# 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_9 #TrackingRef '15.cif' # start Validation Reply Form _vrf_PLAT029_9 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.740 RESPONSE: Many crytals tried - all multiple independent molecules with long unit cell parameters and twinning issues. Best overall result presented with unambiguous chiral centres. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration ad _chemical_formula_moiety 'C18 H12 Br F3 O2' _chemical_formula_sum 'C18 H12 Br F3 O2' _chemical_formula_weight 397.19 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.822(3) _cell_length_b 47.948(9) _cell_length_c 12.119(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.545(6) _cell_angle_gamma 90.00 _cell_volume 6649(2) _cell_formula_units_Z 16 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 7901 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 28.4 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3168 _exptl_absorpt_coefficient_mu 2.511 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.603 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20958 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.1432 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 57 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.34 _reflns_number_total 12425 _reflns_number_gt 7833 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.006(12) _refine_ls_number_reflns 12425 _refine_ls_number_parameters 1729 _refine_ls_number_restraints 43 _refine_ls_R_factor_all 0.1084 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1668 _refine_ls_wR_factor_gt 0.1433 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.969 _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 Br1 Br 0.61807(15) 0.22754(4) 0.99606(15) 0.0448(5) Uani 1 1 d . . . F1 F 0.1245(10) 0.4152(3) 0.9945(9) 0.076(4) Uani 1 1 d . . . O1 O 0.3224(9) 0.3829(2) 1.0109(9) 0.043(3) Uani 1 1 d . . . F2 F 0.2790(9) 0.4335(2) 1.0970(10) 0.071(3) Uani 1 1 d . . . C2 C 0.3777(16) 0.3585(4) 0.9953(15) 0.049(5) Uani 1 1 d . . . F3 F 0.1518(10) 0.4159(2) 1.1748(10) 0.074(4) Uani 1 1 d . . . C3 C 0.3319(14) 0.3324(3) 1.0475(14) 0.038(4) Uani 1 1 d . . . H3A H 0.2487 0.3291 1.0053 0.045 Uiso 1 1 calc R . . C4 C 0.3356(13) 0.3393(3) 1.1756(13) 0.029(4) Uani 1 1 d . . . H4A H 0.4187 0.3419 1.2193 0.035 Uiso 1 1 calc R . . C5 C 0.2686(14) 0.3662(3) 1.1794(14) 0.038(4) Uani 1 1 d . . . H5A H 0.2304 0.3697 1.2383 0.045 Uiso 1 1 calc R . . C6 C 0.2656(15) 0.3846(4) 1.0981(15) 0.041(5) Uani 1 1 d . . . C7 C 0.3986(13) 0.3079(3) 1.0364(13) 0.031(4) Uani 1 1 d . . . C8 C 0.5234(14) 0.3071(4) 1.0785(13) 0.043(5) Uani 1 1 d . . . H8A H 0.5641 0.3232 1.1131 0.051 Uiso 1 1 calc R . . C9 C 0.5860(12) 0.2826(3) 1.0691(12) 0.031(4) Uani 1 1 d . . . H9A H 0.6681 0.2817 1.1007 0.037 Uiso 1 1 calc R . . C10 C 0.5268(13) 0.2601(4) 1.0139(13) 0.033(4) Uani 1 1 d U . . C11 C 0.4080(14) 0.2599(3) 0.9719(14) 0.039(4) Uani 1 1 d . . . H11A H 0.3688 0.2437 0.9366 0.047 Uiso 1 1 calc R . . C12 C 0.3481(13) 0.2833(3) 0.9821(12) 0.030(4) Uani 1 1 d . . . H12A H 0.2660 0.2832 0.9505 0.036 Uiso 1 1 calc R . . C13 C 0.2817(13) 0.3153(3) 1.2291(13) 0.032(4) Uani 1 1 d . . . C14 C 0.3603(15) 0.2957(4) 1.2999(14) 0.047(5) Uani 1 1 d . . . H14A H 0.4423 0.2976 1.3098 0.056 Uiso 1 1 calc R . . C15 C 0.3183(17) 0.2748(4) 1.3520(14) 0.050(5) Uani 1 1 d . . . H15A H 0.3708 0.2627 1.4022 0.060 Uiso 1 1 calc R . . C16 C 0.2000(15) 0.2708(4) 1.3328(15) 0.048(5) Uani 1 1 d . . . H16A H 0.1708 0.2551 1.3648 0.057 Uiso 1 1 calc R . . C17 C 0.1240(14) 0.2894(4) 1.2677(13) 0.036(4) Uani 1 1 d . . . H17A H 0.0424 0.2877 1.2606 0.043 Uiso 1 1 calc R . . C18 C 0.1662(14) 0.3107(4) 1.2124(13) 0.042(5) Uani 1 1 d . . . H18A H 0.1125 0.3223 1.1612 0.051 Uiso 1 1 calc R . . C19 C 0.2054(17) 0.4126(5) 1.0924(19) 0.059(6) Uani 1 1 d . . . O20 O 0.4355(10) 0.3590(3) 0.9296(10) 0.052(3) Uani 1 1 d . . . Br2 Br -0.10691(15) 0.28202(4) 0.99283(15) 0.0434(5) Uani 1 1 d . . . F4 F 0.2973(10) 0.0876(2) 0.7865(9) 0.079(4) Uani 1 1 d . . . F5 F 0.1421(10) 0.0750(2) 0.8377(9) 0.072(3) Uani 1 1 d . . . F6 F 0.3057(9) 0.0815(3) 0.9638(10) 0.072(4) Uani 1 1 d . . . O21 O 0.1394(10) 0.1238(2) 0.9502(9) 0.044(3) Uani 1 1 d . . . C22 C 0.0859(15) 0.1491(4) 0.9550(14) 0.040(4) Uani 1 1 d . . . C23 C 0.0978(13) 0.1713(3) 0.8719(13) 0.035(4) Uani 1 1 d . . . H23A H 0.0474 0.1655 0.7961 0.042 Uiso 1 1 calc R . . C24 C 0.2231(13) 0.1710(3) 0.8609(13) 0.031(4) Uani 1 1 d . . . H24A H 0.2758 0.1753 0.9373 0.037 Uiso 1 1 calc R . . C25 C 0.2518(13) 0.1427(4) 0.8279(13) 0.033(4) Uani 1 1 d . . . H25A H 0.2991 0.1403 0.7758 0.039 Uiso 1 1 calc R . . C26 C 0.2097(16) 0.1202(4) 0.8733(15) 0.045(5) Uani 1 1 d . . . C27 C 0.0507(12) 0.1990(3) 0.9007(13) 0.028(4) Uani 1 1 d . . . C28 C -0.0627(13) 0.2064(3) 0.8500(12) 0.029(4) Uani 1 1 d . . . H28A H -0.1096 0.1940 0.7962 0.035 Uiso 1 1 calc R . . C29 C -0.1125(15) 0.2318(4) 0.8749(14) 0.047(5) Uani 1 1 d . . . H29A H -0.1903 0.2371 0.8380 0.057 Uiso 1 1 calc R . . C30 C -0.0404(12) 0.2485(3) 0.9564(12) 0.026(3) Uani 1 1 d U . . C31 C 0.0752(12) 0.2428(3) 1.0106(12) 0.029(4) Uani 1 1 d . . . H31A H 0.1226 0.2552 1.0639 0.035 Uiso 1 1 calc R . . C32 C 0.1170(13) 0.2166(3) 0.9790(12) 0.025(3) Uani 1 1 d U . . H32A H 0.1950 0.2113 1.0148 0.030 Uiso 1 1 calc R . . C33 C 0.2455(15) 0.1938(3) 0.7719(14) 0.034(4) Uani 1 1 d . . . C34 C 0.1575(15) 0.2041(3) 0.6881(14) 0.039(5) Uani 1 1 d . . . H34A H 0.0791 0.1986 0.6835 0.047 Uiso 1 1 calc R . . C35 C 0.1808(15) 0.2220(4) 0.6108(13) 0.044(5) Uani 1 1 d . . . H35A H 0.1197 0.2287 0.5498 0.053 Uiso 1 1 calc R . . C36 C 0.3015(17) 0.2311(3) 0.6224(14) 0.045(5) Uani 1 1 d . . . H36A H 0.3189 0.2449 0.5727 0.054 Uiso 1 1 calc R . . C37 C 0.3879(17) 0.2197(4) 0.7045(16) 0.051(5) Uani 1 1 d . . . H37A H 0.4672 0.2247 0.7119 0.061 Uiso 1 1 calc R . . C38 C 0.3580(14) 0.2002(3) 0.7783(14) 0.035(4) Uani 1 1 d . . . H38A H 0.4182 0.1913 0.8340 0.042 Uiso 1 1 calc R . . C39 C 0.2386(16) 0.0916(4) 0.8649(16) 0.043(5) Uani 1 1 d . . . O40 O 0.0273(8) 0.1508(2) 1.0255(9) 0.036(3) Uani 1 1 d . . . Br3 Br 0.50758(16) 0.07153(4) 0.66381(17) 0.0579(6) Uani 1 1 d . . . F7 F -0.2152(8) 0.2063(3) 0.2783(10) 0.085(5) Uani 1 1 d . . . F8 F -0.1116(9) 0.2296(3) 0.1890(9) 0.076(4) Uani 1 1 d . . . F9 F -0.0933(9) 0.2343(3) 0.3684(11) 0.078(4) Uani 1 1 d . . . O41 O -0.0214(9) 0.1805(3) 0.4126(9) 0.044(3) Uani 1 1 d . . . C42 C 0.0694(14) 0.1628(4) 0.4631(14) 0.035(4) Uani 1 1 d . . . C43 C 0.1793(13) 0.1651(3) 0.4182(13) 0.031(4) Uani 1 1 d . . . H43A H 0.2178 0.1832 0.4466 0.038 Uiso 1 1 calc R . . C44 C 0.1511(13) 0.1660(3) 0.2867(12) 0.034(4) Uani 1 1 d U . . H44A H 0.1178 0.1477 0.2543 0.040 Uiso 1 1 calc R . . C45 C 0.0564(12) 0.1897(3) 0.2518(14) 0.035(4) Uani 1 1 d . . . H45A H 0.0530 0.2005 0.1852 0.042 Uiso 1 1 calc R . . C46 C -0.0149(14) 0.1946(4) 0.3113(16) 0.048(5) Uani 1 1 d . . . C47 C 0.2626(13) 0.1424(3) 0.4702(13) 0.027(4) Uani 1 1 d . . . C48 C 0.3619(13) 0.1486(3) 0.5611(12) 0.029(4) Uani 1 1 d . . . H48A H 0.3780 0.1675 0.5836 0.035 Uiso 1 1 calc R . . C49 C 0.4334(14) 0.1284(3) 0.6158(14) 0.035(4) Uani 1 1 d . . . H49A H 0.4980 0.1329 0.6777 0.041 Uiso 1 1 calc R . . C50 C 0.4113(15) 0.1010(4) 0.5805(14) 0.039(4) Uani 1 1 d . . . C51 C 0.3217(14) 0.0929(4) 0.4946(15) 0.045(5) Uani 1 1 d . . . H51A H 0.3093 0.0739 0.4723 0.054 Uiso 1 1 calc R . . C52 C 0.2460(15) 0.1147(4) 0.4391(14) 0.040(4) Uani 1 1 d . . . H52A H 0.1814 0.1100 0.3778 0.048 Uiso 1 1 calc R . . C53 C 0.2593(15) 0.1729(4) 0.2457(14) 0.039(4) Uani 1 1 d . . . C54 C 0.3096(15) 0.1513(5) 0.1966(13) 0.057(6) Uani 1 1 d . . . H54A H 0.2754 0.1333 0.1890 0.068 Uiso 1 1 calc R . . C55 C 0.4082(18) 0.1562(6) 0.1595(15) 0.067(7) Uani 1 1 d . . . H55A H 0.4413 0.1416 0.1245 0.081 Uiso 1 1 calc R . . C56 C 0.4595(15) 0.1824(6) 0.1732(16) 0.067(8) Uani 1 1 d . . . H56A H 0.5304 0.1852 0.1513 0.081 Uiso 1 1 calc R . . C57 C 0.4103(14) 0.2049(5) 0.2182(15) 0.058(6) Uani 1 1 d . . . H57A H 0.4415 0.2232 0.2231 0.070 Uiso 1 1 calc R . . C58 C 0.3103(14) 0.1978(4) 0.2556(13) 0.045(5) Uani 1 1 d . . . H58A H 0.2763 0.2121 0.2910 0.054 Uiso 1 1 calc R . . C59 C -0.1117(18) 0.2160(5) 0.2834(17) 0.058(6) Uani 1 1 d . . . O60 O 0.0589(9) 0.1497(2) 0.5425(9) 0.034(3) Uani 1 1 d . . . Br4 Br 0.15329(18) 0.49150(5) 0.61369(19) 0.0718(7) Uani 1 1 d . . . F10 F 0.9009(9) 0.3611(4) 0.9628(12) 0.123(6) Uani 1 1 d . . . F11 F 0.7813(11) 0.3382(3) 1.0371(10) 0.093(4) Uani 1 1 d . . . F12 F 0.8870(15) 0.3694(4) 1.1327(11) 0.147(8) Uani 1 1 d . . . O61 O 0.6693(9) 0.3749(3) 0.8765(10) 0.045(3) Uani 1 1 d . . . C62 C 0.5869(16) 0.3929(4) 0.8124(17) 0.042(5) Uani 1 1 d . . . C63 C 0.5832(14) 0.4208(4) 0.8566(13) 0.037(4) Uani 1 1 d . . . H63A H 0.6515 0.4307 0.8400 0.044 Uiso 1 1 calc R . . C64 C 0.5999(14) 0.4234(3) 0.9883(12) 0.035(4) Uani 1 1 d . . . H64A H 0.5283 0.4166 1.0096 0.042 Uiso 1 1 calc R . . C65 C 0.7043(15) 0.4040(4) 1.0399(14) 0.044(5) Uani 1 1 d . . . H65A H 0.7503 0.4079 1.1145 0.053 Uiso 1 1 calc R . . C66 C 0.7313(16) 0.3831(5) 0.9874(16) 0.051(5) Uani 1 1 d . . . C67 C 0.4756(13) 0.4373(3) 0.7937(12) 0.029(4) Uani 1 1 d . . . C68 C 0.4825(15) 0.4593(4) 0.7167(13) 0.038(4) Uani 1 1 d . . . H68A H 0.5561 0.4631 0.7017 0.046 Uiso 1 1 calc R . . C69 C 0.3891(13) 0.4752(4) 0.6631(14) 0.038(4) Uani 1 1 d . . . H69A H 0.3972 0.4898 0.6128 0.046 Uiso 1 1 calc R . . C70 C 0.2853(14) 0.4694(4) 0.6841(13) 0.044(5) Uani 1 1 d . . . C71 C 0.2702(14) 0.4482(4) 0.7624(14) 0.036(4) Uani 1 1 d . . . H71A H 0.1973 0.4452 0.7800 0.043 Uiso 1 1 calc R . . C72 C 0.3660(13) 0.4328(4) 0.8097(13) 0.035(4) Uani 1 1 d . . . H72A H 0.3569 0.4178 0.8577 0.042 Uiso 1 1 calc R . . C73 C 0.6210(15) 0.4535(3) 1.0218(13) 0.036(4) Uani 1 1 d . . . C74 C 0.7162(16) 0.4688(4) 1.0174(15) 0.055(5) Uani 1 1 d . . . H74A H 0.7799 0.4598 0.9977 0.066 Uiso 1 1 calc R . . C75 C 0.7242(19) 0.4979(5) 1.0412(18) 0.077(7) Uani 1 1 d . . . H75A H 0.7914 0.5084 1.0374 0.092 Uiso 1 1 calc R . . C76 C 0.6313(19) 0.5101(4) 1.0698(18) 0.075(7) Uani 1 1 d . . . H76A H 0.6347 0.5296 1.0848 0.090 Uiso 1 1 calc R . . C77 C 0.537(2) 0.4963(5) 1.0776(17) 0.069(6) Uani 1 1 d . . . H77A H 0.4759 0.5059 1.0997 0.083 Uiso 1 1 calc R . . C78 C 0.5259(17) 0.4687(4) 1.0546(14) 0.053(5) Uani 1 1 d . . . H78A H 0.4571 0.4591 1.0595 0.063 Uiso 1 1 calc R . . C79 C 0.838(2) 0.3634(6) 1.028(2) 0.075(7) Uani 1 1 d U . . O80 O 0.5341(10) 0.3841(3) 0.7191(10) 0.046(3) Uani 1 1 d . . . Br5 Br -0.04535(15) 0.42937(4) 0.31456(17) 0.0531(5) Uani 1 1 d . . . F13 F 0.6445(11) 0.2770(3) 0.6316(11) 0.093(5) Uani 1 1 d . . . F14 F 0.6944(9) 0.3132(3) 0.7400(10) 0.081(4) Uani 1 1 d . . . F15 F 0.6027(9) 0.2786(3) 0.7923(10) 0.081(4) Uani 1 1 d . . . O81 O 0.5069(9) 0.3235(2) 0.5611(8) 0.036(3) Uani 1 1 d . . . C82 C 0.4259(14) 0.3436(4) 0.5160(15) 0.039(5) Uani 1 1 d . . . C83 C 0.3305(13) 0.3482(4) 0.5792(13) 0.036(5) Uani 1 1 d . . . H83A H 0.3671 0.3585 0.6511 0.043 Uiso 1 1 calc R . . C84 C 0.2893(12) 0.3185(4) 0.6154(14) 0.038(4) Uani 1 1 d . . . H84A H 0.2553 0.3075 0.5449 0.045 Uiso 1 1 calc R . . C85 C 0.3967(13) 0.3040(3) 0.6823(13) 0.036(4) Uani 1 1 d . . . H85A H 0.3926 0.2927 0.7455 0.043 Uiso 1 1 calc R . . C86 C 0.5005(14) 0.3068(4) 0.6536(13) 0.037(4) Uani 1 1 d . . . C87 C 0.2338(13) 0.3663(3) 0.5115(13) 0.027(4) Uani 1 1 d . . . C88 C 0.2526(13) 0.3958(4) 0.5271(13) 0.034(4) Uani 1 1 d . . . H88A H 0.3215 0.4028 0.5779 0.041 Uiso 1 1 calc R . . C89 C 0.1699(13) 0.4134(4) 0.4677(15) 0.041(5) Uani 1 1 d . . . H89A H 0.1821 0.4330 0.4759 0.049 Uiso 1 1 calc R . . C90 C 0.0714(14) 0.4039(5) 0.3979(15) 0.048(6) Uani 1 1 d . . . C91 C 0.0451(14) 0.3759(4) 0.3784(14) 0.037(4) Uani 1 1 d . . . H91A H -0.0259 0.3693 0.3297 0.044 Uiso 1 1 calc R . . C92 C 0.1327(15) 0.3584(4) 0.4369(13) 0.040(5) Uani 1 1 d . . . H92A H 0.1212 0.3389 0.4237 0.048 Uiso 1 1 calc R . . C93 C 0.1970(15) 0.3219(4) 0.6815(14) 0.044(5) Uani 1 1 d . . . C94 C 0.1239(16) 0.2994(4) 0.6812(15) 0.058(6) Uani 1 1 d . . . H94A H 0.1319 0.2832 0.6391 0.070 Uiso 1 1 calc R . . C95 C 0.0369(15) 0.3004(5) 0.7431(17) 0.059(6) Uani 1 1 d . . . H95A H -0.0093 0.2844 0.7475 0.071 Uiso 1 1 calc R . . C96 C 0.0200(17) 0.3250(6) 0.7974(18) 0.073(8) Uani 1 1 d . . . H96A H -0.0417 0.3264 0.8344 0.088 Uiso 1 1 calc R . . C97 C 0.0894(15) 0.3465(5) 0.7976(15) 0.059(6) Uani 1 1 d . . . H97A H 0.0785 0.3631 0.8367 0.071 Uiso 1 1 calc R . . C98 C 0.1809(13) 0.3453(4) 0.7399(13) 0.047(5) Uani 1 1 d . . . H98A H 0.2309 0.3609 0.7423 0.056 Uiso 1 1 calc R . . C99 C 0.6116(18) 0.2931(5) 0.7058(19) 0.061(6) Uani 1 1 d . . . O100 O 0.4371(9) 0.3556(3) 0.4332(9) 0.039(3) Uani 1 1 d . . . Br6 Br 0.36679(15) 0.50268(4) 0.34132(18) 0.0535(5) Uani 1 1 d . . . F16 F 0.6891(10) 0.2943(2) 0.3606(9) 0.071(3) Uani 1 1 d . . . F17 F 0.8400(10) 0.3127(3) 0.3227(10) 0.088(4) Uani 1 1 d . . . F18 F 0.8424(10) 0.3021(2) 0.4970(10) 0.080(4) Uani 1 1 d . . . O101 O 0.6605(10) 0.3499(3) 0.3072(10) 0.046(3) Uani 1 1 d . . . C102 C 0.6220(17) 0.3762(4) 0.2982(15) 0.038(5) Uani 1 1 d . . . C103 C 0.6747(13) 0.3977(3) 0.3892(12) 0.033(4) Uani 1 1 d . . . H10A H 0.7509 0.4036 0.3750 0.039 Uiso 1 1 calc R . . C104 C 0.7028(13) 0.3841(4) 0.5104(13) 0.036(4) Uani 1 1 d . . . H10B H 0.6291 0.3830 0.5364 0.043 Uiso 1 1 calc R . . C105 C 0.7517(13) 0.3548(3) 0.5075(14) 0.035(4) Uani 1 1 d . . . H10C H 0.7963 0.3463 0.5755 0.043 Uiso 1 1 calc R . . C106 C 0.7317(15) 0.3413(4) 0.4106(16) 0.042(5) Uani 1 1 d . . . C107 C 0.6005(14) 0.4225(4) 0.3762(13) 0.038(4) Uani 1 1 d . . . C108 C 0.4835(14) 0.4217(4) 0.3812(16) 0.055(5) Uani 1 1 d . . . H10D H 0.4490 0.4043 0.3912 0.066 Uiso 1 1 calc R . . C109 C 0.4176(15) 0.4454(4) 0.3721(15) 0.050(5) Uani 1 1 d . . . H10E H 0.3386 0.4443 0.3765 0.060 Uiso 1 1 calc R . . C110 C 0.4641(14) 0.4705(3) 0.3569(13) 0.032(4) Uani 1 1 d . . . C111 C 0.5776(14) 0.4729(4) 0.3502(14) 0.041(5) Uani 1 1 d . . . H11B H 0.6095 0.4904 0.3376 0.049 Uiso 1 1 calc R . . C112 C 0.6438(13) 0.4490(3) 0.3624(14) 0.034(4) Uani 1 1 d . . . H11C H 0.7236 0.4507 0.3613 0.041 Uiso 1 1 calc R . . C113 C 0.7884(13) 0.4024(3) 0.5917(14) 0.034(4) Uani 1 1 d . . . C114 C 0.7437(16) 0.4255(4) 0.6402(14) 0.050(5) Uani 1 1 d . . . H11D H 0.6622 0.4291 0.6228 0.060 Uiso 1 1 calc R . . C115 C 0.8255(17) 0.4431(4) 0.7163(16) 0.063(6) Uani 1 1 d . . . H11E H 0.7973 0.4582 0.7527 0.076 Uiso 1 1 calc R . . C116 C 0.9350(16) 0.4390(5) 0.736(2) 0.094(10) Uani 1 1 d . . . H11F H 0.9868 0.4520 0.7818 0.113 Uiso 1 1 calc R . . C117 C 0.9823(17) 0.4154(5) 0.6916(17) 0.079(8) Uani 1 1 d . . . H11G H 1.0631 0.4109 0.7140 0.095 Uiso 1 1 calc R . . C118 C 0.9019(17) 0.3991(4) 0.6128(16) 0.063(6) Uani 1 1 d . . . H11H H 0.9313 0.3850 0.5725 0.076 Uiso 1 1 calc R . . C119 C 0.778(2) 0.3123(5) 0.4009(19) 0.071(7) Uani 1 1 d . . . O120 O 0.5535(9) 0.3820(2) 0.2082(9) 0.042(3) Uani 1 1 d . . . Br7 Br 1.11522(16) 0.00382(4) 0.63938(16) 0.0526(5) Uani 1 1 d . . . F19 F 0.5748(10) 0.1951(2) 0.4729(9) 0.077(4) Uani 1 1 d . . . F20 F 0.7546(10) 0.2070(3) 0.5410(10) 0.075(3) Uani 1 1 d . . . F21 F 0.6484(9) 0.1966(3) 0.6517(9) 0.070(4) Uani 1 1 d . . . O121 O 0.8045(10) 0.1545(3) 0.6380(9) 0.041(3) Uani 1 1 d . . . C122 C 0.8588(16) 0.1293(4) 0.6416(17) 0.043(5) Uani 1 1 d . . . C123 C 0.8259(13) 0.1122(4) 0.5332(14) 0.037(4) Uani 1 1 d . . . H12B H 0.8558 0.1225 0.4744 0.044 Uiso 1 1 calc R . . C124 C 0.6911(13) 0.1110(4) 0.4897(14) 0.039(4) Uani 1 1 d . . . H12C H 0.6594 0.1015 0.5489 0.047 Uiso 1 1 calc R . . C125 C 0.6500(15) 0.1396(4) 0.4803(14) 0.043(5) Uani 1 1 d . . . H12D H 0.5815 0.1443 0.4233 0.051 Uiso 1 1 calc R . . C126 C 0.7058(17) 0.1595(4) 0.5496(17) 0.049(5) Uani 1 1 d . . . C127 C 0.8874(13) 0.0846(3) 0.5513(13) 0.034(4) Uani 1 1 d . . . C128 C 1.0018(12) 0.0834(4) 0.5356(14) 0.045(5) Uani 1 1 d . . . H12E H 1.0334 0.0989 0.5048 0.054 Uiso 1 1 calc R . . C129 C 1.0683(13) 0.0591(4) 0.5657(14) 0.043(5) Uani 1 1 d . . . H12F H 1.1464 0.0585 0.5583 0.051 Uiso 1 1 calc R . . C130 C 1.0204(15) 0.0359(4) 0.6065(14) 0.040(4) Uani 1 1 d . . . C131 C 0.9101(14) 0.0374(3) 0.6201(13) 0.036(4) Uani 1 1 d . . . H13A H 0.8767 0.0215 0.6467 0.044 Uiso 1 1 calc R . . C132 C 0.8480(15) 0.0609(4) 0.5965(13) 0.038(4) Uani 1 1 d . . . H13B H 0.7728 0.0614 0.6113 0.046 Uiso 1 1 calc R . . C133 C 0.6477(15) 0.0949(4) 0.3754(15) 0.041(4) Uani 1 1 d . . . C134 C 0.6089(13) 0.0681(4) 0.3782(14) 0.043(4) Uani 1 1 d . . . H13C H 0.6112 0.0592 0.4488 0.051 Uiso 1 1 calc R . . C135 C 0.5649(15) 0.0539(4) 0.2728(16) 0.054(5) Uani 1 1 d . . . H13D H 0.5366 0.0354 0.2735 0.065 Uiso 1 1 calc R . . C136 C 0.5627(13) 0.0664(4) 0.1702(14) 0.046(5) Uani 1 1 d . . . H13E H 0.5372 0.0565 0.1003 0.055 Uiso 1 1 calc R . . C137 C 0.6003(14) 0.0948(4) 0.1726(16) 0.044(4) Uani 1 1 d . . . H13F H 0.5922 0.1047 0.1031 0.053 Uiso 1 1 calc R . . C138 C 0.6467(13) 0.1076(4) 0.2717(13) 0.039(4) Uani 1 1 d . . . H13G H 0.6795 0.1257 0.2715 0.046 Uiso 1 1 calc R . . C139 C 0.6718(19) 0.1885(4) 0.5508(19) 0.060(6) Uani 1 1 d . . . O140 O 0.9278(10) 0.1235(3) 0.7282(10) 0.049(3) Uani 1 1 d . . . Br8 Br 0.33023(16) 0.01208(4) 0.39744(16) 0.0530(5) Uani 1 1 d . . . F22 F -0.3941(9) 0.1504(3) -0.0319(11) 0.085(4) Uani 1 1 d . . . F23 F -0.3307(9) 0.1381(3) -0.1764(9) 0.081(4) Uani 1 1 d . . . F24 F -0.2344(8) 0.1677(2) -0.0544(10) 0.067(3) Uani 1 1 d . . . O141 O -0.1792(9) 0.1286(2) 0.1096(10) 0.038(3) Uani 1 1 d . . . C142 C -0.0895(15) 0.1127(4) 0.1743(16) 0.036(4) Uani 1 1 d . . . C143 C -0.0562(12) 0.0871(3) 0.1089(13) 0.029(4) Uani 1 1 d . . . H14B H -0.0218 0.0951 0.0483 0.035 Uiso 1 1 calc R . . C144 C -0.1683(12) 0.0738(3) 0.0476(12) 0.027(4) Uani 1 1 d . . . H14C H -0.2134 0.0702 0.1057 0.033 Uiso 1 1 calc R . . C145 C -0.2360(14) 0.0934(4) -0.0329(14) 0.041(5) Uani 1 1 d . . . H14D H -0.2808 0.0875 -0.1056 0.049 Uiso 1 1 calc R . . C146 C -0.2332(16) 0.1220(4) 0.0004(16) 0.049(5) Uani 1 1 d . . . C147 C 0.0389(13) 0.0698(4) 0.1832(13) 0.038(4) Uani 1 1 d . . . C148 C 0.0143(13) 0.0512(3) 0.2602(13) 0.032(4) Uani 1 1 d U . . H14E H -0.0624 0.0505 0.2710 0.039 Uiso 1 1 calc R . . C149 C 0.1001(14) 0.0335(4) 0.3227(13) 0.043(5) Uani 1 1 d . . . H14F H 0.0836 0.0206 0.3762 0.051 Uiso 1 1 calc R . . C150 C 0.2110(15) 0.0354(4) 0.3035(14) 0.042(4) Uani 1 1 d U . . C151 C 0.2371(15) 0.0530(4) 0.2296(15) 0.049(5) Uani 1 1 d . . . H15B H 0.3145 0.0539 0.2203 0.058 Uiso 1 1 calc R . . C152 C 0.1504(13) 0.0699(5) 0.1658(13) 0.047(5) Uani 1 1 d . . . H15C H 0.1674 0.0819 0.1094 0.056 Uiso 1 1 calc R . . C153 C -0.1475(15) 0.0453(4) -0.0023(14) 0.042(5) Uani 1 1 d . . . C154 C -0.1993(17) 0.0218(4) 0.0306(17) 0.061(6) Uani 1 1 d . . . H15D H -0.2541 0.0237 0.0756 0.073 Uiso 1 1 calc R . . C155 C -0.1711(19) -0.0047(5) -0.0023(16) 0.076(7) Uani 1 1 d . . . H15E H -0.2030 -0.0207 0.0252 0.091 Uiso 1 1 calc R . . C156 C -0.0996(18) -0.0082(6) -0.0725(17) 0.076(7) Uani 1 1 d . . . H15F H -0.0828 -0.0263 -0.0955 0.091 Uiso 1 1 calc R . . C157 C -0.0521(16) 0.0145(5) -0.1096(15) 0.056(6) Uani 1 1 d . . . H15G H -0.0018 0.0119 -0.1587 0.067 Uiso 1 1 calc R . . C158 C -0.0748(15) 0.0425(4) -0.0777(13) 0.047(5) Uani 1 1 d . . . H15H H -0.0424 0.0583 -0.1060 0.056 Uiso 1 1 calc R . . C159 C -0.2990(16) 0.1439(4) -0.0614(16) 0.047(5) Uani 1 1 d . . . O160 O -0.0447(9) 0.1191(2) 0.2703(10) 0.040(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 Br1 0.0443(10) 0.0362(10) 0.0549(12) -0.0008(9) 0.0146(10) 0.0036(9) F1 0.075(8) 0.082(10) 0.064(8) 0.027(7) 0.003(7) 0.052(7) O1 0.050(7) 0.041(8) 0.046(7) 0.010(6) 0.028(7) 0.011(6) F2 0.086(8) 0.036(7) 0.108(9) 0.006(7) 0.054(8) 0.003(6) C2 0.056(12) 0.034(11) 0.050(13) 0.015(9) 0.002(11) 0.029(10) F3 0.087(8) 0.058(8) 0.096(9) 0.017(6) 0.057(8) 0.033(6) C3 0.034(10) 0.043(11) 0.045(11) 0.005(9) 0.028(9) 0.015(8) C4 0.028(9) 0.022(8) 0.040(10) 0.005(7) 0.013(8) 0.001(7) C5 0.055(12) 0.014(9) 0.043(10) 0.006(8) 0.010(10) 0.004(8) C6 0.040(11) 0.041(12) 0.047(11) -0.004(9) 0.019(10) -0.001(9) C7 0.025(9) 0.023(9) 0.047(11) 0.009(8) 0.010(9) 0.004(7) C8 0.048(11) 0.045(11) 0.047(11) -0.007(9) 0.035(10) -0.003(9) C9 0.018(8) 0.032(9) 0.037(9) 0.004(8) -0.003(8) 0.014(7) C10 0.033(4) 0.034(4) 0.033(4) -0.0001(11) 0.0088(14) 0.0003(11) C11 0.039(10) 0.023(9) 0.058(12) -0.002(8) 0.016(10) -0.003(8) C12 0.026(9) 0.035(10) 0.024(8) 0.004(8) -0.004(8) -0.002(8) C13 0.036(10) 0.020(8) 0.045(10) 0.007(8) 0.019(9) 0.000(7) C14 0.049(11) 0.044(12) 0.052(12) -0.003(10) 0.021(10) 0.002(10) C15 0.070(14) 0.042(12) 0.031(10) 0.019(9) -0.001(10) 0.001(10) C16 0.056(12) 0.040(11) 0.058(13) 0.004(10) 0.035(11) -0.004(10) C17 0.038(10) 0.047(12) 0.034(10) -0.008(9) 0.027(9) -0.005(9) C18 0.034(10) 0.065(14) 0.025(9) 0.005(9) 0.003(9) 0.012(10) C19 0.044(13) 0.058(15) 0.074(16) 0.027(12) 0.012(13) 0.018(11) O20 0.063(8) 0.040(8) 0.066(9) 0.003(7) 0.036(7) -0.010(7) Br2 0.0472(11) 0.0323(10) 0.0538(11) 0.0025(9) 0.0183(10) 0.0093(9) F4 0.128(10) 0.033(7) 0.104(9) 0.006(6) 0.083(9) 0.018(7) F5 0.100(9) 0.033(7) 0.101(9) -0.014(6) 0.056(8) -0.009(7) F6 0.080(8) 0.062(9) 0.080(8) 0.020(7) 0.031(7) 0.049(7) O21 0.070(8) 0.035(7) 0.041(7) 0.007(6) 0.038(7) 0.005(6) C22 0.048(11) 0.030(10) 0.044(11) -0.001(8) 0.014(10) -0.015(8) C23 0.035(10) 0.033(10) 0.035(10) 0.006(8) 0.006(8) -0.004(8) C24 0.039(10) 0.023(9) 0.033(9) -0.004(7) 0.017(8) -0.008(8) C25 0.042(10) 0.029(9) 0.034(10) -0.002(8) 0.022(9) -0.007(8) C26 0.066(13) 0.026(10) 0.051(11) 0.001(9) 0.030(11) 0.007(9) C27 0.024(8) 0.027(8) 0.037(9) 0.011(7) 0.016(8) 0.000(7) C28 0.039(10) 0.025(9) 0.028(9) -0.005(7) 0.016(8) -0.006(7) C29 0.058(12) 0.029(11) 0.053(11) 0.008(9) 0.010(10) 0.019(9) C30 0.026(4) 0.025(4) 0.026(4) -0.0003(11) 0.0068(14) 0.0005(11) C31 0.024(8) 0.032(10) 0.035(9) 0.008(8) 0.014(8) 0.001(7) C32 0.025(4) 0.025(4) 0.025(4) 0.0000(11) 0.0066(14) 0.0003(11) C33 0.049(11) 0.013(8) 0.047(11) 0.005(8) 0.024(10) 0.002(8) C34 0.053(11) 0.028(10) 0.051(11) -0.015(9) 0.039(10) -0.014(9) C35 0.060(12) 0.048(13) 0.030(10) 0.001(9) 0.020(10) 0.004(10) C36 0.086(14) 0.019(9) 0.042(11) -0.003(8) 0.043(11) -0.010(9) C37 0.054(12) 0.029(11) 0.073(14) -0.001(10) 0.024(12) 0.004(9) C38 0.050(11) 0.005(7) 0.050(11) 0.001(7) 0.012(9) -0.004(7) C39 0.064(13) 0.028(10) 0.054(12) 0.020(9) 0.044(11) 0.020(9) O40 0.041(7) 0.027(6) 0.043(7) 0.001(5) 0.018(6) 0.005(5) Br3 0.0543(12) 0.0583(14) 0.0692(14) 0.0204(11) 0.0309(11) 0.0224(11) F7 0.030(6) 0.140(14) 0.081(8) 0.049(9) 0.011(6) 0.038(7) F8 0.053(7) 0.118(12) 0.057(7) 0.047(8) 0.012(6) 0.024(8) F9 0.073(8) 0.067(10) 0.099(9) 0.022(8) 0.035(8) 0.041(7) O41 0.038(7) 0.045(8) 0.051(7) 0.010(6) 0.018(6) 0.010(6) C42 0.042(11) 0.032(10) 0.033(10) -0.022(8) 0.010(9) -0.014(9) C43 0.035(9) 0.018(8) 0.038(10) -0.012(7) 0.004(9) -0.004(7) C44 0.034(4) 0.034(4) 0.033(4) -0.0002(11) 0.0085(14) -0.0005(11) C45 0.031(9) 0.025(9) 0.048(11) -0.012(8) 0.006(9) -0.004(7) C46 0.028(10) 0.052(13) 0.062(13) 0.025(10) 0.008(10) 0.006(9) C47 0.030(9) 0.018(8) 0.035(10) -0.006(7) 0.013(9) -0.004(7) C48 0.038(10) 0.025(9) 0.028(9) 0.008(7) 0.015(9) 0.010(8) C49 0.035(10) 0.017(9) 0.053(11) 0.003(8) 0.013(9) 0.010(7) C50 0.046(11) 0.030(10) 0.042(11) 0.012(9) 0.012(10) 0.009(9) C51 0.039(10) 0.041(12) 0.056(12) -0.009(10) 0.014(10) -0.018(9) C52 0.040(10) 0.042(11) 0.031(10) 0.005(9) -0.001(9) -0.003(9) C53 0.048(11) 0.039(11) 0.037(10) 0.014(8) 0.024(9) 0.006(9) C54 0.050(12) 0.097(19) 0.028(11) 0.009(11) 0.019(10) -0.003(12) C55 0.068(15) 0.11(2) 0.027(11) 0.008(12) 0.008(11) 0.008(15) C56 0.024(11) 0.14(3) 0.046(13) 0.035(15) 0.016(10) -0.003(13) C57 0.027(10) 0.094(19) 0.053(13) 0.028(12) 0.011(10) -0.004(11) C58 0.037(10) 0.067(14) 0.025(9) 0.024(9) 0.000(9) 0.024(10) C59 0.054(14) 0.087(19) 0.039(12) 0.017(13) 0.024(12) 0.020(13) O60 0.042(7) 0.033(7) 0.030(6) 0.004(6) 0.016(6) 0.001(5) Br4 0.0627(14) 0.0664(17) 0.0820(15) 0.0106(13) 0.0102(13) 0.0319(13) F10 0.051(7) 0.170(18) 0.141(12) -0.037(12) 0.011(8) 0.060(9) F11 0.103(10) 0.077(11) 0.086(9) 0.008(8) 0.001(8) 0.044(9) F12 0.205(17) 0.118(15) 0.073(9) -0.032(9) -0.051(10) 0.097(13) O61 0.037(7) 0.043(8) 0.051(8) -0.007(7) 0.007(7) 0.010(6) C62 0.042(12) 0.040(11) 0.052(12) -0.002(10) 0.025(11) -0.014(10) C63 0.041(10) 0.031(10) 0.036(10) -0.011(8) 0.005(9) -0.005(8) C64 0.051(11) 0.020(9) 0.031(9) -0.002(7) 0.005(9) 0.003(8) C65 0.050(12) 0.042(12) 0.035(10) -0.003(9) 0.003(9) 0.019(9) C66 0.041(11) 0.059(15) 0.050(13) -0.010(11) 0.008(11) 0.002(10) C67 0.031(9) 0.019(8) 0.026(9) 0.001(7) -0.013(8) -0.008(7) C68 0.039(10) 0.037(11) 0.029(9) 0.016(8) -0.009(8) -0.020(9) C69 0.030(10) 0.039(11) 0.044(11) 0.009(9) 0.007(9) 0.006(9) C70 0.029(10) 0.068(15) 0.025(9) 0.003(9) -0.012(9) 0.009(9) C71 0.029(9) 0.037(10) 0.042(10) 0.005(8) 0.008(9) -0.005(8) C72 0.030(9) 0.039(11) 0.033(10) -0.003(8) 0.004(8) -0.006(8) C73 0.050(11) 0.025(10) 0.026(9) -0.004(7) -0.004(9) 0.003(9) C74 0.045(12) 0.056(14) 0.057(13) -0.007(11) -0.002(11) -0.007(10) C75 0.069(15) 0.063(17) 0.097(18) -0.038(14) 0.019(15) -0.043(13) C76 0.096(17) 0.022(11) 0.093(17) 0.000(12) -0.001(16) -0.008(12) C77 0.090(17) 0.043(14) 0.082(15) -0.019(12) 0.037(14) -0.015(12) C78 0.068(14) 0.047(13) 0.036(11) -0.007(9) 0.002(11) -0.006(11) C79 0.075(7) 0.075(7) 0.075(7) -0.0003(11) 0.019(2) 0.0003(11) O80 0.043(7) 0.049(9) 0.045(8) -0.004(7) 0.011(7) -0.002(7) Br5 0.0369(10) 0.0456(12) 0.0780(14) 0.0084(11) 0.0168(11) 0.0114(9) F13 0.101(10) 0.092(12) 0.099(10) 0.036(8) 0.051(9) 0.062(9) F14 0.037(6) 0.102(12) 0.095(9) 0.032(8) -0.001(7) -0.013(7) F15 0.055(7) 0.103(12) 0.086(8) 0.061(8) 0.016(7) 0.001(7) O81 0.029(6) 0.042(8) 0.035(6) 0.010(6) 0.003(5) 0.002(6) C82 0.037(10) 0.045(12) 0.034(11) -0.002(9) 0.009(9) 0.019(9) C83 0.040(10) 0.051(12) 0.028(10) -0.005(8) 0.028(9) -0.014(9) C84 0.027(9) 0.040(11) 0.048(11) -0.006(9) 0.014(9) -0.011(8) C85 0.045(10) 0.030(9) 0.042(10) -0.005(8) 0.028(9) -0.013(8) C86 0.046(11) 0.037(11) 0.030(10) 0.007(8) 0.011(9) 0.001(9) C87 0.026(9) 0.035(10) 0.022(9) 0.019(8) 0.011(8) 0.005(8) C88 0.019(9) 0.041(11) 0.039(10) -0.011(9) 0.002(8) 0.007(8) C89 0.026(10) 0.038(11) 0.066(12) -0.009(9) 0.027(10) -0.015(8) C90 0.015(9) 0.089(17) 0.039(11) 0.024(11) 0.007(9) 0.026(10) C91 0.021(9) 0.033(11) 0.043(10) 0.021(9) -0.018(9) -0.008(8) C92 0.060(12) 0.025(10) 0.031(10) -0.006(8) 0.004(10) -0.030(10) C93 0.048(12) 0.049(12) 0.039(11) 0.002(9) 0.017(10) 0.005(10) C94 0.070(14) 0.055(14) 0.042(11) -0.009(10) -0.001(11) -0.019(12) C95 0.045(12) 0.058(15) 0.072(15) 0.026(12) 0.012(12) -0.004(11) C96 0.048(13) 0.12(3) 0.065(15) 0.011(15) 0.035(12) 0.007(14) C97 0.042(12) 0.092(19) 0.039(12) 0.026(12) 0.001(10) 0.012(12) C98 0.031(10) 0.082(16) 0.035(11) -0.004(10) 0.023(9) 0.000(10) C99 0.047(13) 0.050(15) 0.078(16) 0.029(13) -0.002(13) 0.004(12) O100 0.037(7) 0.042(8) 0.038(7) 0.006(6) 0.009(6) -0.003(6) Br6 0.0471(11) 0.0350(11) 0.0825(14) 0.0020(11) 0.0239(11) 0.0055(9) F16 0.077(8) 0.028(7) 0.094(9) -0.008(6) -0.004(7) 0.008(6) F17 0.087(9) 0.091(12) 0.091(9) -0.008(8) 0.034(8) 0.036(8) F18 0.103(10) 0.042(8) 0.073(8) -0.012(7) -0.018(7) 0.031(7) O101 0.041(7) 0.048(9) 0.048(8) -0.002(7) 0.008(7) -0.002(6) C102 0.061(13) 0.032(10) 0.028(10) 0.007(9) 0.025(11) 0.002(9) C103 0.041(10) 0.029(9) 0.033(10) 0.023(8) 0.019(9) 0.011(8) C104 0.024(9) 0.046(11) 0.035(10) 0.005(9) 0.002(9) 0.005(8) C105 0.033(10) 0.025(9) 0.039(10) 0.025(8) -0.008(9) 0.004(8) C106 0.040(11) 0.048(12) 0.035(11) -0.001(10) 0.006(10) -0.008(9) C107 0.038(10) 0.047(12) 0.028(10) 0.001(9) 0.004(9) -0.012(9) C108 0.038(11) 0.036(11) 0.088(15) 0.037(11) 0.009(11) 0.005(9) C109 0.049(11) 0.039(11) 0.076(14) 0.027(10) 0.041(11) 0.025(9) C110 0.042(10) 0.016(8) 0.039(10) 0.000(7) 0.010(9) 0.018(8) C111 0.043(11) 0.023(9) 0.063(12) -0.006(9) 0.024(10) -0.009(8) C112 0.014(8) 0.038(10) 0.051(11) -0.016(9) 0.009(8) -0.006(7) C113 0.019(9) 0.031(9) 0.051(11) 0.004(8) 0.005(9) 0.004(7) C114 0.060(12) 0.046(13) 0.044(11) 0.007(10) 0.012(10) -0.005(10) C115 0.072(14) 0.063(15) 0.062(13) -0.031(11) 0.031(12) -0.018(12) C116 0.027(11) 0.056(16) 0.19(3) -0.075(17) 0.008(15) -0.007(10) C117 0.052(14) 0.10(2) 0.080(15) -0.053(15) 0.014(12) -0.025(13) C118 0.076(15) 0.049(14) 0.065(14) -0.032(11) 0.018(13) -0.026(12) C119 0.096(19) 0.078(18) 0.057(15) -0.008(13) 0.054(16) 0.020(15) O120 0.041(7) 0.047(8) 0.032(7) -0.006(6) 0.001(6) 0.008(6) Br7 0.0498(11) 0.0413(12) 0.0695(13) 0.0097(11) 0.0204(11) 0.0108(10) F19 0.087(8) 0.049(8) 0.073(8) -0.016(6) -0.022(7) 0.028(7) F20 0.094(9) 0.041(7) 0.091(9) -0.006(7) 0.023(8) 0.002(7) F21 0.079(8) 0.062(9) 0.071(7) -0.017(7) 0.020(7) 0.028(7) O121 0.041(7) 0.043(8) 0.034(7) 0.008(6) -0.001(6) 0.004(6) C122 0.043(12) 0.033(11) 0.066(14) 0.023(10) 0.034(11) 0.019(9) C123 0.028(9) 0.048(11) 0.038(10) -0.012(9) 0.015(9) -0.012(8) C124 0.026(9) 0.034(10) 0.057(12) 0.008(9) 0.009(9) 0.002(8) C125 0.047(11) 0.046(12) 0.042(11) -0.003(9) 0.023(10) -0.003(10) C126 0.057(13) 0.043(13) 0.052(13) 0.024(10) 0.021(12) 0.013(10) C127 0.031(10) 0.021(9) 0.045(10) -0.004(8) -0.002(9) -0.009(7) C128 0.018(8) 0.043(11) 0.071(13) -0.018(10) 0.004(9) -0.004(8) C129 0.025(9) 0.033(10) 0.070(13) -0.026(10) 0.011(10) -0.007(8) C130 0.048(11) 0.024(10) 0.044(11) 0.004(8) 0.004(10) 0.003(8) C131 0.050(11) 0.024(10) 0.032(10) 0.005(8) 0.006(9) 0.001(8) C132 0.046(11) 0.040(11) 0.031(10) 0.016(8) 0.012(9) 0.003(9) C133 0.039(10) 0.026(10) 0.055(12) -0.023(9) 0.004(10) -0.011(8) C134 0.037(10) 0.045(12) 0.042(11) 0.014(9) 0.002(9) 0.012(9) C135 0.051(12) 0.045(13) 0.065(14) -0.007(11) 0.012(11) -0.004(10) C136 0.037(11) 0.062(14) 0.031(10) -0.022(10) -0.006(9) -0.009(10) C137 0.044(11) 0.029(10) 0.057(12) -0.007(9) 0.010(10) -0.013(8) C138 0.042(10) 0.043(11) 0.034(10) 0.012(9) 0.014(9) 0.007(9) C139 0.063(15) 0.030(12) 0.075(15) -0.010(11) -0.006(14) 0.024(11) O140 0.050(8) 0.052(9) 0.043(7) 0.011(7) 0.012(7) 0.013(7) Br8 0.0496(11) 0.0508(13) 0.0538(11) 0.0033(10) 0.0040(10) 0.0218(10) F22 0.044(6) 0.070(9) 0.149(12) 0.056(9) 0.036(8) 0.022(6) F23 0.072(8) 0.102(12) 0.058(8) 0.022(7) -0.004(7) 0.019(8) F24 0.050(7) 0.042(7) 0.095(8) 0.027(7) -0.006(6) -0.004(6) O141 0.032(7) 0.026(7) 0.050(7) 0.008(6) 0.001(6) 0.007(5) C142 0.043(11) 0.019(9) 0.043(11) 0.006(8) 0.005(10) -0.006(8) C143 0.028(9) 0.023(9) 0.039(10) 0.003(7) 0.013(8) 0.016(7) C144 0.021(8) 0.025(9) 0.031(9) -0.005(7) -0.002(8) -0.009(7) C145 0.038(10) 0.041(11) 0.041(11) 0.006(9) 0.004(9) 0.006(9) C146 0.039(12) 0.039(12) 0.053(12) 0.026(10) -0.020(11) 0.008(10) C147 0.031(9) 0.047(11) 0.037(10) -0.005(9) 0.010(9) -0.013(9) C148 0.032(4) 0.033(4) 0.032(4) 0.0004(11) 0.0086(14) -0.0001(11) C149 0.042(10) 0.044(12) 0.033(10) 0.019(9) -0.009(9) -0.012(9) C150 0.042(5) 0.043(5) 0.042(5) -0.0001(11) 0.0103(15) 0.0001(11) C151 0.033(10) 0.054(13) 0.056(12) -0.004(10) 0.006(10) 0.013(9) C152 0.023(9) 0.090(16) 0.025(9) -0.002(10) 0.003(8) -0.009(10) C153 0.050(11) 0.023(10) 0.044(11) -0.019(8) -0.005(10) 0.003(9) C154 0.075(14) 0.027(11) 0.090(16) -0.009(11) 0.037(13) -0.018(10) C155 0.092(17) 0.079(19) 0.061(14) -0.002(13) 0.029(14) -0.017(15) C156 0.078(16) 0.09(2) 0.062(15) -0.004(14) 0.017(13) 0.046(15) C157 0.045(12) 0.088(19) 0.027(10) 0.005(11) -0.003(9) 0.012(13) C158 0.043(11) 0.069(15) 0.027(10) -0.004(10) 0.006(9) 0.004(10) C159 0.047(12) 0.041(12) 0.044(12) 0.010(10) -0.007(11) -0.009(10) O160 0.044(7) 0.026(7) 0.049(7) -0.001(6) 0.011(7) -0.008(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C10 1.941(16) . ? F1 C19 1.33(2) . ? O1 C2 1.378(19) . ? O1 C6 1.389(18) . ? F2 C19 1.32(2) . ? C2 O20 1.173(18) . ? C2 C3 1.56(2) . ? F3 C19 1.32(2) . ? C3 C7 1.44(2) . ? C3 C4 1.58(2) . ? C3 H3A 1.0000 . ? C4 C5 1.52(2) . ? C4 C13 1.534(19) . ? C4 H4A 1.0000 . ? C5 C6 1.31(2) . ? C5 H5A 0.9500 . ? C6 C19 1.51(3) . ? C7 C12 1.41(2) . ? C7 C8 1.43(2) . ? C8 C9 1.41(2) . ? C8 H8A 0.9500 . ? C9 C10 1.37(2) . ? C9 H9A 0.9500 . ? C10 C11 1.37(2) . ? C11 C12 1.35(2) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C18 1.35(2) . ? C13 C14 1.44(2) . ? C14 C15 1.35(2) . ? C14 H14A 0.9500 . ? C15 C16 1.37(2) . ? C15 H15A 0.9500 . ? C16 C17 1.37(2) . ? C16 H16A 0.9500 . ? C17 C18 1.38(2) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? Br2 C30 1.890(15) . ? F4 C39 1.323(16) . ? F5 C39 1.36(2) . ? F6 C39 1.351(19) . ? O21 C22 1.38(2) . ? O21 C26 1.407(17) . ? C22 O40 1.230(17) . ? C22 C23 1.49(2) . ? C23 C27 1.52(2) . ? C23 C24 1.520(19) . ? C23 H23A 1.0000 . ? C24 C25 1.48(2) . ? C24 C33 1.60(2) . ? C24 H24A 1.0000 . ? C25 C26 1.36(2) . ? C25 H25A 0.9500 . ? C26 C39 1.42(2) . ? C27 C32 1.36(2) . ? C27 C28 1.374(19) . ? C28 C29 1.42(2) . ? C28 H28A 0.9500 . ? C29 C30 1.38(2) . ? C29 H29A 0.9500 . ? C30 C31 1.386(18) . ? C31 C32 1.44(2) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? C33 C38 1.35(2) . ? C33 C34 1.35(2) . ? C34 C35 1.35(2) . ? C34 H34A 0.9500 . ? C35 C36 1.47(2) . ? C35 H35A 0.9500 . ? C36 C37 1.35(2) . ? C36 H36A 0.9500 . ? C37 C38 1.40(2) . ? C37 H37A 0.9500 . ? C38 H38A 0.9500 . ? Br3 C50 1.934(17) . ? F7 C59 1.30(2) . ? F8 C59 1.32(2) . ? F9 C59 1.33(2) . ? O41 C42 1.38(2) . ? O41 C46 1.42(2) . ? C42 O60 1.183(19) . ? C42 C43 1.53(2) . ? C43 C47 1.50(2) . ? C43 C44 1.54(2) . ? C43 H43A 1.0000 . ? C44 C53 1.521(19) . ? C44 C45 1.58(2) . ? C44 H44A 1.0000 . ? C45 C46 1.26(2) . ? C45 H45A 0.9500 . ? C46 C59 1.51(3) . ? C47 C52 1.38(2) . ? C47 C48 1.43(2) . ? C48 C49 1.35(2) . ? C48 H48A 0.9500 . ? C49 C50 1.39(2) . ? C49 H49A 0.9500 . ? C50 C51 1.34(2) . ? C51 C52 1.43(2) . ? C51 H51A 0.9500 . ? C52 H52A 0.9500 . ? C53 C58 1.33(2) . ? C53 C54 1.40(2) . ? C54 C55 1.37(2) . ? C54 H54A 0.9500 . ? C55 C56 1.39(3) . ? C55 H55A 0.9500 . ? C56 C57 1.40(3) . ? C56 H56A 0.9500 . ? C57 C58 1.41(2) . ? C57 H57A 0.9500 . ? C58 H58A 0.9500 . ? Br4 C70 1.901(17) . ? F10 C79 1.22(2) . ? F11 C79 1.40(3) . ? F12 C79 1.29(3) . ? O61 C62 1.39(2) . ? O61 C66 1.42(2) . ? C62 O80 1.22(2) . ? C62 C63 1.45(2) . ? C63 C67 1.53(2) . ? C63 C64 1.56(2) . ? C63 H63A 1.0000 . ? C64 C73 1.50(2) . ? C64 C65 1.55(2) . ? C64 H64A 1.0000 . ? C65 C66 1.27(2) . ? C65 H65A 0.9500 . ? C66 C79 1.55(3) . ? C67 C72 1.374(19) . ? C67 C68 1.42(2) . ? C68 C69 1.36(2) . ? C68 H68A 0.9500 . ? C69 C70 1.34(2) . ? C69 H69A 0.9500 . ? C70 C71 1.43(2) . ? C71 C72 1.35(2) . ? C71 H71A 0.9500 . ? C72 H72A 0.9500 . ? C73 C74 1.36(2) . ? C73 C78 1.47(2) . ? C74 C75 1.42(3) . ? C74 H74A 0.9500 . ? C75 C76 1.36(3) . ? C75 H75A 0.9500 . ? C76 C77 1.32(3) . ? C76 H76A 0.9500 . ? C77 C78 1.35(3) . ? C77 H77A 0.9500 . ? C78 H78A 0.9500 . ? Br5 C90 1.929(18) . ? F13 C99 1.31(3) . ? F14 C99 1.36(2) . ? F15 C99 1.28(2) . ? O81 C82 1.370(19) . ? O81 C86 1.394(17) . ? C82 O100 1.194(19) . ? C82 C83 1.53(2) . ? C83 C87 1.50(2) . ? C83 C84 1.60(2) . ? C83 H83A 1.0000 . ? C84 C85 1.50(2) . ? C84 C93 1.515(19) . ? C84 H84A 1.0000 . ? C85 C86 1.363(19) . ? C85 H85A 0.9500 . ? C86 C99 1.46(2) . ? C87 C92 1.36(2) . ? C87 C88 1.44(2) . ? C88 C89 1.35(2) . ? C88 H88A 0.9500 . ? C89 C90 1.34(2) . ? C89 H89A 0.9500 . ? C90 C91 1.39(3) . ? C91 C92 1.38(2) . ? C91 H91A 0.9500 . ? C92 H92A 0.9500 . ? C93 C98 1.36(2) . ? C93 C94 1.38(2) . ? C94 C95 1.42(2) . ? C94 H94A 0.9500 . ? C95 C96 1.39(3) . ? C95 H95A 0.9500 . ? C96 C97 1.31(3) . ? C96 H96A 0.9500 . ? C97 C98 1.43(2) . ? C97 H97A 0.9500 . ? C98 H98A 0.9500 . ? Br6 C110 1.904(14) . ? F16 C119 1.36(3) . ? F17 C119 1.334(19) . ? F18 C119 1.31(2) . ? O101 C102 1.34(2) . ? O101 C106 1.385(19) . ? C102 O120 1.215(18) . ? C102 C103 1.52(2) . ? C103 C107 1.46(2) . ? C103 C104 1.564(19) . ? C103 H10A 1.0000 . ? C104 C113 1.50(2) . ? C104 C105 1.53(2) . ? C104 H10B 1.0000 . ? C105 C106 1.31(2) . ? C105 H10C 0.9500 . ? C106 C119 1.51(3) . ? C107 C108 1.40(2) . ? C107 C112 1.40(2) . ? C108 C109 1.37(2) . ? C108 H10D 0.9500 . ? C109 C110 1.36(2) . ? C109 H10E 0.9500 . ? C110 C111 1.37(2) . ? C111 C112 1.37(2) . ? C111 H11B 0.9500 . ? C112 H11C 0.9500 . ? C113 C118 1.31(2) . ? C113 C114 1.42(2) . ? C114 C115 1.43(2) . ? C114 H11D 0.9500 . ? C115 C116 1.27(2) . ? C115 H11E 0.9500 . ? C116 C117 1.43(3) . ? C116 H11F 0.9500 . ? C117 C118 1.40(2) . ? C117 H11G 0.9500 . ? C118 H11H 0.9500 . ? Br7 C130 1.887(17) . ? F19 C139 1.33(2) . ? F20 C139 1.35(2) . ? F21 C139 1.37(2) . ? O121 C122 1.360(19) . ? O121 C126 1.39(2) . ? C122 O140 1.190(19) . ? C122 C123 1.51(2) . ? C123 C127 1.50(2) . ? C123 C124 1.55(2) . ? C123 H12B 1.0000 . ? C124 C125 1.45(2) . ? C124 C133 1.56(2) . ? C124 H12C 1.0000 . ? C125 C126 1.33(2) . ? C125 H12D 0.9500 . ? C126 C139 1.45(3) . ? C127 C132 1.39(2) . ? C127 C128 1.414(19) . ? C128 C129 1.40(2) . ? C128 H12E 0.9500 . ? C129 C130 1.39(2) . ? C129 H12F 0.9500 . ? C130 C131 1.36(2) . ? C131 C132 1.34(2) . ? C131 H13A 0.9500 . ? C132 H13B 0.9500 . ? C133 C134 1.37(2) . ? C133 C138 1.39(2) . ? C134 C135 1.43(2) . ? C134 H13C 0.9500 . ? C135 C136 1.38(2) . ? C135 H13D 0.9500 . ? C136 C137 1.43(2) . ? C136 H13E 0.9500 . ? C137 C138 1.34(2) . ? C137 H13F 0.9500 . ? C138 H13G 0.9500 . ? Br8 C150 1.932(18) . ? F22 C159 1.301(19) . ? F23 C159 1.38(2) . ? F24 C159 1.362(19) . ? O141 C146 1.36(2) . ? O141 C142 1.380(19) . ? C142 O160 1.191(18) . ? C142 C143 1.56(2) . ? C143 C144 1.490(19) . ? C143 C147 1.50(2) . ? C143 H14B 1.0000 . ? C144 C145 1.44(2) . ? C144 C153 1.54(2) . ? C144 H14C 1.0000 . ? C145 C146 1.43(3) . ? C145 H14D 0.9500 . ? C146 C159 1.41(2) . ? C147 C148 1.37(2) . ? C147 C152 1.386(19) . ? C148 C149 1.39(2) . ? C148 H14E 0.9500 . ? C149 C150 1.39(2) . ? C149 H14F 0.9500 . ? C150 C151 1.32(2) . ? C151 C152 1.38(2) . ? C151 H15B 0.9500 . ? C152 H15C 0.9500 . ? C153 C154 1.39(2) . ? C153 C158 1.41(2) . ? C154 C155 1.40(3) . ? C154 H15D 0.9500 . ? C155 C156 1.35(2) . ? C155 H15E 0.9500 . ? C156 C157 1.35(3) . ? C156 H15F 0.9500 . ? C157 C158 1.44(3) . ? C157 H15G 0.9500 . ? C158 H15H 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C6 119.3(14) . . ? O20 C2 O1 116.9(16) . . ? O20 C2 C3 127.9(16) . . ? O1 C2 C3 113.7(14) . . ? C7 C3 C2 111.2(12) . . ? C7 C3 C4 112.4(14) . . ? C2 C3 C4 107.8(14) . . ? C7 C3 H3A 108.4 . . ? C2 C3 H3A 108.4 . . ? C4 C3 H3A 108.4 . . ? C5 C4 C13 110.4(12) . . ? C5 C4 C3 108.7(13) . . ? C13 C4 C3 110.4(13) . . ? C5 C4 H4A 109.1 . . ? C13 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C6 C5 C4 117.5(15) . . ? C6 C5 H5A 121.2 . . ? C4 C5 H5A 121.2 . . ? C5 C6 O1 127.2(17) . . ? C5 C6 C19 123.5(16) . . ? O1 C6 C19 109.2(15) . . ? C12 C7 C8 114.7(14) . . ? C12 C7 C3 123.3(14) . . ? C8 C7 C3 121.9(15) . . ? C9 C8 C7 120.7(15) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C10 C9 C8 118.8(14) . . ? C10 C9 H9A 120.6 . . ? C8 C9 H9A 120.6 . . ? C9 C10 C11 122.7(15) . . ? C9 C10 Br1 117.3(11) . . ? C11 C10 Br1 120.0(13) . . ? C12 C11 C10 118.2(16) . . ? C12 C11 H11A 120.9 . . ? C10 C11 H11A 120.9 . . ? C11 C12 C7 124.7(14) . . ? C11 C12 H12A 117.6 . . ? C7 C12 H12A 117.6 . . ? C18 C13 C14 117.3(16) . . ? C18 C13 C4 125.0(15) . . ? C14 C13 C4 117.7(13) . . ? C15 C14 C13 120.4(16) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? C14 C15 C16 120.3(18) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C17 C16 C15 120.1(17) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C16 C17 C18 119.8(15) . . ? C16 C17 H17A 120.1 . . ? C18 C17 H17A 120.1 . . ? C13 C18 C17 121.7(17) . . ? C13 C18 H18A 119.2 . . ? C17 C18 H18A 119.2 . . ? F3 C19 F2 108.3(19) . . ? F3 C19 F1 106.9(15) . . ? F2 C19 F1 106.5(17) . . ? F3 C19 C6 112.5(16) . . ? F2 C19 C6 112.0(15) . . ? F1 C19 C6 110.4(19) . . ? C22 O21 C26 119.3(13) . . ? O40 C22 O21 115.6(14) . . ? O40 C22 C23 125.9(16) . . ? O21 C22 C23 118.4(14) . . ? C22 C23 C27 111.4(13) . . ? C22 C23 C24 108.2(14) . . ? C27 C23 C24 116.8(13) . . ? C22 C23 H23A 106.6 . . ? C27 C23 H23A 106.6 . . ? C24 C23 H23A 106.6 . . ? C25 C24 C23 109.2(13) . . ? C25 C24 C33 110.9(11) . . ? C23 C24 C33 112.4(13) . . ? C25 C24 H24A 108.1 . . ? C23 C24 H24A 108.1 . . ? C33 C24 H24A 108.1 . . ? C26 C25 C24 119.1(13) . . ? C26 C25 H25A 120.4 . . ? C24 C25 H25A 120.4 . . ? C25 C26 O21 120.5(15) . . ? C25 C26 C39 128.1(15) . . ? O21 C26 C39 111.0(14) . . ? C32 C27 C28 118.6(15) . . ? C32 C27 C23 121.6(14) . . ? C28 C27 C23 119.7(14) . . ? C27 C28 C29 122.4(15) . . ? C27 C28 H28A 118.8 . . ? C29 C28 H28A 118.8 . . ? C30 C29 C28 115.7(15) . . ? C30 C29 H29A 122.2 . . ? C28 C29 H29A 122.2 . . ? C29 C30 C31 125.6(15) . . ? C29 C30 Br2 116.1(11) . . ? C31 C30 Br2 118.3(12) . . ? C30 C31 C32 114.2(14) . . ? C30 C31 H31A 122.9 . . ? C32 C31 H31A 122.9 . . ? C27 C32 C31 123.5(14) . . ? C27 C32 H32A 118.3 . . ? C31 C32 H32A 118.3 . . ? C38 C33 C34 121.5(15) . . ? C38 C33 C24 116.4(15) . . ? C34 C33 C24 121.8(14) . . ? C35 C34 C33 120.0(15) . . ? C35 C34 H34A 120.0 . . ? C33 C34 H34A 120.0 . . ? C34 C35 C36 119.2(16) . . ? C34 C35 H35A 120.4 . . ? C36 C35 H35A 120.4 . . ? C37 C36 C35 119.2(15) . . ? C37 C36 H36A 120.4 . . ? C35 C36 H36A 120.4 . . ? C36 C37 C38 118.5(17) . . ? C36 C37 H37A 120.8 . . ? C38 C37 H37A 120.8 . . ? C33 C38 C37 121.3(17) . . ? C33 C38 H38A 119.3 . . ? C37 C38 H38A 119.3 . . ? F4 C39 F6 106.7(14) . . ? F4 C39 F5 107.4(15) . . ? F6 C39 F5 105.8(14) . . ? F4 C39 C26 111.8(14) . . ? F6 C39 C26 112.5(17) . . ? F5 C39 C26 112.3(15) . . ? C42 O41 C46 118.0(12) . . ? O60 C42 O41 117.2(14) . . ? O60 C42 C43 126.8(17) . . ? O41 C42 C43 115.5(14) . . ? C47 C43 C42 108.9(13) . . ? C47 C43 C44 113.7(12) . . ? C42 C43 C44 112.7(13) . . ? C47 C43 H43A 107.0 . . ? C42 C43 H43A 107.0 . . ? C44 C43 H43A 107.0 . . ? C53 C44 C43 111.2(13) . . ? C53 C44 C45 110.7(13) . . ? C43 C44 C45 104.5(12) . . ? C53 C44 H44A 110.1 . . ? C43 C44 H44A 110.1 . . ? C45 C44 H44A 110.1 . . ? C46 C45 C44 120.7(16) . . ? C46 C45 H45A 119.7 . . ? C44 C45 H45A 119.7 . . ? C45 C46 O41 126.6(17) . . ? C45 C46 C59 125.0(17) . . ? O41 C46 C59 108.3(15) . . ? C52 C47 C48 116.5(15) . . ? C52 C47 C43 123.5(15) . . ? C48 C47 C43 119.9(14) . . ? C49 C48 C47 121.5(16) . . ? C49 C48 H48A 119.2 . . ? C47 C48 H48A 119.2 . . ? C48 C49 C50 118.9(17) . . ? C48 C49 H49A 120.5 . . ? C50 C49 H49A 120.5 . . ? C51 C50 C49 124.5(17) . . ? C51 C50 Br3 116.0(14) . . ? C49 C50 Br3 119.4(14) . . ? C50 C51 C52 115.4(18) . . ? C50 C51 H51A 122.3 . . ? C52 C51 H51A 122.3 . . ? C47 C52 C51 123.2(17) . . ? C47 C52 H52A 118.4 . . ? C51 C52 H52A 118.4 . . ? C58 C53 C54 118.1(15) . . ? C58 C53 C44 124.4(16) . . ? C54 C53 C44 117.4(16) . . ? C55 C54 C53 120(2) . . ? C55 C54 H54A 119.9 . . ? C53 C54 H54A 119.9 . . ? C54 C55 C56 120(2) . . ? C54 C55 H55A 120.2 . . ? C56 C55 H55A 120.2 . . ? C55 C56 C57 122.2(17) . . ? C55 C56 H56A 118.9 . . ? C57 C56 H56A 118.9 . . ? C56 C57 C58 114(2) . . ? C56 C57 H57A 123.0 . . ? C58 C57 H57A 123.0 . . ? C53 C58 C57 125.7(19) . . ? C53 C58 H58A 117.1 . . ? C57 C58 H58A 117.1 . . ? F7 C59 F8 110.1(17) . . ? F7 C59 F9 104.0(15) . . ? F8 C59 F9 108(2) . . ? F7 C59 C46 115(2) . . ? F8 C59 C46 111.4(15) . . ? F9 C59 C46 107.9(16) . . ? C62 O61 C66 118.8(15) . . ? O80 C62 O61 115.4(18) . . ? O80 C62 C63 127.3(19) . . ? O61 C62 C63 116.8(17) . . ? C62 C63 C67 113.2(15) . . ? C62 C63 C64 116.5(15) . . ? C67 C63 C64 110.0(12) . . ? C62 C63 H63A 105.3 . . ? C67 C63 H63A 105.3 . . ? C64 C63 H63A 105.3 . . ? C73 C64 C65 114.1(15) . . ? C73 C64 C63 108.9(13) . . ? C65 C64 C63 104.2(12) . . ? C73 C64 H64A 109.8 . . ? C65 C64 H64A 109.8 . . ? C63 C64 H64A 109.8 . . ? C66 C65 C64 123.3(17) . . ? C66 C65 H65A 118.4 . . ? C64 C65 H65A 118.4 . . ? C65 C66 O61 124.1(18) . . ? C65 C66 C79 128(2) . . ? O61 C66 C79 108.3(18) . . ? C72 C67 C68 114.8(15) . . ? C72 C67 C63 122.9(14) . . ? C68 C67 C63 122.2(14) . . ? C69 C68 C67 123.5(15) . . ? C69 C68 H68A 118.2 . . ? C67 C68 H68A 118.2 . . ? C70 C69 C68 117.6(17) . . ? C70 C69 H69A 121.2 . . ? C68 C69 H69A 121.2 . . ? C69 C70 C71 122.9(17) . . ? C69 C70 Br4 119.1(15) . . ? C71 C70 Br4 117.9(12) . . ? C72 C71 C70 116.0(14) . . ? C72 C71 H71A 122.0 . . ? C70 C71 H71A 122.0 . . ? C71 C72 C67 125.0(16) . . ? C71 C72 H72A 117.5 . . ? C67 C72 H72A 117.5 . . ? C74 C73 C78 116.2(17) . . ? C74 C73 C64 126.3(17) . . ? C78 C73 C64 117.4(16) . . ? C73 C74 C75 122.4(19) . . ? C73 C74 H74A 118.8 . . ? C75 C74 H74A 118.8 . . ? C76 C75 C74 117.2(19) . . ? C76 C75 H75A 121.4 . . ? C74 C75 H75A 121.4 . . ? C77 C76 C75 123(2) . . ? C77 C76 H76A 118.3 . . ? C75 C76 H76A 118.3 . . ? C76 C77 C78 121(2) . . ? C76 C77 H77A 119.5 . . ? C78 C77 H77A 119.5 . . ? C77 C78 C73 119.8(19) . . ? C77 C78 H78A 120.1 . . ? C73 C78 H78A 120.1 . . ? F10 C79 F12 117(2) . . ? F10 C79 F11 111(2) . . ? F12 C79 F11 103(2) . . ? F10 C79 C66 115(2) . . ? F12 C79 C66 108(2) . . ? F11 C79 C66 100.8(18) . . ? C82 O81 C86 123.3(13) . . ? O100 C82 O81 117.5(14) . . ? O100 C82 C83 127.0(16) . . ? O81 C82 C83 115.5(14) . . ? C87 C83 C82 111.4(12) . . ? C87 C83 C84 114.9(12) . . ? C82 C83 C84 108.8(14) . . ? C87 C83 H83A 107.1 . . ? C82 C83 H83A 107.1 . . ? C84 C83 H83A 107.1 . . ? C85 C84 C93 112.9(13) . . ? C85 C84 C83 106.7(12) . . ? C93 C84 C83 111.1(14) . . ? C85 C84 H84A 108.7 . . ? C93 C84 H84A 108.7 . . ? C83 C84 H84A 108.7 . . ? C86 C85 C84 120.7(14) . . ? C86 C85 H85A 119.6 . . ? C84 C85 H85A 119.6 . . ? C85 C86 O81 119.8(15) . . ? C85 C86 C99 127.7(16) . . ? O81 C86 C99 112.4(14) . . ? C92 C87 C88 116.3(15) . . ? C92 C87 C83 128.5(17) . . ? C88 C87 C83 115.2(15) . . ? C89 C88 C87 118.5(16) . . ? C89 C88 H88A 120.7 . . ? C87 C88 H88A 120.7 . . ? C90 C89 C88 121.4(18) . . ? C90 C89 H89A 119.3 . . ? C88 C89 H89A 119.3 . . ? C89 C90 C91 124.2(17) . . ? C89 C90 Br5 120.6(17) . . ? C91 C90 Br5 115.2(14) . . ? C92 C91 C90 113.2(16) . . ? C92 C91 H91A 123.4 . . ? C90 C91 H91A 123.4 . . ? C87 C92 C91 126.3(17) . . ? C87 C92 H92A 116.8 . . ? C91 C92 H92A 116.8 . . ? C98 C93 C94 118.2(16) . . ? C98 C93 C84 125.1(17) . . ? C94 C93 C84 116.7(17) . . ? C93 C94 C95 120.7(19) . . ? C93 C94 H94A 119.7 . . ? C95 C94 H94A 119.7 . . ? C96 C95 C94 119.2(19) . . ? C96 C95 H95A 120.4 . . ? C94 C95 H95A 120.4 . . ? C97 C96 C95 120.1(19) . . ? C97 C96 H96A 119.9 . . ? C95 C96 H96A 119.9 . . ? C96 C97 C98 121(2) . . ? C96 C97 H97A 119.5 . . ? C98 C97 H97A 119.5 . . ? C93 C98 C97 120.6(19) . . ? C93 C98 H98A 119.7 . . ? C97 C98 H98A 119.7 . . ? F15 C99 F13 110(2) . . ? F15 C99 F14 109.6(18) . . ? F13 C99 F14 108.0(18) . . ? F15 C99 C86 110.3(17) . . ? F13 C99 C86 110.8(18) . . ? F14 C99 C86 108.1(18) . . ? C102 O101 C106 118.0(14) . . ? O120 C102 O101 115.1(16) . . ? O120 C102 C103 123.8(16) . . ? O101 C102 C103 120.7(16) . . ? C107 C103 C102 110.2(14) . . ? C107 C103 C104 114.8(13) . . ? C102 C103 C104 110.6(13) . . ? C107 C103 H10A 106.9 . . ? C102 C103 H10A 106.9 . . ? C104 C103 H10A 106.9 . . ? C113 C104 C105 110.8(13) . . ? C113 C104 C103 108.9(14) . . ? C105 C104 C103 110.7(13) . . ? C113 C104 H10B 108.8 . . ? C105 C104 H10B 108.8 . . ? C103 C104 H10B 108.8 . . ? C106 C105 C104 119.5(15) . . ? C106 C105 H10C 120.3 . . ? C104 C105 H10C 120.3 . . ? C105 C106 O101 126.7(18) . . ? C105 C106 C119 122.5(19) . . ? O101 C106 C119 110.6(17) . . ? C108 C107 C112 115.1(16) . . ? C108 C107 C103 123.1(15) . . ? C112 C107 C103 121.7(14) . . ? C109 C108 C107 121.6(16) . . ? C109 C108 H10D 119.2 . . ? C107 C108 H10D 119.2 . . ? C110 C109 C108 120.5(15) . . ? C110 C109 H10E 119.7 . . ? C108 C109 H10E 119.7 . . ? C109 C110 C111 121.2(14) . . ? C109 C110 Br6 118.5(12) . . ? C111 C110 Br6 120.3(12) . . ? C110 C111 C112 117.8(15) . . ? C110 C111 H11B 121.1 . . ? C112 C111 H11B 121.1 . . ? C111 C112 C107 123.8(14) . . ? C111 C112 H11C 118.1 . . ? C107 C112 H11C 118.1 . . ? C118 C113 C114 118.8(17) . . ? C118 C113 C104 123.2(16) . . ? C114 C113 C104 117.8(14) . . ? C113 C114 C115 117.8(17) . . ? C113 C114 H11D 121.1 . . ? C115 C114 H11D 121.1 . . ? C116 C115 C114 121.3(19) . . ? C116 C115 H11E 119.3 . . ? C114 C115 H11E 119.3 . . ? C115 C116 C117 122(2) . . ? C115 C116 H11F 119.0 . . ? C117 C116 H11F 119.0 . . ? C118 C117 C116 115.8(19) . . ? C118 C117 H11G 122.1 . . ? C116 C117 H11G 122.1 . . ? C113 C118 C117 123.6(19) . . ? C113 C118 H11H 118.2 . . ? C117 C118 H11H 118.2 . . ? F18 C119 F17 109.8(18) . . ? F18 C119 F16 108(2) . . ? F17 C119 F16 105.6(17) . . ? F18 C119 C106 114.5(18) . . ? F17 C119 C106 108.4(19) . . ? F16 C119 C106 110.4(18) . . ? C122 O121 C126 118.3(15) . . ? O140 C122 O121 116.8(18) . . ? O140 C122 C123 127.3(16) . . ? O121 C122 C123 115.9(16) . . ? C127 C123 C122 110.0(14) . . ? C127 C123 C124 115.9(13) . . ? C122 C123 C124 109.4(13) . . ? C127 C123 H12B 107.0 . . ? C122 C123 H12B 107.0 . . ? C124 C123 H12B 107.0 . . ? C125 C124 C123 106.8(14) . . ? C125 C124 C133 111.8(14) . . ? C123 C124 C133 113.7(13) . . ? C125 C124 H12C 108.1 . . ? C123 C124 H12C 108.1 . . ? C133 C124 H12C 108.1 . . ? C126 C125 C124 121.6(18) . . ? C126 C125 H12D 119.2 . . ? C124 C125 H12D 119.2 . . ? C125 C126 O121 123.4(18) . . ? C125 C126 C139 127(2) . . ? O121 C126 C139 109.7(18) . . ? C132 C127 C128 116.5(16) . . ? C132 C127 C123 125.5(14) . . ? C128 C127 C123 117.5(14) . . ? C129 C128 C127 119.5(16) . . ? C129 C128 H12E 120.3 . . ? C127 C128 H12E 120.3 . . ? C130 C129 C128 120.3(14) . . ? C130 C129 H12F 119.9 . . ? C128 C129 H12F 119.9 . . ? C131 C130 C129 119.4(16) . . ? C131 C130 Br7 123.7(13) . . ? C129 C130 Br7 117.0(12) . . ? C132 C131 C130 120.7(16) . . ? C132 C131 H13A 119.6 . . ? C130 C131 H13A 119.6 . . ? C131 C132 C127 123.5(15) . . ? C131 C132 H13B 118.2 . . ? C127 C132 H13B 118.2 . . ? C134 C133 C138 120.5(16) . . ? C134 C133 C124 118.8(16) . . ? C138 C133 C124 120.7(15) . . ? C133 C134 C135 118.4(16) . . ? C133 C134 H13C 120.8 . . ? C135 C134 H13C 120.8 . . ? C136 C135 C134 121.5(18) . . ? C136 C135 H13D 119.3 . . ? C134 C135 H13D 119.3 . . ? C135 C136 C137 117.4(16) . . ? C135 C136 H13E 121.3 . . ? C137 C136 H13E 121.3 . . ? C138 C137 C136 120.7(17) . . ? C138 C137 H13F 119.6 . . ? C136 C137 H13F 119.6 . . ? C137 C138 C133 121.1(17) . . ? C137 C138 H13G 119.4 . . ? C133 C138 H13G 119.4 . . ? F19 C139 F20 107.3(18) . . ? F19 C139 F21 103.5(14) . . ? F20 C139 F21 101.9(16) . . ? F19 C139 C126 114.4(18) . . ? F20 C139 C126 114.9(17) . . ? F21 C139 C126 113.5(18) . . ? C146 O141 C142 122.1(14) . . ? O160 C142 O141 120.0(16) . . ? O160 C142 C143 126.3(16) . . ? O141 C142 C143 113.7(14) . . ? C144 C143 C147 120.1(14) . . ? C144 C143 C142 106.3(12) . . ? C147 C143 C142 112.1(14) . . ? C144 C143 H14B 105.8 . . ? C147 C143 H14B 105.8 . . ? C142 C143 H14B 105.8 . . ? C145 C144 C143 109.5(14) . . ? C145 C144 C153 115.4(14) . . ? C143 C144 C153 111.4(12) . . ? C145 C144 H14C 106.7 . . ? C143 C144 H14C 106.7 . . ? C153 C144 H14C 106.7 . . ? C146 C145 C144 117.7(16) . . ? C146 C145 H14D 121.2 . . ? C144 C145 H14D 121.2 . . ? O141 C146 C159 114.0(19) . . ? O141 C146 C145 118.2(15) . . ? C159 C146 C145 126.7(19) . . ? C148 C147 C152 118.7(17) . . ? C148 C147 C143 120.8(13) . . ? C152 C147 C143 120.1(15) . . ? C147 C148 C149 121.1(14) . . ? C147 C148 H14E 119.5 . . ? C149 C148 H14E 119.5 . . ? C148 C149 C150 117.1(15) . . ? C148 C149 H14F 121.4 . . ? C150 C149 H14F 121.4 . . ? C151 C150 C149 123.2(17) . . ? C151 C150 Br8 120.6(13) . . ? C149 C150 Br8 116.2(13) . . ? C150 C151 C152 119.1(16) . . ? C150 C151 H15B 120.4 . . ? C152 C151 H15B 120.4 . . ? C147 C152 C151 120.7(17) . . ? C147 C152 H15C 119.6 . . ? C151 C152 H15C 119.6 . . ? C154 C153 C158 119.7(17) . . ? C154 C153 C144 118.9(15) . . ? C158 C153 C144 121.4(17) . . ? C153 C154 C155 120.2(18) . . ? C153 C154 H15D 119.9 . . ? C155 C154 H15D 119.9 . . ? C156 C155 C154 122(2) . . ? C156 C155 H15E 119.2 . . ? C154 C155 H15E 119.2 . . ? C155 C156 C157 119(2) . . ? C155 C156 H15F 120.4 . . ? C157 C156 H15F 120.4 . . ? C156 C157 C158 122.7(19) . . ? C156 C157 H15G 118.6 . . ? C158 C157 H15G 118.6 . . ? C153 C158 C157 116.5(18) . . ? C153 C158 H15H 121.7 . . ? C157 C158 H15H 121.7 . . ? F22 C159 F24 106.9(16) . . ? F22 C159 F23 107.0(15) . . ? F24 C159 F23 103.7(14) . . ? F22 C159 C146 115.8(16) . . ? F24 C159 C146 111.5(15) . . ? F23 C159 C146 111.1(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O1 C2 O20 -171.6(15) . . . . ? C6 O1 C2 C3 21(2) . . . . ? O20 C2 C3 C7 19(3) . . . . ? O1 C2 C3 C7 -175.5(14) . . . . ? O20 C2 C3 C4 143.0(18) . . . . ? O1 C2 C3 C4 -51.9(19) . . . . ? C7 C3 C4 C5 176.9(13) . . . . ? C2 C3 C4 C5 54.0(16) . . . . ? C7 C3 C4 C13 -61.9(17) . . . . ? C2 C3 C4 C13 175.2(12) . . . . ? C13 C4 C5 C6 -150.1(16) . . . . ? C3 C4 C5 C6 -29(2) . . . . ? C4 C5 C6 O1 -4(3) . . . . ? C4 C5 C6 C19 -178.2(16) . . . . ? C2 O1 C6 C5 9(3) . . . . ? C2 O1 C6 C19 -176.2(16) . . . . ? C2 C3 C7 C12 -123.9(16) . . . . ? C4 C3 C7 C12 115.1(17) . . . . ? C2 C3 C7 C8 55(2) . . . . ? C4 C3 C7 C8 -66.1(18) . . . . ? C12 C7 C8 C9 -3(2) . . . . ? C3 C7 C8 C9 178.3(14) . . . . ? C7 C8 C9 C10 3(2) . . . . ? C8 C9 C10 C11 -3(2) . . . . ? C8 C9 C10 Br1 176.8(11) . . . . ? C9 C10 C11 C12 3(2) . . . . ? Br1 C10 C11 C12 -177.5(12) . . . . ? C10 C11 C12 C7 -2(2) . . . . ? C8 C7 C12 C11 2(2) . . . . ? C3 C7 C12 C11 -178.9(15) . . . . ? C5 C4 C13 C18 42(2) . . . . ? C3 C4 C13 C18 -78.0(19) . . . . ? C5 C4 C13 C14 -140.0(15) . . . . ? C3 C4 C13 C14 99.9(17) . . . . ? C18 C13 C14 C15 -4(3) . . . . ? C4 C13 C14 C15 178.0(15) . . . . ? C13 C14 C15 C16 4(3) . . . . ? C14 C15 C16 C17 -5(3) . . . . ? C15 C16 C17 C18 6(3) . . . . ? C14 C13 C18 C17 5(3) . . . . ? C4 C13 C18 C17 -177.0(15) . . . . ? C16 C17 C18 C13 -6(3) . . . . ? C5 C6 C19 F3 -3(3) . . . . ? O1 C6 C19 F3 -178.4(15) . . . . ? C5 C6 C19 F2 119(2) . . . . ? O1 C6 C19 F2 -56(2) . . . . ? C5 C6 C19 F1 -122(2) . . . . ? O1 C6 C19 F1 62.4(19) . . . . ? C26 O21 C22 O40 -179.0(14) . . . . ? C26 O21 C22 C23 4(2) . . . . ? O40 C22 C23 C27 13(2) . . . . ? O21 C22 C23 C27 -170.9(14) . . . . ? O40 C22 C23 C24 142.4(16) . . . . ? O21 C22 C23 C24 -41(2) . . . . ? C22 C23 C24 C25 55.8(18) . . . . ? C27 C23 C24 C25 -177.6(13) . . . . ? C22 C23 C24 C33 179.3(13) . . . . ? C27 C23 C24 C33 -54.1(18) . . . . ? C23 C24 C25 C26 -38(2) . . . . ? C33 C24 C25 C26 -162.4(15) . . . . ? C24 C25 C26 O21 0(3) . . . . ? C24 C25 C26 C39 -171.1(19) . . . . ? C22 O21 C26 C25 19(2) . . . . ? C22 O21 C26 C39 -168.8(16) . . . . ? C22 C23 C27 C32 83.7(17) . . . . ? C24 C23 C27 C32 -41(2) . . . . ? C22 C23 C27 C28 -94.0(17) . . . . ? C24 C23 C27 C28 141.0(14) . . . . ? C32 C27 C28 C29 1(2) . . . . ? C23 C27 C28 C29 178.9(13) . . . . ? C27 C28 C29 C30 -2(2) . . . . ? C28 C29 C30 C31 3(2) . . . . ? C28 C29 C30 Br2 -178.6(10) . . . . ? C29 C30 C31 C32 -3(2) . . . . ? Br2 C30 C31 C32 178.8(10) . . . . ? C28 C27 C32 C31 -1(2) . . . . ? C23 C27 C32 C31 -178.7(13) . . . . ? C30 C31 C32 C27 2(2) . . . . ? C25 C24 C33 C38 -74.4(19) . . . . ? C23 C24 C33 C38 163.1(14) . . . . ? C25 C24 C33 C34 99.4(17) . . . . ? C23 C24 C33 C34 -23(2) . . . . ? C38 C33 C34 C35 -3(2) . . . . ? C24 C33 C34 C35 -176.1(14) . . . . ? C33 C34 C35 C36 -3(2) . . . . ? C34 C35 C36 C37 5(2) . . . . ? C35 C36 C37 C38 -2(2) . . . . ? C34 C33 C38 C37 6(2) . . . . ? C24 C33 C38 C37 179.5(14) . . . . ? C36 C37 C38 C33 -3(3) . . . . ? C25 C26 C39 F4 -13(3) . . . . ? O21 C26 C39 F4 175.2(14) . . . . ? C25 C26 C39 F6 107(2) . . . . ? O21 C26 C39 F6 -65(2) . . . . ? C25 C26 C39 F5 -133.5(19) . . . . ? O21 C26 C39 F5 54(2) . . . . ? C46 O41 C42 O60 -174.5(15) . . . . ? C46 O41 C42 C43 12(2) . . . . ? O60 C42 C43 C47 15(2) . . . . ? O41 C42 C43 C47 -172.9(13) . . . . ? O60 C42 C43 C44 142.1(16) . . . . ? O41 C42 C43 C44 -45.7(18) . . . . ? C47 C43 C44 C53 -64.5(18) . . . . ? C42 C43 C44 C53 170.9(14) . . . . ? C47 C43 C44 C45 176.0(12) . . . . ? C42 C43 C44 C45 51.4(16) . . . . ? C53 C44 C45 C46 -151.1(16) . . . . ? C43 C44 C45 C46 -31(2) . . . . ? C44 C45 C46 O41 0(3) . . . . ? C44 C45 C46 C59 -177.6(18) . . . . ? C42 O41 C46 C45 11(3) . . . . ? C42 O41 C46 C59 -170.7(16) . . . . ? C42 C43 C47 C52 73.4(18) . . . . ? C44 C43 C47 C52 -53.2(19) . . . . ? C42 C43 C47 C48 -103.1(15) . . . . ? C44 C43 C47 C48 130.3(13) . . . . ? C52 C47 C48 C49 -2(2) . . . . ? C43 C47 C48 C49 174.7(13) . . . . ? C47 C48 C49 C50 2(2) . . . . ? C48 C49 C50 C51 -1(2) . . . . ? C48 C49 C50 Br3 -176.4(10) . . . . ? C49 C50 C51 C52 0(2) . . . . ? Br3 C50 C51 C52 175.6(11) . . . . ? C48 C47 C52 C51 1(2) . . . . ? C43 C47 C52 C51 -175.5(13) . . . . ? C50 C51 C52 C47 0(2) . . . . ? C43 C44 C53 C58 -71(2) . . . . ? C45 C44 C53 C58 45(2) . . . . ? C43 C44 C53 C54 107.4(17) . . . . ? C45 C44 C53 C54 -136.8(15) . . . . ? C58 C53 C54 C55 0(3) . . . . ? C44 C53 C54 C55 -179.1(15) . . . . ? C53 C54 C55 C56 2(3) . . . . ? C54 C55 C56 C57 -4(3) . . . . ? C55 C56 C57 C58 5(3) . . . . ? C54 C53 C58 C57 2(3) . . . . ? C44 C53 C58 C57 -179.8(15) . . . . ? C56 C57 C58 C53 -4(3) . . . . ? C45 C46 C59 F7 125(2) . . . . ? O41 C46 C59 F7 -53(2) . . . . ? C45 C46 C59 F8 -1(3) . . . . ? O41 C46 C59 F8 -179.2(17) . . . . ? C45 C46 C59 F9 -120(2) . . . . ? O41 C46 C59 F9 62(2) . . . . ? C66 O61 C62 O80 -177.7(14) . . . . ? C66 O61 C62 C63 9(2) . . . . ? O80 C62 C63 C67 19(2) . . . . ? O61 C62 C63 C67 -168.8(12) . . . . ? O80 C62 C63 C64 148.5(16) . . . . ? O61 C62 C63 C64 -40(2) . . . . ? C62 C63 C64 C73 167.1(15) . . . . ? C67 C63 C64 C73 -62.3(17) . . . . ? C62 C63 C64 C65 45.0(19) . . . . ? C67 C63 C64 C65 175.6(13) . . . . ? C73 C64 C65 C66 -144.7(19) . . . . ? C63 C64 C65 C66 -26(2) . . . . ? C64 C65 C66 O61 -1(3) . . . . ? C64 C65 C66 C79 176.1(18) . . . . ? C62 O61 C66 C65 12(3) . . . . ? C62 O61 C66 C79 -165.7(15) . . . . ? C62 C63 C67 C72 75.8(19) . . . . ? C64 C63 C67 C72 -57(2) . . . . ? C62 C63 C67 C68 -106.3(18) . . . . ? C64 C63 C67 C68 121.3(16) . . . . ? C72 C67 C68 C69 1(3) . . . . ? C63 C67 C68 C69 -177.1(16) . . . . ? C67 C68 C69 C70 -1(3) . . . . ? C68 C69 C70 C71 2(3) . . . . ? C68 C69 C70 Br4 178.8(14) . . . . ? C69 C70 C71 C72 -4(3) . . . . ? Br4 C70 C71 C72 179.4(13) . . . . ? C70 C71 C72 C67 4(3) . . . . ? C68 C67 C72 C71 -3(2) . . . . ? C63 C67 C72 C71 175.0(16) . . . . ? C65 C64 C73 C74 49(2) . . . . ? C63 C64 C73 C74 -67(2) . . . . ? C65 C64 C73 C78 -136.2(15) . . . . ? C63 C64 C73 C78 107.8(17) . . . . ? C78 C73 C74 C75 -1(3) . . . . ? C64 C73 C74 C75 174.2(18) . . . . ? C73 C74 C75 C76 0(3) . . . . ? C74 C75 C76 C77 1(4) . . . . ? C75 C76 C77 C78 -2(4) . . . . ? C76 C77 C78 C73 1(3) . . . . ? C74 C73 C78 C77 0(3) . . . . ? C64 C73 C78 C77 -175.3(17) . . . . ? C65 C66 C79 F10 -124(3) . . . . ? O61 C66 C79 F10 53(3) . . . . ? C65 C66 C79 F12 9(3) . . . . ? O61 C66 C79 F12 -174.0(18) . . . . ? C65 C66 C79 F11 116(2) . . . . ? O61 C66 C79 F11 -67(2) . . . . ? C86 O81 C82 O100 -176.3(15) . . . . ? C86 O81 C82 C83 4(2) . . . . ? O100 C82 C83 C87 12(3) . . . . ? O81 C82 C83 C87 -169.0(15) . . . . ? O100 C82 C83 C84 139.3(19) . . . . ? O81 C82 C83 C84 -41.3(19) . . . . ? C87 C83 C84 C85 -179.4(13) . . . . ? C82 C83 C84 C85 54.9(16) . . . . ? C87 C83 C84 C93 -56.0(18) . . . . ? C82 C83 C84 C93 178.4(13) . . . . ? C93 C84 C85 C86 -158.9(16) . . . . ? C83 C84 C85 C86 -37(2) . . . . ? C84 C85 C86 O81 0(2) . . . . ? C84 C85 C86 C99 -176.6(19) . . . . ? C82 O81 C86 C85 19(2) . . . . ? C82 O81 C86 C99 -163.4(17) . . . . ? C82 C83 C87 C92 92.8(18) . . . . ? C84 C83 C87 C92 -32(2) . . . . ? C82 C83 C87 C88 -86.1(17) . . . . ? C84 C83 C87 C88 149.5(13) . . . . ? C92 C87 C88 C89 0(2) . . . . ? C83 C87 C88 C89 179.2(12) . . . . ? C87 C88 C89 C90 1(2) . . . . ? C88 C89 C90 C91 -1(3) . . . . ? C88 C89 C90 Br5 179.8(11) . . . . ? C89 C90 C91 C92 -1(2) . . . . ? Br5 C90 C91 C92 178.0(10) . . . . ? C88 C87 C92 C91 -3(2) . . . . ? C83 C87 C92 C91 178.5(14) . . . . ? C90 C91 C92 C87 3(2) . . . . ? C85 C84 C93 C98 97(2) . . . . ? C83 C84 C93 C98 -23(2) . . . . ? C85 C84 C93 C94 -83.7(19) . . . . ? C83 C84 C93 C94 156.5(16) . . . . ? C98 C93 C94 C95 -2(3) . . . . ? C84 C93 C94 C95 178.4(15) . . . . ? C93 C94 C95 C96 5(3) . . . . ? C94 C95 C96 C97 -5(3) . . . . ? C95 C96 C97 C98 2(3) . . . . ? C94 C93 C98 C97 -1(3) . . . . ? C84 C93 C98 C97 178.6(15) . . . . ? C96 C97 C98 C93 1(3) . . . . ? C85 C86 C99 F15 -5(3) . . . . ? O81 C86 C99 F15 178.2(17) . . . . ? C85 C86 C99 F13 117(2) . . . . ? O81 C86 C99 F13 -60(2) . . . . ? C85 C86 C99 F14 -125(2) . . . . ? O81 C86 C99 F14 58(2) . . . . ? C106 O101 C102 O120 -175.1(13) . . . . ? C106 O101 C102 C103 13(2) . . . . ? O120 C102 C103 C107 23(2) . . . . ? O101 C102 C103 C107 -165.9(13) . . . . ? O120 C102 C103 C104 150.6(14) . . . . ? O101 C102 C103 C104 -37.9(19) . . . . ? C107 C103 C104 C113 -73.0(17) . . . . ? C102 C103 C104 C113 161.5(13) . . . . ? C107 C103 C104 C105 164.9(14) . . . . ? C102 C103 C104 C105 39.5(17) . . . . ? C113 C104 C105 C106 -141.9(15) . . . . ? C103 C104 C105 C106 -21(2) . . . . ? C104 C105 C106 O101 -6(3) . . . . ? C104 C105 C106 C119 179.4(16) . . . . ? C102 O101 C106 C105 12(2) . . . . ? C102 O101 C106 C119 -173.2(15) . . . . ? C102 C103 C107 C108 59(2) . . . . ? C104 C103 C107 C108 -67(2) . . . . ? C102 C103 C107 C112 -123.7(16) . . . . ? C104 C103 C107 C112 110.6(17) . . . . ? C112 C107 C108 C109 1(3) . . . . ? C103 C107 C108 C109 178.0(17) . . . . ? C107 C108 C109 C110 1(3) . . . . ? C108 C109 C110 C111 0(3) . . . . ? C108 C109 C110 Br6 178.6(14) . . . . ? C109 C110 C111 C112 -2(3) . . . . ? Br6 C110 C111 C112 179.9(12) . . . . ? C110 C111 C112 C107 3(3) . . . . ? C108 C107 C112 C111 -2(3) . . . . ? C103 C107 C112 C111 -179.8(15) . . . . ? C105 C104 C113 C118 30(2) . . . . ? C103 C104 C113 C118 -92(2) . . . . ? C105 C104 C113 C114 -154.8(15) . . . . ? C103 C104 C113 C114 83.2(17) . . . . ? C118 C113 C114 C115 -4(3) . . . . ? C104 C113 C114 C115 -179.0(15) . . . . ? C113 C114 C115 C116 3(3) . . . . ? C114 C115 C116 C117 -5(4) . . . . ? C115 C116 C117 C118 8(4) . . . . ? C114 C113 C118 C117 8(3) . . . . ? C104 C113 C118 C117 -177.5(19) . . . . ? C116 C117 C118 C113 -10(3) . . . . ? C105 C106 C119 F18 -1(3) . . . . ? O101 C106 C119 F18 -176.9(16) . . . . ? C105 C106 C119 F17 -124(2) . . . . ? O101 C106 C119 F17 60(2) . . . . ? C105 C106 C119 F16 120(2) . . . . ? O101 C106 C119 F16 -55(2) . . . . ? C126 O121 C122 O140 -165.8(14) . . . . ? C126 O121 C122 C123 15.5(19) . . . . ? O140 C122 C123 C127 4(2) . . . . ? O121 C122 C123 C127 -177.1(12) . . . . ? O140 C122 C123 C124 132.7(17) . . . . ? O121 C122 C123 C124 -48.7(19) . . . . ? C127 C123 C124 C125 179.0(14) . . . . ? C122 C123 C124 C125 53.9(18) . . . . ? C127 C123 C124 C133 -57.3(19) . . . . ? C122 C123 C124 C133 177.6(14) . . . . ? C123 C124 C125 C126 -31(2) . . . . ? C133 C124 C125 C126 -156.2(15) . . . . ? C124 C125 C126 O121 -2(2) . . . . ? C124 C125 C126 C139 -178.2(18) . . . . ? C122 O121 C126 C125 12(2) . . . . ? C122 O121 C126 C139 -171.4(15) . . . . ? C122 C123 C127 C132 85.6(19) . . . . ? C124 C123 C127 C132 -39(2) . . . . ? C122 C123 C127 C128 -85.6(18) . . . . ? C124 C123 C127 C128 149.7(15) . . . . ? C132 C127 C128 C129 0(2) . . . . ? C123 C127 C128 C129 171.7(15) . . . . ? C127 C128 C129 C130 3(3) . . . . ? C128 C129 C130 C131 -2(3) . . . . ? C128 C129 C130 Br7 177.7(13) . . . . ? C129 C130 C131 C132 -1(3) . . . . ? Br7 C130 C131 C132 179.2(12) . . . . ? C130 C131 C132 C127 4(3) . . . . ? C128 C127 C132 C131 -3(3) . . . . ? C123 C127 C132 C131 -174.1(16) . . . . ? C125 C124 C133 C134 -137.9(16) . . . . ? C123 C124 C133 C134 101.1(18) . . . . ? C125 C124 C133 C138 41(2) . . . . ? C123 C124 C133 C138 -80(2) . . . . ? C138 C133 C134 C135 -2(3) . . . . ? C124 C133 C134 C135 177.5(15) . . . . ? C133 C134 C135 C136 1(3) . . . . ? C134 C135 C136 C137 -3(3) . . . . ? C135 C136 C137 C138 7(3) . . . . ? C136 C137 C138 C133 -7(3) . . . . ? C134 C133 C138 C137 5(3) . . . . ? C124 C133 C138 C137 -174.2(15) . . . . ? C125 C126 C139 F19 0(3) . . . . ? O121 C126 C139 F19 -176.9(15) . . . . ? C125 C126 C139 F20 -125(2) . . . . ? O121 C126 C139 F20 58(2) . . . . ? C125 C126 C139 F21 118(2) . . . . ? O121 C126 C139 F21 -58(2) . . . . ? C146 O141 C142 O160 -179.6(15) . . . . ? C146 O141 C142 C143 1(2) . . . . ? O160 C142 C143 C144 135.7(17) . . . . ? O141 C142 C143 C144 -45.0(16) . . . . ? O160 C142 C143 C147 3(2) . . . . ? O141 C142 C143 C147 -178.1(12) . . . . ? C147 C143 C144 C145 -169.8(13) . . . . ? C142 C143 C144 C145 61.7(16) . . . . ? C147 C143 C144 C153 -40.9(18) . . . . ? C142 C143 C144 C153 -169.5(13) . . . . ? C143 C144 C145 C146 -38(2) . . . . ? C153 C144 C145 C146 -164.4(15) . . . . ? C142 O141 C146 C159 -163.8(15) . . . . ? C142 O141 C146 C145 27(2) . . . . ? C144 C145 C146 O141 -8(2) . . . . ? C144 C145 C146 C159 -175.0(16) . . . . ? C144 C143 C147 C148 -47(2) . . . . ? C142 C143 C147 C148 79(2) . . . . ? C144 C143 C147 C152 125.6(17) . . . . ? C142 C143 C147 C152 -108.5(17) . . . . ? C152 C147 C148 C149 2(3) . . . . ? C143 C147 C148 C149 174.7(16) . . . . ? C147 C148 C149 C150 0(3) . . . . ? C148 C149 C150 C151 0(3) . . . . ? C148 C149 C150 Br8 176.7(13) . . . . ? C149 C150 C151 C152 -1(3) . . . . ? Br8 C150 C151 C152 -178.3(14) . . . . ? C148 C147 C152 C151 -4(3) . . . . ? C143 C147 C152 C151 -176.6(17) . . . . ? C150 C151 C152 C147 4(3) . . . . ? C145 C144 C153 C154 -112.7(18) . . . . ? C143 C144 C153 C154 121.7(18) . . . . ? C145 C144 C153 C158 69(2) . . . . ? C143 C144 C153 C158 -57(2) . . . . ? C158 C153 C154 C155 6(3) . . . . ? C144 C153 C154 C155 -172.4(18) . . . . ? C153 C154 C155 C156 -4(3) . . . . ? C154 C155 C156 C157 1(3) . . . . ? C155 C156 C157 C158 0(3) . . . . ? C154 C153 C158 C157 -4(2) . . . . ? C144 C153 C158 C157 173.8(16) . . . . ? C156 C157 C158 C153 2(3) . . . . ? O141 C146 C159 F22 -71(2) . . . . ? C145 C146 C159 F22 97(2) . . . . ? O141 C146 C159 F24 52(2) . . . . ? C145 C146 C159 F24 -140.4(19) . . . . ? O141 C146 C159 F23 167.2(14) . . . . ? C145 C146 C159 F23 -25(3) . . . . ? _diffrn_measured_fraction_theta_max 0.740 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.740 _refine_diff_density_max 0.459 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.105 _database_code_depnum_ccdc_archive 'CCDC 907808' ####################################################################### # # 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_41 #TrackingRef '47.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration rm _chemical_formula_moiety 'C22 H19 F3 O2' _chemical_formula_sum 'C22 H19 F3 O2' _chemical_formula_weight 372.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.039(5) _cell_length_b 27.449(18) _cell_length_c 11.299(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.404(13) _cell_angle_gamma 90.00 _cell_volume 1814(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1776 _cell_measurement_theta_min 21.2 _cell_measurement_theta_max 67.5 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.902 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.572 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24420 _diffrn_reflns_av_R_equivalents 0.1915 _diffrn_reflns_av_sigmaI/netI 0.1200 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 67.80 _reflns_number_total 6439 _reflns_number_gt 3884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1709P)^2^+0.2700P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0087(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(3) _refine_ls_number_reflns 6439 _refine_ls_number_parameters 488 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1492 _refine_ls_R_factor_gt 0.1131 _refine_ls_wR_factor_ref 0.3357 _refine_ls_wR_factor_gt 0.2972 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.053 _refine_ls_shift/su_mean 0.014 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 O1 O 0.3495(10) 0.4089(2) 0.0253(5) 0.0809(15) Uani 1 1 d . . . C2 C 0.2052(14) 0.3676(3) 0.0065(8) 0.076(2) Uani 1 1 d . . . O2 O -0.0124(11) 0.3765(2) -0.0690(6) 0.0904(17) Uani 1 1 d . . . H2O H -0.1267 0.3586 -0.0382 0.136 Uiso 1 1 calc R . . C3 C 0.1761(14) 0.3441(3) 0.1246(7) 0.0689(19) Uani 1 1 d . . . H3A H 0.3237 0.3301 0.1706 0.083 Uiso 1 1 calc R . . H3B H 0.0632 0.3173 0.1046 0.083 Uiso 1 1 calc R . . C4 C 0.0940(13) 0.3824(3) 0.2036(7) 0.0694(19) Uani 1 1 d . . . H4A H -0.0616 0.3936 0.1582 0.083 Uiso 1 1 calc R . . C5 C 0.2591(13) 0.4275(3) 0.2207(8) 0.074(2) Uani 1 1 d . . . H5A H 0.4155 0.4158 0.2630 0.089 Uiso 1 1 calc R . . C6 C 0.2694(16) 0.4463(3) 0.0950(7) 0.077(2) Uani 1 1 d . . . H6A H 0.1153 0.4572 0.0498 0.092 Uiso 1 1 calc R . . H6B H 0.3734 0.4747 0.1049 0.092 Uiso 1 1 calc R . . C7 C 0.3310(18) 0.3314(3) -0.0582(9) 0.086(2) Uani 1 1 d . . . F1 F 0.3514(11) 0.3505(2) -0.1678(5) 0.1002(16) Uani 1 1 d . . . F2 F 0.2147(11) 0.2901(2) -0.0880(6) 0.1046(17) Uani 1 1 d . . . F3 F 0.5429(10) 0.3210(2) 0.0046(5) 0.1010(17) Uani 1 1 d . . . C8 C 0.0742(13) 0.3600(2) 0.3238(7) 0.0651(18) Uani 1 1 d . . . C9 C 0.2588(13) 0.3575(3) 0.4247(8) 0.071(2) Uani 1 1 d . . . H9A H 0.3996 0.3723 0.4219 0.085 Uiso 1 1 calc R . . C10 C 0.2404(16) 0.3333(3) 0.5303(8) 0.078(2) Uani 1 1 d . . . H10A H 0.3700 0.3310 0.5978 0.094 Uiso 1 1 calc R . . C11 C 0.0387(16) 0.3131(3) 0.5378(9) 0.081(2) Uani 1 1 d . . . H11A H 0.0256 0.2976 0.6108 0.097 Uiso 1 1 calc R . . C12 C -0.1484(17) 0.3156(4) 0.4371(10) 0.091(3) Uani 1 1 d . . . H12A H -0.2886 0.3008 0.4411 0.110 Uiso 1 1 calc R . . C13 C -0.1330(15) 0.3391(3) 0.3309(10) 0.083(2) Uani 1 1 d . . . H13A H -0.2628 0.3411 0.2633 0.100 Uiso 1 1 calc R . . C14 C 0.2012(12) 0.4692(3) 0.2948(8) 0.071(2) Uani 1 1 d . . . C15 C -0.0248(13) 0.4891(3) 0.2728(8) 0.077(2) Uani 1 1 d . . . H15A H -0.1449 0.4742 0.2132 0.093 Uiso 1 1 calc R . . C16 C -0.0724(14) 0.5286(3) 0.3344(8) 0.073(2) Uani 1 1 d . . . H16A H -0.2238 0.5411 0.3168 0.088 Uiso 1 1 calc R . . C17 C 0.1049(13) 0.5517(3) 0.4260(8) 0.075(2) Uani 1 1 d . . . C18 C 0.0667(15) 0.5936(4) 0.4954(8) 0.080(2) Uani 1 1 d . . . H18A H -0.0806 0.6082 0.4797 0.096 Uiso 1 1 calc R . . C19 C 0.2470(16) 0.6128(3) 0.5856(9) 0.082(2) Uani 1 1 d . . . H19A H 0.2196 0.6393 0.6343 0.098 Uiso 1 1 calc R . . C20 C 0.4664(15) 0.5936(3) 0.6050(8) 0.077(2) Uani 1 1 d . . . H20A H 0.5895 0.6091 0.6613 0.092 Uiso 1 1 calc R . . C21 C 0.5077(14) 0.5528(3) 0.5443(9) 0.075(2) Uani 1 1 d . . . H21A H 0.6560 0.5387 0.5638 0.090 Uiso 1 1 calc R . . C22 C 0.3306(13) 0.5314(3) 0.4522(8) 0.073(2) Uani 1 1 d . . . C23 C 0.3683(12) 0.4897(3) 0.3853(7) 0.0694(19) Uani 1 1 d . . . H23A H 0.5164 0.4755 0.4042 0.083 Uiso 1 1 calc R . . O31 O 0.4321(9) 0.6303(2) 0.2105(5) 0.0773(15) Uani 1 1 d . . . C32 C 0.3118(15) 0.6731(3) 0.2281(8) 0.081(2) Uani 1 1 d . . . O32 O 0.1600(10) 0.6638(3) 0.3017(6) 0.0948(18) Uani 1 1 d . . . H32O H 0.0136 0.6525 0.2505 0.142 Uiso 1 1 calc R . . C33 C 0.1787(14) 0.6948(3) 0.1082(7) 0.075(2) Uani 1 1 d . . . H33A H 0.2870 0.7068 0.0619 0.090 Uiso 1 1 calc R . . H33B H 0.0888 0.7230 0.1251 0.090 Uiso 1 1 calc R . . C34 C 0.0153(14) 0.6571(3) 0.0298(7) 0.0704(19) Uani 1 1 d . . . H34A H -0.0999 0.6469 0.0750 0.085 Uiso 1 1 calc R . . C35 C 0.1607(14) 0.6118(3) 0.0142(7) 0.071(2) Uani 1 1 d . . . H35A H 0.2770 0.6225 -0.0298 0.085 Uiso 1 1 calc R . . C36 C 0.2881(16) 0.5940(3) 0.1410(9) 0.085(2) Uani 1 1 d . . . H36A H 0.1752 0.5835 0.1861 0.102 Uiso 1 1 calc R . . H36B H 0.3820 0.5654 0.1320 0.102 Uiso 1 1 calc R . . C37 C 0.4981(17) 0.7075(3) 0.2960(9) 0.086(3) Uani 1 1 d . . . F31 F 0.6106(11) 0.6892(2) 0.4076(5) 0.1066(17) Uani 1 1 d . . . F32 F 0.4110(11) 0.7489(2) 0.3204(6) 0.1125(19) Uani 1 1 d . . . F33 F 0.6570(9) 0.7166(2) 0.2357(5) 0.1053(17) Uani 1 1 d . . . C38 C -0.1104(13) 0.6788(3) -0.0921(8) 0.075(2) Uani 1 1 d . . . C39 C -0.0083(15) 0.6844(4) -0.1897(9) 0.090(3) Uani 1 1 d . . . H39A H 0.1437 0.6731 -0.1809 0.109 Uiso 1 1 calc R . . C40 C -0.1243(16) 0.7061(4) -0.3001(9) 0.087(2) Uani 1 1 d . . . H40A H -0.0568 0.7074 -0.3675 0.105 Uiso 1 1 calc R . . C41 C -0.3381(16) 0.7256(3) -0.3087(9) 0.086(2) Uani 1 1 d . . . H41A H -0.4168 0.7413 -0.3819 0.103 Uiso 1 1 calc R . . C42 C -0.4389(15) 0.7224(4) -0.2121(9) 0.088(3) Uani 1 1 d . . . H42A H -0.5850 0.7366 -0.2191 0.105 Uiso 1 1 calc R . . C43 C -0.3308(14) 0.6989(3) -0.1054(9) 0.085(2) Uani 1 1 d . . . H43A H -0.4048 0.6962 -0.0406 0.102 Uiso 1 1 calc R . . C44 C 0.0270(13) 0.5696(3) -0.0567(8) 0.076(2) Uani 1 1 d . . . C45 C -0.1761(14) 0.5516(3) -0.0297(8) 0.076(2) Uani 1 1 d . . . H45A H -0.2345 0.5672 0.0312 0.091 Uiso 1 1 calc R . . C46 C -0.2866(14) 0.5126(3) -0.0895(7) 0.074(2) Uani 1 1 d . . . H46A H -0.4175 0.5006 -0.0666 0.088 Uiso 1 1 calc R . . C47 C -0.2134(13) 0.4881(3) -0.1880(8) 0.072(2) Uani 1 1 d . . . C48 C -0.3237(16) 0.4475(3) -0.2515(8) 0.079(2) Uani 1 1 d . . . H48A H -0.4563 0.4347 -0.2321 0.095 Uiso 1 1 calc R . . C49 C -0.2400(17) 0.4262(4) -0.3425(9) 0.087(2) Uani 1 1 d . . . H49A H -0.3161 0.3990 -0.3864 0.104 Uiso 1 1 calc R . . C50 C -0.0419(16) 0.4450(4) -0.3700(8) 0.087(3) Uani 1 1 d . . . H50A H 0.0169 0.4296 -0.4310 0.104 Uiso 1 1 calc R . . C51 C 0.0674(14) 0.4847(3) -0.3112(8) 0.078(2) Uani 1 1 d . . . H51A H 0.1979 0.4974 -0.3332 0.094 Uiso 1 1 calc R . . C52 C -0.0138(13) 0.5070(3) -0.2170(7) 0.0677(19) Uani 1 1 d . . . C53 C 0.1005(13) 0.5487(3) -0.1486(7) 0.072(2) Uani 1 1 d . . . H53A H 0.2318 0.5617 -0.1691 0.087 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 O1 0.085(4) 0.075(3) 0.091(4) -0.011(3) 0.036(3) -0.012(3) C2 0.076(5) 0.077(5) 0.073(5) 0.003(4) 0.015(4) 0.010(4) O2 0.088(4) 0.093(4) 0.090(4) -0.005(3) 0.022(3) -0.001(3) C3 0.069(4) 0.069(4) 0.070(5) 0.011(4) 0.021(4) 0.006(3) C4 0.063(4) 0.070(4) 0.080(5) 0.006(4) 0.027(4) 0.005(4) C5 0.059(4) 0.085(5) 0.082(5) -0.005(4) 0.025(4) 0.005(4) C6 0.087(5) 0.081(5) 0.072(5) 0.006(4) 0.037(4) 0.001(4) C7 0.103(7) 0.069(5) 0.091(6) -0.006(5) 0.035(5) 0.001(5) F1 0.133(4) 0.095(4) 0.082(3) 0.003(3) 0.046(3) -0.002(3) F2 0.134(4) 0.078(3) 0.114(4) -0.019(3) 0.054(3) -0.012(3) F3 0.088(3) 0.117(4) 0.109(4) -0.002(3) 0.048(3) 0.011(3) C8 0.068(4) 0.053(4) 0.080(5) -0.006(3) 0.030(4) 0.003(3) C9 0.061(4) 0.081(5) 0.073(5) 0.008(4) 0.020(4) -0.003(4) C10 0.084(5) 0.076(5) 0.078(5) 0.005(4) 0.025(4) 0.003(4) C11 0.087(6) 0.078(5) 0.088(6) -0.013(5) 0.039(5) -0.009(4) C12 0.087(6) 0.090(6) 0.109(8) -0.007(6) 0.048(6) -0.009(5) C13 0.069(5) 0.086(6) 0.104(6) 0.009(5) 0.038(5) 0.000(4) C14 0.061(4) 0.077(5) 0.080(5) 0.005(4) 0.028(4) -0.003(4) C15 0.060(4) 0.095(6) 0.082(5) 0.007(5) 0.030(4) -0.004(4) C16 0.073(5) 0.075(5) 0.081(5) 0.004(4) 0.036(4) 0.000(4) C17 0.066(4) 0.081(5) 0.088(6) -0.006(4) 0.038(4) -0.008(4) C18 0.079(5) 0.093(6) 0.076(5) -0.001(5) 0.033(4) 0.001(4) C19 0.089(6) 0.080(5) 0.083(6) -0.008(4) 0.035(5) -0.005(5) C20 0.075(5) 0.086(6) 0.072(5) 0.009(4) 0.023(4) -0.003(4) C21 0.068(4) 0.060(4) 0.098(6) 0.011(4) 0.023(4) 0.005(4) C22 0.067(5) 0.078(5) 0.083(5) 0.007(4) 0.035(4) 0.002(4) C23 0.057(4) 0.080(5) 0.073(5) 0.003(4) 0.019(4) -0.002(4) O31 0.074(3) 0.082(4) 0.076(4) -0.007(3) 0.018(3) 0.002(3) C32 0.087(5) 0.097(6) 0.071(5) -0.023(5) 0.041(4) -0.013(5) O32 0.084(4) 0.122(5) 0.089(4) 0.002(3) 0.043(3) -0.011(3) C33 0.084(5) 0.073(5) 0.073(5) 0.000(4) 0.033(4) -0.003(4) C34 0.083(5) 0.070(5) 0.065(5) 0.000(4) 0.030(4) -0.003(4) C35 0.086(5) 0.070(4) 0.063(5) 0.008(4) 0.032(4) 0.007(4) C36 0.086(5) 0.083(5) 0.093(6) -0.004(5) 0.035(5) -0.012(5) C37 0.106(6) 0.074(5) 0.088(6) -0.021(5) 0.042(6) -0.024(5) F31 0.122(4) 0.112(4) 0.077(3) -0.001(3) 0.009(3) -0.007(3) F32 0.119(4) 0.084(3) 0.124(5) -0.026(3) 0.010(4) 0.001(3) F33 0.086(3) 0.127(4) 0.103(4) 0.006(3) 0.024(3) -0.028(3) C38 0.064(4) 0.090(5) 0.083(5) -0.014(4) 0.040(4) -0.014(4) C39 0.073(5) 0.108(7) 0.102(7) -0.004(6) 0.045(5) 0.001(5) C40 0.079(5) 0.103(7) 0.084(6) 0.018(5) 0.028(5) 0.008(5) C41 0.092(6) 0.076(5) 0.093(6) 0.002(5) 0.031(5) 0.010(5) C42 0.066(5) 0.101(6) 0.105(7) 0.010(5) 0.040(5) 0.007(4) C43 0.079(5) 0.087(6) 0.100(7) 0.021(5) 0.044(5) 0.013(4) C44 0.066(4) 0.079(5) 0.087(6) -0.003(4) 0.027(4) 0.003(4) C45 0.077(5) 0.084(6) 0.076(5) -0.003(4) 0.036(4) -0.008(4) C46 0.067(4) 0.088(6) 0.073(5) -0.002(4) 0.031(4) 0.002(4) C47 0.064(4) 0.079(5) 0.078(5) 0.001(4) 0.026(4) 0.000(4) C48 0.084(5) 0.068(5) 0.087(6) 0.002(4) 0.024(5) -0.013(4) C49 0.087(6) 0.090(6) 0.082(6) -0.009(5) 0.019(5) 0.008(5) C50 0.087(6) 0.097(6) 0.077(6) -0.025(5) 0.021(5) 0.005(5) C51 0.077(5) 0.091(6) 0.072(5) 0.001(5) 0.030(4) 0.003(4) C52 0.059(4) 0.083(5) 0.064(4) -0.010(4) 0.021(3) -0.003(4) C53 0.070(4) 0.087(5) 0.067(5) 0.005(4) 0.030(4) 0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.413(10) . ? O1 C6 1.447(10) . ? C2 O2 1.399(10) . ? C2 C3 1.531(11) . ? C2 C7 1.541(12) . ? O2 H2O 0.9800 . ? C3 C4 1.540(11) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C8 1.522(11) . ? C4 C5 1.570(12) . ? C4 H4A 1.0000 . ? C5 C14 1.509(12) . ? C5 C6 1.527(12) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 F3 1.331(12) . ? C7 F2 1.333(11) . ? C7 F1 1.378(11) . ? C8 C9 1.384(11) . ? C8 C13 1.397(11) . ? C9 C10 1.394(11) . ? C9 H9A 0.9500 . ? C10 C11 1.360(12) . ? C10 H10A 0.9500 . ? C11 C12 1.391(14) . ? C11 H11A 0.9500 . ? C12 C13 1.386(14) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C23 1.367(11) . ? C14 C15 1.434(11) . ? C15 C16 1.357(12) . ? C15 H15A 0.9500 . ? C16 C17 1.438(12) . ? C16 H16A 0.9500 . ? C17 C22 1.434(11) . ? C17 C18 1.443(12) . ? C18 C19 1.396(13) . ? C18 H18A 0.9500 . ? C19 C20 1.392(13) . ? C19 H19A 0.9500 . ? C20 C21 1.368(12) . ? C20 H20A 0.9500 . ? C21 C22 1.421(12) . ? C21 H21A 0.9500 . ? C22 C23 1.419(11) . ? C23 H23A 0.9500 . ? O31 C32 1.421(11) . ? O31 C36 1.422(11) . ? C32 O32 1.406(10) . ? C32 C33 1.515(13) . ? C32 C37 1.523(12) . ? O32 H32O 0.9800 . ? C33 C34 1.548(12) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C38 1.519(12) . ? C34 C35 1.558(11) . ? C34 H34A 1.0000 . ? C35 C44 1.521(12) . ? C35 C36 1.527(13) . ? C35 H35A 1.0000 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 F32 1.311(11) . ? C37 F33 1.332(10) . ? C37 F31 1.370(12) . ? C38 C39 1.399(11) . ? C38 C43 1.414(11) . ? C39 C40 1.403(14) . ? C39 H39A 0.9500 . ? C40 C41 1.378(13) . ? C40 H40A 0.9500 . ? C41 C42 1.379(12) . ? C41 H41A 0.9500 . ? C42 C43 1.380(13) . ? C42 H42A 0.9500 . ? C43 H43A 0.9500 . ? C44 C53 1.354(11) . ? C44 C45 1.424(11) . ? C45 C46 1.349(12) . ? C45 H45A 0.9500 . ? C46 C47 1.460(11) . ? C46 H46A 0.9500 . ? C47 C48 1.399(12) . ? C47 C52 1.424(10) . ? C48 C49 1.383(12) . ? C48 H48A 0.9500 . ? C49 C50 1.406(14) . ? C49 H49A 0.9500 . ? C50 C51 1.358(13) . ? C50 H50A 0.9500 . ? C51 C52 1.418(11) . ? C51 H51A 0.9500 . ? C52 C53 1.455(12) . ? C53 H53A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C6 111.9(6) . . ? O2 C2 O1 113.7(7) . . ? O2 C2 C3 108.1(7) . . ? O1 C2 C3 114.1(7) . . ? O2 C2 C7 108.8(7) . . ? O1 C2 C7 103.3(6) . . ? C3 C2 C7 108.6(7) . . ? C2 O2 H2O 109.5 . . ? C2 C3 C4 109.9(6) . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C8 C4 C3 110.4(6) . . ? C8 C4 C5 113.4(7) . . ? C3 C4 C5 108.9(6) . . ? C8 C4 H4A 108.0 . . ? C3 C4 H4A 108.0 . . ? C5 C4 H4A 108.0 . . ? C14 C5 C6 109.2(7) . . ? C14 C5 C4 116.0(6) . . ? C6 C5 C4 108.8(7) . . ? C14 C5 H5A 107.5 . . ? C6 C5 H5A 107.5 . . ? C4 C5 H5A 107.5 . . ? O1 C6 C5 111.4(7) . . ? O1 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? O1 C6 H6B 109.3 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? F3 C7 F2 109.2(8) . . ? F3 C7 F1 105.7(7) . . ? F2 C7 F1 104.8(8) . . ? F3 C7 C2 114.1(8) . . ? F2 C7 C2 112.2(8) . . ? F1 C7 C2 110.3(7) . . ? C9 C8 C13 118.8(7) . . ? C9 C8 C4 122.0(6) . . ? C13 C8 C4 119.2(8) . . ? C8 C9 C10 120.7(7) . . ? C8 C9 H9A 119.7 . . ? C10 C9 H9A 119.7 . . ? C11 C10 C9 120.7(9) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C10 C11 C12 119.2(9) . . ? C10 C11 H11A 120.4 . . ? C12 C11 H11A 120.4 . . ? C13 C12 C11 120.9(9) . . ? C13 C12 H12A 119.5 . . ? C11 C12 H12A 119.5 . . ? C12 C13 C8 119.7(9) . . ? C12 C13 H13A 120.2 . . ? C8 C13 H13A 120.1 . . ? C23 C14 C15 117.8(8) . . ? C23 C14 C5 119.9(7) . . ? C15 C14 C5 122.3(8) . . ? C16 C15 C14 122.0(8) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C15 C16 C17 120.4(7) . . ? C15 C16 H16A 119.8 . . ? C17 C16 H16A 119.8 . . ? C22 C17 C16 118.4(7) . . ? C22 C17 C18 118.1(8) . . ? C16 C17 C18 123.5(7) . . ? C19 C18 C17 119.7(8) . . ? C19 C18 H18A 120.1 . . ? C17 C18 H18A 120.1 . . ? C20 C19 C18 120.7(9) . . ? C20 C19 H19A 119.6 . . ? C18 C19 H19A 119.6 . . ? C21 C20 C19 121.1(9) . . ? C21 C20 H20A 119.5 . . ? C19 C20 H20A 119.5 . . ? C20 C21 C22 120.6(8) . . ? C20 C21 H21A 119.7 . . ? C22 C21 H21A 119.7 . . ? C21 C22 C23 122.1(7) . . ? C21 C22 C17 119.6(7) . . ? C23 C22 C17 118.3(8) . . ? C14 C23 C22 123.0(7) . . ? C14 C23 H23A 118.5 . . ? C22 C23 H23A 118.5 . . ? C32 O31 C36 113.1(6) . . ? O32 C32 O31 111.5(8) . . ? O32 C32 C33 108.7(7) . . ? O31 C32 C33 112.1(6) . . ? O32 C32 C37 108.8(7) . . ? O31 C32 C37 104.2(7) . . ? C33 C32 C37 111.5(8) . . ? C32 O32 H32O 109.5 . . ? C32 C33 C34 111.7(7) . . ? C32 C33 H33A 109.3 . . ? C34 C33 H33A 109.3 . . ? C32 C33 H33B 109.3 . . ? C34 C33 H33B 109.3 . . ? H33A C33 H33B 107.9 . . ? C38 C34 C33 111.2(6) . . ? C38 C34 C35 112.3(6) . . ? C33 C34 C35 107.5(7) . . ? C38 C34 H34A 108.6 . . ? C33 C34 H34A 108.6 . . ? C35 C34 H34A 108.6 . . ? C44 C35 C36 109.2(7) . . ? C44 C35 C34 115.3(7) . . ? C36 C35 C34 108.4(6) . . ? C44 C35 H35A 107.9 . . ? C36 C35 H35A 107.9 . . ? C34 C35 H35A 107.9 . . ? O31 C36 C35 113.0(7) . . ? O31 C36 H36A 109.0 . . ? C35 C36 H36A 109.0 . . ? O31 C36 H36B 109.0 . . ? C35 C36 H36B 109.0 . . ? H36A C36 H36B 107.8 . . ? F32 C37 F33 108.8(8) . . ? F32 C37 F31 104.9(7) . . ? F33 C37 F31 106.5(8) . . ? F32 C37 C32 111.1(8) . . ? F33 C37 C32 113.3(7) . . ? F31 C37 C32 111.8(7) . . ? C39 C38 C43 117.5(8) . . ? C39 C38 C34 122.6(7) . . ? C43 C38 C34 119.6(7) . . ? C40 C39 C38 121.8(8) . . ? C40 C39 H39A 119.1 . . ? C38 C39 H39A 119.1 . . ? C41 C40 C39 118.6(8) . . ? C41 C40 H40A 120.7 . . ? C39 C40 H40A 120.7 . . ? C42 C41 C40 120.7(9) . . ? C42 C41 H41A 119.7 . . ? C40 C41 H41A 119.7 . . ? C41 C42 C43 121.0(8) . . ? C41 C42 H42A 119.5 . . ? C43 C42 H42A 119.5 . . ? C42 C43 C38 120.2(8) . . ? C42 C43 H43A 119.9 . . ? C38 C43 H43A 119.9 . . ? C53 C44 C45 118.7(8) . . ? C53 C44 C35 119.6(7) . . ? C45 C44 C35 121.7(7) . . ? C46 C45 C44 120.9(8) . . ? C46 C45 H45A 119.5 . . ? C44 C45 H45A 119.5 . . ? C45 C46 C47 122.8(7) . . ? C45 C46 H46A 118.6 . . ? C47 C46 H46A 118.6 . . ? C48 C47 C52 119.7(7) . . ? C48 C47 C46 124.2(7) . . ? C52 C47 C46 116.1(7) . . ? C49 C48 C47 120.1(8) . . ? C49 C48 H48A 119.9 . . ? C47 C48 H48A 119.9 . . ? C48 C49 C50 119.8(9) . . ? C48 C49 H49A 120.1 . . ? C50 C49 H49A 120.1 . . ? C51 C50 C49 121.5(8) . . ? C51 C50 H50A 119.2 . . ? C49 C50 H50A 119.2 . . ? C50 C51 C52 119.8(8) . . ? C50 C51 H51A 120.1 . . ? C52 C51 H51A 120.1 . . ? C51 C52 C47 119.0(7) . . ? C51 C52 C53 122.2(7) . . ? C47 C52 C53 118.8(7) . . ? C44 C53 C52 122.5(7) . . ? C44 C53 H53A 118.7 . . ? C52 C53 H53A 118.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O1 C2 O2 67.0(9) . . . . ? C6 O1 C2 C3 -57.6(8) . . . . ? C6 O1 C2 C7 -175.2(7) . . . . ? O2 C2 C3 C4 -73.0(8) . . . . ? O1 C2 C3 C4 54.5(8) . . . . ? C7 C2 C3 C4 169.1(7) . . . . ? C2 C3 C4 C8 -177.6(7) . . . . ? C2 C3 C4 C5 -52.4(8) . . . . ? C8 C4 C5 C14 -57.5(9) . . . . ? C3 C4 C5 C14 179.1(7) . . . . ? C8 C4 C5 C6 178.9(6) . . . . ? C3 C4 C5 C6 55.5(8) . . . . ? C2 O1 C6 C5 59.9(9) . . . . ? C14 C5 C6 O1 173.5(6) . . . . ? C4 C5 C6 O1 -58.9(9) . . . . ? O2 C2 C7 F3 178.7(7) . . . . ? O1 C2 C7 F3 57.6(9) . . . . ? C3 C2 C7 F3 -63.9(9) . . . . ? O2 C2 C7 F2 -56.6(10) . . . . ? O1 C2 C7 F2 -177.6(8) . . . . ? C3 C2 C7 F2 60.9(10) . . . . ? O2 C2 C7 F1 59.8(9) . . . . ? O1 C2 C7 F1 -61.2(9) . . . . ? C3 C2 C7 F1 177.3(7) . . . . ? C3 C4 C8 C9 86.3(9) . . . . ? C5 C4 C8 C9 -36.3(9) . . . . ? C3 C4 C8 C13 -90.3(8) . . . . ? C5 C4 C8 C13 147.1(7) . . . . ? C13 C8 C9 C10 1.7(12) . . . . ? C4 C8 C9 C10 -174.9(7) . . . . ? C8 C9 C10 C11 -2.0(12) . . . . ? C9 C10 C11 C12 1.9(13) . . . . ? C10 C11 C12 C13 -1.5(14) . . . . ? C11 C12 C13 C8 1.2(14) . . . . ? C9 C8 C13 C12 -1.3(12) . . . . ? C4 C8 C13 C12 175.4(8) . . . . ? C6 C5 C14 C23 -104.1(9) . . . . ? C4 C5 C14 C23 132.6(8) . . . . ? C6 C5 C14 C15 74.8(9) . . . . ? C4 C5 C14 C15 -48.6(11) . . . . ? C23 C14 C15 C16 3.3(12) . . . . ? C5 C14 C15 C16 -175.6(7) . . . . ? C14 C15 C16 C17 -0.7(12) . . . . ? C15 C16 C17 C22 -1.3(11) . . . . ? C15 C16 C17 C18 -179.8(8) . . . . ? C22 C17 C18 C19 -0.6(12) . . . . ? C16 C17 C18 C19 177.9(8) . . . . ? C17 C18 C19 C20 3.5(13) . . . . ? C18 C19 C20 C21 -6.0(13) . . . . ? C19 C20 C21 C22 5.3(13) . . . . ? C20 C21 C22 C23 178.5(8) . . . . ? C20 C21 C22 C17 -2.3(12) . . . . ? C16 C17 C22 C21 -178.6(7) . . . . ? C18 C17 C22 C21 -0.1(11) . . . . ? C16 C17 C22 C23 0.7(11) . . . . ? C18 C17 C22 C23 179.2(7) . . . . ? C15 C14 C23 C22 -4.0(12) . . . . ? C5 C14 C23 C22 175.0(7) . . . . ? C21 C22 C23 C14 -178.7(8) . . . . ? C17 C22 C23 C14 2.0(11) . . . . ? C36 O31 C32 O32 66.5(9) . . . . ? C36 O31 C32 C33 -55.6(9) . . . . ? C36 O31 C32 C37 -176.4(7) . . . . ? O32 C32 C33 C34 -68.9(8) . . . . ? O31 C32 C33 C34 54.8(8) . . . . ? C37 C32 C33 C34 171.1(7) . . . . ? C32 C33 C34 C38 -177.8(6) . . . . ? C32 C33 C34 C35 -54.6(8) . . . . ? C38 C34 C35 C44 -59.8(8) . . . . ? C33 C34 C35 C44 177.6(6) . . . . ? C38 C34 C35 C36 177.5(6) . . . . ? C33 C34 C35 C36 54.9(8) . . . . ? C32 O31 C36 C35 58.6(9) . . . . ? C44 C35 C36 O31 175.4(6) . . . . ? C34 C35 C36 O31 -58.3(9) . . . . ? O32 C32 C37 F32 -60.2(10) . . . . ? O31 C32 C37 F32 -179.2(7) . . . . ? C33 C32 C37 F32 59.7(9) . . . . ? O32 C32 C37 F33 177.0(8) . . . . ? O31 C32 C37 F33 58.1(10) . . . . ? C33 C32 C37 F33 -63.0(10) . . . . ? O32 C32 C37 F31 56.6(10) . . . . ? O31 C32 C37 F31 -62.3(8) . . . . ? C33 C32 C37 F31 176.6(7) . . . . ? C33 C34 C38 C39 78.3(10) . . . . ? C35 C34 C38 C39 -42.3(11) . . . . ? C33 C34 C38 C43 -95.0(9) . . . . ? C35 C34 C38 C43 144.5(8) . . . . ? C43 C38 C39 C40 -4.2(14) . . . . ? C34 C38 C39 C40 -177.6(9) . . . . ? C38 C39 C40 C41 4.8(15) . . . . ? C39 C40 C41 C42 -2.0(15) . . . . ? C40 C41 C42 C43 -1.3(15) . . . . ? C41 C42 C43 C38 1.9(15) . . . . ? C39 C38 C43 C42 0.8(13) . . . . ? C34 C38 C43 C42 174.4(9) . . . . ? C36 C35 C44 C53 -106.8(9) . . . . ? C34 C35 C44 C53 131.0(8) . . . . ? C36 C35 C44 C45 73.8(10) . . . . ? C34 C35 C44 C45 -48.5(11) . . . . ? C53 C44 C45 C46 3.8(13) . . . . ? C35 C44 C45 C46 -176.8(8) . . . . ? C44 C45 C46 C47 -2.9(14) . . . . ? C45 C46 C47 C48 179.8(9) . . . . ? C45 C46 C47 C52 1.1(13) . . . . ? C52 C47 C48 C49 -0.4(13) . . . . ? C46 C47 C48 C49 -179.1(9) . . . . ? C47 C48 C49 C50 0.8(14) . . . . ? C48 C49 C50 C51 -1.7(15) . . . . ? C49 C50 C51 C52 2.2(14) . . . . ? C50 C51 C52 C47 -1.7(13) . . . . ? C50 C51 C52 C53 178.1(8) . . . . ? C48 C47 C52 C51 0.8(12) . . . . ? C46 C47 C52 C51 179.6(8) . . . . ? C48 C47 C52 C53 -179.0(8) . . . . ? C46 C47 C52 C53 -0.2(11) . . . . ? C45 C44 C53 C52 -3.0(13) . . . . ? C35 C44 C53 C52 177.5(7) . . . . ? C51 C52 C53 C44 -178.5(8) . . . . ? C47 C52 C53 C44 1.3(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O F3 0.98 2.40 3.367(8) 169.2 1_455 O32 H32O F33 0.98 2.75 3.280(9) 114.1 1_455 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.300 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 907809' ####################################################################### # # 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_6 _chemical_formula_sum 'C19 H20 N2 S' _chemical_formula_moiety 'C19 H20 N2 S' _chemical_formula_weight 308.44 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 7.934(2) _cell_length_b 10.719(3) _cell_length_c 18.419(5) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1566.6(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5540 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 25.35 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.285 _exptl_crystal_size_mid 0.155 _exptl_crystal_size_min 0.065 _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656.00 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.751 _exptl_absorpt_correction_T_max 0.987 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.629 _diffrn_reflns_number 9995 _diffrn_reflns_av_R_equivalents 0.0786 _diffrn_reflns_theta_max 25.35 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2855 _reflns_number_gt 2492 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1333 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2855 _refine_ls_number_parameters 199 _refine_ls_goodness_of_fit_ref 0.661 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1212P)^2^+0.9917P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.190 _refine_diff_density_min -0.280 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1194 Friedel Pairs' _refine_ls_abs_structure_Flack 0.03(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.1246 0.1234 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S9 S 0.50977(9) 0.61978(6) 0.63237(4) 0.0332(3) Uani 1.0 4 d . . . N1 N 0.6154(3) 0.4018(2) 0.68713(12) 0.0279(6) Uani 1.0 4 d . . . N4A N 0.6348(4) 0.4360(2) 0.55843(12) 0.0282(6) Uani 1.0 4 d . . . C2 C 0.6865(4) 0.2756(3) 0.67616(14) 0.0265(6) Uani 1.0 4 d . . . C3 C 0.6331(4) 0.2206(3) 0.60134(14) 0.0262(6) Uani 1.0 4 d . . . C4 C 0.6880(4) 0.3086(3) 0.54087(14) 0.0278(6) Uani 1.0 4 d . . . C4B C 0.6036(4) 0.5291(3) 0.50718(15) 0.0279(6) Uani 1.0 4 d . . . C5 C 0.6321(4) 0.5223(3) 0.43297(15) 0.0341(7) Uani 1.0 4 d . . . C6 C 0.5858(5) 0.6251(3) 0.39053(17) 0.0427(8) Uani 1.0 4 d . . . C7 C 0.5136(6) 0.7295(3) 0.42117(17) 0.0466(9) Uani 1.0 4 d . . . C8 C 0.4844(5) 0.7362(3) 0.49520(17) 0.0399(8) Uani 1.0 4 d . . . C8A C 0.5309(4) 0.6358(3) 0.53822(15) 0.0311(7) Uani 1.0 4 d . . . C9A C 0.5963(4) 0.4671(3) 0.62960(15) 0.0267(6) Uani 1.0 4 d . . . C10 C 0.8751(4) 0.2748(3) 0.68855(13) 0.0262(6) Uani 1.0 4 d . . . C11 C 0.9782(4) 0.3733(3) 0.66721(14) 0.0294(6) Uani 1.0 4 d . . . C12 C 1.1502(4) 0.3708(3) 0.67971(15) 0.0349(7) Uani 1.0 4 d . . . C13 C 1.2236(4) 0.2684(3) 0.71383(15) 0.0354(7) Uani 1.0 4 d . . . C14 C 1.1232(4) 0.1693(3) 0.73483(16) 0.0351(7) Uani 1.0 4 d . . . C15 C 0.9506(4) 0.1722(3) 0.72265(16) 0.0321(7) Uani 1.0 4 d . . . C16 C 0.6942(4) 0.0857(3) 0.58896(15) 0.0301(7) Uani 1.0 4 d . . . C17 C 0.6096(4) -0.0060(3) 0.64073(17) 0.0386(8) Uani 1.0 4 d . . . C18 C 0.6678(5) 0.0424(3) 0.51062(16) 0.0374(8) Uani 1.0 4 d . . . H2 H 0.6358 0.2208 0.7143 0.0318 Uiso 1.0 4 calc R . . H3 H 0.5071 0.2185 0.6007 0.0314 Uiso 1.0 4 calc R . . H4A H 0.8121 0.3056 0.5355 0.0334 Uiso 1.0 4 calc R . . H4B H 0.6367 0.2822 0.4943 0.0334 Uiso 1.0 4 calc R . . H5 H 0.6814 0.4503 0.4117 0.0409 Uiso 1.0 4 calc R . . H6 H 0.6045 0.6229 0.3396 0.0513 Uiso 1.0 4 calc R . . H7 H 0.4835 0.7980 0.3911 0.0559 Uiso 1.0 4 calc R . . H8 H 0.4335 0.8080 0.5161 0.0478 Uiso 1.0 4 calc R . . H11 H 0.9297 0.4435 0.6437 0.0353 Uiso 1.0 4 calc R . . H12 H 1.2183 0.4391 0.6650 0.0419 Uiso 1.0 4 calc R . . H13 H 1.3415 0.2666 0.7226 0.0425 Uiso 1.0 4 calc R . . H14 H 1.1726 0.0988 0.7577 0.0421 Uiso 1.0 4 calc R . . H15 H 0.8828 0.1038 0.7376 0.0386 Uiso 1.0 4 calc R . . H16 H 0.8180 0.0837 0.5990 0.0361 Uiso 1.0 4 calc R . . H17A H 0.6591 -0.0890 0.6343 0.0463 Uiso 1.0 4 calc R . . H17B H 0.4886 -0.0095 0.6303 0.0463 Uiso 1.0 4 calc R . . H17C H 0.6267 0.0217 0.6909 0.0463 Uiso 1.0 4 calc R . . H18A H 0.5468 0.0392 0.5000 0.0448 Uiso 1.0 4 calc R . . H18B H 0.7168 -0.0408 0.5043 0.0448 Uiso 1.0 4 calc R . . H18C H 0.7228 0.1010 0.4774 0.0448 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S9 0.0379(5) 0.0275(4) 0.0343(4) 0.0037(4) -0.0008(4) -0.0024(3) N1 0.0279(12) 0.0291(13) 0.0267(12) 0.0034(10) -0.0005(10) -0.0013(10) N4A 0.0352(14) 0.0260(12) 0.0234(11) 0.0014(11) 0.0008(11) 0.0023(9) C2 0.0264(14) 0.0283(13) 0.0248(13) 0.0022(12) 0.0003(11) 0.0007(12) C3 0.0229(13) 0.0262(14) 0.0294(14) -0.0008(12) -0.0007(12) 0.0006(12) C4 0.0290(15) 0.0285(14) 0.0260(14) 0.0023(12) -0.0001(12) -0.0009(11) C4B 0.0295(15) 0.0246(13) 0.0296(14) -0.0059(13) -0.0070(13) 0.0031(12) C5 0.0395(17) 0.0343(16) 0.0285(15) -0.0079(15) -0.0034(14) 0.0038(12) C6 0.061(3) 0.0372(17) 0.0301(15) -0.0102(17) -0.0077(15) 0.0054(13) C7 0.062(3) 0.0346(16) 0.0430(17) -0.0080(18) -0.0136(18) 0.0101(13) C8 0.0447(19) 0.0300(15) 0.0449(17) -0.0018(16) -0.0083(16) 0.0045(13) C8A 0.0351(17) 0.0264(14) 0.0318(15) -0.0042(14) -0.0057(13) 0.0001(12) C9A 0.0223(14) 0.0274(14) 0.0303(14) 0.0003(12) -0.0008(12) -0.0016(12) C10 0.0274(15) 0.0301(15) 0.0210(12) 0.0001(12) -0.0007(11) -0.0012(11) C11 0.0308(15) 0.0296(14) 0.0279(14) -0.0056(15) 0.0023(12) -0.0012(11) C12 0.0319(16) 0.0377(16) 0.0352(15) -0.0079(15) 0.0010(13) -0.0040(13) C13 0.0278(16) 0.0490(18) 0.0296(15) -0.0015(15) -0.0020(13) -0.0050(14) C14 0.0346(17) 0.0399(17) 0.0308(14) 0.0041(15) -0.0034(14) 0.0015(13) C15 0.0346(16) 0.0328(15) 0.0290(15) -0.0024(13) -0.0037(13) 0.0019(12) C16 0.0277(15) 0.0272(14) 0.0353(16) -0.0001(12) -0.0043(13) -0.0006(12) C17 0.0414(18) 0.0284(16) 0.0460(18) -0.0035(13) -0.0059(15) 0.0067(13) C18 0.0433(19) 0.0305(15) 0.0383(16) 0.0034(15) -0.0037(15) -0.0049(13) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S9 C8A 1.751(3) yes . . S9 C9A 1.776(3) yes . . N1 C2 1.479(4) yes . . N1 C9A 1.279(4) yes . . N4A C4 1.466(4) yes . . N4A C4B 1.395(4) yes . . N4A C9A 1.386(4) yes . . C2 C3 1.558(4) yes . . C2 C10 1.514(4) yes . . C3 C4 1.523(4) yes . . C3 C16 1.542(4) yes . . C4B C5 1.387(4) yes . . C4B C8A 1.403(4) yes . . C5 C6 1.400(5) yes . . C6 C7 1.378(5) yes . . C7 C8 1.385(5) yes . . C8 C8A 1.386(4) yes . . C10 C11 1.392(4) yes . . C10 C15 1.401(4) yes . . C11 C12 1.384(4) yes . . C12 C13 1.392(5) yes . . C13 C14 1.383(5) yes . . C14 C15 1.388(5) yes . . C16 C17 1.525(5) yes . . C16 C18 1.530(4) yes . . C2 H2 1.000 no . . C3 H3 1.000 no . . C4 H4A 0.990 no . . C4 H4B 0.990 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C7 H7 0.950 no . . C8 H8 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C13 H13 0.950 no . . C14 H14 0.950 no . . C15 H15 0.950 no . . C16 H16 1.000 no . . C17 H17A 0.980 no . . C17 H17B 0.980 no . . C17 H17C 0.980 no . . C18 H18A 0.980 no . . C18 H18B 0.980 no . . C18 H18C 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C8A S9 C9A 91.44(13) yes . . . C2 N1 C9A 115.6(3) yes . . . C4 N4A C4B 124.6(3) yes . . . C4 N4A C9A 119.7(3) yes . . . C4B N4A C9A 115.4(3) yes . . . N1 C2 C3 111.3(3) yes . . . N1 C2 C10 111.2(3) yes . . . C3 C2 C10 113.6(3) yes . . . C2 C3 C4 109.6(3) yes . . . C2 C3 C16 113.6(3) yes . . . C4 C3 C16 112.5(3) yes . . . N4A C4 C3 109.4(3) yes . . . N4A C4B C5 126.9(3) yes . . . N4A C4B C8A 112.3(3) yes . . . C5 C4B C8A 120.7(3) yes . . . C4B C5 C6 117.8(3) yes . . . C5 C6 C7 121.3(3) yes . . . C6 C7 C8 121.0(3) yes . . . C7 C8 C8A 118.6(3) yes . . . S9 C8A C4B 111.3(2) yes . . . S9 C8A C8 128.1(3) yes . . . C4B C8A C8 120.6(3) yes . . . S9 C9A N1 121.8(3) yes . . . S9 C9A N4A 109.48(19) yes . . . N1 C9A N4A 128.7(3) yes . . . C2 C10 C11 122.3(3) yes . . . C2 C10 C15 119.6(3) yes . . . C11 C10 C15 118.1(3) yes . . . C10 C11 C12 121.2(3) yes . . . C11 C12 C13 120.2(3) yes . . . C12 C13 C14 119.4(3) yes . . . C13 C14 C15 120.4(3) yes . . . C10 C15 C14 120.8(3) yes . . . C3 C16 C17 111.9(3) yes . . . C3 C16 C18 112.4(3) yes . . . C17 C16 C18 109.5(3) yes . . . N1 C2 H2 106.768 no . . . C3 C2 H2 106.775 no . . . C10 C2 H2 106.775 no . . . C2 C3 H3 106.941 no . . . C4 C3 H3 106.941 no . . . C16 C3 H3 106.944 no . . . N4A C4 H4A 109.784 no . . . N4A C4 H4B 109.790 no . . . C3 C4 H4A 109.780 no . . . C3 C4 H4B 109.785 no . . . H4A C4 H4B 108.240 no . . . C4B C5 H5 121.098 no . . . C6 C5 H5 121.118 no . . . C5 C6 H6 119.346 no . . . C7 C6 H6 119.349 no . . . C6 C7 H7 119.516 no . . . C8 C7 H7 119.515 no . . . C7 C8 H8 120.716 no . . . C8A C8 H8 120.710 no . . . C10 C11 H11 119.420 no . . . C12 C11 H11 119.410 no . . . C11 C12 H12 119.904 no . . . C13 C12 H12 119.892 no . . . C12 C13 H13 120.311 no . . . C14 C13 H13 120.298 no . . . C13 C14 H14 119.822 no . . . C15 C14 H14 119.811 no . . . C10 C15 H15 119.604 no . . . C14 C15 H15 119.598 no . . . C3 C16 H16 107.594 no . . . C17 C16 H16 107.603 no . . . C18 C16 H16 107.597 no . . . C16 C17 H17A 109.473 no . . . C16 C17 H17B 109.477 no . . . C16 C17 H17C 109.468 no . . . H17A C17 H17B 109.472 no . . . H17A C17 H17C 109.473 no . . . H17B C17 H17C 109.464 no . . . C16 C18 H18A 109.476 no . . . C16 C18 H18B 109.477 no . . . C16 C18 H18C 109.471 no . . . H18A C18 H18B 109.468 no . . . H18A C18 H18C 109.465 no . . . H18B C18 H18C 109.470 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C8A S9 C9A N1 179.7(3) no . . . . C8A S9 C9A N4A -0.56(18) no . . . . C9A S9 C8A C4B -0.9(2) no . . . . C9A S9 C8A C8 178.5(3) no . . . . C2 N1 C9A S9 179.04(19) no . . . . C2 N1 C9A N4A -0.7(4) no . . . . C9A N1 C2 C3 -31.7(3) no . . . . C9A N1 C2 C10 96.1(3) no . . . . C4 N4A C4B C5 -6.6(5) no . . . . C4 N4A C4B C8A 171.2(3) no . . . . C4B N4A C4 C3 -153.9(3) no . . . . C4 N4A C9A S9 -172.3(2) no . . . . C4 N4A C9A N1 7.5(5) no . . . . C9A N4A C4 C3 19.7(4) no . . . . C4B N4A C9A S9 2.0(3) no . . . . C4B N4A C9A N1 -178.3(3) no . . . . C9A N4A C4B C5 179.4(3) no . . . . C9A N4A C4B C8A -2.7(4) no . . . . N1 C2 C3 C4 57.0(3) no . . . . N1 C2 C3 C16 -176.31(19) no . . . . N1 C2 C10 C11 -37.7(3) no . . . . N1 C2 C10 C15 142.3(2) no . . . . C3 C2 C10 C11 88.8(3) no . . . . C3 C2 C10 C15 -91.3(3) no . . . . C10 C2 C3 C4 -69.4(3) no . . . . C10 C2 C3 C16 57.3(3) no . . . . C2 C3 C4 N4A -49.2(3) no . . . . C2 C3 C16 C17 66.5(3) no . . . . C2 C3 C16 C18 -169.8(2) no . . . . C4 C3 C16 C17 -168.3(2) no . . . . C4 C3 C16 C18 -44.6(3) no . . . . C16 C3 C4 N4A -176.5(2) no . . . . N4A C4B C5 C6 177.6(3) no . . . . N4A C4B C8A S9 2.1(4) no . . . . N4A C4B C8A C8 -177.3(3) no . . . . C5 C4B C8A S9 -179.8(3) no . . . . C5 C4B C8A C8 0.7(5) no . . . . C8A C4B C5 C6 -0.1(5) no . . . . C4B C5 C6 C7 -0.3(5) no . . . . C5 C6 C7 C8 -0.0(6) no . . . . C6 C7 C8 C8A 0.7(6) no . . . . C7 C8 C8A S9 179.7(3) no . . . . C7 C8 C8A C4B -1.0(5) no . . . . C2 C10 C11 C12 179.5(2) no . . . . C2 C10 C15 C14 -179.8(3) no . . . . C11 C10 C15 C14 0.1(4) no . . . . C15 C10 C11 C12 -0.5(4) no . . . . C10 C11 C12 C13 0.3(4) no . . . . C11 C12 C13 C14 0.2(4) no . . . . C12 C13 C14 C15 -0.6(5) no . . . . C13 C14 C15 C10 0.4(5) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 N1 C4 2.930(4) no . . N1 C4B 3.586(4) no . . N1 C11 2.918(4) no . . N4A C2 2.798(4) no . . N4A C10 3.516(4) no . . N4A C11 3.449(4) no . . C2 C17 3.148(4) no . . C3 C9A 2.708(4) no . . C3 C11 3.413(4) no . . C3 C15 3.407(4) no . . C4 C5 3.065(4) no . . C4 C10 3.120(4) no . . C4 C11 3.346(4) no . . C4 C18 2.912(4) no . . C4B C7 2.763(5) no . . C5 C8 2.818(5) no . . C6 C8A 2.757(5) no . . C9A C10 3.212(4) no . . C9A C11 3.267(4) no . . C10 C13 2.805(4) no . . C10 C16 3.088(4) no . . C11 C14 2.767(5) no . . C12 C15 2.768(5) no . . C15 C16 3.326(5) no . . N1 C13 3.457(4) no . 1_455 C4B C18 3.557(5) no . 2_456 C8A C18 3.572(5) no . 2_456 C13 N1 3.457(4) no . 1_655 C18 C4B 3.557(5) no . 2_556 C18 C8A 3.572(5) no . 2_556 S9 H8 3.0043 no . . N1 H3 2.6706 no . . N1 H4A 3.3616 no . . N1 H11 2.6572 no . . N4A H3 2.6587 no . . N4A H5 2.7326 no . . N4A H11 2.8190 no . . C2 H4A 2.7948 no . . C2 H4B 3.3729 no . . C2 H11 2.7057 no . . C2 H15 2.6644 no . . C2 H16 2.7096 no . . C2 H17B 3.5389 no . . C2 H17C 2.7759 no . . C3 H11 3.4431 no . . C3 H15 3.4344 no . . C3 H17A 3.3803 no . . C3 H17B 2.7722 no . . C3 H17C 2.6962 no . . C3 H18A 2.7815 no . . C3 H18B 3.3896 no . . C3 H18C 2.7138 no . . C4 H2 3.3550 no . . C4 H5 2.8240 no . . C4 H11 3.0582 no . . C4 H16 2.8324 no . . C4 H18A 3.1875 no . . C4 H18C 2.5287 no . . C4B H4A 2.9576 no . . C4B H4B 2.6701 no . . C4B H6 3.2462 no . . C4B H8 3.2840 no . . C5 H4A 3.3168 no . . C5 H4B 2.8115 no . . C5 H7 3.2736 no . . C6 H8 3.2629 no . . C7 H5 3.2802 no . . C8 H6 3.2555 no . . C8A H5 3.2882 no . . C8A H7 3.2416 no . . C9A H2 3.0825 no . . C9A H3 2.8079 no . . C9A H4A 2.9888 no . . C9A H4B 3.1997 no . . C9A H11 2.6699 no . . C10 H3 3.3926 no . . C10 H4A 2.8823 no . . C10 H12 3.2720 no . . C10 H14 3.2799 no . . C10 H16 2.6692 no . . C10 H17C 3.3534 no . . C11 H2 3.2874 no . . C11 H4A 2.8549 no . . C11 H13 3.2648 no . . C11 H15 3.2558 no . . C11 H16 3.5824 no . . C12 H14 3.2553 no . . C13 H11 3.2604 no . . C13 H15 3.2581 no . . C14 H12 3.2544 no . . C15 H2 2.5558 no . . C15 H11 3.2560 no . . C15 H13 3.2631 no . . C15 H16 2.6820 no . . C15 H17C 3.0895 no . . C16 H2 2.7632 no . . C16 H4A 2.7207 no . . C16 H4B 2.7714 no . . C16 H15 3.1265 no . . C17 H2 2.7898 no . . C17 H3 2.6451 no . . C17 H15 3.0444 no . . C17 H18A 2.6842 no . . C17 H18B 2.6784 no . . C17 H18C 3.3428 no . . C18 H3 2.8184 no . . C18 H4A 3.0797 no . . C18 H4B 2.5999 no . . C18 H17A 2.6790 no . . C18 H17B 2.6811 no . . C18 H17C 3.3438 no . . H2 H3 2.3280 no . . H2 H11 3.5820 no . . H2 H15 2.3658 no . . H2 H16 2.9589 no . . H2 H17B 3.1385 no . . H2 H17C 2.1775 no . . H3 H4A 2.8587 no . . H3 H4B 2.3153 no . . H3 H16 2.8596 no . . H3 H17A 3.5644 no . . H3 H17B 2.5090 no . . H3 H17C 2.8484 no . . H3 H18A 2.6900 no . . H3 H18C 3.1105 no . . H4A H5 2.9467 no . . H4A H11 2.6504 no . . H4A H16 2.6519 no . . H4A H18C 2.5413 no . . H4B H5 2.3858 no . . H4B H16 3.2116 no . . H4B H18A 2.7025 no . . H4B H18B 3.5254 no . . H4B H18C 2.0824 no . . H5 H6 2.3568 no . . H6 H7 2.3118 no . . H7 H8 2.3384 no . . H11 H12 2.3240 no . . H12 H13 2.3451 no . . H13 H14 2.3351 no . . H14 H15 2.3297 no . . H15 H16 2.6132 no . . H15 H17A 3.3232 no . . H15 H17C 2.3753 no . . H16 H17A 2.3319 no . . H16 H17B 2.8568 no . . H16 H17C 2.3682 no . . H16 H18A 2.8609 no . . H16 H18B 2.3382 no . . H16 H18C 2.3715 no . . H17A H18A 2.9672 no . . H17A H18B 2.4911 no . . H17A H18C 3.5717 no . . H17B H18A 2.4995 no . . H17B H18B 2.9616 no . . H17B H18C 3.5760 no . . H17C H18A 3.5785 no . . H17C H18B 3.5732 no . . S9 H2 3.2384 no . 3_656 S9 H12 3.0757 no . 1_455 S9 H13 3.3172 no . 3_756 S9 H14 3.2405 no . 3_756 S9 H17A 3.3393 no . 1_565 S9 H17C 3.5880 no . 3_656 S9 H18B 3.5301 no . 2_456 N1 H6 3.5909 no . 4_665 N1 H12 3.2020 no . 1_455 N1 H13 2.6923 no . 1_455 N1 H14 2.8845 no . 3_756 N1 H17B 3.5912 no . 3_656 N1 H17C 3.2238 no . 3_656 N4A H18A 3.4520 no . 2_556 N4A H18C 3.3582 no . 2_456 C2 H13 2.8694 no . 1_455 C3 H4A 3.5937 no . 2_456 C3 H13 3.2533 no . 1_455 C4 H4A 3.5176 no . 2_456 C4 H18A 3.3663 no . 2_556 C4B H8 3.1759 no . 2_566 C4B H16 3.2281 no . 2_456 C4B H18A 3.5949 no . 2_556 C4B H18B 3.0790 no . 2_456 C4B H18C 3.3396 no . 2_456 C5 H8 3.1482 no . 2_566 C5 H16 2.8014 no . 2_456 C5 H17B 3.0622 no . 2_556 C5 H18A 3.5766 no . 2_556 C5 H18B 3.4973 no . 2_456 C6 H8 3.3296 no . 2_566 C6 H16 3.0922 no . 2_456 C6 H17A 3.4384 no . 2_456 C6 H17B 3.4491 no . 2_556 C7 H8 3.5493 no . 2_566 C7 H17A 3.3508 no . 2_456 C7 H18B 3.3171 no . 1_565 C7 H18B 3.3944 no . 2_456 C8 H17A 3.4639 no . 1_565 C8 H18A 3.2872 no . 1_565 C8 H18B 3.0235 no . 1_565 C8 H18B 2.9821 no . 2_456 C8A H8 3.4007 no . 2_566 C8A H17A 3.5871 no . 1_565 C8A H18B 2.8044 no . 2_456 C8A H18C 3.5363 no . 2_456 C9A H12 3.0838 no . 1_455 C9A H13 3.4118 no . 1_455 C9A H14 3.1083 no . 3_756 C10 H6 2.9949 no . 4_665 C11 H6 3.2427 no . 4_665 C11 H14 3.0307 no . 3_756 C11 H15 3.2240 no . 3_756 C11 H18A 3.2644 no . 2_556 C11 H18C 3.3067 no . 2_556 C12 H3 3.5778 no . 1_655 C12 H6 3.5723 no . 4_665 C12 H15 2.9374 no . 3_756 C12 H17C 3.3812 no . 3_756 C12 H18A 3.5433 no . 2_556 C12 H18C 2.9658 no . 2_556 C13 H2 3.3105 no . 1_655 C13 H3 3.1127 no . 1_655 C13 H5 3.3095 no . 2_556 C13 H17A 3.3211 no . 3_756 C13 H17C 3.4446 no . 3_756 C14 H5 3.0229 no . 2_556 C14 H6 3.4215 no . 2_556 C14 H6 3.4573 no . 4_665 C14 H7 3.0201 no . 4_665 C14 H11 3.3230 no . 3_746 C15 H5 3.3466 no . 2_556 C15 H6 3.5793 no . 2_556 C15 H6 3.1075 no . 4_665 C15 H7 3.1622 no . 4_665 C15 H12 3.5109 no . 3_746 C17 H5 3.5822 no . 2_456 C17 H8 3.3474 no . 1_545 C17 H13 3.5254 no . 3_746 C18 H4A 3.3673 no . 2_456 C18 H8 3.1272 no . 1_545 C18 H11 3.4154 no . 2_456 C18 H12 3.2650 no . 2_456 H2 S9 3.2384 no . 3_646 H2 C13 3.3105 no . 1_455 H2 H6 3.5194 no . 4_665 H2 H13 2.3911 no . 1_455 H3 C12 3.5778 no . 1_455 H3 C13 3.1127 no . 1_455 H3 H4A 2.9580 no . 2_456 H3 H4B 3.4202 no . 2_456 H3 H5 3.1634 no . 2_456 H3 H12 3.4984 no . 1_455 H3 H13 2.6525 no . 1_455 H3 H18C 3.3009 no . 2_456 H4A C3 3.5937 no . 2_556 H4A C4 3.5176 no . 2_556 H4A C18 3.3673 no . 2_556 H4A H3 2.9580 no . 2_556 H4A H4B 2.7968 no . 2_556 H4A H18A 2.5808 no . 2_556 H4A H18C 3.4171 no . 2_556 H4B H3 3.4202 no . 2_556 H4B H4A 2.7968 no . 2_456 H4B H16 3.3792 no . 2_456 H4B H18C 3.5532 no . 2_456 H5 C13 3.3095 no . 2_456 H5 C14 3.0229 no . 2_456 H5 C15 3.3466 no . 2_456 H5 C17 3.5822 no . 2_556 H5 H3 3.1634 no . 2_556 H5 H8 3.5337 no . 2_566 H5 H14 3.1648 no . 2_456 H5 H16 2.9127 no . 2_456 H5 H17B 2.6347 no . 2_556 H5 H18A 3.3274 no . 2_556 H6 N1 3.5909 no . 4_664 H6 C10 2.9949 no . 4_664 H6 C11 3.2427 no . 4_664 H6 C12 3.5723 no . 4_664 H6 C14 3.4215 no . 2_456 H6 C14 3.4573 no . 4_664 H6 C15 3.5793 no . 2_456 H6 C15 3.1075 no . 4_664 H6 H2 3.5194 no . 4_664 H6 H14 3.0248 no . 2_456 H6 H15 3.3200 no . 2_456 H6 H15 3.4817 no . 4_664 H6 H16 3.3686 no . 2_456 H6 H17A 3.5853 no . 2_456 H6 H17B 3.3273 no . 2_556 H7 C14 3.0201 no . 4_664 H7 C15 3.1622 no . 4_664 H7 H11 2.8759 no . 2_466 H7 H12 3.5332 no . 2_466 H7 H14 2.9650 no . 4_664 H7 H15 3.1973 no . 4_664 H7 H17A 3.4442 no . 2_456 H7 H18A 3.3110 no . 1_565 H7 H18B 3.2809 no . 1_565 H8 C4B 3.1759 no . 2_466 H8 C5 3.1482 no . 2_466 H8 C6 3.3296 no . 2_466 H8 C7 3.5493 no . 2_466 H8 C8A 3.4007 no . 2_466 H8 C17 3.3474 no . 1_565 H8 C18 3.1272 no . 1_565 H8 H5 3.5337 no . 2_466 H8 H17A 3.0279 no . 1_565 H8 H17B 2.9060 no . 1_565 H8 H18A 2.6536 no . 1_565 H8 H18B 2.7794 no . 1_565 H8 H18B 3.3612 no . 2_456 H11 C14 3.3230 no . 3_756 H11 C18 3.4154 no . 2_556 H11 H7 2.8759 no . 2_566 H11 H14 2.5941 no . 3_756 H11 H15 3.1542 no . 3_756 H11 H18A 2.8098 no . 2_556 H11 H18C 3.2566 no . 2_556 H12 S9 3.0757 no . 1_655 H12 N1 3.2020 no . 1_655 H12 C9A 3.0838 no . 1_655 H12 C15 3.5109 no . 3_756 H12 C18 3.2650 no . 2_556 H12 H3 3.4984 no . 1_655 H12 H7 3.5332 no . 2_566 H12 H15 2.6423 no . 3_756 H12 H17C 3.0568 no . 3_756 H12 H18A 3.3368 no . 2_556 H12 H18B 3.3038 no . 2_556 H12 H18C 2.6571 no . 2_556 H13 S9 3.3172 no . 3_746 H13 N1 2.6923 no . 1_655 H13 C2 2.8694 no . 1_655 H13 C3 3.2533 no . 1_655 H13 C9A 3.4118 no . 1_655 H13 C17 3.5254 no . 3_756 H13 H2 2.3911 no . 1_655 H13 H3 2.6525 no . 1_655 H13 H17A 3.0563 no . 3_756 H13 H17C 3.5148 no . 1_655 H13 H17C 3.1747 no . 3_756 H14 S9 3.2405 no . 3_746 H14 N1 2.8845 no . 3_746 H14 C9A 3.1083 no . 3_746 H14 C11 3.0307 no . 3_746 H14 H5 3.1648 no . 2_556 H14 H6 3.0248 no . 2_556 H14 H7 2.9650 no . 4_665 H14 H11 2.5941 no . 3_746 H15 C11 3.2240 no . 3_746 H15 C12 2.9374 no . 3_746 H15 H6 3.3200 no . 2_556 H15 H6 3.4817 no . 4_665 H15 H7 3.1973 no . 4_665 H15 H11 3.1542 no . 3_746 H15 H12 2.6423 no . 3_746 H16 C4B 3.2281 no . 2_556 H16 C5 2.8014 no . 2_556 H16 C6 3.0922 no . 2_556 H16 H4B 3.3792 no . 2_556 H16 H5 2.9127 no . 2_556 H16 H6 3.3686 no . 2_556 H17A S9 3.3393 no . 1_545 H17A C6 3.4384 no . 2_556 H17A C7 3.3508 no . 2_556 H17A C8 3.4639 no . 1_545 H17A C8A 3.5871 no . 1_545 H17A C13 3.3211 no . 3_746 H17A H6 3.5853 no . 2_556 H17A H7 3.4442 no . 2_556 H17A H8 3.0279 no . 1_545 H17A H13 3.0563 no . 3_746 H17B N1 3.5912 no . 3_646 H17B C5 3.0622 no . 2_456 H17B C6 3.4491 no . 2_456 H17B H5 2.6347 no . 2_456 H17B H6 3.3273 no . 2_456 H17B H8 2.9060 no . 1_545 H17C S9 3.5880 no . 3_646 H17C N1 3.2238 no . 3_646 H17C C12 3.3812 no . 3_746 H17C C13 3.4446 no . 3_746 H17C H12 3.0568 no . 3_746 H17C H13 3.5148 no . 1_455 H17C H13 3.1747 no . 3_746 H18A N4A 3.4520 no . 2_456 H18A C4 3.3663 no . 2_456 H18A C4B 3.5949 no . 2_456 H18A C5 3.5766 no . 2_456 H18A C8 3.2872 no . 1_545 H18A C11 3.2644 no . 2_456 H18A C12 3.5433 no . 2_456 H18A H4A 2.5808 no . 2_456 H18A H5 3.3274 no . 2_456 H18A H7 3.3110 no . 1_545 H18A H8 2.6536 no . 1_545 H18A H11 2.8098 no . 2_456 H18A H12 3.3368 no . 2_456 H18B S9 3.5301 no . 2_556 H18B C4B 3.0790 no . 2_556 H18B C5 3.4973 no . 2_556 H18B C7 3.3171 no . 1_545 H18B C7 3.3944 no . 2_556 H18B C8 3.0235 no . 1_545 H18B C8 2.9821 no . 2_556 H18B C8A 2.8044 no . 2_556 H18B H7 3.2809 no . 1_545 H18B H8 2.7794 no . 1_545 H18B H8 3.3612 no . 2_556 H18B H12 3.3038 no . 2_456 H18C N4A 3.3582 no . 2_556 H18C C4B 3.3396 no . 2_556 H18C C8A 3.5363 no . 2_556 H18C C11 3.3067 no . 2_456 H18C C12 2.9658 no . 2_456 H18C H3 3.3009 no . 2_556 H18C H4A 3.4171 no . 2_456 H18C H4B 3.5532 no . 2_556 H18C H11 3.2566 no . 2_456 H18C H12 2.6571 no . 2_456 _database_code_depnum_ccdc_archive 'CCDC 907070' ####################################################################### # # 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_67 _chemical_formula_sum 'C18 H17 F3 O2' _chemical_formula_moiety 'C18 H17 F3 O2' _chemical_formula_weight 322.33 _chemical_melting_point ? _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,-Z 3 1/2+X,1/2+Y,+Z 4 1/2-X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 19.358(10) _cell_length_b 9.419(5) _cell_length_c 8.186(4) _cell_angle_alpha 90.0000 _cell_angle_beta 90.979(16) _cell_angle_gamma 90.0000 _cell_volume 1492.4(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2688 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 25.35 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672.00 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.421 _exptl_absorpt_correction_T_max 0.998 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.629 _diffrn_reflns_number 4694 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_theta_max 25.33 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2405 _reflns_number_gt 1953 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1899 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 2405 _refine_ls_number_parameters 213 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1071P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.002 _refine_diff_density_max 0.280 _refine_diff_density_min -0.340 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(3) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.42805(13) 0.4874(3) 1.3926(3) 0.0452(8) Uani 1.0 4 d . . . F2 F 0.51060(12) 0.3616(4) 1.2947(3) 0.0485(8) Uani 1.0 4 d . . . F3 F 0.44580(14) 0.4864(4) 1.1336(3) 0.0474(8) Uani 1.0 4 d . . . O1 O 0.33251(13) 0.3409(3) 1.2111(3) 0.0318(8) Uani 1.0 4 d . . . O2 O 0.39566(15) 0.2015(4) 1.3958(3) 0.0376(9) Uani 1.0 4 d . . . C2 C 0.3964(2) 0.2765(5) 1.2478(5) 0.0293(10) Uani 1.0 4 d . . . C3 C 0.4205(2) 0.1778(5) 1.1147(5) 0.0301(10) Uani 1.0 4 d . . . C4 C 0.3636(2) 0.0698(5) 1.0669(5) 0.0312(10) Uani 1.0 4 d . . . C5 C 0.2930(2) 0.1459(5) 1.0312(5) 0.0322(10) Uani 1.0 4 d . . . C6 C 0.2779(2) 0.2392(6) 1.1794(5) 0.0350(10) Uani 1.0 4 d . . . C7 C 0.4453(3) 0.4036(6) 1.2667(5) 0.0384(12) Uani 1.0 4 d . . . C8 C 0.3877(2) -0.0290(6) 0.9327(5) 0.0300(10) Uani 1.0 4 d . . . C9 C 0.3995(3) -0.1708(6) 0.9701(6) 0.0363(11) Uani 1.0 4 d . . . C10 C 0.4229(3) -0.2663(6) 0.8538(6) 0.0399(11) Uani 1.0 4 d . . . C11 C 0.4355(3) -0.2201(6) 0.6953(6) 0.0377(11) Uani 1.0 4 d . . . C12 C 0.4246(3) -0.0784(6) 0.6579(6) 0.0399(12) Uani 1.0 4 d . . . C13 C 0.4015(3) 0.0179(6) 0.7738(5) 0.0369(11) Uani 1.0 4 d . . . C14 C 0.28321(19) 0.2274(5) 0.8699(5) 0.0294(10) Uani 1.0 4 d . . . C15 C 0.3200(2) 0.3496(5) 0.8319(5) 0.0334(11) Uani 1.0 4 d . . . C16 C 0.3068(3) 0.4216(5) 0.6853(5) 0.0338(11) Uani 1.0 4 d . . . C17 C 0.2553(3) 0.3751(6) 0.5794(6) 0.0378(11) Uani 1.0 4 d . . . C18 C 0.2186(3) 0.2536(6) 0.6159(5) 0.0382(11) Uani 1.0 4 d . . . C19 C 0.2336(2) 0.1794(6) 0.7588(5) 0.0363(11) Uani 1.0 4 d . . . H2o H 0.380(3) 0.265(6) 1.482(5) 0.073(19) Uiso 1.0 4 d . . . H3A H 0.4622 0.1262 1.1533 0.0361 Uiso 1.0 4 calc R . . H3B H 0.4330 0.2341 1.0175 0.0361 Uiso 1.0 4 calc R . . H4 H 0.3565 0.0090 1.1653 0.0374 Uiso 1.0 4 calc R . . H5 H 0.2571 0.0695 1.0302 0.0387 Uiso 1.0 4 calc R . . H6A H 0.2339 0.2906 1.1600 0.0420 Uiso 1.0 4 calc R . . H6B H 0.2723 0.1782 1.2767 0.0420 Uiso 1.0 4 calc R . . H9 H 0.3914 -0.2034 1.0779 0.0436 Uiso 1.0 4 calc R . . H10 H 0.4303 -0.3629 0.8825 0.0479 Uiso 1.0 4 calc R . . H11 H 0.4512 -0.2845 0.6146 0.0452 Uiso 1.0 4 calc R . . H12 H 0.4332 -0.0460 0.5502 0.0479 Uiso 1.0 4 calc R . . H13 H 0.3951 0.1149 0.7455 0.0443 Uiso 1.0 4 calc R . . H15 H 0.3543 0.3843 0.9060 0.0401 Uiso 1.0 4 calc R . . H16 H 0.3334 0.5028 0.6584 0.0406 Uiso 1.0 4 calc R . . H17 H 0.2452 0.4265 0.4821 0.0453 Uiso 1.0 4 calc R . . H18 H 0.1832 0.2209 0.5433 0.0459 Uiso 1.0 4 calc R . . H19 H 0.2094 0.0940 0.7809 0.0436 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.0537(18) 0.0352(18) 0.0467(15) -0.0009(14) 0.0001(11) -0.0097(14) F2 0.0362(15) 0.049(2) 0.0600(17) -0.0043(14) -0.0074(11) -0.0112(13) F3 0.0613(18) 0.0394(18) 0.0413(15) -0.0171(15) -0.0011(11) 0.0109(14) O1 0.0342(16) 0.0229(17) 0.0383(16) -0.0038(13) 0.0008(12) -0.0046(14) O2 0.0522(19) 0.034(3) 0.0267(16) 0.0053(15) 0.0006(12) 0.0069(14) C2 0.031(3) 0.027(3) 0.030(3) -0.0024(18) -0.0018(15) 0.0003(18) C3 0.033(3) 0.025(3) 0.032(3) 0.0067(19) 0.0005(15) 0.0027(19) C4 0.032(2) 0.026(3) 0.035(2) 0.0014(19) -0.0026(16) 0.0035(19) C5 0.032(3) 0.024(3) 0.041(3) 0.0007(19) 0.0051(16) 0.0003(19) C6 0.034(3) 0.030(3) 0.041(3) -0.003(2) 0.0023(16) 0.000(2) C7 0.041(3) 0.034(3) 0.040(3) 0.002(3) -0.0011(19) -0.008(3) C8 0.031(3) 0.027(3) 0.032(3) -0.0021(19) -0.0047(15) -0.0002(19) C9 0.033(3) 0.036(3) 0.040(3) 0.006(2) 0.0017(17) 0.009(2) C10 0.039(3) 0.029(3) 0.052(3) 0.006(3) 0.0002(18) 0.001(3) C11 0.039(3) 0.029(3) 0.045(3) 0.005(2) -0.0033(18) -0.009(2) C12 0.042(3) 0.034(3) 0.044(3) 0.003(3) 0.0010(18) -0.003(3) C13 0.043(3) 0.025(3) 0.043(3) 0.000(2) 0.0008(18) -0.004(2) C14 0.029(2) 0.022(3) 0.037(3) 0.0050(19) -0.0007(15) 0.0029(19) C15 0.033(3) 0.028(3) 0.039(3) 0.004(2) -0.0002(16) 0.002(2) C16 0.042(3) 0.027(3) 0.033(3) -0.001(2) 0.0021(17) -0.0020(19) C17 0.044(3) 0.031(3) 0.039(3) 0.008(3) -0.0026(18) 0.003(2) C18 0.045(3) 0.038(3) 0.032(3) -0.001(3) -0.0067(17) -0.011(2) C19 0.040(3) 0.030(3) 0.039(3) -0.002(2) 0.0001(18) -0.006(2) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc13' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc13' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C7 1.345(6) yes . . F2 C7 1.340(5) yes . . F3 C7 1.341(6) yes . . O1 C2 1.405(5) yes . . O1 C6 1.447(6) yes . . O2 C2 1.402(5) yes . . C2 C3 1.512(6) yes . . C2 C7 1.532(7) yes . . C3 C4 1.543(6) yes . . C4 C5 1.567(6) yes . . C4 C8 1.519(6) yes . . C5 C6 1.531(7) yes . . C5 C14 1.536(6) yes . . C8 C9 1.388(7) yes . . C8 C13 1.404(6) yes . . C9 C10 1.391(7) yes . . C10 C11 1.395(7) yes . . C11 C12 1.385(7) yes . . C12 C13 1.392(7) yes . . C14 C15 1.392(7) yes . . C14 C19 1.388(6) yes . . C15 C16 1.398(6) yes . . C16 C17 1.381(6) yes . . C17 C18 1.383(7) yes . . C18 C19 1.389(6) yes . . O2 H2o 0.98(5) no . . C3 H3A 0.990 no . . C3 H3B 0.990 no . . C4 H4 1.000 no . . C5 H5 1.000 no . . C6 H6A 0.990 no . . C6 H6B 0.990 no . . C9 H9 0.950 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C13 H13 0.950 no . . C15 H15 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 O1 C6 113.0(4) yes . . . O1 C2 O2 112.3(3) yes . . . O1 C2 C3 113.1(4) yes . . . O1 C2 C7 103.0(4) yes . . . O2 C2 C3 108.7(4) yes . . . O2 C2 C7 108.7(4) yes . . . C3 C2 C7 110.8(4) yes . . . C2 C3 C4 111.2(4) yes . . . C3 C4 C5 111.2(4) yes . . . C3 C4 C8 111.2(4) yes . . . C5 C4 C8 115.0(4) yes . . . C4 C5 C6 107.0(4) yes . . . C4 C5 C14 118.9(4) yes . . . C6 C5 C14 111.8(4) yes . . . O1 C6 C5 111.9(4) yes . . . F1 C7 F2 106.7(4) yes . . . F1 C7 F3 106.7(4) yes . . . F1 C7 C2 112.0(4) yes . . . F2 C7 F3 106.9(4) yes . . . F2 C7 C2 111.5(4) yes . . . F3 C7 C2 112.6(4) yes . . . C4 C8 C9 118.8(4) yes . . . C4 C8 C13 122.9(5) yes . . . C9 C8 C13 118.3(4) yes . . . C8 C9 C10 121.7(4) yes . . . C9 C10 C11 119.9(5) yes . . . C10 C11 C12 118.5(5) yes . . . C11 C12 C13 121.8(5) yes . . . C8 C13 C12 119.7(5) yes . . . C5 C14 C15 123.3(4) yes . . . C5 C14 C19 118.3(4) yes . . . C15 C14 C19 118.3(4) yes . . . C14 C15 C16 120.4(4) yes . . . C15 C16 C17 120.3(5) yes . . . C16 C17 C18 119.7(4) yes . . . C17 C18 C19 119.8(4) yes . . . C14 C19 C18 121.4(5) yes . . . C2 O2 H2o 109(3) no . . . C2 C3 H3A 109.403 no . . . C2 C3 H3B 109.400 no . . . C4 C3 H3A 109.404 no . . . C4 C3 H3B 109.409 no . . . H3A C3 H3B 108.013 no . . . C3 C4 H4 106.278 no . . . C5 C4 H4 106.268 no . . . C8 C4 H4 106.274 no . . . C4 C5 H5 106.085 no . . . C6 C5 H5 106.094 no . . . C14 C5 H5 106.088 no . . . O1 C6 H6A 109.231 no . . . O1 C6 H6B 109.230 no . . . C5 C6 H6A 109.221 no . . . C5 C6 H6B 109.230 no . . . H6A C6 H6B 107.904 no . . . C8 C9 H9 119.129 no . . . C10 C9 H9 119.134 no . . . C9 C10 H10 120.041 no . . . C11 C10 H10 120.030 no . . . C10 C11 H11 120.730 no . . . C12 C11 H11 120.730 no . . . C11 C12 H12 119.089 no . . . C13 C12 H12 119.094 no . . . C8 C13 H13 120.164 no . . . C12 C13 H13 120.178 no . . . C14 C15 H15 119.796 no . . . C16 C15 H15 119.803 no . . . C15 C16 H16 119.839 no . . . C17 C16 H16 119.837 no . . . C16 C17 H17 120.171 no . . . C18 C17 H17 120.163 no . . . C17 C18 H18 120.083 no . . . C19 C18 H18 120.083 no . . . C14 C19 H19 119.310 no . . . C18 C19 H19 119.310 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 O1 C6 C5 -61.8(4) no . . . . C6 O1 C2 O2 -66.1(4) no . . . . C6 O1 C2 C3 57.4(4) no . . . . C6 O1 C2 C7 177.1(3) no . . . . O1 C2 C3 C4 -51.6(5) no . . . . O1 C2 C7 F1 63.5(4) no . . . . O1 C2 C7 F2 -177.0(3) no . . . . O1 C2 C7 F3 -56.8(4) no . . . . O2 C2 C3 C4 73.8(4) no . . . . O2 C2 C7 F1 -55.9(5) no . . . . O2 C2 C7 F2 63.7(4) no . . . . O2 C2 C7 F3 -176.1(3) no . . . . C3 C2 C7 F1 -175.3(3) no . . . . C3 C2 C7 F2 -55.7(4) no . . . . C3 C2 C7 F3 64.5(5) no . . . . C7 C2 C3 C4 -166.7(3) no . . . . C2 C3 C4 C5 50.2(4) no . . . . C2 C3 C4 C8 179.8(3) no . . . . C3 C4 C5 C6 -52.7(4) no . . . . C3 C4 C5 C14 75.1(5) no . . . . C3 C4 C8 C9 110.8(4) no . . . . C3 C4 C8 C13 -66.3(5) no . . . . C5 C4 C8 C9 -121.7(4) no . . . . C5 C4 C8 C13 61.2(5) no . . . . C8 C4 C5 C6 179.8(4) no . . . . C8 C4 C5 C14 -52.4(5) no . . . . C4 C5 C6 O1 57.8(5) no . . . . C4 C5 C14 C15 -66.3(6) no . . . . C4 C5 C14 C19 115.9(4) no . . . . C6 C5 C14 C15 59.2(5) no . . . . C6 C5 C14 C19 -118.6(4) no . . . . C14 C5 C6 O1 -74.1(4) no . . . . C4 C8 C9 C10 -178.7(4) no . . . . C4 C8 C13 C12 178.8(4) no . . . . C9 C8 C13 C12 1.7(6) no . . . . C13 C8 C9 C10 -1.4(6) no . . . . C8 C9 C10 C11 0.4(7) no . . . . C9 C10 C11 C12 0.4(7) no . . . . C10 C11 C12 C13 -0.1(7) no . . . . C11 C12 C13 C8 -0.9(7) no . . . . C5 C14 C15 C16 -177.7(4) no . . . . C5 C14 C19 C18 175.4(4) no . . . . C15 C14 C19 C18 -2.6(6) no . . . . C19 C14 C15 C16 0.2(6) no . . . . C14 C15 C16 C17 2.4(7) no . . . . C15 C16 C17 C18 -2.6(7) no . . . . C16 C17 C18 C19 0.2(7) no . . . . C17 C18 C19 C14 2.4(7) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 O1 2.728(4) no . . F1 O2 2.765(5) no . . F2 O1 3.509(4) no . . F2 O2 2.823(5) no . . F2 C3 2.850(5) no . . F3 O1 2.672(4) no . . F3 O2 3.580(5) no . . F3 C3 2.951(6) no . . O1 C4 2.881(6) no . . O1 C14 3.125(5) no . . O1 C15 3.111(5) no . . O2 C4 3.019(5) no . . O2 C5 3.596(5) no . . O2 C6 2.885(5) no . . C2 C5 2.923(6) no . . C3 C6 2.878(6) no . . C3 C9 3.511(7) no . . C3 C13 3.187(6) no . . C3 C14 3.334(6) no . . C3 C15 3.407(6) no . . C4 C15 3.362(7) no . . C5 C13 3.233(6) no . . C6 C15 3.149(6) no . . C6 C19 3.579(6) no . . C8 C11 2.817(7) no . . C8 C14 3.186(7) no . . C9 C12 2.751(7) no . . C10 C13 2.786(8) no . . C13 C14 3.133(7) no . . C13 C15 3.535(7) no . . C13 C19 3.589(7) no . . C14 C17 2.800(6) no . . C15 C18 2.772(6) no . . C16 C19 2.757(7) no . . F1 F1 3.268(4) no . 2_658 F1 F2 3.043(4) no . 2_658 F1 C16 3.439(5) no . 1_556 F2 F1 3.043(4) no . 2_658 F2 F2 3.393(4) no . 2_658 F2 O2 3.439(4) no . 2_658 F2 C15 3.458(5) no . 2_657 F2 C16 3.581(6) no . 2_657 F3 F3 3.057(4) no . 2_657 F3 C10 3.291(6) no . 1_565 F3 C10 3.448(6) no . 2_667 O1 C17 3.403(6) no . 1_556 O1 C19 3.446(6) no . 4_557 O2 F2 3.439(4) no . 2_658 O2 C12 3.439(6) no . 1_556 O2 C13 3.545(6) no . 1_556 O2 C17 3.529(6) no . 1_556 C6 C16 3.595(7) no . 4_547 C6 C17 3.550(7) no . 1_556 C10 F3 3.291(6) no . 1_545 C10 F3 3.448(6) no . 2_647 C12 O2 3.439(6) no . 1_554 C13 O2 3.545(6) no . 1_554 C15 F2 3.458(5) no . 2_657 C16 F1 3.439(5) no . 1_554 C16 F2 3.581(6) no . 2_657 C16 C6 3.595(7) no . 4_557 C17 O1 3.403(6) no . 1_554 C17 O2 3.529(6) no . 1_554 C17 C6 3.550(7) no . 1_554 C19 O1 3.446(6) no . 4_547 F1 H2o 2.41(5) no . . F2 H2o 3.12(5) no . . F2 H3A 2.6636 no . . F2 H3B 2.9550 no . . F3 H3A 3.4106 no . . F3 H3B 2.5692 no . . F3 H15 2.7232 no . . O1 H2o 2.48(5) no . . O1 H3A 3.2647 no . . O1 H3B 2.7225 no . . O1 H4 3.1831 no . . O1 H5 3.2839 no . . O1 H15 2.5730 no . . O2 H3A 2.4885 no . . O2 H3B 3.2064 no . . O2 H4 2.7152 no . . O2 H6B 2.5734 no . . C2 H4 2.7167 no . . C2 H6A 3.2176 no . . C2 H6B 2.5893 no . . C2 H15 3.0732 no . . C3 H2o 3.23(5) no . . C3 H5 3.3832 no . . C3 H6B 3.1805 no . . C3 H13 3.1107 no . . C3 H15 2.8755 no . . C4 H6A 3.3587 no . . C4 H6B 2.6875 no . . C4 H9 2.6299 no . . C4 H13 2.7435 no . . C4 H15 3.2456 no . . C5 H3A 3.4138 no . . C5 H3B 2.8386 no . . C5 H13 3.1011 no . . C5 H15 2.7468 no . . C5 H19 2.6354 no . . C6 H2o 3.14(5) no . . C6 H3B 3.3029 no . . C6 H4 2.6527 no . . C6 H15 3.0296 no . . C7 H2o 2.55(5) no . . C7 H3A 2.7936 no . . C7 H3B 2.5980 no . . C7 H15 3.4170 no . . C8 H3A 2.7183 no . . C8 H3B 2.7149 no . . C8 H5 2.8216 no . . C8 H10 3.2795 no . . C8 H12 3.2707 no . . C9 H3A 3.3888 no . . C9 H4 2.4821 no . . C9 H11 3.2737 no . . C9 H13 3.2589 no . . C10 H12 3.2468 no . . C11 H9 3.2644 no . . C11 H13 3.2791 no . . C12 H10 3.2511 no . . C13 H3A 3.4564 no . . C13 H3B 2.9080 no . . C13 H4 3.3367 no . . C13 H5 3.5576 no . . C13 H9 3.2551 no . . C13 H11 3.2836 no . . C14 H3B 3.1226 no . . C14 H4 3.4604 no . . C14 H6A 2.6424 no . . C14 H6B 3.3724 no . . C14 H13 2.6315 no . . C14 H16 3.2754 no . . C14 H18 3.2744 no . . C15 H3B 2.8567 no . . C15 H5 3.3384 no . . C15 H6A 3.2335 no . . C15 H13 2.7446 no . . C15 H17 3.2690 no . . C15 H19 3.2448 no . . C16 H13 3.3879 no . . C16 H18 3.2483 no . . C17 H15 3.2642 no . . C17 H19 3.2516 no . . C18 H16 3.2467 no . . C19 H5 2.4859 no . . C19 H6A 3.4474 no . . C19 H13 3.1883 no . . C19 H15 3.2474 no . . C19 H17 3.2581 no . . H2o H3A 3.4128 no . . H2o H4 3.5611 no . . H2o H6B 2.7700 no . . H3A H4 2.3286 no . . H3A H9 3.4451 no . . H3A H13 3.5629 no . . H3B H4 2.8655 no . . H3B H13 2.5886 no . . H3B H15 2.2596 no . . H4 H5 2.2761 no . . H4 H6A 3.5592 no . . H4 H6B 2.4654 no . . H4 H9 2.2333 no . . H5 H6A 2.3840 no . . H5 H6B 2.2773 no . . H5 H19 2.2380 no . . H6A H15 3.2716 no . . H9 H10 2.3294 no . . H10 H11 2.3556 no . . H11 H12 2.3325 no . . H12 H13 2.3317 no . . H13 H15 2.9704 no . . H15 H16 2.3432 no . . H16 H17 2.3311 no . . H17 H18 2.3363 no . . H18 H19 2.3307 no . . F1 H11 2.8442 no . 1_566 F1 H11 3.1753 no . 2_667 F1 H16 2.8724 no . 1_556 F1 H18 3.1285 no . 4_557 F1 H19 3.1576 no . 4_557 F2 H2o 2.93(5) no . 2_658 F2 H3B 3.0437 no . 2_657 F2 H10 3.1940 no . 2_667 F2 H11 3.4917 no . 2_667 F2 H13 2.9765 no . 2_657 F2 H15 3.1194 no . 2_657 F2 H16 3.3166 no . 2_657 F3 H3B 3.5749 no . 2_657 F3 H9 3.1370 no . 1_565 F3 H10 2.5118 no . 1_565 F3 H10 2.7915 no . 2_667 F3 H11 3.5694 no . 2_667 F3 H19 3.2576 no . 4_557 O1 H5 3.3812 no . 4_557 O1 H17 2.9252 no . 1_556 O1 H19 2.5194 no . 4_557 O2 H12 2.7439 no . 1_556 O2 H13 2.9774 no . 1_556 C3 H3A 3.2211 no . 2_657 C3 H3B 3.0993 no . 2_657 C6 H16 3.3846 no . 4_547 C6 H17 3.1155 no . 1_556 C6 H18 3.5286 no . 1_556 C6 H19 3.3663 no . 4_557 C7 H10 3.4964 no . 2_667 C7 H19 3.5062 no . 4_557 C8 H3A 3.3375 no . 2_657 C8 H6A 2.9905 no . 4_547 C9 H6A 2.8003 no . 4_547 C10 H6A 3.0826 no . 4_547 C10 H15 3.5768 no . 1_545 C10 H16 3.1934 no . 1_545 C11 H6A 3.5073 no . 4_547 C11 H11 3.4345 no . 2_656 C11 H16 3.2849 no . 1_545 C11 H18 3.0420 no . 4_546 C12 H3A 3.2839 no . 2_657 C12 H12 3.2763 no . 2_656 C12 H17 3.4623 no . 4_546 C12 H18 3.2449 no . 4_546 C13 H2o 3.36(5) no . 1_554 C13 H3A 2.8810 no . 2_657 C13 H6A 3.4345 no . 4_547 C14 H5 3.4183 no . 4_557 C14 H9 3.4761 no . 4_557 C15 H2o 3.21(5) no . 1_554 C15 H5 2.8020 no . 4_557 C15 H10 3.4687 no . 1_565 C16 H2o 2.65(5) no . 1_554 C16 H4 3.5071 no . 4_557 C16 H5 2.9990 no . 4_557 C16 H6B 2.8805 no . 4_557 C16 H10 3.5086 no . 1_565 C16 H18 3.3916 no . 4_556 C17 H2o 2.75(5) no . 1_554 C17 H4 3.2858 no . 4_557 C17 H6A 3.5424 no . 1_554 C17 H6B 3.1178 no . 1_554 C17 H6B 3.1367 no . 4_557 C18 H2o 3.32(5) no . 1_554 C18 H4 3.3467 no . 4_557 C18 H6B 3.0647 no . 1_554 C18 H9 3.3419 no . 4_557 C18 H16 3.3996 no . 4_546 C18 H17 3.2631 no . 4_546 C19 H9 2.9956 no . 4_557 C19 H17 3.1239 no . 4_546 H2o F2 2.93(5) no . 2_658 H2o C13 3.36(5) no . 1_556 H2o C15 3.21(5) no . 1_556 H2o C16 2.65(5) no . 1_556 H2o C17 2.75(5) no . 1_556 H2o C18 3.32(5) no . 1_556 H2o H12 3.1564 no . 1_556 H2o H13 2.5962 no . 1_556 H2o H16 2.8195 no . 1_556 H2o H17 3.0123 no . 1_556 H3A C3 3.2211 no . 2_657 H3A C8 3.3375 no . 2_657 H3A C12 3.2839 no . 2_657 H3A C13 2.8810 no . 2_657 H3A H3A 2.9259 no . 2_657 H3A H3B 2.6830 no . 2_657 H3A H12 3.5293 no . 2_657 H3A H13 2.8719 no . 2_657 H3B F2 3.0437 no . 2_657 H3B F3 3.5749 no . 2_657 H3B C3 3.0993 no . 2_657 H3B H3A 2.6830 no . 2_657 H3B H3B 2.6150 no . 2_657 H4 C16 3.5071 no . 4_547 H4 C17 3.2858 no . 4_547 H4 C18 3.3467 no . 4_547 H4 H12 3.4982 no . 1_556 H5 O1 3.3812 no . 4_547 H5 C14 3.4183 no . 4_547 H5 C15 2.8020 no . 4_547 H5 C16 2.9990 no . 4_547 H5 H6A 3.0604 no . 4_547 H5 H15 2.8295 no . 4_547 H5 H16 3.1798 no . 4_547 H6A C8 2.9905 no . 4_557 H6A C9 2.8003 no . 4_557 H6A C10 3.0826 no . 4_557 H6A C11 3.5073 no . 4_557 H6A C13 3.4345 no . 4_557 H6A C17 3.5424 no . 1_556 H6A H5 3.0604 no . 4_557 H6A H9 3.0847 no . 4_557 H6A H10 3.5041 no . 4_557 H6A H16 3.3641 no . 4_547 H6A H17 2.9356 no . 1_556 H6A H18 3.3684 no . 1_556 H6A H19 3.0968 no . 4_557 H6B C16 2.8805 no . 4_547 H6B C17 3.1178 no . 1_556 H6B C17 3.1367 no . 4_547 H6B C18 3.0647 no . 1_556 H6B H16 2.6888 no . 4_547 H6B H17 2.9330 no . 1_556 H6B H17 3.1074 no . 4_547 H6B H18 2.8333 no . 1_556 H9 F3 3.1370 no . 1_545 H9 C14 3.4761 no . 4_547 H9 C18 3.3419 no . 4_547 H9 C19 2.9956 no . 4_547 H9 H6A 3.0847 no . 4_547 H9 H18 3.5165 no . 4_547 H9 H19 2.9770 no . 4_547 H10 F2 3.1940 no . 2_647 H10 F3 2.5118 no . 1_545 H10 F3 2.7915 no . 2_647 H10 C7 3.4964 no . 2_647 H10 C15 3.4687 no . 1_545 H10 C16 3.5086 no . 1_545 H10 H6A 3.5041 no . 4_547 H10 H10 3.2865 no . 2_657 H10 H15 2.8068 no . 1_545 H10 H16 2.8926 no . 1_545 H11 F1 2.8442 no . 1_544 H11 F1 3.1753 no . 2_647 H11 F2 3.4917 no . 2_647 H11 F3 3.5694 no . 2_647 H11 C11 3.4345 no . 2_656 H11 H11 2.6844 no . 2_656 H11 H12 3.4609 no . 2_656 H11 H16 3.0621 no . 1_545 H11 H18 2.8869 no . 4_546 H12 O2 2.7439 no . 1_554 H12 C12 3.2763 no . 2_656 H12 H2o 3.1564 no . 1_554 H12 H3A 3.5293 no . 2_657 H12 H4 3.4982 no . 1_554 H12 H11 3.4609 no . 2_656 H12 H12 2.7285 no . 2_656 H12 H17 3.4669 no . 4_546 H12 H18 3.2286 no . 4_546 H13 F2 2.9765 no . 2_657 H13 O2 2.9774 no . 1_554 H13 H2o 2.5962 no . 1_554 H13 H3A 2.8719 no . 2_657 H15 F2 3.1194 no . 2_657 H15 C10 3.5768 no . 1_565 H15 H5 2.8295 no . 4_557 H15 H10 2.8068 no . 1_565 H15 H19 3.4783 no . 4_557 H16 F1 2.8724 no . 1_554 H16 F2 3.3166 no . 2_657 H16 C6 3.3846 no . 4_557 H16 C10 3.1934 no . 1_565 H16 C11 3.2849 no . 1_565 H16 C18 3.3996 no . 4_556 H16 H2o 2.8195 no . 1_554 H16 H5 3.1798 no . 4_557 H16 H6A 3.3641 no . 4_557 H16 H6B 2.6888 no . 4_557 H16 H10 2.8926 no . 1_565 H16 H11 3.0621 no . 1_565 H16 H18 2.6520 no . 4_556 H17 O1 2.9252 no . 1_554 H17 C6 3.1155 no . 1_554 H17 C12 3.4623 no . 4_556 H17 C18 3.2631 no . 4_556 H17 C19 3.1239 no . 4_556 H17 H2o 3.0123 no . 1_554 H17 H6A 2.9356 no . 1_554 H17 H6B 2.9330 no . 1_554 H17 H6B 3.1074 no . 4_557 H17 H12 3.4669 no . 4_556 H17 H18 3.1091 no . 4_556 H17 H19 2.8217 no . 4_556 H18 F1 3.1285 no . 4_547 H18 C6 3.5286 no . 1_554 H18 C11 3.0420 no . 4_556 H18 C12 3.2449 no . 4_556 H18 C16 3.3916 no . 4_546 H18 H6A 3.3684 no . 1_554 H18 H6B 2.8333 no . 1_554 H18 H9 3.5165 no . 4_557 H18 H11 2.8869 no . 4_556 H18 H12 3.2286 no . 4_556 H18 H16 2.6520 no . 4_546 H18 H17 3.1091 no . 4_546 H19 F1 3.1576 no . 4_547 H19 F3 3.2576 no . 4_547 H19 O1 2.5194 no . 4_547 H19 C6 3.3663 no . 4_547 H19 C7 3.5062 no . 4_547 H19 H6A 3.0968 no . 4_547 H19 H9 2.9770 no . 4_557 H19 H15 3.4783 no . 4_547 H19 H17 2.8217 no . 4_546 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O2 H2o F1 . . . 2.765(5) 0.979 2.41(5) 101(4) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 907071'