# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_UP4247(1-PhF2) _database_code_depnum_ccdc_archive 'CCDC 900232' #TrackingRef 'UF.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 F40 N4 U' _chemical_formula_weight 1630.55 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' U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_Int_Tables_number 15 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 23.5319(8) _cell_length_b 12.9011(5) _cell_length_c 16.0719(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.846(2) _cell_angle_gamma 90.00 _cell_volume 4669.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3072 _exptl_absorpt_coefficient_mu 3.682 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_absorpt_correction_T_min 0.5683 _exptl_absorpt_correction_T_max 0.7456 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 47650 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0142 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.53 _reflns_number_total 5367 _reflns_number_gt 5068 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0284P)^2^+4.1986P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _refine_ls_extinction_method none _refine_ls_number_reflns 5367 _refine_ls_number_parameters 422 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0204 _refine_ls_R_factor_gt 0.0179 _refine_ls_wR_factor_ref 0.0456 _refine_ls_wR_factor_gt 0.0445 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group U1 U 0.5000 0.620115(7) 0.7500 0.01960(4) Uani 1 2 d S . . N1 N 0.5000 0.43508(18) 0.7500 0.0211(5) Uani 1 2 d S . . N2 N 0.5000 0.80383(18) 0.7500 0.0200(4) Uani 1 2 d S . . N3 N 0.59573(8) 0.63785(14) 0.83412(11) 0.0250(3) Uani 1 1 d . . . C1 C 0.45268(9) 0.38087(14) 0.76612(13) 0.0212(4) Uani 1 1 d . . . C2 C 0.42072(9) 0.43069(15) 0.81506(12) 0.0220(4) Uani 1 1 d . . . C3 C 0.37041(9) 0.39175(16) 0.83085(13) 0.0249(4) Uani 1 1 d . . . C4 C 0.34953(9) 0.29659(18) 0.79684(14) 0.0280(4) Uani 1 1 d . . . C5 C 0.37873(9) 0.24425(17) 0.74679(14) 0.0280(4) Uani 1 1 d . . . C6 C 0.42873(9) 0.28615(16) 0.73075(14) 0.0251(4) Uani 1 1 d . . . C7 C 0.48301(9) 0.85647(15) 0.67071(13) 0.0215(4) Uani 1 1 d . . . C8 C 0.48947(9) 0.80457(15) 0.59807(13) 0.0232(4) Uani 1 1 d . . . C9 C 0.46976(10) 0.84055(18) 0.51416(13) 0.0290(4) Uani 1 1 d . . . C10 C 0.44109(10) 0.93496(19) 0.49952(14) 0.0315(5) Uani 1 1 d . . . C11 C 0.43269(10) 0.98981(17) 0.56873(14) 0.0289(4) Uani 1 1 d . . . C12 C 0.45279(9) 0.95092(16) 0.65270(13) 0.0243(4) Uani 1 1 d . . . C13 C 0.62271(9) 0.54648(17) 0.87817(13) 0.0248(4) Uani 1 1 d . . . C14 C 0.67340(9) 0.50279(18) 0.86378(13) 0.0265(4) Uani 1 1 d . . . C15 C 0.69752(10) 0.4120(2) 0.90274(16) 0.0333(5) Uani 1 1 d . . . C16 C 0.67071(11) 0.35940(19) 0.95642(16) 0.0349(5) Uani 1 1 d . . . C17 C 0.62097(10) 0.40054(19) 0.97217(14) 0.0307(5) Uani 1 1 d . . . C18 C 0.59829(9) 0.49291(17) 0.93435(13) 0.0263(4) Uani 1 1 d . . . C19 C 0.63345(9) 0.72612(17) 0.85150(14) 0.0257(4) Uani 1 1 d . . . C20 C 0.65808(9) 0.76298(18) 0.93559(14) 0.0288(4) Uani 1 1 d . . . C21 C 0.69194(10) 0.8515(2) 0.95360(16) 0.0334(5) Uani 1 1 d . . . C22 C 0.70197(10) 0.90828(19) 0.88677(18) 0.0354(5) Uani 1 1 d . . . C23 C 0.67937(11) 0.87357(18) 0.80253(17) 0.0353(5) Uani 1 1 d . . . C24 C 0.64624(9) 0.78355(19) 0.78590(14) 0.0308(5) Uani 1 1 d . . . F1 F 0.43930(5) 0.52832(9) 0.84458(8) 0.0270(2) Uani 1 1 d . . . F2 F 0.34172(6) 0.44698(11) 0.87623(8) 0.0323(3) Uani 1 1 d . . . F3 F 0.30014(6) 0.25701(11) 0.80963(9) 0.0381(3) Uani 1 1 d . . . F4 F 0.35662(6) 0.15456(11) 0.70992(10) 0.0403(3) Uani 1 1 d . . . F5 F 0.45302(6) 0.23559(10) 0.67661(9) 0.0314(3) Uani 1 1 d . . . F6 F 0.51454(5) 0.70775(9) 0.61203(8) 0.0259(2) Uani 1 1 d . . . F7 F 0.47716(7) 0.78456(12) 0.44838(8) 0.0385(3) Uani 1 1 d . . . F8 F 0.42064(7) 0.97237(12) 0.41860(9) 0.0450(4) Uani 1 1 d . . . F9 F 0.40294(7) 1.07916(11) 0.55428(9) 0.0418(3) Uani 1 1 d . . . F10 F 0.44030(6) 1.00342(10) 0.71698(8) 0.0304(3) Uani 1 1 d . . . F11 F 0.69834(6) 0.54958(11) 0.80868(8) 0.0332(3) Uani 1 1 d . . . F12 F 0.74529(7) 0.37172(12) 0.88559(12) 0.0503(4) Uani 1 1 d . . . F13 F 0.69190(7) 0.26892(14) 0.99167(12) 0.0570(5) Uani 1 1 d . . . F14 F 0.59513(7) 0.35068(12) 1.02453(10) 0.0418(3) Uani 1 1 d . . . F15 F 0.55019(6) 0.53198(11) 0.95242(9) 0.0371(3) Uani 1 1 d . . . F16 F 0.64657(6) 0.71202(11) 1.00222(8) 0.0376(3) Uani 1 1 d . . . F17 F 0.71302(8) 0.88496(12) 1.03589(10) 0.0477(4) Uani 1 1 d . . . F18 F 0.73330(7) 0.99633(12) 0.90366(11) 0.0486(4) Uani 1 1 d . . . F19 F 0.68942(8) 0.92706(14) 0.73728(11) 0.0519(4) Uani 1 1 d . . . F20 F 0.62534(7) 0.75121(12) 0.70351(9) 0.0417(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 U1 0.01913(5) 0.01580(6) 0.02305(6) 0.000 0.00484(4) 0.000 N1 0.0201(11) 0.0192(11) 0.0241(11) 0.000 0.0067(9) 0.000 N2 0.0226(11) 0.0180(11) 0.0192(11) 0.000 0.0060(9) 0.000 N3 0.0211(8) 0.0280(9) 0.0245(8) 0.0007(7) 0.0046(7) 0.0000(7) C1 0.0201(9) 0.0196(9) 0.0231(9) 0.0034(7) 0.0050(7) 0.0008(7) C2 0.0246(9) 0.0183(9) 0.0224(9) 0.0006(7) 0.0056(7) -0.0003(7) C3 0.0243(10) 0.0285(11) 0.0226(9) 0.0025(8) 0.0077(8) 0.0025(8) C4 0.0200(9) 0.0332(12) 0.0312(11) 0.0027(9) 0.0078(8) -0.0052(8) C5 0.0244(10) 0.0229(10) 0.0351(11) -0.0017(9) 0.0059(8) -0.0031(8) C6 0.0237(10) 0.0230(10) 0.0283(10) -0.0014(8) 0.0070(8) 0.0017(8) C7 0.0226(9) 0.0192(9) 0.0230(9) 0.0004(7) 0.0071(7) -0.0033(7) C8 0.0254(10) 0.0202(9) 0.0248(9) 0.0002(8) 0.0086(8) -0.0025(8) C9 0.0313(11) 0.0332(11) 0.0234(10) -0.0033(9) 0.0097(8) -0.0061(9) C10 0.0342(11) 0.0345(12) 0.0223(10) 0.0083(9) 0.0026(8) -0.0058(9) C11 0.0303(11) 0.0226(10) 0.0303(11) 0.0056(8) 0.0031(8) 0.0003(8) C12 0.0263(10) 0.0209(9) 0.0250(10) -0.0003(8) 0.0065(8) -0.0012(8) C13 0.0217(9) 0.0269(10) 0.0222(9) -0.0030(8) 0.0007(7) -0.0005(8) C14 0.0219(9) 0.0332(11) 0.0228(9) -0.0004(8) 0.0038(7) -0.0013(8) C15 0.0238(10) 0.0390(12) 0.0374(12) 0.0033(10) 0.0093(9) 0.0062(9) C16 0.0299(11) 0.0358(12) 0.0364(12) 0.0097(10) 0.0054(9) 0.0064(10) C17 0.0284(11) 0.0377(12) 0.0260(10) 0.0018(9) 0.0080(8) -0.0018(9) C18 0.0214(9) 0.0321(11) 0.0249(10) -0.0016(8) 0.0058(8) 0.0014(8) C19 0.0191(9) 0.0276(11) 0.0292(10) -0.0002(8) 0.0052(8) 0.0027(8) C20 0.0262(10) 0.0299(11) 0.0277(10) 0.0013(9) 0.0038(8) 0.0013(9) C21 0.0245(10) 0.0352(12) 0.0352(12) -0.0055(10) 0.0004(9) -0.0014(9) C22 0.0219(10) 0.0321(12) 0.0522(14) -0.0036(11) 0.0106(10) -0.0036(9) C23 0.0289(11) 0.0379(13) 0.0440(13) 0.0043(10) 0.0181(10) -0.0016(9) C24 0.0244(10) 0.0389(13) 0.0293(11) -0.0016(9) 0.0084(8) 0.0002(9) F1 0.0325(6) 0.0214(6) 0.0306(6) -0.0035(5) 0.0149(5) -0.0027(5) F2 0.0315(6) 0.0373(7) 0.0334(7) -0.0021(6) 0.0177(5) 0.0014(6) F3 0.0271(6) 0.0434(8) 0.0477(8) -0.0026(6) 0.0172(6) -0.0110(6) F4 0.0324(7) 0.0302(7) 0.0601(9) -0.0157(7) 0.0163(7) -0.0128(6) F5 0.0286(6) 0.0272(6) 0.0405(7) -0.0122(5) 0.0132(5) -0.0031(5) F6 0.0331(6) 0.0210(6) 0.0266(6) -0.0018(5) 0.0136(5) 0.0019(5) F7 0.0483(8) 0.0467(8) 0.0224(6) -0.0063(6) 0.0132(6) -0.0017(7) F8 0.0556(9) 0.0502(9) 0.0232(6) 0.0123(6) 0.0016(6) -0.0010(7) F9 0.0517(9) 0.0274(7) 0.0377(8) 0.0077(6) -0.0007(6) 0.0097(6) F10 0.0358(7) 0.0239(6) 0.0303(6) -0.0035(5) 0.0078(5) 0.0069(5) F11 0.0288(6) 0.0405(7) 0.0324(7) 0.0045(6) 0.0124(5) 0.0011(6) F12 0.0342(8) 0.0580(10) 0.0655(10) 0.0214(8) 0.0253(7) 0.0215(7) F13 0.0481(9) 0.0532(10) 0.0759(12) 0.0342(9) 0.0275(8) 0.0222(8) F14 0.0439(8) 0.0439(8) 0.0430(8) 0.0133(7) 0.0212(7) 0.0014(7) F15 0.0324(7) 0.0401(8) 0.0445(8) 0.0057(6) 0.0198(6) 0.0071(6) F16 0.0481(8) 0.0363(8) 0.0243(6) 0.0022(5) 0.0043(6) -0.0052(6) F17 0.0492(9) 0.0466(9) 0.0383(8) -0.0116(7) -0.0017(7) -0.0137(7) F18 0.0367(8) 0.0394(8) 0.0708(11) -0.0073(8) 0.0173(7) -0.0137(7) F19 0.0584(10) 0.0527(10) 0.0550(10) 0.0063(8) 0.0327(8) -0.0138(8) F20 0.0468(8) 0.0528(9) 0.0273(7) -0.0023(6) 0.0136(6) -0.0083(7) 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 U1 N3 2.2781(17) . ? U1 N3 2.2781(17) 2_656 ? U1 N2 2.370(2) . ? U1 N1 2.387(2) . ? U1 F6 2.5985(11) . ? U1 F6 2.5985(11) 2_656 ? U1 F1 2.6480(11) 2_656 ? U1 F1 2.6480(11) . ? N1 C1 1.401(2) 2_656 ? N1 C1 1.401(2) . ? N2 C7 1.396(2) . ? N2 C7 1.396(2) 2_656 ? N3 C19 1.421(3) . ? N3 C13 1.426(3) . ? C1 C2 1.393(3) . ? C1 C6 1.396(3) . ? C2 F1 1.372(2) . ? C2 C3 1.376(3) . ? C3 F2 1.335(2) . ? C3 C4 1.375(3) . ? C4 F3 1.339(2) . ? C4 C5 1.377(3) . ? C5 F4 1.335(2) . ? C5 C6 1.385(3) . ? C6 F5 1.341(2) . ? C7 C8 1.392(3) . ? C7 C12 1.398(3) . ? C8 F6 1.372(2) . ? C8 C9 1.374(3) . ? C9 F7 1.333(2) . ? C9 C10 1.379(3) . ? C10 F8 1.339(2) . ? C10 C11 1.380(3) . ? C11 F9 1.334(3) . ? C11 C12 1.388(3) . ? C12 F10 1.337(2) . ? C13 C18 1.387(3) . ? C13 C14 1.398(3) . ? C14 F11 1.340(2) . ? C14 C15 1.372(3) . ? C15 F12 1.337(3) . ? C15 C16 1.385(3) . ? C16 F13 1.330(3) . ? C16 C17 1.374(3) . ? C17 F14 1.337(3) . ? C17 C18 1.373(3) . ? C18 F15 1.345(2) . ? C19 C20 1.391(3) . ? C19 C24 1.391(3) . ? C20 F16 1.349(3) . ? C20 C21 1.374(3) . ? C21 F17 1.342(3) . ? C21 C22 1.376(4) . ? C22 F18 1.339(3) . ? C22 C23 1.378(4) . ? C23 F19 1.333(3) . ? C23 C24 1.381(3) . ? C24 F20 1.339(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 U1 N3 168.47(9) . 2_656 ? N3 U1 N2 84.24(5) . . ? N3 U1 N2 84.24(5) 2_656 . ? N3 U1 N1 95.76(5) . . ? N3 U1 N1 95.76(5) 2_656 . ? N2 U1 N1 180.000(1) . . ? N3 U1 F6 96.35(5) . . ? N3 U1 F6 78.58(5) 2_656 . ? N2 U1 F6 64.21(3) . . ? N1 U1 F6 115.79(2) . . ? N3 U1 F6 78.58(5) . 2_656 ? N3 U1 F6 96.35(5) 2_656 2_656 ? N2 U1 F6 64.21(3) . 2_656 ? N1 U1 F6 115.79(3) . 2_656 ? F6 U1 F6 128.42(5) . 2_656 ? N3 U1 F1 77.32(5) . 2_656 ? N3 U1 F1 108.02(5) 2_656 2_656 ? N2 U1 F1 116.57(3) . 2_656 ? N1 U1 F1 63.43(3) . 2_656 ? F6 U1 F1 58.56(4) . 2_656 ? F6 U1 F1 155.61(4) 2_656 2_656 ? N3 U1 F1 108.02(5) . . ? N3 U1 F1 77.32(5) 2_656 . ? N2 U1 F1 116.57(3) . . ? N1 U1 F1 63.43(3) . . ? F6 U1 F1 155.61(4) . . ? F6 U1 F1 58.56(4) 2_656 . ? F1 U1 F1 126.87(5) 2_656 . ? C1 N1 C1 120.1(2) 2_656 . ? C1 N1 U1 119.94(12) 2_656 . ? C1 N1 U1 119.94(11) . . ? C7 N2 C7 121.8(2) . 2_656 ? C7 N2 U1 119.10(12) . . ? C7 N2 U1 119.10(12) 2_656 . ? C19 N3 C13 113.71(17) . . ? C19 N3 U1 130.62(13) . . ? C13 N3 U1 115.66(13) . . ? C2 C1 C6 114.43(18) . . ? C2 C1 N1 117.53(18) . . ? C6 C1 N1 127.61(18) . . ? F1 C2 C3 118.45(17) . . ? F1 C2 C1 116.67(17) . . ? C3 C2 C1 124.75(19) . . ? F2 C3 C4 120.97(19) . . ? F2 C3 C2 120.31(19) . . ? C4 C3 C2 118.69(19) . . ? F3 C4 C3 120.36(19) . . ? F3 C4 C5 120.3(2) . . ? C3 C4 C5 119.25(19) . . ? F4 C5 C4 119.21(19) . . ? F4 C5 C6 119.90(19) . . ? C4 C5 C6 120.8(2) . . ? F5 C6 C5 118.41(18) . . ? F5 C6 C1 119.51(18) . . ? C5 C6 C1 122.02(19) . . ? C8 C7 N2 117.36(18) . . ? C8 C7 C12 114.72(18) . . ? N2 C7 C12 127.36(18) . . ? F6 C8 C9 118.36(18) . . ? F6 C8 C7 116.57(17) . . ? C9 C8 C7 125.0(2) . . ? F7 C9 C8 120.7(2) . . ? F7 C9 C10 120.88(19) . . ? C8 C9 C10 118.38(19) . . ? F8 C10 C9 120.3(2) . . ? F8 C10 C11 120.2(2) . . ? C9 C10 C11 119.51(19) . . ? F9 C11 C10 119.56(19) . . ? F9 C11 C12 119.7(2) . . ? C10 C11 C12 120.7(2) . . ? F10 C12 C11 118.60(18) . . ? F10 C12 C7 119.60(18) . . ? C11 C12 C7 121.73(19) . . ? C18 C13 C14 116.2(2) . . ? C18 C13 N3 121.76(18) . . ? C14 C13 N3 121.98(19) . . ? F11 C14 C15 118.95(19) . . ? F11 C14 C13 119.08(19) . . ? C15 C14 C13 121.9(2) . . ? F12 C15 C14 119.9(2) . . ? F12 C15 C16 120.0(2) . . ? C14 C15 C16 120.0(2) . . ? F13 C16 C17 119.7(2) . . ? F13 C16 C15 120.9(2) . . ? C17 C16 C15 119.5(2) . . ? F14 C17 C18 120.4(2) . . ? F14 C17 C16 119.8(2) . . ? C18 C17 C16 119.7(2) . . ? F15 C18 C17 118.21(19) . . ? F15 C18 C13 119.14(19) . . ? C17 C18 C13 122.6(2) . . ? C20 C19 C24 115.7(2) . . ? C20 C19 N3 121.71(19) . . ? C24 C19 N3 122.54(19) . . ? F16 C20 C21 118.4(2) . . ? F16 C20 C19 118.79(19) . . ? C21 C20 C19 122.8(2) . . ? F17 C21 C20 120.1(2) . . ? F17 C21 C22 120.0(2) . . ? C20 C21 C22 119.9(2) . . ? F18 C22 C21 120.2(2) . . ? F18 C22 C23 120.5(2) . . ? C21 C22 C23 119.3(2) . . ? F19 C23 C22 119.9(2) . . ? F19 C23 C24 120.1(2) . . ? C22 C23 C24 119.9(2) . . ? F20 C24 C23 118.6(2) . . ? F20 C24 C19 119.0(2) . . ? C23 C24 C19 122.4(2) . . ? C2 F1 U1 112.51(10) . . ? C8 F6 U1 112.26(10) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.389 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.074 data_UP4279(1-PhPhF) _database_code_depnum_ccdc_archive 'CCDC 900233' #TrackingRef 'UF.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H20 F20 N4 U' _chemical_formula_weight 1270.71 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' U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_Int_Tables_number 15 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 38.651(3) _cell_length_b 12.3736(9) _cell_length_c 19.9570(14) _cell_angle_alpha 90.00 _cell_angle_beta 99.992(3) _cell_angle_gamma 90.00 _cell_volume 9399.7(12) _cell_formula_units_Z 8 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4864 _exptl_absorpt_coefficient_mu 3.572 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_absorpt_correction_T_min 0.5243 _exptl_absorpt_correction_T_max 0.7456 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 103846 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -50 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.56 _refine_special_details ; The data were corrected for the presence of disordered solvent using the program SQUEEZE. ; _reflns_number_total 10719 _reflns_number_gt 9240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0375P)^2^+22.3879P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10719 _refine_ls_number_parameters 689 _refine_ls_number_restraints 246 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0652 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group U1 U 0.632340(3) 0.609113(7) 0.538120(5) 0.02849(4) Uani 1 1 d . A . F1 F 0.72968(5) 0.79643(15) 0.42763(10) 0.0438(4) Uani 1 1 d . . . F2 F 0.74914(5) 0.71187(19) 0.31730(10) 0.0528(5) Uani 1 1 d . . . F3 F 0.71953(5) 0.52824(19) 0.25931(10) 0.0555(5) Uani 1 1 d . . . F4 F 0.66405(5) 0.43817(16) 0.30951(10) 0.0481(5) Uani 1 1 d . . . F5 F 0.64180(4) 0.52939(13) 0.41647(9) 0.0347(4) Uani 1 1 d . . . F6 F 0.61126(5) 0.52102(14) 0.65099(10) 0.0454(4) Uani 1 1 d . . . F7 F 0.59260(6) 0.41176(17) 0.75723(11) 0.0531(5) Uani 1 1 d . . . F8 F 0.62423(6) 0.22064(17) 0.79787(10) 0.0540(5) Uani 1 1 d . . . F9 F 0.67691(6) 0.14628(17) 0.73461(11) 0.0558(5) Uani 1 1 d . . . F10 F 0.69772(5) 0.25648(15) 0.63535(9) 0.0433(4) Uani 1 1 d . . . F11 F 0.58621(6) 0.92229(19) 0.67581(13) 0.0655(6) Uani 1 1 d . . . F12 F 0.62392(8) 0.99175(19) 0.79101(12) 0.0744(7) Uani 1 1 d . . . F13 F 0.68725(8) 0.90349(19) 0.84342(11) 0.0690(7) Uani 1 1 d . . . F14 F 0.71056(5) 0.73063(18) 0.77886(10) 0.0516(5) Uani 1 1 d . . . F15 F 0.67196(5) 0.65532(14) 0.66133(8) 0.0370(4) Uani 1 1 d . . . F16 F 0.51083(6) 0.4565(2) 0.43983(16) 0.0793(8) Uani 1 1 d . A . F17 F 0.46463(7) 0.5726(3) 0.3556(2) 0.1130(12) Uani 1 1 d . . . F18 F 0.48301(7) 0.7665(3) 0.30626(16) 0.1071(11) Uani 1 1 d . A . F19 F 0.55161(6) 0.8354(2) 0.34033(13) 0.0750(7) Uani 1 1 d . . . F20 F 0.59867(4) 0.71596(15) 0.42549(9) 0.0400(4) Uani 1 1 d . A . N1 N 0.67183(6) 0.70044(17) 0.48395(11) 0.0269(4) Uani 1 1 d . . . N2 N 0.66054(6) 0.45770(18) 0.58394(12) 0.0322(5) Uani 1 1 d . . . N3 N 0.61194(6) 0.74086(19) 0.60151(13) 0.0343(5) Uani 1 1 d . . . N4 N 0.58190(7) 0.5289(2) 0.48061(15) 0.0404(6) Uani 1 1 d . . . C1 C 0.68447(7) 0.6654(2) 0.42687(13) 0.0283(5) Uani 1 1 d . . . C2 C 0.71256(7) 0.7091(2) 0.39927(15) 0.0339(6) Uani 1 1 d . . . C3 C 0.72334(7) 0.6638(3) 0.34313(15) 0.0394(7) Uani 1 1 d . . . C4 C 0.70829(8) 0.5718(3) 0.31296(15) 0.0400(7) Uani 1 1 d . . . C5 C 0.68066(8) 0.5260(2) 0.33834(15) 0.0370(6) Uani 1 1 d . . . C6 C 0.66958(7) 0.5738(2) 0.39283(14) 0.0305(6) Uani 1 1 d . . . C7 C 0.67345(7) 0.8134(2) 0.49979(14) 0.0274(5) Uani 1 1 d . . . C8 C 0.65937(7) 0.8914(2) 0.45275(15) 0.0307(6) Uani 1 1 d . . . H8 H 0.6504 0.8715 0.4082 0.037 Uiso 1 1 calc R . . C9 C 0.65863(8) 0.9988(2) 0.47216(17) 0.0370(6) Uani 1 1 d . . . H9 H 0.6497 1.0509 0.4403 0.044 Uiso 1 1 calc R . . C10 C 0.67110(9) 1.0288(3) 0.53839(18) 0.0428(7) Uani 1 1 d . . . H10 H 0.6696 1.1004 0.5516 0.051 Uiso 1 1 calc R . . C11 C 0.68580(9) 0.9527(3) 0.58480(16) 0.0421(7) Uani 1 1 d . . . H11 H 0.6947 0.9733 0.6293 0.050 Uiso 1 1 calc R . . C12 C 0.68742(7) 0.8454(2) 0.56565(15) 0.0331(6) Uani 1 1 d . . . H12 H 0.6979 0.7946 0.5971 0.040 Uiso 1 1 calc R . . C13 C 0.65418(8) 0.3931(2) 0.63703(15) 0.0327(6) Uani 1 1 d . . . C14 C 0.62806(8) 0.4267(2) 0.67265(16) 0.0360(6) Uani 1 1 d . . . C15 C 0.61754(9) 0.3716(3) 0.72505(17) 0.0405(7) Uani 1 1 d . . . C16 C 0.63367(9) 0.2755(3) 0.74586(16) 0.0408(7) Uani 1 1 d . . . C17 C 0.66024(9) 0.2383(2) 0.71383(16) 0.0393(7) Uani 1 1 d . . . C18 C 0.67061(8) 0.2965(2) 0.66175(15) 0.0355(6) Uani 1 1 d . . . C19 C 0.68672(7) 0.4265(2) 0.54445(15) 0.0312(6) Uani 1 1 d . . . C20 C 0.68024(8) 0.3436(2) 0.49654(16) 0.0379(6) Uani 1 1 d . . . H20 H 0.6594 0.3043 0.4916 0.045 Uiso 1 1 calc R . . C21 C 0.70521(9) 0.3206(3) 0.45638(16) 0.0427(7) Uani 1 1 d . . . H21 H 0.7012 0.2650 0.4246 0.051 Uiso 1 1 calc R . . C22 C 0.73595(9) 0.3792(3) 0.46305(19) 0.0452(8) Uani 1 1 d . . . H22 H 0.7525 0.3630 0.4357 0.054 Uiso 1 1 calc R . . C23 C 0.74229(8) 0.4611(3) 0.50970(18) 0.0437(7) Uani 1 1 d . . . H23 H 0.7630 0.5008 0.5138 0.052 Uiso 1 1 calc R . . C24 C 0.71775(8) 0.4849(2) 0.55110(16) 0.0357(6) Uani 1 1 d . . . H24 H 0.7222 0.5400 0.5832 0.043 Uiso 1 1 calc R . . C25 C 0.62803(8) 0.7853(2) 0.66285(16) 0.0367(7) Uani 1 1 d . . . C26 C 0.61677(10) 0.8719(3) 0.69895(19) 0.0469(8) Uani 1 1 d . . . C27 C 0.63653(12) 0.9091(3) 0.7588(2) 0.0530(9) Uani 1 1 d . . . C28 C 0.66779(11) 0.8646(3) 0.78564(18) 0.0505(9) Uani 1 1 d . . . C29 C 0.68018(9) 0.7779(3) 0.75343(16) 0.0427(7) Uani 1 1 d . . . C30 C 0.65990(8) 0.7412(2) 0.69409(15) 0.0361(6) Uani 1 1 d . . . C31 C 0.57904(8) 0.7849(2) 0.56752(16) 0.0356(6) Uani 1 1 d . . . C32 C 0.54789(8) 0.7302(2) 0.57033(18) 0.0429(7) Uani 1 1 d . . . H32 H 0.5481 0.6669 0.5956 0.052 Uiso 1 1 calc R . . C33 C 0.51644(9) 0.7708(3) 0.5351(2) 0.0546(9) Uani 1 1 d . . . H33 H 0.4955 0.7349 0.5371 0.065 Uiso 1 1 calc R . . C34 C 0.51610(10) 0.8631(3) 0.4976(2) 0.0574(10) Uani 1 1 d . . . H34 H 0.4949 0.8896 0.4743 0.069 Uiso 1 1 calc R . . C35 C 0.54675(10) 0.9174(3) 0.4939(2) 0.0538(9) Uani 1 1 d . . . H35 H 0.5463 0.9801 0.4681 0.065 Uiso 1 1 calc R . . C36 C 0.57840(9) 0.8783(2) 0.52897(19) 0.0437(8) Uani 1 1 d . . . H36 H 0.5992 0.9147 0.5266 0.052 Uiso 1 1 calc R . . C37 C 0.55671(8) 0.5825(3) 0.43451(18) 0.0417(7) Uani 1 1 d . A . C38 C 0.52184(9) 0.5483(3) 0.4150(2) 0.0584(10) Uani 1 1 d . . . C39 C 0.49826(11) 0.6076(4) 0.3719(3) 0.0750(14) Uani 1 1 d . A . C40 C 0.50743(10) 0.7047(5) 0.3462(2) 0.0743(14) Uani 1 1 d . . . C41 C 0.54148(10) 0.7417(4) 0.3640(2) 0.0562(9) Uani 1 1 d . A . C42 C 0.56469(8) 0.6801(3) 0.40677(16) 0.0404(7) Uani 1 1 d . . . C43 C 0.5817(4) 0.4137(5) 0.4885(5) 0.054(3) Uani 0.40 1 d PGU A 1 C44 C 0.5776(3) 0.3621(7) 0.5485(5) 0.067(3) Uani 0.40 1 d PGU A 1 H44 H 0.5734 0.4025 0.5856 0.090 Uiso 0.40 1 calc PR A 1 C45 C 0.5797(3) 0.2501(7) 0.5531(5) 0.085(3) Uani 0.40 1 d PGU A 1 H45 H 0.5770 0.2156 0.5932 0.114 Uiso 0.40 1 calc PR A 1 C46 C 0.5860(3) 0.1897(5) 0.4976(6) 0.089(3) Uani 0.40 1 d PGU A 1 H46 H 0.5874 0.1148 0.5007 0.119 Uiso 0.40 1 calc PR A 1 C47 C 0.5901(3) 0.2413(7) 0.4376(5) 0.082(3) Uani 0.40 1 d PGU A 1 H47 H 0.5942 0.2010 0.4006 0.109 Uiso 0.40 1 calc PR A 1 C48 C 0.5879(3) 0.3533(7) 0.4331(5) 0.068(3) Uani 0.40 1 d PGU A 1 H48 H 0.5906 0.3878 0.3929 0.091 Uiso 0.40 1 calc PR A 1 C43' C 0.5813(2) 0.4131(3) 0.4651(3) 0.0442(17) Uani 0.60 1 d PGU A 2 C44' C 0.5836(2) 0.3728(4) 0.4010(3) 0.0559(17) Uani 0.60 1 d PGU A 2 H44' H 0.5836 0.4200 0.3648 0.074 Uiso 0.60 1 calc PR A 2 C45' C 0.58584(17) 0.2620(4) 0.3911(3) 0.0734(19) Uani 0.60 1 d PGU A 2 H45' H 0.5874 0.2351 0.3482 0.098 Uiso 0.60 1 calc PR A 2 C46' C 0.58584(16) 0.1915(3) 0.4453(3) 0.077(2) Uani 0.60 1 d PGU A 2 H46' H 0.5873 0.1174 0.4387 0.102 Uiso 0.60 1 calc PR A 2 C47' C 0.58358(16) 0.2317(4) 0.5094(3) 0.0693(18) Uani 0.60 1 d PGU A 2 H47' H 0.5836 0.1845 0.5457 0.092 Uiso 0.60 1 calc PR A 2 C48' C 0.58133(19) 0.3425(4) 0.5194(2) 0.0521(15) Uani 0.60 1 d PGU A 2 H48' H 0.5798 0.3695 0.5623 0.069 Uiso 0.60 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U1 0.03144(6) 0.02074(6) 0.03702(6) -0.00038(4) 0.01640(4) 0.00010(4) F1 0.0352(9) 0.0457(11) 0.0537(11) -0.0001(9) 0.0167(8) -0.0110(8) F2 0.0373(10) 0.0806(15) 0.0456(10) 0.0118(10) 0.0210(8) -0.0018(9) F3 0.0554(12) 0.0735(15) 0.0428(10) -0.0054(10) 0.0228(9) 0.0171(11) F4 0.0558(11) 0.0396(10) 0.0502(11) -0.0162(9) 0.0127(9) 0.0037(9) F5 0.0343(8) 0.0275(8) 0.0455(9) -0.0055(7) 0.0155(7) -0.0021(7) F6 0.0504(11) 0.0326(9) 0.0618(12) 0.0113(8) 0.0341(9) 0.0093(8) F7 0.0564(12) 0.0566(12) 0.0550(12) 0.0094(10) 0.0339(10) 0.0014(10) F8 0.0725(14) 0.0482(11) 0.0438(10) 0.0147(9) 0.0170(10) -0.0077(10) F9 0.0744(14) 0.0391(10) 0.0540(12) 0.0165(9) 0.0119(10) 0.0111(10) F10 0.0494(10) 0.0347(9) 0.0474(10) 0.0028(8) 0.0126(8) 0.0108(8) F11 0.0689(14) 0.0522(12) 0.0802(16) -0.0224(12) 0.0262(12) 0.0184(11) F12 0.1085(19) 0.0525(14) 0.0685(15) -0.0279(12) 0.0333(14) 0.0057(13) F13 0.103(2) 0.0627(15) 0.0415(11) -0.0173(10) 0.0145(12) -0.0147(13) F14 0.0569(12) 0.0577(13) 0.0421(10) 0.0056(9) 0.0137(9) -0.0076(10) F15 0.0462(10) 0.0312(9) 0.0372(9) -0.0021(7) 0.0176(7) 0.0022(7) F16 0.0409(12) 0.0594(15) 0.141(2) -0.0141(15) 0.0242(13) -0.0205(11) F17 0.0351(13) 0.135(3) 0.159(3) -0.021(2) -0.0115(16) -0.0130(15) F18 0.0560(15) 0.153(3) 0.101(2) 0.022(2) -0.0162(15) 0.0248(18) F19 0.0606(14) 0.0893(19) 0.0741(16) 0.0306(15) 0.0085(12) 0.0162(13) F20 0.0311(8) 0.0409(10) 0.0501(10) 0.0063(8) 0.0128(7) -0.0001(7) N1 0.0283(11) 0.0221(11) 0.0327(11) 0.0007(9) 0.0118(9) 0.0011(8) N2 0.0343(12) 0.0236(11) 0.0425(13) 0.0009(10) 0.0173(10) 0.0002(9) N3 0.0361(12) 0.0252(12) 0.0458(14) -0.0039(10) 0.0188(11) 0.0000(10) N4 0.0332(13) 0.0303(13) 0.0615(17) -0.0048(12) 0.0186(12) -0.0036(10) C1 0.0260(12) 0.0279(13) 0.0320(13) 0.0031(11) 0.0077(10) 0.0035(10) C2 0.0279(13) 0.0367(15) 0.0376(15) 0.0032(12) 0.0072(11) 0.0005(11) C3 0.0287(14) 0.0546(19) 0.0377(15) 0.0117(14) 0.0141(12) 0.0068(13) C4 0.0371(15) 0.0519(19) 0.0325(15) 0.0005(14) 0.0103(12) 0.0150(14) C5 0.0378(15) 0.0347(15) 0.0392(15) -0.0032(13) 0.0085(12) 0.0100(12) C6 0.0280(13) 0.0295(13) 0.0357(14) 0.0025(11) 0.0100(11) 0.0030(11) C7 0.0251(12) 0.0250(13) 0.0344(13) 0.0004(11) 0.0119(10) -0.0026(10) C8 0.0304(13) 0.0297(14) 0.0330(14) 0.0018(11) 0.0081(11) 0.0001(11) C9 0.0366(15) 0.0261(14) 0.0526(18) 0.0061(13) 0.0198(13) 0.0014(11) C10 0.0486(18) 0.0281(15) 0.059(2) -0.0097(14) 0.0290(15) -0.0056(13) C11 0.0462(17) 0.0449(18) 0.0385(16) -0.0129(14) 0.0169(13) -0.0140(14) C12 0.0320(14) 0.0362(15) 0.0328(14) 0.0020(12) 0.0099(11) -0.0085(12) C13 0.0364(14) 0.0244(13) 0.0390(15) -0.0002(11) 0.0115(12) -0.0054(11) C14 0.0410(16) 0.0263(13) 0.0439(16) 0.0033(12) 0.0161(13) -0.0006(12) C15 0.0431(17) 0.0413(17) 0.0405(16) 0.0009(13) 0.0170(13) -0.0063(13) C16 0.0503(18) 0.0367(16) 0.0365(15) 0.0053(13) 0.0107(13) -0.0094(14) C17 0.0503(18) 0.0247(14) 0.0411(16) 0.0033(12) 0.0025(13) -0.0030(13) C18 0.0401(15) 0.0270(14) 0.0399(15) -0.0034(12) 0.0082(12) -0.0008(11) C19 0.0342(14) 0.0229(12) 0.0387(15) 0.0033(11) 0.0129(12) 0.0046(11) C20 0.0378(15) 0.0273(14) 0.0501(18) -0.0027(13) 0.0118(13) 0.0013(12) C21 0.0537(19) 0.0340(16) 0.0420(16) -0.0038(13) 0.0125(14) 0.0130(14) C22 0.0435(18) 0.0441(18) 0.054(2) 0.0086(15) 0.0241(15) 0.0157(14) C23 0.0316(15) 0.0411(17) 0.062(2) 0.0069(16) 0.0185(14) 0.0034(13) C24 0.0345(14) 0.0279(14) 0.0461(16) 0.0000(12) 0.0109(12) 0.0018(11) C25 0.0470(17) 0.0273(14) 0.0425(16) -0.0042(12) 0.0262(13) -0.0058(12) C26 0.057(2) 0.0347(16) 0.055(2) -0.0067(15) 0.0271(17) 0.0041(15) C27 0.082(3) 0.0336(17) 0.051(2) -0.0143(15) 0.0328(19) -0.0058(17) C28 0.073(2) 0.0434(18) 0.0394(17) -0.0066(15) 0.0217(17) -0.0143(17) C29 0.060(2) 0.0368(16) 0.0371(16) 0.0029(13) 0.0231(15) -0.0103(15) C30 0.0482(17) 0.0284(14) 0.0375(15) -0.0012(12) 0.0243(13) -0.0044(12) C31 0.0367(15) 0.0245(13) 0.0513(17) -0.0056(12) 0.0233(13) 0.0024(11) C32 0.0401(16) 0.0278(15) 0.068(2) -0.0047(14) 0.0287(15) -0.0012(12) C33 0.0354(17) 0.0406(19) 0.093(3) -0.0121(19) 0.0254(18) -0.0033(14) C34 0.0421(19) 0.046(2) 0.085(3) -0.0075(19) 0.0136(18) 0.0124(15) C35 0.050(2) 0.0371(17) 0.078(3) 0.0099(17) 0.0218(18) 0.0126(15) C36 0.0415(17) 0.0297(15) 0.066(2) 0.0054(14) 0.0257(16) 0.0030(13) C37 0.0313(15) 0.0426(17) 0.0543(19) -0.0139(15) 0.0159(14) -0.0016(13) C38 0.0337(17) 0.060(2) 0.084(3) -0.018(2) 0.0162(18) -0.0058(16) C39 0.0327(19) 0.092(4) 0.097(4) -0.020(3) 0.003(2) -0.007(2) C40 0.037(2) 0.111(4) 0.068(3) -0.005(3) -0.0066(18) 0.017(2) C41 0.047(2) 0.067(3) 0.055(2) 0.0076(19) 0.0102(16) 0.0069(18) C42 0.0281(14) 0.0516(19) 0.0428(16) -0.0054(15) 0.0101(12) 0.0016(13) C43 0.030(5) 0.036(4) 0.093(7) -0.010(4) 0.003(5) -0.002(4) C44 0.046(6) 0.044(4) 0.104(7) 0.008(5) -0.011(6) -0.023(4) C45 0.057(6) 0.049(5) 0.134(7) 0.014(5) -0.028(6) -0.012(5) C46 0.045(5) 0.040(5) 0.168(8) -0.003(5) -0.024(7) -0.002(5) C47 0.041(5) 0.040(4) 0.161(7) -0.029(6) 0.007(6) -0.002(4) C48 0.039(5) 0.043(4) 0.124(7) -0.024(5) 0.020(6) -0.005(4) C43' 0.031(3) 0.033(3) 0.073(4) -0.011(2) 0.020(3) -0.011(2) C44' 0.050(4) 0.044(3) 0.078(4) -0.024(3) 0.023(4) -0.014(3) C45' 0.053(4) 0.046(3) 0.124(5) -0.036(4) 0.023(5) -0.013(3) C46' 0.038(3) 0.033(3) 0.160(6) -0.014(4) 0.021(5) -0.011(3) C47' 0.033(3) 0.035(3) 0.133(5) 0.007(4) -0.005(4) -0.009(3) C48' 0.029(3) 0.042(3) 0.082(4) 0.007(3) 0.003(3) -0.009(3) 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 U1 N2 2.278(2) . ? U1 N3 2.286(2) . ? U1 N4 2.308(3) . ? U1 N1 2.313(2) . ? U1 F5 2.7034(16) . ? U1 F15 2.7225(17) . ? U1 F20 2.7347(18) . ? U1 F6 2.7502(17) . ? F1 C2 1.340(3) . ? F2 C3 1.339(3) . ? F3 C4 1.337(3) . ? F4 C5 1.340(4) . ? F5 C6 1.361(3) . ? F6 C14 1.368(3) . ? F7 C15 1.343(4) . ? F8 C16 1.342(3) . ? F9 C17 1.339(4) . ? F10 C18 1.346(3) . ? F11 C26 1.345(4) . ? F12 C27 1.344(4) . ? F13 C28 1.352(4) . ? F14 C29 1.331(4) . ? F15 C30 1.371(3) . ? F16 C38 1.338(5) . ? F17 C39 1.355(5) . ? F18 C40 1.360(5) . ? F19 C41 1.336(5) . ? F20 C42 1.375(3) . ? N1 C1 1.384(3) . ? N1 C7 1.432(3) . ? N2 C13 1.383(4) . ? N2 C19 1.439(3) . ? N3 C25 1.387(4) . ? N3 C31 1.440(4) . ? N4 C37 1.387(4) . ? N4 C43 1.434(7) . ? N4 C43' 1.465(5) . ? C1 C6 1.394(4) . ? C1 C2 1.408(4) . ? C2 C3 1.380(4) . ? C3 C4 1.370(5) . ? C4 C5 1.381(5) . ? C5 C6 1.371(4) . ? C7 C12 1.389(4) . ? C7 C8 1.390(4) . ? C8 C9 1.386(4) . ? C9 C10 1.377(5) . ? C10 C11 1.372(5) . ? C11 C12 1.386(5) . ? C13 C14 1.395(4) . ? C13 C18 1.402(4) . ? C14 C15 1.368(4) . ? C15 C16 1.373(5) . ? C16 C17 1.379(5) . ? C17 C18 1.379(4) . ? C19 C24 1.386(4) . ? C19 C20 1.395(4) . ? C20 C21 1.387(4) . ? C21 C22 1.379(5) . ? C22 C23 1.369(5) . ? C23 C24 1.393(4) . ? C25 C30 1.392(5) . ? C25 C26 1.402(4) . ? C26 C27 1.380(6) . ? C27 C28 1.351(6) . ? C28 C29 1.378(5) . ? C29 C30 1.379(5) . ? C31 C36 1.387(4) . ? C31 C32 1.391(4) . ? C32 C33 1.389(5) . ? C33 C34 1.364(6) . ? C34 C35 1.375(5) . ? C35 C36 1.386(5) . ? C37 C42 1.386(5) . ? C37 C38 1.402(5) . ? C38 C39 1.354(7) . ? C39 C40 1.378(7) . ? C40 C41 1.380(6) . ? C41 C42 1.360(5) . ? C43 C44 1.3900 . ? C43 C48 1.3900 . ? C44 C45 1.3900 . ? C45 C46 1.3900 . ? C46 C47 1.3900 . ? C47 C48 1.3900 . ? C43' C44' 1.3900 . ? C43' C48' 1.3900 . ? C44' C45' 1.3900 . ? C45' C46' 1.3900 . ? C46' C47' 1.3900 . ? C47' C48' 1.3900 . ? 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 U1 N3 123.46(9) . . ? N2 U1 N4 98.62(9) . . ? N3 U1 N4 103.85(9) . . ? N2 U1 N1 106.31(8) . . ? N3 U1 N1 103.25(8) . . ? N4 U1 N1 123.15(9) . . ? N2 U1 F5 86.02(7) . . ? N3 U1 F5 150.52(7) . . ? N4 U1 F5 68.32(7) . . ? N1 U1 F5 63.60(6) . . ? N2 U1 F15 69.83(7) . . ? N3 U1 F15 62.89(7) . . ? N4 U1 F15 146.48(8) . . ? N1 U1 F15 90.35(7) . . ? F5 U1 F15 138.17(5) . . ? N2 U1 F20 148.64(7) . . ? N3 U1 F20 87.11(8) . . ? N4 U1 F20 63.82(8) . . ? N1 U1 F20 68.78(7) . . ? F5 U1 F20 63.74(5) . . ? F15 U1 F20 138.91(5) . . ? N2 U1 F6 62.25(7) . . ? N3 U1 F6 69.49(7) . . ? N4 U1 F6 83.80(8) . . ? N1 U1 F6 152.87(7) . . ? F5 U1 F6 134.14(5) . . ? F15 U1 F6 62.85(6) . . ? F20 U1 F6 134.30(5) . . ? C6 F5 U1 113.67(15) . . ? C14 F6 U1 113.88(15) . . ? C30 F15 U1 114.13(17) . . ? C42 F20 U1 111.29(17) . . ? C1 N1 C7 118.6(2) . . ? C1 N1 U1 125.98(17) . . ? C7 N1 U1 112.37(15) . . ? C13 N2 C19 120.0(2) . . ? C13 N2 U1 130.29(18) . . ? C19 N2 U1 109.48(17) . . ? C25 N3 C31 119.3(2) . . ? C25 N3 U1 128.8(2) . . ? C31 N3 U1 111.72(18) . . ? C37 N4 C43 122.1(6) . . ? C37 N4 C43' 110.2(4) . . ? C43 N4 C43' 18.4(5) . . ? C37 N4 U1 124.0(2) . . ? C43 N4 U1 113.2(6) . . ? C43' N4 U1 120.4(4) . . ? N1 C1 C6 118.7(2) . . ? N1 C1 C2 127.4(3) . . ? C6 C1 C2 113.8(2) . . ? F1 C2 C3 118.3(3) . . ? F1 C2 C1 120.2(3) . . ? C3 C2 C1 121.6(3) . . ? F2 C3 C4 119.2(3) . . ? F2 C3 C2 118.8(3) . . ? C4 C3 C2 122.0(3) . . ? F3 C4 C3 121.0(3) . . ? F3 C4 C5 120.5(3) . . ? C3 C4 C5 118.5(3) . . ? F4 C5 C6 119.9(3) . . ? F4 C5 C4 121.3(3) . . ? C6 C5 C4 118.8(3) . . ? F5 C6 C5 118.3(3) . . ? F5 C6 C1 116.3(2) . . ? C5 C6 C1 125.4(3) . . ? C12 C7 C8 118.9(3) . . ? C12 C7 N1 118.8(2) . . ? C8 C7 N1 122.1(2) . . ? C9 C8 C7 120.1(3) . . ? C10 C9 C8 120.4(3) . . ? C11 C10 C9 119.9(3) . . ? C10 C11 C12 120.3(3) . . ? C11 C12 C7 120.3(3) . . ? N2 C13 C14 117.3(3) . . ? N2 C13 C18 129.2(3) . . ? C14 C13 C18 113.5(3) . . ? F6 C14 C15 118.6(3) . . ? F6 C14 C13 116.1(2) . . ? C15 C14 C13 125.3(3) . . ? F7 C15 C14 120.9(3) . . ? F7 C15 C16 120.1(3) . . ? C14 C15 C16 118.9(3) . . ? F8 C16 C15 120.1(3) . . ? F8 C16 C17 121.0(3) . . ? C15 C16 C17 118.9(3) . . ? F9 C17 C16 119.8(3) . . ? F9 C17 C18 119.4(3) . . ? C16 C17 C18 120.8(3) . . ? F10 C18 C17 116.8(3) . . ? F10 C18 C13 120.8(3) . . ? C17 C18 C13 122.5(3) . . ? C24 C19 C20 119.9(3) . . ? C24 C19 N2 119.1(3) . . ? C20 C19 N2 120.8(3) . . ? C21 C20 C19 119.2(3) . . ? C22 C21 C20 120.7(3) . . ? C23 C22 C21 120.3(3) . . ? C22 C23 C24 120.0(3) . . ? C19 C24 C23 120.0(3) . . ? N3 C25 C30 117.8(3) . . ? N3 C25 C26 128.7(3) . . ? C30 C25 C26 113.5(3) . . ? F11 C26 C27 117.6(3) . . ? F11 C26 C25 120.7(3) . . ? C27 C26 C25 121.7(3) . . ? F12 C27 C28 119.6(4) . . ? F12 C27 C26 118.4(4) . . ? C28 C27 C26 122.0(3) . . ? F13 C28 C27 121.3(3) . . ? F13 C28 C29 119.2(4) . . ? C27 C28 C29 119.4(3) . . ? F14 C29 C28 121.3(3) . . ? F14 C29 C30 121.0(3) . . ? C28 C29 C30 117.7(3) . . ? F15 C30 C29 118.4(3) . . ? F15 C30 C25 116.0(3) . . ? C29 C30 C25 125.6(3) . . ? C36 C31 C32 119.7(3) . . ? C36 C31 N3 120.4(3) . . ? C32 C31 N3 119.8(3) . . ? C33 C32 C31 119.4(3) . . ? C34 C33 C32 120.3(3) . . ? C33 C34 C35 120.8(4) . . ? C34 C35 C36 119.7(4) . . ? C35 C36 C31 120.0(3) . . ? C42 C37 N4 120.2(3) . . ? C42 C37 C38 114.9(3) . . ? N4 C37 C38 124.8(3) . . ? F16 C38 C39 118.2(4) . . ? F16 C38 C37 120.3(4) . . ? C39 C38 C37 121.5(4) . . ? C38 C39 F17 119.4(5) . . ? C38 C39 C40 121.4(4) . . ? F17 C39 C40 119.1(4) . . ? F18 C40 C39 120.8(4) . . ? F18 C40 C41 119.9(5) . . ? C39 C40 C41 119.2(4) . . ? F19 C41 C42 120.4(3) . . ? F19 C41 C40 121.4(4) . . ? C42 C41 C40 118.2(4) . . ? C41 C42 F20 119.0(3) . . ? C41 C42 C37 124.8(3) . . ? F20 C42 C37 116.2(3) . . ? C44 C43 C48 120.0 . . ? C44 C43 N4 123.7(6) . . ? C48 C43 N4 116.2(6) . . ? C43 C44 C45 120.0 . . ? C46 C45 C44 120.0 . . ? C45 C46 C47 120.0 . . ? C48 C47 C46 120.0 . . ? C47 C48 C43 120.0 . . ? C44' C43' C48' 120.0 . . ? C44' C43' N4 122.9(4) . . ? C48' C43' N4 116.9(4) . . ? C43' C44' C45' 120.0 . . ? C46' C45' C44' 120.0 . . ? C45' C46' C47' 120.0 . . ? C48' C47' C46' 120.0 . . ? C47' C48' C43' 120.0 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.112 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.081 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.197 0.250 216 54 ' ' 2 0.500 -0.197 0.750 216 54 ' ' 3 0.000 0.303 0.750 216 54 ' ' 4 0.000 0.697 0.250 216 54 ' ' data_UP4230(2) _database_code_depnum_ccdc_archive 'CCDC 900234' #TrackingRef 'UF.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H16 F30 N3 O2 U' _chemical_formula_weight 1426.63 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' U U -9.6767 9.6646 '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 11.0728(3) _cell_length_b 11.7379(4) _cell_length_c 20.3378(6) _cell_angle_alpha 79.419(2) _cell_angle_beta 80.1890(10) _cell_angle_gamma 84.540(2) _cell_volume 2554.82(13) _cell_formula_units_Z 2 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.855 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1358 _exptl_absorpt_coefficient_mu 3.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_absorpt_correction_T_min 0.6555 _exptl_absorpt_correction_T_max 0.7456 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 83358 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.55 _refine_special_details ; The data were corrected for the presence of disordered solvent using the program SQUEEZE. ; _reflns_number_total 11723 _reflns_number_gt 10844 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0283P)^2^+0.6176P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11723 _refine_ls_number_parameters 721 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0213 _refine_ls_R_factor_gt 0.0184 _refine_ls_wR_factor_ref 0.0466 _refine_ls_wR_factor_gt 0.0457 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group U1 U -0.315649(6) -0.052561(6) 0.751824(3) 0.02147(3) Uani 1 1 d . . . F1 F 0.02952(12) -0.23702(12) 0.85510(7) 0.0419(3) Uani 1 1 d . . . F2 F 0.17302(12) -0.40478(14) 0.80199(9) 0.0563(4) Uani 1 1 d . . . F3 F 0.08314(15) -0.53801(13) 0.72889(10) 0.0666(5) Uani 1 1 d . . . F4 F -0.15794(16) -0.50458(15) 0.71183(10) 0.0662(5) Uani 1 1 d . . . F5 F -0.30140(13) -0.33146(14) 0.76205(8) 0.0507(4) Uani 1 1 d . . . F6 F -0.15031(15) 0.00082(14) 0.88596(8) 0.0532(4) Uani 1 1 d . . . F7 F -0.1591(2) 0.0002(2) 1.01797(10) 0.0883(7) Uani 1 1 d . . . F8 F -0.2298(2) -0.1893(2) 1.11065(8) 0.1088(9) Uani 1 1 d . . . F9 F -0.29295(18) -0.3805(2) 1.06694(9) 0.0957(8) Uani 1 1 d . . . F10 F -0.29049(14) -0.37727(14) 0.93432(8) 0.0603(4) Uani 1 1 d . . . F11 F -0.11834(11) -0.14349(11) 0.66835(6) 0.0346(3) Uani 1 1 d . . . F12 F 0.07016(11) -0.14825(13) 0.56419(7) 0.0434(3) Uani 1 1 d . . . F13 F 0.02267(12) -0.12618(14) 0.43418(7) 0.0472(3) Uani 1 1 d . . . F14 F -0.21404(13) -0.09704(15) 0.41184(6) 0.0512(4) Uani 1 1 d . . . F15 F -0.40005(11) -0.08710(13) 0.51401(7) 0.0427(3) Uani 1 1 d . . . F16 F -0.33782(11) -0.34853(11) 0.62390(7) 0.0388(3) Uani 1 1 d . . . F17 F -0.53521(14) -0.46251(12) 0.62087(8) 0.0485(3) Uani 1 1 d . . . F18 F -0.76540(13) -0.36088(14) 0.64887(8) 0.0524(4) Uani 1 1 d . . . F19 F -0.79438(11) -0.14380(14) 0.68010(8) 0.0491(4) Uani 1 1 d . . . F20 F -0.59704(11) -0.02444(11) 0.67740(7) 0.0390(3) Uani 1 1 d . . . F21 F -0.28554(11) 0.12251(11) 0.62856(6) 0.0326(3) Uani 1 1 d . . . F22 F -0.37561(14) 0.20103(14) 0.51178(6) 0.0496(4) Uani 1 1 d . . . F23 F -0.60303(14) 0.31662(14) 0.51451(7) 0.0521(4) Uani 1 1 d . . . F24 F -0.74005(12) 0.34261(13) 0.63515(7) 0.0458(3) Uani 1 1 d . . . F25 F -0.65436(11) 0.25896(12) 0.75185(6) 0.0381(3) Uani 1 1 d . . . F26 F -0.44293(15) 0.39354(12) 0.74246(7) 0.0475(3) Uani 1 1 d . . . F27 F -0.45764(18) 0.49096(12) 0.85184(8) 0.0627(5) Uani 1 1 d . . . F28 F -0.44145(17) 0.36066(14) 0.97552(8) 0.0602(4) Uani 1 1 d . . . F29 F -0.41174(15) 0.12317(13) 0.98674(7) 0.0525(4) Uani 1 1 d . . . F30 F -0.39832(12) 0.02319(10) 0.87624(6) 0.0342(3) Uani 1 1 d . . . O1 O -0.13062(13) 0.06352(12) 0.73580(7) 0.0311(3) Uani 1 1 d . . . O2 O -0.51428(13) -0.12348(13) 0.81256(8) 0.0324(3) Uani 1 1 d . . . N1 N -0.21708(16) -0.18701(15) 0.83527(8) 0.0298(4) Uani 1 1 d . . . N2 N -0.35732(15) -0.12082(15) 0.65210(8) 0.0274(3) Uani 1 1 d . . . N3 N -0.41622(15) 0.14119(14) 0.75261(8) 0.0256(3) Uani 1 1 d . . . C1 C -0.14218(19) -0.27948(17) 0.81123(10) 0.0284(4) Uani 1 1 d . . . C2 C -0.01933(19) -0.30183(19) 0.81966(11) 0.0326(4) Uani 1 1 d . . . C3 C 0.0555(2) -0.3876(2) 0.79259(13) 0.0391(5) Uani 1 1 d . . . C4 C 0.0100(2) -0.4554(2) 0.75549(14) 0.0448(6) Uani 1 1 d . . . C5 C -0.1113(2) -0.4372(2) 0.74604(13) 0.0429(6) Uani 1 1 d . . . C6 C -0.1842(2) -0.3503(2) 0.77354(12) 0.0353(5) Uani 1 1 d . . . C7 C -0.22027(19) -0.1877(2) 0.90493(10) 0.0355(5) Uani 1 1 d . . . C8 C -0.1880(2) -0.0934(2) 0.92941(12) 0.0439(6) Uani 1 1 d . . . C9 C -0.1920(3) -0.0929(3) 0.99765(14) 0.0607(8) Uani 1 1 d . . . C10 C -0.2274(3) -0.1891(4) 1.04392(13) 0.0700(10) Uani 1 1 d . . . C11 C -0.2589(3) -0.2842(3) 1.02262(14) 0.0663(10) Uani 1 1 d . . . C12 C -0.2567(2) -0.2834(3) 0.95391(13) 0.0486(7) Uani 1 1 d . . . C13 C -0.26553(18) -0.12169(17) 0.59588(10) 0.0258(4) Uani 1 1 d . . . C14 C -0.14251(18) -0.13332(18) 0.60360(10) 0.0278(4) Uani 1 1 d . . . C15 C -0.04558(18) -0.13566(19) 0.55156(11) 0.0314(4) Uani 1 1 d . . . C16 C -0.06960(19) -0.1251(2) 0.48650(11) 0.0333(5) Uani 1 1 d . . . C17 C -0.1900(2) -0.1103(2) 0.47544(10) 0.0341(5) Uani 1 1 d . . . C18 C -0.28481(18) -0.10711(19) 0.52860(10) 0.0307(4) Uani 1 1 d . . . C19 C -0.45968(18) -0.18206(18) 0.65051(9) 0.0257(4) Uani 1 1 d . . . C20 C -0.44956(18) -0.29508(18) 0.63713(10) 0.0292(4) Uani 1 1 d . . . C21 C -0.5505(2) -0.35509(19) 0.63600(11) 0.0337(5) Uani 1 1 d . . . C22 C -0.6670(2) -0.3036(2) 0.65019(11) 0.0362(5) Uani 1 1 d . . . C23 C -0.68089(18) -0.1938(2) 0.66515(11) 0.0339(5) Uani 1 1 d . . . C24 C -0.57909(19) -0.13416(18) 0.66470(10) 0.0295(4) Uani 1 1 d . . . C25 C -0.46532(18) 0.19098(17) 0.69396(10) 0.0254(4) Uani 1 1 d . . . C26 C -0.40002(18) 0.17787(17) 0.63074(10) 0.0273(4) Uani 1 1 d . . . C27 C -0.4443(2) 0.2174(2) 0.57090(10) 0.0341(5) Uani 1 1 d . . . C28 C -0.5580(2) 0.2747(2) 0.57225(11) 0.0352(5) Uani 1 1 d . . . C29 C -0.62756(19) 0.28886(19) 0.63363(11) 0.0321(4) Uani 1 1 d . . . C30 C -0.58252(18) 0.24672(18) 0.69300(10) 0.0281(4) Uani 1 1 d . . . C31 C -0.42734(17) 0.20295(17) 0.80539(10) 0.0259(4) Uani 1 1 d . . . C32 C -0.4389(2) 0.32377(19) 0.80201(11) 0.0327(4) Uani 1 1 d . . . C33 C -0.4441(2) 0.37510(19) 0.85819(12) 0.0391(5) Uani 1 1 d . . . C34 C -0.4353(2) 0.3095(2) 0.92079(12) 0.0400(5) Uani 1 1 d . . . C35 C -0.4210(2) 0.1913(2) 0.92659(11) 0.0362(5) Uani 1 1 d . . . C36 C -0.41681(18) 0.14092(17) 0.86995(10) 0.0279(4) Uani 1 1 d . . . C37 C -0.00520(19) 0.0111(2) 0.73353(12) 0.0355(5) Uani 1 1 d . . . H37A H 0.0287 -0.0039 0.6874 0.043 Uiso 1 1 calc R . . H37B H -0.0031 -0.0632 0.7656 0.043 Uiso 1 1 calc R . . C38 C 0.0675(2) 0.0983(2) 0.75336(14) 0.0478(6) Uani 1 1 d . . . H38A H 0.1554 0.0903 0.7338 0.057 Uiso 1 1 calc R . . H38B H 0.0596 0.0905 0.8032 0.057 Uiso 1 1 calc R . . C39 C 0.0065(2) 0.2120(2) 0.72266(18) 0.0598(8) Uani 1 1 d . . . H39A H 0.0210 0.2763 0.7452 0.072 Uiso 1 1 calc R . . H39B H 0.0370 0.2317 0.6735 0.072 Uiso 1 1 calc R . . C40 C -0.1276(2) 0.1877(2) 0.73557(15) 0.0455(6) Uani 1 1 d . . . H40A H -0.1678 0.2078 0.7797 0.055 Uiso 1 1 calc R . . H40B H -0.1705 0.2336 0.6995 0.055 Uiso 1 1 calc R . . C41 C -0.6253(2) -0.0511(2) 0.83459(13) 0.0419(5) Uani 1 1 d . . . H41A H -0.6386 0.0165 0.7990 0.050 Uiso 1 1 calc R . . H41B H -0.6178 -0.0228 0.8766 0.050 Uiso 1 1 calc R . . C42 C -0.7283(2) -0.1299(2) 0.84683(13) 0.0434(6) Uani 1 1 d . . . H42A H -0.7565 -0.1359 0.8040 0.052 Uiso 1 1 calc R . . H42B H -0.7987 -0.1032 0.8786 0.052 Uiso 1 1 calc R . . C43 C -0.6684(2) -0.2444(2) 0.87765(13) 0.0471(6) Uani 1 1 d . . . H43A H -0.6666 -0.2473 0.9264 0.056 Uiso 1 1 calc R . . H43B H -0.7122 -0.3109 0.8720 0.056 Uiso 1 1 calc R . . C44 C -0.5405(2) -0.2453(2) 0.83803(13) 0.0418(5) Uani 1 1 d . . . H44A H -0.4806 -0.2834 0.8675 0.050 Uiso 1 1 calc R . . H44B H -0.5357 -0.2881 0.7999 0.050 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 U1 0.02184(4) 0.02241(4) 0.02023(4) -0.00466(3) -0.00277(2) -0.00077(3) F1 0.0330(6) 0.0493(8) 0.0463(8) -0.0151(6) -0.0068(6) -0.0027(6) F2 0.0305(7) 0.0611(10) 0.0774(11) -0.0209(8) -0.0049(7) 0.0081(6) F3 0.0554(9) 0.0389(8) 0.1033(14) -0.0318(9) 0.0129(9) 0.0007(7) F4 0.0626(10) 0.0574(10) 0.0897(13) -0.0412(10) -0.0086(9) -0.0106(8) F5 0.0386(7) 0.0650(10) 0.0541(9) -0.0186(8) -0.0162(6) 0.0003(7) F6 0.0650(10) 0.0548(9) 0.0439(8) -0.0190(7) -0.0086(7) -0.0046(8) F7 0.0939(14) 0.1270(18) 0.0595(11) -0.0594(12) -0.0276(10) 0.0279(13) F8 0.1080(16) 0.181(2) 0.0222(8) -0.0189(11) -0.0087(9) 0.0669(16) F9 0.0721(12) 0.1245(18) 0.0485(10) 0.0441(11) 0.0213(9) 0.0364(12) F10 0.0501(9) 0.0531(10) 0.0607(10) 0.0186(8) 0.0061(7) 0.0011(7) F11 0.0304(6) 0.0496(8) 0.0264(6) -0.0101(5) -0.0061(5) -0.0062(5) F12 0.0242(6) 0.0635(9) 0.0423(7) -0.0088(7) -0.0036(5) -0.0051(6) F13 0.0373(7) 0.0701(10) 0.0311(7) -0.0111(7) 0.0095(5) -0.0097(7) F14 0.0469(8) 0.0841(11) 0.0213(6) -0.0025(7) -0.0049(6) -0.0114(7) F15 0.0313(6) 0.0605(9) 0.0348(7) -0.0017(6) -0.0096(5) -0.0005(6) F16 0.0362(7) 0.0360(7) 0.0448(7) -0.0143(6) -0.0019(6) 0.0018(5) F17 0.0612(9) 0.0339(7) 0.0551(9) -0.0157(6) -0.0078(7) -0.0142(6) F18 0.0426(8) 0.0664(10) 0.0541(9) -0.0137(8) -0.0065(6) -0.0285(7) F19 0.0245(6) 0.0691(10) 0.0570(9) -0.0205(8) -0.0061(6) -0.0006(6) F20 0.0360(7) 0.0367(7) 0.0471(8) -0.0167(6) -0.0070(6) 0.0034(5) F21 0.0306(6) 0.0360(7) 0.0291(6) -0.0068(5) -0.0010(5) 0.0040(5) F22 0.0570(9) 0.0670(10) 0.0215(6) -0.0101(6) -0.0013(6) 0.0098(7) F23 0.0649(9) 0.0616(10) 0.0306(7) -0.0039(7) -0.0230(7) 0.0131(8) F24 0.0362(7) 0.0542(9) 0.0461(8) -0.0064(7) -0.0151(6) 0.0137(6) F25 0.0327(6) 0.0492(8) 0.0286(6) -0.0063(6) 0.0001(5) 0.0063(6) F26 0.0748(10) 0.0297(7) 0.0382(7) 0.0015(6) -0.0144(7) -0.0076(7) F27 0.1056(14) 0.0284(8) 0.0602(10) -0.0160(7) -0.0239(9) 0.0008(8) F28 0.0927(12) 0.0518(9) 0.0465(9) -0.0300(7) -0.0254(8) 0.0105(8) F29 0.0839(11) 0.0488(9) 0.0273(7) -0.0075(6) -0.0209(7) 0.0065(8) F30 0.0505(7) 0.0257(6) 0.0272(6) -0.0031(5) -0.0126(5) 0.0025(5) O1 0.0264(7) 0.0281(8) 0.0383(8) -0.0044(6) -0.0049(6) -0.0022(6) O2 0.0297(7) 0.0305(8) 0.0363(8) -0.0064(6) -0.0012(6) -0.0041(6) N1 0.0327(9) 0.0303(9) 0.0250(8) -0.0030(7) -0.0066(7) 0.0046(7) N2 0.0245(8) 0.0324(9) 0.0263(8) -0.0093(7) -0.0007(6) -0.0057(7) N3 0.0289(8) 0.0258(8) 0.0217(8) -0.0042(7) -0.0040(6) 0.0009(7) C1 0.0324(10) 0.0241(10) 0.0245(10) 0.0023(8) -0.0014(8) 0.0010(8) C2 0.0321(10) 0.0311(11) 0.0323(11) -0.0014(9) -0.0019(8) -0.0040(8) C3 0.0277(10) 0.0359(12) 0.0495(14) -0.0040(10) 0.0008(9) 0.0003(9) C4 0.0425(13) 0.0282(12) 0.0588(16) -0.0103(11) 0.0080(11) -0.0009(10) C5 0.0507(14) 0.0301(12) 0.0490(14) -0.0116(10) -0.0022(11) -0.0094(10) C6 0.0339(11) 0.0336(12) 0.0373(12) -0.0027(9) -0.0053(9) -0.0029(9) C7 0.0313(10) 0.0455(13) 0.0241(10) -0.0009(9) -0.0026(8) 0.0123(9) C8 0.0403(12) 0.0613(16) 0.0291(11) -0.0125(11) -0.0069(10) 0.0143(11) C9 0.0570(16) 0.092(2) 0.0352(14) -0.0278(15) -0.0130(12) 0.0274(16) C10 0.0623(18) 0.112(3) 0.0247(13) -0.0116(16) -0.0036(12) 0.0415(19) C11 0.0483(15) 0.093(2) 0.0329(14) 0.0194(15) 0.0103(12) 0.0313(16) C12 0.0346(12) 0.0598(17) 0.0384(13) 0.0079(12) 0.0042(10) 0.0127(12) C13 0.0284(9) 0.0238(10) 0.0257(10) -0.0071(8) -0.0008(8) -0.0049(8) C14 0.0297(10) 0.0321(11) 0.0229(9) -0.0067(8) -0.0043(8) -0.0052(8) C15 0.0252(9) 0.0343(11) 0.0350(11) -0.0068(9) -0.0027(8) -0.0051(8) C16 0.0323(10) 0.0384(12) 0.0271(10) -0.0067(9) 0.0044(8) -0.0061(9) C17 0.0385(11) 0.0419(13) 0.0217(10) -0.0036(9) -0.0041(8) -0.0070(9) C18 0.0280(10) 0.0346(11) 0.0289(10) -0.0024(9) -0.0053(8) -0.0038(8) C19 0.0284(9) 0.0299(10) 0.0198(9) -0.0050(8) -0.0038(7) -0.0054(8) C20 0.0307(10) 0.0322(11) 0.0244(10) -0.0061(8) -0.0015(8) -0.0029(8) C21 0.0454(12) 0.0289(11) 0.0281(10) -0.0059(9) -0.0038(9) -0.0104(9) C22 0.0350(11) 0.0465(13) 0.0293(11) -0.0053(10) -0.0044(9) -0.0177(10) C23 0.0256(10) 0.0477(13) 0.0292(11) -0.0082(9) -0.0044(8) -0.0032(9) C24 0.0310(10) 0.0321(11) 0.0265(10) -0.0078(8) -0.0040(8) -0.0029(8) C25 0.0294(9) 0.0225(9) 0.0239(9) -0.0023(7) -0.0042(7) -0.0032(7) C26 0.0286(10) 0.0249(10) 0.0270(10) -0.0032(8) -0.0031(8) 0.0008(8) C27 0.0423(12) 0.0371(12) 0.0212(10) -0.0055(9) -0.0005(8) -0.0003(9) C28 0.0446(12) 0.0358(12) 0.0262(10) -0.0022(9) -0.0142(9) 0.0019(9) C29 0.0309(10) 0.0306(11) 0.0353(11) -0.0057(9) -0.0091(9) 0.0029(8) C30 0.0291(10) 0.0285(10) 0.0250(10) -0.0048(8) -0.0011(8) 0.0011(8) C31 0.0251(9) 0.0282(10) 0.0244(9) -0.0064(8) -0.0025(7) -0.0001(8) C32 0.0402(11) 0.0268(11) 0.0302(11) -0.0014(9) -0.0071(9) -0.0027(9) C33 0.0498(13) 0.0264(11) 0.0448(13) -0.0125(10) -0.0122(11) 0.0007(10) C34 0.0477(13) 0.0423(13) 0.0361(12) -0.0200(10) -0.0133(10) 0.0039(10) C35 0.0432(12) 0.0406(13) 0.0265(10) -0.0070(9) -0.0118(9) 0.0025(10) C36 0.0312(10) 0.0250(10) 0.0284(10) -0.0066(8) -0.0064(8) 0.0009(8) C37 0.0269(10) 0.0361(12) 0.0433(13) -0.0053(10) -0.0063(9) -0.0025(9) C38 0.0375(12) 0.0525(16) 0.0583(16) -0.0151(13) -0.0109(11) -0.0104(11) C39 0.0427(14) 0.0437(16) 0.095(2) -0.0164(15) -0.0033(14) -0.0158(12) C40 0.0386(12) 0.0276(12) 0.0726(18) -0.0130(12) -0.0067(12) -0.0079(9) C41 0.0291(11) 0.0489(14) 0.0470(14) -0.0160(11) 0.0029(9) -0.0006(10) C42 0.0307(11) 0.0608(16) 0.0400(13) -0.0163(12) 0.0014(9) -0.0066(11) C43 0.0461(14) 0.0591(17) 0.0359(13) -0.0021(12) -0.0036(10) -0.0201(12) C44 0.0388(12) 0.0362(13) 0.0471(14) 0.0024(10) -0.0033(10) -0.0111(10) 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 U1 N1 2.4252(17) . ? U1 N3 2.4367(16) . ? U1 N2 2.4401(16) . ? U1 O2 2.4700(14) . ? U1 O1 2.5101(14) . ? U1 F11 2.7843(12) . ? U1 F30 2.8131(12) . ? U1 F21 2.9279(12) . ? F1 C2 1.343(3) . ? F2 C3 1.338(3) . ? F3 C4 1.335(3) . ? F4 C5 1.334(3) . ? F5 C6 1.348(3) . ? F6 C8 1.335(3) . ? F7 C9 1.339(4) . ? F8 C10 1.352(3) . ? F9 C11 1.350(4) . ? F10 C12 1.343(4) . ? F11 C14 1.370(2) . ? F12 C15 1.339(2) . ? F13 C16 1.345(2) . ? F14 C17 1.343(2) . ? F15 C18 1.348(2) . ? F16 C20 1.341(2) . ? F17 C21 1.341(2) . ? F18 C22 1.340(2) . ? F19 C23 1.346(2) . ? F20 C24 1.349(2) . ? F21 C26 1.366(2) . ? F22 C27 1.344(2) . ? F23 C28 1.346(2) . ? F24 C29 1.340(2) . ? F25 C30 1.343(2) . ? F26 C32 1.337(2) . ? F27 C33 1.339(3) . ? F28 C34 1.347(2) . ? F29 C35 1.347(3) . ? F30 C36 1.363(2) . ? O1 C40 1.461(3) . ? O1 C37 1.461(2) . ? O2 C44 1.468(3) . ? O2 C41 1.479(3) . ? N1 C7 1.410(3) . ? N1 C1 1.411(3) . ? N2 C13 1.395(2) . ? N2 C19 1.407(2) . ? N3 C31 1.384(2) . ? N3 C25 1.402(2) . ? C1 C6 1.387(3) . ? C1 C2 1.394(3) . ? C2 C3 1.376(3) . ? C3 C4 1.372(4) . ? C4 C5 1.380(4) . ? C5 C6 1.379(3) . ? C7 C8 1.392(4) . ? C7 C12 1.398(3) . ? C8 C9 1.382(3) . ? C9 C10 1.371(5) . ? C10 C11 1.364(5) . ? C11 C12 1.392(4) . ? C13 C14 1.389(3) . ? C13 C18 1.398(3) . ? C14 C15 1.375(3) . ? C15 C16 1.375(3) . ? C16 C17 1.379(3) . ? C17 C18 1.376(3) . ? C19 C24 1.391(3) . ? C19 C20 1.393(3) . ? C20 C21 1.382(3) . ? C21 C22 1.378(3) . ? C22 C23 1.367(3) . ? C23 C24 1.380(3) . ? C25 C26 1.391(3) . ? C25 C30 1.398(3) . ? C26 C27 1.375(3) . ? C27 C28 1.368(3) . ? C28 C29 1.380(3) . ? C29 C30 1.375(3) . ? C31 C36 1.397(3) . ? C31 C32 1.402(3) . ? C32 C33 1.377(3) . ? C33 C34 1.375(3) . ? C34 C35 1.367(3) . ? C35 C36 1.380(3) . ? C37 C38 1.508(3) . ? C38 C39 1.514(4) . ? C39 C40 1.509(3) . ? C41 C42 1.496(3) . ? C42 C43 1.518(4) . ? C43 C44 1.505(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 U1 N3 132.45(6) . . ? N1 U1 N2 118.98(6) . . ? N3 U1 N2 107.84(6) . . ? N1 U1 O2 87.80(5) . . ? N3 U1 O2 85.61(5) . . ? N2 U1 O2 88.36(5) . . ? N1 U1 O1 86.07(5) . . ? N3 U1 O1 80.15(5) . . ? N2 U1 O1 116.51(5) . . ? O2 U1 O1 154.12(5) . . ? N1 U1 F11 79.56(5) . . ? N3 U1 F11 133.68(5) . . ? N2 U1 F11 61.94(4) . . ? O2 U1 F11 134.85(4) . . ? O1 U1 F11 68.38(4) . . ? N1 U1 F30 74.08(5) . . ? N3 U1 F30 60.59(4) . . ? N2 U1 F30 150.55(5) . . ? O2 U1 F30 64.80(4) . . ? O1 U1 F30 89.35(4) . . ? F11 U1 F30 146.53(3) . . ? N1 U1 F21 147.27(5) . . ? N3 U1 F21 60.14(4) . . ? N2 U1 F21 66.46(5) . . ? O2 U1 F21 124.90(4) . . ? O1 U1 F21 65.05(4) . . ? F11 U1 F21 75.76(3) . . ? F30 U1 F21 118.20(3) . . ? C14 F11 U1 111.27(11) . . ? C26 F21 U1 102.06(10) . . ? C36 F30 U1 113.15(11) . . ? C40 O1 C37 108.39(16) . . ? C40 O1 U1 127.90(12) . . ? C37 O1 U1 123.31(12) . . ? C44 O2 C41 107.41(16) . . ? C44 O2 U1 126.05(13) . . ? C41 O2 U1 126.38(13) . . ? C7 N1 C1 113.36(16) . . ? C7 N1 U1 130.57(13) . . ? C1 N1 U1 116.07(12) . . ? C13 N2 C19 114.37(15) . . ? C13 N2 U1 119.80(12) . . ? C19 N2 U1 124.61(12) . . ? C31 N3 C25 119.39(16) . . ? C31 N3 U1 125.22(13) . . ? C25 N3 U1 115.39(12) . . ? C6 C1 C2 115.17(19) . . ? C6 C1 N1 121.81(19) . . ? C2 C1 N1 122.90(19) . . ? F1 C2 C3 117.95(19) . . ? F1 C2 C1 119.32(19) . . ? C3 C2 C1 122.7(2) . . ? F2 C3 C4 119.8(2) . . ? F2 C3 C2 120.1(2) . . ? C4 C3 C2 120.1(2) . . ? F3 C4 C3 119.9(2) . . ? F3 C4 C5 120.7(2) . . ? C3 C4 C5 119.4(2) . . ? F4 C5 C6 120.5(2) . . ? F4 C5 C4 120.2(2) . . ? C6 C5 C4 119.4(2) . . ? F5 C6 C5 118.5(2) . . ? F5 C6 C1 118.2(2) . . ? C5 C6 C1 123.3(2) . . ? C8 C7 C12 115.7(2) . . ? C8 C7 N1 122.4(2) . . ? C12 C7 N1 121.9(2) . . ? F6 C8 C9 117.6(3) . . ? F6 C8 C7 119.6(2) . . ? C9 C8 C7 122.7(3) . . ? F7 C9 C10 120.6(3) . . ? F7 C9 C8 119.9(3) . . ? C10 C9 C8 119.6(3) . . ? F8 C10 C11 120.3(3) . . ? F8 C10 C9 119.6(4) . . ? C11 C10 C9 120.1(3) . . ? F9 C11 C10 121.4(3) . . ? F9 C11 C12 118.5(4) . . ? C10 C11 C12 120.0(3) . . ? F10 C12 C11 118.9(3) . . ? F10 C12 C7 119.3(2) . . ? C11 C12 C7 121.8(3) . . ? C14 C13 N2 120.45(18) . . ? C14 C13 C18 113.96(17) . . ? N2 C13 C18 125.54(18) . . ? F11 C14 C15 118.79(17) . . ? F11 C14 C13 116.37(17) . . ? C15 C14 C13 124.84(18) . . ? F12 C15 C16 120.67(18) . . ? F12 C15 C14 120.44(19) . . ? C16 C15 C14 118.89(19) . . ? F13 C16 C15 120.69(19) . . ? F13 C16 C17 120.36(19) . . ? C15 C16 C17 118.92(19) . . ? F14 C17 C18 120.06(19) . . ? F14 C17 C16 119.24(19) . . ? C18 C17 C16 120.69(19) . . ? F15 C18 C17 117.70(18) . . ? F15 C18 C13 119.68(18) . . ? C17 C18 C13 122.62(19) . . ? C24 C19 C20 115.40(18) . . ? C24 C19 N2 121.59(18) . . ? C20 C19 N2 122.98(18) . . ? F16 C20 C21 117.90(19) . . ? F16 C20 C19 119.36(18) . . ? C21 C20 C19 122.73(19) . . ? F17 C21 C22 120.22(19) . . ? F17 C21 C20 120.2(2) . . ? C22 C21 C20 119.6(2) . . ? F18 C22 C23 120.5(2) . . ? F18 C22 C21 120.0(2) . . ? C23 C22 C21 119.45(19) . . ? F19 C23 C22 119.69(19) . . ? F19 C23 C24 120.1(2) . . ? C22 C23 C24 120.2(2) . . ? F20 C24 C23 118.22(18) . . ? F20 C24 C19 119.20(17) . . ? C23 C24 C19 122.6(2) . . ? C26 C25 C30 115.00(18) . . ? C26 C25 N3 119.73(18) . . ? C30 C25 N3 125.05(18) . . ? F21 C26 C27 118.65(17) . . ? F21 C26 C25 117.66(17) . . ? C27 C26 C25 123.69(19) . . ? F22 C27 C28 120.59(19) . . ? F22 C27 C26 120.1(2) . . ? C28 C27 C26 119.28(19) . . ? F23 C28 C27 120.8(2) . . ? F23 C28 C29 119.7(2) . . ? C27 C28 C29 119.52(19) . . ? F24 C29 C30 120.11(19) . . ? F24 C29 C28 119.62(19) . . ? C30 C29 C28 120.27(19) . . ? F25 C30 C29 118.57(18) . . ? F25 C30 C25 119.24(18) . . ? C29 C30 C25 122.19(18) . . ? N3 C31 C36 118.02(18) . . ? N3 C31 C32 127.94(18) . . ? C36 C31 C32 113.84(18) . . ? F26 C32 C33 117.65(19) . . ? F26 C32 C31 119.95(18) . . ? C33 C32 C31 122.4(2) . . ? F27 C33 C34 119.3(2) . . ? F27 C33 C32 119.5(2) . . ? C34 C33 C32 121.2(2) . . ? F28 C34 C35 120.5(2) . . ? F28 C34 C33 120.7(2) . . ? C35 C34 C33 118.8(2) . . ? F29 C35 C34 121.09(19) . . ? F29 C35 C36 119.5(2) . . ? C34 C35 C36 119.4(2) . . ? F30 C36 C35 118.61(18) . . ? F30 C36 C31 117.06(17) . . ? C35 C36 C31 124.32(19) . . ? O1 C37 C38 105.60(18) . . ? C37 C38 C39 101.5(2) . . ? C40 C39 C38 103.0(2) . . ? O1 C40 C39 105.76(19) . . ? O2 C41 C42 104.86(19) . . ? C41 C42 C43 101.9(2) . . ? C44 C43 C42 103.3(2) . . ? O2 C44 C43 106.6(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.902 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.065 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 1.000 205 51 ' ' 2 0.000 0.500 0.500 211 47 ' ' data_UP4056(3) _database_code_depnum_ccdc_archive 'CCDC 900235' #TrackingRef 'UF.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C88.50 H66 F18 N3 O2 P2 U' _chemical_formula_weight 1845.41 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' P P 0.1023 0.0942 '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' U U -9.6767 9.6646 '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 13.4814(8) _cell_length_b 16.1925(10) _cell_length_c 19.0979(11) _cell_angle_alpha 76.559(3) _cell_angle_beta 87.948(3) _cell_angle_gamma 84.674(3) _cell_volume 4036.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1836 _exptl_absorpt_coefficient_mu 2.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_absorpt_correction_T_min 0.5265 _exptl_absorpt_correction_T_max 0.7456 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 96002 _diffrn_reflns_av_R_equivalents 0.0788 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 27.83 _reflns_number_total 18420 _reflns_number_gt 13324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0910P)^2^+4.1392P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 18420 _refine_ls_number_parameters 999 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1670 _refine_ls_wR_factor_gt 0.1441 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.057 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group U1 U 0.289260(16) 0.318712(15) 0.770346(12) 0.03064(9) Uani 1 1 d . . . P1 P 0.15473(12) 0.11374(11) 0.78323(9) 0.0350(4) Uani 1 1 d . . . P2 P 0.38115(11) 0.53698(11) 0.77752(8) 0.0313(3) Uani 1 1 d . . . F1 F 0.6078(4) 0.0679(4) 0.5205(3) 0.0847(17) Uani 1 1 d . . . F2 F 0.6327(5) 0.0371(4) 0.6345(3) 0.106(2) Uani 1 1 d . . . F3 F 0.5307(5) -0.0286(3) 0.5880(3) 0.0900(18) Uani 1 1 d . . . F4 F 0.2267(5) 0.2528(4) 0.4638(3) 0.099(2) Uani 1 1 d . . . F5 F 0.1430(4) 0.2078(4) 0.5585(3) 0.0924(18) Uani 1 1 d . . . F6 F 0.2097(5) 0.1199(4) 0.4982(3) 0.095(2) Uani 1 1 d . . . F7 F 0.6688(5) 0.2341(5) 1.0414(4) 0.112(2) Uani 1 1 d . . . F8 F 0.5413(5) 0.2343(6) 1.1073(4) 0.139(3) Uani 1 1 d . . . F9 F 0.6320(5) 0.1197(4) 1.1049(4) 0.106(2) Uani 1 1 d . . . F10 F 0.6147(6) 0.0875(4) 0.8123(4) 0.119(3) Uani 1 1 d . . . F11 F 0.4911(4) 0.0214(5) 0.8317(5) 0.145(4) Uani 1 1 d . . . F12 F 0.6119(6) -0.0134(4) 0.8997(4) 0.131(3) Uani 1 1 d . . . F13 F -0.1636(6) 0.6387(4) 0.7672(4) 0.111(2) Uani 1 1 d . . . F14 F -0.1401(5) 0.6263(5) 0.6627(3) 0.132(3) Uani 1 1 d . . . F15 F -0.2591(4) 0.5735(4) 0.7224(5) 0.126(3) Uani 1 1 d . . . F16 F -0.1659(6) 0.2772(6) 0.9060(4) 0.171(5) Uani 1 1 d . . . F17 F -0.1281(9) 0.3597(6) 0.9626(4) 0.184(5) Uani 1 1 d . . . F18 F -0.0258(4) 0.2685(5) 0.9452(3) 0.116(3) Uani 1 1 d . . . O1 O 0.2171(3) 0.1881(3) 0.7756(2) 0.0401(10) Uani 1 1 d . . . O2 O 0.3536(3) 0.4508(3) 0.7718(2) 0.0348(9) Uani 1 1 d . . . N1 N 0.4237(4) 0.2802(3) 0.6959(3) 0.0319(11) Uani 1 1 d . . . N2 N 0.3070(4) 0.2759(4) 0.9000(3) 0.0381(12) Uani 1 1 d . . . N3 N 0.1418(3) 0.3962(3) 0.7151(3) 0.0327(11) Uani 1 1 d . . . C1 C 0.5170(4) 0.3108(4) 0.6987(3) 0.0322(13) Uani 1 1 d . . . C2 C 0.5537(5) 0.3212(4) 0.7633(3) 0.0377(14) Uani 1 1 d . . . H2 H 0.5179 0.3035 0.8059 0.050 Uiso 1 1 calc R . . C3 C 0.6411(5) 0.3571(5) 0.7651(4) 0.0478(17) Uani 1 1 d . . . H3 H 0.6634 0.3636 0.8088 0.064 Uiso 1 1 calc R . . C4 C 0.6970(5) 0.3837(5) 0.7036(4) 0.0526(19) Uani 1 1 d . . . H4 H 0.7553 0.4096 0.7052 0.070 Uiso 1 1 calc R . . C5 C 0.6642(5) 0.3710(5) 0.6393(4) 0.0481(17) Uani 1 1 d . . . H5 H 0.7032 0.3855 0.5979 0.064 Uiso 1 1 calc R . . C6 C 0.5745(5) 0.3373(4) 0.6356(3) 0.0365(14) Uani 1 1 d . . . H6 H 0.5521 0.3321 0.5915 0.049 Uiso 1 1 calc R . . C7 C 0.4149(5) 0.2281(4) 0.6478(3) 0.0319(13) Uani 1 1 d . . . C8 C 0.4904(5) 0.1659(4) 0.6393(3) 0.0396(15) Uani 1 1 d . . . H8 H 0.5494 0.1605 0.6644 0.053 Uiso 1 1 calc R . . C9 C 0.4788(6) 0.1123(4) 0.5943(4) 0.0473(17) Uani 1 1 d . . . C10 C 0.3930(6) 0.1169(4) 0.5561(4) 0.0499(18) Uani 1 1 d . . . H10 H 0.3861 0.0806 0.5256 0.066 Uiso 1 1 calc R . . C11 C 0.3183(6) 0.1770(4) 0.5646(3) 0.0437(16) Uani 1 1 d . . . C12 C 0.3277(5) 0.2327(4) 0.6091(3) 0.0350(14) Uani 1 1 d . . . H12 H 0.2756 0.2733 0.6132 0.046 Uiso 1 1 calc R . . C13 C 0.5631(8) 0.0478(6) 0.5853(5) 0.069(3) Uani 1 1 d . . . C14 C 0.2252(7) 0.1884(5) 0.5218(5) 0.063(2) Uani 1 1 d . . . C15 C 0.2476(5) 0.3164(5) 0.9473(3) 0.0382(15) Uani 1 1 d . . . C16 C 0.2243(5) 0.2744(5) 1.0182(4) 0.0463(17) Uani 1 1 d . . . H16 H 0.2504 0.2186 1.0364 0.062 Uiso 1 1 calc R . . C17 C 0.1623(5) 0.3161(6) 1.0614(4) 0.0529(19) Uani 1 1 d . . . H17 H 0.1485 0.2884 1.1086 0.070 Uiso 1 1 calc R . . C18 C 0.1209(5) 0.3986(6) 1.0347(4) 0.059(2) Uani 1 1 d . . . H18 H 0.0799 0.4263 1.0639 0.079 Uiso 1 1 calc R . . C19 C 0.1410(5) 0.4391(5) 0.9646(4) 0.0540(19) Uani 1 1 d . . . H19 H 0.1120 0.4938 0.9458 0.072 Uiso 1 1 calc R . . C20 C 0.2044(5) 0.3983(5) 0.9220(4) 0.0441(16) Uani 1 1 d . . . H20 H 0.2182 0.4270 0.8751 0.059 Uiso 1 1 calc R . . C21 C 0.3892(5) 0.2221(4) 0.9268(3) 0.0380(14) Uani 1 1 d . . . C22 C 0.4433(5) 0.2286(5) 0.9858(3) 0.0412(15) Uani 1 1 d . . . H22 H 0.4200 0.2676 1.0127 0.055 Uiso 1 1 calc R . . C23 C 0.5313(5) 0.1782(5) 1.0052(4) 0.0506(18) Uani 1 1 d . . . C24 C 0.5693(5) 0.1194(5) 0.9670(4) 0.0520(18) Uani 1 1 d . . . H24 H 0.6291 0.0866 0.9796 0.069 Uiso 1 1 calc R . . C25 C 0.5145(5) 0.1111(5) 0.9089(4) 0.0461(17) Uani 1 1 d . . . C26 C 0.4263(5) 0.1595(5) 0.8896(4) 0.0434(16) Uani 1 1 d . . . H26 H 0.3905 0.1509 0.8516 0.058 Uiso 1 1 calc R . . C27 C 0.5891(7) 0.1903(7) 1.0658(5) 0.075(3) Uani 1 1 d . . . C28 C 0.5566(6) 0.0515(6) 0.8643(5) 0.060(2) Uani 1 1 d . . . C29 C 0.1572(4) 0.4245(4) 0.6403(3) 0.0324(13) Uani 1 1 d . . . C30 C 0.0889(5) 0.4151(4) 0.5891(3) 0.0375(14) Uani 1 1 d . . . H30 H 0.0270 0.3962 0.6045 0.050 Uiso 1 1 calc R . . C31 C 0.1123(5) 0.4334(5) 0.5165(4) 0.0459(17) Uani 1 1 d . . . H31 H 0.0663 0.4266 0.4836 0.061 Uiso 1 1 calc R . . C32 C 0.2045(5) 0.4620(5) 0.4924(4) 0.0486(17) Uani 1 1 d . . . H32 H 0.2208 0.4735 0.4436 0.065 Uiso 1 1 calc R . . C33 C 0.2701(5) 0.4729(5) 0.5410(3) 0.0436(16) Uani 1 1 d . . . H33 H 0.3316 0.4920 0.5249 0.058 Uiso 1 1 calc R . . C34 C 0.2476(5) 0.4562(4) 0.6141(3) 0.0366(14) Uani 1 1 d . . . H34 H 0.2931 0.4663 0.6460 0.049 Uiso 1 1 calc R . . C35 C 0.0503(4) 0.4142(4) 0.7455(3) 0.0312(13) Uani 1 1 d . . . C36 C -0.0139(4) 0.4866(4) 0.7177(3) 0.0342(14) Uani 1 1 d . . . H36 H 0.0019 0.5228 0.6741 0.046 Uiso 1 1 calc R . . C37 C -0.1012(4) 0.5052(4) 0.7544(3) 0.0359(14) Uani 1 1 d . . . C38 C -0.1279(5) 0.4524(5) 0.8189(3) 0.0398(15) Uani 1 1 d . . . H38 H -0.1857 0.4654 0.8437 0.053 Uiso 1 1 calc R . . C39 C -0.0663(5) 0.3803(5) 0.8454(3) 0.0389(15) Uani 1 1 d . . . C40 C 0.0208(4) 0.3606(4) 0.8098(3) 0.0367(14) Uani 1 1 d . . . H40 H 0.0603 0.3108 0.8289 0.049 Uiso 1 1 calc R . . C41 C -0.1646(5) 0.5851(5) 0.7256(4) 0.0472(17) Uani 1 1 d . . . C42 C -0.0955(6) 0.3184(6) 0.9126(4) 0.062(2) Uani 1 1 d . . . C43 C 0.2027(5) 0.0410(5) 0.7283(4) 0.0480(18) Uani 1 1 d . . . C44 C 0.2987(6) 0.0076(6) 0.7369(5) 0.068(2) Uani 1 1 d . . . H44 H 0.3403 0.0257 0.7671 0.091 Uiso 1 1 calc R . . C45 C 0.3344(8) -0.0537(7) 0.7004(6) 0.086(3) Uani 1 1 d . . . H45 H 0.3999 -0.0775 0.7064 0.114 Uiso 1 1 calc R . . C46 C 0.2724(10) -0.0797(7) 0.6550(6) 0.090(3) Uani 1 1 d . . . H46 H 0.2961 -0.1222 0.6317 0.120 Uiso 1 1 calc R . . C47 C 0.1769(10) -0.0437(7) 0.6441(6) 0.096(4) Uani 1 1 d . . . H47 H 0.1357 -0.0617 0.6136 0.127 Uiso 1 1 calc R . . C48 C 0.1395(6) 0.0236(6) 0.6809(4) 0.057(2) Uani 1 1 d . . . H48 H 0.0766 0.0523 0.6723 0.076 Uiso 1 1 calc R . . C49 C 0.1541(4) 0.0528(5) 0.8749(4) 0.0410(16) Uani 1 1 d . . . C50 C 0.1392(6) -0.0336(5) 0.8903(5) 0.060(2) Uani 1 1 d . . . H50 H 0.1332 -0.0607 0.8529 0.079 Uiso 1 1 calc R . . C51 C 0.1335(7) -0.0787(6) 0.9601(6) 0.077(3) Uani 1 1 d . . . H51 H 0.1216 -0.1360 0.9703 0.102 Uiso 1 1 calc R . . C52 C 0.1452(7) -0.0391(7) 1.0147(5) 0.074(3) Uani 1 1 d . . . H52 H 0.1433 -0.0702 1.0622 0.098 Uiso 1 1 calc R . . C53 C 0.1600(7) 0.0468(7) 1.0002(5) 0.075(3) Uani 1 1 d . . . H53 H 0.1667 0.0731 1.0380 0.100 Uiso 1 1 calc R . . C54 C 0.1649(6) 0.0938(6) 0.9294(4) 0.057(2) Uani 1 1 d . . . H54 H 0.1752 0.1514 0.9192 0.076 Uiso 1 1 calc R . . C55 C 0.0281(5) 0.1463(4) 0.7584(4) 0.0403(15) Uani 1 1 d . . . C56 C -0.0493(6) 0.1031(7) 0.7932(5) 0.076(3) Uani 1 1 d . . . H56 H -0.0367 0.0578 0.8328 0.101 Uiso 1 1 calc R . . C57 C -0.1446(6) 0.1263(8) 0.7699(6) 0.084(3) Uani 1 1 d . . . H57 H -0.1961 0.0955 0.7930 0.112 Uiso 1 1 calc R . . C58 C -0.1655(6) 0.1936(6) 0.7137(6) 0.074(3) Uani 1 1 d . . . H58 H -0.2311 0.2106 0.7000 0.098 Uiso 1 1 calc R . . C59 C -0.0900(7) 0.2355(6) 0.6778(6) 0.088(4) Uani 1 1 d . . . H59 H -0.1037 0.2795 0.6375 0.118 Uiso 1 1 calc R . . C60 C 0.0066(6) 0.2140(6) 0.7002(5) 0.070(3) Uani 1 1 d . . . H60 H 0.0576 0.2448 0.6762 0.093 Uiso 1 1 calc R . . C61 C 0.4766(4) 0.5260(4) 0.8431(3) 0.0337(13) Uani 1 1 d . . . C62 C 0.5419(5) 0.5886(5) 0.8390(4) 0.0496(18) Uani 1 1 d . . . H62 H 0.5353 0.6384 0.8030 0.066 Uiso 1 1 calc R . . C63 C 0.6166(5) 0.5761(6) 0.8889(4) 0.058(2) Uani 1 1 d . . . H63 H 0.6594 0.6184 0.8872 0.077 Uiso 1 1 calc R . . C64 C 0.6285(6) 0.5020(6) 0.9409(4) 0.058(2) Uani 1 1 d . . . H64 H 0.6799 0.4935 0.9737 0.077 Uiso 1 1 calc R . . C65 C 0.5643(6) 0.4403(6) 0.9446(4) 0.059(2) Uani 1 1 d . . . H65 H 0.5724 0.3901 0.9801 0.078 Uiso 1 1 calc R . . C66 C 0.4882(5) 0.4514(5) 0.8964(3) 0.0448(16) Uani 1 1 d . . . H66 H 0.4448 0.4093 0.8995 0.060 Uiso 1 1 calc R . . C67 C 0.4275(5) 0.5960(4) 0.6934(3) 0.0349(14) Uani 1 1 d . . . C68 C 0.4921(6) 0.5542(5) 0.6532(5) 0.061(2) Uani 1 1 d . . . H68 H 0.5074 0.4957 0.6685 0.081 Uiso 1 1 calc R . . C69 C 0.5340(6) 0.5979(6) 0.5913(5) 0.068(2) Uani 1 1 d . . . H69 H 0.5803 0.5689 0.5664 0.090 Uiso 1 1 calc R . . C70 C 0.5104(6) 0.6813(6) 0.5652(4) 0.064(2) Uani 1 1 d . . . H70 H 0.5368 0.7095 0.5214 0.085 Uiso 1 1 calc R . . C71 C 0.4465(10) 0.7241(7) 0.6046(5) 0.102(4) Uani 1 1 d . . . H71 H 0.4303 0.7824 0.5883 0.135 Uiso 1 1 calc R . . C72 C 0.4056(9) 0.6801(6) 0.6696(5) 0.088(4) Uani 1 1 d . . . H72 H 0.3627 0.7095 0.6964 0.118 Uiso 1 1 calc R . . C73 C 0.2738(5) 0.5997(4) 0.8018(4) 0.0395(15) Uani 1 1 d . . . C74 C 0.2740(6) 0.6436(6) 0.8542(4) 0.060(2) Uani 1 1 d . . . H74 H 0.3320 0.6419 0.8795 0.080 Uiso 1 1 calc R . . C75 C 0.1894(6) 0.6907(6) 0.8704(5) 0.067(2) Uani 1 1 d . . . H75 H 0.1905 0.7200 0.9068 0.089 Uiso 1 1 calc R . . C76 C 0.1057(6) 0.6942(6) 0.8337(6) 0.068(3) Uani 1 1 d . . . H76 H 0.0493 0.7278 0.8432 0.091 Uiso 1 1 calc R . . C77 C 0.1034(7) 0.6485(8) 0.7825(8) 0.109(5) Uani 1 1 d . . . H77 H 0.0443 0.6488 0.7587 0.145 Uiso 1 1 calc R . . C78 C 0.1868(6) 0.6023(7) 0.7656(6) 0.092(4) Uani 1 1 d . . . H78 H 0.1849 0.5726 0.7296 0.122 Uiso 1 1 calc R . . C79 C 0.1294(5) 0.8494(4) 0.4865(4) 0.103(4) Uani 1 1 d G . . C80 C 0.2145(5) 0.7933(5) 0.4870(5) 0.116(4) Uani 1 1 d G . . H80 H 0.2718 0.8125 0.4624 0.154 Uiso 1 1 calc R . . C81 C 0.2137(6) 0.7084(5) 0.5244(5) 0.118(5) Uani 1 1 d G . . H81 H 0.2705 0.6710 0.5247 0.157 Uiso 1 1 calc R . . C82 C 0.1278(7) 0.6796(4) 0.5613(5) 0.110(4) Uani 1 1 d G . . H82 H 0.1273 0.6230 0.5862 0.146 Uiso 1 1 calc R . . C83 C 0.0427(6) 0.7356(6) 0.5608(6) 0.170(8) Uani 1 1 d G . . H83 H -0.0146 0.7164 0.5854 0.227 Uiso 1 1 calc R . . C84 C 0.0434(5) 0.8206(5) 0.5234(5) 0.133(5) Uani 1 1 d G . . H84 H -0.0133 0.8579 0.5231 0.177 Uiso 1 1 calc R . . C85 C 0.1302(9) 0.9431(4) 0.4452(6) 0.134(5) Uani 1 1 d G . . H85a H 0.1945 0.9524 0.4229 0.201 Uiso 1 1 calc R . . H85b H 0.1165 0.9796 0.4780 0.201 Uiso 1 1 calc R . . H85c H 0.0802 0.9558 0.4088 0.201 Uiso 1 1 calc R . . C86 C 0.7367(10) -0.1540(8) 0.7389(7) 0.085(6) Uiso 0.50 1 d PG . . C87 C 0.7629(12) -0.1204(11) 0.7959(8) 0.132(10) Uiso 0.50 1 d PG . . H87 H 0.7156 -0.1120 0.8308 0.176 Uiso 0.50 1 calc PR . . C88 C 0.8601(14) -0.0993(12) 0.8005(10) 0.182(16) Uiso 0.50 1 d PG . . H88 H 0.8776 -0.0769 0.8385 0.243 Uiso 0.50 1 calc PR . . C89 C 0.9310(11) -0.1119(11) 0.7481(11) 0.110(8) Uiso 0.50 1 d PG . . H89 H 0.9958 -0.0978 0.7512 0.146 Uiso 0.50 1 calc PR . . C90 C 0.9048(11) -0.1455(13) 0.6911(10) 0.176(15) Uiso 0.50 1 d PG . . H90 H 0.9521 -0.1539 0.6562 0.235 Uiso 0.50 1 calc PR . . C91 C 0.8076(12) -0.1666(12) 0.6865(8) 0.142(11) Uiso 0.50 1 d PG . . H91 H 0.7901 -0.1890 0.6485 0.189 Uiso 0.50 1 calc PR . . C92 C 0.6294(11) -0.1773(13) 0.7338(12) 0.132(10) Uiso 0.50 1 d PG . . H92a H 0.6238 -0.1994 0.6918 0.198 Uiso 0.50 1 calc PR . . H92b H 0.5839 -0.1273 0.7305 0.198 Uiso 0.50 1 calc PR . . H92c H 0.6135 -0.2196 0.7759 0.198 Uiso 0.50 1 calc 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 U1 0.02274(12) 0.04332(15) 0.02651(12) -0.01184(9) 0.00634(8) 0.00085(8) P1 0.0275(8) 0.0399(9) 0.0357(8) -0.0060(7) 0.0048(6) -0.0011(7) P2 0.0247(7) 0.0418(9) 0.0304(8) -0.0161(7) 0.0033(6) 0.0000(6) F1 0.094(4) 0.079(4) 0.083(4) -0.036(3) 0.029(3) 0.015(3) F2 0.119(5) 0.107(5) 0.100(4) -0.064(4) -0.036(4) 0.067(4) F3 0.127(5) 0.047(3) 0.097(4) -0.030(3) 0.019(4) 0.014(3) F4 0.135(6) 0.090(4) 0.066(3) 0.003(3) -0.046(4) -0.020(4) F5 0.062(3) 0.131(5) 0.100(4) -0.056(4) -0.029(3) -0.003(3) F6 0.116(5) 0.076(4) 0.109(5) -0.048(3) -0.049(4) -0.008(3) F7 0.094(5) 0.147(6) 0.108(5) -0.038(5) -0.024(4) -0.039(4) F8 0.095(5) 0.241(9) 0.106(5) -0.114(6) -0.056(4) 0.071(5) F9 0.104(5) 0.109(5) 0.098(5) -0.009(4) -0.059(4) 0.014(4) F10 0.134(6) 0.109(5) 0.126(6) -0.058(4) 0.081(5) -0.023(4) F11 0.054(3) 0.176(7) 0.260(10) -0.174(8) -0.013(5) 0.018(4) F12 0.162(7) 0.108(5) 0.114(5) -0.046(4) -0.020(5) 0.088(5) F13 0.153(6) 0.075(4) 0.111(5) -0.049(4) -0.040(4) 0.048(4) F14 0.130(5) 0.138(6) 0.070(4) 0.042(4) 0.048(4) 0.097(5) F15 0.039(3) 0.092(4) 0.235(9) -0.018(5) -0.030(4) 0.016(3) F16 0.125(6) 0.226(9) 0.120(6) 0.097(6) -0.050(5) -0.133(7) F17 0.303(13) 0.133(7) 0.084(5) 0.008(5) 0.116(7) 0.016(8) F18 0.067(4) 0.151(6) 0.084(4) 0.064(4) 0.015(3) -0.007(4) O1 0.041(3) 0.041(2) 0.036(2) -0.004(2) 0.003(2) -0.004(2) O2 0.030(2) 0.046(3) 0.031(2) -0.0161(19) 0.0016(17) 0.0012(19) N1 0.026(2) 0.041(3) 0.033(3) -0.018(2) 0.011(2) -0.005(2) N2 0.035(3) 0.049(3) 0.029(3) -0.011(2) 0.002(2) 0.005(2) N3 0.021(2) 0.042(3) 0.031(3) -0.003(2) 0.007(2) -0.002(2) C1 0.026(3) 0.036(3) 0.037(3) -0.015(3) 0.005(2) 0.000(2) C2 0.034(3) 0.047(4) 0.035(3) -0.015(3) 0.004(3) -0.003(3) C3 0.034(4) 0.062(5) 0.054(4) -0.026(4) -0.003(3) -0.005(3) C4 0.027(3) 0.077(5) 0.062(5) -0.030(4) 0.009(3) -0.016(3) C5 0.042(4) 0.045(4) 0.055(4) -0.010(3) 0.016(3) -0.003(3) C6 0.033(3) 0.039(4) 0.037(3) -0.008(3) 0.010(3) -0.002(3) C7 0.034(3) 0.036(3) 0.028(3) -0.012(3) 0.007(2) -0.006(3) C8 0.044(4) 0.043(4) 0.034(3) -0.016(3) 0.004(3) 0.001(3) C9 0.066(5) 0.044(4) 0.033(3) -0.015(3) 0.005(3) 0.006(3) C10 0.078(5) 0.037(4) 0.037(4) -0.016(3) -0.005(4) 0.002(4) C11 0.060(5) 0.040(4) 0.033(3) -0.010(3) -0.003(3) -0.010(3) C12 0.041(4) 0.036(3) 0.028(3) -0.008(3) 0.003(3) -0.004(3) C13 0.094(7) 0.059(5) 0.056(5) -0.030(4) 0.003(5) 0.017(5) C14 0.084(7) 0.057(5) 0.055(5) -0.023(4) -0.021(5) -0.010(5) C15 0.027(3) 0.060(4) 0.032(3) -0.018(3) 0.003(2) -0.004(3) C16 0.038(4) 0.070(5) 0.035(3) -0.021(3) 0.002(3) -0.004(3) C17 0.037(4) 0.086(6) 0.040(4) -0.025(4) 0.011(3) -0.004(4) C18 0.032(4) 0.099(7) 0.057(5) -0.042(5) 0.012(3) -0.004(4) C19 0.037(4) 0.065(5) 0.062(5) -0.025(4) 0.009(3) 0.007(3) C20 0.035(4) 0.057(4) 0.042(4) -0.018(3) 0.009(3) -0.007(3) C21 0.032(3) 0.047(4) 0.033(3) -0.005(3) 0.007(3) -0.005(3) C22 0.035(3) 0.054(4) 0.034(3) -0.011(3) 0.003(3) 0.002(3) C23 0.039(4) 0.068(5) 0.044(4) -0.013(4) 0.000(3) -0.001(4) C24 0.035(4) 0.059(5) 0.061(5) -0.014(4) -0.004(3) 0.003(3) C25 0.035(4) 0.051(4) 0.052(4) -0.011(3) 0.006(3) -0.004(3) C26 0.034(3) 0.055(4) 0.039(4) -0.006(3) 0.007(3) -0.003(3) C27 0.054(5) 0.105(8) 0.065(6) -0.028(6) -0.023(5) 0.020(5) C28 0.035(4) 0.064(5) 0.086(6) -0.028(5) 0.004(4) 0.004(4) C29 0.025(3) 0.037(3) 0.033(3) -0.007(3) 0.005(2) 0.002(2) C30 0.026(3) 0.048(4) 0.039(3) -0.012(3) 0.002(3) -0.005(3) C31 0.042(4) 0.061(5) 0.038(4) -0.018(3) 0.001(3) -0.008(3) C32 0.048(4) 0.068(5) 0.030(3) -0.014(3) 0.009(3) -0.006(4) C33 0.034(3) 0.062(5) 0.035(3) -0.012(3) 0.016(3) -0.009(3) C34 0.028(3) 0.047(4) 0.037(3) -0.014(3) 0.007(3) -0.007(3) C35 0.022(3) 0.048(4) 0.026(3) -0.014(3) 0.002(2) -0.007(3) C36 0.023(3) 0.052(4) 0.027(3) -0.012(3) 0.005(2) 0.000(3) C37 0.025(3) 0.051(4) 0.035(3) -0.018(3) 0.004(2) 0.000(3) C38 0.027(3) 0.065(4) 0.031(3) -0.018(3) 0.007(2) -0.005(3) C39 0.028(3) 0.059(4) 0.030(3) -0.008(3) 0.006(2) -0.012(3) C40 0.026(3) 0.046(4) 0.038(3) -0.007(3) 0.003(3) -0.007(3) C41 0.038(4) 0.057(4) 0.045(4) -0.015(3) 0.008(3) 0.009(3) C42 0.037(4) 0.090(6) 0.046(4) 0.008(4) 0.013(3) -0.005(4) C43 0.036(4) 0.044(4) 0.058(4) -0.007(3) 0.015(3) 0.005(3) C44 0.045(5) 0.087(7) 0.064(5) -0.009(5) 0.009(4) 0.016(4) C45 0.075(7) 0.081(7) 0.089(7) -0.011(6) 0.031(6) 0.029(6) C46 0.114(9) 0.071(7) 0.081(7) -0.025(6) 0.034(7) 0.017(6) C47 0.105(9) 0.094(8) 0.099(8) -0.053(7) 0.019(7) 0.010(7) C48 0.045(4) 0.078(6) 0.043(4) 0.000(4) -0.018(3) -0.002(4) C49 0.022(3) 0.053(4) 0.042(4) 0.000(3) 0.009(3) -0.001(3) C50 0.058(5) 0.056(5) 0.054(5) 0.005(4) 0.015(4) 0.000(4) C51 0.072(6) 0.063(6) 0.074(6) 0.018(5) 0.030(5) 0.009(5) C52 0.056(5) 0.095(7) 0.050(5) 0.017(5) 0.014(4) 0.006(5) C53 0.070(6) 0.107(8) 0.039(4) 0.001(5) 0.004(4) -0.006(6) C54 0.053(5) 0.075(6) 0.041(4) -0.008(4) 0.003(3) -0.007(4) C55 0.031(3) 0.048(4) 0.041(4) -0.011(3) 0.001(3) 0.001(3) C56 0.038(4) 0.108(8) 0.062(5) 0.015(5) 0.011(4) 0.005(5) C57 0.035(5) 0.113(8) 0.093(7) 0.001(6) 0.007(5) -0.005(5) C58 0.038(4) 0.060(5) 0.120(8) -0.014(6) -0.018(5) 0.004(4) C59 0.061(6) 0.070(6) 0.120(9) 0.014(6) -0.045(6) -0.005(5) C60 0.044(5) 0.061(5) 0.090(7) 0.015(5) -0.018(4) -0.011(4) C61 0.026(3) 0.049(4) 0.029(3) -0.016(3) 0.004(2) -0.001(3) C62 0.036(4) 0.068(5) 0.049(4) -0.021(4) 0.006(3) -0.010(3) C63 0.029(4) 0.095(6) 0.061(5) -0.040(5) 0.001(3) -0.014(4) C64 0.036(4) 0.104(7) 0.041(4) -0.037(5) -0.004(3) 0.003(4) C65 0.060(5) 0.073(6) 0.042(4) -0.017(4) -0.010(4) 0.010(4) C66 0.043(4) 0.061(5) 0.033(3) -0.018(3) -0.002(3) 0.003(3) C67 0.033(3) 0.040(4) 0.033(3) -0.013(3) 0.004(3) 0.000(3) C68 0.057(5) 0.049(4) 0.069(5) -0.007(4) 0.035(4) 0.008(4) C69 0.063(5) 0.066(6) 0.067(5) -0.011(4) 0.037(4) 0.009(4) C70 0.062(5) 0.083(6) 0.043(4) -0.009(4) 0.015(4) -0.010(5) C71 0.140(10) 0.068(6) 0.070(6) 0.013(5) 0.051(7) 0.036(6) C72 0.132(9) 0.053(5) 0.062(5) 0.003(4) 0.047(6) 0.034(5) C73 0.028(3) 0.053(4) 0.043(4) -0.024(3) 0.004(3) 0.000(3) C74 0.040(4) 0.095(6) 0.054(5) -0.042(5) -0.001(3) 0.012(4) C75 0.049(5) 0.097(7) 0.063(5) -0.044(5) 0.013(4) 0.015(4) C76 0.032(4) 0.076(6) 0.107(7) -0.050(5) 0.010(4) 0.007(4) C77 0.042(5) 0.126(9) 0.192(13) -0.113(10) -0.044(7) 0.032(5) C78 0.046(5) 0.119(8) 0.140(9) -0.101(8) -0.036(6) 0.034(5) C79 0.105(10) 0.091(9) 0.129(11) -0.060(8) 0.005(8) -0.007(7) C80 0.131(12) 0.089(9) 0.125(11) -0.026(8) 0.023(9) -0.008(8) C81 0.132(12) 0.088(9) 0.137(12) -0.033(8) 0.023(10) -0.010(8) C82 0.087(9) 0.097(9) 0.131(11) -0.004(8) 0.003(8) 0.012(7) C83 0.119(13) 0.099(11) 0.28(2) -0.001(13) 0.021(14) -0.036(10) C84 0.087(10) 0.143(14) 0.183(16) -0.061(12) 0.006(10) -0.020(9) C85 0.147(13) 0.095(10) 0.161(14) -0.036(10) 0.008(11) -0.003(9) 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 U1 O2 2.387(4) . ? U1 O1 2.388(5) . ? U1 N1 2.390(5) . ? U1 N3 2.390(5) . ? U1 N2 2.426(5) . ? P1 O1 1.509(5) . ? P1 C55 1.787(7) . ? P1 C49 1.799(7) . ? P1 C43 1.814(7) . ? P2 O2 1.506(5) . ? P2 C67 1.791(6) . ? P2 C61 1.796(6) . ? P2 C73 1.799(6) . ? F1 C13 1.341(10) . ? F2 C13 1.322(11) . ? F3 C13 1.339(11) . ? F4 C14 1.335(10) . ? F5 C14 1.342(11) . ? F6 C14 1.326(9) . ? F7 C27 1.351(12) . ? F8 C27 1.300(11) . ? F9 C27 1.308(11) . ? F10 C28 1.303(10) . ? F11 C28 1.291(10) . ? F12 C28 1.296(10) . ? F13 C41 1.306(9) . ? F14 C41 1.281(9) . ? F15 C41 1.310(9) . ? F16 C42 1.236(11) . ? F17 C42 1.329(12) . ? F18 C42 1.261(10) . ? N1 C7 1.398(7) . ? N1 C1 1.402(8) . ? N2 C21 1.379(8) . ? N2 C15 1.418(8) . ? N3 C35 1.380(7) . ? N3 C29 1.408(8) . ? C1 C2 1.397(9) . ? C1 C6 1.412(8) . ? C2 C3 1.366(9) . ? C3 C4 1.375(10) . ? C4 C5 1.385(11) . ? C5 C6 1.382(10) . ? C7 C8 1.397(9) . ? C7 C12 1.398(9) . ? C8 C9 1.377(9) . ? C9 C10 1.377(11) . ? C9 C13 1.503(11) . ? C10 C11 1.366(10) . ? C11 C12 1.393(9) . ? C11 C14 1.496(11) . ? C15 C20 1.383(10) . ? C15 C16 1.406(9) . ? C16 C17 1.392(10) . ? C17 C18 1.385(12) . ? C18 C19 1.376(11) . ? C19 C20 1.386(9) . ? C21 C22 1.392(9) . ? C21 C26 1.414(10) . ? C22 C23 1.385(10) . ? C23 C24 1.380(11) . ? C23 C27 1.479(11) . ? C24 C25 1.392(10) . ? C25 C26 1.374(10) . ? C25 C28 1.491(11) . ? C29 C34 1.397(8) . ? C29 C30 1.409(9) . ? C30 C31 1.380(9) . ? C31 C32 1.391(10) . ? C32 C33 1.356(10) . ? C33 C34 1.388(9) . ? C35 C40 1.397(8) . ? C35 C36 1.401(9) . ? C36 C37 1.393(8) . ? C37 C38 1.383(9) . ? C37 C41 1.485(9) . ? C38 C39 1.373(10) . ? C39 C40 1.384(9) . ? C39 C42 1.499(10) . ? C43 C44 1.356(10) . ? C43 C48 1.358(11) . ? C44 C45 1.382(14) . ? C45 C46 1.383(16) . ? C46 C47 1.366(15) . ? C47 C48 1.471(13) . ? C49 C54 1.378(11) . ? C49 C50 1.393(11) . ? C50 C51 1.366(12) . ? C51 C52 1.367(14) . ? C52 C53 1.385(14) . ? C53 C54 1.392(11) . ? C55 C56 1.376(11) . ? C55 C60 1.385(10) . ? C56 C57 1.365(12) . ? C57 C58 1.356(13) . ? C58 C59 1.353(14) . ? C59 C60 1.373(11) . ? C61 C66 1.386(9) . ? C61 C62 1.391(9) . ? C62 C63 1.380(10) . ? C63 C64 1.369(12) . ? C64 C65 1.369(12) . ? C65 C66 1.375(10) . ? C67 C72 1.339(10) . ? C67 C68 1.375(9) . ? C68 C69 1.362(10) . ? C69 C70 1.339(12) . ? C70 C71 1.369(12) . ? C71 C72 1.402(12) . ? C73 C74 1.355(10) . ? C73 C78 1.375(10) . ? C74 C75 1.379(10) . ? C75 C76 1.340(12) . ? C76 C77 1.360(13) . ? C77 C78 1.363(12) . ? C79 C84 1.3949 . ? C79 C80 1.3950 . ? C79 C85 1.5402 . ? C80 C81 1.3950 . ? C81 C82 1.3950 . ? C82 C83 1.3950 . ? C83 C84 1.3951 . ? C86 C87 1.3949 . ? C86 C91 1.3950 . ? C86 C92 1.5401 . ? C87 C88 1.3951 . ? C88 C89 1.3949 . ? C89 C90 1.3950 . ? C90 C91 1.3950 . ? 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 O2 U1 O1 175.99(14) . . ? O2 U1 N1 92.45(15) . . ? O1 U1 N1 91.46(16) . . ? O2 U1 N3 89.15(16) . . ? O1 U1 N3 89.70(16) . . ? N1 U1 N3 119.20(17) . . ? O2 U1 N2 89.14(17) . . ? O1 U1 N2 88.23(17) . . ? N1 U1 N2 118.53(17) . . ? N3 U1 N2 122.26(17) . . ? O1 P1 C55 112.6(3) . . ? O1 P1 C49 110.6(3) . . ? C55 P1 C49 107.5(3) . . ? O1 P1 C43 112.1(3) . . ? C55 P1 C43 107.1(3) . . ? C49 P1 C43 106.6(3) . . ? O2 P2 C67 111.5(3) . . ? O2 P2 C61 110.6(3) . . ? C67 P2 C61 107.7(3) . . ? O2 P2 C73 110.6(3) . . ? C67 P2 C73 106.7(3) . . ? C61 P2 C73 109.6(3) . . ? P1 O1 U1 169.7(3) . . ? P2 O2 U1 172.3(3) . . ? C7 N1 C1 116.6(5) . . ? C7 N1 U1 123.4(4) . . ? C1 N1 U1 120.0(4) . . ? C21 N2 C15 119.0(5) . . ? C21 N2 U1 117.9(4) . . ? C15 N2 U1 122.0(4) . . ? C35 N3 C29 119.8(5) . . ? C35 N3 U1 129.8(4) . . ? C29 N3 U1 110.4(3) . . ? C2 C1 N1 121.3(5) . . ? C2 C1 C6 117.4(6) . . ? N1 C1 C6 121.1(6) . . ? C3 C2 C1 121.2(6) . . ? C2 C3 C4 121.5(7) . . ? C3 C4 C5 118.4(7) . . ? C6 C5 C4 121.2(7) . . ? C5 C6 C1 120.1(6) . . ? C8 C7 N1 121.7(6) . . ? C8 C7 C12 116.9(6) . . ? N1 C7 C12 121.3(5) . . ? C9 C8 C7 121.0(7) . . ? C8 C9 C10 122.1(7) . . ? C8 C9 C13 119.1(7) . . ? C10 C9 C13 118.8(7) . . ? C11 C10 C9 117.4(6) . . ? C10 C11 C12 122.1(7) . . ? C10 C11 C14 120.1(7) . . ? C12 C11 C14 117.7(7) . . ? C11 C12 C7 120.5(6) . . ? F2 C13 F3 107.5(8) . . ? F2 C13 F1 107.5(9) . . ? F3 C13 F1 103.9(7) . . ? F2 C13 C9 113.4(7) . . ? F3 C13 C9 111.6(8) . . ? F1 C13 C9 112.4(7) . . ? F6 C14 F4 106.4(7) . . ? F6 C14 F5 107.2(8) . . ? F4 C14 F5 104.4(8) . . ? F6 C14 C11 112.8(7) . . ? F4 C14 C11 112.2(7) . . ? F5 C14 C11 113.3(7) . . ? C20 C15 C16 117.6(6) . . ? C20 C15 N2 119.6(6) . . ? C16 C15 N2 122.6(6) . . ? C17 C16 C15 120.3(7) . . ? C18 C17 C16 120.7(7) . . ? C19 C18 C17 119.3(7) . . ? C18 C19 C20 120.1(8) . . ? C15 C20 C19 122.0(7) . . ? N2 C21 C22 124.5(6) . . ? N2 C21 C26 118.6(6) . . ? C22 C21 C26 116.7(6) . . ? C23 C22 C21 121.4(7) . . ? C24 C23 C22 121.6(7) . . ? C24 C23 C27 118.7(7) . . ? C22 C23 C27 119.6(7) . . ? C23 C24 C25 117.4(7) . . ? C26 C25 C24 121.8(7) . . ? C26 C25 C28 119.6(7) . . ? C24 C25 C28 118.5(7) . . ? C25 C26 C21 120.9(7) . . ? F8 C27 F9 109.8(9) . . ? F8 C27 F7 104.3(10) . . ? F9 C27 F7 101.3(8) . . ? F8 C27 C23 115.2(7) . . ? F9 C27 C23 114.0(9) . . ? F7 C27 C23 110.8(8) . . ? F11 C28 F12 106.5(8) . . ? F11 C28 F10 103.8(9) . . ? F12 C28 F10 104.1(8) . . ? F11 C28 C25 114.7(6) . . ? F12 C28 C25 114.0(8) . . ? F10 C28 C25 112.8(7) . . ? C34 C29 N3 119.7(6) . . ? C34 C29 C30 117.1(6) . . ? N3 C29 C30 122.9(5) . . ? C31 C30 C29 121.2(6) . . ? C30 C31 C32 120.3(7) . . ? C33 C32 C31 119.2(6) . . ? C32 C33 C34 121.6(6) . . ? C33 C34 C29 120.6(6) . . ? N3 C35 C40 119.3(6) . . ? N3 C35 C36 123.7(5) . . ? C40 C35 C36 117.0(5) . . ? C37 C36 C35 120.9(6) . . ? C38 C37 C36 121.3(6) . . ? C38 C37 C41 119.2(6) . . ? C36 C37 C41 119.5(6) . . ? C39 C38 C37 118.0(6) . . ? C38 C39 C40 121.7(6) . . ? C38 C39 C42 119.8(6) . . ? C40 C39 C42 118.4(7) . . ? C39 C40 C35 121.2(6) . . ? F14 C41 F13 105.7(8) . . ? F14 C41 F15 105.9(7) . . ? F13 C41 F15 104.0(7) . . ? F14 C41 C37 115.3(6) . . ? F13 C41 C37 111.5(6) . . ? F15 C41 C37 113.5(7) . . ? F16 C42 F18 109.4(9) . . ? F16 C42 F17 103.4(9) . . ? F18 C42 F17 101.3(9) . . ? F16 C42 C39 114.9(7) . . ? F18 C42 C39 116.0(6) . . ? F17 C42 C39 110.2(8) . . ? C44 C43 C48 124.2(8) . . ? C44 C43 P1 118.4(7) . . ? C48 C43 P1 117.4(6) . . ? C43 C44 C45 119.4(10) . . ? C44 C45 C46 119.9(10) . . ? C47 C46 C45 120.7(10) . . ? C46 C47 C48 119.6(11) . . ? C43 C48 C47 115.8(8) . . ? C54 C49 C50 120.9(7) . . ? C54 C49 P1 118.7(6) . . ? C50 C49 P1 120.4(6) . . ? C51 C50 C49 120.2(9) . . ? C50 C51 C52 119.6(9) . . ? C51 C52 C53 120.7(8) . . ? C52 C53 C54 120.3(10) . . ? C49 C54 C53 118.2(9) . . ? C56 C55 C60 118.5(7) . . ? C56 C55 P1 121.7(6) . . ? C60 C55 P1 119.7(6) . . ? C57 C56 C55 120.2(8) . . ? C58 C57 C56 121.1(9) . . ? C59 C58 C57 119.4(8) . . ? C58 C59 C60 120.8(9) . . ? C59 C60 C55 119.9(8) . . ? C66 C61 C62 119.7(6) . . ? C66 C61 P2 118.9(5) . . ? C62 C61 P2 121.2(5) . . ? C63 C62 C61 119.4(8) . . ? C64 C63 C62 120.6(8) . . ? C65 C64 C63 119.8(7) . . ? C64 C65 C66 120.9(8) . . ? C65 C66 C61 119.5(7) . . ? C72 C67 C68 118.5(7) . . ? C72 C67 P2 122.8(5) . . ? C68 C67 P2 118.7(5) . . ? C69 C68 C67 120.5(7) . . ? C70 C69 C68 122.0(7) . . ? C69 C70 C71 118.3(8) . . ? C70 C71 C72 119.9(9) . . ? C67 C72 C71 120.7(8) . . ? C74 C73 C78 118.4(7) . . ? C74 C73 P2 123.6(5) . . ? C78 C73 P2 118.0(5) . . ? C73 C74 C75 121.0(8) . . ? C76 C75 C74 120.0(8) . . ? C75 C76 C77 119.8(8) . . ? C76 C77 C78 120.6(8) . . ? C77 C78 C73 120.1(8) . . ? C84 C79 C80 120.0 . . ? C84 C79 C85 120.0 . . ? C80 C79 C85 120.0 . . ? C81 C80 C79 120.0 . . ? C80 C81 C82 120.0 . . ? C81 C82 C83 120.0 . . ? C82 C83 C84 120.0 . . ? C79 C84 C83 120.0 . . ? C87 C86 C91 120.0 . . ? C87 C86 C92 120.0 . . ? C91 C86 C92 120.0 . . ? C86 C87 C88 120.0 . . ? C89 C88 C87 120.0 . . ? C88 C89 C90 120.0 . . ? C89 C90 C91 120.0 . . ? C86 C91 C90 120.0 . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.83 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 2.449 _refine_diff_density_min -3.167 _refine_diff_density_rms 0.159 data_UP4043(cmpd-S1) _database_code_depnum_ccdc_archive 'CCDC 900236' #TrackingRef 'UF.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H9 F6 N' _chemical_formula_weight 305.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P c a 21 ' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' '-x, -y, z+1/2' _cell_length_a 10.0174(7) _cell_length_b 15.9406(12) _cell_length_c 7.9776(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1273.89(16) _cell_formula_units_Z 4 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_absorpt_correction_T_min 0.6650 _exptl_absorpt_correction_T_max 0.7449 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 16275 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 23.55 _reflns_number_total 1889 _reflns_number_gt 1823 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0422P)^2^+0.1733P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1889 _refine_ls_number_parameters 233 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0655 _refine_ls_wR_factor_gt 0.0642 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.111 _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 0.13517(16) 0.17051(10) 0.3333(2) 0.0254(4) Uani 1 1 d . . . C2 C 0.21062(17) 0.09928(11) 0.2990(2) 0.0320(4) Uani 1 1 d . . . H2 H 0.2853 0.1029 0.2302 0.043 Uiso 1 1 calc R . . C3 C 0.17382(19) 0.02327(11) 0.3677(3) 0.0392(5) Uani 1 1 d . . . H3 H 0.2253 -0.0241 0.3470 0.052 Uiso 1 1 calc R . . C4 C 0.0611(2) 0.01683(12) 0.4672(3) 0.0410(5) Uani 1 1 d . . . H4 H 0.0368 -0.0346 0.5127 0.055 Uiso 1 1 calc R . . C5 C -0.01415(18) 0.08673(14) 0.4980(3) 0.0395(5) Uani 1 1 d . . . H5 H -0.0908 0.0824 0.5632 0.053 Uiso 1 1 calc R . . C6 C 0.02248(17) 0.16379(12) 0.4331(2) 0.0301(4) Uani 1 1 d . . . H6 H -0.0285 0.2111 0.4564 0.040 Uiso 1 1 calc R . . C7 C 0.29339(16) 0.28367(10) 0.2470(2) 0.0248(4) Uani 1 1 d . . . C8 C 0.30958(18) 0.35383(10) 0.1438(2) 0.0270(4) Uani 1 1 d . . . H8 H 0.2366 0.3753 0.0859 0.036 Uiso 1 1 calc R . . C9 C 0.43348(18) 0.39161(11) 0.1272(2) 0.0283(4) Uani 1 1 d . A . C10 C 0.54351(19) 0.36143(11) 0.2129(2) 0.0296(4) Uani 1 1 d . . . H10 H 0.6267 0.3866 0.2013 0.039 Uiso 1 1 calc R . . C11 C 0.52624(17) 0.29294(10) 0.3161(2) 0.0264(4) Uani 1 1 d . B . C12 C 0.40344(17) 0.25408(11) 0.3345(2) 0.0264(4) Uani 1 1 d . . . H12 H 0.3948 0.2081 0.4055 0.035 Uiso 1 1 calc R . . C13 C 0.4458(2) 0.46494(13) 0.0143(3) 0.0426(5) Uani 1 1 d D . . C14 C 0.64191(18) 0.25949(12) 0.4141(3) 0.0389(5) Uani 1 1 d D . . N1 N 0.16685(14) 0.24880(9) 0.2612(2) 0.0301(4) Uani 1 1 d . . . H1 H 0.1014 0.2778 0.2223 0.040 Uiso 1 1 calc R . . F1 F 0.3881(3) 0.4551(2) -0.1317(3) 0.0760(12) Uani 0.70 1 d PGD A 1 F2 F 0.5682(2) 0.4939(3) -0.0103(5) 0.0489(9) Uani 0.70 1 d PGD A 1 F3 F 0.3790(3) 0.5335(2) 0.0855(4) 0.0706(10) Uani 0.70 1 d PGD A 1 F1' F 0.4643(9) 0.4281(5) -0.1534(9) 0.096(3) Uani 0.30 1 d PGD A 2 F2' F 0.5598(7) 0.5000(8) 0.0384(12) 0.059(3) Uani 0.30 1 d PGD A 2 F3' F 0.3497(7) 0.5123(6) -0.0022(13) 0.102(4) Uani 0.30 1 d PGD A 2 F4 F 0.7451(12) 0.3086(5) 0.4262(9) 0.0431(13) Uani 0.55 1 d PGD B 1 F5 F 0.6897(7) 0.1881(3) 0.3316(6) 0.0496(11) Uani 0.55 1 d PGD B 1 F6 F 0.6117(5) 0.2308(3) 0.5661(5) 0.0744(15) Uani 0.55 1 d PGD B 1 F4' F 0.7531(15) 0.3040(6) 0.3834(13) 0.0403(15) Uani 0.45 1 d PGD B 2 F5' F 0.6659(9) 0.1819(3) 0.4007(8) 0.077(2) Uani 0.45 1 d PGD B 2 F6' F 0.6158(6) 0.2761(3) 0.5809(6) 0.0609(13) Uani 0.45 1 d PGD B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0218(8) 0.0315(9) 0.0230(9) -0.0011(8) -0.0029(7) -0.0020(7) C2 0.0271(9) 0.0358(10) 0.0331(11) -0.0080(8) 0.0009(8) -0.0010(8) C3 0.0356(10) 0.0299(10) 0.0521(12) -0.0082(9) -0.0119(9) 0.0001(8) C4 0.0419(11) 0.0361(11) 0.0450(13) 0.0043(9) -0.0091(10) -0.0135(9) C5 0.0299(10) 0.0511(12) 0.0375(11) 0.0028(9) -0.0017(10) -0.0135(9) C6 0.0242(9) 0.0360(9) 0.0300(9) -0.0028(8) -0.0006(8) -0.0016(8) C7 0.0236(9) 0.0277(9) 0.0232(9) -0.0034(7) 0.0030(8) 0.0002(7) C8 0.0297(9) 0.0285(9) 0.0227(9) -0.0026(7) -0.0028(8) 0.0015(7) C9 0.0327(10) 0.0271(9) 0.0250(10) -0.0027(7) -0.0014(8) 0.0000(7) C10 0.0278(9) 0.0309(9) 0.0302(10) -0.0057(8) 0.0032(8) -0.0047(8) C11 0.0266(9) 0.0293(9) 0.0234(9) -0.0062(8) -0.0011(7) 0.0030(7) C12 0.0291(9) 0.0279(9) 0.0223(9) -0.0010(7) 0.0000(8) 0.0015(7) C13 0.0445(13) 0.0410(12) 0.0422(14) 0.0106(10) -0.0081(10) -0.0139(11) C14 0.0277(10) 0.0470(12) 0.0420(13) 0.0056(10) -0.0055(10) -0.0018(9) N1 0.0223(7) 0.0341(9) 0.0338(9) 0.0064(7) -0.0009(6) 0.0022(6) F1 0.111(3) 0.067(2) 0.0498(17) 0.0333(15) -0.049(2) -0.052(2) F2 0.0438(14) 0.0612(18) 0.042(3) 0.0254(14) -0.0015(11) -0.0145(11) F3 0.095(3) 0.0392(11) 0.077(2) 0.0223(14) 0.0079(16) 0.0183(14) F1' 0.170(9) 0.083(5) 0.036(3) 0.027(3) -0.035(5) -0.037(5) F2' 0.088(6) 0.070(4) 0.020(4) 0.008(3) -0.003(3) -0.052(4) F3' 0.044(3) 0.107(9) 0.154(10) 0.101(8) 0.023(6) 0.025(4) F4 0.031(3) 0.045(2) 0.053(4) -0.008(2) -0.017(2) -0.0008(17) F5 0.0396(17) 0.0294(16) 0.080(3) -0.0001(17) -0.017(2) 0.0090(12) F6 0.0359(17) 0.138(4) 0.050(2) 0.050(3) -0.0022(15) 0.015(3) F4' 0.026(2) 0.054(3) 0.041(4) -0.002(2) -0.002(3) 0.000(2) F5' 0.075(5) 0.031(2) 0.125(6) 0.013(3) -0.051(5) 0.003(2) F6' 0.042(2) 0.098(3) 0.042(2) 0.030(2) -0.0137(15) -0.006(3) 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 C6 1.385(3) . ? C1 C2 1.391(2) . ? C1 N1 1.410(2) . ? C2 C3 1.380(3) . ? C3 C4 1.383(3) . ? C4 C5 1.368(3) . ? C5 C6 1.382(3) . ? C7 C12 1.387(2) . ? C7 N1 1.389(2) . ? C7 C8 1.398(3) . ? C8 C9 1.386(3) . ? C9 C10 1.384(3) . ? C9 C13 1.481(3) . ? C10 C11 1.378(3) . ? C11 C12 1.385(2) . ? C11 C14 1.496(3) . ? C13 F3' 1.230(6) . ? C13 F2' 1.286(7) . ? C13 F1 1.310(3) . ? C13 F2 1.324(4) . ? C13 F3 1.402(4) . ? C13 F1' 1.473(8) . ? C14 F5' 1.265(5) . ? C14 F4 1.301(7) . ? C14 F6 1.331(4) . ? C14 F4' 1.343(7) . ? C14 F6' 1.382(5) . ? C14 F5 1.400(5) . ? 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 C6 C1 C2 119.52(16) . . ? C6 C1 N1 119.08(15) . . ? C2 C1 N1 121.31(16) . . ? C3 C2 C1 119.55(17) . . ? C2 C3 C4 120.72(17) . . ? C5 C4 C3 119.51(18) . . ? C4 C5 C6 120.67(18) . . ? C5 C6 C1 120.01(17) . . ? C12 C7 N1 123.25(16) . . ? C12 C7 C8 118.42(15) . . ? N1 C7 C8 118.30(15) . . ? C9 C8 C7 120.52(16) . . ? C10 C9 C8 120.99(17) . . ? C10 C9 C13 120.59(17) . . ? C8 C9 C13 118.42(17) . . ? C11 C10 C9 118.09(16) . . ? C10 C11 C12 121.93(15) . . ? C10 C11 C14 119.82(16) . . ? C12 C11 C14 118.25(16) . . ? C11 C12 C7 120.04(16) . . ? F3' C13 F2' 116.4(6) . . ? F3' C13 F1 68.4(5) . . ? F2' C13 F1 125.2(5) . . ? F3' C13 F2 119.7(5) . . ? F2' C13 F2 18.0(5) . . ? F1 C13 F2 108.6(2) . . ? F3' C13 F3 36.1(5) . . ? F2' C13 F3 91.4(5) . . ? F1 C13 F3 104.1(2) . . ? F2 C13 F3 103.3(2) . . ? F3' C13 F1' 104.3(4) . . ? F2' C13 F1' 101.4(4) . . ? F1 C13 F1' 36.9(3) . . ? F2 C13 F1' 83.6(4) . . ? F3 C13 F1' 137.7(3) . . ? F3' C13 C9 118.9(4) . . ? F2' C13 C9 109.0(6) . . ? F1 C13 C9 114.2(2) . . ? F2 C13 C9 116.3(3) . . ? F3 C13 C9 109.2(2) . . ? F1' C13 C9 104.3(4) . . ? F5' C14 F4 116.4(8) . . ? F5' C14 F6 77.5(3) . . ? F4 C14 F6 108.7(4) . . ? F5' C14 F4' 110.1(6) . . ? F4 C14 F4' 15.5(6) . . ? F6 C14 F4' 122.5(7) . . ? F5' C14 F6' 107.7(3) . . ? F4 C14 F6' 87.9(4) . . ? F6 C14 F6' 31.3(2) . . ? F4' C14 F6' 103.4(4) . . ? F5' C14 F5 25.8(3) . . ? F4 C14 F5 104.7(4) . . ? F6 C14 F5 103.1(2) . . ? F4' C14 F5 93.5(6) . . ? F6' C14 F5 132.3(3) . . ? F5' C14 C11 116.8(5) . . ? F4 C14 C11 116.1(6) . . ? F6 C14 C11 115.0(3) . . ? F4' C14 C11 111.0(8) . . ? F6' C14 C11 106.8(3) . . ? F5 C14 C11 108.0(3) . . ? C7 N1 C1 126.36(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.55 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.180 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.028 data_4188(cmpd-S2) _database_code_depnum_ccdc_archive 'CCDC 900237' #TrackingRef 'UF.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H32 F6 K N O3' _chemical_formula_weight 559.63 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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 10.8866(7) _cell_length_b 11.9211(7) _cell_length_c 12.8559(8) _cell_angle_alpha 111.365(3) _cell_angle_beta 100.052(3) _cell_angle_gamma 109.196(3) _cell_volume 1382.78(15) _cell_formula_units_Z 2 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_absorpt_correction_T_min 0.7007 _exptl_absorpt_correction_T_max 0.7456 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 44236 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6325 _reflns_number_gt 5358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0790P)^2^+0.8207P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6325 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1545 _refine_ls_wR_factor_gt 0.1458 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 K1 K 0.42852(4) 0.29948(4) 0.38189(3) 0.03621(13) Uani 1 1 d . . . F1 F -0.19005(17) 0.19613(19) 0.02904(17) 0.0858(6) Uani 1 1 d . . . F2 F -0.08360(18) 0.08809(16) 0.06126(17) 0.0853(6) Uani 1 1 d . . . F3 F -0.17654(18) 0.1639(2) 0.18225(15) 0.0995(8) Uani 1 1 d . . . F4 F 0.2108(6) 0.5398(4) 0.0246(3) 0.0994(18) Uani 0.80 1 d P . . F5 F 0.3842(3) 0.6700(5) 0.1818(4) 0.0829(10) Uani 0.80 1 d P . . F6 F 0.1996(5) 0.6929(4) 0.1619(5) 0.0941(11) Uani 0.80 1 d P . . F4' F 0.1792(16) 0.576(3) 0.046(2) 0.149(13) Uani 0.20 1 d P . . F5' F 0.346(3) 0.567(3) 0.094(3) 0.146(8) Uani 0.20 1 d P . . F6' F 0.306(4) 0.7153(11) 0.2075(12) 0.156(11) Uani 0.20 1 d P . . O1 O 0.39666(18) 0.2164(2) 0.15291(14) 0.0578(4) Uani 1 1 d . . . O2 O 0.56109(19) 0.14638(19) 0.3913(2) 0.0704(6) Uani 1 1 d . . . O3 O 0.20117(17) 0.09630(18) 0.34919(15) 0.0617(5) Uani 1 1 d . . . N1 N 0.31652(15) 0.48941(15) 0.46756(13) 0.0307(3) Uani 1 1 d . . . C1 C 0.26636(18) 0.45082(16) 0.54660(15) 0.0297(3) Uani 1 1 d . . . C2 C 0.3537(2) 0.43235(18) 0.62726(16) 0.0355(4) Uani 1 1 d . . . H2 H 0.4411 0.4387 0.6207 0.043 Uiso 1 1 calc R . . C3 C 0.3157(3) 0.4053(2) 0.71565(18) 0.0476(5) Uani 1 1 d . . . H3 H 0.3765 0.3921 0.7679 0.057 Uiso 1 1 calc R . . C4 C 0.1900(3) 0.3971(2) 0.72884(19) 0.0533(6) Uani 1 1 d . . . H4 H 0.1643 0.3791 0.7900 0.064 Uiso 1 1 calc R . . C5 C 0.1020(2) 0.4155(2) 0.6512(2) 0.0486(5) Uani 1 1 d . . . H5 H 0.0157 0.4107 0.6597 0.058 Uiso 1 1 calc R . . C6 C 0.1384(2) 0.4409(2) 0.56164(17) 0.0383(4) Uani 1 1 d . . . H6 H 0.0759 0.4520 0.5089 0.046 Uiso 1 1 calc R . . C7 C 0.22977(17) 0.45900(17) 0.36123(15) 0.0289(3) Uani 1 1 d . . . C8 C 0.10025(18) 0.34634(18) 0.29544(16) 0.0316(4) Uani 1 1 d . . . H8 H 0.0649 0.2884 0.3285 0.038 Uiso 1 1 calc R . . C9 C 0.02478(18) 0.31972(19) 0.18393(16) 0.0341(4) Uani 1 1 d . . . C10 C 0.0696(2) 0.4004(2) 0.13050(16) 0.0360(4) Uani 1 1 d . . . H10 H 0.0161 0.3813 0.0543 0.043 Uiso 1 1 calc R . . C11 C 0.1965(2) 0.51021(19) 0.19364(17) 0.0352(4) Uani 1 1 d . . . C12 C 0.27454(18) 0.53954(18) 0.30494(16) 0.0328(4) Uani 1 1 d . . . H12 H 0.3607 0.6159 0.3449 0.039 Uiso 1 1 calc R . . C13 C -0.1072(2) 0.1955(2) 0.11633(19) 0.0466(5) Uani 1 1 d . . . C14 C 0.2495(3) 0.6009(2) 0.1403(2) 0.0512(5) Uani 1 1 d . . . C15 C 0.3231(3) 0.2494(3) 0.0759(3) 0.0666(7) Uani 1 1 d . . . H15a H 0.3252 0.3379 0.1208 0.080 Uiso 1 1 calc R . . H15b H 0.2256 0.1825 0.0376 0.080 Uiso 1 1 calc R . . C16 C 0.3895(4) 0.2517(5) -0.0140(3) 0.0974(13) Uani 1 1 d . . . H16a H 0.3208 0.1929 -0.0946 0.117 Uiso 1 1 calc R . . H16b H 0.4318 0.3434 -0.0053 0.117 Uiso 1 1 calc R . . C17 C 0.4929(5) 0.2054(6) 0.0046(4) 0.1078(15) Uani 1 1 d . . . H17a H 0.5822 0.2686 0.0094 0.129 Uiso 1 1 calc R . . H17b H 0.4664 0.1173 -0.0621 0.129 Uiso 1 1 calc R . . C18 C 0.5053(4) 0.1953(4) 0.1144(3) 0.0801(10) Uani 1 1 d . . . H18a H 0.4982 0.1060 0.1016 0.096 Uiso 1 1 calc R . . H18b H 0.5958 0.2631 0.1749 0.096 Uiso 1 1 calc R . . C19 C 0.7077(3) 0.2032(3) 0.4234(3) 0.0597(6) Uani 1 1 d . . . H19a H 0.7496 0.2955 0.4880 0.072 Uiso 1 1 calc R . . H19b H 0.7360 0.2044 0.3545 0.072 Uiso 1 1 calc R . . C20 C 0.7494(3) 0.1169(3) 0.4626(4) 0.0854(11) Uani 1 1 d . . . H20a H 0.7617 0.1451 0.5478 0.102 Uiso 1 1 calc R . . H20b H 0.8368 0.1184 0.4498 0.102 Uiso 1 1 calc R . . C21 C 0.6313(3) -0.0213(3) 0.3866(4) 0.0823(10) Uani 1 1 d . . . H21a H 0.6542 -0.0745 0.3200 0.099 Uiso 1 1 calc R . . H21b H 0.6099 -0.0696 0.4343 0.099 Uiso 1 1 calc R . . C22 C 0.5127(3) 0.0058(3) 0.3422(3) 0.0689(7) Uani 1 1 d . . . H22a H 0.4806 -0.0346 0.2545 0.083 Uiso 1 1 calc R . . H22b H 0.4349 -0.0324 0.3673 0.083 Uiso 1 1 calc R . . C23 C 0.1495(3) -0.0029(3) 0.2292(2) 0.0662(7) Uani 1 1 d . . . H23a H 0.2180 -0.0380 0.2114 0.079 Uiso 1 1 calc R . . H23b H 0.1308 0.0356 0.1751 0.079 Uiso 1 1 calc R . . C24 C 0.0218(3) -0.1100(3) 0.2131(3) 0.0722(8) Uani 1 1 d . . . H24a H 0.0405 -0.1804 0.2264 0.087 Uiso 1 1 calc R . . H24b H -0.0451 -0.1504 0.1324 0.087 Uiso 1 1 calc R . . C25 C -0.0311(3) -0.0410(3) 0.3051(3) 0.0693(8) Uani 1 1 d . . . H25a H -0.0850 -0.1025 0.3324 0.083 Uiso 1 1 calc R . . H25b H -0.0895 -0.0040 0.2743 0.083 Uiso 1 1 calc R . . C26 C 0.1004(2) 0.0693(2) 0.4043(2) 0.0484(5) Uani 1 1 d . . . H26a H 0.0861 0.1498 0.4449 0.058 Uiso 1 1 calc R . . H26b H 0.1296 0.0400 0.4633 0.058 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 K1 0.0312(2) 0.0352(2) 0.0329(2) 0.00876(16) 0.00644(15) 0.01330(16) F1 0.0512(9) 0.0837(12) 0.0808(12) 0.0397(10) -0.0245(8) 0.0024(8) F2 0.0688(10) 0.0464(9) 0.0890(12) -0.0001(8) 0.0035(9) 0.0123(8) F3 0.0572(9) 0.1127(15) 0.0524(9) 0.0186(10) 0.0134(8) -0.0268(10) F4 0.156(5) 0.0686(15) 0.0395(12) 0.0262(12) 0.034(2) 0.007(2) F5 0.0522(12) 0.107(3) 0.098(2) 0.083(2) 0.0136(13) 0.0090(14) F6 0.142(3) 0.089(2) 0.121(3) 0.082(2) 0.067(2) 0.078(2) F4' 0.060(6) 0.26(3) 0.17(2) 0.20(2) -0.005(10) 0.029(11) F5' 0.155(15) 0.214(18) 0.28(2) 0.222(19) 0.176(17) 0.140(15) F6' 0.28(3) 0.037(5) 0.071(8) 0.028(5) 0.034(15) -0.014(12) O1 0.0583(10) 0.0799(12) 0.0425(8) 0.0269(8) 0.0226(8) 0.0359(9) O2 0.0550(10) 0.0525(10) 0.0968(15) 0.0232(10) 0.0144(10) 0.0326(9) O3 0.0462(9) 0.0554(10) 0.0485(9) 0.0061(8) 0.0180(7) 0.0003(7) N1 0.0264(7) 0.0354(8) 0.0300(7) 0.0160(6) 0.0059(6) 0.0133(6) C1 0.0311(8) 0.0253(8) 0.0271(8) 0.0084(6) 0.0058(6) 0.0115(7) C2 0.0383(9) 0.0345(9) 0.0292(8) 0.0128(7) 0.0056(7) 0.0151(8) C3 0.0609(13) 0.0406(11) 0.0313(9) 0.0173(8) 0.0057(9) 0.0141(10) C4 0.0671(15) 0.0461(12) 0.0342(10) 0.0169(9) 0.0205(10) 0.0098(11) C5 0.0481(12) 0.0435(11) 0.0435(11) 0.0118(9) 0.0230(10) 0.0125(9) C6 0.0377(10) 0.0383(10) 0.0373(9) 0.0133(8) 0.0133(8) 0.0183(8) C7 0.0270(8) 0.0320(8) 0.0299(8) 0.0141(7) 0.0075(6) 0.0163(7) C8 0.0299(8) 0.0336(9) 0.0330(9) 0.0162(7) 0.0094(7) 0.0148(7) C9 0.0292(8) 0.0382(9) 0.0310(9) 0.0117(7) 0.0071(7) 0.0161(7) C10 0.0360(9) 0.0439(10) 0.0297(8) 0.0164(8) 0.0070(7) 0.0213(8) C11 0.0387(9) 0.0390(9) 0.0355(9) 0.0205(8) 0.0126(8) 0.0208(8) C12 0.0301(8) 0.0336(9) 0.0345(9) 0.0163(7) 0.0081(7) 0.0138(7) C13 0.0354(10) 0.0526(12) 0.0360(10) 0.0157(9) 0.0039(8) 0.0100(9) C14 0.0588(13) 0.0526(13) 0.0437(11) 0.0296(11) 0.0115(10) 0.0199(11) C15 0.0684(17) 0.0803(19) 0.0592(15) 0.0264(14) 0.0202(13) 0.0472(15) C16 0.095(3) 0.164(4) 0.082(2) 0.084(3) 0.041(2) 0.074(3) C17 0.122(3) 0.194(5) 0.101(3) 0.103(3) 0.083(3) 0.111(4) C18 0.093(2) 0.126(3) 0.0773(19) 0.062(2) 0.0518(18) 0.082(2) C19 0.0599(15) 0.0546(14) 0.0718(16) 0.0264(13) 0.0313(13) 0.0306(12) C20 0.0566(16) 0.0589(17) 0.126(3) 0.0392(19) 0.0035(17) 0.0244(14) C21 0.0690(18) 0.0485(15) 0.113(3) 0.0261(16) 0.0083(18) 0.0288(14) C22 0.0594(15) 0.0532(14) 0.0748(18) 0.0151(13) 0.0102(14) 0.0239(12) C23 0.0524(14) 0.0646(16) 0.0533(14) 0.0086(12) 0.0218(12) 0.0109(12) C24 0.0574(15) 0.0597(16) 0.0606(16) 0.0059(13) 0.0201(13) 0.0049(13) C25 0.0528(14) 0.0615(16) 0.0704(17) 0.0165(14) 0.0285(13) 0.0090(12) C26 0.0562(13) 0.0467(12) 0.0464(12) 0.0232(10) 0.0217(10) 0.0222(10) 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 K1 O1 2.6572(17) . ? K1 O3 2.6687(17) . ? K1 O2 2.6947(18) . ? K1 N1 2.7867(15) 2_666 ? K1 N1 2.8797(15) . ? F1 C13 1.315(3) . ? F2 C13 1.351(3) . ? F3 C13 1.303(3) . ? F4 F4' 0.65(3) . ? F4 C14 1.308(4) . ? F4 F5' 1.44(2) . ? F5 F6' 1.18(4) . ? F5 F5' 1.20(3) . ? F5 C14 1.313(3) . ? F6 F6' 1.10(4) . ? F6 C14 1.341(4) . ? F6 F4' 1.54(3) . ? F4' C14 1.183(13) . ? F5' C14 1.395(13) . ? F6' C14 1.178(11) . ? O1 C15 1.411(3) . ? O1 C18 1.420(3) . ? O2 C22 1.420(3) . ? O2 C19 1.426(3) . ? O3 C26 1.419(3) . ? O3 C23 1.423(3) . ? N1 C7 1.362(2) . ? N1 C1 1.383(2) . ? N1 K1 2.7868(15) 2_666 ? C1 C2 1.410(2) . ? C1 C6 1.412(3) . ? C2 C3 1.382(3) . ? C3 C4 1.384(4) . ? C4 C5 1.389(4) . ? C5 C6 1.382(3) . ? C7 C12 1.416(2) . ? C7 C8 1.421(2) . ? C8 C9 1.384(2) . ? C9 C10 1.387(3) . ? C9 C13 1.497(3) . ? C10 C11 1.388(3) . ? C11 C12 1.381(3) . ? C11 C14 1.497(3) . ? C15 C16 1.470(4) . ? C16 C17 1.428(5) . ? C17 C18 1.447(4) . ? C19 C20 1.457(4) . ? C20 C21 1.522(4) . ? C21 C22 1.500(4) . ? C23 C24 1.464(4) . ? C24 C25 1.500(4) . ? C25 C26 1.519(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 O1 K1 O3 95.13(6) . . ? O1 K1 O2 89.63(6) . . ? O3 K1 O2 86.43(6) . . ? O1 K1 N1 114.08(5) . 2_666 ? O3 K1 N1 149.19(5) . 2_666 ? O2 K1 N1 84.28(5) . 2_666 ? O1 K1 N1 112.55(5) . . ? O3 K1 N1 92.63(5) . . ? O2 K1 N1 157.78(6) . . ? N1 K1 N1 85.28(4) 2_666 . ? F4' F4 C14 64.4(13) . . ? F4' F4 F5' 120.6(18) . . ? C14 F4 F5' 60.7(9) . . ? F6' F5 F5' 120.7(11) . . ? F6' F5 C14 56.1(8) . . ? F5' F5 C14 67.2(7) . . ? F6' F6 C14 56.8(9) . . ? F6' F6 F4' 96.3(12) . . ? C14 F6 F4' 47.9(5) . . ? F4 F4' C14 85.8(12) . . ? F4 F4' F6 140.0(18) . . ? C14 F4' F6 57.2(12) . . ? F5 F5' C14 60.3(9) . . ? F5 F5' F4 106.6(9) . . ? C14 F5' F4 54.9(6) . . ? F6 F6' C14 72.1(13) . . ? F6 F6' F5 134.3(13) . . ? C14 F6' F5 67.6(14) . . ? C15 O1 C18 109.2(2) . . ? C15 O1 K1 125.54(15) . . ? C18 O1 K1 118.20(16) . . ? C22 O2 C19 107.76(19) . . ? C22 O2 K1 131.29(16) . . ? C19 O2 K1 118.97(15) . . ? C26 O3 C23 109.74(18) . . ? C26 O3 K1 139.12(14) . . ? C23 O3 K1 109.14(14) . . ? C7 N1 C1 121.08(15) . . ? C7 N1 K1 132.76(11) . 2_666 ? C1 N1 K1 101.23(10) . 2_666 ? C7 N1 K1 98.01(10) . . ? C1 N1 K1 99.15(10) . . ? K1 N1 K1 94.72(4) 2_666 . ? N1 C1 C2 118.35(16) . . ? N1 C1 C6 125.05(16) . . ? C2 C1 C6 116.29(17) . . ? C2 C3 C4 120.7(2) . . ? C3 C4 C5 118.9(2) . . ? C6 C5 C4 120.8(2) . . ? C5 C6 C1 121.56(19) . . ? N1 C7 C12 118.38(16) . . ? N1 C7 C8 125.85(16) . . ? C12 C7 C8 115.59(15) . . ? C9 C8 C7 121.04(17) . . ? C8 C9 C10 122.63(17) . . ? C8 C9 C13 118.49(18) . . ? C10 C9 C13 118.82(17) . . ? C9 C10 C11 116.82(16) . . ? C12 C11 C10 122.05(17) . . ? C12 C11 C14 118.90(18) . . ? C10 C11 C14 119.04(17) . . ? C11 C12 C7 121.87(17) . . ? F3 C13 F1 108.9(2) . . ? F3 C13 F2 104.1(2) . . ? F1 C13 F2 103.34(19) . . ? F3 C13 C9 114.10(18) . . ? F1 C13 C9 114.1(2) . . ? F2 C13 C9 111.35(18) . . ? F6' C14 F4' 114.5(15) . . ? F6' C14 F4 130.9(7) . . ? F4' C14 F4 29.8(15) . . ? F6' C14 F5 56.3(19) . . ? F4' C14 F5 123.6(9) . . ? F4 C14 F5 108.2(3) . . ? F6' C14 F6 51.1(19) . . ? F4' C14 F6 74.9(15) . . ? F4 C14 F6 103.6(3) . . ? F5 C14 F6 104.6(3) . . ? F6' C14 F5' 106.9(16) . . ? F4' C14 F5' 92.1(14) . . ? F4 C14 F5' 64.4(13) . . ? F5 C14 F5' 52.5(13) . . ? F6 C14 F5' 141.1(6) . . ? F6' C14 C11 115.0(7) . . ? F4' C14 C11 117.7(9) . . ? F4 C14 C11 113.5(3) . . ? F5 C14 C11 114.4(2) . . ? F6 C14 C11 111.6(2) . . ? F5' C14 C11 106.9(5) . . ? O1 C15 C16 107.6(2) . . ? C17 C16 C15 106.8(3) . . ? C16 C17 C18 107.9(3) . . ? O1 C18 C17 107.6(2) . . ? O2 C19 C20 104.8(2) . . ? C19 C20 C21 104.6(3) . . ? C22 C21 C20 103.8(2) . . ? O2 C22 C21 107.1(2) . . ? O3 C23 C24 107.7(2) . . ? C24 C23 K1 155.28(18) . . ? C23 C24 C25 103.6(2) . . ? C24 C25 C26 103.0(2) . . ? O3 C26 C25 105.84(19) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.661 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.053 data_UP4258(cmpd-S3) _database_code_depnum_ccdc_archive 'CCDC 900238' #TrackingRef 'UF.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 F10 K N O' _chemical_formula_weight 461.35 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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 8.4008(5) _cell_length_b 10.5747(6) _cell_length_c 11.1333(7) _cell_angle_alpha 77.131(3) _cell_angle_beta 69.962(3) _cell_angle_gamma 75.663(2) _cell_volume 889.84(9) _cell_formula_units_Z 2 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.406 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_absorpt_correction_T_min 0.6891 _exptl_absorpt_correction_T_max 0.7456 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 28678 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0103 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4061 _reflns_number_gt 3735 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0410P)^2^+0.3210P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4061 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 K1 K 0.85317(3) 0.37781(2) 0.52472(2) 0.02387(8) Uani 1 1 d . . . N1 N 0.82088(12) 0.66081(10) 0.44627(9) 0.02166(19) Uani 1 1 d . . . C1 C 0.82884(14) 0.68729(11) 0.31836(11) 0.0206(2) Uani 1 1 d . . . C2 C 0.73423(15) 0.79318(11) 0.25454(11) 0.0238(2) Uani 1 1 d . . . C3 C 0.76360(16) 0.81473(12) 0.12238(12) 0.0269(2) Uani 1 1 d . . . C4 C 0.89181(16) 0.73319(13) 0.04417(11) 0.0289(3) Uani 1 1 d . . . C5 C 0.99095(15) 0.62943(13) 0.10116(11) 0.0265(2) Uani 1 1 d . . . C6 C 0.95813(14) 0.60819(11) 0.23311(11) 0.0229(2) Uani 1 1 d . . . C7 C 0.67589(14) 0.71281(11) 0.53829(10) 0.0206(2) Uani 1 1 d . . . C8 C 0.69287(14) 0.76444(11) 0.63813(11) 0.0221(2) Uani 1 1 d . . . C9 C 0.55599(16) 0.80849(12) 0.73963(11) 0.0249(2) Uani 1 1 d . . . C10 C 0.38979(15) 0.80358(13) 0.74741(12) 0.0275(2) Uani 1 1 d . . . C11 C 0.36629(14) 0.75241(13) 0.65256(12) 0.0268(2) Uani 1 1 d . . . C12 C 0.50548(15) 0.70813(12) 0.55246(11) 0.0233(2) Uani 1 1 d . . . F1 F 0.61248(10) 0.88241(7) 0.32300(7) 0.03197(17) Uani 1 1 d . . . F2 F 0.66652(11) 0.91773(8) 0.06949(8) 0.03803(19) Uani 1 1 d . . . F3 F 0.91879(11) 0.75365(9) -0.08433(7) 0.0410(2) Uani 1 1 d . . . F4 F 1.12035(10) 0.54976(9) 0.02801(7) 0.03674(19) Uani 1 1 d . . . F5 F 1.06027(9) 0.50538(7) 0.28511(7) 0.02960(16) Uani 1 1 d . . . F6 F 0.85251(9) 0.77315(7) 0.63421(7) 0.02822(16) Uani 1 1 d . . . F7 F 0.58331(10) 0.85769(8) 0.83007(7) 0.03439(18) Uani 1 1 d . . . F8 F 0.25479(10) 0.84733(9) 0.84507(8) 0.0395(2) Uani 1 1 d . . . F9 F 0.20649(9) 0.74211(9) 0.65872(8) 0.0387(2) Uani 1 1 d . . . F10 F 0.47402(9) 0.65315(8) 0.46554(7) 0.03037(17) Uani 1 1 d . . . O1 O 0.72946(13) 0.24966(9) 0.76304(9) 0.0336(2) Uani 1 1 d . . . C13 C 0.60941(19) 0.30570(16) 0.87220(13) 0.0380(3) Uani 1 1 d . . . H13a H 0.6697 0.3144 0.9294 0.051 Uiso 1 1 calc R . . H13b H 0.5269 0.2485 0.9198 0.051 Uiso 1 1 calc R . . C14 C 0.5172(2) 0.43852(17) 0.82706(16) 0.0460(4) Uani 1 1 d . . . H14a H 0.5992 0.4953 0.7815 0.069 Uiso 1 1 calc R . . H14b H 0.4352 0.4761 0.9003 0.069 Uiso 1 1 calc R . . H14c H 0.4580 0.4294 0.7703 0.069 Uiso 1 1 calc R . . C15 C 0.8077(2) 0.11666(15) 0.79817(15) 0.0433(3) Uani 1 1 d . . . H15a H 0.7192 0.0640 0.8440 0.058 Uiso 1 1 calc R . . H15b H 0.8741 0.1142 0.8550 0.058 Uiso 1 1 calc R . . C16 C 0.9232(3) 0.06108(15) 0.67873(19) 0.0532(4) Uani 1 1 d . . . H16a H 0.8571 0.0650 0.6222 0.080 Uiso 1 1 calc R . . H16b H 0.9738 -0.0291 0.7020 0.080 Uiso 1 1 calc R . . H16c H 1.0128 0.1117 0.6353 0.080 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 K1 0.01984(12) 0.02819(14) 0.02384(13) -0.00244(9) -0.00645(9) -0.00659(9) N1 0.0191(4) 0.0262(5) 0.0186(4) -0.0050(4) -0.0053(4) -0.0015(3) C1 0.0195(5) 0.0239(5) 0.0196(5) -0.0042(4) -0.0052(4) -0.0062(4) C2 0.0224(5) 0.0249(5) 0.0222(5) -0.0047(4) -0.0046(4) -0.0032(4) C3 0.0273(6) 0.0299(6) 0.0241(6) 0.0014(5) -0.0100(5) -0.0078(5) C4 0.0290(6) 0.0430(7) 0.0168(5) -0.0030(5) -0.0050(5) -0.0147(5) C5 0.0200(5) 0.0367(6) 0.0232(6) -0.0130(5) -0.0004(4) -0.0074(5) C6 0.0188(5) 0.0262(5) 0.0235(5) -0.0053(4) -0.0059(4) -0.0034(4) C7 0.0216(5) 0.0208(5) 0.0185(5) -0.0022(4) -0.0057(4) -0.0031(4) C8 0.0195(5) 0.0256(5) 0.0219(5) -0.0037(4) -0.0065(4) -0.0049(4) C9 0.0283(6) 0.0283(6) 0.0204(5) -0.0078(4) -0.0080(4) -0.0046(4) C10 0.0226(6) 0.0347(6) 0.0216(5) -0.0097(5) -0.0006(4) -0.0027(5) C11 0.0182(5) 0.0360(6) 0.0264(6) -0.0075(5) -0.0054(5) -0.0050(5) C12 0.0237(5) 0.0289(6) 0.0197(5) -0.0069(4) -0.0074(4) -0.0052(4) F1 0.0340(4) 0.0274(4) 0.0267(4) -0.0048(3) -0.0071(3) 0.0059(3) F2 0.0429(5) 0.0386(4) 0.0293(4) 0.0055(3) -0.0168(3) -0.0029(3) F3 0.0424(5) 0.0642(6) 0.0162(3) -0.0039(3) -0.0064(3) -0.0150(4) F4 0.0265(4) 0.0529(5) 0.0294(4) -0.0219(3) 0.0004(3) -0.0036(3) F5 0.0244(3) 0.0309(4) 0.0290(4) -0.0078(3) -0.0069(3) 0.0040(3) F6 0.0213(3) 0.0376(4) 0.0303(4) -0.0121(3) -0.0083(3) -0.0067(3) F7 0.0337(4) 0.0474(5) 0.0277(4) -0.0197(3) -0.0082(3) -0.0067(3) F8 0.0253(4) 0.0608(5) 0.0304(4) -0.0240(4) 0.0023(3) -0.0045(4) F9 0.0180(3) 0.0639(6) 0.0377(4) -0.0222(4) -0.0032(3) -0.0084(3) F10 0.0241(3) 0.0457(4) 0.0271(4) -0.0158(3) -0.0071(3) -0.0087(3) O1 0.0405(5) 0.0325(5) 0.0249(4) 0.0022(4) -0.0066(4) -0.0119(4) C13 0.0355(7) 0.0565(9) 0.0235(6) -0.0043(6) -0.0030(5) -0.0212(6) C14 0.0359(8) 0.0537(9) 0.0424(8) -0.0149(7) 0.0005(6) -0.0088(7) C15 0.0539(9) 0.0334(7) 0.0430(8) 0.0095(6) -0.0197(7) -0.0158(6) C16 0.0661(11) 0.0282(7) 0.0635(11) -0.0046(7) -0.0199(9) -0.0075(7) 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 K1 O1 2.6763(9) . ? K1 N1 2.7861(10) 2_766 ? K1 N1 2.8963(10) . ? N1 C1 1.3702(14) . ? N1 C7 1.3782(14) . ? N1 K1 2.7861(10) 2_766 ? C1 C6 1.4062(15) . ? C1 C2 1.4079(16) . ? C2 F1 1.3511(13) . ? C2 C3 1.3812(16) . ? C3 F2 1.3423(14) . ? C3 C4 1.3760(18) . ? C4 F3 1.3450(13) . ? C4 C5 1.3783(18) . ? C5 F4 1.3417(14) . ? C5 C6 1.3750(16) . ? C6 F5 1.3607(13) . ? C7 C12 1.3978(16) . ? C7 C8 1.4041(15) . ? C8 F6 1.3521(13) . ? C8 C9 1.3766(16) . ? C9 F7 1.3371(13) . ? C9 C10 1.3823(17) . ? C10 F8 1.3423(13) . ? C10 C11 1.3774(17) . ? C11 F9 1.3509(13) . ? C11 C12 1.3773(16) . ? C12 F10 1.3587(13) . ? O1 C13 1.4248(17) . ? O1 C15 1.4270(17) . ? C13 C14 1.496(2) . ? C15 C16 1.496(3) . ? 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 K1 N1 91.64(3) . 2_766 ? O1 K1 N1 127.08(3) . . ? N1 K1 N1 95.30(3) 2_766 . ? C1 N1 C7 120.36(9) . . ? C1 N1 K1 111.31(7) . 2_766 ? C7 N1 K1 120.70(7) . 2_766 ? C1 N1 K1 107.64(7) . . ? C7 N1 K1 104.31(7) . . ? K1 N1 K1 84.70(3) 2_766 . ? N1 C1 C6 118.04(10) . . ? N1 C1 C2 128.76(10) . . ? C6 C1 C2 112.89(10) . . ? F1 C2 C3 117.07(10) . . ? F1 C2 C1 119.65(10) . . ? C3 C2 C1 123.23(11) . . ? F2 C3 C4 119.60(11) . . ? F2 C3 C2 119.34(11) . . ? C4 C3 C2 121.05(11) . . ? F3 C4 C3 120.87(12) . . ? F3 C4 C5 120.90(12) . . ? C3 C4 C5 118.22(11) . . ? F4 C5 C6 119.94(11) . . ? F4 C5 C4 120.12(11) . . ? C6 C5 C4 119.94(11) . . ? F5 C6 C5 117.96(10) . . ? F5 C6 C1 117.39(10) . . ? C5 C6 C1 124.64(11) . . ? N1 C7 C12 126.20(10) . . ? N1 C7 C8 119.97(10) . . ? C12 C7 C8 113.48(10) . . ? F6 C8 C9 117.69(10) . . ? F6 C8 C7 118.43(10) . . ? C9 C8 C7 123.88(10) . . ? F7 C9 C8 120.07(11) . . ? F7 C9 C10 119.84(11) . . ? C8 C9 C10 120.09(11) . . ? F8 C10 C11 120.86(11) . . ? F8 C10 C9 120.82(11) . . ? C11 C10 C9 118.32(11) . . ? F9 C11 C10 120.17(10) . . ? F9 C11 C12 119.32(10) . . ? C10 C11 C12 120.49(11) . . ? F10 C12 C11 117.45(10) . . ? F10 C12 C7 118.78(10) . . ? C11 C12 C7 123.74(10) . . ? C13 O1 C15 112.06(11) . . ? C13 O1 K1 126.89(8) . . ? C15 O1 K1 120.03(9) . . ? O1 C13 C14 109.26(11) . . ? O1 C15 C16 109.33(12) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.304 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.043 data_UP4046(cmpd-S4) _database_code_depnum_ccdc_archive 'CCDC 900239' #TrackingRef 'UF.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H42 F25 K N6 U' _chemical_formula_weight 1671.19 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' U U -9.6767 9.6646 '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 24.2328(16) _cell_length_b 12.7508(8) _cell_length_c 24.1585(15) _cell_angle_alpha 90.00 _cell_angle_beta 109.123(3) _cell_angle_gamma 90.00 _cell_volume 7052.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3264 _exptl_absorpt_coefficient_mu 2.469 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_absorpt_correction_T_min 0.5875 _exptl_absorpt_correction_T_max 0.7456 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 117168 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.51 _refine_special_details ; The data were corrected for the presence of disordered solvent using the program SQUEEZE. ; _reflns_number_total 16218 _reflns_number_gt 14217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0248P)^2^+34.1033P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 16218 _refine_ls_number_parameters 946 _refine_ls_number_restraints 132 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group U1 U 0.218758(7) 0.736450(12) 0.352531(7) 0.02422(5) Uani 1 1 d . . . N1 N 0.14912(17) 0.6540(3) 0.26931(17) 0.0299(8) Uani 1 1 d . . . N2 N 0.18403(17) 0.6315(3) 0.41588(16) 0.0285(8) Uani 1 1 d . . . N3 N 0.30464(16) 0.7711(3) 0.43088(17) 0.0281(8) Uani 1 1 d . . . N4 N 0.26004(16) 0.8103(3) 0.28440(15) 0.0254(8) Uani 1 1 d . . . N5 N 0.1592(2) 0.8991(3) 0.3689(2) 0.0424(11) Uani 1 1 d . . . N6 N 0.3568(4) 0.2647(6) 0.2853(3) 0.092(2) Uani 1 1 d . B . C1 C 0.0902(2) 0.6835(6) 0.2636(3) 0.0513(16) Uani 1 1 d . . . C2 C 0.0584(3) 0.7511(6) 0.2182(4) 0.086(3) Uani 1 1 d . . . H2 H 0.0746 0.7739 0.1904 0.114 Uiso 1 1 calc R . . C3 C 0.0023(4) 0.7839(9) 0.2151(6) 0.123(5) Uani 1 1 d . . . H3 H -0.0192 0.8276 0.1849 0.164 Uiso 1 1 calc R . . C4 C -0.0203(4) 0.7506(14) 0.2569(6) 0.154(7) Uani 1 1 d . . . H4 H -0.0568 0.7748 0.2560 0.204 Uiso 1 1 calc R . . C5 C 0.0085(4) 0.6849(15) 0.2987(4) 0.161(7) Uani 1 1 d . . . H5 H -0.0082 0.6620 0.3261 0.214 Uiso 1 1 calc R . . C6 C 0.0643(3) 0.6495(10) 0.3017(3) 0.101(4) Uani 1 1 d . . . H6 H 0.0837 0.6017 0.3306 0.134 Uiso 1 1 calc R . . C7 C 0.1561(2) 0.5874(4) 0.22716(19) 0.0298(10) Uani 1 1 d . . . C8 C 0.1097(2) 0.5291(4) 0.1879(2) 0.0383(12) Uani 1 1 d . . . H8 H 0.0719 0.5381 0.1889 0.051 Uiso 1 1 calc R . . C9 C 0.1193(3) 0.4598(5) 0.1484(2) 0.0455(14) Uani 1 1 d . . . C10 C 0.1745(3) 0.4430(4) 0.1445(2) 0.0410(12) Uani 1 1 d . . . H10 H 0.1806 0.3952 0.1180 0.055 Uiso 1 1 calc R . . C11 C 0.2200(2) 0.5005(4) 0.1816(2) 0.0320(10) Uani 1 1 d . . . C12 C 0.2111(2) 0.5714(4) 0.22155(19) 0.0276(9) Uani 1 1 d . . . H12 H 0.2427 0.6094 0.2453 0.037 Uiso 1 1 calc R . . C13 C 0.0687(4) 0.4009(7) 0.1072(4) 0.079(3) Uani 1 1 d . . . C14 C 0.2800(2) 0.4889(4) 0.1785(2) 0.0389(12) Uani 1 1 d . . . C15 C 0.1722(2) 0.6912(3) 0.4609(2) 0.0293(10) Uani 1 1 d . . . C16 C 0.1161(2) 0.7266(4) 0.4540(2) 0.0391(11) Uani 1 1 d . . . H16 H 0.0857 0.7096 0.4201 0.052 Uiso 1 1 calc R . . C17 C 0.1049(3) 0.7869(5) 0.4970(3) 0.0514(15) Uani 1 1 d . . . H17 H 0.0672 0.8108 0.4914 0.068 Uiso 1 1 calc R . . C18 C 0.1486(3) 0.8113(4) 0.5471(3) 0.0480(14) Uani 1 1 d . . . H18 H 0.1409 0.8519 0.5757 0.064 Uiso 1 1 calc R . . C19 C 0.2046(3) 0.7755(5) 0.5555(2) 0.0474(14) Uani 1 1 d . . . H19 H 0.2345 0.7914 0.5900 0.063 Uiso 1 1 calc R . . C20 C 0.2165(2) 0.7158(4) 0.5124(2) 0.0363(11) Uani 1 1 d . . . H20 H 0.2543 0.6922 0.5183 0.048 Uiso 1 1 calc R . . C21 C 0.1827(2) 0.5237(4) 0.4218(2) 0.0286(10) Uani 1 1 d . . . C22 C 0.1812(2) 0.4733(4) 0.4731(2) 0.0398(12) Uani 1 1 d . . . H22 H 0.1778 0.5131 0.5040 0.053 Uiso 1 1 calc R . . C23 C 0.1847(3) 0.3648(4) 0.4780(2) 0.0474(14) Uani 1 1 d D A . C24 C 0.1881(3) 0.3014(4) 0.4327(3) 0.0465(14) Uani 1 1 d . . . H24 H 0.1907 0.2289 0.4365 0.062 Uiso 1 1 calc R . . C25 C 0.1875(2) 0.3511(4) 0.3814(2) 0.0383(12) Uani 1 1 d . . . C26 C 0.1846(2) 0.4585(4) 0.3753(2) 0.0351(11) Uani 1 1 d . . . H26 H 0.1840 0.4885 0.3399 0.047 Uiso 1 1 calc R . . C27 C 0.1854(3) 0.3147(5) 0.5344(3) 0.074(2) Uani 1 1 d DU . . C28 C 0.1945(3) 0.2869(5) 0.3330(3) 0.0525(15) Uani 1 1 d . . . C29 C 0.3152(2) 0.8773(3) 0.4462(2) 0.0296(10) Uani 1 1 d . . . C30 C 0.3185(3) 0.9518(4) 0.4055(2) 0.0412(13) Uani 1 1 d . . . H30 H 0.3176 0.9303 0.3684 0.055 Uiso 1 1 calc R . . C31 C 0.3231(3) 1.0585(5) 0.4192(3) 0.064(2) Uani 1 1 d . . . H31 H 0.3256 1.1069 0.3913 0.085 Uiso 1 1 calc R . . C32 C 0.3240(4) 1.0922(5) 0.4728(3) 0.068(2) Uani 1 1 d . . . H32 H 0.3251 1.1635 0.4812 0.090 Uiso 1 1 calc R . . C33 C 0.3234(3) 1.0188(5) 0.5148(3) 0.0624(19) Uani 1 1 d . . . H33 H 0.3260 1.0412 0.5523 0.083 Uiso 1 1 calc R . . C34 C 0.3188(3) 0.9135(4) 0.5022(2) 0.0461(14) Uani 1 1 d . . . H34 H 0.3181 0.8657 0.5310 0.061 Uiso 1 1 calc R . . C35 C 0.34844(19) 0.7037(4) 0.46546(17) 0.0244(9) Uani 1 1 d . . . C36 C 0.4071(2) 0.7328(4) 0.49349(19) 0.0294(9) Uani 1 1 d . . . H36 H 0.4181 0.8020 0.4906 0.039 Uiso 1 1 calc R . . C37 C 0.4486(2) 0.6625(4) 0.5250(2) 0.0332(10) Uani 1 1 d . . . C38 C 0.4352(2) 0.5594(4) 0.5319(2) 0.0321(10) Uani 1 1 d . . . H38 H 0.4635 0.5128 0.5538 0.043 Uiso 1 1 calc R . . C39 C 0.3779(2) 0.5278(4) 0.50509(19) 0.0280(9) Uani 1 1 d . . . C40 C 0.3351(2) 0.5970(3) 0.47254(19) 0.0252(9) Uani 1 1 d . . . H40 H 0.2971 0.5730 0.4551 0.034 Uiso 1 1 calc R . . C41 C 0.5097(2) 0.7009(5) 0.5548(3) 0.0483(14) Uani 1 1 d . . . C42 C 0.3595(2) 0.4184(4) 0.5123(2) 0.0359(11) Uani 1 1 d . . . C43 C 0.2185(2) 0.8765(3) 0.24336(19) 0.0265(9) Uani 1 1 d . . . C44 C 0.2070(3) 0.9756(4) 0.2591(3) 0.0562(18) Uani 1 1 d . . . H44 H 0.2267 1.0000 0.2966 0.075 Uiso 1 1 calc R . . C45 C 0.1665(4) 1.0396(5) 0.2200(3) 0.081(3) Uani 1 1 d . . . H45 H 0.1589 1.1057 0.2320 0.107 Uiso 1 1 calc R . . C46 C 0.1377(3) 1.0079(5) 0.1647(3) 0.0498(15) Uani 1 1 d . . . H46 H 0.1113 1.0521 0.1385 0.066 Uiso 1 1 calc R . . C47 C 0.1482(3) 0.9094(5) 0.1481(2) 0.0497(15) Uani 1 1 d . . . H47 H 0.1290 0.8867 0.1100 0.066 Uiso 1 1 calc R . . C48 C 0.1871(3) 0.8434(4) 0.1874(2) 0.0472(14) Uani 1 1 d . . . H48 H 0.1922 0.7754 0.1760 0.063 Uiso 1 1 calc R . . C49 C 0.3111(2) 0.7896(3) 0.27281(19) 0.0265(9) Uani 1 1 d . . . C50 C 0.3227(2) 0.8257(4) 0.22243(19) 0.0293(10) Uani 1 1 d . . . H50 H 0.2956 0.8684 0.1958 0.039 Uiso 1 1 calc R . . C51 C 0.3739(2) 0.7987(4) 0.2120(2) 0.0340(11) Uani 1 1 d . . . C52 C 0.4159(2) 0.7359(4) 0.2501(2) 0.0342(10) Uani 1 1 d . . . H52 H 0.4495 0.7167 0.2422 0.045 Uiso 1 1 calc R . . C53 C 0.4058(2) 0.7027(4) 0.3005(2) 0.0334(10) Uani 1 1 d D B . C54 C 0.3555(2) 0.7301(4) 0.31228(19) 0.0283(9) Uani 1 1 d . . . H54 H 0.3510 0.7084 0.3473 0.038 Uiso 1 1 calc R . . C55 C 0.3837(3) 0.8361(5) 0.1573(2) 0.0465(14) Uani 1 1 d . . . C56 C 0.4498(2) 0.6353(5) 0.3430(2) 0.0527(14) Uani 1 1 d DU . . C57 C 0.1123(3) 0.9357(5) 0.3278(4) 0.073(2) Uani 1 1 d . . . H57 H 0.1021 0.9078 0.2902 0.097 Uiso 1 1 calc R . . C58 C 0.0779(4) 1.0149(7) 0.3393(5) 0.100(4) Uani 1 1 d . . . H58 H 0.0448 1.0377 0.3097 0.133 Uiso 1 1 calc R . . C59 C 0.0919(4) 1.0583(6) 0.3925(5) 0.091(3) Uani 1 1 d . . . H59 H 0.0698 1.1129 0.3999 0.121 Uiso 1 1 calc R . . C60 C 0.1388(4) 1.0207(5) 0.4351(4) 0.070(2) Uani 1 1 d . . . H60 H 0.1488 1.0475 0.4729 0.093 Uiso 1 1 calc R . . C61 C 0.1719(3) 0.9420(4) 0.4222(3) 0.0498(15) Uani 1 1 d . . . H61 H 0.2046 0.9177 0.4519 0.066 Uiso 1 1 calc R . . F1 F 0.0651(2) 0.4086(5) 0.0533(2) 0.121(2) Uani 1 1 d . . . F2 F 0.0207(2) 0.4098(6) 0.1172(3) 0.136(3) Uani 1 1 d . . . F3 F 0.0780(3) 0.2940(5) 0.1154(3) 0.124(2) Uani 1 1 d . . . F4 F 0.29624(18) 0.5684(3) 0.1516(2) 0.0784(13) Uani 1 1 d . . . F5 F 0.28785(17) 0.4036(3) 0.15150(18) 0.0714(12) Uani 1 1 d . . . F6 F 0.32119(16) 0.4874(4) 0.23153(15) 0.0690(12) Uani 1 1 d . B . F7 F 0.1624(8) 0.3738(8) 0.5647(5) 0.090(3) Uani 0.40 1 d PDU A 1 F8 F 0.1447(5) 0.2368(7) 0.5221(4) 0.103(3) Uani 0.60 1 d PDU A 1 F9 F 0.2328(5) 0.2604(10) 0.5589(6) 0.123(5) Uani 0.60 1 d PDU A 1 F7' F 0.2148(5) 0.3737(6) 0.5820(3) 0.093(3) Uani 0.60 1 d PDU A 2 F8' F 0.1355(5) 0.3117(14) 0.5439(6) 0.106(4) Uani 0.40 1 d PDU A 2 F9' F 0.2111(9) 0.2231(9) 0.5433(8) 0.114(6) Uani 0.40 1 d PDU A 2 F10 F 0.1645(3) 0.3190(4) 0.28084(18) 0.0913(15) Uani 1 1 d . . . F11 F 0.1841(3) 0.1869(3) 0.3358(2) 0.0905(16) Uani 1 1 d . . . F12 F 0.2504(2) 0.2904(4) 0.3327(3) 0.1036(19) Uani 1 1 d . B . F13 F 0.52945(17) 0.7617(4) 0.5207(2) 0.0876(15) Uani 1 1 d . . . F14 F 0.54885(16) 0.6246(4) 0.5707(2) 0.0900(16) Uani 1 1 d . . . F15 F 0.51476(19) 0.7572(5) 0.6012(2) 0.1039(19) Uani 1 1 d . . . F16 F 0.31843(17) 0.4146(3) 0.53813(18) 0.0609(10) Uani 1 1 d . . . F17 F 0.40280(15) 0.3574(3) 0.54384(16) 0.0569(9) Uani 1 1 d . . . F18 F 0.33575(16) 0.3699(2) 0.46023(14) 0.0501(8) Uani 1 1 d . B . F19 F 0.3480(3) 0.9084(5) 0.1297(2) 0.137(3) Uani 1 1 d . . . F20 F 0.4340(2) 0.8743(6) 0.1655(2) 0.141(3) Uani 1 1 d . . . F21 F 0.3765(4) 0.7652(5) 0.1188(2) 0.139(3) Uani 1 1 d . . . F22 F 0.4555(4) 0.6441(9) 0.3974(3) 0.088(3) Uani 0.60 1 d PDU B 1 F23 F 0.5015(3) 0.6335(8) 0.3373(5) 0.064(3) Uani 0.60 1 d PDU B 1 F24 F 0.4335(3) 0.5306(5) 0.3325(4) 0.090(3) Uani 0.60 1 d PDU B 1 F22' F 0.4822(5) 0.7021(9) 0.3873(5) 0.092(4) Uani 0.40 1 d PDU B 2 F23' F 0.4880(6) 0.5921(12) 0.3244(7) 0.085(4) Uani 0.40 1 d PDU B 2 F24' F 0.4296(4) 0.5738(11) 0.3742(6) 0.074(3) Uani 0.40 1 d PDU B 2 F25 F 0.26864(11) 0.5997(2) 0.34823(11) 0.0284(5) Uani 1 1 d . B . K1 K 0.33587(6) 0.43828(10) 0.35004(5) 0.0447(3) Uani 1 1 d . . . C62 C 0.4000(5) 0.2870(10) 0.2636(5) 0.119(4) Uani 1 1 d . . . H62 H 0.4274 0.3373 0.2827 0.159 Uiso 1 1 calc R B . C63 C 0.4059(6) 0.2399(12) 0.2151(5) 0.146(6) Uani 1 1 d . B . H63 H 0.4361 0.2583 0.2011 0.194 Uiso 1 1 calc R . . C64 C 0.3658(8) 0.1644(12) 0.1874(5) 0.151(7) Uani 1 1 d . . . H64 H 0.3684 0.1301 0.1544 0.200 Uiso 1 1 calc R B . C65 C 0.3223(7) 0.1408(10) 0.2094(5) 0.141(5) Uani 1 1 d . B . H65 H 0.2952 0.0890 0.1918 0.187 Uiso 1 1 calc R . . C66 C 0.3183(6) 0.1924(8) 0.2568(4) 0.114(4) Uani 1 1 d . . . H66 H 0.2874 0.1767 0.2701 0.152 Uiso 1 1 calc R B . 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 U1 0.02795(9) 0.02537(8) 0.02023(8) 0.00027(7) 0.00912(6) 0.00048(7) N1 0.026(2) 0.037(2) 0.027(2) -0.0012(16) 0.0099(16) 0.0040(16) N2 0.032(2) 0.031(2) 0.0238(19) 0.0000(15) 0.0109(16) -0.0036(16) N3 0.0250(19) 0.0245(18) 0.035(2) 0.0016(16) 0.0097(16) 0.0048(15) N4 0.031(2) 0.0268(19) 0.0198(17) 0.0020(14) 0.0098(15) 0.0013(15) N5 0.040(3) 0.028(2) 0.061(3) 0.007(2) 0.020(2) 0.0067(18) N6 0.117(6) 0.087(5) 0.066(4) -0.014(4) 0.023(4) 0.044(5) C1 0.031(3) 0.078(4) 0.042(3) -0.027(3) 0.008(2) 0.001(3) C2 0.042(4) 0.072(5) 0.123(7) -0.003(5) -0.001(4) 0.016(4) C3 0.057(6) 0.106(8) 0.167(12) -0.045(8) -0.018(6) 0.031(5) C4 0.051(6) 0.28(2) 0.125(10) -0.113(12) 0.023(6) 0.009(8) C5 0.039(5) 0.39(2) 0.053(5) -0.061(9) 0.006(4) 0.013(8) C6 0.035(4) 0.225(12) 0.041(4) -0.016(5) 0.010(3) -0.009(5) C7 0.035(3) 0.031(2) 0.023(2) -0.0011(18) 0.0093(19) -0.0011(19) C8 0.033(3) 0.053(3) 0.029(2) -0.008(2) 0.011(2) -0.006(2) C9 0.047(3) 0.052(3) 0.037(3) -0.017(3) 0.014(3) -0.014(3) C10 0.059(4) 0.037(3) 0.029(3) -0.014(2) 0.018(2) -0.005(2) C11 0.042(3) 0.030(2) 0.025(2) -0.0010(18) 0.012(2) 0.000(2) C12 0.032(2) 0.027(2) 0.022(2) -0.0004(17) 0.0073(18) 0.0004(18) C13 0.072(5) 0.104(7) 0.073(5) -0.059(5) 0.038(4) -0.040(5) C14 0.049(3) 0.041(3) 0.029(3) -0.003(2) 0.016(2) 0.010(2) C15 0.039(3) 0.021(2) 0.032(2) 0.0027(18) 0.017(2) -0.0010(18) C16 0.038(3) 0.037(3) 0.046(3) 0.005(2) 0.017(2) 0.003(2) C17 0.058(4) 0.046(3) 0.062(4) 0.006(3) 0.035(3) 0.019(3) C18 0.075(4) 0.035(3) 0.045(3) -0.002(2) 0.034(3) 0.009(3) C19 0.070(4) 0.043(3) 0.034(3) -0.005(2) 0.024(3) -0.003(3) C20 0.039(3) 0.042(3) 0.031(2) 0.001(2) 0.017(2) 0.001(2) C21 0.028(2) 0.028(2) 0.029(2) 0.0012(18) 0.0099(19) -0.0063(18) C22 0.052(3) 0.032(3) 0.043(3) 0.002(2) 0.027(3) -0.002(2) C23 0.064(4) 0.036(3) 0.050(3) 0.009(2) 0.030(3) -0.004(3) C24 0.059(4) 0.028(3) 0.058(4) 0.001(2) 0.027(3) -0.010(2) C25 0.045(3) 0.028(3) 0.042(3) -0.010(2) 0.016(2) -0.012(2) C26 0.038(3) 0.037(3) 0.030(2) -0.005(2) 0.011(2) -0.011(2) C27 0.127(6) 0.044(4) 0.066(4) 0.014(3) 0.053(4) 0.001(3) C28 0.074(4) 0.034(3) 0.051(4) -0.014(3) 0.022(3) -0.019(3) C29 0.036(3) 0.021(2) 0.031(2) -0.0036(18) 0.010(2) -0.0004(18) C30 0.063(4) 0.030(3) 0.026(2) 0.000(2) 0.008(2) -0.006(2) C31 0.104(6) 0.028(3) 0.048(4) 0.006(3) 0.007(4) -0.006(3) C32 0.103(6) 0.025(3) 0.065(4) -0.014(3) 0.013(4) -0.002(3) C33 0.096(5) 0.043(4) 0.055(4) -0.025(3) 0.034(4) -0.013(3) C34 0.074(4) 0.033(3) 0.037(3) -0.007(2) 0.027(3) -0.010(3) C35 0.032(2) 0.034(2) 0.0103(17) -0.0003(16) 0.0108(16) -0.0004(18) C36 0.033(2) 0.028(2) 0.026(2) -0.0018(18) 0.0082(18) -0.0043(19) C37 0.029(2) 0.040(3) 0.030(2) -0.001(2) 0.008(2) -0.001(2) C38 0.034(3) 0.032(2) 0.028(2) 0.0012(19) 0.008(2) 0.007(2) C39 0.034(2) 0.030(2) 0.021(2) 0.0012(17) 0.0093(18) 0.0028(19) C40 0.027(2) 0.022(2) 0.026(2) -0.0002(17) 0.0088(18) -0.0016(17) C41 0.032(3) 0.054(4) 0.049(3) 0.000(3) 0.000(2) 0.000(3) C42 0.043(3) 0.031(3) 0.030(2) 0.004(2) 0.008(2) 0.005(2) C43 0.033(2) 0.025(2) 0.024(2) 0.0030(17) 0.0128(19) 0.0017(18) C44 0.087(5) 0.034(3) 0.032(3) -0.005(2) -0.001(3) 0.020(3) C45 0.125(7) 0.045(4) 0.051(4) -0.006(3) -0.001(4) 0.044(4) C46 0.052(4) 0.055(4) 0.039(3) 0.011(3) 0.011(3) 0.022(3) C47 0.057(4) 0.042(3) 0.035(3) 0.003(2) -0.006(3) 0.005(3) C48 0.059(4) 0.031(3) 0.038(3) -0.001(2) -0.004(3) 0.006(2) C49 0.030(2) 0.026(2) 0.024(2) -0.0029(17) 0.0094(18) -0.0053(17) C50 0.034(3) 0.032(2) 0.022(2) 0.0019(18) 0.0093(19) -0.0012(19) C51 0.040(3) 0.038(3) 0.026(2) 0.000(2) 0.014(2) -0.007(2) C52 0.032(2) 0.040(3) 0.035(2) 0.001(2) 0.017(2) 0.000(2) C53 0.028(2) 0.039(3) 0.032(2) 0.004(2) 0.009(2) 0.001(2) C54 0.032(2) 0.031(2) 0.025(2) 0.0043(18) 0.0128(18) -0.0007(19) C55 0.047(3) 0.066(4) 0.031(3) 0.008(3) 0.020(2) -0.001(3) C56 0.038(3) 0.074(4) 0.051(3) 0.023(3) 0.022(3) 0.014(3) C57 0.053(4) 0.046(4) 0.101(6) -0.003(4) -0.001(4) 0.008(3) C58 0.053(5) 0.052(5) 0.176(11) 0.004(6) 0.011(6) 0.021(4) C59 0.070(5) 0.032(4) 0.188(11) -0.013(5) 0.064(6) 0.010(4) C60 0.099(6) 0.030(3) 0.111(6) -0.005(4) 0.076(5) 0.000(3) C61 0.066(4) 0.028(3) 0.066(4) 0.005(3) 0.037(3) 0.007(3) F1 0.112(4) 0.183(6) 0.048(3) -0.036(3) -0.001(3) -0.069(4) F2 0.054(3) 0.193(6) 0.161(5) -0.127(5) 0.033(3) -0.046(3) F3 0.129(5) 0.099(4) 0.150(6) -0.061(4) 0.056(4) -0.065(4) F4 0.067(3) 0.075(3) 0.115(4) 0.033(3) 0.058(3) 0.016(2) F5 0.062(2) 0.075(3) 0.081(3) -0.042(2) 0.029(2) 0.007(2) F6 0.047(2) 0.117(4) 0.041(2) -0.012(2) 0.0120(16) 0.023(2) F7 0.179(10) 0.062(6) 0.064(6) 0.009(5) 0.087(7) -0.010(7) F8 0.160(7) 0.079(6) 0.101(6) 0.017(5) 0.083(6) -0.039(6) F9 0.147(8) 0.122(10) 0.094(9) 0.068(8) 0.032(6) 0.027(7) F7' 0.162(8) 0.078(5) 0.051(4) 0.012(3) 0.050(5) -0.017(6) F8' 0.129(7) 0.124(10) 0.094(9) 0.026(8) 0.075(7) -0.035(7) F9' 0.228(15) 0.061(7) 0.071(9) 0.025(6) 0.072(11) 0.043(10) F10 0.151(5) 0.067(3) 0.048(2) -0.013(2) 0.022(3) 0.007(3) F11 0.169(5) 0.033(2) 0.079(3) -0.023(2) 0.054(3) -0.029(3) F12 0.096(4) 0.097(4) 0.141(5) -0.072(3) 0.071(3) -0.029(3) F13 0.044(2) 0.119(4) 0.091(3) 0.033(3) 0.010(2) -0.027(2) F14 0.033(2) 0.074(3) 0.134(4) 0.017(3) -0.013(2) 0.0015(19) F15 0.055(3) 0.157(5) 0.090(3) -0.073(3) 0.009(2) -0.034(3) F16 0.073(3) 0.045(2) 0.081(3) 0.0161(18) 0.046(2) -0.0033(17) F17 0.058(2) 0.0364(18) 0.060(2) 0.0188(16) -0.0029(17) 0.0083(15) F18 0.070(2) 0.0292(16) 0.0411(18) 0.0005(13) 0.0045(16) -0.0094(15) F19 0.177(6) 0.177(6) 0.106(4) 0.101(4) 0.111(4) 0.096(5) F20 0.090(4) 0.277(8) 0.056(3) 0.048(4) 0.022(3) -0.085(5) F21 0.285(9) 0.106(4) 0.065(3) -0.026(3) 0.112(5) -0.058(5) F22 0.088(6) 0.139(8) 0.043(4) 0.032(4) 0.027(4) 0.067(5) F23 0.032(3) 0.089(6) 0.076(6) 0.036(5) 0.024(4) 0.016(3) F24 0.067(5) 0.057(4) 0.117(7) 0.039(4) -0.007(5) 0.003(3) F22' 0.072(8) 0.106(9) 0.066(7) 0.026(5) -0.019(6) 0.013(6) F23' 0.076(8) 0.108(11) 0.086(8) 0.040(7) 0.047(7) 0.059(7) F24' 0.051(6) 0.092(8) 0.080(7) 0.060(6) 0.022(5) 0.017(5) F25 0.0320(14) 0.0257(13) 0.0275(13) 0.0001(10) 0.0099(11) 0.0025(11) K1 0.0547(7) 0.0395(6) 0.0400(6) 0.0003(5) 0.0157(5) 0.0121(5) C62 0.099(7) 0.159(11) 0.090(7) -0.021(7) 0.017(6) 0.076(8) C63 0.159(12) 0.184(14) 0.088(8) -0.029(8) 0.032(8) 0.101(11) C64 0.236(18) 0.141(12) 0.071(7) -0.027(7) 0.045(9) 0.077(12) C65 0.243(17) 0.097(8) 0.098(8) -0.029(7) 0.076(10) 0.023(10) C66 0.207(13) 0.069(6) 0.077(6) -0.017(5) 0.061(7) 0.019(7) 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 U1 F25 2.143(3) . ? U1 N3 2.351(4) . ? U1 N4 2.382(4) . ? U1 N2 2.385(4) . ? U1 N1 2.402(4) . ? U1 N5 2.630(4) . ? N1 C7 1.379(6) . ? N1 C1 1.438(7) . ? N2 C21 1.383(6) . ? N2 C15 1.432(6) . ? N3 C29 1.406(6) . ? N3 C35 1.408(6) . ? N4 C49 1.381(6) . ? N4 C43 1.433(6) . ? N5 C57 1.325(8) . ? N5 C61 1.338(8) . ? N6 C66 1.333(13) . ? N6 C62 1.345(14) . ? N6 K1 2.850(7) . ? C1 C6 1.344(10) . ? C1 C2 1.410(11) . ? C2 C3 1.399(12) . ? C3 C4 1.367(18) . ? C4 C5 1.32(2) . ? C5 C6 1.404(12) . ? C7 C12 1.397(7) . ? C7 C8 1.421(7) . ? C8 C9 1.375(7) . ? C9 C10 1.389(8) . ? C9 C13 1.504(8) . ? C10 C11 1.380(7) . ? C11 C12 1.391(6) . ? C11 C14 1.487(7) . ? C13 F2 1.268(8) . ? C13 F1 1.280(9) . ? C13 F3 1.385(11) . ? C14 F5 1.314(6) . ? C14 F4 1.331(7) . ? C14 F6 1.342(6) . ? C15 C20 1.386(7) . ? C15 C16 1.389(7) . ? C16 C17 1.389(8) . ? C17 C18 1.358(9) . ? C18 C19 1.382(9) . ? C19 C20 1.393(7) . ? C21 C22 1.407(7) . ? C21 C26 1.411(7) . ? C22 C23 1.389(7) . ? C23 C24 1.383(8) . ? C23 C27 1.501(7) . ? C24 C25 1.387(8) . ? C25 C26 1.377(7) . ? C25 C28 1.482(8) . ? C27 F7 1.296(8) . ? C27 F8' 1.302(8) . ? C27 F9 1.306(8) . ? C27 F9' 1.308(8) . ? C27 F8 1.361(7) . ? C27 F7' 1.363(7) . ? C28 F10 1.297(8) . ? C28 F11 1.306(7) . ? C28 F12 1.360(8) . ? C29 C30 1.389(7) . ? C29 C34 1.405(7) . ? C30 C31 1.395(8) . ? C31 C32 1.359(9) . ? C32 C33 1.385(10) . ? C33 C34 1.374(8) . ? C35 C36 1.410(6) . ? C35 C40 1.421(6) . ? C36 C37 1.375(7) . ? C37 C38 1.378(7) . ? C37 C41 1.502(7) . ? C38 C39 1.387(7) . ? C39 C40 1.392(6) . ? C39 C42 1.491(7) . ? C41 F15 1.303(7) . ? C41 F14 1.324(7) . ? C41 F13 1.330(7) . ? C42 F17 1.329(6) . ? C42 F16 1.338(6) . ? C42 F18 1.349(6) . ? C43 C44 1.374(7) . ? C43 C48 1.382(7) . ? C44 C45 1.384(8) . ? C45 C46 1.349(9) . ? C46 C47 1.367(8) . ? C47 C48 1.384(7) . ? C49 C54 1.404(6) . ? C49 C50 1.413(6) . ? C50 C51 1.387(7) . ? C51 C52 1.381(7) . ? C51 C55 1.496(7) . ? C52 C53 1.386(6) . ? C53 C54 1.382(6) . ? C53 C56 1.488(7) . ? C55 F20 1.266(7) . ? C55 F21 1.268(7) . ? C55 F19 1.292(8) . ? C56 F22 1.278(7) . ? C56 F23' 1.280(8) . ? C56 F24' 1.289(7) . ? C56 F23 1.307(7) . ? C56 F22' 1.390(8) . ? C56 F24 1.392(7) . ? C57 C58 1.396(11) . ? C58 C59 1.336(14) . ? C59 C60 1.347(12) . ? C60 C61 1.383(8) . ? F6 K1 2.837(4) . ? F12 K1 2.729(5) . ? F14 K1 2.934(4) 3_666 ? F18 K1 2.802(3) . ? F24 K1 2.796(9) . ? F24' K1 2.760(12) . ? F25 K1 2.616(3) . ? K1 F14 2.934(4) 3_666 ? C62 C63 1.365(13) . ? C63 C64 1.37(2) . ? C64 C65 1.36(2) . ? C65 C66 1.349(13) . ? 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 F25 U1 N3 80.05(11) . . ? F25 U1 N4 85.24(11) . . ? N3 U1 N4 91.18(13) . . ? F25 U1 N2 84.12(12) . . ? N3 U1 N2 89.66(13) . . ? N4 U1 N2 169.02(13) . . ? F25 U1 N1 81.74(11) . . ? N3 U1 N1 161.76(13) . . ? N4 U1 N1 86.19(13) . . ? N2 U1 N1 89.58(13) . . ? F25 U1 N5 174.19(12) . . ? N3 U1 N5 96.63(14) . . ? N4 U1 N5 99.65(13) . . ? N2 U1 N5 91.12(14) . . ? N1 U1 N5 101.60(14) . . ? C7 N1 C1 116.7(4) . . ? C7 N1 U1 131.7(3) . . ? C1 N1 U1 111.6(3) . . ? C21 N2 C15 115.7(4) . . ? C21 N2 U1 130.5(3) . . ? C15 N2 U1 112.9(3) . . ? C29 N3 C35 113.3(4) . . ? C29 N3 U1 115.4(3) . . ? C35 N3 U1 131.3(3) . . ? C49 N4 C43 116.4(4) . . ? C49 N4 U1 132.2(3) . . ? C43 N4 U1 110.6(3) . . ? C57 N5 C61 116.7(6) . . ? C57 N5 U1 122.8(5) . . ? C61 N5 U1 120.1(4) . . ? C66 N6 C62 116.5(9) . . ? C66 N6 K1 126.9(7) . . ? C62 N6 K1 110.6(7) . . ? C6 C1 C2 118.0(7) . . ? C6 C1 N1 121.5(7) . . ? C2 C1 N1 120.5(6) . . ? C3 C2 C1 119.9(11) . . ? C4 C3 C2 119.0(12) . . ? C5 C4 C3 121.4(10) . . ? C4 C5 C6 120.2(11) . . ? C1 C6 C5 121.3(10) . . ? N1 C7 C12 120.9(4) . . ? N1 C7 C8 123.6(4) . . ? C12 C7 C8 115.5(4) . . ? C9 C8 C7 121.4(5) . . ? C8 C9 C10 122.2(5) . . ? C8 C9 C13 119.6(6) . . ? C10 C9 C13 118.3(5) . . ? C11 C10 C9 117.2(5) . . ? C10 C11 C12 121.5(5) . . ? C10 C11 C14 120.1(4) . . ? C12 C11 C14 118.4(4) . . ? C11 C12 C7 122.2(4) . . ? F2 C13 F1 115.3(8) . . ? F2 C13 F3 100.1(7) . . ? F1 C13 F3 100.1(6) . . ? F2 C13 C9 115.4(6) . . ? F1 C13 C9 113.9(6) . . ? F3 C13 C9 109.7(8) . . ? F5 C14 F4 106.0(4) . . ? F5 C14 F6 106.2(5) . . ? F4 C14 F6 103.3(5) . . ? F5 C14 C11 114.2(5) . . ? F4 C14 C11 113.5(4) . . ? F6 C14 C11 112.8(4) . . ? C20 C15 C16 118.3(5) . . ? C20 C15 N2 121.0(4) . . ? C16 C15 N2 120.8(4) . . ? C17 C16 C15 120.8(5) . . ? C18 C17 C16 120.5(6) . . ? C17 C18 C19 119.8(5) . . ? C18 C19 C20 120.3(6) . . ? C15 C20 C19 120.4(5) . . ? N2 C21 C22 123.6(4) . . ? N2 C21 C26 119.7(4) . . ? C22 C21 C26 116.7(4) . . ? C23 C22 C21 120.8(5) . . ? C24 C23 C22 122.1(5) . . ? C24 C23 C27 118.9(5) . . ? C22 C23 C27 118.9(5) . . ? C23 C24 C25 117.0(5) . . ? C26 C25 C24 122.4(5) . . ? C26 C25 C28 118.6(5) . . ? C24 C25 C28 118.9(5) . . ? C25 C26 C21 120.9(5) . . ? F7 C27 F8' 47.4(8) . . ? F7 C27 F9 122.0(10) . . ? F8' C27 F9 129.4(11) . . ? F7 C27 F9' 134.1(11) . . ? F8' C27 F9' 111.4(11) . . ? F9 C27 F9' 31.9(11) . . ? F7 C27 F8 97.6(8) . . ? F8' C27 F8 50.9(8) . . ? F9 C27 F8 100.4(8) . . ? F9' C27 F8 69.9(10) . . ? F7 C27 F7' 53.5(8) . . ? F8' C27 F7' 97.3(8) . . ? F9 C27 F7' 76.7(8) . . ? F9' C27 F7' 105.4(10) . . ? F8 C27 F7' 136.7(7) . . ? F7 C27 C23 112.7(6) . . ? F8' C27 C23 116.0(7) . . ? F9 C27 C23 112.5(8) . . ? F9' C27 C23 113.1(9) . . ? F8 C27 C23 108.7(6) . . ? F7' C27 C23 112.2(5) . . ? F10 C28 F11 107.6(5) . . ? F10 C28 F12 103.1(6) . . ? F11 C28 F12 104.0(6) . . ? F10 C28 C25 114.9(6) . . ? F11 C28 C25 115.1(5) . . ? F12 C28 C25 111.0(5) . . ? C30 C29 C34 117.2(4) . . ? C30 C29 N3 121.4(4) . . ? C34 C29 N3 121.2(4) . . ? C29 C30 C31 121.2(5) . . ? C32 C31 C30 120.7(6) . . ? C31 C32 C33 119.0(6) . . ? C34 C33 C32 121.1(6) . . ? C33 C34 C29 120.7(5) . . ? N3 C35 C36 124.7(4) . . ? N3 C35 C40 119.9(4) . . ? C36 C35 C40 115.3(4) . . ? C37 C36 C35 122.2(4) . . ? C36 C37 C38 122.1(5) . . ? C36 C37 C41 118.7(5) . . ? C38 C37 C41 119.1(5) . . ? C37 C38 C39 117.4(4) . . ? C38 C39 C40 121.7(4) . . ? C38 C39 C42 120.6(4) . . ? C40 C39 C42 117.6(4) . . ? C39 C40 C35 121.3(4) . . ? F15 C41 F14 107.4(5) . . ? F15 C41 F13 105.1(6) . . ? F14 C41 F13 103.9(5) . . ? F15 C41 C37 113.1(5) . . ? F14 C41 C37 113.6(5) . . ? F13 C41 C37 113.0(5) . . ? F17 C42 F16 106.2(4) . . ? F17 C42 F18 106.4(4) . . ? F16 C42 F18 105.3(4) . . ? F17 C42 C39 113.9(4) . . ? F16 C42 C39 112.6(4) . . ? F18 C42 C39 111.9(4) . . ? C44 C43 C48 117.0(5) . . ? C44 C43 N4 120.7(4) . . ? C48 C43 N4 122.3(4) . . ? C43 C44 C45 121.1(5) . . ? C46 C45 C44 121.3(6) . . ? C45 C46 C47 118.8(5) . . ? C46 C47 C48 120.4(5) . . ? C43 C48 C47 121.3(5) . . ? N4 C49 C54 120.3(4) . . ? N4 C49 C50 123.9(4) . . ? C54 C49 C50 115.9(4) . . ? C51 C50 C49 121.2(4) . . ? C52 C51 C50 122.1(4) . . ? C52 C51 C55 118.5(5) . . ? C50 C51 C55 119.5(5) . . ? C51 C52 C53 117.3(4) . . ? C54 C53 C52 121.7(4) . . ? C54 C53 C56 119.0(4) . . ? C52 C53 C56 119.4(4) . . ? C53 C54 C49 121.9(4) . . ? F20 C55 F21 106.4(6) . . ? F20 C55 F19 104.8(6) . . ? F21 C55 F19 102.7(6) . . ? F20 C55 C51 114.2(5) . . ? F21 C55 C51 113.4(5) . . ? F19 C55 C51 114.2(5) . . ? F22 C56 F23' 123.5(10) . . ? F22 C56 F24' 52.3(7) . . ? F23' C56 F24' 113.6(10) . . ? F22 C56 F23 108.9(7) . . ? F23' C56 F23 28.9(9) . . ? F24' C56 F23 127.7(8) . . ? F22 C56 F22' 46.6(6) . . ? F23' C56 F22' 104.0(9) . . ? F24' C56 F22' 98.7(8) . . ? F23 C56 F22' 76.8(8) . . ? F22 C56 F24 101.6(7) . . ? F23' C56 F24 73.5(9) . . ? F24' C56 F24 52.0(7) . . ? F23 C56 F24 100.9(6) . . ? F22' C56 F24 141.6(7) . . ? F22 C56 C53 118.1(5) . . ? F23' C56 C53 116.3(9) . . ? F24' C56 C53 115.6(6) . . ? F23 C56 C53 115.6(6) . . ? F22' C56 C53 105.8(6) . . ? F24 C56 C53 109.4(5) . . ? N5 C57 C58 121.7(8) . . ? C59 C58 C57 120.8(8) . . ? C58 C59 C60 118.2(7) . . ? C59 C60 C61 119.5(8) . . ? N5 C61 C60 123.0(7) . . ? C14 F6 K1 140.8(3) . . ? C28 F12 K1 136.8(4) . . ? C41 F14 K1 145.9(4) . 3_666 ? C42 F18 K1 127.6(3) . . ? C56 F24 K1 125.4(6) . . ? C56 F24' K1 134.5(9) . . ? U1 F25 K1 175.59(13) . . ? F25 K1 F12 95.99(13) . . ? F25 K1 F24' 88.6(3) . . ? F12 K1 F24' 174.5(2) . . ? F25 K1 F24 102.68(16) . . ? F12 K1 F24 154.7(2) . . ? F24' K1 F24 24.5(3) . . ? F25 K1 F18 93.79(10) . . ? F12 K1 F18 72.21(15) . . ? F24' K1 F18 104.5(3) . . ? F24 K1 F18 122.6(2) . . ? F25 K1 F6 86.43(10) . . ? F12 K1 F6 99.18(16) . . ? F24' K1 F6 84.1(3) . . ? F24 K1 F6 65.6(2) . . ? F18 K1 F6 171.36(12) . . ? F25 K1 N6 145.45(17) . . ? F12 K1 N6 69.0(2) . . ? F24' K1 N6 108.7(4) . . ? F24 K1 N6 86.1(3) . . ? F18 K1 N6 109.62(18) . . ? F6 K1 N6 66.65(18) . . ? F25 K1 F14 132.87(13) . 3_666 ? F12 K1 F14 115.06(17) . 3_666 ? F24' K1 F14 59.4(2) . 3_666 ? F24 K1 F14 62.74(17) . 3_666 ? F18 K1 F14 65.93(13) . 3_666 ? F6 K1 F14 119.78(14) . 3_666 ? N6 K1 F14 80.98(19) . 3_666 ? N6 C62 C63 123.7(13) . . ? C62 C63 C64 118.0(15) . . ? C65 C64 C63 118.6(11) . . ? C66 C65 C64 120.1(14) . . ? N6 C66 C65 122.9(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.642 _refine_diff_density_min -2.516 _refine_diff_density_rms 0.106 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.000 218 40 ' ' 2 0.500 0.000 0.500 308 66 ' ' 3 1.000 0.500 0.500 218 40 ' ' 4 0.500 0.500 0.000 308 66 ' ' #===END