15 -1.3(10) . . . . ? C11 N3 C15 C14 0.1(8) . . . . ? Cu1 N3 C15 C14 -176.9(4) . . . . ? C11 N3 C15 C16 -179.1(5) . . . . ? Cu1 N3 C15 C16 3.9(6) . . . . ? C13 C14 C15 N3 0.2(9) . . . . ? C13 C14 C15 C16 179.4(6) . . . . ? C20 N4 C16 C17 -1.4(8) . . . . ? Cu1 N4 C16 C17 174.8(4) . . . . ? C20 N4 C16 C15 178.1(5) . . . . ? Cu1 N4 C16 C15 -5.6(6) . . . . ? N3 C15 C16 N4 1.0(7) . . . . ? C14 C15 C16 N4 -178.3(5) . . . . ? N3 C15 C16 C17 -179.5(5) . . . . ? C14 C15 C16 C17 1.3(9) . . . . ? N4 C16 C17 C18 0.6(9) . . . . ? C15 C16 C17 C18 -178.9(6) . . . . ? C16 C17 C18 C19 0.6(10) . . . . ? C17 C18 C19 C20 -0.9(11) . . . . ? C16 N4 C20 C19 1.1(9) . . . . ? Cu1 N4 C20 C19 -174.9(5) . . . . ? C18 C19 C20 N4 0.1(10) . . . . ? N4 Cu1 C21 N5 -150(8) . . . . ? N1 Cu1 C21 N5 32(8) . . . . ? N3 Cu1 C21 N5 -69(8) . . . . ? N2 Cu1 C21 N5 108(8) . . . . ? C42 Cu2 N6 C22 50.3(5) . . . . ? N8 Cu2 N6 C22 -136.4(19) . . . . ? N7 Cu2 N6 C22 179.2(5) . . . . ? N9 Cu2 N6 C22 -77.9(5) . . . . ? C42 Cu2 N6 C26 -127.6(4) . . . . ? N8 Cu2 N6 C26 46(2) . . . . ? N7 Cu2 N6 C26 1.4(4) . . . . ? N9 Cu2 N6 C26 104.3(4) . . . . ? C42 Cu2 N7 C31 -90.9(5) . . . . ? N6 Cu2 N7 C31 -178.0(5) . . . . ? N8 Cu2 N7 C31 6.4(5) . . . . ? N9 Cu2 N7 C31 86.0(5) . . . . ? C42 Cu2 N7 C27 85.0(4) . . . . ? N6 Cu2 N7 C27 -2.1(3) . . . . ? N8 Cu2 N7 C27 -177.7(4) . . . . ? N9 Cu2 N7 C27 -98.0(4) . . . . ? C42 Cu2 N8 C36 -127.5(4) . . . . ? N6 Cu2 N8 C36 59(2) . . . . ? N7 Cu2 N8 C36 102.9(4) . . . . ? N9 Cu2 N8 C36 -0.2(4) . . . . ? C42 Cu2 N8 C32 51.9(5) . . . . ? N6 Cu2 N8 C32 -121.4(19) . . . . ? N7 Cu2 N8 C32 -77.7(5) . . . . ? N9 Cu2 N8 C32 179.1(6) . . . . ? C42 Cu2 N9 C41 -96.0(5) . . . . ? N6 Cu2 N9 C41 5.7(5) . . . . ? N8 Cu2 N9 C41 -179.7(5) . . . . ? N7 Cu2 N9 C41 86.9(5) . . . . ? C42 Cu2 N9 C37 85.0(4) . . . . ? N6 Cu2 N9 C37 -173.3(4) . . . . ? N8 Cu2 N9 C37 1.3(4) . . . . ? N7 Cu2 N9 C37 -92.0(4) . . . . ? C26 N6 C22 C23 0.1(9) . . . . ? Cu2 N6 C22 C23 -177.8(5) . . . . ? N6 C22 C23 C24 0.6(10) . . . . ? C22 C23 C24 C25 -1.2(10) . . . . ? C23 C24 C25 C26 1.1(10) . . . . ? C22 N6 C26 C25 -0.2(8) . . . . ? Cu2 N6 C26 C25 177.8(4) . . . . ? C22 N6 C26 C27 -178.5(5) . . . . ? Cu2 N6 C26 C27 -0.5(6) . . . . ? C24 C25 C26 N6 -0.4(9) . . . . ? C24 C25 C26 C27 177.7(5) . . . . ? C31 N7 C27 C28 -0.4(8) . . . . ? Cu2 N7 C27 C28 -176.8(4) . . . . ? C31 N7 C27 C26 178.7(4) . . . . ? Cu2 N7 C27 C26 2.4(5) . . . . ? N6 C26 C27 N7 -1.3(6) . . . . ? C25 C26 C27 N7 -179.6(5) . . . . ? N6 C26 C27 C28 177.8(5) . . . . ? C25 C26 C27 C28 -0.4(8) . . . . ? N7 C27 C28 C29 1.4(9) . . . . ? C26 C27 C28 C29 -177.7(5) . . . . ? C27 C28 C29 C30 -2.5(10) . . . . ? C28 C29 C30 C31 2.5(11) . . . . ? C27 N7 C31 C30 0.4(8) . . . . ? Cu2 N7 C31 C30 176.2(5) . . . . ? C29 C30 C31 N7 -1.5(10) . . . . ? C36 N8 C32 C33 1.3(10) . . . . ? Cu2 N8 C32 C33 -178.0(5) . . . . ? N8 C32 C33 C34 -0.5(11) . . . . ? C32 C33 C34 C35 -1.5(12) . . . . ? C33 C34 C35 C36 2.4(11) . . . . ? C32 N8 C36 C35 -0.3(9) . . . . ? Cu2 N8 C36 C35 179.1(4) . . . . ? C32 N8 C36 C37 179.8(5) . . . . ? Cu2 N8 C36 C37 -0.8(7) . . . . ? C34 C35 C36 N8 -1.5(10) . . . . ? C34 C35 C36 C37 178.4(6) . . . . ? C41 N9 C37 C38 -0.9(8) . . . . ? Cu2 N9 C37 C38 178.1(4) . . . . ? C41 N9 C37 C36 178.8(5) . . . . ? Cu2 N9 C37 C36 -2.1(6) . . . . ? N8 C36 C37 N9 2.0(7) . . . . ? C35 C36 C37 N9 -177.9(5) . . . . ? N8 C36 C37 C38 -178.3(5) . . . . ? C35 C36 C37 C38 1.8(9) . . . . ? N9 C37 C38 C39 1.2(10) . . . . ? C36 C37 C38 C39 -178.5(6) . . . . ? C37 C38 C39 C40 -1.4(11) . . . . ? C38 C39 C40 C41 1.3(11) . . . . ? C37 N9 C41 C40 0.9(9) . . . . ? Cu2 N9 C41 C40 -178.0(4) . . . . ? C39 C40 C41 N9 -1.0(10) . . . . ? N6 Cu2 C42 N10 -180(100) . . . . ? N8 Cu2 C42 N10 1(8) . . . . ? N7 Cu2 C42 N10 100(8) . . . . ? N9 Cu2 C42 N10 -76(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.880 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.071 data_4 _database_code_depnum_ccdc_archive 'CCDC 869861' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C41 H32 Cu2 N9), 6(B F4), 3(H2 O)' _chemical_formula_sum 'C82 H70 B6 Cu4 F24 N18 O3' _chemical_formula_weight 2130.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 21.781(3) _cell_length_b 13.119(2) _cell_length_c 16.471(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.610(2) _cell_angle_gamma 90.00 _cell_volume 4510.0(12) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3821 _cell_measurement_theta_min 2.485 _cell_measurement_theta_max 21.471 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2148 _exptl_absorpt_coefficient_mu 1.039 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8854 _exptl_absorpt_correction_T_max 0.9032 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22145 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0858 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7927 _reflns_number_gt 4217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^2^] 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 7927 _refine_ls_number_parameters 665 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 0.834 _refine_ls_restrained_S_all 0.860 _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 0.24935(2) 0.09457(4) 0.20477(3) 0.05089(17) Uani 1 1 d . . . Cu2 Cu 0.23338(2) 0.44358(4) 0.33506(3) 0.05245(18) Uani 1 1 d . . . B1 B 0.1110(4) 0.2705(6) 0.4185(6) 0.099(2) Uani 1 1 d . . . B2 B 0.5000 0.8376(8) 0.2500 0.135(7) Uani 1 2 d S . . B3 B 0.0000 0.7743(11) 0.2500 0.127(5) Uani 1 2 d S . . B4 B 0.5948(3) 0.2834(5) 0.4348(4) 0.108(3) Uani 1 1 d D . . C1 C 0.3225(2) -0.0200(3) 0.1002(3) 0.0607(12) Uani 1 1 d . . . H1 H 0.3598 -0.0055 0.1430 0.073 Uiso 1 1 calc R . . C2 C 0.3259(3) -0.0851(3) 0.0364(4) 0.0781(15) Uani 1 1 d . . . H2 H 0.3647 -0.1142 0.0359 0.094 Uiso 1 1 calc R . . C3 C 0.2709(4) -0.1062(4) -0.0264(4) 0.0870(18) Uani 1 1 d . . . H3 H 0.2718 -0.1519 -0.0692 0.104 Uiso 1 1 calc R . . C4 C 0.2148(3) -0.0602(4) -0.0262(3) 0.0758(15) Uani 1 1 d . . . H4 H 0.1776 -0.0723 -0.0699 0.091 Uiso 1 1 calc R . . C5 C 0.2140(2) 0.0044(3) 0.0395(3) 0.0570(12) Uani 1 1 d . . . C6 C 0.1563(2) 0.0545(3) 0.0486(3) 0.0592(12) Uani 1 1 d . . . C7 C 0.0989(3) 0.0592(4) -0.0161(3) 0.0842(16) Uani 1 1 d . . . H7 H 0.0952 0.0295 -0.0685 0.101 Uiso 1 1 calc R . . C8 C 0.0477(3) 0.1085(5) -0.0006(5) 0.107(2) Uani 1 1 d . . . H8 H 0.0093 0.1144 -0.0433 0.128 Uiso 1 1 calc R . . C9 C 0.0534(3) 0.1489(4) 0.0773(5) 0.105(2) Uani 1 1 d . . . H9 H 0.0186 0.1806 0.0888 0.126 Uiso 1 1 calc R . . C10 C 0.1113(2) 0.1423(4) 0.1390(4) 0.0793(15) Uani 1 1 d . . . H10 H 0.1151 0.1704 0.1921 0.095 Uiso 1 1 calc R . . C11 C 0.3856(2) 0.1425(3) 0.2774(3) 0.0632(12) Uani 1 1 d . . . H11 H 0.3771 0.1964 0.2392 0.076 Uiso 1 1 calc R . . C12 C 0.4464(2) 0.1299(4) 0.3284(3) 0.0728(14) Uani 1 1 d . . . H12 H 0.4788 0.1744 0.3251 0.087 Uiso 1 1 calc R . . C13 C 0.4591(2) 0.0507(4) 0.3847(3) 0.0849(16) Uani 1 1 d . . . H13 H 0.5003 0.0407 0.4203 0.102 Uiso 1 1 calc R . . C14 C 0.4103(2) -0.0137(4) 0.3881(3) 0.0683(13) Uani 1 1 d . . . H14 H 0.4183 -0.0683 0.4257 0.082 Uiso 1 1 calc R . . C15 C 0.34952(19) 0.0027(3) 0.3357(2) 0.0470(10) Uani 1 1 d . . . C16 C 0.29333(19) -0.0603(3) 0.3355(3) 0.0468(10) Uani 1 1 d . . . C17 C 0.2959(2) -0.1406(3) 0.3905(3) 0.0606(12) Uani 1 1 d . . . H17 H 0.3344 -0.1584 0.4297 0.073 Uiso 1 1 calc R . . C18 C 0.2408(2) -0.1937(3) 0.3867(3) 0.0696(13) Uani 1 1 d . . . H18 H 0.2418 -0.2482 0.4232 0.084 Uiso 1 1 calc R . . C19 C 0.1848(2) -0.1664(3) 0.3295(3) 0.0692(13) Uani 1 1 d . . . H19 H 0.1471 -0.2018 0.3260 0.083 Uiso 1 1 calc R . . C20 C 0.1852(2) -0.0855(3) 0.2769(3) 0.0601(12) Uani 1 1 d . . . H20 H 0.1468 -0.0670 0.2379 0.072 Uiso 1 1 calc R . . C21 C 0.24193(18) 0.2335(3) 0.2500(2) 0.0559(10) Uani 0.50 1 d P . . C22 C 0.1027(2) 0.4436(4) 0.2179(3) 0.0744(14) Uani 1 1 d . . . H22 H 0.0968 0.3862 0.2481 0.089 Uiso 1 1 calc R . . C23 C 0.0513(3) 0.4802(6) 0.1519(4) 0.102(2) Uani 1 1 d . . . H23 H 0.0115 0.4486 0.1378 0.122 Uiso 1 1 calc R . . C24 C 0.0624(4) 0.5649(7) 0.1089(5) 0.125(3) Uani 1 1 d . . . H24 H 0.0294 0.5909 0.0647 0.150 Uiso 1 1 calc R . . C25 C 0.1199(3) 0.6107(5) 0.1293(4) 0.1012(19) Uani 1 1 d . . . H25 H 0.1263 0.6680 0.0995 0.121 Uiso 1 1 calc R . . C26 C 0.1699(3) 0.5725(3) 0.1951(3) 0.0650(13) Uani 1 1 d . . . C27 C 0.2347(3) 0.6151(3) 0.2208(3) 0.0637(13) Uani 1 1 d . . . C28 C 0.2538(3) 0.6997(4) 0.1819(3) 0.0826(16) Uani 1 1 d . . . H28 H 0.2250 0.7323 0.1365 0.099 Uiso 1 1 calc R . . C29 C 0.3150(4) 0.7331(4) 0.2116(4) 0.096(2) Uani 1 1 d . . . H29 H 0.3283 0.7893 0.1866 0.116 Uiso 1 1 calc R . . C30 C 0.3574(3) 0.6852(4) 0.2778(4) 0.0897(17) Uani 1 1 d . . . H30 H 0.3995 0.7077 0.2987 0.108 Uiso 1 1 calc R . . C31 C 0.3356(3) 0.6029(3) 0.3122(3) 0.0714(14) Uani 1 1 d . . . H31 H 0.3643 0.5696 0.3572 0.086 Uiso 1 1 calc R . . C32 C 0.1501(2) 0.5750(3) 0.4130(3) 0.0571(12) Uani 1 1 d . . . H32 H 0.1204 0.5744 0.3597 0.068 Uiso 1 1 calc R . . C33 C 0.1359(2) 0.6308(3) 0.4756(3) 0.0652(13) Uani 1 1 d . . . H33 H 0.0979 0.6676 0.4653 0.078 Uiso 1 1 calc R . . C34 C 0.1800(3) 0.6302(3) 0.5542(3) 0.0695(14) Uani 1 1 d . . . H34 H 0.1720 0.6669 0.5984 0.083 Uiso 1 1 calc R . . C35 C 0.2351(3) 0.5765(3) 0.5675(3) 0.0652(13) Uani 1 1 d . . . H35 H 0.2651 0.5769 0.6206 0.078 Uiso 1 1 calc R . . C36 C 0.2466(2) 0.5210(3) 0.5016(3) 0.0509(11) Uani 1 1 d . . . C37 C 0.3044(2) 0.4598(3) 0.5081(3) 0.0552(11) Uani 1 1 d . . . C38 C 0.3540(2) 0.4483(4) 0.5822(3) 0.0729(14) Uani 1 1 d . . . H38 H 0.3515 0.4787 0.6322 0.087 Uiso 1 1 calc R . . C39 C 0.4061(3) 0.3922(4) 0.5810(4) 0.0902(18) Uani 1 1 d . . . H39 H 0.4396 0.3844 0.6304 0.108 Uiso 1 1 calc R . . C40 C 0.4096(3) 0.3472(4) 0.5077(4) 0.0887(17) Uani 1 1 d . . . H40 H 0.4450 0.3086 0.5061 0.106 Uiso 1 1 calc R . . C41 C 0.3586(2) 0.3611(4) 0.4360(3) 0.0753(14) Uani 1 1 d . . . H41 H 0.3604 0.3308 0.3856 0.090 Uiso 1 1 calc R . . C21' C 0.23995(18) 0.3108(3) 0.2805(2) 0.0572(10) Uani 0.50 1 d P . . F1 F 0.1740(2) 0.2982(3) 0.4462(3) 0.1639(18) Uani 1 1 d . . . F2 F 0.0760(2) 0.3520(4) 0.4099(4) 0.207(2) Uani 1 1 d . . . F3 F 0.10040(17) 0.2092(3) 0.4788(2) 0.1210(12) Uani 1 1 d . . . F4 F 0.1049(3) 0.2127(4) 0.3496(3) 0.197(2) Uani 1 1 d . . . F5 F 0.5000 0.7423(5) 0.2500 0.176(3) Uani 1 2 d S . . F6 F 0.5004(4) 0.8181(6) 0.3463(5) 0.131(3) Uani 0.50 1 d P . . F7 F 0.44673(17) 0.8874(3) 0.2273(2) 0.1421(14) Uani 1 1 d . . . F8 F 0.0335(3) 0.8342(5) 0.2115(4) 0.239(3) Uani 1 1 d . . . F9 F 0.04180(19) 0.7238(4) 0.3066(3) 0.187(2) Uani 1 1 d . . . F10 F 0.6270(5) 0.3351(6) 0.5021(4) 0.118(5) Uani 0.551(11) 1 d PD A 1 F11 F 0.5452(6) 0.3401(9) 0.3875(10) 0.205(9) Uani 0.551(11) 1 d PD A 1 F12 F 0.5724(6) 0.1977(7) 0.4561(8) 0.220(10) Uani 0.551(11) 1 d PD A 1 F13 F 0.6400(7) 0.2710(13) 0.3915(10) 0.315(12) Uani 0.551(11) 1 d PD A 1 F10' F 0.6540(4) 0.3134(10) 0.4635(10) 0.169(9) Uani 0.449(11) 1 d PD A 2 F11' F 0.5679(7) 0.3146(10) 0.3545(5) 0.143(7) Uani 0.449(11) 1 d PD A 2 F12' F 0.5950(6) 0.1781(5) 0.4309(9) 0.119(5) Uani 0.449(11) 1 d PD A 2 F13' F 0.5596(8) 0.3101(14) 0.4861(10) 0.315(14) Uani 0.449(11) 1 d PD A 2 N1 N 0.26739(17) 0.0237(2) 0.1034(2) 0.0517(9) Uani 1 1 d . . . N2 N 0.16211(17) 0.0965(2) 0.1247(2) 0.0562(9) Uani 1 1 d . . . N3 N 0.33752(15) 0.0799(2) 0.2802(2) 0.0476(8) Uani 1 1 d . . . N4 N 0.23758(15) -0.0318(2) 0.2786(2) 0.0493(9) Uani 1 1 d . . . N5 N 0.23995(18) 0.3108(3) 0.2805(2) 0.0572(10) Uani 0.50 1 d P . . N6 N 0.16006(17) 0.4897(3) 0.2384(2) 0.0565(9) Uani 1 1 d . . . N7 N 0.27615(19) 0.5672(2) 0.2858(2) 0.0570(9) Uani 1 1 d . . . N8 N 0.20380(17) 0.5215(2) 0.4238(2) 0.0488(9) Uani 1 1 d . . . N9 N 0.30689(17) 0.4157(2) 0.4357(2) 0.0540(9) Uani 1 1 d . . . N5' N 0.24193(18) 0.2335(3) 0.2500(2) 0.0559(10) Uani 0.50 1 d P . . O1 O 0.5697(5) 0.4191(6) 0.2221(6) 0.363(6) Uani 1 1 d . . . H1A H 0.5349 0.4086 0.1835 0.545 Uiso 1 1 d R . . H1B H 0.5694 0.3860 0.2663 0.545 Uiso 1 1 d R . . O2 O 0.0496(9) 0.0573(17) 0.2838(14) 0.385(13) Uani 0.50 1 d P . . H2A H 0.0586 0.0458 0.2378 0.578 Uiso 0.50 1 d PR . . H2B H 0.0685 0.1113 0.3065 0.578 Uiso 0.50 1 d PR . . 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 0.0502(3) 0.0412(3) 0.0575(4) -0.0032(2) 0.0093(3) 0.0015(2) Cu2 0.0599(4) 0.0423(3) 0.0526(3) -0.0041(2) 0.0122(3) 0.0010(2) B1 0.084(6) 0.086(5) 0.126(7) 0.011(5) 0.028(5) 0.004(5) B2 0.063(8) 0.051(7) 0.29(2) 0.000 0.049(10) 0.000 B3 0.051(7) 0.108(10) 0.217(17) 0.000 0.032(9) 0.000 B4 0.109(7) 0.089(6) 0.116(8) 0.023(6) 0.013(6) 0.000(5) C1 0.071(3) 0.057(3) 0.057(3) 0.003(2) 0.023(3) 0.008(2) C2 0.112(5) 0.059(3) 0.080(4) 0.003(3) 0.054(4) 0.013(3) C3 0.150(6) 0.057(3) 0.067(4) -0.015(3) 0.052(4) -0.026(4) C4 0.104(5) 0.063(3) 0.060(3) -0.004(3) 0.024(3) -0.023(3) C5 0.077(3) 0.042(2) 0.050(3) 0.003(2) 0.014(3) -0.013(2) C6 0.056(3) 0.050(3) 0.064(3) 0.015(2) 0.004(3) -0.011(2) C7 0.072(4) 0.088(4) 0.076(4) 0.013(3) -0.005(3) -0.018(3) C8 0.065(4) 0.099(5) 0.125(6) 0.035(4) -0.021(4) -0.020(4) C9 0.049(4) 0.086(4) 0.162(7) 0.032(5) 0.002(4) 0.008(3) C10 0.059(3) 0.064(3) 0.112(4) 0.003(3) 0.018(3) 0.000(3) C11 0.062(3) 0.059(3) 0.068(3) 0.002(2) 0.017(3) -0.011(2) C12 0.050(3) 0.086(4) 0.079(4) 0.000(3) 0.012(3) -0.021(3) C13 0.053(3) 0.105(4) 0.086(4) 0.010(3) 0.004(3) -0.009(3) C14 0.052(3) 0.076(3) 0.070(3) 0.011(3) 0.006(3) -0.005(3) C15 0.045(3) 0.049(3) 0.046(3) -0.008(2) 0.013(2) 0.000(2) C16 0.047(3) 0.040(2) 0.054(3) -0.005(2) 0.015(2) 0.001(2) C17 0.066(3) 0.048(3) 0.063(3) 0.011(2) 0.011(2) -0.001(2) C18 0.082(4) 0.051(3) 0.076(4) 0.014(2) 0.023(3) -0.007(3) C19 0.061(3) 0.056(3) 0.092(4) 0.006(3) 0.023(3) -0.012(2) C20 0.051(3) 0.055(3) 0.071(3) 0.003(2) 0.013(2) -0.001(2) C21 0.062(3) 0.047(2) 0.057(3) 0.000(2) 0.014(2) 0.003(2) C22 0.061(3) 0.086(4) 0.071(4) -0.020(3) 0.011(3) -0.002(3) C23 0.063(4) 0.134(6) 0.101(5) -0.035(4) 0.011(4) 0.004(4) C24 0.091(6) 0.160(7) 0.105(6) 0.002(5) -0.004(5) 0.033(5) C25 0.105(5) 0.101(5) 0.086(4) 0.022(4) 0.009(4) 0.029(4) C26 0.088(4) 0.055(3) 0.049(3) 0.001(2) 0.015(3) 0.024(3) C27 0.089(4) 0.049(3) 0.060(3) -0.010(2) 0.032(3) 0.002(3) C28 0.128(5) 0.055(3) 0.070(4) 0.010(3) 0.038(4) 0.007(3) C29 0.154(6) 0.061(4) 0.096(5) 0.001(3) 0.072(5) -0.021(4) C30 0.113(5) 0.069(4) 0.105(5) -0.014(3) 0.061(4) -0.033(3) C31 0.077(4) 0.063(3) 0.079(4) -0.008(3) 0.030(3) -0.014(3) C32 0.061(3) 0.046(3) 0.064(3) -0.004(2) 0.018(2) -0.003(2) C33 0.071(3) 0.055(3) 0.076(4) -0.005(3) 0.030(3) 0.001(2) C34 0.096(4) 0.058(3) 0.063(4) -0.008(3) 0.038(3) -0.004(3) C35 0.092(4) 0.058(3) 0.043(3) -0.001(2) 0.016(3) -0.009(3) C36 0.069(3) 0.039(2) 0.047(3) 0.001(2) 0.020(2) -0.017(2) C37 0.060(3) 0.043(2) 0.059(3) 0.011(2) 0.013(3) -0.008(2) C38 0.079(4) 0.073(3) 0.055(3) 0.004(3) 0.000(3) 0.002(3) C39 0.078(4) 0.088(4) 0.082(4) 0.022(3) -0.013(3) 0.003(3) C40 0.069(4) 0.076(4) 0.105(5) 0.012(4) -0.001(4) 0.017(3) C41 0.070(4) 0.068(3) 0.083(4) 0.001(3) 0.013(3) 0.007(3) C21' 0.069(3) 0.046(2) 0.054(3) -0.001(2) 0.013(2) 0.002(2) F1 0.117(3) 0.094(3) 0.298(6) 0.019(3) 0.085(3) -0.011(2) F2 0.165(4) 0.170(4) 0.290(6) 0.083(4) 0.070(4) 0.101(4) F3 0.132(3) 0.105(2) 0.147(3) 0.005(2) 0.074(3) -0.019(2) F4 0.257(6) 0.217(5) 0.100(3) -0.021(3) 0.022(3) 0.029(4) F5 0.097(4) 0.115(5) 0.285(9) 0.000 0.004(5) 0.000 F6 0.149(7) 0.128(6) 0.122(6) 0.045(5) 0.048(5) 0.025(5) F7 0.100(3) 0.145(3) 0.161(4) -0.001(3) 0.004(2) 0.048(2) F8 0.171(5) 0.268(6) 0.241(6) 0.101(5) -0.003(4) -0.051(4) F9 0.096(3) 0.201(5) 0.215(5) 0.087(4) -0.034(3) -0.007(3) F10 0.188(12) 0.085(5) 0.072(5) -0.011(4) 0.025(6) -0.047(6) F11 0.149(9) 0.133(10) 0.271(19) 0.088(12) -0.040(11) -0.027(7) F12 0.136(11) 0.148(10) 0.275(17) 0.160(11) -0.103(10) -0.079(8) F13 0.38(2) 0.38(2) 0.218(15) -0.195(16) 0.138(17) -0.184(19) F10' 0.076(7) 0.163(13) 0.214(17) 0.107(12) -0.044(9) -0.069(8) F11' 0.206(18) 0.117(8) 0.062(6) 0.032(6) -0.033(7) 0.012(9) F12' 0.072(7) 0.087(7) 0.173(10) -0.037(7) -0.007(6) -0.008(5) F13' 0.138(13) 0.64(4) 0.191(15) -0.09(2) 0.089(12) 0.06(2) N1 0.058(2) 0.0417(19) 0.053(2) 0.0042(16) 0.013(2) 0.0007(17) N2 0.051(2) 0.045(2) 0.069(3) 0.0018(19) 0.010(2) 0.0011(18) N3 0.048(2) 0.0431(19) 0.051(2) 0.0014(17) 0.0125(17) -0.0061(16) N4 0.044(2) 0.045(2) 0.058(2) -0.0057(16) 0.0141(18) -0.0040(16) N5 0.069(3) 0.046(2) 0.054(3) -0.001(2) 0.013(2) 0.002(2) N6 0.062(3) 0.056(2) 0.050(2) -0.0117(19) 0.0145(19) 0.0061(19) N7 0.064(3) 0.048(2) 0.062(3) 0.0004(19) 0.024(2) -0.0012(19) N8 0.062(2) 0.0394(19) 0.045(2) 0.0015(16) 0.0155(19) -0.0086(17) N9 0.058(2) 0.044(2) 0.058(2) 0.0033(18) 0.0148(19) 0.0044(18) N5' 0.062(3) 0.047(2) 0.057(3) 0.000(2) 0.014(2) 0.003(2) O1 0.526(17) 0.308(10) 0.301(11) -0.058(8) 0.190(12) -0.191(11) O2 0.37(3) 0.44(3) 0.39(3) 0.07(2) 0.17(3) 0.03(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 N3 1.976(3) . ? Cu1 N2 1.980(3) . ? Cu1 C21 1.992(4) . ? Cu1 N1 2.046(3) . ? Cu1 N4 2.114(3) . ? Cu2 N9 1.981(3) . ? Cu2 C21' 1.984(4) . ? Cu2 N6 2.000(3) . ? Cu2 N8 2.034(3) . ? Cu2 N7 2.142(3) . ? B1 F2 1.298(8) . ? B1 F4 1.339(9) . ? B1 F3 1.349(8) . ? B1 F1 1.365(8) . ? B2 F5 1.250(10) . ? B2 F7 1.290(6) 2_655 ? B2 F7 1.290(6) . ? B2 F6 1.604(8) . ? B2 F6 1.604(8) 2_655 ? B3 F9 1.285(7) 2 ? B3 F9 1.285(7) . ? B3 F8 1.348(8) 2 ? B3 F8 1.348(8) . ? B4 F10' 1.300(7) . ? B4 F12 1.313(7) . ? B4 F10 1.317(7) . ? B4 F13' 1.341(8) . ? B4 F11' 1.348(8) . ? B4 F11 1.359(8) . ? B4 F13 1.380(8) . ? B4 F12' 1.383(8) . ? C1 N1 1.345(5) . ? C1 C2 1.372(6) . ? C1 H1 0.9300 . ? C2 C3 1.369(7) . ? C2 H2 0.9300 . ? C3 C4 1.362(7) . ? C3 H3 0.9300 . ? C4 C5 1.380(6) . ? C4 H4 0.9300 . ? C5 N1 1.350(5) . ? C5 C6 1.463(6) . ? C6 N2 1.341(5) . ? C6 C7 1.394(6) . ? C7 C8 1.373(8) . ? C7 H7 0.9300 . ? C8 C9 1.361(8) . ? C8 H8 0.9300 . ? C9 C10 1.377(7) . ? C9 H9 0.9300 . ? C10 N2 1.339(6) . ? C10 H10 0.9300 . ? C11 N3 1.342(5) . ? C11 C12 1.360(6) . ? C11 H11 0.9300 . ? C12 C13 1.366(6) . ? C12 H12 0.9300 . ? C13 C14 1.371(6) . ? C13 H13 0.9300 . ? C14 C15 1.375(5) . ? C14 H14 0.9300 . ? C15 N3 1.338(5) . ? C15 C16 1.477(5) . ? C16 N4 1.358(5) . ? C16 C17 1.380(5) . ? C17 C18 1.374(6) . ? C17 H17 0.9300 . ? C18 C19 1.359(6) . ? C18 H18 0.9300 . ? C19 C20 1.372(6) . ? C19 H19 0.9300 . ? C20 N4 1.334(5) . ? C20 H20 0.9300 . ? C21 C21' 1.138(5) . ? C22 N6 1.342(5) . ? C22 C23 1.403(7) . ? C22 H22 0.9300 . ? C23 C24 1.376(8) . ? C23 H23 0.9300 . ? C24 C25 1.342(8) . ? C24 H24 0.9300 . ? C25 C26 1.392(7) . ? C25 H25 0.9300 . ? C26 N6 1.349(5) . ? C26 C27 1.464(6) . ? C27 N7 1.343(5) . ? C27 C28 1.404(6) . ? C28 C29 1.354(7) . ? C28 H28 0.9300 . ? C29 C30 1.364(7) . ? C29 H29 0.9300 . ? C30 C31 1.367(6) . ? C30 H30 0.9300 . ? C31 N7 1.327(5) . ? C31 H31 0.9300 . ? C32 N8 1.332(5) . ? C32 C33 1.370(6) . ? C32 H32 0.9300 . ? C33 C34 1.374(6) . ? C33 H33 0.9300 . ? C34 C35 1.355(6) . ? C34 H34 0.9300 . ? C35 C36 1.389(6) . ? C35 H35 0.9300 . ? C36 N8 1.352(5) . ? C36 C37 1.471(6) . ? C37 N9 1.340(5) . ? C37 C38 1.388(6) . ? C38 C39 1.358(7) . ? C38 H38 0.9300 . ? C39 C40 1.366(7) . ? C39 H39 0.9300 . ? C40 C41 1.383(6) . ? C40 H40 0.9300 . ? C41 N9 1.333(5) . ? C41 H41 0.9300 . ? O1 H1A 0.8498 . ? O1 H1B 0.8501 . ? O2 H2A 0.8499 . ? O2 H2B 0.8499 . ? 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 N3 Cu1 N2 174.56(14) . . ? N3 Cu1 C21 91.27(14) . . ? N2 Cu1 C21 94.16(15) . . ? N3 Cu1 N1 95.17(14) . . ? N2 Cu1 N1 80.42(15) . . ? C21 Cu1 N1 140.89(14) . . ? N3 Cu1 N4 79.50(13) . . ? N2 Cu1 N4 98.17(13) . . ? C21 Cu1 N4 117.78(14) . . ? N1 Cu1 N4 101.32(12) . . ? N9 Cu2 C21' 94.08(15) . . ? N9 Cu2 N6 172.88(14) . . ? C21' Cu2 N6 92.84(14) . . ? N9 Cu2 N8 80.68(15) . . ? C21' Cu2 N8 147.75(14) . . ? N6 Cu2 N8 94.32(14) . . ? N9 Cu2 N7 96.97(14) . . ? C21' Cu2 N7 113.43(15) . . ? N6 Cu2 N7 78.69(15) . . ? N8 Cu2 N7 98.81(12) . . ? F2 B1 F4 117.4(8) . . ? F2 B1 F3 110.6(7) . . ? F4 B1 F3 106.8(6) . . ? F2 B1 F1 108.7(7) . . ? F4 B1 F1 106.4(7) . . ? F3 B1 F1 106.2(7) . . ? F5 B2 F7 120.4(5) . 2_655 ? F5 B2 F7 120.4(5) . . ? F7 B2 F7 119.2(9) 2_655 . ? F5 B2 F6 80.8(5) . . ? F7 B2 F6 92.5(4) 2_655 . ? F7 B2 F6 96.8(4) . . ? F5 B2 F6 80.8(5) . 2_655 ? F7 B2 F6 96.8(4) 2_655 2_655 ? F7 B2 F6 92.5(4) . 2_655 ? F6 B2 F6 161.7(10) . 2_655 ? F9 B3 F9 118.0(12) 2 . ? F9 B3 F8 106.0(3) 2 2 ? F9 B3 F8 109.0(4) . 2 ? F9 B3 F8 109.0(4) 2 . ? F9 B3 F8 106.0(3) . . ? F8 B3 F8 108.6(11) 2 . ? F10' B4 F12 124.6(8) . . ? F10' B4 F10 46.0(7) . . ? F12 B4 F10 111.4(7) . . ? F10' B4 F13' 112.2(8) . . ? F12 B4 F13' 74.4(9) . . ? F10 B4 F13' 66.3(7) . . ? F10' B4 F11' 111.8(8) . . ? F12 B4 F11' 115.6(9) . . ? F10 B4 F11' 130.3(9) . . ? F13' B4 F11' 111.9(8) . . ? F10' B4 F11 125.9(9) . . ? F12 B4 F11 109.0(7) . . ? F10 B4 F11 110.2(7) . . ? F13' B4 F11 73.4(9) . . ? F11' B4 F11 38.7(8) . . ? F10' B4 F13 56.2(7) . . ? F12 B4 F13 114.3(8) . . ? F10 B4 F13 102.1(6) . . ? F13' B4 F13 167.9(9) . . ? F11' B4 F13 72.8(8) . . ? F11 B4 F13 109.7(7) . . ? F10' B4 F12' 107.7(7) . . ? F12 B4 F12' 33.2(8) . . ? F10 B4 F12' 123.0(8) . . ? F13' B4 F12' 107.5(8) . . ? F11' B4 F12' 105.3(7) . . ? F11 B4 F12' 122.1(9) . . ? F13 B4 F12' 81.1(9) . . ? N1 C1 C2 122.6(5) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 118.5(5) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C4 C3 C2 120.1(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.1(5) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 121.7(5) . . ? N1 C5 C6 114.2(4) . . ? C4 C5 C6 124.1(5) . . ? N2 C6 C7 121.3(5) . . ? N2 C6 C5 115.2(4) . . ? C7 C6 C5 123.4(5) . . ? C8 C7 C6 118.5(6) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C9 C8 C7 119.9(6) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 119.2(6) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? N2 C10 C9 121.8(6) . . ? N2 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? N3 C11 C12 122.4(4) . . ? N3 C11 H11 118.8 . . ? C12 C11 H11 118.8 . . ? C11 C12 C13 118.9(4) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C12 C13 C14 119.2(5) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C15 119.7(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? N3 C15 C14 120.8(4) . . ? N3 C15 C16 115.0(3) . . ? C14 C15 C16 124.2(4) . . ? N4 C16 C17 121.6(4) . . ? N4 C16 C15 115.1(3) . . ? C17 C16 C15 123.3(4) . . ? C18 C17 C16 119.1(4) . . ? C18 C17 H17 120.5 . . ? C16 C17 H17 120.5 . . ? C19 C18 C17 119.8(4) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C20 118.4(4) . . ? C18 C19 H19 120.8 . . ? C20 C19 H19 120.8 . . ? N4 C20 C19 123.7(4) . . ? N4 C20 H20 118.1 . . ? C19 C20 H20 118.1 . . ? C21' C21 Cu1 175.8(4) . . ? N6 C22 C23 121.3(5) . . ? N6 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 117.2(6) . . ? C24 C23 H23 121.4 . . ? C22 C23 H23 121.4 . . ? C25 C24 C23 121.4(7) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 C26 120.1(6) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? N6 C26 C25 119.6(5) . . ? N6 C26 C27 116.1(4) . . ? C25 C26 C27 124.3(5) . . ? N7 C27 C28 121.0(5) . . ? N7 C27 C26 115.1(4) . . ? C28 C27 C26 123.8(5) . . ? C29 C28 C27 118.7(5) . . ? C29 C28 H28 120.7 . . ? C27 C28 H28 120.7 . . ? C28 C29 C30 120.8(5) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C29 C30 C31 117.3(6) . . ? C29 C30 H30 121.3 . . ? C31 C30 H30 121.3 . . ? N7 C31 C30 124.4(5) . . ? N7 C31 H31 117.8 . . ? C30 C31 H31 117.8 . . ? N8 C32 C33 124.0(4) . . ? N8 C32 H32 118.0 . . ? C33 C32 H32 118.0 . . ? C32 C33 C34 117.3(5) . . ? C32 C33 H33 121.4 . . ? C34 C33 H33 121.4 . . ? C35 C34 C33 120.3(5) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C34 C35 C36 119.7(5) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? N8 C36 C35 120.5(4) . . ? N8 C36 C37 114.6(4) . . ? C35 C36 C37 124.8(4) . . ? N9 C37 C38 121.2(4) . . ? N9 C37 C36 114.9(4) . . ? C38 C37 C36 123.9(5) . . ? C39 C38 C37 119.3(5) . . ? C39 C38 H38 120.3 . . ? C37 C38 H38 120.3 . . ? C38 C39 C40 120.3(5) . . ? C38 C39 H39 119.8 . . ? C40 C39 H39 119.8 . . ? C39 C40 C41 117.7(5) . . ? C39 C40 H40 121.2 . . ? C41 C40 H40 121.2 . . ? N9 C41 C40 123.0(5) . . ? N9 C41 H41 118.5 . . ? C40 C41 H41 118.5 . . ? C21 C21' Cu2 177.7(4) . . ? C1 N1 C5 118.0(4) . . ? C1 N1 Cu1 127.4(3) . . ? C5 N1 Cu1 113.4(3) . . ? C10 N2 C6 119.2(4) . . ? C10 N2 Cu1 124.9(4) . . ? C6 N2 Cu1 115.7(3) . . ? C15 N3 C11 118.9(4) . . ? C15 N3 Cu1 117.9(3) . . ? C11 N3 Cu1 123.2(3) . . ? C20 N4 C16 117.4(4) . . ? C20 N4 Cu1 130.2(3) . . ? C16 N4 Cu1 112.4(3) . . ? C22 N6 C26 120.5(4) . . ? C22 N6 Cu2 122.5(3) . . ? C26 N6 Cu2 116.9(3) . . ? C31 N7 C27 117.8(4) . . ? C31 N7 Cu2 129.2(3) . . ? C27 N7 Cu2 113.0(3) . . ? C32 N8 C36 118.2(4) . . ? C32 N8 Cu2 128.0(3) . . ? C36 N8 Cu2 113.8(3) . . ? C41 N9 C37 118.5(4) . . ? C41 N9 Cu2 125.6(3) . . ? C37 N9 Cu2 115.9(3) . . ? H1A O1 H1B 109.5 . . ? H2A O2 H2B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.521 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.060 data_5 _database_code_depnum_ccdc_archive 'CCDC 869862' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H32 Cu2 N9, 2(C30 H24 Cu N6), 7(F6 P), C2 H3 N' _chemical_formula_sum 'C103 H83 Cu4 F42 N22 P7' _chemical_formula_weight 2897.86 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 15.148(3) _cell_length_b 16.542(3) _cell_length_c 24.379(4) _cell_angle_alpha 104.058(3) _cell_angle_beta 92.414(3) _cell_angle_gamma 98.864(3) _cell_volume 5834.6(18) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3315 _cell_measurement_theta_min 2.372 _cell_measurement_theta_max 18.592 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2908 _exptl_absorpt_coefficient_mu 0.940 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8956 _exptl_absorpt_correction_T_max 0.9119 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29608 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.1628 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 20247 _reflns_number_gt 7314 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0783P)^2^] 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 20247 _refine_ls_number_parameters 1604 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1576 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1536 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 0.665 _refine_ls_restrained_S_all 0.665 _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 0.34641(4) 0.65888(4) 0.43670(3) 0.0519(2) Uani 1 1 d . . . Cu2 Cu 0.17487(4) 0.85857(4) 0.56837(3) 0.0545(2) Uani 1 1 d . . . Cu3 Cu 0.52451(5) 0.23980(4) 0.16349(3) 0.0672(2) Uani 1 1 d . . . Cu4 Cu 0.08681(5) 0.29917(5) 0.84971(3) 0.0674(2) Uani 1 1 d . . . C1 C 0.1735(4) 0.5445(4) 0.4258(3) 0.0673(17) Uani 1 1 d . . . H1 H 0.1854 0.5498 0.4643 0.081 Uiso 1 1 calc R . . C2 C 0.0965(4) 0.4937(4) 0.3990(3) 0.079(2) Uani 1 1 d . . . H2 H 0.0570 0.4652 0.4189 0.095 Uiso 1 1 calc R . . C3 C 0.0790(4) 0.4855(4) 0.3432(4) 0.082(2) Uani 1 1 d . . . H3 H 0.0268 0.4515 0.3239 0.098 Uiso 1 1 calc R . . C4 C 0.1390(4) 0.5280(4) 0.3150(3) 0.0735(18) Uani 1 1 d . . . H4 H 0.1274 0.5224 0.2763 0.088 Uiso 1 1 calc R . . C5 C 0.2166(3) 0.5790(3) 0.3432(2) 0.0515(14) Uani 1 1 d . . . C6 C 0.2846(4) 0.6286(3) 0.3180(2) 0.0487(14) Uani 1 1 d . . . C7 C 0.2807(4) 0.6271(4) 0.2611(3) 0.0721(18) Uani 1 1 d . . . H7 H 0.2331 0.5938 0.2364 0.086 Uiso 1 1 calc R . . C8 C 0.3483(5) 0.6756(4) 0.2416(3) 0.0782(19) Uani 1 1 d . . . H8 H 0.3465 0.6753 0.2033 0.094 Uiso 1 1 calc R . . C9 C 0.4172(4) 0.7236(4) 0.2776(3) 0.0676(17) Uani 1 1 d . . . H9 H 0.4629 0.7569 0.2648 0.081 Uiso 1 1 calc R . . C10 C 0.4179(4) 0.7218(3) 0.3345(2) 0.0530(14) Uani 1 1 d . . . H10 H 0.4655 0.7542 0.3596 0.064 Uiso 1 1 calc R . . C11 C 0.3842(4) 0.4765(4) 0.4096(2) 0.0622(16) Uani 1 1 d . . . H11 H 0.3233 0.4587 0.3988 0.075 Uiso 1 1 calc R . . C12 C 0.4412(5) 0.4167(4) 0.4005(2) 0.0730(18) Uani 1 1 d . . . H12 H 0.4186 0.3599 0.3843 0.088 Uiso 1 1 calc R . . C13 C 0.5297(5) 0.4426(4) 0.4155(3) 0.0770(19) Uani 1 1 d . . . H13 H 0.5688 0.4038 0.4090 0.092 Uiso 1 1 calc R . . C14 C 0.5619(4) 0.5263(4) 0.4404(2) 0.0670(17) Uani 1 1 d . . . H14 H 0.6227 0.5445 0.4512 0.080 Uiso 1 1 calc R . . C15 C 0.5028(4) 0.5835(4) 0.4492(2) 0.0521(14) Uani 1 1 d . . . C16 C 0.5297(4) 0.6737(4) 0.4749(2) 0.0521(14) Uani 1 1 d . . . C17 C 0.6132(4) 0.7114(4) 0.5030(2) 0.0670(17) Uani 1 1 d . . . H17 H 0.6561 0.6784 0.5074 0.080 Uiso 1 1 calc R . . C18 C 0.6321(4) 0.7978(5) 0.5243(2) 0.0739(19) Uani 1 1 d . . . H18 H 0.6871 0.8234 0.5441 0.089 Uiso 1 1 calc R . . C19 C 0.5699(4) 0.8449(4) 0.5160(3) 0.0720(18) Uani 1 1 d . . . H19 H 0.5823 0.9036 0.5285 0.086 Uiso 1 1 calc R . . C20 C 0.4878(4) 0.8044(4) 0.4889(2) 0.0597(16) Uani 1 1 d . . . H20 H 0.4449 0.8372 0.4839 0.072 Uiso 1 1 calc R . . C21 C 0.3465(4) 0.9705(4) 0.5711(3) 0.0627(16) Uani 1 1 d . . . H21 H 0.3341 0.9574 0.5319 0.075 Uiso 1 1 calc R . . C22 C 0.4258(4) 1.0220(4) 0.5941(3) 0.0720(18) Uani 1 1 d . . . H22 H 0.4666 1.0430 0.5714 0.086 Uiso 1 1 calc R . . C23 C 0.4422(4) 1.0409(4) 0.6510(3) 0.080(2) Uani 1 1 d . . . H23 H 0.4955 1.0754 0.6680 0.096 Uiso 1 1 calc R . . C24 C 0.3823(4) 1.0105(4) 0.6836(3) 0.0730(18) Uani 1 1 d . . . H24 H 0.3934 1.0249 0.7229 0.088 Uiso 1 1 calc R . . C25 C 0.3037(4) 0.9573(4) 0.6577(3) 0.0566(15) Uani 1 1 d . . . C26 C 0.2355(4) 0.9156(4) 0.6880(3) 0.0571(15) Uani 1 1 d . . . C27 C 0.2400(4) 0.9315(5) 0.7465(3) 0.084(2) Uani 1 1 d . . . H27 H 0.2852 0.9719 0.7689 0.101 Uiso 1 1 calc R . . C28 C 0.1752(6) 0.8853(6) 0.7707(3) 0.107(3) Uani 1 1 d . . . H28 H 0.1774 0.8947 0.8100 0.128 Uiso 1 1 calc R . . C29 C 0.1090(5) 0.8269(5) 0.7382(4) 0.099(2) Uani 1 1 d . . . H29 H 0.0659 0.7953 0.7541 0.119 Uiso 1 1 calc R . . C30 C 0.1082(4) 0.8163(4) 0.6795(3) 0.0780(19) Uani 1 1 d . . . H30 H 0.0625 0.7775 0.6563 0.094 Uiso 1 1 calc R . . C31 C 0.1270(4) 1.0366(4) 0.5876(2) 0.0631(16) Uani 1 1 d . . . H31 H 0.1878 1.0575 0.5967 0.076 Uiso 1 1 calc R . . C32 C 0.0669(4) 1.0929(4) 0.5936(2) 0.0724(18) Uani 1 1 d . . . H32 H 0.0874 1.1509 0.6055 0.087 Uiso 1 1 calc R . . C33 C -0.0229(4) 1.0620(4) 0.5818(3) 0.0742(19) Uani 1 1 d . . . H33 H -0.0643 1.0987 0.5867 0.089 Uiso 1 1 calc R . . C34 C -0.0511(4) 0.9766(4) 0.5629(2) 0.0701(18) Uani 1 1 d . . . H34 H -0.1118 0.9548 0.5547 0.084 Uiso 1 1 calc R . . C35 C 0.0111(3) 0.9231(3) 0.5561(2) 0.0514(14) Uani 1 1 d . . . C36 C -0.0117(4) 0.8308(4) 0.5344(2) 0.0518(14) Uani 1 1 d . . . C37 C -0.0953(4) 0.7886(4) 0.5102(2) 0.0700(18) Uani 1 1 d . . . H37 H -0.1417 0.8186 0.5075 0.084 Uiso 1 1 calc R . . C38 C -0.1095(4) 0.7022(4) 0.4900(3) 0.0788(19) Uani 1 1 d . . . H38 H -0.1653 0.6730 0.4730 0.095 Uiso 1 1 calc R . . C39 C -0.0406(5) 0.6600(4) 0.4954(2) 0.0744(18) Uani 1 1 d . . . H39 H -0.0489 0.6014 0.4825 0.089 Uiso 1 1 calc R . . C40 C 0.0415(4) 0.7049(4) 0.5201(3) 0.0710(18) Uani 1 1 d . . . H40 H 0.0882 0.6757 0.5239 0.085 Uiso 1 1 calc R . . C41 C 0.2426(3) 0.7807(3) 0.5188(2) 0.0563(14) Uani 0.50 1 d P . . N9' N 0.2426(3) 0.7807(3) 0.5188(2) 0.0563(14) Uani 0.50 1 d P . . C42 C 0.7266(5) 0.2948(4) 0.1640(2) 0.0725(18) Uani 1 1 d . . . H42 H 0.7267 0.2428 0.1386 0.087 Uiso 1 1 calc R . . C43 C 0.8066(4) 0.3454(5) 0.1833(3) 0.081(2) Uani 1 1 d . . . H43 H 0.8600 0.3275 0.1723 0.097 Uiso 1 1 calc R . . C44 C 0.8072(5) 0.4226(5) 0.2189(3) 0.0808(19) Uani 1 1 d . . . H44 H 0.8611 0.4590 0.2325 0.097 Uiso 1 1 calc R . . C45 C 0.7269(5) 0.4462(4) 0.2347(2) 0.0725(18) Uani 1 1 d . . . H45 H 0.7264 0.4990 0.2591 0.087 Uiso 1 1 calc R . . C46 C 0.6476(4) 0.3925(4) 0.2148(2) 0.0581(15) Uani 1 1 d . . . C47 C 0.5593(4) 0.4108(4) 0.2306(2) 0.0590(15) Uani 1 1 d . . . C48 C 0.5459(5) 0.4886(4) 0.2627(3) 0.083(2) Uani 1 1 d . . . H48 H 0.5935 0.5330 0.2756 0.100 Uiso 1 1 calc R . . C49 C 0.4600(6) 0.4977(5) 0.2746(3) 0.099(2) Uani 1 1 d . . . H49 H 0.4494 0.5496 0.2958 0.118 Uiso 1 1 calc R . . C50 C 0.3904(5) 0.4340(5) 0.2566(3) 0.091(2) Uani 1 1 d . . . H50 H 0.3322 0.4413 0.2648 0.109 Uiso 1 1 calc R . . C51 C 0.4084(4) 0.3566(4) 0.2254(3) 0.0753(19) Uani 1 1 d . . . H51 H 0.3616 0.3110 0.2137 0.090 Uiso 1 1 calc R . . C52 C 0.6152(5) 0.2260(4) 0.2863(3) 0.0783(19) Uani 1 1 d . . . H52 H 0.6691 0.2525 0.2769 0.094 Uiso 1 1 calc R . . C53 C 0.6100(5) 0.2210(4) 0.3415(3) 0.080(2) Uani 1 1 d . . . H53 H 0.6581 0.2430 0.3687 0.096 Uiso 1 1 calc R . . C54 C 0.5299(7) 0.1818(5) 0.3543(3) 0.105(3) Uani 1 1 d . . . H54 H 0.5227 0.1774 0.3912 0.126 Uiso 1 1 calc R . . C55 C 0.4604(5) 0.1491(5) 0.3134(4) 0.095(2) Uani 1 1 d . . . H55 H 0.4064 0.1217 0.3219 0.114 Uiso 1 1 calc R . . C56 C 0.4721(5) 0.1576(4) 0.2589(3) 0.0702(18) Uani 1 1 d . . . C57 C 0.4000(5) 0.1269(4) 0.2122(3) 0.0728(19) Uani 1 1 d . . . C58 C 0.3271(6) 0.0669(5) 0.2142(4) 0.101(2) Uani 1 1 d . . . H58 H 0.3214 0.0447 0.2457 0.122 Uiso 1 1 calc R . . C59 C 0.2629(6) 0.0403(5) 0.1693(5) 0.118(3) Uani 1 1 d . . . H59 H 0.2143 -0.0014 0.1697 0.142 Uiso 1 1 calc R . . C60 C 0.2707(6) 0.0753(6) 0.1238(4) 0.120(3) Uani 1 1 d . . . H60 H 0.2270 0.0594 0.0935 0.143 Uiso 1 1 calc R . . C61 C 0.3429(5) 0.1329(5) 0.1246(3) 0.099(2) Uani 1 1 d . . . H61 H 0.3483 0.1559 0.0934 0.118 Uiso 1 1 calc R . . C62 C 0.5884(5) 0.0825(5) 0.1129(3) 0.090(2) Uani 1 1 d . . . H62 H 0.5847 0.0747 0.1493 0.108 Uiso 1 1 calc R . . C63 C 0.6189(5) 0.0219(5) 0.0716(4) 0.109(3) Uani 1 1 d . . . H63 H 0.6353 -0.0259 0.0800 0.131 Uiso 1 1 calc R . . C64 C 0.6242(6) 0.0341(6) 0.0187(4) 0.116(3) Uani 1 1 d . . . H64 H 0.6445 -0.0056 -0.0097 0.139 Uiso 1 1 calc R . . C65 C 0.5998(5) 0.1045(6) 0.0073(3) 0.105(3) Uani 1 1 d . . . H65 H 0.6033 0.1132 -0.0289 0.125 Uiso 1 1 calc R . . C66 C 0.5697(4) 0.1630(5) 0.0498(3) 0.0752(19) Uani 1 1 d . . . C67 C 0.5412(5) 0.2396(5) 0.0402(3) 0.082(2) Uani 1 1 d . . . C68 C 0.5604(6) 0.2717(6) -0.0061(3) 0.113(3) Uani 1 1 d . . . H68 H 0.5968 0.2463 -0.0325 0.136 Uiso 1 1 calc R . . C69 C 0.5250(7) 0.3429(7) -0.0133(4) 0.135(3) Uani 1 1 d . . . H69 H 0.5368 0.3643 -0.0447 0.162 Uiso 1 1 calc R . . C70 C 0.4739(6) 0.3794(6) 0.0262(4) 0.119(3) Uani 1 1 d . . . H70 H 0.4490 0.4259 0.0225 0.143 Uiso 1 1 calc R . . C71 C 0.4595(5) 0.3460(6) 0.0722(4) 0.107(2) Uani 1 1 d . . . H71 H 0.4251 0.3724 0.0996 0.128 Uiso 1 1 calc R . . C72 C -0.0858(5) 0.2383(4) 0.8932(3) 0.087(2) Uani 1 1 d . . . H72 H -0.0522 0.2461 0.9275 0.105 Uiso 1 1 calc R . . C73 C -0.1753(6) 0.2060(5) 0.8893(4) 0.111(3) Uani 1 1 d . . . H73 H -0.2022 0.1946 0.9208 0.133 Uiso 1 1 calc R . . C74 C -0.2236(5) 0.1911(5) 0.8395(4) 0.108(3) Uani 1 1 d . . . H74 H -0.2840 0.1673 0.8356 0.130 Uiso 1 1 calc R . . C75 C -0.1824(5) 0.2115(4) 0.7940(3) 0.089(2) Uani 1 1 d . . . H75 H -0.2146 0.2008 0.7590 0.107 Uiso 1 1 calc R . . C76 C -0.0938(4) 0.2477(4) 0.8010(3) 0.0635(16) Uani 1 1 d . . . C77 C -0.0447(4) 0.2748(3) 0.7560(3) 0.0609(16) Uani 1 1 d . . . C78 C -0.0828(4) 0.2681(4) 0.7022(3) 0.0755(19) Uani 1 1 d . . . H78 H -0.1427 0.2439 0.6921 0.091 Uiso 1 1 calc R . . C79 C -0.0311(6) 0.2976(5) 0.6638(3) 0.088(2) Uani 1 1 d . . . H79 H -0.0553 0.2932 0.6273 0.106 Uiso 1 1 calc R . . C80 C 0.0573(5) 0.3336(4) 0.6805(3) 0.081(2) Uani 1 1 d . . . H80 H 0.0930 0.3558 0.6557 0.098 Uiso 1 1 calc R . . C81 C 0.0918(4) 0.3365(4) 0.7335(3) 0.0701(17) Uani 1 1 d . . . H81 H 0.1521 0.3586 0.7438 0.084 Uiso 1 1 calc R . . C82 C 0.0265(5) 0.4717(5) 0.9152(3) 0.092(2) Uani 1 1 d . . . H82 H -0.0311 0.4405 0.9104 0.111 Uiso 1 1 calc R . . C83 C 0.0379(7) 0.5569(5) 0.9412(3) 0.108(3) Uani 1 1 d . . . H83 H -0.0105 0.5825 0.9540 0.130 Uiso 1 1 calc R . . C84 C 0.1207(8) 0.6018(5) 0.9474(3) 0.111(3) Uani 1 1 d . . . H84 H 0.1307 0.6595 0.9645 0.133 Uiso 1 1 calc R . . C85 C 0.1913(5) 0.5619(5) 0.9282(3) 0.092(2) Uani 1 1 d . . . H85 H 0.2493 0.5922 0.9325 0.111 Uiso 1 1 calc R . . C86 C 0.1746(5) 0.4763(4) 0.9027(2) 0.0698(17) Uani 1 1 d . . . C87 C 0.2446(4) 0.4280(5) 0.8792(3) 0.0693(17) Uani 1 1 d . . . C88 C 0.3342(5) 0.4634(5) 0.8864(3) 0.093(2) Uani 1 1 d . . . H88 H 0.3526 0.5198 0.9059 0.112 Uiso 1 1 calc R . . C89 C 0.3962(5) 0.4140(7) 0.8643(4) 0.111(3) Uani 1 1 d . . . H89 H 0.4571 0.4359 0.8712 0.134 Uiso 1 1 calc R . . C90 C 0.3693(5) 0.3353(7) 0.8333(3) 0.107(3) Uani 1 1 d . . . H90 H 0.4105 0.3031 0.8162 0.129 Uiso 1 1 calc R . . C91 C 0.2784(5) 0.3022(5) 0.8270(3) 0.092(2) Uani 1 1 d . . . H91 H 0.2594 0.2464 0.8066 0.110 Uiso 1 1 calc R . . C92 C 0.1584(5) 0.2845(5) 0.9601(3) 0.094(2) Uani 1 1 d . . . H92 H 0.1675 0.3432 0.9674 0.113 Uiso 1 1 calc R . . C93 C 0.1839(6) 0.2464(7) 1.0020(3) 0.138(3) Uani 1 1 d . . . H93 H 0.2115 0.2789 1.0369 0.166 Uiso 1 1 calc R . . C94 C 0.1673(8) 0.1606(7) 0.9905(5) 0.163(4) Uani 1 1 d . . . H94 H 0.1840 0.1344 1.0181 0.195 Uiso 1 1 calc R . . C95 C 0.1268(7) 0.1115(6) 0.9394(4) 0.141(4) Uani 1 1 d . . . H95 H 0.1128 0.0529 0.9324 0.169 Uiso 1 1 calc R . . C96 C 0.1074(5) 0.1542(5) 0.8983(3) 0.089(2) Uani 1 1 d . . . C97 C 0.0682(5) 0.1061(5) 0.8414(3) 0.082(2) Uani 1 1 d . . . C98 C 0.0135(6) 0.0289(5) 0.8324(4) 0.117(3) Uani 1 1 d . . . H98 H -0.0001 0.0053 0.8626 0.140 Uiso 1 1 calc R . . C99 C -0.0210(6) -0.0131(6) 0.7780(5) 0.127(3) Uani 1 1 d . . . H99 H -0.0574 -0.0658 0.7708 0.153 Uiso 1 1 calc R . . C100 C -0.0007(7) 0.0244(6) 0.7342(4) 0.128(3) Uani 1 1 d . . . H100 H -0.0233 -0.0022 0.6971 0.154 Uiso 1 1 calc R . . C101 C 0.0549(5) 0.1033(5) 0.7473(3) 0.109(3) Uani 1 1 d . . . H101 H 0.0696 0.1286 0.7180 0.131 Uiso 1 1 calc R . . C41' C 0.2828(3) 0.7358(3) 0.4903(2) 0.0558(14) Uani 0.50 1 d P . . F1 F 0.2223(3) 0.8572(3) 0.4036(2) 0.168(2) Uani 1 1 d . . . F2 F 0.2557(2) 0.9934(3) 0.43916(18) 0.145(2) Uani 1 1 d . . . F3 F 0.1983(2) 0.9387(3) 0.34939(15) 0.1087(13) Uani 1 1 d . . . F4 F 0.3428(3) 1.0050(3) 0.3707(2) 0.1403(16) Uani 1 1 d . . . F5 F 0.3654(2) 0.9216(3) 0.42496(15) 0.1032(13) Uani 1 1 d . . . F6 F 0.3093(3) 0.8682(3) 0.33512(19) 0.160(2) Uani 1 1 d . . . F7 F 0.7775(3) 0.5162(3) 0.4388(2) 0.167(2) Uani 1 1 d . . . F8 F 0.7485(3) 0.3872(4) 0.4300(2) 0.195(3) Uani 1 1 d . . . F9 F 0.8578(3) 0.5002(4) 0.3676(2) 0.166(2) Uani 1 1 d . . . F10 F 0.8319(4) 0.3657(4) 0.3572(3) 0.234(4) Uani 1 1 d . . . F11 F 0.7182(2) 0.4293(3) 0.35597(16) 0.1200(15) Uani 1 1 d . . . F12 F 0.8904(2) 0.4506(2) 0.43956(16) 0.1029(12) Uani 1 1 d . . . F13 F 0.5535(4) 0.9607(3) 0.18347(19) 0.176(2) Uani 1 1 d . . . F14 F 0.4431(3) 0.8939(3) 0.21725(18) 0.1418(17) Uani 1 1 d . . . F15 F 0.5684(4) 0.8460(3) 0.2026(2) 0.186(2) Uani 1 1 d U . . F16 F 0.5567(4) 0.8535(4) 0.1138(2) 0.200(3) Uani 1 1 d . . . F17 F 0.4305(3) 0.9030(3) 0.12779(17) 0.1493(18) Uani 1 1 d . . . F18 F 0.4487(3) 0.7805(3) 0.14687(19) 0.1498(18) Uani 1 1 d . . . F19 F 0.2668(6) 0.6038(5) 0.0733(4) 0.267(4) Uani 1 1 d . . . F20 F 0.2170(4) 0.5431(5) 0.1344(2) 0.231(4) Uani 1 1 d . . . F21 F 0.3586(4) 0.5461(4) 0.1148(2) 0.208(3) Uani 1 1 d . . . F22 F 0.2705(5) 0.4284(5) 0.0900(3) 0.233(3) Uani 1 1 d . . . F23 F 0.3113(4) 0.4901(4) 0.0264(2) 0.186(2) Uani 1 1 d . . . F24 F 0.1741(3) 0.4809(4) 0.0474(2) 0.197(3) Uani 1 1 d . . . F25 F 0.6139(3) 0.6775(3) 0.36744(17) 0.1222(15) Uani 1 1 d . . . F26 F 0.6676(4) 0.8109(3) 0.3874(2) 0.175(2) Uani 1 1 d . . . F27 F 0.7584(3) 0.7263(4) 0.3921(2) 0.173(2) Uani 1 1 d . . . F28 F 0.7131(3) 0.6539(2) 0.3036(2) 0.147(2) Uani 1 1 d . . . F29 F 0.7684(3) 0.7886(2) 0.32324(18) 0.1225(15) Uani 1 1 d . . . F30 F 0.6252(3) 0.7432(4) 0.3002(2) 0.180(2) Uani 1 1 d . . . F31 F 0.1035(4) 0.2761(4) 0.3397(4) 0.291(5) Uani 1 1 d . . . F32 F 0.2236(4) 0.3005(4) 0.3935(2) 0.213(3) Uani 1 1 d . . . F33 F 0.1508(7) 0.1752(4) 0.3531(3) 0.286(4) Uani 1 1 d . . . F34 F 0.2825(5) 0.2355(5) 0.3266(4) 0.300(5) Uani 1 1 d . . . F35 F 0.1657(6) 0.1994(5) 0.2745(3) 0.266(4) Uani 1 1 d . . . F36 F 0.2221(4) 0.3344(4) 0.3166(2) 0.187(2) Uani 1 1 d . . . F37 F 0.9739(4) 0.0986(3) 0.0605(3) 0.180(2) Uani 1 1 d . . . F38 F 0.8687(7) 0.0749(5) -0.0056(3) 0.312(6) Uani 1 1 d . . . F39 F 0.8348(4) 0.0851(6) 0.0771(4) 0.262(4) Uani 1 1 d . . . F40 F 0.8116(3) 0.1823(3) 0.0330(3) 0.178(2) Uani 1 1 d . . . F41 F 0.9133(5) 0.2044(5) 0.1034(3) 0.253(4) Uani 1 1 d . . . F42 F 0.9534(4) 0.2013(5) 0.0234(3) 0.226(3) Uani 1 1 d . . . N1 N 0.2328(3) 0.5873(3) 0.3993(2) 0.0523(12) Uani 1 1 d . . . N2 N 0.3535(3) 0.6758(3) 0.35414(17) 0.0465(11) Uani 1 1 d . . . N3 N 0.4141(3) 0.5580(3) 0.43323(17) 0.0512(11) Uani 1 1 d . . . N4 N 0.4663(3) 0.7206(3) 0.46921(17) 0.0514(11) Uani 1 1 d . . . N5 N 0.2860(3) 0.9380(3) 0.6016(2) 0.0534(12) Uani 1 1 d . . . N6 N 0.1703(3) 0.8594(3) 0.65540(19) 0.0555(12) Uani 1 1 d . . . N7 N 0.0998(3) 0.9529(3) 0.56893(16) 0.0495(11) Uani 1 1 d . . . N8 N 0.0563(3) 0.7893(3) 0.53870(17) 0.0523(12) Uani 1 1 d . . . N9 N 0.2828(3) 0.7358(3) 0.4903(2) 0.0558(14) Uani 0.50 1 d P . . N10 N 0.6473(3) 0.3153(3) 0.17929(19) 0.0613(13) Uani 1 1 d . . . N11 N 0.4908(3) 0.3465(3) 0.21178(18) 0.0618(13) Uani 1 1 d . . . N12 N 0.5487(4) 0.1955(3) 0.2451(2) 0.0663(14) Uani 1 1 d . . . N13 N 0.4082(4) 0.1602(3) 0.1668(3) 0.0750(15) Uani 1 1 d . . . N14 N 0.5644(3) 0.1513(3) 0.1021(2) 0.0712(14) Uani 1 1 d . . . N15 N 0.4913(4) 0.2787(4) 0.0802(2) 0.0831(16) Uani 1 1 d . . . N16 N -0.0441(3) 0.2595(3) 0.8496(2) 0.0687(14) Uani 1 1 d . . . N17 N 0.0424(3) 0.3087(3) 0.7712(2) 0.0608(13) Uani 1 1 d . . . N18 N 0.0928(4) 0.4317(3) 0.8967(2) 0.0687(14) Uani 1 1 d . . . N19 N 0.2171(3) 0.3484(3) 0.8494(2) 0.0681(14) Uani 1 1 d . . . N20 N 0.1213(3) 0.2378(4) 0.9098(2) 0.0752(15) Uani 1 1 d . . . N21 N 0.0878(4) 0.1441(4) 0.8004(3) 0.0898(17) Uani 1 1 d . . . P1 P 0.28249(11) 0.93062(11) 0.38682(7) 0.0671(5) Uani 1 1 d . . . P2 P 0.80489(12) 0.43916(12) 0.39601(8) 0.0720(5) Uani 1 1 d . . . P3 P 0.49536(16) 0.87370(15) 0.16549(9) 0.0974(7) Uani 1 1 d U . . P4 P 0.26592(17) 0.5162(2) 0.08217(10) 0.1165(8) Uani 1 1 d . . . P5 P 0.69170(12) 0.73344(11) 0.34651(8) 0.0702(5) Uani 1 1 d . . . P6 P 0.19069(15) 0.25086(15) 0.33325(10) 0.0970(7) Uani 1 1 d . . . P7 P 0.89260(18) 0.13928(15) 0.04626(11) 0.1049(7) Uani 1 1 d . . . N22 N 0.0306(9) 0.4093(16) 0.1974(7) 0.351(13) Uani 1 1 d . . . C102 C 0.0764(11) 0.3530(13) 0.1805(7) 0.263(14) Uani 1 1 d D . . C103 C 0.1297(11) 0.3001(12) 0.1600(7) 0.275(10) Uani 1 1 d D . . H10A H 0.1525 0.3124 0.1262 0.413 Uiso 1 1 calc R . . H10B H 0.0970 0.2434 0.1510 0.413 Uiso 1 1 calc R . . H10C H 0.1787 0.3056 0.1877 0.413 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 0.0498(4) 0.0568(4) 0.0459(4) 0.0077(3) 0.0055(3) 0.0070(3) Cu2 0.0442(4) 0.0542(5) 0.0607(5) 0.0071(3) -0.0003(3) 0.0081(3) Cu3 0.0764(5) 0.0607(5) 0.0589(5) 0.0052(4) 0.0147(4) 0.0082(4) Cu4 0.0662(5) 0.0726(5) 0.0606(5) 0.0139(4) 0.0051(4) 0.0079(4) C1 0.053(4) 0.068(4) 0.076(5) 0.015(4) 0.013(4) -0.001(3) C2 0.058(4) 0.078(5) 0.097(6) 0.020(4) 0.019(4) -0.003(4) C3 0.044(4) 0.077(5) 0.114(7) 0.013(5) -0.009(4) 0.001(3) C4 0.058(4) 0.087(5) 0.069(5) 0.012(4) -0.013(4) 0.010(4) C5 0.045(3) 0.050(4) 0.055(4) 0.002(3) -0.002(3) 0.013(3) C6 0.050(3) 0.054(4) 0.041(4) 0.009(3) 0.005(3) 0.011(3) C7 0.075(4) 0.087(5) 0.050(4) 0.012(4) -0.002(3) 0.012(4) C8 0.102(5) 0.092(5) 0.044(4) 0.020(4) 0.009(4) 0.024(5) C9 0.078(5) 0.075(5) 0.058(4) 0.027(4) 0.019(4) 0.021(4) C10 0.053(4) 0.055(4) 0.052(4) 0.012(3) 0.012(3) 0.014(3) C11 0.059(4) 0.062(4) 0.065(4) 0.017(3) 0.002(3) 0.010(3) C12 0.096(5) 0.044(4) 0.080(5) 0.015(3) 0.004(4) 0.020(4) C13 0.077(5) 0.070(5) 0.094(5) 0.024(4) 0.020(4) 0.032(4) C14 0.057(4) 0.072(5) 0.075(4) 0.021(4) 0.005(3) 0.018(4) C15 0.053(4) 0.056(4) 0.051(4) 0.021(3) 0.008(3) 0.008(3) C16 0.048(4) 0.063(4) 0.045(3) 0.016(3) 0.011(3) 0.005(3) C17 0.055(4) 0.072(5) 0.076(5) 0.025(4) 0.010(3) 0.008(3) C18 0.064(4) 0.088(6) 0.059(4) 0.014(4) 0.000(3) -0.009(4) C19 0.067(4) 0.056(4) 0.078(5) 0.000(3) 0.004(4) -0.011(4) C20 0.059(4) 0.067(4) 0.053(4) 0.015(3) 0.012(3) 0.010(3) C21 0.057(4) 0.063(4) 0.066(4) 0.010(3) 0.007(3) 0.012(3) C22 0.056(4) 0.071(5) 0.087(5) 0.025(4) 0.007(4) -0.003(3) C23 0.060(4) 0.074(5) 0.096(6) 0.020(4) -0.007(4) -0.010(4) C24 0.067(4) 0.075(5) 0.064(4) 0.003(4) -0.007(4) 0.000(4) C25 0.051(4) 0.062(4) 0.057(4) 0.014(3) 0.002(3) 0.014(3) C26 0.051(4) 0.069(4) 0.053(4) 0.011(3) 0.006(3) 0.025(3) C27 0.076(5) 0.110(6) 0.068(5) 0.025(4) 0.016(4) 0.018(4) C28 0.106(6) 0.155(8) 0.065(5) 0.031(5) 0.016(5) 0.036(6) C29 0.086(6) 0.124(7) 0.102(7) 0.052(6) 0.036(5) 0.020(5) C30 0.060(4) 0.087(5) 0.092(6) 0.035(4) 0.007(4) 0.009(4) C31 0.053(4) 0.056(4) 0.075(4) 0.009(3) 0.005(3) 0.005(3) C32 0.083(5) 0.049(4) 0.085(5) 0.007(3) 0.011(4) 0.025(4) C33 0.061(4) 0.069(5) 0.091(5) 0.009(4) 0.011(4) 0.023(4) C34 0.042(3) 0.074(5) 0.091(5) 0.011(4) 0.009(3) 0.012(3) C35 0.042(3) 0.058(4) 0.055(4) 0.014(3) 0.003(3) 0.008(3) C36 0.049(4) 0.056(4) 0.050(4) 0.011(3) 0.008(3) 0.007(3) C37 0.048(4) 0.061(4) 0.096(5) 0.017(4) -0.006(3) 0.001(3) C38 0.056(4) 0.076(5) 0.100(5) 0.028(4) -0.014(4) -0.008(4) C39 0.080(5) 0.055(4) 0.079(5) 0.016(3) -0.005(4) -0.010(4) C40 0.071(4) 0.052(4) 0.090(5) 0.017(4) -0.011(4) 0.017(3) C41 0.053(3) 0.052(3) 0.062(4) 0.011(3) 0.003(3) 0.008(3) N9' 0.053(3) 0.052(3) 0.062(4) 0.011(3) 0.003(3) 0.008(3) C42 0.076(5) 0.070(5) 0.068(4) 0.010(3) 0.018(4) 0.013(4) C43 0.064(5) 0.096(6) 0.088(5) 0.030(4) 0.015(4) 0.014(4) C44 0.083(5) 0.085(5) 0.071(5) 0.018(4) 0.005(4) 0.004(4) C45 0.083(5) 0.067(4) 0.064(4) 0.013(3) 0.013(4) 0.007(4) C46 0.075(4) 0.055(4) 0.046(4) 0.015(3) 0.011(3) 0.011(3) C47 0.072(4) 0.056(4) 0.051(4) 0.015(3) 0.017(3) 0.014(4) C48 0.084(5) 0.065(5) 0.091(5) 0.000(4) 0.023(4) 0.011(4) C49 0.119(7) 0.064(5) 0.114(6) 0.015(4) 0.031(5) 0.026(5) C50 0.083(5) 0.085(6) 0.109(6) 0.018(5) 0.036(4) 0.025(5) C51 0.074(5) 0.062(4) 0.087(5) 0.014(4) 0.021(4) 0.007(4) C52 0.087(5) 0.073(5) 0.075(5) 0.015(4) 0.017(4) 0.016(4) C53 0.113(6) 0.072(5) 0.062(5) 0.028(4) 0.005(4) 0.025(4) C54 0.137(8) 0.121(7) 0.074(6) 0.045(5) 0.035(6) 0.034(6) C55 0.093(6) 0.106(6) 0.098(7) 0.047(5) 0.038(5) 0.013(5) C56 0.077(5) 0.061(4) 0.078(5) 0.018(4) 0.023(4) 0.021(4) C57 0.071(5) 0.054(4) 0.091(6) 0.010(4) 0.038(4) 0.010(4) C58 0.098(6) 0.089(6) 0.123(7) 0.036(5) 0.032(5) 0.011(5) C59 0.086(6) 0.084(6) 0.176(10) 0.032(7) 0.026(7) -0.013(5) C60 0.090(7) 0.104(7) 0.138(9) 0.004(6) -0.010(6) -0.016(5) C61 0.090(6) 0.106(6) 0.086(6) 0.013(5) -0.007(5) -0.003(5) C62 0.119(6) 0.075(5) 0.075(5) 0.016(4) 0.021(4) 0.013(5) C63 0.135(7) 0.076(6) 0.110(7) -0.003(5) 0.022(6) 0.033(5) C64 0.137(7) 0.114(8) 0.078(7) -0.017(6) 0.026(5) 0.025(6) C65 0.127(7) 0.099(6) 0.074(6) -0.001(5) 0.019(5) 0.010(5) C66 0.079(5) 0.079(5) 0.052(5) -0.005(4) 0.001(4) -0.001(4) C67 0.089(5) 0.095(6) 0.056(5) 0.021(4) 0.011(4) -0.001(4) C68 0.128(7) 0.145(8) 0.063(6) 0.033(5) 0.011(5) 0.002(6) C69 0.158(10) 0.152(10) 0.106(8) 0.066(7) -0.011(7) 0.009(7) C70 0.157(9) 0.126(8) 0.095(7) 0.058(6) 0.005(6) 0.038(6) C71 0.116(7) 0.109(7) 0.097(7) 0.033(5) -0.001(5) 0.011(5) C72 0.090(6) 0.101(6) 0.077(5) 0.032(4) 0.011(4) 0.019(5) C73 0.095(7) 0.123(7) 0.126(8) 0.051(6) 0.044(6) 0.012(6) C74 0.066(5) 0.127(7) 0.133(8) 0.054(6) 0.008(6) -0.011(5) C75 0.067(5) 0.094(6) 0.104(6) 0.033(4) -0.003(4) -0.006(4) C76 0.057(4) 0.054(4) 0.075(5) 0.013(3) -0.004(4) 0.003(3) C77 0.072(5) 0.047(4) 0.064(5) 0.009(3) 0.012(4) 0.015(3) C78 0.076(5) 0.072(5) 0.080(5) 0.019(4) -0.006(4) 0.022(4) C79 0.110(6) 0.097(6) 0.066(5) 0.023(4) 0.000(5) 0.040(5) C80 0.106(6) 0.078(5) 0.075(5) 0.039(4) 0.023(5) 0.023(4) C81 0.068(4) 0.072(5) 0.074(5) 0.024(4) 0.020(4) 0.011(3) C82 0.092(5) 0.082(6) 0.099(6) 0.010(4) 0.018(4) 0.020(4) C83 0.147(8) 0.078(6) 0.101(6) 0.007(5) 0.018(6) 0.051(6) C84 0.171(9) 0.059(5) 0.099(6) 0.016(4) 0.018(7) 0.011(6) C85 0.110(6) 0.072(6) 0.089(6) 0.023(4) 0.009(5) -0.007(5) C86 0.082(5) 0.069(5) 0.055(4) 0.020(4) -0.009(4) 0.001(4) C87 0.066(5) 0.090(5) 0.052(4) 0.026(4) -0.001(3) 0.003(4) C88 0.072(5) 0.111(6) 0.089(6) 0.029(4) -0.003(4) -0.013(5) C89 0.068(5) 0.175(10) 0.094(7) 0.047(6) 0.000(5) 0.008(6) C90 0.071(6) 0.166(9) 0.084(6) 0.019(6) 0.012(5) 0.033(6) C91 0.093(6) 0.115(6) 0.071(5) 0.017(4) 0.010(4) 0.038(5) C92 0.117(6) 0.096(6) 0.063(5) 0.029(5) -0.010(4) -0.005(5) C93 0.188(9) 0.144(9) 0.073(6) 0.044(6) -0.037(6) -0.015(8) C94 0.246(12) 0.135(9) 0.117(9) 0.075(8) -0.038(8) 0.008(9) C95 0.223(10) 0.109(7) 0.097(7) 0.045(6) -0.037(7) 0.035(7) C96 0.111(6) 0.064(5) 0.088(6) 0.017(5) -0.007(4) 0.013(4) C97 0.105(6) 0.056(5) 0.082(6) 0.012(4) 0.000(4) 0.011(4) C98 0.146(7) 0.087(6) 0.105(7) 0.011(5) 0.016(6) 0.001(6) C99 0.129(7) 0.087(7) 0.141(10) 0.000(7) -0.003(7) -0.008(5) C100 0.166(9) 0.084(7) 0.113(8) -0.012(6) -0.025(7) 0.020(6) C101 0.152(7) 0.090(6) 0.075(6) 0.002(5) -0.011(5) 0.029(6) C41' 0.053(3) 0.055(3) 0.055(3) 0.009(3) 0.005(3) 0.003(3) F1 0.119(4) 0.178(5) 0.225(6) 0.136(4) -0.040(4) -0.042(3) F2 0.089(3) 0.200(5) 0.119(4) -0.032(3) 0.000(2) 0.061(3) F3 0.087(3) 0.136(4) 0.104(3) 0.027(3) -0.019(2) 0.034(2) F4 0.129(4) 0.136(4) 0.165(4) 0.083(3) -0.002(3) -0.017(3) F5 0.059(2) 0.164(4) 0.096(3) 0.045(3) -0.004(2) 0.029(2) F6 0.136(4) 0.190(5) 0.123(4) -0.045(4) -0.018(3) 0.078(4) F7 0.103(3) 0.150(5) 0.212(5) -0.027(4) -0.019(3) 0.039(3) F8 0.172(5) 0.252(7) 0.153(5) 0.138(5) -0.059(4) -0.108(5) F9 0.125(4) 0.217(6) 0.186(5) 0.150(4) -0.002(3) -0.038(4) F10 0.250(7) 0.175(6) 0.228(7) -0.092(5) -0.054(5) 0.129(5) F11 0.090(3) 0.179(4) 0.092(3) 0.062(3) -0.020(2) -0.007(3) F12 0.080(2) 0.110(3) 0.126(3) 0.047(2) -0.009(2) 0.015(2) F13 0.226(5) 0.160(5) 0.115(4) 0.061(3) -0.044(4) -0.075(4) F14 0.163(4) 0.180(5) 0.085(3) 0.036(3) 0.022(3) 0.029(4) F15 0.215(6) 0.157(5) 0.168(5) 0.009(4) -0.050(4) 0.042(4) F16 0.187(5) 0.234(7) 0.153(5) 0.027(4) 0.054(4) -0.019(5) F17 0.153(4) 0.217(6) 0.087(3) 0.058(3) -0.014(3) 0.034(4) F18 0.184(4) 0.122(4) 0.120(4) 0.024(3) 0.003(3) -0.035(3) F19 0.314(10) 0.139(6) 0.360(11) 0.053(6) 0.058(8) 0.082(6) F20 0.148(5) 0.394(10) 0.092(4) -0.033(5) 0.019(3) 0.019(5) F21 0.122(4) 0.276(8) 0.177(5) -0.015(5) -0.042(4) 0.015(5) F22 0.239(7) 0.192(7) 0.288(9) 0.120(6) -0.002(6) 0.014(6) F23 0.198(5) 0.262(7) 0.099(4) 0.023(4) 0.039(4) 0.066(5) F24 0.115(4) 0.274(7) 0.137(4) -0.052(4) -0.022(3) 0.008(4) F25 0.113(3) 0.132(4) 0.123(4) 0.040(3) 0.056(3) -0.001(3) F26 0.245(6) 0.111(4) 0.168(5) -0.001(3) 0.081(4) 0.066(4) F27 0.125(4) 0.261(7) 0.151(4) 0.097(4) -0.036(3) 0.024(4) F28 0.133(4) 0.091(3) 0.185(5) -0.020(3) 0.081(3) -0.007(3) F29 0.116(3) 0.096(3) 0.139(4) 0.021(3) 0.027(3) -0.024(3) F30 0.103(3) 0.321(8) 0.141(4) 0.103(5) 0.009(3) 0.038(4) F31 0.083(4) 0.193(7) 0.584(16) 0.079(8) 0.026(6) 0.021(4) F32 0.219(6) 0.252(7) 0.124(5) 0.027(5) 0.004(4) -0.056(5) F33 0.434(12) 0.123(5) 0.279(9) 0.095(5) 0.012(8) -0.084(7) F34 0.163(6) 0.242(8) 0.445(13) -0.052(8) 0.029(7) 0.102(6) F35 0.359(10) 0.224(7) 0.121(5) -0.043(5) -0.009(5) -0.089(7) F36 0.213(6) 0.139(5) 0.203(6) 0.071(4) 0.001(4) -0.033(4) F37 0.164(5) 0.165(5) 0.260(7) 0.113(5) 0.038(4) 0.073(4) F38 0.458(12) 0.227(8) 0.182(7) -0.115(6) -0.132(8) 0.158(8) F39 0.176(6) 0.336(11) 0.367(11) 0.265(10) 0.066(6) 0.029(6) F40 0.130(4) 0.137(4) 0.295(7) 0.100(5) 0.016(4) 0.036(4) F41 0.296(9) 0.234(8) 0.196(7) -0.036(6) 0.018(6) 0.094(7) F42 0.170(5) 0.257(8) 0.348(10) 0.227(8) 0.109(6) 0.068(5) N1 0.041(3) 0.058(3) 0.053(3) 0.008(2) 0.002(2) 0.003(2) N2 0.047(3) 0.052(3) 0.042(3) 0.012(2) 0.009(2) 0.012(2) N3 0.056(3) 0.040(3) 0.056(3) 0.011(2) 0.005(2) 0.006(2) N4 0.054(3) 0.054(3) 0.044(3) 0.009(2) 0.007(2) 0.005(3) N5 0.042(3) 0.060(3) 0.055(3) 0.010(3) 0.003(2) 0.008(2) N6 0.046(3) 0.061(3) 0.059(3) 0.014(3) 0.009(3) 0.008(3) N7 0.048(3) 0.044(3) 0.052(3) 0.007(2) 0.000(2) 0.002(2) N8 0.051(3) 0.035(3) 0.065(3) 0.005(2) -0.003(2) 0.004(2) N9 0.053(3) 0.055(3) 0.055(3) 0.009(3) 0.005(3) 0.003(3) N10 0.068(3) 0.058(3) 0.062(3) 0.016(3) 0.017(3) 0.019(3) N11 0.070(3) 0.060(3) 0.055(3) 0.013(2) 0.012(3) 0.011(3) N12 0.073(4) 0.057(3) 0.068(4) 0.016(3) 0.019(3) 0.004(3) N13 0.086(4) 0.068(4) 0.065(4) 0.008(3) 0.018(3) 0.006(3) N14 0.080(4) 0.068(4) 0.063(4) 0.013(3) 0.012(3) 0.006(3) N15 0.092(4) 0.092(5) 0.069(4) 0.026(3) 0.010(3) 0.018(4) N16 0.076(4) 0.067(4) 0.061(4) 0.018(3) 0.019(3) 0.002(3) N17 0.057(3) 0.057(3) 0.066(3) 0.011(3) 0.012(3) 0.006(3) N18 0.068(4) 0.070(4) 0.067(4) 0.011(3) 0.006(3) 0.015(3) N19 0.072(4) 0.073(4) 0.060(3) 0.018(3) 0.007(3) 0.011(3) N20 0.085(4) 0.077(4) 0.058(4) 0.014(3) -0.006(3) 0.006(3) N21 0.121(5) 0.081(4) 0.063(4) 0.013(4) 0.000(4) 0.016(4) P1 0.0551(10) 0.0693(12) 0.0721(12) 0.0084(10) 0.0003(9) 0.0123(9) P2 0.0698(12) 0.0681(12) 0.0789(13) 0.0263(11) 0.0023(11) 0.0028(10) P3 0.1184(18) 0.0990(18) 0.0617(14) 0.0218(12) -0.0129(14) -0.0180(14) P4 0.112(2) 0.133(3) 0.0812(18) -0.0061(16) 0.0048(15) 0.0058(17) P5 0.0650(11) 0.0742(13) 0.0672(12) 0.0100(10) 0.0084(10) 0.0111(10) P6 0.0848(16) 0.0839(16) 0.112(2) 0.0120(14) 0.0035(13) 0.0039(13) P7 0.128(2) 0.0827(16) 0.116(2) 0.0407(17) 0.0344(16) 0.0241(15) N22 0.139(12) 0.64(4) 0.140(11) -0.076(14) -0.011(8) -0.055(14) C102 0.147(19) 0.48(4) 0.108(15) 0.021(18) 0.022(11) -0.032(18) C103 0.217(19) 0.43(3) 0.158(15) 0.076(16) 0.053(11) -0.016(17) _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 N4 1.971(4) . ? Cu1 N1 1.978(4) . ? Cu1 C41' 1.983(5) . ? Cu1 N3 2.076(4) . ? Cu1 N2 2.103(4) . ? Cu2 N5 1.975(4) . ? Cu2 N8 1.979(4) . ? Cu2 C41 1.982(5) . ? Cu2 N7 2.065(4) . ? Cu2 N6 2.123(5) . ? Cu3 N14 2.008(5) . ? Cu3 N11 2.021(4) . ? Cu3 N10 2.039(5) . ? Cu3 N13 2.047(5) . ? Cu3 N12 2.314(5) . ? Cu3 N15 2.332(6) . ? Cu4 N16 1.990(5) . ? Cu4 N19 2.016(5) . ? Cu4 N17 2.053(5) . ? Cu4 N20 2.067(5) . ? Cu4 N18 2.199(5) . ? Cu4 N21 2.558(6) . ? C1 N1 1.341(6) . ? C1 C2 1.363(7) . ? C1 H1 0.9300 . ? C2 C3 1.346(8) . ? C2 H2 0.9300 . ? C3 C4 1.373(8) . ? C3 H3 0.9300 . ? C4 C5 1.382(7) . ? C4 H4 0.9300 . ? C5 N1 1.350(6) . ? C5 C6 1.467(7) . ? C6 N2 1.346(6) . ? C6 C7 1.379(7) . ? C7 C8 1.376(8) . ? C7 H7 0.9300 . ? C8 C9 1.349(7) . ? C8 H8 0.9300 . ? C9 C10 1.395(7) . ? C9 H9 0.9300 . ? C10 N2 1.323(6) . ? C10 H10 0.9300 . ? C11 N3 1.329(6) . ? C11 C12 1.395(7) . ? C11 H11 0.9300 . ? C12 C13 1.349(7) . ? C12 H12 0.9300 . ? C13 C14 1.372(7) . ? C13 H13 0.9300 . ? C14 C15 1.386(7) . ? C14 H14 0.9300 . ? C15 N3 1.355(6) . ? C15 C16 1.457(7) . ? C16 N4 1.347(6) . ? C16 C17 1.390(7) . ? C17 C18 1.377(8) . ? C17 H17 0.9300 . ? C18 C19 1.350(8) . ? C18 H18 0.9300 . ? C19 C20 1.375(7) . ? C19 H19 0.9300 . ? C20 N4 1.334(6) . ? C20 H20 0.9300 . ? C21 N5 1.335(6) . ? C21 C22 1.372(7) . ? C21 H21 0.9300 . ? C22 C23 1.348(8) . ? C22 H22 0.9300 . ? C23 C24 1.350(8) . ? C23 H23 0.9300 . ? C24 C25 1.391(7) . ? C24 H24 0.9300 . ? C25 N5 1.331(6) . ? C25 C26 1.477(8) . ? C26 N6 1.328(6) . ? C26 C27 1.382(8) . ? C27 C28 1.391(9) . ? C27 H27 0.9300 . ? C28 C29 1.354(9) . ? C28 H28 0.9300 . ? C29 C30 1.397(9) . ? C29 H29 0.9300 . ? C30 N6 1.335(7) . ? C30 H30 0.9300 . ? C31 N7 1.340(6) . ? C31 C32 1.387(7) . ? C31 H31 0.9300 . ? C32 C33 1.370(7) . ? C32 H32 0.9300 . ? C33 C34 1.369(7) . ? C33 H33 0.9300 . ? C34 C35 1.376(7) . ? C34 H34 0.9300 . ? C35 N7 1.354(6) . ? C35 C36 1.470(7) . ? C36 N8 1.336(6) . ? C36 C37 1.379(7) . ? C37 C38 1.374(7) . ? C37 H37 0.9300 . ? C38 C39 1.360(7) . ? C38 H38 0.9300 . ? C39 C40 1.377(7) . ? C39 H39 0.9300 . ? C40 N8 1.338(6) . ? C40 H40 0.9300 . ? C41 C41' 1.153(5) . ? C42 N10 1.340(6) . ? C42 C43 1.357(7) . ? C42 H42 0.9300 . ? C43 C44 1.358(8) . ? C43 H43 0.9300 . ? C44 C45 1.376(8) . ? C44 H44 0.9300 . ? C45 C46 1.372(7) . ? C45 H45 0.9300 . ? C46 N10 1.357(6) . ? C46 C47 1.464(7) . ? C47 N11 1.341(6) . ? C47 C48 1.383(7) . ? C48 C49 1.367(8) . ? C48 H48 0.9300 . ? C49 C50 1.345(8) . ? C49 H49 0.9300 . ? C50 C51 1.394(8) . ? C50 H50 0.9300 . ? C51 N11 1.329(6) . ? C51 H51 0.9300 . ? C52 N12 1.340(7) . ? C52 C53 1.372(8) . ? C52 H52 0.9300 . ? C53 C54 1.370(9) . ? C53 H53 0.9300 . ? C54 C55 1.368(9) . ? C54 H54 0.9300 . ? C55 C56 1.385(9) . ? C55 H55 0.9300 . ? C56 N12 1.328(7) . ? C56 C57 1.480(9) . ? C57 N13 1.354(8) . ? C57 C58 1.377(9) . ? C58 C59 1.371(10) . ? C58 H58 0.9300 . ? C59 C60 1.373(11) . ? C59 H59 0.9300 . ? C60 C61 1.330(9) . ? C60 H60 0.9300 . ? C61 N13 1.338(8) . ? C61 H61 0.9300 . ? C62 N14 1.326(8) . ? C62 C63 1.387(8) . ? C62 H62 0.9300 . ? C63 C64 1.356(10) . ? C63 H63 0.9300 . ? C64 C65 1.362(10) . ? C64 H64 0.9300 . ? C65 C66 1.381(8) . ? C65 H65 0.9300 . ? C66 N14 1.341(7) . ? C66 C67 1.465(9) . ? C67 N15 1.359(7) . ? C67 C68 1.383(9) . ? C68 C69 1.412(11) . ? C68 H68 0.9300 . ? C69 C70 1.348(10) . ? C69 H69 0.9300 . ? C70 C71 1.374(10) . ? C70 H70 0.9300 . ? C71 N15 1.333(9) . ? C71 H71 0.9300 . ? C72 N16 1.348(7) . ? C72 C73 1.369(9) . ? C72 H72 0.9300 . ? C73 C74 1.340(9) . ? C73 H73 0.9300 . ? C74 C75 1.380(9) . ? C74 H74 0.9300 . ? C75 C76 1.368(8) . ? C75 H75 0.9300 . ? C76 N16 1.333(7) . ? C76 C77 1.471(8) . ? C77 N17 1.349(7) . ? C77 C78 1.382(8) . ? C78 C79 1.376(8) . ? C78 H78 0.9300 . ? C79 C80 1.380(8) . ? C79 H79 0.9300 . ? C80 C81 1.361(8) . ? C80 H80 0.9300 . ? C81 N17 1.331(7) . ? C81 H81 0.9300 . ? C82 N18 1.321(7) . ? C82 C83 1.379(9) . ? C82 H82 0.9300 . ? C83 C84 1.339(10) . ? C83 H83 0.9300 . ? C84 C85 1.381(9) . ? C84 H84 0.9300 . ? C85 C86 1.380(8) . ? C85 H85 0.9300 . ? C86 N18 1.324(7) . ? C86 C87 1.477(8) . ? C87 N19 1.333(7) . ? C87 C88 1.379(8) . ? C88 C89 1.380(9) . ? C88 H88 0.9300 . ? C89 C90 1.328(10) . ? C89 H89 0.9300 . ? C90 C91 1.390(9) . ? C90 H90 0.9300 . ? C91 N19 1.342(7) . ? C91 H91 0.9300 . ? C92 N20 1.328(7) . ? C92 C93 1.395(10) . ? C92 H92 0.9300 . ? C93 C94 1.360(11) . ? C93 H93 0.9300 . ? C94 C95 1.370(10) . ? C94 H94 0.9300 . ? C95 C96 1.404(10) . ? C95 H95 0.9300 . ? C96 N20 1.325(7) . ? C96 C97 1.469(9) . ? C97 N21 1.324(8) . ? C97 C98 1.375(9) . ? C98 C99 1.377(10) . ? C98 H98 0.9300 . ? C99 C100 1.381(11) . ? C99 H99 0.9300 . ? C100 C101 1.397(10) . ? C100 H100 0.9300 . ? C101 N21 1.340(8) . ? C101 H101 0.9300 . ? F1 P1 1.550(5) . ? F2 P1 1.549(4) . ? F3 P1 1.579(4) . ? F4 P1 1.556(4) . ? F5 P1 1.578(4) . ? F6 P1 1.536(4) . ? F7 P2 1.561(4) . ? F8 P2 1.528(5) . ? F9 P2 1.509(4) . ? F10 P2 1.471(4) . ? F11 P2 1.566(4) . ? F12 P2 1.598(4) . ? F13 P3 1.519(5) . ? F14 P3 1.514(4) . ? F15 P3 1.591(6) . ? F16 P3 1.598(5) . ? F17 P3 1.526(5) . ? F18 P3 1.543(5) . ? F19 P4 1.513(8) . ? F20 P4 1.509(5) . ? F21 P4 1.532(5) . ? F22 P4 1.523(7) . ? F23 P4 1.546(5) . ? F24 P4 1.551(5) . ? F25 P5 1.565(4) . ? F26 P5 1.524(4) . ? F27 P5 1.508(4) . ? F28 P5 1.557(4) . ? F29 P5 1.576(4) . ? F30 P5 1.536(5) . ? F31 P6 1.449(6) . ? F32 P6 1.519(5) . ? F33 P6 1.500(6) . ? F34 P6 1.461(6) . ? F35 P6 1.477(5) . ? F36 P6 1.544(6) . ? F37 P7 1.555(5) . ? F38 P7 1.433(5) . ? F39 P7 1.508(6) . ? F40 P7 1.570(5) . ? F41 P7 1.526(6) . ? F42 P7 1.497(6) . ? N22 C102 1.25(3) . ? C102 C103 1.306(10) . ? C103 H10A 0.9600 . ? C103 H10B 0.9600 . ? C103 H10C 0.9600 . ? 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 N1 173.79(18) . . ? N4 Cu1 C41' 93.76(18) . . ? N1 Cu1 C41' 92.36(18) . . ? N4 Cu1 N3 80.00(19) . . ? N1 Cu1 N3 94.58(17) . . ? C41' Cu1 N3 140.45(19) . . ? N4 Cu1 N2 98.52(17) . . ? N1 Cu1 N2 79.57(19) . . ? C41' Cu1 N2 117.28(18) . . ? N3 Cu1 N2 102.27(15) . . ? N5 Cu2 N8 173.60(17) . . ? N5 Cu2 C41 91.92(18) . . ? N8 Cu2 C41 94.26(18) . . ? N5 Cu2 N7 94.20(17) . . ? N8 Cu2 N7 79.84(17) . . ? C41 Cu2 N7 142.82(19) . . ? N5 Cu2 N6 79.0(2) . . ? N8 Cu2 N6 99.34(18) . . ? C41 Cu2 N6 119.89(19) . . ? N7 Cu2 N6 97.26(16) . . ? N14 Cu3 N11 166.0(2) . . ? N14 Cu3 N10 93.91(19) . . ? N11 Cu3 N10 80.3(2) . . ? N14 Cu3 N13 91.32(19) . . ? N11 Cu3 N13 97.2(2) . . ? N10 Cu3 N13 166.1(2) . . ? N14 Cu3 N12 103.9(2) . . ? N11 Cu3 N12 88.96(17) . . ? N10 Cu3 N12 90.30(19) . . ? N13 Cu3 N12 76.0(2) . . ? N14 Cu3 N15 75.8(2) . . ? N11 Cu3 N15 91.7(2) . . ? N10 Cu3 N15 93.38(19) . . ? N13 Cu3 N15 100.4(2) . . ? N12 Cu3 N15 176.32(19) . . ? N16 Cu4 N19 175.4(2) . . ? N16 Cu4 N17 79.4(2) . . ? N19 Cu4 N17 98.5(2) . . ? N16 Cu4 N20 93.8(2) . . ? N19 Cu4 N20 89.7(2) . . ? N17 Cu4 N20 156.1(2) . . ? N16 Cu4 N18 98.7(2) . . ? N19 Cu4 N18 77.5(2) . . ? N17 Cu4 N18 98.53(18) . . ? N20 Cu4 N18 105.1(2) . . ? N16 Cu4 N21 83.45(19) . . ? N19 Cu4 N21 100.5(2) . . ? N17 Cu4 N21 85.19(19) . . ? N20 Cu4 N21 71.2(2) . . ? N18 Cu4 N21 175.98(19) . . ? N1 C1 C2 123.3(6) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.6(6) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.2(6) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 120.9(6) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? N1 C5 C4 119.2(5) . . ? N1 C5 C6 115.0(5) . . ? C4 C5 C6 125.8(6) . . ? N2 C6 C7 121.2(5) . . ? N2 C6 C5 115.4(5) . . ? C7 C6 C5 123.4(5) . . ? C8 C7 C6 118.8(6) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C9 C8 C7 120.3(6) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 118.2(6) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? N2 C10 C9 122.4(5) . . ? N2 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? N3 C11 C12 122.1(5) . . ? N3 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? C13 C12 C11 118.9(6) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 119.9(6) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 119.3(6) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? N3 C15 C14 121.0(5) . . ? N3 C15 C16 115.2(5) . . ? C14 C15 C16 123.8(5) . . ? N4 C16 C17 120.7(5) . . ? N4 C16 C15 114.4(5) . . ? C17 C16 C15 124.8(6) . . ? C18 C17 C16 119.8(6) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 119.2(6) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 118.7(6) . . ? C18 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? N4 C20 C19 123.6(6) . . ? N4 C20 H20 118.2 . . ? C19 C20 H20 118.2 . . ? N5 C21 C22 123.8(6) . . ? N5 C21 H21 118.1 . . ? C22 C21 H21 118.1 . . ? C23 C22 C21 117.3(6) . . ? C23 C22 H22 121.4 . . ? C21 C22 H22 121.4 . . ? C22 C23 C24 120.9(6) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C23 C24 C25 119.1(6) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? N5 C25 C24 120.9(6) . . ? N5 C25 C26 114.5(5) . . ? C24 C25 C26 124.6(6) . . ? N6 C26 C27 121.6(6) . . ? N6 C26 C25 115.7(5) . . ? C27 C26 C25 122.6(6) . . ? C26 C27 C28 118.1(7) . . ? C26 C27 H27 120.9 . . ? C28 C27 H27 120.9 . . ? C29 C28 C27 121.1(7) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C28 C29 C30 116.9(7) . . ? C28 C29 H29 121.5 . . ? C30 C29 H29 121.5 . . ? N6 C30 C29 122.8(6) . . ? N6 C30 H30 118.6 . . ? C29 C30 H30 118.6 . . ? N7 C31 C32 121.8(5) . . ? N7 C31 H31 119.1 . . ? C32 C31 H31 119.1 . . ? C33 C32 C31 119.1(6) . . ? C33 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? C34 C33 C32 119.3(5) . . ? C34 C33 H33 120.3 . . ? C32 C33 H33 120.3 . . ? C33 C34 C35 119.6(5) . . ? C33 C34 H34 120.2 . . ? C35 C34 H34 120.2 . . ? N7 C35 C34 121.5(5) . . ? N7 C35 C36 114.4(5) . . ? C34 C35 C36 124.1(5) . . ? N8 C36 C37 121.4(5) . . ? N8 C36 C35 114.7(5) . . ? C37 C36 C35 123.9(5) . . ? C38 C37 C36 119.7(6) . . ? C38 C37 H37 120.2 . . ? C36 C37 H37 120.2 . . ? C39 C38 C37 118.8(6) . . ? C39 C38 H38 120.6 . . ? C37 C38 H38 120.6 . . ? C38 C39 C40 119.3(6) . . ? C38 C39 H39 120.3 . . ? C40 C39 H39 120.3 . . ? N8 C40 C39 122.1(5) . . ? N8 C40 H40 118.9 . . ? C39 C40 H40 118.9 . . ? C41' C41 Cu2 179.3(5) . . ? N10 C42 C43 123.9(6) . . ? N10 C42 H42 118.0 . . ? C43 C42 H42 118.0 . . ? C42 C43 C44 118.6(6) . . ? C42 C43 H43 120.7 . . ? C44 C43 H43 120.7 . . ? C43 C44 C45 118.9(6) . . ? C43 C44 H44 120.5 . . ? C45 C44 H44 120.5 . . ? C46 C45 C44 120.5(6) . . ? C46 C45 H45 119.8 . . ? C44 C45 H45 119.8 . . ? N10 C46 C45 120.4(5) . . ? N10 C46 C47 115.1(5) . . ? C45 C46 C47 124.4(6) . . ? N11 C47 C48 121.4(5) . . ? N11 C47 C46 115.5(5) . . ? C48 C47 C46 123.1(6) . . ? C49 C48 C47 117.5(6) . . ? C49 C48 H48 121.2 . . ? C47 C48 H48 121.2 . . ? C50 C49 C48 122.2(6) . . ? C50 C49 H49 118.9 . . ? C48 C49 H49 118.9 . . ? C49 C50 C51 117.6(6) . . ? C49 C50 H50 121.2 . . ? C51 C50 H50 121.2 . . ? N11 C51 C50 121.5(6) . . ? N11 C51 H51 119.2 . . ? C50 C51 H51 119.2 . . ? N12 C52 C53 124.9(7) . . ? N12 C52 H52 117.6 . . ? C53 C52 H52 117.6 . . ? C54 C53 C52 116.4(7) . . ? C54 C53 H53 121.8 . . ? C52 C53 H53 121.8 . . ? C55 C54 C53 120.6(7) . . ? C55 C54 H54 119.7 . . ? C53 C54 H54 119.7 . . ? C54 C55 C56 118.7(7) . . ? C54 C55 H55 120.6 . . ? C56 C55 H55 120.6 . . ? N12 C56 C55 122.2(7) . . ? N12 C56 C57 115.1(7) . . ? C55 C56 C57 122.7(7) . . ? N13 C57 C58 120.7(7) . . ? N13 C57 C56 117.3(6) . . ? C58 C57 C56 122.0(8) . . ? C59 C58 C57 119.3(8) . . ? C59 C58 H58 120.3 . . ? C57 C58 H58 120.3 . . ? C58 C59 C60 119.8(8) . . ? C58 C59 H59 120.1 . . ? C60 C59 H59 120.1 . . ? C61 C60 C59 117.7(9) . . ? C61 C60 H60 121.2 . . ? C59 C60 H60 121.2 . . ? C60 C61 N13 125.1(8) . . ? C60 C61 H61 117.5 . . ? N13 C61 H61 117.5 . . ? N14 C62 C63 122.1(7) . . ? N14 C62 H62 119.0 . . ? C63 C62 H62 119.0 . . ? C64 C63 C62 118.5(8) . . ? C64 C63 H63 120.8 . . ? C62 C63 H63 120.8 . . ? C63 C64 C65 119.9(8) . . ? C63 C64 H64 120.1 . . ? C65 C64 H64 120.1 . . ? C64 C65 C66 119.5(8) . . ? C64 C65 H65 120.2 . . ? C66 C65 H65 120.2 . . ? N14 C66 C65 120.7(8) . . ? N14 C66 C67 116.9(6) . . ? C65 C66 C67 122.4(8) . . ? N15 C67 C68 120.0(8) . . ? N15 C67 C66 115.4(7) . . ? C68 C67 C66 124.5(8) . . ? C67 C68 C69 120.2(9) . . ? C67 C68 H68 119.9 . . ? C69 C68 H68 119.9 . . ? C70 C69 C68 118.6(9) . . ? C70 C69 H69 120.7 . . ? C68 C69 H69 120.7 . . ? C69 C70 C71 118.4(10) . . ? C69 C70 H70 120.8 . . ? C71 C70 H70 120.8 . . ? N15 C71 C70 124.6(8) . . ? N15 C71 H71 117.7 . . ? C70 C71 H71 117.7 . . ? N16 C72 C73 122.9(7) . . ? N16 C72 H72 118.5 . . ? C73 C72 H72 118.5 . . ? C74 C73 C72 119.2(8) . . ? C74 C73 H73 120.4 . . ? C72 C73 H73 120.4 . . ? C73 C74 C75 119.1(7) . . ? C73 C74 H74 120.5 . . ? C75 C74 H74 120.5 . . ? C76 C75 C74 119.4(7) . . ? C76 C75 H75 120.3 . . ? C74 C75 H75 120.3 . . ? N16 C76 C75 122.0(6) . . ? N16 C76 C77 114.3(6) . . ? C75 C76 C77 123.7(7) . . ? N17 C77 C78 121.2(6) . . ? N17 C77 C76 114.7(6) . . ? C78 C77 C76 124.0(6) . . ? C79 C78 C77 119.1(6) . . ? C79 C78 H78 120.4 . . ? C77 C78 H78 120.4 . . ? C78 C79 C80 118.8(7) . . ? C78 C79 H79 120.6 . . ? C80 C79 H79 120.6 . . ? C81 C80 C79 119.3(7) . . ? C81 C80 H80 120.3 . . ? C79 C80 H80 120.3 . . ? N17 C81 C80 122.5(6) . . ? N17 C81 H81 118.8 . . ? C80 C81 H81 118.8 . . ? N18 C82 C83 123.8(7) . . ? N18 C82 H82 118.1 . . ? C83 C82 H82 118.1 . . ? C84 C83 C82 118.0(8) . . ? C84 C83 H83 121.0 . . ? C82 C83 H83 121.0 . . ? C83 C84 C85 119.6(8) . . ? C83 C84 H84 120.2 . . ? C85 C84 H84 120.2 . . ? C86 C85 C84 119.1(7) . . ? C86 C85 H85 120.5 . . ? C84 C85 H85 120.5 . . ? N18 C86 C85 121.5(7) . . ? N18 C86 C87 115.0(6) . . ? C85 C86 C87 123.5(7) . . ? N19 C87 C88 121.1(6) . . ? N19 C87 C86 116.8(6) . . ? C88 C87 C86 122.1(7) . . ? C87 C88 C89 118.9(7) . . ? C87 C88 H88 120.5 . . ? C89 C88 H88 120.5 . . ? C90 C89 C88 120.4(8) . . ? C90 C89 H89 119.8 . . ? C88 C89 H89 119.8 . . ? C89 C90 C91 118.6(8) . . ? C89 C90 H90 120.7 . . ? C91 C90 H90 120.7 . . ? N19 C91 C90 122.0(7) . . ? N19 C91 H91 119.0 . . ? C90 C91 H91 119.0 . . ? N20 C92 C93 120.7(7) . . ? N20 C92 H92 119.7 . . ? C93 C92 H92 119.7 . . ? C94 C93 C92 118.1(8) . . ? C94 C93 H93 120.9 . . ? C92 C93 H93 120.9 . . ? C93 C94 C95 122.0(9) . . ? C93 C94 H94 119.0 . . ? C95 C94 H94 119.0 . . ? C94 C95 C96 116.5(8) . . ? C94 C95 H95 121.8 . . ? C96 C95 H95 121.8 . . ? N20 C96 C95 121.6(7) . . ? N20 C96 C97 118.2(7) . . ? C95 C96 C97 120.1(8) . . ? N21 C97 C98 123.2(7) . . ? N21 C97 C96 114.8(7) . . ? C98 C97 C96 121.9(8) . . ? C97 C98 C99 119.1(9) . . ? C97 C98 H98 120.5 . . ? C99 C98 H98 120.5 . . ? C98 C99 C100 119.0(9) . . ? C98 C99 H99 120.5 . . ? C100 C99 H99 120.5 . . ? C99 C100 C101 118.2(9) . . ? C99 C100 H100 120.9 . . ? C101 C100 H100 120.9 . . ? N21 C101 C100 122.6(8) . . ? N21 C101 H101 118.7 . . ? C100 C101 H101 118.7 . . ? C41 C41' Cu1 175.9(5) . . ? C1 N1 C5 118.7(5) . . ? C1 N1 Cu1 124.1(4) . . ? C5 N1 Cu1 117.1(4) . . ? C10 N2 C6 119.0(5) . . ? C10 N2 Cu1 128.1(4) . . ? C6 N2 Cu1 112.8(4) . . ? C11 N3 C15 118.8(5) . . ? C11 N3 Cu1 127.9(4) . . ? C15 N3 Cu1 112.4(3) . . ? C20 N4 C16 117.9(5) . . ? C20 N4 Cu1 125.1(4) . . ? C16 N4 Cu1 116.9(4) . . ? C25 N5 C21 117.9(5) . . ? C25 N5 Cu2 118.0(4) . . ? C21 N5 Cu2 123.9(4) . . ? C26 N6 C30 119.4(5) . . ? C26 N6 Cu2 112.3(4) . . ? C30 N6 Cu2 128.1(4) . . ? C31 N7 C35 118.6(5) . . ? C31 N7 Cu2 127.6(4) . . ? C35 N7 Cu2 113.2(3) . . ? C36 N8 C40 118.7(5) . . ? C36 N8 Cu2 117.0(3) . . ? C40 N8 Cu2 124.2(4) . . ? C42 N10 C46 117.6(5) . . ? C42 N10 Cu3 128.1(4) . . ? C46 N10 Cu3 113.9(4) . . ? C51 N11 C47 119.7(5) . . ? C51 N11 Cu3 125.4(4) . . ? C47 N11 Cu3 115.0(4) . . ? C56 N12 C52 117.2(6) . . ? C56 N12 Cu3 110.3(5) . . ? C52 N12 Cu3 128.3(4) . . ? C61 N13 C57 117.4(6) . . ? C61 N13 Cu3 124.2(5) . . ? C57 N13 Cu3 118.1(5) . . ? C62 N14 C66 119.3(6) . . ? C62 N14 Cu3 121.1(5) . . ? C66 N14 Cu3 119.5(5) . . ? C71 N15 C67 118.1(7) . . ? C71 N15 Cu3 130.7(5) . . ? C67 N15 Cu3 107.2(5) . . ? C76 N16 C72 117.3(6) . . ? C76 N16 Cu4 116.9(4) . . ? C72 N16 Cu4 125.7(5) . . ? C81 N17 C77 118.9(5) . . ? C81 N17 Cu4 126.9(4) . . ? C77 N17 Cu4 113.8(4) . . ? C82 N18 C86 118.1(6) . . ? C82 N18 Cu4 129.0(5) . . ? C86 N18 Cu4 112.7(4) . . ? C87 N19 C91 118.9(6) . . ? C87 N19 Cu4 117.3(4) . . ? C91 N19 Cu4 123.2(5) . . ? C96 N20 C92 120.9(6) . . ? C96 N20 Cu4 120.9(5) . . ? C92 N20 Cu4 118.2(5) . . ? C97 N21 C101 118.0(7) . . ? C97 N21 Cu4 102.1(4) . . ? C101 N21 Cu4 126.8(5) . . ? F6 P1 F2 179.7(3) . . ? F6 P1 F1 90.6(3) . . ? F2 P1 F1 89.3(3) . . ? F6 P1 F4 90.0(3) . . ? F2 P1 F4 90.1(3) . . ? F1 P1 F4 179.4(3) . . ? F6 P1 F5 91.4(2) . . ? F2 P1 F5 88.3(2) . . ? F1 P1 F5 91.6(2) . . ? F4 P1 F5 88.3(2) . . ? F6 P1 F3 89.0(2) . . ? F2 P1 F3 91.3(2) . . ? F1 P1 F3 87.4(2) . . ? F4 P1 F3 92.8(3) . . ? F5 P1 F3 178.9(3) . . ? F10 P2 F9 92.2(4) . . ? F10 P2 F8 95.0(4) . . ? F9 P2 F8 172.7(4) . . ? F10 P2 F7 178.2(4) . . ? F9 P2 F7 88.8(3) . . ? F8 P2 F7 84.0(4) . . ? F10 P2 F11 90.3(3) . . ? F9 P2 F11 92.7(3) . . ? F8 P2 F11 87.7(2) . . ? F7 P2 F11 91.2(3) . . ? F10 P2 F12 92.0(3) . . ? F9 P2 F12 89.0(2) . . ? F8 P2 F12 90.4(2) . . ? F7 P2 F12 86.5(2) . . ? F11 P2 F12 177.1(2) . . ? F14 P3 F13 91.1(3) . . ? F14 P3 F17 94.1(3) . . ? F13 P3 F17 92.4(3) . . ? F14 P3 F18 93.6(3) . . ? F13 P3 F18 172.0(4) . . ? F17 P3 F18 93.7(3) . . ? F14 P3 F15 89.1(3) . . ? F13 P3 F15 85.1(3) . . ? F17 P3 F15 176.0(4) . . ? F18 P3 F15 88.5(3) . . ? F14 P3 F16 176.0(3) . . ? F13 P3 F16 86.9(3) . . ? F17 P3 F16 89.5(3) . . ? F18 P3 F16 88.0(3) . . ? F15 P3 F16 87.3(4) . . ? F20 P4 F19 87.7(4) . . ? F20 P4 F22 94.8(5) . . ? F19 P4 F22 176.7(5) . . ? F20 P4 F21 93.4(3) . . ? F19 P4 F21 89.8(4) . . ? F22 P4 F21 87.9(4) . . ? F20 P4 F23 176.3(4) . . ? F19 P4 F23 90.3(4) . . ? F22 P4 F23 87.3(4) . . ? F21 P4 F23 89.7(3) . . ? F20 P4 F24 89.0(3) . . ? F19 P4 F24 92.8(5) . . ? F22 P4 F24 89.3(4) . . ? F21 P4 F24 176.5(4) . . ? F23 P4 F24 88.0(3) . . ? F27 P5 F26 89.0(3) . . ? F27 P5 F30 178.4(4) . . ? F26 P5 F30 90.2(3) . . ? F27 P5 F28 92.8(3) . . ? F26 P5 F28 178.1(3) . . ? F30 P5 F28 88.0(3) . . ? F27 P5 F25 92.3(3) . . ? F26 P5 F25 88.6(3) . . ? F30 P5 F25 89.1(3) . . ? F28 P5 F25 90.6(2) . . ? F27 P5 F29 89.5(3) . . ? F26 P5 F29 92.4(3) . . ? F30 P5 F29 89.2(3) . . ? F28 P5 F29 88.4(2) . . ? F25 P5 F29 178.0(3) . . ? F31 P6 F34 173.4(5) . . ? F31 P6 F35 93.5(5) . . ? F34 P6 F35 88.7(5) . . ? F31 P6 F33 85.7(5) . . ? F34 P6 F33 100.7(6) . . ? F35 P6 F33 87.7(4) . . ? F31 P6 F32 91.3(5) . . ? F34 P6 F32 86.6(4) . . ? F35 P6 F32 175.1(5) . . ? F33 P6 F32 91.8(4) . . ? F31 P6 F36 87.5(4) . . ? F34 P6 F36 86.1(5) . . ? F35 P6 F36 95.4(4) . . ? F33 P6 F36 172.6(5) . . ? F32 P6 F36 85.7(3) . . ? F38 P7 F42 98.0(6) . . ? F38 P7 F39 89.7(6) . . ? F42 P7 F39 172.2(6) . . ? F38 P7 F41 176.1(6) . . ? F42 P7 F41 85.9(5) . . ? F39 P7 F41 86.4(5) . . ? F38 P7 F37 91.3(4) . . ? F42 P7 F37 90.2(3) . . ? F39 P7 F37 89.1(3) . . ? F41 P7 F37 89.2(4) . . ? F38 P7 F40 90.0(4) . . ? F42 P7 F40 89.2(3) . . ? F39 P7 F40 91.3(3) . . ? F41 P7 F40 89.5(4) . . ? F37 P7 F40 178.6(4) . . ? N22 C102 C103 173(2) . . ? C102 C103 H10A 109.5 . . ? C102 C103 H10B 109.5 . . ? H10A C103 H10B 109.5 . . ? C102 C103 H10C 109.5 . . ? H10A C103 H10C 109.5 . . ? H10B C103 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.501 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.064 data_7 _database_code_depnum_ccdc_archive 'CCDC 869863' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H24 Cu N5, 0.5(C12 H12 N2), C5 H6 N2, B F4' _chemical_formula_sum 'C36 H36 B Cu F4 N8' _chemical_formula_weight 731.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 10.6386(12) _cell_length_b 25.035(3) _cell_length_c 13.8438(15) _cell_angle_alpha 90.00 _cell_angle_beta 107.581(2) _cell_angle_gamma 90.00 _cell_volume 3514.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1442 _cell_measurement_theta_min 2.281 _cell_measurement_theta_max 18.015 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 0.681 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9288 _exptl_absorpt_correction_T_max 0.9350 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17753 _diffrn_reflns_av_R_equivalents 0.0988 _diffrn_reflns_av_sigmaI/netI 0.1558 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6198 _reflns_number_gt 2474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0204P)^2^] 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 6198 _refine_ls_number_parameters 493 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1381 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0716 _refine_ls_goodness_of_fit_ref 0.731 _refine_ls_restrained_S_all 0.745 _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 0.47425(4) -0.00324(2) 0.75172(3) 0.05285(17) Uani 1 1 d . . . B1 B 0.3257(6) 0.2616(2) 0.2681(4) 0.086(2) Uani 1 1 d D . . C1 C 0.2658(4) -0.08280(19) 0.7844(3) 0.0580(12) Uani 1 1 d . . . H1 H 0.2819 -0.1033 0.7334 0.070 Uiso 1 1 calc R . . C2 C 0.1749(4) -0.10126(18) 0.8287(3) 0.0608(13) Uani 1 1 d . . . H2 H 0.1315 -0.1335 0.8080 0.073 Uiso 1 1 calc R . . C3 C 0.1486(4) -0.0716(2) 0.9040(3) 0.0597(13) Uani 1 1 d . . . C4 C 0.0500(4) -0.08962(19) 0.9555(3) 0.0888(16) Uani 1 1 d . . . H4A H 0.0483 -0.1279 0.9573 0.133 Uiso 1 1 calc R . . H4B H -0.0359 -0.0765 0.9186 0.133 Uiso 1 1 calc R . . H4C H 0.0746 -0.0759 1.0234 0.133 Uiso 1 1 calc R . . C5 C 0.2158(4) -0.02441(18) 0.9308(3) 0.0571(12) Uani 1 1 d . . . H5 H 0.1993 -0.0034 0.9810 0.069 Uiso 1 1 calc R . . C6 C 0.3077(4) -0.00753(17) 0.8847(3) 0.0461(10) Uani 1 1 d . . . C7 C 0.3847(4) 0.04184(17) 0.9104(3) 0.0497(11) Uani 1 1 d . . . C8 C 0.3690(4) 0.07924(18) 0.9798(3) 0.0621(13) Uani 1 1 d . . . H8 H 0.3076 0.0733 1.0142 0.074 Uiso 1 1 calc R . . C9 C 0.4441(5) 0.1251(2) 0.9979(3) 0.0675(14) Uani 1 1 d . . . C10 C 0.4249(5) 0.16763(18) 1.0707(3) 0.1069(18) Uani 1 1 d . . . H10A H 0.5088 0.1769 1.1176 0.160 Uiso 1 1 calc R . . H10B H 0.3682 0.1540 1.1073 0.160 Uiso 1 1 calc R . . H10C H 0.3856 0.1988 1.0332 0.160 Uiso 1 1 calc R . . C11 C 0.5369(5) 0.13114(18) 0.9482(3) 0.0709(14) Uani 1 1 d . . . H11 H 0.5908 0.1612 0.9598 0.085 Uiso 1 1 calc R . . C12 C 0.5501(4) 0.0926(2) 0.8811(3) 0.0637(13) Uani 1 1 d . . . H12 H 0.6148 0.0969 0.8492 0.076 Uiso 1 1 calc R . . C13 C 0.3261(3) 0.09526(17) 0.6318(3) 0.0493(11) Uani 1 1 d . . . H13 H 0.3444 0.1125 0.6939 0.059 Uiso 1 1 calc R . . C14 C 0.2605(3) 0.12358(16) 0.5451(3) 0.0527(11) Uani 1 1 d . . . H14 H 0.2361 0.1589 0.5496 0.063 Uiso 1 1 calc R . . C15 C 0.2320(3) 0.09887(18) 0.4524(3) 0.0485(11) Uani 1 1 d . . . C16 C 0.1618(4) 0.12729(16) 0.3555(3) 0.0693(13) Uani 1 1 d . . . H16A H 0.0775 0.1395 0.3583 0.104 Uiso 1 1 calc R . . H16B H 0.1497 0.1032 0.2995 0.104 Uiso 1 1 calc R . . H16C H 0.2135 0.1573 0.3469 0.104 Uiso 1 1 calc R . . C17 C 0.2705(3) 0.04596(17) 0.4514(3) 0.0445(10) Uani 1 1 d . . . H17 H 0.2514 0.0278 0.3901 0.053 Uiso 1 1 calc R . . C18 C 0.3367(3) 0.02006(16) 0.5399(3) 0.0388(10) Uani 1 1 d . . . C19 C 0.3803(3) -0.03546(16) 0.5430(3) 0.0400(10) Uani 1 1 d . . . C20 C 0.3579(3) -0.06884(17) 0.4595(3) 0.0459(11) Uani 1 1 d . . . H20 H 0.3133 -0.0555 0.3956 0.055 Uiso 1 1 calc R . . C21 C 0.4001(4) -0.12133(18) 0.4688(3) 0.0514(11) Uani 1 1 d . . . C22 C 0.3711(4) -0.15811(17) 0.3781(3) 0.0755(14) Uani 1 1 d . . . H22A H 0.4525 -0.1707 0.3699 0.113 Uiso 1 1 calc R . . H22B H 0.3224 -0.1390 0.3184 0.113 Uiso 1 1 calc R . . H22C H 0.3200 -0.1880 0.3884 0.113 Uiso 1 1 calc R . . C23 C 0.4694(4) -0.13893(17) 0.5637(4) 0.0588(12) Uani 1 1 d . . . H23 H 0.5005 -0.1738 0.5733 0.071 Uiso 1 1 calc R . . C24 C 0.4925(4) -0.10440(18) 0.6450(3) 0.0558(12) Uani 1 1 d . . . H24 H 0.5412 -0.1167 0.7087 0.067 Uiso 1 1 calc R . . C25 C 0.6683(4) -0.0078(2) 0.7925(3) 0.0627(13) Uani 1 1 d . . . C26 C 0.9206(3) 0.11250(17) 0.4882(3) 0.0532(11) Uani 1 1 d . . . H26 H 0.8865 0.1397 0.4419 0.064 Uiso 1 1 calc R . . C27 C 0.9506(3) 0.12450(17) 0.5896(3) 0.0542(11) Uani 1 1 d . . . H27 H 0.9380 0.1589 0.6102 0.065 Uiso 1 1 calc R . . C28 C 0.9993(4) 0.08508(19) 0.6602(3) 0.0513(11) Uani 1 1 d . . . C29 C 1.0296(4) 0.09557(18) 0.7718(3) 0.0840(15) Uani 1 1 d . . . H29A H 1.1213 0.1043 0.8000 0.126 Uiso 1 1 calc R . . H29B H 1.0099 0.0643 0.8046 0.126 Uiso 1 1 calc R . . H29C H 0.9770 0.1249 0.7822 0.126 Uiso 1 1 calc R . . C30 C 1.0183(3) 0.03538(16) 0.6232(3) 0.0484(11) Uani 1 1 d . . . H30 H 1.0514 0.0076 0.6682 0.058 Uiso 1 1 calc R . . C31 C 0.9887(4) 0.02654(15) 0.5204(3) 0.0446(11) Uani 1 1 d . . . C32 C 0.7595(5) 0.25101(18) 0.4067(5) 0.0781(15) Uani 1 1 d . . . H32 H 0.6719 0.2488 0.4058 0.094 Uiso 1 1 calc R . . C33 C 0.7843(5) 0.24472(17) 0.3154(3) 0.0678(14) Uani 1 1 d . . . H33 H 0.7164 0.2372 0.2566 0.081 Uiso 1 1 calc R . . C34 C 0.9141(5) 0.24995(17) 0.3136(3) 0.0616(13) Uani 1 1 d . . . C35 C 1.0102(4) 0.25961(17) 0.4067(4) 0.0652(13) Uani 1 1 d . . . H35 H 1.0985 0.2629 0.4101 0.078 Uiso 1 1 calc R . . C36 C 0.9727(6) 0.26407(18) 0.4910(4) 0.0809(16) Uani 1 1 d . . . H36 H 1.0388 0.2706 0.5514 0.097 Uiso 1 1 calc R . . F1 F 0.303(2) 0.2670(7) 0.3570(11) 0.184(12) Uani 0.312(12) 1 d PD A 1 F2 F 0.4186(12) 0.2977(6) 0.2596(11) 0.116(7) Uani 0.312(12) 1 d PD A 1 F3 F 0.2172(13) 0.2675(8) 0.1906(13) 0.224(11) Uani 0.312(12) 1 d PD A 1 F4 F 0.378(2) 0.2118(4) 0.2638(12) 0.154(9) Uani 0.312(12) 1 d PD A 1 F1' F 0.3731(8) 0.2495(3) 0.3666(4) 0.136(3) Uani 0.688(12) 1 d PD A 2 F2' F 0.4205(7) 0.2743(3) 0.2291(7) 0.177(4) Uani 0.688(12) 1 d PD A 2 F3' F 0.2468(8) 0.3049(3) 0.2626(7) 0.161(4) Uani 0.688(12) 1 d PD A 2 F4' F 0.2551(10) 0.2208(3) 0.2176(5) 0.145(4) Uani 0.688(12) 1 d PD A 2 N1 N 0.3329(3) -0.03700(14) 0.8104(2) 0.0469(9) Uani 1 1 d . . . N2 N 0.4734(3) 0.04925(14) 0.8602(2) 0.0525(9) Uani 1 1 d . . . N3 N 0.3643(3) 0.04467(13) 0.6307(2) 0.0420(8) Uani 1 1 d . . . N4 N 0.4478(3) -0.05398(13) 0.6362(2) 0.0456(9) Uani 1 1 d . . . N5 N 0.7810(4) -0.00803(19) 0.8143(3) 0.0940(14) Uani 1 1 d . . . N6 N 0.9370(3) 0.06462(14) 0.4516(2) 0.0506(9) Uani 1 1 d . . . N7 N 0.8484(5) 0.25996(16) 0.4962(3) 0.0803(13) Uani 1 1 d . . . N8 N 0.9489(3) 0.24420(14) 0.2275(3) 0.0833(12) Uani 1 1 d . . . H8A H 0.8898 0.2370 0.1712 0.100 Uiso 1 1 calc R . . H8B H 1.0300 0.2477 0.2294 0.100 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 0.0559(3) 0.0580(4) 0.0443(3) -0.0036(3) 0.0146(2) 0.0003(3) B1 0.117(7) 0.069(6) 0.079(6) 0.011(5) 0.043(6) -0.014(6) C1 0.060(3) 0.066(4) 0.046(3) -0.007(3) 0.013(2) 0.000(3) C2 0.060(3) 0.061(3) 0.056(3) 0.005(3) 0.008(2) -0.011(3) C3 0.053(3) 0.067(4) 0.058(3) 0.019(3) 0.016(2) -0.005(3) C4 0.092(4) 0.098(4) 0.093(4) 0.007(3) 0.052(3) -0.020(3) C5 0.067(3) 0.069(4) 0.040(3) 0.006(2) 0.024(2) 0.006(3) C6 0.053(3) 0.049(3) 0.031(2) 0.001(2) 0.0057(19) -0.001(2) C7 0.062(3) 0.051(3) 0.032(2) 0.003(2) 0.007(2) 0.003(3) C8 0.092(4) 0.051(3) 0.050(3) -0.004(3) 0.030(3) 0.005(3) C9 0.104(4) 0.049(3) 0.043(3) 0.003(3) 0.012(3) 0.014(3) C10 0.193(6) 0.055(4) 0.077(4) -0.020(3) 0.048(4) 0.011(4) C11 0.095(4) 0.047(3) 0.059(3) -0.004(3) 0.007(3) -0.014(3) C12 0.070(3) 0.063(4) 0.055(3) 0.002(3) 0.014(2) 0.000(3) C13 0.049(3) 0.052(3) 0.049(3) -0.012(3) 0.020(2) -0.003(2) C14 0.052(3) 0.048(3) 0.059(3) 0.000(3) 0.017(2) 0.007(2) C15 0.041(3) 0.053(3) 0.053(3) 0.009(3) 0.016(2) -0.004(2) C16 0.073(3) 0.068(3) 0.064(3) 0.017(3) 0.016(2) 0.013(3) C17 0.037(2) 0.050(3) 0.047(3) -0.006(2) 0.014(2) -0.005(2) C18 0.030(2) 0.047(3) 0.039(2) -0.001(2) 0.0106(19) -0.001(2) C19 0.035(2) 0.041(3) 0.047(3) -0.002(2) 0.019(2) -0.006(2) C20 0.046(3) 0.052(3) 0.042(3) -0.007(2) 0.016(2) -0.005(2) C21 0.044(3) 0.052(3) 0.064(3) -0.012(3) 0.027(2) -0.010(2) C22 0.076(3) 0.065(3) 0.092(4) -0.034(3) 0.034(3) -0.014(3) C23 0.061(3) 0.040(3) 0.082(4) -0.005(3) 0.032(3) 0.002(2) C24 0.059(3) 0.054(3) 0.057(3) 0.008(3) 0.022(2) 0.005(3) C25 0.062(3) 0.085(4) 0.040(2) -0.008(3) 0.013(2) -0.001(3) C26 0.051(3) 0.046(3) 0.064(3) 0.014(3) 0.018(2) 0.003(2) C27 0.050(3) 0.040(3) 0.075(3) -0.005(3) 0.023(2) 0.001(2) C28 0.046(3) 0.053(3) 0.054(3) -0.004(3) 0.015(2) 0.001(2) C29 0.101(4) 0.073(4) 0.073(3) -0.016(3) 0.019(3) 0.012(3) C30 0.041(2) 0.041(3) 0.060(3) 0.006(2) 0.010(2) 0.002(2) C31 0.035(2) 0.042(3) 0.057(3) 0.001(2) 0.014(2) -0.002(2) C32 0.083(4) 0.059(4) 0.102(4) 0.015(4) 0.043(4) 0.014(3) C33 0.075(4) 0.059(3) 0.063(3) 0.011(3) 0.011(3) 0.003(3) C34 0.081(4) 0.050(3) 0.055(3) 0.011(3) 0.022(3) 0.010(3) C35 0.066(3) 0.065(4) 0.066(3) 0.011(3) 0.022(3) 0.003(3) C36 0.098(5) 0.080(4) 0.064(3) -0.011(3) 0.022(3) -0.007(4) F1 0.21(2) 0.20(3) 0.20(2) -0.082(18) 0.155(18) -0.020(17) F2 0.152(14) 0.071(10) 0.113(10) 0.003(8) 0.021(9) -0.034(9) F3 0.182(15) 0.17(2) 0.208(18) 0.016(16) -0.104(12) -0.025(15) F4 0.28(2) 0.085(11) 0.120(12) 0.048(9) 0.096(13) 0.113(13) F1' 0.195(7) 0.101(5) 0.093(5) 0.023(4) 0.013(4) 0.048(5) F2' 0.185(8) 0.136(8) 0.279(10) -0.059(7) 0.172(7) -0.050(5) F3' 0.163(7) 0.134(7) 0.206(9) 0.085(6) 0.083(6) 0.086(5) F4' 0.183(8) 0.136(7) 0.117(5) -0.008(5) 0.044(5) -0.071(6) N1 0.051(2) 0.052(2) 0.035(2) -0.0024(18) 0.0088(16) -0.0046(19) N2 0.061(2) 0.050(3) 0.042(2) -0.0075(19) 0.0084(18) -0.007(2) N3 0.046(2) 0.041(2) 0.042(2) -0.0072(19) 0.0183(16) -0.0030(18) N4 0.052(2) 0.044(2) 0.045(2) -0.0001(19) 0.0204(17) 0.0035(19) N5 0.087(3) 0.122(4) 0.072(3) -0.024(3) 0.023(2) 0.008(3) N6 0.052(2) 0.038(2) 0.063(2) 0.006(2) 0.0197(18) 0.0024(19) N7 0.102(4) 0.079(3) 0.066(3) -0.002(2) 0.035(3) 0.007(3) N8 0.091(3) 0.098(3) 0.067(3) 0.006(2) 0.032(2) 0.003(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 C25 1.972(4) . ? Cu1 N4 1.995(3) . ? Cu1 N2 1.997(3) . ? Cu1 N1 2.091(3) . ? Cu1 N3 2.104(3) . ? B1 F2' 1.320(7) . ? B1 F3 1.326(8) . ? B1 F1 1.328(8) . ? B1 F4' 1.333(6) . ? B1 F1' 1.337(7) . ? B1 F3' 1.360(6) . ? B1 F2 1.371(8) . ? B1 F4 1.375(8) . ? C1 N1 1.341(4) . ? C1 C2 1.372(5) . ? C1 H1 0.9300 . ? C2 C3 1.376(5) . ? C2 H2 0.9300 . ? C3 C5 1.372(5) . ? C3 C4 1.505(5) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.385(5) . ? C5 H5 0.9300 . ? C6 N1 1.357(4) . ? C6 C7 1.466(5) . ? C7 N2 1.343(4) . ? C7 C8 1.387(5) . ? C8 C9 1.378(6) . ? C8 H8 0.9300 . ? C9 C11 1.373(5) . ? C9 C10 1.522(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.375(5) . ? C11 H11 0.9300 . ? C12 N2 1.335(5) . ? C12 H12 0.9300 . ? C13 N3 1.332(4) . ? C13 C14 1.387(5) . ? C13 H13 0.9300 . ? C14 C15 1.373(5) . ? C14 H14 0.9300 . ? C15 C17 1.388(5) . ? C15 C16 1.502(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.377(4) . ? C17 H17 0.9300 . ? C18 N3 1.351(4) . ? C18 C19 1.462(5) . ? C19 N4 1.355(4) . ? C19 C20 1.388(5) . ? C20 C21 1.382(5) . ? C20 H20 0.9300 . ? C21 C23 1.371(5) . ? C21 C22 1.512(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.381(5) . ? C23 H23 0.9300 . ? C24 N4 1.341(4) . ? C24 H24 0.9300 . ? C25 N5 1.145(4) . ? C26 N6 1.333(4) . ? C26 C27 1.376(5) . ? C26 H26 0.9300 . ? C27 C28 1.375(5) . ? C27 H27 0.9300 . ? C28 C30 1.384(5) . ? C28 C29 1.503(5) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.379(5) . ? C30 H30 0.9300 . ? C31 N6 1.342(4) . ? C31 C31 1.492(7) 3_756 ? C32 N7 1.331(5) . ? C32 C33 1.376(5) . ? C32 H32 0.9300 . ? C33 C34 1.395(5) . ? C33 H33 0.9300 . ? C34 N8 1.358(5) . ? C34 C35 1.402(5) . ? C35 C36 1.348(5) . ? C35 H35 0.9300 . ? C36 N7 1.349(5) . ? C36 H36 0.9300 . ? N8 H8A 0.8600 . ? N8 H8B 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 Cu1 N4 94.32(15) . . ? C25 Cu1 N2 93.69(16) . . ? N4 Cu1 N2 171.93(13) . . ? C25 Cu1 N1 132.74(15) . . ? N4 Cu1 N1 96.32(13) . . ? N2 Cu1 N1 78.86(14) . . ? C25 Cu1 N3 122.87(15) . . ? N4 Cu1 N3 79.33(13) . . ? N2 Cu1 N3 95.50(13) . . ? N1 Cu1 N3 104.34(11) . . ? F2' B1 F3 103.1(10) . . ? F2' B1 F1 136.7(10) . . ? F3 B1 F1 112.6(8) . . ? F2' B1 F4' 110.4(6) . . ? F3 B1 F4' 56.4(7) . . ? F1 B1 F4' 109.6(9) . . ? F2' B1 F1' 111.8(6) . . ? F3 B1 F1' 145.0(10) . . ? F1 B1 F1' 36.6(8) . . ? F4' B1 F1' 110.0(6) . . ? F2' B1 F3' 108.6(6) . . ? F3 B1 F3' 59.5(9) . . ? F1 B1 F3' 72.0(8) . . ? F4' B1 F3' 110.0(6) . . ? F1' B1 F3' 105.9(5) . . ? F2' B1 F2 31.2(7) . . ? F3 B1 F2 109.2(8) . . ? F1 B1 F2 110.4(8) . . ? F4' B1 F2 140.0(9) . . ? F1' B1 F2 100.2(9) . . ? F3' B1 F2 85.3(7) . . ? F2' B1 F4 80.1(8) . . ? F3 B1 F4 109.5(8) . . ? F1 B1 F4 108.8(8) . . ? F4' B1 F4 57.1(7) . . ? F1' B1 F4 78.9(7) . . ? F3' B1 F4 166.8(9) . . ? F2 B1 F4 106.2(7) . . ? N1 C1 C2 123.9(4) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 119.2(4) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C5 C3 C2 117.5(4) . . ? C5 C3 C4 120.7(5) . . ? C2 C3 C4 121.8(5) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 C6 121.3(4) . . ? C3 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? N1 C6 C5 120.8(4) . . ? N1 C6 C7 114.7(4) . . ? C5 C6 C7 124.5(4) . . ? N2 C7 C8 121.0(4) . . ? N2 C7 C6 114.8(4) . . ? C8 C7 C6 124.1(4) . . ? C9 C8 C7 120.3(4) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C11 C9 C8 117.8(5) . . ? C11 C9 C10 121.1(5) . . ? C8 C9 C10 121.2(5) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 C12 119.8(5) . . ? C9 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? N2 C12 C11 122.5(4) . . ? N2 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? N3 C13 C14 123.5(4) . . ? N3 C13 H13 118.2 . . ? C14 C13 H13 118.2 . . ? C15 C14 C13 119.3(4) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C17 117.2(4) . . ? C14 C15 C16 122.1(4) . . ? C17 C15 C16 120.8(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C15 120.9(4) . . ? C18 C17 H17 119.5 . . ? C15 C17 H17 119.5 . . ? N3 C18 C17 121.5(4) . . ? N3 C18 C19 115.4(3) . . ? C17 C18 C19 123.1(4) . . ? N4 C19 C20 119.7(4) . . ? N4 C19 C18 115.2(4) . . ? C20 C19 C18 125.1(4) . . ? C21 C20 C19 121.7(4) . . ? C21 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? C23 C21 C20 117.4(4) . . ? C23 C21 C22 121.1(4) . . ? C20 C21 C22 121.5(4) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 C24 119.5(4) . . ? C21 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? N4 C24 C23 123.0(4) . . ? N4 C24 H24 118.5 . . ? C23 C24 H24 118.5 . . ? N5 C25 Cu1 176.8(5) . . ? N6 C26 C27 124.6(4) . . ? N6 C26 H26 117.7 . . ? C27 C26 H26 117.7 . . ? C28 C27 C26 119.3(4) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C27 C28 C30 116.6(4) . . ? C27 C28 C29 121.5(4) . . ? C30 C28 C29 121.9(4) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 C30 C28 120.9(4) . . ? C31 C30 H30 119.6 . . ? C28 C30 H30 119.6 . . ? N6 C31 C30 122.4(3) . . ? N6 C31 C31 116.3(5) . 3_756 ? C30 C31 C31 121.4(5) . 3_756 ? N7 C32 C33 126.5(5) . . ? N7 C32 H32 116.8 . . ? C33 C32 H32 116.8 . . ? C32 C33 C34 118.1(4) . . ? C32 C33 H33 121.0 . . ? C34 C33 H33 121.0 . . ? N8 C34 C33 122.6(5) . . ? N8 C34 C35 120.5(5) . . ? C33 C34 C35 116.8(4) . . ? C36 C35 C34 119.0(5) . . ? C36 C35 H35 120.5 . . ? C34 C35 H35 120.5 . . ? C35 C36 N7 126.2(5) . . ? C35 C36 H36 116.9 . . ? N7 C36 H36 116.9 . . ? C1 N1 C6 117.2(3) . . ? C1 N1 Cu1 128.9(3) . . ? C6 N1 Cu1 113.9(3) . . ? C12 N2 C7 118.6(4) . . ? C12 N2 Cu1 123.8(3) . . ? C7 N2 Cu1 117.5(3) . . ? C13 N3 C18 117.5(3) . . ? C13 N3 Cu1 129.2(3) . . ? C18 N3 Cu1 113.2(3) . . ? C24 N4 C19 118.6(3) . . ? C24 N4 Cu1 124.5(3) . . ? C19 N4 Cu1 116.8(3) . . ? C26 N6 C31 116.2(3) . . ? C32 N7 C36 113.3(4) . . ? C34 N8 H8A 120.0 . . ? C34 N8 H8B 120.0 . . ? H8A N8 H8B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.4(6) . . . . ? C1 C2 C3 C5 0.1(6) . . . . ? C1 C2 C3 C4 180.0(4) . . . . ? C2 C3 C5 C6 -0.7(6) . . . . ? C4 C3 C5 C6 179.4(4) . . . . ? C3 C5 C6 N1 0.8(6) . . . . ? C3 C5 C6 C7 -179.0(4) . . . . ? N1 C6 C7 N2 -3.2(5) . . . . ? C5 C6 C7 N2 176.7(3) . . . . ? N1 C6 C7 C8 176.1(4) . . . . ? C5 C6 C7 C8 -4.1(6) . . . . ? N2 C7 C8 C9 0.5(6) . . . . ? C6 C7 C8 C9 -178.8(4) . . . . ? C7 C8 C9 C11 -2.4(6) . . . . ? C7 C8 C9 C10 177.7(4) . . . . ? C8 C9 C11 C12 1.5(6) . . . . ? C10 C9 C11 C12 -178.6(4) . . . . ? C9 C11 C12 N2 1.4(6) . . . . ? N3 C13 C14 C15 0.2(6) . . . . ? C13 C14 C15 C17 0.4(5) . . . . ? C13 C14 C15 C16 -179.6(3) . . . . ? C14 C15 C17 C18 -1.1(5) . . . . ? C16 C15 C17 C18 178.9(3) . . . . ? C15 C17 C18 N3 1.2(5) . . . . ? C15 C17 C18 C19 -179.6(3) . . . . ? N3 C18 C19 N4 -2.8(4) . . . . ? C17 C18 C19 N4 177.9(3) . . . . ? N3 C18 C19 C20 177.4(3) . . . . ? C17 C18 C19 C20 -1.9(5) . . . . ? N4 C19 C20 C21 1.5(5) . . . . ? C18 C19 C20 C21 -178.7(3) . . . . ? C19 C20 C21 C23 -2.2(6) . . . . ? C19 C20 C21 C22 177.7(3) . . . . ? C20 C21 C23 C24 0.7(6) . . . . ? C22 C21 C23 C24 -179.1(4) . . . . ? C21 C23 C24 N4 1.4(6) . . . . ? N4 Cu1 C25 N5 106(7) . . . . ? N2 Cu1 C25 N5 -73(7) . . . . ? N1 Cu1 C25 N5 -151(7) . . . . ? N3 Cu1 C25 N5 26(7) . . . . ? N6 C26 C27 C28 -1.0(6) . . . . ? C26 C27 C28 C30 1.7(5) . . . . ? C26 C27 C28 C29 -178.0(3) . . . . ? C27 C28 C30 C31 -0.3(6) . . . . ? C29 C28 C30 C31 179.4(3) . . . . ? C28 C30 C31 N6 -2.0(6) . . . . ? C28 C30 C31 C31 178.7(4) . . . 3_756 ? N7 C32 C33 C34 -2.5(8) . . . . ? C32 C33 C34 N8 179.6(4) . . . . ? C32 C33 C34 C35 2.0(6) . . . . ? N8 C34 C35 C36 -178.7(4) . . . . ? C33 C34 C35 C36 -1.0(6) . . . . ? C34 C35 C36 N7 0.2(8) . . . . ? C2 C1 N1 C6 -0.3(6) . . . . ? C2 C1 N1 Cu1 179.8(3) . . . . ? C5 C6 N1 C1 -0.3(5) . . . . ? C7 C6 N1 C1 179.5(3) . . . . ? C5 C6 N1 Cu1 179.6(3) . . . . ? C7 C6 N1 Cu1 -0.5(4) . . . . ? C25 Cu1 N1 C1 -92.8(4) . . . . ? N4 Cu1 N1 C1 9.1(3) . . . . ? N2 Cu1 N1 C1 -177.5(3) . . . . ? N3 Cu1 N1 C1 89.7(3) . . . . ? C25 Cu1 N1 C6 87.3(3) . . . . ? N4 Cu1 N1 C6 -170.8(2) . . . . ? N2 Cu1 N1 C6 2.6(2) . . . . ? N3 Cu1 N1 C6 -90.3(3) . . . . ? C11 C12 N2 C7 -3.4(6) . . . . ? C11 C12 N2 Cu1 172.4(3) . . . . ? C8 C7 N2 C12 2.4(6) . . . . ? C6 C7 N2 C12 -178.3(3) . . . . ? C8 C7 N2 Cu1 -173.7(3) . . . . ? C6 C7 N2 Cu1 5.6(4) . . . . ? C25 Cu1 N2 C12 46.6(3) . . . . ? N4 Cu1 N2 C12 -126.6(10) . . . . ? N1 Cu1 N2 C12 179.5(3) . . . . ? N3 Cu1 N2 C12 -76.9(3) . . . . ? C25 Cu1 N2 C7 -137.5(3) . . . . ? N4 Cu1 N2 C7 49.3(11) . . . . ? N1 Cu1 N2 C7 -4.6(3) . . . . ? N3 Cu1 N2 C7 99.0(3) . . . . ? C14 C13 N3 C18 -0.2(5) . . . . ? C14 C13 N3 Cu1 175.8(3) . . . . ? C17 C18 N3 C13 -0.5(5) . . . . ? C19 C18 N3 C13 -179.8(3) . . . . ? C17 C18 N3 Cu1 -177.1(3) . . . . ? C19 C18 N3 Cu1 3.6(4) . . . . ? C25 Cu1 N3 C13 -90.5(3) . . . . ? N4 Cu1 N3 C13 -178.7(3) . . . . ? N2 Cu1 N3 C13 7.5(3) . . . . ? N1 Cu1 N3 C13 87.4(3) . . . . ? C25 Cu1 N3 C18 85.7(3) . . . . ? N4 Cu1 N3 C18 -2.6(2) . . . . ? N2 Cu1 N3 C18 -176.3(2) . . . . ? N1 Cu1 N3 C18 -96.4(2) . . . . ? C23 C24 N4 C19 -2.1(6) . . . . ? C23 C24 N4 Cu1 178.2(3) . . . . ? C20 C19 N4 C24 0.6(5) . . . . ? C18 C19 N4 C24 -179.2(3) . . . . ? C20 C19 N4 Cu1 -179.7(2) . . . . ? C18 C19 N4 Cu1 0.5(4) . . . . ? C25 Cu1 N4 C24 58.1(3) . . . . ? N2 Cu1 N4 C24 -128.7(10) . . . . ? N1 Cu1 N4 C24 -75.8(3) . . . . ? N3 Cu1 N4 C24 -179.3(3) . . . . ? C25 Cu1 N4 C19 -121.6(3) . . . . ? N2 Cu1 N4 C19 51.7(11) . . . . ? N1 Cu1 N4 C19 104.5(3) . . . . ? N3 Cu1 N4 C19 1.1(2) . . . . ? C27 C26 N6 C31 -1.2(6) . . . . ? C30 C31 N6 C26 2.7(5) . . . . ? C31 C31 N6 C26 -178.0(4) 3_756 . . . ? C33 C32 N7 C36 1.6(7) . . . . ? C35 C36 N7 C32 -0.5(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.276 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.064 data_8 _database_code_depnum_ccdc_archive 'CCDC 869864' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C49 H48 Cu2 N9, 2(Cl O4), N O2' _chemical_formula_sum 'C49 H48 Cl2 Cu2 N10 O10' _chemical_formula_weight 1134.95 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.041(4) _cell_length_b 22.998(6) _cell_length_c 18.190(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.702(16) _cell_angle_gamma 90.00 _cell_volume 5419(2) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2239 _cell_measurement_theta_min 2.428 _cell_measurement_theta_max 20.224 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2336 _exptl_absorpt_coefficient_mu 0.947 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8948 _exptl_absorpt_correction_T_max 0.9112 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13475 _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4750 _reflns_number_gt 2239 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1578P)^2^] 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 4750 _refine_ls_number_parameters 334 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1442 _refine_ls_R_factor_gt 0.0838 _refine_ls_wR_factor_ref 0.2515 _refine_ls_wR_factor_gt 0.2256 _refine_ls_goodness_of_fit_ref 0.891 _refine_ls_restrained_S_all 0.907 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.44244(6) 0.72747(3) 0.56512(5) 0.0767(4) Uani 1 1 d . . . C1 C 0.6194(5) 0.7376(3) 0.7283(4) 0.0775(19) Uani 1 1 d . . . H1 H 0.6119 0.7777 0.7226 0.093 Uiso 1 1 calc R . . C2 C 0.6990(5) 0.7152(4) 0.7931(4) 0.092(2) Uani 1 1 d . . . H2 H 0.7448 0.7402 0.8302 0.111 Uiso 1 1 calc R . . C3 C 0.7115(5) 0.6549(3) 0.8038(4) 0.089(2) Uani 1 1 d . . . C4 C 0.6436(5) 0.6206(3) 0.7469(4) 0.081(2) Uani 1 1 d . . . H4 H 0.6507 0.5804 0.7512 0.097 Uiso 1 1 calc R . . C5 C 0.5632(4) 0.6447(3) 0.6824(4) 0.0691(17) Uani 1 1 d . . . C6 C 0.4861(5) 0.6104(3) 0.6190(4) 0.0759(19) Uani 1 1 d . . . C7 C 0.4774(6) 0.5509(3) 0.6208(5) 0.095(2) Uani 1 1 d . . . H7 H 0.5230 0.5298 0.6636 0.114 Uiso 1 1 calc R . . C8 C 0.4014(7) 0.5224(3) 0.5594(6) 0.106(3) Uani 1 1 d . . . C9 C 0.3362(6) 0.5555(3) 0.4954(6) 0.112(3) Uani 1 1 d . . . H9 H 0.2855 0.5375 0.4522 0.134 Uiso 1 1 calc R . . C10 C 0.3476(5) 0.6142(3) 0.4970(5) 0.102(3) Uani 1 1 d . . . H10 H 0.3031 0.6359 0.4546 0.123 Uiso 1 1 calc R . . C11 C 0.8014(6) 0.6305(4) 0.8722(5) 0.130(3) Uani 1 1 d . . . H11A H 0.8645 0.6408 0.8665 0.194 Uiso 1 1 calc R . . H11B H 0.7956 0.5889 0.8727 0.194 Uiso 1 1 calc R . . H11C H 0.8018 0.6461 0.9213 0.194 Uiso 1 1 calc R . . C12 C 0.3904(9) 0.4563(3) 0.5576(8) 0.165(5) Uani 1 1 d . . . H12A H 0.4472 0.4397 0.6011 0.248 Uiso 1 1 calc R . . H12B H 0.3901 0.4416 0.5081 0.248 Uiso 1 1 calc R . . H12C H 0.3268 0.4460 0.5625 0.248 Uiso 1 1 calc R . . C13 C 0.5375(8) 0.6928(4) 0.4436(6) 0.123(3) Uani 1 1 d . . . H13 H 0.5097 0.6561 0.4436 0.147 Uiso 1 1 calc R . . C14 C 0.5925(10) 0.7022(6) 0.3975(8) 0.154(4) Uani 1 1 d . . . H14 H 0.6047 0.6719 0.3683 0.184 Uiso 1 1 calc R . . C15 C 0.6308(9) 0.7585(7) 0.3945(9) 0.149(4) Uani 1 1 d . . . C16 C 0.6161(8) 0.8007(4) 0.4401(7) 0.121(3) Uani 1 1 d . . . H16 H 0.6421 0.8379 0.4399 0.146 Uiso 1 1 calc R . . C17 C 0.5622(6) 0.7883(3) 0.4869(5) 0.092(2) Uani 1 1 d . . . C18 C 0.5360(5) 0.8317(3) 0.5387(5) 0.083(2) Uani 1 1 d . . . C19 C 0.5682(6) 0.8885(3) 0.5463(5) 0.102(3) Uani 1 1 d . . . H19 H 0.6089 0.9010 0.5194 0.123 Uiso 1 1 calc R . . C20 C 0.5419(6) 0.9274(3) 0.5927(5) 0.092(2) Uani 1 1 d . . . C21 C 0.4789(7) 0.9070(3) 0.6281(5) 0.099(3) Uani 1 1 d . . . H21 H 0.4562 0.9322 0.6578 0.119 Uiso 1 1 calc R . . C22 C 0.4483(6) 0.8499(3) 0.6207(4) 0.089(2) Uani 1 1 d . . . H22 H 0.4067 0.8371 0.6467 0.106 Uiso 1 1 calc R . . C23 C 0.5789(8) 0.9878(4) 0.6031(6) 0.142(4) Uani 1 1 d . . . H23A H 0.5242 1.0133 0.6022 0.213 Uiso 1 1 calc R . . H23B H 0.6003 0.9980 0.5606 0.213 Uiso 1 1 calc R . . H23C H 0.6363 0.9916 0.6532 0.213 Uiso 1 1 calc R . . C24 C 0.6919(13) 0.7728(6) 0.3424(11) 0.225(8) Uani 1 1 d . . . H24A H 0.6649 0.8077 0.3127 0.337 Uiso 1 1 calc R . . H24B H 0.6854 0.7413 0.3062 0.337 Uiso 1 1 calc R . . H24C H 0.7633 0.7784 0.3758 0.337 Uiso 1 1 calc R . . C25 C 0.2933(4) 0.7448(2) 0.5151(4) 0.0764(18) Uani 0.50 1 d P . . Cl1 Cl 0.7055(2) 0.39659(17) 0.7280(2) 0.1511(12) Uani 1 1 d . . . N1 N 0.5523(4) 0.7030(2) 0.6732(3) 0.0714(14) Uani 1 1 d . . . N2 N 0.4207(4) 0.6419(2) 0.5577(3) 0.0820(17) Uani 1 1 d . . . N3 N 0.5223(5) 0.7345(2) 0.4887(4) 0.0866(18) Uani 1 1 d . . . N4 N 0.4773(5) 0.8115(2) 0.5763(3) 0.0769(15) Uani 1 1 d . . . N5 N 0.2933(4) 0.7448(2) 0.5151(4) 0.0764(18) Uani 0.50 1 d P . . N6 N 1.0000 0.5321(6) 0.7500 0.222(8) Uani 1 2 d SD . . O1 O 0.7868(9) 0.3868(6) 0.7108(7) 0.248(6) Uani 1 1 d . . . O2 O 0.6691(17) 0.4456(8) 0.7067(14) 0.415(14) Uani 1 1 d . . . O3 O 0.7298(8) 0.3829(5) 0.8078(6) 0.224(4) Uani 1 1 d . . . O4 O 0.6230(14) 0.3723(11) 0.6808(10) 0.429(14) Uani 1 1 d . . . O5 O 0.9143(7) 0.5722(2) 0.6872(4) 0.187(4) Uani 1 1 d 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 0.0740(6) 0.0538(5) 0.0754(6) -0.0064(3) -0.0010(4) 0.0116(3) C1 0.073(4) 0.072(4) 0.068(4) -0.007(3) 0.005(4) 0.007(3) C2 0.061(4) 0.115(6) 0.074(5) -0.016(4) -0.002(4) 0.003(4) C3 0.077(5) 0.101(5) 0.070(5) -0.002(4) 0.008(4) 0.036(4) C4 0.074(4) 0.076(4) 0.080(5) 0.009(4) 0.015(4) 0.035(3) C5 0.064(4) 0.063(4) 0.074(4) 0.004(3) 0.019(3) 0.011(3) C6 0.066(4) 0.062(4) 0.090(5) 0.002(3) 0.019(4) 0.018(3) C7 0.090(5) 0.056(4) 0.115(6) 0.011(4) 0.015(5) 0.018(4) C8 0.108(6) 0.047(4) 0.149(8) -0.004(4) 0.035(6) 0.001(4) C9 0.081(5) 0.068(5) 0.148(8) -0.033(5) 0.002(5) 0.003(4) C10 0.081(5) 0.077(5) 0.108(6) -0.015(4) -0.009(4) 0.013(4) C11 0.106(6) 0.153(8) 0.089(6) -0.001(5) -0.008(5) 0.056(6) C12 0.164(8) 0.050(4) 0.260(14) -0.008(6) 0.057(9) 0.002(5) C13 0.140(8) 0.094(7) 0.148(9) -0.027(6) 0.071(7) 0.008(5) C14 0.141(9) 0.155(11) 0.183(12) -0.055(9) 0.083(9) 0.011(8) C15 0.137(10) 0.154(11) 0.192(13) -0.019(9) 0.103(9) 0.005(8) C16 0.112(7) 0.111(7) 0.160(9) -0.023(7) 0.074(7) -0.014(6) C17 0.068(5) 0.084(5) 0.101(6) -0.016(4) 0.009(4) 0.007(4) C18 0.066(4) 0.062(4) 0.090(5) -0.007(4) -0.003(4) 0.007(3) C19 0.094(5) 0.075(5) 0.100(6) 0.001(4) -0.004(4) -0.004(4) C20 0.100(6) 0.061(4) 0.086(6) -0.002(4) 0.002(4) -0.005(4) C21 0.121(7) 0.064(5) 0.074(5) -0.011(4) -0.005(5) 0.025(4) C22 0.105(5) 0.063(4) 0.079(5) -0.010(4) 0.015(4) 0.014(4) C23 0.164(9) 0.090(6) 0.124(8) -0.029(5) 0.004(6) -0.003(6) C24 0.231(18) 0.233(17) 0.30(2) 0.032(12) 0.197(18) 0.020(11) C25 0.078(4) 0.052(3) 0.076(4) -0.006(3) 0.006(3) 0.008(3) Cl1 0.105(2) 0.170(3) 0.124(2) 0.014(2) -0.0149(18) -0.0154(19) N1 0.064(3) 0.072(3) 0.064(3) 0.001(3) 0.010(3) 0.011(3) N2 0.075(4) 0.063(3) 0.083(4) -0.009(3) 0.003(3) 0.013(3) N3 0.083(4) 0.066(4) 0.101(5) -0.019(3) 0.025(3) 0.007(3) N4 0.076(4) 0.056(3) 0.075(4) -0.005(3) 0.004(3) 0.007(3) N5 0.078(4) 0.052(3) 0.076(4) -0.006(3) 0.006(3) 0.008(3) N6 0.36(2) 0.136(12) 0.240(19) 0.000 0.193(19) 0.000 O1 0.180(9) 0.374(16) 0.202(11) 0.044(9) 0.088(8) 0.098(10) O2 0.45(3) 0.36(2) 0.47(3) 0.24(2) 0.21(2) 0.26(2) O3 0.201(9) 0.266(11) 0.151(8) 0.017(7) 0.008(7) -0.057(8) O4 0.280(16) 0.55(3) 0.287(17) -0.061(19) -0.082(14) -0.185(19) O5 0.352(11) 0.091(4) 0.191(7) 0.090(4) 0.187(7) 0.123(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C25 1.975(5) . ? Cu1 N4 1.986(5) . ? Cu1 N2 1.987(5) . ? Cu1 N1 2.054(5) . ? Cu1 N3 2.102(7) . ? C1 N1 1.340(7) . ? C1 C2 1.373(9) . ? C1 H1 0.9300 . ? C2 C3 1.402(10) . ? C2 H2 0.9300 . ? C3 C4 1.357(9) . ? C3 C11 1.499(9) . ? C4 C5 1.392(8) . ? C4 H4 0.9300 . ? C5 N1 1.353(7) . ? C5 C6 1.470(9) . ? C6 N2 1.351(8) . ? C6 C7 1.376(9) . ? C7 C8 1.377(10) . ? C7 H7 0.9300 . ? C8 C9 1.397(11) . ? C8 C12 1.527(9) . ? C9 C10 1.357(10) . ? C9 H9 0.9300 . ? C10 N2 1.343(8) . ? C10 H10 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N3 1.332(10) . ? C13 C14 1.357(15) . ? C13 H13 0.9300 . ? C14 C15 1.411(16) . ? C14 H14 0.9300 . ? C15 C16 1.345(13) . ? C15 C24 1.538(16) . ? C16 C17 1.370(12) . ? C16 H16 0.9300 . ? C17 N3 1.364(10) . ? C17 C18 1.511(11) . ? C18 N4 1.341(9) . ? C18 C19 1.372(9) . ? C19 C20 1.376(11) . ? C19 H19 0.9300 . ? C20 C21 1.362(11) . ? C20 C23 1.470(11) . ? C21 C22 1.371(10) . ? C21 H21 0.9300 . ? C22 N4 1.359(8) . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 N5 1.150(10) 7_566 ? C25 C25 1.150(10) 7_566 ? Cl1 O2 1.235(13) . ? Cl1 O4 1.275(12) . ? Cl1 O1 1.315(10) . ? Cl1 O3 1.393(10) . ? N6 O5 1.595(7) 2_756 ? N6 O5 1.595(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 C25 Cu1 N4 91.5(2) . . ? C25 Cu1 N2 93.5(2) . . ? N4 Cu1 N2 175.0(2) . . ? C25 Cu1 N1 140.1(2) . . ? N4 Cu1 N1 96.0(2) . . ? N2 Cu1 N1 80.4(2) . . ? C25 Cu1 N3 114.9(3) . . ? N4 Cu1 N3 79.6(3) . . ? N2 Cu1 N3 97.9(2) . . ? N1 Cu1 N3 105.0(2) . . ? N1 C1 C2 121.6(6) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C1 C2 C3 120.4(6) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 117.1(6) . . ? C4 C3 C11 122.3(7) . . ? C2 C3 C11 120.4(7) . . ? C3 C4 C5 120.9(6) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? N1 C5 C4 121.1(6) . . ? N1 C5 C6 115.0(5) . . ? C4 C5 C6 123.9(6) . . ? N2 C6 C7 121.1(6) . . ? N2 C6 C5 114.8(5) . . ? C7 C6 C5 124.1(6) . . ? C6 C7 C8 120.1(7) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C9 118.1(6) . . ? C7 C8 C12 122.1(8) . . ? C9 C8 C12 119.8(8) . . ? C10 C9 C8 119.3(7) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? N2 C10 C9 122.5(7) . . ? N2 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 122.0(10) . . ? N3 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C13 C14 C15 119.1(10) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 119.1(11) . . ? C16 C15 C24 118.7(13) . . ? C14 C15 C24 122.2(13) . . ? C15 C16 C17 119.1(10) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? N3 C17 C16 122.3(7) . . ? N3 C17 C18 112.5(8) . . ? C16 C17 C18 125.1(8) . . ? N4 C18 C19 121.4(7) . . ? N4 C18 C17 115.8(7) . . ? C19 C18 C17 122.8(9) . . ? C18 C19 C20 121.7(9) . . ? C18 C19 H19 119.1 . . ? C20 C19 H19 119.1 . . ? C21 C20 C19 116.3(7) . . ? C21 C20 C23 121.8(9) . . ? C19 C20 C23 121.9(9) . . ? C20 C21 C22 121.3(8) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? N4 C22 C21 121.7(8) . . ? N4 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C15 C24 H24A 109.5 . . ? C15 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C15 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N5 C25 C25 0.0(3) 7_566 7_566 ? N5 C25 Cu1 178.8(9) 7_566 . ? C25 C25 Cu1 178.8(9) 7_566 . ? O2 Cl1 O4 91.7(14) . . ? O2 Cl1 O1 112.0(11) . . ? O4 Cl1 O1 114.3(14) . . ? O2 Cl1 O3 115.9(13) . . ? O4 Cl1 O3 113.3(11) . . ? O1 Cl1 O3 108.9(7) . . ? C1 N1 C5 118.8(5) . . ? C1 N1 Cu1 127.3(4) . . ? C5 N1 Cu1 113.4(4) . . ? C10 N2 C6 118.9(6) . . ? C10 N2 Cu1 125.1(5) . . ? C6 N2 Cu1 116.0(4) . . ? C13 N3 C17 118.2(8) . . ? C13 N3 Cu1 127.3(6) . . ? C17 N3 Cu1 114.5(5) . . ? C18 N4 C22 117.6(6) . . ? C18 N4 Cu1 117.4(5) . . ? C22 N4 Cu1 125.1(6) . . ? O5 N6 O5 109.3(11) 2_756 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.6(12) . . . . ? C1 C2 C3 C4 1.3(12) . . . . ? C1 C2 C3 C11 176.9(8) . . . . ? C2 C3 C4 C5 -1.9(11) . . . . ? C11 C3 C4 C5 -177.4(7) . . . . ? C3 C4 C5 N1 1.8(10) . . . . ? C3 C4 C5 C6 -179.3(7) . . . . ? N1 C5 C6 N2 5.2(9) . . . . ? C4 C5 C6 N2 -173.7(6) . . . . ? N1 C5 C6 C7 -173.5(7) . . . . ? C4 C5 C6 C7 7.6(11) . . . . ? N2 C6 C7 C8 0.1(12) . . . . ? C5 C6 C7 C8 178.7(7) . . . . ? C6 C7 C8 C9 1.5(13) . . . . ? C6 C7 C8 C12 178.4(8) . . . . ? C7 C8 C9 C10 -2.1(13) . . . . ? C12 C8 C9 C10 -179.0(9) . . . . ? C8 C9 C10 N2 1.0(13) . . . . ? N3 C13 C14 C15 -2.9(17) . . . . ? C13 C14 C15 C16 3.1(19) . . . . ? C13 C14 C15 C24 -178.8(13) . . . . ? C14 C15 C16 C17 -1.5(17) . . . . ? C24 C15 C16 C17 -179.7(11) . . . . ? C15 C16 C17 N3 -0.3(14) . . . . ? C15 C16 C17 C18 -177.5(9) . . . . ? N3 C17 C18 N4 -1.4(8) . . . . ? C16 C17 C18 N4 176.1(7) . . . . ? N3 C17 C18 C19 179.8(6) . . . . ? C16 C17 C18 C19 -2.7(11) . . . . ? N4 C18 C19 C20 0.0(10) . . . . ? C17 C18 C19 C20 178.8(7) . . . . ? C18 C19 C20 C21 -2.5(10) . . . . ? C18 C19 C20 C23 178.0(7) . . . . ? C19 C20 C21 C22 3.2(11) . . . . ? C23 C20 C21 C22 -177.3(7) . . . . ? C20 C21 C22 N4 -1.6(11) . . . . ? N4 Cu1 C25 N5 75(37) . . . 7_566 ? N2 Cu1 C25 N5 -104(37) . . . 7_566 ? N1 Cu1 C25 N5 177(100) . . . 7_566 ? N3 Cu1 C25 N5 -4(37) . . . 7_566 ? N4 Cu1 C25 C25 75(37) . . . 7_566 ? N2 Cu1 C25 C25 -104(37) . . . 7_566 ? N1 Cu1 C25 C25 177(100) . . . 7_566 ? N3 Cu1 C25 C25 -4(37) . . . 7_566 ? C2 C1 N1 C5 0.5(10) . . . . ? C2 C1 N1 Cu1 -170.4(6) . . . . ? C4 C5 N1 C1 -1.1(9) . . . . ? C6 C5 N1 C1 180.0(6) . . . . ? C4 C5 N1 Cu1 171.0(5) . . . . ? C6 C5 N1 Cu1 -7.9(7) . . . . ? C25 Cu1 N1 C1 -98.4(6) . . . . ? N4 Cu1 N1 C1 1.1(6) . . . . ? N2 Cu1 N1 C1 177.6(6) . . . . ? N3 Cu1 N1 C1 81.9(6) . . . . ? C25 Cu1 N1 C5 90.3(5) . . . . ? N4 Cu1 N1 C5 -170.2(5) . . . . ? N2 Cu1 N1 C5 6.3(4) . . . . ? N3 Cu1 N1 C5 -89.4(5) . . . . ? C9 C10 N2 C6 0.7(12) . . . . ? C9 C10 N2 Cu1 -179.7(6) . . . . ? C7 C6 N2 C10 -1.2(10) . . . . ? C5 C6 N2 C10 -180.0(6) . . . . ? C7 C6 N2 Cu1 179.1(6) . . . . ? C5 C6 N2 Cu1 0.3(8) . . . . ? C25 Cu1 N2 C10 36.6(7) . . . . ? N4 Cu1 N2 C10 -139(3) . . . . ? N1 Cu1 N2 C10 176.8(7) . . . . ? N3 Cu1 N2 C10 -79.2(6) . . . . ? C25 Cu1 N2 C6 -143.8(5) . . . . ? N4 Cu1 N2 C6 40(3) . . . . ? N1 Cu1 N2 C6 -3.5(5) . . . . ? N3 Cu1 N2 C6 100.5(5) . . . . ? C14 C13 N3 C17 1.1(13) . . . . ? C14 C13 N3 Cu1 -178.6(8) . . . . ? C16 C17 N3 C13 0.5(11) . . . . ? C18 C17 N3 C13 178.1(7) . . . . ? C16 C17 N3 Cu1 -179.7(7) . . . . ? C18 C17 N3 Cu1 -2.1(7) . . . . ? C25 Cu1 N3 C13 -90.0(7) . . . . ? N4 Cu1 N3 C13 -176.8(7) . . . . ? N2 Cu1 N3 C13 7.6(7) . . . . ? N1 Cu1 N3 C13 89.7(7) . . . . ? C25 Cu1 N3 C17 90.2(5) . . . . ? N4 Cu1 N3 C17 3.4(5) . . . . ? N2 Cu1 N3 C17 -172.2(5) . . . . ? N1 Cu1 N3 C17 -90.0(5) . . . . ? C19 C18 N4 C22 1.7(9) . . . . ? C17 C18 N4 C22 -177.2(5) . . . . ? C19 C18 N4 Cu1 -176.7(5) . . . . ? C17 C18 N4 Cu1 4.4(7) . . . . ? C21 C22 N4 C18 -0.9(10) . . . . ? C21 C22 N4 Cu1 177.3(5) . . . . ? C25 Cu1 N4 C18 -119.4(5) . . . . ? N2 Cu1 N4 C18 56(3) . . . . ? N1 Cu1 N4 C18 99.9(5) . . . . ? N3 Cu1 N4 C18 -4.3(5) . . . . ? C25 Cu1 N4 C22 62.4(5) . . . . ? N2 Cu1 N4 C22 -122(3) . . . . ? N1 Cu1 N4 C22 -78.3(5) . . . . ? N3 Cu1 N4 C22 177.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.921 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.110 data_9 _database_code_depnum_ccdc_archive 'CCDC 869865' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C62 H60 Cu3 N12, 3(Cl O4), 7(H2 O)' _chemical_formula_sum 'C62 H74 Cl3 Cu3 N12 O19' _chemical_formula_weight 1588.30 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 16.6925(18) _cell_length_b 33.626(4) _cell_length_c 14.1498(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7942.4(15) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4544 _cell_measurement_theta_min 2.242 _cell_measurement_theta_max 20.292 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3280 _exptl_absorpt_coefficient_mu 0.966 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8766 _exptl_absorpt_correction_T_max 0.8929 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 38493 _diffrn_reflns_av_R_equivalents 0.0914 _diffrn_reflns_av_sigmaI/netI 0.0740 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7095 _reflns_number_gt 3473 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1118P)^2^] 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 7095 _refine_ls_number_parameters 482 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1190 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1912 _refine_ls_wR_factor_gt 0.1731 _refine_ls_goodness_of_fit_ref 0.879 _refine_ls_restrained_S_all 0.880 _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 0.4326(3) 0.04511(15) 0.3330(4) 0.0651(14) Uani 1 1 d . . . H1 H 0.4544 0.0557 0.2780 0.078 Uiso 1 1 calc R . . C2 C 0.4444(3) 0.00553(15) 0.3511(4) 0.0730(16) Uani 1 1 d . . . H2 H 0.4744 -0.0100 0.3098 0.088 Uiso 1 1 calc R . . C3 C 0.4120(3) -0.01086(15) 0.4302(4) 0.0685(15) Uani 1 1 d . . . C4 C 0.4220(4) -0.05435(14) 0.4547(4) 0.095(2) Uani 1 1 d . . . H4A H 0.4571 -0.0667 0.4098 0.142 Uiso 1 1 calc R . . H4B H 0.3707 -0.0673 0.4530 0.142 Uiso 1 1 calc R . . H4C H 0.4444 -0.0567 0.5169 0.142 Uiso 1 1 calc R . . C5 C 0.3692(3) 0.01391(15) 0.4902(4) 0.0676(14) Uani 1 1 d . . . H5 H 0.3469 0.0038 0.5453 0.081 Uiso 1 1 calc R . . C6 C 0.3598(3) 0.05371(14) 0.4681(4) 0.0576(13) Uani 1 1 d . . . C7 C 0.3176(3) 0.08250(15) 0.5296(4) 0.0627(13) Uani 1 1 d . . . C8 C 0.2773(4) 0.07259(19) 0.6114(4) 0.0881(19) Uani 1 1 d . . . H8 H 0.2743 0.0461 0.6298 0.106 Uiso 1 1 calc R . . C9 C 0.2421(4) 0.1008(2) 0.6651(5) 0.097(2) Uani 1 1 d . . . C10 C 0.1955(6) 0.0894(3) 0.7555(5) 0.161(4) Uani 1 1 d . . . H10A H 0.2251 0.0980 0.8100 0.241 Uiso 1 1 calc R . . H10B H 0.1886 0.0611 0.7577 0.241 Uiso 1 1 calc R . . H10C H 0.1440 0.1021 0.7549 0.241 Uiso 1 1 calc R . . C11 C 0.2484(4) 0.1390(2) 0.6381(5) 0.0883(18) Uani 1 1 d . . . H11 H 0.2265 0.1591 0.6750 0.106 Uiso 1 1 calc R . . C12 C 0.2875(3) 0.14804(17) 0.5559(5) 0.0776(16) Uani 1 1 d . . . H12 H 0.2911 0.1746 0.5378 0.093 Uiso 1 1 calc R . . C13 C 0.5146(4) 0.15206(14) 0.5222(4) 0.0668(14) Uani 1 1 d . . . H13 H 0.4756 0.1530 0.5691 0.080 Uiso 1 1 calc R . . C14 C 0.5939(4) 0.15612(14) 0.5480(4) 0.0715(15) Uani 1 1 d . . . H14 H 0.6071 0.1599 0.6112 0.086 Uiso 1 1 calc R . . C15 C 0.6531(4) 0.15470(15) 0.4814(5) 0.0735(15) Uani 1 1 d . . . C16 C 0.7400(4) 0.1592(2) 0.5071(5) 0.119(2) Uani 1 1 d . . . H16A H 0.7448 0.1763 0.5612 0.178 Uiso 1 1 calc R . . H16B H 0.7686 0.1707 0.4548 0.178 Uiso 1 1 calc R . . H16C H 0.7622 0.1336 0.5217 0.178 Uiso 1 1 calc R . . C17 C 0.6290(3) 0.14974(15) 0.3887(5) 0.0738(16) Uani 1 1 d . . . H17 H 0.6672 0.1488 0.3409 0.089 Uiso 1 1 calc R . . C18 C 0.5488(3) 0.14618(13) 0.3662(4) 0.0569(13) Uani 1 1 d . . . C19 C 0.5195(3) 0.14108(14) 0.2697(4) 0.0619(14) Uani 1 1 d . . . C20 C 0.5677(4) 0.14404(16) 0.1891(5) 0.0794(17) Uani 1 1 d . . . H20 H 0.6219 0.1498 0.1954 0.095 Uiso 1 1 calc R . . C21 C 0.5356(4) 0.13857(18) 0.1011(5) 0.0852(18) Uani 1 1 d . . . C22 C 0.5894(5) 0.1405(3) 0.0151(5) 0.135(3) Uani 1 1 d . . . H22A H 0.5638 0.1560 -0.0333 0.203 Uiso 1 1 calc R . . H22B H 0.5991 0.1141 -0.0081 0.203 Uiso 1 1 calc R . . H22C H 0.6394 0.1527 0.0320 0.203 Uiso 1 1 calc R . . C23 C 0.4557(4) 0.13088(19) 0.0942(4) 0.0893(19) Uani 1 1 d . . . H23 H 0.4329 0.1269 0.0351 0.107 Uiso 1 1 calc R . . C24 C 0.4093(4) 0.12893(17) 0.1723(5) 0.0843(18) Uani 1 1 d . . . H24 H 0.3547 0.1242 0.1657 0.101 Uiso 1 1 calc R . . C25 C 0.2702(3) 0.20098(15) 0.3176(4) 0.0590(13) Uani 1 1 d . . . C26 C 0.1357(5) 0.2500 0.1003(5) 0.0626(19) Uani 1 2 d S . . H26 H 0.1878 0.2500 0.0772 0.075 Uiso 1 2 calc SR . . C27 C 0.0733(5) 0.2500 0.0367(6) 0.068(2) Uani 1 2 d S . . H27 H 0.0838 0.2500 -0.0278 0.081 Uiso 1 2 calc SR . . C28 C -0.0063(5) 0.2500 0.0691(6) 0.065(2) Uani 1 2 d S . . C29 C -0.0756(5) 0.2500 0.0028(6) 0.092(3) Uani 1 2 d S . . H29A H -0.1227 0.2411 0.0355 0.139 Uiso 0.50 1 calc PR . . H29B H -0.0646 0.2324 -0.0491 0.139 Uiso 0.50 1 calc PR . . H29C H -0.0841 0.2764 -0.0207 0.139 Uiso 0.50 1 calc PR . . C30 C -0.0167(4) 0.2500 0.1643(6) 0.0617(19) Uani 1 2 d S . . H30 H -0.0685 0.2500 0.1885 0.074 Uiso 1 2 calc SR . . C31 C 0.0472(4) 0.2500 0.2261(5) 0.0524(17) Uani 1 2 d S . . C32 C 0.0391(5) 0.2500 0.3285(5) 0.0608(18) Uani 1 2 d S . . C33 C -0.0352(5) 0.2500 0.3761(7) 0.084(2) Uani 1 2 d S . . H33 H -0.0820 0.2500 0.3406 0.101 Uiso 1 2 calc SR . . C34 C -0.0409(6) 0.2500 0.4715(7) 0.092(3) Uani 1 2 d S . . C35 C -0.1201(6) 0.2500 0.5228(8) 0.140(4) Uani 1 2 d S . . H35A H -0.1216 0.2718 0.5665 0.211 Uiso 0.50 1 calc PR . . H35B H -0.1261 0.2255 0.5567 0.211 Uiso 0.50 1 calc PR . . H35C H -0.1629 0.2527 0.4779 0.211 Uiso 0.50 1 calc PR . . C36 C 0.0292(7) 0.2500 0.5227(7) 0.108(3) Uani 1 2 d S . . H36 H 0.0280 0.2500 0.5884 0.130 Uiso 1 2 calc SR . . C37 C 0.1028(5) 0.2500 0.4739(6) 0.085(2) Uani 1 2 d S . . H37 H 0.1499 0.2500 0.5091 0.101 Uiso 1 2 calc SR . . Cl1 Cl 0.20286(19) 0.04866(9) 0.2450(3) 0.1785(13) Uani 1 1 d . . . Cl2 Cl 0.1869(6) 0.2500 0.7554(4) 0.243(3) Uani 1 2 d SDU . . Cu1 Cu 0.37564(4) 0.129370(17) 0.37738(5) 0.0629(3) Uani 1 1 d . . . Cu2 Cu 0.21325(5) 0.2500 0.29852(6) 0.0598(3) Uani 1 2 d S . . N1 N 0.3917(2) 0.06907(11) 0.3898(3) 0.0552(10) Uani 1 1 d . . . N2 N 0.3211(3) 0.12020(12) 0.5000(3) 0.0640(11) Uani 1 1 d . . . N3 N 0.4916(2) 0.14692(11) 0.4336(3) 0.0588(11) Uani 1 1 d . . . N4 N 0.4407(3) 0.13377(12) 0.2610(3) 0.0664(12) Uani 1 1 d . . . N5 N 0.3058(3) 0.17305(13) 0.3386(3) 0.0712(12) Uani 1 1 d . . . N6 N 0.1246(3) 0.2500 0.1943(4) 0.0565(15) Uani 1 2 d S . . N7 N 0.1085(4) 0.2500 0.3786(5) 0.0662(16) Uani 1 2 d S . . O1 O 0.2421(11) 0.0752(6) 0.199(2) 0.64(3) Uani 1 1 d . . . O2 O 0.2390(6) 0.0146(2) 0.2552(8) 0.266(5) Uani 1 1 d . . . O3 O 0.1293(4) 0.0470(3) 0.2103(6) 0.225(4) Uani 1 1 d . . . O4 O 0.2177(8) 0.0752(5) 0.2994(13) 0.494(18) Uani 1 1 d . . . O5 O 0.2238(13) 0.2500 0.6600(10) 0.315(7) Uani 1 2 d SU . . O6 O 0.2198(10) 0.2272(4) 0.8239(9) 0.250(9) Uani 0.50 1 d P . . O7 O 0.1433(11) 0.2164(4) 0.7410(12) 0.218(8) Uani 0.50 1 d P . . O8 O 0.2623(8) 0.2500 0.7386(12) 0.315(7) Uani 1 2 d SD . . O9 O 0.4492(12) 0.0894(8) 0.817(3) 0.81(2) Uani 1 1 d . . . H9A H 0.4985 0.0920 0.8309 1.210 Uiso 1 1 d R . . H9B H 0.4439 0.0890 0.7573 1.210 Uiso 1 1 d R . . O10 O 0.460(2) 0.1846(11) 0.7638(12) 0.95(4) Uani 1 1 d . . . H10E H 0.4445 0.1643 0.7949 1.424 Uiso 1 1 d R . . H10D H 0.5106 0.1850 0.7613 1.424 Uiso 1 1 d R . . O11 O 0.3452(12) 0.0369(7) -0.015(3) 0.81(2) Uani 1 1 d . . . H11A H 0.3821 0.0395 0.0255 1.210 Uiso 1 1 d R . . H11B H 0.3032 0.0487 0.0037 1.210 Uiso 1 1 d R . . O12 O 0.502(5) 0.016(2) 0.074(2) 1.00(9) Uani 0.50 1 d P . . H12A H 0.5314 -0.0005 0.0438 1.495 Uiso 0.50 1 d PR . . H12B H 0.5028 0.0103 0.1328 1.495 Uiso 0.50 1 d PR . . 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 0.065(4) 0.056(3) 0.074(4) 0.001(3) 0.003(3) 0.008(3) C2 0.084(4) 0.059(4) 0.076(4) -0.009(3) -0.003(3) 0.013(3) C3 0.072(4) 0.050(3) 0.084(4) -0.008(3) -0.022(3) 0.009(3) C4 0.119(5) 0.044(3) 0.120(5) 0.006(3) -0.027(4) 0.005(3) C5 0.072(4) 0.055(3) 0.076(4) 0.016(3) -0.006(3) -0.003(3) C6 0.054(3) 0.050(3) 0.069(4) 0.001(3) -0.004(3) 0.002(2) C7 0.057(3) 0.064(3) 0.067(4) 0.001(3) -0.007(3) 0.002(3) C8 0.111(5) 0.082(4) 0.072(4) 0.008(3) 0.028(4) -0.002(4) C9 0.112(5) 0.098(5) 0.081(5) 0.002(4) 0.024(4) 0.008(4) C10 0.209(10) 0.161(8) 0.113(6) 0.007(5) 0.080(7) 0.008(7) C11 0.089(5) 0.094(5) 0.082(5) -0.017(4) 0.009(4) 0.008(4) C12 0.072(4) 0.066(4) 0.095(5) -0.012(3) 0.000(4) 0.008(3) C13 0.079(4) 0.044(3) 0.076(4) 0.009(3) 0.005(3) 0.002(3) C14 0.081(4) 0.054(3) 0.079(4) 0.007(3) -0.015(4) 0.001(3) C15 0.068(4) 0.057(3) 0.096(5) 0.006(3) -0.007(4) 0.006(3) C16 0.063(4) 0.146(7) 0.147(7) -0.006(5) -0.019(4) -0.007(4) C17 0.065(4) 0.052(3) 0.105(5) -0.003(3) 0.008(4) -0.001(3) C18 0.057(4) 0.038(3) 0.076(4) 0.006(2) 0.002(3) 0.002(2) C19 0.056(4) 0.047(3) 0.083(4) 0.011(3) 0.004(3) 0.005(2) C20 0.064(4) 0.075(4) 0.100(5) -0.001(3) 0.017(4) -0.006(3) C21 0.090(5) 0.088(5) 0.078(5) 0.004(3) 0.016(4) -0.001(4) C22 0.127(6) 0.182(8) 0.096(6) -0.009(5) 0.038(5) -0.029(6) C23 0.090(5) 0.118(5) 0.059(4) 0.009(3) 0.002(4) 0.000(4) C24 0.069(4) 0.098(5) 0.086(5) 0.013(4) -0.012(4) -0.001(3) C25 0.052(3) 0.050(3) 0.075(4) -0.001(3) -0.005(3) -0.004(3) C26 0.068(5) 0.052(4) 0.068(6) 0.000 0.002(4) 0.000 C27 0.097(7) 0.036(4) 0.070(5) 0.000 -0.014(5) 0.000 C28 0.084(6) 0.037(4) 0.073(6) 0.000 -0.019(5) 0.000 C29 0.101(7) 0.062(5) 0.115(7) 0.000 -0.048(6) 0.000 C30 0.054(5) 0.056(4) 0.075(5) 0.000 -0.008(4) 0.000 C31 0.054(5) 0.035(3) 0.069(5) 0.000 -0.002(4) 0.000 C32 0.055(5) 0.056(4) 0.071(5) 0.000 -0.002(4) 0.000 C33 0.054(5) 0.100(7) 0.097(7) 0.000 0.001(5) 0.000 C34 0.064(6) 0.121(8) 0.092(7) 0.000 0.017(6) 0.000 C35 0.091(8) 0.200(13) 0.131(9) 0.000 0.041(7) 0.000 C36 0.106(8) 0.144(9) 0.075(6) 0.000 0.017(7) 0.000 C37 0.067(6) 0.115(7) 0.072(6) 0.000 -0.013(5) 0.000 Cl1 0.157(2) 0.1047(18) 0.273(4) -0.047(2) -0.113(3) 0.0167(18) Cl2 0.460(11) 0.123(4) 0.146(4) 0.000 -0.033(6) 0.000 Cu1 0.0576(4) 0.0528(4) 0.0782(5) 0.0124(3) 0.0069(3) 0.0107(3) Cu2 0.0509(5) 0.0436(5) 0.0850(7) 0.000 -0.0081(5) 0.000 N1 0.054(3) 0.047(2) 0.065(3) 0.007(2) 0.003(2) 0.005(2) N2 0.063(3) 0.049(3) 0.080(3) 0.001(2) 0.008(2) 0.008(2) N3 0.061(3) 0.044(2) 0.071(3) 0.009(2) -0.001(2) 0.003(2) N4 0.056(3) 0.063(3) 0.081(3) 0.016(2) 0.002(2) 0.008(2) N5 0.060(3) 0.050(3) 0.103(3) 0.012(2) 0.002(3) 0.008(2) N6 0.060(4) 0.035(3) 0.074(4) 0.000 0.000(3) 0.000 N7 0.061(4) 0.073(4) 0.065(4) 0.000 -0.005(3) 0.000 O1 0.308(18) 0.40(2) 1.22(7) 0.53(4) -0.08(3) -0.085(19) O2 0.261(9) 0.100(5) 0.436(14) -0.031(6) -0.096(9) 0.068(6) O3 0.149(6) 0.238(9) 0.288(10) -0.020(7) -0.099(6) -0.033(5) O4 0.324(16) 0.412(19) 0.75(3) -0.45(2) -0.38(2) 0.229(15) O5 0.44(2) 0.364(17) 0.141(8) 0.000 -0.064(9) 0.000 O6 0.309(18) 0.273(18) 0.167(11) 0.192(12) -0.105(12) -0.076(13) O7 0.31(2) 0.084(8) 0.258(18) -0.004(9) -0.001(16) -0.075(11) O8 0.44(2) 0.364(17) 0.141(8) 0.000 -0.064(9) 0.000 O9 0.392(18) 0.55(3) 1.48(6) -0.56(3) 0.14(3) -0.138(16) O10 0.95(6) 1.57(9) 0.33(2) -0.49(4) -0.11(3) 0.52(6) O11 0.392(18) 0.55(3) 1.48(6) -0.56(3) 0.14(3) -0.138(16) O12 1.45(16) 1.25(15) 0.30(3) -0.09(5) -0.08(6) 1.15(14) _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 N1 1.328(6) . ? C1 C2 1.370(7) . ? C1 H1 0.9300 . ? C2 C3 1.360(7) . ? C2 H2 0.9300 . ? C3 C5 1.387(7) . ? C3 C4 1.512(7) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.383(6) . ? C5 H5 0.9300 . ? C6 N1 1.333(6) . ? C6 C7 1.480(7) . ? C7 N2 1.336(6) . ? C7 C8 1.379(7) . ? C8 C9 1.350(8) . ? C8 H8 0.9300 . ? C9 C11 1.343(9) . ? C9 C10 1.545(9) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.368(8) . ? C11 H11 0.9300 . ? C12 N2 1.347(6) . ? C12 H12 0.9300 . ? C13 N3 1.322(6) . ? C13 C14 1.380(7) . ? C13 H13 0.9300 . ? C14 C15 1.366(8) . ? C14 H14 0.9300 . ? C15 C17 1.382(7) . ? C15 C16 1.504(8) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.381(7) . ? C17 H17 0.9300 . ? C18 N3 1.350(6) . ? C18 C19 1.461(7) . ? C19 N4 1.344(6) . ? C19 C20 1.399(7) . ? C20 C21 1.368(8) . ? C20 H20 0.9300 . ? C21 C23 1.362(9) . ? C21 C22 1.513(9) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.351(8) . ? C23 H23 0.9300 . ? C24 N4 1.370(7) . ? C24 H24 0.9300 . ? C25 N5 1.150(6) . ? C25 Cu2 1.922(5) . ? C26 N6 1.343(8) . ? C26 C27 1.376(10) . ? C26 H26 0.9300 . ? C27 C28 1.405(10) . ? C27 H27 0.9300 . ? C28 C30 1.358(10) . ? C28 C29 1.490(10) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.379(9) . ? C30 H30 0.9300 . ? C31 N6 1.368(8) . ? C31 C32 1.455(10) . ? C32 N7 1.359(8) . ? C32 C33 1.411(10) . ? C33 C34 1.353(11) . ? C33 H33 0.9300 . ? C34 C36 1.377(12) . ? C34 C35 1.507(12) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 C37 1.410(12) . ? C36 H36 0.9300 . ? C37 N7 1.353(9) . ? C37 H37 0.9300 . ? Cl1 O4 1.204(8) . ? Cl1 O1 1.284(14) . ? Cl1 O2 1.302(7) . ? Cl1 O3 1.324(6) . ? Cl2 O8 1.280(10) . ? Cl2 O6 1.351(10) 7_565 ? Cl2 O6 1.351(10) . ? Cl2 O7 1.361(13) . ? Cl2 O7 1.361(13) 7_565 ? Cl2 O5 1.484(17) . ? Cu1 N5 1.954(4) . ? Cu1 N4 1.978(4) . ? Cu1 N2 1.984(4) . ? Cu1 N1 2.053(4) . ? Cu1 N3 2.175(4) . ? Cu2 C25 1.922(5) 7_565 ? Cu2 N7 2.083(6) . ? Cu2 N6 2.090(6) . ? O6 O6 1.53(3) 7_565 ? O8 O6 1.595(17) 7_565 ? O9 H9A 0.8501 . ? O9 H9B 0.8500 . ? O10 H10E 0.8499 . ? O10 H10D 0.8500 . ? O11 H11A 0.8499 . ? O11 H11B 0.8504 . ? O12 H12A 0.8501 . ? O12 H12B 0.8502 . ? 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 C1 C2 123.4(5) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 119.4(5) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C5 117.7(5) . . ? C2 C3 C4 122.5(5) . . ? C5 C3 C4 119.8(6) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C3 120.1(5) . . ? C6 C5 H5 119.9 . . ? C3 C5 H5 119.9 . . ? N1 C6 C5 121.1(5) . . ? N1 C6 C7 115.2(4) . . ? C5 C6 C7 123.7(5) . . ? N2 C7 C8 120.9(5) . . ? N2 C7 C6 114.5(5) . . ? C8 C7 C6 124.6(5) . . ? C9 C8 C7 121.0(6) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C11 C9 C8 118.5(6) . . ? C11 C9 C10 120.8(7) . . ? C8 C9 C10 120.7(7) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 C12 119.4(6) . . ? C9 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? N2 C12 C11 122.9(6) . . ? N2 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? N3 C13 C14 122.8(5) . . ? N3 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C15 C14 C13 120.5(6) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C17 116.6(5) . . ? C14 C15 C16 121.9(6) . . ? C17 C15 C16 121.5(6) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C15 120.7(6) . . ? C18 C17 H17 119.6 . . ? C15 C17 H17 119.6 . . ? N3 C18 C17 121.4(5) . . ? N3 C18 C19 115.2(5) . . ? C17 C18 C19 123.4(5) . . ? N4 C19 C20 120.1(5) . . ? N4 C19 C18 115.7(5) . . ? C20 C19 C18 124.1(5) . . ? C21 C20 C19 120.5(6) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C23 C21 C20 118.3(6) . . ? C23 C21 C22 122.1(7) . . ? C20 C21 C22 119.6(7) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C21 120.8(6) . . ? C24 C23 H23 119.6 . . ? C21 C23 H23 119.6 . . ? C23 C24 N4 121.6(6) . . ? C23 C24 H24 119.2 . . ? N4 C24 H24 119.2 . . ? N5 C25 Cu2 172.7(5) . . ? N6 C26 C27 122.9(7) . . ? N6 C26 H26 118.5 . . ? C27 C26 H26 118.5 . . ? C26 C27 C28 120.1(7) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C30 C28 C27 116.4(7) . . ? C30 C28 C29 121.7(8) . . ? C27 C28 C29 121.9(8) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 C31 122.0(7) . . ? C28 C30 H30 119.0 . . ? C31 C30 H30 119.0 . . ? N6 C31 C30 121.4(7) . . ? N6 C31 C32 114.5(6) . . ? C30 C31 C32 124.0(7) . . ? N7 C32 C33 120.0(7) . . ? N7 C32 C31 116.1(7) . . ? C33 C32 C31 123.9(7) . . ? C34 C33 C32 122.7(8) . . ? C34 C33 H33 118.7 . . ? C32 C33 H33 118.7 . . ? C33 C34 C36 117.7(8) . . ? C33 C34 C35 122.9(10) . . ? C36 C34 C35 119.4(10) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 C37 118.9(9) . . ? C34 C36 H36 120.5 . . ? C37 C36 H36 120.5 . . ? N7 C37 C36 123.3(8) . . ? N7 C37 H37 118.3 . . ? C36 C37 H37 118.3 . . ? O4 Cl1 O1 72.8(17) . . ? O4 Cl1 O2 119.0(8) . . ? O1 Cl1 O2 115.5(12) . . ? O4 Cl1 O3 117.4(7) . . ? O1 Cl1 O3 108.4(10) . . ? O2 Cl1 O3 115.7(6) . . ? O8 Cl2 O6 74.6(11) . 7_565 ? O8 Cl2 O6 74.6(11) . . ? O6 Cl2 O6 69.1(15) 7_565 . ? O8 Cl2 O7 119.9(9) . . ? O6 Cl2 O7 142.8(12) 7_565 . ? O6 Cl2 O7 81.6(9) . . ? O8 Cl2 O7 119.9(9) . 7_565 ? O6 Cl2 O7 81.6(9) 7_565 7_565 ? O6 Cl2 O7 142.8(12) . 7_565 ? O7 Cl2 O7 112.4(18) . 7_565 ? O8 Cl2 O5 54.8(10) . . ? O6 Cl2 O5 119.0(11) 7_565 . ? O6 Cl2 O5 119.0(11) . . ? O7 Cl2 O5 94.9(8) . . ? O7 Cl2 O5 94.9(8) 7_565 . ? N5 Cu1 N4 92.14(18) . . ? N5 Cu1 N2 95.10(18) . . ? N4 Cu1 N2 172.65(17) . . ? N5 Cu1 N1 147.60(17) . . ? N4 Cu1 N1 94.22(16) . . ? N2 Cu1 N1 80.29(16) . . ? N5 Cu1 N3 115.47(16) . . ? N4 Cu1 N3 78.21(18) . . ? N2 Cu1 N3 97.49(17) . . ? N1 Cu1 N3 96.92(14) . . ? C25 Cu2 C25 118.1(3) 7_565 . ? C25 Cu2 N7 109.81(16) 7_565 . ? C25 Cu2 N7 109.81(16) . . ? C25 Cu2 N6 116.71(15) 7_565 . ? C25 Cu2 N6 116.71(15) . . ? N7 Cu2 N6 77.8(2) . . ? C1 N1 C6 118.3(4) . . ? C1 N1 Cu1 127.9(3) . . ? C6 N1 Cu1 113.7(3) . . ? C7 N2 C12 117.2(5) . . ? C7 N2 Cu1 116.2(3) . . ? C12 N2 Cu1 126.6(4) . . ? C13 N3 C18 117.8(5) . . ? C13 N3 Cu1 129.8(4) . . ? C18 N3 Cu1 111.5(3) . . ? C19 N4 C24 118.7(5) . . ? C19 N4 Cu1 118.4(4) . . ? C24 N4 Cu1 122.9(4) . . ? C25 N5 Cu1 173.9(4) . . ? C26 N6 C31 117.1(6) . . ? C26 N6 Cu2 127.0(5) . . ? C31 N6 Cu2 115.9(5) . . ? C37 N7 C32 117.4(7) . . ? C37 N7 Cu2 127.0(5) . . ? C32 N7 Cu2 115.6(5) . . ? Cl2 O6 O6 55.5(8) . 7_565 ? Cl2 O8 O6 54.7(8) . 7_565 ? H9A O9 H9B 109.5 . . ? H10E O10 H10D 109.5 . . ? H11A O11 H11B 109.4 . . ? H12A O12 H12B 110.1 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.511 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.087 data_6 _database_code_depnum_ccdc_archive 'CCDC 869866' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H16 Cu N5, B F4, H2 O' _chemical_formula_sum 'C25 H18 B Cu F4 N5 O' _chemical_formula_weight 554.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0341(13) _cell_length_b 11.5133(15) _cell_length_c 12.2062(16) _cell_angle_alpha 64.138(2) _cell_angle_beta 72.057(2) _cell_angle_gamma 69.254(2) _cell_volume 1166.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1564 _cell_measurement_theta_min 2.208 _cell_measurement_theta_max 22.084 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 562 _exptl_absorpt_coefficient_mu 0.998 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8896 _exptl_absorpt_correction_T_max 0.9068 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5918 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0850 _diffrn_reflns_limit_h_min -7 _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 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4040 _reflns_number_gt 2568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0768P)^2^] 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 4040 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1576 _refine_ls_wR_factor_gt 0.1407 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.28597(7) 0.23060(6) 0.73269(5) 0.0460(2) Uani 1 1 d . . . B1 B 0.9182(11) 0.2546(9) 0.1657(8) 0.082(2) Uani 1 1 d . . . C1 C 0.2019(6) -0.0292(5) 0.9299(5) 0.0526(13) Uani 1 1 d . . . H1 H 0.1720 -0.0372 0.8692 0.063 Uiso 1 1 calc R . . C2 C 0.1902(6) -0.1258(5) 1.0494(5) 0.0597(15) Uani 1 1 d . . . H2 H 0.1526 -0.1965 1.0672 0.072 Uiso 1 1 calc R . . C3 C 0.2329(6) -0.1170(5) 1.1381(5) 0.0552(14) Uani 1 1 d . . . H3 H 0.2247 -0.1815 1.2176 0.066 Uiso 1 1 calc R . . C4 C 0.2900(5) -0.0114(5) 1.1122(4) 0.0436(11) Uani 1 1 d . . . C5 C 0.3365(6) 0.0084(5) 1.2007(5) 0.0578(14) Uani 1 1 d . . . H5 H 0.3313 -0.0533 1.2816 0.069 Uiso 1 1 calc R . . C6 C 0.3876(6) 0.1141(6) 1.1699(5) 0.0589(15) Uani 1 1 d . . . H6 H 0.4170 0.1240 1.2299 0.071 Uiso 1 1 calc R . . C7 C 0.3976(5) 0.2115(5) 1.0467(4) 0.0470(12) Uani 1 1 d . . . C8 C 0.4483(6) 0.3240(6) 1.0079(5) 0.0596(15) Uani 1 1 d . . . H8 H 0.4814 0.3386 1.0629 0.072 Uiso 1 1 calc R . . C9 C 0.4491(6) 0.4118(6) 0.8895(6) 0.0668(17) Uani 1 1 d . . . H9 H 0.4812 0.4878 0.8638 0.080 Uiso 1 1 calc R . . C10 C 0.4021(6) 0.3893(5) 0.8057(5) 0.0588(14) Uani 1 1 d . . . H10 H 0.4046 0.4501 0.7245 0.071 Uiso 1 1 calc R . . C11 C 0.3520(5) 0.1955(4) 0.9582(4) 0.0387(11) Uani 1 1 d . . . C12 C 0.2977(5) 0.0831(4) 0.9907(4) 0.0375(10) Uani 1 1 d . . . C13 C 0.0118(6) 0.4520(5) 0.7922(5) 0.0561(14) Uani 1 1 d . . . H13 H 0.0605 0.4579 0.8424 0.067 Uiso 1 1 calc R . . C14 C -0.1259(7) 0.5366(6) 0.7753(6) 0.0721(17) Uani 1 1 d . . . H14 H -0.1669 0.5988 0.8135 0.087 Uiso 1 1 calc R . . C15 C -0.1996(7) 0.5297(6) 0.7052(6) 0.079(2) Uani 1 1 d . . . H15 H -0.2915 0.5865 0.6950 0.095 Uiso 1 1 calc R . . C16 C -0.1380(6) 0.4358(5) 0.6463(5) 0.0560(14) Uani 1 1 d . . . C17 C -0.2056(7) 0.4201(7) 0.5676(6) 0.078(2) Uani 1 1 d . . . H17 H -0.2965 0.4757 0.5519 0.093 Uiso 1 1 calc R . . C18 C -0.1416(8) 0.3280(7) 0.5163(6) 0.077(2) Uani 1 1 d . . . H18 H -0.1890 0.3198 0.4665 0.093 Uiso 1 1 calc R . . C19 C -0.0014(7) 0.2419(6) 0.5367(4) 0.0603(16) Uani 1 1 d . . . C20 C 0.0725(9) 0.1420(7) 0.4869(5) 0.077(2) Uani 1 1 d . . . H20 H 0.0308 0.1294 0.4360 0.092 Uiso 1 1 calc R . . C21 C 0.2039(9) 0.0645(7) 0.5128(6) 0.082(2) Uani 1 1 d . . . H21 H 0.2524 -0.0025 0.4808 0.098 Uiso 1 1 calc R . . C22 C 0.2670(7) 0.0847(6) 0.5873(5) 0.0658(16) Uani 1 1 d . . . H22 H 0.3583 0.0310 0.6035 0.079 Uiso 1 1 calc R . . C23 C 0.0683(6) 0.2563(5) 0.6125(4) 0.0467(12) Uani 1 1 d . . . C24 C 0.0002(5) 0.3549(5) 0.6672(4) 0.0445(12) Uani 1 1 d . . . C25 C 0.4460(6) 0.2702(5) 0.5941(5) 0.0568(14) Uani 1 1 d . . . F1 F 0.8648(6) 0.3053(6) 0.2535(5) 0.149(2) Uani 1 1 d . . . F2 F 0.9591(7) 0.1229(5) 0.2186(7) 0.175(2) Uani 1 1 d . . . F3 F 1.0289(7) 0.3034(7) 0.0888(6) 0.188(3) Uani 1 1 d . . . F4 F 0.8034(7) 0.2892(6) 0.1072(5) 0.153(2) Uani 1 1 d . . . N1 N 0.2539(4) 0.0733(4) 0.9004(3) 0.0433(10) Uani 1 1 d . . . N2 N 0.3537(4) 0.2823(4) 0.8400(4) 0.0449(10) Uani 1 1 d . . . N3 N 0.0742(4) 0.3634(4) 0.7378(3) 0.0443(10) Uani 1 1 d . . . N4 N 0.2015(5) 0.1779(4) 0.6361(3) 0.0489(10) Uani 1 1 d . . . N5 N 0.5351(6) 0.2916(7) 0.5098(5) 0.0934(19) Uani 1 1 d . . . O1 O 0.5510(5) 0.2432(4) 0.2903(4) 0.0940(14) Uani 1 1 d . . . H1B H 0.5462 0.2566 0.3548 0.141 Uiso 1 1 d R . . H1A H 0.6254 0.2636 0.2376 0.141 Uiso 1 1 d 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 0.0521(4) 0.0508(4) 0.0408(4) -0.0173(3) -0.0109(3) -0.0170(3) B1 0.092(6) 0.094(6) 0.076(5) -0.048(5) -0.002(5) -0.031(5) C1 0.067(4) 0.050(3) 0.049(3) -0.018(3) -0.010(3) -0.024(3) C2 0.068(4) 0.050(3) 0.063(4) -0.019(3) -0.003(3) -0.029(3) C3 0.062(4) 0.049(3) 0.041(3) -0.008(2) -0.004(3) -0.015(3) C4 0.042(3) 0.048(3) 0.040(3) -0.020(2) -0.009(2) -0.005(2) C5 0.063(4) 0.065(3) 0.042(3) -0.018(3) -0.018(3) -0.006(3) C6 0.055(3) 0.079(4) 0.050(3) -0.033(3) -0.024(3) -0.001(3) C7 0.042(3) 0.056(3) 0.052(3) -0.031(3) -0.013(2) -0.005(2) C8 0.063(4) 0.068(4) 0.069(4) -0.042(3) -0.019(3) -0.011(3) C9 0.071(4) 0.060(3) 0.098(5) -0.046(4) -0.023(4) -0.021(3) C10 0.074(4) 0.053(3) 0.054(3) -0.017(3) -0.011(3) -0.027(3) C11 0.036(3) 0.041(3) 0.041(3) -0.020(2) -0.007(2) -0.006(2) C12 0.032(3) 0.043(3) 0.039(3) -0.020(2) -0.005(2) -0.006(2) C13 0.064(4) 0.051(3) 0.054(3) -0.019(3) -0.005(3) -0.021(3) C14 0.062(4) 0.055(4) 0.086(5) -0.030(3) 0.001(4) -0.008(3) C15 0.046(4) 0.060(4) 0.088(5) 0.004(4) -0.005(3) -0.013(3) C16 0.049(3) 0.050(3) 0.053(3) 0.002(3) -0.012(3) -0.019(3) C17 0.062(4) 0.088(5) 0.065(4) 0.014(4) -0.033(3) -0.035(4) C18 0.087(5) 0.092(5) 0.058(4) 0.005(4) -0.032(4) -0.055(5) C19 0.075(4) 0.076(4) 0.033(3) 0.003(3) -0.016(3) -0.048(4) C20 0.121(6) 0.089(5) 0.050(3) -0.023(3) -0.023(4) -0.057(5) C21 0.117(6) 0.093(5) 0.059(4) -0.046(4) -0.008(4) -0.039(5) C22 0.080(4) 0.074(4) 0.057(3) -0.038(3) -0.009(3) -0.022(3) C23 0.056(3) 0.054(3) 0.032(3) -0.007(2) -0.011(2) -0.026(3) C24 0.049(3) 0.046(3) 0.031(2) 0.002(2) -0.012(2) -0.021(3) C25 0.053(3) 0.074(4) 0.045(3) -0.020(3) -0.013(3) -0.017(3) F1 0.167(5) 0.204(5) 0.125(4) -0.100(4) -0.016(4) -0.062(4) F2 0.173(6) 0.099(4) 0.246(7) -0.048(4) -0.062(5) -0.027(4) F3 0.143(5) 0.209(6) 0.146(5) -0.035(4) 0.025(4) -0.054(5) F4 0.157(5) 0.192(5) 0.155(5) -0.090(4) -0.069(4) -0.025(4) N1 0.047(2) 0.043(2) 0.045(2) -0.0175(19) -0.0110(19) -0.014(2) N2 0.052(3) 0.041(2) 0.047(2) -0.017(2) -0.011(2) -0.015(2) N3 0.048(2) 0.044(2) 0.038(2) -0.0091(19) -0.0084(19) -0.017(2) N4 0.054(3) 0.057(3) 0.044(2) -0.025(2) -0.006(2) -0.018(2) N5 0.072(4) 0.161(6) 0.060(3) -0.046(4) -0.001(3) -0.046(4) O1 0.087(3) 0.113(3) 0.106(3) -0.059(3) -0.035(3) -0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C25 1.955(6) . ? Cu1 N2 2.011(4) . ? Cu1 N4 2.020(4) . ? Cu1 N1 2.085(4) . ? Cu1 N3 2.135(4) . ? B1 F1 1.321(9) . ? B1 F2 1.324(9) . ? B1 F3 1.330(10) . ? B1 F4 1.389(10) . ? C1 N1 1.321(6) . ? C1 C2 1.396(7) . ? C1 H1 0.9300 . ? C2 C3 1.333(7) . ? C2 H2 0.9300 . ? C3 C4 1.398(7) . ? C3 H3 0.9300 . ? C4 C12 1.404(6) . ? C4 C5 1.428(6) . ? C5 C6 1.345(7) . ? C5 H5 0.9300 . ? C6 C7 1.431(7) . ? C6 H6 0.9300 . ? C7 C8 1.394(7) . ? C7 C11 1.396(6) . ? C8 C9 1.355(8) . ? C8 H8 0.9300 . ? C9 C10 1.397(7) . ? C9 H9 0.9300 . ? C10 N2 1.333(6) . ? C10 H10 0.9300 . ? C11 N2 1.349(6) . ? C11 C12 1.431(6) . ? C12 N1 1.364(5) . ? C13 N3 1.324(6) . ? C13 C14 1.396(8) . ? C13 H13 0.9300 . ? C14 C15 1.333(9) . ? C14 H14 0.9300 . ? C15 C16 1.413(8) . ? C15 H15 0.9300 . ? C16 C24 1.397(7) . ? C16 C17 1.434(8) . ? C17 C18 1.334(9) . ? C17 H17 0.9300 . ? C18 C19 1.427(9) . ? C18 H18 0.9300 . ? C19 C20 1.403(8) . ? C19 C23 1.410(7) . ? C20 C21 1.346(9) . ? C20 H20 0.9300 . ? C21 C22 1.387(8) . ? C21 H21 0.9300 . ? C22 N4 1.325(6) . ? C22 H22 0.9300 . ? C23 N4 1.356(6) . ? C23 C24 1.425(7) . ? C24 N3 1.351(6) . ? C25 N5 1.135(7) . ? O1 H1B 0.8499 . ? O1 H1A 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 Cu1 N2 94.21(19) . . ? C25 Cu1 N4 90.79(19) . . ? N2 Cu1 N4 174.92(17) . . ? C25 Cu1 N1 136.6(2) . . ? N2 Cu1 N1 80.72(15) . . ? N4 Cu1 N1 96.23(15) . . ? C25 Cu1 N3 123.00(19) . . ? N2 Cu1 N3 96.51(15) . . ? N4 Cu1 N3 79.98(16) . . ? N1 Cu1 N3 100.35(15) . . ? F1 B1 F2 108.5(8) . . ? F1 B1 F3 110.2(7) . . ? F2 B1 F3 111.1(8) . . ? F1 B1 F4 105.4(8) . . ? F2 B1 F4 108.9(7) . . ? F3 B1 F4 112.5(8) . . ? N1 C1 C2 122.1(5) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 120.2(5) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.3(5) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C12 116.8(4) . . ? C3 C4 C5 124.7(5) . . ? C12 C4 C5 118.5(4) . . ? C6 C5 C4 121.6(5) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C7 121.2(5) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C8 C7 C11 116.8(5) . . ? C8 C7 C6 124.6(5) . . ? C11 C7 C6 118.6(5) . . ? C9 C8 C7 119.5(5) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.6(5) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? N2 C10 C9 121.2(5) . . ? N2 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? N2 C11 C7 123.7(4) . . ? N2 C11 C12 115.9(4) . . ? C7 C11 C12 120.3(4) . . ? N1 C12 C4 122.5(4) . . ? N1 C12 C11 117.6(4) . . ? C4 C12 C11 119.8(4) . . ? N3 C13 C14 121.1(6) . . ? N3 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 121.1(6) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 119.9(6) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C24 C16 C15 115.9(5) . . ? C24 C16 C17 119.1(6) . . ? C15 C16 C17 125.0(6) . . ? C18 C17 C16 121.7(6) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C17 C18 C19 120.9(6) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C23 117.2(6) . . ? C20 C19 C18 124.4(6) . . ? C23 C19 C18 118.5(6) . . ? C21 C20 C19 119.9(6) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 120.0(6) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? N4 C22 C21 122.2(6) . . ? N4 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? N4 C23 C19 121.8(5) . . ? N4 C23 C24 117.5(4) . . ? C19 C23 C24 120.7(5) . . ? N3 C24 C16 123.7(5) . . ? N3 C24 C23 117.3(4) . . ? C16 C24 C23 119.0(5) . . ? N5 C25 Cu1 176.0(5) . . ? C1 N1 C12 118.1(4) . . ? C1 N1 Cu1 131.0(3) . . ? C12 N1 Cu1 110.9(3) . . ? C10 N2 C11 118.1(4) . . ? C10 N2 Cu1 127.1(3) . . ? C11 N2 Cu1 114.8(3) . . ? C13 N3 C24 118.4(5) . . ? C13 N3 Cu1 130.9(4) . . ? C24 N3 Cu1 110.7(3) . . ? C22 N4 C23 118.9(5) . . ? C22 N4 Cu1 126.8(4) . . ? C23 N4 Cu1 114.1(3) . . ? H1B O1 H1A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.097 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.081 data_11 _database_code_depnum_ccdc_archive 'CCDC 869867' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 Cu N4, F6 P' _chemical_formula_sum 'C24 H16 Cu F6 N4 P' _chemical_formula_weight 568.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' P P 0.1023 0.0942 '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 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 10.4565(15) _cell_length_b 14.390(2) _cell_length_c 7.5675(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.177(2) _cell_angle_gamma 90.00 _cell_volume 1129.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 933 _cell_measurement_theta_min 2.420 _cell_measurement_theta_max 19.653 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 1.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8972 _exptl_absorpt_correction_T_max 0.9165 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5635 _diffrn_reflns_av_R_equivalents 0.0689 _diffrn_reflns_av_sigmaI/netI 0.0987 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1997 _reflns_number_gt 1064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0311P)^2^] 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 1997 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0908 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 0.818 _refine_ls_restrained_S_all 0.818 _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 1.0000 0.21664(4) 0.2500 0.0584(3) Uani 1 2 d S . . C1 C 0.7658(4) 0.1080(3) 0.0675(5) 0.0589(11) Uani 1 1 d . . . H1 H 0.7280 0.1649 0.0339 0.071 Uiso 1 1 calc R . . C2 C 0.6948(4) 0.0275(3) 0.0247(5) 0.0626(12) Uani 1 1 d . . . H2 H 0.6113 0.0312 -0.0340 0.075 Uiso 1 1 calc R . . C3 C 0.7483(4) -0.0566(3) 0.0691(5) 0.0600(12) Uani 1 1 d . . . H3 H 0.7022 -0.1109 0.0405 0.072 Uiso 1 1 calc R . . C4 C 0.8739(4) -0.0605(2) 0.1587(5) 0.0472(10) Uani 1 1 d . . . C5 C 0.9401(3) -0.1452(2) 0.2090(6) 0.0634(12) Uani 1 1 d . . . H5 H 0.8982 -0.2016 0.1836 0.076 Uiso 1 1 calc R . . C6 C 0.9367(3) 0.0238(2) 0.2014(5) 0.0397(9) Uani 1 1 d . . . C7 C 1.2357(4) 0.3259(3) 0.1497(5) 0.0612(11) Uani 1 1 d . . . H7 H 1.2745 0.2692 0.1313 0.073 Uiso 1 1 calc R . . C8 C 1.3056(4) 0.4065(3) 0.1289(6) 0.0679(13) Uani 1 1 d . . . H8 H 1.3892 0.4032 0.0995 0.082 Uiso 1 1 calc R . . C9 C 1.2503(4) 0.4900(3) 0.1521(6) 0.0665(12) Uani 1 1 d . . . H9 H 1.2952 0.5445 0.1362 0.080 Uiso 1 1 calc R . . C10 C 1.1250(4) 0.4940(3) 0.2000(5) 0.0497(10) Uani 1 1 d . . . C11 C 1.0593(3) 0.5793(2) 0.2271(6) 0.0656(13) Uani 1 1 d . . . H11 H 1.1004 0.6355 0.2123 0.079 Uiso 1 1 calc R . . C12 C 1.0633(3) 0.4092(2) 0.2231(4) 0.0405(9) Uani 1 1 d . . . F1 F 0.34781(18) 0.26834(15) 0.7511(3) 0.0852(8) Uani 1 1 d . . . F2 F 0.4812(2) 0.2663(2) 0.5410(4) 0.1229(11) Uani 1 1 d . . . F3 F 0.5000 0.1597(2) 0.7500 0.1063(13) Uani 1 2 d S . . F4 F 0.5000 0.3767(2) 0.7500 0.1369(19) Uani 1 2 d S . . N1 N 0.8843(3) 0.10800(18) 0.1537(4) 0.0454(8) Uani 1 1 d . . . N2 N 1.1167(3) 0.32493(19) 0.1943(4) 0.0503(8) Uani 1 1 d . . . P1 P 0.5000 0.26863(11) 0.7500 0.0599(5) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0615(5) 0.0329(4) 0.0798(6) 0.000 0.0057(4) 0.000 C1 0.051(3) 0.056(3) 0.068(3) 0.008(2) 0.000(2) 0.000(2) C2 0.045(2) 0.076(3) 0.066(3) 0.005(3) 0.002(2) -0.016(2) C3 0.059(3) 0.058(3) 0.066(3) -0.003(2) 0.017(2) -0.020(2) C4 0.049(2) 0.041(2) 0.055(3) -0.004(2) 0.020(2) -0.011(2) C5 0.078(3) 0.034(2) 0.082(4) 0.000(2) 0.025(3) -0.0088(19) C6 0.042(2) 0.038(2) 0.042(2) 0.0004(18) 0.0150(18) -0.0022(17) C7 0.052(3) 0.058(3) 0.075(3) -0.014(2) 0.012(2) 0.002(2) C8 0.048(3) 0.083(4) 0.074(3) -0.011(3) 0.013(2) -0.014(3) C9 0.067(3) 0.063(3) 0.070(3) -0.012(2) 0.009(2) -0.029(2) C10 0.062(3) 0.040(2) 0.046(3) -0.0035(19) 0.006(2) -0.011(2) C11 0.096(4) 0.033(2) 0.066(3) -0.004(2) 0.006(3) -0.008(2) C12 0.047(2) 0.034(2) 0.041(2) -0.0026(18) 0.0037(19) -0.0057(17) F1 0.0409(13) 0.0784(17) 0.136(2) 0.0004(15) 0.0115(14) -0.0008(12) F2 0.093(2) 0.195(3) 0.079(2) 0.023(2) 0.0023(17) -0.036(2) F3 0.087(2) 0.049(2) 0.189(4) 0.000 0.040(3) 0.000 F4 0.054(2) 0.042(2) 0.304(6) 0.000 -0.018(3) 0.000 N1 0.0435(18) 0.0404(19) 0.052(2) 0.0041(16) 0.0043(16) 0.0033(15) N2 0.0471(19) 0.0386(19) 0.065(2) -0.0037(16) 0.0076(17) 0.0017(16) P1 0.0419(9) 0.0491(11) 0.0875(15) 0.000 0.0036(9) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.054(3) . ? Cu1 N1 2.054(3) 2_755 ? Cu1 N2 2.055(3) . ? Cu1 N2 2.055(3) 2_755 ? C1 N1 1.326(4) . ? C1 C2 1.393(5) . ? C1 H1 0.9300 . ? C2 C3 1.357(5) . ? C2 H2 0.9300 . ? C3 C4 1.401(5) . ? C3 H3 0.9300 . ? C4 C6 1.398(4) . ? C4 C5 1.430(4) . ? C5 C5 1.327(7) 2_755 ? C5 H5 0.9300 . ? C6 N1 1.360(4) . ? C6 C6 1.433(6) 2_755 ? C7 N2 1.329(4) . ? C7 C8 1.391(5) . ? C7 H7 0.9300 . ? C8 C9 1.353(5) . ? C8 H8 0.9300 . ? C9 C10 1.404(5) . ? C9 H9 0.9300 . ? C10 C12 1.401(4) . ? C10 C11 1.433(4) . ? C11 C11 1.329(7) 2_755 ? C11 H11 0.9300 . ? C12 N2 1.364(4) . ? C12 C12 1.432(6) 2_755 ? F1 P1 1.5924(19) . ? F2 P1 1.569(3) . ? F3 P1 1.567(3) . ? F4 P1 1.555(3) . ? P1 F2 1.569(3) 2_656 ? P1 F1 1.5924(19) 2_656 ? 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 N1 80.88(16) . 2_755 ? N1 Cu1 N2 147.45(12) . . ? N1 Cu1 N2 108.13(11) 2_755 . ? N1 Cu1 N2 108.13(11) . 2_755 ? N1 Cu1 N2 147.45(12) 2_755 2_755 ? N2 Cu1 N2 81.40(17) . 2_755 ? N1 C1 C2 123.5(4) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 119.5(4) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 119.2(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C6 C4 C3 117.5(3) . . ? C6 C4 C5 118.7(4) . . ? C3 C4 C5 123.8(3) . . ? C5 C5 C4 121.5(2) 2_755 . ? C5 C5 H5 119.3 2_755 . ? C4 C5 H5 119.3 . . ? N1 C6 C4 123.3(3) . . ? N1 C6 C6 116.89(19) . 2_755 ? C4 C6 C6 119.8(2) . 2_755 ? N2 C7 C8 124.0(4) . . ? N2 C7 H7 118.0 . . ? C8 C7 H7 118.0 . . ? C9 C8 C7 119.1(4) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 119.9(4) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C12 C10 C9 117.1(4) . . ? C12 C10 C11 119.5(3) . . ? C9 C10 C11 123.4(4) . . ? C11 C11 C10 121.1(2) 2_755 . ? C11 C11 H11 119.5 2_755 . ? C10 C11 H11 119.5 . . ? N2 C12 C10 123.4(3) . . ? N2 C12 C12 117.20(18) . 2_755 ? C10 C12 C12 119.4(2) . 2_755 ? C1 N1 C6 116.9(3) . . ? C1 N1 Cu1 130.3(3) . . ? C6 N1 Cu1 112.6(2) . . ? C7 N2 C12 116.5(3) . . ? C7 N2 Cu1 131.2(3) . . ? C12 N2 Cu1 112.0(2) . . ? F4 P1 F3 180.000(1) . . ? F4 P1 F2 91.23(13) . 2_656 ? F3 P1 F2 88.77(13) . 2_656 ? F4 P1 F2 91.23(13) . . ? F3 P1 F2 88.77(13) . . ? F2 P1 F2 177.5(3) 2_656 . ? F4 P1 F1 90.15(10) . 2_656 ? F3 P1 F1 89.85(10) . 2_656 ? F2 P1 F1 90.34(13) 2_656 2_656 ? F2 P1 F1 89.66(13) . 2_656 ? F4 P1 F1 90.15(10) . . ? F3 P1 F1 89.85(10) . . ? F2 P1 F1 89.66(13) 2_656 . ? F2 P1 F1 90.34(13) . . ? F1 P1 F1 179.7(2) 2_656 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -1.2(6) . . . . ? C1 C2 C3 C4 0.5(6) . . . . ? C2 C3 C4 C6 1.5(5) . . . . ? C2 C3 C4 C5 -178.9(4) . . . . ? C6 C4 C5 C5 -1.5(7) . . . 2_755 ? C3 C4 C5 C5 178.9(5) . . . 2_755 ? C3 C4 C6 N1 -3.0(5) . . . . ? C5 C4 C6 N1 177.4(3) . . . . ? C3 C4 C6 C6 177.7(4) . . . 2_755 ? C5 C4 C6 C6 -1.9(6) . . . 2_755 ? N2 C7 C8 C9 -1.1(6) . . . . ? C7 C8 C9 C10 1.3(6) . . . . ? C8 C9 C10 C12 0.5(6) . . . . ? C8 C9 C10 C11 -180.0(4) . . . . ? C12 C10 C11 C11 -0.3(7) . . . 2_755 ? C9 C10 C11 C11 -179.8(5) . . . 2_755 ? C9 C10 C12 N2 -2.8(5) . . . . ? C11 C10 C12 N2 177.7(3) . . . . ? C9 C10 C12 C12 178.3(4) . . . 2_755 ? C11 C10 C12 C12 -1.3(6) . . . 2_755 ? C2 C1 N1 C6 -0.1(5) . . . . ? C2 C1 N1 Cu1 -173.9(3) . . . . ? C4 C6 N1 C1 2.3(5) . . . . ? C6 C6 N1 C1 -178.4(4) 2_755 . . . ? C4 C6 N1 Cu1 177.1(3) . . . . ? C6 C6 N1 Cu1 -3.6(5) 2_755 . . . ? N1 Cu1 N1 C1 175.2(4) 2_755 . . . ? N2 Cu1 N1 C1 -75.3(4) . . . . ? N2 Cu1 N1 C1 27.5(4) 2_755 . . . ? N1 Cu1 N1 C6 1.27(16) 2_755 . . . ? N2 Cu1 N1 C6 110.8(3) . . . . ? N2 Cu1 N1 C6 -146.5(2) 2_755 . . . ? C8 C7 N2 C12 -1.0(5) . . . . ? C8 C7 N2 Cu1 -175.0(3) . . . . ? C10 C12 N2 C7 3.0(5) . . . . ? C12 C12 N2 C7 -178.0(4) 2_755 . . . ? C10 C12 N2 Cu1 178.1(3) . . . . ? C12 C12 N2 Cu1 -2.9(5) 2_755 . . . ? N1 Cu1 N2 C7 -74.5(4) . . . . ? N1 Cu1 N2 C7 27.3(4) 2_755 . . . ? N2 Cu1 N2 C7 175.2(4) 2_755 . . . ? N1 Cu1 N2 C12 111.4(3) . . . . ? N1 Cu1 N2 C12 -146.9(2) 2_755 . . . ? N2 Cu1 N2 C12 1.03(17) 2_755 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.389 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.067 data_12 _database_code_depnum_ccdc_archive 'CCDC 869868' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C80 H92 Cu2 N8, 2(Cl O4)' _chemical_formula_sum 'C80 H92 Cl2 Cu2 N8 O8' _chemical_formula_weight 1491.60 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3756(13) _cell_length_b 13.2455(14) _cell_length_c 14.4389(16) _cell_angle_alpha 104.478(2) _cell_angle_beta 109.096(2) _cell_angle_gamma 92.224(2) _cell_volume 1973.2(4) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2606 _cell_measurement_theta_min 2.327 _cell_measurement_theta_max 20.937 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.664 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9245 _exptl_absorpt_correction_T_max 0.9365 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11119 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6897 _reflns_number_gt 3395 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1731P)^2^] 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 6897 _refine_ls_number_parameters 554 _refine_ls_number_restraints 166 _refine_ls_R_factor_all 0.1327 _refine_ls_R_factor_gt 0.0859 _refine_ls_wR_factor_ref 0.2562 _refine_ls_wR_factor_gt 0.2345 _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_restrained_S_all 0.920 _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 0.64498(6) 0.79834(5) 0.30452(5) 0.0914(4) Uani 1 1 d . D . C1 C 0.3813(7) 0.7022(5) 0.1544(6) 0.127(2) Uani 1 1 d D D . C2 C 0.2637(9) 0.6405(7) 0.1286(8) 0.166(4) Uani 1 1 d . . . H2 H 0.2035 0.6283 0.0639 0.199 Uiso 1 1 calc R . . C3 C 0.2400(8) 0.5994(7) 0.1992(10) 0.170(4) Uani 1 1 d . . . H3 H 0.1629 0.5596 0.1821 0.204 Uiso 1 1 calc R . . C4 C 0.3278(8) 0.6156(5) 0.2958(8) 0.136(3) Uani 1 1 d . . . C5 C 0.3179(10) 0.5755(7) 0.3785(11) 0.164(4) Uani 1 1 d . . . H5 H 0.2449 0.5322 0.3660 0.197 Uiso 1 1 calc R . . C6 C 0.4064(12) 0.5966(8) 0.4713(10) 0.160(3) Uani 1 1 d U . . H6 H 0.3923 0.5691 0.5206 0.192 Uiso 1 1 calc R . . C7 C 0.5223(9) 0.6610(6) 0.4957(8) 0.133(2) Uani 1 1 d U . . C8 C 0.6215(13) 0.6829(8) 0.5874(7) 0.154(4) Uani 1 1 d . . . H8 H 0.6145 0.6573 0.6401 0.185 Uiso 1 1 calc R . . C9 C 0.7280(12) 0.7413(7) 0.6001(6) 0.144(3) Uani 1 1 d . . . H9 H 0.7942 0.7567 0.6620 0.173 Uiso 1 1 calc R . . C10 C 0.7398(7) 0.7783(5) 0.5225(5) 0.114(2) Uani 1 1 d . D . C11 C 0.5375(6) 0.7000(4) 0.4157(5) 0.0958(16) Uani 1 1 d . D . C12 C 0.4428(6) 0.6799(4) 0.3179(5) 0.0983(17) Uani 1 1 d . D . C13 C 0.4158(9) 0.7449(7) 0.0786(6) 0.161(3) Uani 1 1 d DU . . C17 C 0.8578(8) 0.8437(7) 0.5365(6) 0.151(3) Uani 1 1 d DU . . H17A H 0.8800 0.8997 0.5996 0.181 Uiso 1 1 calc R A 1 H17B H 0.8420 0.8761 0.4810 0.181 Uiso 1 1 calc R A 1 C21 C 0.7878(8) 0.6456(6) 0.1981(5) 0.121(2) Uani 1 1 d . D . C22 C 0.8600(10) 0.6214(8) 0.1330(7) 0.162(4) Uani 1 1 d . . . H22 H 0.8784 0.5533 0.1129 0.194 Uiso 1 1 calc R . . C23 C 0.9023(10) 0.7011(10) 0.0999(7) 0.163(4) Uani 1 1 d . . . H23 H 0.9507 0.6861 0.0584 0.196 Uiso 1 1 calc R . . C24 C 0.8739(8) 0.8008(7) 0.1275(6) 0.134(3) Uani 1 1 d . . . C25 C 0.9152(10) 0.8858(11) 0.0980(7) 0.171(4) Uani 1 1 d . . . H25 H 0.9618 0.8742 0.0550 0.205 Uiso 1 1 calc R . . C26 C 0.8879(10) 0.9846(9) 0.1317(8) 0.154(3) Uani 1 1 d . . . H26 H 0.9217 1.0406 0.1162 0.185 Uiso 1 1 calc R . . C27 C 0.8110(8) 1.0016(7) 0.1879(6) 0.123(2) Uani 1 1 d . . . C28 C 0.7714(9) 1.1014(6) 0.2216(8) 0.143(3) Uani 1 1 d . . . H28 H 0.7958 1.1583 0.2021 0.172 Uiso 1 1 calc R . . C29 C 0.7018(9) 1.1146(6) 0.2789(7) 0.136(3) Uani 1 1 d . . . H29 H 0.6787 1.1806 0.3001 0.163 Uiso 1 1 calc R . . C30 C 0.6616(6) 1.0313(5) 0.3087(5) 0.1078(19) Uani 1 1 d . D . C31 C 0.7661(6) 0.9207(5) 0.2213(5) 0.0989(17) Uani 1 1 d . D . C32 C 0.8007(6) 0.8181(6) 0.1915(4) 0.1053(18) Uani 1 1 d . D . C33 C 0.7391(9) 0.5612(5) 0.2376(6) 0.139(3) Uani 1 1 d D . . H33A H 0.7267 0.4920 0.1902 0.167 Uiso 1 1 calc R B 1 H33B H 0.6604 0.5757 0.2473 0.167 Uiso 1 1 calc R B 1 C37 C 0.5799(9) 1.0463(6) 0.3729(6) 0.139(3) Uani 1 1 d DU . . H37A H 0.6054 1.1152 0.4220 0.167 Uiso 1 1 calc R C 1 H37B H 0.5908 0.9939 0.4103 0.167 Uiso 1 1 calc R C 1 Cl1 Cl 0.98809(18) 0.32535(15) 0.15755(14) 0.1126(6) Uani 1 1 d . . . N1 N 0.4663(4) 0.7206(3) 0.2476(4) 0.0979(13) Uani 1 1 d . . . N2 N 0.6488(5) 0.7610(3) 0.4326(3) 0.0891(12) Uani 1 1 d . . . N3 N 0.7587(5) 0.7420(4) 0.2241(3) 0.0978(13) Uani 1 1 d . . . N4 N 0.6935(4) 0.9348(3) 0.2800(3) 0.0886(12) Uani 1 1 d . . . O1 O 1.0091(16) 0.2351(8) 0.1302(11) 0.352(9) Uani 1 1 d . . . O2 O 1.0364(11) 0.3808(11) 0.2608(6) 0.303(6) Uani 1 1 d . . . O3 O 0.9905(7) 0.3907(5) 0.0957(5) 0.168(2) Uani 1 1 d . . . O4 O 0.8584(7) 0.3167(8) 0.1526(7) 0.234(4) Uani 1 1 d . . . C14 C 0.4757(15) 0.6666(11) 0.0069(10) 0.143(5) Uani 0.540(3) 1 d PD D 1 H14A H 0.5478 0.6436 0.0507 0.171 Uiso 0.540(3) 1 calc PR D 1 H14B H 0.4145 0.6048 -0.0322 0.171 Uiso 0.540(3) 1 calc PR D 1 C15 C 0.518(2) 0.7102(14) -0.0690(12) 0.187(8) Uani 0.540(3) 1 d PD D 1 H15A H 0.4447 0.7246 -0.1186 0.225 Uiso 0.540(3) 1 calc PR D 1 H15B H 0.5716 0.7768 -0.0314 0.225 Uiso 0.540(3) 1 calc PR D 1 C16 C 0.5868(19) 0.6423(16) -0.1246(15) 0.178(5) Uani 0.540(3) 1 d PD D 1 H16A H 0.6609 0.6282 -0.0765 0.268 Uiso 0.540(3) 1 d PR D 1 H16B H 0.6102 0.6771 -0.1681 0.268 Uiso 0.540(3) 1 d PR D 1 H16C H 0.5342 0.5773 -0.1653 0.268 Uiso 0.540(3) 1 d PR D 1 C18 C 0.9676(16) 0.7828(15) 0.5396(15) 0.183(5) Uani 0.540(3) 1 d PDU D 1 H18A H 1.0084 0.8115 0.5006 0.220 Uiso 0.540(3) 1 calc PR D 1 H18B H 1.0236 0.8083 0.6100 0.220 Uiso 0.540(3) 1 calc PR D 1 C19 C 0.979(2) 0.6745(16) 0.513(2) 0.249(13) Uani 0.540(3) 1 d PDU D 1 H19A H 0.9214 0.6467 0.4433 0.298 Uiso 0.540(3) 1 calc PR D 1 H19B H 0.9439 0.6449 0.5547 0.298 Uiso 0.540(3) 1 calc PR D 1 C20 C 1.098(2) 0.623(2) 0.516(2) 0.248(10) Uani 0.540(3) 1 d PDU . 1 H20A H 1.0801 0.5481 0.4934 0.372 Uiso 0.540(3) 1 d PR D 1 H20C H 1.1356 0.6476 0.4737 0.372 Uiso 0.540(3) 1 d PR D 1 H20B H 1.1537 0.6452 0.5855 0.372 Uiso 0.540(3) 1 d PR D 1 C34 C 0.8427(16) 0.5679(14) 0.3400(13) 0.178(5) Uani 0.540(3) 1 d PDU D 1 H34A H 0.8744 0.6412 0.3760 0.214 Uiso 0.540(3) 1 calc PR D 1 H34B H 0.9116 0.5334 0.3269 0.214 Uiso 0.540(3) 1 calc PR D 1 C35 C 0.794(2) 0.5148(15) 0.4101(16) 0.198(5) Uani 0.540(3) 1 d PDU D 1 H35A H 0.8457 0.5453 0.4811 0.238 Uiso 0.540(3) 1 calc PR D 1 H35B H 0.7083 0.5281 0.4023 0.238 Uiso 0.540(3) 1 calc PR D 1 C36 C 0.798(2) 0.4001(15) 0.3813(18) 0.204(6) Uani 0.540(3) 1 d PDU . 1 H36C H 0.7691 0.3639 0.4211 0.306 Uiso 0.540(3) 1 d PR D 1 H36B H 0.7446 0.3751 0.3110 0.306 Uiso 0.540(3) 1 d PR D 1 H36A H 0.8825 0.3872 0.3872 0.306 Uiso 0.540(3) 1 d PR D 1 C38 C 0.4439(18) 1.0371(19) 0.3088(15) 0.195(9) Uani 0.540(3) 1 d PDU D 1 H38A H 0.4079 0.9708 0.3116 0.234 Uiso 0.540(3) 1 calc PR D 1 H38B H 0.4118 1.0910 0.3497 0.234 Uiso 0.540(3) 1 calc PR D 1 C39 C 0.3800(19) 1.040(2) 0.2089(16) 0.234(12) Uani 0.540(3) 1 d PDU D 1 H39A H 0.4052 0.9846 0.1638 0.281 Uiso 0.540(3) 1 calc PR D 1 H39B H 0.4102 1.1062 0.2021 0.281 Uiso 0.540(3) 1 calc PR D 1 C40 C 0.2380(18) 1.0284(19) 0.1686(19) 0.199(8) Uani 0.540(3) 1 d PDU D 1 H40A H 0.2097 1.0087 0.2182 0.299 Uiso 0.540(3) 1 d PR D 1 H40B H 0.2017 0.9762 0.1040 0.299 Uiso 0.540(3) 1 d PR D 1 H40C H 0.2126 1.0953 0.1618 0.299 Uiso 0.540(3) 1 d PR D 1 C14' C 0.417(3) 0.8632(13) 0.087(2) 0.228(10) Uani 0.460(3) 1 d PDU D 2 H14C H 0.5016 0.8989 0.1245 0.273 Uiso 0.460(3) 1 calc PR D 2 H14D H 0.3921 0.8727 0.0188 0.273 Uiso 0.460(3) 1 calc PR D 2 C15' C 0.333(2) 0.9111(18) 0.1375(18) 0.178(5) Uani 0.460(3) 1 d PDU D 2 H15C H 0.3701 0.9140 0.2090 0.214 Uiso 0.460(3) 1 calc PR D 2 H15D H 0.2555 0.8626 0.1104 0.214 Uiso 0.460(3) 1 calc PR D 2 C16' C 0.294(3) 1.023(2) 0.133(3) 0.228(10) Uani 0.460(3) 1 d PDU D 2 H16E H 0.2055 1.0177 0.1213 0.342 Uiso 0.460(3) 1 d PR D 2 H16D H 0.3108 1.0492 0.0819 0.342 Uiso 0.460(3) 1 d PR D 2 H16F H 0.3386 1.0703 0.1994 0.342 Uiso 0.460(3) 1 d PR D 2 C18' C 0.839(3) 0.9563(15) 0.598(2) 0.230(10) Uani 0.460(3) 1 d PDU D 2 H18C H 0.7489 0.9584 0.5735 0.276 Uiso 0.460(3) 1 calc PR D 2 H18D H 0.8599 0.9529 0.6682 0.276 Uiso 0.460(3) 1 calc PR D 2 C19' C 0.895(3) 1.061(2) 0.607(2) 0.236(10) Uani 0.460(3) 1 d PDU D 2 H19C H 0.8875 1.0648 0.5387 0.283 Uiso 0.460(3) 1 calc PR D 2 H19D H 0.9840 1.0691 0.6461 0.283 Uiso 0.460(3) 1 calc PR D 2 C20' C 0.836(3) 1.1556(18) 0.658(2) 0.227(13) Uani 0.460(3) 1 d PDU D 2 H20D H 0.8235 1.1444 0.7172 0.341 Uiso 0.460(3) 1 d PR D 2 H20F H 0.7570 1.1644 0.6109 0.341 Uiso 0.460(3) 1 d PR D 2 H20E H 0.8946 1.2175 0.6769 0.341 Uiso 0.460(3) 1 d PR D 2 C34' C 0.6025(14) 0.4927(10) 0.1588(10) 0.119(5) Uani 0.460(3) 1 d PD D 2 H34C H 0.5465 0.5438 0.1410 0.143 Uiso 0.460(3) 1 calc PR D 2 H34D H 0.6161 0.4561 0.0968 0.143 Uiso 0.460(3) 1 calc PR D 2 C35' C 0.527(3) 0.409(2) 0.186(2) 0.239(11) Uani 0.460(3) 1 d PDU D 2 H35C H 0.4401 0.3984 0.1404 0.287 Uiso 0.460(3) 1 calc PR D 2 H35D H 0.5600 0.3431 0.1723 0.287 Uiso 0.460(3) 1 calc PR D 2 C36' C 0.528(4) 0.438(3) 0.297(2) 0.308(13) Uani 0.460(3) 1 d PDU D 2 H36E H 0.5280 0.3750 0.3193 0.462 Uiso 0.460(3) 1 d PR D 2 H36F H 0.4546 0.4698 0.2999 0.462 Uiso 0.460(3) 1 d PR D 2 H36D H 0.6018 0.4858 0.3411 0.462 Uiso 0.460(3) 1 d PR D 2 C38' C 0.6615(18) 1.0754(17) 0.4916(12) 0.167(5) Uani 0.460(3) 1 d PDU D 2 H38C H 0.6099 1.1084 0.5293 0.201 Uiso 0.460(3) 1 calc PR D 2 H38D H 0.6790 1.0101 0.5092 0.201 Uiso 0.460(3) 1 calc PR D 2 C39' C 0.786(2) 1.1469(18) 0.5299(15) 0.199(8) Uani 0.460(3) 1 d PDU D 2 H39D H 0.7665 1.2175 0.5291 0.238 Uiso 0.460(3) 1 calc PR D 2 H39C H 0.8274 1.1245 0.4809 0.238 Uiso 0.460(3) 1 calc PR D 2 C40' C 0.880(2) 1.153(3) 0.6370(19) 0.187(10) Uani 0.460(3) 1 d PDU D 2 H40D H 0.8712 1.2133 0.6865 0.281 Uiso 0.460(3) 1 d PR D 2 H40E H 0.9639 1.1606 0.6351 0.281 Uiso 0.460(3) 1 d PR D 2 H40F H 0.8661 1.0906 0.6556 0.281 Uiso 0.460(3) 1 d PR D 2 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 0.0955(6) 0.0807(5) 0.0939(5) 0.0340(4) 0.0214(4) 0.0014(3) C1 0.116(5) 0.092(4) 0.127(5) 0.035(4) -0.019(5) -0.010(4) C2 0.122(7) 0.132(7) 0.179(8) 0.054(6) -0.035(6) -0.016(5) C3 0.091(5) 0.113(6) 0.237(11) 0.032(7) -0.018(7) -0.011(4) C4 0.117(6) 0.089(4) 0.223(9) 0.056(5) 0.075(7) 0.019(4) C5 0.136(8) 0.131(7) 0.281(13) 0.098(8) 0.115(9) 0.018(5) C6 0.180(8) 0.140(6) 0.223(8) 0.088(6) 0.121(7) 0.049(6) C7 0.166(7) 0.110(5) 0.182(7) 0.073(5) 0.111(6) 0.055(5) C8 0.236(13) 0.156(8) 0.109(6) 0.066(6) 0.083(8) 0.088(8) C9 0.213(11) 0.124(6) 0.100(5) 0.051(5) 0.044(6) 0.054(6) C10 0.136(6) 0.094(4) 0.094(4) 0.024(3) 0.014(4) 0.030(4) C11 0.111(5) 0.074(3) 0.119(4) 0.039(3) 0.051(4) 0.029(3) C12 0.090(4) 0.077(4) 0.131(5) 0.038(3) 0.034(4) 0.011(3) C13 0.173(8) 0.153(7) 0.106(5) 0.045(5) -0.020(5) 0.000(6) C17 0.136(6) 0.149(6) 0.131(5) 0.049(4) -0.008(5) 0.007(5) C21 0.145(6) 0.120(6) 0.099(4) 0.032(4) 0.037(4) 0.039(5) C22 0.198(10) 0.154(8) 0.143(7) 0.027(6) 0.077(7) 0.085(7) C23 0.192(10) 0.213(11) 0.125(6) 0.073(7) 0.085(6) 0.069(8) C24 0.157(7) 0.142(7) 0.129(6) 0.061(5) 0.062(5) 0.052(5) C25 0.177(9) 0.250(13) 0.149(7) 0.117(9) 0.090(7) 0.030(8) C26 0.157(8) 0.172(9) 0.162(8) 0.097(7) 0.056(7) 0.010(6) C27 0.125(6) 0.136(7) 0.117(5) 0.063(4) 0.033(4) -0.008(4) C28 0.158(8) 0.100(6) 0.177(8) 0.081(5) 0.035(6) 0.004(5) C29 0.147(7) 0.081(5) 0.169(7) 0.048(5) 0.034(6) 0.005(4) C30 0.116(5) 0.073(4) 0.118(4) 0.031(3) 0.016(4) 0.005(3) C31 0.109(5) 0.084(4) 0.091(4) 0.037(3) 0.010(3) 0.001(3) C32 0.115(5) 0.123(5) 0.087(4) 0.044(4) 0.035(4) 0.022(4) C33 0.195(9) 0.092(5) 0.138(6) 0.040(4) 0.061(6) 0.035(5) C37 0.166(8) 0.107(5) 0.146(6) 0.032(4) 0.057(6) 0.032(5) Cl1 0.1178(14) 0.1148(13) 0.1113(12) 0.0523(10) 0.0333(10) 0.0055(9) N1 0.083(3) 0.080(3) 0.110(3) 0.035(2) 0.002(3) -0.003(2) N2 0.101(3) 0.077(3) 0.082(3) 0.027(2) 0.018(3) 0.018(2) N3 0.121(4) 0.082(3) 0.094(3) 0.033(2) 0.035(3) 0.021(3) N4 0.091(3) 0.079(3) 0.089(3) 0.028(2) 0.021(3) -0.002(2) O1 0.61(2) 0.182(8) 0.460(18) 0.158(10) 0.372(19) 0.180(12) O2 0.269(11) 0.467(17) 0.145(6) 0.075(8) 0.044(7) 0.048(11) O3 0.210(6) 0.154(5) 0.166(5) 0.083(4) 0.071(5) 0.015(4) O4 0.140(6) 0.297(10) 0.287(10) 0.145(8) 0.060(6) 0.002(6) C14 0.167(14) 0.118(10) 0.114(9) 0.019(8) 0.021(9) 0.007(9) C15 0.26(2) 0.183(17) 0.122(11) 0.027(11) 0.081(14) -0.011(15) C16 0.179(8) 0.191(9) 0.176(8) 0.057(7) 0.072(7) 0.020(7) C18 0.167(8) 0.175(8) 0.179(8) 0.045(7) 0.027(7) 0.006(7) C19 0.192(19) 0.18(2) 0.36(4) -0.01(2) 0.15(2) -0.006(13) C20 0.225(12) 0.256(14) 0.261(14) 0.049(9) 0.097(10) 0.051(9) C34 0.184(11) 0.154(9) 0.232(11) 0.107(8) 0.081(9) 0.017(8) C35 0.207(8) 0.185(8) 0.223(8) 0.086(7) 0.081(7) 0.018(6) C36 0.210(9) 0.195(9) 0.221(9) 0.065(7) 0.088(7) 0.020(7) C38 0.140(16) 0.31(3) 0.198(15) 0.126(19) 0.094(13) 0.094(16) C39 0.157(12) 0.32(3) 0.174(15) 0.040(19) 0.013(15) 0.028(19) C40 0.173(10) 0.209(12) 0.211(12) 0.058(9) 0.060(9) 0.025(9) C14' 0.236(14) 0.202(10) 0.229(14) 0.065(10) 0.055(9) 0.027(10) C15' 0.179(8) 0.191(9) 0.176(8) 0.057(7) 0.072(7) 0.020(7) C16' 0.227(11) 0.227(11) 0.225(11) 0.061(6) 0.072(6) 0.029(6) C18' 0.240(14) 0.195(11) 0.232(13) 0.056(8) 0.055(10) 0.031(10) C19' 0.238(13) 0.226(13) 0.219(13) 0.043(9) 0.060(9) 0.040(9) C20' 0.224(19) 0.187(17) 0.185(17) -0.038(14) 0.021(16) 0.081(15) C34' 0.171(15) 0.082(9) 0.123(10) 0.037(8) 0.069(11) 0.009(8) C35' 0.255(14) 0.237(14) 0.241(14) 0.075(9) 0.100(9) 0.032(9) C36' 0.302(15) 0.295(15) 0.313(16) 0.087(10) 0.087(10) 0.037(10) C38' 0.176(11) 0.159(10) 0.155(9) 0.015(9) 0.064(9) 0.024(9) C39' 0.229(18) 0.182(15) 0.140(13) 0.005(12) 0.039(13) 0.005(14) C40' 0.192(13) 0.174(12) 0.175(12) 0.030(9) 0.049(9) 0.034(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 2.017(4) . ? Cu1 N2 2.018(4) . ? Cu1 N1 2.047(5) . ? Cu1 N3 2.050(5) . ? C1 N1 1.332(8) . ? C1 C2 1.426(11) . ? C1 C13 1.498(12) . ? C2 C3 1.361(14) . ? C2 H2 0.9300 . ? C3 C4 1.383(13) . ? C3 H3 0.9300 . ? C4 C12 1.429(9) . ? C4 C5 1.456(13) . ? C5 C6 1.339(14) . ? C5 H5 0.9300 . ? C6 C7 1.431(13) . ? C6 H6 0.9300 . ? C7 C8 1.385(13) . ? C7 C11 1.433(10) . ? C8 C9 1.346(13) . ? C8 H8 0.9300 . ? C9 C10 1.372(11) . ? C9 H9 0.9300 . ? C10 N2 1.327(7) . ? C10 C17 1.496(11) . ? C11 N2 1.391(7) . ? C11 C12 1.421(9) . ? C12 N1 1.352(8) . ? C13 C14' 1.541(14) . ? C13 C14 1.611(13) . ? C17 C18 1.507(15) . ? C17 C18' 1.599(16) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C21 N3 1.325(8) . ? C21 C22 1.426(11) . ? C21 C33 1.537(10) . ? C22 C23 1.392(13) . ? C22 H22 0.9300 . ? C23 C24 1.366(12) . ? C23 H23 0.9300 . ? C24 C25 1.414(12) . ? C24 C32 1.418(9) . ? C25 C26 1.362(13) . ? C25 H25 0.9300 . ? C26 C27 1.365(11) . ? C26 H26 0.9300 . ? C27 C31 1.421(9) . ? C27 C28 1.434(11) . ? C28 C29 1.307(11) . ? C28 H28 0.9300 . ? C29 C30 1.392(10) . ? C29 H29 0.9300 . ? C30 N4 1.344(7) . ? C30 C37 1.499(10) . ? C31 N4 1.352(7) . ? C31 C32 1.430(9) . ? C32 N3 1.347(8) . ? C33 C34 1.539(15) . ? C33 C34' 1.658(14) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C37 C38 1.50(2) . ? C37 C38' 1.597(15) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? Cl1 O1 1.220(8) . ? Cl1 O3 1.395(5) . ? Cl1 O2 1.396(9) . ? Cl1 O4 1.452(8) . ? C14 C15 1.554(15) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.469(16) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C18 C19 1.411(16) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.524(17) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C36 1.68(3) 2_766 ? C20 H20A 0.9600 . ? C20 H20C 0.9602 . ? C20 H20B 0.9599 . ? C34 C35 1.589(16) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.479(17) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C20 1.68(3) 2_766 ? C36 H36C 0.9599 . ? C36 H36B 0.9600 . ? C36 H36A 0.9600 . ? C38 C39 1.398(17) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.514(17) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C39 H16F 0.6352 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C40 H16E 0.6363 . ? C40 H16F 1.1449 . ? C14' C15' 1.461(16) . ? C14' H14C 0.9700 . ? C14' H14D 0.9700 . ? C15' C16' 1.572(18) . ? C15' H15C 0.9700 . ? C15' H15D 0.9700 . ? C16' H40B 1.0909 . ? C16' H40C 1.4357 . ? C16' H16E 0.9600 . ? C16' H16D 0.9600 . ? C16' H16F 0.9600 . ? C18' C19' 1.464(18) . ? C18' H18C 0.9700 . ? C18' H18D 0.9700 . ? C19' C20' 1.583(18) . ? C19' H19C 0.9700 . ? C19' H19D 0.9700 . ? C19' H40E 1.4014 . ? C19' H40F 0.8886 . ? C20' H20D 0.9600 . ? C20' H20F 0.9600 . ? C20' H20E 0.9600 . ? C20' H40D 0.7926 . ? C20' H40F 0.9378 . ? C34' C35' 1.575(18) . ? C34' H34C 0.9700 . ? C34' H34D 0.9700 . ? C35' C36' 1.549(18) . ? C35' H35C 0.9700 . ? C35' H35D 0.9700 . ? C36' H36E 0.9600 . ? C36' H36F 0.9600 . ? C36' H36D 0.9600 . ? C38' C39' 1.522(17) . ? C38' H38C 0.9700 . ? C38' H38D 0.9700 . ? C39' C40' 1.549(18) . ? C39' H20F 1.2829 . ? C39' H39D 0.9700 . ? C39' H39C 0.9700 . ? C40' H20D 1.5256 . ? C40' H20F 1.3539 . ? C40' H20E 0.8734 . ? C40' H40D 0.9600 . ? C40' H40E 0.9600 . ? C40' H40F 0.9600 . ? 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 132.03(18) . . ? N4 Cu1 N1 124.46(18) . . ? N2 Cu1 N1 83.3(2) . . ? N4 Cu1 N3 82.8(2) . . ? N2 Cu1 N3 123.11(18) . . ? N1 Cu1 N3 115.3(2) . . ? N1 C1 C2 119.8(8) . . ? N1 C1 C13 117.9(6) . . ? C2 C1 C13 122.3(8) . . ? C3 C2 C1 119.7(8) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 121.5(8) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C4 C12 116.3(8) . . ? C3 C4 C5 128.1(9) . . ? C12 C4 C5 115.6(9) . . ? C6 C5 C4 124.7(9) . . ? C6 C5 H5 117.7 . . ? C4 C5 H5 117.7 . . ? C5 C6 C7 120.9(10) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 125.1(10) . . ? C8 C7 C11 118.5(9) . . ? C6 C7 C11 116.3(10) . . ? C9 C8 C7 119.7(9) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.6(9) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? N2 C10 C9 123.2(8) . . ? N2 C10 C17 116.0(7) . . ? C9 C10 C17 120.7(8) . . ? N2 C11 C12 117.2(5) . . ? N2 C11 C7 119.8(7) . . ? C12 C11 C7 123.0(7) . . ? N1 C12 C11 118.4(5) . . ? N1 C12 C4 122.1(7) . . ? C11 C12 C4 119.4(7) . . ? C1 C13 C14' 119.6(11) . . ? C1 C13 C14 115.9(8) . . ? C14' C13 C14 123.4(12) . . ? C10 C17 C18 113.9(10) . . ? C10 C17 C18' 101.2(13) . . ? C18 C17 C18' 135.3(15) . . ? C10 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? C18' C17 H17A 30.0 . . ? C10 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? C18' C17 H17B 83.5 . . ? H17A C17 H17B 107.7 . . ? N3 C21 C22 120.3(8) . . ? N3 C21 C33 118.2(6) . . ? C22 C21 C33 121.5(8) . . ? C23 C22 C21 119.1(8) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C24 C23 C22 120.9(8) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 124.0(9) . . ? C23 C24 C32 116.5(8) . . ? C25 C24 C32 119.5(8) . . ? C26 C25 C24 121.1(8) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C27 120.2(8) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C26 C27 C31 122.1(8) . . ? C26 C27 C28 124.2(8) . . ? C31 C27 C28 113.8(8) . . ? C29 C28 C27 121.8(7) . . ? C29 C28 H28 119.1 . . ? C27 C28 H28 119.1 . . ? C28 C29 C30 121.1(8) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? N4 C30 C29 121.2(7) . . ? N4 C30 C37 117.9(6) . . ? C29 C30 C37 120.9(7) . . ? N4 C31 C27 124.1(7) . . ? N4 C31 C32 118.1(5) . . ? C27 C31 C32 117.9(7) . . ? N3 C32 C24 123.5(6) . . ? N3 C32 C31 117.6(6) . . ? C24 C32 C31 118.9(7) . . ? C21 C33 C34 104.5(8) . . ? C21 C33 C34' 114.0(7) . . ? C34 C33 C34' 141.5(9) . . ? C21 C33 H33A 110.8 . . ? C34 C33 H33A 110.8 . . ? C34' C33 H33A 53.7 . . ? C21 C33 H33B 110.8 . . ? C34 C33 H33B 110.8 . . ? C34' C33 H33B 57.5 . . ? H33A C33 H33B 108.9 . . ? C30 C37 C38 111.5(9) . . ? C30 C37 C38' 111.4(10) . . ? C38 C37 C38' 136.9(12) . . ? C30 C37 H37A 109.3 . . ? C38 C37 H37A 109.3 . . ? C38' C37 H37A 51.6 . . ? C30 C37 H37B 109.3 . . ? C38 C37 H37B 109.3 . . ? C38' C37 H37B 58.4 . . ? H37A C37 H37B 108.0 . . ? O1 Cl1 O3 117.6(6) . . ? O1 Cl1 O2 119.7(9) . . ? O3 Cl1 O2 111.4(6) . . ? O1 Cl1 O4 105.5(8) . . ? O3 Cl1 O4 103.3(5) . . ? O2 Cl1 O4 94.7(6) . . ? C1 N1 C12 120.6(6) . . ? C1 N1 Cu1 128.9(5) . . ? C12 N1 Cu1 110.4(4) . . ? C10 N2 C11 118.2(6) . . ? C10 N2 Cu1 131.1(5) . . ? C11 N2 Cu1 110.5(4) . . ? C21 N3 C32 119.7(6) . . ? C21 N3 Cu1 129.7(5) . . ? C32 N3 Cu1 110.4(4) . . ? C30 N4 C31 118.1(5) . . ? C30 N4 Cu1 130.8(5) . . ? C31 N4 Cu1 111.0(4) . . ? C15 C14 C13 117.2(11) . . ? C15 C14 H14A 108.0 . . ? C13 C14 H14A 108.0 . . ? C15 C14 H14B 108.0 . . ? C13 C14 H14B 108.0 . . ? H14A C14 H14B 107.2 . . ? C16 C15 C14 116.3(15) . . ? C16 C15 H15A 108.2 . . ? C14 C15 H15A 108.2 . . ? C16 C15 H15B 108.2 . . ? C14 C15 H15B 108.2 . . ? H15A C15 H15B 107.4 . . ? C15 C16 H16A 109.2 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.6 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C19 C18 C17 133.7(17) . . ? C19 C18 H18A 103.8 . . ? C17 C18 H18A 103.8 . . ? C19 C18 H18B 103.8 . . ? C17 C18 H18B 103.8 . . ? H18A C18 H18B 105.4 . . ? C18 C19 C20 128.1(19) . . ? C18 C19 H19A 105.3 . . ? C20 C19 H19A 105.3 . . ? C18 C19 H19B 105.3 . . ? C20 C19 H19B 105.3 . . ? H19A C19 H19B 106.0 . . ? C19 C20 C36 126(2) . 2_766 ? C19 C20 H20A 111.8 . . ? C36 C20 H20A 82.7 2_766 . ? C19 C20 H20C 109.6 . . ? C36 C20 H20C 113.4 2_766 . ? H20A C20 H20C 109.5 . . ? C19 C20 H20B 106.9 . . ? C36 C20 H20B 27.8 2_766 . ? H20A C20 H20B 109.5 . . ? H20C C20 H20B 109.5 . . ? C33 C34 C35 112.3(14) . . ? C33 C34 H34A 109.1 . . ? C35 C34 H34A 109.1 . . ? C33 C34 H34B 109.1 . . ? C35 C34 H34B 109.1 . . ? H34A C34 H34B 107.9 . . ? C36 C35 C34 110.0(16) . . ? C36 C35 H35A 109.7 . . ? C34 C35 H35A 109.7 . . ? C36 C35 H35B 109.7 . . ? C34 C35 H35B 109.7 . . ? H35A C35 H35B 108.2 . . ? C35 C36 C20 105.3(19) . 2_766 ? C35 C36 H36C 113.6 . . ? C20 C36 H36C 60.7 2_766 . ? C35 C36 H36B 105.3 . . ? C20 C36 H36B 149.2 2_766 . ? H36C C36 H36B 109.5 . . ? C35 C36 H36A 109.5 . . ? C20 C36 H36A 55.7 2_766 . ? H36C C36 H36A 109.5 . . ? H36B C36 H36A 109.5 . . ? C39 C38 C37 134.4(16) . . ? C39 C38 H38A 103.6 . . ? C37 C38 H38A 103.6 . . ? C39 C38 H38B 103.6 . . ? C37 C38 H38B 103.6 . . ? H38A C38 H38B 105.3 . . ? C38 C39 C40 120(2) . . ? C38 C39 H39A 107.3 . . ? C40 C39 H39A 107.3 . . ? C38 C39 H39B 107.3 . . ? C40 C39 H39B 107.3 . . ? H39A C39 H39B 106.9 . . ? C38 C39 H16F 121.2 . . ? C40 C39 H16F 43.9 . . ? H39A C39 H16F 131.2 . . ? H39B C39 H16F 65.4 . . ? C39 C40 H40A 107.2 . . ? C39 C40 H40B 112.7 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 108.4 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C40 H16E 123.2 . . ? H40A C40 H16E 124.1 . . ? H40B C40 H16E 31.9 . . ? H40C C40 H16E 77.6 . . ? C39 C40 H16F 22.6 . . ? H40A C40 H16F 115.2 . . ? H40B C40 H16F 124.0 . . ? H40C C40 H16F 85.9 . . ? H16E C40 H16F 120.6 . . ? C15' C14' C13 112.3(16) . . ? C15' C14' H14C 109.1 . . ? C13 C14' H14C 109.1 . . ? C15' C14' H14D 109.1 . . ? C13 C14' H14D 109.1 . . ? H14C C14' H14D 107.9 . . ? C14' C15' C16' 121.7(16) . . ? C14' C15' H15C 106.9 . . ? C16' C15' H15C 106.9 . . ? C14' C15' H15D 106.9 . . ? C16' C15' H15D 106.9 . . ? H15C C15' H15D 106.7 . . ? C15' C16' H40B 79.4 . . ? C15' C16' H40C 141.7 . . ? H40B C16' H40C 75.3 . . ? C15' C16' H16E 106.3 . . ? H40B C16' H16E 29.5 . . ? H40C C16' H16E 45.9 . . ? C15' C16' H16D 115.3 . . ? H40B C16' H16D 111.9 . . ? H40C C16' H16D 100.7 . . ? H16E C16' H16D 109.5 . . ? C15' C16' H16F 106.6 . . ? H40B C16' H16F 130.2 . . ? H40C C16' H16F 70.7 . . ? H16E C16' H16F 109.5 . . ? H16D C16' H16F 109.5 . . ? C19' C18' C17 129(2) . . ? C19' C18' H18C 105.0 . . ? C17 C18' H18C 105.0 . . ? C19' C18' H18D 105.0 . . ? C17 C18' H18D 105.0 . . ? H18C C18' H18D 105.9 . . ? C18' C19' C20' 114.9(18) . . ? C18' C19' H19C 108.6 . . ? C20' C19' H19C 108.6 . . ? C18' C19' H19D 108.6 . . ? C20' C19' H19D 108.6 . . ? H19C C19' H19D 107.5 . . ? C18' C19' H40E 168.1 . . ? C20' C19' H40E 64.4 . . ? H19C C19' H40E 82.3 . . ? H19D C19' H40E 62.3 . . ? C18' C19' H40F 91.4 . . ? C20' C19' H40F 30.8 . . ? H19C C19' H40F 138.0 . . ? H19D C19' H40F 99.9 . . ? H40E C19' H40F 83.2 . . ? C19' C20' H20D 110.3 . . ? C19' C20' H20F 111.6 . . ? H20D C20' H20F 109.5 . . ? C19' C20' H20E 106.5 . . ? H20D C20' H20E 109.5 . . ? H20F C20' H20E 109.5 . . ? C19' C20' H40D 124.8 . . ? H20D C20' H40D 93.5 . . ? H20F C20' H40D 105.3 . . ? H20E C20' H40D 20.0 . . ? C19' C20' H40F 29.0 . . ? H20D C20' H40F 81.2 . . ? H20F C20' H40F 123.6 . . ? H20E C20' H40F 118.6 . . ? H40D C20' H40F 129.7 . . ? C35' C34' C33 123.8(15) . . ? C35' C34' H34C 106.4 . . ? C33 C34' H34C 106.4 . . ? C35' C34' H34D 106.4 . . ? C33 C34' H34D 106.4 . . ? H34C C34' H34D 106.5 . . ? C36' C35' C34' 116.1(18) . . ? C36' C35' H35C 108.3 . . ? C34' C35' H35C 108.3 . . ? C36' C35' H35D 108.3 . . ? C34' C35' H35D 108.3 . . ? H35C C35' H35D 107.4 . . ? C35' C36' H36E 109.8 . . ? C35' C36' H36F 109.0 . . ? H36E C36' H36F 109.5 . . ? C35' C36' H36D 109.5 . . ? H36E C36' H36D 109.5 . . ? H36F C36' H36D 109.5 . . ? C39' C38' C37 118.2(15) . . ? C39' C38' H38C 107.8 . . ? C37 C38' H38C 107.8 . . ? C39' C38' H38D 107.8 . . ? C37 C38' H38D 107.8 . . ? H38C C38' H38D 107.1 . . ? C38' C39' C40' 118.6(17) . . ? C38' C39' H20F 78.7 . . ? C40' C39' H20F 56.2 . . ? C38' C39' H39D 107.7 . . ? C40' C39' H39D 107.7 . . ? H20F C39' H39D 85.5 . . ? C38' C39' H39C 107.7 . . ? C40' C39' H39C 107.7 . . ? H20F C39' H39C 162.7 . . ? H39D C39' H39C 107.1 . . ? C39' C40' H20D 115.8 . . ? C39' C40' H20F 51.9 . . ? H20D C40' H20F 65.7 . . ? C39' C40' H20E 110.6 . . ? H20D C40' H20E 76.3 . . ? H20F C40' H20E 86.7 . . ? C39' C40' H40D 109.9 . . ? H20D C40' H40D 56.8 . . ? H20F C40' H40D 72.0 . . ? H20E C40' H40D 21.1 . . ? C39' C40' H40E 108.7 . . ? H20D C40' H40E 135.5 . . ? H20F C40' H40E 156.8 . . ? H20E C40' H40E 90.0 . . ? H40D C40' H40E 109.5 . . ? C39' C40' H40F 109.9 . . ? H20D C40' H40F 54.0 . . ? H20F C40' H40F 91.0 . . ? H20E C40' H40F 125.7 . . ? H40D C40' H40F 109.5 . . ? H40E C40' H40F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -1.0(14) . . . . ? C13 C1 C2 C3 176.8(9) . . . . ? C1 C2 C3 C4 -0.4(15) . . . . ? C2 C3 C4 C12 1.6(13) . . . . ? C2 C3 C4 C5 -178.6(9) . . . . ? C3 C4 C5 C6 -178.4(10) . . . . ? C12 C4 C5 C6 1.4(13) . . . . ? C4 C5 C6 C7 -1.2(15) . . . . ? C5 C6 C7 C8 -176.6(9) . . . . ? C5 C6 C7 C11 -0.4(12) . . . . ? C6 C7 C8 C9 177.4(8) . . . . ? C11 C7 C8 C9 1.2(12) . . . . ? C7 C8 C9 C10 -0.8(14) . . . . ? C8 C9 C10 N2 1.1(12) . . . . ? C8 C9 C10 C17 179.7(8) . . . . ? C8 C7 C11 N2 -1.9(9) . . . . ? C6 C7 C11 N2 -178.4(6) . . . . ? C8 C7 C11 C12 178.4(6) . . . . ? C6 C7 C11 C12 1.9(9) . . . . ? N2 C11 C12 N1 0.1(8) . . . . ? C7 C11 C12 N1 179.8(5) . . . . ? N2 C11 C12 C4 178.5(5) . . . . ? C7 C11 C12 C4 -1.8(9) . . . . ? C3 C4 C12 N1 -1.7(10) . . . . ? C5 C4 C12 N1 178.5(6) . . . . ? C3 C4 C12 C11 180.0(6) . . . . ? C5 C4 C12 C11 0.2(9) . . . . ? N1 C1 C13 C14' -75.7(16) . . . . ? C2 C1 C13 C14' 106.5(15) . . . . ? N1 C1 C13 C14 92.6(9) . . . . ? C2 C1 C13 C14 -85.2(11) . . . . ? N2 C10 C17 C18 -109.4(11) . . . . ? C9 C10 C17 C18 72.0(13) . . . . ? N2 C10 C17 C18' 99.0(12) . . . . ? C9 C10 C17 C18' -79.7(13) . . . . ? N3 C21 C22 C23 1.9(13) . . . . ? C33 C21 C22 C23 -179.6(8) . . . . ? C21 C22 C23 C24 -1.1(15) . . . . ? C22 C23 C24 C25 179.0(9) . . . . ? C22 C23 C24 C32 0.5(14) . . . . ? C23 C24 C25 C26 -177.2(10) . . . . ? C32 C24 C25 C26 1.2(14) . . . . ? C24 C25 C26 C27 -5.4(15) . . . . ? C25 C26 C27 C31 5.8(14) . . . . ? C25 C26 C27 C28 -176.3(9) . . . . ? C26 C27 C28 C29 -177.1(9) . . . . ? C31 C27 C28 C29 0.9(12) . . . . ? C27 C28 C29 C30 -0.9(14) . . . . ? C28 C29 C30 N4 0.4(12) . . . . ? C28 C29 C30 C37 -178.9(8) . . . . ? C26 C27 C31 N4 177.6(7) . . . . ? C28 C27 C31 N4 -0.4(10) . . . . ? C26 C27 C31 C32 -2.0(10) . . . . ? C28 C27 C31 C32 180.0(6) . . . . ? C23 C24 C32 N3 -0.7(11) . . . . ? C25 C24 C32 N3 -179.2(7) . . . . ? C23 C24 C32 C31 -178.9(7) . . . . ? C25 C24 C32 C31 2.6(11) . . . . ? N4 C31 C32 N3 -0.1(8) . . . . ? C27 C31 C32 N3 179.5(5) . . . . ? N4 C31 C32 C24 178.2(6) . . . . ? C27 C31 C32 C24 -2.2(9) . . . . ? N3 C21 C33 C34 -90.0(11) . . . . ? C22 C21 C33 C34 91.5(11) . . . . ? N3 C21 C33 C34' 92.1(9) . . . . ? C22 C21 C33 C34' -86.3(10) . . . . ? N4 C30 C37 C38 -95.5(12) . . . . ? C29 C30 C37 C38 83.8(13) . . . . ? N4 C30 C37 C38' 88.3(11) . . . . ? C29 C30 C37 C38' -92.5(11) . . . . ? C2 C1 N1 C12 1.0(10) . . . . ? C13 C1 N1 C12 -176.9(6) . . . . ? C2 C1 N1 Cu1 176.3(6) . . . . ? C13 C1 N1 Cu1 -1.6(10) . . . . ? C11 C12 N1 C1 178.8(5) . . . . ? C4 C12 N1 C1 0.4(9) . . . . ? C11 C12 N1 Cu1 2.6(6) . . . . ? C4 C12 N1 Cu1 -175.7(5) . . . . ? N4 Cu1 N1 C1 43.6(6) . . . . ? N2 Cu1 N1 C1 -178.9(6) . . . . ? N3 Cu1 N1 C1 -55.4(6) . . . . ? N4 Cu1 N1 C12 -140.7(4) . . . . ? N2 Cu1 N1 C12 -3.2(4) . . . . ? N3 Cu1 N1 C12 120.3(4) . . . . ? C9 C10 N2 C11 -1.8(9) . . . . ? C17 C10 N2 C11 179.6(6) . . . . ? C9 C10 N2 Cu1 -175.9(5) . . . . ? C17 C10 N2 Cu1 5.5(9) . . . . ? C12 C11 N2 C10 -178.2(5) . . . . ? C7 C11 N2 C10 2.1(8) . . . . ? C12 C11 N2 Cu1 -2.9(6) . . . . ? C7 C11 N2 Cu1 177.4(4) . . . . ? N4 Cu1 N2 C10 -50.8(6) . . . . ? N1 Cu1 N2 C10 177.8(5) . . . . ? N3 Cu1 N2 C10 61.9(5) . . . . ? N4 Cu1 N2 C11 134.7(3) . . . . ? N1 Cu1 N2 C11 3.3(3) . . . . ? N3 Cu1 N2 C11 -112.6(4) . . . . ? C22 C21 N3 C32 -2.1(10) . . . . ? C33 C21 N3 C32 179.5(6) . . . . ? C22 C21 N3 Cu1 173.9(6) . . . . ? C33 C21 N3 Cu1 -4.6(9) . . . . ? C24 C32 N3 C21 1.5(10) . . . . ? C31 C32 N3 C21 179.7(6) . . . . ? C24 C32 N3 Cu1 -175.2(6) . . . . ? C31 C32 N3 Cu1 3.0(7) . . . . ? N4 Cu1 N3 C21 -179.8(6) . . . . ? N2 Cu1 N3 C21 43.9(6) . . . . ? N1 Cu1 N3 C21 -55.0(6) . . . . ? N4 Cu1 N3 C32 -3.5(4) . . . . ? N2 Cu1 N3 C32 -139.8(4) . . . . ? N1 Cu1 N3 C32 121.3(4) . . . . ? C29 C30 N4 C31 0.1(9) . . . . ? C37 C30 N4 C31 179.4(6) . . . . ? C29 C30 N4 Cu1 -176.8(5) . . . . ? C37 C30 N4 Cu1 2.4(8) . . . . ? C27 C31 N4 C30 0.0(8) . . . . ? C32 C31 N4 C30 179.6(5) . . . . ? C27 C31 N4 Cu1 177.5(5) . . . . ? C32 C31 N4 Cu1 -2.9(6) . . . . ? N2 Cu1 N4 C30 -50.6(6) . . . . ? N1 Cu1 N4 C30 64.8(5) . . . . ? N3 Cu1 N4 C30 -179.4(5) . . . . ? N2 Cu1 N4 C31 132.3(4) . . . . ? N1 Cu1 N4 C31 -112.3(4) . . . . ? N3 Cu1 N4 C31 3.5(4) . . . . ? C1 C13 C14 C15 -177.1(12) . . . . ? C14' C13 C14 C15 -9(2) . . . . ? C13 C14 C15 C16 172.7(14) . . . . ? C10 C17 C18 C19 15(3) . . . . ? C18' C17 C18 C19 153(3) . . . . ? C17 C18 C19 C20 177(2) . . . . ? C18 C19 C20 C36 83(4) . . . 2_766 ? C21 C33 C34 C35 161.4(13) . . . . ? C34' C33 C34 C35 -22(3) . . . . ? C33 C34 C35 C36 84(2) . . . . ? C34 C35 C36 C20 116.1(18) . . . 2_766 ? C30 C37 C38 C39 -16(3) . . . . ? C38' C37 C38 C39 159(3) . . . . ? C37 C38 C39 C40 -179(2) . . . . ? C1 C13 C14' C15' -26(3) . . . . ? C14 C13 C14' C15' 166.8(17) . . . . ? C13 C14' C15' C16' -166(2) . . . . ? C10 C17 C18' C19' -157(3) . . . . ? C18 C17 C18' C19' 61(4) . . . . ? C17 C18' C19' C20' 169(2) . . . . ? C21 C33 C34' C35' -174.0(16) . . . . ? C34 C33 C34' C35' 9(3) . . . . ? C33 C34' C35' C36' 38(4) . . . . ? C30 C37 C38' C39' 37(2) . . . . ? C38 C37 C38' C39' -138(2) . . . . ? C37 C38' C39' C40' -164.9(19) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.841 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.085 #===END data_10 _database_code_depnum_ccdc_archive 'CCDC 900482' #TrackingRef '1-12-OK-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 Cu N6, 2(Cl O4)' _chemical_formula_sum 'C25 H22 Cl2 Cu N6 O8' _chemical_formula_weight 668.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M '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 17.7849(15) _cell_length_b 9.4814(8) _cell_length_c 18.1854(15) _cell_angle_alpha 90.00 _cell_angle_beta 113.7140(10) _cell_angle_gamma 90.00 _cell_volume 2807.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4945 _cell_measurement_theta_min 2.447 _cell_measurement_theta_max 26.108 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1364 _exptl_absorpt_coefficient_mu 1.028 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8695 _exptl_absorpt_correction_T_max 0.9042 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 'Bruker Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13693 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4926 _reflns_number_gt 3757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement 'SHELXTL (BRUKER 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0642P)^2^] 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 4926 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.25844(2) 0.09271(4) 0.42032(2) 0.04777(15) Uani 1 1 d . . . C1 C 0.2942(2) -0.0312(4) 0.2886(2) 0.0594(8) Uani 1 1 d . . . H1 H 0.2506 0.0239 0.2550 0.071 Uiso 1 1 calc R . . C2 C 0.3317(2) -0.1197(4) 0.2549(2) 0.0646(9) Uani 1 1 d . . . H2 H 0.3148 -0.1239 0.1994 0.078 Uiso 1 1 calc R . . C3 C 0.3949(2) -0.2024(4) 0.3045(2) 0.0681(10) Uani 1 1 d . . . H3 H 0.4217 -0.2636 0.2831 0.082 Uiso 1 1 calc R . . C4 C 0.41837(19) -0.1945(3) 0.3861(2) 0.0600(8) Uani 1 1 d . . . H4 H 0.4603 -0.2517 0.4203 0.072 Uiso 1 1 calc R . . C5 C 0.37920(17) -0.1007(3) 0.41712(18) 0.0442(7) Uani 1 1 d . . . C6 C 0.40222(17) -0.0785(3) 0.50369(18) 0.0456(7) Uani 1 1 d . . . C7 C 0.46340(19) -0.1533(3) 0.5629(2) 0.0589(8) Uani 1 1 d . . . H7 H 0.4926 -0.2229 0.5495 0.071 Uiso 1 1 calc R . . C8 C 0.4806(2) -0.1233(4) 0.6422(2) 0.0693(10) Uani 1 1 d . . . H8 H 0.5207 -0.1740 0.6830 0.083 Uiso 1 1 calc R . . C9 C 0.4385(2) -0.0193(4) 0.66040(19) 0.0624(9) Uani 1 1 d . . . H9 H 0.4508 0.0044 0.7136 0.075 Uiso 1 1 calc R . . C10 C 0.37701(19) 0.0512(3) 0.59875(19) 0.0544(8) Uani 1 1 d . . . H10 H 0.3474 0.1210 0.6114 0.065 Uiso 1 1 calc R . . C11 C 0.1720(2) -0.2011(4) 0.3906(2) 0.0660(9) Uani 1 1 d . . . H11 H 0.1968 -0.2200 0.3554 0.079 Uiso 1 1 calc R . . C12 C 0.1283(2) -0.3068(4) 0.4073(2) 0.0751(10) Uani 1 1 d . . . H12 H 0.1230 -0.3945 0.3829 0.090 Uiso 1 1 calc R . . C13 C 0.0931(2) -0.2818(4) 0.4599(2) 0.0761(10) Uani 1 1 d . . . H13 H 0.0641 -0.3523 0.4728 0.091 Uiso 1 1 calc R . . C14 C 0.1014(2) -0.1491(4) 0.4940(2) 0.0646(9) Uani 1 1 d . . . H14 H 0.0778 -0.1296 0.5302 0.078 Uiso 1 1 calc R . . C15 C 0.14424(17) -0.0465(3) 0.47443(17) 0.0478(7) Uani 1 1 d . . . C16 C 0.15508(17) 0.0992(3) 0.50613(17) 0.0464(7) Uani 1 1 d . . . C17 C 0.1214(2) 0.1482(4) 0.5574(2) 0.0616(8) Uani 1 1 d . . . H17 H 0.0898 0.0888 0.5743 0.074 Uiso 1 1 calc R . . C18 C 0.1348(2) 0.2853(4) 0.5836(2) 0.0718(10) Uani 1 1 d . . . H18 H 0.1124 0.3191 0.6184 0.086 Uiso 1 1 calc R . . C19 C 0.1810(2) 0.3719(4) 0.5586(2) 0.0641(9) Uani 1 1 d . . . H19 H 0.1900 0.4652 0.5757 0.077 Uiso 1 1 calc R . . C20 C 0.21390(18) 0.3187(3) 0.50771(19) 0.0546(8) Uani 1 1 d . . . H20 H 0.2454 0.3774 0.4904 0.066 Uiso 1 1 calc R . . C21 C 0.16377(17) 0.3026(3) 0.30202(16) 0.0435(7) Uani 1 1 d . . . H21 H 0.1199 0.2497 0.3024 0.052 Uiso 1 1 calc R . . C22 C 0.14701(19) 0.4248(3) 0.25550(18) 0.0491(7) Uani 1 1 d . . . C23 C 0.2136(2) 0.5009(3) 0.2563(2) 0.0637(9) Uani 1 1 d . . . H23 H 0.2055 0.5837 0.2266 0.076 Uiso 1 1 calc R . . C24 C 0.2915(2) 0.4536(4) 0.3009(2) 0.0705(10) Uani 1 1 d . . . H24 H 0.3365 0.5038 0.3011 0.085 Uiso 1 1 calc R . . C25 C 0.30309(19) 0.3323(4) 0.34525(19) 0.0586(8) Uani 1 1 d . . . H25 H 0.3562 0.3012 0.3755 0.070 Uiso 1 1 calc R . . Cl1 Cl 0.41861(5) 0.03158(9) 0.09781(5) 0.0653(2) Uani 1 1 d . . . Cl2 Cl 0.05676(5) 0.87535(8) 0.16379(5) 0.0571(2) Uani 1 1 d . . . N1 N 0.31719(14) -0.0202(2) 0.36807(14) 0.0474(6) Uani 1 1 d . . . N2 N 0.35887(14) 0.0220(2) 0.52188(14) 0.0460(6) Uani 1 1 d . . . N3 N 0.18021(15) -0.0726(3) 0.42283(14) 0.0490(6) Uani 1 1 d . . . N4 N 0.20170(14) 0.1836(2) 0.48211(14) 0.0466(6) Uani 1 1 d . . . N5 N 0.23972(13) 0.2582(2) 0.34585(14) 0.0443(6) Uani 1 1 d . . . N6 N 0.06785(17) 0.4651(3) 0.21051(16) 0.0668(8) Uani 1 1 d . . . H6A H 0.0583 0.5399 0.1815 0.080 Uiso 1 1 calc R . . H6B H 0.0277 0.4155 0.2113 0.080 Uiso 1 1 calc R . . O1 O 0.35799(17) -0.0742(3) 0.0741(2) 0.1001(10) Uani 1 1 d . . . O2 O 0.40798(17) 0.1253(3) 0.03373(17) 0.1002(10) Uani 1 1 d . . . O3 O 0.49907(15) -0.0264(3) 0.13127(18) 0.0939(9) Uani 1 1 d . . . O4 O 0.4079(2) 0.1176(3) 0.15911(18) 0.1069(10) Uani 1 1 d . . . O5 O 0.0207(3) 0.7767(4) 0.1948(3) 0.1618(18) Uani 1 1 d . . . O6 O 0.12939(17) 0.8171(4) 0.1642(2) 0.1094(10) Uani 1 1 d . . . O7 O 0.0081(3) 0.9161(4) 0.0869(2) 0.1528(17) Uani 1 1 d . . . O8 O 0.0757(2) 0.9982(3) 0.2137(2) 0.1143(11) 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 0.0523(2) 0.0491(2) 0.0493(2) 0.01109(16) 0.02815(19) 0.01411(16) C1 0.0621(19) 0.067(2) 0.056(2) 0.0083(17) 0.0301(16) 0.0070(17) C2 0.077(2) 0.068(2) 0.061(2) -0.0086(18) 0.042(2) -0.0068(19) C3 0.071(2) 0.060(2) 0.090(3) -0.017(2) 0.050(2) -0.0019(18) C4 0.0536(18) 0.0495(19) 0.078(2) -0.0011(17) 0.0272(17) 0.0103(15) C5 0.0425(15) 0.0360(15) 0.0578(18) 0.0045(13) 0.0242(14) -0.0007(12) C6 0.0411(15) 0.0351(16) 0.0588(19) 0.0085(13) 0.0182(14) -0.0012(12) C7 0.0565(19) 0.0478(18) 0.069(2) 0.0099(16) 0.0219(17) 0.0100(15) C8 0.062(2) 0.062(2) 0.066(2) 0.0211(18) 0.0080(18) 0.0045(18) C9 0.069(2) 0.065(2) 0.0443(19) 0.0075(16) 0.0128(16) -0.0082(18) C10 0.0585(19) 0.0503(19) 0.0509(19) -0.0014(15) 0.0183(16) -0.0013(15) C11 0.078(2) 0.065(2) 0.062(2) -0.0133(18) 0.0353(18) -0.0109(19) C12 0.092(3) 0.055(2) 0.078(2) -0.0101(19) 0.034(2) -0.018(2) C13 0.084(3) 0.069(3) 0.081(3) 0.008(2) 0.039(2) -0.019(2) C14 0.070(2) 0.070(2) 0.063(2) 0.0066(19) 0.0370(18) -0.0058(18) C15 0.0448(16) 0.0564(19) 0.0430(16) 0.0052(14) 0.0184(13) -0.0003(14) C16 0.0430(15) 0.0553(19) 0.0408(16) 0.0060(14) 0.0166(13) 0.0079(13) C17 0.0587(19) 0.074(2) 0.061(2) 0.0011(18) 0.0341(17) 0.0041(17) C18 0.081(2) 0.084(3) 0.064(2) -0.007(2) 0.043(2) 0.017(2) C19 0.070(2) 0.060(2) 0.058(2) -0.0117(17) 0.0214(18) 0.0111(18) C20 0.0507(17) 0.051(2) 0.060(2) 0.0031(16) 0.0202(15) 0.0051(15) C21 0.0463(16) 0.0416(16) 0.0474(16) 0.0012(13) 0.0239(14) 0.0014(13) C22 0.0606(19) 0.0447(17) 0.0448(17) 0.0018(13) 0.0243(15) 0.0115(15) C23 0.083(2) 0.048(2) 0.065(2) 0.0131(16) 0.0345(19) -0.0027(18) C24 0.073(2) 0.065(2) 0.077(2) 0.0091(19) 0.033(2) -0.0216(19) C25 0.0446(17) 0.069(2) 0.059(2) 0.0058(17) 0.0171(15) -0.0022(16) Cl1 0.0580(5) 0.0602(5) 0.0686(6) 0.0069(4) 0.0161(4) -0.0037(4) Cl2 0.0575(5) 0.0524(5) 0.0647(5) 0.0125(4) 0.0280(4) 0.0094(4) N1 0.0509(14) 0.0501(14) 0.0486(15) 0.0077(12) 0.0276(12) 0.0102(12) N2 0.0474(13) 0.0412(13) 0.0467(15) 0.0039(11) 0.0160(11) 0.0023(11) N3 0.0515(14) 0.0506(15) 0.0478(14) -0.0045(12) 0.0229(12) -0.0048(12) N4 0.0469(13) 0.0476(15) 0.0471(14) 0.0032(11) 0.0206(11) 0.0069(11) N5 0.0430(13) 0.0451(14) 0.0476(14) 0.0053(11) 0.0212(11) 0.0050(11) N6 0.0669(18) 0.0711(19) 0.0633(18) 0.0212(15) 0.0272(15) 0.0235(15) O1 0.0743(17) 0.0708(18) 0.147(3) -0.0078(17) 0.0364(18) -0.0154(14) O2 0.0864(19) 0.129(2) 0.0746(18) 0.0354(17) 0.0219(15) -0.0132(17) O3 0.0613(15) 0.0814(18) 0.113(2) -0.0050(16) 0.0077(15) 0.0085(14) O4 0.131(3) 0.099(2) 0.088(2) -0.0082(17) 0.0414(19) 0.0220(19) O5 0.183(4) 0.090(2) 0.291(5) 0.045(3) 0.177(4) 0.003(2) O6 0.0743(17) 0.125(3) 0.130(3) -0.018(2) 0.0425(18) 0.0214(18) O7 0.170(4) 0.140(3) 0.090(2) 0.006(2) -0.009(2) 0.065(3) O8 0.147(3) 0.088(2) 0.120(3) -0.0323(19) 0.066(2) -0.0043(19) _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 N4 1.984(2) . ? Cu1 N1 1.985(2) . ? Cu1 N5 2.011(2) . ? Cu1 N2 2.097(2) . ? Cu1 N3 2.108(2) . ? C1 N1 1.338(4) . ? C1 C2 1.362(4) . ? C1 H1 0.9300 . ? C2 C3 1.370(5) . ? C2 H2 0.9300 . ? C3 C4 1.372(5) . ? C3 H3 0.9300 . ? C4 C5 1.382(4) . ? C4 H4 0.9300 . ? C5 N1 1.343(3) . ? C5 C6 1.474(4) . ? C6 N2 1.348(4) . ? C6 C7 1.380(4) . ? C7 C8 1.379(5) . ? C7 H7 0.9300 . ? C8 C9 1.357(5) . ? C8 H8 0.9300 . ? C9 C10 1.383(4) . ? C9 H9 0.9300 . ? C10 N2 1.331(4) . ? C10 H10 0.9300 . ? C11 N3 1.335(4) . ? C11 C12 1.373(5) . ? C11 H11 0.9300 . ? C12 C13 1.359(5) . ? C12 H12 0.9300 . ? C13 C14 1.384(5) . ? C13 H13 0.9300 . ? C14 C15 1.367(4) . ? C14 H14 0.9300 . ? C15 N3 1.354(4) . ? C15 C16 1.479(4) . ? C16 N4 1.345(4) . ? C16 C17 1.376(4) . ? C17 C18 1.372(5) . ? C17 H17 0.9300 . ? C18 C19 1.362(5) . ? C18 H18 0.9300 . ? C19 C20 1.375(4) . ? C19 H19 0.9300 . ? C20 N4 1.350(4) . ? C20 H20 0.9300 . ? C21 N5 1.331(3) . ? C21 C22 1.395(4) . ? C21 H21 0.9300 . ? C22 N6 1.368(4) . ? C22 C23 1.382(4) . ? C23 C24 1.369(5) . ? C23 H23 0.9300 . ? C24 C25 1.372(5) . ? C24 H24 0.9300 . ? C25 N5 1.332(4) . ? C25 H25 0.9300 . ? Cl1 O1 1.407(3) . ? Cl1 O2 1.416(3) . ? Cl1 O3 1.421(3) . ? Cl1 O4 1.454(3) . ? Cl2 O7 1.372(3) . ? Cl2 O5 1.376(3) . ? Cl2 O6 1.402(3) . ? Cl2 O8 1.431(3) . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? 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 N1 172.36(10) . . ? N4 Cu1 N5 93.35(9) . . ? N1 Cu1 N5 94.29(9) . . ? N4 Cu1 N2 94.99(9) . . ? N1 Cu1 N2 79.82(10) . . ? N5 Cu1 N2 133.96(9) . . ? N4 Cu1 N3 79.64(10) . . ? N1 Cu1 N3 95.08(10) . . ? N5 Cu1 N3 131.50(9) . . ? N2 Cu1 N3 94.54(9) . . ? N1 C1 C2 122.8(3) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 118.4(3) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C2 C3 C4 119.6(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 119.5(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 120.6(3) . . ? N1 C5 C6 115.4(2) . . ? C4 C5 C6 124.0(3) . . ? N2 C6 C7 121.4(3) . . ? N2 C6 C5 115.0(2) . . ? C7 C6 C5 123.6(3) . . ? C8 C7 C6 118.9(3) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C9 C8 C7 119.5(3) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 119.2(3) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? N2 C10 C9 122.0(3) . . ? N2 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? N3 C11 C12 122.8(3) . . ? N3 C11 H11 118.6 . . ? C12 C11 H11 118.6 . . ? C13 C12 C11 119.3(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 118.5(3) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? N3 C15 C14 121.2(3) . . ? N3 C15 C16 114.6(3) . . ? C14 C15 C16 124.2(3) . . ? N4 C16 C17 120.8(3) . . ? N4 C16 C15 115.4(2) . . ? C17 C16 C15 123.8(3) . . ? C18 C17 C16 119.6(3) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C19 C18 C17 119.9(3) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 118.8(3) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? N4 C20 C19 121.8(3) . . ? N4 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? N5 C21 C22 123.0(3) . . ? N5 C21 H21 118.5 . . ? C22 C21 H21 118.5 . . ? N6 C22 C23 122.1(3) . . ? N6 C22 C21 120.8(3) . . ? C23 C22 C21 117.0(3) . . ? C24 C23 C22 119.6(3) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 120.0(3) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? N5 C25 C24 121.3(3) . . ? N5 C25 H25 119.4 . . ? C24 C25 H25 119.3 . . ? O1 Cl1 O2 111.27(19) . . ? O1 Cl1 O3 111.77(17) . . ? O2 Cl1 O3 111.91(19) . . ? O1 Cl1 O4 108.3(2) . . ? O2 Cl1 O4 105.27(19) . . ? O3 Cl1 O4 107.94(19) . . ? O7 Cl2 O5 113.7(3) . . ? O7 Cl2 O6 108.6(2) . . ? O5 Cl2 O6 108.0(2) . . ? O7 Cl2 O8 108.0(2) . . ? O5 Cl2 O8 108.8(3) . . ? O6 Cl2 O8 109.6(2) . . ? C1 N1 C5 119.0(3) . . ? C1 N1 Cu1 124.6(2) . . ? C5 N1 Cu1 116.02(19) . . ? C10 N2 C6 118.9(3) . . ? C10 N2 Cu1 128.3(2) . . ? C6 N2 Cu1 112.24(19) . . ? C11 N3 C15 118.1(3) . . ? C11 N3 Cu1 128.8(2) . . ? C15 N3 Cu1 112.27(19) . . ? C16 N4 C20 119.1(3) . . ? C16 N4 Cu1 116.48(19) . . ? C20 N4 Cu1 124.0(2) . . ? C21 N5 C25 119.1(2) . . ? C21 N5 Cu1 120.22(18) . . ? C25 N5 Cu1 120.4(2) . . ? C22 N6 H6A 120.0 . . ? C22 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.476 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.056