# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is © The Royal Society of Chemistry and Owner Societies 2010 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_Cambridge 0171 _publ_contact_author_name 'Irie, Masahiro' _publ_contact_author_email iriem@rikkyo.ne.jp _publ_section_title ; Photochromism of dithienylethene single crystals having anthracene substituents ; loop_ _publ_author_name H.Ohara M.Morimoto M.Irie # Attachment '- c003355c_cif1a.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 764005' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-Bis(2-(9-anthryl)-5-ethylthien-3-yl)perfluorocyclopentene ; _chemical_name_common 1,2-Bis(2-(9-anthryl)-5-ethylthien-3-yl)perfluorocyclopentene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H30 F6 S2' _chemical_formula_weight 748.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 26.732(2) _cell_length_b 8.0585(7) _cell_length_c 16.3195(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3515.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6878 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.47 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25214 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.58 _reflns_number_total 3937 _reflns_number_gt 3111 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3937 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1040 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.68118(5) 0.17179(19) 0.39616(8) 0.0183(3) Uani 1 1 d . . . C2 C 0.68943(5) 0.28670(18) 0.33563(8) 0.0169(3) Uani 1 1 d . . . C3 C 0.65606(5) 0.42553(18) 0.34042(9) 0.0182(3) Uani 1 1 d . . . H3 H 0.6567 0.5151 0.3026 0.022 Uiso 1 1 calc R . . C4 C 0.62349(5) 0.41741(18) 0.40386(8) 0.0183(3) Uani 1 1 d . . . C5 C 0.72533(5) 0.26739(17) 0.26801(9) 0.0171(3) Uani 1 1 d . . . C6 C 0.70654(6) 0.2832(2) 0.18182(10) 0.0310(4) Uani 1 1 d . . . C7 C 0.7500 0.2500 0.12720(14) 0.0373(6) Uani 1 2 d S . . C8 C 0.58374(5) 0.53646(17) 0.42807(8) 0.0173(3) Uani 1 1 d . . . C9 C 0.53847(5) 0.53937(18) 0.38353(8) 0.0179(3) Uani 1 1 d . . . C10 C 0.52938(5) 0.43559(18) 0.31435(9) 0.0201(3) Uani 1 1 d . . . H10 H 0.5547 0.3613 0.2965 0.024 Uiso 1 1 calc R . . C11 C 0.48504(6) 0.4409(2) 0.27336(9) 0.0230(3) Uani 1 1 d . . . H11 H 0.4798 0.3702 0.2276 0.028 Uiso 1 1 calc R . . C12 C 0.44663(6) 0.55122(19) 0.29836(9) 0.0232(3) Uani 1 1 d . . . H12 H 0.4160 0.5546 0.2689 0.028 Uiso 1 1 calc R . . C13 C 0.45335(5) 0.65162(18) 0.36385(9) 0.0208(3) Uani 1 1 d . . . H13 H 0.4272 0.7243 0.3801 0.025 Uiso 1 1 calc R . . C14 C 0.49921(5) 0.65001(18) 0.40892(8) 0.0182(3) Uani 1 1 d . . . C15 C 0.50654(5) 0.75095(17) 0.47731(9) 0.0193(3) Uani 1 1 d . . . H15 H 0.4803 0.8226 0.4944 0.023 Uiso 1 1 calc R . . C16 C 0.55108(6) 0.74959(17) 0.52112(9) 0.0195(3) Uani 1 1 d . . . C17 C 0.55799(6) 0.85084(19) 0.59203(9) 0.0244(3) Uani 1 1 d . . . H17 H 0.5316 0.9210 0.6098 0.029 Uiso 1 1 calc R . . C18 C 0.60156(6) 0.8485(2) 0.63439(10) 0.0289(4) Uani 1 1 d . . . H18 H 0.6055 0.9165 0.6815 0.035 Uiso 1 1 calc R . . C19 C 0.64132(6) 0.7449(2) 0.60841(10) 0.0266(4) Uani 1 1 d . . . H19 H 0.6719 0.7453 0.6380 0.032 Uiso 1 1 calc R . . C20 C 0.63630(5) 0.64514(19) 0.54198(9) 0.0226(3) Uani 1 1 d . . . H20 H 0.6635 0.5770 0.5256 0.027 Uiso 1 1 calc R . . C21 C 0.59083(5) 0.64101(17) 0.49639(8) 0.0179(3) Uani 1 1 d . . . C22 C 0.70439(6) 0.00418(19) 0.40939(9) 0.0235(3) Uani 1 1 d . . . H22A H 0.6977 -0.0322 0.4663 0.028 Uiso 1 1 calc R . . H22B H 0.7411 0.0132 0.4025 0.028 Uiso 1 1 calc R . . C23 C 0.68448(7) -0.1256(2) 0.35050(12) 0.0424(5) Uani 1 1 d . . . H23A H 0.6481 -0.1345 0.3566 0.064 Uiso 1 1 calc R . . H23B H 0.6999 -0.2331 0.3627 0.064 Uiso 1 1 calc R . . H23C H 0.6925 -0.0932 0.2941 0.064 Uiso 1 1 calc R . . F1 F 0.74596(9) 0.1928(3) 0.05532(11) 0.0395(7) Uani 0.50 1 d P . . F2 F 0.76266(7) 0.4313(3) 0.11088(13) 0.0389(5) Uani 0.50 1 d P . . F3A F 0.67375(9) 0.3931(3) 0.16424(11) 0.0304(9) Uani 0.494(5) 1 d P A 1 F4A F 0.67812(9) 0.1251(4) 0.16487(11) 0.0295(7) Uani 0.494(5) 1 d P A 1 F3B F 0.70560(11) 0.4697(3) 0.16708(12) 0.0379(9) Uani 0.506(5) 1 d P A 2 F4B F 0.66290(8) 0.2402(4) 0.16751(12) 0.0414(11) Uani 0.506(5) 1 d P A 2 S1 S 0.632830(13) 0.23536(5) 0.45843(2) 0.02088(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0132(7) 0.0240(8) 0.0177(7) -0.0009(6) -0.0001(5) 0.0013(6) C2 0.0117(7) 0.0210(8) 0.0179(7) -0.0012(6) -0.0016(6) 0.0002(5) C3 0.0156(7) 0.0201(7) 0.0187(7) 0.0011(6) -0.0012(6) 0.0013(6) C4 0.0149(7) 0.0208(8) 0.0192(7) 0.0007(6) -0.0013(6) 0.0007(6) C5 0.0173(7) 0.0158(7) 0.0181(7) 0.0003(6) 0.0000(6) 0.0008(5) C6 0.0154(8) 0.0559(12) 0.0217(8) 0.0044(8) -0.0013(6) 0.0120(7) C7 0.0217(12) 0.073(2) 0.0172(12) 0.000 0.000 0.0061(12) C8 0.0143(7) 0.0191(7) 0.0185(7) 0.0026(6) 0.0036(6) 0.0012(5) C9 0.0154(7) 0.0208(7) 0.0175(7) 0.0026(6) 0.0040(5) 0.0003(6) C10 0.0169(7) 0.0237(8) 0.0196(7) -0.0003(6) 0.0035(6) 0.0014(6) C11 0.0224(8) 0.0288(9) 0.0178(7) -0.0021(6) 0.0011(6) -0.0020(6) C12 0.0151(7) 0.0317(9) 0.0227(8) 0.0050(6) -0.0021(6) -0.0003(6) C13 0.0140(7) 0.0255(8) 0.0228(8) 0.0041(6) 0.0042(6) 0.0034(6) C14 0.0153(7) 0.0212(8) 0.0180(7) 0.0053(6) 0.0040(6) 0.0015(6) C15 0.0183(7) 0.0188(8) 0.0208(8) 0.0022(6) 0.0055(6) 0.0040(6) C16 0.0196(7) 0.0191(8) 0.0197(7) 0.0025(6) 0.0032(6) -0.0009(6) C17 0.0258(8) 0.0211(8) 0.0262(8) -0.0030(6) 0.0031(6) 0.0010(6) C18 0.0337(9) 0.0258(9) 0.0271(9) -0.0061(7) -0.0020(7) -0.0052(7) C19 0.0218(8) 0.0284(9) 0.0295(9) 0.0007(7) -0.0056(7) -0.0058(6) C20 0.0170(7) 0.0257(8) 0.0252(8) 0.0023(6) 0.0005(6) -0.0001(6) C21 0.0165(7) 0.0192(8) 0.0181(7) 0.0032(6) 0.0029(6) -0.0017(6) C22 0.0208(8) 0.0233(8) 0.0264(8) 0.0060(6) 0.0043(6) 0.0038(6) C23 0.0538(12) 0.0226(9) 0.0508(12) -0.0034(8) -0.0050(10) 0.0039(8) F1 0.0233(11) 0.076(2) 0.0190(9) -0.0130(9) -0.0011(9) 0.0118(15) F2 0.0324(11) 0.0470(13) 0.0373(12) 0.0213(10) 0.0026(9) -0.0077(9) F3A 0.0295(16) 0.0405(17) 0.0213(10) 0.0034(9) -0.0022(9) 0.0182(14) F4A 0.0247(12) 0.0376(16) 0.0263(11) -0.0045(9) -0.0045(8) -0.0118(11) F3B 0.0346(17) 0.0451(15) 0.0340(12) 0.0172(10) 0.0065(10) 0.0196(13) F4B 0.0147(10) 0.084(3) 0.0253(11) -0.0021(12) -0.0033(8) -0.0060(12) S1 0.0181(2) 0.0245(2) 0.0200(2) 0.00378(15) 0.00475(14) 0.00348(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.372(2) . ? C1 C22 1.502(2) . ? C1 S1 1.7220(14) . ? C2 C3 1.4328(19) . ? C2 C5 1.4708(19) . ? C3 C4 1.3544(19) . ? C3 H3 0.9500 . ? C4 C8 1.4852(19) . ? C4 S1 1.7342(15) . ? C5 C5 1.348(3) 2_655 ? C5 C6 1.499(2) . ? C6 F4B 1.239(2) . ? C6 F3A 1.279(2) . ? C6 C7 1.489(2) . ? C6 F4A 1.509(3) . ? C6 F3B 1.522(3) . ? C7 F1 1.265(3) . ? C7 F1 1.265(3) 2_655 ? C7 C6 1.489(2) 2_655 ? C7 F2 1.523(2) 2_655 ? C7 F2 1.523(2) . ? C8 C21 1.410(2) . ? C8 C9 1.4117(19) . ? C9 C10 1.426(2) . ? C9 C14 1.4381(19) . ? C10 C11 1.362(2) . ? C10 H10 0.9500 . ? C11 C12 1.418(2) . ? C11 H11 0.9500 . ? C12 C13 1.352(2) . ? C12 H12 0.9500 . ? C13 C14 1.4297(19) . ? C13 H13 0.9500 . ? C14 C15 1.395(2) . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 C17 1.428(2) . ? C16 C21 1.434(2) . ? C17 C18 1.355(2) . ? C17 H17 0.9500 . ? C18 C19 1.417(2) . ? C18 H18 0.9500 . ? C19 C20 1.356(2) . ? C19 H19 0.9500 . ? C20 C21 1.4256(19) . ? C20 H20 0.9500 . ? C22 C23 1.517(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? F1 F1 0.947(4) 2_655 ? F1 F2 1.369(3) 2_655 ? F2 F1 1.369(3) 2_655 ? 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 C1 C22 130.10(13) . . ? C2 C1 S1 110.17(11) . . ? C22 C1 S1 119.52(11) . . ? C1 C2 C3 112.81(12) . . ? C1 C2 C5 125.01(13) . . ? C3 C2 C5 121.99(12) . . ? C4 C3 C2 113.84(13) . . ? C4 C3 H3 123.1 . . ? C2 C3 H3 123.1 . . ? C3 C4 C8 129.21(13) . . ? C3 C4 S1 109.93(11) . . ? C8 C4 S1 120.85(10) . . ? C5 C5 C2 131.33(8) 2_655 . ? C5 C5 C6 110.21(8) 2_655 . ? C2 C5 C6 118.45(12) . . ? F4B C6 F3A 60.41(18) . . ? F4B C6 C7 124.85(18) . . ? F3A C6 C7 121.68(17) . . ? F4B C6 C5 117.94(17) . . ? F3A C6 C5 119.95(16) . . ? C7 C6 C5 106.56(13) . . ? F4B C6 F4A 41.86(14) . . ? F3A C6 F4A 101.45(18) . . ? C7 C6 F4A 97.54(15) . . ? C5 C6 F4A 105.60(14) . . ? F4B C6 F3B 103.4(2) . . ? F3A C6 F3B 43.06(13) . . ? C7 C6 F3B 95.50(14) . . ? C5 C6 F3B 103.76(15) . . ? F4A C6 F3B 142.78(16) . . ? F1 C7 F1 44.0(2) . 2_655 ? F1 C7 C6 123.80(14) . 2_655 ? F1 C7 C6 123.66(13) 2_655 2_655 ? F1 C7 C6 123.66(13) . . ? F1 C7 C6 123.81(14) 2_655 . ? C6 C7 C6 106.43(18) 2_655 . ? F1 C7 F2 57.95(13) . 2_655 ? F1 C7 F2 101.91(19) 2_655 2_655 ? C6 C7 F2 96.05(12) 2_655 2_655 ? C6 C7 F2 95.96(11) . 2_655 ? F1 C7 F2 101.91(19) . . ? F1 C7 F2 57.95(13) 2_655 . ? C6 C7 F2 95.96(11) 2_655 . ? C6 C7 F2 96.06(12) . . ? F2 C7 F2 159.9(2) 2_655 . ? C21 C8 C9 120.82(12) . . ? C21 C8 C4 120.00(12) . . ? C9 C8 C4 119.15(12) . . ? C8 C9 C10 122.96(13) . . ? C8 C9 C14 119.17(13) . . ? C10 C9 C14 117.87(13) . . ? C11 C10 C9 121.24(14) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.59(14) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 120.41(13) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 121.00(13) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 121.79(13) . . ? C15 C14 C9 119.32(13) . . ? C13 C14 C9 118.89(13) . . ? C16 C15 C14 121.85(13) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C17 121.57(13) . . ? C15 C16 C21 119.67(13) . . ? C17 C16 C21 118.74(13) . . ? C18 C17 C16 121.12(14) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 120.03(15) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 120.97(15) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 121.02(14) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C8 C21 C20 122.77(13) . . ? C8 C21 C16 119.17(13) . . ? C20 C21 C16 118.06(13) . . ? C1 C22 C23 112.60(13) . . ? C1 C22 H22A 109.1 . . ? C23 C22 H22A 109.1 . . ? C1 C22 H22B 109.1 . . ? C23 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? F1 F1 C7 68.02(11) 2_655 . ? F1 F1 F2 138.53(11) 2_655 2_655 ? C7 F1 F2 70.51(13) . 2_655 ? F1 F2 C7 51.53(14) 2_655 . ? C1 S1 C4 93.25(7) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.485 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.054 # Attachment '- c003355c_cif2a.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 764006' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-Bis(2-(1-anthryl)-5-ethylthien-3-yl)perfluorocyclopentene ; _chemical_name_common 1,2-Bis(2-(1-anthryl)-5-ethylthien-3-yl)perfluorocyclopentene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H30 F6 S2' _chemical_formula_weight 748.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8648(9) _cell_length_b 11.9212(10) _cell_length_c 15.7333(14) _cell_angle_alpha 70.4600(10) _cell_angle_beta 82.3160(10) _cell_angle_gamma 82.2090(10) _cell_volume 1719.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 5666 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 26.95 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19251 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 27.04 _reflns_number_total 7320 _reflns_number_gt 5608 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7320 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.68031(18) 0.38722(15) 0.27008(11) 0.0186(4) Uani 1 1 d . . . C2 C 0.55423(17) 0.34329(15) 0.28710(11) 0.0180(4) Uani 1 1 d . . . C3 C 0.51922(18) 0.30984(15) 0.21366(11) 0.0189(4) Uani 1 1 d . . . H3 H 0.4353 0.2785 0.2146 0.023 Uiso 1 1 calc R . . C4 C 0.61793(18) 0.32751(15) 0.14273(11) 0.0186(4) Uani 1 1 d . . . C5 C 0.46259(17) 0.33502(15) 0.37031(11) 0.0175(4) Uani 1 1 d . . . C6 C 0.31950(18) 0.39819(16) 0.36443(11) 0.0202(4) Uani 1 1 d . . . C7 C 0.24936(18) 0.35369(16) 0.46116(12) 0.0228(4) Uani 1 1 d . . . C8 C 0.37044(18) 0.31471(15) 0.51905(11) 0.0201(4) Uani 1 1 d . . . C9 C 0.48933(17) 0.28471(15) 0.45778(11) 0.0180(4) Uani 1 1 d . . . C10 C 0.67757(18) 0.11476(16) 0.47603(11) 0.0206(4) Uani 1 1 d . . . C11 C 0.61308(17) 0.21281(15) 0.49735(11) 0.0185(4) Uani 1 1 d . . . C12 C 0.67293(17) 0.23577(16) 0.56737(11) 0.0198(4) Uani 1 1 d . . . H12 H 0.6392 0.2998 0.5901 0.024 Uiso 1 1 calc R . . C13 C 0.78296(18) 0.15665(16) 0.59816(12) 0.0207(4) Uani 1 1 d . . . C14 C 0.63059(17) 0.30193(16) 0.05570(11) 0.0188(4) Uani 1 1 d . . . C15 C 0.65447(18) 0.39201(16) -0.02356(12) 0.0207(4) Uani 1 1 d . . . H15 H 0.6479 0.4719 -0.0228 0.025 Uiso 1 1 calc R . . C16 C 0.68882(18) 0.36938(17) -0.10718(12) 0.0226(4) Uani 1 1 d . . . H16 H 0.7037 0.4339 -0.1616 0.027 Uiso 1 1 calc R . . C17 C 0.70046(18) 0.25585(16) -0.10959(12) 0.0213(4) Uani 1 1 d . . . H17 H 0.7274 0.2413 -0.1655 0.026 Uiso 1 1 calc R . . C18 C 0.67287(17) 0.15793(16) -0.02951(11) 0.0184(4) Uani 1 1 d . . . C19 C 0.68339(17) 0.04097(16) -0.03100(12) 0.0202(4) Uani 1 1 d . . . H19 H 0.7123 0.0259 -0.0865 0.024 Uiso 1 1 calc R . . C20 C 0.65276(17) -0.05462(16) 0.04647(12) 0.0199(4) Uani 1 1 d . . . C21 C 0.66345(18) -0.17477(17) 0.04638(13) 0.0233(4) Uani 1 1 d . . . H21 H 0.6941 -0.1919 -0.0082 0.028 Uiso 1 1 calc R . . C22 C 0.63051(18) -0.26575(17) 0.12313(13) 0.0264(4) Uani 1 1 d . . . H22 H 0.6404 -0.3456 0.1220 0.032 Uiso 1 1 calc R . . C23 C 0.58141(19) -0.24156(17) 0.20499(13) 0.0262(4) Uani 1 1 d . . . H23 H 0.5569 -0.3052 0.2580 0.031 Uiso 1 1 calc R . . C24 C 0.56933(18) -0.12848(16) 0.20793(12) 0.0229(4) Uani 1 1 d . . . H24 H 0.5354 -0.1138 0.2630 0.028 Uiso 1 1 calc R . . C25 C 0.60650(17) -0.03097(16) 0.12997(12) 0.0198(4) Uani 1 1 d . . . C26 C 0.59966(17) 0.08554(16) 0.13198(12) 0.0201(4) Uani 1 1 d . . . H26 H 0.5711 0.1005 0.1876 0.024 Uiso 1 1 calc R . . C27 C 0.63327(17) 0.18074(15) 0.05517(11) 0.0180(4) Uani 1 1 d . . . C28 C 0.87447(18) 0.16242(16) 0.66357(12) 0.0196(4) Uani 1 1 d . . . C29 C 0.92506(18) 0.26895(16) 0.64990(12) 0.0228(4) Uani 1 1 d . . . H29 H 0.9018 0.3352 0.5986 0.027 Uiso 1 1 calc R . . C30 C 1.01088(19) 0.28363(17) 0.70983(13) 0.0247(4) Uani 1 1 d . . . H30 H 1.0441 0.3590 0.6984 0.030 Uiso 1 1 calc R . . C31 C 1.04600(18) 0.19021(16) 0.78381(12) 0.0222(4) Uani 1 1 d . . . H31 H 1.1040 0.2008 0.8236 0.027 Uiso 1 1 calc R . . C32 C 0.99659(17) 0.07674(15) 0.80227(11) 0.0179(4) Uani 1 1 d . . . C33 C 1.02927(17) -0.01911(15) 0.87877(11) 0.0193(4) Uani 1 1 d . . . H33 H 1.0852 -0.0079 0.9194 0.023 Uiso 1 1 calc R . . C34 C 0.98271(17) -0.13076(16) 0.89757(12) 0.0199(4) Uani 1 1 d . . . C35 C 1.01159(18) -0.22837(16) 0.97761(12) 0.0232(4) Uani 1 1 d . . . H35 H 1.0657 -0.2180 1.0195 0.028 Uiso 1 1 calc R . . C36 C 0.96289(19) -0.33519(17) 0.99443(13) 0.0264(4) Uani 1 1 d . . . H36 H 0.9810 -0.3983 1.0488 0.032 Uiso 1 1 calc R . . C37 C 0.88531(19) -0.35361(17) 0.93177(13) 0.0277(4) Uani 1 1 d . . . H37 H 0.8544 -0.4299 0.9434 0.033 Uiso 1 1 calc R . . C38 C 0.85436(18) -0.26344(16) 0.85499(13) 0.0245(4) Uani 1 1 d . . . H38 H 0.8021 -0.2774 0.8136 0.029 Uiso 1 1 calc R . . C39 C 0.89962(18) -0.14788(16) 0.83584(12) 0.0202(4) Uani 1 1 d . . . C40 C 0.86333(18) -0.05146(16) 0.76047(12) 0.0201(4) Uani 1 1 d . . . H40 H 0.8052 -0.0626 0.7210 0.024 Uiso 1 1 calc R . . C41 C 0.90954(17) 0.06071(15) 0.74119(11) 0.0184(4) Uani 1 1 d . . . C42 C 0.75209(18) 0.43647(16) 0.32595(12) 0.0228(4) Uani 1 1 d . . . H42A H 0.6931 0.4328 0.3827 0.027 Uiso 1 1 calc R . . H42B H 0.7634 0.5217 0.2924 0.027 Uiso 1 1 calc R . . C43 C 0.8925(2) 0.37102(18) 0.34987(14) 0.0309(5) Uani 1 1 d . . . H43A H 0.8825 0.2865 0.3834 0.046 Uiso 1 1 calc R . . H43B H 0.9321 0.4069 0.3874 0.046 Uiso 1 1 calc R . . H43C H 0.9533 0.3775 0.2942 0.046 Uiso 1 1 calc R . . C44 C 0.64499(18) 0.05522(16) 0.41214(12) 0.0220(4) Uani 1 1 d . . . H44A H 0.5672 0.1030 0.3786 0.026 Uiso 1 1 calc R . . H44B H 0.6154 -0.0247 0.4476 0.026 Uiso 1 1 calc R . . C45 C 0.7660(2) 0.04069(18) 0.34423(12) 0.0285(5) Uani 1 1 d . . . H45A H 0.7928 0.1197 0.3065 0.043 Uiso 1 1 calc R . . H45B H 0.7393 -0.0007 0.3057 0.043 Uiso 1 1 calc R . . H45C H 0.8437 -0.0062 0.3768 0.043 Uiso 1 1 calc R . . F1 F 0.24851(10) 0.37720(10) 0.30447(7) 0.0286(3) Uani 1 1 d . . . F2 F 0.32268(11) 0.51898(9) 0.33775(7) 0.0286(3) Uani 1 1 d . . . F3 F 0.18334(11) 0.25722(10) 0.47086(7) 0.0310(3) Uani 1 1 d . . . F4 F 0.15679(11) 0.43587(9) 0.48255(7) 0.0310(3) Uani 1 1 d . . . F5 F 0.34219(11) 0.22345(9) 0.59555(7) 0.0292(3) Uani 1 1 d . . . F6 F 0.39350(11) 0.40697(10) 0.54665(7) 0.0304(3) Uani 1 1 d . . . S1 S 0.75579(5) 0.38577(4) 0.16524(3) 0.02124(12) Uani 1 1 d . . . S2 S 0.81325(5) 0.05198(4) 0.54133(3) 0.02379(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0189(9) 0.0187(9) 0.0173(9) -0.0065(7) -0.0007(7) 0.0018(7) C2 0.0178(9) 0.0185(9) 0.0170(9) -0.0058(7) -0.0032(7) 0.0023(7) C3 0.0171(9) 0.0215(9) 0.0171(9) -0.0055(7) -0.0029(7) 0.0013(7) C4 0.0195(9) 0.0185(9) 0.0169(9) -0.0045(7) -0.0042(7) 0.0007(7) C5 0.0163(9) 0.0194(9) 0.0174(9) -0.0078(7) -0.0006(7) -0.0001(7) C6 0.0196(9) 0.0228(10) 0.0170(9) -0.0065(8) -0.0028(7) 0.0027(8) C7 0.0203(10) 0.0241(10) 0.0222(10) -0.0080(8) 0.0006(8) 0.0037(8) C8 0.0243(10) 0.0205(10) 0.0148(9) -0.0062(7) -0.0007(8) 0.0010(8) C9 0.0185(9) 0.0185(9) 0.0182(9) -0.0080(7) -0.0020(7) 0.0003(7) C10 0.0194(9) 0.0238(10) 0.0161(9) -0.0041(8) -0.0024(7) 0.0008(8) C11 0.0164(9) 0.0222(10) 0.0153(9) -0.0045(7) -0.0008(7) -0.0009(7) C12 0.0193(9) 0.0229(10) 0.0161(9) -0.0059(7) -0.0020(7) 0.0008(8) C13 0.0214(10) 0.0240(10) 0.0164(9) -0.0070(8) -0.0015(7) 0.0002(8) C14 0.0144(9) 0.0267(10) 0.0156(9) -0.0075(8) -0.0021(7) 0.0001(7) C15 0.0193(9) 0.0216(10) 0.0209(10) -0.0063(8) -0.0028(8) -0.0020(8) C16 0.0212(10) 0.0288(10) 0.0147(9) -0.0019(8) -0.0026(7) -0.0042(8) C17 0.0172(9) 0.0329(11) 0.0137(9) -0.0074(8) -0.0021(7) -0.0013(8) C18 0.0119(8) 0.0276(10) 0.0159(9) -0.0073(8) -0.0033(7) 0.0000(7) C19 0.0141(9) 0.0313(11) 0.0175(9) -0.0113(8) -0.0030(7) 0.0007(8) C20 0.0123(9) 0.0270(10) 0.0212(9) -0.0086(8) -0.0046(7) 0.0007(7) C21 0.0154(9) 0.0305(11) 0.0272(10) -0.0139(9) -0.0045(8) 0.0014(8) C22 0.0203(10) 0.0239(10) 0.0364(12) -0.0109(9) -0.0080(9) 0.0014(8) C23 0.0227(10) 0.0271(11) 0.0255(10) -0.0019(8) -0.0071(8) -0.0028(8) C24 0.0198(10) 0.0287(11) 0.0192(10) -0.0058(8) -0.0042(8) -0.0011(8) C25 0.0144(9) 0.0266(10) 0.0183(9) -0.0064(8) -0.0058(7) 0.0001(7) C26 0.0182(9) 0.0271(10) 0.0152(9) -0.0074(8) -0.0033(7) 0.0008(8) C27 0.0137(9) 0.0244(10) 0.0154(9) -0.0058(7) -0.0035(7) -0.0003(7) C28 0.0169(9) 0.0244(10) 0.0169(9) -0.0071(8) -0.0008(7) 0.0010(7) C29 0.0227(10) 0.0232(10) 0.0190(9) -0.0040(8) -0.0016(8) 0.0015(8) C30 0.0240(10) 0.0232(10) 0.0280(10) -0.0092(8) 0.0010(8) -0.0068(8) C31 0.0186(9) 0.0265(10) 0.0241(10) -0.0111(8) -0.0028(8) -0.0028(8) C32 0.0129(8) 0.0231(10) 0.0181(9) -0.0084(8) 0.0009(7) -0.0009(7) C33 0.0148(9) 0.0273(10) 0.0172(9) -0.0088(8) -0.0028(7) -0.0013(7) C34 0.0162(9) 0.0235(10) 0.0190(9) -0.0069(8) -0.0008(7) 0.0005(7) C35 0.0164(9) 0.0293(11) 0.0218(10) -0.0063(8) -0.0024(8) 0.0011(8) C36 0.0216(10) 0.0239(10) 0.0272(11) -0.0027(8) -0.0002(8) 0.0038(8) C37 0.0214(10) 0.0213(10) 0.0379(12) -0.0083(9) 0.0018(9) -0.0017(8) C38 0.0193(10) 0.0271(10) 0.0299(11) -0.0130(9) -0.0025(8) -0.0019(8) C39 0.0166(9) 0.0228(10) 0.0220(10) -0.0095(8) 0.0003(7) -0.0004(7) C40 0.0160(9) 0.0280(10) 0.0192(9) -0.0108(8) -0.0039(7) -0.0009(8) C41 0.0147(9) 0.0236(10) 0.0169(9) -0.0079(8) -0.0004(7) 0.0006(7) C42 0.0238(10) 0.0253(10) 0.0214(10) -0.0098(8) -0.0021(8) -0.0037(8) C43 0.0274(11) 0.0368(12) 0.0331(11) -0.0150(9) -0.0081(9) -0.0035(9) C44 0.0219(10) 0.0222(10) 0.0221(10) -0.0083(8) -0.0053(8) 0.0034(8) C45 0.0307(11) 0.0351(12) 0.0223(10) -0.0146(9) -0.0007(8) -0.0004(9) F1 0.0201(6) 0.0443(7) 0.0220(6) -0.0116(5) -0.0060(5) 0.0011(5) F2 0.0334(6) 0.0220(6) 0.0237(6) -0.0028(5) 0.0000(5) 0.0060(5) F3 0.0253(6) 0.0371(7) 0.0282(6) -0.0057(5) -0.0023(5) -0.0076(5) F4 0.0264(6) 0.0356(7) 0.0230(6) -0.0068(5) 0.0014(5) 0.0139(5) F5 0.0299(6) 0.0330(6) 0.0164(6) -0.0007(5) 0.0007(5) 0.0036(5) F6 0.0325(6) 0.0342(6) 0.0311(6) -0.0214(5) -0.0034(5) 0.0032(5) S1 0.0210(2) 0.0249(3) 0.0188(2) -0.00847(19) 0.00089(18) -0.00437(19) S2 0.0233(3) 0.0271(3) 0.0224(3) -0.0113(2) -0.0078(2) 0.0067(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.374(2) . ? C1 C42 1.498(2) . ? C1 S1 1.7212(17) . ? C2 C3 1.437(2) . ? C2 C5 1.471(2) . ? C3 C4 1.359(2) . ? C3 H3 0.9500 . ? C4 C14 1.486(2) . ? C4 S1 1.7340(18) . ? C5 C9 1.351(2) . ? C5 C6 1.506(2) . ? C6 F1 1.3510(19) . ? C6 F2 1.362(2) . ? C6 C7 1.534(2) . ? C7 F4 1.343(2) . ? C7 F3 1.352(2) . ? C7 C8 1.526(2) . ? C8 F5 1.3514(19) . ? C8 F6 1.3652(19) . ? C8 C9 1.499(2) . ? C9 C11 1.475(2) . ? C10 C11 1.374(2) . ? C10 C44 1.498(2) . ? C10 S2 1.7289(17) . ? C11 C12 1.434(2) . ? C12 C13 1.364(2) . ? C12 H12 0.9500 . ? C13 C28 1.480(2) . ? C13 S2 1.7377(18) . ? C14 C15 1.363(2) . ? C14 C27 1.444(2) . ? C15 C16 1.418(2) . ? C15 H15 0.9500 . ? C16 C17 1.356(2) . ? C16 H16 0.9500 . ? C17 C18 1.426(2) . ? C17 H17 0.9500 . ? C18 C19 1.392(2) . ? C18 C27 1.441(2) . ? C19 C20 1.393(2) . ? C19 H19 0.9500 . ? C20 C21 1.422(2) . ? C20 C25 1.437(2) . ? C21 C22 1.362(3) . ? C21 H21 0.9500 . ? C22 C23 1.421(3) . ? C22 H22 0.9500 . ? C23 C24 1.353(3) . ? C23 H23 0.9500 . ? C24 C25 1.425(2) . ? C24 H24 0.9500 . ? C25 C26 1.392(2) . ? C26 C27 1.391(2) . ? C26 H26 0.9500 . ? C28 C29 1.367(2) . ? C28 C41 1.446(2) . ? C29 C30 1.414(3) . ? C29 H29 0.9500 . ? C30 C31 1.361(2) . ? C30 H30 0.9500 . ? C31 C32 1.425(2) . ? C31 H31 0.9500 . ? C32 C33 1.394(2) . ? C32 C41 1.444(2) . ? C33 C34 1.391(2) . ? C33 H33 0.9500 . ? C34 C35 1.431(2) . ? C34 C39 1.431(2) . ? C35 C36 1.352(2) . ? C35 H35 0.9500 . ? C36 C37 1.414(3) . ? C36 H36 0.9500 . ? C37 C38 1.360(3) . ? C37 H37 0.9500 . ? C38 C39 1.429(2) . ? C38 H38 0.9500 . ? C39 C40 1.395(2) . ? C40 C41 1.395(2) . ? C40 H40 0.9500 . ? C42 C43 1.523(3) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 C45 1.524(2) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? 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 C1 C42 130.07(16) . . ? C2 C1 S1 110.30(13) . . ? C42 C1 S1 119.59(13) . . ? C1 C2 C3 112.87(15) . . ? C1 C2 C5 123.65(15) . . ? C3 C2 C5 123.45(16) . . ? C4 C3 C2 113.39(16) . . ? C4 C3 H3 123.3 . . ? C2 C3 H3 123.3 . . ? C3 C4 C14 132.72(16) . . ? C3 C4 S1 110.23(13) . . ? C14 C4 S1 116.98(13) . . ? C9 C5 C2 129.52(16) . . ? C9 C5 C6 110.35(15) . . ? C2 C5 C6 119.91(14) . . ? F1 C6 F2 106.02(13) . . ? F1 C6 C5 113.78(14) . . ? F2 C6 C5 111.00(14) . . ? F1 C6 C7 111.50(14) . . ? F2 C6 C7 109.84(14) . . ? C5 C6 C7 104.75(14) . . ? F4 C7 F3 107.70(14) . . ? F4 C7 C8 114.03(15) . . ? F3 C7 C8 109.20(14) . . ? F4 C7 C6 113.46(14) . . ? F3 C7 C6 109.38(14) . . ? C8 C7 C6 102.94(14) . . ? F5 C8 F6 105.96(13) . . ? F5 C8 C9 114.06(14) . . ? F6 C8 C9 111.47(14) . . ? F5 C8 C7 111.32(15) . . ? F6 C8 C7 109.18(14) . . ? C9 C8 C7 104.86(14) . . ? C5 C9 C11 130.36(16) . . ? C5 C9 C8 110.23(15) . . ? C11 C9 C8 119.38(15) . . ? C11 C10 C44 131.14(16) . . ? C11 C10 S2 110.06(13) . . ? C44 C10 S2 118.72(13) . . ? C10 C11 C12 113.26(16) . . ? C10 C11 C9 124.69(16) . . ? C12 C11 C9 121.94(15) . . ? C13 C12 C11 113.38(16) . . ? C13 C12 H12 123.3 . . ? C11 C12 H12 123.3 . . ? C12 C13 C28 126.56(16) . . ? C12 C13 S2 110.14(13) . . ? C28 C13 S2 123.05(13) . . ? C15 C14 C27 119.93(16) . . ? C15 C14 C4 119.25(16) . . ? C27 C14 C4 120.45(15) . . ? C14 C15 C16 121.62(17) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 120.10(16) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 121.07(17) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C19 C18 C17 121.75(16) . . ? C19 C18 C27 119.15(16) . . ? C17 C18 C27 119.09(16) . . ? C18 C19 C20 122.02(16) . . ? C18 C19 H19 119.0 . . ? C20 C19 H19 119.0 . . ? C19 C20 C21 122.84(17) . . ? C19 C20 C25 118.76(16) . . ? C21 C20 C25 118.39(16) . . ? C22 C21 C20 121.23(17) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 120.19(18) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 C22 120.45(17) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 121.29(17) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 119.4 . . ? C26 C25 C24 122.44(16) . . ? C26 C25 C20 119.16(16) . . ? C24 C25 C20 118.40(16) . . ? C27 C26 C25 122.15(16) . . ? C27 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? C26 C27 C18 118.64(16) . . ? C26 C27 C14 123.38(16) . . ? C18 C27 C14 117.98(15) . . ? C29 C28 C41 119.56(16) . . ? C29 C28 C13 118.05(16) . . ? C41 C28 C13 122.39(16) . . ? C28 C29 C30 122.05(17) . . ? C28 C29 H29 119.0 . . ? C30 C29 H29 119.0 . . ? C31 C30 C29 120.22(17) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C30 C31 C32 120.66(17) . . ? C30 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C33 C32 C31 121.35(16) . . ? C33 C32 C41 119.13(16) . . ? C31 C32 C41 119.51(16) . . ? C34 C33 C32 122.15(16) . . ? C34 C33 H33 118.9 . . ? C32 C33 H33 118.9 . . ? C33 C34 C35 122.50(16) . . ? C33 C34 C39 118.85(16) . . ? C35 C34 C39 118.62(16) . . ? C36 C35 C34 120.94(17) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C35 C36 C37 120.47(18) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C38 C37 C36 120.80(18) . . ? C38 C37 H37 119.6 . . ? C36 C37 H37 119.6 . . ? C37 C38 C39 120.70(18) . . ? C37 C38 H38 119.7 . . ? C39 C38 H38 119.7 . . ? C40 C39 C38 122.30(16) . . ? C40 C39 C34 119.31(16) . . ? C38 C39 C34 118.38(16) . . ? C41 C40 C39 122.14(16) . . ? C41 C40 H40 118.9 . . ? C39 C40 H40 118.9 . . ? C40 C41 C32 118.37(15) . . ? C40 C41 C28 123.64(16) . . ? C32 C41 C28 117.99(16) . . ? C1 C42 C43 114.12(15) . . ? C1 C42 H42A 108.7 . . ? C43 C42 H42A 108.7 . . ? C1 C42 H42B 108.7 . . ? C43 C42 H42B 108.7 . . ? H42A C42 H42B 107.6 . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C10 C44 C45 113.31(15) . . ? C10 C44 H44A 108.9 . . ? C45 C44 H44A 108.9 . . ? C10 C44 H44B 108.9 . . ? C45 C44 H44B 108.9 . . ? H44A C44 H44B 107.7 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C1 S1 C4 93.20(8) . . ? C10 S2 C13 93.15(8) . . ? 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 C42 C1 C2 C3 177.01(17) . . . . ? S1 C1 C2 C3 -0.67(19) . . . . ? C42 C1 C2 C5 -1.1(3) . . . . ? S1 C1 C2 C5 -178.75(13) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? C5 C2 C3 C4 178.54(16) . . . . ? C2 C3 C4 C14 176.88(17) . . . . ? C2 C3 C4 S1 -0.02(19) . . . . ? C1 C2 C5 C9 -52.1(3) . . . . ? C3 C2 C5 C9 130.0(2) . . . . ? C1 C2 C5 C6 121.80(19) . . . . ? C3 C2 C5 C6 -56.1(2) . . . . ? C9 C5 C6 F1 -135.51(16) . . . . ? C2 C5 C6 F1 49.5(2) . . . . ? C9 C5 C6 F2 105.01(17) . . . . ? C2 C5 C6 F2 -70.0(2) . . . . ? C9 C5 C6 C7 -13.5(2) . . . . ? C2 C5 C6 C7 171.50(15) . . . . ? F1 C6 C7 F4 -89.05(18) . . . . ? F2 C6 C7 F4 28.2(2) . . . . ? C5 C6 C7 F4 147.45(15) . . . . ? F1 C6 C7 F3 31.22(19) . . . . ? F2 C6 C7 F3 148.45(13) . . . . ? C5 C6 C7 F3 -92.28(16) . . . . ? F1 C6 C7 C8 147.23(14) . . . . ? F2 C6 C7 C8 -95.54(16) . . . . ? C5 C6 C7 C8 23.73(18) . . . . ? F4 C7 C8 F5 87.31(18) . . . . ? F3 C7 C8 F5 -33.21(19) . . . . ? C6 C7 C8 F5 -149.35(14) . . . . ? F4 C7 C8 F6 -29.3(2) . . . . ? F3 C7 C8 F6 -149.84(13) . . . . ? C6 C7 C8 F6 94.01(16) . . . . ? F4 C7 C8 C9 -148.88(15) . . . . ? F3 C7 C8 C9 90.60(16) . . . . ? C6 C7 C8 C9 -25.54(17) . . . . ? C2 C5 C9 C11 -6.7(3) . . . . ? C6 C5 C9 C11 178.93(17) . . . . ? C2 C5 C9 C8 171.21(16) . . . . ? C6 C5 C9 C8 -3.2(2) . . . . ? F5 C8 C9 C5 140.71(16) . . . . ? F6 C8 C9 C5 -99.34(17) . . . . ? C7 C8 C9 C5 18.67(19) . . . . ? F5 C8 C9 C11 -41.1(2) . . . . ? F6 C8 C9 C11 78.81(19) . . . . ? C7 C8 C9 C11 -163.18(15) . . . . ? C44 C10 C11 C12 175.99(18) . . . . ? S2 C10 C11 C12 -0.73(19) . . . . ? C44 C10 C11 C9 -0.3(3) . . . . ? S2 C10 C11 C9 -177.05(14) . . . . ? C5 C9 C11 C10 -50.8(3) . . . . ? C8 C9 C11 C10 131.53(18) . . . . ? C5 C9 C11 C12 133.2(2) . . . . ? C8 C9 C11 C12 -44.5(2) . . . . ? C10 C11 C12 C13 0.7(2) . . . . ? C9 C11 C12 C13 177.18(16) . . . . ? C11 C12 C13 C28 173.97(16) . . . . ? C11 C12 C13 S2 -0.4(2) . . . . ? C3 C4 C14 C15 125.9(2) . . . . ? S1 C4 C14 C15 -57.4(2) . . . . ? C3 C4 C14 C27 -61.1(3) . . . . ? S1 C4 C14 C27 115.62(16) . . . . ? C27 C14 C15 C16 -3.1(3) . . . . ? C4 C14 C15 C16 169.93(16) . . . . ? C14 C15 C16 C17 -0.9(3) . . . . ? C15 C16 C17 C18 2.7(3) . . . . ? C16 C17 C18 C19 179.52(16) . . . . ? C16 C17 C18 C27 -0.6(3) . . . . ? C17 C18 C19 C20 -178.12(16) . . . . ? C27 C18 C19 C20 2.0(3) . . . . ? C18 C19 C20 C21 -179.72(16) . . . . ? C18 C19 C20 C25 1.2(3) . . . . ? C19 C20 C21 C22 -178.92(16) . . . . ? C25 C20 C21 C22 0.2(3) . . . . ? C20 C21 C22 C23 1.4(3) . . . . ? C21 C22 C23 C24 -1.2(3) . . . . ? C22 C23 C24 C25 -0.7(3) . . . . ? C23 C24 C25 C26 -177.68(17) . . . . ? C23 C24 C25 C20 2.3(3) . . . . ? C19 C20 C25 C26 -2.9(2) . . . . ? C21 C20 C25 C26 177.95(16) . . . . ? C19 C20 C25 C24 177.15(16) . . . . ? C21 C20 C25 C24 -2.0(2) . . . . ? C24 C25 C26 C27 -178.59(16) . . . . ? C20 C25 C26 C27 1.5(3) . . . . ? C25 C26 C27 C18 1.7(3) . . . . ? C25 C26 C27 C14 -178.33(16) . . . . ? C19 C18 C27 C26 -3.4(2) . . . . ? C17 C18 C27 C26 176.70(15) . . . . ? C19 C18 C27 C14 176.62(15) . . . . ? C17 C18 C27 C14 -3.3(2) . . . . ? C15 C14 C27 C26 -174.89(16) . . . . ? C4 C14 C27 C26 12.2(3) . . . . ? C15 C14 C27 C18 5.1(2) . . . . ? C4 C14 C27 C18 -167.86(15) . . . . ? C12 C13 C28 C29 -48.0(3) . . . . ? S2 C13 C28 C29 125.70(16) . . . . ? C12 C13 C28 C41 131.0(2) . . . . ? S2 C13 C28 C41 -55.3(2) . . . . ? C41 C28 C29 C30 -0.3(3) . . . . ? C13 C28 C29 C30 178.67(16) . . . . ? C28 C29 C30 C31 0.1(3) . . . . ? C29 C30 C31 C32 -0.3(3) . . . . ? C30 C31 C32 C33 -178.64(17) . . . . ? C30 C31 C32 C41 0.6(3) . . . . ? C31 C32 C33 C34 -179.56(16) . . . . ? C41 C32 C33 C34 1.1(3) . . . . ? C32 C33 C34 C35 -177.66(16) . . . . ? C32 C33 C34 C39 0.6(3) . . . . ? C33 C34 C35 C36 178.96(16) . . . . ? C39 C34 C35 C36 0.7(3) . . . . ? C34 C35 C36 C37 1.8(3) . . . . ? C35 C36 C37 C38 -2.2(3) . . . . ? C36 C37 C38 C39 0.0(3) . . . . ? C37 C38 C39 C40 -176.28(17) . . . . ? C37 C38 C39 C34 2.4(3) . . . . ? C33 C34 C39 C40 -2.3(2) . . . . ? C35 C34 C39 C40 175.98(16) . . . . ? C33 C34 C39 C38 178.93(15) . . . . ? C35 C34 C39 C38 -2.8(2) . . . . ? C38 C39 C40 C41 -178.93(16) . . . . ? C34 C39 C40 C41 2.4(3) . . . . ? C39 C40 C41 C32 -0.6(2) . . . . ? C39 C40 C41 C28 179.75(16) . . . . ? C33 C32 C41 C40 -1.1(2) . . . . ? C31 C32 C41 C40 179.57(15) . . . . ? C33 C32 C41 C28 178.50(15) . . . . ? C31 C32 C41 C28 -0.8(2) . . . . ? C29 C28 C41 C40 -179.75(16) . . . . ? C13 C28 C41 C40 1.3(3) . . . . ? C29 C28 C41 C32 0.6(2) . . . . ? C13 C28 C41 C32 -178.29(15) . . . . ? C2 C1 C42 C43 122.2(2) . . . . ? S1 C1 C42 C43 -60.3(2) . . . . ? C11 C10 C44 C45 126.6(2) . . . . ? S2 C10 C44 C45 -56.90(19) . . . . ? C2 C1 S1 C4 0.57(14) . . . . ? C42 C1 S1 C4 -177.40(14) . . . . ? C3 C4 S1 C1 -0.31(14) . . . . ? C14 C4 S1 C1 -177.75(13) . . . . ? C11 C10 S2 C13 0.43(14) . . . . ? C44 C10 S2 C13 -176.75(14) . . . . ? C12 C13 S2 C10 -0.02(14) . . . . ? C28 C13 S2 C10 -174.61(15) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.04 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.374 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.062 # Attachment '- c003355c_cif3a.cif' data_3a _database_code_depnum_ccdc_archive 'CCDC 764007' #TrackingRef '- c003355c_cif3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-Bis(2-(2-anthryl)-5-ethylthien-3-yl)perfluorocyclopentene ; _chemical_name_common 1,2-Bis(2-(2-anthryl)-5-ethylthien-3-yl)perfluorocyclopentene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H30 F6 S2' _chemical_formula_weight 748.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8101(10) _cell_length_b 11.5143(11) _cell_length_c 16.5482(16) _cell_angle_alpha 72.389(2) _cell_angle_beta 86.286(2) _cell_angle_gamma 81.997(2) _cell_volume 1763.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4959 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16074 _diffrn_reflns_av_R_equivalents 0.1364 _diffrn_reflns_av_sigmaI/netI 0.1142 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7470 _reflns_number_gt 6213 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+1.8424P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7470 _refine_ls_number_parameters 564 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.2004 _refine_ls_wR_factor_gt 0.1889 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1767(3) 0.1522(3) 0.6362(3) 0.0426(9) Uani 1 1 d . . . C2 C 0.2897(3) 0.1578(3) 0.67984(19) 0.0279(6) Uani 1 1 d . B . C3 C 0.2562(3) 0.1628(3) 0.7641(2) 0.0298(6) Uani 1 1 d . . . H3 H 0.3223 0.1658 0.8026 0.036 Uiso 1 1 calc R B . C4 C 0.1176(3) 0.1627(3) 0.7833(2) 0.0343(7) Uani 1 1 d . B . C5 C 0.4302(3) 0.1485(3) 0.64477(18) 0.0262(6) Uani 1 1 d . . . C6 C 0.5406(4) 0.0575(3) 0.6949(2) 0.0400(8) Uani 1 1 d . A . C8 C 0.6245(3) 0.1540(3) 0.5542(2) 0.0313(7) Uani 1 1 d . . . C9 C 0.4798(3) 0.2073(3) 0.56754(18) 0.0267(6) Uani 1 1 d . A . C10 C 0.3434(3) 0.4159(3) 0.51077(18) 0.0285(6) Uani 1 1 d . A . C11 C 0.4115(3) 0.3092(3) 0.49979(18) 0.0301(6) Uani 1 1 d . . . C12 C 0.4120(3) 0.3069(3) 0.41369(18) 0.0340(7) Uani 1 1 d . A . H12 H 0.4574 0.2407 0.3952 0.041 Uiso 1 1 calc R . . C13 C 0.3411(3) 0.4087(3) 0.36107(19) 0.0330(7) Uani 1 1 d . . . C14 C 0.0435(3) 0.1600(3) 0.8638(2) 0.0370(8) Uani 1 1 d . . . C15 C 0.0974(3) 0.1923(3) 0.9266(2) 0.0358(7) Uani 1 1 d . B . H15 H 0.1857 0.2196 0.9179 0.043 Uiso 1 1 calc R . . C16 C 0.0244(3) 0.1861(3) 1.0052(2) 0.0392(8) Uani 1 1 d . . . C17 C 0.0786(4) 0.2183(3) 1.0703(2) 0.0429(9) Uani 1 1 d . B . H17 H 0.1679 0.2437 1.0630 0.051 Uiso 1 1 calc R . . C18 C 0.0042(4) 0.2139(3) 1.1462(2) 0.0472(10) Uani 1 1 d . . . C19 C 0.0556(4) 0.2490(3) 1.2121(2) 0.0507(10) Uani 1 1 d . B . H19 H 0.1455 0.2729 1.2063 0.061 Uiso 1 1 calc R . . C20 C -0.0214(5) 0.2492(4) 1.2839(3) 0.0646(13) Uani 1 1 d . . . H20 H 0.0140 0.2748 1.3270 0.078 Uiso 1 1 calc R B . C21 C -0.1546(5) 0.2108(4) 1.2939(3) 0.0737(17) Uani 1 1 d . B . H21 H -0.2074 0.2107 1.3442 0.088 Uiso 1 1 calc R . . C22 C -0.2078(5) 0.1745(4) 1.2336(3) 0.0666(15) Uani 1 1 d . . . H22 H -0.2965 0.1480 1.2424 0.080 Uiso 1 1 calc R B . C23 C -0.1318(4) 0.1755(3) 1.1565(3) 0.0527(11) Uani 1 1 d . B . C24 C -0.1837(4) 0.1415(3) 1.0923(3) 0.0519(11) Uani 1 1 d . . . H24 H -0.2718 0.1137 1.1004 0.062 Uiso 1 1 calc R B . C25 C -0.1113(4) 0.1466(3) 1.0162(3) 0.0462(9) Uani 1 1 d . B . C26 C -0.1636(4) 0.1134(3) 0.9498(3) 0.0486(10) Uani 1 1 d . . . H26 H -0.2515 0.0855 0.9569 0.058 Uiso 1 1 calc R B . C27 C -0.0917(4) 0.1203(3) 0.8765(3) 0.0466(9) Uani 1 1 d . B . H27 H -0.1306 0.0988 0.8327 0.056 Uiso 1 1 calc R . . C28 C 0.3111(4) 0.4369(3) 0.27071(18) 0.0335(7) Uani 1 1 d . A . C29 C 0.3936(3) 0.3805(3) 0.21975(18) 0.0326(7) Uani 1 1 d . . . H29 H 0.4718 0.3246 0.2430 0.039 Uiso 1 1 calc R A . C30 C 0.3641(3) 0.4042(3) 0.13269(18) 0.0316(7) Uani 1 1 d . A . C31 C 0.4470(3) 0.3487(3) 0.07972(18) 0.0335(7) Uani 1 1 d . . . H31 H 0.5258 0.2930 0.1022 0.040 Uiso 1 1 calc R A . C32 C 0.4169(3) 0.3730(3) -0.00574(18) 0.0316(7) Uani 1 1 d . A . C33 C 0.5028(4) 0.3175(3) -0.0607(2) 0.0379(7) Uani 1 1 d . . . H33 H 0.5818 0.2616 -0.0389 0.045 Uiso 1 1 calc R A . C34 C 0.4723(4) 0.3444(3) -0.1437(2) 0.0389(8) Uani 1 1 d . A . H34 H 0.5295 0.3062 -0.1794 0.047 Uiso 1 1 calc R . . C35 C 0.3563(4) 0.4284(3) -0.17755(19) 0.0380(8) Uani 1 1 d . . . H35 H 0.3373 0.4469 -0.2360 0.046 Uiso 1 1 calc R A . C36 C 0.2717(4) 0.4832(3) -0.12810(18) 0.0332(7) Uani 1 1 d . A . H36 H 0.1938 0.5391 -0.1520 0.040 Uiso 1 1 calc R . . C37 C 0.2992(3) 0.4573(3) -0.03985(18) 0.0314(7) Uani 1 1 d . . . C38 C 0.2162(3) 0.5136(3) 0.01288(18) 0.0322(7) Uani 1 1 d . A . H38 H 0.1377 0.5696 -0.0098 0.039 Uiso 1 1 calc R . . C39 C 0.2458(3) 0.4897(3) 0.09784(18) 0.0312(7) Uani 1 1 d . . . C40 C 0.1631(3) 0.5467(3) 0.15277(19) 0.0333(7) Uani 1 1 d . A . H40 H 0.0844 0.6031 0.1310 0.040 Uiso 1 1 calc R . . C41 C 0.1942(4) 0.5222(3) 0.23516(19) 0.0345(7) Uani 1 1 d . . . H41 H 0.1376 0.5623 0.2700 0.041 Uiso 1 1 calc R A . C44 C 0.3216(3) 0.4572(3) 0.58889(18) 0.0314(7) Uani 1 1 d . . . H44A H 0.3682 0.5312 0.5803 0.038 Uiso 1 1 calc R A . H44B H 0.3651 0.3918 0.6373 0.038 Uiso 1 1 calc R . . C45 C 0.1694(4) 0.4871(3) 0.6113(2) 0.0398(8) Uani 1 1 d . A . H45A H 0.1251 0.5510 0.5634 0.060 Uiso 1 1 calc R . . H45B H 0.1620 0.5166 0.6613 0.060 Uiso 1 1 calc R . . H45C H 0.1238 0.4130 0.6235 0.060 Uiso 1 1 calc R . . C7A C 0.6565(11) 0.0393(8) 0.6396(7) 0.0227(19) Uani 0.483(4) 1 d P A 1 C42A C 0.1742(11) 0.1554(10) 0.5364(5) 0.033(2) Uani 0.493(9) 1 d P B 3 H42A H 0.2532 0.1950 0.5052 0.039 Uiso 0.493(9) 1 calc PR B 3 H42B H 0.1842 0.0702 0.5330 0.039 Uiso 0.493(9) 1 calc PR B 3 C43A C 0.0682(7) 0.2109(7) 0.5033(4) 0.039(2) Uani 0.493(9) 1 d P B 3 H43A H -0.0089 0.1933 0.5439 0.058 Uiso 0.493(9) 1 calc PR B 3 H43B H 0.0531 0.1851 0.4536 0.058 Uiso 0.493(9) 1 calc PR B 3 H43C H 0.0748 0.2993 0.4855 0.058 Uiso 0.493(9) 1 calc PR B 3 C7B C 0.6731(10) 0.0829(8) 0.6371(7) 0.031(2) Uani 0.517(4) 1 d P A 2 C42B C 0.1599(9) 0.1157(9) 0.5659(6) 0.0311(18) Uani 0.507(9) 1 d P B 4 H42C H 0.2006 0.1799 0.5202 0.037 Uiso 0.507(9) 1 calc PR B 4 H42D H 0.2291 0.0420 0.5749 0.037 Uiso 0.507(9) 1 calc PR B 4 C43B C 0.0609(6) 0.0869(6) 0.5236(4) 0.0310(16) Uani 0.507(9) 1 d P B 4 H43D H 0.0469 0.0007 0.5498 0.046 Uiso 0.507(9) 1 calc PR B 4 H43E H 0.0901 0.0994 0.4642 0.046 Uiso 0.507(9) 1 calc PR B 4 H43F H -0.0255 0.1397 0.5265 0.046 Uiso 0.507(9) 1 calc PR B 4 F1A F 0.625(2) 0.0908(13) 0.4973(11) 0.049(3) Uani 0.483(4) 1 d P A 1 F2A F 0.7093(7) 0.2427(6) 0.5109(3) 0.0329(12) Uani 0.483(4) 1 d P A 1 F3A F 0.7858(6) 0.0263(5) 0.6644(3) 0.0399(13) Uani 0.483(4) 1 d P A 1 F4A F 0.5431(4) 0.0409(4) 0.7704(2) 0.0362(10) Uani 0.483(4) 1 d P A 1 F5A F 0.5074(4) -0.0435(4) 0.7543(3) 0.0399(11) Uani 0.483(4) 1 d P A 1 F6A F 0.6398(4) -0.0636(3) 0.6199(2) 0.0378(11) Uani 0.483(4) 1 d P A 1 F1B F 0.648(2) 0.1065(15) 0.4905(9) 0.063(5) Uani 0.517(4) 1 d P A 2 F2B F 0.7139(7) 0.2338(5) 0.5515(4) 0.0496(15) Uani 0.517(4) 1 d P A 2 F3B F 0.7289(4) 0.1547(4) 0.6743(2) 0.0487(12) Uani 0.517(4) 1 d P A 2 F4B F 0.5973(4) 0.1166(4) 0.7544(2) 0.0432(11) Uani 0.517(4) 1 d P A 2 F5B F 0.5107(4) -0.0616(3) 0.6851(3) 0.0440(11) Uani 0.517(4) 1 d P A 2 F6B F 0.7613(6) -0.0159(5) 0.6408(4) 0.0563(15) Uani 0.517(4) 1 d P A 2 S1 S 0.03032(9) 0.15479(9) 0.69854(7) 0.0467(3) Uani 1 1 d . B . S2 S 0.27730(9) 0.51173(7) 0.41638(4) 0.0312(2) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0289(17) 0.0448(19) 0.065(2) -0.0359(18) -0.0065(16) 0.0039(15) C2 0.0265(15) 0.0229(13) 0.0360(16) -0.0128(12) -0.0031(12) 0.0019(11) C3 0.0309(16) 0.0208(13) 0.0344(16) -0.0048(11) 0.0018(13) -0.0014(12) C4 0.0298(16) 0.0243(14) 0.0474(19) -0.0111(13) 0.0046(14) 0.0000(12) C5 0.0284(15) 0.0231(13) 0.0301(15) -0.0131(11) -0.0022(12) -0.0004(11) C6 0.0356(18) 0.0328(16) 0.0394(19) 0.0042(14) 0.0042(15) 0.0007(14) C8 0.0348(16) 0.0268(14) 0.0320(16) -0.0109(12) 0.0039(13) 0.0000(13) C9 0.0320(15) 0.0277(14) 0.0231(14) -0.0123(11) -0.0027(12) -0.0013(12) C10 0.0339(16) 0.0311(14) 0.0202(13) -0.0087(11) -0.0017(12) -0.0001(13) C11 0.0347(16) 0.0363(16) 0.0204(14) -0.0124(12) -0.0002(12) 0.0005(13) C12 0.0387(17) 0.0419(17) 0.0224(15) -0.0169(13) -0.0035(13) 0.0095(14) C13 0.0377(17) 0.0377(16) 0.0244(15) -0.0156(13) -0.0035(13) 0.0079(14) C14 0.0294(16) 0.0209(14) 0.052(2) -0.0017(13) 0.0091(15) 0.0009(12) C15 0.0307(16) 0.0252(14) 0.0409(18) 0.0031(13) 0.0073(14) -0.0012(13) C16 0.0343(17) 0.0257(15) 0.0429(19) 0.0064(13) 0.0117(15) 0.0020(13) C17 0.0407(19) 0.0322(16) 0.0388(18) 0.0064(14) 0.0177(15) 0.0056(15) C18 0.050(2) 0.0306(16) 0.0395(19) 0.0115(14) 0.0172(17) 0.0109(15) C19 0.055(2) 0.0399(19) 0.0360(19) 0.0087(15) 0.0146(17) 0.0130(17) C20 0.083(3) 0.044(2) 0.043(2) 0.0070(17) 0.031(2) 0.013(2) C21 0.082(3) 0.048(2) 0.050(3) 0.023(2) 0.043(3) 0.026(2) C22 0.060(3) 0.049(2) 0.052(3) 0.025(2) 0.034(2) 0.017(2) C23 0.048(2) 0.0313(17) 0.049(2) 0.0188(16) 0.0261(18) 0.0112(16) C24 0.0364(19) 0.0324(17) 0.061(3) 0.0166(17) 0.0211(18) 0.0049(15) C25 0.0332(18) 0.0257(15) 0.060(2) 0.0087(15) 0.0175(17) 0.0049(14) C26 0.0305(17) 0.0252(16) 0.078(3) -0.0001(17) 0.0086(18) -0.0003(14) C27 0.0323(18) 0.0281(16) 0.072(3) -0.0063(16) 0.0100(17) -0.0033(14) C28 0.0426(18) 0.0375(16) 0.0193(14) -0.0108(12) -0.0031(13) 0.0055(14) C29 0.0377(17) 0.0357(16) 0.0209(14) -0.0082(12) -0.0062(13) 0.0089(13) C30 0.0410(18) 0.0312(15) 0.0192(14) -0.0057(11) -0.0030(13) 0.0045(13) C31 0.0390(17) 0.0350(16) 0.0223(14) -0.0076(12) -0.0015(13) 0.0075(14) C32 0.0398(17) 0.0328(15) 0.0210(14) -0.0093(12) 0.0010(13) 0.0019(13) C33 0.0449(19) 0.0407(17) 0.0260(16) -0.0119(13) 0.0017(14) 0.0048(15) C34 0.054(2) 0.0397(17) 0.0245(15) -0.0141(13) 0.0038(15) -0.0028(16) C35 0.055(2) 0.0412(17) 0.0178(14) -0.0084(13) -0.0022(14) -0.0053(16) C36 0.0441(18) 0.0317(15) 0.0217(14) -0.0055(12) -0.0031(13) -0.0020(14) C37 0.0431(18) 0.0293(14) 0.0200(14) -0.0060(11) -0.0014(13) -0.0011(13) C38 0.0399(17) 0.0305(15) 0.0231(14) -0.0061(12) -0.0065(13) 0.0054(13) C39 0.0384(17) 0.0317(15) 0.0215(14) -0.0075(12) -0.0018(12) 0.0019(13) C40 0.0400(18) 0.0324(15) 0.0244(15) -0.0095(12) -0.0034(13) 0.0101(13) C41 0.0456(19) 0.0350(16) 0.0205(14) -0.0114(12) 0.0001(13) 0.0095(14) C44 0.0433(18) 0.0294(14) 0.0218(14) -0.0112(12) -0.0050(13) 0.0044(13) C45 0.048(2) 0.0446(18) 0.0277(16) -0.0181(14) 0.0014(15) 0.0082(16) C7A 0.025(4) 0.013(4) 0.027(4) 0.000(4) -0.006(3) -0.006(4) C42A 0.049(5) 0.047(5) 0.012(4) -0.014(3) 0.011(4) -0.034(4) C43A 0.042(4) 0.050(4) 0.019(3) -0.002(3) -0.013(3) -0.005(3) C7B 0.022(4) 0.028(5) 0.034(4) 0.003(4) 0.003(3) -0.002(4) C42B 0.031(4) 0.036(5) 0.031(5) -0.019(4) 0.004(4) 0.002(4) C43B 0.027(3) 0.040(3) 0.028(3) -0.010(3) 0.002(2) -0.009(3) F1A 0.043(5) 0.051(4) 0.062(7) -0.044(5) -0.006(4) 0.024(4) F2A 0.033(2) 0.035(2) 0.024(2) -0.001(2) 0.009(2) -0.0031(18) F3A 0.030(2) 0.049(3) 0.040(3) -0.012(2) -0.0056(19) -0.002(2) F4A 0.031(2) 0.042(2) 0.025(2) 0.0037(17) -0.0007(16) -0.0008(19) F5A 0.038(2) 0.038(2) 0.032(2) 0.0035(17) 0.0013(17) 0.0025(18) F6A 0.053(3) 0.0287(19) 0.036(2) -0.0166(16) -0.0008(18) -0.0020(18) F1B 0.058(7) 0.104(9) 0.023(3) -0.027(4) -0.001(4) 0.024(5) F2B 0.040(3) 0.031(2) 0.070(4) -0.005(3) 0.009(4) -0.0038(19) F3B 0.036(2) 0.073(3) 0.035(2) -0.0048(19) -0.0119(17) -0.019(2) F4B 0.045(2) 0.057(3) 0.034(2) -0.028(2) -0.0154(18) 0.013(2) F5B 0.044(2) 0.0229(17) 0.058(3) -0.0045(17) 0.0103(19) -0.0011(16) F6B 0.042(3) 0.052(3) 0.046(3) 0.014(2) 0.008(2) 0.021(3) S1 0.0264(4) 0.0481(5) 0.0765(7) -0.0359(5) -0.0011(4) -0.0026(4) S2 0.0433(5) 0.0299(4) 0.0190(3) -0.0092(3) -0.0018(3) 0.0044(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C42B 1.377(9) . ? C1 C2 1.381(4) . ? C1 C42A 1.642(9) . ? C1 S1 1.715(4) . ? C2 C3 1.428(4) . ? C2 C5 1.463(4) . ? C3 C4 1.376(4) . ? C3 H3 0.9500 . ? C4 C14 1.469(5) . ? C4 S1 1.722(4) . ? C5 C9 1.348(4) . ? C5 C6 1.495(4) . ? C6 F4A 1.207(5) . ? C6 F5A 1.340(5) . ? C6 C7A 1.445(12) . ? C6 F5B 1.500(5) . ? C6 F4B 1.523(5) . ? C6 C7B 1.569(10) . ? C8 F1B 1.321(13) . ? C8 F2B 1.346(7) . ? C8 F1A 1.351(13) . ? C8 F2A 1.402(7) . ? C8 C7B 1.441(11) . ? C8 C9 1.497(4) . ? C8 C7A 1.629(10) . ? C9 C11 1.471(4) . ? C10 C11 1.371(4) . ? C10 C44 1.501(4) . ? C10 S2 1.722(3) . ? C11 C12 1.433(4) . ? C12 C13 1.360(4) . ? C12 H12 0.9500 . ? C13 C28 1.471(4) . ? C13 S2 1.736(3) . ? C14 C15 1.363(5) . ? C14 C27 1.445(5) . ? C15 C16 1.432(5) . ? C15 H15 0.9500 . ? C16 C17 1.396(5) . ? C16 C25 1.449(5) . ? C17 C18 1.402(5) . ? C17 H17 0.9500 . ? C18 C19 1.415(6) . ? C18 C23 1.447(6) . ? C19 C20 1.368(5) . ? C19 H19 0.9500 . ? C20 C21 1.421(7) . ? C20 H20 0.9500 . ? C21 C22 1.351(7) . ? C21 H21 0.9500 . ? C22 C23 1.433(5) . ? C22 H22 0.9500 . ? C23 C24 1.386(6) . ? C24 C25 1.395(5) . ? C24 H24 0.9500 . ? C25 C26 1.413(6) . ? C26 C27 1.349(5) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.372(4) . ? C28 C41 1.432(4) . ? C29 C30 1.424(4) . ? C29 H29 0.9500 . ? C30 C31 1.393(4) . ? C30 C39 1.440(4) . ? C31 C32 1.399(4) . ? C31 H31 0.9500 . ? C32 C37 1.426(4) . ? C32 C33 1.431(4) . ? C33 C34 1.358(4) . ? C33 H33 0.9500 . ? C34 C35 1.412(5) . ? C34 H34 0.9500 . ? C35 C36 1.355(5) . ? C35 H35 0.9500 . ? C36 C37 1.435(4) . ? C36 H36 0.9500 . ? C37 C38 1.396(4) . ? C38 C39 1.390(4) . ? C38 H38 0.9500 . ? C39 C40 1.425(4) . ? C40 C41 1.352(4) . ? C40 H40 0.9500 . ? C41 H41 0.9500 . ? C44 C45 1.532(5) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C7A F3A 1.333(12) . ? C7A F6A 1.354(9) . ? C42A C43A 1.211(13) . ? C42A H42A 0.9900 . ? C42A H42B 0.9900 . ? C43A H43A 0.9800 . ? C43A H43B 0.9800 . ? C43A H43C 0.9800 . ? C7B F6B 1.318(11) . ? C7B F3B 1.355(11) . ? C42B C43B 1.364(11) . ? C42B H42C 0.9900 . ? C42B H42D 0.9900 . ? C43B H43D 0.9800 . ? C43B H43E 0.9800 . ? C43B H43F 0.9800 . ? 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 C42B C1 C2 134.0(5) . . ? C2 C1 C42A 126.7(4) . . ? C42B C1 S1 113.4(4) . . ? C2 C1 S1 110.2(3) . . ? C42A C1 S1 122.8(4) . . ? C1 C2 C3 113.2(3) . . ? C1 C2 C5 122.5(3) . . ? C3 C2 C5 124.1(3) . . ? C4 C3 C2 112.6(3) . . ? C4 C3 H3 123.7 . . ? C2 C3 H3 123.7 . . ? C3 C4 C14 129.4(3) . . ? C3 C4 S1 110.5(3) . . ? C14 C4 S1 119.9(2) . . ? C9 C5 C2 129.5(3) . . ? C9 C5 C6 110.3(3) . . ? C2 C5 C6 120.1(3) . . ? F4A C6 F5A 55.1(3) . . ? F4A C6 C7A 126.7(5) . . ? F5A C6 C7A 116.0(5) . . ? F4A C6 C5 119.0(3) . . ? F5A C6 C5 120.0(3) . . ? C7A C6 C5 109.7(5) . . ? F4A C6 F5B 105.3(4) . . ? F5A C6 F5B 50.6(3) . . ? C7A C6 F5B 82.3(4) . . ? C5 C6 F5B 102.9(3) . . ? F5A C6 F4B 97.2(4) . . ? C7A C6 F4B 104.0(5) . . ? C5 C6 F4B 107.5(3) . . ? F5B C6 F4B 144.4(3) . . ? F4A C6 C7B 121.3(5) . . ? F5A C6 C7B 131.7(5) . . ? C5 C6 C7B 103.3(4) . . ? F5B C6 C7B 102.3(4) . . ? F4B C6 C7B 88.5(5) . . ? F1B C8 F2B 111.1(10) . . ? F2B C8 F1A 124.1(10) . . ? F1B C8 F2A 87.5(10) . . ? F1A C8 F2A 100.2(10) . . ? F1B C8 C7B 119.3(8) . . ? F2B C8 C7B 89.0(5) . . ? F1A C8 C7B 115.6(8) . . ? F2A C8 C7B 113.2(5) . . ? F1B C8 C9 117.0(8) . . ? F2B C8 C9 111.1(4) . . ? F1A C8 C9 108.8(9) . . ? F2A C8 C9 113.3(4) . . ? C7B C8 C9 105.9(5) . . ? F1B C8 C7A 105.5(8) . . ? F2B C8 C7A 106.8(5) . . ? F1A C8 C7A 99.3(8) . . ? F2A C8 C7A 128.6(5) . . ? C9 C8 C7A 104.4(5) . . ? C5 C9 C11 129.2(3) . . ? C5 C9 C8 110.9(3) . . ? C11 C9 C8 119.9(3) . . ? C11 C10 C44 130.3(3) . . ? C11 C10 S2 110.6(2) . . ? C44 C10 S2 119.1(2) . . ? C10 C11 C12 112.8(3) . . ? C10 C11 C9 124.8(3) . . ? C12 C11 C9 122.5(3) . . ? C13 C12 C11 113.4(3) . . ? C13 C12 H12 123.3 . . ? C11 C12 H12 123.3 . . ? C12 C13 C28 129.6(3) . . ? C12 C13 S2 110.3(2) . . ? C28 C13 S2 120.1(2) . . ? C15 C14 C27 119.1(3) . . ? C15 C14 C4 122.8(3) . . ? C27 C14 C4 118.1(3) . . ? C14 C15 C16 121.7(3) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C17 C16 C15 122.4(3) . . ? C17 C16 C25 119.6(3) . . ? C15 C16 C25 118.0(4) . . ? C16 C17 C18 121.4(4) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C17 C18 C19 122.4(4) . . ? C17 C18 C23 118.8(4) . . ? C19 C18 C23 118.8(3) . . ? C20 C19 C18 121.3(4) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C21 119.7(5) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C22 C21 C20 121.4(4) . . ? C22 C21 H21 119.3 . . ? C20 C21 H21 119.3 . . ? C21 C22 C23 120.7(5) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 122.6(4) . . ? C24 C23 C18 119.3(3) . . ? C22 C23 C18 118.1(5) . . ? C23 C24 C25 122.4(4) . . ? C23 C24 H24 118.8 . . ? C25 C24 H24 118.8 . . ? C24 C25 C26 123.0(4) . . ? C24 C25 C16 118.4(4) . . ? C26 C25 C16 118.6(3) . . ? C27 C26 C25 121.7(3) . . ? C27 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C26 C27 C14 120.8(4) . . ? C26 C27 H27 119.6 . . ? C14 C27 H27 119.6 . . ? C29 C28 C41 119.2(3) . . ? C29 C28 C13 120.5(3) . . ? C41 C28 C13 120.3(3) . . ? C28 C29 C30 121.3(3) . . ? C28 C29 H29 119.4 . . ? C30 C29 H29 119.4 . . ? C31 C30 C29 122.2(3) . . ? C31 C30 C39 118.8(3) . . ? C29 C30 C39 119.0(3) . . ? C30 C31 C32 121.6(3) . . ? C30 C31 H31 119.2 . . ? C32 C31 H31 119.2 . . ? C31 C32 C37 119.4(3) . . ? C31 C32 C33 121.7(3) . . ? C37 C32 C33 118.8(3) . . ? C34 C33 C32 120.4(3) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C34 C35 120.7(3) . . ? C33 C34 H34 119.7 . . ? C35 C34 H34 119.7 . . ? C36 C35 C34 121.1(3) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C35 C36 C37 120.3(3) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C38 C37 C32 119.2(3) . . ? C38 C37 C36 122.1(3) . . ? C32 C37 C36 118.6(3) . . ? C39 C38 C37 121.5(3) . . ? C39 C38 H38 119.2 . . ? C37 C38 H38 119.2 . . ? C38 C39 C40 122.5(3) . . ? C38 C39 C30 119.4(3) . . ? C40 C39 C30 118.0(3) . . ? C41 C40 C39 121.5(3) . . ? C41 C40 H40 119.3 . . ? C39 C40 H40 119.3 . . ? C40 C41 C28 121.1(3) . . ? C40 C41 H41 119.5 . . ? C28 C41 H41 119.5 . . ? C10 C44 C45 113.3(3) . . ? C10 C44 H44A 108.9 . . ? C45 C44 H44A 108.9 . . ? C10 C44 H44B 108.9 . . ? C45 C44 H44B 108.9 . . ? H44A C44 H44B 107.7 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? F3A C7A F6A 107.2(8) . . ? F3A C7A C6 121.5(8) . . ? F6A C7A C6 105.2(6) . . ? F3A C7A C8 112.5(7) . . ? F6A C7A C8 106.7(7) . . ? C6 C7A C8 102.7(6) . . ? C43A C42A C1 111.6(8) . . ? C43A C42A H42A 109.3 . . ? C1 C42A H42A 109.3 . . ? C43A C42A H42B 109.3 . . ? C1 C42A H42B 109.3 . . ? H42A C42A H42B 108.0 . . ? F6B C7B F3B 108.8(8) . . ? F6B C7B C8 116.3(9) . . ? F3B C7B C8 110.4(6) . . ? F6B C7B C6 114.2(7) . . ? F3B C7B C6 100.0(7) . . ? C8 C7B C6 105.9(7) . . ? C43B C42B C1 141.2(8) . . ? C43B C42B H42C 101.7 . . ? C1 C42B H42C 101.7 . . ? C43B C42B H42D 101.7 . . ? C1 C42B H42D 101.7 . . ? H42C C42B H42D 104.7 . . ? C1 S1 C4 93.40(16) . . ? C10 S2 C13 92.84(15) . . ? 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 C42B C1 C2 C3 -160.3(7) . . . . ? C42A C1 C2 C3 175.3(5) . . . . ? S1 C1 C2 C3 0.6(4) . . . . ? C42B C1 C2 C5 14.7(8) . . . . ? C42A C1 C2 C5 -9.7(7) . . . . ? S1 C1 C2 C5 175.6(2) . . . . ? C1 C2 C3 C4 -0.8(4) . . . . ? C5 C2 C3 C4 -175.8(3) . . . . ? C2 C3 C4 C14 176.2(3) . . . . ? C2 C3 C4 S1 0.6(3) . . . . ? C1 C2 C5 C9 47.8(5) . . . . ? C3 C2 C5 C9 -137.7(3) . . . . ? C1 C2 C5 C6 -127.8(3) . . . . ? C3 C2 C5 C6 46.7(4) . . . . ? C9 C5 C6 F4A 144.4(4) . . . . ? C2 C5 C6 F4A -39.2(5) . . . . ? C9 C5 C6 F5A -151.4(4) . . . . ? C2 C5 C6 F5A 24.9(5) . . . . ? C9 C5 C6 C7A -13.4(5) . . . . ? C2 C5 C6 C7A 163.0(4) . . . . ? C9 C5 C6 F5B -99.7(3) . . . . ? C2 C5 C6 F5B 76.7(3) . . . . ? C9 C5 C6 F4B 99.1(3) . . . . ? C2 C5 C6 F4B -84.5(3) . . . . ? C9 C5 C6 C7B 6.5(5) . . . . ? C2 C5 C6 C7B -177.2(4) . . . . ? C2 C5 C9 C11 8.7(5) . . . . ? C6 C5 C9 C11 -175.4(3) . . . . ? C2 C5 C9 C8 -170.4(3) . . . . ? C6 C5 C9 C8 5.5(3) . . . . ? F1B C8 C9 C5 119.4(10) . . . . ? F2B C8 C9 C5 -111.5(4) . . . . ? F1A C8 C9 C5 108.5(9) . . . . ? F2A C8 C9 C5 -141.0(3) . . . . ? C7B C8 C9 C5 -16.3(5) . . . . ? C7A C8 C9 C5 3.3(4) . . . . ? F1B C8 C9 C11 -59.7(10) . . . . ? F2B C8 C9 C11 69.3(4) . . . . ? F1A C8 C9 C11 -70.6(9) . . . . ? F2A C8 C9 C11 39.9(4) . . . . ? C7B C8 C9 C11 164.5(4) . . . . ? C7A C8 C9 C11 -175.9(4) . . . . ? C44 C10 C11 C12 -178.3(3) . . . . ? S2 C10 C11 C12 1.2(4) . . . . ? C44 C10 C11 C9 0.7(5) . . . . ? S2 C10 C11 C9 -179.8(2) . . . . ? C5 C9 C11 C10 50.4(5) . . . . ? C8 C9 C11 C10 -130.6(3) . . . . ? C5 C9 C11 C12 -130.6(3) . . . . ? C8 C9 C11 C12 48.4(4) . . . . ? C10 C11 C12 C13 -2.1(4) . . . . ? C9 C11 C12 C13 178.9(3) . . . . ? C11 C12 C13 C28 -175.8(3) . . . . ? C11 C12 C13 S2 2.0(4) . . . . ? C3 C4 C14 C15 19.5(5) . . . . ? S1 C4 C14 C15 -165.3(2) . . . . ? C3 C4 C14 C27 -159.9(3) . . . . ? S1 C4 C14 C27 15.3(4) . . . . ? C27 C14 C15 C16 1.0(5) . . . . ? C4 C14 C15 C16 -178.5(3) . . . . ? C14 C15 C16 C17 179.6(3) . . . . ? C14 C15 C16 C25 -1.2(5) . . . . ? C15 C16 C17 C18 178.7(3) . . . . ? C25 C16 C17 C18 -0.4(5) . . . . ? C16 C17 C18 C19 -178.4(3) . . . . ? C16 C17 C18 C23 -0.2(5) . . . . ? C17 C18 C19 C20 177.0(3) . . . . ? C23 C18 C19 C20 -1.1(5) . . . . ? C18 C19 C20 C21 1.4(6) . . . . ? C19 C20 C21 C22 -0.4(6) . . . . ? C20 C21 C22 C23 -1.0(6) . . . . ? C21 C22 C23 C24 -178.6(4) . . . . ? C21 C22 C23 C18 1.3(5) . . . . ? C17 C18 C23 C24 1.4(5) . . . . ? C19 C18 C23 C24 179.7(3) . . . . ? C17 C18 C23 C22 -178.5(3) . . . . ? C19 C18 C23 C22 -0.2(5) . . . . ? C22 C23 C24 C25 177.8(3) . . . . ? C18 C23 C24 C25 -2.1(5) . . . . ? C23 C24 C25 C26 -179.3(3) . . . . ? C23 C24 C25 C16 1.5(5) . . . . ? C17 C16 C25 C24 -0.2(5) . . . . ? C15 C16 C25 C24 -179.4(3) . . . . ? C17 C16 C25 C26 -179.4(3) . . . . ? C15 C16 C25 C26 1.4(4) . . . . ? C24 C25 C26 C27 179.4(3) . . . . ? C16 C25 C26 C27 -1.5(5) . . . . ? C25 C26 C27 C14 1.2(5) . . . . ? C15 C14 C27 C26 -0.9(5) . . . . ? C4 C14 C27 C26 178.6(3) . . . . ? C12 C13 C28 C29 -23.9(6) . . . . ? S2 C13 C28 C29 158.5(3) . . . . ? C12 C13 C28 C41 155.2(4) . . . . ? S2 C13 C28 C41 -22.4(4) . . . . ? C41 C28 C29 C30 -0.7(5) . . . . ? C13 C28 C29 C30 178.4(3) . . . . ? C28 C29 C30 C31 179.5(3) . . . . ? C28 C29 C30 C39 0.4(5) . . . . ? C29 C30 C31 C32 -179.9(3) . . . . ? C39 C30 C31 C32 -0.8(5) . . . . ? C30 C31 C32 C37 0.5(5) . . . . ? C30 C31 C32 C33 179.1(3) . . . . ? C31 C32 C33 C34 -178.9(3) . . . . ? C37 C32 C33 C34 -0.3(5) . . . . ? C32 C33 C34 C35 0.8(5) . . . . ? C33 C34 C35 C36 -0.9(5) . . . . ? C34 C35 C36 C37 0.5(5) . . . . ? C31 C32 C37 C38 -0.1(5) . . . . ? C33 C32 C37 C38 -178.8(3) . . . . ? C31 C32 C37 C36 178.6(3) . . . . ? C33 C32 C37 C36 -0.1(5) . . . . ? C35 C36 C37 C38 178.6(3) . . . . ? C35 C36 C37 C32 0.0(5) . . . . ? C32 C37 C38 C39 0.1(5) . . . . ? C36 C37 C38 C39 -178.5(3) . . . . ? C37 C38 C39 C40 179.6(3) . . . . ? C37 C38 C39 C30 -0.4(5) . . . . ? C31 C30 C39 C38 0.7(5) . . . . ? C29 C30 C39 C38 179.9(3) . . . . ? C31 C30 C39 C40 -179.3(3) . . . . ? C29 C30 C39 C40 -0.1(5) . . . . ? C38 C39 C40 C41 -179.8(3) . . . . ? C30 C39 C40 C41 0.2(5) . . . . ? C39 C40 C41 C28 -0.6(5) . . . . ? C29 C28 C41 C40 0.9(5) . . . . ? C13 C28 C41 C40 -178.2(3) . . . . ? C11 C10 C44 C45 -122.3(4) . . . . ? S2 C10 C44 C45 58.3(3) . . . . ? F4A C6 C7A F3A -14.7(10) . . . . ? F5A C6 C7A F3A -79.2(8) . . . . ? C5 C6 C7A F3A 140.9(7) . . . . ? F5B C6 C7A F3A -118.1(8) . . . . ? F4B C6 C7A F3A 26.2(8) . . . . ? C7B C6 C7A F3A 66(2) . . . . ? F4A C6 C7A F6A 107.1(7) . . . . ? F5A C6 C7A F6A 42.6(8) . . . . ? C5 C6 C7A F6A -97.3(6) . . . . ? F5B C6 C7A F6A 3.7(6) . . . . ? F4B C6 C7A F6A 147.9(6) . . . . ? C7B C6 C7A F6A -172(3) . . . . ? F4A C6 C7A C8 -141.5(5) . . . . ? F5A C6 C7A C8 154.0(4) . . . . ? C5 C6 C7A C8 14.1(6) . . . . ? F5B C6 C7A C8 115.2(5) . . . . ? F4B C6 C7A C8 -100.6(5) . . . . ? C7B C6 C7A C8 -60(2) . . . . ? F1B C8 C7A F3A 93.1(12) . . . . ? F2B C8 C7A F3A -25.2(9) . . . . ? F1A C8 C7A F3A 104.7(12) . . . . ? F2A C8 C7A F3A -6.4(11) . . . . ? C7B C8 C7A F3A -46.0(19) . . . . ? C9 C8 C7A F3A -143.0(7) . . . . ? F1B C8 C7A F6A -24.2(12) . . . . ? F2B C8 C7A F6A -142.6(6) . . . . ? F1A C8 C7A F6A -12.6(12) . . . . ? F2A C8 C7A F6A -123.7(6) . . . . ? C7B C8 C7A F6A -163(3) . . . . ? C9 C8 C7A F6A 99.7(7) . . . . ? F1B C8 C7A C6 -134.6(11) . . . . ? F2B C8 C7A C6 107.1(5) . . . . ? F1A C8 C7A C6 -123.0(10) . . . . ? F2A C8 C7A C6 125.9(5) . . . . ? C7B C8 C7A C6 86(2) . . . . ? C9 C8 C7A C6 -10.7(5) . . . . ? C42B C1 C42A C43A 97(2) . . . . ? C2 C1 C42A C43A -144.0(6) . . . . ? S1 C1 C42A C43A 30.0(9) . . . . ? F1B C8 C7B F6B 12.9(15) . . . . ? F2B C8 C7B F6B -100.9(8) . . . . ? F1A C8 C7B F6B 26.9(14) . . . . ? F2A C8 C7B F6B -87.9(8) . . . . ? C9 C8 C7B F6B 147.4(7) . . . . ? C7A C8 C7B F6B 59(2) . . . . ? F1B C8 C7B F3B 137.5(12) . . . . ? F2B C8 C7B F3B 23.7(7) . . . . ? F1A C8 C7B F3B 151.5(12) . . . . ? F2A C8 C7B F3B 36.7(9) . . . . ? C9 C8 C7B F3B -88.0(7) . . . . ? C7A C8 C7B F3B -176(3) . . . . ? F1B C8 C7B C6 -115.1(12) . . . . ? F2B C8 C7B C6 131.1(6) . . . . ? F1A C8 C7B C6 -101.1(12) . . . . ? F2A C8 C7B C6 144.1(5) . . . . ? C9 C8 C7B C6 19.4(6) . . . . ? C7A C8 C7B C6 -69(2) . . . . ? F4A C6 C7B F6B 77.8(10) . . . . ? F5A C6 C7B F6B 8.6(12) . . . . ? C7A C6 C7B F6B -34.3(17) . . . . ? C5 C6 C7B F6B -145.5(8) . . . . ? F5B C6 C7B F6B -38.9(9) . . . . ? F4B C6 C7B F6B 106.9(8) . . . . ? F4A C6 C7B F3B -38.2(8) . . . . ? F5A C6 C7B F3B -107.4(7) . . . . ? C7A C6 C7B F3B -150(3) . . . . ? C5 C6 C7B F3B 98.5(6) . . . . ? F5B C6 C7B F3B -154.9(5) . . . . ? F4B C6 C7B F3B -9.1(6) . . . . ? F4A C6 C7B C8 -152.9(5) . . . . ? F5A C6 C7B C8 137.9(5) . . . . ? C7A C6 C7B C8 95(2) . . . . ? C5 C6 C7B C8 -16.2(6) . . . . ? F5B C6 C7B C8 90.4(6) . . . . ? F4B C6 C7B C8 -123.9(5) . . . . ? C2 C1 C42B C43B 166.3(9) . . . . ? C42A C1 C42B C43B -117(3) . . . . ? S1 C1 C42B C43B 5.8(15) . . . . ? C42B C1 S1 C4 164.9(5) . . . . ? C2 C1 S1 C4 -0.2(3) . . . . ? C42A C1 S1 C4 -175.2(5) . . . . ? C3 C4 S1 C1 -0.2(3) . . . . ? C14 C4 S1 C1 -176.3(3) . . . . ? C11 C10 S2 C13 0.0(3) . . . . ? C44 C10 S2 C13 179.5(3) . . . . ? C12 C13 S2 C10 -1.1(3) . . . . ? C28 C13 S2 C10 176.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.488 _refine_diff_density_min -0.772 _refine_diff_density_rms 0.071