Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global #========================================================= _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Seiya Kobatake' ; Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University and CREST Japan Science and Technology Corporation Hakozaki 6-10-1, Higashi-ku Fukuoka 812-8581, Japan ; 'Kingo Uchida' ; Department of Materials Chemistry, Faculty of Science and Technology, Ryukoku University, Seta, Otsu 520-2194, Japan ; 'Eriko Tsuchida' ; Department of Materials Chemistry, Faculty of Science and Technology, Ryukoku University, Seta, Otsu 520-2194, Japan ; 'Masahiro Irie' ; Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University and CREST Japan Science and Technology Corporation Hakozaki 6-10-1, Higashi-ku Fukuoka 812-8581, Japan ; _publ_contact_author_name 'Prof Masahiro Irie' _publ_contact_author_address ; Department of Chemistry and Biochemistry, Graduate School of Engineering Kyushu University Hakozaki 6-10-1 Higashi-ku Fukuoka 812-8581 JAPAN ; _publ_contact_author_email 'IRIE@CSTF.KYUSHU-U.AC.JP' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Single-crystalline photochromism of diarylethenes: reactivity-structure relationship ; data_compd2a _database_code_CSD 192542 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-bis(2,4-dimethyl-5-methoxyphenyl-3-thienyl)perfluorocyclopentene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H26 F6 O2 S2' _chemical_formula_weight 608.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' 'S' 'S' 0.1246 0.1234 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.564(3) _cell_length_b 9.771(2) _cell_length_c 23.797(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.368(4) _cell_angle_gamma 90.00 _cell_volume 2903.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4202 _cell_measurement_theta_min 1.63 _cell_measurement_theta_max 21.97 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.249 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10956 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 21.97 _reflns_number_total 3545 _reflns_number_gt 2693 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+1.3583P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3545 _refine_ls_number_parameters 438 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.079 _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 S1 S 0.65978(7) 0.35383(9) 0.21689(4) 0.0492(3) Uani 1 1 d . . . S2 S 0.15295(8) 0.52757(11) 0.14814(4) 0.0645(3) Uani 1 1 d . A . F1A F 0.4696(12) -0.0745(18) 0.1609(6) 0.082(4) Uani 0.74(2) 1 d PD A 1 F2A F 0.5118(7) 0.0137(15) 0.0837(5) 0.076(2) Uani 0.74(2) 1 d PD A 1 F3A F 0.3120(4) -0.1718(7) 0.0924(6) 0.100(3) Uani 0.74(2) 1 d PD A 1 F4A F 0.3269(4) -0.0107(11) 0.0313(2) 0.092(2) Uani 0.74(2) 1 d PD A 1 F5A F 0.2028(10) -0.0162(14) 0.1524(4) 0.081(2) Uani 0.74(2) 1 d PD A 1 F6A F 0.1640(8) 0.0790(13) 0.0713(5) 0.087(3) Uani 0.74(2) 1 d PD A 1 C7A C 0.3291(8) -0.0377(13) 0.0859(7) 0.061(3) Uani 0.74(2) 1 d PD A 1 F1B F 0.483(3) 0.014(5) 0.0675(17) 0.118(13) Uani 0.26(2) 1 d PD A 2 F2B F 0.493(3) -0.077(5) 0.1502(17) 0.078(10) Uani 0.26(2) 1 d PD A 2 F3B F 0.3107(16) -0.113(4) 0.0535(15) 0.140(18) Uani 0.26(2) 1 d PD A 2 F4B F 0.3125(11) -0.161(2) 0.1412(18) 0.124(11) Uani 0.26(2) 1 d PD A 2 F5B F 0.177(3) 0.083(3) 0.0660(13) 0.120(14) Uani 0.26(2) 1 d PD A 2 F6B F 0.170(3) 0.009(4) 0.1498(14) 0.113(13) Uani 0.26(2) 1 d PD A 2 C7B C 0.321(2) -0.059(3) 0.1054(12) 0.053(12) Uani 0.26(2) 1 d PD A 2 C1 C 0.5601(2) 0.2326(3) 0.21131(14) 0.0450(8) Uani 1 1 d . . . C2 C 0.5010(3) 0.2425(3) 0.15968(14) 0.0451(9) Uani 1 1 d . . . C3 C 0.5373(3) 0.3461(4) 0.12370(14) 0.0481(9) Uani 1 1 d . . . C4 C 0.6243(3) 0.4154(3) 0.14979(14) 0.0461(9) Uani 1 1 d . . . C5 C 0.4119(3) 0.1494(3) 0.13958(14) 0.0447(8) Uani 1 1 d . A . C6 C 0.4343(3) 0.0108(4) 0.11785(18) 0.0594(10) Uani 1 1 d . . . C8 C 0.2443(3) 0.0513(4) 0.11199(18) 0.0611(11) Uani 1 1 d . . . C9 C 0.3063(3) 0.1751(3) 0.13489(14) 0.0459(9) Uani 1 1 d . A . C10 C 0.2065(3) 0.3938(4) 0.11360(15) 0.0570(10) Uani 1 1 d . A . C11 C 0.2513(2) 0.3009(4) 0.15130(15) 0.0463(9) Uani 1 1 d . . . C12 C 0.2393(2) 0.3340(3) 0.20882(14) 0.0432(8) Uani 1 1 d . A . C13 C 0.1867(2) 0.4558(4) 0.21385(14) 0.0471(9) Uani 1 1 d . . . C14 C 0.5505(3) 0.1364(4) 0.25922(15) 0.0587(10) Uani 1 1 d . . . H14A H 0.4902 0.0770 0.2499 0.088 Uiso 1 1 calc R . . H14B H 0.5405 0.1876 0.2927 0.088 Uiso 1 1 calc R . . H14C H 0.6146 0.0826 0.2659 0.088 Uiso 1 1 calc R . . C15 C 0.1963(4) 0.3937(5) 0.05008(16) 0.0844(14) Uani 1 1 d . . . H15A H 0.2406 0.3227 0.0372 0.127 Uiso 1 1 calc R A . H15B H 0.2188 0.4807 0.0369 0.127 Uiso 1 1 calc R . . H15C H 0.1230 0.3775 0.0356 0.127 Uiso 1 1 calc R . . C16 C 0.4910(3) 0.3688(5) 0.06363(16) 0.0793(13) Uani 1 1 d . . . H16A H 0.4294 0.4272 0.0629 0.119 Uiso 1 1 calc R . . H16B H 0.4702 0.2825 0.0465 0.119 Uiso 1 1 calc R . . H16C H 0.5436 0.4112 0.0431 0.119 Uiso 1 1 calc R . . C17 C 0.2740(3) 0.2401(4) 0.25724(15) 0.0663(11) Uani 1 1 d . . . H17A H 0.3470 0.2596 0.2714 0.099 Uiso 1 1 calc R A . H17B H 0.2684 0.1469 0.2445 0.099 Uiso 1 1 calc R . . H17C H 0.2289 0.2537 0.2868 0.099 Uiso 1 1 calc R . . C18 C 0.6859(2) 0.5270(3) 0.12754(14) 0.0440(8) Uani 1 1 d . . . C19 C 0.6352(3) 0.6393(4) 0.09938(15) 0.0515(9) Uani 1 1 d . . . H19A H 0.5608 0.6436 0.0948 0.062 Uiso 1 1 calc R . . C20 C 0.6929(3) 0.7433(4) 0.07843(15) 0.0523(9) Uani 1 1 d . . . H20A H 0.6575 0.8166 0.0598 0.063 Uiso 1 1 calc R . . C21 C 0.8034(3) 0.7390(4) 0.08506(14) 0.0482(9) Uani 1 1 d . . . C22 C 0.8558(3) 0.6300(4) 0.11284(15) 0.0531(10) Uani 1 1 d . . . H22A H 0.9302 0.6263 0.1175 0.064 Uiso 1 1 calc R . . C23 C 0.7960(3) 0.5264(4) 0.13359(15) 0.0515(9) Uani 1 1 d . . . H23A H 0.8317 0.4534 0.1524 0.062 Uiso 1 1 calc R . . C24 C 0.1595(2) 0.5269(4) 0.26453(15) 0.0483(9) Uani 1 1 d . A . C25 C 0.2271(3) 0.5276(4) 0.31469(16) 0.0528(9) Uani 1 1 d . . . H25A H 0.2912 0.4794 0.3164 0.063 Uiso 1 1 calc R A . C26 C 0.2033(3) 0.5964(4) 0.36209(16) 0.0568(10) Uani 1 1 d . A . H26A H 0.2503 0.5934 0.3951 0.068 Uiso 1 1 calc R . . C27 C 0.1092(3) 0.6701(4) 0.36032(17) 0.0574(10) Uani 1 1 d . . . C28 C 0.0406(3) 0.6719(4) 0.31117(19) 0.0708(12) Uani 1 1 d . A . H28A H -0.0230 0.7212 0.3098 0.085 Uiso 1 1 calc R . . C29 C 0.0644(3) 0.6022(4) 0.26422(18) 0.0651(11) Uani 1 1 d . . . H29A H 0.0166 0.6048 0.2315 0.078 Uiso 1 1 calc R A . C30 C 0.9658(3) 0.8580(5) 0.0754(2) 0.0940(15) Uani 1 1 d . . . H30A H 0.9910 0.9370 0.0569 0.141 Uiso 1 1 calc R . . H30B H 1.0005 0.7776 0.0631 0.141 Uiso 1 1 calc R . . H30C H 0.9820 0.8678 0.1156 0.141 Uiso 1 1 calc R . . C31 C 0.1469(4) 0.7443(5) 0.4557(2) 0.0937(15) Uani 1 1 d . . . H31A H 0.1154 0.7975 0.4835 0.141 Uiso 1 1 calc R A . H31B H 0.2137 0.7849 0.4486 0.141 Uiso 1 1 calc R . . H31C H 0.1593 0.6527 0.4695 0.141 Uiso 1 1 calc R . . O1 O 0.8537(2) 0.8455(3) 0.06176(11) 0.0647(7) Uani 1 1 d . . . O2 O 0.0767(2) 0.7412(3) 0.40505(13) 0.0783(8) 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 S1 0.0427(5) 0.0471(6) 0.0558(6) -0.0026(4) -0.0038(4) -0.0030(4) S2 0.0624(6) 0.0640(7) 0.0643(7) 0.0105(5) -0.0054(5) 0.0205(5) F1A 0.102(8) 0.050(4) 0.093(4) 0.000(4) 0.002(4) 0.018(5) F2A 0.062(3) 0.074(4) 0.096(5) -0.027(4) 0.023(3) 0.001(2) F3A 0.096(3) 0.044(3) 0.158(10) -0.014(4) 0.002(5) -0.020(2) F4A 0.097(3) 0.106(5) 0.069(3) -0.024(3) -0.002(2) -0.001(3) F5A 0.070(6) 0.080(4) 0.093(4) 0.007(3) 0.018(3) -0.028(4) F6A 0.054(4) 0.099(7) 0.102(6) -0.012(4) -0.016(4) -0.022(3) C7A 0.065(5) 0.052(5) 0.066(8) -0.005(8) 0.003(5) -0.006(4) F1B 0.16(3) 0.093(14) 0.11(2) -0.033(14) 0.056(19) -0.03(2) F2B 0.061(11) 0.058(12) 0.11(2) -0.024(14) -0.032(15) 0.030(9) F3B 0.124(13) 0.15(4) 0.13(2) -0.10(3) -0.047(17) 0.01(2) F4B 0.085(8) 0.097(11) 0.19(3) 0.058(14) -0.002(11) -0.011(7) F5B 0.13(2) 0.057(14) 0.15(3) 0.008(14) -0.109(16) -0.004(14) F6B 0.064(17) 0.10(2) 0.19(2) -0.034(14) 0.052(13) -0.050(14) C7B 0.061(13) 0.04(2) 0.05(2) -0.005(15) -0.002(11) -0.023(10) C1 0.0387(19) 0.043(2) 0.053(2) 0.0017(17) 0.0038(16) 0.0033(16) C2 0.0394(19) 0.040(2) 0.055(2) -0.0010(17) 0.0017(17) 0.0006(16) C3 0.044(2) 0.046(2) 0.053(2) 0.0022(19) -0.0028(17) -0.0020(17) C4 0.0391(19) 0.040(2) 0.058(2) -0.0037(18) 0.0027(16) 0.0019(17) C5 0.042(2) 0.041(2) 0.051(2) 0.0008(17) 0.0018(16) -0.0002(17) C6 0.056(3) 0.052(3) 0.071(3) -0.002(2) 0.007(2) -0.002(2) C8 0.047(3) 0.065(3) 0.068(3) 0.003(2) -0.008(2) -0.014(2) C9 0.041(2) 0.046(2) 0.050(2) 0.0033(17) 0.0004(16) -0.0056(17) C10 0.053(2) 0.060(2) 0.057(2) 0.005(2) -0.0007(18) 0.0115(19) C11 0.0301(18) 0.048(2) 0.058(2) 0.0058(19) -0.0046(16) -0.0009(16) C12 0.0297(18) 0.048(2) 0.051(2) 0.0066(18) -0.0010(15) -0.0016(17) C13 0.0337(19) 0.054(2) 0.053(2) 0.0041(18) -0.0023(16) 0.0012(17) C14 0.050(2) 0.056(2) 0.070(3) 0.002(2) 0.0016(18) 0.0007(18) C15 0.094(3) 0.100(4) 0.056(3) 0.009(2) -0.007(2) 0.023(3) C16 0.083(3) 0.080(3) 0.069(3) 0.012(2) -0.016(2) -0.031(2) C17 0.081(3) 0.058(3) 0.061(2) 0.013(2) 0.009(2) 0.018(2) C18 0.034(2) 0.043(2) 0.054(2) -0.0035(18) 0.0035(15) -0.0010(17) C19 0.0364(19) 0.052(2) 0.066(2) -0.001(2) 0.0023(17) -0.0007(19) C20 0.047(2) 0.051(2) 0.058(2) 0.0046(19) 0.0016(17) 0.0029(19) C21 0.050(2) 0.047(2) 0.049(2) -0.0062(18) 0.0111(17) -0.0099(19) C22 0.037(2) 0.055(2) 0.067(2) -0.008(2) 0.0072(17) -0.0024(19) C23 0.046(2) 0.046(2) 0.062(2) -0.0026(19) 0.0030(17) 0.0019(18) C24 0.035(2) 0.047(2) 0.062(2) 0.0080(19) 0.0007(17) 0.0003(17) C25 0.042(2) 0.053(2) 0.062(2) 0.006(2) 0.0029(18) 0.0063(18) C26 0.053(2) 0.058(2) 0.058(3) 0.007(2) 0.0008(19) -0.001(2) C27 0.058(2) 0.052(2) 0.065(3) 0.000(2) 0.015(2) -0.002(2) C28 0.050(2) 0.073(3) 0.090(3) -0.003(3) 0.012(2) 0.015(2) C29 0.044(2) 0.074(3) 0.074(3) -0.005(2) -0.0074(19) 0.012(2) C30 0.059(3) 0.083(3) 0.144(4) 0.004(3) 0.031(3) -0.020(3) C31 0.123(4) 0.089(4) 0.071(3) -0.009(3) 0.022(3) 0.005(3) O1 0.0619(17) 0.0631(17) 0.0710(17) -0.0003(14) 0.0157(13) -0.0178(14) O2 0.083(2) 0.076(2) 0.079(2) -0.0105(17) 0.0216(17) 0.0066(16) _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 S1 C1 1.718(3) . ? S1 C4 1.718(4) . ? S2 C10 1.720(4) . ? S2 C13 1.723(3) . ? F1A C6 1.356(15) . ? F2A C6 1.337(12) . ? F3A C7A 1.340(12) . ? F4A C7A 1.323(19) . ? F5A C8 1.320(10) . ? F6A C8 1.347(10) . ? C7A C6 1.525(11) . ? C7A C8 1.557(11) . ? F1B C6 1.41(4) . ? F2B C6 1.32(4) . ? F3B C7B 1.34(2) . ? F4B C7B 1.32(3) . ? F5B C8 1.34(3) . ? F6B C8 1.42(3) . ? C7B C8 1.46(3) . ? C7B C6 1.58(2) . ? C1 C2 1.367(5) . ? C1 C14 1.493(5) . ? C2 C3 1.433(5) . ? C2 C5 1.480(5) . ? C3 C4 1.375(5) . ? C3 C16 1.499(5) . ? C4 C18 1.469(5) . ? C5 C9 1.343(4) . ? C5 C6 1.487(5) . ? C8 C9 1.507(5) . ? C9 C11 1.484(5) . ? C10 C11 1.354(5) . ? C10 C15 1.503(5) . ? C11 C12 1.431(5) . ? C12 C13 1.373(5) . ? C12 C17 1.499(5) . ? C13 C24 1.465(5) . ? C18 C23 1.375(4) . ? C18 C19 1.401(5) . ? C19 C20 1.373(5) . ? C20 C21 1.380(5) . ? C21 O1 1.367(4) . ? C21 C22 1.382(5) . ? C22 C23 1.384(5) . ? C24 C25 1.386(5) . ? C24 C29 1.402(5) . ? C25 C26 1.374(5) . ? C26 C27 1.381(5) . ? C27 O2 1.371(4) . ? C27 C28 1.374(5) . ? C28 C29 1.370(5) . ? C30 O1 1.415(5) . ? C31 O2 1.413(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 93.33(16) . . ? C10 S2 C13 93.12(17) . . ? F4A C7A F3A 108.7(9) . . ? F4A C7A C6 110.6(9) . . ? F3A C7A C6 112.8(11) . . ? F4A C7A C8 109.9(9) . . ? F3A C7A C8 112.0(10) . . ? C6 C7A C8 102.8(6) . . ? F4B C7B F3B 107(2) . . ? F4B C7B C8 112.9(16) . . ? F3B C7B C8 113.4(19) . . ? F4B C7B C6 109.6(17) . . ? F3B C7B C6 109.4(17) . . ? C8 C7B C6 104.7(14) . . ? C2 C1 C14 130.5(3) . . ? C2 C1 S1 109.9(3) . . ? C14 C1 S1 119.7(2) . . ? C1 C2 C3 114.2(3) . . ? C1 C2 C5 124.3(3) . . ? C3 C2 C5 121.4(3) . . ? C4 C3 C2 111.6(3) . . ? C4 C3 C16 124.3(3) . . ? C2 C3 C16 124.0(3) . . ? C3 C4 C18 128.8(3) . . ? C3 C4 S1 111.0(3) . . ? C18 C4 S1 120.2(2) . . ? C9 C5 C2 128.1(3) . . ? C9 C5 C6 111.4(3) . . ? C2 C5 C6 120.4(3) . . ? F2A C6 F1A 105.8(8) . . ? F2B C6 F1B 104(2) . . ? F2B C6 C5 120(2) . . ? F2A C6 C5 111.8(7) . . ? F1A C6 C5 110.8(8) . . ? F1B C6 C5 113(2) . . ? F2A C6 C7A 110.6(8) . . ? F1A C6 C7A 112.2(9) . . ? C5 C6 C7A 105.6(5) . . ? F2B C6 C7B 105.4(19) . . ? F1B C6 C7B 108.8(17) . . ? C5 C6 C7B 104.7(9) . . ? F5A C8 F6A 107.4(7) . . ? F5B C8 F6B 101.0(17) . . ? F5B C8 C7B 116.4(16) . . ? F6B C8 C7B 109.5(17) . . ? F5A C8 C9 111.6(6) . . ? F5B C8 C9 111.1(15) . . ? F6A C8 C9 114.5(7) . . ? F6B C8 C9 110.7(17) . . ? C7B C8 C9 108.1(10) . . ? F5A C8 C7A 110.8(9) . . ? F6A C8 C7A 108.5(8) . . ? C9 C8 C7A 104.1(5) . . ? C5 C9 C11 128.2(3) . . ? C5 C9 C8 110.2(3) . . ? C11 C9 C8 121.5(3) . . ? C11 C10 C15 130.4(4) . . ? C11 C10 S2 110.4(3) . . ? C15 C10 S2 119.2(3) . . ? C10 C11 C12 113.7(3) . . ? C10 C11 C9 123.6(3) . . ? C12 C11 C9 122.7(3) . . ? C13 C12 C11 112.5(3) . . ? C13 C12 C17 124.4(3) . . ? C11 C12 C17 123.0(3) . . ? C12 C13 C24 129.9(3) . . ? C12 C13 S2 110.3(3) . . ? C24 C13 S2 119.8(3) . . ? C23 C18 C19 116.9(3) . . ? C23 C18 C4 121.5(3) . . ? C19 C18 C4 121.6(3) . . ? C20 C19 C18 121.5(3) . . ? C19 C20 C21 120.0(3) . . ? O1 C21 C20 115.8(3) . . ? O1 C21 C22 124.3(3) . . ? C20 C21 C22 119.9(3) . . ? C21 C22 C23 119.0(3) . . ? C18 C23 C22 122.6(3) . . ? C25 C24 C29 116.3(3) . . ? C25 C24 C13 122.3(3) . . ? C29 C24 C13 121.4(3) . . ? C26 C25 C24 122.7(3) . . ? C25 C26 C27 119.6(3) . . ? O2 C27 C28 116.2(4) . . ? O2 C27 C26 124.7(4) . . ? C28 C27 C26 119.1(4) . . ? C29 C28 C27 121.0(4) . . ? C28 C29 C24 121.3(4) . . ? C21 O1 C30 117.8(3) . . ? C27 O2 C31 117.5(3) . . ? 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 C4 S1 C1 C2 -1.1(3) . . . . ? C4 S1 C1 C14 178.1(3) . . . . ? C14 C1 C2 C3 -177.8(3) . . . . ? S1 C1 C2 C3 1.3(4) . . . . ? C14 C1 C2 C5 -2.2(6) . . . . ? S1 C1 C2 C5 176.9(3) . . . . ? C1 C2 C3 C4 -0.9(4) . . . . ? C5 C2 C3 C4 -176.6(3) . . . . ? C1 C2 C3 C16 175.0(4) . . . . ? C5 C2 C3 C16 -0.7(5) . . . . ? C2 C3 C4 C18 179.3(3) . . . . ? C16 C3 C4 C18 3.4(6) . . . . ? C2 C3 C4 S1 0.0(4) . . . . ? C16 C3 C4 S1 -175.9(3) . . . . ? C1 S1 C4 C3 0.7(3) . . . . ? C1 S1 C4 C18 -178.7(3) . . . . ? C1 C2 C5 C9 105.5(4) . . . . ? C3 C2 C5 C9 -79.2(5) . . . . ? C1 C2 C5 C6 -78.5(5) . . . . ? C3 C2 C5 C6 96.7(4) . . . . ? C9 C5 C6 F2B -126(2) . . . . ? C2 C5 C6 F2B 58(2) . . . . ? C9 C5 C6 F2A 133.0(6) . . . . ? C2 C5 C6 F2A -43.5(7) . . . . ? C9 C5 C6 F1A -109.2(8) . . . . ? C2 C5 C6 F1A 74.3(8) . . . . ? C9 C5 C6 F1B 111(2) . . . . ? C2 C5 C6 F1B -66(2) . . . . ? C9 C5 C6 C7A 12.6(8) . . . . ? C2 C5 C6 C7A -163.9(8) . . . . ? C9 C5 C6 C7B -7.6(11) . . . . ? C2 C5 C6 C7B 175.8(11) . . . . ? F4A C7A C6 F2A -25.9(10) . . . . ? F3A C7A C6 F2A 96.1(13) . . . . ? C8 C7A C6 F2A -143.2(10) . . . . ? F4A C7A C6 F1A -143.9(10) . . . . ? F3A C7A C6 F1A -21.9(14) . . . . ? C8 C7A C6 F1A 98.9(13) . . . . ? C8 C7A C6 F1B -136(2) . . . . ? F4A C7A C6 C5 95.2(7) . . . . ? F3A C7A C6 C5 -142.8(9) . . . . ? C8 C7A C6 C5 -22.0(11) . . . . ? F4B C7B C6 F2B 15(3) . . . . ? F3B C7B C6 F2B -101(3) . . . . ? C8 C7B C6 F2B 137(3) . . . . ? F4B C7B C6 F1B 126(3) . . . . ? F3B C7B C6 F1B 10(3) . . . . ? C8 C7B C6 F1B -112(3) . . . . ? F4B C7B C6 C5 -112.4(19) . . . . ? F3B C7B C6 C5 131(2) . . . . ? C8 C7B C6 C5 9.0(17) . . . . ? F4B C7B C8 F5B -122(2) . . . . ? F3B C7B C8 F5B -1(3) . . . . ? C6 C7B C8 F5B 118(2) . . . . ? F4B C7B C8 F6B -9(3) . . . . ? F3B C7B C8 F6B 113(3) . . . . ? C6 C7B C8 F6B -128(2) . . . . ? F4B C7B C8 C9 112(2) . . . . ? F3B C7B C8 C9 -127(2) . . . . ? C6 C7B C8 C9 -7.4(17) . . . . ? F4A C7A C8 F5A 145.8(8) . . . . ? F3A C7A C8 F5A 24.8(13) . . . . ? C6 C7A C8 F5A -96.5(11) . . . . ? F4A C7A C8 F6A 28.1(9) . . . . ? F3A C7A C8 F6A -92.8(13) . . . . ? C6 C7A C8 F6A 145.8(10) . . . . ? F4A C7A C8 C9 -94.2(7) . . . . ? F3A C7A C8 C9 144.9(9) . . . . ? C6 C7A C8 C9 23.5(11) . . . . ? C2 C5 C9 C11 -3.4(6) . . . . ? C6 C5 C9 C11 -179.6(3) . . . . ? C2 C5 C9 C8 179.4(3) . . . . ? C6 C5 C9 C8 3.2(4) . . . . ? F5A C8 C9 C5 102.3(7) . . . . ? F5B C8 C9 C5 -125.7(17) . . . . ? F6A C8 C9 C5 -135.5(6) . . . . ? F6B C8 C9 C5 123.0(17) . . . . ? C7B C8 C9 C5 3.1(13) . . . . ? C7A C8 C9 C5 -17.3(8) . . . . ? F5A C8 C9 C11 -75.2(7) . . . . ? F5B C8 C9 C11 56.9(17) . . . . ? F6A C8 C9 C11 47.1(7) . . . . ? F6B C8 C9 C11 -54.4(17) . . . . ? C7B C8 C9 C11 -174.3(12) . . . . ? C7A C8 C9 C11 165.3(8) . . . . ? C13 S2 C10 C11 -2.0(3) . . . . ? C13 S2 C10 C15 176.9(3) . . . . ? C15 C10 C11 C12 -176.4(4) . . . . ? S2 C10 C11 C12 2.3(4) . . . . ? C15 C10 C11 C9 2.6(6) . . . . ? S2 C10 C11 C9 -178.6(3) . . . . ? C5 C9 C11 C10 105.4(4) . . . . ? C8 C9 C11 C10 -77.7(5) . . . . ? C5 C9 C11 C12 -75.7(5) . . . . ? C8 C9 C11 C12 101.2(4) . . . . ? C10 C11 C12 C13 -1.5(4) . . . . ? C9 C11 C12 C13 179.4(3) . . . . ? C10 C11 C12 C17 174.5(3) . . . . ? C9 C11 C12 C17 -4.5(5) . . . . ? C11 C12 C13 C24 -179.1(3) . . . . ? C17 C12 C13 C24 4.9(6) . . . . ? C11 C12 C13 S2 0.0(3) . . . . ? C17 C12 C13 S2 -176.0(3) . . . . ? C10 S2 C13 C12 1.1(3) . . . . ? C10 S2 C13 C24 -179.7(3) . . . . ? C3 C4 C18 C23 -133.6(4) . . . . ? S1 C4 C18 C23 45.6(4) . . . . ? C3 C4 C18 C19 46.7(5) . . . . ? S1 C4 C18 C19 -134.1(3) . . . . ? C23 C18 C19 C20 0.5(5) . . . . ? C4 C18 C19 C20 -179.7(3) . . . . ? C18 C19 C20 C21 -0.3(5) . . . . ? C19 C20 C21 O1 178.7(3) . . . . ? C19 C20 C21 C22 0.0(5) . . . . ? O1 C21 C22 C23 -178.5(3) . . . . ? C20 C21 C22 C23 0.1(5) . . . . ? C19 C18 C23 C22 -0.5(5) . . . . ? C4 C18 C23 C22 179.8(3) . . . . ? C21 C22 C23 C18 0.2(5) . . . . ? C12 C13 C24 C25 36.8(5) . . . . ? S2 C13 C24 C25 -142.2(3) . . . . ? C12 C13 C24 C29 -145.2(4) . . . . ? S2 C13 C24 C29 35.7(4) . . . . ? C29 C24 C25 C26 0.6(5) . . . . ? C13 C24 C25 C26 178.6(3) . . . . ? C24 C25 C26 C27 -0.9(6) . . . . ? C25 C26 C27 O2 179.2(3) . . . . ? C25 C26 C27 C28 0.7(6) . . . . ? O2 C27 C28 C29 -178.8(3) . . . . ? C26 C27 C28 C29 -0.2(6) . . . . ? C27 C28 C29 C24 -0.2(6) . . . . ? C25 C24 C29 C28 0.0(6) . . . . ? C13 C24 C29 C28 -178.1(4) . . . . ? C20 C21 O1 C30 169.6(3) . . . . ? C22 C21 O1 C30 -11.7(5) . . . . ? C28 C27 O2 C31 -178.3(4) . . . . ? C26 C27 O2 C31 3.1(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 21.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.223 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.046 #===END data_compd3a _database_code_CSD 192543 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-Bis(2-isopropyl-4-methyl-3-thienyl)perfluorocyclopentene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H30 F6 S2' _chemical_formula_weight 604.69 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.546(4) _cell_length_b 8.3164(15) _cell_length_c 19.233(4) _cell_angle_alpha 90.00 _cell_angle_beta 127.235(3) _cell_angle_gamma 90.00 _cell_volume 2998.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2631 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 23.25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.236 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.1 _diffrn_reflns_number 6489 _diffrn_reflns_av_R_equivalents 0.0763 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 23.25 _reflns_number_total 2151 _reflns_number_gt 1622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0745P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2151 _refine_ls_number_parameters 214 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.07535(3) 0.94600(7) 0.16571(4) 0.0516(2) Uani 1 1 d . . . F1A F 0.1014(3) 0.3641(8) 0.2535(4) 0.0727(17) Uani 0.50 1 d PD A 1 F2A F -0.0063(3) 0.3614(8) 0.1364(4) 0.0709(14) Uani 0.50 1 d PD B 1 C6A C 0.0305(4) 0.3922(8) 0.2186(5) 0.042(2) Uiso 0.50 1 d PD . 1 F1B F 0.0340(4) 0.3757(8) 0.1582(5) 0.100(3) Uani 0.50 1 d PD . 2 F2B F 0.1092(4) 0.3487(8) 0.2990(5) 0.094(2) Uani 0.50 1 d PD . 2 C6B C 0.0456(4) 0.3962(9) 0.2375(5) 0.048(3) Uiso 0.50 1 d PD . 2 F3 F 0.0160(7) 0.1494(4) 0.2712(8) 0.110(5) Uani 0.50 1 d P . . F4 F 0.0674(2) 0.2592(6) 0.3485(3) 0.0938(12) Uani 0.50 1 d P . . C1 C 0.02116(12) 0.7928(3) 0.15418(15) 0.0433(6) Uani 1 1 d . . . C2 C 0.05569(11) 0.7036(3) 0.22879(14) 0.0410(6) Uani 1 1 d . . . C3 C 0.12723(12) 0.7559(3) 0.29574(15) 0.0458(6) Uani 1 1 d . . . C4 C 0.14435(12) 0.8892(3) 0.27025(15) 0.0482(6) Uani 1 1 d . . . C5 C 0.02297(11) 0.5634(3) 0.24019(14) 0.0400(5) Uani 1 1 d . . . C7 C 0.0117(3) 0.2883(5) 0.2664(4) 0.0499(14) Uiso 0.50 1 d P . . C8 C -0.05101(13) 0.7695(3) 0.06930(15) 0.0512(6) Uani 1 1 d . . . H8 H -0.0747 0.6828 0.0773 0.061 Uiso 1 1 calc R . . C9 C -0.04557(18) 0.7174(4) -0.00298(19) 0.0804(9) Uani 1 1 d . . . H9A H -0.0236 0.8015 -0.0133 0.121 Uiso 1 1 calc R . . H9B H -0.0925 0.6965 -0.0556 0.121 Uiso 1 1 calc R . . H9C H -0.0172 0.6215 0.0148 0.121 Uiso 1 1 calc R . . C10 C -0.09727(15) 0.9190(4) 0.0413(2) 0.0805(9) Uani 1 1 d . . . H10A H -0.1022 0.9475 0.0857 0.121 Uiso 1 1 calc R . . H10B H -0.1435 0.8977 -0.0124 0.121 Uiso 1 1 calc R . . H10C H -0.0753 1.0061 0.0328 0.121 Uiso 1 1 calc R . . C11 C 0.17879(14) 0.6707(3) 0.38067(17) 0.0641(7) Uani 1 1 d . . . H11A H 0.1934 0.5717 0.3702 0.096 Uiso 1 1 calc R . . H11B H 0.1562 0.6482 0.4077 0.096 Uiso 1 1 calc R . . H11C H 0.2198 0.7376 0.4186 0.096 Uiso 1 1 calc R . . C12 C 0.21162(13) 0.9839(3) 0.31995(17) 0.0536(7) Uani 1 1 d . . . C13 C 0.23645(15) 1.0539(4) 0.39858(19) 0.0732(9) Uani 1 1 d . . . H13 H 0.2108 1.0415 0.4207 0.088 Uiso 1 1 calc R . . C14 C 0.29874(16) 1.1423(4) 0.4450(2) 0.0861(10) Uani 1 1 d . . . H14 H 0.3148 1.1886 0.4981 0.103 Uiso 1 1 calc R . . C15 C 0.33676(17) 1.1620(4) 0.4134(2) 0.0831(10) Uani 1 1 d . . . H15 H 0.3786 1.2219 0.4447 0.100 Uiso 1 1 calc R . . C16 C 0.31308(17) 1.0932(4) 0.3357(2) 0.0849(10) Uani 1 1 d . . . H16 H 0.3391 1.1062 0.3142 0.102 Uiso 1 1 calc R . . C17 C 0.25081(15) 1.0047(4) 0.28890(19) 0.0706(8) Uani 1 1 d . . . H17 H 0.2351 0.9586 0.2360 0.085 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0559(4) 0.0450(4) 0.0587(4) 0.0078(3) 0.0372(3) -0.0013(3) F1A 0.071(3) 0.052(2) 0.117(5) 0.006(3) 0.069(4) 0.014(2) F2A 0.108(4) 0.060(3) 0.066(3) -0.0094(17) 0.064(3) -0.002(3) F1B 0.199(8) 0.055(3) 0.139(7) -0.011(3) 0.150(7) -0.001(5) F2B 0.064(3) 0.062(3) 0.138(6) 0.006(4) 0.052(4) 0.022(2) F3 0.178(13) 0.0406(16) 0.200(14) 0.056(5) 0.161(11) 0.049(5) F4 0.096(3) 0.087(3) 0.087(3) 0.038(2) 0.048(2) 0.022(2) C1 0.0484(13) 0.0387(13) 0.0509(14) 0.0015(11) 0.0342(12) 0.0027(10) C2 0.0457(13) 0.0379(13) 0.0482(14) 0.0005(10) 0.0329(12) 0.0014(10) C3 0.0443(13) 0.0508(15) 0.0491(14) 0.0007(11) 0.0319(12) 0.0003(11) C4 0.0488(13) 0.0476(14) 0.0570(15) -0.0024(11) 0.0367(13) -0.0047(11) C5 0.0436(12) 0.0383(12) 0.0403(12) 0.0005(10) 0.0266(11) -0.0005(10) C8 0.0512(14) 0.0487(15) 0.0511(15) 0.0043(11) 0.0295(13) -0.0005(11) C9 0.088(2) 0.084(2) 0.0619(19) -0.0110(16) 0.0417(17) -0.0004(18) C10 0.0563(16) 0.073(2) 0.083(2) 0.0030(16) 0.0268(16) 0.0138(15) C11 0.0550(15) 0.0719(19) 0.0587(17) 0.0099(14) 0.0309(14) -0.0008(14) C12 0.0513(14) 0.0503(15) 0.0652(17) 0.0056(12) 0.0383(14) -0.0030(12) C13 0.0690(18) 0.085(2) 0.079(2) -0.0227(17) 0.0516(17) -0.0266(16) C14 0.075(2) 0.094(3) 0.083(2) -0.0239(18) 0.0447(19) -0.0316(18) C15 0.0658(18) 0.075(2) 0.101(3) -0.0070(19) 0.0465(19) -0.0233(16) C16 0.081(2) 0.087(2) 0.115(3) 0.000(2) 0.075(2) -0.0211(19) C17 0.0753(19) 0.074(2) 0.081(2) -0.0069(15) 0.0573(18) -0.0222(16) _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 S1 C4 1.718(2) . ? S1 C1 1.720(2) . ? F1A C6A 1.392(8) . ? F2A C6A 1.287(9) . ? C6A C7 1.470(9) 2 ? C6A C5 1.524(7) . ? C6A C7 1.511(9) . ? F1B C6B 1.388(9) . ? F2B C6B 1.286(10) . ? C6B C7 1.582(10) 2 ? C6B C5 1.502(8) . ? C6B C7 1.513(10) . ? F3 C7 1.159(5) . ? F3 C7 1.309(8) 2 ? F4 C7 1.329(6) . ? F4 C7 1.852(7) 2 ? C1 C2 1.363(3) . ? C1 C8 1.494(3) . ? C2 C3 1.435(3) . ? C2 C5 1.485(3) . ? C3 C4 1.368(3) . ? C3 C11 1.498(3) . ? C4 C12 1.486(3) . ? C5 C5 1.344(4) 2 ? C7 C7 0.531(11) 2 ? C7 F3 1.309(8) 2 ? C7 C6A 1.470(9) 2 ? C7 C6B 1.582(10) 2 ? C7 F4 1.852(7) 2 ? C8 C10 1.520(4) . ? C8 C9 1.534(4) . ? C12 C13 1.378(4) . ? C12 C17 1.380(4) . ? C13 C14 1.380(4) . ? C14 C15 1.362(4) . ? C15 C16 1.365(5) . ? C16 C17 1.381(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C1 92.85(11) . . ? F2A C6A C7 95.2(6) . 2 ? F2A C6A F1A 106.2(6) . . ? C7 C6A F1A 124.2(6) 2 . ? F2A C6A C5 114.7(6) . . ? C7 C6A C5 107.0(5) 2 . ? F1A C6A C5 109.2(5) . . ? F2A C6A C7 114.0(6) . . ? F1A C6A C7 108.6(6) . . ? C5 C6A C7 104.1(5) . . ? F2B C6B F1B 108.5(7) . . ? F2B C6B C7 110.8(6) . 2 ? F1B C6B C7 106.4(6) . 2 ? F2B C6B C5 119.5(6) . . ? F1B C6B C5 108.3(6) . . ? C7 C6B C5 102.5(5) 2 . ? F2B C6B C7 93.5(6) . . ? F1B C6B C7 122.3(6) . . ? C5 C6B C7 105.0(5) . . ? C2 C1 C8 129.7(2) . . ? C2 C1 S1 110.11(17) . . ? C8 C1 S1 120.08(17) . . ? C1 C2 C3 114.1(2) . . ? C1 C2 C5 123.4(2) . . ? C3 C2 C5 122.53(19) . . ? C4 C3 C2 111.4(2) . . ? C4 C3 C11 123.6(2) . . ? C2 C3 C11 124.9(2) . . ? C3 C4 C12 129.0(2) . . ? C3 C4 S1 111.53(17) . . ? C12 C4 S1 119.49(18) . . ? C5 C5 C2 128.26(12) 2 . ? C5 C5 C6B 111.9(3) 2 . ? C2 C5 C6B 119.7(3) . . ? C5 C5 C6A 108.8(3) 2 . ? C2 C5 C6A 122.5(3) . . ? F3 C7 C6A 127.4(11) . 2 ? F3 C7 C6A 117.3(9) 2 2 ? F3 C7 F4 107.4(5) 2 . ? C6A C7 F4 100.0(5) 2 . ? F3 C7 C6B 126.9(10) . 2 ? F3 C7 C6B 110.5(8) 2 2 ? F4 C7 C6B 111.2(5) . 2 ? F3 C7 C6A 125.0(10) . . ? F3 C7 C6A 113.5(9) 2 . ? C6A C7 C6A 105.4(6) 2 . ? F4 C7 C6A 112.6(5) . . ? C6B C7 C6A 101.7(3) 2 . ? F3 C7 C6B 125.4(11) . . ? F3 C7 C6B 121.1(10) 2 . ? C6A C7 C6B 107.1(3) 2 . ? F4 C7 C6B 100.5(5) . . ? C6B C7 C6B 105.7(6) 2 . ? F3 C7 F4 86.6(6) . 2 ? C6A C7 F4 90.0(4) 2 2 ? C6B C7 F4 78.7(4) 2 2 ? C6A C7 F4 78.6(4) . 2 ? C6B C7 F4 90.7(4) . 2 ? C1 C8 C10 112.3(2) . . ? C1 C8 C9 111.3(2) . . ? C10 C8 C9 110.2(2) . . ? C13 C12 C17 118.1(2) . . ? C13 C12 C4 120.6(2) . . ? C17 C12 C4 121.3(2) . . ? C12 C13 C14 121.0(3) . . ? C15 C14 C13 120.2(3) . . ? C14 C15 C16 119.7(3) . . ? C15 C16 C17 120.5(3) . . ? C12 C17 C16 120.6(3) . . ? 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 C4 S1 C1 C2 0.38(18) . . . . ? C4 S1 C1 C8 -176.92(19) . . . . ? C8 C1 C2 C3 175.6(2) . . . . ? S1 C1 C2 C3 -1.4(3) . . . . ? C8 C1 C2 C5 -3.8(4) . . . . ? S1 C1 C2 C5 179.21(17) . . . . ? C1 C2 C3 C4 1.9(3) . . . . ? C5 C2 C3 C4 -178.6(2) . . . . ? C1 C2 C3 C11 -174.4(2) . . . . ? C5 C2 C3 C11 5.0(4) . . . . ? C2 C3 C4 C12 178.4(2) . . . . ? C11 C3 C4 C12 -5.3(4) . . . . ? C2 C3 C4 S1 -1.6(3) . . . . ? C11 C3 C4 S1 174.8(2) . . . . ? C1 S1 C4 C3 0.71(19) . . . . ? C1 S1 C4 C12 -179.2(2) . . . . ? C1 C2 C5 C5 -80.0(4) . . . 2 ? C3 C2 C5 C5 100.6(3) . . . 2 ? C1 C2 C5 C6B 105.4(4) . . . . ? C3 C2 C5 C6B -73.9(4) . . . . ? C1 C2 C5 C6A 91.6(4) . . . . ? C3 C2 C5 C6A -87.8(4) . . . . ? F2B C6B C5 C5 -107.7(7) . . . 2 ? F1B C6B C5 C5 127.4(6) . . . 2 ? C7 C6B C5 C5 15.2(6) 2 . . 2 ? C7 C6B C5 C5 -4.8(6) . . . 2 ? F2B C6B C5 C2 67.7(7) . . . . ? F1B C6B C5 C2 -57.2(7) . . . . ? C7 C6B C5 C2 -169.4(3) 2 . . . ? C7 C6B C5 C2 170.6(3) . . . . ? F2B C6B C5 C6A 174(3) . . . . ? F1B C6B C5 C6A 50(2) . . . . ? C7 C6B C5 C6A -63(2) 2 . . . ? C7 C6B C5 C6A -83(2) . . . . ? F2A C6A C5 C5 100.2(5) . . . 2 ? C7 C6A C5 C5 -4.0(6) 2 . . 2 ? F1A C6A C5 C5 -140.8(5) . . . 2 ? C7 C6A C5 C5 -25.0(6) . . . 2 ? F2A C6A C5 C2 -72.9(6) . . . . ? C7 C6A C5 C2 -177.1(3) 2 . . . ? F1A C6A C5 C2 46.1(7) . . . . ? C7 C6A C5 C2 161.9(3) . . . . ? F2A C6A C5 C6B -153(3) . . . . ? C7 C6A C5 C6B 103(3) 2 . . . ? F1A C6A C5 C6B -34(2) . . . . ? C7 C6A C5 C6B 82(2) . . . . ? F2A C6A C7 F3 60.1(10) . . . . ? F1A C6A C7 F3 -58.0(10) . . . . ? C5 C6A C7 F3 -174.3(8) . . . . ? F2A C6A C7 F3 25.4(9) . . . 2 ? F1A C6A C7 F3 -92.7(9) . . . 2 ? C5 C6A C7 F3 151.0(7) . . . 2 ? F2A C6A C7 C6A -104.3(7) . . . 2 ? F1A C6A C7 C6A 137.6(7) . . . 2 ? C5 C6A C7 C6A 21.4(4) . . . 2 ? F2A C6A C7 F4 147.7(6) . . . . ? F1A C6A C7 F4 29.6(8) . . . . ? C5 C6A C7 F4 -86.7(6) . . . . ? F2A C6A C7 C6B -93.3(6) . . . 2 ? F1A C6A C7 C6B 148.6(6) . . . 2 ? C5 C6A C7 C6B 32.4(6) . . . 2 ? F2A C6A C7 C6B 156(3) . . . . ? F1A C6A C7 C6B 38(2) . . . . ? C5 C6A C7 C6B -78(2) . . . . ? F2A C6A C7 F4 -17.5(6) . . . 2 ? F1A C6A C7 F4 -135.6(6) . . . 2 ? C5 C6A C7 F4 108.2(4) . . . 2 ? F2B C6B C7 F3 -59.7(10) . . . . ? F1B C6B C7 F3 54.9(12) . . . . ? C5 C6B C7 F3 178.5(8) . . . . ? F2B C6B C7 F3 -98.0(8) . . . 2 ? F1B C6B C7 F3 16.5(12) . . . 2 ? C5 C6B C7 F3 140.2(7) . . . 2 ? F2B C6B C7 C6A 123.8(6) . . . 2 ? F1B C6B C7 C6A -121.6(8) . . . 2 ? C5 C6B C7 C6A 2.0(7) . . . 2 ? F2B C6B C7 F4 19.8(6) . . . . ? F1B C6B C7 F4 134.3(7) . . . . ? C5 C6B C7 F4 -102.0(5) . . . . ? F2B C6B C7 C6B 135.5(6) . . . 2 ? F1B C6B C7 C6B -109.9(9) . . . 2 ? C5 C6B C7 C6B 13.8(4) . . . 2 ? F2B C6B C7 C6A -152(3) . . . . ? F1B C6B C7 C6A -38(2) . . . . ? C5 C6B C7 C6A 86(2) . . . . ? F2B C6B C7 F4 -146.0(5) . . . 2 ? F1B C6B C7 F4 -31.4(8) . . . 2 ? C7 C6B C7 F4 7.1(8) 2 . . 2 ? C5 C6B C7 F4 92.2(5) . . . 2 ? C2 C1 C8 C10 126.1(3) . . . . ? S1 C1 C8 C10 -57.2(3) . . . . ? C2 C1 C8 C9 -109.9(3) . . . . ? S1 C1 C8 C9 66.8(3) . . . . ? C3 C4 C12 C13 -58.5(4) . . . . ? S1 C4 C12 C13 121.4(3) . . . . ? C3 C4 C12 C17 121.7(3) . . . . ? S1 C4 C12 C17 -58.4(3) . . . . ? C17 C12 C13 C14 0.0(4) . . . . ? C4 C12 C13 C14 -179.8(3) . . . . ? C12 C13 C14 C15 0.1(5) . . . . ? C13 C14 C15 C16 -0.2(5) . . . . ? C14 C15 C16 C17 0.2(5) . . . . ? C13 C12 C17 C16 0.0(5) . . . . ? C4 C12 C17 C16 179.8(3) . . . . ? C15 C16 C17 C12 -0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.300 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.059 #===END data_compd4a _database_code_CSD 192544 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-bis(2-isopropyl-4-methyl-5-methoxyphenyl-3-thienyl)perfluorocyclopentene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H34 F6 O2 S2' _chemical_formula_weight 664.74 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.5668(11) _cell_length_b 14.7276(12) _cell_length_c 18.0976(14) _cell_angle_alpha 90.00 _cell_angle_beta 111.9480(10) _cell_angle_gamma 90.00 _cell_volume 3353.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 304(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour 'Pale yellow ' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.907 _exptl_absorpt_correction_T_max 0.936 _exptl_absorpt_process_details ; Empirical absorption correction was applied by a Bruker XPREP program using the value mu*t = 0.055. ; _exptl_special_details ; The crystal was obtained from an ethanol solution and was mounted on a glass capillary with the epoxy grue. A total of 3200 frames of data were collected using a narrow-frame method with scan widths of 0.3 degree in omega and 10 seconds exposure times at a distance of 5.0 cm from the crystal. The total data collection time was approximately 18 hours. Frames were integrated with a Bruker SAINT program. ; _diffrn_ambient_temperature 304(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.6 _diffrn_reflns_number 29012 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3887 _reflns_number_gt 2709 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Since the molecule lies on the two fold axis, a half is in the asymmetric unit. The perfluorocyclopentene ring was disordered around the two fold axis. The bond lengthes of C-F and C-C bonds in the disordered ring were restraind and each occupancy factor was fixed to be 0.5 in the refinement process. ; _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^)+(0.0745P)^2^+0.5892P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3887 _refine_ls_number_parameters 248 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1345 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.27272(4) 0.04979(3) 0.70617(3) 0.06390(18) Uani 1 1 d . . . C6A C 0.4066(4) -0.2692(4) 0.72141(19) 0.061(3) Uani 0.50 1 d PD A 1 F1A F 0.3255(3) -0.2854(2) 0.6525(3) 0.0911(11) Uani 0.50 1 d PD A 1 F2A F 0.3700(3) -0.2880(3) 0.7789(2) 0.0978(12) Uani 0.50 1 d PD A 1 C6B C 0.4058(4) -0.2680(5) 0.7116(3) 0.074(3) Uani 0.50 1 d PD . 2 F1B F 0.3841(4) -0.2977(2) 0.6372(2) 0.1210(16) Uani 0.50 1 d PD B 2 F2B F 0.3193(3) -0.2788(3) 0.7297(4) 0.136(2) Uani 0.50 1 d PD C 2 F3 F 0.5136(3) -0.33318(18) 0.65895(16) 0.1009(9) Uani 0.50 1 d PD A . F4 F 0.498(2) -0.40944(13) 0.7564(10) 0.1082(12) Uani 0.50 1 d PD A . O1 O -0.01761(14) 0.20810(12) 0.35262(11) 0.1045(6) Uani 1 1 d . . . C1 C 0.36077(13) -0.03360(11) 0.75602(10) 0.0516(4) Uani 1 1 d . . . C2 C 0.37473(11) -0.09384(10) 0.70297(9) 0.0448(3) Uani 1 1 d . A . C3 C 0.31283(12) -0.07255(11) 0.62071(9) 0.0473(4) Uani 1 1 d . . . C4 C 0.25406(13) 0.00468(11) 0.61367(10) 0.0519(4) Uani 1 1 d . . . C5 C 0.44730(12) -0.17222(10) 0.72915(9) 0.0455(4) Uani 1 1 d D . . C7 C 0.5039(5) -0.3255(2) 0.7297(2) 0.0698(14) Uani 0.50 1 d PD . . C8 C 0.40501(15) -0.03451(13) 0.84549(10) 0.0621(5) Uani 1 1 d . . . H8A H 0.4632 -0.0787 0.8628 0.075 Uiso 1 1 calc R . . C9 C 0.3216(2) -0.0661(2) 0.87763(13) 0.1026(8) Uani 1 1 d . . . H9A H 0.2973 -0.1257 0.8576 0.154 Uiso 1 1 calc R . . H9B H 0.2627 -0.0246 0.8608 0.154 Uiso 1 1 calc R . . H9C H 0.3523 -0.0678 0.9348 0.154 Uiso 1 1 calc R . . C10 C 0.4508(2) 0.05644(17) 0.88021(14) 0.1006(8) Uani 1 1 d . . . H10A H 0.5030 0.0748 0.8591 0.151 Uiso 1 1 calc R . . H10B H 0.4836 0.0515 0.9371 0.151 Uiso 1 1 calc R . . H10C H 0.3950 0.1008 0.8665 0.151 Uiso 1 1 calc R . . C11 C 0.31621(15) -0.12495(13) 0.55028(10) 0.0627(5) Uani 1 1 d . . . H11A H 0.3029 -0.0845 0.5060 0.094 Uiso 1 1 calc R . . H11B H 0.2629 -0.1715 0.5362 0.094 Uiso 1 1 calc R . . H11C H 0.3850 -0.1522 0.5638 0.094 Uiso 1 1 calc R . . C12 C 0.18287(13) 0.05436(12) 0.54273(10) 0.0561(4) Uani 1 1 d . . . C13 C 0.11109(14) 0.01150(14) 0.47708(11) 0.0624(5) Uani 1 1 d . . . H13A H 0.1084 -0.0516 0.4758 0.075 Uiso 1 1 calc R . . C14 C 0.04224(15) 0.06041(15) 0.41232(11) 0.0679(5) Uani 1 1 d . . . H14A H -0.0057 0.0302 0.3685 0.081 Uiso 1 1 calc R . . C15 C 0.04593(16) 0.15325(15) 0.41383(12) 0.0728(5) Uani 1 1 d . . . C16 C 0.1171(2) 0.19704(16) 0.47766(15) 0.0977(8) Uani 1 1 d . . . H16A H 0.1204 0.2601 0.4780 0.117 Uiso 1 1 calc R . . C17 C 0.18424(19) 0.14886(15) 0.54157(13) 0.0850(7) Uani 1 1 d . . . H17A H 0.2317 0.1800 0.5850 0.102 Uiso 1 1 calc R . . C18 C -0.10345(19) 0.1697(2) 0.29198(15) 0.1044(9) Uani 1 1 d . . . H18A H -0.1395 0.2157 0.2538 0.157 Uiso 1 1 calc R . . H18B H -0.1516 0.1440 0.3139 0.157 Uiso 1 1 calc R . . H18C H -0.0787 0.1230 0.2662 0.157 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 S1 0.0675(3) 0.0619(3) 0.0556(3) -0.0073(2) 0.0153(2) 0.0223(2) C6A 0.073(7) 0.025(3) 0.080(4) -0.012(3) 0.023(4) -0.021(3) F1A 0.080(2) 0.0615(19) 0.112(3) -0.0229(17) 0.013(2) -0.0272(16) F2A 0.103(3) 0.080(2) 0.129(3) 0.014(2) 0.065(2) -0.028(2) C6B 0.056(6) 0.077(6) 0.083(5) 0.016(4) 0.019(4) 0.002(4) F1B 0.182(4) 0.0544(16) 0.082(2) -0.0215(14) -0.003(3) 0.000(3) F2B 0.078(3) 0.0675(19) 0.273(8) 0.032(4) 0.077(3) -0.014(2) F3 0.128(2) 0.0772(17) 0.104(2) -0.0247(15) 0.0495(18) 0.0101(16) F4 0.133(2) 0.0375(9) 0.143(5) 0.027(4) 0.039(4) 0.001(6) O1 0.1006(12) 0.0929(12) 0.0890(11) 0.0244(9) -0.0002(10) 0.0077(10) C1 0.0484(9) 0.0535(9) 0.0500(9) -0.0040(7) 0.0150(7) 0.0069(7) C2 0.0411(8) 0.0421(8) 0.0519(8) -0.0033(6) 0.0183(7) -0.0012(6) C3 0.0451(8) 0.0471(8) 0.0493(8) -0.0046(6) 0.0172(7) -0.0035(6) C4 0.0492(9) 0.0516(9) 0.0510(9) -0.0025(7) 0.0144(7) 0.0017(7) C5 0.0495(8) 0.0373(8) 0.0528(9) -0.0016(6) 0.0229(7) -0.0041(6) C7 0.086(3) 0.0357(15) 0.091(5) -0.0043(17) 0.037(4) -0.002(2) C8 0.0616(11) 0.0720(12) 0.0478(9) -0.0061(8) 0.0147(8) 0.0139(9) C9 0.1009(18) 0.152(2) 0.0576(13) -0.0003(14) 0.0324(13) -0.0110(17) C10 0.125(2) 0.0897(17) 0.0634(13) -0.0232(12) 0.0074(13) -0.0085(15) C11 0.0692(11) 0.0634(11) 0.0552(10) -0.0102(8) 0.0227(9) 0.0047(9) C12 0.0528(10) 0.0582(10) 0.0541(9) 0.0023(8) 0.0163(8) 0.0039(8) C13 0.0590(10) 0.0631(11) 0.0595(10) 0.0007(8) 0.0156(9) 0.0020(8) C14 0.0579(11) 0.0837(14) 0.0553(10) -0.0021(9) 0.0134(8) -0.0029(9) C15 0.0686(12) 0.0712(13) 0.0701(12) 0.0162(10) 0.0161(10) 0.0086(10) C16 0.1107(19) 0.0584(12) 0.0933(17) 0.0093(11) 0.0029(15) 0.0068(12) C17 0.0949(16) 0.0593(12) 0.0726(13) 0.0022(10) -0.0011(12) 0.0044(11) C18 0.0673(14) 0.140(2) 0.0870(17) 0.0293(16) 0.0075(12) 0.0044(15) _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 S1 C1 1.7157(16) . ? S1 C4 1.7294(17) . ? C6A F2A 1.3399(10) . ? C6A F1A 1.3404(10) . ? C6A C7 1.517(7) . ? C6A C5 1.518(5) . ? C6B F2B 1.3403(10) . ? C6B F1B 1.3406(10) . ? C6B C5 1.509(7) . ? C6B C7 1.540(8) 2_656 ? F3 C7 1.3408(10) . ? F4 C7 1.3403(10) . ? O1 C15 1.382(2) . ? O1 C18 1.387(3) . ? C1 C2 1.371(2) . ? C1 C8 1.502(2) . ? C2 C3 1.444(2) . ? C2 C5 1.476(2) . ? C3 C4 1.367(2) . ? C3 C11 1.505(2) . ? C4 C12 1.480(2) . ? C5 C5 1.344(3) 2_656 ? C7 C6A 1.464(9) 2_656 ? C7 C6B 1.540(8) 2_656 ? C8 C10 1.511(3) . ? C8 C9 1.526(3) . ? C12 C13 1.376(2) . ? C12 C17 1.392(3) . ? C13 C14 1.395(3) . ? C14 C15 1.368(3) . ? C15 C16 1.360(3) . ? C16 C17 1.372(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 93.17(8) . . ? F2A C6A F1A 105.7(4) . . ? F2A C6A C7 111.8(4) . . ? F1A C6A C7 112.1(4) . . ? F2A C6A C5 110.5(3) . . ? F1A C6A C5 113.4(4) . . ? C7 C6A C5 103.5(3) . . ? F2B C6B F1B 108.9(5) . . ? F2B C6B C5 110.6(4) . . ? F1B C6B C5 116.1(5) . . ? F2B C6B C7 108.1(5) . 2_656 ? F1B C6B C7 109.4(5) . 2_656 ? C5 C6B C7 103.3(3) . 2_656 ? C15 O1 C18 118.9(2) . . ? C2 C1 C8 130.16(15) . . ? C2 C1 S1 110.25(12) . . ? C8 C1 S1 119.50(12) . . ? C1 C2 C3 113.70(14) . . ? C1 C2 C5 122.10(15) . . ? C3 C2 C5 124.20(13) . . ? C4 C3 C2 111.77(14) . . ? C4 C3 C11 123.28(15) . . ? C2 C3 C11 124.86(15) . . ? C3 C4 C12 131.38(16) . . ? C3 C4 S1 111.10(12) . . ? C12 C4 S1 117.50(12) . . ? C5 C5 C2 128.48(8) 2_656 . ? C5 C5 C6B 110.7(2) 2_656 . ? C2 C5 C6B 120.8(3) . . ? C5 C5 C6A 109.0(2) 2_656 . ? C2 C5 C6A 122.0(2) . . ? F4 C7 F3 107.8(5) . . ? F4 C7 C6A 116.9(12) . 2_656 ? F3 C7 C6A 105.6(4) . 2_656 ? F4 C7 C6A 112.0(11) . . ? F3 C7 C6A 110.1(4) . . ? C6A C7 C6A 104.1(3) 2_656 . ? F4 C7 C6B 113.4(12) . 2_656 ? F3 C7 C6B 111.5(4) . 2_656 ? C6A C7 C6B 5.9(2) 2_656 2_656 ? C6A C7 C6B 101.9(2) . 2_656 ? C1 C8 C10 112.14(17) . . ? C1 C8 C9 111.05(16) . . ? C10 C8 C9 111.1(2) . . ? C13 C12 C17 117.04(17) . . ? C13 C12 C4 122.97(17) . . ? C17 C12 C4 119.96(17) . . ? C12 C13 C14 121.61(19) . . ? C15 C14 C13 119.42(19) . . ? C16 C15 C14 120.00(19) . . ? C16 C15 O1 115.8(2) . . ? C14 C15 O1 124.1(2) . . ? C15 C16 C17 120.5(2) . . ? C16 C17 C12 121.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 S1 C1 C2 -0.11(13) . . . . ? C4 S1 C1 C8 -177.00(15) . . . . ? C4 S1 C1 C1 70.87(9) . . . 2_656 ? C8 C1 C2 C3 176.14(17) . . . . ? S1 C1 C2 C3 -0.32(18) . . . . ? C8 C1 C2 C5 -4.2(3) . . . . ? S1 C1 C2 C5 179.31(11) . . . . ? C1 C2 C3 C4 0.7(2) . . . . ? C5 C2 C3 C4 -178.89(14) . . . . ? C1 C2 C3 C11 177.42(16) . . . . ? C5 C2 C3 C11 -2.2(2) . . . . ? C2 C3 C4 C12 177.43(16) . . . . ? C11 C3 C4 C12 0.7(3) . . . . ? C2 C3 C4 S1 -0.80(18) . . . . ? C11 C3 C4 S1 -177.54(13) . . . . ? C1 S1 C4 C3 0.54(14) . . . . ? C1 S1 C4 C12 -177.96(14) . . . . ? C1 C2 C5 C5 -60.4(3) . . . 2_656 ? C3 C2 C5 C5 119.2(2) . . . 2_656 ? C1 C2 C5 C6B 118.0(2) . . . . ? C3 C2 C5 C6B -62.4(3) . . . . ? C1 C2 C5 C6A 110.4(2) . . . . ? C3 C2 C5 C6A -70.0(2) . . . . ? F2B C6B C5 C5 131.8(5) . . . 2_656 ? F1B C6B C5 C5 -103.5(5) . . . 2_656 ? C7 C6B C5 C5 16.3(3) 2_656 . . 2_656 ? F2B C6B C5 C2 -46.9(5) . . . . ? F1B C6B C5 C2 77.8(4) . . . . ? C7 C6B C5 C2 -162.40(19) 2_656 . . . ? F2B C6B C5 C6A 56(3) . . . . ? F1B C6B C5 C6A -180(100) . . . . ? C7 C6B C5 C6A -60(3) 2_656 . . . ? F2A C6A C5 C5 94.9(4) . . . 2_656 ? F1A C6A C5 C5 -146.5(4) . . . 2_656 ? C7 C6A C5 C5 -24.9(3) . . . 2_656 ? F2A C6A C5 C2 -77.5(4) . . . . ? F1A C6A C5 C2 41.0(4) . . . . ? C7 C6A C5 C2 162.66(19) . . . . ? F2A C6A C5 C6B -159(4) . . . . ? F1A C6A C5 C6B -40(3) . . . . ? C7 C6A C5 C6B 81(3) . . . . ? F2A C6A C7 F4 35.8(10) . . . . ? F1A C6A C7 F4 -82.7(9) . . . . ? C5 C6A C7 F4 154.7(9) . . . . ? F2A C6A C7 F3 155.7(3) . . . . ? F1A C6A C7 F3 37.2(5) . . . . ? C5 C6A C7 F3 -85.3(4) . . . . ? F2A C6A C7 C6A -91.4(4) . . . 2_656 ? F1A C6A C7 C6A 150.1(3) . . . 2_656 ? C5 C6A C7 C6A 27.5(2) . . . 2_656 ? F2A C6A C7 C6B -85.8(3) . . . 2_656 ? F1A C6A C7 C6B 155.7(4) . . . 2_656 ? C5 C6A C7 C6B 33.2(3) . . . 2_656 ? C2 C1 C8 C10 132.5(2) . . . . ? S1 C1 C8 C10 -51.3(2) . . . . ? C2 C1 C8 C9 -102.5(2) . . . . ? S1 C1 C8 C9 73.7(2) . . . . ? C3 C4 C12 C13 42.9(3) . . . . ? S1 C4 C12 C13 -138.93(16) . . . . ? C3 C4 C12 C17 -139.2(2) . . . . ? S1 C4 C12 C17 38.9(2) . . . . ? C17 C12 C13 C14 -0.3(3) . . . . ? C4 C12 C13 C14 177.56(17) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? C13 C14 C15 O1 179.2(2) . . . . ? C18 O1 C15 C16 -169.3(2) . . . . ? C18 O1 C15 C14 12.2(3) . . . . ? C14 C15 C16 C17 -1.3(4) . . . . ? O1 C15 C16 C17 -179.8(2) . . . . ? C15 C16 C17 C12 1.0(4) . . . . ? C13 C12 C17 C16 -0.2(3) . . . . ? C4 C12 C17 C16 -178.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.303 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.041 #===END