# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Seiya Kobatake' 'Hiroyuki Imagawa' 'Seiichiro Nakashima' 'Hidenori Nakatani' _publ_contact_author_name 'Seiya Kobatake' _publ_contact_author_email KOBATAKE@A-CHEM.ENG.OSAKA-CU.AC.JP _publ_section_title ; Irreversible thermo-bleaching function of a photochromic diarylethene having trimethylsilyl groups ; # Attachment '1a.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 719459' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-Bis(2-trimethylsilyl-5-phenyl-3-thienyl)perfluorocyclopentene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H30 F6 S2 Si2' _chemical_formula_sum 'C31 H30 F6 S2 Si2' _chemical_formula_weight 636.85 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.959(16) _cell_length_b 10.52(2) _cell_length_c 17.69(3) _cell_angle_alpha 97.56(9) _cell_angle_beta 97.02(8) _cell_angle_gamma 107.21(8) _cell_volume 1556(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 11239 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 27.41 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8385 _exptl_absorpt_correction_T_max 0.8879 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14375 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.41 _reflns_number_total 6980 _reflns_number_gt 6325 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material 'CrystalStructure 3.8' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0159P)^2^+6.7417P] 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 6980 _refine_ls_number_parameters 377 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1664 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 1.217 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.18247(11) 0.33123(9) 0.05207(5) 0.0212(2) Uani 1 1 d . . . S2 S 0.25375(11) -0.04686(9) 0.29936(5) 0.0213(2) Uani 1 1 d . . . Si1 Si 0.46893(12) 0.38971(11) 0.18152(6) 0.0218(2) Uani 1 1 d . . . Si2 Si -0.05105(12) -0.01553(10) 0.21945(6) 0.0219(2) Uani 1 1 d . . . F1 F -0.0482(3) 0.5040(3) 0.27242(13) 0.0311(5) Uani 1 1 d . . . F2 F 0.2019(3) 0.6116(2) 0.31325(14) 0.0323(6) Uani 1 1 d . . . F3 F -0.0830(3) 0.3942(2) 0.39300(14) 0.0315(5) Uani 1 1 d . . . F4 F 0.1025(3) 0.5825(2) 0.44452(13) 0.0320(6) Uani 1 1 d . . . F5 F 0.1248(3) 0.2986(2) 0.45761(14) 0.0336(6) Uani 1 1 d . . . F6 F 0.3242(3) 0.4668(3) 0.44413(14) 0.0333(6) Uani 1 1 d . . . C1 C 0.2496(4) 0.3568(3) 0.1502(2) 0.0182(7) Uani 1 1 d . . . C2 C 0.1227(4) 0.3495(3) 0.1892(2) 0.0176(7) Uani 1 1 d . . . C3 C -0.0242(4) 0.3252(3) 0.1392(2) 0.0186(7) Uani 1 1 d . . . H3 H -0.1191 0.3195 0.1570 0.022 Uiso 1 1 calc R . . C4 C -0.0118(4) 0.3112(4) 0.0628(2) 0.0199(7) Uani 1 1 d . . . C5 C 0.1329(4) 0.3738(3) 0.2744(2) 0.0162(6) Uani 1 1 d . . . C6 C 0.0864(5) 0.4920(4) 0.3103(2) 0.0206(7) Uani 1 1 d . . . C7 C 0.0687(5) 0.4688(4) 0.3931(2) 0.0239(8) Uani 1 1 d . . . C8 C 0.1777(5) 0.3828(4) 0.4084(2) 0.0217(7) Uani 1 1 d . . . C9 C 0.1814(4) 0.3111(3) 0.3294(2) 0.0174(7) Uani 1 1 d . . . C10 C 0.1504(4) 0.0640(3) 0.2820(2) 0.0191(7) Uani 1 1 d . . . C11 C 0.2353(4) 0.1906(3) 0.3246(2) 0.0172(7) Uani 1 1 d . . . C12 C 0.3796(4) 0.1944(4) 0.3711(2) 0.0192(7) Uani 1 1 d . . . H12 H 0.4476 0.2720 0.4036 0.023 Uiso 1 1 calc R . . C13 C 0.4076(4) 0.0724(4) 0.3629(2) 0.0191(7) Uani 1 1 d . . . C14 C -0.1397(5) 0.2797(4) -0.0042(2) 0.0212(7) Uani 1 1 d . . . C15 C -0.1143(5) 0.3313(4) -0.0713(2) 0.0262(8) Uani 1 1 d . . . H15 H -0.0141 0.3871 -0.0747 0.031 Uiso 1 1 calc R . . C16 C -0.2377(6) 0.3005(4) -0.1339(2) 0.0318(9) Uani 1 1 d . . . H16 H -0.2191 0.3349 -0.1789 0.038 Uiso 1 1 calc R . . C17 C -0.3876(6) 0.2189(5) -0.1292(3) 0.0363(10) Uani 1 1 d . . . H17 H -0.4700 0.1995 -0.1706 0.044 Uiso 1 1 calc R . . C18 C -0.4149(5) 0.1658(5) -0.0624(3) 0.0364(10) Uani 1 1 d . . . H18 H -0.5153 0.1100 -0.0594 0.044 Uiso 1 1 calc R . . C19 C -0.2922(5) 0.1962(4) -0.0004(2) 0.0285(8) Uani 1 1 d . . . H19 H -0.3110 0.1608 0.0443 0.034 Uiso 1 1 calc R . . C20 C 0.5396(4) 0.0337(4) 0.4013(2) 0.0197(7) Uani 1 1 d . . . C21 C 0.6658(4) 0.1299(4) 0.4520(2) 0.0243(8) Uani 1 1 d . . . H21 H 0.6688 0.2198 0.4606 0.029 Uiso 1 1 calc R . . C22 C 0.7869(5) 0.0924(4) 0.4897(2) 0.0277(8) Uani 1 1 d . . . H22 H 0.8710 0.1573 0.5232 0.033 Uiso 1 1 calc R . . C23 C 0.7829(5) -0.0420(4) 0.4774(3) 0.0285(9) Uani 1 1 d . . . H23 H 0.8638 -0.0671 0.5031 0.034 Uiso 1 1 calc R . . C24 C 0.6595(5) -0.1377(4) 0.4274(3) 0.0298(9) Uani 1 1 d . . . H24 H 0.6571 -0.2275 0.4190 0.036 Uiso 1 1 calc R . . C25 C 0.5384(5) -0.1006(4) 0.3894(2) 0.0270(8) Uani 1 1 d . . . H25 H 0.4554 -0.1659 0.3556 0.032 Uiso 1 1 calc R . . C26 C 0.5408(5) 0.5055(5) 0.2774(2) 0.0322(9) Uani 1 1 d . . . H26A H 0.4962 0.4596 0.3169 0.048 Uiso 1 1 calc R . . H26B H 0.5087 0.5845 0.2756 0.048 Uiso 1 1 calc R . . H26C H 0.6544 0.5317 0.2891 0.048 Uiso 1 1 calc R . . C27 C 0.5722(5) 0.4719(4) 0.1064(2) 0.0289(8) Uani 1 1 d . . . H27A H 0.6840 0.4868 0.1193 0.043 Uiso 1 1 calc R . . H27B H 0.5538 0.5570 0.1046 0.043 Uiso 1 1 calc R . . H27C H 0.5318 0.4142 0.0568 0.043 Uiso 1 1 calc R . . C28 C 0.5026(5) 0.2241(5) 0.1839(3) 0.0339(10) Uani 1 1 d . . . H28A H 0.6129 0.2387 0.2018 0.051 Uiso 1 1 calc R . . H28B H 0.4717 0.1708 0.1328 0.051 Uiso 1 1 calc R . . H28C H 0.4405 0.1774 0.2183 0.051 Uiso 1 1 calc R . . C29 C -0.1920(5) 0.0711(4) 0.2519(3) 0.0295(9) Uani 1 1 d . . . H29A H -0.1556 0.1641 0.2458 0.044 Uiso 1 1 calc R . . H29B H -0.1977 0.0664 0.3053 0.044 Uiso 1 1 calc R . . H29C H -0.2952 0.0275 0.2212 0.044 Uiso 1 1 calc R . . C30 C -0.0309(6) -0.0159(4) 0.1160(2) 0.0328(9) Uani 1 1 d . . . H30A H -0.1336 -0.0552 0.0841 0.049 Uiso 1 1 calc R . . H30B H 0.0365 -0.0681 0.1022 0.049 Uiso 1 1 calc R . . H30C H 0.0147 0.0752 0.1082 0.049 Uiso 1 1 calc R . . C31 C -0.1237(5) -0.1947(4) 0.2350(3) 0.0382(11) Uani 1 1 d . . . H31A H -0.1315 -0.1957 0.2886 0.057 Uiso 1 1 calc R . . H31B H -0.0506 -0.2406 0.2207 0.057 Uiso 1 1 calc R . . H31C H -0.2261 -0.2395 0.2038 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0223(4) 0.0243(4) 0.0181(4) 0.0041(3) 0.0070(3) 0.0078(4) S2 0.0210(4) 0.0149(4) 0.0271(5) 0.0023(3) 0.0001(3) 0.0066(3) Si1 0.0186(5) 0.0242(5) 0.0245(5) 0.0072(4) 0.0066(4) 0.0071(4) Si2 0.0193(5) 0.0150(5) 0.0285(5) 0.0029(4) -0.0012(4) 0.0035(4) F1 0.0384(14) 0.0377(13) 0.0255(12) 0.0040(10) 0.0039(10) 0.0257(11) F2 0.0481(15) 0.0138(10) 0.0346(13) 0.0073(9) 0.0148(11) 0.0048(10) F3 0.0296(12) 0.0341(13) 0.0350(13) 0.0109(10) 0.0158(10) 0.0104(10) F4 0.0518(16) 0.0248(12) 0.0223(11) -0.0004(9) 0.0080(11) 0.0181(11) F5 0.0576(17) 0.0298(12) 0.0247(12) 0.0148(10) 0.0195(11) 0.0213(12) F6 0.0324(13) 0.0321(13) 0.0279(12) -0.0077(10) -0.0079(10) 0.0095(10) C1 0.0216(17) 0.0144(15) 0.0186(16) 0.0032(13) 0.0046(13) 0.0052(13) C2 0.0204(17) 0.0140(15) 0.0196(17) 0.0027(12) 0.0053(13) 0.0068(13) C3 0.0198(17) 0.0168(16) 0.0206(17) 0.0046(13) 0.0059(14) 0.0063(13) C4 0.0207(17) 0.0176(16) 0.0220(17) 0.0047(13) 0.0053(14) 0.0058(14) C5 0.0161(15) 0.0123(15) 0.0196(16) 0.0034(12) 0.0051(13) 0.0026(12) C6 0.0266(18) 0.0152(16) 0.0209(17) 0.0042(13) 0.0043(14) 0.0074(14) C7 0.031(2) 0.0207(18) 0.0218(18) 0.0027(14) 0.0077(15) 0.0095(15) C8 0.0296(19) 0.0187(17) 0.0174(17) 0.0049(13) 0.0033(14) 0.0081(15) C9 0.0176(16) 0.0145(15) 0.0189(16) 0.0025(13) 0.0033(13) 0.0034(13) C10 0.0195(17) 0.0158(16) 0.0231(17) 0.0052(13) 0.0042(14) 0.0064(13) C11 0.0180(16) 0.0153(15) 0.0192(16) 0.0039(13) 0.0047(13) 0.0055(13) C12 0.0200(17) 0.0165(16) 0.0195(16) 0.0043(13) 0.0029(13) 0.0032(13) C13 0.0176(16) 0.0172(16) 0.0214(17) 0.0046(13) 0.0025(13) 0.0037(13) C14 0.0264(18) 0.0182(16) 0.0194(17) 0.0007(13) 0.0020(14) 0.0095(14) C15 0.034(2) 0.0211(18) 0.0226(18) 0.0046(15) 0.0029(16) 0.0073(16) C16 0.046(3) 0.026(2) 0.0231(19) 0.0050(16) 0.0004(18) 0.0137(19) C17 0.039(2) 0.038(2) 0.028(2) -0.0033(18) -0.0103(18) 0.016(2) C18 0.026(2) 0.040(2) 0.036(2) -0.0001(19) -0.0029(18) 0.0064(18) C19 0.027(2) 0.034(2) 0.0222(19) 0.0037(16) 0.0056(16) 0.0059(17) C20 0.0186(17) 0.0195(17) 0.0233(18) 0.0076(14) 0.0041(14) 0.0076(14) C21 0.0203(18) 0.0190(17) 0.032(2) 0.0071(15) 0.0018(15) 0.0043(14) C22 0.0212(18) 0.027(2) 0.033(2) 0.0097(16) -0.0005(16) 0.0050(15) C23 0.0215(19) 0.029(2) 0.039(2) 0.0166(17) 0.0042(17) 0.0097(16) C24 0.029(2) 0.0211(18) 0.042(2) 0.0094(17) 0.0043(18) 0.0111(16) C25 0.0239(19) 0.0196(18) 0.035(2) 0.0050(16) 0.0015(16) 0.0050(15) C26 0.0215(19) 0.039(2) 0.029(2) 0.0043(18) 0.0017(16) 0.0010(17) C27 0.0252(19) 0.030(2) 0.032(2) 0.0090(17) 0.0111(17) 0.0059(16) C28 0.032(2) 0.038(2) 0.046(3) 0.021(2) 0.020(2) 0.0205(19) C29 0.0204(18) 0.026(2) 0.042(2) 0.0095(17) 0.0047(17) 0.0062(15) C30 0.040(2) 0.024(2) 0.029(2) -0.0049(16) -0.0067(18) 0.0112(18) C31 0.028(2) 0.0190(19) 0.061(3) 0.0086(19) -0.002(2) 0.0015(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.724(5) . ? S1 C4 1.727(5) . ? S2 C13 1.722(5) . ? S2 C10 1.725(4) . ? Si1 C28 1.859(6) . ? Si1 C27 1.871(5) . ? Si1 C26 1.872(5) . ? Si1 C1 1.889(5) . ? Si2 C30 1.861(6) . ? Si2 C29 1.864(5) . ? Si2 C31 1.872(6) . ? Si2 C10 1.886(5) . ? F1 C6 1.355(5) . ? F2 C6 1.363(5) . ? F3 C7 1.353(5) . ? F4 C7 1.335(5) . ? F5 C8 1.350(5) . ? F6 C8 1.366(5) . ? C1 C2 1.389(5) . ? C2 C3 1.428(5) . ? C2 C5 1.483(5) . ? C3 C4 1.362(5) . ? C4 C14 1.472(6) . ? C5 C9 1.343(5) . ? C5 C6 1.512(5) . ? C6 C7 1.536(6) . ? C7 C8 1.538(6) . ? C8 C9 1.507(5) . ? C9 C11 1.481(5) . ? C10 C11 1.384(6) . ? C11 C12 1.431(5) . ? C12 C13 1.372(5) . ? C13 C20 1.480(5) . ? C14 C15 1.386(6) . ? C14 C19 1.404(6) . ? C15 C16 1.396(6) . ? C16 C17 1.383(7) . ? C17 C18 1.389(7) . ? C18 C19 1.386(6) . ? C20 C21 1.394(6) . ? C20 C25 1.397(6) . ? C21 C22 1.387(6) . ? C22 C23 1.392(6) . ? C23 C24 1.374(6) . ? C24 C25 1.386(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 93.9(2) . . ? C13 S2 C10 94.5(2) . . ? C28 Si1 C27 109.3(2) . . ? C28 Si1 C26 112.2(2) . . ? C27 Si1 C26 109.5(2) . . ? C28 Si1 C1 108.1(2) . . ? C27 Si1 C1 107.1(2) . . ? C26 Si1 C1 110.5(2) . . ? C30 Si2 C29 113.9(2) . . ? C30 Si2 C31 108.7(2) . . ? C29 Si2 C31 107.9(2) . . ? C30 Si2 C10 109.4(2) . . ? C29 Si2 C10 110.1(2) . . ? C31 Si2 C10 106.6(2) . . ? C2 C1 S1 109.1(3) . . ? C2 C1 Si1 134.2(3) . . ? S1 C1 Si1 116.7(2) . . ? C1 C2 C3 113.5(3) . . ? C1 C2 C5 125.6(3) . . ? C3 C2 C5 120.7(3) . . ? C4 C3 C2 113.3(3) . . ? C3 C4 C14 127.8(4) . . ? C3 C4 S1 110.2(3) . . ? C14 C4 S1 122.0(3) . . ? C9 C5 C2 131.9(3) . . ? C9 C5 C6 110.6(3) . . ? C2 C5 C6 117.5(3) . . ? F1 C6 F2 106.0(3) . . ? F1 C6 C5 114.6(3) . . ? F2 C6 C5 111.4(3) . . ? F1 C6 C7 111.0(3) . . ? F2 C6 C7 109.1(3) . . ? C5 C6 C7 104.6(3) . . ? F4 C7 F3 107.9(3) . . ? F4 C7 C6 113.9(3) . . ? F3 C7 C6 108.6(3) . . ? F4 C7 C8 114.7(3) . . ? F3 C7 C8 109.1(3) . . ? C6 C7 C8 102.3(3) . . ? F5 C8 F6 106.3(3) . . ? F5 C8 C9 113.8(3) . . ? F6 C8 C9 112.1(3) . . ? F5 C8 C7 111.2(3) . . ? F6 C8 C7 108.7(3) . . ? C9 C8 C7 104.7(3) . . ? C5 C9 C11 131.7(3) . . ? C5 C9 C8 110.2(3) . . ? C11 C9 C8 118.1(3) . . ? C11 C10 S2 108.8(3) . . ? C11 C10 Si2 135.9(3) . . ? S2 C10 Si2 114.9(2) . . ? C10 C11 C12 113.7(3) . . ? C10 C11 C9 125.3(3) . . ? C12 C11 C9 120.8(3) . . ? C13 C12 C11 113.3(3) . . ? C12 C13 C20 130.1(3) . . ? C12 C13 S2 109.6(3) . . ? C20 C13 S2 120.2(3) . . ? C15 C14 C19 118.6(4) . . ? C15 C14 C4 121.8(4) . . ? C19 C14 C4 119.6(4) . . ? C14 C15 C16 120.7(4) . . ? C17 C16 C15 120.1(4) . . ? C16 C17 C18 120.0(4) . . ? C19 C18 C17 119.9(4) . . ? C18 C19 C14 120.8(4) . . ? C21 C20 C25 118.5(4) . . ? C21 C20 C13 120.6(3) . . ? C25 C20 C13 120.8(3) . . ? C22 C21 C20 120.4(4) . . ? C21 C22 C23 120.1(4) . . ? C24 C23 C22 120.0(4) . . ? C23 C24 C25 120.0(4) . . ? C24 C25 C20 120.9(4) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.432 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.094 # Attachment '1c.cif' data_1c _database_code_depnum_ccdc_archive 'CCDC 719460' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(6,6,7,7,8,8-Hexafluoro-2-phenyl-4-trimethylsilanyl- 7,8-dihydro-6H-3-thia-as-indacen-5-yl)-1-phenyl- ethenethiol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 F6 S2 Si' _chemical_formula_sum 'C28 H22 F6 S2 Si' _chemical_formula_weight 564.67 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.994(12) _cell_length_b 16.162(15) _cell_length_c 23.68(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.73(4) _cell_angle_gamma 90.00 _cell_volume 5337(8) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7585 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 26.8 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9147 _exptl_absorpt_correction_T_max 0.9704 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13639 _diffrn_reflns_av_R_equivalents 0.1719 _diffrn_reflns_av_sigmaI/netI 0.2117 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5741 _reflns_number_gt 1713 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material 'CrystalStructure 3.8' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1866P)^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 5741 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2809 _refine_ls_R_factor_gt 0.1241 _refine_ls_wR_factor_ref 0.3798 _refine_ls_wR_factor_gt 0.3047 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.922 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.42680(16) 0.56090(17) 0.67881(10) 0.0669(8) Uani 1 1 d . A 1 S2 S 0.62278(17) 0.5354(2) 0.47170(11) 0.0796(9) Uani 1 1 d . A 1 H2 H 0.5927 0.4672 0.4609 0.119 Uiso 1 1 calc R A 1 Si1 Si 0.59895(19) 0.66112(18) 0.61274(11) 0.0662(8) Uani 1 1 d . A 1 F1 F 0.5047(4) 0.2369(4) 0.6030(2) 0.0846(17) Uani 1 1 d . A 1 F2 F 0.5627(4) 0.2388(4) 0.6915(3) 0.0900(18) Uani 1 1 d . A 1 F3 F 0.6716(4) 0.1767(4) 0.5872(3) 0.0930(19) Uani 1 1 d . A 1 F4 F 0.7354(4) 0.2333(4) 0.6654(2) 0.0902(19) Uani 1 1 d . A 1 F5 F 0.6867(4) 0.3156(3) 0.5296(2) 0.0769(16) Uani 1 1 d . A 1 F6 F 0.8034(3) 0.3346(3) 0.5949(2) 0.0768(16) Uani 1 1 d . A 1 C1 C 0.5201(6) 0.5058(6) 0.6517(4) 0.060(2) Uani 1 1 d . A 1 C2 C 0.5057(6) 0.4187(6) 0.6599(4) 0.063(3) Uani 1 1 d . A 1 C3 C 0.4222(6) 0.3989(7) 0.6884(3) 0.068(3) Uani 1 1 d . A 1 H3 H 0.4036 0.3444 0.6979 0.082 Uiso 1 1 calc R A 1 C4 C 0.3721(6) 0.4703(6) 0.7003(4) 0.060(2) Uani 1 1 d . A 1 C5 C 0.5728(6) 0.3647(6) 0.6385(4) 0.063(2) Uani 1 1 d . A 1 C6 C 0.5760(7) 0.2702(7) 0.6379(4) 0.072(3) Uani 1 1 d . A 1 C7 C 0.6738(8) 0.2464(7) 0.6185(5) 0.077(3) Uani 1 1 d . A 1 C8 C 0.7026(6) 0.3254(6) 0.5868(4) 0.059(2) Uani 1 1 d . A 1 C9 C 0.6486(6) 0.3968(7) 0.6087(3) 0.066(3) Uani 1 1 d . A 1 C10 C 0.5967(6) 0.5404(7) 0.6223(4) 0.066(3) Uani 1 1 d . A 1 C11 C 0.6616(6) 0.4841(6) 0.6009(3) 0.059(2) Uani 1 1 d . A 1 C12 C 0.7435(6) 0.5091(6) 0.5667(4) 0.062(2) Uani 1 1 d . A 1 H12 H 0.8056 0.5115 0.5861 0.075 Uiso 1 1 calc R A 1 C13 C 0.7364(6) 0.5281(5) 0.5114(4) 0.057(2) Uani 1 1 d . A 1 C14 C 0.2819(7) 0.4745(7) 0.7313(4) 0.066(3) Uani 1 1 d . A 1 C15 C 0.2366(7) 0.4038(7) 0.7486(4) 0.072(3) Uani 1 1 d . A 1 H15 H 0.2623 0.3508 0.7413 0.087 Uiso 1 1 calc R A 1 C16 C 0.1518(7) 0.4106(8) 0.7773(4) 0.078(3) Uani 1 1 d . A 1 H16 H 0.1216 0.3624 0.7904 0.093 Uiso 1 1 calc R A 1 C17 C 0.1132(7) 0.4881(7) 0.7860(4) 0.071(3) Uani 1 1 d . A 1 H17 H 0.0555 0.4921 0.8044 0.086 Uiso 1 1 calc R A 1 C18 C 0.1568(7) 0.5608(7) 0.7686(4) 0.076(3) Uani 1 1 d . A 1 H18 H 0.1310 0.6136 0.7760 0.091 Uiso 1 1 calc R A 1 C19 C 0.2414(7) 0.5528(7) 0.7392(4) 0.075(3) Uani 1 1 d . A 1 H19 H 0.2704 0.6007 0.7249 0.090 Uiso 1 1 calc R A 1 C20 C 0.8201(6) 0.5477(6) 0.4795(4) 0.059(2) Uani 1 1 d . A 1 C21 C 0.8227(6) 0.5257(6) 0.4216(4) 0.064(3) Uani 1 1 d . A 1 H21 H 0.7682 0.4999 0.4025 0.077 Uiso 1 1 calc R A 1 C22 C 0.9028(7) 0.5408(6) 0.3923(4) 0.072(3) Uani 1 1 d . A 1 H22 H 0.9035 0.5238 0.3539 0.086 Uiso 1 1 calc R A 1 C23 C 0.9831(6) 0.5812(6) 0.4195(4) 0.063(2) Uani 1 1 d . A 1 H23 H 1.0376 0.5935 0.3996 0.075 Uiso 1 1 calc R A 1 C24 C 0.9801(6) 0.6028(6) 0.4764(4) 0.067(3) Uani 1 1 d . A 1 H24 H 1.0352 0.6273 0.4956 0.080 Uiso 1 1 calc R A 1 C25 C 0.9010(6) 0.5899(6) 0.5056(4) 0.061(2) Uani 1 1 d . A 1 H25 H 0.9002 0.6093 0.5434 0.073 Uiso 1 1 calc R A 1 C26 C 0.4893(7) 0.6851(7) 0.5647(4) 0.081(3) Uani 1 1 d . A 1 H26A H 0.4778 0.7450 0.5645 0.121 Uiso 1 1 calc R A 1 H26B H 0.4339 0.6565 0.5783 0.121 Uiso 1 1 calc R A 1 H26C H 0.4989 0.6665 0.5262 0.121 Uiso 1 1 calc R A 1 C27 C 0.7078(8) 0.7056(7) 0.5846(4) 0.086(3) Uani 1 1 d . A 1 H27A H 0.7046 0.6974 0.5435 0.129 Uiso 1 1 calc R A 1 H27B H 0.7649 0.6779 0.6024 0.129 Uiso 1 1 calc R A 1 H27C H 0.7113 0.7649 0.5931 0.129 Uiso 1 1 calc R A 1 C28 C 0.5921(8) 0.7124(7) 0.6844(4) 0.086(3) Uani 1 1 d . A 1 H28A H 0.6412 0.6888 0.7117 0.129 Uiso 1 1 calc R A 1 H28B H 0.5285 0.7029 0.6977 0.129 Uiso 1 1 calc R A 1 H28C H 0.6030 0.7720 0.6809 0.129 Uiso 1 1 calc R A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0487(13) 0.090(2) 0.0628(15) -0.0016(13) 0.0086(11) -0.0040(13) S2 0.0437(13) 0.121(3) 0.0739(17) -0.0006(16) 0.0019(12) -0.0047(15) Si1 0.0538(15) 0.076(2) 0.0695(18) 0.0012(14) 0.0086(13) -0.0022(14) F1 0.057(3) 0.083(4) 0.113(4) -0.011(3) 0.000(3) -0.007(3) F2 0.079(4) 0.089(5) 0.104(4) 0.015(3) 0.021(3) 0.007(3) F3 0.069(4) 0.085(5) 0.127(5) -0.022(4) 0.017(4) -0.004(3) F4 0.056(3) 0.113(5) 0.101(4) 0.021(4) 0.003(3) 0.010(3) F5 0.071(4) 0.084(4) 0.075(4) -0.009(3) 0.006(3) 0.009(3) F6 0.043(3) 0.090(4) 0.099(4) -0.005(3) 0.012(3) 0.006(3) C1 0.043(5) 0.078(7) 0.059(5) -0.008(5) 0.003(4) -0.002(5) C2 0.050(5) 0.084(8) 0.055(5) -0.001(5) 0.011(4) -0.007(5) C3 0.059(6) 0.086(8) 0.059(6) 0.003(5) -0.003(5) 0.006(6) C4 0.046(5) 0.071(7) 0.062(6) 0.011(5) -0.001(4) -0.004(5) C5 0.047(5) 0.068(7) 0.075(6) -0.008(5) 0.006(5) 0.003(5) C6 0.048(5) 0.106(9) 0.064(6) -0.012(6) 0.018(5) -0.011(6) C7 0.061(6) 0.082(8) 0.087(7) -0.003(7) -0.001(6) 0.001(6) C8 0.050(5) 0.050(6) 0.076(7) 0.001(5) 0.001(5) 0.006(4) C9 0.044(5) 0.105(9) 0.048(5) 0.011(5) 0.003(4) 0.025(6) C10 0.042(5) 0.107(8) 0.052(5) 0.003(5) 0.008(4) 0.007(5) C11 0.049(5) 0.074(7) 0.054(5) 0.003(5) -0.006(4) -0.004(5) C12 0.042(5) 0.078(7) 0.065(6) 0.001(5) -0.002(4) 0.004(5) C13 0.039(4) 0.061(6) 0.070(6) 0.002(5) 0.005(4) -0.007(4) C14 0.060(6) 0.075(7) 0.062(6) -0.010(5) -0.007(5) -0.013(6) C15 0.061(6) 0.093(8) 0.063(6) -0.001(6) 0.004(5) -0.009(6) C16 0.050(6) 0.111(10) 0.071(6) 0.020(6) 0.000(5) -0.005(6) C17 0.048(5) 0.094(9) 0.071(6) 0.010(6) -0.001(5) 0.006(6) C18 0.066(6) 0.073(8) 0.089(7) 0.000(6) 0.008(6) 0.002(6) C19 0.065(6) 0.096(9) 0.063(6) 0.003(6) 0.006(5) -0.008(6) C20 0.049(5) 0.069(6) 0.060(6) 0.002(5) 0.005(4) -0.006(5) C21 0.035(4) 0.078(7) 0.079(6) -0.009(5) 0.005(4) -0.003(5) C22 0.059(6) 0.089(8) 0.067(6) -0.003(5) 0.005(5) 0.004(6) C23 0.038(5) 0.075(7) 0.076(7) 0.002(5) 0.011(4) -0.003(5) C24 0.049(5) 0.079(7) 0.072(6) -0.002(5) -0.001(5) -0.006(5) C25 0.055(5) 0.076(7) 0.053(5) -0.005(5) 0.011(4) -0.002(5) C26 0.078(7) 0.079(8) 0.086(7) 0.012(6) 0.011(6) 0.008(6) C27 0.080(7) 0.094(8) 0.085(7) -0.003(6) 0.023(6) 0.006(6) C28 0.074(7) 0.106(9) 0.078(7) 0.009(6) 0.006(6) -0.020(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.745(9) . ? S1 C4 1.748(9) . ? S2 C13 1.783(9) . ? Si1 C27 1.857(11) . ? Si1 C26 1.875(11) . ? Si1 C28 1.899(10) . ? Si1 C10 1.965(11) . ? F1 C6 1.354(10) . ? F2 C6 1.394(10) . ? F3 C7 1.348(12) . ? F4 C7 1.365(11) . ? F5 C8 1.364(10) . ? F6 C8 1.416(10) . ? C1 C2 1.437(13) . ? C1 C10 1.439(12) . ? C2 C5 1.408(12) . ? C2 C3 1.433(12) . ? C3 C4 1.391(13) . ? C4 C14 1.513(13) . ? C5 C9 1.419(13) . ? C5 C6 1.529(13) . ? C6 C7 1.527(14) . ? C7 C8 1.551(14) . ? C8 C9 1.496(13) . ? C9 C11 1.437(14) . ? C10 C11 1.410(12) . ? C11 C12 1.511(12) . ? C12 C13 1.341(11) . ? C13 C20 1.479(11) . ? C14 C15 1.386(13) . ? C14 C19 1.406(13) . ? C15 C16 1.420(13) . ? C16 C17 1.386(14) . ? C17 C18 1.401(13) . ? C18 C19 1.426(14) . ? C20 C21 1.419(12) . ? C20 C25 1.419(11) . ? C21 C22 1.389(12) . ? C22 C23 1.409(12) . ? C23 C24 1.396(12) . ? C24 C25 1.369(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 92.2(5) . . ? C27 Si1 C26 110.9(5) . . ? C27 Si1 C28 104.8(5) . . ? C26 Si1 C28 110.7(5) . . ? C27 Si1 C10 116.6(4) . . ? C26 Si1 C10 104.8(4) . . ? C28 Si1 C10 109.1(4) . . ? C2 C1 C10 124.4(8) . . ? C2 C1 S1 109.5(6) . . ? C10 C1 S1 126.1(8) . . ? C5 C2 C3 128.7(10) . . ? C5 C2 C1 117.0(8) . . ? C3 C2 C1 114.3(9) . . ? C4 C3 C2 110.7(10) . . ? C3 C4 C14 126.2(9) . . ? C3 C4 S1 113.3(7) . . ? C14 C4 S1 120.4(8) . . ? C2 C5 C9 120.0(9) . . ? C2 C5 C6 130.1(9) . . ? C9 C5 C6 109.7(8) . . ? F1 C6 F2 105.3(8) . . ? F1 C6 C7 110.5(8) . . ? F2 C6 C7 111.9(9) . . ? F1 C6 C5 112.5(9) . . ? F2 C6 C5 110.4(7) . . ? C7 C6 C5 106.3(8) . . ? F3 C7 F4 107.5(9) . . ? F3 C7 C6 113.3(9) . . ? F4 C7 C6 108.4(9) . . ? F3 C7 C8 114.7(9) . . ? F4 C7 C8 110.4(8) . . ? C6 C7 C8 102.4(9) . . ? F5 C8 F6 103.1(7) . . ? F5 C8 C9 112.8(7) . . ? F6 C8 C9 113.5(8) . . ? F5 C8 C7 111.0(8) . . ? F6 C8 C7 108.5(7) . . ? C9 C8 C7 108.0(8) . . ? C5 C9 C11 122.1(8) . . ? C5 C9 C8 108.0(9) . . ? C11 C9 C8 129.8(8) . . ? C11 C10 C1 116.8(9) . . ? C11 C10 Si1 125.6(7) . . ? C1 C10 Si1 117.5(7) . . ? C10 C11 C9 119.6(8) . . ? C10 C11 C12 124.1(9) . . ? C9 C11 C12 116.2(8) . . ? C13 C12 C11 125.9(8) . . ? C12 C13 C20 123.4(8) . . ? C12 C13 S2 121.4(6) . . ? C20 C13 S2 115.2(6) . . ? C15 C14 C19 120.3(10) . . ? C15 C14 C4 121.8(10) . . ? C19 C14 C4 117.9(9) . . ? C14 C15 C16 119.9(11) . . ? C17 C16 C15 119.6(10) . . ? C16 C17 C18 121.9(10) . . ? C17 C18 C19 117.9(10) . . ? C14 C19 C18 120.4(10) . . ? C21 C20 C25 117.3(7) . . ? C21 C20 C13 121.6(8) . . ? C25 C20 C13 121.1(8) . . ? C22 C21 C20 121.7(8) . . ? C21 C22 C23 119.9(9) . . ? C24 C23 C22 118.1(8) . . ? C25 C24 C23 122.6(8) . . ? C24 C25 C20 120.2(8) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.774 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.120 # Attachment '1d.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 719461' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4,5,6-Tetrafluoro-2,8-diphenyl-4H-1,9-dithia-trindene (1d) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H12 F4 S2' _chemical_formula_sum 'C25 H12 F4 S2' _chemical_formula_weight 452.47 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 'P b a 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z' '-x, -y, z' _cell_length_a 19.245(10) _cell_length_b 24.970(11) _cell_length_c 3.9399(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1893.3(16) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 12278 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.6 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8521 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12987 _diffrn_reflns_av_R_equivalents 0.1461 _diffrn_reflns_av_sigmaI/netI 0.1806 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4257 _reflns_number_gt 2083 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material CrystalStructure _refine_special_details ; The molecules in the crystal have crystallographically two disordered structures with the same occupancies (0.5) for the cyclopentadienyl ring. The ring positions of two structures are the opposite of left-to-right each other. The SHELXL SAME and EADP commands were used for the refinement of the disordered atom pairs with the same displacement parameters. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0342P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.11(11) _refine_ls_number_reflns 4257 _refine_ls_number_parameters 299 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.1303 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 0.803 _refine_ls_restrained_S_all 0.803 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.88008(7) -0.00183(5) 0.9116(3) 0.0363(3) Uani 1 1 d . A . S2 S 0.88545(7) 0.13723(5) 0.7702(3) 0.0374(3) Uani 1 1 d . . . F1 F 0.5911(3) -0.0142(2) 0.6420(15) 0.0405(13) Uani 0.50 1 d PD A 1 F2 F 0.6352(3) -0.0291(2) 0.1343(17) 0.0430(16) Uani 0.50 1 d PD A 1 F3 F 0.5263(4) 0.0574(4) 0.178(2) 0.041(3) Uiso 0.50 1 d PD A 1 F4 F 0.6181(3) 0.1530(2) 0.2330(19) 0.0401(16) Uani 0.50 1 d PD A 1 C6 C 0.6274(7) 0.0102(5) 0.390(4) 0.0356(17) Uiso 0.50 1 d PD A 1 C7 C 0.5916(7) 0.0608(13) 0.284(6) 0.0365(17) Uiso 0.50 1 d PD A 1 C8 C 0.6342(9) 0.1017(5) 0.308(5) 0.0373(17) Uiso 0.50 1 d PD A 1 F1B F 0.6394(3) 0.1423(3) 0.0292(16) 0.0457(17) Uani 0.50 1 d PD A 2 F2B F 0.6011(3) 0.1470(2) 0.5426(15) 0.0463(15) Uani 0.50 1 d PD A 2 F3B F 0.5331(4) 0.0606(3) 0.1026(19) 0.035(3) Uiso 0.50 1 d PD A 2 F4B F 0.6174(4) -0.0312(2) 0.374(2) 0.0450(17) Uani 0.50 1 d PD A 2 C6B C 0.6343(9) 0.1111(5) 0.315(4) 0.0373(17) Uiso 0.50 1 d PD A 2 C7B C 0.5964(7) 0.0601(13) 0.249(6) 0.0365(17) Uiso 0.50 1 d PD A 2 C8B C 0.6359(8) 0.0208(5) 0.375(4) 0.0356(17) Uiso 0.50 1 d PD A 2 C10 C 0.8183(2) 0.09355(18) 0.6791(12) 0.0323(11) Uani 1 1 d . . . C11 C 0.7609(2) 0.12053(18) 0.5380(10) 0.0343(12) Uani 1 1 d . A . C12 C 0.7739(3) 0.17746(18) 0.5042(11) 0.0369(12) Uani 1 1 d . . . H12 H 0.7409 0.2020 0.4151 0.044 Uiso 1 1 calc R . . C13 C 0.8382(3) 0.19204(18) 0.6134(12) 0.0370(12) Uani 1 1 d . . . C9 C 0.7029(2) 0.09045(19) 0.4545(13) 0.0368(12) Uani 1 1 d . . . C5 C 0.7004(2) 0.03469(18) 0.5007(11) 0.0344(12) Uani 1 1 d . A . C1 C 0.8158(2) 0.03767(18) 0.7359(12) 0.0320(11) Uani 1 1 d . A . C2 C 0.7570(2) 0.00781(17) 0.6477(11) 0.0331(11) Uani 1 1 d . . . C3 C 0.7655(2) -0.04807(17) 0.7268(12) 0.0360(11) Uani 1 1 d . A . H3 H 0.7309 -0.0743 0.6827 0.043 Uiso 1 1 calc R . . C4 C 0.8277(2) -0.05963(17) 0.8703(12) 0.0356(12) Uani 1 1 d . . . C14 C 0.8559(2) -0.11188(17) 0.9803(12) 0.0323(11) Uani 1 1 d . A . C15 C 0.8192(2) -0.15861(18) 0.9131(13) 0.0394(12) Uani 1 1 d . . . H15 H 0.7761 -0.1563 0.7965 0.047 Uiso 1 1 calc R A . C16 C 0.8434(2) -0.20839(18) 1.0103(12) 0.0372(12) Uani 1 1 d . A . H16 H 0.8173 -0.2397 0.9605 0.045 Uiso 1 1 calc R . . C17 C 0.9066(3) -0.21219(18) 1.1827(12) 0.0391(13) Uani 1 1 d . . . H17 H 0.9240 -0.2462 1.2487 0.047 Uiso 1 1 calc R A . C18 C 0.9441(2) -0.16593(18) 1.2578(13) 0.0400(12) Uani 1 1 d . A . H18 H 0.9868 -0.1683 1.3775 0.048 Uiso 1 1 calc R . . C19 C 0.9184(2) -0.11605(17) 1.1558(12) 0.0379(12) Uani 1 1 d . . . H19 H 0.9440 -0.0846 1.2071 0.046 Uiso 1 1 calc R A . C20 C 0.8692(3) 0.24571(18) 0.6074(11) 0.0356(12) Uani 1 1 d . . . C21 C 0.8351(3) 0.28829(18) 0.4467(13) 0.0390(12) Uani 1 1 d . . . H21 H 0.7910 0.2826 0.3442 0.047 Uiso 1 1 calc R . . C22 C 0.8654(3) 0.33874(18) 0.4365(13) 0.0419(13) Uani 1 1 d . . . H22 H 0.8421 0.3672 0.3241 0.050 Uiso 1 1 calc R . . C23 C 0.9287(3) 0.34802(19) 0.5870(12) 0.0442(14) Uani 1 1 d . . . H23 H 0.9483 0.3829 0.5844 0.053 Uiso 1 1 calc R . . C24 C 0.9638(3) 0.30586(17) 0.7435(14) 0.0419(12) Uani 1 1 d . . . H24 H 1.0081 0.3120 0.8426 0.050 Uiso 1 1 calc R . . C25 C 0.9348(3) 0.25528(17) 0.7556(12) 0.0387(12) Uani 1 1 d . . . H25 H 0.9590 0.2269 0.8639 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0379(7) 0.0357(6) 0.0353(6) 0.0003(6) -0.0037(6) 0.0046(6) S2 0.0402(7) 0.0381(7) 0.0340(6) 0.0003(7) -0.0021(7) 0.0058(6) F1 0.040(3) 0.035(3) 0.047(3) 0.005(3) 0.006(3) -0.001(3) F2 0.048(4) 0.039(4) 0.042(3) -0.015(4) 0.002(3) -0.005(3) F4 0.035(4) 0.039(4) 0.046(4) 0.006(4) 0.000(4) 0.007(3) F1B 0.049(4) 0.035(4) 0.053(5) 0.012(4) -0.010(4) 0.011(3) F2B 0.045(4) 0.040(3) 0.054(4) -0.009(3) 0.010(3) 0.004(3) F4B 0.053(4) 0.023(3) 0.059(5) 0.003(4) -0.006(4) 0.000(3) C10 0.031(3) 0.036(3) 0.029(3) -0.004(2) -0.001(2) 0.005(2) C11 0.036(3) 0.042(3) 0.025(2) -0.002(2) 0.003(2) 0.006(2) C12 0.041(3) 0.041(3) 0.029(3) 0.007(2) 0.004(2) 0.014(2) C13 0.047(3) 0.035(3) 0.030(3) 0.004(2) 0.004(3) 0.012(2) C9 0.030(3) 0.047(3) 0.034(3) 0.003(3) 0.001(2) 0.010(2) C5 0.038(3) 0.036(3) 0.029(3) -0.005(2) -0.004(2) 0.005(2) C1 0.028(3) 0.042(3) 0.025(2) 0.001(3) -0.004(2) 0.000(2) C2 0.037(3) 0.034(3) 0.028(2) -0.007(2) 0.002(2) 0.008(2) C3 0.039(3) 0.035(3) 0.034(3) -0.007(3) -0.002(3) 0.002(2) C4 0.041(3) 0.031(3) 0.035(3) -0.009(2) 0.005(2) 0.002(2) C14 0.041(3) 0.030(3) 0.026(3) -0.004(2) 0.001(2) 0.000(2) C15 0.038(3) 0.045(3) 0.035(3) -0.002(3) 0.003(3) 0.007(2) C16 0.035(3) 0.035(3) 0.041(3) 0.001(3) 0.007(2) 0.001(2) C17 0.047(3) 0.035(3) 0.035(3) 0.000(3) 0.004(3) 0.004(2) C18 0.043(3) 0.041(3) 0.035(3) -0.001(3) 0.004(3) 0.009(2) C19 0.042(3) 0.037(3) 0.035(3) -0.006(3) -0.002(2) 0.002(2) C20 0.046(3) 0.035(3) 0.025(2) -0.001(2) 0.007(2) 0.003(2) C21 0.046(3) 0.038(3) 0.033(3) 0.001(3) 0.002(3) 0.006(2) C22 0.048(3) 0.036(3) 0.042(3) 0.007(3) 0.000(3) 0.014(3) C23 0.057(4) 0.028(3) 0.048(3) 0.005(3) 0.013(3) 0.003(3) C24 0.044(3) 0.042(3) 0.040(3) 0.000(3) 0.004(3) 0.001(2) C25 0.053(3) 0.031(2) 0.032(3) 0.000(3) -0.002(3) 0.006(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 S1 C1 1.727(4) . ? S1 C4 1.768(5) . ? S2 C10 1.729(5) . ? S2 C13 1.755(5) . ? F1 C6 1.359(14) . ? F2 C6 1.415(16) . ? F3 C7 1.326(10) . ? F4 C8 1.351(15) . ? C6 C7 1.50(3) . ? C6 C5 1.593(15) . ? C7 C8 1.31(3) . ? C8 C9 1.469(17) . ? F1B C6B 1.374(16) . ? F2B C6B 1.420(17) . ? F3B C7B 1.348(10) . ? F4B C8B 1.346(13) . ? C6B C7B 1.49(3) . ? C6B C9 1.520(18) . ? C7B C8B 1.34(3) . ? C8B C5 1.382(15) . ? C10 C11 1.408(6) . ? C10 C1 1.414(6) . ? C11 C9 1.386(6) . ? C11 C12 1.449(6) . ? C12 C13 1.361(6) . ? C13 C20 1.467(6) . ? C9 C5 1.405(6) . ? C5 C2 1.404(6) . ? C1 C2 1.399(6) . ? C2 C3 1.439(6) . ? C3 C4 1.355(6) . ? C4 C14 1.478(6) . ? C14 C15 1.389(6) . ? C14 C19 1.391(6) . ? C15 C16 1.381(6) . ? C16 C17 1.396(6) . ? C17 C18 1.394(6) . ? C18 C19 1.399(6) . ? C20 C21 1.401(6) . ? C20 C25 1.411(6) . ? C21 C22 1.389(6) . ? C22 C23 1.374(6) . ? C23 C24 1.395(6) . ? C24 C25 1.382(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 91.2(2) . . ? C10 S2 C13 91.8(2) . . ? F1 C6 F2 105.2(9) . . ? F1 C6 C7 110.2(14) . . ? F2 C6 C7 115.8(14) . . ? F1 C6 C5 115.1(11) . . ? F2 C6 C5 111.6(10) . . ? C7 C6 C5 99.2(10) . . ? C8 C7 F3 132(2) . . ? C8 C7 C6 110.3(10) . . ? F3 C7 C6 118(2) . . ? C7 C8 F4 125.3(16) . . ? C7 C8 C9 116.2(14) . . ? F4 C8 C9 118.3(11) . . ? F1B C6B F2B 101.0(10) . . ? F1B C6B C7B 112.2(15) . . ? F2B C6B C7B 115.5(14) . . ? F1B C6B C9 115.3(12) . . ? F2B C6B C9 112.1(12) . . ? C7B C6B C9 101.5(11) . . ? C8B C7B F3B 133(2) . . ? C8B C7B C6B 106.6(9) . . ? F3B C7B C6B 121(2) . . ? C7B C8B F4B 123.9(14) . . ? C7B C8B C5 117.3(13) . . ? F4B C8B C5 118.7(11) . . ? C11 C10 C1 120.6(4) . . ? C11 C10 S2 111.5(3) . . ? C1 C10 S2 127.9(3) . . ? C9 C11 C10 117.8(4) . . ? C9 C11 C12 130.4(5) . . ? C10 C11 C12 111.8(4) . . ? C13 C12 C11 112.9(4) . . ? C12 C13 C20 127.5(4) . . ? C12 C13 S2 112.0(4) . . ? C20 C13 S2 120.5(4) . . ? C11 C9 C5 122.2(4) . . ? C11 C9 C8 135.7(7) . . ? C5 C9 C8 102.1(6) . . ? C11 C9 C6B 127.0(7) . . ? C5 C9 C6B 110.7(7) . . ? C8B C5 C2 136.5(7) . . ? C8B C5 C9 103.5(6) . . ? C2 C5 C9 120.1(4) . . ? C2 C5 C6 127.9(6) . . ? C9 C5 C6 111.9(6) . . ? C2 C1 C10 120.9(4) . . ? C2 C1 S1 112.0(3) . . ? C10 C1 S1 127.1(3) . . ? C1 C2 C5 118.4(4) . . ? C1 C2 C3 111.8(4) . . ? C5 C2 C3 129.9(4) . . ? C4 C3 C2 113.4(4) . . ? C3 C4 C14 129.4(4) . . ? C3 C4 S1 111.6(3) . . ? C14 C4 S1 119.0(4) . . ? C15 C14 C19 118.1(4) . . ? C15 C14 C4 119.9(4) . . ? C19 C14 C4 122.0(4) . . ? C16 C15 C14 122.1(5) . . ? C15 C16 C17 119.3(4) . . ? C18 C17 C16 119.8(4) . . ? C17 C18 C19 119.6(5) . . ? C14 C19 C18 121.0(4) . . ? C21 C20 C25 118.6(4) . . ? C21 C20 C13 120.7(5) . . ? C25 C20 C13 120.8(4) . . ? C22 C21 C20 120.3(5) . . ? C23 C22 C21 120.9(5) . . ? C22 C23 C24 119.6(5) . . ? C25 C24 C23 120.5(5) . . ? C24 C25 C20 120.1(4) . . ? 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 F1 C6 C7 C8 124.4(17) . . . . ? F2 C6 C7 C8 -116.3(17) . . . . ? C5 C6 C7 C8 3(2) . . . . ? F1 C6 C7 F3 -57(2) . . . . ? F2 C6 C7 F3 62(2) . . . . ? C5 C6 C7 F3 -178.4(16) . . . . ? F3 C7 C8 F4 2(4) . . . . ? C6 C7 C8 F4 -179.7(13) . . . . ? F3 C7 C8 C9 177(2) . . . . ? C6 C7 C8 C9 -5(3) . . . . ? F1B C6B C7B C8B 130.2(16) . . . . ? F2B C6B C7B C8B -114.9(16) . . . . ? C9 C6B C7B C8B 7(2) . . . . ? F1B C6B C7B F3B -53(2) . . . . ? F2B C6B C7B F3B 62(2) . . . . ? C9 C6B C7B F3B -176.2(17) . . . . ? F3B C7B C8B F4B 1(4) . . . . ? C6B C7B C8B F4B 177.3(13) . . . . ? F3B C7B C8B C5 178(2) . . . . ? C6B C7B C8B C5 -5(2) . . . . ? C13 S2 C10 C11 -1.0(4) . . . . ? C13 S2 C10 C1 -179.8(4) . . . . ? C1 C10 C11 C9 -0.7(7) . . . . ? S2 C10 C11 C9 -179.5(3) . . . . ? C1 C10 C11 C12 179.4(4) . . . . ? S2 C10 C11 C12 0.5(5) . . . . ? C9 C11 C12 C13 -179.5(5) . . . . ? C10 C11 C12 C13 0.4(6) . . . . ? C11 C12 C13 C20 178.2(4) . . . . ? C11 C12 C13 S2 -1.2(5) . . . . ? C10 S2 C13 C12 1.2(4) . . . . ? C10 S2 C13 C20 -178.1(4) . . . . ? C10 C11 C9 C5 -1.2(7) . . . . ? C12 C11 C9 C5 178.7(4) . . . . ? C10 C11 C9 C8 179.9(11) . . . . ? C12 C11 C9 C8 -0.2(14) . . . . ? C10 C11 C9 C6B 177.0(9) . . . . ? C12 C11 C9 C6B -3.0(11) . . . . ? C7 C8 C9 C11 -176.9(13) . . . . ? F4 C8 C9 C11 -2(2) . . . . ? C7 C8 C9 C5 4.1(18) . . . . ? F4 C8 C9 C5 179.3(12) . . . . ? F1B C6B C9 C11 53.6(15) . . . . ? F2B C6B C9 C11 -61.1(13) . . . . ? C7B C6B C9 C11 175.1(11) . . . . ? F1B C6B C9 C5 -128.0(9) . . . . ? F2B C6B C9 C5 117.2(9) . . . . ? C7B C6B C9 C5 -6.5(15) . . . . ? C7B C8B C5 C2 -179.4(13) . . . . ? F4B C8B C5 C2 -1.6(19) . . . . ? C7B C8B C5 C9 0.7(17) . . . . ? F4B C8B C5 C9 178.5(10) . . . . ? C11 C9 C5 C8B -177.6(8) . . . . ? C8 C9 C5 C8B 1.6(12) . . . . ? C6B C9 C5 C8B 3.9(9) . . . . ? C11 C9 C5 C2 2.5(7) . . . . ? C8 C9 C5 C2 -178.3(8) . . . . ? C6B C9 C5 C2 -176.0(8) . . . . ? C11 C9 C5 C6 179.1(7) . . . . ? C8 C9 C5 C6 -1.7(8) . . . . ? F1 C6 C5 C2 58.0(14) . . . . ? F2 C6 C5 C2 -61.8(13) . . . . ? C7 C6 C5 C2 175.6(10) . . . . ? F1 C6 C5 C9 -118.3(9) . . . . ? F2 C6 C5 C9 121.9(9) . . . . ? C7 C6 C5 C9 -0.7(13) . . . . ? C11 C10 C1 C2 1.2(7) . . . . ? S2 C10 C1 C2 179.9(4) . . . . ? C11 C10 C1 S1 -178.9(4) . . . . ? S2 C10 C1 S1 -0.2(7) . . . . ? C4 S1 C1 C2 -0.3(4) . . . . ? C4 S1 C1 C10 179.7(4) . . . . ? C10 C1 C2 C5 0.1(7) . . . . ? S1 C1 C2 C5 -179.8(4) . . . . ? C10 C1 C2 C3 180.0(4) . . . . ? S1 C1 C2 C3 0.0(5) . . . . ? C8B C5 C2 C1 178.3(10) . . . . ? C9 C5 C2 C1 -1.9(7) . . . . ? C6 C5 C2 C1 -177.9(8) . . . . ? C8B C5 C2 C3 -1.6(13) . . . . ? C9 C5 C2 C3 178.3(5) . . . . ? C6 C5 C2 C3 2.2(11) . . . . ? C1 C2 C3 C4 0.4(6) . . . . ? C5 C2 C3 C4 -179.7(5) . . . . ? C2 C3 C4 C14 -178.8(4) . . . . ? C2 C3 C4 S1 -0.7(5) . . . . ? C1 S1 C4 C3 0.6(4) . . . . ? C1 S1 C4 C14 178.9(4) . . . . ? C3 C4 C14 C15 5.7(8) . . . . ? S1 C4 C14 C15 -172.3(4) . . . . ? C3 C4 C14 C19 -173.3(5) . . . . ? S1 C4 C14 C19 8.7(6) . . . . ? C19 C14 C15 C16 -1.0(7) . . . . ? C4 C14 C15 C16 180.0(4) . . . . ? C14 C15 C16 C17 0.2(7) . . . . ? C15 C16 C17 C18 0.7(7) . . . . ? C16 C17 C18 C19 -0.8(7) . . . . ? C15 C14 C19 C18 0.9(7) . . . . ? C4 C14 C19 C18 179.9(4) . . . . ? C17 C18 C19 C14 0.0(7) . . . . ? C12 C13 C20 C21 -6.8(8) . . . . ? S2 C13 C20 C21 172.5(3) . . . . ? C12 C13 C20 C25 174.9(5) . . . . ? S2 C13 C20 C25 -5.9(6) . . . . ? C25 C20 C21 C22 -0.4(7) . . . . ? C13 C20 C21 C22 -178.8(4) . . . . ? C20 C21 C22 C23 -0.9(8) . . . . ? C21 C22 C23 C24 1.9(7) . . . . ? C22 C23 C24 C25 -1.6(7) . . . . ? C23 C24 C25 C20 0.4(7) . . . . ? C21 C20 C25 C24 0.6(7) . . . . ? C13 C20 C25 C24 179.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.312 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.062