#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 loop_ _publ_author_address ; Department of Chemistry and Biochemistry Graduate School of Engineering, Kyushu University Motooka 744, Nishi-ku, Fukuoka 819-0395, Japan ; _publ_contact_author_name 'Irie, Masahiro' _publ_contact_author_email iriem@rikkyo.ne.jp _publ_section_title ; Photoinduced shape changes of diarylethene single crystals: correlation between shape changes and molecular packing ; _publ_contact_author_address ; Department of Chemistry and Research Center for Smart Molecules Rikkyo University Nishi-Ikebukuro 3-43-1, Toshima-ku, Tokyo 171-8501, Japan ; _publ_contact_author_fax ; +81-3-3985-2397 ; _publ_contact_author_phone ; +81-3-3985-2397 ; _publ_author_name M.Irie data_1am _database_code_depnum_ccdc_archive 'CCDC 713390' _publ_section_abstract ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-bis(2-ethyl-5-phenyl-3-thienyl)perfluorocyclopentene ; _chemical_name_common 1,2-bis(2-ethyl-5-phenyl-3-thienyl)perfluorocyclopentene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H22 F6 S2' _chemical_formula_weight 548.61 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 22.339(5) _cell_length_b 10.971(3) _cell_length_c 10.585(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2594.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 179 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 17.22 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.020 _exptl_crystal_size_mid 0.015 _exptl_crystal_size_min 0.008 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; This crystal was prepared by sublimation of the compound. The size order of the crystal is around 10 micrometer. Because of the small size of the crystal, it was impossible to collect enough number of reflection. Although the data quality is poor, the analysis confirms that the micrometer-size crystal has the identical structure as the bulk large crystal. ; _diffrn_ambient_temperature 100 _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 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2601 _diffrn_reflns_av_R_equivalents 0.0977 _diffrn_reflns_av_sigmaI/netI 0.2424 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 23.10 _reflns_number_total 1481 _reflns_number_gt 606 _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. The CF2 groups in the cyclopentene ring were disordered equally. The ethyl groups were also disordered. Geometries of disordered ethyl were restrained by using SADI instractions on the C-C bond lengths and the occupancy of the disordered models was refined. Anisotropic parameters of all non-hydrogen atoms were restrained by SIMU instraction. ; _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^)+(0.0240P)^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 1481 _refine_ls_number_parameters 213 _refine_ls_number_restraints 211 _refine_ls_R_factor_all 0.2024 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0766 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 0.854 _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 0.4193(3) 0.7059(7) 0.2898(7) 0.033(2) Uani 1 1 d DU . . C2 C 0.4303(3) 0.7968(6) 0.2041(6) 0.0179(18) Uani 1 1 d U A . C3 C 0.3938(3) 0.7888(7) 0.0934(6) 0.023(2) Uani 1 1 d U . . H3 H 0.3958 0.8461 0.0262 0.027 Uiso 1 1 calc R A . C4 C 0.3557(3) 0.6909(6) 0.0932(6) 0.026(2) Uani 1 1 d U A . C5 C 0.4722(2) 0.8993(6) 0.2280(6) 0.0185(18) Uani 1 1 d U . . C7 C 0.5000 1.1103(10) 0.2500 0.025(3) Uani 1 2 d SU . . C10 C 0.3121(3) 0.6571(6) -0.0036(7) 0.027(2) Uani 1 1 d U . . C11 C 0.3162(3) 0.7043(6) -0.1266(7) 0.031(2) Uani 1 1 d U A . H11 H 0.3492 0.7541 -0.1497 0.037 Uiso 1 1 calc R . . C12 C 0.2724(3) 0.6779(7) -0.2132(7) 0.031(2) Uani 1 1 d U . . H12 H 0.2751 0.7113 -0.2958 0.037 Uiso 1 1 calc R A . C13 C 0.2251(3) 0.6050(8) -0.1833(7) 0.038(2) Uani 1 1 d U A . H13 H 0.1948 0.5892 -0.2442 0.045 Uiso 1 1 calc R . . C14 C 0.2213(3) 0.5550(7) -0.0661(8) 0.048(3) Uani 1 1 d U . . H14 H 0.1888 0.5024 -0.0464 0.058 Uiso 1 1 calc R A . C15 C 0.2641(3) 0.5797(7) 0.0249(7) 0.038(2) Uani 1 1 d U A . H15 H 0.2609 0.5443 0.1065 0.045 Uiso 1 1 calc R . . C8A C 0.4452(19) 0.685(2) 0.417(2) 0.041(6) Uani 0.709(13) 1 d PDU A 2 H8AA H 0.4770 0.6225 0.4091 0.049 Uiso 0.709(13) 1 calc PR A 2 H8AB H 0.4646 0.7614 0.4451 0.049 Uiso 0.709(13) 1 calc PR A 2 C9A C 0.4030(6) 0.6452(12) 0.5168(11) 0.092(7) Uani 0.709(13) 1 d PDU A 2 H9A H 0.4249 0.6330 0.5961 0.138 Uiso 0.709(13) 1 calc PR A 2 H9B H 0.3840 0.5686 0.4915 0.138 Uiso 0.709(13) 1 calc PR A 2 H9C H 0.3723 0.7079 0.5290 0.138 Uiso 0.709(13) 1 calc PR A 2 C8B C 0.443(5) 0.687(6) 0.419(6) 0.042(12) Uani 0.291(13) 1 d PDU A 3 H8BA H 0.4744 0.7487 0.4347 0.050 Uiso 0.291(13) 1 calc PR A 3 H8BB H 0.4100 0.7033 0.4798 0.050 Uiso 0.291(13) 1 calc PR A 3 C9B C 0.4678(15) 0.566(3) 0.447(3) 0.063(13) Uani 0.291(13) 1 d PDU A 3 H9D H 0.4823 0.5642 0.5347 0.094 Uiso 0.291(13) 1 calc PR A 3 H9E H 0.5011 0.5490 0.3897 0.094 Uiso 0.291(13) 1 calc PR A 3 H9F H 0.4366 0.5039 0.4363 0.094 Uiso 0.291(13) 1 calc PR A 3 F3 F 0.5160(12) 1.2064(15) 0.172(3) 0.031(5) Uani 0.50 1 d PU A . F4 F 0.5233(13) 1.1584(15) 0.144(3) 0.037(5) Uani 0.50 1 d PU A . C6A C 0.4534(14) 1.025(3) 0.188(3) 0.016(7) Uiso 0.50 1 d PU A 1 F1A F 0.4534(7) 1.044(2) 0.0587(16) 0.038(5) Uani 0.50 1 d PU A 1 F2A F 0.3972(7) 1.0568(14) 0.2267(12) 0.032(4) Uani 0.50 1 d PU A 1 C6B C 0.4482(15) 1.025(2) 0.221(2) 0.020(7) Uiso 0.50 1 d PU A 2 F1B F 0.4262(8) 1.053(2) 0.1041(16) 0.040(5) Uani 0.50 1 d PU A 2 F2B F 0.4013(7) 1.0458(15) 0.3048(10) 0.035(4) Uani 0.50 1 d PU A 2 S001 S 0.36451(9) 0.61000(18) 0.23199(18) 0.0421(6) 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 0.041(5) 0.028(5) 0.029(5) 0.005(5) -0.015(5) -0.016(5) C2 0.020(4) 0.017(5) 0.017(4) -0.008(4) -0.001(4) 0.002(4) C3 0.020(5) 0.020(5) 0.028(5) 0.001(4) 0.001(4) 0.003(4) C4 0.039(6) 0.012(5) 0.028(5) -0.003(4) -0.011(4) -0.010(5) C5 0.019(4) 0.017(4) 0.020(4) 0.002(5) 0.006(4) 0.006(3) C7 0.028(7) 0.023(7) 0.025(7) 0.000 -0.009(7) 0.000 C10 0.033(6) 0.025(5) 0.024(5) -0.004(4) -0.012(5) -0.007(4) C11 0.027(5) 0.029(5) 0.036(6) -0.004(5) 0.002(5) -0.008(5) C12 0.027(5) 0.030(5) 0.034(5) -0.007(5) 0.003(5) -0.003(4) C13 0.035(5) 0.049(6) 0.029(5) -0.006(5) -0.007(5) -0.005(6) C14 0.041(6) 0.068(7) 0.036(6) -0.015(6) -0.013(5) -0.035(5) C15 0.051(6) 0.037(6) 0.025(5) 0.008(5) 0.003(5) -0.024(5) C8A 0.047(11) 0.033(11) 0.042(11) 0.004(10) -0.017(10) -0.018(10) C9A 0.108(13) 0.131(16) 0.036(9) 0.022(9) -0.019(9) -0.099(12) C8B 0.05(2) 0.04(2) 0.04(2) 0.01(2) -0.02(2) -0.02(2) C9B 0.12(3) 0.04(2) 0.033(19) -0.003(16) -0.02(2) 0.008(19) F3 0.019(9) 0.020(11) 0.054(11) 0.012(9) -0.006(8) -0.013(9) F4 0.036(9) 0.021(12) 0.055(12) 0.023(10) 0.002(8) 0.002(10) F1A 0.070(13) 0.025(7) 0.019(10) 0.007(8) -0.012(7) -0.007(10) F2A 0.014(7) 0.028(7) 0.054(10) -0.009(10) 0.010(9) 0.002(5) F1B 0.062(13) 0.021(7) 0.036(14) 0.006(10) -0.020(11) -0.008(10) F2B 0.027(8) 0.030(8) 0.049(9) -0.005(9) 0.014(8) 0.004(6) S001 0.0606(14) 0.0312(13) 0.0346(13) 0.0102(15) -0.0096(13) -0.0232(13) _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 1.371(8) . ? C1 C8B 1.48(4) . ? C1 C8A 1.483(16) . ? C1 S001 1.726(6) . ? C2 C3 1.430(8) . ? C2 C5 1.484(7) . ? C3 C4 1.371(8) . ? C3 H3 0.9500 . ? C4 C10 1.462(9) . ? C4 S001 1.728(7) . ? C5 C5 1.326(10) 3_655 ? C5 C6B 1.48(3) . ? C5 C6A 1.51(3) . ? C7 F4 1.34(3) 3_655 ? C7 F4 1.34(3) . ? C7 F3 1.39(3) 3_655 ? C7 F3 1.39(3) . ? C7 C6B 1.52(3) . ? C7 C6B 1.52(3) 3_655 ? C7 C6A 1.54(3) . ? C7 C6A 1.54(3) 3_655 ? C10 C15 1.400(8) . ? C10 C11 1.404(9) . ? C11 C12 1.372(8) . ? C11 H11 0.9500 . ? C12 C13 1.363(8) . ? C12 H12 0.9500 . ? C13 C14 1.359(9) . ? C13 H13 0.9500 . ? C14 C15 1.385(8) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C8A C9A 1.48(4) . ? C8A H8AA 0.9900 . ? C8A H8AB 0.9900 . ? C9A H9A 0.9800 . ? C9A H9B 0.9800 . ? C9A H9C 0.9800 . ? C8B C9B 1.47(4) . ? C8B H8BA 0.9900 . ? C8B H8BB 0.9900 . ? C9B H9D 0.9800 . ? C9B H9E 0.9800 . ? C9B H9F 0.9800 . ? F3 F4 0.63(3) . ? C6A F2A 1.36(3) . ? C6A F1A 1.39(4) . ? C6B F1B 1.36(4) . ? C6B F2B 1.39(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 C2 C1 C8B 130(4) . . ? C2 C1 C8A 130.0(15) . . ? C2 C1 S001 109.6(5) . . ? C8B C1 S001 120(4) . . ? C8A C1 S001 120.3(15) . . ? C1 C2 C3 113.3(7) . . ? C1 C2 C5 123.5(6) . . ? C3 C2 C5 123.1(7) . . ? C4 C3 C2 113.8(7) . . ? C4 C3 H3 123.1 . . ? C2 C3 H3 123.1 . . ? C3 C4 C10 127.9(7) . . ? C3 C4 S001 109.3(5) . . ? C10 C4 S001 122.8(6) . . ? C5 C5 C6B 110.9(12) 3_655 . ? C5 C5 C2 130.6(4) 3_655 . ? C6B C5 C2 117.9(13) . . ? C5 C5 C6A 111.0(13) 3_655 . ? C2 C5 C6A 118.2(13) . . ? F4 C7 F4 133.8(15) 3_655 . ? F4 C7 F3 26.4(11) 3_655 3_655 ? F4 C7 F3 107.5(12) . 3_655 ? F4 C7 F3 107.5(12) 3_655 . ? F4 C7 F3 26.4(11) . . ? F3 C7 F3 81.1(16) 3_655 . ? F4 C7 C6B 96.5(15) 3_655 . ? F4 C7 C6B 111.6(15) . . ? F3 C7 C6B 113.1(15) 3_655 . ? F3 C7 C6B 122.8(14) . . ? F4 C7 C6B 111.6(15) 3_655 3_655 ? F4 C7 C6B 96.6(15) . 3_655 ? F3 C7 C6B 122.8(14) 3_655 3_655 ? F3 C7 C6B 113.1(15) . 3_655 ? C6B C7 C6B 104(2) . 3_655 ? F4 C7 C6A 109.2(14) 3_655 . ? F4 C7 C6A 98.3(15) . . ? F3 C7 C6A 122.6(14) 3_655 . ? F3 C7 C6A 112.3(16) . . ? C6B C7 C6A 103.2(9) 3_655 . ? F4 C7 C6A 98.3(15) 3_655 3_655 ? F4 C7 C6A 109.2(14) . 3_655 ? F3 C7 C6A 112.3(16) 3_655 3_655 ? F3 C7 C6A 122.6(14) . 3_655 ? C6B C7 C6A 103.2(9) . 3_655 ? C6A C7 C6A 106(3) . 3_655 ? C15 C10 C11 118.3(7) . . ? C15 C10 C4 120.9(8) . . ? C11 C10 C4 120.8(8) . . ? C12 C11 C10 119.6(7) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 121.5(8) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C14 C13 C12 119.8(8) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.9(7) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C14 C15 C10 119.9(7) . . ? C14 C15 H15 120.1 . . ? C10 C15 H15 120.1 . . ? C9A C8A C1 116(3) . . ? C9A C8A H8AA 108.2 . . ? C1 C8A H8AA 108.2 . . ? C9A C8A H8AB 108.2 . . ? C1 C8A H8AB 108.2 . . ? H8AA C8A H8AB 107.3 . . ? C8A C9A H9A 109.5 . . ? C8A C9A H9B 109.5 . . ? H9A C9A H9B 109.5 . . ? C8A C9A H9C 109.5 . . ? H9A C9A H9C 109.5 . . ? H9B C9A H9C 109.5 . . ? C9B C8B C1 117(4) . . ? C9B C8B H8BA 108.2 . . ? C1 C8B H8BA 108.2 . . ? C9B C8B H8BB 108.2 . . ? C1 C8B H8BB 108.2 . . ? H8BA C8B H8BB 107.3 . . ? C8B C9B H9D 109.5 . . ? C8B C9B H9E 109.5 . . ? H9D C9B H9E 109.5 . . ? C8B C9B H9F 109.5 . . ? H9D C9B H9F 109.5 . . ? H9E C9B H9F 109.5 . . ? F4 F3 C7 73(5) . . ? F3 F4 C7 81(5) . . ? F2A C6A F1A 105(3) . . ? F2A C6A C5 113.9(19) . . ? F1A C6A C5 114.2(19) . . ? F2A C6A C7 110.1(17) . . ? F1A C6A C7 109.4(19) . . ? C5 C6A C7 104(2) . . ? F1B C6B F2B 106(3) . . ? F1B C6B C5 112(2) . . ? F2B C6B C5 113.1(19) . . ? F1B C6B C7 108.8(18) . . ? F2B C6B C7 110.2(18) . . ? C5 C6B C7 107(2) . . ? C1 S001 C4 94.0(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 C8B C1 C2 C3 -174(5) . . . . ? C8A C1 C2 C3 -177(2) . . . . ? S001 C1 C2 C3 0.7(7) . . . . ? C8B C1 C2 C5 1(5) . . . . ? C8A C1 C2 C5 -2(2) . . . . ? S001 C1 C2 C5 176.0(5) . . . . ? C1 C2 C3 C4 -1.1(9) . . . . ? C5 C2 C3 C4 -176.3(6) . . . . ? C2 C3 C4 C10 179.0(7) . . . . ? C2 C3 C4 S001 0.9(7) . . . . ? C1 C2 C5 C5 48.1(13) . . . 3_655 ? C3 C2 C5 C5 -137.2(10) . . . 3_655 ? C1 C2 C5 C6B -121.7(13) . . . . ? C3 C2 C5 C6B 53.1(14) . . . . ? C1 C2 C5 C6A -137.6(12) . . . . ? C3 C2 C5 C6A 37.2(14) . . . . ? C3 C4 C10 C15 -159.6(7) . . . . ? S001 C4 C10 C15 18.3(10) . . . . ? C3 C4 C10 C11 18.4(11) . . . . ? S001 C4 C10 C11 -163.7(6) . . . . ? C15 C10 C11 C12 2.7(11) . . . . ? C4 C10 C11 C12 -175.4(7) . . . . ? C10 C11 C12 C13 -1.1(11) . . . . ? C11 C12 C13 C14 -1.2(12) . . . . ? C12 C13 C14 C15 1.8(13) . . . . ? C13 C14 C15 C10 -0.1(12) . . . . ? C11 C10 C15 C14 -2.1(11) . . . . ? C4 C10 C15 C14 176.0(7) . . . . ? C2 C1 C8A C9A 138.6(17) . . . . ? C8B C1 C8A C9A 37(100) . . . . ? S001 C1 C8A C9A -39(2) . . . . ? C2 C1 C8B C9B -130(5) . . . . ? C8A C1 C8B C9B -49(97) . . . . ? S001 C1 C8B C9B 56(9) . . . . ? F4 C7 F3 F4 178(3) 3_655 . . . ? F3 C7 F3 F4 177(6) 3_655 . . . ? C6B C7 F3 F4 -72(5) . . . . ? C6B C7 F3 F4 55(5) 3_655 . . . ? C6A C7 F3 F4 -62(5) . . . . ? C6A C7 F3 F4 66(5) 3_655 . . . ? F4 C7 F4 F3 -2(4) 3_655 . . . ? F3 C7 F4 F3 -4(6) 3_655 . . . ? C6B C7 F4 F3 121(5) . . . . ? C6B C7 F4 F3 -131(5) 3_655 . . . ? C6A C7 F4 F3 125(5) . . . . ? C6A C7 F4 F3 -126(5) 3_655 . . . ? C5 C5 C6A F2A -136(2) 3_655 . . . ? C6B C5 C6A F2A -44(8) . . . . ? C2 C5 C6A F2A 49(3) . . . . ? C5 C5 C6A F1A 104(2) 3_655 . . . ? C6B C5 C6A F1A -164(12) . . . . ? C2 C5 C6A F1A -72(2) . . . . ? C5 C5 C6A C7 -15.7(17) 3_655 . . . ? C6B C5 C6A C7 76(10) . . . . ? C2 C5 C6A C7 168.9(8) . . . . ? F4 C7 C6A F2A 23(3) 3_655 . . . ? F4 C7 C6A F2A -119(2) . . . . ? F3 C7 C6A F2A -2(3) 3_655 . . . ? F3 C7 C6A F2A -96(2) . . . . ? C6B C7 C6A F2A 46(8) . . . . ? C6B C7 C6A F2A 142(2) 3_655 . . . ? C6A C7 C6A F2A 128(3) 3_655 . . . ? F4 C7 C6A F1A 138(2) 3_655 . . . ? F4 C7 C6A F1A -5(2) . . . . ? F3 C7 C6A F1A 112(2) 3_655 . . . ? F3 C7 C6A F1A 19(3) . . . . ? C6B C7 C6A F1A 161(11) . . . . ? C6B C7 C6A F1A -103.5(19) 3_655 . . . ? C6A C7 C6A F1A -117(2) 3_655 . . . ? F4 C7 C6A C5 -99.7(16) 3_655 . . . ? F4 C7 C6A C5 117.9(15) . . . . ? F3 C7 C6A C5 -125.1(15) 3_655 . . . ? F3 C7 C6A C5 141.2(14) . . . . ? C6B C7 C6A C5 -76(10) . . . . ? C6B C7 C6A C5 19(2) 3_655 . . . ? C6A C7 C6A C5 5.2(6) 3_655 . . . ? C5 C5 C6B F1B 127(2) 3_655 . . . ? C2 C5 C6B F1B -61(2) . . . . ? C6A C5 C6B F1B 34(8) . . . . ? C5 C5 C6B F2B -113.4(19) 3_655 . . . ? C2 C5 C6B F2B 58(2) . . . . ? C6A C5 C6B F2B 153(11) . . . . ? C5 C5 C6B C7 7.9(19) 3_655 . . . ? C2 C5 C6B C7 179.6(9) . . . . ? C6A C5 C6B C7 -85(10) . . . . ? F4 C7 C6B F1B 122(2) 3_655 . . . ? F4 C7 C6B F1B -21(3) . . . . ? F3 C7 C6B F1B 100(2) 3_655 . . . ? F3 C7 C6B F1B 6(3) . . . . ? C6B C7 C6B F1B -124(3) 3_655 . . . ? C6A C7 C6B F1B -36(8) . . . . ? C6A C7 C6B F1B -138(2) 3_655 . . . ? F4 C7 C6B F2B 6(2) 3_655 . . . ? F4 C7 C6B F2B -136.5(17) . . . . ? F3 C7 C6B F2B -15(2) 3_655 . . . ? F3 C7 C6B F2B -109.5(19) . . . . ? C6B C7 C6B F2B 120(2) 3_655 . . . ? C6A C7 C6B F2B -152(11) . . . . ? C6A C7 C6B F2B 106.4(17) 3_655 . . . ? F4 C7 C6B C5 -116.9(17) 3_655 . . . ? F4 C7 C6B C5 100.4(17) . . . . ? F3 C7 C6B C5 -138.3(16) 3_655 . . . ? F3 C7 C6B C5 127.4(15) . . . . ? C6B C7 C6B C5 -2.7(6) 3_655 . . . ? C6A C7 C6B C5 85(10) . . . . ? C6A C7 C6B C5 -17(2) 3_655 . . . ? C2 C1 S001 C4 -0.2(5) . . . . ? C8B C1 S001 C4 175(4) . . . . ? C8A C1 S001 C4 177.9(17) . . . . ? C3 C4 S001 C1 -0.4(5) . . . . ? C10 C4 S001 C1 -178.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.810 _diffrn_reflns_theta_full 23.10 _diffrn_measured_fraction_theta_full 0.810 _refine_diff_density_max 0.305 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.068 _exptl_crystal_preparation sublimation #===END data_1am' _database_code_depnum_ccdc_archive 'CCDC 713391' _publ_section_abstract ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-bis(2-ethyl-5-phenyl-3-thienyl)perfluorocyclopentene (88%) and 1,2-diethyl-8,8,9,9,10,10-hexafluoro-4,14-diphenyl-3,15-dithiatetracyclo- [10.3.0.0<2,6>.0<7,11>] pentadeca-4,6(7),11(12),13-tetraene (12%) ; _chemical_name_common ; 1,2-bis(2-ethyl-5-phenyl-3-thienyl)perfluorocyclopentene (88%) and 1,2-diethyl-8,8,9,9,10,10-hexafluoro-4,14-diphenyl-3,15- dithiatetracyclo-(10.3.0.0<2,6>.0<7,11>) pentadeca-4,6(7),11(12),13- tetraene (12%) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H22 F6 S2' _chemical_formula_weight 548.61 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 22.30(3) _cell_length_b 11.026(18) _cell_length_c 10.542(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2593(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.020 _exptl_crystal_size_mid 0.015 _exptl_crystal_size_min 0.008 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; This crystal was obtained by UV irradiation of 1,2-bis(2-ethyl-5-phenyl-3-thienyl)perfluorocyclopentene micrometer-size crystal prepared by sublimation. Because of the small size of the crystal, it was impossible to collect enough number of reflection. Although the data quality is poor, the analysis confirms that the molecule underwent the photocyclization reaction to yield the closed-ring isomer in the micrometer-size crystal. ; _diffrn_ambient_temperature 100 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2224 _diffrn_reflns_av_R_equivalents 0.1613 _diffrn_reflns_av_sigmaI/netI 0.2026 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 18.84 _reflns_number_total 1010 _reflns_number_gt 439 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All atoms are refined isotropically and isotropicparameters of all non-hydrogen atoms were restrained by SIMU instraction. The CF2 groups in the cyclopentene ring were disordered equally. The ethyl groups were also disordered. Geometries of disordered ethyl were restrained by using SADI instractions on the C-C bond lengths and the occupancy of the disordered models was refined. Existance of photogenerated isomer was observed by disorder of sulfur and reacting carbon (C1).Bond length between reacting carbons was fixed by DFIX instraction and the occupancy of the disordered model was refined. ; _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^)+(0.1000P)^2^+0.5000P] 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 1010 _refine_ls_number_parameters 107 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.2251 _refine_ls_R_factor_gt 0.1009 _refine_ls_wR_factor_ref 0.2612 _refine_ls_wR_factor_gt 0.2138 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.116 _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 C2 C 0.4323(7) 0.2012(14) 0.2046(15) 0.036(4) Uiso 1 1 d U . . C3 C 0.3935(7) 0.2109(14) 0.0940(16) 0.039(5) Uiso 1 1 d U . . H3 H 0.3930 0.1519 0.0283 0.047 Uiso 1 1 calc R . . C4 C 0.3594(7) 0.3079(14) 0.0926(15) 0.041(5) Uiso 1 1 d U . . C5 C 0.4719(5) 0.1007(13) 0.2264(15) 0.035(4) Uiso 1 1 d U . . C6 C 0.4519(8) -0.0249(14) 0.2040(17) 0.047(5) Uiso 1 1 d U . . C7 C 0.5000 -0.111(2) 0.2500 0.033(6) Uiso 1 2 d SU . . C8A C 0.4515(12) 0.321(3) 0.4107(18) 0.035(10) Uiso 0.66(3) 1 d PDU A 3 H8A1 H 0.4757 0.3960 0.4007 0.041 Uiso 0.66(3) 1 calc PR A 3 H8A2 H 0.4784 0.2542 0.4360 0.041 Uiso 0.66(3) 1 calc PR A 3 C9A C 0.4007(14) 0.341(3) 0.514(3) 0.109(14) Uiso 0.66(3) 1 d PDU A 3 H9A1 H 0.3612 0.3365 0.4732 0.163 Uiso 0.66(3) 1 calc PR A 3 H9A2 H 0.4056 0.4205 0.5537 0.163 Uiso 0.66(3) 1 calc PR A 3 H9A3 H 0.4037 0.2775 0.5789 0.163 Uiso 0.66(3) 1 calc PR A 3 C8B C 0.435(3) 0.299(4) 0.427(3) 0.042(15) Uiso 0.34(3) 1 d PDU A 4 H8B1 H 0.4626 0.2327 0.4522 0.051 Uiso 0.34(3) 1 calc PR A 4 H8B2 H 0.3988 0.2958 0.4804 0.051 Uiso 0.34(3) 1 calc PR A 4 C9B C 0.468(2) 0.427(4) 0.440(6) 0.09(2) Uiso 0.34(3) 1 d PDU A 4 H9B1 H 0.4982 0.4352 0.3740 0.139 Uiso 0.34(3) 1 calc PR A 4 H9B2 H 0.4865 0.4334 0.5238 0.139 Uiso 0.34(3) 1 calc PR A 4 H9B3 H 0.4378 0.4921 0.4305 0.139 Uiso 0.34(3) 1 calc PR A 4 C1P C 0.3125(7) 0.3448(13) -0.0033(16) 0.036(5) Uiso 1 1 d U . . C2P C 0.3168(7) 0.2958(14) -0.1250(16) 0.044(5) Uiso 1 1 d U . . H2P H 0.3498 0.2459 -0.1476 0.053 Uiso 1 1 calc R A . C3P C 0.2712(8) 0.3215(15) -0.2137(18) 0.057(5) Uiso 1 1 d U . . H3P H 0.2730 0.2868 -0.2961 0.069 Uiso 1 1 calc R . . C4P C 0.2253(8) 0.3950(15) -0.1824(16) 0.056(5) Uiso 1 1 d U . . H4P H 0.1940 0.4083 -0.2419 0.067 Uiso 1 1 calc R A . C5P C 0.2230(9) 0.4494(17) -0.0695(19) 0.070(6) Uiso 1 1 d U . . H5P H 0.1926 0.5075 -0.0526 0.084 Uiso 1 1 calc R . . C6P C 0.2650(8) 0.4213(15) 0.0236(18) 0.065(6) Uiso 1 1 d U . . H6P H 0.2610 0.4549 0.1061 0.078 Uiso 1 1 calc R A . F1 F 0.4028(8) -0.0486(16) 0.299(2) 0.042(6) Uiso 0.50 1 d PU A . F2 F 0.4246(9) -0.0507(15) 0.0971(19) 0.036(6) Uiso 0.50 1 d PU A . F3 F 0.5153(7) -0.2057(14) 0.1784(16) 0.026(5) Uiso 0.50 1 d PU . . F4 F 0.5249(8) -0.1519(16) 0.1398(19) 0.043(6) Uiso 0.50 1 d PU . . F1A F 0.3945(9) -0.0520(18) 0.224(2) 0.055(6) Uiso 0.50 1 d PU A . F2A F 0.4555(9) -0.0445(16) 0.0601(17) 0.040(6) Uiso 0.50 1 d PU A . S1 S 0.3637(2) 0.3892(4) 0.2319(5) 0.042(2) Uiso 0.876(11) 1 d PU A 1 C1 C 0.4200(7) 0.2915(15) 0.2901(17) 0.029(5) Uiso 0.876(11) 1 d PDU A 1 S1B S 0.418(2) 0.412(4) 0.185(5) 0.079(18) Uiso 0.124(11) 1 d PU A 2 C1B C 0.4653(5) 0.299(10) 0.245(12) 0.036(19) Uiso 0.124(11) 1 d PDU . 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 C2 C1 1.370(19) . ? C2 C1B 1.37(9) . ? C2 C5 1.436(18) . ? C2 C3 1.46(2) . ? C3 C4 1.313(18) . ? C4 C1P 1.51(2) . ? C4 S1 1.723(16) . ? C4 S1B 2.00(5) . ? C5 C5 1.35(2) 3_655 ? C5 C6 1.475(19) . ? C6 F2 1.31(2) . ? C6 F1A 1.33(2) . ? C6 F1 1.50(2) . ? C6 C7 1.510(19) . ? C6 F2A 1.53(3) . ? C7 F3 1.336(19) . ? C7 F3 1.336(19) 3_655 ? C7 F4 1.366(19) . ? C7 F4 1.366(19) 3_655 ? C7 C6 1.510(19) 3_655 ? C8A C1 1.49(2) . ? C8A C9A 1.59(4) . ? C8B C1 1.49(2) . ? C8B C9B 1.59(4) . ? C1P C6P 1.384(19) . ? C1P C2P 1.39(2) . ? C2P C3P 1.41(2) . ? C3P C4P 1.347(19) . ? C4P C5P 1.33(2) . ? C5P C6P 1.39(2) . ? F1 F1A 0.81(2) . ? F2 F2A 0.79(2) . ? F2 F1A 1.50(3) . ? F3 F4 0.75(2) . ? F3 F3 1.66(3) 3_655 ? S1 C1 1.764(17) . ? S1B C1B 1.75(10) . ? C1B C1B 1.551(11) 3_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 C1 C2 C1B 48(4) . . ? C1 C2 C5 125.3(15) . . ? C1B C2 C5 103(3) . . ? C1 C2 C3 110.8(14) . . ? C1B C2 C3 121(5) . . ? C5 C2 C3 123.4(15) . . ? C4 C3 C2 114.4(16) . . ? C3 C4 C1P 128.9(15) . . ? C3 C4 S1 112.5(13) . . ? C1P C4 S1 118.0(12) . . ? C3 C4 S1B 94.9(17) . . ? C1P C4 S1B 128.6(16) . . ? C5 C5 C2 129.1(9) 3_655 . ? C5 C5 C6 110.0(8) 3_655 . ? C2 C5 C6 120.8(13) . . ? F2 C6 F1A 69.0(15) . . ? F2 C6 C5 118.8(16) . . ? F1A C6 C5 118.5(16) . . ? F2 C6 F1 101.3(16) . . ? C5 C6 F1 106.1(14) . . ? F2 C6 C7 118.0(14) . . ? F1A C6 C7 119.5(16) . . ? C5 C6 C7 108.7(14) . . ? F1 C6 C7 101.2(13) . . ? F1A C6 F2A 100.0(17) . . ? C5 C6 F2A 105.9(14) . . ? F1 C6 F2A 132.1(17) . . ? C7 C6 F2A 101.1(12) . . ? F3 C7 F3 77(2) . 3_655 ? F3 C7 F4 109(2) 3_655 . ? F3 C7 F4 109(2) . 3_655 ? F3 C7 F4 32.2(9) 3_655 3_655 ? F4 C7 F4 141(3) . 3_655 ? F3 C7 C6 119.5(10) . . ? F3 C7 C6 119.4(10) 3_655 . ? F4 C7 C6 103.0(11) . . ? F4 C7 C6 101.1(11) 3_655 . ? F3 C7 C6 119.4(10) . 3_655 ? F3 C7 C6 119.5(10) 3_655 3_655 ? F4 C7 C6 101.1(11) . 3_655 ? F4 C7 C6 103.0(11) 3_655 3_655 ? C6 C7 C6 102.5(18) . 3_655 ? C1 C8A C9A 106(2) . . ? C1 C8B C9B 104(3) . . ? C6P C1P C2P 118.4(17) . . ? C6P C1P C4 123.9(16) . . ? C2P C1P C4 117.7(15) . . ? C1P C2P C3P 119.0(16) . . ? C4P C3P C2P 120.4(19) . . ? C5P C4P C3P 121(2) . . ? C4P C5P C6P 120.2(19) . . ? C1P C6P C5P 120.5(18) . . ? F1A F1 C6 62(2) . . ? F2A F2 C6 90(2) . . ? F2A F2 F1A 146(3) . . ? C6 F2 F1A 56.1(12) . . ? F4 F3 C7 76(2) . . ? F4 F3 F3 128(2) . 3_655 ? C7 F3 F3 51.7(10) . 3_655 ? F3 F4 C7 72(2) . . ? F1 F1A C6 86(3) . . ? F1 F1A F2 140(3) . . ? C6 F1A F2 54.9(12) . . ? F2 F2A C6 59(2) . . ? C4 S1 C1 91.1(8) . . ? C2 C1 C8B 129(2) . . ? C2 C1 C8A 128.8(16) . . ? C2 C1 S1 110.9(12) . . ? C8B C1 S1 118(3) . . ? C8A C1 S1 119.8(15) . . ? C1B S1B C4 99(4) . . ? C2 C1B C1B 124(5) . 3_655 ? C2 C1B S1B 97(4) . . ? C1B C1B S1B 129(6) 3_655 . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 18.84 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.489 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.092 #===END data_3a _database_code_depnum_ccdc_archive 'CCDC 713392' _publ_section_abstract ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-bis(5-ethyl-2-phenyl-4-thiazolyl)perfluorocyclopentene ; _chemical_name_common 1,2-bis(5-ethyl-2-phenyl-4-thiazolyl)perfluorocyclopentene _chemical_melting_point 184 _chemical_formula_moiety ? _chemical_formula_sum 'C27 H20 F6 N2 S2' _chemical_formula_weight 550.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 21.5461(15) _cell_length_b 10.8096(8) _cell_length_c 10.8098(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2517.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 2564 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 23.69 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9219 _exptl_absorpt_correction_T_max 0.9219 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; This crystal was prepared by recrystallization from hexane. ; _diffrn_ambient_temperature 123 _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 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15259 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.90 _reflns_number_total 2727 _reflns_number_gt 1999 _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. The CF2 groups in the cyclopentene ring were disordered equally. The ethyl groups were also disordered and the occupancy of the disordered model was refined. C6A and C6B in the disordered cyclopentene ring and C8B in the minor structure of the disordered ethyl groups were refined isotropically. ; _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^)+(0.0400P)^2^+1.2564P] 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 2727 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.07992(9) 0.20251(17) 0.20100(19) 0.0286(4) Uani 1 1 d . A 4 C2 C 0.07155(8) 0.29414(16) 0.28631(17) 0.0229(4) Uani 1 1 d . A 4 C4 C 0.14508(9) 0.19310(16) 0.38670(18) 0.0247(4) Uani 1 1 d . A 4 C5 C 0.02944(8) 0.39959(15) 0.27057(16) 0.0205(4) Uani 1 1 d . . 4 C7 C 0.0000 0.6136(2) 0.2500 0.0265(6) Uani 1 2 d S . 4 C10 C 0.18986(8) 0.16160(16) 0.48435(18) 0.0251(4) Uani 1 1 d . A 4 C11 C 0.18306(9) 0.21359(17) 0.60141(18) 0.0272(4) Uani 1 1 d . A 4 H11 H 0.1493 0.2675 0.6180 0.033 Uiso 1 1 calc R A 4 C12 C 0.22544(9) 0.18679(18) 0.6934(2) 0.0317(5) Uani 1 1 d . A 4 H12 H 0.2206 0.2224 0.7732 0.038 Uiso 1 1 calc R A 4 C13 C 0.27498(9) 0.10831(18) 0.6703(2) 0.0318(5) Uani 1 1 d . A 4 H13 H 0.3042 0.0910 0.7337 0.038 Uiso 1 1 calc R A 4 C14 C 0.28173(9) 0.05542(19) 0.5548(2) 0.0342(5) Uani 1 1 d . A 4 H14 H 0.3154 0.0008 0.5390 0.041 Uiso 1 1 calc R A 4 C15 C 0.23945(9) 0.08203(18) 0.4619(2) 0.0319(5) Uani 1 1 d . A 4 H15 H 0.2443 0.0458 0.3825 0.038 Uiso 1 1 calc R A 4 N3 N 0.10866(7) 0.29000(13) 0.39061(14) 0.0232(3) Uani 1 1 d . A 4 S1 S 0.13679(2) 0.10348(4) 0.25460(5) 0.03150(16) Uani 1 1 d . A 4 C8A C 0.0488(3) 0.1828(5) 0.0799(5) 0.0380(12) Uani 0.863(5) 1 d P A 1 H8A H 0.0275 0.2600 0.0551 0.046 Uiso 0.863(5) 1 calc PR A 1 H8B H 0.0169 0.1175 0.0891 0.046 Uiso 0.863(5) 1 calc PR A 1 C9A C 0.09442(17) 0.1448(3) -0.0225(3) 0.0765(14) Uani 0.863(5) 1 d P A 1 H9A H 0.0716 0.1311 -0.0997 0.115 Uiso 0.863(5) 1 calc PR A 1 H9B H 0.1157 0.0685 0.0016 0.115 Uiso 0.863(5) 1 calc PR A 1 H9C H 0.1250 0.2108 -0.0347 0.115 Uiso 0.863(5) 1 calc PR A 1 C8B C 0.0618(15) 0.182(3) 0.059(3) 0.021(6) Uiso 0.137(5) 1 d P A 2 H8X H 0.0366 0.2529 0.0303 0.026 Uiso 0.137(5) 1 calc PR A 2 H8Y H 0.1000 0.1784 0.0087 0.026 Uiso 0.137(5) 1 calc PR A 2 C9B C 0.0275(8) 0.0705(14) 0.0442(14) 0.038(5) Uani 0.137(5) 1 d P A 2 H9X H 0.0151 0.0619 -0.0425 0.057 Uiso 0.137(5) 1 calc PR A 2 H9Y H -0.0096 0.0730 0.0966 0.057 Uiso 0.137(5) 1 calc PR A 2 H9Z H 0.0534 0.0000 0.0682 0.057 Uiso 0.137(5) 1 calc PR A 2 C6A C 0.0502(3) 0.5282(5) 0.3096(6) 0.0200(18) Uiso 0.50 1 d P B 3 F1A F 0.1088(2) 0.5560(4) 0.2700(3) 0.0313(9) Uani 0.50 1 d P B 3 F2A F 0.04873(19) 0.5449(6) 0.4285(5) 0.0316(10) Uani 0.50 1 d P B 3 C6B C 0.0524(3) 0.5293(5) 0.2845(6) 0.0221(19) Uiso 0.50 1 d P C 4 F1B F 0.0998(2) 0.5535(5) 0.2092(5) 0.0586(14) Uani 0.50 1 d P C 4 F2B F 0.0735(2) 0.5521(6) 0.4035(6) 0.0574(18) Uani 0.50 1 d P C 4 F3 F 0.01315(14) 0.7104(2) 0.1876(3) 0.0401(7) Uani 0.50 1 d P . . F4 F -0.02779(14) 0.6582(3) 0.3630(3) 0.0400(7) Uani 0.50 1 d P . . 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 0.0335(11) 0.0246(9) 0.0276(11) 0.0002(8) -0.0064(9) 0.0070(8) C2 0.0233(9) 0.0220(9) 0.0235(10) 0.0010(7) -0.0024(8) 0.0018(7) C4 0.0262(10) 0.0231(9) 0.0248(10) 0.0004(7) 0.0005(8) 0.0017(7) C5 0.0214(9) 0.0207(9) 0.0195(9) 0.0001(7) 0.0003(7) 0.0005(7) C7 0.0257(14) 0.0203(12) 0.0336(15) 0.000 -0.0055(12) 0.000 C10 0.0229(9) 0.0235(9) 0.0288(11) 0.0035(8) -0.0017(8) 0.0016(7) C11 0.0223(10) 0.0295(10) 0.0299(11) -0.0002(8) -0.0012(8) 0.0017(8) C12 0.0315(11) 0.0351(11) 0.0285(11) 0.0000(9) -0.0045(9) -0.0018(9) C13 0.0253(10) 0.0349(11) 0.0352(12) 0.0090(9) -0.0072(9) -0.0013(9) C14 0.0257(10) 0.0355(11) 0.0414(13) 0.0053(9) -0.0021(9) 0.0083(9) C15 0.0332(11) 0.0334(11) 0.0291(11) 0.0011(9) 0.0002(9) 0.0079(9) N3 0.0209(8) 0.0244(8) 0.0243(9) 0.0015(6) -0.0013(6) 0.0016(6) S1 0.0406(3) 0.0264(3) 0.0275(3) -0.0033(2) -0.0077(2) 0.0129(2) C8A 0.052(3) 0.0372(18) 0.025(2) -0.0075(15) -0.010(2) 0.0195(19) C9A 0.101(3) 0.098(3) 0.0306(17) -0.0255(17) -0.0199(18) 0.072(2) C9B 0.050(10) 0.045(10) 0.019(8) -0.011(6) -0.007(7) 0.015(8) F1A 0.0168(14) 0.0274(14) 0.050(2) 0.0055(17) 0.0032(17) -0.0044(10) F2A 0.044(3) 0.0270(15) 0.0234(15) -0.0043(11) -0.011(2) -0.002(2) F1B 0.029(2) 0.0341(18) 0.112(4) 0.012(3) 0.035(3) 0.0016(15) F2B 0.065(4) 0.0288(18) 0.078(5) -0.013(3) -0.053(3) 0.005(3) F3 0.0389(19) 0.0263(14) 0.055(2) 0.0143(13) -0.0136(15) -0.0124(12) F4 0.0313(15) 0.0513(19) 0.0375(18) -0.0222(14) -0.0035(13) 0.0071(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 1.365(3) . ? C1 C8A 1.486(5) . ? C1 C8B 1.59(3) . ? C1 S1 1.7272(19) . ? C2 N3 1.383(2) . ? C2 C5 1.467(2) . ? C4 N3 1.309(2) . ? C4 C10 1.470(3) . ? C4 S1 1.7348(19) . ? C5 C5 1.344(3) 3 ? C5 C6B 1.495(6) . ? C5 C6A 1.520(6) . ? C7 F3 1.276(3) 3 ? C7 F3 1.276(3) . ? C7 F4 1.443(3) . ? C7 F4 1.443(3) 3 ? C7 C6B 1.499(6) . ? C7 C6B 1.499(6) 3 ? C7 C6A 1.561(6) . ? C10 C11 1.392(3) . ? C10 C15 1.393(3) . ? C11 C12 1.381(3) . ? C11 H11 0.9500 . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 C14 1.381(3) . ? C13 H13 0.9500 . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C8A C9A 1.536(6) . ? C8A H8A 0.9900 . ? C8A H8B 0.9900 . ? C9A H9A 0.9800 . ? C9A H9B 0.9800 . ? C9A H9C 0.9800 . ? C8B C9B 1.42(4) . ? C8B H8X 0.9900 . ? C8B H8Y 0.9900 . ? C9B H9X 0.9800 . ? C9B H9Y 0.9800 . ? C9B H9Z 0.9800 . ? C6A F2A 1.298(9) . ? C6A F1A 1.366(8) . ? C6B F1B 1.331(8) . ? C6B F2B 1.387(9) . ? F3 F4 0.846(3) 3 ? F3 F3 1.463(7) 3 ? F4 F3 0.846(3) 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 C2 C1 C8A 129.8(2) . . ? C2 C1 C8B 135.7(12) . . ? C2 C1 S1 108.47(14) . . ? C8A C1 S1 121.8(2) . . ? C8B C1 S1 114.2(12) . . ? C1 C2 N3 116.80(16) . . ? C1 C2 C5 124.55(17) . . ? N3 C2 C5 118.52(16) . . ? N3 C4 C10 123.73(17) . . ? N3 C4 S1 114.31(14) . . ? C10 C4 S1 121.96(14) . . ? C5 C5 C2 128.47(10) 3 . ? C5 C5 C6B 110.3(2) 3 . ? C2 C5 C6B 120.8(3) . . ? C5 C5 C6A 111.7(2) 3 . ? C2 C5 C6A 119.8(3) . . ? F3 C7 F3 70.0(3) 3 . ? F3 C7 F4 105.4(3) . . ? F3 C7 F4 105.4(3) 3 3 ? F4 C7 F4 141.0(3) . 3 ? F3 C7 C6B 122.3(3) 3 . ? F3 C7 C6B 117.5(3) . . ? F4 C7 C6B 107.8(3) . . ? F4 C7 C6B 95.8(3) 3 . ? F3 C7 C6B 117.5(3) 3 3 ? F3 C7 C6B 122.3(3) . 3 ? F4 C7 C6B 95.8(3) . 3 ? F4 C7 C6B 107.8(3) 3 3 ? C6B C7 C6B 105.1(5) . 3 ? F3 C7 C6A 114.8(3) 3 . ? F3 C7 C6A 123.3(3) . . ? F4 C7 C6A 97.8(3) . . ? F4 C7 C6A 105.0(3) 3 . ? C6B C7 C6A 105.4(2) 3 . ? C11 C10 C15 119.21(18) . . ? C11 C10 C4 119.34(17) . . ? C15 C10 C4 121.44(18) . . ? C12 C11 C10 120.03(18) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.5(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 119.85(19) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 119.98(19) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 120.4(2) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? C4 N3 C2 110.24(15) . . ? C1 S1 C4 90.17(9) . . ? C1 C8A C9A 112.6(4) . . ? C1 C8A H8A 109.1 . . ? C9A C8A H8A 109.1 . . ? C1 C8A H8B 109.1 . . ? C9A C8A H8B 109.1 . . ? H8A C8A H8B 107.8 . . ? C8A C9A H9A 109.5 . . ? C8A C9A H9B 109.5 . . ? H9A C9A H9B 109.5 . . ? C8A C9A H9C 109.5 . . ? H9A C9A H9C 109.5 . . ? H9B C9A H9C 109.5 . . ? C9B C8B C1 111(2) . . ? C9B C8B H8X 109.5 . . ? C1 C8B H8X 109.5 . . ? C9B C8B H8Y 109.5 . . ? C1 C8B H8Y 109.5 . . ? H8X C8B H8Y 108.1 . . ? C8B C9B H9X 109.5 . . ? C8B C9B H9Y 109.5 . . ? H9X C9B H9Y 109.5 . . ? C8B C9B H9Z 109.5 . . ? H9X C9B H9Z 109.5 . . ? H9Y C9B H9Z 109.5 . . ? F2A C6A F1A 107.6(5) . . ? F2A C6A C5 113.2(5) . . ? F1A C6A C5 112.7(4) . . ? F2A C6A C7 108.0(5) . . ? F1A C6A C7 112.4(4) . . ? C5 C6A C7 102.8(4) . . ? F1B C6B F2B 106.4(5) . . ? F1B C6B C5 112.1(5) . . ? F2B C6B C5 111.6(5) . . ? F1B C6B C7 107.9(5) . . ? F2B C6B C7 111.6(5) . . ? C5 C6B C7 107.2(4) . . ? F4 F3 C7 83.0(3) 3 . ? F4 F3 F3 137.7(3) 3 3 ? C7 F3 F3 55.02(16) . 3 ? F3 F4 C7 61.4(3) 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 C8A C1 C2 N3 -178.5(3) . . . . ? C8B C1 C2 N3 -163.3(16) . . . . ? S1 C1 C2 N3 0.9(2) . . . . ? C8A C1 C2 C5 -2.9(4) . . . . ? C8B C1 C2 C5 12.3(16) . . . . ? S1 C1 C2 C5 176.52(15) . . . . ? C1 C2 C5 C5 45.5(3) . . . 3 ? N3 C2 C5 C5 -138.9(2) . . . 3 ? C1 C2 C5 C6B -125.8(3) . . . . ? N3 C2 C5 C6B 49.7(4) . . . . ? C1 C2 C5 C6A -137.9(3) . . . . ? N3 C2 C5 C6A 37.7(4) . . . . ? N3 C4 C10 C11 18.5(3) . . . . ? S1 C4 C10 C11 -161.98(15) . . . . ? N3 C4 C10 C15 -160.68(18) . . . . ? S1 C4 C10 C15 18.8(3) . . . . ? C15 C10 C11 C12 0.5(3) . . . . ? C4 C10 C11 C12 -178.75(17) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? C11 C12 C13 C14 -0.7(3) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C13 C14 C15 C10 -0.3(3) . . . . ? C11 C10 C15 C14 -0.4(3) . . . . ? C4 C10 C15 C14 178.83(18) . . . . ? C10 C4 N3 C2 -179.49(17) . . . . ? S1 C4 N3 C2 1.0(2) . . . . ? C1 C2 N3 C4 -1.2(2) . . . . ? C5 C2 N3 C4 -177.12(16) . . . . ? C2 C1 S1 C4 -0.25(16) . . . . ? C8A C1 S1 C4 179.2(3) . . . . ? C8B C1 S1 C4 167.7(12) . . . . ? N3 C4 S1 C1 -0.42(16) . . . . ? C10 C4 S1 C1 -179.98(17) . . . . ? C2 C1 C8A C9A 137.0(3) . . . . ? C8B C1 C8A C9A 14(6) . . . . ? S1 C1 C8A C9A -42.3(5) . . . . ? C2 C1 C8B C9B -124.5(17) . . . . ? C8A C1 C8B C9B -57(5) . . . . ? S1 C1 C8B C9B 72(2) . . . . ? C5 C5 C6A F2A 100.7(5) 3 . . . ? C2 C5 C6A F2A -76.4(5) . . . . ? C6B C5 C6A F2A -175(3) . . . . ? C5 C5 C6A F1A -136.9(4) 3 . . . ? C2 C5 C6A F1A 46.0(5) . . . . ? C6B C5 C6A F1A -53(2) . . . . ? C5 C5 C6A C7 -15.6(4) 3 . . . ? C2 C5 C6A C7 167.3(2) . . . . ? C6B C5 C6A C7 69(2) . . . . ? F3 C7 C6A F2A 26.5(5) 3 . . . ? F3 C7 C6A F2A 108.0(5) . . . . ? F4 C7 C6A F2A -6.3(5) . . . . ? F4 C7 C6A F2A 141.8(4) 3 . . . ? C6B C7 C6A F2A 166(3) . . . . ? C6B C7 C6A F2A -104.5(4) 3 . . . ? F3 C7 C6A F1A -92.1(5) 3 . . . ? F3 C7 C6A F1A -10.6(6) . . . . ? F4 C7 C6A F1A -124.8(4) . . . . ? F4 C7 C6A F1A 23.3(5) 3 . . . ? C6B C7 C6A F1A 47(2) . . . . ? C6B C7 C6A F1A 137.0(5) 3 . . . ? F3 C7 C6A C5 146.4(3) 3 . . . ? F3 C7 C6A C5 -132.1(3) . . . . ? F4 C7 C6A C5 113.7(3) . . . . ? F4 C7 C6A C5 -98.3(3) 3 . . . ? C6B C7 C6A C5 -74(2) . . . . ? C6B C7 C6A C5 15.4(5) 3 . . . ? C5 C5 C6B F1B -116.7(4) 3 . . . ? C2 C5 C6B F1B 56.1(5) . . . . ? C6A C5 C6B F1B 143(3) . . . . ? C5 C5 C6B F2B 124.0(4) 3 . . . ? C2 C5 C6B F2B -63.2(5) . . . . ? C6A C5 C6B F2B 24(2) . . . . ? C5 C5 C6B C7 1.5(5) 3 . . . ? C2 C5 C6B C7 174.3(2) . . . . ? C6A C5 C6B C7 -98(2) . . . . ? F3 C7 C6B F1B -102.1(5) 3 . . . ? F3 C7 C6B F1B -19.4(6) . . . . ? F4 C7 C6B F1B -138.3(4) . . . . ? F4 C7 C6B F1B 10.2(5) 3 . . . ? C6B C7 C6B F1B 120.4(5) 3 . . . ? C6A C7 C6B F1B -146(3) . . . . ? F3 C7 C6B F2B 14.4(6) 3 . . . ? F3 C7 C6B F2B 97.1(5) . . . . ? F4 C7 C6B F2B -21.7(5) . . . . ? F4 C7 C6B F2B 126.8(4) 3 . . . ? C6B C7 C6B F2B -123.0(5) 3 . . . ? C6A C7 C6B F2B -30(2) . . . . ? F3 C7 C6B C5 137.0(3) 3 . . . ? F3 C7 C6B C5 -140.4(3) . . . . ? F4 C7 C6B C5 100.8(4) . . . . ? F4 C7 C6B C5 -110.7(4) 3 . . . ? C6B C7 C6B C5 -0.51(16) 3 . . . ? C6A C7 C6B C5 93(2) . . . . ? F3 C7 F3 F4 174.6(5) 3 . . 3 ? F4 C7 F3 F4 177.9(2) . . . 3 ? C6B C7 F3 F4 57.8(5) . . . 3 ? C6B C7 F3 F4 -74.8(5) 3 . . 3 ? C6A C7 F3 F4 67.4(5) . . . 3 ? F4 C7 F3 F3 3.3(3) . . . 3 ? F4 C7 F3 F3 -174.6(5) 3 . . 3 ? C6B C7 F3 F3 -116.8(3) . . . 3 ? C6B C7 F3 F3 110.6(4) 3 . . 3 ? C6A C7 F3 F3 -107.2(3) . . . 3 ? F3 C7 F4 F3 -5.3(5) . . . 3 ? F4 C7 F4 F3 -3.3(3) 3 . . 3 ? C6B C7 F4 F3 121.0(4) . . . 3 ? C6B C7 F4 F3 -131.1(4) 3 . . 3 ? C6A C7 F4 F3 122.5(4) . . . 3 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.90 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.316 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.050 #===END data_3a' _database_code_depnum_ccdc_archive 'CCDC 713393' _publ_section_abstract ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-bis(5-ethyl-2-phenyl-4-thiazolyl)perfluorocyclopentene (94%) and 7,7,8,8,9,9-Hexafluoro-3a,3b-diethyl-2,5-diphenyl-3b,7,8,9- tetrahydro-3aH-3,4-dithia-1,6-diaza-triindene (6%) ; _chemical_name_common ; 1,2-bis(5-ethyl-2-phenyl-4-thiazolyl)perfluorocyclopentene (94%) and 7,7,8,8,9,9-Hexafluoro-3a,3b-diethyl-2,5-diphenyl-3b,7,8,9- tetrahydro-3aH-3,4-dithia-1,6-diaza-triindene (6%) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H20 F6 N2 S2' _chemical_formula_weight 550.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 21.586(2) _cell_length_b 10.8692(11) _cell_length_c 10.7268(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2516.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 1994 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 21.72 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9218 _exptl_absorpt_correction_T_max 0.9469 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; This crystal was obtained by UV irradiation of 1,2-bis(5-ethyl-2-phenyl-4-thiazolyl)perfluorocyclopentene crystal ; _diffrn_ambient_temperature 123 _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 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9707 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 21.84 _reflns_number_total 1514 _reflns_number_gt 1220 _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. The CF2 groups in the cyclopentene ring were disordered equally and the geometries of disordered model were restrained using SAME instraction. The ethyl groups were also disordered and the occupancy of the disordered model was refined. Existance of photogenerated isomer was observed by disorder of sulfur and reacting carbon (C1).Bond length between reacting carbons was fixed by DFIX instraction and the occupancy of the disordered model was refined. ; _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^)+(0.0319P)^2^+1.9747P] 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 1514 _refine_ls_number_parameters 208 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 C2 C 0.57103(11) 0.2938(2) 0.2134(2) 0.0301(6) Uani 1 1 d . . . N3 N 0.60843(9) 0.28904(18) 0.10904(19) 0.0304(5) Uani 1 1 d . . . C4 C 0.64428(12) 0.1920(2) 0.1122(2) 0.0326(7) Uani 1 1 d . . . C5 C 0.52942(11) 0.3989(2) 0.2291(2) 0.0264(6) Uani 1 1 d . . . C7 C 0.5000 0.6112(3) 0.2500 0.0321(9) Uani 1 2 d S . . C10 C 0.68883(11) 0.1612(2) 0.0141(2) 0.0306(7) Uani 1 1 d . . . C11 C 0.68309(12) 0.2135(2) -0.1032(2) 0.0338(7) Uani 1 1 d . . . H11 H 0.6497 0.2678 -0.1201 0.041 Uiso 1 1 calc R A . C12 C 0.72557(12) 0.1871(2) -0.1956(3) 0.0383(7) Uani 1 1 d . . . H12 H 0.7212 0.2235 -0.2757 0.046 Uiso 1 1 calc R . . C13 C 0.77431(12) 0.1085(2) -0.1726(3) 0.0396(7) Uani 1 1 d . . . H13 H 0.8036 0.0914 -0.2363 0.048 Uiso 1 1 calc R A . C14 C 0.78033(13) 0.0549(2) -0.0569(3) 0.0428(8) Uani 1 1 d . . . H14 H 0.8137 0.0000 -0.0410 0.051 Uiso 1 1 calc R . . C15 C 0.73788(13) 0.0807(2) 0.0362(3) 0.0413(8) Uani 1 1 d . . . H15 H 0.7422 0.0433 0.1157 0.050 Uiso 1 1 calc R A . C8A C 0.5491(4) 0.1812(7) 0.4242(7) 0.0457(18) Uani 0.871(6) 1 d P A 1 H8A H 0.5183 0.1142 0.4162 0.055 Uiso 0.871(6) 1 calc PR A 1 H8B H 0.5268 0.2569 0.4488 0.055 Uiso 0.871(6) 1 calc PR A 1 C9A C 0.5949(2) 0.1482(5) 0.5241(4) 0.099(2) Uani 0.871(6) 1 d P A 1 H9A H 0.6144 0.0693 0.5038 0.148 Uiso 0.871(6) 1 calc PR A 1 H9B H 0.5735 0.1415 0.6043 0.148 Uiso 0.871(6) 1 calc PR A 1 H9C H 0.6268 0.2122 0.5294 0.148 Uiso 0.871(6) 1 calc PR A 1 C8B C 0.564(3) 0.199(5) 0.417(6) 0.037(14) Uiso 0.129(6) 1 d P A 2 H8C H 0.5367 0.2693 0.4345 0.044 Uiso 0.129(6) 1 calc PR A 2 H8D H 0.6019 0.2081 0.4685 0.044 Uiso 0.129(6) 1 calc PR A 2 C9B C 0.5290(10) 0.0723(18) 0.456(2) 0.038(7) Uiso 0.129(6) 1 d P A 2 H9D H 0.4910 0.0635 0.4069 0.057 Uiso 0.129(6) 1 calc PR A 2 H9E H 0.5185 0.0753 0.5449 0.057 Uiso 0.129(6) 1 calc PR A 2 H9F H 0.5563 0.0019 0.4402 0.057 Uiso 0.129(6) 1 calc PR A 2 F1A F 0.6087(3) 0.5543(8) 0.2298(5) 0.0412(16) Uani 0.50 1 d PD B 1 F2A F 0.5492(4) 0.5442(11) 0.0685(8) 0.0419(19) Uani 0.50 1 d PD B 1 C6A C 0.5504(4) 0.5259(9) 0.1917(10) 0.027(4) Uiso 0.50 1 d PD B 1 F1B F 0.5995(3) 0.5516(8) 0.2906(7) 0.064(2) Uani 0.50 1 d PD B 2 F2B F 0.5727(4) 0.5496(11) 0.0967(8) 0.061(3) Uani 0.50 1 d PD B 2 C6B C 0.5516(5) 0.5272(10) 0.2143(9) 0.031(5) Uiso 0.50 1 d PD B 2 F3 F 0.4868(2) 0.7080(3) 0.1869(5) 0.0469(11) Uani 0.50 1 d P . 1 F4 F 0.4723(2) 0.6547(4) 0.1370(4) 0.0450(11) Uani 0.50 1 d P B 2 S1 S 0.63639(3) 0.10344(6) 0.24523(7) 0.0371(3) Uani 0.940(3) 1 d P A 3 C1 C 0.58006(13) 0.2017(2) 0.2994(3) 0.0323(7) Uiso 0.940(3) 1 d P A 3 S1B S 0.5825(11) 0.072(2) 0.178(2) 0.110(9) Uiso 0.060(3) 1 d P A 4 C1B C 0.5364(5) 0.192(4) 0.260(4) 0.0323(7) Uiso 0.060(3) 1 d PD A 4 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 C2 0.0277(14) 0.0320(15) 0.0305(16) -0.0013(12) 0.0022(13) -0.0011(12) N3 0.0246(12) 0.0320(12) 0.0345(14) 0.0006(10) 0.0023(10) 0.0003(11) C4 0.0333(16) 0.0327(16) 0.0319(17) -0.0016(12) 0.0001(13) 0.0039(13) C5 0.0253(13) 0.0275(14) 0.0264(16) -0.0002(12) 0.0005(11) 0.0009(11) C7 0.032(2) 0.028(2) 0.037(2) 0.000 0.0032(19) 0.000 C10 0.0289(15) 0.0289(14) 0.0341(17) -0.0043(13) 0.0012(13) 0.0019(13) C11 0.0277(15) 0.0346(15) 0.0390(18) 0.0013(14) 0.0028(13) 0.0025(12) C12 0.0345(16) 0.0422(16) 0.0383(18) -0.0018(14) 0.0067(14) -0.0024(14) C13 0.0280(16) 0.0458(17) 0.045(2) -0.0098(15) 0.0083(13) -0.0005(14) C14 0.0319(17) 0.0447(17) 0.052(2) -0.0090(16) -0.0002(15) 0.0128(14) C15 0.0432(19) 0.0422(17) 0.0386(19) -0.0008(14) 0.0007(15) 0.0100(14) C8A 0.060(5) 0.037(4) 0.040(3) 0.009(2) 0.023(3) 0.010(3) C9A 0.117(4) 0.131(4) 0.048(3) 0.031(3) 0.024(3) 0.090(4) F1A 0.019(2) 0.040(2) 0.064(4) -0.007(3) 0.002(3) -0.0052(16) F2A 0.057(5) 0.042(3) 0.027(3) 0.001(2) 0.009(3) -0.002(4) F1B 0.031(4) 0.039(3) 0.121(7) -0.011(5) -0.032(4) 0.001(2) F2B 0.077(7) 0.037(3) 0.071(7) 0.013(4) 0.045(5) 0.009(4) F3 0.043(3) 0.031(2) 0.067(3) 0.016(2) 0.013(2) 0.008(2) F4 0.034(2) 0.053(3) 0.048(3) 0.020(2) 0.006(2) 0.006(2) S1 0.0447(5) 0.0322(5) 0.0344(5) 0.0039(3) 0.0090(4) 0.0143(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 C2 C1B 1.42(4) . ? C2 C1 1.374(4) . ? C2 N3 1.381(3) . ? C2 C5 1.463(3) . ? N3 C4 1.309(3) . ? C4 C10 1.464(4) . ? C4 S1 1.730(3) . ? C4 S1B 1.99(2) . ? C5 C5 1.347(5) 3_655 ? C5 C6B 1.483(10) . ? C5 C6A 1.507(10) . ? C7 F3 1.284(5) 3_655 ? C7 F3 1.284(5) . ? C7 F4 1.432(4) 3_655 ? C7 F4 1.432(4) . ? C7 C6B 1.490(11) 3_655 ? C7 C6B 1.490(11) . ? C7 C6A 1.560(11) 3_655 ? C7 C6A 1.560(11) . ? C10 C11 1.386(4) . ? C10 C15 1.394(3) . ? C11 C12 1.380(4) . ? C11 H11 0.9500 . ? C12 C13 1.377(4) . ? C12 H12 0.9500 . ? C13 C14 1.377(4) . ? C13 H13 0.9500 . ? C14 C15 1.384(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C8A C1 1.512(8) . ? C8A C9A 1.502(9) . ? C8A H8A 0.9900 . ? C8A H8B 0.9900 . ? C9A H9A 0.9800 . ? C9A H9B 0.9800 . ? C9A H9C 0.9800 . ? C8B C1 1.30(6) . ? C8B C9B 1.63(5) . ? C8B H8C 0.9900 . ? C8B H8D 0.9900 . ? C9B H9D 0.9800 . ? C9B H9E 0.9800 . ? C9B H9F 0.9800 . ? F1A C6A 1.358(10) . ? F2A C6A 1.337(12) . ? F1B C6B 1.345(10) . ? F2B C6B 1.363(11) . ? F3 F3 1.469(10) 3_655 ? S1 C1 1.720(3) . ? S1B C1B 1.86(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 C1B C2 N3 124.2(17) . . ? C1 C2 N3 115.7(2) . . ? C1B C2 C5 104.0(12) . . ? C1 C2 C5 125.3(2) . . ? N3 C2 C5 118.8(2) . . ? C4 N3 C2 110.8(2) . . ? N3 C4 C10 123.6(2) . . ? N3 C4 S1 114.31(19) . . ? C10 C4 S1 122.03(19) . . ? N3 C4 S1B 98.0(7) . . ? C10 C4 S1B 123.1(7) . . ? C5 C5 C2 128.12(14) 3_655 . ? C5 C5 C6B 109.9(4) 3_655 . ? C2 C5 C6B 121.6(4) . . ? C5 C5 C6A 111.8(4) 3_655 . ? C2 C5 C6A 120.0(4) . . ? F3 C7 F3 69.8(5) 3_655 . ? F3 C7 F4 35.88(17) 3_655 3_655 ? F3 C7 F4 105.5(4) . 3_655 ? F3 C7 F4 105.5(4) 3_655 . ? F3 C7 F4 35.88(17) . . ? F4 C7 F4 141.4(5) 3_655 . ? F3 C7 C6B 122.2(4) 3_655 3_655 ? F3 C7 C6B 118.1(4) . 3_655 ? F4 C7 C6B 107.3(4) 3_655 3_655 ? F4 C7 C6B 96.2(4) . 3_655 ? F3 C7 C6B 118.1(4) 3_655 . ? F3 C7 C6B 122.2(4) . . ? F4 C7 C6B 96.2(4) 3_655 . ? F4 C7 C6B 107.3(4) . . ? C6B C7 C6B 104.5(8) 3_655 . ? F3 C7 C6A 115.6(4) 3_655 3_655 ? F3 C7 C6A 122.9(4) . 3_655 ? F4 C7 C6A 98.5(4) 3_655 3_655 ? F4 C7 C6A 104.2(4) . 3_655 ? C6B C7 C6A 105.1(3) . 3_655 ? F3 C7 C6A 122.9(4) 3_655 . ? F3 C7 C6A 115.6(4) . . ? F4 C7 C6A 104.2(4) 3_655 . ? F4 C7 C6A 98.5(4) . . ? C6B C7 C6A 105.1(3) 3_655 . ? C6A C7 C6A 107.1(8) 3_655 . ? C11 C10 C15 118.6(2) . . ? C11 C10 C4 120.0(2) . . ? C15 C10 C4 121.4(2) . . ? C12 C11 C10 120.5(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 120.5(3) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 120.5(3) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? C1 C8A C9A 112.1(5) . . ? C1 C8A H8A 109.2 . . ? C9A C8A H8A 109.2 . . ? C1 C8A H8B 109.2 . . ? C9A C8A H8B 109.2 . . ? H8A C8A H8B 107.9 . . ? C1 C8B C9B 113(4) . . ? C1 C8B H8C 108.9 . . ? C9B C8B H8C 108.9 . . ? C1 C8B H8D 108.9 . . ? C9B C8B H8D 108.9 . . ? H8C C8B H8D 107.7 . . ? C8B C9B H9D 109.5 . . ? C8B C9B H9E 109.5 . . ? H9D C9B H9E 109.5 . . ? C8B C9B H9F 109.5 . . ? H9D C9B H9F 109.5 . . ? H9E C9B H9F 109.5 . . ? F2A C6A F1A 106.4(8) . . ? F2A C6A C5 113.2(8) . . ? F1A C6A C5 114.0(8) . . ? F2A C6A C7 107.1(8) . . ? F1A C6A C7 112.9(7) . . ? C5 C6A C7 103.2(6) . . ? F1B C6B F2B 105.8(7) . . ? F1B C6B C5 111.6(8) . . ? F2B C6B C5 112.0(8) . . ? F1B C6B C7 107.3(8) . . ? F2B C6B C7 112.2(8) . . ? C5 C6B C7 107.9(6) . . ? C7 F3 F3 55.1(2) . 3_655 ? C1 S1 C4 90.15(13) . . ? C8B C1 C2 129(3) . . ? C2 C1 C8A 129.7(3) . . ? C8B C1 S1 120(3) . . ? C2 C1 S1 109.0(2) . . ? C8A C1 S1 121.3(3) . . ? C1B S1B C4 93.9(14) . . ? C2 C1B S1B 95.6(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1B C2 N3 C4 -47.5(12) . . . . ? C1 C2 N3 C4 2.3(3) . . . . ? C5 C2 N3 C4 177.5(2) . . . . ? C2 N3 C4 C10 179.6(2) . . . . ? C2 N3 C4 S1 -2.1(3) . . . . ? C2 N3 C4 S1B 40.4(7) . . . . ? C1B C2 C5 C5 -3.5(16) . . . 3_655 ? C1 C2 C5 C5 -46.0(5) . . . 3_655 ? N3 C2 C5 C5 139.4(3) . . . 3_655 ? C1B C2 C5 C6B 168.4(17) . . . . ? C1 C2 C5 C6B 125.9(5) . . . . ? N3 C2 C5 C6B -48.7(5) . . . . ? C1B C2 C5 C6A 179.1(17) . . . . ? C1 C2 C5 C6A 136.6(5) . . . . ? N3 C2 C5 C6A -38.0(6) . . . . ? N3 C4 C10 C11 -18.5(4) . . . . ? S1 C4 C10 C11 163.2(2) . . . . ? S1B C4 C10 C11 110.8(9) . . . . ? N3 C4 C10 C15 160.8(2) . . . . ? S1 C4 C10 C15 -17.4(3) . . . . ? S1B C4 C10 C15 -69.9(9) . . . . ? C15 C10 C11 C12 -0.7(4) . . . . ? C4 C10 C11 C12 178.6(2) . . . . ? C10 C11 C12 C13 0.0(4) . . . . ? C11 C12 C13 C14 0.7(4) . . . . ? C12 C13 C14 C15 -0.6(4) . . . . ? C13 C14 C15 C10 -0.2(4) . . . . ? C11 C10 C15 C14 0.8(4) . . . . ? C4 C10 C15 C14 -178.6(2) . . . . ? C5 C5 C6A F2A -101.0(8) 3_655 . . . ? C2 C5 C6A F2A 76.8(9) . . . . ? C6B C5 C6A F2A 179(100) . . . . ? C5 C5 C6A F1A 137.2(7) 3_655 . . . ? C2 C5 C6A F1A -45.0(9) . . . . ? C6B C5 C6A F1A 58(4) . . . . ? C5 C5 C6A C7 14.3(7) 3_655 . . . ? C2 C5 C6A C7 -167.9(3) . . . . ? C6B C5 C6A C7 -65(4) . . . . ? F3 C7 C6A F2A -107.6(7) 3_655 . . . ? F3 C7 C6A F2A -26.1(8) . . . . ? F4 C7 C6A F2A -141.3(7) 3_655 . . . ? F4 C7 C6A F2A 7.2(8) . . . . ? C6B C7 C6A F2A 106.0(7) 3_655 . . . ? C6B C7 C6A F2A -167(5) . . . . ? C6A C7 C6A F2A 114.9(8) 3_655 . . . ? F3 C7 C6A F1A 9.1(10) 3_655 . . . ? F3 C7 C6A F1A 90.7(8) . . . . ? F4 C7 C6A F1A -24.6(9) 3_655 . . . ? F4 C7 C6A F1A 123.9(7) . . . . ? C6B C7 C6A F1A -137.2(8) 3_655 . . . ? C6B C7 C6A F1A -50(4) . . . . ? C6A C7 C6A F1A -128.3(9) 3_655 . . . ? F3 C7 C6A C5 132.6(5) 3_655 . . . ? F3 C7 C6A C5 -145.8(5) . . . . ? F4 C7 C6A C5 98.9(5) 3_655 . . . ? F4 C7 C6A C5 -112.6(5) . . . . ? C6B C7 C6A C5 -13.7(7) 3_655 . . . ? C6B C7 C6A C5 73(5) . . . . ? C6A C7 C6A C5 -4.8(2) 3_655 . . . ? C5 C5 C6B F1B 117.0(7) 3_655 . . . ? C2 C5 C6B F1B -56.2(9) . . . . ? C6A C5 C6B F1B -139(5) . . . . ? C5 C5 C6B F2B -124.6(7) 3_655 . . . ? C2 C5 C6B F2B 62.2(8) . . . . ? C6A C5 C6B F2B -21(4) . . . . ? C5 C5 C6B C7 -0.6(7) 3_655 . . . ? C2 C5 C6B C7 -173.8(3) . . . . ? C6A C5 C6B C7 103(5) . . . . ? F3 C7 C6B F1B 19.5(9) 3_655 . . . ? F3 C7 C6B F1B 102.3(7) . . . . ? F4 C7 C6B F1B -10.5(7) 3_655 . . . ? F4 C7 C6B F1B 138.4(6) . . . . ? C6B C7 C6B F1B -120.2(8) 3_655 . . . ? C6A C7 C6B F1B -111.1(7) 3_655 . . . ? C6A C7 C6B F1B 145(5) . . . . ? F3 C7 C6B F2B -96.2(7) 3_655 . . . ? F3 C7 C6B F2B -13.5(9) . . . . ? F4 C7 C6B F2B -126.3(7) 3_655 . . . ? F4 C7 C6B F2B 22.7(8) . . . . ? C6B C7 C6B F2B 124.1(9) 3_655 . . . ? C6A C7 C6B F2B 133.2(8) 3_655 . . . ? C6A C7 C6B F2B 29(4) . . . . ? F3 C7 C6B C5 139.9(5) 3_655 . . . ? F3 C7 C6B C5 -137.4(5) . . . . ? F4 C7 C6B C5 109.9(6) 3_655 . . . ? F4 C7 C6B C5 -101.2(6) . . . . ? C6B C7 C6B C5 0.2(2) 3_655 . . . ? C6A C7 C6B C5 9.3(8) 3_655 . . . ? C6A C7 C6B C5 -95(5) . . . . ? F4 C7 F3 F3 -3.3(5) 3_655 . . 3_655 ? F4 C7 F3 F3 174.6(8) . . . 3_655 ? C6B C7 F3 F3 116.6(5) 3_655 . . 3_655 ? C6B C7 F3 F3 -111.2(5) . . . 3_655 ? C6A C7 F3 F3 108.0(6) 3_655 . . 3_655 ? C6A C7 F3 F3 -117.8(5) . . . 3_655 ? N3 C4 S1 C1 1.1(2) . . . . ? C10 C4 S1 C1 179.5(2) . . . . ? S1B C4 S1 C1 -74.4(9) . . . . ? C9B C8B C1 C2 132(3) . . . . ? C9B C8B C1 C8A 33(10) . . . . ? C9B C8B C1 S1 -68(4) . . . . ? C1B C2 C1 C8B -86(4) . . . . ? N3 C2 C1 C8B 161(3) . . . . ? C5 C2 C1 C8B -14(3) . . . . ? C1B C2 C1 C8A -69(2) . . . . ? N3 C2 C1 C8A 177.9(5) . . . . ? C5 C2 C1 C8A 3.1(6) . . . . ? C1B C2 C1 S1 112(2) . . . . ? N3 C2 C1 S1 -1.5(3) . . . . ? C5 C2 C1 S1 -176.3(2) . . . . ? C9A C8A C1 C8B -43(13) . . . . ? C9A C8A C1 C2 -135.2(4) . . . . ? C9A C8A C1 S1 44.1(7) . . . . ? C4 S1 C1 C8B -164(3) . . . . ? C4 S1 C1 C2 0.2(2) . . . . ? C4 S1 C1 C8A -179.2(4) . . . . ? N3 C4 S1B C1B -27.1(14) . . . . ? C10 C4 S1B C1B -166.5(11) . . . . ? S1 C4 S1B C1B 89.9(15) . . . . ? C1 C2 C1B S1B -73.0(14) . . . . ? N3 C2 C1B S1B 19.7(19) . . . . ? C5 C2 C1B S1B 159.9(11) . . . . ? C4 S1B C1B C2 5.2(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 21.84 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.196 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.038 #===END data_3b _database_code_depnum_ccdc_archive 'CCDC 713394' _publ_section_abstract ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7,7,8,8,9,9-Hexafluoro-3a,3b-diethyl-2,5-diphenyl-3b,7,8,9- tetrahydro-3aH-3,4-dithia-1,6-diaza-triindene ; _chemical_name_common ; 7,7,8,8,9,9-Hexafluoro-3a,3b-diethyl-2,5-diphenyl-3b,7,8,9- tetrahydro-3aH-3,4-dithia-1,6-diaza-triindene ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H20 F6 N2 S2' _chemical_formula_weight 550.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.5508(8) _cell_length_b 19.4249(15) _cell_length_c 13.5268(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.7430(10) _cell_angle_gamma 90.00 _cell_volume 2496.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 4882 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.92 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; This crystal was prepared by recrystallization. ; _diffrn_ambient_temperature 123 _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 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13830 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.44 _reflns_number_total 5649 _reflns_number_gt 4459 _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. The CF2 groups in perfluorocyclopentene part were disordered and the occupancy was refined. All C atoms in disorderd structures and F atoms of minor structures were refined isotropically. ; _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^)+(0.1000P)^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 5649 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 0.13285(16) 0.35418(8) 1.00880(12) 0.0189(3) Uani 1 1 d . A . C2 C 0.09925(16) 0.28664(8) 1.06051(11) 0.0190(3) Uani 1 1 d . A . C4 C -0.01130(16) 0.35536(8) 1.15653(11) 0.0191(3) Uani 1 1 d . A . C5 C 0.15799(16) 0.22789(8) 1.03071(11) 0.0198(3) Uani 1 1 d . . . C9 C 0.26147(16) 0.22952(8) 0.95961(12) 0.0196(3) Uani 1 1 d . A . C10 C 0.29173(15) 0.35409(9) 0.99411(11) 0.0191(3) Uani 1 1 d . A . C11 C 0.32237(16) 0.28904(8) 0.93571(12) 0.0188(3) Uani 1 1 d . . . C13 C 0.43644(16) 0.36107(8) 0.84617(12) 0.0202(3) Uani 1 1 d . . . C14 C 0.03794(17) 0.36071(9) 0.90924(12) 0.0239(4) Uani 1 1 d . . . H14A H 0.0532 0.4067 0.8806 0.029 Uiso 1 1 calc R . . H14B H 0.0684 0.3259 0.8623 0.029 Uiso 1 1 calc R . . C15 C -0.11893(18) 0.35148(10) 0.91685(14) 0.0315(4) Uani 1 1 d . . . H15A H -0.1364 0.3051 0.9414 0.047 Uiso 1 1 calc R . . H15B H -0.1706 0.3577 0.8511 0.047 Uiso 1 1 calc R . . H15C H -0.1508 0.3857 0.9629 0.047 Uiso 1 1 calc R . . C16 C 0.38651(17) 0.35491(9) 1.09420(12) 0.0240(4) Uani 1 1 d . . . H16A H 0.3717 0.3991 1.1282 0.029 Uiso 1 1 calc R A . H16B H 0.3554 0.3175 1.1367 0.029 Uiso 1 1 calc R . . C17 C 0.54331(19) 0.34628(11) 1.08603(15) 0.0346(5) Uani 1 1 d . A . H17A H 0.5604 0.3015 1.0560 0.052 Uiso 1 1 calc R . . H17B H 0.5946 0.3487 1.1524 0.052 Uiso 1 1 calc R . . H17C H 0.5759 0.3831 1.0444 0.052 Uiso 1 1 calc R . . C18 C -0.10717(16) 0.37564(8) 1.22985(11) 0.0201(3) Uani 1 1 d . . . C19 C -0.16747(17) 0.32474(9) 1.28571(12) 0.0239(4) Uani 1 1 d . . . H19 H -0.1437 0.2777 1.2780 0.029 Uiso 1 1 calc R . . C20 C -0.26176(19) 0.34354(10) 1.35210(13) 0.0278(4) Uani 1 1 d . . . H20 H -0.3035 0.3092 1.3896 0.033 Uiso 1 1 calc R . . C21 C -0.29582(18) 0.41216(10) 1.36426(13) 0.0286(4) Uani 1 1 d . . . H21 H -0.3605 0.4247 1.4101 0.034 Uiso 1 1 calc R . . C22 C -0.23590(19) 0.46223(10) 1.30987(14) 0.0301(4) Uani 1 1 d . . . H22 H -0.2596 0.5092 1.3183 0.036 Uiso 1 1 calc R . . C23 C -0.14132(18) 0.44448(9) 1.24296(13) 0.0265(4) Uani 1 1 d . . . H23 H -0.0998 0.4792 1.2060 0.032 Uiso 1 1 calc R . . C24 C 0.53422(16) 0.38329(9) 0.77532(11) 0.0203(3) Uani 1 1 d . A . C25 C 0.59070(18) 0.33355(9) 0.71537(12) 0.0244(4) Uani 1 1 d . . . H25 H 0.5621 0.2868 0.7187 0.029 Uiso 1 1 calc R A . C26 C 0.68792(19) 0.35271(10) 0.65152(13) 0.0283(4) Uani 1 1 d . A . H26 H 0.7260 0.3192 0.6107 0.034 Uiso 1 1 calc R . . C27 C 0.7301(2) 0.42098(9) 0.64688(14) 0.0306(4) Uani 1 1 d . . . H27 H 0.7978 0.4339 0.6034 0.037 Uiso 1 1 calc R A . C28 C 0.67412(19) 0.47028(10) 0.70528(14) 0.0314(4) Uani 1 1 d . A . H28 H 0.7027 0.5170 0.7015 0.038 Uiso 1 1 calc R . . C29 C 0.57612(18) 0.45153(9) 0.76948(13) 0.0266(4) Uani 1 1 d . . . H29 H 0.5376 0.4854 0.8095 0.032 Uiso 1 1 calc R A . C6A C 0.1253(3) 0.15532(15) 1.05610(19) 0.0196(5) Uiso 0.8128(19) 1 d P A 1 C7A C 0.2287(3) 0.11177(13) 1.00269(18) 0.0211(6) Uiso 0.8128(19) 1 d P A 1 C8A C 0.2787(3) 0.15888(15) 0.9197(2) 0.0213(8) Uiso 0.8128(19) 1 d P A 1 F1A F -0.00814(13) 0.13642(7) 1.02649(14) 0.0343(4) Uani 0.8128(19) 1 d P A 1 F2A F 0.1436(2) 0.14213(7) 1.15602(9) 0.0378(4) Uani 0.8128(19) 1 d P A 1 F3A F 0.17318(17) 0.05264(7) 0.96783(12) 0.0430(5) Uani 0.8128(19) 1 d P A 1 F4A F 0.34289(14) 0.09570(8) 1.06594(11) 0.0407(4) Uani 0.8128(19) 1 d P A 1 F5A F 0.19704(16) 0.14658(7) 0.83372(9) 0.0340(4) Uani 0.8128(19) 1 d P A 1 F6A F 0.41178(13) 0.14277(6) 0.90265(11) 0.0302(4) Uani 0.8128(19) 1 d P A 1 C6B C 0.1477(13) 0.1551(7) 1.0727(9) 0.0196(5) Uiso 0.1872(19) 1 d P A 2 C7B C 0.2004(10) 0.1107(5) 0.9761(7) 0.014(2) Uiso 0.1872(19) 1 d P A 2 C8B C 0.3033(13) 0.1586(6) 0.9352(9) 0.015(3) Uiso 0.1872(19) 1 d P A 2 F1B F 0.0133(6) 0.1370(3) 1.0819(5) 0.0255(14) Uiso 0.1872(19) 1 d P A 2 F2B F 0.2279(7) 0.1413(3) 1.1525(4) 0.0275(14) Uiso 0.1872(19) 1 d P A 2 F3B F 0.0938(6) 0.0942(3) 0.9148(4) 0.0339(15) Uiso 0.1872(19) 1 d P A 2 F4B F 0.2703(6) 0.0550(3) 1.0181(4) 0.0330(15) Uiso 0.1872(19) 1 d P A 2 F5B F 0.2946(7) 0.1485(3) 0.8318(4) 0.0343(15) Uiso 0.1872(19) 1 d P A 2 F6B F 0.4380(7) 0.1415(3) 0.9689(5) 0.0365(16) Uiso 0.1872(19) 1 d P A 2 N3 N 0.00810(14) 0.29179(7) 1.13265(10) 0.0201(3) Uani 1 1 d . . . N12 N 0.41332(14) 0.29666(7) 0.86379(10) 0.0204(3) Uani 1 1 d . A . S1 S 0.08123(4) 0.41918(2) 1.09629(3) 0.02225(13) Uani 1 1 d . . . S2 S 0.34659(4) 0.42265(2) 0.91327(3) 0.02251(13) 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 0.0188(8) 0.0178(8) 0.0211(8) -0.0002(6) 0.0066(6) 0.0012(6) C2 0.0159(7) 0.0201(8) 0.0213(8) -0.0007(6) 0.0035(6) -0.0021(6) C4 0.0173(7) 0.0208(8) 0.0195(8) 0.0023(6) 0.0035(6) 0.0003(6) C5 0.0202(8) 0.0184(8) 0.0212(8) 0.0014(6) 0.0045(6) -0.0014(6) C9 0.0198(8) 0.0185(8) 0.0209(8) 0.0008(6) 0.0043(6) 0.0017(6) C10 0.0176(8) 0.0178(8) 0.0223(8) 0.0014(6) 0.0048(6) -0.0020(6) C11 0.0156(7) 0.0186(8) 0.0226(8) 0.0011(6) 0.0033(6) 0.0013(6) C13 0.0169(7) 0.0221(8) 0.0218(8) 0.0007(6) 0.0031(6) -0.0001(6) C14 0.0212(8) 0.0271(9) 0.0235(8) 0.0034(7) 0.0028(7) 0.0022(7) C15 0.0195(9) 0.0432(12) 0.0313(9) 0.0007(8) -0.0001(7) 0.0023(8) C16 0.0216(8) 0.0268(9) 0.0233(8) -0.0009(7) 0.0008(7) -0.0025(7) C17 0.0208(9) 0.0477(13) 0.0344(10) 0.0034(9) -0.0016(7) -0.0019(8) C18 0.0179(7) 0.0220(9) 0.0205(8) -0.0009(6) 0.0026(6) 0.0016(6) C19 0.0240(8) 0.0227(9) 0.0253(8) 0.0006(7) 0.0039(7) 0.0004(7) C20 0.0262(9) 0.0332(10) 0.0251(9) 0.0014(7) 0.0084(7) -0.0013(7) C21 0.0235(9) 0.0376(11) 0.0257(9) -0.0058(8) 0.0072(7) 0.0026(7) C22 0.0293(9) 0.0281(10) 0.0343(10) -0.0066(8) 0.0098(8) 0.0039(7) C23 0.0272(9) 0.0237(9) 0.0300(9) -0.0003(7) 0.0100(7) 0.0005(7) C24 0.0173(7) 0.0231(9) 0.0208(8) 0.0028(6) 0.0038(6) -0.0017(6) C25 0.0258(9) 0.0225(9) 0.0258(9) -0.0005(7) 0.0070(7) -0.0023(7) C26 0.0302(9) 0.0295(10) 0.0270(9) 0.0013(7) 0.0117(7) 0.0026(7) C27 0.0302(10) 0.0317(10) 0.0324(10) 0.0077(8) 0.0154(8) -0.0002(7) C28 0.0328(10) 0.0237(10) 0.0401(11) 0.0065(8) 0.0147(8) -0.0034(7) C29 0.0273(9) 0.0221(9) 0.0323(9) 0.0033(7) 0.0119(7) 0.0004(7) F1A 0.0197(6) 0.0260(7) 0.0587(11) -0.0012(7) 0.0114(7) -0.0061(5) F2A 0.0682(12) 0.0241(7) 0.0231(7) 0.0057(5) 0.0134(7) 0.0031(7) F3A 0.0561(10) 0.0198(7) 0.0589(10) -0.0165(7) 0.0349(8) -0.0169(7) F4A 0.0289(7) 0.0494(10) 0.0447(8) 0.0214(7) 0.0077(6) 0.0106(6) F5A 0.0441(9) 0.0317(8) 0.0245(7) -0.0068(5) -0.0045(6) 0.0001(6) F6A 0.0238(7) 0.0213(7) 0.0490(9) 0.0012(6) 0.0205(6) 0.0039(5) N3 0.0197(7) 0.0196(7) 0.0218(7) 0.0012(5) 0.0060(5) 0.0006(5) N12 0.0201(7) 0.0196(7) 0.0222(7) 0.0019(5) 0.0057(5) -0.0013(5) S1 0.0253(2) 0.0164(2) 0.0266(2) -0.00068(15) 0.01021(17) 0.00000(15) S2 0.0241(2) 0.0171(2) 0.0280(2) 0.00189(16) 0.01048(17) -0.00046(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 C1 C2 1.536(2) . ? C1 C10 1.550(2) . ? C1 C14 1.551(2) . ? C1 S1 1.8316(16) . ? C2 C5 1.351(2) . ? C2 N3 1.3748(19) . ? C4 N3 1.294(2) . ? C4 C18 1.469(2) . ? C4 S1 1.7681(16) . ? C5 C9 1.447(2) . ? C5 C6A 1.491(3) . ? C5 C6B 1.531(13) . ? C9 C11 1.348(2) . ? C9 C8B 1.482(12) . ? C9 C8A 1.490(3) . ? C10 C11 1.534(2) . ? C10 C16 1.552(2) . ? C10 S2 1.8326(16) . ? C11 N12 1.3756(19) . ? C13 N12 1.297(2) . ? C13 C24 1.468(2) . ? C13 S2 1.7739(17) . ? C14 C15 1.523(2) . ? C16 C17 1.522(2) . ? C18 C23 1.392(2) . ? C18 C19 1.403(2) . ? C19 C20 1.383(2) . ? C20 C21 1.386(3) . ? C21 C22 1.378(3) . ? C22 C23 1.385(2) . ? C24 C29 1.389(2) . ? C24 C25 1.403(2) . ? C25 C26 1.381(2) . ? C26 C27 1.389(3) . ? C27 C28 1.383(3) . ? C28 C29 1.388(2) . ? C6A F1A 1.348(3) . ? C6A F2A 1.370(3) . ? C6A C7A 1.534(4) . ? C7A F3A 1.331(3) . ? C7A F4A 1.354(3) . ? C7A C8A 1.560(4) . ? C8A F6A 1.351(3) . ? C8A F5A 1.355(3) . ? C6B F2B 1.287(13) . ? C6B F1B 1.348(14) . ? C6B C7B 1.684(16) . ? C7B F3B 1.288(12) . ? C7B F4B 1.365(11) . ? C7B C8B 1.498(15) . ? C8B F6B 1.362(14) . ? C8B F5B 1.407(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 108.01(12) . . ? C2 C1 C14 109.55(13) . . ? C10 C1 C14 112.54(13) . . ? C2 C1 S1 102.27(10) . . ? C10 C1 S1 114.45(11) . . ? C14 C1 S1 109.45(11) . . ? C5 C2 N3 125.77(14) . . ? C5 C2 C1 118.28(14) . . ? N3 C2 C1 115.93(13) . . ? N3 C4 C18 122.60(14) . . ? N3 C4 S1 117.60(12) . . ? C18 C4 S1 119.80(12) . . ? C2 C5 C9 120.77(14) . . ? C2 C5 C6A 128.85(17) . . ? C9 C5 C6A 110.26(16) . . ? C2 C5 C6B 128.7(5) . . ? C9 C5 C6B 109.9(5) . . ? C11 C9 C5 121.20(14) . . ? C11 C9 C8B 127.7(5) . . ? C5 C9 C8B 110.2(5) . . ? C11 C9 C8A 129.59(17) . . ? C5 C9 C8A 109.16(16) . . ? C11 C10 C1 107.86(12) . . ? C11 C10 C16 109.46(13) . . ? C1 C10 C16 112.42(13) . . ? C11 C10 S2 102.16(10) . . ? C1 C10 S2 114.68(11) . . ? C16 C10 S2 109.66(11) . . ? C9 C11 N12 125.45(14) . . ? C9 C11 C10 118.29(13) . . ? N12 C11 C10 116.24(13) . . ? N12 C13 C24 122.32(15) . . ? N12 C13 S2 117.16(12) . . ? C24 C13 S2 120.51(12) . . ? C15 C14 C1 115.15(14) . . ? C17 C16 C10 115.33(14) . . ? C23 C18 C19 119.64(15) . . ? C23 C18 C4 120.89(15) . . ? C19 C18 C4 119.46(15) . . ? C20 C19 C18 119.52(16) . . ? C19 C20 C21 120.46(17) . . ? C22 C21 C20 120.04(16) . . ? C21 C22 C23 120.40(17) . . ? C22 C23 C18 119.94(17) . . ? C29 C24 C25 119.64(15) . . ? C29 C24 C13 121.54(15) . . ? C25 C24 C13 118.76(15) . . ? C26 C25 C24 119.82(16) . . ? C25 C26 C27 120.11(17) . . ? C28 C27 C26 120.32(17) . . ? C27 C28 C29 119.97(17) . . ? C28 C29 C24 120.14(17) . . ? F1A C6A F2A 105.4(2) . . ? F1A C6A C5 113.72(19) . . ? F2A C6A C5 113.3(2) . . ? F1A C6A C7A 110.1(2) . . ? F2A C6A C7A 109.7(2) . . ? C5 C6A C7A 104.7(2) . . ? F3A C7A F4A 107.0(2) . . ? F3A C7A C6A 113.0(2) . . ? F4A C7A C6A 110.2(2) . . ? F3A C7A C8A 113.0(2) . . ? F4A C7A C8A 107.7(2) . . ? C6A C7A C8A 105.9(2) . . ? F6A C8A F5A 106.5(2) . . ? F6A C8A C9 114.5(2) . . ? F5A C8A C9 113.5(2) . . ? F6A C8A C7A 110.4(2) . . ? F5A C8A C7A 108.8(2) . . ? C9 C8A C7A 103.1(2) . . ? F2B C6B F1B 111.2(10) . . ? F2B C6B C5 116.6(9) . . ? F1B C6B C5 111.8(9) . . ? F2B C6B C7B 110.2(9) . . ? F1B C6B C7B 107.5(9) . . ? C5 C6B C7B 98.6(8) . . ? F3B C7B F4B 113.2(8) . . ? F3B C7B C8B 115.0(9) . . ? F4B C7B C8B 109.5(9) . . ? F3B C7B C6B 110.4(8) . . ? F4B C7B C6B 104.7(8) . . ? C8B C7B C6B 103.1(8) . . ? F6B C8B F5B 105.0(9) . . ? F6B C8B C9 114.8(9) . . ? F5B C8B C9 111.1(8) . . ? F6B C8B C7B 111.0(9) . . ? F5B C8B C7B 107.8(9) . . ? C9 C8B C7B 107.1(8) . . ? C4 N3 C2 111.29(13) . . ? C13 N12 C11 111.41(13) . . ? C4 S1 C1 89.64(7) . . ? C13 S2 C10 89.84(7) . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 28.44 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.402 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.054 #===END data_4a _database_code_depnum_ccdc_archive 'CCDC 713395' _publ_section_abstract ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-bis(2-isopropyl-5-phenyl-3-thienyl)perfluorocyclopentene ; _chemical_name_common 1,2-bis(2-isopropyl-5-phenyl-3-thienyl)perfluorocyclopentene _chemical_melting_point 171 _chemical_formula_moiety ? _chemical_formula_sum 'C31 H26 F6 S2' _chemical_formula_weight 576.66 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 21.307(6) _cell_length_b 12.193(4) _cell_length_c 10.669(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2771.8(14) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 3924 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 27.40 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9283 _exptl_absorpt_correction_T_max 0.9513 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; This crystal was prepared by recrystallization. ; _diffrn_ambient_temperature 123 _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 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14494 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3196 _reflns_number_gt 2444 _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. The CF2 groups in the cyclopentene ring were disordered equally. ; _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^)+(0.0451P)^2^+1.1216P] 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 3196 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.58591(7) 0.27098(12) 0.29151(14) 0.0261(3) Uani 1 1 d . . . C2 C 0.57210(7) 0.19133(12) 0.20513(13) 0.0233(3) Uani 1 1 d . A . C3 C 0.60471(7) 0.20598(12) 0.08921(14) 0.0245(3) Uani 1 1 d . . . H3 H 0.6010 0.1569 0.0205 0.029 Uiso 1 1 calc R . . C4 C 0.64163(7) 0.29724(13) 0.08697(14) 0.0259(3) Uani 1 1 d . . . C5 C 0.52989(7) 0.09853(12) 0.22923(14) 0.0236(3) Uani 1 1 d . . . C7A C 0.5000 -0.09157(18) 0.2500 0.0257(5) Uani 1 2 d S . . C8 C 0.56669(8) 0.28018(13) 0.42664(15) 0.0307(4) Uani 1 1 d . . . H8 H 0.5381 0.2174 0.4459 0.037 Uiso 1 1 calc R . . C9 C 0.62395(9) 0.27154(17) 0.51385(16) 0.0409(4) Uani 1 1 d . . . H9A H 0.6459 0.2022 0.4981 0.061 Uiso 1 1 calc R . . H9B H 0.6100 0.2739 0.6013 0.061 Uiso 1 1 calc R . . H9C H 0.6525 0.3330 0.4977 0.061 Uiso 1 1 calc R . . C10 C 0.53100(10) 0.38535(15) 0.45199(18) 0.0431(5) Uani 1 1 d . . . H10A H 0.5589 0.4483 0.4392 0.065 Uiso 1 1 calc R . . H10B H 0.5158 0.3852 0.5387 0.065 Uiso 1 1 calc R . . H10C H 0.4952 0.3906 0.3945 0.065 Uiso 1 1 calc R . . C11 C 0.68251(7) 0.33763(13) -0.01391(14) 0.0265(3) Uani 1 1 d . . . C12 C 0.68613(7) 0.28282(14) -0.12844(15) 0.0317(4) Uani 1 1 d . . . H12 H 0.6604 0.2205 -0.1429 0.038 Uiso 1 1 calc R . . C13 C 0.72676(8) 0.31806(15) -0.22137(16) 0.0351(4) Uani 1 1 d . . . H13 H 0.7290 0.2792 -0.2984 0.042 Uiso 1 1 calc R . . C14 C 0.76392(8) 0.40892(16) -0.20293(17) 0.0381(4) Uani 1 1 d . . . H14 H 0.7922 0.4322 -0.2664 0.046 Uiso 1 1 calc R . . C15 C 0.75975(9) 0.46591(16) -0.09149(18) 0.0436(5) Uani 1 1 d . . . H15 H 0.7845 0.5297 -0.0791 0.052 Uiso 1 1 calc R . . C16 C 0.71967(8) 0.43066(15) 0.00229(16) 0.0367(4) Uani 1 1 d . . . H16 H 0.7174 0.4704 0.0788 0.044 Uiso 1 1 calc R . . C6A C 0.55804(19) -0.0148(3) 0.2256(4) 0.0243(9) Uiso 0.50 1 d P A 1 F1A F 0.60228(10) -0.03251(19) 0.3149(3) 0.0386(5) Uani 0.50 1 d P A 1 F2A F 0.58587(13) -0.03622(18) 0.1144(2) 0.0443(6) Uani 0.50 1 d P A 1 F3 F 0.48102(15) -0.1314(2) 0.1405(3) 0.0421(7) Uani 0.50 1 d P A 1 C6B C 0.54758(18) -0.0170(3) 0.1920(4) 0.0258(9) Uiso 0.50 1 d P A 2 F1B F 0.60589(10) -0.04227(19) 0.2347(3) 0.0399(6) Uani 0.50 1 d P A 2 F2B F 0.54896(13) -0.03271(17) 0.0660(2) 0.0396(5) Uani 0.50 1 d P A 2 F4 F 0.48305(14) -0.1777(2) 0.1775(3) 0.0381(7) Uani 0.50 1 d P . 2 S1 S 0.637427(19) 0.36521(3) 0.22904(4) 0.02927(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 0.0268(8) 0.0249(8) 0.0267(8) 0.0007(6) 0.0006(6) -0.0010(6) C2 0.0231(7) 0.0225(7) 0.0244(8) 0.0014(6) -0.0010(6) 0.0002(6) C3 0.0234(7) 0.0270(8) 0.0231(7) -0.0007(6) -0.0014(6) 0.0000(6) C4 0.0251(7) 0.0282(8) 0.0245(7) 0.0012(6) -0.0018(6) -0.0003(6) C5 0.0265(7) 0.0227(7) 0.0217(7) -0.0003(6) 0.0000(6) 0.0008(6) C7A 0.0278(11) 0.0226(10) 0.0266(11) 0.000 -0.0035(9) 0.000 C8 0.0372(9) 0.0294(8) 0.0257(8) -0.0034(6) 0.0042(7) -0.0051(7) C9 0.0461(10) 0.0471(11) 0.0294(9) -0.0011(8) -0.0024(8) -0.0049(9) C10 0.0505(11) 0.0388(10) 0.0402(10) -0.0090(8) 0.0077(9) 0.0040(9) C11 0.0222(7) 0.0297(8) 0.0276(8) 0.0052(6) -0.0017(6) -0.0012(6) C12 0.0277(8) 0.0377(9) 0.0296(8) 0.0017(7) 0.0009(7) -0.0044(7) C13 0.0287(8) 0.0487(10) 0.0279(8) 0.0044(7) 0.0019(7) 0.0008(8) C14 0.0266(9) 0.0516(11) 0.0362(10) 0.0142(8) 0.0037(7) -0.0025(8) C15 0.0385(10) 0.0441(11) 0.0482(11) 0.0075(9) 0.0042(9) -0.0143(8) C16 0.0386(9) 0.0372(10) 0.0344(9) 0.0005(7) 0.0033(7) -0.0086(8) F1A 0.0240(10) 0.0318(12) 0.0601(15) 0.0076(12) -0.0125(12) 0.0004(8) F2A 0.0563(16) 0.0279(11) 0.0488(16) -0.0045(11) 0.0305(13) 0.0027(11) F3 0.0400(13) 0.0487(19) 0.0376(16) -0.0227(13) -0.0044(12) -0.0044(15) F1B 0.0213(11) 0.0301(11) 0.0683(17) 0.0032(13) -0.0011(13) 0.0033(8) F2B 0.0606(15) 0.0276(11) 0.0308(12) -0.0059(9) 0.0152(11) -0.0035(11) F4 0.0330(12) 0.0245(14) 0.0569(19) -0.0137(11) 0.0030(12) -0.0035(12) S1 0.0323(2) 0.0283(2) 0.0272(2) -0.00238(15) 0.00172(16) -0.00783(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 C1 C2 1.371(2) . ? C1 C8 1.503(2) . ? C1 S1 1.7231(16) . ? C2 C3 1.430(2) . ? C2 C5 1.468(2) . ? C3 C4 1.363(2) . ? C3 H3 0.9500 . ? C4 C11 1.470(2) . ? C4 S1 1.7297(16) . ? C5 C5 1.348(3) 3_655 ? C5 C6A 1.507(4) . ? C5 C6B 1.511(4) . ? C7A F3 1.328(3) . ? C7A F3 1.328(3) 3_655 ? C7A F4 1.353(3) . ? C7A F4 1.353(3) 3_655 ? C7A C6B 1.496(4) 3_655 ? C7A C6B 1.496(4) . ? C7A C6A 1.573(4) 3_655 ? C7A C6A 1.573(4) . ? C8 C10 1.515(2) . ? C8 C9 1.538(2) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.394(2) . ? C11 C12 1.395(2) . ? C12 C13 1.385(2) . ? C12 H12 0.9500 . ? C13 C14 1.376(3) . ? C13 H13 0.9500 . ? C14 C15 1.380(3) . ? C14 H14 0.9500 . ? C15 C16 1.384(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C6A F2A 1.352(4) . ? C6A F1A 1.357(5) . ? C6B F2B 1.358(5) . ? C6B F1B 1.359(4) . ? F4 F4 1.707(7) 3_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 C8 129.74(14) . . ? C2 C1 S1 110.44(11) . . ? C8 C1 S1 119.66(11) . . ? C1 C2 C3 112.87(13) . . ? C1 C2 C5 124.05(14) . . ? C3 C2 C5 123.06(13) . . ? C4 C3 C2 113.43(13) . . ? C4 C3 H3 123.3 . . ? C2 C3 H3 123.3 . . ? C3 C4 C11 128.94(14) . . ? C3 C4 S1 110.23(11) . . ? C11 C4 S1 120.79(12) . . ? C5 C5 C2 129.51(8) 3_655 . ? C5 C5 C6A 112.60(15) 3_655 . ? C2 C5 C6A 117.28(18) . . ? C5 C5 C6B 108.78(16) 3_655 . ? C2 C5 C6B 121.29(18) . . ? F3 C7A F3 137.1(3) . 3_655 ? F3 C7A F4 29.81(13) . . ? F3 C7A F4 107.5(3) 3_655 . ? F3 C7A F4 107.5(3) . 3_655 ? F3 C7A F4 29.81(13) 3_655 3_655 ? F4 C7A F4 78.2(3) . 3_655 ? F3 C7A C6B 112.3(2) . 3_655 ? F3 C7A C6B 93.7(2) 3_655 3_655 ? F4 C7A C6B 121.8(2) . 3_655 ? F4 C7A C6B 114.6(2) 3_655 3_655 ? F3 C7A C6B 93.7(2) . . ? F3 C7A C6B 112.3(2) 3_655 . ? F4 C7A C6B 114.6(2) . . ? F4 C7A C6B 121.8(2) 3_655 . ? C6B C7A C6B 105.1(3) 3_655 . ? F3 C7A C6A 97.1(2) . 3_655 ? F3 C7A C6A 108.2(2) 3_655 3_655 ? F4 C7A C6A 110.3(2) . 3_655 ? F4 C7A C6A 125.3(2) 3_655 3_655 ? C6B C7A C6A 103.85(18) . 3_655 ? F3 C7A C6A 108.2(2) . . ? F3 C7A C6A 97.1(2) 3_655 . ? F4 C7A C6A 125.3(2) . . ? F4 C7A C6A 110.3(2) 3_655 . ? C6B C7A C6A 103.85(18) 3_655 . ? C6A C7A C6A 106.9(3) 3_655 . ? C1 C8 C10 111.79(14) . . ? C1 C8 C9 111.03(14) . . ? C10 C8 C9 110.37(15) . . ? C1 C8 H8 107.8 . . ? C10 C8 H8 107.8 . . ? C9 C8 H8 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 117.85(15) . . ? C16 C11 C4 121.23(14) . . ? C12 C11 C4 120.92(14) . . ? C13 C12 C11 120.87(16) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C12 120.48(17) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.45(16) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 120.41(17) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.90(16) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? F2A C6A F1A 106.3(3) . . ? F2A C6A C5 112.0(3) . . ? F1A C6A C5 113.9(3) . . ? F2A C6A C7A 112.0(3) . . ? F1A C6A C7A 109.6(3) . . ? C5 C6A C7A 103.2(2) . . ? F2B C6B F1B 106.3(3) . . ? F2B C6B C7A 109.8(3) . . ? F1B C6B C7A 110.1(3) . . ? F2B C6B C5 113.4(3) . . ? F1B C6B C5 110.6(3) . . ? C7A C6B C5 106.8(2) . . ? C7A F4 F4 50.88(14) . 3_655 ? C1 S1 C4 93.01(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 C8 C1 C2 C3 -173.82(15) . . . . ? S1 C1 C2 C3 1.36(17) . . . . ? C8 C1 C2 C5 4.4(3) . . . . ? S1 C1 C2 C5 179.60(12) . . . . ? C1 C2 C3 C4 -1.46(19) . . . . ? C5 C2 C3 C4 -179.72(13) . . . . ? C2 C3 C4 C11 178.79(14) . . . . ? C2 C3 C4 S1 0.85(17) . . . . ? C1 C2 C5 C5 54.1(3) . . . 3_655 ? C3 C2 C5 C5 -127.8(2) . . . 3_655 ? C1 C2 C5 C6A -116.2(2) . . . . ? C3 C2 C5 C6A 61.9(3) . . . . ? C1 C2 C5 C6B -134.1(2) . . . . ? C3 C2 C5 C6B 44.0(3) . . . . ? C2 C1 C8 C10 -121.64(19) . . . . ? S1 C1 C8 C10 63.56(18) . . . . ? C2 C1 C8 C9 114.62(19) . . . . ? S1 C1 C8 C9 -60.18(17) . . . . ? C3 C4 C11 C16 -176.83(16) . . . . ? S1 C4 C11 C16 0.9(2) . . . . ? C3 C4 C11 C12 2.1(2) . . . . ? S1 C4 C11 C12 179.82(12) . . . . ? C16 C11 C12 C13 1.9(2) . . . . ? C4 C11 C12 C13 -177.05(15) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 -1.0(3) . . . . ? C13 C14 C15 C16 1.5(3) . . . . ? C14 C15 C16 C11 -0.4(3) . . . . ? C12 C11 C16 C15 -1.3(3) . . . . ? C4 C11 C16 C15 177.63(16) . . . . ? C5 C5 C6A F2A 130.8(3) 3_655 . . . ? C2 C5 C6A F2A -57.3(4) . . . . ? C6B C5 C6A F2A 51.4(8) . . . . ? C5 C5 C6A F1A -108.6(3) 3_655 . . . ? C2 C5 C6A F1A 63.3(3) . . . . ? C6B C5 C6A F1A 172.0(11) . . . . ? C5 C5 C6A C7A 10.1(3) 3_655 . . . ? C2 C5 C6A C7A -177.99(15) . . . . ? C6B C5 C6A C7A -69.3(9) . . . . ? F3 C7A C6A F2A -20.4(4) . . . . ? F3 C7A C6A F2A 124.5(3) 3_655 . . . ? F4 C7A C6A F2A 7.2(4) . . . . ? F4 C7A C6A F2A 96.9(3) 3_655 . . . ? C6B C7A C6A F2A -139.9(3) 3_655 . . . ? C6B C7A C6A F2A -43.2(8) . . . . ? C6A C7A C6A F2A -124.0(4) 3_655 . . . ? F3 C7A C6A F1A -138.1(3) . . . . ? F3 C7A C6A F1A 6.8(3) 3_655 . . . ? F4 C7A C6A F1A -110.5(3) . . . . ? F4 C7A C6A F1A -20.8(3) 3_655 . . . ? C6B C7A C6A F1A 102.4(3) 3_655 . . . ? C6B C7A C6A F1A -160.9(11) . . . . ? C6A C7A C6A F1A 118.3(3) 3_655 . . . ? F3 C7A C6A C5 100.3(3) . . . . ? F3 C7A C6A C5 -114.8(3) 3_655 . . . ? F4 C7A C6A C5 127.8(2) . . . . ? F4 C7A C6A C5 -142.4(2) 3_655 . . . ? C6B C7A C6A C5 -19.2(3) 3_655 . . . ? C6B C7A C6A C5 77.4(9) . . . . ? C6A C7A C6A C5 -3.36(10) 3_655 . . . ? F3 C7A C6B F2B -3.4(3) . . . . ? F3 C7A C6B F2B 141.8(3) 3_655 . . . ? F4 C7A C6B F2B 18.8(4) . . . . ? F4 C7A C6B F2B 109.9(3) 3_655 . . . ? C6B C7A C6B F2B -117.7(3) 3_655 . . . ? C6A C7A C6B F2B -101.6(3) 3_655 . . . ? C6A C7A C6B F2B 155.0(11) . . . . ? F3 C7A C6B F1B -120.0(3) . . . . ? F3 C7A C6B F1B 25.1(4) 3_655 . . . ? F4 C7A C6B F1B -97.9(3) . . . . ? F4 C7A C6B F1B -6.7(4) 3_655 . . . ? C6B C7A C6B F1B 125.7(4) 3_655 . . . ? C6A C7A C6B F1B 141.8(3) 3_655 . . . ? C6A C7A C6B F1B 38.3(8) . . . . ? F3 C7A C6B C5 120.0(3) . . . . ? F3 C7A C6B C5 -94.9(3) 3_655 . . . ? F4 C7A C6B C5 142.1(2) . . . . ? F4 C7A C6B C5 -126.8(3) 3_655 . . . ? C6B C7A C6B C5 5.66(11) 3_655 . . . ? C6A C7A C6B C5 21.7(3) 3_655 . . . ? C6A C7A C6B C5 -81.7(9) . . . . ? C5 C5 C6B F2B 104.5(3) 3_655 . . . ? C2 C5 C6B F2B -68.8(4) . . . . ? C6A C5 C6B F2B -148.9(11) . . . . ? C5 C5 C6B F1B -136.2(3) 3_655 . . . ? C2 C5 C6B F1B 50.5(4) . . . . ? C6A C5 C6B F1B -29.7(7) . . . . ? C5 C5 C6B C7A -16.5(3) 3_655 . . . ? C2 C5 C6B C7A 170.20(16) . . . . ? C6A C5 C6B C7A 90.0(9) . . . . ? F3 C7A F4 F4 168.9(6) . . . 3_655 ? F3 C7A F4 F4 -5.8(3) 3_655 . . 3_655 ? C6B C7A F4 F4 -111.8(3) 3_655 . . 3_655 ? C6B C7A F4 F4 119.8(2) . . . 3_655 ? C6A C7A F4 F4 -123.5(2) 3_655 . . 3_655 ? C6A C7A F4 F4 106.6(3) . . . 3_655 ? C2 C1 S1 C4 -0.76(12) . . . . ? C8 C1 S1 C4 174.98(13) . . . . ? C3 C4 S1 C1 -0.06(12) . . . . ? C11 C4 S1 C1 -178.20(13) . . . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.367 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.046 #===END