# Electronic Supplementary Material (ESI) for CrystEngComm # 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 919374' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 Cd F3 N3 O5.50' _chemical_formula_weight 606.82 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' Cd Cd -0.8075 1.2024 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.769(2) _cell_length_b 11.6795(12) _cell_length_c 20.382(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.5720(10) _cell_angle_gamma 90.00 _cell_volume 4762.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4233 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 28.15 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2424 _exptl_absorpt_coefficient_mu 0.984 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7308 _exptl_absorpt_correction_T_max 0.8994 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9212 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4251 _reflns_number_gt 3706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+24.1429P] 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 4251 _refine_ls_number_parameters 334 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.059 _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 Cd1 Cd 0.251176(14) 0.35688(2) 0.175834(15) 0.02791(12) Uani 1 1 d . . . F1 F 0.4095(2) 0.1826(4) 0.5222(4) 0.151(3) Uani 1 1 d . . . F2 F 0.4964(2) 0.2291(4) 0.5009(3) 0.1016(15) Uani 1 1 d . . . F3 F 0.4797(4) 0.2881(5) 0.5882(2) 0.187(4) Uani 1 1 d . . . N1 N 0.34744(18) 0.2631(3) 0.1479(2) 0.0374(9) Uani 1 1 d . . . N2 N 0.26983(19) 0.5057(3) 0.1070(2) 0.0368(8) Uani 1 1 d . . . N3 N 0.64906(17) -0.0315(3) 0.16165(19) 0.0359(8) Uani 1 1 d . . . O1 O 0.2498(2) 0.3995(4) 0.2985(3) 0.0807(13) Uani 1 1 d U . . O2 O 0.3400(3) 0.4280(5) 0.2665(2) 0.0852(16) Uani 1 1 d . . . O3 O 0.29212(17) 0.6651(3) 0.31726(17) 0.0428(8) Uani 1 1 d . . . O4 O 0.31210(16) 0.7492(3) 0.41740(17) 0.0414(8) Uani 1 1 d . . . O6W O 0.4598(6) 0.5461(11) 0.2913(7) 0.133(6) Uani 0.50 1 d P . . H1W H 0.4762 0.5939 0.3228 0.200 Uiso 1 1 d R . . H2W H 0.4231 0.5097 0.2811 0.200 Uiso 1 1 d R . . C1 C 0.4046(2) 0.3204(4) 0.1586(2) 0.0371(10) Uani 1 1 d . . . H1 H 0.4042 0.3984 0.1676 0.044 Uiso 1 1 calc R . . C2 C 0.4649(2) 0.2705(4) 0.1571(2) 0.0365(10) Uani 1 1 d . . . H2 H 0.5034 0.3148 0.1649 0.044 Uiso 1 1 calc R . . C3 C 0.4674(2) 0.1541(4) 0.1438(2) 0.0349(10) Uani 1 1 d . . . C4 C 0.4065(2) 0.0942(5) 0.1297(3) 0.0499(13) Uani 1 1 d . . . H4 H 0.4049 0.0168 0.1186 0.060 Uiso 1 1 calc R . . C5 C 0.3490(2) 0.1517(4) 0.1324(3) 0.0504(14) Uani 1 1 d . . . H5 H 0.3092 0.1107 0.1228 0.061 Uiso 1 1 calc R . . C6 C 0.5306(2) 0.0934(4) 0.1473(2) 0.0334(9) Uani 1 1 d . . . C7 C 0.5901(2) 0.1255(4) 0.1927(2) 0.0393(11) Uani 1 1 d . . . H7 H 0.5918 0.1906 0.2194 0.047 Uiso 1 1 calc R . . C8 C 0.6467(2) 0.0616(4) 0.1986(2) 0.0412(11) Uani 1 1 d . . . H8 H 0.6858 0.0846 0.2303 0.049 Uiso 1 1 calc R . . C9 C 0.5928(2) -0.0590(4) 0.1149(3) 0.0467(12) Uani 1 1 d . . . H9 H 0.5936 -0.1204 0.0862 0.056 Uiso 1 1 calc R . . C10 C 0.5338(2) -0.0012(4) 0.1071(3) 0.0496(13) Uani 1 1 d . . . H10 H 0.4956 -0.0256 0.0747 0.060 Uiso 1 1 calc R . . C11 C 0.2468(3) 0.4964(4) 0.0395(3) 0.0446(11) Uani 1 1 d . . . H11 H 0.2354 0.4241 0.0208 0.053 Uiso 1 1 calc R . . C12 C 0.2391(3) 0.5894(4) -0.0040(3) 0.0414(11) Uani 1 1 d . . . H12 H 0.2234 0.5787 -0.0508 0.050 Uiso 1 1 calc R . . C13 C 0.2547(2) 0.6988(4) 0.0224(2) 0.0347(10) Uani 1 1 d . . . C14 C 0.2793(3) 0.7070(4) 0.0927(3) 0.0504(13) Uani 1 1 d . . . H14 H 0.2915 0.7779 0.1130 0.061 Uiso 1 1 calc R . . C15 C 0.2855(3) 0.6102(4) 0.1319(3) 0.0484(12) Uani 1 1 d . . . H15 H 0.3017 0.6182 0.1789 0.058 Uiso 1 1 calc R . . C16 C 0.3093(3) 0.4281(4) 0.3102(3) 0.0502(14) Uani 1 1 d . . . C17 C 0.3471(2) 0.4526(4) 0.3837(2) 0.0323(9) Uani 1 1 d . . . C18 C 0.3790(2) 0.3595(4) 0.4206(2) 0.0378(10) Uani 1 1 d . . . H18 H 0.3761 0.2880 0.3999 0.045 Uiso 1 1 calc R . . C19 C 0.4153(2) 0.3719(4) 0.4885(2) 0.0404(11) Uani 1 1 d . . . C20 C 0.4193(2) 0.4768(4) 0.5202(2) 0.0436(11) Uani 1 1 d . . . H20 H 0.4434 0.4849 0.5655 0.052 Uiso 1 1 calc R . . C21 C 0.3870(2) 0.5699(4) 0.4838(2) 0.0392(10) Uani 1 1 d . . . H21 H 0.3895 0.6407 0.5051 0.047 Uiso 1 1 calc R . . C22 C 0.3508(2) 0.5596(4) 0.4156(2) 0.0297(9) Uani 1 1 d . . . C23 C 0.3161(2) 0.6652(4) 0.3809(2) 0.0311(9) Uani 1 1 d . . . C24 C 0.4488(3) 0.2695(5) 0.5260(3) 0.0512(13) Uani 1 1 d . . . O7W O 0.4241(10) 0.8076(19) 0.2357(9) 0.470(17) Uani 1 1 d . . . H4W H 0.4332 0.7397 0.2503 0.705 Uiso 1 1 d R . . H9W H 0.3953 0.8477 0.2074 0.705 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 Cd1 0.02779(18) 0.02231(18) 0.0325(2) 0.00097(12) 0.00611(12) 0.00280(11) F1 0.066(3) 0.094(3) 0.277(8) 0.123(5) 0.015(4) 0.010(2) F2 0.084(3) 0.091(3) 0.139(4) 0.053(3) 0.046(3) 0.051(2) F3 0.339(10) 0.108(4) 0.055(3) 0.006(3) -0.047(4) 0.122(6) N1 0.0328(19) 0.036(2) 0.042(2) -0.0027(17) 0.0076(16) 0.0088(16) N2 0.039(2) 0.030(2) 0.042(2) 0.0087(16) 0.0100(17) 0.0047(16) N3 0.0287(18) 0.036(2) 0.040(2) -0.0070(17) 0.0048(15) 0.0045(15) O1 0.0809(15) 0.0779(15) 0.0787(15) 0.0043(10) 0.0138(10) -0.0054(10) O2 0.112(4) 0.104(4) 0.034(2) -0.011(2) 0.010(2) 0.046(3) O3 0.052(2) 0.0349(17) 0.0389(19) 0.0065(14) 0.0084(15) 0.0093(15) O4 0.0474(18) 0.0271(16) 0.0468(19) -0.0038(14) 0.0074(15) 0.0021(14) O6W 0.120(9) 0.138(11) 0.176(12) -0.101(10) 0.098(9) -0.069(8) C1 0.043(2) 0.026(2) 0.046(3) 0.004(2) 0.020(2) 0.0089(19) C2 0.033(2) 0.032(2) 0.045(3) 0.002(2) 0.0121(19) 0.0041(18) C3 0.030(2) 0.037(2) 0.035(2) -0.0056(19) 0.0053(18) 0.0065(18) C4 0.033(2) 0.039(3) 0.075(4) -0.021(3) 0.008(2) 0.002(2) C5 0.030(2) 0.046(3) 0.072(4) -0.022(3) 0.007(2) 0.004(2) C6 0.029(2) 0.030(2) 0.040(2) -0.0059(19) 0.0078(18) 0.0051(17) C7 0.036(2) 0.036(2) 0.043(3) -0.013(2) 0.006(2) 0.0033(19) C8 0.032(2) 0.042(3) 0.045(3) -0.013(2) 0.001(2) 0.003(2) C9 0.034(2) 0.042(3) 0.058(3) -0.021(2) 0.002(2) 0.007(2) C10 0.030(2) 0.048(3) 0.062(3) -0.026(3) -0.004(2) 0.004(2) C11 0.062(3) 0.026(2) 0.046(3) 0.003(2) 0.016(2) 0.000(2) C12 0.056(3) 0.030(2) 0.036(2) 0.003(2) 0.009(2) 0.003(2) C13 0.034(2) 0.029(2) 0.043(3) 0.004(2) 0.0124(19) 0.0024(18) C14 0.073(4) 0.028(2) 0.045(3) 0.004(2) 0.006(3) -0.006(2) C15 0.068(3) 0.035(3) 0.037(3) 0.006(2) 0.004(2) -0.003(2) C16 0.069(4) 0.023(2) 0.045(3) 0.007(2) -0.008(3) 0.010(2) C17 0.035(2) 0.029(2) 0.030(2) 0.0027(18) 0.0055(17) 0.0031(18) C18 0.047(3) 0.030(2) 0.036(2) 0.0027(19) 0.010(2) 0.0082(19) C19 0.038(2) 0.045(3) 0.037(3) 0.011(2) 0.0074(19) 0.007(2) C20 0.047(3) 0.046(3) 0.031(2) 0.002(2) -0.002(2) 0.004(2) C21 0.043(2) 0.034(2) 0.037(2) -0.005(2) 0.004(2) -0.001(2) C22 0.030(2) 0.027(2) 0.033(2) 0.0023(18) 0.0092(17) -0.0024(17) C23 0.0245(19) 0.028(2) 0.041(3) 0.0014(19) 0.0091(18) -0.0033(16) C24 0.055(3) 0.048(3) 0.047(3) 0.015(2) 0.006(2) 0.011(3) O7W 0.54(3) 0.54(3) 0.279(18) -0.22(2) 0.01(2) 0.27(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 Cd1 N2 2.331(4) . ? Cd1 O4 2.362(3) 4_545 ? Cd1 O2 2.383(5) . ? Cd1 O3 2.432(3) 4_545 ? Cd1 N3 2.439(3) 3_455 ? Cd1 N1 2.476(4) . ? Cd1 O1 2.557(5) . ? Cd1 C23 2.727(4) 4_545 ? F1 C24 1.292(7) . ? F2 C24 1.316(7) . ? F3 C24 1.277(7) . ? N1 C1 1.328(6) . ? N1 C5 1.342(6) . ? N2 C15 1.329(6) . ? N2 C11 1.335(6) . ? N3 C8 1.332(6) . ? N3 C9 1.334(6) . ? N3 Cd1 2.439(3) 3_545 ? O1 C16 1.239(7) . ? O2 C16 1.226(7) . ? O3 C23 1.258(5) . ? O3 Cd1 2.432(3) 4 ? O4 C23 1.248(5) . ? O4 Cd1 2.362(3) 4 ? O6W H1W 0.8500 . ? O6W H2W 0.8501 . ? C1 C2 1.390(6) . ? C1 H1 0.9300 . ? C2 C3 1.390(6) . ? C2 H2 0.9300 . ? C3 C4 1.406(7) . ? C3 C6 1.476(6) . ? C4 C5 1.384(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.384(6) . ? C6 C10 1.387(6) . ? C7 C8 1.370(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.370(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.384(7) . ? C11 H11 0.9300 . ? C12 C13 1.391(7) . ? C12 H12 0.9300 . ? C13 C14 1.389(7) . ? C13 C13 1.485(9) 7_565 ? C14 C15 1.370(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.520(7) . ? C17 C18 1.385(6) . ? C17 C22 1.403(6) . ? C18 C19 1.394(7) . ? C18 H18 0.9300 . ? C19 C20 1.377(7) . ? C19 C24 1.488(7) . ? C20 C21 1.384(7) . ? C20 H20 0.9300 . ? C21 C22 1.396(6) . ? C21 H21 0.9300 . ? C22 C23 1.505(6) . ? C23 Cd1 2.727(4) 4 ? O7W H4W 0.8500 . ? O7W H9W 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 N2 Cd1 O4 93.41(12) . 4_545 ? N2 Cd1 O2 89.31(16) . . ? O4 Cd1 O2 163.17(14) 4_545 . ? N2 Cd1 O3 147.75(13) . 4_545 ? O4 Cd1 O3 54.65(11) 4_545 4_545 ? O2 Cd1 O3 119.81(15) . 4_545 ? N2 Cd1 N3 79.04(13) . 3_455 ? O4 Cd1 N3 84.90(11) 4_545 3_455 ? O2 Cd1 N3 111.92(14) . 3_455 ? O3 Cd1 N3 100.12(12) 4_545 3_455 ? N2 Cd1 N1 85.23(13) . . ? O4 Cd1 N1 83.61(12) 4_545 . ? O2 Cd1 N1 80.07(14) . . ? O3 Cd1 N1 86.54(12) 4_545 . ? N3 Cd1 N1 159.90(13) 3_455 . ? N2 Cd1 O1 119.38(15) . . ? O4 Cd1 O1 137.78(14) 4_545 . ? O2 Cd1 O1 51.90(16) . . ? O3 Cd1 O1 91.23(14) 4_545 . ? N3 Cd1 O1 76.97(14) 3_455 . ? N1 Cd1 O1 122.15(14) . . ? N2 Cd1 C23 120.43(14) . 4_545 ? O4 Cd1 C23 27.19(12) 4_545 4_545 ? O2 Cd1 C23 144.77(16) . 4_545 ? O3 Cd1 C23 27.47(12) 4_545 4_545 ? N3 Cd1 C23 93.32(12) 3_455 4_545 ? N1 Cd1 C23 83.86(12) . 4_545 ? O1 Cd1 C23 115.81(15) . 4_545 ? C1 N1 C5 116.7(4) . . ? C1 N1 Cd1 118.7(3) . . ? C5 N1 Cd1 123.8(3) . . ? C15 N2 C11 116.9(4) . . ? C15 N2 Cd1 121.2(3) . . ? C11 N2 Cd1 119.2(3) . . ? C8 N3 C9 116.3(4) . . ? C8 N3 Cd1 122.1(3) . 3_545 ? C9 N3 Cd1 121.6(3) . 3_545 ? C16 O1 Cd1 88.2(4) . . ? C16 O2 Cd1 96.8(4) . . ? C23 O3 Cd1 89.4(3) . 4 ? C23 O4 Cd1 92.9(3) . 4 ? H1W O6W H2W 131.6 . . ? N1 C1 C2 123.8(4) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C1 C2 C3 119.7(4) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 116.6(4) . . ? C2 C3 C6 122.7(4) . . ? C4 C3 C6 120.6(4) . . ? C5 C4 C3 119.2(5) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 123.8(5) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C7 C6 C10 115.8(4) . . ? C7 C6 C3 121.7(4) . . ? C10 C6 C3 122.5(4) . . ? C8 C7 C6 120.2(4) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? N3 C8 C7 123.8(4) . . ? N3 C8 H8 118.1 . . ? C7 C8 H8 118.1 . . ? N3 C9 C10 123.4(4) . . ? N3 C9 H9 118.3 . . ? C10 C9 H9 118.3 . . ? C9 C10 C6 120.4(4) . . ? C9 C10 H10 119.8 . . ? C6 C10 H10 119.8 . . ? N2 C11 C12 123.0(5) . . ? N2 C11 H11 118.5 . . ? C12 C11 H11 118.5 . . ? C11 C12 C13 119.9(5) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 116.4(4) . . ? C14 C13 C13 122.0(5) . 7_565 ? C12 C13 C13 121.6(5) . 7_565 ? C15 C14 C13 119.8(5) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? N2 C15 C14 124.0(5) . . ? N2 C15 H15 118.0 . . ? C14 C15 H15 118.0 . . ? O2 C16 O1 123.1(6) . . ? O2 C16 C17 118.9(5) . . ? O1 C16 C17 117.6(6) . . ? C18 C17 C22 119.3(4) . . ? C18 C17 C16 115.7(4) . . ? C22 C17 C16 125.1(4) . . ? C17 C18 C19 120.7(4) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.5(4) . . ? C20 C19 C24 120.8(5) . . ? C18 C19 C24 118.7(5) . . ? C19 C20 C21 119.1(4) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C20 C21 C22 121.4(4) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C21 C22 C17 119.1(4) . . ? C21 C22 C23 117.4(4) . . ? C17 C22 C23 123.5(4) . . ? O4 C23 O3 123.0(4) . . ? O4 C23 C22 117.6(4) . . ? O3 C23 C22 119.4(4) . . ? O4 C23 Cd1 59.9(2) . 4 ? O3 C23 Cd1 63.1(2) . 4 ? C22 C23 Cd1 176.2(3) . 4 ? F3 C24 F1 109.5(6) . . ? F3 C24 F2 102.5(6) . . ? F1 C24 F2 102.9(6) . . ? F3 C24 C19 114.6(5) . . ? F1 C24 C19 113.6(5) . . ? F2 C24 C19 112.6(5) . . ? H4W O7W H9W 143.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cd1 N1 C1 53.2(3) . . . . ? O4 Cd1 N1 C1 147.2(3) 4_545 . . . ? O2 Cd1 N1 C1 -36.9(4) . . . . ? O3 Cd1 N1 C1 -158.0(3) 4_545 . . . ? N3 Cd1 N1 C1 91.7(5) 3_455 . . . ? O1 Cd1 N1 C1 -68.7(4) . . . . ? C23 Cd1 N1 C1 174.6(4) 4_545 . . . ? N2 Cd1 N1 C5 -137.3(4) . . . . ? O4 Cd1 N1 C5 -43.3(4) 4_545 . . . ? O2 Cd1 N1 C5 132.6(4) . . . . ? O3 Cd1 N1 C5 11.5(4) 4_545 . . . ? N3 Cd1 N1 C5 -98.8(5) 3_455 . . . ? O1 Cd1 N1 C5 100.8(4) . . . . ? C23 Cd1 N1 C5 -15.9(4) 4_545 . . . ? O4 Cd1 N2 C15 158.2(4) 4_545 . . . ? O2 Cd1 N2 C15 -38.4(4) . . . . ? O3 Cd1 N2 C15 165.7(3) 4_545 . . . ? N3 Cd1 N2 C15 74.0(4) 3_455 . . . ? N1 Cd1 N2 C15 -118.5(4) . . . . ? O1 Cd1 N2 C15 5.9(4) . . . . ? C23 Cd1 N2 C15 161.5(4) 4_545 . . . ? O4 Cd1 N2 C11 -2.9(4) 4_545 . . . ? O2 Cd1 N2 C11 160.5(4) . . . . ? O3 Cd1 N2 C11 4.7(5) 4_545 . . . ? N3 Cd1 N2 C11 -87.0(4) 3_455 . . . ? N1 Cd1 N2 C11 80.4(4) . . . . ? O1 Cd1 N2 C11 -155.1(3) . . . . ? C23 Cd1 N2 C11 0.4(4) 4_545 . . . ? N2 Cd1 O1 C16 -63.5(4) . . . . ? O4 Cd1 O1 C16 160.3(3) 4_545 . . . ? O2 Cd1 O1 C16 -0.8(3) . . . . ? O3 Cd1 O1 C16 127.1(3) 4_545 . . . ? N3 Cd1 O1 C16 -132.8(4) 3_455 . . . ? N1 Cd1 O1 C16 40.4(4) . . . . ? C23 Cd1 O1 C16 139.9(3) 4_545 . . . ? N2 Cd1 O2 C16 130.1(4) . . . . ? O4 Cd1 O2 C16 -130.3(5) 4_545 . . . ? O3 Cd1 O2 C16 -64.5(4) 4_545 . . . ? N3 Cd1 O2 C16 52.2(4) 3_455 . . . ? N1 Cd1 O2 C16 -144.6(4) . . . . ? O1 Cd1 O2 C16 0.8(3) . . . . ? C23 Cd1 O2 C16 -80.5(4) 4_545 . . . ? C5 N1 C1 C2 -2.7(7) . . . . ? Cd1 N1 C1 C2 167.6(4) . . . . ? N1 C1 C2 C3 0.0(7) . . . . ? C1 C2 C3 C4 2.6(7) . . . . ? C1 C2 C3 C6 -174.6(4) . . . . ? C2 C3 C4 C5 -2.6(8) . . . . ? C6 C3 C4 C5 174.6(5) . . . . ? C1 N1 C5 C4 2.7(8) . . . . ? Cd1 N1 C5 C4 -167.0(5) . . . . ? C3 C4 C5 N1 -0.1(9) . . . . ? C2 C3 C6 C7 32.3(7) . . . . ? C4 C3 C6 C7 -144.8(5) . . . . ? C2 C3 C6 C10 -149.9(5) . . . . ? C4 C3 C6 C10 33.0(7) . . . . ? C10 C6 C7 C8 -3.4(7) . . . . ? C3 C6 C7 C8 174.6(5) . . . . ? C9 N3 C8 C7 2.7(8) . . . . ? Cd1 N3 C8 C7 -179.1(4) 3_545 . . . ? C6 C7 C8 N3 1.2(8) . . . . ? C8 N3 C9 C10 -4.4(8) . . . . ? Cd1 N3 C9 C10 177.4(4) 3_545 . . . ? N3 C9 C10 C6 2.2(9) . . . . ? C7 C6 C10 C9 1.8(8) . . . . ? C3 C6 C10 C9 -176.1(5) . . . . ? C15 N2 C11 C12 0.0(8) . . . . ? Cd1 N2 C11 C12 161.9(4) . . . . ? N2 C11 C12 C13 -0.9(8) . . . . ? C11 C12 C13 C14 1.5(7) . . . . ? C11 C12 C13 C13 -178.2(5) . . . 7_565 ? C12 C13 C14 C15 -1.3(8) . . . . ? C13 C13 C14 C15 178.4(5) 7_565 . . . ? C11 N2 C15 C14 0.1(8) . . . . ? Cd1 N2 C15 C14 -161.3(4) . . . . ? C13 C14 C15 N2 0.6(9) . . . . ? Cd1 O2 C16 O1 -1.6(6) . . . . ? Cd1 O2 C16 C17 171.8(3) . . . . ? Cd1 O1 C16 O2 1.5(6) . . . . ? Cd1 O1 C16 C17 -172.0(4) . . . . ? O2 C16 C17 C18 -84.0(6) . . . . ? O1 C16 C17 C18 89.8(6) . . . . ? O2 C16 C17 C22 97.0(6) . . . . ? O1 C16 C17 C22 -89.2(6) . . . . ? C22 C17 C18 C19 -1.0(7) . . . . ? C16 C17 C18 C19 179.8(5) . . . . ? C17 C18 C19 C20 0.9(7) . . . . ? C17 C18 C19 C24 -179.8(5) . . . . ? C18 C19 C20 C21 -0.2(8) . . . . ? C24 C19 C20 C21 -179.5(5) . . . . ? C19 C20 C21 C22 -0.3(7) . . . . ? C20 C21 C22 C17 0.1(7) . . . . ? C20 C21 C22 C23 178.7(4) . . . . ? C18 C17 C22 C21 0.5(6) . . . . ? C16 C17 C22 C21 179.6(5) . . . . ? C18 C17 C22 C23 -177.9(4) . . . . ? C16 C17 C22 C23 1.1(7) . . . . ? Cd1 O4 C23 O3 2.4(4) 4 . . . ? Cd1 O4 C23 C22 -176.8(3) 4 . . . ? Cd1 O3 C23 O4 -2.4(4) 4 . . . ? Cd1 O3 C23 C22 176.9(3) 4 . . . ? C21 C22 C23 O4 -12.1(6) . . . . ? C17 C22 C23 O4 166.4(4) . . . . ? C21 C22 C23 O3 168.7(4) . . . . ? C17 C22 C23 O3 -12.9(6) . . . . ? C21 C22 C23 Cd1 -59(5) . . . 4 ? C17 C22 C23 Cd1 119(5) . . . 4 ? C20 C19 C24 F3 0.7(9) . . . . ? C18 C19 C24 F3 -178.6(6) . . . . ? C20 C19 C24 F1 127.5(6) . . . . ? C18 C19 C24 F1 -51.7(8) . . . . ? C20 C19 C24 F2 -116.0(6) . . . . ? C18 C19 C24 F2 64.7(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7W H4W O6W 0.85 2.42 3.27(3) 179.6 . O6W H1W F3 0.85 2.27 3.115(12) 176.3 5_666 O6W H2W O2 0.85 1.92 2.771(12) 175.0 . _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 1.358 _refine_diff_density_min -0.767 _refine_diff_density_rms 0.097 data_bbb _database_code_depnum_ccdc_archive 'CCDC 919375' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H15 Cd F3 N3 O4' _chemical_formula_weight 578.79 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' Cd Cd -0.8075 1.2024 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.750(4) _cell_length_b 11.660(2) _cell_length_c 20.045(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.057(2) _cell_angle_gamma 90.00 _cell_volume 4683.3(16) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3197 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 23.05 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2296 _exptl_absorpt_coefficient_mu 0.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7618 _exptl_absorpt_correction_T_max 0.9248 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15454 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4348 _reflns_number_gt 3352 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+13.9064P] 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 4348 _refine_ls_number_parameters 316 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.047 _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 Cd1 Cd 0.251661(15) 0.35573(3) 0.179306(16) 0.02693(12) Uani 1 1 d . . . F1 F 0.4112(2) 0.1957(4) 0.5378(3) 0.138(2) Uani 1 1 d . . . F2 F 0.4954(2) 0.2293(3) 0.5044(2) 0.0909(13) Uani 1 1 d . . . F3 F 0.4881(3) 0.3029(4) 0.5950(2) 0.142(3) Uani 1 1 d . . . N1 N 0.34820(19) 0.2647(3) 0.1465(2) 0.0369(10) Uani 1 1 d . . . N2 N 0.27047(19) 0.5074(3) 0.11043(19) 0.0332(9) Uani 1 1 d . . . N3 N 0.64870(18) -0.0348(3) 0.1635(2) 0.0363(10) Uani 1 1 d . . . O1 O 0.2537(2) 0.4033(4) 0.2998(2) 0.0728(12) Uani 1 1 d U . . O2 O 0.3451(3) 0.4218(5) 0.2688(2) 0.0862(16) Uani 1 1 d U . . O3 O 0.29192(17) 0.6643(3) 0.31691(17) 0.0417(8) Uani 1 1 d . . . O4 O 0.31017(17) 0.7514(3) 0.41738(17) 0.0402(8) Uani 1 1 d . . . C1 C 0.4066(2) 0.3204(4) 0.1605(2) 0.0335(11) Uani 1 1 d . . . H1 H 0.4069 0.3978 0.1719 0.040 Uiso 1 1 calc R . . C2 C 0.4656(2) 0.2702(4) 0.1591(2) 0.0336(11) Uani 1 1 d . . . H2 H 0.5046 0.3135 0.1696 0.040 Uiso 1 1 calc R . . C3 C 0.4679(2) 0.1553(4) 0.1423(2) 0.0364(11) Uani 1 1 d . . . C4 C 0.4067(2) 0.0981(5) 0.1240(3) 0.0516(15) Uani 1 1 d . . . H4 H 0.4045 0.0219 0.1098 0.062 Uiso 1 1 calc R . . C5 C 0.3495(3) 0.1554(5) 0.1271(3) 0.0519(15) Uani 1 1 d . . . H5 H 0.3094 0.1155 0.1149 0.062 Uiso 1 1 calc R . . C6 C 0.5311(2) 0.0928(4) 0.1467(2) 0.0331(11) Uani 1 1 d . . . C7 C 0.5894(2) 0.1228(4) 0.1937(3) 0.0400(12) Uani 1 1 d . . . H7 H 0.5907 0.1881 0.2207 0.048 Uiso 1 1 calc R . . C8 C 0.6459(2) 0.0578(5) 0.2014(3) 0.0436(13) Uani 1 1 d . . . H8 H 0.6842 0.0795 0.2347 0.052 Uiso 1 1 calc R . . C9 C 0.5935(2) -0.0608(5) 0.1153(3) 0.0509(15) Uani 1 1 d . . . H9 H 0.5947 -0.1230 0.0865 0.061 Uiso 1 1 calc R . . C10 C 0.5350(2) -0.0013(5) 0.1055(3) 0.0520(15) Uani 1 1 d . . . H10 H 0.4977 -0.0239 0.0711 0.062 Uiso 1 1 calc R . . C11 C 0.2493(3) 0.4969(4) 0.0420(3) 0.0396(12) Uani 1 1 d . . . H11 H 0.2397 0.4238 0.0235 0.048 Uiso 1 1 calc R . . C12 C 0.2407(2) 0.5888(4) -0.0029(2) 0.0376(11) Uani 1 1 d . . . H12 H 0.2257 0.5771 -0.0503 0.045 Uiso 1 1 calc R . . C13 C 0.2547(2) 0.6986(4) 0.0233(2) 0.0287(10) Uani 1 1 d . . . C14 C 0.2777(3) 0.7091(4) 0.0943(2) 0.0404(12) Uani 1 1 d . . . H14 H 0.2885 0.7809 0.1143 0.048 Uiso 1 1 calc R . . C15 C 0.2845(3) 0.6130(4) 0.1351(3) 0.0415(12) Uani 1 1 d . . . H15 H 0.2997 0.6223 0.1826 0.050 Uiso 1 1 calc R . . C16 C 0.3138(3) 0.4277(4) 0.3120(3) 0.0449(13) Uani 1 1 d . . . C17 C 0.3505(2) 0.4552(4) 0.3856(2) 0.0286(10) Uani 1 1 d . . . C18 C 0.3834(2) 0.3639(4) 0.4245(2) 0.0368(11) Uani 1 1 d . . . H18 H 0.3824 0.2920 0.4041 0.044 Uiso 1 1 calc R . . C19 C 0.4177(2) 0.3785(4) 0.4934(2) 0.0383(12) Uani 1 1 d . . . C20 C 0.4208(3) 0.4844(5) 0.5241(3) 0.0463(13) Uani 1 1 d . . . H20 H 0.4451 0.4949 0.5697 0.056 Uiso 1 1 calc R . . C21 C 0.3872(2) 0.5749(4) 0.4862(2) 0.0381(12) Uani 1 1 d . . . H21 H 0.3882 0.6463 0.5072 0.046 Uiso 1 1 calc R . . C22 C 0.3519(2) 0.5622(4) 0.4174(2) 0.0276(10) Uani 1 1 d . . . C23 C 0.3157(2) 0.6667(4) 0.3809(2) 0.0293(10) Uani 1 1 d . . . C24 C 0.4517(3) 0.2774(5) 0.5328(3) 0.0526(15) 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 Cd1 0.02916(19) 0.02142(19) 0.02927(19) 0.00131(14) 0.00590(13) 0.00235(14) F1 0.066(3) 0.100(4) 0.245(7) 0.121(4) 0.034(3) 0.020(3) F2 0.088(3) 0.081(3) 0.110(3) 0.036(2) 0.035(3) 0.050(2) F3 0.232(6) 0.095(3) 0.055(3) 0.007(2) -0.041(3) 0.072(4) N1 0.032(2) 0.038(2) 0.040(2) -0.0034(18) 0.0077(18) 0.0090(18) N2 0.036(2) 0.029(2) 0.035(2) 0.0073(17) 0.0113(18) 0.0032(17) N3 0.029(2) 0.032(2) 0.046(2) -0.0074(19) 0.0059(18) 0.0040(17) O1 0.0728(15) 0.0711(15) 0.0709(15) 0.0046(10) 0.0122(10) -0.0059(10) O2 0.104(4) 0.116(4) 0.035(2) -0.014(2) 0.013(2) 0.041(3) O3 0.053(2) 0.034(2) 0.036(2) 0.0048(15) 0.0081(16) 0.0099(16) O4 0.045(2) 0.0272(19) 0.046(2) -0.0030(16) 0.0081(16) 0.0030(15) C1 0.039(3) 0.028(3) 0.036(3) 0.005(2) 0.015(2) 0.009(2) C2 0.033(3) 0.031(3) 0.037(3) 0.003(2) 0.008(2) 0.005(2) C3 0.031(3) 0.039(3) 0.036(3) -0.010(2) 0.005(2) 0.009(2) C4 0.034(3) 0.040(3) 0.077(4) -0.025(3) 0.008(3) 0.006(2) C5 0.031(3) 0.046(3) 0.073(4) -0.026(3) 0.003(3) 0.005(2) C6 0.028(2) 0.031(3) 0.038(3) -0.004(2) 0.005(2) 0.004(2) C7 0.035(3) 0.035(3) 0.045(3) -0.016(2) 0.001(2) 0.006(2) C8 0.028(3) 0.051(3) 0.045(3) -0.017(3) -0.003(2) 0.006(2) C9 0.036(3) 0.044(3) 0.066(4) -0.028(3) 0.001(3) 0.008(2) C10 0.029(3) 0.054(4) 0.064(4) -0.030(3) -0.004(3) 0.008(2) C11 0.054(3) 0.025(3) 0.042(3) 0.002(2) 0.017(2) 0.003(2) C12 0.052(3) 0.029(3) 0.029(2) 0.002(2) 0.007(2) -0.001(2) C13 0.030(2) 0.024(2) 0.035(3) 0.004(2) 0.013(2) 0.0020(19) C14 0.062(3) 0.022(3) 0.035(3) 0.000(2) 0.009(2) -0.002(2) C15 0.057(3) 0.031(3) 0.036(3) 0.003(2) 0.011(2) 0.000(2) C16 0.063(4) 0.023(3) 0.043(3) 0.010(2) 0.002(3) 0.012(2) C17 0.031(2) 0.029(3) 0.026(2) 0.0026(19) 0.0065(18) 0.0010(19) C18 0.045(3) 0.030(3) 0.035(3) 0.001(2) 0.009(2) 0.008(2) C19 0.038(3) 0.042(3) 0.032(3) 0.009(2) 0.006(2) 0.009(2) C20 0.051(3) 0.047(3) 0.034(3) -0.001(2) -0.001(2) 0.007(3) C21 0.045(3) 0.033(3) 0.032(3) -0.006(2) 0.002(2) -0.001(2) C22 0.028(2) 0.025(2) 0.031(2) 0.0012(19) 0.0088(19) -0.0029(19) C23 0.027(2) 0.027(3) 0.035(3) 0.002(2) 0.009(2) -0.0044(19) C24 0.056(4) 0.051(4) 0.047(3) 0.014(3) 0.009(3) 0.019(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 Cd1 N2 2.338(4) . ? Cd1 O4 2.364(3) 4_545 ? Cd1 O2 2.401(5) . ? Cd1 O3 2.417(3) 4_545 ? Cd1 N3 2.437(4) 3_455 ? Cd1 O1 2.467(5) . ? Cd1 N1 2.502(4) . ? Cd1 C23 2.720(4) 4_545 ? F1 C24 1.292(7) . ? F2 C24 1.314(7) . ? F3 C24 1.313(7) . ? N1 C5 1.335(6) . ? N1 C1 1.338(6) . ? N2 C15 1.330(6) . ? N2 C11 1.333(6) . ? N3 C9 1.327(6) . ? N3 C8 1.330(6) . ? N3 Cd1 2.437(4) 3_545 ? O1 C16 1.238(7) . ? O2 C16 1.213(7) . ? O3 C23 1.250(5) . ? O3 Cd1 2.417(3) 4 ? O4 C23 1.252(5) . ? O4 Cd1 2.364(3) 4 ? C1 C2 1.364(6) . ? C1 H1 0.9300 . ? C2 C3 1.386(6) . ? C2 H2 0.9300 . ? C3 C4 1.397(7) . ? C3 C6 1.483(6) . ? C4 C5 1.376(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.372(6) . ? C6 C10 1.389(7) . ? C7 C8 1.371(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.368(7) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.380(6) . ? C11 H11 0.9300 . ? C12 C13 1.386(7) . ? C12 H12 0.9300 . ? C13 C14 1.384(6) . ? C13 C13 1.502(8) 7_565 ? C14 C15 1.372(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.509(7) . ? C17 C18 1.389(6) . ? C17 C22 1.398(6) . ? C18 C19 1.391(6) . ? C18 H18 0.9300 . ? C19 C20 1.374(7) . ? C19 C24 1.490(7) . ? C20 C21 1.378(7) . ? C20 H20 0.9300 . ? C21 C22 1.391(6) . ? C21 H21 0.9300 . ? C22 C23 1.516(6) . ? C23 Cd1 2.720(4) 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 N2 Cd1 O4 92.49(12) . 4_545 ? N2 Cd1 O2 88.39(16) . . ? O4 Cd1 O2 159.79(14) 4_545 . ? N2 Cd1 O3 146.97(13) . 4_545 ? O4 Cd1 O3 54.74(11) 4_545 4_545 ? O2 Cd1 O3 120.61(15) . 4_545 ? N2 Cd1 N3 78.59(13) . 3_455 ? O4 Cd1 N3 83.80(12) 4_545 3_455 ? O2 Cd1 N3 116.10(14) . 3_455 ? O3 Cd1 N3 99.50(13) 4_545 3_455 ? N2 Cd1 O1 116.41(15) . . ? O4 Cd1 O1 141.79(14) 4_545 . ? O2 Cd1 O1 52.52(15) . . ? O3 Cd1 O1 95.07(14) 4_545 . ? N3 Cd1 O1 78.56(14) 3_455 . ? N2 Cd1 N1 84.12(13) . . ? O4 Cd1 N1 82.37(12) 4_545 . ? O2 Cd1 N1 77.64(14) . . ? O3 Cd1 N1 87.04(13) 4_545 . ? N3 Cd1 N1 157.30(13) 3_455 . ? O1 Cd1 N1 122.78(14) . . ? N2 Cd1 C23 119.76(14) . 4_545 ? O4 Cd1 C23 27.38(12) 4_545 4_545 ? O2 Cd1 C23 144.51(16) . 4_545 ? O3 Cd1 C23 27.37(12) 4_545 4_545 ? N3 Cd1 C23 91.97(13) 3_455 4_545 ? O1 Cd1 C23 119.54(15) . 4_545 ? N1 Cd1 C23 83.90(13) . 4_545 ? C5 N1 C1 116.0(4) . . ? C5 N1 Cd1 124.1(3) . . ? C1 N1 Cd1 118.8(3) . . ? C15 N2 C11 116.7(4) . . ? C15 N2 Cd1 122.3(3) . . ? C11 N2 Cd1 118.5(3) . . ? C9 N3 C8 116.3(4) . . ? C9 N3 Cd1 122.4(3) . 3_545 ? C8 N3 Cd1 121.1(3) . 3_545 ? C16 O1 Cd1 90.3(4) . . ? C16 O2 Cd1 94.1(4) . . ? C23 O3 Cd1 89.9(3) . 4 ? C23 O4 Cd1 92.3(3) . 4 ? N1 C1 C2 123.8(4) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C1 C2 C3 120.5(5) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C3 C4 116.0(4) . . ? C2 C3 C6 123.1(4) . . ? C4 C3 C6 120.7(4) . . ? C5 C4 C3 119.4(5) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N1 C5 C4 124.1(5) . . ? N1 C5 H5 118.0 . . ? C4 C5 H5 118.0 . . ? C7 C6 C10 115.7(4) . . ? C7 C6 C3 121.6(4) . . ? C10 C6 C3 122.7(4) . . ? C8 C7 C6 120.8(4) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? N3 C8 C7 123.2(4) . . ? N3 C8 H8 118.4 . . ? C7 C8 H8 118.4 . . ? N3 C9 C10 123.7(5) . . ? N3 C9 H9 118.2 . . ? C10 C9 H9 118.2 . . ? C9 C10 C6 120.1(5) . . ? C9 C10 H10 119.9 . . ? C6 C10 H10 119.9 . . ? N2 C11 C12 123.4(5) . . ? N2 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C11 C12 C13 119.4(4) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 117.0(4) . . ? C14 C13 C13 121.6(5) . 7_565 ? C12 C13 C13 121.4(5) . 7_565 ? C15 C14 C13 119.6(5) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? N2 C15 C14 123.8(5) . . ? N2 C15 H15 118.1 . . ? C14 C15 H15 118.1 . . ? O2 C16 O1 123.0(6) . . ? O2 C16 C17 118.8(5) . . ? O1 C16 C17 117.9(5) . . ? C18 C17 C22 118.6(4) . . ? C18 C17 C16 115.8(4) . . ? C22 C17 C16 125.6(4) . . ? C17 C18 C19 120.9(4) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C20 C19 C18 120.5(4) . . ? C20 C19 C24 120.9(5) . . ? C18 C19 C24 118.6(5) . . ? C19 C20 C21 118.9(5) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C22 121.7(5) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C21 C22 C17 119.4(4) . . ? C21 C22 C23 117.4(4) . . ? C17 C22 C23 123.2(4) . . ? O3 C23 O4 123.0(4) . . ? O3 C23 C22 119.5(4) . . ? O4 C23 C22 117.5(4) . . ? O3 C23 Cd1 62.7(2) . 4 ? O4 C23 Cd1 60.3(2) . 4 ? C22 C23 Cd1 177.3(3) . 4 ? F1 C24 F2 104.7(5) . . ? F1 C24 F3 108.6(6) . . ? F2 C24 F3 102.4(5) . . ? F1 C24 C19 113.4(5) . . ? F2 C24 C19 113.1(5) . . ? F3 C24 C19 113.6(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 N2 Cd1 N1 C5 -135.6(4) . . . . ? O4 Cd1 N1 C5 -42.3(4) 4_545 . . . ? O2 Cd1 N1 C5 134.8(4) . . . . ? O3 Cd1 N1 C5 12.6(4) 4_545 . . . ? N3 Cd1 N1 C5 -95.2(5) 3_455 . . . ? O1 Cd1 N1 C5 106.7(4) . . . . ? C23 Cd1 N1 C5 -14.7(4) 4_545 . . . ? N2 Cd1 N1 C1 57.1(3) . . . . ? O4 Cd1 N1 C1 150.4(3) 4_545 . . . ? O2 Cd1 N1 C1 -32.6(3) . . . . ? O3 Cd1 N1 C1 -154.8(3) 4_545 . . . ? N3 Cd1 N1 C1 97.5(4) 3_455 . . . ? O1 Cd1 N1 C1 -60.7(4) . . . . ? C23 Cd1 N1 C1 177.9(4) 4_545 . . . ? O4 Cd1 N2 C15 157.0(4) 4_545 . . . ? O2 Cd1 N2 C15 -43.2(4) . . . . ? O3 Cd1 N2 C15 163.7(3) 4_545 . . . ? N3 Cd1 N2 C15 73.8(4) 3_455 . . . ? O1 Cd1 N2 C15 2.8(4) . . . . ? N1 Cd1 N2 C15 -121.0(4) . . . . ? C23 Cd1 N2 C15 159.5(4) 4_545 . . . ? O4 Cd1 N2 C11 -4.5(4) 4_545 . . . ? O2 Cd1 N2 C11 155.3(4) . . . . ? O3 Cd1 N2 C11 2.3(5) 4_545 . . . ? N3 Cd1 N2 C11 -87.6(4) 3_455 . . . ? O1 Cd1 N2 C11 -158.6(3) . . . . ? N1 Cd1 N2 C11 77.6(4) . . . . ? C23 Cd1 N2 C11 -1.9(4) 4_545 . . . ? N2 Cd1 O1 C16 -65.4(4) . . . . ? O4 Cd1 O1 C16 159.5(3) 4_545 . . . ? O2 Cd1 O1 C16 -0.2(3) . . . . ? O3 Cd1 O1 C16 125.0(3) 4_545 . . . ? N3 Cd1 O1 C16 -136.3(4) 3_455 . . . ? N1 Cd1 O1 C16 35.2(4) . . . . ? C23 Cd1 O1 C16 137.9(3) 4_545 . . . ? N2 Cd1 O2 C16 125.8(4) . . . . ? O4 Cd1 O2 C16 -141.3(4) 4_545 . . . ? O3 Cd1 O2 C16 -70.8(4) 4_545 . . . ? N3 Cd1 O2 C16 49.4(4) 3_455 . . . ? O1 Cd1 O2 C16 0.2(3) . . . . ? N1 Cd1 O2 C16 -149.8(4) . . . . ? C23 Cd1 O2 C16 -89.5(4) 4_545 . . . ? C5 N1 C1 C2 -3.2(7) . . . . ? Cd1 N1 C1 C2 165.2(4) . . . . ? N1 C1 C2 C3 0.2(7) . . . . ? C1 C2 C3 C4 3.0(7) . . . . ? C1 C2 C3 C6 -173.6(4) . . . . ? C2 C3 C4 C5 -3.3(8) . . . . ? C6 C3 C4 C5 173.4(5) . . . . ? C1 N1 C5 C4 2.9(8) . . . . ? Cd1 N1 C5 C4 -164.8(5) . . . . ? C3 C4 C5 N1 0.3(10) . . . . ? C2 C3 C6 C7 29.4(8) . . . . ? C4 C3 C6 C7 -147.0(5) . . . . ? C2 C3 C6 C10 -152.5(5) . . . . ? C4 C3 C6 C10 31.1(8) . . . . ? C10 C6 C7 C8 -4.2(8) . . . . ? C3 C6 C7 C8 174.1(5) . . . . ? C9 N3 C8 C7 1.8(8) . . . . ? Cd1 N3 C8 C7 179.1(4) 3_545 . . . ? C6 C7 C8 N3 1.9(9) . . . . ? C8 N3 C9 C10 -3.1(9) . . . . ? Cd1 N3 C9 C10 179.6(5) 3_545 . . . ? N3 C9 C10 C6 0.6(10) . . . . ? C7 C6 C10 C9 3.0(8) . . . . ? C3 C6 C10 C9 -175.2(5) . . . . ? C15 N2 C11 C12 -0.8(8) . . . . ? Cd1 N2 C11 C12 161.7(4) . . . . ? N2 C11 C12 C13 0.1(8) . . . . ? C11 C12 C13 C14 0.8(7) . . . . ? C11 C12 C13 C13 -179.1(5) . . . 7_565 ? C12 C13 C14 C15 -1.1(7) . . . . ? C13 C13 C14 C15 178.9(5) 7_565 . . . ? C11 N2 C15 C14 0.6(8) . . . . ? Cd1 N2 C15 C14 -161.2(4) . . . . ? C13 C14 C15 N2 0.4(8) . . . . ? Cd1 O2 C16 O1 -0.4(6) . . . . ? Cd1 O2 C16 C17 173.7(4) . . . . ? Cd1 O1 C16 O2 0.4(6) . . . . ? Cd1 O1 C16 C17 -173.8(4) . . . . ? O2 C16 C17 C18 -80.6(6) . . . . ? O1 C16 C17 C18 93.8(6) . . . . ? O2 C16 C17 C22 101.7(6) . . . . ? O1 C16 C17 C22 -83.9(6) . . . . ? C22 C17 C18 C19 -0.8(7) . . . . ? C16 C17 C18 C19 -178.7(5) . . . . ? C17 C18 C19 C20 -1.1(8) . . . . ? C17 C18 C19 C24 179.5(5) . . . . ? C18 C19 C20 C21 2.3(8) . . . . ? C24 C19 C20 C21 -178.3(5) . . . . ? C19 C20 C21 C22 -1.7(8) . . . . ? C20 C21 C22 C17 -0.2(7) . . . . ? C20 C21 C22 C23 178.9(5) . . . . ? C18 C17 C22 C21 1.5(7) . . . . ? C16 C17 C22 C21 179.1(5) . . . . ? C18 C17 C22 C23 -177.6(4) . . . . ? C16 C17 C22 C23 0.0(7) . . . . ? Cd1 O3 C23 O4 -0.5(5) 4 . . . ? Cd1 O3 C23 C22 178.1(3) 4 . . . ? Cd1 O4 C23 O3 0.6(5) 4 . . . ? Cd1 O4 C23 C22 -178.2(3) 4 . . . ? C21 C22 C23 O3 169.3(4) . . . . ? C17 C22 C23 O3 -11.6(7) . . . . ? C21 C22 C23 O4 -12.0(6) . . . . ? C17 C22 C23 O4 167.2(4) . . . . ? C21 C22 C23 Cd1 -48(7) . . . 4 ? C17 C22 C23 Cd1 131(7) . . . 4 ? C20 C19 C24 F1 118.8(7) . . . . ? C18 C19 C24 F1 -61.8(7) . . . . ? C20 C19 C24 F2 -122.1(6) . . . . ? C18 C19 C24 F2 57.2(7) . . . . ? C20 C19 C24 F3 -5.8(8) . . . . ? C18 C19 C24 F3 173.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.211 _refine_diff_density_min -0.780 _refine_diff_density_rms 0.096 data_2 _database_code_depnum_ccdc_archive 'CCDC 919376' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C57 H51 Co2 F6 N6 O10' _chemical_formula_weight 1211.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 '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 Tetragonal _symmetry_space_group_name_H-M I-4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 27.5676(9) _cell_length_b 27.5676(9) _cell_length_c 14.3113(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10876.2(9) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5990 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 20.03 _exptl_crystal_description Needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4984 _exptl_absorpt_coefficient_mu 0.696 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7268 _exptl_absorpt_correction_T_max 0.8792 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41971 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_sigmaI/netI 0.0897 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.50 _reflns_number_total 10129 _reflns_number_gt 6644 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+0.7164P] 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 0.441(13) _refine_ls_number_reflns 10129 _refine_ls_number_parameters 762 _refine_ls_number_restraints 123 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.0877 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.056 _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 F1 F 0.1074(2) 1.05226(19) 0.5526(4) 0.111(2) Uani 0.765(6) 1 d PDU A 1 F2 F 0.1071(3) 1.00309(19) 0.4333(4) 0.133(3) Uani 0.765(6) 1 d PDU A 1 F3 F 0.17427(19) 1.0336(2) 0.4822(6) 0.130(3) Uani 0.765(6) 1 d PDU A 1 F1' F 0.0880(4) 1.0345(7) 0.5212(16) 0.111(2) Uani 0.235(6) 1 d PD A 2 F2' F 0.1452(8) 1.0124(8) 0.4241(8) 0.133(3) Uani 0.235(6) 1 d PD A 2 F3' F 0.1635(6) 1.0474(6) 0.5553(12) 0.130(3) Uani 0.235(6) 1 d PD A 2 Co1 Co 0.10532(2) 0.79980(2) 0.92454(4) 0.03744(16) Uani 1 1 d . . . Co2 Co 0.32250(2) 0.87331(2) 0.65272(5) 0.04213(18) Uani 1 1 d . . . O1 O 0.12063(11) 0.84922(11) 0.8211(2) 0.0449(9) Uani 1 1 d . . . O2 O 0.17131(12) 0.81221(12) 0.7224(2) 0.0549(10) Uani 1 1 d . . . O3 O 0.25640(11) 0.89386(11) 0.7231(2) 0.0454(9) Uani 1 1 d . . . O4 O 0.25403(11) 0.86520(11) 0.5791(2) 0.0463(8) Uani 1 1 d . . . O5 O 0.34312(13) 0.83831(12) 0.4226(3) 0.0569(9) Uani 1 1 d . B . O6 O 0.37513(11) 0.85410(11) 0.5640(3) 0.0540(9) Uani 1 1 d . B . O7 O 0.41469(11) 0.74747(11) 0.5284(2) 0.0477(9) Uani 1 1 d . . . O8 O 0.47311(13) 0.77516(13) 0.6200(3) 0.0737(12) Uani 1 1 d . . . O9 O 0.12696(10) 0.74355(10) 0.8272(2) 0.0451(8) Uani 1 1 d . . . H1W H 0.1459 0.7237 0.8544 0.068 Uiso 1 1 d R . . H2W H 0.1439 0.7568 0.7848 0.068 Uiso 1 1 d R . . O10 O 0.55053(17) 0.71021(19) 0.6331(4) 0.141(2) Uani 1 1 d . . . H3W H 0.5656 0.7241 0.6775 0.211 Uiso 1 1 d R . . H4W H 0.5268 0.7298 0.6299 0.211 Uiso 1 1 d R . . N1 N 0.03201(14) 0.79785(13) 0.8624(3) 0.0421(10) Uani 1 1 d . . . N3 N 0.17923(13) 0.80107(14) 0.9776(3) 0.0395(10) Uani 1 1 d . . . N4 N 0.55124(13) 0.81789(14) 0.9099(3) 0.0431(10) Uani 1 1 d . . . N5 N 0.08565(14) 0.86019(14) 1.0156(3) 0.0424(10) Uani 1 1 d . . . N6 N 0.37394(15) 0.89950(14) 0.7528(3) 0.0476(11) Uani 1 1 d . . . C1 C 0.14412(17) 0.89119(16) 0.6879(3) 0.0371(12) Uani 1 1 d . . . C2 C 0.18357(17) 0.90698(16) 0.6364(3) 0.0406(12) Uani 1 1 d . . . C3 C 0.17928(18) 0.94730(17) 0.5789(4) 0.0515(14) Uani 1 1 d . . . H3 H 0.2058 0.9577 0.5440 0.062 Uiso 1 1 calc R . . C4 C 0.1366(2) 0.97150(17) 0.5736(4) 0.0541(14) Uani 1 1 d . A . C5 C 0.0965(2) 0.9563(2) 0.6239(4) 0.0569(15) Uani 1 1 d . . . H5 H 0.0673 0.9731 0.6199 0.068 Uiso 1 1 calc R . . C6 C 0.10068(18) 0.91634(18) 0.6793(4) 0.0502(14) Uani 1 1 d . . . H6 H 0.0737 0.9056 0.7123 0.060 Uiso 1 1 calc R . . C7 C 0.14631(17) 0.84709(18) 0.7480(4) 0.0380(12) Uani 1 1 d . . . C8 C 0.23407(16) 0.88561(16) 0.6468(4) 0.0394(12) Uani 1 1 d . . . C9 C 0.1324(2) 1.0162(2) 0.5120(5) 0.094(2) Uani 1 1 d DU . . C10 C 0.42814(18) 0.84366(18) 0.4374(4) 0.0482(13) Uani 1 1 d . B . C11 C 0.46269(17) 0.81207(17) 0.4726(3) 0.0436(13) Uani 1 1 d . . . C12 C 0.50967(19) 0.81409(19) 0.4371(4) 0.0599(15) Uani 1 1 d . B . H12 H 0.5335 0.7938 0.4612 0.072 Uiso 1 1 calc R . . C13 C 0.5212(2) 0.8465(2) 0.3652(4) 0.0653(16) Uani 1 1 d D . . C18' C 0.5057(4) 0.9232(4) 0.2862(9) 0.076(2) Uani 0.291(2) 1 d PD B 2 F4' F 0.4746(4) 0.9602(4) 0.2793(9) 0.135(2) Uani 0.291(2) 1 d PD B 2 F5' F 0.5470(3) 0.9450(5) 0.3111(8) 0.119(2) Uani 0.291(2) 1 d PD B 2 F6' F 0.5139(4) 0.9108(5) 0.1983(8) 0.124(2) Uani 0.291(2) 1 d PD B 2 C14 C 0.4878(2) 0.8787(2) 0.3312(5) 0.087(2) Uani 1 1 d D B . C18 C 0.5698(3) 0.8476(3) 0.3270(5) 0.076(2) Uani 0.709(2) 1 d PD B 1 F4 F 0.5908(2) 0.8898(2) 0.3419(4) 0.135(2) Uani 0.709(2) 1 d PD B 1 F5 F 0.59974(18) 0.8141(2) 0.3614(4) 0.119(2) Uani 0.709(2) 1 d PD B 1 F6 F 0.57199(19) 0.8416(2) 0.2362(4) 0.124(2) Uani 0.709(2) 1 d PD B 1 C15 C 0.4413(2) 0.8765(2) 0.3683(4) 0.0755(19) Uani 1 1 d . . . H15 H 0.4180 0.8979 0.3459 0.091 Uiso 1 1 calc R B . C16 C 0.3774(2) 0.84489(17) 0.4759(4) 0.0456(14) Uani 1 1 d . . . C17 C 0.44985(18) 0.77605(18) 0.5462(4) 0.0439(13) Uani 1 1 d . . . C19 C 0.0265(2) 0.7865(2) 0.7722(4) 0.0628(16) Uani 1 1 d . . . H19 H 0.0542 0.7805 0.7369 0.075 Uiso 1 1 calc R . . C20 C -0.0177(2) 0.7834(2) 0.7290(4) 0.0730(19) Uani 1 1 d . . . H20 H -0.0193 0.7756 0.6658 0.088 Uiso 1 1 calc R . . C21 C -0.0602(2) 0.7916(2) 0.7787(5) 0.0623(16) Uani 1 1 d . . . C22 C -0.05491(19) 0.80407(18) 0.8704(4) 0.0548(15) Uani 1 1 d . . . H22 H -0.0820 0.8111 0.9067 0.066 Uiso 1 1 calc R . . C23 C -0.00941(18) 0.80618(16) 0.9085(4) 0.0482(13) Uani 1 1 d . . . H23 H -0.0071 0.8140 0.9715 0.058 Uiso 1 1 calc R . . C24 C -0.11036(19) 0.7873(2) 0.7332(5) 0.0778(19) Uani 1 1 d . . . H24A H -0.1112 0.7584 0.6946 0.093 Uiso 1 1 calc R . . H24B H -0.1347 0.7837 0.7816 0.093 Uiso 1 1 calc R . . C25 C -0.12243(18) 0.8300(2) 0.6750(4) 0.0695(18) Uani 1 1 d . . . H25A H -0.0961 0.8358 0.6315 0.083 Uiso 1 1 calc R . . H25B H -0.1252 0.8583 0.7150 0.083 Uiso 1 1 calc R . . C26 C -0.16947(17) 0.8241(2) 0.6200(4) 0.0657(17) Uani 1 1 d . . . H26A H -0.1722 0.8508 0.5763 0.079 Uiso 1 1 calc R . . H26B H -0.1675 0.7944 0.5838 0.079 Uiso 1 1 calc R . . C27 C -0.27523(18) 0.86108(18) 0.7730(3) 0.0458(13) Uani 1 1 d . . . H27 H -0.2855 0.8890 0.8036 0.055 Uiso 1 1 calc R . . C28 C -0.23224(17) 0.8624(2) 0.7265(4) 0.0525(14) Uani 1 1 d . . . H28 H -0.2142 0.8909 0.7266 0.063 Uiso 1 1 calc R . . C29 C -0.21484(17) 0.8225(2) 0.6791(3) 0.0479(14) Uani 1 1 d . . . C30 C -0.24339(18) 0.78120(19) 0.6855(3) 0.0490(13) Uani 1 1 d . . . H30 H -0.2333 0.7526 0.6569 0.059 Uiso 1 1 calc R . . C31 C -0.28639(18) 0.78210(18) 0.7337(3) 0.0471(13) Uani 1 1 d . . . H31 H -0.3047 0.7538 0.7365 0.056 Uiso 1 1 calc R . . N2 N -0.30339(14) 0.82194(15) 0.7771(3) 0.0428(10) Uani 1 1 d . . . C33 C 0.20992(17) 0.83730(17) 0.9635(3) 0.0448(13) Uani 1 1 d . . . H33 H 0.1989 0.8645 0.9315 0.054 Uiso 1 1 calc R . . C34 C 0.25757(17) 0.83654(18) 0.9940(4) 0.0503(14) Uani 1 1 d . . . H34 H 0.2775 0.8631 0.9828 0.060 Uiso 1 1 calc R . . C35 C 0.27568(17) 0.79675(19) 1.0407(3) 0.0442(13) Uani 1 1 d . . . C36 C 0.24431(17) 0.75865(19) 1.0531(3) 0.0483(14) Uani 1 1 d . . . H36 H 0.2546 0.7306 1.0832 0.058 Uiso 1 1 calc R . . C37 C 0.19765(17) 0.76227(18) 1.0208(3) 0.0471(13) Uani 1 1 d . . . H37 H 0.1773 0.7357 1.0296 0.057 Uiso 1 1 calc R . . C38 C 0.32674(17) 0.7931(2) 1.0778(4) 0.0688(17) Uani 1 1 d . . . H38A H 0.3315 0.7603 1.1006 0.083 Uiso 1 1 calc R . . H38B H 0.3293 0.8147 1.1312 0.083 Uiso 1 1 calc R . . C39 C 0.36853(15) 0.80483(18) 1.0115(4) 0.0498(14) Uani 1 1 d D . . H39A H 0.3653 0.7857 0.9550 0.060 Uiso 1 1 calc R . . H39B H 0.3673 0.8388 0.9943 0.060 Uiso 1 1 calc R . . C40 C 0.41641(17) 0.7939(2) 1.0574(4) 0.080(2) Uani 1 1 d D . . H40A H 0.4167 0.7598 1.0737 0.096 Uiso 1 1 calc R . . H40B H 0.4178 0.8121 1.1154 0.096 Uiso 1 1 calc R . . C41 C 0.51132(19) 0.80588(18) 0.8639(4) 0.0557(15) Uani 1 1 d . . . H41 H 0.5131 0.8017 0.7995 0.067 Uiso 1 1 calc R . . C42 C 0.46681(18) 0.7993(2) 0.9079(4) 0.0611(16) Uani 1 1 d . . . H42 H 0.4398 0.7911 0.8723 0.073 Uiso 1 1 calc R . . C43 C 0.46206(16) 0.80459(19) 1.0032(4) 0.0487(14) Uani 1 1 d D . . C44 C 0.50308(19) 0.81638(19) 1.0485(4) 0.0635(17) Uani 1 1 d . . . H44 H 0.5022 0.8203 1.1130 0.076 Uiso 1 1 calc R . . C45 C 0.54616(19) 0.8228(2) 1.0021(4) 0.0644(17) Uani 1 1 d . . . H45 H 0.5734 0.8310 1.0371 0.077 Uiso 1 1 calc R . . C46 C 0.09278(16) 0.90600(18) 0.9913(4) 0.0453(14) Uani 1 1 d . . . H46 H 0.1076 0.9122 0.9342 0.054 Uiso 1 1 calc R . . C47 C 0.07933(18) 0.94509(19) 1.0462(4) 0.0583(16) Uani 1 1 d . . . H47 H 0.0850 0.9766 1.0258 0.070 Uiso 1 1 calc R . . C48 C 0.05751(18) 0.9369(2) 1.1313(4) 0.0576(16) Uani 1 1 d D . . C49 C 0.05016(18) 0.8896(2) 1.1567(4) 0.0568(15) Uani 1 1 d . . . H49 H 0.0351 0.8827 1.2132 0.068 Uiso 1 1 calc R . . C50 C 0.06473(19) 0.8525(2) 1.0999(4) 0.0568(15) Uani 1 1 d . . . H50 H 0.0601 0.8207 1.1200 0.068 Uiso 1 1 calc R . . C51 C 0.0413(3) 0.9789(2) 1.1915(5) 0.104(2) Uani 1 1 d DU . . H51A H 0.0693 0.9886 1.2267 0.124 Uiso 1 1 d R . . H51B H 0.0184 0.9657 1.2353 0.124 Uiso 1 1 d R . . C52 C 0.0195(4) 1.0206(3) 1.1543(8) 0.072(3) Uani 0.50 1 d PDU . . H52A H 0.0116 1.0423 1.2044 0.108 Uiso 0.50 1 d PR . . H52B H 0.0427 1.0357 1.1136 0.108 Uiso 0.50 1 d PR . . C53 C 0.3606(2) 0.9251(2) 0.8276(4) 0.0615(16) Uani 1 1 d . . . H53 H 0.3276 0.9291 0.8386 0.074 Uiso 1 1 calc R . . C54 C 0.3927(3) 0.9459(2) 0.8896(4) 0.0753(19) Uani 1 1 d . . . H54 H 0.3814 0.9649 0.9388 0.090 Uiso 1 1 calc R . . C55 C 0.4412(2) 0.9383(2) 0.8775(4) 0.0682(18) Uani 1 1 d D . . C56 C 0.4555(2) 0.91230(19) 0.8013(4) 0.0634(17) Uani 1 1 d . . . H56 H 0.4883 0.9072 0.7898 0.076 Uiso 1 1 calc R . . C57 C 0.42138(19) 0.89386(18) 0.7418(4) 0.0538(15) Uani 1 1 d . . . H57 H 0.4321 0.8762 0.6904 0.065 Uiso 1 1 calc R . . C58 C 0.4762(3) 0.9596(3) 0.9482(5) 0.125(3) Uani 1 1 d DU . . H58A H 0.4884 0.9334 0.9857 0.150 Uiso 1 1 d R . . H58B H 0.4583 0.9811 0.9881 0.150 Uiso 1 1 d R . . C59 C 0.5160(4) 0.9854(5) 0.9037(9) 0.109(5) Uani 0.50 1 d PDU . . H59A H 0.5365 0.9978 0.9525 0.164 Uiso 0.50 1 d PR . . H59B H 0.5343 0.9638 0.8648 0.164 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 F1 0.162(5) 0.054(4) 0.118(5) 0.020(3) 0.014(4) 0.040(3) F2 0.200(6) 0.107(4) 0.093(3) 0.044(3) -0.033(4) 0.011(4) F3 0.123(4) 0.115(4) 0.152(6) 0.092(4) 0.033(4) 0.005(3) F1' 0.162(5) 0.054(4) 0.118(5) 0.020(3) 0.014(4) 0.040(3) F2' 0.200(6) 0.107(4) 0.093(3) 0.044(3) -0.033(4) 0.011(4) F3' 0.123(4) 0.115(4) 0.152(6) 0.092(4) 0.033(4) 0.005(3) Co1 0.0354(4) 0.0365(4) 0.0403(4) 0.0029(3) 0.0032(3) -0.0002(3) Co2 0.0420(4) 0.0379(4) 0.0465(4) 0.0008(3) 0.0018(4) 0.0019(3) O1 0.047(2) 0.048(2) 0.040(2) 0.0040(17) 0.0105(18) 0.0006(16) O2 0.056(2) 0.048(2) 0.060(2) 0.0090(19) 0.0182(19) 0.0065(19) O3 0.046(2) 0.045(2) 0.045(2) 0.0043(17) 0.0018(18) 0.0020(17) O4 0.048(2) 0.042(2) 0.049(2) -0.0105(18) 0.0115(19) 0.0029(16) O5 0.059(2) 0.051(2) 0.060(2) -0.001(2) -0.003(2) 0.0117(18) O6 0.056(2) 0.051(2) 0.056(2) -0.004(2) 0.010(2) 0.0130(17) O7 0.047(2) 0.045(2) 0.052(2) -0.0126(17) -0.0042(18) -0.0042(17) O8 0.069(3) 0.076(3) 0.076(3) 0.002(2) -0.033(2) -0.006(2) O9 0.048(2) 0.042(2) 0.045(2) 0.0090(17) 0.0090(17) 0.0048(15) O10 0.111(4) 0.177(5) 0.134(5) -0.080(4) -0.058(4) 0.069(4) N1 0.045(3) 0.044(3) 0.037(3) 0.005(2) 0.005(2) 0.0046(19) N3 0.037(2) 0.035(2) 0.047(3) 0.006(2) 0.003(2) -0.001(2) N4 0.029(2) 0.052(3) 0.048(3) -0.003(2) 0.004(2) -0.0005(19) N5 0.044(3) 0.038(3) 0.046(3) 0.001(2) -0.002(2) 0.002(2) N6 0.043(3) 0.048(3) 0.051(3) -0.001(2) 0.002(2) 0.002(2) C1 0.032(3) 0.040(3) 0.040(3) -0.004(2) 0.004(2) 0.001(2) C2 0.042(3) 0.032(3) 0.048(3) 0.001(2) 0.000(3) 0.004(2) C3 0.057(4) 0.047(3) 0.050(3) 0.008(3) 0.013(3) 0.002(3) C4 0.065(4) 0.043(3) 0.054(3) 0.016(3) -0.001(3) 0.015(3) C5 0.052(4) 0.059(4) 0.060(4) 0.004(3) -0.013(3) 0.013(3) C6 0.041(3) 0.058(4) 0.051(4) 0.009(3) -0.007(3) -0.005(3) C7 0.032(3) 0.039(3) 0.043(3) 0.002(3) 0.000(2) -0.001(2) C8 0.035(3) 0.030(3) 0.053(3) 0.009(3) 0.007(3) -0.002(2) C9 0.089(5) 0.085(5) 0.109(5) 0.015(4) -0.018(4) 0.024(4) C10 0.046(3) 0.047(3) 0.052(3) -0.004(3) 0.007(3) 0.006(3) C11 0.039(3) 0.040(3) 0.052(3) -0.010(3) -0.002(3) -0.002(3) C12 0.051(4) 0.050(4) 0.078(4) -0.017(3) -0.003(3) 0.000(3) C13 0.044(4) 0.083(5) 0.069(4) -0.006(4) 0.006(3) -0.003(3) C18' 0.055(6) 0.097(7) 0.077(7) 0.025(6) 0.003(5) -0.012(5) F4' 0.122(4) 0.140(5) 0.142(5) -0.014(4) 0.038(4) -0.072(4) F5' 0.063(3) 0.161(5) 0.133(5) 0.033(4) 0.018(3) -0.009(3) F6' 0.091(4) 0.203(6) 0.077(4) -0.009(4) 0.018(3) -0.049(4) C14 0.074(5) 0.093(5) 0.095(5) 0.019(4) 0.015(4) 0.001(4) C18 0.055(6) 0.097(7) 0.077(7) 0.025(6) 0.003(5) -0.012(5) F4 0.122(4) 0.140(5) 0.142(5) -0.014(4) 0.038(4) -0.072(4) F5 0.063(3) 0.161(5) 0.133(5) 0.033(4) 0.018(3) -0.009(3) F6 0.091(4) 0.203(6) 0.077(4) -0.009(4) 0.018(3) -0.049(4) C15 0.065(4) 0.087(5) 0.074(5) 0.029(4) 0.021(4) 0.020(4) C16 0.061(4) 0.030(3) 0.046(3) 0.006(3) 0.006(3) 0.010(3) C17 0.036(3) 0.039(3) 0.057(4) -0.015(3) -0.007(3) 0.009(2) C19 0.048(4) 0.088(5) 0.052(4) -0.008(3) 0.001(3) 0.006(3) C20 0.058(4) 0.114(6) 0.047(4) -0.003(4) -0.013(3) 0.005(4) C21 0.043(4) 0.065(4) 0.079(5) 0.001(4) -0.012(3) 0.004(3) C22 0.041(3) 0.056(4) 0.067(4) -0.003(3) -0.004(3) 0.004(3) C23 0.049(3) 0.049(3) 0.046(3) 0.000(3) 0.000(3) -0.003(3) C24 0.048(4) 0.082(5) 0.103(5) 0.012(4) -0.020(4) -0.011(3) C25 0.039(3) 0.089(5) 0.081(5) 0.008(4) -0.005(3) 0.007(3) C26 0.034(3) 0.104(5) 0.059(4) 0.004(3) 0.002(3) 0.006(3) C27 0.044(3) 0.046(3) 0.047(3) -0.003(3) -0.004(3) 0.001(3) C28 0.033(3) 0.064(4) 0.060(4) 0.004(3) -0.008(3) -0.007(3) C29 0.029(3) 0.071(4) 0.044(3) -0.001(3) -0.008(2) 0.004(3) C30 0.042(3) 0.056(4) 0.049(3) -0.005(3) 0.001(3) 0.009(3) C31 0.043(3) 0.045(3) 0.053(3) 0.000(3) -0.004(3) -0.008(3) N2 0.046(3) 0.040(3) 0.042(3) -0.001(2) -0.002(2) -0.002(2) C33 0.041(3) 0.039(3) 0.055(3) -0.001(3) -0.001(3) 0.003(3) C34 0.034(3) 0.045(3) 0.072(4) 0.008(3) -0.001(3) -0.015(3) C35 0.036(3) 0.056(4) 0.041(3) 0.009(3) 0.009(2) 0.004(3) C36 0.035(3) 0.057(4) 0.053(4) 0.015(3) 0.007(3) 0.006(3) C37 0.040(3) 0.045(3) 0.057(3) 0.005(3) 0.004(3) -0.009(3) C38 0.039(3) 0.091(4) 0.076(4) 0.030(4) 0.009(3) -0.001(3) C39 0.032(3) 0.058(4) 0.059(4) 0.004(3) 0.004(3) -0.004(3) C40 0.032(3) 0.138(6) 0.070(4) 0.021(4) -0.004(3) -0.004(3) C41 0.041(3) 0.074(4) 0.052(4) 0.001(3) -0.006(3) -0.006(3) C42 0.031(3) 0.084(4) 0.068(4) 0.001(3) -0.010(3) -0.009(3) C43 0.030(3) 0.059(4) 0.056(4) 0.001(3) 0.000(3) -0.005(3) C44 0.044(3) 0.094(5) 0.053(4) -0.007(3) 0.008(3) -0.016(3) C45 0.038(3) 0.094(5) 0.061(4) -0.013(4) -0.004(3) -0.020(3) C46 0.039(3) 0.046(3) 0.052(3) -0.008(3) 0.004(3) -0.001(3) C47 0.047(3) 0.047(3) 0.081(5) -0.009(3) 0.012(3) -0.006(3) C48 0.044(3) 0.069(4) 0.060(4) -0.022(3) -0.002(3) 0.005(3) C49 0.058(4) 0.063(4) 0.049(3) -0.001(3) 0.009(3) 0.010(3) C50 0.067(4) 0.057(4) 0.046(4) 0.002(3) 0.005(3) 0.015(3) C51 0.115(6) 0.084(5) 0.112(5) -0.042(4) 0.043(4) -0.013(4) C52 0.078(7) 0.070(7) 0.069(7) -0.010(6) 0.009(6) 0.013(5) C53 0.056(4) 0.074(4) 0.054(4) -0.004(3) 0.013(3) 0.001(3) C54 0.090(5) 0.079(5) 0.056(4) -0.019(3) -0.006(4) 0.003(4) C55 0.071(5) 0.049(4) 0.084(5) -0.009(3) -0.027(4) -0.008(3) C56 0.051(4) 0.043(4) 0.097(5) -0.011(3) -0.012(4) 0.005(3) C57 0.048(4) 0.044(3) 0.069(4) -0.009(3) 0.001(3) 0.005(3) C58 0.119(6) 0.112(6) 0.142(6) -0.034(5) -0.026(5) 0.009(4) C59 0.098(9) 0.103(9) 0.126(9) -0.051(7) 0.023(7) -0.037(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C9 1.340(6) . ? F2 C9 1.373(6) . ? F3 C9 1.321(6) . ? F1' C9 1.330(8) . ? F2' C9 1.312(8) . ? F3' C9 1.362(8) . ? Co1 O7 2.052(3) 6_565 ? Co1 O1 2.055(3) . ? Co1 O9 2.168(3) . ? Co1 N3 2.175(4) . ? Co1 N5 2.182(4) . ? Co1 N1 2.209(4) . ? Co2 O6 1.999(3) . ? Co2 N6 2.141(4) . ? Co2 O3 2.158(3) . ? Co2 O4 2.173(3) . ? Co2 N2 2.173(4) 7_456 ? Co2 N4 2.268(4) 7_466 ? Co2 C8 2.463(5) . ? O1 C7 1.265(5) . ? O2 C7 1.239(5) . ? O3 C8 1.274(5) . ? O4 C8 1.248(5) . ? O5 C16 1.229(6) . ? O6 C16 1.288(6) . ? O7 C17 1.275(5) . ? O7 Co1 2.052(3) 6_564 ? O8 C17 1.235(5) . ? O9 H1W 0.8499 . ? O9 H2W 0.8500 . ? O10 H3W 0.8501 . ? O10 H4W 0.8497 . ? N1 C19 1.335(6) . ? N1 C23 1.339(5) . ? N3 C33 1.325(5) . ? N3 C37 1.336(5) . ? N4 C41 1.324(6) . ? N4 C45 1.334(6) . ? N4 Co2 2.268(4) 8_656 ? N5 C46 1.324(5) . ? N5 C50 1.355(6) . ? N6 C57 1.326(6) . ? N6 C53 1.333(6) . ? C1 C2 1.384(6) . ? C1 C6 1.389(6) . ? C1 C7 1.491(6) . ? C2 C3 1.388(6) . ? C2 C8 1.519(6) . ? C3 C4 1.356(6) . ? C3 H3 0.9300 . ? C4 C5 1.383(7) . ? C4 C9 1.520(8) . ? C5 C6 1.363(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C10 C15 1.389(7) . ? C10 C11 1.385(6) . ? C10 C16 1.503(6) . ? C11 C12 1.393(6) . ? C11 C17 1.490(7) . ? C12 C13 1.399(7) . ? C12 H12 0.9300 . ? C13 C14 1.367(8) . ? C13 C18 1.448(9) . ? C18' F6' 1.322(8) . ? C18' F5' 1.334(8) . ? C18' F4' 1.336(8) . ? C18' C14 1.472(11) . ? C18' F4' 1.941(17) 8_655 ? F4' F5' 1.542(17) 7_465 ? F4' C18' 1.941(17) 7_465 ? F5' F4' 1.542(17) 8_655 ? C14 C15 1.389(7) . ? C18 F6 1.311(7) . ? C18 F4 1.318(6) . ? C18 F5 1.333(6) . ? C15 H15 0.9300 . ? C19 C20 1.369(7) . ? C19 H19 0.9300 . ? C20 C21 1.389(7) . ? C20 H20 0.9300 . ? C21 C22 1.365(7) . ? C21 C24 1.533(7) . ? C22 C23 1.369(6) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.480(7) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.526(7) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C29 1.510(6) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 N2 1.331(5) . ? C27 C28 1.360(6) . ? C27 H27 0.9300 . ? C28 C29 1.380(6) . ? C28 H28 0.9300 . ? C29 C30 1.387(6) . ? C30 C31 1.372(6) . ? C30 H30 0.9300 . ? C31 N2 1.346(6) . ? C31 H31 0.9300 . ? N2 Co2 2.173(4) 8_556 ? C33 C34 1.385(6) . ? C33 H33 0.9300 . ? C34 C35 1.379(6) . ? C34 H34 0.9300 . ? C35 C36 1.372(6) . ? C35 C38 1.507(6) . ? C36 C37 1.371(6) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C38 C39 1.526(6) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.504(6) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 C43 1.508(6) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 C42 1.391(6) . ? C41 H41 0.9300 . ? C42 C43 1.378(7) . ? C42 H42 0.9300 . ? C43 C44 1.343(6) . ? C44 C45 1.371(6) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 C47 1.384(6) . ? C46 H46 0.9300 . ? C47 C48 1.377(7) . ? C47 H47 0.9300 . ? C48 C49 1.368(7) . ? C48 C51 1.510(5) . ? C49 C50 1.367(6) . ? C49 H49 0.9300 . ? C50 H50 0.9300 . ? C51 C52 1.401(8) . ? C51 C52 1.758(12) 2_575 ? C51 H51A 0.9600 . ? C51 H51B 0.9599 . ? C52 C52 1.56(2) 2_575 ? C52 C51 1.758(12) 2_575 ? C52 H52A 0.9600 . ? C52 H52B 0.9599 . ? C53 C54 1.378(7) . ? C53 H53 0.9300 . ? C54 C55 1.365(8) . ? C54 H54 0.9300 . ? C55 C56 1.364(8) . ? C55 C58 1.515(7) . ? C56 C57 1.365(7) . ? C56 H56 0.9300 . ? C57 H57 0.9300 . ? C58 C59 1.456(9) . ? C58 C59 1.658(15) 2_675 ? C58 H58A 0.9599 . ? C58 H58B 0.9601 . ? C59 C59 1.19(2) 2_675 ? C59 C58 1.658(15) 2_675 ? C59 H59A 0.9600 . ? C59 H59B 0.9599 . ? 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 O7 Co1 O1 176.03(13) 6_565 . ? O7 Co1 O9 94.87(12) 6_565 . ? O1 Co1 O9 87.43(12) . . ? O7 Co1 N3 90.53(14) 6_565 . ? O1 Co1 N3 92.77(14) . . ? O9 Co1 N3 88.74(13) . . ? O7 Co1 N5 89.16(14) 6_565 . ? O1 Co1 N5 88.58(14) . . ? O9 Co1 N5 175.93(14) . . ? N3 Co1 N5 90.68(14) . . ? O7 Co1 N1 91.74(14) 6_565 . ? O1 Co1 N1 85.06(13) . . ? O9 Co1 N1 88.60(13) . . ? N3 Co1 N1 176.64(15) . . ? N5 Co1 N1 91.83(14) . . ? O6 Co2 N6 91.93(16) . . ? O6 Co2 O3 168.20(14) . . ? N6 Co2 O3 99.10(15) . . ? O6 Co2 O4 107.18(14) . . ? N6 Co2 O4 159.11(14) . . ? O3 Co2 O4 61.31(12) . . ? O6 Co2 N2 93.64(15) . 7_456 ? N6 Co2 N2 89.70(15) . 7_456 ? O3 Co2 N2 90.64(14) . 7_456 ? O4 Co2 N2 97.26(14) . 7_456 ? O6 Co2 N4 91.88(14) . 7_466 ? N6 Co2 N4 89.56(15) . 7_466 ? O3 Co2 N4 84.05(13) . 7_466 ? O4 Co2 N4 81.61(13) . 7_466 ? N2 Co2 N4 174.45(16) 7_456 7_466 ? O6 Co2 C8 137.15(17) . . ? N6 Co2 C8 129.20(18) . . ? O3 Co2 C8 31.13(14) . . ? O4 Co2 C8 30.43(14) . . ? N2 Co2 C8 97.52(15) 7_456 . ? N4 Co2 C8 78.74(14) 7_466 . ? C7 O1 Co1 132.8(3) . . ? C8 O3 Co2 87.7(3) . . ? C8 O4 Co2 87.7(3) . . ? C16 O6 Co2 135.2(4) . . ? C17 O7 Co1 137.9(3) . 6_564 ? Co1 O9 H1W 109.6 . . ? Co1 O9 H2W 107.6 . . ? H1W O9 H2W 105.4 . . ? H3W O10 H4W 97.5 . . ? C19 N1 C23 114.8(5) . . ? C19 N1 Co1 119.9(4) . . ? C23 N1 Co1 125.3(3) . . ? C33 N3 C37 115.6(4) . . ? C33 N3 Co1 123.9(3) . . ? C37 N3 Co1 120.3(3) . . ? C41 N4 C45 115.4(4) . . ? C41 N4 Co2 125.4(3) . 8_656 ? C45 N4 Co2 118.8(3) . 8_656 ? C46 N5 C50 116.6(5) . . ? C46 N5 Co1 122.3(3) . . ? C50 N5 Co1 121.2(4) . . ? C57 N6 C53 115.4(5) . . ? C57 N6 Co2 122.3(4) . . ? C53 N6 Co2 122.2(4) . . ? C2 C1 C6 118.2(5) . . ? C2 C1 C7 122.2(4) . . ? C6 C1 C7 119.5(4) . . ? C1 C2 C3 120.1(4) . . ? C1 C2 C8 123.1(4) . . ? C3 C2 C8 116.5(4) . . ? C4 C3 C2 120.1(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 121.0(5) . . ? C3 C4 C9 119.8(5) . . ? C5 C4 C9 119.1(5) . . ? C6 C5 C4 118.7(5) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C1 121.9(5) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? O2 C7 O1 126.3(5) . . ? O2 C7 C1 119.0(5) . . ? O1 C7 C1 114.6(4) . . ? O4 C8 O3 122.2(4) . . ? O4 C8 C2 120.2(5) . . ? O3 C8 C2 117.2(4) . . ? O4 C8 Co2 61.8(2) . . ? O3 C8 Co2 61.1(2) . . ? C2 C8 Co2 164.6(3) . . ? F2' C9 F3 58.9(9) . . ? F2' C9 F1' 111.9(8) . . ? F3 C9 F1' 134.4(11) . . ? F2' C9 F1 127.8(12) . . ? F3 C9 F1 108.7(6) . . ? F1' C9 F1 37.3(8) . . ? F2' C9 F3' 108.5(8) . . ? F3 C9 F3' 50.8(7) . . ? F1' C9 F3' 107.2(7) . . ? F1 C9 F3' 70.0(8) . . ? F2' C9 F2 47.8(9) . . ? F3 C9 F2 105.9(6) . . ? F1' C9 F2 73.4(9) . . ? F1 C9 F2 106.9(5) . . ? F3' C9 F2 149.1(10) . . ? F2' C9 C4 118.0(10) . . ? F3 C9 C4 114.5(5) . . ? F1' C9 C4 108.6(10) . . ? F1 C9 C4 112.9(6) . . ? F3' C9 C4 101.6(9) . . ? F2 C9 C4 107.4(5) . . ? C15 C10 C11 119.3(5) . . ? C15 C10 C16 119.3(5) . . ? C11 C10 C16 121.3(5) . . ? C10 C11 C12 118.8(5) . . ? C10 C11 C17 120.8(5) . . ? C12 C11 C17 120.4(5) . . ? C13 C12 C11 120.3(5) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 121.6(5) . . ? C14 C13 C18 118.3(6) . . ? C12 C13 C18 120.0(6) . . ? F6' C18' F5' 103.0(8) . . ? F6' C18' F4' 103.7(8) . . ? F5' C18' F4' 102.9(8) . . ? F6' C18' C14 104.9(10) . . ? F5' C18' C14 123.0(11) . . ? F4' C18' C14 116.9(11) . . ? F6' C18' F4' 69.4(8) . 8_655 ? F5' C18' F4' 52.3(7) . 8_655 ? F4' C18' F4' 73.6(9) . 8_655 ? C14 C18' F4' 169.3(8) . 8_655 ? C18' F4' F5' 107.7(8) . 7_465 ? C18' F4' C18' 150.9(8) . 7_465 ? F5' F4' C18' 43.2(5) 7_465 7_465 ? C18' F5' F4' 84.5(9) . 8_655 ? C13 C14 C15 117.1(6) . . ? C13 C14 C18' 118.1(7) . . ? C15 C14 C18' 120.9(7) . . ? F6 C18 F4 104.5(6) . . ? F6 C18 F5 104.5(6) . . ? F4 C18 F5 106.2(6) . . ? F6 C18 C13 114.6(7) . . ? F4 C18 C13 111.3(7) . . ? F5 C18 C13 114.9(6) . . ? C14 C15 C10 122.8(6) . . ? C14 C15 H15 118.6 . . ? C10 C15 H15 118.6 . . ? O5 C16 O6 126.8(5) . . ? O5 C16 C10 119.0(5) . . ? O6 C16 C10 114.2(5) . . ? O8 C17 O7 123.6(5) . . ? O8 C17 C11 119.6(5) . . ? O7 C17 C11 116.8(5) . . ? N1 C19 C20 123.6(5) . . ? N1 C19 H19 118.2 . . ? C20 C19 H19 118.2 . . ? C19 C20 C21 120.6(5) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C22 C21 C20 116.3(5) . . ? C22 C21 C24 121.6(6) . . ? C20 C21 C24 122.1(6) . . ? C21 C22 C23 119.4(5) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? N1 C23 C22 125.3(5) . . ? N1 C23 H23 117.3 . . ? C22 C23 H23 117.3 . . ? C25 C24 C21 112.4(5) . . ? C25 C24 H24A 109.1 . . ? C21 C24 H24A 109.1 . . ? C25 C24 H24B 109.1 . . ? C21 C24 H24B 109.1 . . ? H24A C24 H24B 107.9 . . ? C24 C25 C26 113.4(5) . . ? C24 C25 H25A 108.9 . . ? C26 C25 H25A 108.9 . . ? C24 C25 H25B 108.9 . . ? C26 C25 H25B 108.9 . . ? H25A C25 H25B 107.7 . . ? C29 C26 C25 114.7(4) . . ? C29 C26 H26A 108.6 . . ? C25 C26 H26A 108.6 . . ? C29 C26 H26B 108.6 . . ? C25 C26 H26B 108.6 . . ? H26A C26 H26B 107.6 . . ? N2 C27 C28 123.5(5) . . ? N2 C27 H27 118.2 . . ? C28 C27 H27 118.2 . . ? C27 C28 C29 121.5(5) . . ? C27 C28 H28 119.3 . . ? C29 C28 H28 119.3 . . ? C28 C29 C30 115.1(5) . . ? C28 C29 C26 122.7(5) . . ? C30 C29 C26 122.1(5) . . ? C31 C30 C29 120.6(5) . . ? C31 C30 H30 119.7 . . ? C29 C30 H30 119.7 . . ? N2 C31 C30 123.2(5) . . ? N2 C31 H31 118.4 . . ? C30 C31 H31 118.4 . . ? C27 N2 C31 116.0(4) . . ? C27 N2 Co2 122.2(3) . 8_556 ? C31 N2 Co2 121.9(3) . 8_556 ? N3 C33 C34 123.1(5) . . ? N3 C33 H33 118.4 . . ? C34 C33 H33 118.4 . . ? C35 C34 C33 120.6(5) . . ? C35 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? C36 C35 C34 116.3(5) . . ? C36 C35 C38 119.5(5) . . ? C34 C35 C38 124.2(5) . . ? C37 C36 C35 119.5(5) . . ? C37 C36 H36 120.3 . . ? C35 C36 H36 120.3 . . ? N3 C37 C36 124.8(5) . . ? N3 C37 H37 117.6 . . ? C36 C37 H37 117.6 . . ? C35 C38 C39 118.2(5) . . ? C35 C38 H38A 107.8 . . ? C39 C38 H38A 107.8 . . ? C35 C38 H38B 107.8 . . ? C39 C38 H38B 107.8 . . ? H38A C38 H38B 107.1 . . ? C40 C39 C38 110.4(4) . . ? C40 C39 H39A 109.6 . . ? C38 C39 H39A 109.6 . . ? C40 C39 H39B 109.6 . . ? C38 C39 H39B 109.6 . . ? H39A C39 H39B 108.1 . . ? C39 C40 C43 117.9(4) . . ? C39 C40 H40A 107.8 . . ? C43 C40 H40A 107.8 . . ? C39 C40 H40B 107.8 . . ? C43 C40 H40B 107.8 . . ? H40A C40 H40B 107.2 . . ? N4 C41 C42 122.8(5) . . ? N4 C41 H41 118.6 . . ? C42 C41 H41 118.6 . . ? C43 C42 C41 121.2(5) . . ? C43 C42 H42 119.4 . . ? C41 C42 H42 119.4 . . ? C44 C43 C42 115.0(5) . . ? C44 C43 C40 120.1(5) . . ? C42 C43 C40 124.6(5) . . ? C43 C44 C45 121.8(5) . . ? C43 C44 H44 119.1 . . ? C45 C44 H44 119.1 . . ? N4 C45 C44 123.8(5) . . ? N4 C45 H45 118.1 . . ? C44 C45 H45 118.1 . . ? N5 C46 C47 123.6(5) . . ? N5 C46 H46 118.2 . . ? C47 C46 H46 118.2 . . ? C48 C47 C46 119.4(5) . . ? C48 C47 H47 120.3 . . ? C46 C47 H47 120.3 . . ? C49 C48 C47 117.1(5) . . ? C49 C48 C51 122.4(5) . . ? C47 C48 C51 120.5(5) . . ? C48 C49 C50 120.8(5) . . ? C48 C49 H49 119.6 . . ? C50 C49 H49 119.6 . . ? N5 C50 C49 122.4(5) . . ? N5 C50 H50 118.8 . . ? C49 C50 H50 118.8 . . ? C52 C51 C48 122.6(7) . . ? C52 C51 C52 58.0(8) . 2_575 ? C48 C51 C52 96.7(5) . 2_575 ? C52 C51 H51A 108.3 . . ? C48 C51 H51A 106.0 . . ? C52 C51 H51A 157.3 2_575 . ? C52 C51 H51B 106.1 . . ? C48 C51 H51B 106.0 . . ? C52 C51 H51B 64.9 2_575 . ? H51A C51 H51B 106.9 . . ? C51 C52 C52 72.5(7) . 2_575 ? C51 C52 C51 107.5(8) . 2_575 ? C52 C52 C51 49.5(5) 2_575 2_575 ? C51 C52 H52A 109.1 . . ? C52 C52 H52A 107.2 2_575 . ? C51 C52 H52A 63.3 2_575 . ? C51 C52 H52B 107.6 . . ? C52 C52 H52B 140.6 2_575 . ? C51 C52 H52B 144.4 2_575 . ? H52A C52 H52B 109.5 . . ? N6 C53 C54 124.1(5) . . ? N6 C53 H53 118.0 . . ? C54 C53 H53 118.0 . . ? C55 C54 C53 118.9(6) . . ? C55 C54 H54 120.6 . . ? C53 C54 H54 120.6 . . ? C56 C55 C54 117.7(5) . . ? C56 C55 C58 123.6(6) . . ? C54 C55 C58 118.7(6) . . ? C55 C56 C57 119.7(6) . . ? C55 C56 H56 120.1 . . ? C57 C56 H56 120.1 . . ? N6 C57 C56 124.1(5) . . ? N6 C57 H57 118.0 . . ? C56 C57 H57 118.0 . . ? C59 C58 C55 112.2(8) . . ? C59 C58 C59 44.5(9) . 2_675 ? C55 C58 C59 100.4(6) . 2_675 ? C59 C58 H58A 110.4 . . ? C55 C58 H58A 107.8 . . ? C59 C58 H58A 148.9 2_675 . ? C59 C58 H58B 110.2 . . ? C55 C58 H58B 108.0 . . ? C59 C58 H58B 74.3 2_675 . ? H58A C58 H58B 108.2 . . ? C59 C59 C58 76.7(10) 2_675 . ? C59 C59 C58 58.8(9) 2_675 2_675 ? C58 C59 C58 112.2(9) . 2_675 ? C59 C59 H59A 101.4 2_675 . ? C58 C59 H59A 107.4 . . ? C58 C59 H59A 47.3 2_675 . ? C59 C59 H59B 143.8 2_675 . ? C58 C59 H59B 110.2 . . ? C58 C59 H59B 136.3 2_675 . ? H59A C59 H59B 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 O7 Co1 O1 C7 -145.4(18) 6_565 . . . ? O9 Co1 O1 C7 -20.0(4) . . . . ? N3 Co1 O1 C7 68.6(4) . . . . ? N5 Co1 O1 C7 159.2(4) . . . . ? N1 Co1 O1 C7 -108.8(4) . . . . ? O6 Co2 O3 C8 7.7(8) . . . . ? N6 Co2 O3 C8 166.6(3) . . . . ? O4 Co2 O3 C8 -5.6(2) . . . . ? N2 Co2 O3 C8 -103.6(3) 7_456 . . . ? N4 Co2 O3 C8 78.0(3) 7_466 . . . ? O6 Co2 O4 C8 -171.4(2) . . . . ? N6 Co2 O4 C8 -16.1(5) . . . . ? O3 Co2 O4 C8 5.8(2) . . . . ? N2 Co2 O4 C8 92.5(3) 7_456 . . . ? N4 Co2 O4 C8 -82.0(3) 7_466 . . . ? N6 Co2 O6 C16 -160.9(5) . . . . ? O3 Co2 O6 C16 -1.7(10) . . . . ? O4 Co2 O6 C16 10.6(5) . . . . ? N2 Co2 O6 C16 109.3(5) 7_456 . . . ? N4 Co2 O6 C16 -71.2(5) 7_466 . . . ? C8 Co2 O6 C16 4.2(5) . . . . ? O7 Co1 N1 C19 -125.7(4) 6_565 . . . ? O1 Co1 N1 C19 56.7(4) . . . . ? O9 Co1 N1 C19 -30.9(4) . . . . ? N3 Co1 N1 C19 7(3) . . . . ? N5 Co1 N1 C19 145.1(4) . . . . ? O7 Co1 N1 C23 52.7(4) 6_565 . . . ? O1 Co1 N1 C23 -125.0(4) . . . . ? O9 Co1 N1 C23 147.5(4) . . . . ? N3 Co1 N1 C23 -175(31) . . . . ? N5 Co1 N1 C23 -36.6(4) . . . . ? O7 Co1 N3 C33 -155.6(4) 6_565 . . . ? O1 Co1 N3 C33 22.2(4) . . . . ? O9 Co1 N3 C33 109.5(4) . . . . ? N5 Co1 N3 C33 -66.4(4) . . . . ? N1 Co1 N3 C33 72(3) . . . . ? O7 Co1 N3 C37 30.2(4) 6_565 . . . ? O1 Co1 N3 C37 -152.0(3) . . . . ? O9 Co1 N3 C37 -64.7(4) . . . . ? N5 Co1 N3 C37 119.3(4) . . . . ? N1 Co1 N3 C37 -102(3) . . . . ? O7 Co1 N5 C46 175.8(4) 6_565 . . . ? O1 Co1 N5 C46 -7.4(4) . . . . ? O9 Co1 N5 C46 3(2) . . . . ? N3 Co1 N5 C46 85.3(4) . . . . ? N1 Co1 N5 C46 -92.5(4) . . . . ? O7 Co1 N5 C50 -5.1(4) 6_565 . . . ? O1 Co1 N5 C50 171.6(4) . . . . ? O9 Co1 N5 C50 -177(32) . . . . ? N3 Co1 N5 C50 -95.6(4) . . . . ? N1 Co1 N5 C50 86.6(4) . . . . ? O6 Co2 N6 C57 -6.3(4) . . . . ? O3 Co2 N6 C57 177.9(4) . . . . ? O4 Co2 N6 C57 -162.8(4) . . . . ? N2 Co2 N6 C57 87.3(4) 7_456 . . . ? N4 Co2 N6 C57 -98.2(4) 7_466 . . . ? C8 Co2 N6 C57 -173.2(3) . . . . ? O6 Co2 N6 C53 169.6(4) . . . . ? O3 Co2 N6 C53 -6.1(4) . . . . ? O4 Co2 N6 C53 13.2(7) . . . . ? N2 Co2 N6 C53 -96.7(4) 7_456 . . . ? N4 Co2 N6 C53 77.8(4) 7_466 . . . ? C8 Co2 N6 C53 2.7(5) . . . . ? C6 C1 C2 C3 0.8(7) . . . . ? C7 C1 C2 C3 177.8(4) . . . . ? C6 C1 C2 C8 173.9(5) . . . . ? C7 C1 C2 C8 -9.1(7) . . . . ? C1 C2 C3 C4 0.4(8) . . . . ? C8 C2 C3 C4 -173.1(5) . . . . ? C2 C3 C4 C5 -0.8(8) . . . . ? C2 C3 C4 C9 178.7(5) . . . . ? C3 C4 C5 C6 0.0(8) . . . . ? C9 C4 C5 C6 -179.6(5) . . . . ? C4 C5 C6 C1 1.3(8) . . . . ? C2 C1 C6 C5 -1.7(7) . . . . ? C7 C1 C6 C5 -178.7(5) . . . . ? Co1 O1 C7 O2 -2.9(7) . . . . ? Co1 O1 C7 C1 175.4(3) . . . . ? C2 C1 C7 O2 -34.6(7) . . . . ? C6 C1 C7 O2 142.3(5) . . . . ? C2 C1 C7 O1 146.8(4) . . . . ? C6 C1 C7 O1 -36.2(6) . . . . ? Co2 O4 C8 O3 -10.1(4) . . . . ? Co2 O4 C8 C2 162.5(4) . . . . ? Co2 O3 C8 O4 10.2(4) . . . . ? Co2 O3 C8 C2 -162.6(3) . . . . ? C1 C2 C8 O4 118.4(5) . . . . ? C3 C2 C8 O4 -68.3(6) . . . . ? C1 C2 C8 O3 -68.7(6) . . . . ? C3 C2 C8 O3 104.7(5) . . . . ? C1 C2 C8 Co2 -148.5(13) . . . . ? C3 C2 C8 Co2 24.8(17) . . . . ? O6 Co2 C8 O4 12.1(3) . . . . ? N6 Co2 C8 O4 172.7(2) . . . . ? O3 Co2 C8 O4 -170.2(4) . . . . ? N2 Co2 C8 O4 -91.6(3) 7_456 . . . ? N4 Co2 C8 O4 92.6(3) 7_466 . . . ? O6 Co2 C8 O3 -177.7(2) . . . . ? N6 Co2 C8 O3 -17.1(3) . . . . ? O4 Co2 C8 O3 170.2(4) . . . . ? N2 Co2 C8 O3 78.6(3) 7_456 . . . ? N4 Co2 C8 O3 -97.2(3) 7_466 . . . ? O6 Co2 C8 C2 -89.6(15) . . . . ? N6 Co2 C8 C2 71.0(15) . . . . ? O3 Co2 C8 C2 88.1(15) . . . . ? O4 Co2 C8 C2 -101.7(15) . . . . ? N2 Co2 C8 C2 166.8(15) 7_456 . . . ? N4 Co2 C8 C2 -9.1(15) 7_466 . . . ? C3 C4 C9 F2' 53.7(13) . . . . ? C5 C4 C9 F2' -126.7(12) . . . . ? C3 C4 C9 F3 -12.7(8) . . . . ? C5 C4 C9 F3 166.9(6) . . . . ? C3 C4 C9 F1' -177.6(10) . . . . ? C5 C4 C9 F1' 2.0(11) . . . . ? C3 C4 C9 F1 -137.8(6) . . . . ? C5 C4 C9 F1 41.8(8) . . . . ? C3 C4 C9 F3' -64.8(11) . . . . ? C5 C4 C9 F3' 114.8(10) . . . . ? C3 C4 C9 F2 104.5(6) . . . . ? C5 C4 C9 F2 -75.9(7) . . . . ? C15 C10 C11 C12 -0.4(8) . . . . ? C16 C10 C11 C12 -177.1(5) . . . . ? C15 C10 C11 C17 -179.5(5) . . . . ? C16 C10 C11 C17 3.8(7) . . . . ? C10 C11 C12 C13 -1.8(7) . . . . ? C17 C11 C12 C13 177.3(5) . . . . ? C11 C12 C13 C14 3.4(9) . . . . ? C11 C12 C13 C18 -178.4(5) . . . . ? F6' C18' F4' F5' 28.6(13) . . . 7_465 ? F5' C18' F4' F5' 135.7(10) . . . 7_465 ? C14 C18' F4' F5' -86.3(11) . . . 7_465 ? F4' C18' F4' F5' 91.9(12) 8_655 . . 7_465 ? F6' C18' F4' C18' 28(2) . . . 7_465 ? F5' C18' F4' C18' 135.5(18) . . . 7_465 ? C14 C18' F4' C18' -87(2) . . . 7_465 ? F4' C18' F4' C18' 92(2) 8_655 . . 7_465 ? F6' C18' F5' F4' 50.5(11) . . . 8_655 ? F4' C18' F5' F4' -57.2(12) . . . 8_655 ? C14 C18' F5' F4' 168.2(11) . . . 8_655 ? C12 C13 C14 C15 -2.6(10) . . . . ? C18 C13 C14 C15 179.2(6) . . . . ? C12 C13 C14 C18' 155.6(7) . . . . ? C18 C13 C14 C18' -22.6(10) . . . . ? F6' C18' C14 C13 85.6(10) . . . . ? F5' C18' C14 C13 -31.3(13) . . . . ? F4' C18' C14 C13 -160.2(8) . . . . ? F4' C18' C14 C13 29(6) 8_655 . . . ? F6' C18' C14 C15 -117.1(9) . . . . ? F5' C18' C14 C15 126.1(10) . . . . ? F4' C18' C14 C15 -2.8(13) . . . . ? F4' C18' C14 C15 -174(5) 8_655 . . . ? C14 C13 C18 F6 -56.9(9) . . . . ? C12 C13 C18 F6 125.0(6) . . . . ? C14 C13 C18 F4 61.5(8) . . . . ? C12 C13 C18 F4 -116.7(6) . . . . ? C14 C13 C18 F5 -177.9(6) . . . . ? C12 C13 C18 F5 3.9(9) . . . . ? C13 C14 C15 C10 0.4(10) . . . . ? C18' C14 C15 C10 -157.2(7) . . . . ? C11 C10 C15 C14 1.1(9) . . . . ? C16 C10 C15 C14 177.9(6) . . . . ? Co2 O6 C16 O5 -12.6(8) . . . . ? Co2 O6 C16 C10 165.8(3) . . . . ? C15 C10 C16 O5 59.9(7) . . . . ? C11 C10 C16 O5 -123.3(5) . . . . ? C15 C10 C16 O6 -118.6(6) . . . . ? C11 C10 C16 O6 58.1(6) . . . . ? Co1 O7 C17 O8 -126.9(5) 6_564 . . . ? Co1 O7 C17 C11 53.1(6) 6_564 . . . ? C10 C11 C17 O8 -124.9(5) . . . . ? C12 C11 C17 O8 56.0(7) . . . . ? C10 C11 C17 O7 55.1(6) . . . . ? C12 C11 C17 O7 -124.0(5) . . . . ? C23 N1 C19 C20 -0.2(8) . . . . ? Co1 N1 C19 C20 178.3(4) . . . . ? N1 C19 C20 C21 -0.6(9) . . . . ? C19 C20 C21 C22 1.8(9) . . . . ? C19 C20 C21 C24 -178.7(6) . . . . ? C20 C21 C22 C23 -2.2(8) . . . . ? C24 C21 C22 C23 178.3(5) . . . . ? C19 N1 C23 C22 -0.3(7) . . . . ? Co1 N1 C23 C22 -178.7(4) . . . . ? C21 C22 C23 N1 1.5(8) . . . . ? C22 C21 C24 C25 102.0(7) . . . . ? C20 C21 C24 C25 -77.4(7) . . . . ? C21 C24 C25 C26 173.3(5) . . . . ? C24 C25 C26 C29 67.6(7) . . . . ? N2 C27 C28 C29 0.4(8) . . . . ? C27 C28 C29 C30 -2.2(7) . . . . ? C27 C28 C29 C26 174.6(5) . . . . ? C25 C26 C29 C28 69.4(7) . . . . ? C25 C26 C29 C30 -114.0(6) . . . . ? C28 C29 C30 C31 2.1(7) . . . . ? C26 C29 C30 C31 -174.7(4) . . . . ? C29 C30 C31 N2 -0.2(8) . . . . ? C28 C27 N2 C31 1.5(7) . . . . ? C28 C27 N2 Co2 -177.3(4) . . . 8_556 ? C30 C31 N2 C27 -1.6(7) . . . . ? C30 C31 N2 Co2 177.2(4) . . . 8_556 ? C37 N3 C33 C34 -2.4(7) . . . . ? Co1 N3 C33 C34 -176.8(4) . . . . ? N3 C33 C34 C35 0.7(8) . . . . ? C33 C34 C35 C36 1.1(7) . . . . ? C33 C34 C35 C38 -178.9(5) . . . . ? C34 C35 C36 C37 -1.1(7) . . . . ? C38 C35 C36 C37 178.9(5) . . . . ? C33 N3 C37 C36 2.4(7) . . . . ? Co1 N3 C37 C36 177.1(4) . . . . ? C35 C36 C37 N3 -0.7(8) . . . . ? C36 C35 C38 C39 129.2(5) . . . . ? C34 C35 C38 C39 -50.8(8) . . . . ? C35 C38 C39 C40 -173.7(5) . . . . ? C38 C39 C40 C43 -178.3(5) . . . . ? C45 N4 C41 C42 0.7(7) . . . . ? Co2 N4 C41 C42 173.8(4) 8_656 . . . ? N4 C41 C42 C43 -0.5(9) . . . . ? C41 C42 C43 C44 0.0(8) . . . . ? C41 C42 C43 C40 -174.5(5) . . . . ? C39 C40 C43 C44 150.6(5) . . . . ? C39 C40 C43 C42 -35.3(9) . . . . ? C42 C43 C44 C45 0.3(8) . . . . ? C40 C43 C44 C45 175.0(5) . . . . ? C41 N4 C45 C44 -0.4(8) . . . . ? Co2 N4 C45 C44 -174.0(4) 8_656 . . . ? C43 C44 C45 N4 -0.1(9) . . . . ? C50 N5 C46 C47 -1.2(7) . . . . ? Co1 N5 C46 C47 177.9(4) . . . . ? N5 C46 C47 C48 0.4(8) . . . . ? C46 C47 C48 C49 -0.3(8) . . . . ? C46 C47 C48 C51 -178.4(5) . . . . ? C47 C48 C49 C50 1.0(8) . . . . ? C51 C48 C49 C50 179.1(5) . . . . ? C46 N5 C50 C49 1.9(7) . . . . ? Co1 N5 C50 C49 -177.2(4) . . . . ? C48 C49 C50 N5 -1.9(8) . . . . ? C49 C48 C51 C52 -138.2(8) . . . . ? C47 C48 C51 C52 39.9(11) . . . . ? C49 C48 C51 C52 -82.1(7) . . . 2_575 ? C47 C48 C51 C52 95.9(6) . . . 2_575 ? C48 C51 C52 C52 76.3(8) . . . 2_575 ? C48 C51 C52 C51 111.9(9) . . . 2_575 ? C52 C51 C52 C51 35.6(7) 2_575 . . 2_575 ? C57 N6 C53 C54 1.7(8) . . . . ? Co2 N6 C53 C54 -174.5(4) . . . . ? N6 C53 C54 C55 -3.4(9) . . . . ? C53 C54 C55 C56 3.3(9) . . . . ? C53 C54 C55 C58 -177.5(6) . . . . ? C54 C55 C56 C57 -1.8(8) . . . . ? C58 C55 C56 C57 179.0(6) . . . . ? C53 N6 C57 C56 0.0(8) . . . . ? Co2 N6 C57 C56 176.2(4) . . . . ? C55 C56 C57 N6 0.1(8) . . . . ? C56 C55 C58 C59 47.7(11) . . . . ? C54 C55 C58 C59 -131.5(8) . . . . ? C56 C55 C58 C59 92.6(8) . . . 2_675 ? C54 C55 C58 C59 -86.6(8) . . . 2_675 ? C55 C58 C59 C59 82.0(8) . . . 2_675 ? C55 C58 C59 C58 129.8(9) . . . 2_675 ? C59 C58 C59 C58 47.8(9) 2_675 . . 2_675 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9 H1W O5 0.85 1.99 2.764(4) 150.5 6_565 O9 H2W O2 0.85 1.92 2.707(4) 152.9 . O10 H3W O3 0.85 2.02 2.865(5) 175.5 8_656 O10 H4W O8 0.85 1.94 2.792(6) 178.7 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.435 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.048 data_2a _database_code_depnum_ccdc_archive 'CCDC 919377' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C57 H51 F6 N6 Ni2 O10' _chemical_formula_weight 1211.46 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' Ni Ni 0.3393 1.1124 '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 I-4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'y, -x, -z' '-x, -y, z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-x+1/2, -y+1/2, z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 27.4279(14) _cell_length_b 27.4279(14) _cell_length_c 14.3090(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10764.5(16) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2079 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 15.94 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5000 _exptl_absorpt_coefficient_mu 0.786 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7186 _exptl_absorpt_correction_T_max 0.9116 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30982 _diffrn_reflns_av_R_equivalents 0.1005 _diffrn_reflns_av_sigmaI/netI 0.1176 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.50 _reflns_number_total 9924 _reflns_number_gt 5890 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+11.0122P] 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 0.525(19) _refine_ls_number_reflns 9924 _refine_ls_number_parameters 776 _refine_ls_number_restraints 56 _refine_ls_R_factor_all 0.1227 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.057 _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 Ni1 Ni 0.10522(3) 0.80012(3) 0.92400(6) 0.0383(2) Uani 1 1 d . . . Ni2 Ni 0.32231(3) 0.87470(3) 0.65334(6) 0.0412(2) Uani 1 1 d . . . O1 O 0.12025(17) 0.84968(16) 0.8221(3) 0.0449(13) Uani 1 1 d . . . O2 O 0.17128(19) 0.81151(18) 0.7236(4) 0.0534(14) Uani 1 1 d . . . O3 O 0.25673(17) 0.89474(17) 0.7221(4) 0.0448(13) Uani 1 1 d . . . O4 O 0.25475(16) 0.86466(16) 0.5802(3) 0.0426(12) Uani 1 1 d . . . O5 O 0.34276(18) 0.83807(18) 0.4253(4) 0.0535(13) Uani 1 1 d . A . O6 O 0.37568(17) 0.85603(18) 0.5649(4) 0.0511(13) Uani 1 1 d . A . O7 O 0.41489(17) 0.74747(17) 0.5287(3) 0.0459(13) Uani 1 1 d . . . O8 O 0.4739(2) 0.7752(2) 0.6185(4) 0.0704(17) Uani 1 1 d . . . O9 O 0.12650(16) 0.74418(16) 0.8302(3) 0.0465(13) Uani 1 1 d . . . H1W H 0.1454 0.7243 0.8574 0.070 Uiso 1 1 d R . . H2W H 0.1435 0.7575 0.7878 0.070 Uiso 1 1 d R . . O10 O 0.5493(3) 0.7084(3) 0.6348(6) 0.138(4) Uani 1 1 d . . . H3W H 0.5644 0.7223 0.6792 0.207 Uiso 1 1 d R . . H4W H 0.5256 0.7280 0.6316 0.207 Uiso 1 1 d R . . F1 F 0.1044(3) 1.0502(2) 0.5475(5) 0.136(3) Uani 1 1 d U . . F2 F 0.1113(3) 1.0046(3) 0.4311(6) 0.163(3) Uani 1 1 d U . . F3 F 0.1722(3) 1.0345(3) 0.4846(7) 0.166(3) Uani 1 1 d U . . N1 N 0.0337(2) 0.7978(2) 0.8638(4) 0.0400(14) Uani 1 1 d . . . N3 N 0.1779(2) 0.8008(2) 0.9757(4) 0.0427(15) Uani 1 1 d . . . N4 N 0.5529(2) 0.8174(2) 0.9088(4) 0.0429(15) Uani 1 1 d . . . N5 N 0.0862(2) 0.8593(2) 1.0132(4) 0.0446(15) Uani 1 1 d . . . N6 N 0.3735(2) 0.8995(2) 0.7510(4) 0.0465(16) Uani 1 1 d . . . C1 C 0.1438(2) 0.8911(2) 0.6876(5) 0.0376(17) Uani 1 1 d . . . C2 C 0.1837(2) 0.9066(2) 0.6354(5) 0.0382(17) Uani 1 1 d . . . C3 C 0.1791(3) 0.9468(3) 0.5792(6) 0.052(2) Uani 1 1 d . . . H3 H 0.2058 0.9567 0.5437 0.062 Uiso 1 1 calc R . . C4 C 0.1371(3) 0.9724(3) 0.5737(6) 0.057(2) Uani 1 1 d . . . C5 C 0.0966(3) 0.9567(3) 0.6229(6) 0.056(2) Uani 1 1 d . . . H5 H 0.0671 0.9732 0.6179 0.067 Uiso 1 1 calc R . . C6 C 0.1005(3) 0.9165(3) 0.6791(5) 0.049(2) Uani 1 1 d . . . H6 H 0.0734 0.9060 0.7124 0.059 Uiso 1 1 calc R . . C7 C 0.1459(3) 0.8467(3) 0.7492(6) 0.0416(18) Uani 1 1 d . . . C8 C 0.2343(2) 0.8856(2) 0.6470(5) 0.0344(16) Uani 1 1 d . . . C9 C 0.1334(4) 1.0167(4) 0.5148(9) 0.096(3) Uani 1 1 d U . . C10 C 0.4284(3) 0.8442(3) 0.4382(5) 0.0447(19) Uani 1 1 d . A . C11 C 0.4632(2) 0.8125(2) 0.4714(5) 0.0414(18) Uani 1 1 d . . . C12 C 0.5104(3) 0.8138(3) 0.4353(6) 0.055(2) Uani 1 1 d . A . H12 H 0.5340 0.7926 0.4583 0.066 Uiso 1 1 calc R . . C13 C 0.5223(3) 0.8463(3) 0.3659(7) 0.068(3) Uani 1 1 d . . . C18' C 0.5034(14) 0.9217(18) 0.280(3) 0.110(15) Uani 0.317(6) 1 d P A 2 F4' F 0.4745(12) 0.9636(11) 0.286(2) 0.178(13) Uani 0.317(6) 1 d P A 2 F5' F 0.5483(8) 0.9443(11) 0.3080(16) 0.141(11) Uani 0.317(6) 1 d P A 2 F6' F 0.5145(13) 0.9119(12) 0.199(2) 0.195(14) Uani 0.317(6) 1 d P A 2 C14 C 0.4880(3) 0.8792(4) 0.3330(7) 0.081(3) Uani 1 1 d . A . C18 C 0.5712(4) 0.8472(6) 0.3261(10) 0.062(4) Uani 0.683(6) 1 d P A 1 F4 F 0.5922(3) 0.8893(3) 0.3402(7) 0.106(3) Uani 0.683(6) 1 d P A 1 F5 F 0.6004(3) 0.8126(4) 0.3613(7) 0.104(3) Uani 0.683(6) 1 d P A 1 F6 F 0.5727(3) 0.8405(3) 0.2358(6) 0.096(3) Uani 0.683(6) 1 d P A 1 C15 C 0.4408(3) 0.8775(3) 0.3699(7) 0.074(3) Uani 1 1 d . . . H15 H 0.4173 0.8992 0.3481 0.089 Uiso 1 1 calc R A . C16 C 0.3773(3) 0.8459(3) 0.4780(6) 0.046(2) Uani 1 1 d . . . C17 C 0.4503(3) 0.7757(3) 0.5448(6) 0.046(2) Uani 1 1 d . . . C19 C 0.0282(3) 0.7872(3) 0.7733(6) 0.061(2) Uani 1 1 d . . . H19 H 0.0559 0.7817 0.7374 0.073 Uiso 1 1 calc R . . C20 C -0.0173(3) 0.7841(3) 0.7300(7) 0.072(3) Uani 1 1 d . . . H20 H -0.0191 0.7764 0.6668 0.086 Uiso 1 1 calc R . . C21 C -0.0596(3) 0.7923(3) 0.7803(7) 0.064(2) Uani 1 1 d . . . C22 C -0.0532(3) 0.8045(3) 0.8724(6) 0.060(2) Uani 1 1 d . . . H22 H -0.0803 0.8114 0.9093 0.072 Uiso 1 1 calc R . . C23 C -0.0076(3) 0.8065(2) 0.9106(6) 0.0458(19) Uani 1 1 d . . . H23 H -0.0051 0.8146 0.9736 0.055 Uiso 1 1 calc R . . C24 C -0.1103(3) 0.7878(4) 0.7350(8) 0.083(3) Uani 1 1 d . . . H24A H -0.1109 0.7590 0.6955 0.100 Uiso 1 1 calc R . . H24B H -0.1346 0.7836 0.7835 0.100 Uiso 1 1 calc R . . C25 C -0.1229(3) 0.8311(3) 0.6781(7) 0.075(3) Uani 1 1 d . . . H25A H -0.0968 0.8374 0.6339 0.090 Uiso 1 1 calc R . . H25B H -0.1255 0.8593 0.7188 0.090 Uiso 1 1 calc R . . C26 C -0.1705(3) 0.8249(3) 0.6250(6) 0.064(2) Uani 1 1 d . . . H26A H -0.1737 0.8517 0.5813 0.076 Uiso 1 1 calc R . . H26B H -0.1684 0.7951 0.5886 0.076 Uiso 1 1 calc R . . C27 C -0.2775(3) 0.8622(3) 0.7773(5) 0.0430(19) Uani 1 1 d . . . H27 H -0.2881 0.8902 0.8077 0.052 Uiso 1 1 calc R . . C28 C -0.2338(3) 0.8632(3) 0.7301(6) 0.050(2) Uani 1 1 d . . . H28 H -0.2156 0.8919 0.7295 0.060 Uiso 1 1 calc R . . C29 C -0.2161(3) 0.8227(3) 0.6835(5) 0.049(2) Uani 1 1 d . . . C30 C -0.2444(3) 0.7811(3) 0.6899(5) 0.049(2) Uani 1 1 d . . . H30 H -0.2342 0.7524 0.6615 0.059 Uiso 1 1 calc R . . C31 C -0.2877(3) 0.7823(3) 0.7382(5) 0.049(2) Uani 1 1 d . . . H31 H -0.3059 0.7537 0.7412 0.058 Uiso 1 1 calc R . . N2 N -0.3054(2) 0.8216(2) 0.7809(4) 0.0416(15) Uani 1 1 d . . . C33 C 0.2085(3) 0.8379(3) 0.9622(5) 0.0462(19) Uani 1 1 d . . . H33 H 0.1970 0.8656 0.9317 0.055 Uiso 1 1 calc R . . C34 C 0.2559(3) 0.8373(3) 0.9911(6) 0.051(2) Uani 1 1 d . . . H34 H 0.2757 0.8641 0.9791 0.062 Uiso 1 1 calc R . . C35 C 0.2749(3) 0.7975(3) 1.0380(5) 0.0452(19) Uani 1 1 d . . . C36 C 0.2432(3) 0.7585(3) 1.0500(5) 0.049(2) Uani 1 1 d . . . H36 H 0.2541 0.7300 1.0782 0.059 Uiso 1 1 calc R . . C37 C 0.1961(3) 0.7620(3) 1.0203(5) 0.0439(19) Uani 1 1 d . . . H37 H 0.1754 0.7359 1.0317 0.053 Uiso 1 1 calc R . . C38 C 0.3264(3) 0.7927(3) 1.0749(6) 0.069(3) Uani 1 1 d . . . H38A H 0.3309 0.7594 1.0961 0.083 Uiso 1 1 calc R . . H38B H 0.3295 0.8137 1.1292 0.083 Uiso 1 1 calc R . . C39 C 0.3679(2) 0.8048(3) 1.0080(6) 0.050(2) Uani 1 1 d . . . H39A H 0.3664 0.8389 0.9906 0.060 Uiso 1 1 calc R . . H39B H 0.3648 0.7854 0.9516 0.060 Uiso 1 1 calc R . . C40 C 0.4167(3) 0.7941(4) 1.0551(6) 0.075(3) Uani 1 1 d . . . H40A H 0.4178 0.8124 1.1129 0.090 Uiso 1 1 calc R . . H40B H 0.4171 0.7598 1.0716 0.090 Uiso 1 1 calc R . . C41 C 0.5124(3) 0.8069(3) 0.8625(6) 0.055(2) Uani 1 1 d . . . H41 H 0.5140 0.8039 0.7979 0.066 Uiso 1 1 calc R . . C42 C 0.4673(3) 0.8000(3) 0.9064(6) 0.057(2) Uani 1 1 d . . . H42 H 0.4401 0.7921 0.8706 0.068 Uiso 1 1 calc R . . C43 C 0.4626(3) 0.8048(3) 1.0017(6) 0.0448(19) Uani 1 1 d . . . C44 C 0.5043(3) 0.8156(3) 1.0481(6) 0.059(2) Uani 1 1 d . . . H44 H 0.5036 0.8189 1.1127 0.071 Uiso 1 1 calc R . . C45 C 0.5477(3) 0.8216(3) 1.0010(6) 0.061(2) Uani 1 1 d . . . H45 H 0.5752 0.8292 1.0360 0.074 Uiso 1 1 calc R . . C46 C 0.0929(2) 0.9058(3) 0.9891(6) 0.047(2) Uani 1 1 d . . . H46 H 0.1078 0.9125 0.9322 0.056 Uiso 1 1 calc R . . C47 C 0.0789(3) 0.9442(3) 1.0439(6) 0.057(2) Uani 1 1 d . . . H47 H 0.0837 0.9759 1.0227 0.068 Uiso 1 1 calc R . . C48 C 0.0578(3) 0.9367(3) 1.1301(6) 0.057(2) Uani 1 1 d . . . C49 C 0.0509(3) 0.8889(3) 1.1554(6) 0.061(2) Uani 1 1 d . . . H49 H 0.0360 0.8818 1.2122 0.073 Uiso 1 1 calc R . . C50 C 0.0654(3) 0.8514(3) 1.0988(5) 0.056(2) Uani 1 1 d . . . H50 H 0.0609 0.8195 1.1191 0.067 Uiso 1 1 calc R . . C51 C 0.0415(4) 0.9786(4) 1.1894(8) 0.101(4) Uani 1 1 d U . . H51A H 0.0695 0.9883 1.2247 0.121 Uiso 1 1 d R . . H51B H 0.0186 0.9654 1.2332 0.121 Uiso 1 1 d R . . C52 C 0.0210(5) 1.0156(7) 1.1548(13) 0.064(5) Uani 0.50 1 d PU . . H52A H 0.0130 1.0374 1.2049 0.096 Uiso 0.50 1 d PR . . H52B H 0.0441 1.0308 1.1141 0.096 Uiso 0.50 1 d PR . . C53 C 0.3594(3) 0.9243(3) 0.8264(6) 0.062(2) Uani 1 1 d . . . H53 H 0.3261 0.9282 0.8365 0.074 Uiso 1 1 calc R . . C54 C 0.3911(4) 0.9444(3) 0.8900(6) 0.074(3) Uani 1 1 d . . . H54 H 0.3791 0.9618 0.9408 0.088 Uiso 1 1 calc R . . C55 C 0.4404(4) 0.9387(3) 0.8783(7) 0.065(3) Uani 1 1 d . . . C56 C 0.4551(3) 0.9128(3) 0.7996(7) 0.061(2) Uani 1 1 d . . . H56 H 0.4882 0.9079 0.7885 0.073 Uiso 1 1 calc R . . C57 C 0.4216(3) 0.8945(3) 0.7384(6) 0.056(2) Uani 1 1 d . . . H57 H 0.4326 0.8778 0.6858 0.067 Uiso 1 1 calc R . . C58 C 0.4758(4) 0.9593(4) 0.9488(9) 0.112(4) Uani 1 1 d U . . H58A H 0.4880 0.9331 0.9863 0.135 Uiso 1 1 d R . . H58B H 0.4579 0.9808 0.9887 0.135 Uiso 1 1 d R . . C59 C 0.5132(8) 0.9834(7) 0.9072(14) 0.095(7) Uani 0.50 1 d PU . . H59A H 0.5337 0.9957 0.9560 0.142 Uiso 0.50 1 d PR . . H59B H 0.5315 0.9617 0.8682 0.142 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 Ni1 0.0359(5) 0.0380(5) 0.0409(5) 0.0025(4) 0.0034(4) 0.0001(4) Ni2 0.0412(6) 0.0382(5) 0.0441(6) 0.0000(5) 0.0037(5) 0.0031(4) O1 0.050(3) 0.043(3) 0.042(3) 0.005(2) 0.011(3) 0.001(2) O2 0.056(3) 0.047(3) 0.058(4) 0.004(3) 0.015(3) 0.005(3) O3 0.043(3) 0.046(3) 0.045(3) 0.000(2) 0.005(3) 0.009(2) O4 0.045(3) 0.037(3) 0.046(3) -0.007(3) 0.008(3) 0.000(2) O5 0.049(3) 0.054(3) 0.057(3) -0.008(3) 0.001(3) 0.010(3) O6 0.047(3) 0.052(3) 0.055(4) -0.005(3) 0.006(3) 0.010(2) O7 0.043(3) 0.045(3) 0.049(3) -0.011(2) -0.001(3) -0.004(2) O8 0.071(4) 0.071(4) 0.068(4) 0.005(3) -0.028(3) -0.012(3) O9 0.047(3) 0.044(3) 0.049(3) 0.008(2) 0.004(3) 0.006(2) O10 0.102(6) 0.177(8) 0.135(7) -0.081(6) -0.063(5) 0.063(5) F1 0.190(6) 0.082(4) 0.137(5) 0.037(4) 0.027(5) 0.062(4) F2 0.251(7) 0.123(5) 0.117(5) 0.040(4) -0.039(5) 0.021(5) F3 0.138(5) 0.129(5) 0.231(7) 0.108(5) 0.034(5) 0.011(4) N1 0.041(4) 0.043(4) 0.036(4) 0.003(3) 0.000(3) 0.003(3) N3 0.042(4) 0.045(4) 0.041(4) 0.002(3) 0.003(3) -0.001(3) N4 0.029(3) 0.052(4) 0.047(4) -0.007(3) 0.003(3) -0.001(3) N5 0.045(4) 0.042(4) 0.047(4) 0.001(3) -0.006(3) 0.001(3) N6 0.049(4) 0.039(4) 0.052(4) 0.005(3) 0.002(3) 0.006(3) C1 0.035(4) 0.037(4) 0.042(5) -0.005(3) 0.003(3) -0.001(3) C2 0.041(4) 0.033(4) 0.041(5) 0.001(3) 0.001(3) 0.004(3) C3 0.057(5) 0.050(5) 0.049(5) 0.008(4) 0.005(4) -0.004(4) C4 0.060(6) 0.045(5) 0.066(6) 0.025(5) -0.005(5) 0.007(4) C5 0.051(5) 0.056(5) 0.060(6) 0.001(4) -0.014(4) 0.013(4) C6 0.041(5) 0.056(5) 0.050(5) 0.004(4) 0.000(4) -0.004(4) C7 0.035(4) 0.039(5) 0.051(5) 0.004(4) -0.001(4) -0.003(4) C8 0.036(4) 0.024(4) 0.043(5) 0.004(3) 0.009(4) -0.006(3) C9 0.086(6) 0.089(7) 0.113(7) 0.026(6) -0.001(5) 0.022(5) C10 0.045(5) 0.041(4) 0.048(5) -0.001(4) 0.006(4) 0.008(4) C11 0.034(4) 0.036(4) 0.054(5) -0.009(4) -0.002(4) 0.002(3) C12 0.041(5) 0.051(5) 0.073(6) -0.013(5) -0.005(5) 0.005(4) C13 0.054(6) 0.076(6) 0.073(7) -0.003(5) -0.005(5) -0.004(5) C18' 0.06(3) 0.15(4) 0.12(4) 0.02(3) 0.06(2) 0.03(3) F4' 0.17(3) 0.17(3) 0.20(3) 0.10(2) 0.09(3) -0.02(2) F5' 0.087(17) 0.24(3) 0.094(17) 0.005(18) 0.036(13) -0.069(18) F6' 0.25(4) 0.19(3) 0.15(3) -0.01(2) 0.05(3) -0.08(3) C14 0.057(6) 0.111(8) 0.074(7) 0.026(7) 0.013(5) -0.001(6) C18 0.041(8) 0.090(11) 0.055(10) 0.000(8) -0.002(7) -0.019(7) F4 0.074(6) 0.118(7) 0.126(8) -0.017(7) 0.024(6) -0.043(6) F5 0.046(5) 0.143(8) 0.124(7) 0.022(7) 0.017(5) 0.004(5) F6 0.070(6) 0.148(8) 0.070(6) -0.007(5) 0.015(5) -0.018(5) C15 0.052(6) 0.089(7) 0.082(7) 0.033(6) 0.015(5) 0.012(5) C16 0.060(6) 0.029(4) 0.049(5) 0.006(4) 0.005(4) 0.016(4) C17 0.038(5) 0.041(5) 0.059(6) -0.013(4) -0.011(4) 0.004(4) C19 0.049(5) 0.081(7) 0.054(6) -0.004(5) 0.001(4) 0.003(5) C20 0.065(7) 0.097(8) 0.054(6) -0.005(5) -0.017(5) -0.002(5) C21 0.051(6) 0.068(6) 0.073(7) 0.002(5) -0.011(5) 0.000(5) C22 0.051(5) 0.058(6) 0.070(7) 0.004(5) 0.006(5) 0.004(4) C23 0.038(4) 0.046(5) 0.054(5) 0.001(4) -0.007(4) 0.005(3) C24 0.070(7) 0.080(7) 0.099(8) 0.014(6) -0.022(6) -0.013(5) C25 0.055(6) 0.081(7) 0.089(8) 0.016(6) 0.001(5) -0.002(5) C26 0.039(5) 0.092(7) 0.061(6) 0.002(5) -0.004(4) -0.002(5) C27 0.042(5) 0.046(5) 0.041(5) 0.000(4) -0.009(4) 0.008(4) C28 0.032(4) 0.050(5) 0.068(6) 0.004(4) -0.008(4) -0.010(4) C29 0.036(5) 0.062(5) 0.047(5) 0.000(4) -0.010(4) 0.003(4) C30 0.045(5) 0.053(5) 0.050(5) -0.008(4) 0.000(4) 0.009(4) C31 0.051(5) 0.037(5) 0.057(5) 0.006(4) -0.006(4) -0.005(4) N2 0.040(4) 0.040(4) 0.044(4) 0.001(3) -0.002(3) -0.006(3) C33 0.040(5) 0.047(5) 0.051(5) 0.008(4) -0.004(4) -0.004(4) C34 0.034(4) 0.048(5) 0.072(6) 0.006(4) -0.001(4) -0.014(4) C35 0.034(4) 0.061(5) 0.040(5) 0.008(4) 0.010(3) -0.002(4) C36 0.038(4) 0.061(5) 0.050(5) 0.006(4) 0.005(4) 0.009(4) C37 0.037(4) 0.040(5) 0.055(5) 0.013(4) 0.003(4) -0.006(4) C38 0.044(5) 0.097(7) 0.067(6) 0.023(6) 0.001(5) -0.009(5) C39 0.033(4) 0.059(5) 0.057(5) -0.008(4) 0.001(4) 0.000(4) C40 0.037(5) 0.123(8) 0.067(7) 0.018(6) 0.000(5) 0.000(5) C41 0.046(5) 0.072(6) 0.047(5) 0.003(4) -0.004(4) 0.002(4) C42 0.039(5) 0.075(6) 0.056(6) 0.010(5) -0.011(4) -0.006(4) C43 0.033(4) 0.056(5) 0.046(5) 0.007(4) -0.002(4) -0.007(4) C44 0.049(5) 0.078(6) 0.050(6) -0.005(4) 0.002(4) -0.012(4) C45 0.036(5) 0.078(6) 0.070(7) -0.011(5) -0.004(4) -0.011(4) C46 0.034(4) 0.052(5) 0.054(5) -0.005(4) 0.005(4) -0.001(4) C47 0.049(5) 0.046(5) 0.074(7) -0.015(4) 0.009(5) -0.004(4) C48 0.052(5) 0.063(6) 0.057(6) -0.017(5) -0.003(4) 0.005(4) C49 0.068(6) 0.072(6) 0.044(5) -0.005(5) 0.001(5) 0.009(5) C50 0.067(6) 0.054(5) 0.046(5) 0.004(4) -0.001(4) 0.012(4) C51 0.107(7) 0.073(6) 0.122(8) -0.028(6) 0.031(6) 0.002(5) C52 0.056(8) 0.072(8) 0.063(8) -0.012(7) 0.014(7) 0.012(6) C53 0.053(5) 0.072(6) 0.060(6) -0.003(5) 0.009(5) 0.009(5) C54 0.093(8) 0.074(7) 0.055(6) -0.006(5) -0.005(6) 0.005(6) C55 0.069(7) 0.047(5) 0.078(7) -0.011(5) -0.023(5) -0.009(5) C56 0.046(5) 0.048(5) 0.089(7) 0.000(5) -0.014(5) -0.001(4) C57 0.045(5) 0.050(5) 0.072(6) -0.008(4) -0.005(4) 0.003(4) C58 0.096(7) 0.108(7) 0.133(8) -0.027(6) -0.008(6) -0.005(6) C59 0.112(10) 0.075(10) 0.097(10) -0.026(8) 0.014(8) -0.022(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 Ni1 O1 2.035(5) . ? Ni1 O7 2.062(5) 7_565 ? Ni1 O9 2.120(5) . ? Ni1 N3 2.125(6) . ? Ni1 N5 2.130(6) . ? Ni1 N1 2.144(6) . ? Ni2 O6 2.001(5) . ? Ni2 N6 2.093(6) . ? Ni2 O3 2.123(5) . ? Ni2 N2 2.121(6) 6_456 ? Ni2 O4 2.146(5) . ? Ni2 N4 2.181(6) 6_466 ? Ni2 C8 2.435(7) . ? O1 C7 1.261(8) . ? O2 C7 1.244(8) . ? O3 C8 1.265(8) . ? O4 C8 1.248(8) . ? O5 C16 1.230(9) . ? O6 C16 1.275(9) . ? O7 C17 1.262(8) . ? O7 Ni1 2.062(5) 7_564 ? O8 C17 1.238(8) . ? O9 H1W 0.8465 . ? O9 H2W 0.8478 . ? O10 H3W 0.8481 . ? O10 H4W 0.8454 . ? F1 C9 1.302(12) . ? F2 C9 1.383(14) . ? F3 C9 1.249(12) . ? N1 C19 1.336(9) . ? N1 C23 1.337(8) . ? N3 C33 1.335(8) . ? N3 C37 1.336(8) . ? N4 C41 1.325(9) . ? N4 C45 1.331(10) . ? N4 Ni2 2.181(6) 8_656 ? N5 C46 1.335(8) . ? N5 C50 1.369(9) . ? N6 C53 1.332(10) . ? N6 C57 1.339(9) . ? C1 C6 1.381(9) . ? C1 C2 1.390(9) . ? C1 C7 1.506(10) . ? C2 C3 1.370(9) . ? C2 C8 1.512(9) . ? C3 C4 1.354(10) . ? C3 H3 0.9300 . ? C4 C5 1.384(11) . ? C4 C9 1.482(13) . ? C5 C6 1.367(10) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C10 C11 1.376(9) . ? C10 C15 1.380(10) . ? C10 C16 1.513(10) . ? C11 C12 1.394(10) . ? C11 C17 1.501(10) . ? C12 C13 1.374(12) . ? C12 H12 0.9300 . ? C13 C14 1.386(12) . ? C13 C18 1.459(14) . ? C18' F6' 1.23(4) . ? C18' F4' 1.40(4) . ? C18' F5' 1.44(5) . ? C18' C14 1.45(4) . ? F4' F5' 1.61(4) 6_465 ? F5' F4' 1.61(4) 8_655 ? C14 C15 1.399(11) . ? C18 F6 1.305(14) . ? C18 F4 1.306(13) . ? C18 F5 1.341(15) . ? C15 H15 0.9300 . ? C19 C20 1.394(11) . ? C19 H19 0.9300 . ? C20 C21 1.385(12) . ? C20 H20 0.9300 . ? C21 C22 1.370(11) . ? C21 C24 1.538(11) . ? C22 C23 1.367(10) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.482(11) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.520(11) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C29 1.506(10) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 N2 1.353(8) . ? C27 C28 1.376(10) . ? C27 H27 0.9300 . ? C28 C29 1.385(10) . ? C28 H28 0.9300 . ? C29 C30 1.382(10) . ? C30 C31 1.374(10) . ? C30 H30 0.9300 . ? C31 N2 1.330(9) . ? C31 H31 0.9300 . ? N2 Ni2 2.121(6) 8_556 ? C33 C34 1.364(9) . ? C33 H33 0.9300 . ? C34 C35 1.383(10) . ? C34 H34 0.9300 . ? C35 C36 1.390(10) . ? C35 C38 1.514(10) . ? C36 C37 1.362(9) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C38 C39 1.523(10) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.526(9) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 C43 1.503(10) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 C42 1.400(10) . ? C41 H41 0.9300 . ? C42 C43 1.376(10) . ? C42 H42 0.9300 . ? C43 C44 1.353(10) . ? C44 C45 1.377(10) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 C47 1.368(10) . ? C46 H46 0.9300 . ? C47 C48 1.378(11) . ? C47 H47 0.9300 . ? C48 C49 1.373(11) . ? C48 C51 1.498(12) . ? C49 C50 1.368(10) . ? C49 H49 0.9300 . ? C50 H50 0.9300 . ? C51 C52 1.262(18) . ? C51 C52 1.791(18) 3_575 ? C51 H51A 0.9564 . ? C51 H51B 0.9570 . ? C52 C52 1.44(3) 3_575 ? C52 C51 1.791(18) 3_575 ? C52 H52A 0.9577 . ? C52 H52B 0.9568 . ? C53 C54 1.373(11) . ? C53 H53 0.9300 . ? C54 C55 1.374(12) . ? C54 H54 0.9300 . ? C55 C56 1.390(12) . ? C55 C58 1.510(13) . ? C56 C57 1.366(11) . ? C56 H56 0.9300 . ? C57 H57 0.9300 . ? C58 C59 1.36(2) . ? C58 C59 1.71(2) 3_675 ? C58 H58A 0.9566 . ? C58 H58B 0.9569 . ? C59 C59 1.17(4) 3_675 ? C59 C58 1.71(2) 3_675 ? C59 H59A 0.9576 . ? C59 H59B 0.9566 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ni1 O7 175.74(19) . 7_565 ? O1 Ni1 O9 88.52(18) . . ? O7 Ni1 O9 94.31(19) 7_565 . ? O1 Ni1 N3 93.1(2) . . ? O7 Ni1 N3 90.2(2) 7_565 . ? O9 Ni1 N3 88.2(2) . . ? O1 Ni1 N5 88.3(2) . . ? O7 Ni1 N5 89.0(2) 7_565 . ? O9 Ni1 N5 176.6(2) . . ? N3 Ni1 N5 90.9(2) . . ? O1 Ni1 N1 85.3(2) . . ? O7 Ni1 N1 91.6(2) 7_565 . ? O9 Ni1 N1 88.6(2) . . ? N3 Ni1 N1 176.4(2) . . ? N5 Ni1 N1 92.2(2) . . ? O6 Ni2 N6 90.9(2) . . ? O6 Ni2 O3 168.2(2) . . ? N6 Ni2 O3 100.0(2) . . ? O6 Ni2 N2 93.3(2) . 6_456 ? N6 Ni2 N2 90.0(2) . 6_456 ? O3 Ni2 N2 91.0(2) . 6_456 ? O6 Ni2 O4 106.9(2) . . ? N6 Ni2 O4 161.1(2) . . ? O3 Ni2 O4 61.81(18) . . ? N2 Ni2 O4 95.4(2) 6_456 . ? O6 Ni2 N4 91.2(2) . 6_466 ? N6 Ni2 N4 91.0(2) . 6_466 ? O3 Ni2 N4 84.3(2) . 6_466 ? N2 Ni2 N4 175.3(2) 6_456 6_466 ? O4 Ni2 N4 82.2(2) . 6_466 ? O6 Ni2 C8 137.1(2) . . ? N6 Ni2 C8 130.5(3) . . ? O3 Ni2 C8 31.3(2) . . ? N2 Ni2 C8 96.7(2) 6_456 . ? O4 Ni2 C8 30.8(2) . . ? N4 Ni2 C8 79.2(2) 6_466 . ? C7 O1 Ni1 131.4(5) . . ? C8 O3 Ni2 88.1(4) . . ? C8 O4 Ni2 87.5(4) . . ? C16 O6 Ni2 134.3(5) . . ? C17 O7 Ni1 136.6(5) . 7_564 ? Ni1 O9 H1W 110.1 . . ? Ni1 O9 H2W 107.1 . . ? H1W O9 H2W 105.6 . . ? H3W O10 H4W 97.5 . . ? C19 N1 C23 115.4(7) . . ? C19 N1 Ni1 120.0(5) . . ? C23 N1 Ni1 124.6(5) . . ? C33 N3 C37 116.1(6) . . ? C33 N3 Ni1 123.1(5) . . ? C37 N3 Ni1 120.7(5) . . ? C41 N4 C45 115.1(7) . . ? C41 N4 Ni2 125.0(5) . 8_656 ? C45 N4 Ni2 119.7(5) . 8_656 ? C46 N5 C50 116.1(7) . . ? C46 N5 Ni1 122.7(5) . . ? C50 N5 Ni1 121.2(5) . . ? C53 N6 C57 116.5(7) . . ? C53 N6 Ni2 120.8(6) . . ? C57 N6 Ni2 122.5(6) . . ? C6 C1 C2 118.3(7) . . ? C6 C1 C7 119.5(6) . . ? C2 C1 C7 122.1(6) . . ? C3 C2 C1 119.3(6) . . ? C3 C2 C8 117.0(6) . . ? C1 C2 C8 123.2(6) . . ? C4 C3 C2 121.9(7) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 119.5(7) . . ? C3 C4 C9 121.1(8) . . ? C5 C4 C9 119.4(8) . . ? C6 C5 C4 119.2(7) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C1 121.7(7) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? O2 C7 O1 127.3(7) . . ? O2 C7 C1 118.5(7) . . ? O1 C7 C1 114.2(6) . . ? O4 C8 O3 121.5(6) . . ? O4 C8 C2 120.3(7) . . ? O3 C8 C2 117.7(6) . . ? O4 C8 Ni2 61.7(3) . . ? O3 C8 Ni2 60.6(3) . . ? C2 C8 Ni2 164.0(4) . . ? F3 C9 F1 111.7(11) . . ? F3 C9 F2 99.7(11) . . ? F1 C9 F2 102.4(9) . . ? F3 C9 C4 117.3(10) . . ? F1 C9 C4 114.5(10) . . ? F2 C9 C4 109.0(10) . . ? C11 C10 C15 119.5(7) . . ? C11 C10 C16 122.1(7) . . ? C15 C10 C16 118.3(7) . . ? C10 C11 C12 120.0(7) . . ? C10 C11 C17 120.2(6) . . ? C12 C11 C17 119.8(7) . . ? C13 C12 C11 120.3(8) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.5(9) . . ? C12 C13 C18 120.7(10) . . ? C14 C13 C18 118.8(10) . . ? F6' C18' F4' 112(4) . . ? F6' C18' F5' 98(3) . . ? F4' C18' F5' 96(4) . . ? F6' C18' C14 113(4) . . ? F4' C18' C14 117(2) . . ? F5' C18' C14 117(4) . . ? C18' F4' F5' 94(3) . 6_465 ? C18' F5' F4' 79(3) . 8_655 ? C13 C14 C15 118.5(9) . . ? C13 C14 C18' 120.1(18) . . ? C15 C14 C18' 119.6(17) . . ? F6 C18 F4 105.3(12) . . ? F6 C18 F5 104.7(12) . . ? F4 C18 F5 107.8(11) . . ? F6 C18 C13 114.4(10) . . ? F4 C18 C13 111.0(11) . . ? F5 C18 C13 113.0(11) . . ? C10 C15 C14 121.1(8) . . ? C10 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? O5 C16 O6 127.5(8) . . ? O5 C16 C10 118.5(7) . . ? O6 C16 C10 114.0(7) . . ? O8 C17 O7 123.6(8) . . ? O8 C17 C11 118.5(7) . . ? O7 C17 C11 117.8(7) . . ? N1 C19 C20 123.0(8) . . ? N1 C19 H19 118.5 . . ? C20 C19 H19 118.5 . . ? C21 C20 C19 120.6(8) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 115.6(8) . . ? C22 C21 C24 122.7(9) . . ? C20 C21 C24 121.7(9) . . ? C23 C22 C21 120.8(8) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? N1 C23 C22 124.5(8) . . ? N1 C23 H23 117.7 . . ? C22 C23 H23 117.7 . . ? C25 C24 C21 112.2(7) . . ? C25 C24 H24A 109.2 . . ? C21 C24 H24A 109.2 . . ? C25 C24 H24B 109.2 . . ? C21 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? C24 C25 C26 112.6(7) . . ? C24 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? C24 C25 H25B 109.1 . . ? C26 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? C29 C26 C25 116.1(7) . . ? C29 C26 H26A 108.3 . . ? C25 C26 H26A 108.3 . . ? C29 C26 H26B 108.3 . . ? C25 C26 H26B 108.3 . . ? H26A C26 H26B 107.4 . . ? N2 C27 C28 121.9(7) . . ? N2 C27 H27 119.1 . . ? C28 C27 H27 119.1 . . ? C27 C28 C29 121.7(7) . . ? C27 C28 H28 119.2 . . ? C29 C28 H28 119.2 . . ? C30 C29 C28 115.7(7) . . ? C30 C29 C26 122.5(7) . . ? C28 C29 C26 121.7(7) . . ? C31 C30 C29 120.0(7) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? N2 C31 C30 124.4(7) . . ? N2 C31 H31 117.8 . . ? C30 C31 H31 117.8 . . ? C31 N2 C27 116.3(6) . . ? C31 N2 Ni2 122.6(5) . 8_556 ? C27 N2 Ni2 121.1(5) . 8_556 ? N3 C33 C34 123.1(7) . . ? N3 C33 H33 118.5 . . ? C34 C33 H33 118.5 . . ? C33 C34 C35 121.2(7) . . ? C33 C34 H34 119.4 . . ? C35 C34 H34 119.4 . . ? C34 C35 C36 115.4(7) . . ? C34 C35 C38 126.3(7) . . ? C36 C35 C38 118.3(7) . . ? C37 C36 C35 120.1(7) . . ? C37 C36 H36 120.0 . . ? C35 C36 H36 120.0 . . ? N3 C37 C36 124.1(7) . . ? N3 C37 H37 118.0 . . ? C36 C37 H37 118.0 . . ? C35 C38 C39 117.3(7) . . ? C35 C38 H38A 108.0 . . ? C39 C38 H38A 108.0 . . ? C35 C38 H38B 108.0 . . ? C39 C38 H38B 108.0 . . ? H38A C38 H38B 107.2 . . ? C38 C39 C40 109.6(6) . . ? C38 C39 H39A 109.8 . . ? C40 C39 H39A 109.8 . . ? C38 C39 H39B 109.8 . . ? C40 C39 H39B 109.8 . . ? H39A C39 H39B 108.2 . . ? C43 C40 C39 118.2(7) . . ? C43 C40 H40A 107.7 . . ? C39 C40 H40A 107.7 . . ? C43 C40 H40B 107.7 . . ? C39 C40 H40B 107.7 . . ? H40A C40 H40B 107.1 . . ? N4 C41 C42 123.1(7) . . ? N4 C41 H41 118.5 . . ? C42 C41 H41 118.5 . . ? C43 C42 C41 120.8(7) . . ? C43 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? C44 C43 C42 115.4(7) . . ? C44 C43 C40 120.1(7) . . ? C42 C43 C40 124.2(7) . . ? C43 C44 C45 121.0(8) . . ? C43 C44 H44 119.5 . . ? C45 C44 H44 119.5 . . ? N4 C45 C44 124.5(8) . . ? N4 C45 H45 117.7 . . ? C44 C45 H45 117.7 . . ? N5 C46 C47 123.3(8) . . ? N5 C46 H46 118.3 . . ? C47 C46 H46 118.3 . . ? C46 C47 C48 121.0(8) . . ? C46 C47 H47 119.5 . . ? C48 C47 H47 119.5 . . ? C47 C48 C49 115.9(8) . . ? C47 C48 C51 121.1(9) . . ? C49 C48 C51 122.8(9) . . ? C50 C49 C48 121.4(8) . . ? C50 C49 H49 119.3 . . ? C48 C49 H49 119.3 . . ? N5 C50 C49 122.2(8) . . ? N5 C50 H50 118.9 . . ? C49 C50 H50 118.9 . . ? C52 C51 C48 121.9(13) . . ? C52 C51 C52 52.7(13) . 3_575 ? C48 C51 C52 101.4(9) . 3_575 ? C52 C51 H51A 109.8 . . ? C48 C51 H51A 105.8 . . ? C52 C51 H51A 152.8 3_575 . ? C52 C51 H51B 105.7 . . ? C48 C51 H51B 106.1 . . ? C52 C51 H51B 65.7 3_575 . ? H51A C51 H51B 106.6 . . ? C51 C52 C52 82.9(16) . 3_575 ? C51 C52 C51 112.8(14) . 3_575 ? C52 C52 C51 44.4(9) 3_575 3_575 ? C51 C52 H52A 108.0 . . ? C52 C52 H52A 100.9 3_575 . ? C51 C52 H52A 61.3 3_575 . ? C51 C52 H52B 107.1 . . ? C52 C52 H52B 142.3 3_575 . ? C51 C52 H52B 139.9 3_575 . ? H52A C52 H52B 109.7 . . ? N6 C53 C54 124.0(8) . . ? N6 C53 H53 118.0 . . ? C54 C53 H53 118.0 . . ? C55 C54 C53 119.8(9) . . ? C55 C54 H54 120.1 . . ? C53 C54 H54 120.1 . . ? C54 C55 C56 116.2(8) . . ? C54 C55 C58 120.6(9) . . ? C56 C55 C58 123.1(9) . . ? C57 C56 C55 120.8(8) . . ? C57 C56 H56 119.6 . . ? C55 C56 H56 119.6 . . ? N6 C57 C56 122.6(8) . . ? N6 C57 H57 118.7 . . ? C56 C57 H57 118.7 . . ? C59 C58 C55 112.0(13) . . ? C59 C58 C59 42.8(15) . 3_675 ? C55 C58 C59 103.1(11) . 3_675 ? C59 C58 H58A 110.3 . . ? C55 C58 H58A 108.5 . . ? C59 C58 H58A 145.6 3_675 . ? C59 C58 H58B 110.5 . . ? C55 C58 H58B 107.5 . . ? C59 C58 H58B 74.4 3_675 . ? H58A C58 H58B 107.9 . . ? C59 C59 C58 85(2) 3_675 . ? C59 C59 C58 52.3(16) 3_675 3_675 ? C58 C59 C58 115.3(15) . 3_675 ? C59 C59 H59A 95.1 3_675 . ? C58 C59 H59A 107.1 . . ? C58 C59 H59A 47.0 3_675 . ? C59 C59 H59B 144.4 3_675 . ? C58 C59 H59B 110.5 . . ? C58 C59 H59B 133.0 3_675 . ? H59A C59 H59B 109.6 . . ? 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 O7 Ni1 O1 C7 -151(2) 7_565 . . . ? O9 Ni1 O1 C7 -19.2(6) . . . . ? N3 Ni1 O1 C7 68.9(6) . . . . ? N5 Ni1 O1 C7 159.6(6) . . . . ? N1 Ni1 O1 C7 -108.0(6) . . . . ? O6 Ni2 O3 C8 10.7(12) . . . . ? N6 Ni2 O3 C8 168.5(4) . . . . ? N2 Ni2 O3 C8 -101.3(4) 6_456 . . . ? O4 Ni2 O3 C8 -5.8(3) . . . . ? N4 Ni2 O3 C8 78.5(4) 6_466 . . . ? O6 Ni2 O4 C8 -170.7(4) . . . . ? N6 Ni2 O4 C8 -11.8(8) . . . . ? O3 Ni2 O4 C8 5.8(4) . . . . ? N2 Ni2 O4 C8 94.1(4) 6_456 . . . ? N4 Ni2 O4 C8 -81.9(4) 6_466 . . . ? N6 Ni2 O6 C16 -163.9(7) . . . . ? O3 Ni2 O6 C16 -5.7(14) . . . . ? N2 Ni2 O6 C16 106.0(7) 6_456 . . . ? O4 Ni2 O6 C16 9.4(7) . . . . ? N4 Ni2 O6 C16 -72.8(7) 6_466 . . . ? C8 Ni2 O6 C16 2.5(8) . . . . ? O1 Ni1 N1 C19 55.8(6) . . . . ? O7 Ni1 N1 C19 -127.1(6) 7_565 . . . ? O9 Ni1 N1 C19 -32.9(6) . . . . ? N3 Ni1 N1 C19 -7(4) . . . . ? N5 Ni1 N1 C19 143.8(6) . . . . ? O1 Ni1 N1 C23 -123.8(6) . . . . ? O7 Ni1 N1 C23 53.3(6) 7_565 . . . ? O9 Ni1 N1 C23 147.5(6) . . . . ? N3 Ni1 N1 C23 173(4) . . . . ? N5 Ni1 N1 C23 -35.8(6) . . . . ? O1 Ni1 N3 C33 23.0(6) . . . . ? O7 Ni1 N3 C33 -154.3(6) 7_565 . . . ? O9 Ni1 N3 C33 111.4(6) . . . . ? N5 Ni1 N3 C33 -65.3(6) . . . . ? N1 Ni1 N3 C33 86(4) . . . . ? O1 Ni1 N3 C37 -153.7(5) . . . . ? O7 Ni1 N3 C37 29.1(6) 7_565 . . . ? O9 Ni1 N3 C37 -65.2(5) . . . . ? N5 Ni1 N3 C37 118.0(6) . . . . ? N1 Ni1 N3 C37 -91(4) . . . . ? O1 Ni1 N5 C46 -6.9(6) . . . . ? O7 Ni1 N5 C46 176.4(6) 7_565 . . . ? O9 Ni1 N5 C46 13(4) . . . . ? N3 Ni1 N5 C46 86.2(6) . . . . ? N1 Ni1 N5 C46 -92.1(6) . . . . ? O1 Ni1 N5 C50 172.0(6) . . . . ? O7 Ni1 N5 C50 -4.7(5) 7_565 . . . ? O9 Ni1 N5 C50 -169(3) . . . . ? N3 Ni1 N5 C50 -94.9(6) . . . . ? N1 Ni1 N5 C50 86.8(6) . . . . ? O6 Ni2 N6 C53 170.3(6) . . . . ? O3 Ni2 N6 C53 -5.3(6) . . . . ? N2 Ni2 N6 C53 -96.4(6) 6_456 . . . ? O4 Ni2 N6 C53 10.4(10) . . . . ? N4 Ni2 N6 C53 79.1(6) 6_466 . . . ? C8 Ni2 N6 C53 2.5(7) . . . . ? O6 Ni2 N6 C57 -4.9(6) . . . . ? O3 Ni2 N6 C57 179.5(6) . . . . ? N2 Ni2 N6 C57 88.5(6) 6_456 . . . ? O4 Ni2 N6 C57 -164.7(6) . . . . ? N4 Ni2 N6 C57 -96.1(6) 6_466 . . . ? C8 Ni2 N6 C57 -172.7(5) . . . . ? C6 C1 C2 C3 1.3(10) . . . . ? C7 C1 C2 C3 178.6(7) . . . . ? C6 C1 C2 C8 172.8(7) . . . . ? C7 C1 C2 C8 -9.9(10) . . . . ? C1 C2 C3 C4 1.0(11) . . . . ? C8 C2 C3 C4 -171.0(7) . . . . ? C2 C3 C4 C5 -2.9(13) . . . . ? C2 C3 C4 C9 178.0(9) . . . . ? C3 C4 C5 C6 2.5(13) . . . . ? C9 C4 C5 C6 -178.3(9) . . . . ? C4 C5 C6 C1 -0.3(12) . . . . ? C2 C1 C6 C5 -1.6(11) . . . . ? C7 C1 C6 C5 -179.0(7) . . . . ? Ni1 O1 C7 O2 -4.1(11) . . . . ? Ni1 O1 C7 C1 174.9(4) . . . . ? C6 C1 C7 O2 142.9(7) . . . . ? C2 C1 C7 O2 -34.4(10) . . . . ? C6 C1 C7 O1 -36.1(9) . . . . ? C2 C1 C7 O1 146.6(7) . . . . ? Ni2 O4 C8 O3 -10.2(6) . . . . ? Ni2 O4 C8 C2 161.7(5) . . . . ? Ni2 O3 C8 O4 10.3(6) . . . . ? Ni2 O3 C8 C2 -161.8(5) . . . . ? C3 C2 C8 O4 -69.5(8) . . . . ? C1 C2 C8 O4 118.8(7) . . . . ? C3 C2 C8 O3 102.7(8) . . . . ? C1 C2 C8 O3 -69.0(8) . . . . ? C3 C2 C8 Ni2 23(2) . . . . ? C1 C2 C8 Ni2 -148.4(17) . . . . ? O6 Ni2 C8 O4 13.1(5) . . . . ? N6 Ni2 C8 O4 175.0(3) . . . . ? O3 Ni2 C8 O4 -170.1(6) . . . . ? N2 Ni2 C8 O4 -89.2(4) 6_456 . . . ? N4 Ni2 C8 O4 93.0(4) 6_466 . . . ? O6 Ni2 C8 O3 -176.8(3) . . . . ? N6 Ni2 C8 O3 -14.9(5) . . . . ? N2 Ni2 C8 O3 80.9(4) 6_456 . . . ? O4 Ni2 C8 O3 170.1(6) . . . . ? N4 Ni2 C8 O3 -96.9(4) 6_466 . . . ? O6 Ni2 C8 C2 -89(2) . . . . ? N6 Ni2 C8 C2 73(2) . . . . ? O3 Ni2 C8 C2 88(2) . . . . ? N2 Ni2 C8 C2 169(2) 6_456 . . . ? O4 Ni2 C8 C2 -102(2) . . . . ? N4 Ni2 C8 C2 -9(2) 6_466 . . . ? C3 C4 C9 F3 -12.9(17) . . . . ? C5 C4 C9 F3 168.0(11) . . . . ? C3 C4 C9 F1 -146.8(10) . . . . ? C5 C4 C9 F1 34.1(15) . . . . ? C3 C4 C9 F2 99.2(11) . . . . ? C5 C4 C9 F2 -79.9(12) . . . . ? C15 C10 C11 C12 -0.9(11) . . . . ? C16 C10 C11 C12 -177.1(7) . . . . ? C15 C10 C11 C17 -179.3(7) . . . . ? C16 C10 C11 C17 4.5(11) . . . . ? C10 C11 C12 C13 -0.6(11) . . . . ? C17 C11 C12 C13 177.8(7) . . . . ? C11 C12 C13 C14 2.1(13) . . . . ? C11 C12 C13 C18 -178.5(9) . . . . ? F6' C18' F4' F5' 38(4) . . . 6_465 ? F5' C18' F4' F5' 139(2) . . . 6_465 ? C14 C18' F4' F5' -96(4) . . . 6_465 ? F6' C18' F5' F4' 52(3) . . . 8_655 ? F4' C18' F5' F4' -62(3) . . . 8_655 ? C14 C18' F5' F4' 173(3) . . . 8_655 ? C12 C13 C14 C15 -2.0(15) . . . . ? C18 C13 C14 C15 178.6(10) . . . . ? C12 C13 C14 C18' 163(2) . . . . ? C18 C13 C14 C18' -17(3) . . . . ? F6' C18' C14 C13 76(5) . . . . ? F4' C18' C14 C13 -150(3) . . . . ? F5' C18' C14 C13 -37(4) . . . . ? F6' C18' C14 C15 -119(3) . . . . ? F4' C18' C14 C15 14(5) . . . . ? F5' C18' C14 C15 128(2) . . . . ? C12 C13 C18 F6 122.5(12) . . . . ? C14 C13 C18 F6 -58.1(16) . . . . ? C12 C13 C18 F4 -118.4(12) . . . . ? C14 C13 C18 F4 61.0(14) . . . . ? C12 C13 C18 F5 2.8(16) . . . . ? C14 C13 C18 F5 -177.8(10) . . . . ? C11 C10 C15 C14 0.9(13) . . . . ? C16 C10 C15 C14 177.3(9) . . . . ? C13 C14 C15 C10 0.5(15) . . . . ? C18' C14 C15 C10 -164(3) . . . . ? Ni2 O6 C16 O5 -11.7(12) . . . . ? Ni2 O6 C16 C10 167.8(4) . . . . ? C11 C10 C16 O5 -121.0(8) . . . . ? C15 C10 C16 O5 62.7(10) . . . . ? C11 C10 C16 O6 59.5(10) . . . . ? C15 C10 C16 O6 -116.7(8) . . . . ? Ni1 O7 C17 O8 -127.8(7) 7_564 . . . ? Ni1 O7 C17 C11 54.0(9) 7_564 . . . ? C10 C11 C17 O8 -124.0(8) . . . . ? C12 C11 C17 O8 57.6(10) . . . . ? C10 C11 C17 O7 54.3(9) . . . . ? C12 C11 C17 O7 -124.0(7) . . . . ? C23 N1 C19 C20 -1.7(12) . . . . ? Ni1 N1 C19 C20 178.7(6) . . . . ? N1 C19 C20 C21 0.4(14) . . . . ? C19 C20 C21 C22 1.4(13) . . . . ? C19 C20 C21 C24 -178.4(8) . . . . ? C20 C21 C22 C23 -2.0(12) . . . . ? C24 C21 C22 C23 177.9(8) . . . . ? C19 N1 C23 C22 1.2(11) . . . . ? Ni1 N1 C23 C22 -179.2(6) . . . . ? C21 C22 C23 N1 0.7(12) . . . . ? C22 C21 C24 C25 101.7(11) . . . . ? C20 C21 C24 C25 -78.5(12) . . . . ? C21 C24 C25 C26 174.1(8) . . . . ? C24 C25 C26 C29 67.9(11) . . . . ? N2 C27 C28 C29 0.2(11) . . . . ? C27 C28 C29 C30 -1.8(11) . . . . ? C27 C28 C29 C26 174.7(7) . . . . ? C25 C26 C29 C30 -113.9(9) . . . . ? C25 C26 C29 C28 69.9(10) . . . . ? C28 C29 C30 C31 1.7(11) . . . . ? C26 C29 C30 C31 -174.8(7) . . . . ? C29 C30 C31 N2 0.1(12) . . . . ? C30 C31 N2 C27 -1.8(11) . . . . ? C30 C31 N2 Ni2 175.8(6) . . . 8_556 ? C28 C27 N2 C31 1.7(10) . . . . ? C28 C27 N2 Ni2 -176.0(5) . . . 8_556 ? C37 N3 C33 C34 0.3(11) . . . . ? Ni1 N3 C33 C34 -176.4(6) . . . . ? N3 C33 C34 C35 -0.9(12) . . . . ? C33 C34 C35 C36 2.2(11) . . . . ? C33 C34 C35 C38 -179.0(8) . . . . ? C34 C35 C36 C37 -3.1(11) . . . . ? C38 C35 C36 C37 178.0(7) . . . . ? C33 N3 C37 C36 -1.3(11) . . . . ? Ni1 N3 C37 C36 175.6(6) . . . . ? C35 C36 C37 N3 2.8(12) . . . . ? C34 C35 C38 C39 -49.5(12) . . . . ? C36 C35 C38 C39 129.3(8) . . . . ? C35 C38 C39 C40 -175.7(8) . . . . ? C38 C39 C40 C43 -178.4(8) . . . . ? C45 N4 C41 C42 -0.7(11) . . . . ? Ni2 N4 C41 C42 174.4(6) 8_656 . . . ? N4 C41 C42 C43 1.1(13) . . . . ? C41 C42 C43 C44 -1.1(12) . . . . ? C41 C42 C43 C40 -174.7(8) . . . . ? C39 C40 C43 C44 152.6(8) . . . . ? C39 C40 C43 C42 -34.0(13) . . . . ? C42 C43 C44 C45 0.7(12) . . . . ? C40 C43 C44 C45 174.7(8) . . . . ? C41 N4 C45 C44 0.3(12) . . . . ? Ni2 N4 C45 C44 -175.0(6) 8_656 . . . ? C43 C44 C45 N4 -0.4(14) . . . . ? C50 N5 C46 C47 -1.9(11) . . . . ? Ni1 N5 C46 C47 177.1(6) . . . . ? N5 C46 C47 C48 1.8(12) . . . . ? C46 C47 C48 C49 -1.6(12) . . . . ? C46 C47 C48 C51 -178.6(8) . . . . ? C47 C48 C49 C50 1.7(12) . . . . ? C51 C48 C49 C50 178.7(9) . . . . ? C46 N5 C50 C49 1.9(11) . . . . ? Ni1 N5 C50 C49 -177.1(6) . . . . ? C48 C49 C50 N5 -1.9(13) . . . . ? C47 C48 C51 C52 39.6(17) . . . . ? C49 C48 C51 C52 -137.2(13) . . . . ? C47 C48 C51 C52 92.6(10) . . . 3_575 ? C49 C48 C51 C52 -84.2(11) . . . 3_575 ? C48 C51 C52 C52 79.5(12) . . . 3_575 ? C48 C51 C52 C51 113.0(15) . . . 3_575 ? C52 C51 C52 C51 33.5(12) 3_575 . . 3_575 ? C57 N6 C53 C54 -0.1(12) . . . . ? Ni2 N6 C53 C54 -175.5(7) . . . . ? N6 C53 C54 C55 -1.0(14) . . . . ? C53 C54 C55 C56 1.0(13) . . . . ? C53 C54 C55 C58 -178.4(9) . . . . ? C54 C55 C56 C57 0.0(12) . . . . ? C58 C55 C56 C57 179.4(9) . . . . ? C53 N6 C57 C56 1.2(11) . . . . ? Ni2 N6 C57 C56 176.5(6) . . . . ? C55 C56 C57 N6 -1.2(12) . . . . ? C54 C55 C58 C59 -133.8(12) . . . . ? C56 C55 C58 C59 46.8(16) . . . . ? C54 C55 C58 C59 -89.8(12) . . . 3_675 ? C56 C55 C58 C59 90.9(12) . . . 3_675 ? C55 C58 C59 C59 85.5(13) . . . 3_675 ? C55 C58 C59 C58 129.3(15) . . . 3_675 ? C59 C58 C59 C58 43.8(13) 3_675 . . 3_675 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O10 H4W O8 0.85 1.93 2.773(9) 176.2 . O10 H3W O3 0.85 2.04 2.881(8) 175.1 8_656 O9 H2W O2 0.85 1.90 2.691(6) 154.2 . O9 H1W O5 0.85 1.99 2.766(7) 151.0 7_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.395 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.063 data_3 _database_code_depnum_ccdc_archive 'CCDC 919378' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H15 Cu F3 N2 O4' _chemical_formula_weight 479.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.023(16) _cell_length_b 10.525(13) _cell_length_c 14.555(19) _cell_angle_alpha 90.00 _cell_angle_beta 95.706(15) _cell_angle_gamma 90.00 _cell_volume 1985(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1116 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 17.48 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 1.160 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7079 _exptl_absorpt_correction_T_max 0.8098 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13925 _diffrn_reflns_av_R_equivalents 0.1864 _diffrn_reflns_av_sigmaI/netI 0.1929 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3588 _reflns_number_gt 1494 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+0.0588P] 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 3588 _refine_ls_number_parameters 308 _refine_ls_number_restraints 84 _refine_ls_R_factor_all 0.1948 _refine_ls_R_factor_gt 0.0745 _refine_ls_wR_factor_ref 0.1871 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.021 _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 F1 F 0.6651(10) 0.3790(9) 0.7632(8) 0.133(5) Uani 0.657(12) 1 d PDU A 1 F2 F 0.6423(8) 0.1850(10) 0.7286(6) 0.105(4) Uani 0.657(12) 1 d PDU A 1 F3 F 0.7861(7) 0.2458(13) 0.7972(7) 0.132(4) Uani 0.657(12) 1 d PDU A 1 F1' F 0.7539(15) 0.3649(16) 0.7930(10) 0.104(7) Uani 0.343(12) 1 d PDU A 2 F2' F 0.6123(8) 0.286(2) 0.7330(14) 0.131(7) Uani 0.343(12) 1 d PDU A 2 F3' F 0.7435(18) 0.1669(13) 0.7682(14) 0.129(7) Uani 0.343(12) 1 d PDU A 2 Cu1 Cu 0.85859(8) 0.50966(8) 0.22045(6) 0.0510(4) Uani 1 1 d . . . O1 O 0.8073(4) 0.4185(4) 0.3217(3) 0.0504(14) Uani 1 1 d . . . O2 O 0.9684(5) 0.3724(5) 0.3811(4) 0.0692(17) Uani 1 1 d . . . O3 O 0.6378(5) 0.1158(5) 0.3914(3) 0.0579(15) Uani 1 1 d . . . O4 O 0.7978(4) 0.1174(5) 0.3542(4) 0.0617(16) Uani 1 1 d . . . N1 N 0.8836(5) 0.3548(6) 0.1468(4) 0.0553(18) Uani 1 1 d . . . N2 N 0.9021(6) 0.6629(6) 0.2961(5) 0.0577(19) Uani 1 1 d . . . C1 C 0.8303(6) 0.3440(7) 0.4746(6) 0.053(2) Uani 1 1 d . . . C2 C 0.7626(6) 0.2427(7) 0.4834(5) 0.051(2) Uani 1 1 d . . . C3 C 0.7206(7) 0.2202(8) 0.5674(6) 0.066(3) Uani 1 1 d . . . H3 H 0.6749 0.1536 0.5738 0.079 Uiso 1 1 calc R . . C4 C 0.7499(8) 0.3006(10) 0.6394(6) 0.071(3) Uani 1 1 d . A . C5 C 0.8185(8) 0.3951(9) 0.6325(6) 0.072(3) Uani 1 1 d . . . H5 H 0.8376 0.4458 0.6836 0.086 Uiso 1 1 calc R . . C6 C 0.8610(7) 0.4180(8) 0.5504(5) 0.060(2) Uani 1 1 d . . . H6 H 0.9094 0.4822 0.5466 0.072 Uiso 1 1 calc R . . C7 C 0.8738(9) 0.3766(7) 0.3856(6) 0.055(2) Uani 1 1 d . . . C8 C 0.7328(8) 0.1522(7) 0.4032(6) 0.047(2) Uani 1 1 d . . . C9 C 0.7132(7) 0.2786(8) 0.7319(8) 0.104(3) Uani 1 1 d DU . . C10 C 0.8768(7) 0.6827(7) 0.3817(6) 0.065(3) Uani 1 1 d . . . H10 H 0.8340 0.6241 0.4068 0.078 Uiso 1 1 calc R . . C11 C 0.9125(7) 0.7899(8) 0.4366(6) 0.066(3) Uani 1 1 d . . . H11 H 0.8957 0.7984 0.4970 0.080 Uiso 1 1 calc R . . C12 C 0.9715(7) 0.8793(8) 0.3988(7) 0.061(2) Uani 1 1 d . . . C13 C 0.9963(8) 0.8578(9) 0.3120(7) 0.079(3) Uani 1 1 d . . . H13 H 1.0381 0.9151 0.2846 0.095 Uiso 1 1 calc R . . C14 C 0.9603(8) 0.7527(9) 0.2646(6) 0.078(3) Uani 1 1 d . . . H14 H 0.9783 0.7432 0.2047 0.094 Uiso 1 1 calc R . . C15 C 1.0146(7) 0.9952(9) 0.4534(5) 0.074(3) Uani 1 1 d . . . H15A H 1.0893 0.9929 0.4563 0.089 Uiso 1 1 calc R . . H15B H 0.9916 1.0713 0.4198 0.089 Uiso 1 1 calc R . . C16 C 0.8726(7) 0.2381(8) 0.1795(6) 0.068(3) Uani 1 1 d . . . H16 H 0.8517 0.2298 0.2385 0.081 Uiso 1 1 calc R . . C17 C 0.8903(7) 0.1282(8) 0.1314(6) 0.075(3) Uani 1 1 d . . . H17 H 0.8802 0.0492 0.1577 0.090 Uiso 1 1 calc R . . C18 C 0.9227(7) 0.1361(8) 0.0451(6) 0.069(3) Uani 1 1 d . . . C19 C 0.9335(9) 0.2536(9) 0.0117(6) 0.094(4) Uani 1 1 d . . . H19 H 0.9543 0.2635 -0.0472 0.112 Uiso 1 1 calc R . . C20 C 0.9145(8) 0.3606(9) 0.0630(6) 0.091(4) Uani 1 1 d . . . H20 H 0.9239 0.4402 0.0374 0.109 Uiso 1 1 calc R . . C21 C 0.9445(6) 0.0184(8) -0.0077(6) 0.070(3) Uani 1 1 d . . . H21A H 0.9022 -0.0508 0.0113 0.085 Uiso 1 1 calc R . . H21B H 0.9261 0.0331 -0.0731 0.085 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 F1 0.156(9) 0.136(7) 0.119(7) -0.014(6) 0.068(6) 0.012(6) F2 0.117(7) 0.122(7) 0.084(6) 0.011(5) 0.045(5) -0.009(5) F3 0.132(7) 0.174(9) 0.089(6) 0.034(6) 0.008(5) -0.008(6) F1' 0.122(10) 0.120(9) 0.074(9) -0.010(7) 0.026(7) 0.000(8) F2' 0.119(8) 0.153(12) 0.122(11) -0.002(9) 0.022(8) 0.003(7) F3' 0.147(12) 0.117(8) 0.124(11) 0.012(8) 0.019(9) 0.005(8) Cu1 0.0699(7) 0.0365(5) 0.0482(6) -0.0057(5) 0.0138(5) 0.0005(6) O1 0.082(4) 0.032(3) 0.038(3) -0.002(3) 0.008(3) 0.002(3) O2 0.076(5) 0.063(4) 0.072(4) 0.004(3) 0.022(4) -0.005(3) O3 0.078(4) 0.049(3) 0.048(3) 0.000(3) 0.014(3) -0.003(3) O4 0.072(4) 0.048(3) 0.070(4) -0.003(3) 0.028(3) -0.002(3) N1 0.078(5) 0.042(4) 0.049(4) -0.009(3) 0.024(4) -0.007(3) N2 0.087(6) 0.037(4) 0.047(4) 0.002(3) -0.001(4) -0.003(4) C1 0.060(6) 0.044(5) 0.052(5) -0.007(4) -0.006(4) 0.005(4) C2 0.054(6) 0.053(5) 0.045(5) -0.005(4) 0.002(4) 0.006(4) C3 0.075(7) 0.069(6) 0.055(6) 0.006(5) 0.020(5) 0.006(5) C4 0.096(8) 0.078(7) 0.042(5) 0.006(5) 0.020(6) 0.015(6) C5 0.097(8) 0.067(7) 0.051(6) -0.016(5) 0.000(6) 0.019(6) C6 0.075(6) 0.056(5) 0.047(5) -0.015(5) -0.003(5) 0.002(5) C7 0.081(8) 0.031(4) 0.057(6) -0.013(4) 0.022(6) -0.011(5) C8 0.064(7) 0.028(4) 0.049(5) 0.002(4) 0.006(5) 0.001(4) C9 0.112(7) 0.101(6) 0.099(7) -0.003(5) 0.010(6) 0.001(5) C10 0.093(8) 0.042(5) 0.061(6) -0.006(5) 0.020(6) 0.004(5) C11 0.085(7) 0.065(6) 0.048(5) -0.009(5) 0.001(5) 0.005(5) C12 0.064(6) 0.043(5) 0.074(6) -0.010(5) -0.002(5) 0.004(4) C13 0.108(8) 0.063(6) 0.066(6) -0.005(6) 0.012(6) -0.019(6) C14 0.113(9) 0.059(6) 0.059(6) -0.010(5) -0.006(6) -0.006(6) C15 0.091(7) 0.064(6) 0.067(6) 0.006(6) 0.004(5) -0.004(6) C16 0.097(8) 0.050(6) 0.065(6) -0.004(5) 0.047(5) -0.004(5) C17 0.101(8) 0.045(5) 0.084(7) -0.010(5) 0.038(6) 0.000(5) C18 0.086(7) 0.052(6) 0.074(6) -0.015(5) 0.031(6) 0.014(5) C19 0.171(12) 0.059(7) 0.061(6) -0.006(5) 0.061(7) 0.008(7) C20 0.161(11) 0.044(6) 0.078(7) 0.007(5) 0.060(7) 0.012(6) C21 0.078(6) 0.060(6) 0.076(6) -0.026(5) 0.022(6) 0.001(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 F1 C9 1.332(8) . ? F2 C9 1.347(8) . ? F3 C9 1.321(8) . ? F1' C9 1.344(9) . ? F2' C9 1.317(9) . ? F3' C9 1.333(9) . ? Cu1 O1 1.932(5) . ? Cu1 O3 1.979(5) 2_655 ? Cu1 N1 1.995(6) . ? Cu1 N2 2.003(7) . ? Cu1 C8 2.546(8) 2_655 ? O1 C7 1.285(10) . ? O2 C7 1.240(10) . ? O3 C8 1.290(9) . ? O3 Cu1 1.979(5) 2_645 ? O4 C8 1.218(9) . ? N1 C20 1.323(9) . ? N1 C16 1.330(9) . ? N2 C14 1.322(10) . ? N2 C10 1.335(9) . ? C1 C6 1.376(10) . ? C1 C2 1.397(10) . ? C1 C7 1.505(11) . ? C2 C3 1.409(10) . ? C2 C8 1.526(10) . ? C3 C4 1.371(12) . ? C3 H3 0.9300 . ? C4 C5 1.347(12) . ? C4 C9 1.491(14) . ? C5 C6 1.387(11) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 Cu1 2.546(8) 2_645 ? C10 C11 1.434(11) . ? C10 H10 0.9300 . ? C11 C12 1.365(11) . ? C11 H11 0.9300 . ? C12 C13 1.354(11) . ? C12 C15 1.532(11) . ? C13 C14 1.362(11) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C15 1.448(15) 3_776 ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.383(11) . ? C16 H16 0.9300 . ? C17 C18 1.366(11) . ? C17 H17 0.9300 . ? C18 C19 1.342(11) . ? C18 C21 1.500(10) . ? C19 C20 1.388(11) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C21 1.491(16) 3_755 ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O3 161.1(3) . 2_655 ? O1 Cu1 N1 95.2(2) . . ? O3 Cu1 N1 90.0(3) 2_655 . ? O1 Cu1 N2 94.6(3) . . ? O3 Cu1 N2 88.2(3) 2_655 . ? N1 Cu1 N2 154.3(3) . . ? O1 Cu1 C8 131.2(3) . 2_655 ? O3 Cu1 C8 29.9(2) 2_655 2_655 ? N1 Cu1 C8 101.0(3) . 2_655 ? N2 Cu1 C8 90.1(3) . 2_655 ? C7 O1 Cu1 117.6(6) . . ? C8 O3 Cu1 100.2(5) . 2_645 ? C20 N1 C16 115.2(7) . . ? C20 N1 Cu1 122.6(6) . . ? C16 N1 Cu1 122.2(5) . . ? C14 N2 C10 114.5(7) . . ? C14 N2 Cu1 121.7(6) . . ? C10 N2 Cu1 123.8(6) . . ? C6 C1 C2 119.6(8) . . ? C6 C1 C7 117.2(8) . . ? C2 C1 C7 123.2(7) . . ? C1 C2 C3 120.7(8) . . ? C1 C2 C8 121.4(7) . . ? C3 C2 C8 117.9(8) . . ? C4 C3 C2 117.2(9) . . ? C4 C3 H3 121.4 . . ? C2 C3 H3 121.4 . . ? C5 C4 C3 122.3(9) . . ? C5 C4 C9 117.2(9) . . ? C3 C4 C9 120.3(9) . . ? C4 C5 C6 121.1(9) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.9(9) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? O2 C7 O1 125.2(8) . . ? O2 C7 C1 119.9(9) . . ? O1 C7 C1 114.6(9) . . ? O4 C8 O3 123.1(7) . . ? O4 C8 C2 119.8(8) . . ? O3 C8 C2 117.1(8) . . ? O4 C8 Cu1 73.2(5) . 2_645 ? O3 C8 Cu1 49.9(4) . 2_645 ? C2 C8 Cu1 166.9(7) . 2_645 ? F2' C9 F3 130.7(15) . . ? F2' C9 F1 56.5(8) . . ? F3 C9 F1 106.8(9) . . ? F2' C9 F3' 107.6(10) . . ? F3 C9 F3' 47.2(8) . . ? F1 C9 F3' 134.1(16) . . ? F2' C9 F1' 106.4(9) . . ? F3 C9 F1' 59.5(7) . . ? F1 C9 F1' 53.4(7) . . ? F3' C9 F1' 104.6(9) . . ? F2' C9 F2 50.3(9) . . ? F3 C9 F2 106.0(8) . . ? F1 C9 F2 104.5(8) . . ? F3' C9 F2 62.9(9) . . ? F1' C9 F2 137.9(14) . . ? F2' C9 C4 114.3(12) . . ? F3 C9 C4 114.7(10) . . ? F1 C9 C4 112.9(9) . . ? F3' C9 C4 112.7(13) . . ? F1' C9 C4 110.6(11) . . ? F2 C9 C4 111.2(9) . . ? N2 C10 C11 123.2(8) . . ? N2 C10 H10 118.4 . . ? C11 C10 H10 118.4 . . ? C12 C11 C10 118.8(8) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C13 C12 C11 117.2(8) . . ? C13 C12 C15 120.6(9) . . ? C11 C12 C15 122.1(8) . . ? C12 C13 C14 120.5(9) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? N2 C14 C13 125.8(9) . . ? N2 C14 H14 117.1 . . ? C13 C14 H14 117.1 . . ? C15 C15 C12 115.1(10) 3_776 . ? C15 C15 H15A 108.5 3_776 . ? C12 C15 H15A 108.5 . . ? C15 C15 H15B 108.5 3_776 . ? C12 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? N1 C16 C17 124.2(8) . . ? N1 C16 H16 117.9 . . ? C17 C16 H16 117.9 . . ? C18 C17 C16 119.8(8) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 116.3(8) . . ? C19 C18 C21 122.9(8) . . ? C17 C18 C21 120.9(8) . . ? C18 C19 C20 121.5(8) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? N1 C20 C19 123.1(8) . . ? N1 C20 H20 118.5 . . ? C19 C20 H20 118.5 . . ? C21 C21 C18 111.5(9) 3_755 . ? C21 C21 H21A 109.3 3_755 . ? C18 C21 H21A 109.3 . . ? C21 C21 H21B 109.3 3_755 . ? C18 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? 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 O3 Cu1 O1 C7 -168.8(6) 2_655 . . . ? N1 Cu1 O1 C7 85.6(5) . . . . ? N2 Cu1 O1 C7 -70.7(5) . . . . ? C8 Cu1 O1 C7 -164.8(5) 2_655 . . . ? O1 Cu1 N1 C20 175.4(7) . . . . ? O3 Cu1 N1 C20 13.6(8) 2_655 . . . ? N2 Cu1 N1 C20 -72.4(10) . . . . ? C8 Cu1 N1 C20 41.6(8) 2_655 . . . ? O1 Cu1 N1 C16 -6.2(7) . . . . ? O3 Cu1 N1 C16 -168.0(7) 2_655 . . . ? N2 Cu1 N1 C16 106.0(8) . . . . ? C8 Cu1 N1 C16 -140.0(7) 2_655 . . . ? O1 Cu1 N2 C14 168.4(7) . . . . ? O3 Cu1 N2 C14 -30.3(7) 2_655 . . . ? N1 Cu1 N2 C14 56.1(10) . . . . ? C8 Cu1 N2 C14 -60.1(7) 2_655 . . . ? O1 Cu1 N2 C10 -10.6(7) . . . . ? O3 Cu1 N2 C10 150.6(7) 2_655 . . . ? N1 Cu1 N2 C10 -122.9(8) . . . . ? C8 Cu1 N2 C10 120.8(7) 2_655 . . . ? C6 C1 C2 C3 3.9(12) . . . . ? C7 C1 C2 C3 -177.1(8) . . . . ? C6 C1 C2 C8 -175.4(7) . . . . ? C7 C1 C2 C8 3.6(12) . . . . ? C1 C2 C3 C4 -0.7(12) . . . . ? C8 C2 C3 C4 178.6(7) . . . . ? C2 C3 C4 C5 -2.2(13) . . . . ? C2 C3 C4 C9 -176.7(8) . . . . ? C3 C4 C5 C6 1.9(15) . . . . ? C9 C4 C5 C6 176.5(8) . . . . ? C2 C1 C6 C5 -4.2(12) . . . . ? C7 C1 C6 C5 176.7(8) . . . . ? C4 C5 C6 C1 1.4(13) . . . . ? Cu1 O1 C7 O2 -11.7(10) . . . . ? Cu1 O1 C7 C1 161.8(5) . . . . ? C6 C1 C7 O2 60.8(10) . . . . ? C2 C1 C7 O2 -118.3(9) . . . . ? C6 C1 C7 O1 -113.1(8) . . . . ? C2 C1 C7 O1 67.9(10) . . . . ? Cu1 O3 C8 O4 -2.4(8) 2_645 . . . ? Cu1 O3 C8 C2 177.9(5) 2_645 . . . ? C1 C2 C8 O4 40.3(10) . . . . ? C3 C2 C8 O4 -139.0(8) . . . . ? C1 C2 C8 O3 -140.0(7) . . . . ? C3 C2 C8 O3 40.8(10) . . . . ? C1 C2 C8 Cu1 -133(2) . . . 2_645 ? C3 C2 C8 Cu1 48(3) . . . 2_645 ? C5 C4 C9 F2' 122.9(14) . . . . ? C3 C4 C9 F2' -62.3(14) . . . . ? C5 C4 C9 F3 -62.0(12) . . . . ? C3 C4 C9 F3 112.7(11) . . . . ? C5 C4 C9 F1 60.7(12) . . . . ? C3 C4 C9 F1 -124.5(10) . . . . ? C5 C4 C9 F3' -113.8(14) . . . . ? C3 C4 C9 F3' 60.9(14) . . . . ? C5 C4 C9 F1' 2.9(14) . . . . ? C3 C4 C9 F1' 177.6(12) . . . . ? C5 C4 C9 F2 177.7(9) . . . . ? C3 C4 C9 F2 -7.5(12) . . . . ? C14 N2 C10 C11 -2.1(12) . . . . ? Cu1 N2 C10 C11 177.0(6) . . . . ? N2 C10 C11 C12 2.9(13) . . . . ? C10 C11 C12 C13 -2.6(13) . . . . ? C10 C11 C12 C15 -178.7(8) . . . . ? C11 C12 C13 C14 1.9(14) . . . . ? C15 C12 C13 C14 178.1(8) . . . . ? C10 N2 C14 C13 1.4(14) . . . . ? Cu1 N2 C14 C13 -177.8(8) . . . . ? C12 C13 C14 N2 -1.4(16) . . . . ? C13 C12 C15 C15 -177.8(10) . . . 3_776 ? C11 C12 C15 C15 -1.9(15) . . . 3_776 ? C20 N1 C16 C17 -0.7(14) . . . . ? Cu1 N1 C16 C17 -179.2(7) . . . . ? N1 C16 C17 C18 1.0(16) . . . . ? C16 C17 C18 C19 -1.2(15) . . . . ? C16 C17 C18 C21 178.7(9) . . . . ? C17 C18 C19 C20 1.1(17) . . . . ? C21 C18 C19 C20 -178.8(9) . . . . ? C16 N1 C20 C19 0.6(15) . . . . ? Cu1 N1 C20 C19 179.1(8) . . . . ? C18 C19 C20 N1 -0.8(18) . . . . ? C19 C18 C21 C21 87.0(13) . . . 3_755 ? C17 C18 C21 C21 -92.9(12) . . . 3_755 ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.715 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.092 data_3a _database_code_depnum_ccdc_archive 'CCDC 919379' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H10 Cu F4 N2 O4' _chemical_formula_weight 481.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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 13.567(3) _cell_length_b 11.779(2) _cell_length_c 11.206(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1790.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5160 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 24.68 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.787 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 1.294 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7552 _exptl_absorpt_correction_T_max 0.8498 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18709 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3346 _reflns_number_gt 2869 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0066P)^2^+1.3198P] 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 0.016(13) _refine_ls_number_reflns 3346 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0609 _refine_ls_wR_factor_gt 0.0563 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 -0.03420(2) 0.36311(3) 1.00323(4) 0.03047(10) Uani 1 1 d . . . F1 F -0.35343(16) 0.4889(2) 0.9580(2) 0.0664(7) Uani 1 1 d . . . F2 F -0.50745(16) 0.5502(2) 0.8213(3) 0.0724(8) Uani 1 1 d . . . F3 F -0.47949(16) 0.6042(2) 0.5890(2) 0.0671(7) Uani 1 1 d . . . F4 F -0.29887(14) 0.59830(19) 0.4946(2) 0.0593(6) Uani 1 1 d . . . N1 N 0.3900(2) 0.1471(2) 0.1585(2) 0.0318(6) Uani 1 1 d . . . N2 N 0.0297(2) 0.3075(3) 0.8509(2) 0.0374(7) Uani 1 1 d . . . O1 O -0.15864(17) 0.3728(2) 0.9141(2) 0.0377(6) Uani 1 1 d . . . O2 O -0.09609(19) 0.5455(2) 0.9030(2) 0.0472(7) Uani 1 1 d . . . O3 O -0.09556(16) 0.6305(2) 0.5778(2) 0.0377(6) Uani 1 1 d . . . O4 O -0.07714(18) 0.4490(2) 0.6318(2) 0.0448(6) Uani 1 1 d . . . C1 C -0.1583(3) 0.4746(3) 0.8759(3) 0.0339(8) Uani 1 1 d . . . C2 C -0.2432(3) 0.5087(3) 0.7959(3) 0.0332(8) Uani 1 1 d . . . C3 C -0.3374(3) 0.5136(3) 0.8417(3) 0.0434(9) Uani 1 1 d . . . C4 C -0.4159(3) 0.5460(3) 0.7740(4) 0.0471(10) Uani 1 1 d . . . C5 C -0.4021(3) 0.5735(3) 0.6574(4) 0.0461(10) Uani 1 1 d . . . C6 C -0.3079(3) 0.5716(3) 0.6098(3) 0.0390(9) Uani 1 1 d . . . C7 C -0.2280(2) 0.5399(3) 0.6772(3) 0.0316(7) Uani 1 1 d . . . C8 C -0.1241(2) 0.5369(3) 0.6248(3) 0.0334(8) Uani 1 1 d . . . C9 C -0.0184(3) 0.2397(3) 0.7757(3) 0.0405(9) Uani 1 1 d . . . H9 H -0.0804 0.2134 0.7981 0.049 Uiso 1 1 calc R . . C10 C 0.0183(3) 0.2063(3) 0.6669(3) 0.0422(9) Uani 1 1 d . . . H10 H -0.0183 0.1586 0.6177 0.051 Uiso 1 1 calc R . . C11 C 0.1099(3) 0.2443(3) 0.6315(3) 0.0414(9) Uani 1 1 d . . . C12 C 0.1597(3) 0.3153(4) 0.7079(4) 0.0579(12) Uani 1 1 d . . . H12 H 0.2215 0.3430 0.6869 0.069 Uiso 1 1 calc R . . C13 C 0.1176(3) 0.3462(4) 0.8172(4) 0.0570(12) Uani 1 1 d . . . H13 H 0.1518 0.3949 0.8676 0.068 Uiso 1 1 calc R . . C14 C 0.1515(3) 0.2130(3) 0.5134(4) 0.0454(9) Uani 1 1 d . . . H14 H 0.1076 0.1972 0.4518 0.055 Uiso 1 1 calc R . . C15 C 0.2446(2) 0.2063(3) 0.4907(3) 0.0419(8) Uani 1 1 d . . . H15 H 0.2872 0.2189 0.5544 0.050 Uiso 1 1 calc R . . C16 C 0.4381(3) 0.1535(3) 0.2622(3) 0.0400(9) Uani 1 1 d . . . H16 H 0.5064 0.1466 0.2615 0.048 Uiso 1 1 calc R . . C17 C 0.3921(3) 0.1696(3) 0.3695(3) 0.0440(10) Uani 1 1 d . . . H17 H 0.4290 0.1729 0.4394 0.053 Uiso 1 1 calc R . . C18 C 0.2906(3) 0.1809(3) 0.3743(3) 0.0391(9) Uani 1 1 d . . . C19 C 0.2412(3) 0.1732(3) 0.2676(3) 0.0466(10) Uani 1 1 d . . . H19 H 0.1728 0.1793 0.2666 0.056 Uiso 1 1 calc R . . C20 C 0.2914(3) 0.1564(3) 0.1618(3) 0.0410(9) Uani 1 1 d . . . H20 H 0.2560 0.1515 0.0910 0.049 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 0.03225(18) 0.0407(2) 0.01849(14) -0.0006(2) 0.0055(2) 0.00126(18) F1 0.0480(13) 0.101(2) 0.0503(13) 0.0103(13) 0.0205(11) 0.0095(14) F2 0.0293(12) 0.088(2) 0.100(2) -0.0047(16) 0.0131(13) 0.0085(12) F3 0.0389(13) 0.0738(17) 0.0885(17) 0.0025(14) -0.0264(13) 0.0051(12) F4 0.0492(12) 0.0850(16) 0.0436(13) 0.0177(16) -0.0179(14) -0.0032(10) N1 0.0330(16) 0.0399(18) 0.0225(14) 0.0013(12) 0.0084(12) 0.0008(13) N2 0.0358(16) 0.051(2) 0.0253(13) -0.0007(13) 0.0043(13) 0.0039(16) O1 0.0363(14) 0.0459(17) 0.0310(12) 0.0045(12) 0.0044(11) 0.0026(12) O2 0.0433(15) 0.0538(18) 0.0445(15) -0.0037(13) -0.0079(12) -0.0039(14) O3 0.0326(14) 0.0518(16) 0.0287(12) 0.0101(12) -0.0040(10) -0.0004(12) O4 0.0395(14) 0.0499(17) 0.0449(14) 0.0000(12) 0.0070(12) 0.0089(13) C1 0.0316(18) 0.049(3) 0.0206(16) -0.0018(16) 0.0050(14) 0.0064(18) C2 0.0284(17) 0.035(2) 0.0361(18) -0.0031(15) -0.0012(14) 0.0010(15) C3 0.036(2) 0.047(3) 0.048(2) 0.0030(18) 0.0029(17) 0.0037(18) C4 0.028(2) 0.050(3) 0.063(3) -0.003(2) 0.0083(18) 0.0071(18) C5 0.035(2) 0.041(2) 0.062(3) -0.0032(19) -0.0169(19) 0.0023(17) C6 0.040(2) 0.040(2) 0.037(2) 0.0013(17) -0.0082(16) 0.0015(17) C7 0.0304(17) 0.033(2) 0.0317(17) -0.0016(15) -0.0038(14) 0.0032(15) C8 0.0289(18) 0.054(3) 0.0168(14) -0.0041(16) -0.0067(13) 0.0001(17) C9 0.046(2) 0.044(2) 0.0312(17) -0.0021(16) 0.0088(16) 0.0051(18) C10 0.049(2) 0.048(2) 0.0297(17) -0.0052(16) 0.0015(16) 0.0037(18) C11 0.048(2) 0.049(2) 0.0266(16) -0.0028(17) 0.0065(17) 0.0123(18) C12 0.046(2) 0.088(3) 0.039(2) -0.009(2) 0.0171(19) -0.009(2) C13 0.050(3) 0.085(4) 0.036(2) -0.016(2) 0.0119(19) -0.010(2) C14 0.052(2) 0.053(2) 0.0310(17) 0.000(2) 0.007(2) 0.0038(17) C15 0.0464(19) 0.053(2) 0.0263(19) -0.0001(19) 0.0112(19) 0.0023(16) C16 0.0402(19) 0.053(3) 0.0267(16) -0.0001(16) 0.0065(15) 0.0076(18) C17 0.051(2) 0.057(3) 0.0234(17) -0.0017(16) 0.0048(16) 0.0119(19) C18 0.055(2) 0.036(2) 0.0254(17) 0.0044(15) 0.0133(16) 0.0069(18) C19 0.040(2) 0.065(3) 0.0351(19) -0.0011(18) 0.0152(17) 0.0028(19) C20 0.038(2) 0.057(3) 0.0278(18) -0.0014(17) 0.0072(16) -0.0005(18) _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 O3 1.950(2) 2_565 ? Cu1 O1 1.965(2) . ? Cu1 N2 2.024(3) . ? Cu1 N1 2.025(2) 3_456 ? F1 C3 1.353(4) . ? F2 C4 1.351(4) . ? F3 C5 1.350(4) . ? F4 C6 1.334(4) . ? N1 C16 1.335(4) . ? N1 C20 1.343(4) . ? N1 Cu1 2.025(2) 3_554 ? N2 C13 1.330(5) . ? N2 C9 1.333(4) . ? O1 C1 1.273(4) . ? O2 C1 1.225(4) . ? O3 C8 1.282(4) . ? O3 Cu1 1.950(2) 2_564 ? O4 C8 1.218(4) . ? C1 C2 1.514(5) . ? C2 C3 1.379(5) . ? C2 C7 1.396(5) . ? C3 C4 1.362(5) . ? C4 C5 1.360(5) . ? C5 C6 1.385(5) . ? C6 C7 1.372(4) . ? C7 C8 1.528(4) . ? C9 C10 1.374(4) . ? C9 H9 0.9300 . ? C10 C11 1.380(5) . ? C10 H10 0.9300 . ? C11 C12 1.374(5) . ? C11 C14 1.485(5) . ? C12 C13 1.399(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.291(5) . ? C14 H14 0.9300 . ? C15 C18 1.477(5) . ? C15 H15 0.9300 . ? C16 C17 1.368(4) . ? C16 H16 0.9300 . ? C17 C18 1.384(5) . ? C17 H17 0.9300 . ? C18 C19 1.374(5) . ? C19 C20 1.381(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 O3 Cu1 O1 172.39(11) 2_565 . ? O3 Cu1 N2 89.27(10) 2_565 . ? O1 Cu1 N2 87.59(11) . . ? O3 Cu1 N1 95.29(11) 2_565 3_456 ? O1 Cu1 N1 90.24(11) . 3_456 ? N2 Cu1 N1 157.45(12) . 3_456 ? C16 N1 C20 117.3(3) . . ? C16 N1 Cu1 120.2(2) . 3_554 ? C20 N1 Cu1 122.3(2) . 3_554 ? C13 N2 C9 117.7(3) . . ? C13 N2 Cu1 120.8(3) . . ? C9 N2 Cu1 121.2(2) . . ? C1 O1 Cu1 102.8(2) . . ? C8 O3 Cu1 118.8(2) . 2_564 ? O2 C1 O1 124.2(3) . . ? O2 C1 C2 119.3(3) . . ? O1 C1 C2 116.5(3) . . ? C3 C2 C7 118.7(3) . . ? C3 C2 C1 119.7(3) . . ? C7 C2 C1 121.5(3) . . ? F1 C3 C4 118.1(3) . . ? F1 C3 C2 119.9(3) . . ? C4 C3 C2 122.0(3) . . ? F2 C4 C3 120.7(4) . . ? F2 C4 C5 119.7(4) . . ? C3 C4 C5 119.6(3) . . ? F3 C5 C4 120.2(4) . . ? F3 C5 C6 120.3(4) . . ? C4 C5 C6 119.6(3) . . ? F4 C6 C7 121.6(3) . . ? F4 C6 C5 116.9(3) . . ? C7 C6 C5 121.4(3) . . ? C6 C7 C2 118.7(3) . . ? C6 C7 C8 121.5(3) . . ? C2 C7 C8 119.7(3) . . ? O4 C8 O3 126.8(3) . . ? O4 C8 C7 118.6(3) . . ? O3 C8 C7 114.6(3) . . ? N2 C9 C10 123.7(3) . . ? N2 C9 H9 118.1 . . ? C10 C9 H9 118.1 . . ? C9 C10 C11 119.2(4) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 117.5(3) . . ? C12 C11 C14 121.3(3) . . ? C10 C11 C14 121.2(3) . . ? C11 C12 C13 120.1(4) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? N2 C13 C12 121.7(4) . . ? N2 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C15 C14 C11 124.2(4) . . ? C15 C14 H14 117.9 . . ? C11 C14 H14 117.9 . . ? C14 C15 C18 126.9(4) . . ? C14 C15 H15 116.6 . . ? C18 C15 H15 116.6 . . ? N1 C16 C17 123.4(3) . . ? N1 C16 H16 118.3 . . ? C17 C16 H16 118.3 . . ? C16 C17 C18 120.1(3) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 116.5(3) . . ? C19 C18 C15 125.1(3) . . ? C17 C18 C15 118.3(3) . . ? C18 C19 C20 121.0(3) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? N1 C20 C19 121.8(3) . . ? N1 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.209 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.048 data_3b _database_code_depnum_ccdc_archive 'CCDC 919380' #TrackingRef '7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H10 Cl4 Cu N2 O4' _chemical_formula_weight 547.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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 14.162(3) _cell_length_b 13.601(3) _cell_length_c 10.898(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2099.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8190 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.15 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.733 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1092 _exptl_absorpt_coefficient_mu 1.581 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6748 _exptl_absorpt_correction_T_max 0.8208 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22400 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3471 _reflns_number_gt 3178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0275P)^2^+0.5192P] 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 0.015(11) _refine_ls_number_reflns 3471 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0291 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0565 _refine_ls_wR_factor_gt 0.0540 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.028344(18) 0.87085(2) 0.72098(3) 0.02644(8) Uani 1 1 d . . . N1 N 0.45570(15) 0.68909(19) -0.1367(2) 0.0337(6) Uani 1 1 d . . . N2 N 0.11609(15) 0.85501(17) 0.5752(2) 0.0293(5) Uani 1 1 d . . . O1 O -0.08649(12) 0.86572(14) 0.62194(19) 0.0336(5) Uani 1 1 d . . . O2 O -0.09160(15) 1.02918(17) 0.6293(2) 0.0487(6) Uani 1 1 d . . . O3 O -0.13628(12) 1.09279(15) 0.32446(18) 0.0314(4) Uani 1 1 d . . . O4 O -0.07913(14) 0.94112(16) 0.3141(2) 0.0447(5) Uani 1 1 d . . . C1 C -0.12516(18) 0.9495(2) 0.6027(2) 0.0299(6) Uani 1 1 d . . . C2 C -0.21993(17) 0.9452(2) 0.5378(3) 0.0300(6) Uani 1 1 d . . . C3 C -0.30194(19) 0.9216(2) 0.6023(3) 0.0390(7) Uani 1 1 d . . . C4 C -0.38723(19) 0.9109(2) 0.5425(4) 0.0439(8) Uani 1 1 d . . . C5 C -0.39202(19) 0.9243(2) 0.4163(4) 0.0458(9) Uani 1 1 d . . . C6 C -0.31130(19) 0.9520(2) 0.3522(3) 0.0392(7) Uani 1 1 d . . . C7 C -0.22600(17) 0.9652(2) 0.4132(3) 0.0305(6) Uani 1 1 d . . . C8 C -0.13922(17) 0.9997(2) 0.3436(2) 0.0283(6) Uani 1 1 d . . . C9 C 0.38165(19) 0.7485(2) -0.1551(3) 0.0372(7) Uani 1 1 d . . . H9 H 0.3665 0.7659 -0.2353 0.045 Uiso 1 1 calc R . . C10 C 0.3270(2) 0.7849(2) -0.0615(3) 0.0383(7) Uani 1 1 d . . . H10 H 0.2761 0.8256 -0.0796 0.046 Uiso 1 1 calc R . . C11 C 0.3467(2) 0.7618(2) 0.0586(3) 0.0346(7) Uani 1 1 d . . . C12 C 0.4255(2) 0.7025(3) 0.0783(3) 0.0616(11) Uani 1 1 d . . . H12 H 0.4435 0.6857 0.1576 0.074 Uiso 1 1 calc R . . C13 C 0.4764(2) 0.6691(3) -0.0206(3) 0.0575(10) Uani 1 1 d . . . H13 H 0.5289 0.6299 -0.0052 0.069 Uiso 1 1 calc R . . C14 C 0.2849(2) 0.7966(3) 0.1589(3) 0.0377(7) Uani 1 1 d . . . H14 H 0.2325 0.8341 0.1372 0.045 Uiso 1 1 calc R . . C15 C 0.29800(19) 0.7789(2) 0.2769(3) 0.0345(7) Uani 1 1 d . . . H15 H 0.3520 0.7441 0.2985 0.041 Uiso 1 1 calc R . . C16 C 0.20518(17) 0.8254(2) 0.5929(3) 0.0322(6) Uani 1 1 d . . . H16 H 0.2278 0.8210 0.6728 0.039 Uiso 1 1 calc R . . C17 C 0.26460(18) 0.8013(2) 0.4976(3) 0.0333(6) Uani 1 1 d . . . H17 H 0.3254 0.7793 0.5143 0.040 Uiso 1 1 calc R . . C18 C 0.23475(18) 0.8094(2) 0.3776(3) 0.0306(6) Uani 1 1 d . . . C19 C 0.1431(2) 0.8421(3) 0.3602(3) 0.0469(8) Uani 1 1 d . . . H19 H 0.1194 0.8499 0.2812 0.056 Uiso 1 1 calc R . . C20 C 0.0872(2) 0.8631(3) 0.4598(3) 0.0447(8) Uani 1 1 d . . . H20 H 0.0257 0.8841 0.4456 0.054 Uiso 1 1 calc R . . Cl1 Cl -0.29543(6) 0.90652(8) 0.75945(9) 0.0608(3) Uani 1 1 d . . . Cl2 Cl -0.48673(6) 0.87868(7) 0.62348(13) 0.0710(3) Uani 1 1 d . . . Cl3 Cl -0.49672(6) 0.90610(9) 0.34016(13) 0.0847(4) Uani 1 1 d . . . Cl4 Cl -0.31570(6) 0.96891(7) 0.19597(8) 0.0614(3) 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 0.01957(13) 0.03911(17) 0.02064(14) -0.00087(17) 0.00300(14) -0.00206(12) N1 0.0295(11) 0.0483(15) 0.0232(12) 0.0048(12) 0.0055(9) 0.0113(10) N2 0.0227(11) 0.0409(14) 0.0242(13) 0.0014(11) 0.0036(9) 0.0032(10) O1 0.0220(9) 0.0455(12) 0.0333(12) 0.0025(10) 0.0006(8) 0.0005(8) O2 0.0503(13) 0.0483(13) 0.0474(14) -0.0022(12) -0.0073(11) -0.0123(11) O3 0.0247(9) 0.0391(12) 0.0304(11) 0.0059(10) -0.0009(8) -0.0044(8) O4 0.0315(10) 0.0537(13) 0.0489(14) 0.0012(11) 0.0067(9) 0.0082(10) C1 0.0230(13) 0.0460(18) 0.0208(14) 0.0048(13) 0.0053(10) -0.0006(12) C2 0.0213(12) 0.0303(15) 0.0385(17) 0.0024(13) 0.0042(11) 0.0008(10) C3 0.0292(15) 0.0397(17) 0.048(2) 0.0058(15) 0.0110(13) 0.0032(12) C4 0.0189(13) 0.0361(17) 0.077(3) 0.0094(17) 0.0094(15) 0.0018(12) C5 0.0198(13) 0.0409(18) 0.077(3) 0.0104(17) -0.0093(14) -0.0035(12) C6 0.0284(14) 0.0384(16) 0.051(2) 0.0120(15) -0.0105(13) -0.0020(12) C7 0.0212(12) 0.0312(15) 0.0392(17) 0.0040(13) -0.0015(12) 0.0012(10) C8 0.0206(12) 0.0431(17) 0.0213(14) 0.0019(13) -0.0059(10) -0.0012(12) C9 0.0357(15) 0.0514(18) 0.0246(14) 0.0049(14) 0.0021(12) 0.0144(13) C10 0.0394(15) 0.0443(18) 0.0314(16) 0.0015(14) 0.0018(13) 0.0152(13) C11 0.0342(15) 0.0444(17) 0.0251(15) 0.0051(14) 0.0097(11) 0.0103(13) C12 0.059(2) 0.102(3) 0.0232(16) 0.0086(19) 0.0090(15) 0.043(2) C13 0.053(2) 0.088(3) 0.0306(18) 0.0090(19) 0.0081(16) 0.0439(19) C14 0.0321(15) 0.051(2) 0.0303(18) 0.0016(15) 0.0091(12) 0.0141(14) C15 0.0270(13) 0.0438(17) 0.0328(17) -0.0006(14) 0.0092(12) 0.0047(13) C16 0.0255(13) 0.0473(17) 0.0239(14) -0.0012(13) -0.0010(11) 0.0043(12) C17 0.0238(12) 0.0453(18) 0.0310(16) -0.0028(14) 0.0005(11) 0.0080(12) C18 0.0274(13) 0.0371(16) 0.0273(15) 0.0015(13) 0.0063(11) 0.0044(11) C19 0.0343(16) 0.085(2) 0.0209(15) 0.0068(16) 0.0015(12) 0.0187(16) C20 0.0286(14) 0.077(2) 0.0289(16) 0.0087(16) 0.0020(13) 0.0199(14) Cl1 0.0488(5) 0.0843(7) 0.0494(5) 0.0101(5) 0.0250(4) 0.0038(4) Cl2 0.0281(4) 0.0704(6) 0.1146(9) 0.0093(6) 0.0289(5) -0.0032(4) Cl3 0.0285(4) 0.1038(8) 0.1220(11) 0.0349(8) -0.0278(5) -0.0215(5) Cl4 0.0454(4) 0.0819(6) 0.0569(7) 0.0169(5) -0.0265(4) -0.0134(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9532(19) . ? Cu1 O3 1.9629(18) 2_575 ? Cu1 N2 2.029(2) . ? Cu1 N1 2.032(2) 3_466 ? N1 C13 1.327(4) . ? N1 C9 1.339(3) . ? N1 Cu1 2.032(2) 3_564 ? N2 C20 1.327(4) . ? N2 C16 1.338(3) . ? O1 C1 1.282(3) . ? O2 C1 1.218(3) . ? O3 C8 1.284(3) . ? O3 Cu1 1.9629(18) 2_574 ? O4 C8 1.209(3) . ? C1 C2 1.518(3) . ? C2 C7 1.388(4) . ? C2 C3 1.395(4) . ? C3 C4 1.380(4) . ? C3 Cl1 1.727(4) . ? C4 C5 1.390(5) . ? C4 Cl2 1.719(3) . ? C5 C6 1.391(4) . ? C5 Cl3 1.717(3) . ? C6 C7 1.390(4) . ? C6 Cl4 1.719(3) . ? C7 C8 1.518(4) . ? C9 C10 1.373(4) . ? C9 H9 0.9300 . ? C10 C11 1.376(4) . ? C10 H10 0.9300 . ? C11 C12 1.393(4) . ? C11 C14 1.478(4) . ? C12 C13 1.374(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.322(4) . ? C14 H14 0.9300 . ? C15 C18 1.476(4) . ? C15 H15 0.9300 . ? C16 C17 1.376(4) . ? C16 H16 0.9300 . ? C17 C18 1.379(4) . ? C17 H17 0.9300 . ? C18 C19 1.386(4) . ? C19 C20 1.373(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O3 167.15(8) . 2_575 ? O1 Cu1 N2 94.21(9) . . ? O3 Cu1 N2 89.99(9) 2_575 . ? O1 Cu1 N1 89.19(9) . 3_466 ? O3 Cu1 N1 93.27(9) 2_575 3_466 ? N2 Cu1 N1 149.93(10) . 3_466 ? C13 N1 C9 116.1(2) . . ? C13 N1 Cu1 122.23(19) . 3_564 ? C9 N1 Cu1 121.64(19) . 3_564 ? C20 N2 C16 116.9(2) . . ? C20 N2 Cu1 123.02(18) . . ? C16 N2 Cu1 119.75(19) . . ? C1 O1 Cu1 114.49(17) . . ? C8 O3 Cu1 111.53(16) . 2_574 ? O2 C1 O1 125.8(3) . . ? O2 C1 C2 119.3(3) . . ? O1 C1 C2 114.8(2) . . ? C7 C2 C3 119.1(3) . . ? C7 C2 C1 120.2(2) . . ? C3 C2 C1 120.7(3) . . ? C4 C3 C2 121.0(3) . . ? C4 C3 Cl1 120.1(2) . . ? C2 C3 Cl1 118.9(2) . . ? C3 C4 C5 119.7(3) . . ? C3 C4 Cl2 120.1(3) . . ? C5 C4 Cl2 120.1(2) . . ? C4 C5 C6 119.5(3) . . ? C4 C5 Cl3 120.1(2) . . ? C6 C5 Cl3 120.4(3) . . ? C7 C6 C5 120.6(3) . . ? C7 C6 Cl4 119.2(2) . . ? C5 C6 Cl4 120.2(2) . . ? C2 C7 C6 119.7(3) . . ? C2 C7 C8 119.9(2) . . ? C6 C7 C8 120.3(3) . . ? O4 C8 O3 125.7(3) . . ? O4 C8 C7 120.0(3) . . ? O3 C8 C7 114.3(2) . . ? N1 C9 C10 123.3(3) . . ? N1 C9 H9 118.4 . . ? C10 C9 H9 118.4 . . ? C9 C10 C11 120.6(3) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C12 116.2(3) . . ? C10 C11 C14 120.6(3) . . ? C12 C11 C14 123.1(3) . . ? C13 C12 C11 119.4(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? N1 C13 C12 124.3(3) . . ? N1 C13 H13 117.8 . . ? C12 C13 H13 117.8 . . ? C15 C14 C11 125.3(3) . . ? C15 C14 H14 117.4 . . ? C11 C14 H14 117.4 . . ? C14 C15 C18 126.0(3) . . ? C14 C15 H15 117.0 . . ? C18 C15 H15 117.0 . . ? N2 C16 C17 122.6(3) . . ? N2 C16 H16 118.7 . . ? C17 C16 H16 118.7 . . ? C16 C17 C18 120.6(2) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C17 C18 C19 116.3(3) . . ? C17 C18 C15 119.8(2) . . ? C19 C18 C15 123.9(3) . . ? C20 C19 C18 119.9(3) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? N2 C20 C19 123.7(3) . . ? N2 C20 H20 118.2 . . ? C19 C20 H20 118.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.227 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.043