# Electronic Supplementary Material (ESI) for Chemical Communications # 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_i0792 _database_code_depnum_ccdc_archive 'CCDC 919918' #TrackingRef 'chemcomm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H14 F8 N2' _chemical_formula_sum 'C35 H14 F8 N2' _chemical_formula_weight 614.48 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2909(6) _cell_length_b 22.2679(11) _cell_length_c 12.5448(8) _cell_angle_alpha 90.00 _cell_angle_beta 106.708(5) _cell_angle_gamma 90.00 _cell_volume 2753.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 14198 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 25.68 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9509 _exptl_absorpt_correction_T_max 0.9790 _exptl_absorpt_process_details 'X-red ver. 1.31 (Stoe & Cie. 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 30 _diffrn_source_power 1.50 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 130 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 12673 _diffrn_reflns_av_R_equivalents 0.0758 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.12 _reflns_number_total 4884 _reflns_number_gt 3882 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0965P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4884 _refine_ls_number_parameters 407 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 C1 C 0.15081(18) 0.76136(8) -0.09412(15) 0.0394(4) Uani 1 1 d . . . C2 C 0.02454(18) 0.76503(8) -0.19514(15) 0.0400(4) Uani 1 1 d . . . C3 C -0.02720(18) 0.81495(8) -0.25964(15) 0.0410(4) Uani 1 1 d . . . H3A H 0.0200 0.8521 -0.2468 0.049 Uiso 1 1 calc R . . C4 C -0.15077(18) 0.80969(9) -0.34450(15) 0.0428(4) Uani 1 1 d . . . C5 C -0.2193(2) 0.75409(9) -0.36387(16) 0.0463(4) Uani 1 1 d . . . H5A H -0.3019 0.7507 -0.4220 0.056 Uiso 1 1 calc R . . C6 C -0.1675(2) 0.70402(9) -0.29885(16) 0.0454(4) Uani 1 1 d . . . H6A H -0.2140 0.6667 -0.3119 0.055 Uiso 1 1 calc R . . C7 C -0.04490(18) 0.70992(8) -0.21359(15) 0.0415(4) Uani 1 1 d . . . C8 C 0.02693(18) 0.66743(8) -0.12688(15) 0.0408(4) Uani 1 1 d . . . C9 C 0.00121(19) 0.60713(8) -0.10946(16) 0.0434(4) Uani 1 1 d . . . H9A H -0.0698 0.5861 -0.1612 0.052 Uiso 1 1 calc R . . C10 C 0.08175(18) 0.57858(8) -0.01478(16) 0.0427(4) Uani 1 1 d . . . H10A H 0.0652 0.5376 -0.0023 0.051 Uiso 1 1 calc R . . C11 C 0.18722(17) 0.60908(8) 0.06291(15) 0.0391(4) Uani 1 1 d . . . C12 C 0.21682(18) 0.66910(8) 0.04336(15) 0.0388(4) Uani 1 1 d . . . H12A H 0.2896 0.6898 0.0940 0.047 Uiso 1 1 calc R . . C13 C 0.13666(18) 0.69752(7) -0.05223(15) 0.0383(4) Uani 1 1 d . . . C14 C -0.21545(18) 0.86294(9) -0.41078(16) 0.0454(4) Uani 1 1 d . . . C15 C -0.2730(2) 0.86009(10) -0.52616(17) 0.0511(5) Uani 1 1 d . . . C16 C -0.3380(2) 0.91011(12) -0.58295(19) 0.0622(6) Uani 1 1 d . . . C17 C -0.2957(2) 0.96529(10) -0.4282(2) 0.0563(5) Uani 1 1 d . . . C18 C -0.22725(19) 0.91857(9) -0.36302(18) 0.0479(5) Uani 1 1 d . . . C19 C 0.26680(18) 0.57677(7) 0.16505(15) 0.0396(4) Uani 1 1 d . . . C20 C 0.20551(18) 0.54114(8) 0.22858(16) 0.0414(4) Uani 1 1 d . . . C21 C 0.2836(2) 0.50990(8) 0.32046(17) 0.0469(5) Uani 1 1 d . . . C22 C 0.47635(19) 0.54535(8) 0.29655(17) 0.0456(4) Uani 1 1 d . . . C23 C 0.40840(19) 0.57803(8) 0.20291(16) 0.0421(4) Uani 1 1 d . . . C24 C 0.28587(18) 0.76892(8) -0.12245(15) 0.0415(4) Uani 1 1 d . . . C25 C 0.3362(2) 0.73531(9) -0.19499(17) 0.0464(4) Uani 1 1 d . . . H25A H 0.2853 0.7031 -0.2362 0.056 Uiso 1 1 calc R . . C26 C 0.4637(2) 0.75011(10) -0.20578(18) 0.0523(5) Uani 1 1 d . . . H26A H 0.4994 0.7279 -0.2556 0.063 Uiso 1 1 calc R . . C27 C 0.5395(2) 0.79716(10) -0.1444(2) 0.0557(6) Uani 1 1 d . . . H27A H 0.6259 0.8065 -0.1531 0.067 Uiso 1 1 calc R . . C28 C 0.4899(2) 0.83039(9) -0.07089(18) 0.0525(5) Uani 1 1 d . . . H28A H 0.5423 0.8620 -0.0286 0.063 Uiso 1 1 calc R . . C29 C 0.36136(19) 0.81662(8) -0.06003(16) 0.0439(4) Uani 1 1 d . . . C30 C 0.2811(2) 0.84456(8) 0.00616(16) 0.0453(4) Uani 1 1 d . . . C31 C 0.3058(2) 0.89577(9) 0.07451(19) 0.0554(5) Uani 1 1 d . . . H31A H 0.3883 0.9175 0.0871 0.066 Uiso 1 1 calc R . . C32 C 0.2071(3) 0.91385(9) 0.12313(19) 0.0591(6) Uani 1 1 d . . . H32A H 0.2221 0.9486 0.1689 0.071 Uiso 1 1 calc R . . C33 C 0.0858(3) 0.88184(9) 0.10618(18) 0.0558(5) Uani 1 1 d . . . H33A H 0.0199 0.8950 0.1408 0.067 Uiso 1 1 calc R . . C34 C 0.0607(2) 0.83055(8) 0.03845(16) 0.0474(5) Uani 1 1 d . . . H34A H -0.0215 0.8087 0.0267 0.057 Uiso 1 1 calc R . . C35 C 0.15853(19) 0.81254(8) -0.01076(15) 0.0413(4) Uani 1 1 d . . . F1 F -0.26103(13) 0.80990(6) -0.58250(10) 0.0603(4) Uani 1 1 d . . . F2 F -0.39030(16) 0.90607(7) -0.69505(12) 0.0824(5) Uani 1 1 d . . . F3 F -0.30961(14) 1.01797(6) -0.38025(13) 0.0697(4) Uani 1 1 d . . . F4 F -0.17645(12) 0.92694(5) -0.25262(10) 0.0544(3) Uani 1 1 d . . . F5 F 0.06847(11) 0.53594(5) 0.20139(10) 0.0484(3) Uani 1 1 d . . . F6 F 0.22207(14) 0.47449(5) 0.37786(11) 0.0604(3) Uani 1 1 d . . . F7 F 0.61304(12) 0.54734(6) 0.33154(11) 0.0578(3) Uani 1 1 d . . . F8 F 0.48078(11) 0.60913(5) 0.14752(10) 0.0486(3) Uani 1 1 d . . . N1 N -0.35031(19) 0.96169(9) -0.53667(18) 0.0636(5) Uani 1 1 d . . . N2 N 0.41740(18) 0.51173(7) 0.35471(14) 0.0496(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0449(9) 0.0343(9) 0.0377(9) 0.0013(7) 0.0098(7) -0.0042(7) C2 0.0446(9) 0.0385(9) 0.0385(9) -0.0012(7) 0.0144(7) -0.0027(7) C3 0.0445(9) 0.0390(9) 0.0405(9) 0.0014(7) 0.0139(7) -0.0041(7) C4 0.0437(9) 0.0465(10) 0.0403(9) 0.0030(8) 0.0156(8) -0.0021(8) C5 0.0472(10) 0.0498(10) 0.0413(10) 0.0009(8) 0.0116(8) -0.0069(8) C6 0.0494(10) 0.0429(10) 0.0430(10) -0.0019(8) 0.0118(8) -0.0093(8) C7 0.0471(10) 0.0378(9) 0.0414(10) -0.0011(7) 0.0156(8) -0.0046(7) C8 0.0451(9) 0.0367(9) 0.0422(9) -0.0023(7) 0.0150(8) -0.0041(7) C9 0.0474(9) 0.0377(9) 0.0454(10) -0.0036(8) 0.0138(8) -0.0068(7) C10 0.0473(9) 0.0311(8) 0.0515(11) -0.0005(8) 0.0174(8) -0.0034(7) C11 0.0430(9) 0.0346(9) 0.0429(9) -0.0018(7) 0.0173(7) -0.0008(7) C12 0.0429(9) 0.0340(8) 0.0411(9) -0.0021(7) 0.0145(7) -0.0028(7) C13 0.0453(9) 0.0322(9) 0.0398(9) 0.0001(7) 0.0161(7) -0.0030(7) C14 0.0405(9) 0.0515(11) 0.0452(10) 0.0083(8) 0.0140(8) -0.0057(8) C15 0.0505(10) 0.0559(12) 0.0459(11) 0.0074(9) 0.0123(8) -0.0135(9) C16 0.0530(11) 0.0799(16) 0.0472(12) 0.0247(11) 0.0041(9) -0.0182(11) C17 0.0489(11) 0.0534(12) 0.0685(14) 0.0160(10) 0.0199(10) -0.0003(9) C18 0.0432(9) 0.0514(11) 0.0515(11) 0.0092(9) 0.0177(8) -0.0014(8) C19 0.0477(9) 0.0280(8) 0.0449(10) -0.0046(7) 0.0161(8) 0.0006(7) C20 0.0457(9) 0.0316(8) 0.0491(10) -0.0017(7) 0.0170(8) 0.0010(7) C21 0.0618(12) 0.0336(9) 0.0490(11) 0.0018(8) 0.0219(9) -0.0011(8) C22 0.0466(10) 0.0381(9) 0.0517(11) -0.0037(8) 0.0134(8) 0.0040(7) C23 0.0475(9) 0.0337(9) 0.0483(10) -0.0031(7) 0.0190(8) -0.0022(7) C24 0.0438(9) 0.0362(9) 0.0425(10) 0.0089(7) 0.0088(8) -0.0013(7) C25 0.0486(10) 0.0446(10) 0.0458(10) 0.0066(8) 0.0132(8) 0.0011(8) C26 0.0519(11) 0.0535(11) 0.0538(11) 0.0141(9) 0.0190(9) 0.0097(9) C27 0.0446(10) 0.0547(12) 0.0681(14) 0.0238(10) 0.0165(10) 0.0010(8) C28 0.0470(10) 0.0444(10) 0.0599(13) 0.0161(9) 0.0057(9) -0.0067(8) C29 0.0474(10) 0.0368(9) 0.0449(10) 0.0091(8) 0.0089(8) -0.0035(7) C30 0.0542(10) 0.0337(9) 0.0430(10) 0.0068(7) 0.0059(8) -0.0055(8) C31 0.0671(13) 0.0374(10) 0.0546(12) 0.0004(9) 0.0065(10) -0.0123(9) C32 0.0852(15) 0.0377(10) 0.0521(12) -0.0066(9) 0.0158(11) -0.0077(10) C33 0.0793(14) 0.0399(10) 0.0508(11) -0.0023(9) 0.0230(10) 0.0017(9) C34 0.0594(11) 0.0382(9) 0.0449(10) 0.0013(8) 0.0157(9) -0.0032(8) C35 0.0510(10) 0.0321(8) 0.0391(9) 0.0033(7) 0.0101(8) -0.0024(7) F1 0.0664(7) 0.0703(8) 0.0417(6) 0.0018(6) 0.0116(5) -0.0192(6) F2 0.0885(10) 0.0918(11) 0.0519(8) 0.0296(7) -0.0036(7) -0.0243(8) F3 0.0702(8) 0.0510(7) 0.0915(10) 0.0163(7) 0.0288(7) 0.0095(6) F4 0.0607(7) 0.0539(7) 0.0513(7) 0.0020(5) 0.0204(5) 0.0061(5) F5 0.0496(6) 0.0416(6) 0.0592(7) 0.0037(5) 0.0236(5) -0.0032(4) F6 0.0778(8) 0.0497(7) 0.0573(7) 0.0119(6) 0.0251(6) -0.0061(6) F7 0.0479(6) 0.0554(7) 0.0659(8) 0.0005(6) 0.0096(5) 0.0064(5) F8 0.0465(6) 0.0458(6) 0.0572(7) 0.0007(5) 0.0209(5) -0.0020(4) N1 0.0539(10) 0.0597(12) 0.0728(13) 0.0254(10) 0.0114(9) -0.0076(9) N2 0.0596(10) 0.0376(8) 0.0493(9) -0.0008(7) 0.0122(8) 0.0038(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 C1 C35 1.533(2) . ? C1 C2 1.534(2) . ? C1 C13 1.537(2) . ? C1 C24 1.540(3) . ? C2 C3 1.388(3) . ? C2 C7 1.405(3) . ? C3 C4 1.409(3) . ? C3 H3A 0.9500 . ? C4 C5 1.411(3) . ? C4 C14 1.491(3) . ? C5 C6 1.394(3) . ? C5 H5A 0.9500 . ? C6 C7 1.406(3) . ? C6 H6A 0.9500 . ? C7 C8 1.471(3) . ? C8 C9 1.398(3) . ? C8 C13 1.412(2) . ? C9 C10 1.391(3) . ? C9 H9A 0.9500 . ? C10 C11 1.407(3) . ? C10 H10A 0.9500 . ? C11 C12 1.408(3) . ? C11 C19 1.492(3) . ? C12 C13 1.397(2) . ? C12 H12A 0.9500 . ? C14 C18 1.396(3) . ? C14 C15 1.399(3) . ? C15 F1 1.347(3) . ? C15 C16 1.386(3) . ? C16 N1 1.309(3) . ? C16 F2 1.357(3) . ? C17 N1 1.317(3) . ? C17 F3 1.344(3) . ? C17 C18 1.384(3) . ? C18 F4 1.345(2) . ? C19 C20 1.397(3) . ? C19 C23 1.397(3) . ? C20 F5 1.357(2) . ? C20 C21 1.388(3) . ? C21 N2 1.320(3) . ? C21 F6 1.343(2) . ? C22 N2 1.310(3) . ? C22 F7 1.348(2) . ? C22 C23 1.388(3) . ? C23 F8 1.347(2) . ? C24 C25 1.389(3) . ? C24 C29 1.412(3) . ? C25 C26 1.396(3) . ? C25 H25A 0.9500 . ? C26 C27 1.398(3) . ? C26 H26A 0.9500 . ? C27 C28 1.389(3) . ? C27 H27A 0.9500 . ? C28 C29 1.402(3) . ? C28 H28A 0.9500 . ? C29 C30 1.467(3) . ? C30 C31 1.405(3) . ? C30 C35 1.411(3) . ? C31 C32 1.387(4) . ? C31 H31A 0.9500 . ? C32 C33 1.400(3) . ? C32 H32A 0.9500 . ? C33 C34 1.402(3) . ? C33 H33A 0.9500 . ? C34 C35 1.383(3) . ? C34 H34A 0.9500 . ? 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 C35 C1 C2 112.90(14) . . ? C35 C1 C13 116.47(15) . . ? C2 C1 C13 100.99(13) . . ? C35 C1 C24 101.71(14) . . ? C2 C1 C24 114.20(15) . . ? C13 C1 C24 111.14(14) . . ? C3 C2 C7 120.78(17) . . ? C3 C2 C1 128.02(16) . . ? C7 C2 C1 111.06(15) . . ? C2 C3 C4 119.04(16) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C3 C4 C5 120.07(17) . . ? C3 C4 C14 121.10(16) . . ? C5 C4 C14 118.75(16) . . ? C6 C5 C4 120.86(17) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C5 C6 C7 118.62(17) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? C2 C7 C6 120.63(17) . . ? C2 C7 C8 108.44(15) . . ? C6 C7 C8 130.75(16) . . ? C9 C8 C13 120.23(16) . . ? C9 C8 C7 131.01(16) . . ? C13 C8 C7 108.75(15) . . ? C10 C9 C8 118.63(16) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? C9 C10 C11 121.48(16) . . ? C9 C10 H10A 119.3 . . ? C11 C10 H10A 119.3 . . ? C10 C11 C12 119.99(17) . . ? C10 C11 C19 119.05(16) . . ? C12 C11 C19 120.96(16) . . ? C13 C12 C11 118.41(16) . . ? C13 C12 H12A 120.8 . . ? C11 C12 H12A 120.8 . . ? C12 C13 C8 121.12(16) . . ? C12 C13 C1 128.47(15) . . ? C8 C13 C1 110.40(15) . . ? C18 C14 C15 114.90(18) . . ? C18 C14 C4 123.11(17) . . ? C15 C14 C4 121.96(19) . . ? F1 C15 C16 120.03(19) . . ? F1 C15 C14 120.35(18) . . ? C16 C15 C14 119.6(2) . . ? N1 C16 F2 117.2(2) . . ? N1 C16 C15 124.8(2) . . ? F2 C16 C15 117.9(2) . . ? N1 C17 F3 116.53(19) . . ? N1 C17 C18 123.9(2) . . ? F3 C17 C18 119.6(2) . . ? F4 C18 C17 119.00(19) . . ? F4 C18 C14 120.58(17) . . ? C17 C18 C14 120.4(2) . . ? C20 C19 C23 114.54(16) . . ? C20 C19 C11 122.51(16) . . ? C23 C19 C11 122.93(17) . . ? F5 C20 C21 118.54(17) . . ? F5 C20 C19 120.80(16) . . ? C21 C20 C19 120.67(17) . . ? N2 C21 F6 116.88(17) . . ? N2 C21 C20 123.76(18) . . ? F6 C21 C20 119.35(18) . . ? N2 C22 F7 116.39(17) . . ? N2 C22 C23 124.74(18) . . ? F7 C22 C23 118.87(18) . . ? F8 C23 C22 119.17(16) . . ? F8 C23 C19 120.81(16) . . ? C22 C23 C19 119.98(17) . . ? C25 C24 C29 121.28(18) . . ? C25 C24 C1 128.62(16) . . ? C29 C24 C1 110.09(17) . . ? C24 C25 C26 118.32(19) . . ? C24 C25 H25A 120.8 . . ? C26 C25 H25A 120.8 . . ? C25 C26 C27 121.0(2) . . ? C25 C26 H26A 119.5 . . ? C27 C26 H26A 119.5 . . ? C28 C27 C26 120.76(19) . . ? C28 C27 H27A 119.6 . . ? C26 C27 H27A 119.6 . . ? C27 C28 C29 119.02(19) . . ? C27 C28 H28A 120.5 . . ? C29 C28 H28A 120.5 . . ? C28 C29 C24 119.63(19) . . ? C28 C29 C30 131.49(18) . . ? C24 C29 C30 108.86(16) . . ? C31 C30 C35 119.9(2) . . ? C31 C30 C29 131.06(19) . . ? C35 C30 C29 108.97(16) . . ? C32 C31 C30 118.5(2) . . ? C32 C31 H31A 120.7 . . ? C30 C31 H31A 120.7 . . ? C31 C32 C33 121.30(19) . . ? C31 C32 H32A 119.3 . . ? C33 C32 H32A 119.3 . . ? C32 C33 C34 120.5(2) . . ? C32 C33 H33A 119.8 . . ? C34 C33 H33A 119.8 . . ? C35 C34 C33 118.43(19) . . ? C35 C34 H34A 120.8 . . ? C33 C34 H34A 120.8 . . ? C34 C35 C30 121.36(17) . . ? C34 C35 C1 128.20(17) . . ? C30 C35 C1 110.30(17) . . ? C16 N1 C17 116.41(19) . . ? C22 N2 C21 116.31(17) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.12 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.215 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.058 data_i0798 _database_code_depnum_ccdc_archive 'CCDC 919919' #TrackingRef 'chemcomm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C59 H32 F8 N4' _chemical_formula_sum 'C59 H32 F8 N4' _chemical_formula_weight 948.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 16.1222(9) _cell_length_b 16.8188(10) _cell_length_c 17.5167(10) _cell_angle_alpha 106.194(4) _cell_angle_beta 93.136(5) _cell_angle_gamma 90.734(5) _cell_volume 4552.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 28771 _cell_measurement_theta_min 1.26 _cell_measurement_theta_max 25.61 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9633 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details 'X-red ver. 1.31 (Stoe & Cie. 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 30 _diffrn_source_power 1.50 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 228 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 37189 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 15985 _reflns_number_gt 10838 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 15985 _refine_ls_number_parameters 1279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 0.879 _refine_ls_restrained_S_all 0.879 _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 C1 C -0.52385(11) -0.36969(10) 0.22965(9) 0.0270(4) Uani 1 1 d . . . C2 C -0.59061(11) -0.42503(10) 0.25006(10) 0.0272(4) Uani 1 1 d . . . C3 C -0.63953(11) -0.48692(10) 0.19788(10) 0.0307(4) Uani 1 1 d . . . H3A H -0.6326 -0.5009 0.1422 0.037 Uiso 1 1 calc R . . C4 C -0.69931(11) -0.52846(10) 0.22841(10) 0.0318(4) Uani 1 1 d . . . C5 C -0.70859(12) -0.50741(10) 0.31071(11) 0.0333(4) Uani 1 1 d . . . H5A H -0.7501 -0.5353 0.3309 0.040 Uiso 1 1 calc R . . C6 C -0.65812(12) -0.44634(10) 0.36342(10) 0.0327(4) Uani 1 1 d . . . H6A H -0.6644 -0.4331 0.4191 0.039 Uiso 1 1 calc R . . C7 C -0.59818(11) -0.40482(10) 0.33320(10) 0.0282(4) Uani 1 1 d . . . C8 C -0.53652(11) -0.33870(10) 0.37205(10) 0.0286(4) Uani 1 1 d . . . C9 C -0.51689(12) -0.29852(11) 0.45256(10) 0.0336(4) Uani 1 1 d . . . H9A H -0.5457 -0.3131 0.4929 0.040 Uiso 1 1 calc R . . C10 C -0.45480(12) -0.23718(11) 0.47255(11) 0.0368(4) Uani 1 1 d . . . H10A H -0.4405 -0.2102 0.5271 0.044 Uiso 1 1 calc R . . C11 C -0.41284(12) -0.21435(10) 0.41369(11) 0.0339(4) Uani 1 1 d . . . C12 C -0.43213(11) -0.25448(10) 0.33271(10) 0.0308(4) Uani 1 1 d . . . H12A H -0.4041 -0.2391 0.2924 0.037 Uiso 1 1 calc R . . C13 C -0.49275(11) -0.31678(10) 0.31302(9) 0.0272(4) Uani 1 1 d . . . C14 C -0.71263(12) -0.66075(10) 0.12325(10) 0.0330(4) Uani 1 1 d . . . C15 C -0.63774(12) -0.68850(10) 0.14904(11) 0.0341(4) Uani 1 1 d . . . H15A H -0.6125 -0.6606 0.1999 0.041 Uiso 1 1 calc R . . C16 C -0.59944(13) -0.75710(11) 0.10055(11) 0.0379(4) Uani 1 1 d . . . H16A H -0.5487 -0.7756 0.1189 0.045 Uiso 1 1 calc R . . C17 C -0.63532(14) -0.79822(11) 0.02571(11) 0.0426(5) Uani 1 1 d . . . H17A H -0.6097 -0.8452 -0.0069 0.051 Uiso 1 1 calc R . . C18 C -0.70845(14) -0.77028(12) -0.00084(12) 0.0466(5) Uani 1 1 d . . . H18A H -0.7327 -0.7978 -0.0523 0.056 Uiso 1 1 calc R . . C19 C -0.74751(13) -0.70167(12) 0.04730(11) 0.0418(5) Uani 1 1 d . . . H19A H -0.7978 -0.6830 0.0282 0.050 Uiso 1 1 calc R . . C20 C -0.83168(12) -0.56750(11) 0.15042(11) 0.0384(4) Uani 1 1 d . . . C21 C -0.84037(13) -0.49301(12) 0.13079(12) 0.0421(5) Uani 1 1 d . . . H21A H -0.7933 -0.4573 0.1344 0.051 Uiso 1 1 calc R . . C22 C -0.91804(14) -0.47121(13) 0.10585(13) 0.0492(5) Uani 1 1 d . . . H22A H -0.9238 -0.4200 0.0933 0.059 Uiso 1 1 calc R . . C23 C -0.98634(15) -0.52247(14) 0.09908(14) 0.0550(6) Uani 1 1 d . . . H23A H -1.0391 -0.5073 0.0816 0.066 Uiso 1 1 calc R . . C24 C -0.97775(15) -0.59686(15) 0.11807(16) 0.0648(7) Uani 1 1 d . . . H24A H -1.0248 -0.6329 0.1130 0.078 Uiso 1 1 calc R . . C25 C -0.90098(14) -0.61900(13) 0.14436(15) 0.0557(6) Uani 1 1 d . . . H25A H -0.8959 -0.6695 0.1582 0.067 Uiso 1 1 calc R . . C26 C -0.27141(12) -0.16929(11) 0.46666(10) 0.0359(4) Uani 1 1 d . . . C27 C -0.24046(13) -0.24886(12) 0.43752(11) 0.0411(5) Uani 1 1 d . . . H27A H -0.2726 -0.2898 0.3983 0.049 Uiso 1 1 calc R . . C28 C -0.16319(13) -0.26852(12) 0.46555(11) 0.0428(5) Uani 1 1 d . . . H28A H -0.1431 -0.3227 0.4453 0.051 Uiso 1 1 calc R . . C29 C -0.11538(13) -0.20975(12) 0.52270(11) 0.0407(5) Uani 1 1 d . . . H29A H -0.0620 -0.2227 0.5407 0.049 Uiso 1 1 calc R . . C30 C -0.14705(13) -0.13085(12) 0.55357(11) 0.0402(5) Uani 1 1 d . . . H30A H -0.1152 -0.0905 0.5937 0.048 Uiso 1 1 calc R . . C31 C -0.22413(13) -0.11077(12) 0.52649(11) 0.0402(5) Uani 1 1 d . . . H31A H -0.2450 -0.0572 0.5485 0.048 Uiso 1 1 calc R . . C32 C -0.36628(13) -0.07291(11) 0.41922(10) 0.0363(4) Uani 1 1 d . . . C33 C -0.30245(13) -0.02000(12) 0.40915(11) 0.0400(4) Uani 1 1 d . . . H33A H -0.2462 -0.0352 0.4131 0.048 Uiso 1 1 calc R . . C34 C -0.32085(14) 0.05436(12) 0.39342(11) 0.0440(5) Uani 1 1 d . . . H34A H -0.2767 0.0907 0.3893 0.053 Uiso 1 1 calc R . . C35 C -0.40220(15) 0.07684(13) 0.38353(13) 0.0505(5) Uani 1 1 d . . . H35A H -0.4141 0.1275 0.3718 0.061 Uiso 1 1 calc R . . C36 C -0.46618(15) 0.02374(12) 0.39111(13) 0.0510(5) Uani 1 1 d . . . H36A H -0.5223 0.0377 0.3834 0.061 Uiso 1 1 calc R . . C37 C -0.44874(13) -0.04963(12) 0.40987(12) 0.0440(5) Uani 1 1 d . . . H37A H -0.4931 -0.0844 0.4164 0.053 Uiso 1 1 calc R . . C38 C -0.45784(11) -0.42047(10) 0.17903(10) 0.0281(4) Uani 1 1 d . . . C39 C -0.41228(11) -0.48422(10) 0.19452(10) 0.0320(4) Uani 1 1 d . . . H39A H -0.4149 -0.4964 0.2441 0.038 Uiso 1 1 calc R . . C40 C -0.36212(11) -0.53058(10) 0.13594(10) 0.0329(4) Uani 1 1 d . . . C41 C -0.35524(12) -0.50892(11) 0.06473(11) 0.0357(4) Uani 1 1 d . . . H41A H -0.3193 -0.5388 0.0264 0.043 Uiso 1 1 calc R . . C42 C -0.40059(12) -0.44388(11) 0.04923(10) 0.0345(4) Uani 1 1 d . . . H42A H -0.3951 -0.4292 0.0011 0.041 Uiso 1 1 calc R . . C43 C -0.45409(11) -0.40098(10) 0.10605(10) 0.0287(4) Uani 1 1 d . . . C44 C -0.51686(11) -0.33819(10) 0.10327(9) 0.0268(4) Uani 1 1 d . . . C45 C -0.54114(11) -0.30125(10) 0.04378(10) 0.0308(4) Uani 1 1 d . . . H45A H -0.5130 -0.3125 -0.0042 0.037 Uiso 1 1 calc R . . C46 C -0.60744(12) -0.24744(10) 0.05592(10) 0.0316(4) Uani 1 1 d . . . H46A H -0.6250 -0.2225 0.0155 0.038 Uiso 1 1 calc R . . C47 C -0.64850(11) -0.22970(10) 0.12730(10) 0.0288(4) Uani 1 1 d . . . C48 C -0.62338(11) -0.26585(10) 0.18723(10) 0.0272(4) Uani 1 1 d . . . H48A H -0.6505 -0.2534 0.2358 0.033 Uiso 1 1 calc R . . C49 C -0.55827(11) -0.32012(9) 0.17466(9) 0.0255(4) Uani 1 1 d . . . C50 C -0.32328(12) -0.60709(11) 0.14789(10) 0.0339(4) Uani 1 1 d . . . C51 C -0.24177(12) -0.62922(11) 0.13074(11) 0.0363(4) Uani 1 1 d . . . C52 C -0.21218(13) -0.70236(11) 0.14247(11) 0.0389(4) Uani 1 1 d . . . C53 C -0.33268(13) -0.73485(11) 0.18486(11) 0.0373(4) Uani 1 1 d . . . C54 C -0.36926(12) -0.66316(10) 0.17551(10) 0.0326(4) Uani 1 1 d . . . C55 C -0.72034(12) -0.17354(11) 0.14033(10) 0.0335(4) Uani 1 1 d . . . C56 C -0.79366(13) -0.19250(13) 0.09240(12) 0.0435(5) Uani 1 1 d . . . C57 C -0.85996(14) -0.14022(17) 0.10782(15) 0.0561(6) Uani 1 1 d . . . C58 C -0.79089(16) -0.05291(12) 0.21190(14) 0.0503(6) Uani 1 1 d . . . C59 C -0.72056(13) -0.10083(11) 0.20277(12) 0.0389(5) Uani 1 1 d . . . C60 C -0.07233(11) 0.11389(10) 0.26332(9) 0.0258(4) Uani 1 1 d . . . C61 C -0.05810(10) 0.04590(10) 0.30508(9) 0.0256(4) Uani 1 1 d . . . C62 C -0.03087(11) -0.03376(10) 0.27218(10) 0.0281(4) Uani 1 1 d . . . H62A H -0.0165 -0.0514 0.2183 0.034 Uiso 1 1 calc R . . C63 C -0.02512(11) -0.08715(10) 0.32040(10) 0.0312(4) Uani 1 1 d . . . C64 C -0.04826(12) -0.06187(10) 0.39903(10) 0.0333(4) Uani 1 1 d . . . H64A H -0.0449 -0.0994 0.4307 0.040 Uiso 1 1 calc R . . C65 C -0.07632(12) 0.01823(10) 0.43172(10) 0.0324(4) Uani 1 1 d . . . H65A H -0.0923 0.0351 0.4851 0.039 Uiso 1 1 calc R . . C66 C -0.08051(11) 0.07276(10) 0.38473(9) 0.0270(4) Uani 1 1 d . . . C67 C -0.10689(10) 0.15958(10) 0.40133(9) 0.0258(4) Uani 1 1 d . . . C68 C -0.13450(11) 0.21471(10) 0.47026(10) 0.0317(4) Uani 1 1 d . . . H68A H -0.1379 0.1983 0.5177 0.038 Uiso 1 1 calc R . . C69 C -0.15692(12) 0.29369(10) 0.46850(10) 0.0323(4) Uani 1 1 d . . . H69A H -0.1766 0.3310 0.5148 0.039 Uiso 1 1 calc R . . C70 C -0.15083(11) 0.31897(10) 0.39934(10) 0.0299(4) Uani 1 1 d . . . C71 C -0.12153(11) 0.26459(10) 0.33048(10) 0.0272(4) Uani 1 1 d . . . H71A H -0.1159 0.2819 0.2838 0.033 Uiso 1 1 calc R . . C72 C -0.10090(10) 0.18516(10) 0.33171(9) 0.0245(3) Uani 1 1 d . . . C73 C 0.08464(12) -0.19019(10) 0.30874(10) 0.0310(4) Uani 1 1 d . . . C74 C 0.14304(12) -0.12776(10) 0.34929(10) 0.0316(4) Uani 1 1 d . . . H74A H 0.1283 -0.0713 0.3604 0.038 Uiso 1 1 calc R . . C75 C 0.22195(12) -0.14730(11) 0.37330(10) 0.0344(4) Uani 1 1 d . . . H75A H 0.2602 -0.1042 0.4013 0.041 Uiso 1 1 calc R . . C76 C 0.24568(12) -0.23001(11) 0.35664(10) 0.0363(4) Uani 1 1 d . . . H76A H 0.2994 -0.2435 0.3736 0.044 Uiso 1 1 calc R . . C77 C 0.18937(13) -0.29152(11) 0.31514(11) 0.0377(4) Uani 1 1 d . . . H77A H 0.2052 -0.3477 0.3027 0.045 Uiso 1 1 calc R . . C78 C 0.10996(12) -0.27319(11) 0.29108(11) 0.0364(4) Uani 1 1 d . . . H78A H 0.0725 -0.3167 0.2626 0.044 Uiso 1 1 calc R . . C79 C -0.05492(12) -0.22859(10) 0.23548(11) 0.0360(4) Uani 1 1 d . . . C80 C -0.03457(13) -0.27541(11) 0.15980(11) 0.0412(5) Uani 1 1 d . . . H80A H 0.0193 -0.2696 0.1422 0.049 Uiso 1 1 calc R . . C81 C -0.09280(15) -0.33046(12) 0.11022(13) 0.0493(5) Uani 1 1 d . . . H81A H -0.0785 -0.3622 0.0590 0.059 Uiso 1 1 calc R . . C82 C -0.17145(15) -0.33918(13) 0.13527(14) 0.0553(6) Uani 1 1 d . . . H82A H -0.2110 -0.3773 0.1016 0.066 Uiso 1 1 calc R . . C83 C -0.19240(15) -0.29187(14) 0.21004(14) 0.0577(6) Uani 1 1 d . . . H83A H -0.2466 -0.2972 0.2270 0.069 Uiso 1 1 calc R . . C84 C -0.13455(13) -0.23687(13) 0.25993(13) 0.0473(5) Uani 1 1 d . . . H84A H -0.1493 -0.2048 0.3109 0.057 Uiso 1 1 calc R . . C85 C -0.26075(12) 0.41927(11) 0.40056(10) 0.0355(4) Uani 1 1 d . . . C86 C -0.32179(12) 0.35598(12) 0.37869(10) 0.0379(4) Uani 1 1 d . . . H86A H -0.3058 0.2999 0.3625 0.046 Uiso 1 1 calc R . . C87 C -0.40572(14) 0.37422(14) 0.38032(11) 0.0460(5) Uani 1 1 d . . . H87A H -0.4466 0.3307 0.3654 0.055 Uiso 1 1 calc R . . C88 C -0.43002(15) 0.45701(15) 0.40392(12) 0.0539(6) Uani 1 1 d . . . H88A H -0.4873 0.4698 0.4045 0.065 Uiso 1 1 calc R . . C89 C -0.36979(15) 0.51965(14) 0.42626(12) 0.0523(6) Uani 1 1 d . . . H89A H -0.3861 0.5757 0.4422 0.063 Uiso 1 1 calc R . . C90 C -0.28611(14) 0.50231(12) 0.42591(11) 0.0439(5) Uani 1 1 d . . . H90A H -0.2456 0.5462 0.4427 0.053 Uiso 1 1 calc R . . C91 C -0.11433(14) 0.45004(10) 0.37360(11) 0.0385(5) Uani 1 1 d . . . C92 C -0.03165(14) 0.44828(12) 0.40149(13) 0.0490(5) Uani 1 1 d . . . H92A H -0.0178 0.4175 0.4381 0.059 Uiso 1 1 calc R . . C93 C 0.03048(18) 0.49114(15) 0.37618(18) 0.0733(8) Uani 1 1 d . . . H93A H 0.0866 0.4890 0.3949 0.088 Uiso 1 1 calc R . . C94 C 0.0105(2) 0.53663(17) 0.3240(2) 0.0836(9) Uani 1 1 d . . . H94A H 0.0531 0.5659 0.3067 0.100 Uiso 1 1 calc R . . C95 C -0.0709(2) 0.54019(14) 0.29648(15) 0.0678(8) Uani 1 1 d . . . H95A H -0.0840 0.5725 0.2610 0.081 Uiso 1 1 calc R . . C96 C -0.13445(16) 0.49642(11) 0.32064(12) 0.0483(5) Uani 1 1 d . . . H96A H -0.1904 0.4983 0.3012 0.058 Uiso 1 1 calc R . . C97 C -0.13665(11) 0.08358(9) 0.19364(9) 0.0260(4) Uani 1 1 d . . . C98 C -0.21765(11) 0.05725(10) 0.19660(10) 0.0271(4) Uani 1 1 d . . . H98A H -0.2395 0.0581 0.2461 0.033 Uiso 1 1 calc R . . C99 C -0.26687(11) 0.02947(10) 0.12593(10) 0.0287(4) Uani 1 1 d . . . C100 C -0.23337(11) 0.02593(10) 0.05254(10) 0.0311(4) Uani 1 1 d . . . H100 H -0.2672 0.0068 0.0046 0.037 Uiso 1 1 calc R . . C101 C -0.15098(12) 0.05031(10) 0.04970(10) 0.0310(4) Uani 1 1 d . . . H101 H -0.1283 0.0470 0.0000 0.037 Uiso 1 1 calc R . . C102 C -0.10215(11) 0.07960(10) 0.12051(9) 0.0270(4) Uani 1 1 d . . . C103 C -0.01459(11) 0.10996(10) 0.13767(10) 0.0278(4) Uani 1 1 d . . . C104 C 0.04847(11) 0.11773(10) 0.08806(10) 0.0307(4) Uani 1 1 d . . . H104 H 0.0376 0.1038 0.0320 0.037 Uiso 1 1 calc R . . C105 C 0.12718(11) 0.14616(10) 0.12199(10) 0.0316(4) Uani 1 1 d . . . H105 H 0.1707 0.1494 0.0884 0.038 Uiso 1 1 calc R . . C106 C 0.14358(11) 0.17024(10) 0.20522(10) 0.0292(4) Uani 1 1 d . . . C107 C 0.07937(11) 0.16372(10) 0.25465(10) 0.0280(4) Uani 1 1 d . . . H107 H 0.0891 0.1808 0.3109 0.034 Uiso 1 1 calc R . . C108 C 0.00256(11) 0.13241(9) 0.22098(9) 0.0260(4) Uani 1 1 d . . . C109 C -0.35427(11) 0.00239(10) 0.13059(9) 0.0281(4) Uani 1 1 d . . . C110 C -0.42239(12) 0.03515(10) 0.09873(10) 0.0307(4) Uani 1 1 d . . . C111 C -0.50163(12) 0.00782(11) 0.10581(10) 0.0330(4) Uani 1 1 d . . . C112 C -0.45614(12) -0.07997(11) 0.17283(10) 0.0340(4) Uani 1 1 d . . . C113 C -0.37412(11) -0.05695(10) 0.16937(10) 0.0310(4) Uani 1 1 d . . . C114 C 0.22750(11) 0.19778(10) 0.24399(10) 0.0299(4) Uani 1 1 d . . . C115 C 0.29831(11) 0.15225(10) 0.22261(10) 0.0309(4) Uani 1 1 d . . . C116 C 0.37286(12) 0.17676(12) 0.26523(11) 0.0367(4) Uani 1 1 d . . . C117 C 0.31780(13) 0.28798(11) 0.34721(10) 0.0360(4) Uani 1 1 d . . . C118 C 0.24024(12) 0.26849(10) 0.30884(10) 0.0329(4) Uani 1 1 d . . . N1 N -0.75197(10) -0.59252(9) 0.17521(9) 0.0350(3) Uani 1 1 d . . . N2 N -0.35019(10) -0.14934(9) 0.43674(9) 0.0401(4) Uani 1 1 d . . . N3 N -0.25606(11) -0.75495(9) 0.16879(9) 0.0392(4) Uani 1 1 d . . . N4 N -0.85876(13) -0.07084(13) 0.16591(13) 0.0577(5) Uani 1 1 d . . . N5 N 0.00391(10) -0.17032(8) 0.28712(9) 0.0342(3) Uani 1 1 d . . . N6 N -0.17477(10) 0.40100(8) 0.39884(9) 0.0348(4) Uani 1 1 d . . . N7 N -0.51969(10) -0.04894(9) 0.14124(9) 0.0353(4) Uani 1 1 d . . . N8 N 0.38430(10) 0.24341(10) 0.32681(9) 0.0391(4) Uani 1 1 d . . . F1 F -0.19172(7) -0.57968(6) 0.10430(7) 0.0440(3) Uani 1 1 d . . . F2 F -0.13328(7) -0.72299(7) 0.12658(7) 0.0501(3) Uani 1 1 d . . . F3 F -0.37738(7) -0.78766(6) 0.21259(6) 0.0462(3) Uani 1 1 d . . . F4 F -0.44858(7) -0.65024(6) 0.19277(6) 0.0425(3) Uani 1 1 d . . . F5 F -0.80148(8) -0.26401(8) 0.03297(7) 0.0577(3) Uani 1 1 d . . . F6 F -0.93091(8) -0.16050(11) 0.06112(9) 0.0773(5) Uani 1 1 d . . . F7 F -0.79035(9) 0.01676(7) 0.27318(8) 0.0686(4) Uani 1 1 d . . . F8 F -0.65477(8) -0.07707(6) 0.25469(7) 0.0465(3) Uani 1 1 d . . . F9 F -0.41163(7) 0.09478(6) 0.06126(6) 0.0365(2) Uani 1 1 d . . . F10 F -0.56641(7) 0.04082(6) 0.07437(6) 0.0405(3) Uani 1 1 d . . . F11 F -0.47321(7) -0.13815(6) 0.20879(6) 0.0446(3) Uani 1 1 d . . . F12 F -0.31348(7) -0.09430(6) 0.20158(6) 0.0389(2) Uani 1 1 d . . . F13 F 0.29377(7) 0.08177(6) 0.16156(6) 0.0388(2) Uani 1 1 d . . . F14 F 0.44109(7) 0.13114(7) 0.24541(7) 0.0490(3) Uani 1 1 d . . . F15 F 0.32853(8) 0.35564(7) 0.40958(6) 0.0491(3) Uani 1 1 d . . . F16 F 0.17623(7) 0.31877(6) 0.33478(6) 0.0404(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 C1 0.0314(10) 0.0253(8) 0.0248(8) 0.0074(7) 0.0036(7) 0.0040(7) C2 0.0304(10) 0.0229(8) 0.0297(9) 0.0093(7) 0.0030(7) 0.0066(7) C3 0.0364(11) 0.0265(8) 0.0288(9) 0.0066(7) 0.0042(8) 0.0033(8) C4 0.0344(11) 0.0242(8) 0.0371(10) 0.0088(7) 0.0022(8) 0.0029(8) C5 0.0317(11) 0.0307(9) 0.0415(10) 0.0155(8) 0.0073(8) 0.0027(8) C6 0.0382(11) 0.0333(9) 0.0295(9) 0.0120(8) 0.0077(8) 0.0070(8) C7 0.0326(10) 0.0255(8) 0.0278(9) 0.0092(7) 0.0032(7) 0.0079(7) C8 0.0309(10) 0.0274(8) 0.0291(9) 0.0104(7) 0.0024(7) 0.0066(7) C9 0.0386(11) 0.0349(9) 0.0283(9) 0.0103(8) 0.0036(8) 0.0054(8) C10 0.0465(12) 0.0348(10) 0.0266(9) 0.0049(7) -0.0023(8) 0.0057(9) C11 0.0348(11) 0.0277(9) 0.0370(10) 0.0070(8) -0.0064(8) 0.0019(8) C12 0.0338(11) 0.0303(9) 0.0296(9) 0.0104(7) 0.0015(8) 0.0040(8) C13 0.0302(10) 0.0241(8) 0.0274(8) 0.0072(7) 0.0014(7) 0.0065(7) C14 0.0381(11) 0.0260(9) 0.0355(10) 0.0091(7) 0.0068(8) -0.0019(8) C15 0.0399(11) 0.0294(9) 0.0336(9) 0.0094(8) 0.0051(8) -0.0015(8) C16 0.0400(12) 0.0323(9) 0.0423(11) 0.0110(8) 0.0079(9) 0.0017(8) C17 0.0536(14) 0.0324(10) 0.0392(11) 0.0041(8) 0.0122(10) 0.0012(9) C18 0.0568(15) 0.0396(11) 0.0381(11) 0.0019(9) 0.0043(10) -0.0028(10) C19 0.0426(12) 0.0397(10) 0.0413(11) 0.0087(9) 0.0002(9) -0.0012(9) C20 0.0363(12) 0.0328(10) 0.0444(11) 0.0075(8) 0.0044(9) 0.0012(8) C21 0.0430(13) 0.0366(10) 0.0453(11) 0.0096(9) -0.0003(9) 0.0001(9) C22 0.0497(14) 0.0429(11) 0.0528(12) 0.0103(10) -0.0017(10) 0.0074(10) C23 0.0422(14) 0.0536(13) 0.0660(14) 0.0119(11) -0.0012(11) 0.0092(11) C24 0.0370(14) 0.0594(15) 0.0979(19) 0.0231(14) -0.0002(13) -0.0036(11) C25 0.0419(14) 0.0444(12) 0.0846(17) 0.0244(12) 0.0044(12) -0.0010(10) C26 0.0391(12) 0.0359(10) 0.0318(9) 0.0094(8) -0.0031(8) -0.0035(9) C27 0.0420(12) 0.0416(11) 0.0353(10) 0.0045(8) -0.0035(9) -0.0020(9) C28 0.0436(13) 0.0412(11) 0.0413(11) 0.0082(9) 0.0006(9) 0.0045(9) C29 0.0390(12) 0.0500(12) 0.0371(10) 0.0196(9) -0.0017(9) -0.0022(9) C30 0.0449(13) 0.0411(11) 0.0347(10) 0.0130(8) -0.0075(9) -0.0091(9) C31 0.0478(13) 0.0363(10) 0.0352(10) 0.0094(8) -0.0054(9) -0.0025(9) C32 0.0443(12) 0.0315(9) 0.0303(9) 0.0048(8) -0.0001(8) -0.0006(9) C33 0.0416(12) 0.0437(11) 0.0342(10) 0.0105(8) 0.0001(9) -0.0015(9) C34 0.0540(14) 0.0426(11) 0.0364(10) 0.0131(9) 0.0032(9) -0.0081(10) C35 0.0603(16) 0.0374(11) 0.0562(13) 0.0168(10) 0.0058(11) 0.0060(10) C36 0.0476(14) 0.0396(11) 0.0667(14) 0.0162(10) 0.0041(11) 0.0068(10) C37 0.0427(13) 0.0350(10) 0.0538(12) 0.0110(9) 0.0050(10) 0.0005(9) C38 0.0276(10) 0.0277(8) 0.0279(9) 0.0060(7) 0.0013(7) -0.0003(7) C39 0.0352(11) 0.0293(9) 0.0309(9) 0.0073(7) 0.0017(8) 0.0022(8) C40 0.0318(11) 0.0312(9) 0.0346(9) 0.0076(8) 0.0006(8) 0.0032(8) C41 0.0313(11) 0.0350(9) 0.0383(10) 0.0048(8) 0.0068(8) 0.0051(8) C42 0.0362(11) 0.0368(10) 0.0311(9) 0.0092(8) 0.0078(8) 0.0027(8) C43 0.0289(10) 0.0265(8) 0.0299(9) 0.0063(7) 0.0029(7) -0.0004(7) C44 0.0275(10) 0.0252(8) 0.0266(8) 0.0055(7) 0.0029(7) -0.0029(7) C45 0.0345(11) 0.0315(9) 0.0267(9) 0.0077(7) 0.0062(8) -0.0002(8) C46 0.0369(11) 0.0327(9) 0.0280(9) 0.0134(7) 0.0004(8) -0.0004(8) C47 0.0286(10) 0.0288(9) 0.0305(9) 0.0106(7) 0.0020(7) -0.0002(7) C48 0.0296(10) 0.0268(8) 0.0257(8) 0.0073(7) 0.0056(7) 0.0008(7) C49 0.0274(10) 0.0237(8) 0.0248(8) 0.0063(6) 0.0006(7) -0.0028(7) C50 0.0340(11) 0.0350(9) 0.0290(9) 0.0034(7) -0.0020(8) 0.0041(8) C51 0.0365(11) 0.0336(9) 0.0379(10) 0.0091(8) 0.0003(8) -0.0003(8) C52 0.0389(12) 0.0363(10) 0.0400(10) 0.0083(8) -0.0009(9) 0.0108(9) C53 0.0463(13) 0.0332(10) 0.0314(9) 0.0086(8) -0.0033(9) -0.0031(9) C54 0.0329(11) 0.0310(9) 0.0314(9) 0.0045(7) 0.0029(8) 0.0021(8) C55 0.0354(11) 0.0373(10) 0.0347(10) 0.0201(8) 0.0085(8) 0.0069(8) C56 0.0383(12) 0.0566(13) 0.0434(11) 0.0260(10) 0.0065(9) 0.0087(10) C57 0.0342(13) 0.0888(18) 0.0663(15) 0.0553(15) 0.0052(11) 0.0121(12) C58 0.0634(17) 0.0410(11) 0.0596(14) 0.0297(11) 0.0327(13) 0.0185(11) C59 0.0447(13) 0.0359(10) 0.0435(11) 0.0210(9) 0.0138(10) 0.0072(9) C60 0.0274(10) 0.0264(8) 0.0240(8) 0.0072(7) 0.0033(7) 0.0027(7) C61 0.0227(9) 0.0283(8) 0.0266(8) 0.0095(7) 0.0002(7) 0.0000(7) C62 0.0280(10) 0.0296(8) 0.0270(8) 0.0079(7) 0.0030(7) 0.0015(7) C63 0.0307(10) 0.0270(9) 0.0355(10) 0.0081(7) 0.0018(8) 0.0034(7) C64 0.0380(11) 0.0309(9) 0.0351(10) 0.0161(8) 0.0018(8) 0.0038(8) C65 0.0377(11) 0.0334(9) 0.0278(9) 0.0109(7) 0.0051(8) 0.0025(8) C66 0.0247(9) 0.0300(9) 0.0272(8) 0.0098(7) 0.0014(7) 0.0001(7) C67 0.0254(9) 0.0267(8) 0.0260(8) 0.0084(7) 0.0020(7) -0.0002(7) C68 0.0371(11) 0.0341(9) 0.0251(9) 0.0098(7) 0.0050(8) 0.0016(8) C69 0.0375(11) 0.0289(9) 0.0296(9) 0.0054(7) 0.0091(8) 0.0025(8) C70 0.0313(10) 0.0255(8) 0.0330(9) 0.0077(7) 0.0052(8) 0.0011(7) C71 0.0285(10) 0.0287(8) 0.0255(8) 0.0093(7) 0.0025(7) -0.0020(7) C72 0.0209(9) 0.0269(8) 0.0252(8) 0.0067(7) -0.0003(7) -0.0011(7) C73 0.0379(11) 0.0282(9) 0.0304(9) 0.0129(7) 0.0077(8) 0.0049(8) C74 0.0401(11) 0.0283(9) 0.0302(9) 0.0132(7) 0.0082(8) 0.0051(8) C75 0.0349(11) 0.0375(10) 0.0335(9) 0.0133(8) 0.0080(8) 0.0006(8) C76 0.0350(11) 0.0453(11) 0.0336(10) 0.0172(8) 0.0108(8) 0.0097(9) C77 0.0446(12) 0.0322(9) 0.0398(10) 0.0142(8) 0.0107(9) 0.0108(9) C78 0.0414(12) 0.0295(9) 0.0403(10) 0.0127(8) 0.0041(9) 0.0029(8) C79 0.0442(12) 0.0274(9) 0.0392(10) 0.0139(8) 0.0001(9) 0.0048(8) C80 0.0466(13) 0.0369(10) 0.0407(11) 0.0121(9) 0.0014(9) 0.0043(9) C81 0.0582(15) 0.0416(11) 0.0441(12) 0.0070(9) -0.0062(11) 0.0056(10) C82 0.0532(15) 0.0455(12) 0.0619(14) 0.0104(11) -0.0178(12) -0.0030(11) C83 0.0446(14) 0.0578(14) 0.0679(15) 0.0141(12) -0.0003(12) -0.0030(11) C84 0.0428(13) 0.0466(12) 0.0509(12) 0.0106(10) 0.0052(10) -0.0007(10) C85 0.0440(12) 0.0350(10) 0.0280(9) 0.0086(8) 0.0056(8) 0.0095(9) C86 0.0425(12) 0.0423(10) 0.0322(10) 0.0140(8) 0.0085(8) 0.0102(9) C87 0.0437(13) 0.0609(13) 0.0368(10) 0.0182(10) 0.0063(9) 0.0069(10) C88 0.0497(14) 0.0785(16) 0.0388(11) 0.0222(11) 0.0122(10) 0.0312(13) C89 0.0627(16) 0.0504(13) 0.0420(12) 0.0087(10) 0.0041(11) 0.0265(12) C90 0.0572(14) 0.0374(10) 0.0352(10) 0.0065(8) 0.0027(9) 0.0150(10) C91 0.0558(14) 0.0249(9) 0.0337(10) 0.0049(7) 0.0105(9) 0.0022(9) C92 0.0546(15) 0.0391(11) 0.0547(13) 0.0159(10) 0.0033(11) -0.0096(10) C93 0.0644(18) 0.0562(14) 0.106(2) 0.0336(15) 0.0114(16) -0.0146(13) C94 0.081(2) 0.0652(17) 0.121(2) 0.0504(17) 0.0306(19) -0.0071(16) C95 0.098(2) 0.0501(13) 0.0684(16) 0.0335(12) 0.0276(16) 0.0096(14) C96 0.0726(16) 0.0361(10) 0.0391(11) 0.0135(9) 0.0131(11) 0.0052(10) C97 0.0321(10) 0.0220(8) 0.0254(8) 0.0085(7) 0.0031(7) 0.0047(7) C98 0.0306(10) 0.0254(8) 0.0261(8) 0.0080(7) 0.0038(7) 0.0028(7) C99 0.0310(10) 0.0245(8) 0.0302(9) 0.0072(7) 0.0014(7) 0.0018(7) C100 0.0352(11) 0.0308(9) 0.0265(9) 0.0074(7) -0.0021(8) 0.0009(8) C101 0.0376(11) 0.0322(9) 0.0244(9) 0.0092(7) 0.0054(8) 0.0030(8) C102 0.0303(10) 0.0249(8) 0.0268(9) 0.0085(7) 0.0031(7) 0.0044(7) C103 0.0303(10) 0.0261(8) 0.0284(9) 0.0095(7) 0.0039(7) 0.0046(7) C104 0.0343(11) 0.0338(9) 0.0255(9) 0.0107(7) 0.0031(8) 0.0019(8) C105 0.0321(11) 0.0332(9) 0.0322(9) 0.0120(7) 0.0095(8) 0.0034(8) C106 0.0310(10) 0.0268(8) 0.0323(9) 0.0117(7) 0.0050(8) 0.0035(7) C107 0.0335(11) 0.0260(8) 0.0257(8) 0.0084(7) 0.0053(7) 0.0033(8) C108 0.0276(10) 0.0238(8) 0.0279(8) 0.0087(7) 0.0048(7) 0.0031(7) C109 0.0311(10) 0.0268(8) 0.0236(8) 0.0029(7) 0.0003(7) -0.0016(7) C110 0.0375(11) 0.0271(8) 0.0270(9) 0.0070(7) 0.0014(8) -0.0023(8) C111 0.0324(11) 0.0355(9) 0.0289(9) 0.0060(8) -0.0022(8) 0.0024(8) C112 0.0401(12) 0.0317(9) 0.0305(9) 0.0097(8) 0.0004(8) -0.0071(8) C113 0.0341(11) 0.0288(9) 0.0292(9) 0.0074(7) -0.0028(8) 0.0017(8) C114 0.0320(10) 0.0307(9) 0.0301(9) 0.0134(7) 0.0044(8) -0.0033(8) C115 0.0333(11) 0.0316(9) 0.0275(9) 0.0079(7) 0.0019(8) -0.0006(8) C116 0.0331(11) 0.0429(11) 0.0367(10) 0.0147(9) 0.0056(8) 0.0065(9) C117 0.0431(13) 0.0334(10) 0.0315(9) 0.0097(8) 0.0003(9) -0.0010(9) C118 0.0334(11) 0.0317(9) 0.0363(10) 0.0131(8) 0.0067(8) 0.0026(8) N1 0.0338(9) 0.0280(8) 0.0422(9) 0.0080(7) 0.0034(7) 0.0000(7) N2 0.0415(10) 0.0324(8) 0.0439(9) 0.0093(7) -0.0107(8) -0.0038(7) N3 0.0429(10) 0.0333(8) 0.0392(9) 0.0072(7) -0.0029(7) 0.0075(7) N4 0.0533(13) 0.0693(13) 0.0721(14) 0.0495(12) 0.0283(11) 0.0258(11) N5 0.0382(10) 0.0251(7) 0.0391(8) 0.0090(6) 0.0005(7) 0.0055(7) N6 0.0424(10) 0.0249(7) 0.0390(8) 0.0105(6) 0.0090(7) 0.0043(7) N7 0.0344(9) 0.0359(8) 0.0343(8) 0.0081(7) 0.0020(7) -0.0040(7) N8 0.0372(10) 0.0458(9) 0.0364(9) 0.0159(8) -0.0008(7) -0.0019(8) F1 0.0369(7) 0.0411(6) 0.0573(7) 0.0181(5) 0.0076(5) 0.0040(5) F2 0.0386(7) 0.0482(7) 0.0662(8) 0.0197(6) 0.0041(6) 0.0131(5) F3 0.0567(8) 0.0353(6) 0.0481(6) 0.0142(5) 0.0044(6) -0.0019(5) F4 0.0383(7) 0.0405(6) 0.0497(6) 0.0140(5) 0.0044(5) 0.0023(5) F5 0.0465(8) 0.0783(9) 0.0468(7) 0.0181(7) -0.0105(6) -0.0026(6) F6 0.0368(8) 0.1297(13) 0.0934(10) 0.0770(10) 0.0029(7) 0.0131(8) F7 0.0951(11) 0.0432(7) 0.0813(9) 0.0301(7) 0.0545(8) 0.0308(7) F8 0.0569(8) 0.0352(6) 0.0454(6) 0.0057(5) 0.0150(6) 0.0008(5) F9 0.0408(6) 0.0342(5) 0.0380(5) 0.0162(4) 0.0001(5) 0.0010(5) F10 0.0337(6) 0.0480(6) 0.0402(6) 0.0135(5) -0.0014(5) 0.0056(5) F11 0.0483(7) 0.0436(6) 0.0470(6) 0.0226(5) -0.0005(5) -0.0118(5) F12 0.0415(7) 0.0362(5) 0.0424(6) 0.0180(5) -0.0046(5) -0.0001(5) F13 0.0364(6) 0.0395(6) 0.0377(6) 0.0054(5) 0.0062(5) 0.0049(5) F14 0.0329(7) 0.0595(7) 0.0525(7) 0.0118(6) 0.0016(5) 0.0112(5) F15 0.0537(8) 0.0448(6) 0.0420(6) 0.0028(5) -0.0064(5) -0.0047(6) F16 0.0399(7) 0.0329(5) 0.0461(6) 0.0061(5) 0.0077(5) 0.0035(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 C1 C49 1.527(2) . ? C1 C38 1.534(2) . ? C1 C2 1.534(2) . ? C1 C13 1.536(2) . ? C2 C3 1.382(2) . ? C2 C7 1.413(2) . ? C3 C4 1.397(2) . ? C3 H3A 0.9500 . ? C4 C5 1.402(2) . ? C4 N1 1.442(2) . ? C5 C6 1.392(3) . ? C5 H5A 0.9500 . ? C6 C7 1.395(2) . ? C6 H6A 0.9500 . ? C7 C8 1.471(3) . ? C8 C9 1.400(2) . ? C8 C13 1.410(2) . ? C9 C10 1.387(3) . ? C9 H9A 0.9500 . ? C10 C11 1.399(3) . ? C10 H10A 0.9500 . ? C11 C12 1.406(2) . ? C11 N2 1.435(2) . ? C12 C13 1.381(2) . ? C12 H12A 0.9500 . ? C14 C15 1.397(3) . ? C14 C19 1.399(3) . ? C14 N1 1.431(2) . ? C15 C16 1.401(2) . ? C15 H15A 0.9500 . ? C16 C17 1.390(3) . ? C16 H16A 0.9500 . ? C17 C18 1.380(3) . ? C17 H17A 0.9500 . ? C18 C19 1.405(3) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C25 1.386(3) . ? C20 C21 1.395(3) . ? C20 N1 1.439(3) . ? C21 C22 1.391(3) . ? C21 H21A 0.9500 . ? C22 C23 1.369(3) . ? C22 H22A 0.9500 . ? C23 C24 1.388(3) . ? C23 H23A 0.9500 . ? C24 C25 1.388(3) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 C27 1.402(3) . ? C26 C31 1.402(3) . ? C26 N2 1.427(3) . ? C27 C28 1.392(3) . ? C27 H27A 0.9500 . ? C28 C29 1.385(3) . ? C28 H28A 0.9500 . ? C29 C30 1.400(3) . ? C29 H29A 0.9500 . ? C30 C31 1.385(3) . ? C30 H30A 0.9500 . ? C31 H31A 0.9500 . ? C32 C33 1.402(3) . ? C32 C37 1.404(3) . ? C32 N2 1.426(2) . ? C33 C34 1.386(3) . ? C33 H33A 0.9500 . ? C34 C35 1.385(3) . ? C34 H34A 0.9500 . ? C35 C36 1.392(3) . ? C35 H35A 0.9500 . ? C36 C37 1.391(3) . ? C36 H36A 0.9500 . ? C37 H37A 0.9500 . ? C38 C39 1.387(2) . ? C38 C43 1.410(2) . ? C39 C40 1.405(2) . ? C39 H39A 0.9500 . ? C40 C41 1.403(2) . ? C40 C50 1.499(2) . ? C41 C42 1.403(3) . ? C41 H41A 0.9500 . ? C42 C43 1.402(2) . ? C42 H42A 0.9500 . ? C43 C44 1.481(2) . ? C44 C45 1.396(2) . ? C44 C49 1.410(2) . ? C45 C46 1.396(3) . ? C45 H45A 0.9500 . ? C46 C47 1.406(2) . ? C46 H46A 0.9500 . ? C47 C48 1.397(2) . ? C47 C55 1.491(2) . ? C48 C49 1.386(2) . ? C48 H48A 0.9500 . ? C50 C54 1.396(2) . ? C50 C51 1.396(3) . ? C51 F1 1.341(2) . ? C51 C52 1.389(3) . ? C52 N3 1.320(2) . ? C52 F2 1.346(2) . ? C53 N3 1.310(2) . ? C53 F3 1.344(2) . ? C53 C54 1.395(3) . ? C54 F4 1.337(2) . ? C55 C56 1.392(3) . ? C55 C59 1.395(3) . ? C56 F5 1.353(2) . ? C56 C57 1.383(3) . ? C57 N4 1.316(3) . ? C57 F6 1.351(3) . ? C58 N4 1.303(3) . ? C58 F7 1.350(3) . ? C58 C59 1.390(3) . ? C59 F8 1.339(2) . ? C60 C108 1.524(2) . ? C60 C97 1.525(2) . ? C60 C61 1.533(2) . ? C60 C72 1.535(2) . ? C61 C62 1.390(2) . ? C61 C66 1.410(2) . ? C62 C63 1.395(2) . ? C62 H62A 0.9500 . ? C63 C64 1.397(2) . ? C63 N5 1.452(2) . ? C64 C65 1.401(2) . ? C64 H64A 0.9500 . ? C65 C66 1.393(2) . ? C65 H65A 0.9500 . ? C66 C67 1.480(2) . ? C67 C68 1.400(2) . ? C67 C72 1.409(2) . ? C68 C69 1.389(2) . ? C68 H68A 0.9500 . ? C69 C70 1.399(2) . ? C69 H69A 0.9500 . ? C70 C71 1.404(2) . ? C70 N6 1.439(2) . ? C71 C72 1.387(2) . ? C71 H71A 0.9500 . ? C73 N5 1.406(2) . ? C73 C74 1.407(3) . ? C73 C78 1.414(2) . ? C74 C75 1.390(3) . ? C74 H74A 0.9500 . ? C75 C76 1.402(3) . ? C75 H75A 0.9500 . ? C76 C77 1.381(3) . ? C76 H76A 0.9500 . ? C77 C78 1.391(3) . ? C77 H77A 0.9500 . ? C78 H78A 0.9500 . ? C79 C84 1.393(3) . ? C79 C80 1.399(3) . ? C79 N5 1.437(2) . ? C80 C81 1.390(3) . ? C80 H80A 0.9500 . ? C81 C82 1.384(3) . ? C81 H81A 0.9500 . ? C82 C83 1.392(3) . ? C82 H82A 0.9500 . ? C83 C84 1.388(3) . ? C83 H83A 0.9500 . ? C84 H84A 0.9500 . ? C85 C86 1.397(3) . ? C85 C90 1.415(3) . ? C85 N6 1.424(2) . ? C86 C87 1.392(3) . ? C86 H86A 0.9500 . ? C87 C88 1.405(3) . ? C87 H87A 0.9500 . ? C88 C89 1.381(3) . ? C88 H88A 0.9500 . ? C89 C90 1.384(3) . ? C89 H89A 0.9500 . ? C90 H90A 0.9500 . ? C91 C96 1.397(3) . ? C91 C92 1.398(3) . ? C91 N6 1.434(2) . ? C92 C93 1.389(3) . ? C92 H92A 0.9500 . ? C93 C94 1.374(4) . ? C93 H93A 0.9500 . ? C94 C95 1.381(4) . ? C94 H94A 0.9500 . ? C95 C96 1.404(3) . ? C95 H95A 0.9500 . ? C96 H96A 0.9500 . ? C97 C98 1.382(2) . ? C97 C102 1.409(2) . ? C98 C99 1.393(2) . ? C98 H98A 0.9500 . ? C99 C100 1.408(2) . ? C99 C109 1.489(2) . ? C100 C101 1.393(3) . ? C100 H100 0.9500 . ? C101 C102 1.394(2) . ? C101 H101 0.9500 . ? C102 C103 1.481(2) . ? C103 C104 1.401(2) . ? C103 C108 1.412(2) . ? C104 C105 1.391(3) . ? C104 H104 0.9500 . ? C105 C106 1.409(2) . ? C105 H105 0.9500 . ? C106 C107 1.408(2) . ? C106 C114 1.488(3) . ? C107 C108 1.374(2) . ? C107 H107 0.9500 . ? C109 C110 1.393(3) . ? C109 C113 1.398(2) . ? C110 F9 1.3572(18) . ? C110 C111 1.376(3) . ? C111 N7 1.313(2) . ? C111 F10 1.351(2) . ? C112 N7 1.320(2) . ? C112 F11 1.3364(19) . ? C112 C113 1.382(3) . ? C113 F12 1.350(2) . ? C114 C115 1.393(2) . ? C114 C118 1.401(2) . ? C115 F13 1.3551(19) . ? C115 C116 1.374(3) . ? C116 N8 1.324(2) . ? C116 F14 1.354(2) . ? C117 N8 1.324(2) . ? C117 F15 1.341(2) . ? C117 C118 1.377(3) . ? C118 F16 1.359(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C49 C1 C38 101.33(12) . . ? C49 C1 C2 112.51(14) . . ? C38 C1 C2 112.08(13) . . ? C49 C1 C13 114.47(13) . . ? C38 C1 C13 115.68(14) . . ? C2 C1 C13 101.27(12) . . ? C3 C2 C7 121.52(15) . . ? C3 C2 C1 127.63(14) . . ? C7 C2 C1 110.85(14) . . ? C2 C3 C4 118.82(15) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C3 C4 C5 120.00(16) . . ? C3 C4 N1 119.98(15) . . ? C5 C4 N1 120.01(15) . . ? C6 C5 C4 121.18(16) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C7 119.01(15) . . ? C5 C6 H6A 120.5 . . ? C7 C6 H6A 120.5 . . ? C6 C7 C2 119.43(16) . . ? C6 C7 C8 132.21(15) . . ? C2 C7 C8 108.35(14) . . ? C9 C8 C13 119.76(16) . . ? C9 C8 C7 131.28(15) . . ? C13 C8 C7 108.95(14) . . ? C10 C9 C8 118.96(16) . . ? C10 C9 H9A 120.5 . . ? C8 C9 H9A 120.5 . . ? C9 C10 C11 121.05(17) . . ? C9 C10 H10A 119.5 . . ? C11 C10 H10A 119.5 . . ? C10 C11 C12 120.32(17) . . ? C10 C11 N2 119.38(16) . . ? C12 C11 N2 120.30(16) . . ? C13 C12 C11 118.50(15) . . ? C13 C12 H12A 120.7 . . ? C11 C12 H12A 120.7 . . ? C12 C13 C8 121.37(15) . . ? C12 C13 C1 128.07(14) . . ? C8 C13 C1 110.54(14) . . ? C15 C14 C19 118.61(17) . . ? C15 C14 N1 119.44(16) . . ? C19 C14 N1 121.94(17) . . ? C14 C15 C16 120.64(18) . . ? C14 C15 H15A 119.7 . . ? C16 C15 H15A 119.7 . . ? C17 C16 C15 120.31(19) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C18 C17 C16 119.44(18) . . ? C18 C17 H17A 120.3 . . ? C16 C17 H17A 120.3 . . ? C17 C18 C19 120.76(19) . . ? C17 C18 H18A 119.6 . . ? C19 C18 H18A 119.6 . . ? C14 C19 C18 120.2(2) . . ? C14 C19 H19A 119.9 . . ? C18 C19 H19A 119.9 . . ? C25 C20 C21 119.20(19) . . ? C25 C20 N1 119.51(17) . . ? C21 C20 N1 121.27(17) . . ? C22 C21 C20 119.88(19) . . ? C22 C21 H21A 120.1 . . ? C20 C21 H21A 120.1 . . ? C23 C22 C21 120.9(2) . . ? C23 C22 H22A 119.5 . . ? C21 C22 H22A 119.5 . . ? C22 C23 C24 119.3(2) . . ? C22 C23 H23A 120.3 . . ? C24 C23 H23A 120.3 . . ? C23 C24 C25 120.6(2) . . ? C23 C24 H24A 119.7 . . ? C25 C24 H24A 119.7 . . ? C20 C25 C24 120.1(2) . . ? C20 C25 H25A 119.9 . . ? C24 C25 H25A 119.9 . . ? C27 C26 C31 118.61(18) . . ? C27 C26 N2 120.27(17) . . ? C31 C26 N2 121.11(17) . . ? C28 C27 C26 120.66(19) . . ? C28 C27 H27A 119.7 . . ? C26 C27 H27A 119.7 . . ? C29 C28 C27 120.58(19) . . ? C29 C28 H28A 119.7 . . ? C27 C28 H28A 119.7 . . ? C28 C29 C30 118.94(19) . . ? C28 C29 H29A 120.5 . . ? C30 C29 H29A 120.5 . . ? C31 C30 C29 120.95(19) . . ? C31 C30 H30A 119.5 . . ? C29 C30 H30A 119.5 . . ? C30 C31 C26 120.19(18) . . ? C30 C31 H31A 119.9 . . ? C26 C31 H31A 119.9 . . ? C33 C32 C37 118.00(17) . . ? C33 C32 N2 122.39(18) . . ? C37 C32 N2 119.60(17) . . ? C34 C33 C32 120.48(19) . . ? C34 C33 H33A 119.8 . . ? C32 C33 H33A 119.8 . . ? C35 C34 C33 121.36(19) . . ? C35 C34 H34A 119.3 . . ? C33 C34 H34A 119.3 . . ? C34 C35 C36 118.69(19) . . ? C34 C35 H35A 120.7 . . ? C36 C35 H35A 120.7 . . ? C37 C36 C35 120.6(2) . . ? C37 C36 H36A 119.7 . . ? C35 C36 H36A 119.7 . . ? C36 C37 C32 120.76(19) . . ? C36 C37 H37A 119.6 . . ? C32 C37 H37A 119.6 . . ? C39 C38 C43 121.20(15) . . ? C39 C38 C1 127.64(14) . . ? C43 C38 C1 110.80(14) . . ? C38 C39 C40 119.22(15) . . ? C38 C39 H39A 120.4 . . ? C40 C39 H39A 120.4 . . ? C41 C40 C39 119.71(16) . . ? C41 C40 C50 121.17(15) . . ? C39 C40 C50 118.88(15) . . ? C40 C41 C42 121.12(16) . . ? C40 C41 H41A 119.4 . . ? C42 C41 H41A 119.4 . . ? C43 C42 C41 118.77(15) . . ? C43 C42 H42A 120.6 . . ? C41 C42 H42A 120.6 . . ? C42 C43 C38 119.81(16) . . ? C42 C43 C44 131.56(15) . . ? C38 C43 C44 108.47(14) . . ? C45 C44 C49 120.08(15) . . ? C45 C44 C43 131.64(14) . . ? C49 C44 C43 108.20(14) . . ? C44 C45 C46 118.91(15) . . ? C44 C45 H45A 120.5 . . ? C46 C45 H45A 120.5 . . ? C45 C46 C47 120.71(15) . . ? C45 C46 H46A 119.6 . . ? C47 C46 H46A 119.6 . . ? C48 C47 C46 120.31(15) . . ? C48 C47 C55 118.50(14) . . ? C46 C47 C55 121.18(15) . . ? C49 C48 C47 118.91(14) . . ? C49 C48 H48A 120.5 . . ? C47 C48 H48A 120.5 . . ? C48 C49 C44 121.07(15) . . ? C48 C49 C1 127.70(14) . . ? C44 C49 C1 111.18(14) . . ? C54 C50 C51 115.27(16) . . ? C54 C50 C40 120.63(16) . . ? C51 C50 C40 124.08(16) . . ? F1 C51 C52 120.01(17) . . ? F1 C51 C50 120.39(16) . . ? C52 C51 C50 119.59(17) . . ? N3 C52 F2 115.93(15) . . ? N3 C52 C51 124.74(18) . . ? F2 C52 C51 119.34(17) . . ? N3 C53 F3 116.42(16) . . ? N3 C53 C54 124.34(17) . . ? F3 C53 C54 119.24(17) . . ? F4 C54 C53 118.66(15) . . ? F4 C54 C50 121.40(15) . . ? C53 C54 C50 119.93(17) . . ? C56 C55 C59 115.36(17) . . ? C56 C55 C47 121.67(17) . . ? C59 C55 C47 122.92(18) . . ? F5 C56 C57 119.9(2) . . ? F5 C56 C55 119.97(17) . . ? C57 C56 C55 120.1(2) . . ? N4 C57 F6 117.0(2) . . ? N4 C57 C56 124.0(2) . . ? F6 C57 C56 119.0(2) . . ? N4 C58 F7 116.8(2) . . ? N4 C58 C59 124.7(2) . . ? F7 C58 C59 118.5(2) . . ? F8 C59 C58 119.46(19) . . ? F8 C59 C55 121.21(17) . . ? C58 C59 C55 119.3(2) . . ? C108 C60 C97 101.28(12) . . ? C108 C60 C61 113.83(13) . . ? C97 C60 C61 109.74(13) . . ? C108 C60 C72 116.45(13) . . ? C97 C60 C72 114.40(14) . . ? C61 C60 C72 101.50(12) . . ? C62 C61 C66 121.62(14) . . ? C62 C61 C60 127.62(14) . . ? C66 C61 C60 110.70(13) . . ? C61 C62 C63 118.25(15) . . ? C61 C62 H62A 120.9 . . ? C63 C62 H62A 120.9 . . ? C62 C63 C64 120.80(15) . . ? C62 C63 N5 118.92(15) . . ? C64 C63 N5 120.27(14) . . ? C63 C64 C65 120.72(15) . . ? C63 C64 H64A 119.6 . . ? C65 C64 H64A 119.6 . . ? C66 C65 C64 119.01(15) . . ? C66 C65 H65A 120.5 . . ? C64 C65 H65A 120.5 . . ? C65 C66 C61 119.57(15) . . ? C65 C66 C67 131.93(15) . . ? C61 C66 C67 108.48(13) . . ? C68 C67 C72 119.80(15) . . ? C68 C67 C66 131.61(14) . . ? C72 C67 C66 108.59(13) . . ? C69 C68 C67 119.27(15) . . ? C69 C68 H68A 120.4 . . ? C67 C68 H68A 120.4 . . ? C68 C69 C70 120.81(15) . . ? C68 C69 H69A 119.6 . . ? C70 C69 H69A 119.6 . . ? C69 C70 C71 120.22(15) . . ? C69 C70 N6 119.81(14) . . ? C71 C70 N6 119.97(14) . . ? C72 C71 C70 118.94(14) . . ? C72 C71 H71A 120.5 . . ? C70 C71 H71A 120.5 . . ? C71 C72 C67 120.92(14) . . ? C71 C72 C60 128.44(14) . . ? C67 C72 C60 110.62(13) . . ? N5 C73 C74 120.88(15) . . ? N5 C73 C78 121.47(17) . . ? C74 C73 C78 117.65(17) . . ? C75 C74 C73 121.06(16) . . ? C75 C74 H74A 119.5 . . ? C73 C74 H74A 119.5 . . ? C74 C75 C76 120.63(18) . . ? C74 C75 H75A 119.7 . . ? C76 C75 H75A 119.7 . . ? C77 C76 C75 118.61(18) . . ? C77 C76 H76A 120.7 . . ? C75 C76 H76A 120.7 . . ? C76 C77 C78 121.55(17) . . ? C76 C77 H77A 119.2 . . ? C78 C77 H77A 119.2 . . ? C77 C78 C73 120.45(18) . . ? C77 C78 H78A 119.8 . . ? C73 C78 H78A 119.8 . . ? C84 C79 C80 119.18(19) . . ? C84 C79 N5 119.62(17) . . ? C80 C79 N5 121.17(17) . . ? C81 C80 C79 120.3(2) . . ? C81 C80 H80A 119.8 . . ? C79 C80 H80A 119.8 . . ? C82 C81 C80 120.2(2) . . ? C82 C81 H81A 119.9 . . ? C80 C81 H81A 119.9 . . ? C81 C82 C83 119.7(2) . . ? C81 C82 H82A 120.2 . . ? C83 C82 H82A 120.2 . . ? C84 C83 C82 120.4(2) . . ? C84 C83 H83A 119.8 . . ? C82 C83 H83A 119.8 . . ? C83 C84 C79 120.2(2) . . ? C83 C84 H84A 119.9 . . ? C79 C84 H84A 119.9 . . ? C86 C85 C90 118.57(18) . . ? C86 C85 N6 121.00(16) . . ? C90 C85 N6 120.42(18) . . ? C87 C86 C85 120.75(18) . . ? C87 C86 H86A 119.6 . . ? C85 C86 H86A 119.6 . . ? C86 C87 C88 120.1(2) . . ? C86 C87 H87A 120.0 . . ? C88 C87 H87A 120.0 . . ? C89 C88 C87 119.3(2) . . ? C89 C88 H88A 120.4 . . ? C87 C88 H88A 120.4 . . ? C88 C89 C90 121.2(2) . . ? C88 C89 H89A 119.4 . . ? C90 C89 H89A 119.4 . . ? C89 C90 C85 120.1(2) . . ? C89 C90 H90A 120.0 . . ? C85 C90 H90A 120.0 . . ? C96 C91 C92 119.44(18) . . ? C96 C91 N6 122.7(2) . . ? C92 C91 N6 117.80(16) . . ? C93 C92 C91 120.6(2) . . ? C93 C92 H92A 119.7 . . ? C91 C92 H92A 119.7 . . ? C94 C93 C92 119.8(3) . . ? C94 C93 H93A 120.1 . . ? C92 C93 H93A 120.1 . . ? C93 C94 C95 120.6(2) . . ? C93 C94 H94A 119.7 . . ? C95 C94 H94A 119.7 . . ? C94 C95 C96 120.4(2) . . ? C94 C95 H95A 119.8 . . ? C96 C95 H95A 119.8 . . ? C91 C96 C95 119.1(2) . . ? C91 C96 H96A 120.4 . . ? C95 C96 H96A 120.4 . . ? C98 C97 C102 121.29(16) . . ? C98 C97 C60 127.22(14) . . ? C102 C97 C60 111.37(14) . . ? C97 C98 C99 119.04(14) . . ? C97 C98 H98A 120.5 . . ? C99 C98 H98A 120.5 . . ? C98 C99 C100 120.18(16) . . ? C98 C99 C109 118.15(14) . . ? C100 C99 C109 121.66(15) . . ? C101 C100 C99 120.53(16) . . ? C101 C100 H100 119.7 . . ? C99 C100 H100 119.7 . . ? C100 C101 C102 119.31(15) . . ? C100 C101 H101 120.3 . . ? C102 C101 H101 120.3 . . ? C101 C102 C97 119.60(16) . . ? C101 C102 C103 132.50(14) . . ? C97 C102 C103 107.90(14) . . ? C104 C103 C108 119.46(16) . . ? C104 C103 C102 132.24(15) . . ? C108 C103 C102 108.29(14) . . ? C105 C104 C103 119.15(15) . . ? C105 C104 H104 120.4 . . ? C103 C104 H104 120.4 . . ? C104 C105 C106 121.23(15) . . ? C104 C105 H105 119.4 . . ? C106 C105 H105 119.4 . . ? C107 C106 C105 119.16(17) . . ? C107 C106 C114 117.65(15) . . ? C105 C106 C114 123.08(15) . . ? C108 C107 C106 119.57(15) . . ? C108 C107 H107 120.2 . . ? C106 C107 H107 120.2 . . ? C107 C108 C103 121.35(15) . . ? C107 C108 C60 127.60(14) . . ? C103 C108 C60 111.01(15) . . ? C110 C109 C113 114.84(16) . . ? C110 C109 C99 123.11(15) . . ? C113 C109 C99 122.04(16) . . ? F9 C110 C111 119.25(16) . . ? F9 C110 C109 120.66(15) . . ? C111 C110 C109 120.09(15) . . ? N7 C111 F10 116.59(16) . . ? N7 C111 C110 124.70(17) . . ? F10 C111 C110 118.71(15) . . ? N7 C112 F11 117.14(16) . . ? N7 C112 C113 123.91(15) . . ? F11 C112 C113 118.94(16) . . ? F12 C113 C112 119.26(15) . . ? F12 C113 C109 120.47(16) . . ? C112 C113 C109 120.23(16) . . ? C115 C114 C118 114.76(17) . . ? C115 C114 C106 122.75(15) . . ? C118 C114 C106 122.34(16) . . ? F13 C115 C116 119.37(16) . . ? F13 C115 C114 120.37(16) . . ? C116 C115 C114 120.21(16) . . ? N8 C116 F14 115.35(17) . . ? N8 C116 C115 124.67(17) . . ? F14 C116 C115 119.98(16) . . ? N8 C117 F15 116.45(17) . . ? N8 C117 C118 124.03(17) . . ? F15 C117 C118 119.52(17) . . ? F16 C118 C117 119.10(16) . . ? F16 C118 C114 120.43(17) . . ? C117 C118 C114 120.47(17) . . ? C14 N1 C20 119.25(15) . . ? C14 N1 C4 117.75(15) . . ? C20 N1 C4 116.38(14) . . ? C32 N2 C26 123.78(15) . . ? C32 N2 C11 118.55(15) . . ? C26 N2 C11 117.16(14) . . ? C53 N3 C52 116.14(16) . . ? C58 N4 C57 116.56(19) . . ? C73 N5 C79 124.14(14) . . ? C73 N5 C63 119.54(15) . . ? C79 N5 C63 116.28(15) . . ? C85 N6 C91 122.74(14) . . ? C85 N6 C70 118.37(14) . . ? C91 N6 C70 116.35(14) . . ? C111 N7 C112 116.22(16) . . ? C117 N8 C116 115.85(17) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.342 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.037 data_i0822 _database_code_depnum_ccdc_archive 'CCDC 919920' #TrackingRef 'chemcomm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H12 Br2 F8 N2' _chemical_formula_weight 772.29 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.1657(6) _cell_length_b 17.9898(6) _cell_length_c 23.0292(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.717(3) _cell_angle_gamma 90.00 _cell_volume 5868.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 32969 _cell_measurement_theta_min 1.44 _cell_measurement_theta_max 25.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3024 _exptl_absorpt_coefficient_mu 2.844 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.2444 _exptl_absorpt_correction_T_max 0.4118 _exptl_absorpt_process_details 'X-red ver. 1.31 (Stoe & Cie. 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 30 _diffrn_source_power 1.50 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 180 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 37657 _diffrn_reflns_av_R_equivalents 0.0868 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 10139 _reflns_number_gt 8261 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1252P)^2^+30.6080P] 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 10139 _refine_ls_number_parameters 847 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0809 _refine_ls_wR_factor_ref 0.2266 _refine_ls_wR_factor_gt 0.2164 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3948(4) 0.0095(4) 0.2927(3) 0.0348(15) Uani 1 1 d . . . C2 C 0.4486(4) -0.0583(4) 0.2679(4) 0.0412(17) Uani 1 1 d . . . C3 C 0.4307(5) -0.0972(4) 0.2179(4) 0.0443(17) Uani 1 1 d . . . H3A H 0.3765 -0.0868 0.1946 0.053 Uiso 1 1 calc R . . C4 C 0.4942(6) -0.1525(4) 0.2021(4) 0.0487(19) Uani 1 1 d . . . C5 C 0.5719(5) -0.1701(4) 0.2370(4) 0.050(2) Uani 1 1 d . . . H5A H 0.6137 -0.2084 0.2253 0.060 Uiso 1 1 calc R . . C6 C 0.5887(5) -0.1330(4) 0.2877(4) 0.0458(19) Uani 1 1 d . . . H6A H 0.6418 -0.1455 0.3114 0.055 Uiso 1 1 calc R . . C7 C 0.5262(5) -0.0756(4) 0.3046(3) 0.0387(16) Uani 1 1 d . . . C8 C 0.5259(4) -0.0254(4) 0.3544(3) 0.0392(17) Uani 1 1 d . . . C9 C 0.5867(5) -0.0184(4) 0.4028(4) 0.0431(17) Uani 1 1 d . . . H9A H 0.6393 -0.0506 0.4074 0.052 Uiso 1 1 calc R . . C10 C 0.5696(5) 0.0348(4) 0.4430(4) 0.0437(18) Uani 1 1 d . . . H10A H 0.6099 0.0391 0.4761 0.052 Uiso 1 1 calc R . . C11 C 0.4927(5) 0.0838(4) 0.4363(3) 0.0431(17) Uani 1 1 d . . . C12 C 0.4313(5) 0.0781(4) 0.3887(3) 0.0401(16) Uani 1 1 d . . . H12A H 0.3792 0.1110 0.3841 0.048 Uiso 1 1 calc R . . C13 C 0.4488(5) 0.0234(4) 0.3486(3) 0.0371(15) Uani 1 1 d . . . C14 C 0.3990(4) 0.0749(3) 0.2502(3) 0.0333(14) Uani 1 1 d . . . C15 C 0.4786(5) 0.1108(3) 0.2313(3) 0.0341(14) Uani 1 1 d . . . H15A H 0.5394 0.0965 0.2452 0.041 Uiso 1 1 calc R . . C16 C 0.4685(5) 0.1683(4) 0.1913(3) 0.0348(14) Uani 1 1 d . . . C17 C 0.3774(5) 0.1873(3) 0.1706(3) 0.0327(14) Uani 1 1 d . . . H17A H 0.3708 0.2251 0.1421 0.039 Uiso 1 1 calc R . . C18 C 0.2976(5) 0.1522(3) 0.1911(3) 0.0329(14) Uani 1 1 d . . . H18A H 0.2368 0.1669 0.1775 0.039 Uiso 1 1 calc R . . C19 C 0.3069(4) 0.0953(3) 0.2315(3) 0.0307(13) Uani 1 1 d . . . C20 C 0.2387(4) 0.0476(3) 0.2612(3) 0.0300(13) Uani 1 1 d . . . C21 C 0.1396(4) 0.0441(3) 0.2593(3) 0.0315(14) Uani 1 1 d . . . H21A H 0.1047 0.0760 0.2342 0.038 Uiso 1 1 calc R . . C22 C 0.0934(4) -0.0060(4) 0.2942(3) 0.0326(14) Uani 1 1 d . . . H22A H 0.0264 -0.0087 0.2923 0.039 Uiso 1 1 calc R . . C23 C 0.1430(4) -0.0533(4) 0.3323(3) 0.0326(14) Uani 1 1 d . . . C24 C 0.2426(4) -0.0502(3) 0.3342(3) 0.0327(14) Uani 1 1 d . . . H24A H 0.2774 -0.0813 0.3600 0.039 Uiso 1 1 calc R . . C25 C 0.2884(4) -0.0013(3) 0.2982(3) 0.0323(14) Uani 1 1 d . . . C26 C 0.5547(5) 0.2067(3) 0.1692(3) 0.0346(15) Uani 1 1 d . . . C27 C 0.6331(5) 0.2223(4) 0.2060(4) 0.0398(16) Uani 1 1 d . . . C28 C 0.7129(5) 0.2546(4) 0.1827(4) 0.0455(18) Uani 1 1 d . . . C29 C 0.6515(6) 0.2564(4) 0.0942(4) 0.0484(19) Uani 1 1 d . . . C30 C 0.5664(5) 0.2266(4) 0.1131(3) 0.0402(16) Uani 1 1 d . . . C31 C 0.0943(4) -0.1072(4) 0.3706(3) 0.0346(14) Uani 1 1 d . . . C32 C 0.0251(5) -0.1554(4) 0.3500(3) 0.0379(15) Uani 1 1 d . . . C33 C -0.0162(5) -0.2063(4) 0.3874(4) 0.0464(18) Uani 1 1 d . . . C34 C 0.0716(5) -0.1687(5) 0.4626(4) 0.0472(19) Uani 1 1 d . . . C35 C 0.1182(5) -0.1165(4) 0.4292(3) 0.0401(16) Uani 1 1 d . . . C36 C 0.8151(4) -0.0142(3) 0.1459(3) 0.0230(12) Uani 1 1 d . . . C37 C 0.7283(4) 0.0169(3) 0.1129(3) 0.0270(13) Uani 1 1 d . . . C38 C 0.6334(4) 0.0037(3) 0.1236(3) 0.0298(13) Uani 1 1 d . . . H38A H 0.6141 -0.0244 0.1563 0.036 Uiso 1 1 calc R . . C39 C 0.5665(5) 0.0339(4) 0.0838(3) 0.0394(16) Uani 1 1 d . . . C40 C 0.5926(6) 0.0757(5) 0.0369(4) 0.050(2) Uani 1 1 d . . . H40A H 0.5457 0.0948 0.0111 0.059 Uiso 1 1 calc R . . C41 C 0.6868(6) 0.0899(4) 0.0271(3) 0.0475(19) Uani 1 1 d . . . H41A H 0.7049 0.1197 -0.0050 0.057 Uiso 1 1 calc R . . C42 C 0.7559(5) 0.0600(3) 0.0650(3) 0.0336(14) Uani 1 1 d . . . C43 C 0.8590(5) 0.0624(3) 0.0641(3) 0.0339(14) Uani 1 1 d . . . C44 C 0.9191(6) 0.0986(4) 0.0263(3) 0.0461(18) Uani 1 1 d . . . H44A H 0.8945 0.1289 -0.0040 0.055 Uiso 1 1 calc R . . C45 C 1.0145(6) 0.0897(4) 0.0335(4) 0.050(2) Uani 1 1 d . . . H45A H 1.0566 0.1140 0.0079 0.060 Uiso 1 1 calc R . . C46 C 1.0500(5) 0.0451(5) 0.0783(4) 0.051(2) Uani 1 1 d . . . C47 C 0.9920(5) 0.0082(4) 0.1176(3) 0.0381(16) Uani 1 1 d . . . H47A H 1.0171 -0.0223 0.1477 0.046 Uiso 1 1 calc R . . C48 C 0.8963(4) 0.0183(3) 0.1101(3) 0.0288(13) Uani 1 1 d . . . C49 C 0.8135(4) -0.0992(3) 0.1487(3) 0.0224(11) Uani 1 1 d . . . C50 C 0.8121(4) -0.1490(3) 0.1028(3) 0.0249(12) Uani 1 1 d . . . H50A H 0.8112 -0.1315 0.0638 0.030 Uiso 1 1 calc R . . C51 C 0.8120(4) -0.2256(3) 0.1144(3) 0.0277(13) Uani 1 1 d . . . C52 C 0.8107(4) -0.2507(3) 0.1727(3) 0.0287(13) Uani 1 1 d . . . H52A H 0.8090 -0.3025 0.1806 0.034 Uiso 1 1 calc R . . C53 C 0.8118(4) -0.2001(3) 0.2187(3) 0.0277(13) Uani 1 1 d . . . H53A H 0.8117 -0.2170 0.2578 0.033 Uiso 1 1 calc R . . C54 C 0.8129(4) -0.1238(3) 0.2062(3) 0.0255(12) Uani 1 1 d . . . C55 C 0.8166(4) -0.0584(3) 0.2446(3) 0.0254(12) Uani 1 1 d . . . C56 C 0.8192(4) -0.0530(4) 0.3054(3) 0.0292(13) Uani 1 1 d . . . H56A H 0.8166 -0.0964 0.3289 0.035 Uiso 1 1 calc R . . C57 C 0.8256(4) 0.0173(4) 0.3306(3) 0.0308(13) Uani 1 1 d . . . H57A H 0.8261 0.0219 0.3717 0.037 Uiso 1 1 calc R . . C58 C 0.8315(4) 0.0820(3) 0.2960(3) 0.0275(13) Uani 1 1 d . . . C59 C 0.8283(4) 0.0754(3) 0.2353(3) 0.0251(12) Uani 1 1 d . . . H59A H 0.8318 0.1185 0.2116 0.030 Uiso 1 1 calc R . . C60 C 0.8200(4) 0.0056(3) 0.2104(3) 0.0241(12) Uani 1 1 d . . . C61 C 0.8139(4) -0.2806(3) 0.0656(3) 0.0301(13) Uani 1 1 d . . . C62 C 0.7643(5) -0.2713(3) 0.0142(3) 0.0336(14) Uani 1 1 d . . . C63 C 0.7712(5) -0.3239(4) -0.0293(3) 0.0391(16) Uani 1 1 d . . . C64 C 0.8733(5) -0.3925(4) 0.0217(3) 0.0377(15) Uani 1 1 d . . . C65 C 0.8712(5) -0.3439(3) 0.0679(3) 0.0338(14) Uani 1 1 d . . . C66 C 0.8389(4) 0.1564(4) 0.3246(3) 0.0298(13) Uani 1 1 d . . . C67 C 0.9079(4) 0.2075(4) 0.3104(3) 0.0306(13) Uani 1 1 d . . . C68 C 0.9120(5) 0.2760(4) 0.3384(3) 0.0371(15) Uani 1 1 d . . . C69 C 0.7882(5) 0.2486(4) 0.3924(3) 0.0439(17) Uani 1 1 d . . . C70 C 0.7779(5) 0.1792(4) 0.3673(3) 0.0353(14) Uani 1 1 d . . . Br1 Br 0.47805(7) -0.20466(5) 0.13024(5) 0.0666(3) Uani 1 1 d . . . Br2 Br 0.47305(6) 0.15890(5) 0.49062(4) 0.0554(3) Uani 1 1 d . . . Br3 Br 0.43548(5) 0.01678(5) 0.09411(4) 0.0571(3) Uani 1 1 d . . . Br4 Br 1.18332(6) 0.03283(7) 0.08595(5) 0.0780(4) Uani 1 1 d . . . F1 F 0.6325(3) 0.2066(2) 0.2623(2) 0.0469(10) Uani 1 1 d . . . F2 F 0.7865(3) 0.2706(3) 0.2180(2) 0.0599(13) Uani 1 1 d . . . F3 F 0.6640(4) 0.2714(3) 0.0381(2) 0.0662(14) Uani 1 1 d . . . F4 F 0.4963(3) 0.2146(2) 0.07288(19) 0.0484(10) Uani 1 1 d . . . F5 F -0.0016(3) -0.1542(2) 0.29378(19) 0.0439(10) Uani 1 1 d . . . F6 F -0.0846(3) -0.2514(3) 0.3669(3) 0.0650(14) Uani 1 1 d . . . F7 F 0.0942(4) -0.1751(3) 0.5186(2) 0.0656(14) Uani 1 1 d . . . F8 F 0.1864(3) -0.0743(3) 0.45464(19) 0.0495(11) Uani 1 1 d . . . F9 F 0.7061(3) -0.2130(2) 0.00556(19) 0.0429(10) Uani 1 1 d . . . F10 F 0.7213(3) -0.3137(2) -0.0797(2) 0.0532(11) Uani 1 1 d . . . F11 F 0.9318(3) -0.4512(2) 0.0239(2) 0.0519(11) Uani 1 1 d . . . F12 F 0.9276(3) -0.3580(2) 0.11446(18) 0.0402(9) Uani 1 1 d . . . F13 F 0.9726(3) 0.1918(2) 0.26959(18) 0.0394(9) Uani 1 1 d . . . F14 F 0.9792(3) 0.3250(2) 0.3246(2) 0.0492(11) Uani 1 1 d . . . F15 F 0.7294(4) 0.2685(3) 0.4347(2) 0.0642(14) Uani 1 1 d . . . F16 F 0.7068(3) 0.1348(2) 0.3842(2) 0.0508(11) Uani 1 1 d . . . N1 N 0.7232(4) 0.2711(3) 0.1284(3) 0.0493(17) Uani 1 1 d . . . N2 N 0.0052(4) -0.2130(4) 0.4425(3) 0.0518(17) Uani 1 1 d . . . N3 N 0.8237(4) -0.3836(3) -0.0269(3) 0.0416(14) Uani 1 1 d . . . N4 N 0.8538(4) 0.2964(3) 0.3788(3) 0.0405(14) 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 C1 0.020(3) 0.034(3) 0.050(4) 0.009(3) -0.003(3) -0.001(2) C2 0.020(3) 0.037(4) 0.067(5) 0.013(3) 0.007(3) -0.001(3) C3 0.037(4) 0.034(4) 0.062(5) 0.000(3) 0.008(3) 0.001(3) C4 0.044(4) 0.038(4) 0.064(6) -0.004(3) 0.014(4) 0.006(3) C5 0.038(4) 0.034(4) 0.077(6) 0.002(4) 0.012(4) 0.006(3) C6 0.023(3) 0.038(4) 0.076(6) 0.022(4) 0.009(3) 0.006(3) C7 0.025(3) 0.032(3) 0.060(5) 0.009(3) 0.002(3) 0.001(3) C8 0.023(3) 0.038(4) 0.057(5) 0.023(3) 0.002(3) -0.003(3) C9 0.031(3) 0.040(4) 0.058(5) 0.012(3) -0.005(3) 0.000(3) C10 0.033(3) 0.049(4) 0.049(5) 0.020(3) -0.004(3) -0.011(3) C11 0.040(4) 0.049(4) 0.040(4) 0.005(3) 0.002(3) -0.012(3) C12 0.030(3) 0.043(4) 0.048(4) 0.010(3) 0.001(3) 0.000(3) C13 0.026(3) 0.037(3) 0.048(4) 0.009(3) 0.000(3) -0.005(3) C14 0.023(3) 0.031(3) 0.046(4) 0.000(3) -0.003(3) 0.004(2) C15 0.031(3) 0.030(3) 0.042(4) 0.001(3) -0.002(3) 0.004(3) C16 0.029(3) 0.035(3) 0.041(4) -0.004(3) 0.005(3) -0.001(3) C17 0.038(3) 0.023(3) 0.036(4) -0.003(3) -0.005(3) 0.004(3) C18 0.035(3) 0.027(3) 0.037(4) -0.006(3) -0.006(3) 0.007(2) C19 0.026(3) 0.027(3) 0.039(4) -0.004(3) -0.002(3) 0.003(2) C20 0.026(3) 0.029(3) 0.035(4) -0.003(3) -0.001(3) 0.002(2) C21 0.026(3) 0.031(3) 0.038(4) -0.005(3) -0.006(3) 0.005(2) C22 0.023(3) 0.037(3) 0.038(4) -0.005(3) -0.003(3) 0.002(2) C23 0.025(3) 0.037(3) 0.036(4) -0.001(3) -0.001(3) 0.003(3) C24 0.027(3) 0.030(3) 0.040(4) -0.003(3) -0.002(3) 0.002(2) C25 0.018(3) 0.031(3) 0.048(4) -0.001(3) -0.002(3) 0.001(2) C26 0.031(3) 0.028(3) 0.045(4) -0.004(3) 0.005(3) -0.001(3) C27 0.029(3) 0.031(3) 0.059(5) 0.001(3) 0.000(3) 0.000(3) C28 0.040(4) 0.035(4) 0.062(6) 0.000(3) 0.002(4) -0.001(3) C29 0.056(5) 0.040(4) 0.049(5) -0.002(3) 0.017(4) -0.004(3) C30 0.038(4) 0.033(3) 0.049(5) -0.007(3) -0.001(3) -0.003(3) C31 0.026(3) 0.035(3) 0.043(4) -0.004(3) 0.002(3) 0.007(3) C32 0.027(3) 0.040(4) 0.047(4) 0.005(3) 0.000(3) 0.002(3) C33 0.033(4) 0.041(4) 0.065(6) 0.009(4) -0.003(3) -0.004(3) C34 0.032(4) 0.066(5) 0.043(5) 0.013(4) 0.002(3) 0.012(3) C35 0.030(3) 0.046(4) 0.045(4) -0.001(3) -0.001(3) 0.006(3) C36 0.022(3) 0.023(3) 0.023(3) 0.001(2) 0.003(2) 0.000(2) C37 0.036(3) 0.021(3) 0.024(3) -0.004(2) -0.003(2) 0.002(2) C38 0.026(3) 0.028(3) 0.035(4) -0.009(3) -0.002(3) 0.002(2) C39 0.029(3) 0.044(4) 0.044(4) -0.016(3) -0.008(3) 0.012(3) C40 0.050(4) 0.057(5) 0.042(5) -0.003(4) -0.013(3) 0.027(4) C41 0.081(6) 0.035(4) 0.027(4) 0.007(3) 0.002(4) 0.020(4) C42 0.046(4) 0.028(3) 0.027(4) 0.003(2) 0.001(3) 0.006(3) C43 0.051(4) 0.023(3) 0.028(4) -0.004(2) 0.010(3) -0.003(3) C44 0.063(5) 0.036(4) 0.039(4) 0.001(3) 0.016(4) -0.010(3) C45 0.062(5) 0.045(4) 0.044(5) -0.008(3) 0.020(4) -0.019(4) C46 0.034(4) 0.062(5) 0.056(5) -0.036(4) 0.016(3) -0.020(3) C47 0.033(3) 0.049(4) 0.033(4) -0.017(3) 0.006(3) -0.007(3) C48 0.029(3) 0.032(3) 0.025(3) -0.009(2) 0.011(2) -0.008(2) C49 0.017(2) 0.023(3) 0.027(3) 0.001(2) 0.004(2) 0.002(2) C50 0.024(3) 0.026(3) 0.025(3) 0.000(2) 0.003(2) 0.001(2) C51 0.023(3) 0.024(3) 0.036(4) -0.003(2) -0.002(2) -0.001(2) C52 0.025(3) 0.025(3) 0.036(4) 0.007(2) 0.002(2) 0.002(2) C53 0.028(3) 0.027(3) 0.029(3) 0.002(2) 0.003(2) 0.001(2) C54 0.017(3) 0.032(3) 0.028(3) 0.001(2) 0.000(2) 0.000(2) C55 0.020(3) 0.028(3) 0.029(3) 0.003(2) 0.002(2) -0.001(2) C56 0.025(3) 0.035(3) 0.028(4) 0.006(3) -0.001(2) 0.000(2) C57 0.027(3) 0.039(3) 0.026(4) 0.000(3) 0.003(2) -0.002(3) C58 0.020(3) 0.034(3) 0.028(3) -0.003(2) 0.002(2) -0.001(2) C59 0.020(3) 0.026(3) 0.029(3) -0.001(2) 0.000(2) 0.001(2) C60 0.018(3) 0.030(3) 0.024(3) -0.001(2) 0.001(2) 0.002(2) C61 0.031(3) 0.025(3) 0.035(4) -0.002(2) 0.004(3) -0.004(2) C62 0.032(3) 0.026(3) 0.042(4) -0.004(3) -0.004(3) -0.001(2) C63 0.040(4) 0.035(3) 0.042(4) -0.004(3) -0.007(3) -0.002(3) C64 0.040(4) 0.027(3) 0.046(4) -0.004(3) 0.008(3) 0.003(3) C65 0.035(3) 0.026(3) 0.040(4) 0.001(3) 0.001(3) 0.002(3) C66 0.026(3) 0.040(3) 0.023(3) 0.000(3) -0.003(2) -0.001(3) C67 0.025(3) 0.040(3) 0.027(3) -0.005(3) 0.000(2) -0.001(3) C68 0.029(3) 0.042(4) 0.040(4) -0.004(3) -0.004(3) -0.002(3) C69 0.047(4) 0.055(4) 0.030(4) -0.013(3) 0.010(3) -0.001(3) C70 0.034(3) 0.039(3) 0.034(4) -0.005(3) 0.007(3) -0.007(3) Br1 0.0722(6) 0.0530(5) 0.0749(7) -0.0144(4) 0.0143(5) 0.0072(4) Br2 0.0573(5) 0.0563(5) 0.0525(5) -0.0073(4) 0.0016(4) -0.0047(4) Br3 0.0342(4) 0.0663(5) 0.0705(6) -0.0260(4) -0.0160(4) 0.0124(3) Br4 0.0292(4) 0.1341(10) 0.0712(7) -0.0501(6) 0.0161(4) -0.0288(5) F1 0.038(2) 0.048(2) 0.054(3) 0.009(2) -0.0086(19) -0.0031(18) F2 0.034(2) 0.053(3) 0.092(4) 0.016(2) -0.012(2) -0.0103(19) F3 0.067(3) 0.082(4) 0.050(3) 0.002(3) 0.013(2) -0.018(3) F4 0.052(3) 0.052(2) 0.041(3) -0.0004(19) 0.0008(19) -0.013(2) F5 0.037(2) 0.045(2) 0.050(3) -0.0012(18) -0.0067(18) -0.0038(17) F6 0.047(3) 0.058(3) 0.090(4) 0.018(3) -0.007(2) -0.023(2) F7 0.054(3) 0.095(4) 0.048(3) 0.022(3) 0.003(2) 0.005(3) F8 0.037(2) 0.069(3) 0.042(3) -0.005(2) -0.0053(18) 0.000(2) F9 0.048(2) 0.0310(19) 0.049(3) -0.0078(17) -0.0166(19) 0.0103(17) F10 0.065(3) 0.049(2) 0.045(3) -0.012(2) -0.015(2) -0.001(2) F11 0.055(3) 0.032(2) 0.069(3) -0.0092(19) 0.006(2) 0.0147(18) F12 0.041(2) 0.0329(19) 0.047(2) -0.0015(17) -0.0036(18) 0.0112(16) F13 0.0273(18) 0.041(2) 0.050(3) -0.0106(18) 0.0129(16) -0.0034(16) F14 0.038(2) 0.046(2) 0.065(3) -0.012(2) 0.007(2) -0.0169(18) F15 0.078(3) 0.057(3) 0.059(3) -0.027(2) 0.036(3) -0.013(2) F16 0.053(3) 0.047(2) 0.053(3) -0.013(2) 0.028(2) -0.015(2) N1 0.035(3) 0.038(3) 0.075(5) 0.000(3) 0.009(3) -0.005(3) N2 0.036(3) 0.060(4) 0.059(5) 0.019(3) 0.008(3) -0.002(3) N3 0.046(3) 0.033(3) 0.047(4) -0.010(3) 0.007(3) -0.003(3) N4 0.046(3) 0.042(3) 0.033(3) -0.010(2) -0.003(3) -0.004(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 C1 C13 1.509(10) . ? C1 C25 1.527(8) . ? C1 C14 1.533(9) . ? C1 C2 1.551(10) . ? C2 C3 1.369(11) . ? C2 C7 1.414(10) . ? C3 C4 1.391(10) . ? C3 H3A 0.9500 . ? C4 C5 1.390(12) . ? C4 Br1 1.915(9) . ? C5 C6 1.364(12) . ? C5 H5A 0.9500 . ? C6 C7 1.419(10) . ? C6 H6A 0.9500 . ? C7 C8 1.458(11) . ? C8 C13 1.408(9) . ? C8 C9 1.406(11) . ? C9 C10 1.355(12) . ? C9 H9A 0.9500 . ? C10 C11 1.408(11) . ? C10 H10A 0.9500 . ? C11 C12 1.394(11) . ? C11 Br2 1.865(8) . ? C12 C13 1.373(11) . ? C12 H12A 0.9500 . ? C14 C15 1.375(9) . ? C14 C19 1.417(9) . ? C15 C16 1.391(10) . ? C15 H15A 0.9500 . ? C16 C17 1.412(9) . ? C16 C26 1.498(9) . ? C17 C18 1.382(10) . ? C17 H17A 0.9500 . ? C18 C19 1.388(9) . ? C18 H18A 0.9500 . ? C19 C20 1.468(9) . ? C20 C25 1.407(9) . ? C20 C21 1.406(9) . ? C21 C22 1.377(10) . ? C21 H21A 0.9500 . ? C22 C23 1.405(9) . ? C22 H22A 0.9500 . ? C23 C24 1.411(9) . ? C23 C31 1.487(10) . ? C24 C25 1.377(10) . ? C24 H24A 0.9500 . ? C26 C30 1.352(11) . ? C26 C27 1.417(10) . ? C27 F1 1.326(9) . ? C27 C28 1.385(10) . ? C28 N1 1.295(11) . ? C28 F2 1.345(9) . ? C29 N1 1.305(11) . ? C29 F3 1.333(10) . ? C29 C30 1.395(11) . ? C30 F4 1.367(8) . ? C31 C32 1.387(10) . ? C31 C35 1.397(10) . ? C32 F5 1.345(9) . ? C32 C33 1.390(11) . ? C33 N2 1.307(11) . ? C33 F6 1.346(9) . ? C34 N2 1.313(11) . ? C34 F7 1.331(9) . ? C34 C35 1.387(11) . ? C35 F8 1.356(8) . ? C36 C60 1.529(8) . ? C36 C49 1.531(8) . ? C36 C48 1.539(8) . ? C36 C37 1.543(8) . ? C37 C38 1.390(9) . ? C37 C42 1.407(9) . ? C38 C39 1.419(9) . ? C38 H38A 0.9500 . ? C39 C40 1.369(12) . ? C39 Br3 1.900(7) . ? C40 C41 1.381(12) . ? C40 H40A 0.9500 . ? C41 C42 1.411(10) . ? C41 H41A 0.9500 . ? C42 C43 1.461(10) . ? C43 C44 1.387(10) . ? C43 C48 1.421(10) . ? C44 C45 1.368(12) . ? C44 H44A 0.9500 . ? C45 C46 1.397(13) . ? C45 H45A 0.9500 . ? C46 C47 1.397(11) . ? C46 Br4 1.908(8) . ? C47 C48 1.376(10) . ? C47 H47A 0.9500 . ? C49 C50 1.386(8) . ? C49 C54 1.398(9) . ? C50 C51 1.403(8) . ? C50 H50A 0.9500 . ? C51 C52 1.417(9) . ? C51 C61 1.499(9) . ? C52 C53 1.397(9) . ? C52 H52A 0.9500 . ? C53 C54 1.401(8) . ? C53 H53A 0.9500 . ? C54 C55 1.473(8) . ? C55 C60 1.397(8) . ? C55 C56 1.403(9) . ? C56 C57 1.395(9) . ? C56 H56A 0.9500 . ? C57 C58 1.412(9) . ? C57 H57A 0.9500 . ? C58 C59 1.402(9) . ? C58 C66 1.495(9) . ? C59 C60 1.385(8) . ? C59 H59A 0.9500 . ? C61 C62 1.378(10) . ? C61 C65 1.399(9) . ? C62 F9 1.348(7) . ? C62 C63 1.383(10) . ? C63 N3 1.308(9) . ? C63 F10 1.363(8) . ? C64 N3 1.323(10) . ? C64 F11 1.344(8) . ? C64 C65 1.379(10) . ? C65 F12 1.353(8) . ? C66 C70 1.381(9) . ? C66 C67 1.384(9) . ? C67 F13 1.351(7) . ? C67 C68 1.391(9) . ? C68 N4 1.304(9) . ? C68 F14 1.339(8) . ? C69 N4 1.306(10) . ? C69 F15 1.338(8) . ? C69 C70 1.383(10) . ? C70 F16 1.347(8) . ? 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 C13 C1 C25 116.2(6) . . ? C13 C1 C14 113.3(5) . . ? C25 C1 C14 101.3(5) . . ? C13 C1 C2 101.5(5) . . ? C25 C1 C2 114.8(5) . . ? C14 C1 C2 110.2(6) . . ? C3 C2 C7 121.7(7) . . ? C3 C2 C1 128.8(6) . . ? C7 C2 C1 109.5(7) . . ? C2 C3 C4 118.1(8) . . ? C2 C3 H3A 120.9 . . ? C4 C3 H3A 120.9 . . ? C5 C4 C3 121.5(8) . . ? C5 C4 Br1 118.2(6) . . ? C3 C4 Br1 120.3(7) . . ? C6 C5 C4 120.7(7) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C5 C6 C7 119.3(7) . . ? C5 C6 H6A 120.4 . . ? C7 C6 H6A 120.4 . . ? C2 C7 C6 118.6(7) . . ? C2 C7 C8 108.9(6) . . ? C6 C7 C8 132.4(7) . . ? C13 C8 C9 119.0(7) . . ? C13 C8 C7 108.8(6) . . ? C9 C8 C7 132.2(6) . . ? C10 C9 C8 119.5(7) . . ? C10 C9 H9A 120.2 . . ? C8 C9 H9A 120.2 . . ? C9 C10 C11 120.7(7) . . ? C9 C10 H10A 119.6 . . ? C11 C10 H10A 119.6 . . ? C12 C11 C10 121.0(7) . . ? C12 C11 Br2 119.0(6) . . ? C10 C11 Br2 120.0(6) . . ? C13 C12 C11 117.7(7) . . ? C13 C12 H12A 121.2 . . ? C11 C12 H12A 121.2 . . ? C12 C13 C8 122.1(7) . . ? C12 C13 C1 126.7(6) . . ? C8 C13 C1 111.1(6) . . ? C15 C14 C19 122.6(6) . . ? C15 C14 C1 126.9(6) . . ? C19 C14 C1 110.5(5) . . ? C14 C15 C16 118.7(6) . . ? C14 C15 H15A 120.7 . . ? C16 C15 H15A 120.7 . . ? C15 C16 C17 119.3(6) . . ? C15 C16 C26 119.3(6) . . ? C17 C16 C26 121.3(6) . . ? C18 C17 C16 121.5(6) . . ? C18 C17 H17A 119.3 . . ? C16 C17 H17A 119.3 . . ? C17 C18 C19 119.6(6) . . ? C17 C18 H18A 120.2 . . ? C19 C18 H18A 120.2 . . ? C18 C19 C14 118.2(6) . . ? C18 C19 C20 133.3(6) . . ? C14 C19 C20 108.4(5) . . ? C25 C20 C21 118.9(6) . . ? C25 C20 C19 108.7(5) . . ? C21 C20 C19 132.5(6) . . ? C22 C21 C20 119.6(6) . . ? C22 C21 H21A 120.2 . . ? C20 C21 H21A 120.2 . . ? C21 C22 C23 121.5(6) . . ? C21 C22 H22A 119.3 . . ? C23 C22 H22A 119.3 . . ? C22 C23 C24 119.2(6) . . ? C22 C23 C31 122.2(6) . . ? C24 C23 C31 118.6(6) . . ? C25 C24 C23 119.0(6) . . ? C25 C24 H24A 120.5 . . ? C23 C24 H24A 120.5 . . ? C24 C25 C20 121.8(6) . . ? C24 C25 C1 127.2(6) . . ? C20 C25 C1 111.0(6) . . ? C30 C26 C27 114.5(6) . . ? C30 C26 C16 123.8(6) . . ? C27 C26 C16 121.6(7) . . ? F1 C27 C28 118.9(7) . . ? F1 C27 C26 121.9(6) . . ? C28 C27 C26 119.2(7) . . ? N1 C28 F2 115.9(7) . . ? N1 C28 C27 125.0(7) . . ? F2 C28 C27 119.1(8) . . ? N1 C29 F3 115.7(7) . . ? N1 C29 C30 123.9(8) . . ? F3 C29 C30 120.4(8) . . ? C26 C30 F4 120.6(6) . . ? C26 C30 C29 121.2(7) . . ? F4 C30 C29 118.2(7) . . ? C32 C31 C35 114.6(6) . . ? C32 C31 C23 122.5(6) . . ? C35 C31 C23 122.8(6) . . ? F5 C32 C33 119.5(6) . . ? F5 C32 C31 120.5(6) . . ? C33 C32 C31 120.1(7) . . ? N2 C33 F6 116.2(7) . . ? N2 C33 C32 124.6(7) . . ? F6 C33 C32 119.1(7) . . ? N2 C34 F7 116.9(7) . . ? N2 C34 C35 124.0(7) . . ? F7 C34 C35 119.1(7) . . ? F8 C35 C34 118.7(7) . . ? F8 C35 C31 120.9(6) . . ? C34 C35 C31 120.4(7) . . ? C60 C36 C49 101.1(5) . . ? C60 C36 C48 114.0(5) . . ? C49 C36 C48 114.4(5) . . ? C60 C36 C37 114.9(5) . . ? C49 C36 C37 111.8(5) . . ? C48 C36 C37 101.3(5) . . ? C38 C37 C42 120.8(6) . . ? C38 C37 C36 128.1(6) . . ? C42 C37 C36 111.0(5) . . ? C37 C38 C39 117.3(6) . . ? C37 C38 H38A 121.3 . . ? C39 C38 H38A 121.3 . . ? C40 C39 C38 122.4(7) . . ? C40 C39 Br3 117.5(5) . . ? C38 C39 Br3 120.2(6) . . ? C39 C40 C41 120.1(7) . . ? C39 C40 H40A 119.9 . . ? C41 C40 H40A 119.9 . . ? C40 C41 C42 119.5(7) . . ? C40 C41 H41A 120.2 . . ? C42 C41 H41A 120.2 . . ? C37 C42 C41 119.8(7) . . ? C37 C42 C43 108.4(6) . . ? C41 C42 C43 131.7(7) . . ? C44 C43 C48 120.3(7) . . ? C44 C43 C42 130.1(7) . . ? C48 C43 C42 109.6(5) . . ? C45 C44 C43 118.9(8) . . ? C45 C44 H44A 120.6 . . ? C43 C44 H44A 120.6 . . ? C44 C45 C46 120.1(7) . . ? C44 C45 H45A 119.9 . . ? C46 C45 H45A 119.9 . . ? C45 C46 C47 122.8(7) . . ? C45 C46 Br4 118.8(6) . . ? C47 C46 Br4 118.4(7) . . ? C48 C47 C46 116.3(7) . . ? C48 C47 H47A 121.9 . . ? C46 C47 H47A 121.9 . . ? C47 C48 C43 121.6(6) . . ? C47 C48 C36 128.7(6) . . ? C43 C48 C36 109.7(5) . . ? C50 C49 C54 121.2(5) . . ? C50 C49 C36 127.9(5) . . ? C54 C49 C36 110.9(5) . . ? C49 C50 C51 119.2(6) . . ? C49 C50 H50A 120.4 . . ? C51 C50 H50A 120.4 . . ? C50 C51 C52 119.7(6) . . ? C50 C51 C61 120.3(6) . . ? C52 C51 C61 120.1(5) . . ? C53 C52 C51 120.6(5) . . ? C53 C52 H52A 119.7 . . ? C51 C52 H52A 119.7 . . ? C52 C53 C54 118.9(6) . . ? C52 C53 H53A 120.6 . . ? C54 C53 H53A 120.6 . . ? C49 C54 C53 120.4(6) . . ? C49 C54 C55 108.4(5) . . ? C53 C54 C55 131.2(6) . . ? C60 C55 C56 120.4(6) . . ? C60 C55 C54 108.7(5) . . ? C56 C55 C54 130.9(5) . . ? C57 C56 C55 118.6(6) . . ? C57 C56 H56A 120.7 . . ? C55 C56 H56A 120.7 . . ? C56 C57 C58 121.1(6) . . ? C56 C57 H57A 119.4 . . ? C58 C57 H57A 119.4 . . ? C59 C58 C57 119.4(6) . . ? C59 C58 C66 121.0(5) . . ? C57 C58 C66 119.6(6) . . ? C60 C59 C58 119.4(6) . . ? C60 C59 H59A 120.3 . . ? C58 C59 H59A 120.3 . . ? C59 C60 C55 121.1(6) . . ? C59 C60 C36 128.1(5) . . ? C55 C60 C36 110.8(5) . . ? C62 C61 C65 114.9(6) . . ? C62 C61 C51 123.4(6) . . ? C65 C61 C51 121.6(6) . . ? F9 C62 C61 121.8(6) . . ? F9 C62 C63 118.2(6) . . ? C61 C62 C63 120.0(6) . . ? N3 C63 F10 115.8(6) . . ? N3 C63 C62 125.2(7) . . ? F10 C63 C62 119.0(6) . . ? N3 C64 F11 116.7(6) . . ? N3 C64 C65 124.0(6) . . ? F11 C64 C65 119.2(6) . . ? F12 C65 C64 118.4(6) . . ? F12 C65 C61 121.3(6) . . ? C64 C65 C61 120.3(6) . . ? C70 C66 C67 114.9(6) . . ? C70 C66 C58 122.6(6) . . ? C67 C66 C58 122.5(6) . . ? F13 C67 C66 120.8(6) . . ? F13 C67 C68 118.9(6) . . ? C66 C67 C68 120.4(6) . . ? N4 C68 F14 116.2(6) . . ? N4 C68 C67 123.8(6) . . ? F14 C68 C67 120.0(6) . . ? N4 C69 F15 116.7(6) . . ? N4 C69 C70 124.4(7) . . ? F15 C69 C70 118.8(7) . . ? F16 C70 C66 120.4(6) . . ? F16 C70 C69 119.4(6) . . ? C66 C70 C69 120.2(6) . . ? C28 N1 C29 116.1(7) . . ? C33 N2 C34 116.2(7) . . ? C63 N3 C64 115.5(6) . . ? C69 N4 C68 116.4(6) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 2.601 _refine_diff_density_min -1.965 _refine_diff_density_rms 0.179