# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_0.00GPaBenzothiopheneDTENOTINCELL _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 11.4349(6) _cell_length_b 15.5450(6) _cell_length_c 12.8179(6) _cell_angle_alpha 90.00 _cell_angle_beta 113.755(6) _cell_angle_gamma 90.00 _cell_volume 2085.41(17) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7250 _cell_measurement_theta_min 3.0802 _cell_measurement_theta_max 29.2228 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.89102 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method \w _diffrn_reflns_number 27119 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 29.29 _reflns_number_total 5221 _reflns_number_gt 3850 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.851 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.057 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0877P)^2^+0.3336P] 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 5221 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1517 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.5523(2) 0.11883(15) 0.80545(19) 0.0372(5) Uani 1 1 d . . . C2 C 0.4824(2) 0.1673(2) 0.8639(2) 0.0560(7) Uani 1 1 d . . . C3 C 0.5859(3) 0.2050(2) 0.9707(3) 0.0612(8) Uani 1 1 d . . . C4 C 0.7041(2) 0.15234(17) 0.9878(2) 0.0460(6) Uani 1 1 d . . . C5 C 0.6763(2) 0.11160(13) 0.87398(17) 0.0337(4) Uani 1 1 d . . . C11 C 0.5863(3) 0.20214(19) 0.6011(2) 0.0562(7) Uani 1 1 d . . . H11A H 0.6201 0.2277 0.6756 0.084 Uiso 1 1 calc R . . H11B H 0.5402 0.2447 0.5456 0.084 Uiso 1 1 calc R . . H11C H 0.6552 0.1802 0.5843 0.084 Uiso 1 1 calc R . . C12 C 0.4983(2) 0.13034(16) 0.5980(2) 0.0426(5) Uani 1 1 d . . . C13 C 0.4834(2) 0.09063(15) 0.68638(19) 0.0374(5) Uani 1 1 d . . . C14 C 0.3852(2) 0.02571(15) 0.6507(2) 0.0407(5) Uani 1 1 d . . . C15 C 0.3451(3) -0.03016(18) 0.7160(2) 0.0527(6) Uani 1 1 d . . . H15 H 0.3834 -0.0279 0.7951 0.063 Uiso 1 1 calc R . . C16 C 0.2494(3) -0.0880(2) 0.6624(3) 0.0684(8) Uani 1 1 d . . . H16 H 0.2227 -0.1249 0.7056 0.082 Uiso 1 1 calc R . . C17 C 0.1915(3) -0.0922(2) 0.5440(3) 0.0771(10) Uani 1 1 d . . . H17 H 0.1260 -0.1316 0.5092 0.093 Uiso 1 1 calc R . . C18 C 0.2292(3) -0.0395(2) 0.4780(3) 0.0665(8) Uani 1 1 d . . . H18 H 0.1903 -0.0428 0.3989 0.080 Uiso 1 1 calc R . . C19 C 0.3273(2) 0.01938(17) 0.5318(2) 0.0473(6) Uani 1 1 d . . . C31 C 0.7054(3) -0.08621(18) 0.8796(3) 0.0649(8) Uani 1 1 d . . . H31A H 0.7558 -0.1230 0.9415 0.097 Uiso 1 1 calc R . . H31B H 0.6638 -0.1201 0.8120 0.097 Uiso 1 1 calc R . . H31C H 0.6423 -0.0573 0.8983 0.097 Uiso 1 1 calc R . . C32 C 0.7899(2) -0.02138(16) 0.8591(2) 0.0443(5) Uani 1 1 d . . . C33 C 0.7783(2) 0.06590(14) 0.85435(17) 0.0349(4) Uani 1 1 d . . . C34 C 0.8799(2) 0.10813(15) 0.83525(17) 0.0367(5) Uani 1 1 d . . . C35 C 0.8997(2) 0.19568(17) 0.8231(2) 0.0462(6) Uani 1 1 d . . . H35 H 0.8442 0.2364 0.8309 0.055 Uiso 1 1 calc R . . C36 C 1.0018(3) 0.2215(2) 0.7996(3) 0.0626(8) Uani 1 1 d . . . H36 H 1.0149 0.2798 0.7918 0.075 Uiso 1 1 calc R . . C37 C 1.0853(3) 0.1616(3) 0.7873(3) 0.0743(10) Uani 1 1 d . . . H37 H 1.1531 0.1802 0.7706 0.089 Uiso 1 1 calc R . . C38 C 1.0694(3) 0.0755(2) 0.7995(3) 0.0663(9) Uani 1 1 d . . . H38 H 1.1257 0.0356 0.7914 0.080 Uiso 1 1 calc R . . C39 C 0.9671(2) 0.04872(18) 0.8243(2) 0.0477(6) Uani 1 1 d . . . F1A F 0.4018(2) 0.22473(17) 0.7987(2) 0.1097(9) Uani 1 1 d . . . F2A F 0.4096(2) 0.11417(17) 0.8986(2) 0.1026(9) Uani 1 1 d . . . F3A F 0.6072(2) 0.28721(14) 0.9447(3) 0.1135(9) Uani 1 1 d . . . F4A F 0.5571(2) 0.2110(2) 1.05849(19) 0.1153(10) Uani 1 1 d . . . F5A F 0.80992(16) 0.20020(13) 1.02784(15) 0.0736(5) Uani 1 1 d . . . F6A F 0.7206(2) 0.09121(14) 1.06779(14) 0.0814(6) Uani 1 1 d . . . S1 S 0.39285(7) 0.09089(5) 0.46732(5) 0.0530(2) Uani 1 1 d . . . S2 S 0.92411(7) -0.05551(5) 0.84013(7) 0.0583(2) 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 0.0318(11) 0.0437(12) 0.0377(11) -0.0022(9) 0.0156(9) 0.0011(9) C2 0.0382(13) 0.0733(18) 0.0581(16) -0.0122(13) 0.0210(12) 0.0082(12) C3 0.0560(17) 0.0710(19) 0.0618(17) -0.0238(14) 0.0293(14) 0.0029(14) C4 0.0432(13) 0.0574(15) 0.0371(12) -0.0099(10) 0.0159(10) -0.0040(10) C5 0.0339(11) 0.0365(11) 0.0320(10) -0.0028(8) 0.0146(8) -0.0019(8) C11 0.0511(15) 0.0597(16) 0.0528(15) 0.0097(12) 0.0159(12) -0.0028(12) C12 0.0371(12) 0.0462(13) 0.0396(12) 0.0027(10) 0.0102(9) 0.0066(9) C13 0.0287(10) 0.0429(12) 0.0376(11) -0.0016(9) 0.0103(8) 0.0052(8) C14 0.0333(11) 0.0456(12) 0.0403(12) -0.0033(9) 0.0117(9) 0.0023(9) C15 0.0517(15) 0.0598(16) 0.0491(14) -0.0051(12) 0.0227(12) -0.0089(12) C16 0.069(2) 0.0705(19) 0.0679(19) -0.0067(15) 0.0300(16) -0.0226(16) C17 0.073(2) 0.078(2) 0.072(2) -0.0187(17) 0.0208(17) -0.0343(18) C18 0.0619(18) 0.075(2) 0.0483(15) -0.0136(14) 0.0074(13) -0.0144(15) C19 0.0426(13) 0.0515(14) 0.0407(12) -0.0025(10) 0.0095(10) 0.0016(10) C31 0.0658(19) 0.0446(14) 0.081(2) 0.0023(14) 0.0264(16) -0.0059(13) C32 0.0420(13) 0.0439(13) 0.0431(12) -0.0025(10) 0.0129(10) 0.0055(10) C33 0.0303(10) 0.0419(11) 0.0291(10) -0.0022(8) 0.0085(8) 0.0030(8) C34 0.0278(10) 0.0504(13) 0.0278(10) 0.0008(9) 0.0072(8) 0.0045(9) C35 0.0357(12) 0.0546(15) 0.0444(13) 0.0034(11) 0.0121(10) 0.0004(10) C36 0.0434(15) 0.076(2) 0.0634(18) 0.0194(15) 0.0164(13) -0.0078(13) C37 0.0389(15) 0.113(3) 0.074(2) 0.0321(19) 0.0257(14) 0.0060(16) C38 0.0395(14) 0.101(3) 0.0636(18) 0.0174(17) 0.0266(13) 0.0237(15) C39 0.0355(12) 0.0656(16) 0.0399(12) 0.0064(11) 0.0130(10) 0.0147(11) F1A 0.0893(15) 0.135(2) 0.0857(15) -0.0179(14) 0.0160(12) 0.0709(15) F2A 0.0815(14) 0.139(2) 0.1222(19) -0.0581(16) 0.0777(14) -0.0432(14) F3A 0.0930(16) 0.0586(12) 0.174(3) -0.0275(14) 0.0385(17) 0.0022(11) F4A 0.0812(14) 0.202(3) 0.0736(13) -0.0560(16) 0.0425(12) 0.0147(16) F5A 0.0525(9) 0.0979(14) 0.0670(11) -0.0436(10) 0.0207(8) -0.0232(9) F6A 0.1132(16) 0.0934(14) 0.0397(9) 0.0094(9) 0.0331(10) 0.0159(12) S1 0.0551(4) 0.0591(4) 0.0351(3) 0.0057(3) 0.0079(3) 0.0002(3) S2 0.0560(4) 0.0539(4) 0.0656(5) 0.0022(3) 0.0252(3) 0.0218(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C5 1.338(3) . ? C1 C13 1.474(3) . ? C1 C2 1.501(3) . ? C2 F1A 1.314(4) . ? C2 F2A 1.367(4) . ? C2 C3 1.521(4) . ? C3 F4A 1.297(3) . ? C3 F3A 1.366(4) . ? C3 C4 1.518(4) . ? C4 F5A 1.335(3) . ? C4 F6A 1.354(3) . ? C4 C5 1.503(3) . ? C5 C33 1.471(3) . ? C11 C12 1.492(4) . ? C12 C13 1.360(3) . ? C12 S1 1.735(2) . ? C13 C14 1.440(3) . ? C14 C19 1.400(3) . ? C14 C15 1.404(4) . ? C15 C16 1.368(4) . ? C16 C17 1.391(5) . ? C17 C18 1.366(5) . ? C18 C19 1.396(4) . ? C19 S1 1.727(3) . ? C31 C32 1.490(4) . ? C32 C33 1.362(3) . ? C32 S2 1.731(2) . ? C33 C34 1.438(3) . ? C34 C35 1.399(3) . ? C34 C39 1.407(3) . ? C35 C36 1.377(4) . ? C36 C37 1.387(5) . ? C37 C38 1.368(5) . ? C38 C39 1.393(4) . ? C39 S2 1.729(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 C5 C1 C13 129.6(2) . . ? C5 C1 C2 110.6(2) . . ? C13 C1 C2 119.7(2) . . ? F1A C2 F2A 104.7(2) . . ? F1A C2 C1 113.7(2) . . ? F2A C2 C1 112.1(2) . . ? F1A C2 C3 113.8(3) . . ? F2A C2 C3 107.2(2) . . ? C1 C2 C3 105.3(2) . . ? F4A C3 F3A 106.1(3) . . ? F4A C3 C4 115.8(3) . . ? F3A C3 C4 107.7(2) . . ? F4A C3 C2 115.5(3) . . ? F3A C3 C2 107.0(3) . . ? C4 C3 C2 104.3(2) . . ? F5A C4 F6A 105.8(2) . . ? F5A C4 C5 114.33(19) . . ? F6A C4 C5 110.5(2) . . ? F5A C4 C3 111.8(2) . . ? F6A C4 C3 109.5(2) . . ? C5 C4 C3 105.0(2) . . ? C1 C5 C33 129.16(19) . . ? C1 C5 C4 110.82(19) . . ? C33 C5 C4 119.85(19) . . ? C13 C12 C11 128.8(2) . . ? C13 C12 S1 111.84(18) . . ? C11 C12 S1 119.31(18) . . ? C12 C13 C14 113.4(2) . . ? C12 C13 C1 122.2(2) . . ? C14 C13 C1 124.1(2) . . ? C19 C14 C15 118.7(2) . . ? C19 C14 C13 111.2(2) . . ? C15 C14 C13 130.1(2) . . ? C16 C15 C14 119.6(3) . . ? C15 C16 C17 120.8(3) . . ? C18 C17 C16 121.1(3) . . ? C17 C18 C19 118.6(3) . . ? C18 C19 C14 121.2(3) . . ? C18 C19 S1 127.1(2) . . ? C14 C19 S1 111.71(19) . . ? C33 C32 C31 128.6(2) . . ? C33 C32 S2 111.99(19) . . ? C31 C32 S2 119.44(19) . . ? C32 C33 C34 113.1(2) . . ? C32 C33 C5 122.9(2) . . ? C34 C33 C5 123.97(19) . . ? C35 C34 C39 118.3(2) . . ? C35 C34 C33 129.9(2) . . ? C39 C34 C33 111.8(2) . . ? C36 C35 C34 119.8(3) . . ? C35 C36 C37 120.8(3) . . ? C38 C37 C36 121.0(3) . . ? C37 C38 C39 118.7(3) . . ? C38 C39 C34 121.4(3) . . ? C38 C39 S2 127.7(2) . . ? C34 C39 S2 110.91(18) . . ? C19 S1 C12 91.87(12) . . ? C39 S2 C32 92.26(12) . . ? 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 C5 C1 C2 F1A 136.3(3) . . . . ? C13 C1 C2 F1A -40.8(4) . . . . ? C5 C1 C2 F2A -105.1(3) . . . . ? C13 C1 C2 F2A 77.7(3) . . . . ? C5 C1 C2 C3 11.1(3) . . . . ? C13 C1 C2 C3 -166.0(2) . . . . ? F1A C2 C3 F4A 88.1(4) . . . . ? F2A C2 C3 F4A -27.2(4) . . . . ? C1 C2 C3 F4A -146.8(3) . . . . ? F1A C2 C3 F3A -29.8(3) . . . . ? F2A C2 C3 F3A -145.1(2) . . . . ? C1 C2 C3 F3A 95.4(3) . . . . ? F1A C2 C3 C4 -143.7(3) . . . . ? F2A C2 C3 C4 101.0(3) . . . . ? C1 C2 C3 C4 -18.5(3) . . . . ? F4A C3 C4 F5A -88.2(3) . . . . ? F3A C3 C4 F5A 30.3(3) . . . . ? C2 C3 C4 F5A 143.8(2) . . . . ? F4A C3 C4 F6A 28.7(3) . . . . ? F3A C3 C4 F6A 147.2(2) . . . . ? C2 C3 C4 F6A -99.4(3) . . . . ? F4A C3 C4 C5 147.3(3) . . . . ? F3A C3 C4 C5 -94.2(3) . . . . ? C2 C3 C4 C5 19.3(3) . . . . ? C13 C1 C5 C33 -6.6(4) . . . . ? C2 C1 C5 C33 176.6(2) . . . . ? C13 C1 C5 C4 178.2(2) . . . . ? C2 C1 C5 C4 1.4(3) . . . . ? F5A C4 C5 C1 -136.3(2) . . . . ? F6A C4 C5 C1 104.5(2) . . . . ? C3 C4 C5 C1 -13.4(3) . . . . ? F5A C4 C5 C33 48.0(3) . . . . ? F6A C4 C5 C33 -71.2(3) . . . . ? C3 C4 C5 C33 170.9(2) . . . . ? C11 C12 C13 C14 177.6(2) . . . . ? S1 C12 C13 C14 0.3(3) . . . . ? C11 C12 C13 C1 3.8(4) . . . . ? S1 C12 C13 C1 -173.51(17) . . . . ? C5 C1 C13 C12 -71.2(3) . . . . ? C2 C1 C13 C12 105.4(3) . . . . ? C5 C1 C13 C14 115.7(3) . . . . ? C2 C1 C13 C14 -67.8(3) . . . . ? C12 C13 C14 C19 -0.4(3) . . . . ? C1 C13 C14 C19 173.3(2) . . . . ? C12 C13 C14 C15 177.7(2) . . . . ? C1 C13 C14 C15 -8.6(4) . . . . ? C19 C14 C15 C16 -1.3(4) . . . . ? C13 C14 C15 C16 -179.2(3) . . . . ? C14 C15 C16 C17 0.1(5) . . . . ? C15 C16 C17 C18 0.6(6) . . . . ? C16 C17 C18 C19 -0.2(6) . . . . ? C17 C18 C19 C14 -0.9(5) . . . . ? C17 C18 C19 S1 178.8(3) . . . . ? C15 C14 C19 C18 1.7(4) . . . . ? C13 C14 C19 C18 -180.0(3) . . . . ? C15 C14 C19 S1 -178.08(19) . . . . ? C13 C14 C19 S1 0.3(3) . . . . ? C31 C32 C33 C34 178.8(3) . . . . ? S2 C32 C33 C34 -0.2(2) . . . . ? C31 C32 C33 C5 2.3(4) . . . . ? S2 C32 C33 C5 -176.64(16) . . . . ? C1 C5 C33 C32 -74.7(3) . . . . ? C4 C5 C33 C32 100.1(3) . . . . ? C1 C5 C33 C34 109.2(3) . . . . ? C4 C5 C33 C34 -76.0(3) . . . . ? C32 C33 C34 C35 178.6(2) . . . . ? C5 C33 C34 C35 -5.0(4) . . . . ? C32 C33 C34 C39 0.8(3) . . . . ? C5 C33 C34 C39 177.2(2) . . . . ? C39 C34 C35 C36 0.8(3) . . . . ? C33 C34 C35 C36 -176.8(2) . . . . ? C34 C35 C36 C37 0.2(4) . . . . ? C35 C36 C37 C38 -0.7(5) . . . . ? C36 C37 C38 C39 0.2(5) . . . . ? C37 C38 C39 C34 0.9(4) . . . . ? C37 C38 C39 S2 178.3(2) . . . . ? C35 C34 C39 C38 -1.4(4) . . . . ? C33 C34 C39 C38 176.7(2) . . . . ? C35 C34 C39 S2 -179.13(17) . . . . ? C33 C34 C39 S2 -1.1(2) . . . . ? C18 C19 S1 C12 -179.8(3) . . . . ? C14 C19 S1 C12 -0.1(2) . . . . ? C13 C12 S1 C19 -0.16(19) . . . . ? C11 C12 S1 C19 -177.7(2) . . . . ? C38 C39 S2 C32 -176.7(3) . . . . ? C34 C39 S2 C32 0.86(19) . . . . ? C33 C32 S2 C39 -0.4(2) . . . . ? C31 C32 S2 C39 -179.4(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961251' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_0.86GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 11.262(6) _cell_length_b 14.9356(12) _cell_length_c 12.497(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.73(6) _cell_angle_gamma 90.00 _cell_volume 1924.3(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used 881 _cell_measurement_theta_min 3.3580 _cell_measurement_theta_max 22.5022 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.84497 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 6487 _diffrn_reflns_av_R_equivalents 0.0846 _diffrn_reflns_av_sigmaI/netI 0.0919 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 25.55 _reflns_number_total 1294 _reflns_number_gt 865 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.327 _diffrn_reflns_theta_full 25.55 _diffrn_measured_fraction_theta_full 0.327 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0877P)^2^+0.3336P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1294 _refine_ls_number_parameters 137 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.1415 _refine_ls_R_factor_gt 0.0989 _refine_ls_wR_factor_ref 0.2625 _refine_ls_wR_factor_gt 0.2333 _refine_ls_goodness_of_fit_ref 1.555 _refine_ls_restrained_S_all 1.524 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_hydrogen_treatment constr _refine_diff_density_max 0.463 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.076 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.5565(12) 0.1187(5) 0.8053(9) 0.028(2) Uiso 1 1 d D . . C2 C 0.4831(11) 0.1691(5) 0.8632(9) 0.038(2) Uiso 1 1 d D . . C3 C 0.5903(10) 0.2129(5) 0.9709(10) 0.049(3) Uiso 1 1 d D . . C4 C 0.7104(9) 0.1567(4) 0.9900(7) 0.031(2) Uiso 1 1 d D . . C5 C 0.6820(10) 0.1134(4) 0.8755(7) 0.0236(19) Uiso 1 1 d D . . C11 C 0.5966(14) 0.1993(5) 0.5941(10) 0.039(2) Uiso 1 1 d D . . H11A H 0.6089 0.2407 0.6564 0.059 Uiso 1 1 calc R . . H11B H 0.5642 0.2308 0.5209 0.059 Uiso 1 1 calc R . . H11C H 0.6779 0.1717 0.6061 0.059 Uiso 1 1 calc R . . C12 C 0.5009(11) 0.1287(5) 0.5921(8) 0.030(2) Uiso 1 1 d D . . C13 C 0.4840(11) 0.0892(5) 0.6835(8) 0.027(2) Uiso 1 1 d D . . C14 C 0.3804(11) 0.0238(5) 0.6467(8) 0.029(2) Uiso 1 1 d D . . C15 C 0.3383(12) -0.0317(5) 0.7147(9) 0.037(2) Uiso 1 1 d D . . H15 H 0.3785 -0.0297 0.7959 0.044 Uiso 1 1 calc R . . C16 C 0.2364(15) -0.0892(6) 0.6596(11) 0.058(3) Uiso 1 1 d D . . H16 H 0.2081 -0.1273 0.7034 0.069 Uiso 1 1 calc R . . C17 C 0.1754(14) -0.0903(6) 0.5375(9) 0.046(3) Uiso 1 1 d D . . H17 H 0.1059 -0.1290 0.5022 0.056 Uiso 1 1 calc R . . C18 C 0.2126(12) -0.0377(5) 0.4684(10) 0.040(2) Uiso 1 1 d D . . H18 H 0.1700 -0.0394 0.3873 0.048 Uiso 1 1 calc R . . C19 C 0.3184(11) 0.0193(5) 0.5246(7) 0.030(2) Uiso 1 1 d D . . C31 C 0.7111(13) -0.0918(5) 0.8819(10) 0.038(2) Uiso 1 1 d D . . H31A H 0.7617 -0.1301 0.9457 0.056 Uiso 1 1 calc R . . H31B H 0.6671 -0.1273 0.8132 0.056 Uiso 1 1 calc R . . H31C H 0.6484 -0.0601 0.9015 0.056 Uiso 1 1 calc R . . C32 C 0.7977(10) -0.0267(5) 0.8591(9) 0.036(2) Uiso 1 1 d D . . C33 C 0.7842(11) 0.0651(5) 0.8546(8) 0.027(2) Uiso 1 1 d D . . C34 C 0.8888(11) 0.1073(5) 0.8368(8) 0.028(2) Uiso 1 1 d D . . C35 C 0.9079(14) 0.1991(5) 0.8210(9) 0.035(2) Uiso 1 1 d D . . H35 H 0.8507 0.2415 0.8275 0.042 Uiso 1 1 calc R . . C36 C 1.0104(13) 0.2255(7) 0.7963(10) 0.046(3) Uiso 1 1 d D . . H36 H 1.0225 0.2861 0.7864 0.055 Uiso 1 1 calc R . . C37 C 1.0972(15) 0.1630(6) 0.7855(11) 0.058(3) Uiso 1 1 d D . . H37 H 1.1660 0.1822 0.7682 0.070 Uiso 1 1 calc R . . C38 C 1.0814(14) 0.0744(7) 0.8003(11) 0.059(3) Uiso 1 1 d D . . H38 H 1.1388 0.0327 0.7926 0.071 Uiso 1 1 calc R . . C39 C 0.9795(12) 0.0469(5) 0.8267(9) 0.034(2) Uiso 1 1 d D . . F1 F 0.4008(10) 0.2287(3) 0.7940(8) 0.0641(19) Uiso 1 1 d D . . F2 F 0.4147(11) 0.1133(4) 0.9045(8) 0.076(2) Uiso 1 1 d D . . F3 F 0.6100(10) 0.2973(3) 0.9430(7) 0.0611(18) Uiso 1 1 d D . . F4 F 0.5630(10) 0.2169(4) 1.0643(9) 0.088(3) Uiso 1 1 d D . . F5 F 0.8187(9) 0.2075(3) 1.0304(7) 0.0490(16) Uiso 1 1 d D . . F6 F 0.7277(10) 0.0947(3) 1.0731(7) 0.0518(16) Uiso 1 1 d D . . S1 S 0.3906(4) 0.08999(13) 0.4585(3) 0.042(4) Uani 1 1 d D . . S2 S 0.9348(5) -0.06182(14) 0.8427(3) 0.035(4) Uani 1 1 d 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 S1 0.043(6) 0.0392(13) 0.032(3) 0.0032(12) 0.004(4) -0.0044(16) S2 0.028(6) 0.0380(14) 0.051(4) 0.0044(12) 0.029(4) 0.0129(17) 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 C5 1.333(12) . ? C1 C13 1.475(10) . ? C1 C2 1.502(16) . ? C2 F1 1.324(8) . ? C2 F2 1.369(12) . ? C2 C3 1.546(9) . ? C3 F4 1.322(13) . ? C3 F3 1.349(10) . ? C3 C4 1.527(10) . ? C4 F5 1.350(10) . ? C4 F6 1.346(10) . ? C4 C5 1.483(11) . ? C5 C33 1.469(12) . ? C11 C12 1.502(12) . ? C12 C13 1.364(12) . ? C12 S1 1.731(7) . ? C13 C14 1.448(10) . ? C14 C15 1.399(13) . ? C14 C19 1.401(10) . ? C15 C16 1.376(11) . ? C16 C17 1.398(11) . ? C17 C18 1.353(13) . ? C18 C19 1.402(10) . ? C19 S1 1.732(11) . ? C31 C32 1.483(12) . ? C32 C33 1.378(9) . ? C32 S2 1.720(12) . ? C33 C34 1.430(12) . ? C34 C39 1.405(12) . ? C34 C35 1.413(9) . ? C35 C36 1.368(14) . ? C36 C37 1.396(13) . ? C37 C38 1.357(10) . ? C38 C39 1.379(14) . ? C39 S2 1.735(9) . ? 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 C5 C1 C13 131.4(13) . . ? C5 C1 C2 110.9(9) . . ? C13 C1 C2 117.6(9) . . ? F1 C2 F2 107.7(10) . . ? F1 C2 C1 113.5(11) . . ? F2 C2 C1 112.2(8) . . ? F1 C2 C3 112.3(7) . . ? F2 C2 C3 106.8(9) . . ? C1 C2 C3 104.1(9) . . ? F4 C3 F3 107.9(10) . . ? F4 C3 C4 113.1(9) . . ? F3 C3 C4 109.1(10) . . ? F4 C3 C2 114.2(11) . . ? F3 C3 C2 108.8(8) . . ? C4 C3 C2 103.6(8) . . ? F5 C4 F6 105.7(6) . . ? F5 C4 C5 114.7(10) . . ? F6 C4 C5 110.7(6) . . ? F5 C4 C3 111.0(7) . . ? F6 C4 C3 110.0(10) . . ? C5 C4 C3 104.8(7) . . ? C1 C5 C33 127.7(9) . . ? C1 C5 C4 111.7(10) . . ? C33 C5 C4 120.3(7) . . ? C13 C12 C11 129.1(7) . . ? C13 C12 S1 112.1(7) . . ? C11 C12 S1 118.8(8) . . ? C12 C13 C14 113.1(7) . . ? C12 C13 C1 122.0(9) . . ? C14 C13 C1 124.7(11) . . ? C15 C14 C19 119.4(8) . . ? C15 C14 C13 129.3(8) . . ? C19 C14 C13 111.2(9) . . ? C16 C15 C14 118.9(11) . . ? C15 C16 C17 119.9(13) . . ? C18 C17 C16 123.2(11) . . ? C17 C18 C19 116.8(10) . . ? C14 C19 C18 121.7(10) . . ? C14 C19 S1 111.5(6) . . ? C18 C19 S1 126.8(8) . . ? C33 C32 C31 126.2(11) . . ? C33 C32 S2 112.8(9) . . ? C31 C32 S2 121.0(7) . . ? C32 C33 C34 111.2(10) . . ? C32 C33 C5 124.2(10) . . ? C34 C33 C5 124.4(7) . . ? C39 C34 C35 116.9(12) . . ? C39 C34 C33 113.9(8) . . ? C35 C34 C33 129.1(11) . . ? C36 C35 C34 120.1(13) . . ? C35 C36 C37 121.0(12) . . ? C38 C37 C36 120.3(15) . . ? C37 C38 C39 119.3(14) . . ? C38 C39 C34 122.4(9) . . ? C38 C39 S2 127.9(9) . . ? C34 C39 S2 109.6(9) . . ? C19 S1 C12 92.0(5) . . ? C32 S2 C39 92.5(6) . . ? _database_code_depnum_ccdc_archive 'CCDC 961252' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2.09GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 11.096(2) _cell_length_b 14.494(3) _cell_length_c 12.262(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.85(3) _cell_angle_gamma 90.00 _cell_volume 1803.7(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1025 _cell_measurement_theta_min 3.3363 _cell_measurement_theta_max 25.8419 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.90894 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 4474 _diffrn_reflns_av_R_equivalents 0.0789 _diffrn_reflns_av_sigmaI/netI 0.0842 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 22.53 _reflns_number_total 933 _reflns_number_gt 688 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.359 _diffrn_reflns_theta_full 22.53 _diffrn_measured_fraction_theta_full 0.359 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0339P)^2^+1.4145P] 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 933 _refine_ls_number_parameters 137 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.1037 _refine_ls_R_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.1713 _refine_ls_wR_factor_gt 0.1535 _refine_ls_goodness_of_fit_ref 1.536 _refine_ls_restrained_S_all 1.489 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.363 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.062 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.5594(13) 0.1191(5) 0.8041(9) 0.021(2) Uiso 1 1 d D . . C2 C 0.4841(11) 0.1700(6) 0.8632(9) 0.028(3) Uiso 1 1 d D . . C3 C 0.5898(11) 0.2172(5) 0.9738(10) 0.036(3) Uiso 1 1 d D . . C4 C 0.7120(10) 0.1607(5) 0.9920(8) 0.021(2) Uiso 1 1 d D . . C5 C 0.6860(11) 0.1136(5) 0.8751(8) 0.018(2) Uiso 1 1 d D . . C11 C 0.6022(14) 0.1986(5) 0.5924(12) 0.033(3) Uiso 1 1 d D . . H11A H 0.6505 0.2179 0.6734 0.050 Uiso 1 1 calc R . . H11B H 0.5575 0.2507 0.5449 0.050 Uiso 1 1 calc R . . H11C H 0.6620 0.1733 0.5615 0.050 Uiso 1 1 calc R . . C12 C 0.5035(12) 0.1269(5) 0.5881(9) 0.021(2) Uiso 1 1 d D . . C13 C 0.4845(12) 0.0877(5) 0.6807(9) 0.018(2) Uiso 1 1 d D . . C14 C 0.3758(12) 0.0232(5) 0.6435(8) 0.022(2) Uiso 1 1 d D . . C15 C 0.3312(13) -0.0331(5) 0.7118(10) 0.031(3) Uiso 1 1 d D . . H15 H 0.3736 -0.0332 0.7946 0.037 Uiso 1 1 calc R . . C16 C 0.2237(15) -0.0880(6) 0.6545(11) 0.042(3) Uiso 1 1 d D . . H16 H 0.1941 -0.1269 0.6987 0.050 Uiso 1 1 calc R . . C17 C 0.1582(15) -0.0865(6) 0.5309(10) 0.041(3) Uiso 1 1 d D . . H17 H 0.0830 -0.1224 0.4946 0.049 Uiso 1 1 calc R . . C18 C 0.2011(13) -0.0341(6) 0.4617(11) 0.035(3) Uiso 1 1 d D . . H18 H 0.1572 -0.0343 0.3790 0.042 Uiso 1 1 calc R . . C19 C 0.3132(11) 0.0200(5) 0.5188(8) 0.021(2) Uiso 1 1 d D . . C31 C 0.7111(14) -0.0954(6) 0.8846(11) 0.034(3) Uiso 1 1 d D . . H31A H 0.7511 -0.1164 0.9657 0.051 Uiso 1 1 calc R . . H31B H 0.6946 -0.1472 0.8317 0.051 Uiso 1 1 calc R . . H31C H 0.6294 -0.0649 0.8711 0.051 Uiso 1 1 calc R . . C32 C 0.8012(10) -0.0297(5) 0.8618(9) 0.026(3) Uiso 1 1 d D . . C33 C 0.7905(11) 0.0644(5) 0.8565(9) 0.017(2) Uiso 1 1 d D . . C34 C 0.8959(11) 0.1090(5) 0.8382(9) 0.023(2) Uiso 1 1 d D . . C35 C 0.9130(15) 0.2032(5) 0.8215(10) 0.028(3) Uiso 1 1 d D . . H35 H 0.8547 0.2471 0.8273 0.034 Uiso 1 1 calc R . . C36 C 1.0183(14) 0.2285(7) 0.7966(10) 0.032(3) Uiso 1 1 d D . . H36 H 1.0308 0.2909 0.7866 0.038 Uiso 1 1 calc R . . C37 C 1.1068(15) 0.1660(6) 0.7855(11) 0.047(3) Uiso 1 1 d D . . H37 H 1.1758 0.1860 0.7667 0.057 Uiso 1 1 calc R . . C38 C 1.0914(14) 0.0737(7) 0.8026(11) 0.045(3) Uiso 1 1 d D . . H38 H 1.1507 0.0307 0.7969 0.054 Uiso 1 1 calc R . . C39 C 0.9864(12) 0.0453(5) 0.8285(9) 0.026(3) Uiso 1 1 d D . . F1 F 0.3973(11) 0.2299(3) 0.7922(8) 0.0486(18) Uiso 1 1 d D . . F2 F 0.4162(11) 0.1127(4) 0.9066(8) 0.063(2) Uiso 1 1 d D . . F3 F 0.6070(11) 0.3039(3) 0.9422(7) 0.0471(18) Uiso 1 1 d D . . F4 F 0.5613(11) 0.2220(4) 1.0681(9) 0.068(2) Uiso 1 1 d D . . F5 F 0.8233(9) 0.2131(3) 1.0333(7) 0.0367(16) Uiso 1 1 d D . . F6 F 0.7302(10) 0.0967(3) 1.0795(7) 0.0435(17) Uiso 1 1 d D . . S1 S 0.3899(5) 0.08971(15) 0.4511(3) 0.040(5) Uani 1 1 d D . . S2 S 0.9403(5) -0.06677(15) 0.8452(3) 0.034(5) Uani 1 1 d 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 S1 0.048(6) 0.0285(13) 0.026(4) 0.0016(13) -0.002(5) -0.0039(17) S2 0.037(7) 0.0289(14) 0.038(4) 0.0037(14) 0.018(5) 0.0116(18) _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 C5 1.323(12) . ? C1 C13 1.474(10) . ? C1 C2 1.502(16) . ? C2 F1 1.327(8) . ? C2 F2 1.365(12) . ? C2 C3 1.547(10) . ? C3 F4 1.317(13) . ? C3 F3 1.352(10) . ? C3 C4 1.522(12) . ? C4 F5 1.361(10) . ? C4 F6 1.369(10) . ? C4 C5 1.507(11) . ? C5 C33 1.455(12) . ? C11 C12 1.495(12) . ? C12 C13 1.360(13) . ? C12 S1 1.729(7) . ? C13 C14 1.447(11) . ? C14 C15 1.395(13) . ? C14 C19 1.401(10) . ? C15 C16 1.369(11) . ? C16 C17 1.391(11) . ? C17 C18 1.360(13) . ? C18 C19 1.397(10) . ? C19 S1 1.734(12) . ? C31 C32 1.486(13) . ? C32 C33 1.368(9) . ? C32 S2 1.722(12) . ? C33 C34 1.432(13) . ? C34 C39 1.404(12) . ? C34 C35 1.405(10) . ? C35 C36 1.373(14) . ? C36 C37 1.383(13) . ? C37 C38 1.376(10) . ? C38 C39 1.388(14) . ? C39 S2 1.739(9) . ? 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 C5 C1 C13 131.6(14) . . ? C5 C1 C2 111.3(9) . . ? C13 C1 C2 117.1(10) . . ? F1 C2 F2 106.6(11) . . ? F1 C2 C1 113.7(11) . . ? F2 C2 C1 113.0(8) . . ? F1 C2 C3 112.2(7) . . ? F2 C2 C3 105.6(9) . . ? C1 C2 C3 105.6(10) . . ? F4 C3 F3 108.3(10) . . ? F4 C3 C4 114.5(9) . . ? F3 C3 C4 108.7(10) . . ? F4 C3 C2 115.3(11) . . ? F3 C3 C2 107.7(8) . . ? C4 C3 C2 101.9(8) . . ? F5 C4 F6 105.2(6) . . ? F5 C4 C5 113.7(10) . . ? F6 C4 C5 110.4(7) . . ? F5 C4 C3 112.0(7) . . ? F6 C4 C3 108.6(10) . . ? C5 C4 C3 106.7(7) . . ? C1 C5 C33 129.0(9) . . ? C1 C5 C4 110.0(11) . . ? C33 C5 C4 120.8(7) . . ? C13 C12 C11 128.3(8) . . ? C13 C12 S1 112.5(7) . . ? C11 C12 S1 119.1(8) . . ? C12 C13 C14 113.4(8) . . ? C12 C13 C1 121.0(9) . . ? C14 C13 C1 125.1(11) . . ? C15 C14 C19 119.8(9) . . ? C15 C14 C13 129.9(8) . . ? C19 C14 C13 110.3(9) . . ? C16 C15 C14 118.6(11) . . ? C15 C16 C17 120.9(14) . . ? C18 C17 C16 121.9(13) . . ? C17 C18 C19 117.8(11) . . ? C14 C19 C18 120.9(11) . . ? C14 C19 S1 112.4(7) . . ? C18 C19 S1 126.7(8) . . ? C33 C32 C31 126.5(11) . . ? C33 C32 S2 111.7(9) . . ? C31 C32 S2 121.7(7) . . ? C32 C33 C34 113.4(10) . . ? C32 C33 C5 122.7(11) . . ? C34 C33 C5 123.8(8) . . ? C39 C34 C35 119.0(12) . . ? C39 C34 C33 111.9(8) . . ? C35 C34 C33 128.9(12) . . ? C36 C35 C34 118.0(13) . . ? C35 C36 C37 123.3(12) . . ? C38 C37 C36 119.0(15) . . ? C37 C38 C39 119.4(14) . . ? C38 C39 C34 121.3(9) . . ? C38 C39 S2 128.2(9) . . ? C34 C39 S2 110.5(9) . . ? C12 S1 C19 91.3(6) . . ? C32 S2 C39 92.5(6) . . ? _database_code_depnum_ccdc_archive 'CCDC 961253' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2.55GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 11.053(2) _cell_length_b 14.338(3) _cell_length_c 12.136(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.76(3) _cell_angle_gamma 90.00 _cell_volume 1760.4(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 943 _cell_measurement_theta_min 3.2925 _cell_measurement_theta_max 25.7659 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.50977 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 4747 _diffrn_reflns_av_R_equivalents 0.1017 _diffrn_reflns_av_sigmaI/netI 0.0996 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 23.97 _reflns_number_total 976 _reflns_number_gt 631 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.323 _diffrn_reflns_theta_full 23.97 _diffrn_measured_fraction_theta_full 0.323 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0415P)^2^+1.4160P] 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 976 _refine_ls_number_parameters 137 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.1241 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.1864 _refine_ls_wR_factor_gt 0.1592 _refine_ls_goodness_of_fit_ref 1.490 _refine_ls_restrained_S_all 1.445 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.397 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.073 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.5596(14) 0.1183(6) 0.8045(10) 0.023(2) Uiso 1 1 d D . . C2 C 0.4839(12) 0.1706(6) 0.8625(10) 0.033(3) Uiso 1 1 d D . . C3 C 0.5900(11) 0.2190(6) 0.9727(11) 0.042(3) Uiso 1 1 d D . . C4 C 0.7126(11) 0.1613(5) 0.9933(8) 0.022(2) Uiso 1 1 d D . . C5 C 0.6865(12) 0.1129(5) 0.8766(9) 0.022(2) Uiso 1 1 d D . . C11 C 0.6062(15) 0.1981(6) 0.5909(13) 0.037(3) Uiso 1 1 d D . . H11A H 0.6591 0.2140 0.6733 0.056 Uiso 1 1 calc R . . H11B H 0.5618 0.2529 0.5482 0.056 Uiso 1 1 calc R . . H11C H 0.6620 0.1737 0.5543 0.056 Uiso 1 1 calc R . . C12 C 0.5059(13) 0.1261(6) 0.5862(9) 0.025(2) Uiso 1 1 d D . . C13 C 0.4852(12) 0.0872(5) 0.6796(9) 0.023(2) Uiso 1 1 d D . . C14 C 0.3757(12) 0.0229(5) 0.6432(9) 0.024(2) Uiso 1 1 d D . . C15 C 0.3287(13) -0.0337(6) 0.7116(11) 0.030(3) Uiso 1 1 d D . . H15 H 0.3715 -0.0348 0.7951 0.036 Uiso 1 1 calc R . . C16 C 0.2184(16) -0.0875(6) 0.6531(13) 0.047(3) Uiso 1 1 d D . . H16 H 0.1883 -0.1267 0.6978 0.056 Uiso 1 1 calc R . . C17 C 0.1507(16) -0.0845(7) 0.5283(11) 0.040(3) Uiso 1 1 d D . . H17 H 0.0735 -0.1189 0.4915 0.048 Uiso 1 1 calc R . . C18 C 0.1959(13) -0.0322(6) 0.4597(12) 0.032(3) Uiso 1 1 d D . . H18 H 0.1508 -0.0310 0.3764 0.039 Uiso 1 1 calc R . . C19 C 0.3111(11) 0.0198(5) 0.5162(8) 0.020(2) Uiso 1 1 d D . . C31 C 0.7100(14) -0.0963(6) 0.8852(11) 0.033(3) Uiso 1 1 d D . . H31A H 0.7480 -0.1163 0.9677 0.050 Uiso 1 1 calc R . . H31B H 0.6942 -0.1496 0.8334 0.050 Uiso 1 1 calc R . . H31C H 0.6280 -0.0648 0.8692 0.050 Uiso 1 1 calc R . . C32 C 0.8023(11) -0.0318(5) 0.8628(9) 0.022(2) Uiso 1 1 d D . . C33 C 0.7912(12) 0.0629(5) 0.8570(9) 0.021(2) Uiso 1 1 d D . . C34 C 0.8982(12) 0.1083(5) 0.8380(10) 0.026(2) Uiso 1 1 d D . . C35 C 0.9164(16) 0.2037(6) 0.8222(11) 0.030(3) Uiso 1 1 d D . . H35 H 0.8585 0.2480 0.8293 0.036 Uiso 1 1 calc R . . C36 C 1.0216(15) 0.2301(8) 0.7961(11) 0.037(3) Uiso 1 1 d D . . H36 H 1.0334 0.2931 0.7850 0.044 Uiso 1 1 calc R . . C37 C 1.1105(16) 0.1667(6) 0.7857(12) 0.049(3) Uiso 1 1 d D . . H37 H 1.1793 0.1866 0.7659 0.059 Uiso 1 1 calc R . . C38 C 1.0957(14) 0.0743(6) 0.8048(11) 0.039(3) Uiso 1 1 d D . . H38 H 1.1572 0.0314 0.8014 0.047 Uiso 1 1 calc R . . C39 C 0.9899(12) 0.0437(5) 0.8293(10) 0.025(3) Uiso 1 1 d D . . F1 F 0.3969(11) 0.2300(3) 0.7897(9) 0.0447(17) Uiso 1 1 d D . . F2 F 0.4171(12) 0.1122(5) 0.9073(9) 0.062(2) Uiso 1 1 d D . . F3 F 0.6056(11) 0.3067(3) 0.9396(8) 0.0441(17) Uiso 1 1 d D . . F4 F 0.5617(11) 0.2236(4) 1.0676(10) 0.067(2) Uiso 1 1 d D . . F5 F 0.8233(10) 0.2155(3) 1.0346(8) 0.0375(16) Uiso 1 1 d D . . F6 F 0.7301(11) 0.0977(3) 1.0818(8) 0.0436(17) Uiso 1 1 d D . . S1 S 0.3894(5) 0.08937(15) 0.4484(4) 0.055(6) Uani 1 1 d D . . S2 S 0.9425(6) -0.06892(16) 0.8465(4) 0.044(6) Uani 1 1 d 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 S1 0.064(8) 0.0271(13) 0.040(5) 0.0006(15) -0.014(6) -0.0025(19) S2 0.044(8) 0.0333(15) 0.046(5) 0.0044(16) 0.008(6) 0.011(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C5 1.323(13) . ? C1 C13 1.472(10) . ? C1 C2 1.494(16) . ? C2 F1 1.322(9) . ? C2 F2 1.366(13) . ? C2 C3 1.543(10) . ? C3 F4 1.311(13) . ? C3 F3 1.352(10) . ? C3 C4 1.520(12) . ? C4 F5 1.362(10) . ? C4 F6 1.361(10) . ? C4 C5 1.496(11) . ? C5 C33 1.460(13) . ? C11 C12 1.499(13) . ? C12 C13 1.363(13) . ? C12 S1 1.731(7) . ? C13 C14 1.442(11) . ? C14 C15 1.401(13) . ? C14 C19 1.414(10) . ? C15 C16 1.375(12) . ? C16 C17 1.393(12) . ? C17 C18 1.358(13) . ? C18 C19 1.394(11) . ? C19 S1 1.730(12) . ? C31 C32 1.481(13) . ? C32 C33 1.363(9) . ? C32 S2 1.724(13) . ? C33 C34 1.448(13) . ? C34 C35 1.406(10) . ? C34 C39 1.408(12) . ? C35 C36 1.376(14) . ? C36 C37 1.380(13) . ? C37 C38 1.366(11) . ? C38 C39 1.389(14) . ? C39 S2 1.736(10) . ? 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 C5 C1 C13 131.8(15) . . ? C5 C1 C2 111.3(10) . . ? C13 C1 C2 116.8(10) . . ? F1 C2 F2 107.2(12) . . ? F1 C2 C1 113.8(12) . . ? F2 C2 C1 112.1(9) . . ? F1 C2 C3 112.6(7) . . ? F2 C2 C3 105.9(10) . . ? C1 C2 C3 105.1(10) . . ? F4 C3 F3 108.5(11) . . ? F4 C3 C4 113.3(9) . . ? F3 C3 C4 110.1(11) . . ? F4 C3 C2 114.6(12) . . ? F3 C3 C2 107.7(8) . . ? C4 C3 C2 102.3(9) . . ? F5 C4 F6 105.7(7) . . ? F5 C4 C5 114.6(11) . . ? F6 C4 C5 110.3(7) . . ? F5 C4 C3 111.0(7) . . ? F6 C4 C3 109.2(11) . . ? C5 C4 C3 106.1(8) . . ? C1 C5 C33 128.3(10) . . ? C1 C5 C4 110.4(11) . . ? C33 C5 C4 121.2(8) . . ? C13 C12 C11 128.3(9) . . ? C13 C12 S1 111.7(8) . . ? C11 C12 S1 119.8(9) . . ? C12 C13 C14 114.1(8) . . ? C12 C13 C1 121.4(10) . . ? C14 C13 C1 124.1(12) . . ? C15 C14 C19 118.8(9) . . ? C15 C14 C13 130.8(8) . . ? C19 C14 C13 110.3(10) . . ? C16 C15 C14 118.9(12) . . ? C15 C16 C17 121.3(15) . . ? C18 C17 C16 121.0(13) . . ? C17 C18 C19 118.9(11) . . ? C18 C19 C14 120.9(11) . . ? C18 C19 S1 127.4(9) . . ? C14 C19 S1 111.7(7) . . ? C33 C32 C31 125.3(11) . . ? C33 C32 S2 111.6(10) . . ? C31 C32 S2 123.1(8) . . ? C32 C33 C34 113.2(11) . . ? C32 C33 C5 122.7(12) . . ? C34 C33 C5 123.9(8) . . ? C35 C34 C39 118.9(13) . . ? C35 C34 C33 129.0(12) . . ? C39 C34 C33 112.0(9) . . ? C36 C35 C34 118.6(14) . . ? C35 C36 C37 122.6(13) . . ? C38 C37 C36 119.0(16) . . ? C37 C38 C39 120.7(15) . . ? C38 C39 C34 120.1(9) . . ? C38 C39 S2 129.8(9) . . ? C34 C39 S2 110.0(10) . . ? C19 S1 C12 92.1(6) . . ? C32 S2 C39 93.2(6) . . ? _database_code_depnum_ccdc_archive 'CCDC 961254' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3.375GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 10.991(6) _cell_length_b 14.1391(8) _cell_length_c 12.033(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.83(5) _cell_angle_gamma 90.00 _cell_volume 1710.6(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1126 _cell_measurement_theta_min 3.3344 _cell_measurement_theta_max 25.5144 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.55854 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 5749 _diffrn_reflns_av_R_equivalents 0.0769 _diffrn_reflns_av_sigmaI/netI 0.0730 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 25.52 _reflns_number_total 1116 _reflns_number_gt 847 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.319 _diffrn_reflns_theta_full 25.52 _diffrn_measured_fraction_theta_full 0.319 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 1116 _refine_ls_number_parameters 137 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0974 _refine_ls_R_factor_gt 0.0758 _refine_ls_wR_factor_ref ? _refine_ls_wR_factor_gt 0.1681 _refine_ls_goodness_of_fit_ref 1.422 _refine_ls_restrained_S_all 1.387 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.423 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.065 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.5583(11) 0.1176(4) 0.8041(9) 0.0217(17) Uiso 1 1 d D . . C2 C 0.4821(10) 0.1696(5) 0.8641(8) 0.033(2) Uiso 1 1 d D . . C3 C 0.5891(9) 0.2206(5) 0.9725(10) 0.039(2) Uiso 1 1 d D . . C4 C 0.7138(9) 0.1631(4) 0.9941(7) 0.0203(17) Uiso 1 1 d D . . C5 C 0.6858(10) 0.1138(4) 0.8763(7) 0.0202(16) Uiso 1 1 d D . . C11 C 0.6087(12) 0.1973(5) 0.5899(11) 0.035(2) Uiso 1 1 d D . . H11A H 0.6534 0.2193 0.6719 0.053 Uiso 1 1 calc R . . H11B H 0.5660 0.2495 0.5378 0.053 Uiso 1 1 calc R . . H11C H 0.6723 0.1692 0.5638 0.053 Uiso 1 1 calc R . . C12 C 0.5067(10) 0.1253(4) 0.5838(8) 0.0238(17) Uiso 1 1 d D . . C13 C 0.4860(10) 0.0858(4) 0.6778(8) 0.0215(17) Uiso 1 1 d D . . C14 C 0.3726(9) 0.0229(4) 0.6400(7) 0.0208(17) Uiso 1 1 d D . . C15 C 0.3270(10) -0.0340(4) 0.7098(9) 0.0287(19) Uiso 1 1 d D . . H15 H 0.3719 -0.0366 0.7939 0.034 Uiso 1 1 calc R . . C16 C 0.2132(13) -0.0864(5) 0.6500(10) 0.042(2) Uiso 1 1 d D . . H16 H 0.1818 -0.1255 0.6948 0.051 Uiso 1 1 calc R . . C17 C 0.1443(13) -0.0823(5) 0.5246(9) 0.041(2) Uiso 1 1 d D . . H17 H 0.0648 -0.1153 0.4877 0.049 Uiso 1 1 calc R . . C18 C 0.1911(11) -0.0307(5) 0.4552(10) 0.032(2) Uiso 1 1 d D . . H18 H 0.1464 -0.0299 0.3711 0.039 Uiso 1 1 calc R . . C19 C 0.3080(9) 0.0211(4) 0.5131(7) 0.0245(17) Uiso 1 1 d D . . C31 C 0.7097(12) -0.0989(5) 0.8859(10) 0.032(2) Uiso 1 1 d D . . H31A H 0.7508 -0.1224 0.9676 0.048 Uiso 1 1 calc R . . H31B H 0.6887 -0.1508 0.8299 0.048 Uiso 1 1 calc R . . H31C H 0.6295 -0.0657 0.8753 0.048 Uiso 1 1 calc R . . C32 C 0.8025(9) -0.0335(4) 0.8628(8) 0.0243(18) Uiso 1 1 d D . . C33 C 0.7917(9) 0.0636(4) 0.8583(8) 0.0205(16) Uiso 1 1 d D . . C34 C 0.8998(10) 0.1078(4) 0.8399(8) 0.0225(17) Uiso 1 1 d D . . C35 C 0.9178(12) 0.2041(5) 0.8210(9) 0.029(2) Uiso 1 1 d D . . H35 H 0.8580 0.2489 0.8256 0.035 Uiso 1 1 calc R . . C36 C 1.0230(12) 0.2320(6) 0.7957(9) 0.034(2) Uiso 1 1 d D . . H36 H 1.0343 0.2958 0.7839 0.041 Uiso 1 1 calc R . . C37 C 1.1133(13) 0.1670(5) 0.7872(11) 0.047(3) Uiso 1 1 d D . . H37 H 1.1832 0.1869 0.7681 0.057 Uiso 1 1 calc R . . C38 C 1.0986(12) 0.0726(5) 0.8071(10) 0.043(2) Uiso 1 1 d D . . H38 H 1.1603 0.0289 0.8038 0.052 Uiso 1 1 calc R . . C39 C 0.9928(10) 0.0425(4) 0.8320(8) 0.0260(19) Uiso 1 1 d D . . F1 F 0.3925(8) 0.2295(3) 0.7887(7) 0.0431(13) Uiso 1 1 d D . . F2 F 0.4152(9) 0.1107(3) 0.9091(7) 0.0558(16) Uiso 1 1 d D . . F3 F 0.6041(8) 0.3092(3) 0.9369(6) 0.0418(13) Uiso 1 1 d D . . F4 F 0.5599(8) 0.2256(4) 1.0681(8) 0.0625(18) Uiso 1 1 d D . . F5 F 0.8238(7) 0.2184(3) 1.0347(6) 0.0365(12) Uiso 1 1 d D . . F6 F 0.7310(9) 0.0996(3) 1.0839(6) 0.0442(13) Uiso 1 1 d D . . S1 S 0.3886(4) 0.08929(11) 0.4447(3) 0.038(4) Uani 1 1 d D . . S2 S 0.9442(4) -0.07165(12) 0.8485(3) 0.037(4) Uani 1 1 d 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 S1 0.050(5) 0.0276(9) 0.024(3) 0.0011(10) 0.002(4) -0.0043(13) S2 0.044(5) 0.0299(10) 0.035(3) 0.0063(11) 0.015(4) 0.0105(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 C5 1.318(11) . ? C1 C13 1.472(9) . ? C1 C2 1.500(15) . ? C2 F1 1.337(7) . ? C2 F2 1.361(12) . ? C2 C3 1.538(9) . ? C3 F4 1.315(12) . ? C3 F3 1.355(9) . ? C3 C4 1.523(11) . ? C4 F5 1.354(9) . ? C4 F6 1.359(9) . ? C4 C5 1.496(10) . ? C5 C33 1.453(12) . ? C11 C12 1.494(11) . ? C12 C13 1.361(12) . ? C12 S1 1.729(6) . ? C13 C14 1.447(10) . ? C14 C15 1.394(12) . ? C14 C19 1.400(9) . ? C15 C16 1.380(10) . ? C16 C17 1.389(10) . ? C17 C18 1.357(13) . ? C18 C19 1.397(9) . ? C19 S1 1.727(11) . ? C31 C32 1.484(12) . ? C32 C33 1.377(7) . ? C32 S2 1.722(11) . ? C33 C34 1.437(12) . ? C34 C35 1.408(9) . ? C34 C39 1.410(11) . ? C35 C36 1.368(13) . ? C36 C37 1.387(12) . ? C37 C38 1.377(10) . ? C38 C39 1.380(13) . ? C39 S2 1.736(8) . ? 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 C5 C1 C13 130.9(13) . . ? C5 C1 C2 110.7(8) . . ? C13 C1 C2 118.2(8) . . ? F1 C2 F2 106.8(9) . . ? F1 C2 C1 112.7(9) . . ? F2 C2 C1 112.8(7) . . ? F1 C2 C3 112.3(6) . . ? F2 C2 C3 107.5(8) . . ? C1 C2 C3 104.7(8) . . ? F4 C3 F3 109.4(8) . . ? F4 C3 C4 113.6(8) . . ? F3 C3 C4 109.3(9) . . ? F4 C3 C2 113.2(10) . . ? F3 C3 C2 108.3(7) . . ? C4 C3 C2 102.8(7) . . ? F5 C4 F6 106.1(5) . . ? F5 C4 C5 115.1(9) . . ? F6 C4 C5 110.8(5) . . ? F5 C4 C3 111.4(6) . . ? F6 C4 C3 108.3(9) . . ? C5 C4 C3 105.1(6) . . ? C1 C5 C33 128.6(8) . . ? C1 C5 C4 111.3(10) . . ? C33 C5 C4 119.9(6) . . ? C13 C12 C11 127.8(7) . . ? C13 C12 S1 111.8(6) . . ? C11 C12 S1 120.2(7) . . ? C12 C13 C14 113.8(7) . . ? C12 C13 C1 122.1(8) . . ? C14 C13 C1 123.3(10) . . ? C15 C14 C19 120.0(7) . . ? C15 C14 C13 129.7(7) . . ? C19 C14 C13 110.3(8) . . ? C16 C15 C14 117.8(9) . . ? C15 C16 C17 121.7(12) . . ? C18 C17 C16 121.0(11) . . ? C17 C18 C19 118.4(9) . . ? C14 C19 C18 120.8(9) . . ? C14 C19 S1 112.3(6) . . ? C18 C19 S1 126.9(8) . . ? C33 C32 C31 125.0(9) . . ? C33 C32 S2 112.1(8) . . ? C31 C32 S2 122.8(6) . . ? C32 C33 C34 112.1(9) . . ? C32 C33 C5 122.9(9) . . ? C34 C33 C5 124.9(6) . . ? C35 C34 C39 118.0(11) . . ? C35 C34 C33 128.7(9) . . ? C39 C34 C33 113.1(7) . . ? C36 C35 C34 120.1(11) . . ? C35 C36 C37 121.4(9) . . ? C38 C37 C36 119.5(13) . . ? C39 C38 C37 120.4(12) . . ? C38 C39 C34 120.7(8) . . ? C38 C39 S2 129.5(7) . . ? C34 C39 S2 109.7(8) . . ? C19 S1 C12 91.8(5) . . ? C32 S2 C39 93.0(5) . . ? _database_code_depnum_ccdc_archive 'CCDC 961255' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4.08GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 10.954(2) _cell_length_b 14.032(3) _cell_length_c 11.962(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.77(3) _cell_angle_gamma 90.00 _cell_volume 1682.7(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1494 _cell_measurement_theta_min 3.3601 _cell_measurement_theta_max 25.7611 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.849 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.80191 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 4815 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 22.42 _reflns_number_total 873 _reflns_number_gt 759 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.363 _diffrn_reflns_theta_full 22.42 _diffrn_measured_fraction_theta_full 0.363 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0547P)^2^+3.8984P] 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 873 _refine_ls_number_parameters 137 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.1687 _refine_ls_wR_factor_gt 0.1630 _refine_ls_goodness_of_fit_ref 1.488 _refine_ls_restrained_S_all 1.439 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.379 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.061 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.5582(11) 0.1170(4) 0.8042(9) 0.0203(18) Uiso 1 1 d D . . C2 C 0.4810(10) 0.1696(5) 0.8643(8) 0.029(2) Uiso 1 1 d D . . C3 C 0.5883(9) 0.2216(5) 0.9708(10) 0.035(2) Uiso 1 1 d D . . C4 C 0.7136(9) 0.1644(4) 0.9938(7) 0.0173(17) Uiso 1 1 d D . . C5 C 0.6866(10) 0.1144(4) 0.8758(8) 0.0189(18) Uiso 1 1 d D . . C11 C 0.6096(13) 0.1959(5) 0.5887(11) 0.033(2) Uiso 1 1 d D . . H11A H 0.6568 0.2171 0.6714 0.049 Uiso 1 1 calc R . . H11B H 0.5676 0.2494 0.5377 0.049 Uiso 1 1 calc R . . H11C H 0.6712 0.1668 0.5604 0.049 Uiso 1 1 calc R . . C12 C 0.5061(10) 0.1250(4) 0.5836(8) 0.0217(19) Uiso 1 1 d D . . C13 C 0.4858(10) 0.0851(4) 0.6776(8) 0.0210(18) Uiso 1 1 d D . . C14 C 0.3716(10) 0.0227(4) 0.6390(8) 0.0209(18) Uiso 1 1 d D . . C15 C 0.3249(11) -0.0345(5) 0.7085(9) 0.026(2) Uiso 1 1 d D . . H15 H 0.3704 -0.0377 0.7930 0.031 Uiso 1 1 calc R . . C16 C 0.2099(13) -0.0861(5) 0.6491(11) 0.040(2) Uiso 1 1 d D . . H16 H 0.1781 -0.1251 0.6943 0.048 Uiso 1 1 calc R . . C17 C 0.1400(13) -0.0812(6) 0.5230(9) 0.039(2) Uiso 1 1 d D . . H17 H 0.0597 -0.1138 0.4858 0.047 Uiso 1 1 calc R . . C18 C 0.1878(11) -0.0295(5) 0.4543(10) 0.028(2) Uiso 1 1 d D . . H18 H 0.1422 -0.0279 0.3698 0.033 Uiso 1 1 calc R . . C19 C 0.3065(9) 0.0215(5) 0.5116(7) 0.0232(19) Uiso 1 1 d D . . C31 C 0.7094(12) -0.1004(5) 0.8860(10) 0.031(2) Uiso 1 1 d D . . H31A H 0.7511 -0.1255 0.9674 0.047 Uiso 1 1 calc R . . H31B H 0.6870 -0.1518 0.8283 0.047 Uiso 1 1 calc R . . H31C H 0.6297 -0.0668 0.8771 0.047 Uiso 1 1 calc R . . C32 C 0.8027(9) -0.0341(4) 0.8632(8) 0.0224(19) Uiso 1 1 d D . . C33 C 0.7924(9) 0.0629(4) 0.8576(8) 0.0192(18) Uiso 1 1 d D . . C34 C 0.9005(10) 0.1073(4) 0.8401(9) 0.0227(19) Uiso 1 1 d D . . C35 C 0.9178(13) 0.2043(5) 0.8210(9) 0.028(2) Uiso 1 1 d D . . H35 H 0.8574 0.2490 0.8256 0.033 Uiso 1 1 calc R . . C36 C 1.0236(12) 0.2331(6) 0.7956(9) 0.033(2) Uiso 1 1 d D . . H36 H 1.0345 0.2975 0.7838 0.040 Uiso 1 1 calc R . . C37 C 1.1143(14) 0.1679(6) 0.7872(11) 0.052(3) Uiso 1 1 d D . . H37 H 1.1841 0.1881 0.7675 0.062 Uiso 1 1 calc R . . C38 C 1.1004(13) 0.0724(6) 0.8082(10) 0.045(3) Uiso 1 1 d D . . H38 H 1.1628 0.0286 0.8052 0.053 Uiso 1 1 calc R . . C39 C 0.9948(10) 0.0416(5) 0.8335(8) 0.025(2) Uiso 1 1 d D . . F1 F 0.3901(9) 0.2286(3) 0.7876(7) 0.0427(14) Uiso 1 1 d D . . F2 F 0.4147(9) 0.1099(4) 0.9105(7) 0.0511(16) Uiso 1 1 d D . . F3 F 0.6033(8) 0.3107(3) 0.9348(6) 0.0399(14) Uiso 1 1 d D . . F4 F 0.5600(9) 0.2271(4) 1.0670(8) 0.0590(18) Uiso 1 1 d D . . F5 F 0.8242(8) 0.2199(3) 1.0346(6) 0.0347(13) Uiso 1 1 d D . . F6 F 0.7318(9) 0.1003(3) 1.0844(7) 0.0430(14) Uiso 1 1 d D . . S1 S 0.3881(4) 0.08936(12) 0.4427(3) 0.039(4) Uani 1 1 d D . . S2 S 0.9453(4) -0.07334(13) 0.8494(3) 0.031(4) Uani 1 1 d 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 S1 0.050(4) 0.0245(10) 0.027(3) 0.0016(10) -0.001(4) -0.0051(13) S2 0.040(5) 0.0276(11) 0.031(3) 0.0058(10) 0.018(4) 0.0105(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 C5 1.320(11) . ? C1 C13 1.468(9) . ? C1 C2 1.506(15) . ? C2 F1 1.336(8) . ? C2 F2 1.362(12) . ? C2 C3 1.527(9) . ? C3 F4 1.310(12) . ? C3 F3 1.353(9) . ? C3 C4 1.517(11) . ? C4 F5 1.354(9) . ? C4 F6 1.360(10) . ? C4 C5 1.495(10) . ? C5 C33 1.454(12) . ? C11 C12 1.491(12) . ? C12 C13 1.352(12) . ? C12 S1 1.734(6) . ? C13 C14 1.443(10) . ? C14 C15 1.392(12) . ? C14 C19 1.398(10) . ? C15 C16 1.377(11) . ? C16 C17 1.391(11) . ? C17 C18 1.349(13) . ? C18 C19 1.399(10) . ? C19 S1 1.725(11) . ? C31 C32 1.487(12) . ? C32 C33 1.365(8) . ? C32 S2 1.726(11) . ? C33 C34 1.427(12) . ? C34 C35 1.405(9) . ? C34 C39 1.411(12) . ? C35 C36 1.373(13) . ? C36 C37 1.384(13) . ? C37 C38 1.383(10) . ? C38 C39 1.378(13) . ? C39 S2 1.736(8) . ? 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 C5 C1 C13 130.7(13) . . ? C5 C1 C2 111.1(8) . . ? C13 C1 C2 118.0(9) . . ? F1 C2 F2 106.8(9) . . ? F1 C2 C1 112.5(9) . . ? F2 C2 C1 112.7(7) . . ? F1 C2 C3 112.8(6) . . ? F2 C2 C3 108.3(8) . . ? C1 C2 C3 103.9(9) . . ? F4 C3 F3 109.1(8) . . ? F4 C3 C4 113.0(8) . . ? F3 C3 C4 109.2(9) . . ? F4 C3 C2 112.7(10) . . ? F3 C3 C2 109.1(7) . . ? C4 C3 C2 103.6(8) . . ? F5 C4 F6 105.7(5) . . ? F5 C4 C5 114.8(9) . . ? F6 C4 C5 110.5(6) . . ? F5 C4 C3 111.9(6) . . ? F6 C4 C3 109.0(9) . . ? C5 C4 C3 104.9(6) . . ? C1 C5 C33 128.4(8) . . ? C1 C5 C4 110.7(10) . . ? C33 C5 C4 120.5(6) . . ? C13 C12 C11 128.3(7) . . ? C13 C12 S1 112.4(6) . . ? C11 C12 S1 119.3(7) . . ? C12 C13 C14 113.4(7) . . ? C12 C13 C1 122.0(8) . . ? C14 C13 C1 123.6(10) . . ? C15 C14 C19 119.7(7) . . ? C15 C14 C13 129.6(7) . . ? C19 C14 C13 110.6(8) . . ? C16 C15 C14 118.3(9) . . ? C15 C16 C17 121.6(13) . . ? C18 C17 C16 120.5(11) . . ? C17 C18 C19 119.3(9) . . ? C14 C19 C18 120.3(10) . . ? C14 C19 S1 112.3(6) . . ? C18 C19 S1 127.4(8) . . ? C33 C32 C31 125.7(9) . . ? C33 C32 S2 112.0(8) . . ? C31 C32 S2 122.2(6) . . ? C32 C33 C34 112.7(9) . . ? C32 C33 C5 122.9(10) . . ? C34 C33 C5 124.3(6) . . ? C35 C34 C39 118.3(11) . . ? C35 C34 C33 128.4(10) . . ? C39 C34 C33 113.1(7) . . ? C36 C35 C34 120.2(11) . . ? C35 C36 C37 121.0(10) . . ? C38 C37 C36 119.5(14) . . ? C39 C38 C37 120.5(13) . . ? C38 C39 C34 120.4(8) . . ? C38 C39 S2 130.0(8) . . ? C34 C39 S2 109.4(8) . . ? C19 S1 C12 91.3(5) . . ? C32 S2 C39 92.8(5) . . ? _database_code_depnum_ccdc_archive 'CCDC 961256' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4.45GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 10.930(2) _cell_length_b 13.961(3) _cell_length_c 11.922(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.76(3) _cell_angle_gamma 90.00 _cell_volume 1665.0(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1166 _cell_measurement_theta_min 3.3384 _cell_measurement_theta_max 25.4159 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.61187 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 4932 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 22.63 _reflns_number_total 891 _reflns_number_gt 756 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.367 _diffrn_reflns_theta_full 22.63 _diffrn_measured_fraction_theta_full 0.367 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0621P)^2^+3.0769P] 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 891 _refine_ls_number_parameters 137 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.1730 _refine_ls_wR_factor_gt 0.1658 _refine_ls_goodness_of_fit_ref 1.434 _refine_ls_restrained_S_all 1.388 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.459 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.069 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.5587(12) 0.1169(5) 0.8035(9) 0.0195(19) Uiso 1 1 d D . . C2 C 0.4804(11) 0.1691(5) 0.8631(9) 0.028(2) Uiso 1 1 d D . . C3 C 0.5870(9) 0.2222(5) 0.9707(10) 0.031(2) Uiso 1 1 d D . . C4 C 0.7127(9) 0.1650(4) 0.9941(7) 0.0163(17) Uiso 1 1 d D . . C5 C 0.6872(10) 0.1142(4) 0.8758(8) 0.0171(18) Uiso 1 1 d D . . C11 C 0.6104(13) 0.1957(5) 0.5878(11) 0.031(2) Uiso 1 1 d D . . H11A H 0.6482 0.2239 0.6680 0.046 Uiso 1 1 calc R . . H11B H 0.5704 0.2449 0.5279 0.046 Uiso 1 1 calc R . . H11C H 0.6794 0.1642 0.5712 0.046 Uiso 1 1 calc R . . C12 C 0.5065(10) 0.1247(5) 0.5821(8) 0.0195(19) Uiso 1 1 d D . . C13 C 0.4858(10) 0.0852(4) 0.6764(8) 0.0188(19) Uiso 1 1 d D . . C14 C 0.3712(10) 0.0228(5) 0.6381(8) 0.0210(19) Uiso 1 1 d D . . C15 C 0.3239(11) -0.0344(5) 0.7079(9) 0.025(2) Uiso 1 1 d D . . H15 H 0.3701 -0.0380 0.7926 0.030 Uiso 1 1 calc R . . C16 C 0.2073(13) -0.0857(5) 0.6491(10) 0.040(3) Uiso 1 1 d D . . H16 H 0.1747 -0.1242 0.6945 0.048 Uiso 1 1 calc R . . C17 C 0.1382(13) -0.0802(6) 0.5224(9) 0.037(2) Uiso 1 1 d D . . H17 H 0.0573 -0.1123 0.4851 0.044 Uiso 1 1 calc R . . C18 C 0.1860(11) -0.0291(5) 0.4523(10) 0.026(2) Uiso 1 1 d D . . H18 H 0.1408 -0.0281 0.3674 0.031 Uiso 1 1 calc R . . C19 C 0.3046(10) 0.0219(5) 0.5102(7) 0.0208(19) Uiso 1 1 d D . . C31 C 0.7093(12) -0.1010(5) 0.8862(10) 0.031(2) Uiso 1 1 d D . . H31A H 0.7512 -0.1270 0.9675 0.047 Uiso 1 1 calc R . . H31B H 0.6856 -0.1522 0.8275 0.047 Uiso 1 1 calc R . . H31C H 0.6302 -0.0665 0.8783 0.047 Uiso 1 1 calc R . . C32 C 0.8034(9) -0.0350(4) 0.8638(9) 0.0210(19) Uiso 1 1 d D . . C33 C 0.7927(10) 0.0621(4) 0.8579(8) 0.0165(18) Uiso 1 1 d D . . C34 C 0.9012(10) 0.1069(4) 0.8401(8) 0.0195(19) Uiso 1 1 d D . . C35 C 0.9181(13) 0.2041(5) 0.8207(9) 0.026(2) Uiso 1 1 d D . . H35 H 0.8574 0.2489 0.8253 0.032 Uiso 1 1 calc R . . C36 C 1.0234(12) 0.2333(6) 0.7952(9) 0.031(2) Uiso 1 1 d D . . H36 H 1.0336 0.2980 0.7826 0.037 Uiso 1 1 calc R . . C37 C 1.1155(14) 0.1678(5) 0.7878(11) 0.049(3) Uiso 1 1 d D . . H37 H 1.1858 0.1882 0.7687 0.058 Uiso 1 1 calc R . . C38 C 1.1016(13) 0.0724(6) 0.8088(10) 0.043(3) Uiso 1 1 d D . . H38 H 1.1643 0.0285 0.8058 0.051 Uiso 1 1 calc R . . C39 C 0.9960(10) 0.0409(5) 0.8342(8) 0.023(2) Uiso 1 1 d D . . F1 F 0.3890(9) 0.2287(3) 0.7873(7) 0.0399(14) Uiso 1 1 d D . . F2 F 0.4144(9) 0.1094(4) 0.9104(7) 0.0508(16) Uiso 1 1 d D . . F3 F 0.6028(9) 0.3116(3) 0.9335(7) 0.0396(14) Uiso 1 1 d D . . F4 F 0.5587(9) 0.2276(4) 1.0674(8) 0.0561(18) Uiso 1 1 d D . . F5 F 0.8237(8) 0.2207(3) 1.0351(6) 0.0334(13) Uiso 1 1 d D . . F6 F 0.7319(9) 0.1007(3) 1.0846(7) 0.0440(15) Uiso 1 1 d D . . S1 S 0.3877(4) 0.08938(12) 0.4412(3) 0.029(4) Uani 1 1 d D . . S2 S 0.9461(4) -0.07441(13) 0.8502(3) 0.027(4) Uani 1 1 d 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 S1 0.036(5) 0.0235(11) 0.024(3) 0.0010(10) 0.007(4) -0.0059(13) S2 0.027(5) 0.0263(11) 0.036(4) 0.0072(11) 0.021(4) 0.0111(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 C5 1.320(11) . ? C1 C13 1.467(9) . ? C1 C2 1.503(15) . ? C2 F1 1.335(8) . ? C2 F2 1.364(12) . ? C2 C3 1.533(9) . ? C3 F4 1.310(12) . ? C3 F3 1.358(9) . ? C3 C4 1.515(11) . ? C4 F5 1.356(9) . ? C4 F6 1.354(9) . ? C4 C5 1.501(11) . ? C5 C33 1.450(12) . ? C11 C12 1.488(12) . ? C12 C13 1.352(12) . ? C12 S1 1.729(6) . ? C13 C14 1.439(10) . ? C14 C15 1.396(13) . ? C14 C19 1.400(10) . ? C15 C16 1.381(11) . ? C16 C17 1.393(11) . ? C17 C18 1.353(13) . ? C18 C19 1.394(10) . ? C19 S1 1.728(11) . ? C31 C32 1.483(12) . ? C32 C33 1.361(8) . ? C32 S2 1.722(11) . ? C33 C34 1.430(12) . ? C34 C35 1.401(9) . ? C34 C39 1.410(12) . ? C35 C36 1.366(13) . ? C36 C37 1.388(13) . ? C37 C38 1.375(10) . ? C38 C39 1.378(13) . ? C39 S2 1.734(8) . ? 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 C5 C1 C13 131.2(13) . . ? C5 C1 C2 111.3(8) . . ? C13 C1 C2 117.3(9) . . ? F1 C2 F2 106.5(9) . . ? F1 C2 C1 113.3(10) . . ? F2 C2 C1 113.3(7) . . ? F1 C2 C3 112.0(6) . . ? F2 C2 C3 107.5(8) . . ? C1 C2 C3 104.2(9) . . ? F4 C3 F3 109.9(8) . . ? F4 C3 C2 113.3(10) . . ? F3 C3 C2 109.0(7) . . ? F4 C3 C4 112.8(8) . . ? F3 C3 C4 108.6(9) . . ? C2 C3 C4 103.0(7) . . ? F5 C4 F6 105.3(5) . . ? F5 C4 C5 114.2(9) . . ? F6 C4 C5 110.2(6) . . ? F5 C4 C3 112.2(6) . . ? F6 C4 C3 109.5(9) . . ? C5 C4 C3 105.4(6) . . ? C1 C5 C33 128.2(8) . . ? C1 C5 C4 110.3(10) . . ? C33 C5 C4 121.2(6) . . ? C13 C12 C11 127.9(7) . . ? C13 C12 S1 112.3(7) . . ? C11 C12 S1 119.7(7) . . ? C12 C13 C14 113.5(7) . . ? C12 C13 C1 122.2(8) . . ? C14 C13 C1 123.5(10) . . ? C15 C14 C19 119.3(7) . . ? C15 C14 C13 129.8(7) . . ? C19 C14 C13 110.8(9) . . ? C16 C15 C14 118.8(9) . . ? C15 C16 C17 120.5(13) . . ? C18 C17 C16 121.6(11) . . ? C17 C18 C19 118.5(9) . . ? C18 C19 C14 121.0(10) . . ? C18 C19 S1 127.2(8) . . ? C14 C19 S1 111.7(6) . . ? C33 C32 C31 125.2(10) . . ? C33 C32 S2 112.1(9) . . ? C31 C32 S2 122.6(6) . . ? C32 C33 C34 112.5(9) . . ? C32 C33 C5 123.4(10) . . ? C34 C33 C5 124.0(6) . . ? C35 C34 C39 118.4(11) . . ? C35 C34 C33 128.3(10) . . ? C39 C34 C33 113.1(7) . . ? C36 C35 C34 120.3(12) . . ? C35 C36 C37 121.0(10) . . ? C38 C37 C36 119.4(14) . . ? C37 C38 C39 120.8(13) . . ? C38 C39 C34 120.0(8) . . ? C38 C39 S2 130.4(8) . . ? C34 C39 S2 109.3(8) . . ? C19 S1 C12 91.5(5) . . ? C32 S2 C39 92.9(5) . . ? _database_code_depnum_ccdc_archive 'CCDC 961257' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5.38GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 10.135(9) _cell_length_b 15.0384(16) _cell_length_c 10.900(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.52(9) _cell_angle_gamma 90.00 _cell_volume 1584.3(17) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1182 _cell_measurement_theta_min 3.3120 _cell_measurement_theta_max 25.4164 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.964 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.86998 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 5277 _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 25.55 _reflns_number_total 1046 _reflns_number_gt 799 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.321 _diffrn_reflns_theta_full 25.55 _diffrn_measured_fraction_theta_full 0.321 _refine_diff_density_max 0.351 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.059 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0339P)^2^+1.4145P] 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 1046 _refine_ls_number_parameters 137 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1193 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.411 _refine_ls_restrained_S_all 1.380 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.5439(10) 0.1663(3) 0.8041(8) 0.0170(14) Uiso 1 1 d D . . C2 C 0.4788(9) 0.2466(3) 0.8392(7) 0.0194(15) Uiso 1 1 d D . . C3 C 0.5510(10) 0.2637(4) 0.9851(8) 0.019(2) Uiso 1 1 d D . . C4 C 0.6677(8) 0.1953(3) 1.0201(7) 0.0173(14) Uiso 1 1 d D . . C5 C 0.6498(9) 0.1379(3) 0.9021(8) 0.0169(14) Uiso 1 1 d D . . C11 C 0.6779(10) 0.2193(4) 0.5926(10) 0.0232(16) Uiso 1 1 d D . . H11A H 0.6964 0.2531 0.6707 0.035 Uiso 1 1 calc R . . H11B H 0.6604 0.2590 0.5206 0.035 Uiso 1 1 calc R . . H11C H 0.7565 0.1827 0.5958 0.035 Uiso 1 1 calc R . . C12 C 0.5540(9) 0.1616(3) 0.5784(8) 0.0171(15) Uiso 1 1 d D . . C13 C 0.4996(9) 0.1315(3) 0.6713(8) 0.0148(14) Uiso 1 1 d D . . C14 C 0.3905(9) 0.0670(3) 0.6236(8) 0.0160(14) Uiso 1 1 d D . . C15 C 0.3227(10) 0.0131(3) 0.6900(9) 0.0246(16) Uiso 1 1 d D . . H15 H 0.3474 0.0152 0.7793 0.030 Uiso 1 1 calc R . . C16 C 0.2179(11) -0.0440(4) 0.6216(9) 0.0303(17) Uiso 1 1 d D . . H16 H 0.1728 -0.0804 0.6651 0.036 Uiso 1 1 calc R . . C17 C 0.1815(10) -0.0463(4) 0.4888(8) 0.0233(16) Uiso 1 1 d D . . H17 H 0.1061 -0.0803 0.4432 0.028 Uiso 1 1 calc R . . C18 C 0.2540(10) 0.0004(3) 0.4238(9) 0.0219(16) Uiso 1 1 d D . . H18 H 0.2329 -0.0053 0.3351 0.026 Uiso 1 1 calc R . . C19 C 0.3599(8) 0.0568(3) 0.4908(7) 0.0137(14) Uiso 1 1 d D . . C31 C 0.6161(10) -0.0702(4) 0.9249(9) 0.0268(17) Uiso 1 1 d D . . H31A H 0.5486 -0.0293 0.9374 0.040 Uiso 1 1 calc R . . H31B H 0.6512 -0.1060 1.0007 0.040 Uiso 1 1 calc R . . H31C H 0.5738 -0.1079 0.8526 0.040 Uiso 1 1 calc R . . C32 C 0.7316(8) -0.0200(3) 0.9003(8) 0.0199(15) Uiso 1 1 d D . . C33 C 0.7486(9) 0.0701(3) 0.8949(8) 0.0177(15) Uiso 1 1 d D . . C34 C 0.8739(9) 0.0930(3) 0.8668(8) 0.0180(15) Uiso 1 1 d D . . C35 C 0.9210(11) 0.1779(3) 0.8471(8) 0.0161(15) Uiso 1 1 d D . . H35 H 0.8725 0.2283 0.8578 0.019 Uiso 1 1 calc R . . C36 C 1.0395(10) 0.1858(4) 0.8118(8) 0.0210(16) Uiso 1 1 d D . . H36 H 1.0700 0.2421 0.7977 0.025 Uiso 1 1 calc R . . C37 C 1.1153(10) 0.1116(3) 0.7966(9) 0.0268(17) Uiso 1 1 d D . . H37 H 1.1949 0.1187 0.7719 0.032 Uiso 1 1 calc R . . C38 C 1.0724(10) 0.0278(4) 0.8180(8) 0.0228(17) Uiso 1 1 d D . . H38 H 1.1239 -0.0218 0.8097 0.027 Uiso 1 1 calc R . . C39 C 0.9517(9) 0.0179(3) 0.8522(8) 0.0146(15) Uiso 1 1 d D . . F1 F 0.4908(6) 0.3181(2) 0.7688(6) 0.0287(10) Uiso 1 1 d D . . F2 F 0.3396(6) 0.23819(19) 0.8209(6) 0.0278(9) Uiso 1 1 d D . . F3 F 0.6022(6) 0.34786(18) 1.0027(6) 0.0259(9) Uiso 1 1 d D . . F4 F 0.4653(8) 0.2542(2) 1.0532(7) 0.0354(14) Uiso 1 1 d D . . F5 F 0.7937(6) 0.23536(19) 1.0529(6) 0.0275(9) Uiso 1 1 d D . . F6 F 0.6664(6) 0.14680(19) 1.1236(6) 0.0282(10) Uiso 1 1 d D . . S1 S 0.4675(3) 0.11770(9) 0.4291(3) 0.027(3) Uani 1 1 d D . . S2 S 0.8677(3) -0.07792(9) 0.8737(3) 0.035(3) Uani 1 1 d 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 S1 0.039(4) 0.0194(8) 0.019(3) -0.0002(9) 0.001(3) 0.0018(11) S2 0.040(4) 0.0162(8) 0.040(4) 0.0005(9) -0.003(4) 0.0015(11) _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 C5 1.336(6) . ? C1 C13 1.477(10) . ? C1 C2 1.481(11) . ? C2 F1 1.348(8) . ? C2 F2 1.370(10) . ? C2 C3 1.558(9) . ? C3 F4 1.310(12) . ? C3 F3 1.359(7) . ? C3 C4 1.527(9) . ? C4 F6 1.347(9) . ? C4 F5 1.358(8) . ? C4 C5 1.514(10) . ? C5 C33 1.448(10) . ? C11 C12 1.496(10) . ? C12 C13 1.368(12) . ? C12 S1 1.729(7) . ? C13 C14 1.445(8) . ? C14 C15 1.397(12) . ? C14 C19 1.394(10) . ? C15 C16 1.394(8) . ? C16 C17 1.382(10) . ? C17 C18 1.360(12) . ? C18 C19 1.390(7) . ? C19 S1 1.709(10) . ? C31 C32 1.483(12) . ? C32 C33 1.368(7) . ? C32 S2 1.729(10) . ? C33 C34 1.435(12) . ? C34 C35 1.403(9) . ? C34 C39 1.414(9) . ? C35 C36 1.372(13) . ? C36 C37 1.392(10) . ? C37 C38 1.375(9) . ? C38 C39 1.390(13) . ? C39 S2 1.725(8) . ? 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 C5 C1 C13 127.2(8) . . ? C5 C1 C2 111.5(7) . . ? C13 C1 C2 121.0(5) . . ? F1 C2 F2 104.8(5) . . ? F1 C2 C1 112.3(9) . . ? F2 C2 C1 114.0(5) . . ? F1 C2 C3 110.7(5) . . ? F2 C2 C3 108.1(8) . . ? C1 C2 C3 106.8(5) . . ? F4 C3 F3 108.2(8) . . ? F4 C3 C4 112.4(7) . . ? F3 C3 C4 111.0(6) . . ? F4 C3 C2 111.9(7) . . ? F3 C3 C2 109.9(6) . . ? C4 C3 C2 103.6(6) . . ? F6 C4 F5 105.4(5) . . ? F6 C4 C5 112.0(5) . . ? F5 C4 C5 109.8(8) . . ? F6 C4 C3 111.8(8) . . ? F5 C4 C3 111.3(5) . . ? C5 C4 C3 106.6(5) . . ? C1 C5 C33 125.7(8) . . ? C1 C5 C4 111.1(7) . . ? C33 C5 C4 122.7(5) . . ? C13 C12 C11 128.9(6) . . ? C13 C12 S1 111.5(5) . . ? C11 C12 S1 119.4(8) . . ? C12 C13 C14 113.0(7) . . ? C12 C13 C1 122.5(7) . . ? C14 C13 C1 124.4(9) . . ? C15 C14 C19 118.9(6) . . ? C15 C14 C13 130.2(7) . . ? C19 C14 C13 110.7(8) . . ? C16 C15 C14 119.6(9) . . ? C17 C16 C15 119.7(10) . . ? C18 C17 C16 121.1(7) . . ? C17 C18 C19 119.6(9) . . ? C18 C19 C14 120.5(9) . . ? C18 C19 S1 127.1(8) . . ? C14 C19 S1 112.4(5) . . ? C33 C32 C31 128.9(8) . . ? C33 C32 S2 111.9(8) . . ? C31 C32 S2 119.1(5) . . ? C32 C33 C34 112.2(8) . . ? C32 C33 C5 126.6(9) . . ? C34 C33 C5 120.8(6) . . ? C35 C34 C39 118.9(10) . . ? C35 C34 C33 128.0(8) . . ? C39 C34 C33 113.0(6) . . ? C36 C35 C34 119.2(8) . . ? C35 C36 C37 121.7(8) . . ? C38 C37 C36 120.0(11) . . ? C37 C38 C39 119.5(8) . . ? C38 C39 C34 120.6(7) . . ? C38 C39 S2 129.6(6) . . ? C34 C39 S2 109.7(8) . . ? C19 S1 C12 92.1(5) . . ? C32 S2 C39 93.1(4) . . ? _database_code_depnum_ccdc_archive 'CCDC 961258' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5.50GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 10.118(18) _cell_length_b 15.012(3) _cell_length_c 10.877(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.53(16) _cell_angle_gamma 90.00 _cell_volume 1575(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1258 _cell_measurement_theta_min 3.3195 _cell_measurement_theta_max 25.4318 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.975 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.323 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.82288 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 5291 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.0728 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 25.57 _reflns_number_total 992 _reflns_number_gt 781 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.305 _diffrn_reflns_theta_full 25.57 _diffrn_measured_fraction_theta_full 0.305 _refine_diff_density_max 0.346 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.058 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0339P)^2^+1.4145P] 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 992 _refine_ls_number_parameters 137 _refine_ls_number_restraints 69 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.456 _refine_ls_restrained_S_all 1.422 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.5434(11) 0.1664(3) 0.8048(8) 0.0158(14) Uiso 1 1 d D . . C2 C 0.4789(9) 0.2469(3) 0.8390(7) 0.0164(14) Uiso 1 1 d D . . C3 C 0.5510(10) 0.2642(4) 0.9854(8) 0.019(2) Uiso 1 1 d D . . C4 C 0.6668(9) 0.1955(3) 1.0204(7) 0.0139(14) Uiso 1 1 d D . . C5 C 0.6497(10) 0.1379(3) 0.9032(8) 0.0144(14) Uiso 1 1 d D . . C11 C 0.6777(11) 0.2193(4) 0.5942(9) 0.0208(15) Uiso 1 1 d D . . H11A H 0.6939 0.2542 0.6713 0.031 Uiso 1 1 calc R . . H11B H 0.6616 0.2582 0.5211 0.031 Uiso 1 1 calc R . . H11C H 0.7573 0.1828 0.6002 0.031 Uiso 1 1 calc R . . C12 C 0.5540(9) 0.1614(3) 0.5787(8) 0.0166(15) Uiso 1 1 d D . . C13 C 0.5000(9) 0.1317(3) 0.6720(7) 0.0140(14) Uiso 1 1 d D . . C14 C 0.3902(9) 0.0672(3) 0.6243(7) 0.0135(14) Uiso 1 1 d D . . C15 C 0.3208(10) 0.0130(3) 0.6904(9) 0.0228(16) Uiso 1 1 d D . . H15 H 0.3441 0.0152 0.7798 0.027 Uiso 1 1 calc R . . C16 C 0.2175(12) -0.0439(4) 0.6208(9) 0.0296(17) Uiso 1 1 d D . . H16 H 0.1717 -0.0808 0.6634 0.036 Uiso 1 1 calc R . . C17 C 0.1825(11) -0.0457(4) 0.4873(8) 0.0201(15) Uiso 1 1 d D . . H17 H 0.1072 -0.0799 0.4410 0.024 Uiso 1 1 calc R . . C18 C 0.2547(10) 0.0006(3) 0.4230(9) 0.0158(15) Uiso 1 1 d D . . H18 H 0.2342 -0.0050 0.3340 0.019 Uiso 1 1 calc R . . C19 C 0.3599(9) 0.0570(3) 0.4912(7) 0.0127(14) Uiso 1 1 d D . . C31 C 0.6155(11) -0.0706(3) 0.9249(9) 0.0228(16) Uiso 1 1 d D . . H31A H 0.5481 -0.0296 0.9378 0.034 Uiso 1 1 calc R . . H31B H 0.6506 -0.1068 1.0005 0.034 Uiso 1 1 calc R . . H31C H 0.5730 -0.1080 0.8522 0.034 Uiso 1 1 calc R . . C32 C 0.7312(9) -0.0203(3) 0.9006(7) 0.0190(15) Uiso 1 1 d D . . C33 C 0.7499(10) 0.0703(3) 0.8949(8) 0.0154(15) Uiso 1 1 d D . . C34 C 0.8744(10) 0.0935(3) 0.8674(7) 0.0162(15) Uiso 1 1 d D . . C35 C 0.9220(12) 0.1784(4) 0.8481(8) 0.0151(16) Uiso 1 1 d D . . H35 H 0.8739 0.2290 0.8592 0.018 Uiso 1 1 calc R . . C36 C 1.0403(11) 0.1858(4) 0.8124(8) 0.0188(17) Uiso 1 1 d D . . H36 H 1.0710 0.2421 0.7982 0.023 Uiso 1 1 calc R . . C37 C 1.1157(11) 0.1117(3) 0.7971(8) 0.0257(16) Uiso 1 1 d D . . H37 H 1.1954 0.1184 0.7722 0.031 Uiso 1 1 calc R . . C38 C 1.0713(11) 0.0274(4) 0.8190(8) 0.0208(17) Uiso 1 1 d D . . H38 H 1.1227 -0.0225 0.8111 0.025 Uiso 1 1 calc R . . C39 C 0.9501(10) 0.0174(3) 0.8528(7) 0.0149(15) Uiso 1 1 d D . . F1 F 0.4905(7) 0.31845(19) 0.7698(5) 0.0250(9) Uiso 1 1 d D . . F2 F 0.3398(7) 0.23855(19) 0.8211(5) 0.0262(9) Uiso 1 1 d D . . F3 F 0.6027(7) 0.34834(18) 1.0029(6) 0.0237(9) Uiso 1 1 d D . . F4 F 0.4662(9) 0.2546(2) 1.0544(7) 0.0320(14) Uiso 1 1 d D . . F5 F 0.7930(7) 0.23568(19) 1.0540(5) 0.0262(9) Uiso 1 1 d D . . F6 F 0.6658(7) 0.14720(18) 1.1259(5) 0.0265(10) Uiso 1 1 d D . . S1 S 0.4685(3) 0.11777(9) 0.4289(3) 0.028(3) Uani 1 1 d D . . S2 S 0.8675(4) -0.07850(8) 0.8740(3) 0.029(4) Uani 1 1 d 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 S1 0.042(5) 0.0167(8) 0.018(3) -0.0004(9) -0.002(4) 0.0022(12) S2 0.036(5) 0.0131(8) 0.032(3) 0.0016(9) 0.000(4) -0.0004(11) _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 C5 1.339(7) . ? C1 C2 1.474(11) . ? C1 C13 1.473(9) . ? C2 F1 1.337(7) . ? C2 F2 1.368(10) . ? C2 C3 1.561(9) . ? C3 F4 1.307(13) . ? C3 F3 1.358(7) . ? C3 C4 1.521(9) . ? C4 F5 1.359(9) . ? C4 F6 1.360(9) . ? C4 C5 1.507(10) . ? C5 C33 1.456(10) . ? C11 C12 1.491(11) . ? C12 C13 1.365(12) . ? C12 S1 1.727(7) . ? C13 C14 1.447(8) . ? C14 C19 1.396(10) . ? C14 C15 1.406(12) . ? C15 C16 1.385(8) . ? C16 C17 1.388(10) . ? C17 C18 1.347(12) . ? C18 C19 1.387(7) . ? C19 S1 1.717(10) . ? C31 C32 1.482(12) . ? C32 C33 1.378(7) . ? C32 S2 1.730(10) . ? C33 C34 1.423(12) . ? C34 C35 1.401(9) . ? C34 C39 1.410(10) . ? C35 C36 1.369(13) . ? C36 C37 1.388(10) . ? C37 C38 1.386(9) . ? C38 C39 1.391(13) . ? C39 S2 1.715(8) . ? 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 C5 C1 C2 111.8(6) . . ? C5 C1 C13 127.0(8) . . ? C2 C1 C13 120.9(5) . . ? F1 C2 F2 104.8(5) . . ? F1 C2 C1 113.3(9) . . ? F2 C2 C1 113.8(5) . . ? F1 C2 C3 110.3(5) . . ? F2 C2 C3 107.8(8) . . ? C1 C2 C3 106.7(5) . . ? F4 C3 F3 108.3(8) . . ? F4 C3 C4 111.8(7) . . ? F3 C3 C4 111.1(7) . . ? F4 C3 C2 112.4(7) . . ? F3 C3 C2 109.9(6) . . ? C4 C3 C2 103.3(6) . . ? F5 C4 F6 104.7(5) . . ? F5 C4 C5 109.9(8) . . ? F6 C4 C5 112.3(5) . . ? F5 C4 C3 110.9(5) . . ? F6 C4 C3 111.9(9) . . ? C5 C4 C3 107.1(5) . . ? C1 C5 C33 125.5(8) . . ? C1 C5 C4 110.6(7) . . ? C33 C5 C4 123.2(5) . . ? C13 C12 C11 128.1(6) . . ? C13 C12 S1 112.2(6) . . ? C11 C12 S1 119.5(8) . . ? C12 C13 C14 112.9(7) . . ? C12 C13 C1 123.1(7) . . ? C14 C13 C1 123.9(9) . . ? C19 C14 C15 118.6(6) . . ? C19 C14 C13 110.5(8) . . ? C15 C14 C13 130.7(7) . . ? C16 C15 C14 119.2(9) . . ? C15 C16 C17 119.8(11) . . ? C18 C17 C16 121.7(7) . . ? C17 C18 C19 119.1(8) . . ? C18 C19 C14 121.0(9) . . ? C18 C19 S1 126.4(8) . . ? C14 C19 S1 112.6(5) . . ? C33 C32 C31 129.6(9) . . ? C33 C32 S2 111.4(8) . . ? C31 C32 S2 119.0(5) . . ? C32 C33 C34 113.1(8) . . ? C32 C33 C5 125.3(10) . . ? C34 C33 C5 121.3(6) . . ? C35 C34 C39 119.8(10) . . ? C35 C34 C33 128.3(8) . . ? C39 C34 C33 111.8(7) . . ? C36 C35 C34 119.1(9) . . ? C35 C36 C37 121.9(9) . . ? C36 C37 C38 119.5(11) . . ? C39 C38 C37 120.1(9) . . ? C38 C39 C34 119.6(7) . . ? C38 C39 S2 129.1(6) . . ? C34 C39 S2 111.2(8) . . ? C19 S1 C12 91.6(5) . . ? C39 S2 C32 92.5(5) . . ? _database_code_depnum_ccdc_archive 'CCDC 961259' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5.60GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 10.117(18) _cell_length_b 15.004(3) _cell_length_c 10.869(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.52(16) _cell_angle_gamma 90.00 _cell_volume 1573(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1460 _cell_measurement_theta_min 3.3227 _cell_measurement_theta_max 25.4345 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.978 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.323 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.21297 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 5013 _diffrn_reflns_av_R_equivalents 0.0671 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 25.51 _reflns_number_total 961 _reflns_number_gt 785 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.298 _diffrn_reflns_theta_full 25.51 _diffrn_measured_fraction_theta_full 0.298 _refine_diff_density_max 0.380 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.058 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0339P)^2^+1.4145P] 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 961 _refine_ls_number_parameters 137 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.530 _refine_ls_restrained_S_all 1.496 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.5440(11) 0.1666(3) 0.8048(8) 0.0129(13) Uiso 1 1 d D . . C2 C 0.4798(9) 0.2473(3) 0.8386(7) 0.0136(13) Uiso 1 1 d D . . C3 C 0.5512(10) 0.2649(4) 0.9851(8) 0.0171(19) Uiso 1 1 d D . . C4 C 0.6677(8) 0.1957(3) 1.0209(6) 0.0115(13) Uiso 1 1 d D . . C5 C 0.6500(10) 0.1379(3) 0.9031(7) 0.0108(12) Uiso 1 1 d D . . C11 C 0.6787(11) 0.2193(4) 0.5946(9) 0.0204(14) Uiso 1 1 d D . . H11A H 0.6899 0.2580 0.6674 0.031 Uiso 1 1 calc R . . H11B H 0.6663 0.2544 0.5181 0.031 Uiso 1 1 calc R . . H11C H 0.7597 0.1827 0.6085 0.031 Uiso 1 1 calc R . . C12 C 0.5546(9) 0.1614(3) 0.5787(7) 0.0145(14) Uiso 1 1 d D . . C13 C 0.5003(9) 0.1320(3) 0.6722(7) 0.0122(13) Uiso 1 1 d D . . C14 C 0.3896(9) 0.0673(3) 0.6246(7) 0.0114(13) Uiso 1 1 d D . . C15 C 0.3206(10) 0.0132(3) 0.6910(8) 0.0199(15) Uiso 1 1 d D . . H15 H 0.3440 0.0155 0.7805 0.024 Uiso 1 1 calc R . . C16 C 0.2165(12) -0.0440(4) 0.6211(8) 0.0265(16) Uiso 1 1 d D . . H16 H 0.1704 -0.0807 0.6636 0.032 Uiso 1 1 calc R . . C17 C 0.1819(11) -0.0459(3) 0.4861(8) 0.0194(14) Uiso 1 1 d D . . H17 H 0.1066 -0.0799 0.4396 0.023 Uiso 1 1 calc R . . C18 C 0.2549(10) 0.0005(3) 0.4217(8) 0.0149(14) Uiso 1 1 d D . . H18 H 0.2350 -0.0053 0.3328 0.018 Uiso 1 1 calc R . . C19 C 0.3603(9) 0.0568(3) 0.4907(7) 0.0104(12) Uiso 1 1 d D . . C31 C 0.6142(11) -0.0705(3) 0.9249(9) 0.0211(15) Uiso 1 1 d D . . H31A H 0.5453 -0.0291 0.9339 0.032 Uiso 1 1 calc R . . H31B H 0.6478 -0.1049 1.0025 0.032 Uiso 1 1 calc R . . H31C H 0.5740 -0.1096 0.8535 0.032 Uiso 1 1 calc R . . C32 C 0.7311(9) -0.0207(3) 0.9013(7) 0.0155(14) Uiso 1 1 d D . . C33 C 0.7494(10) 0.0698(3) 0.8945(7) 0.0129(14) Uiso 1 1 d D . . C34 C 0.8742(10) 0.0933(3) 0.8674(7) 0.0150(14) Uiso 1 1 d D . . C35 C 0.9202(12) 0.1785(3) 0.8480(8) 0.0124(14) Uiso 1 1 d D . . H35 H 0.8714 0.2290 0.8585 0.015 Uiso 1 1 calc R . . C36 C 1.0398(12) 0.1857(4) 0.8131(8) 0.0163(15) Uiso 1 1 d D . . H36 H 1.0708 0.2422 0.7996 0.020 Uiso 1 1 calc R . . C37 C 1.1159(11) 0.1115(3) 0.7971(8) 0.0239(15) Uiso 1 1 d D . . H37 H 1.1955 0.1185 0.7721 0.029 Uiso 1 1 calc R . . C38 C 1.0714(11) 0.0269(4) 0.8192(8) 0.0181(15) Uiso 1 1 d D . . H38 H 1.1226 -0.0231 0.8114 0.022 Uiso 1 1 calc R . . C39 C 0.9502(10) 0.0177(3) 0.8529(7) 0.0126(14) Uiso 1 1 d D . . F1 F 0.4918(7) 0.31862(19) 0.7689(5) 0.0232(9) Uiso 1 1 d D . . F2 F 0.3392(7) 0.23858(19) 0.8215(5) 0.0235(9) Uiso 1 1 d D . . F3 F 0.6035(7) 0.34847(17) 1.0024(6) 0.0217(9) Uiso 1 1 d D . . F4 F 0.4668(8) 0.2547(2) 1.0542(6) 0.0285(12) Uiso 1 1 d D . . F5 F 0.7934(7) 0.23596(18) 1.0542(5) 0.0233(9) Uiso 1 1 d D . . F6 F 0.6658(7) 0.14743(18) 1.1263(5) 0.0230(9) Uiso 1 1 d D . . S1 S 0.4684(3) 0.11786(8) 0.4292(2) 0.023(3) Uani 1 1 d D . . S2 S 0.8675(3) -0.07850(8) 0.8741(3) 0.026(3) Uani 1 1 d 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 S1 0.032(5) 0.0147(7) 0.016(3) 0.0001(8) -0.001(3) 0.0022(11) S2 0.030(5) 0.0114(7) 0.030(3) 0.0023(8) -0.001(4) -0.0004(10) _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 C5 1.337(7) . ? C1 C2 1.471(11) . ? C1 C13 1.469(9) . ? C2 F1 1.338(8) . ? C2 F2 1.384(11) . ? C2 C3 1.561(8) . ? C3 F4 1.305(12) . ? C3 F3 1.352(7) . ? C3 C4 1.531(9) . ? C4 F5 1.355(9) . ? C4 F6 1.360(9) . ? C4 C5 1.512(9) . ? C5 C33 1.455(10) . ? C11 C12 1.494(11) . ? C12 C13 1.365(12) . ? C12 S1 1.725(6) . ? C13 C14 1.454(8) . ? C14 C15 1.404(12) . ? C14 C19 1.404(10) . ? C15 C16 1.393(8) . ? C16 C17 1.402(10) . ? C17 C18 1.354(12) . ? C18 C19 1.390(7) . ? C19 S1 1.710(10) . ? C31 C32 1.484(12) . ? C32 C33 1.377(7) . ? C32 S2 1.729(10) . ? C33 C34 1.424(12) . ? C34 C35 1.397(9) . ? C34 C39 1.407(10) . ? C35 C36 1.377(13) . ? C36 C37 1.394(10) . ? C37 C38 1.391(9) . ? C38 C39 1.389(13) . ? C39 S2 1.717(8) . ? 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 C5 C1 C2 112.0(6) . . ? C5 C1 C13 127.0(8) . . ? C2 C1 C13 120.7(4) . . ? F1 C2 F2 105.3(5) . . ? F1 C2 C1 113.3(9) . . ? F2 C2 C1 113.7(5) . . ? F1 C2 C3 110.4(4) . . ? F2 C2 C3 107.1(8) . . ? C1 C2 C3 106.9(5) . . ? F4 C3 F3 109.0(8) . . ? F4 C3 C4 111.2(7) . . ? F3 C3 C4 110.8(7) . . ? F4 C3 C2 112.6(7) . . ? F3 C3 C2 109.9(6) . . ? C4 C3 C2 103.2(6) . . ? F5 C4 F6 105.2(4) . . ? F5 C4 C5 110.1(8) . . ? F6 C4 C5 112.3(5) . . ? F5 C4 C3 110.8(5) . . ? F6 C4 C3 111.7(8) . . ? C5 C4 C3 106.7(4) . . ? C1 C5 C33 125.4(8) . . ? C1 C5 C4 110.7(7) . . ? C33 C5 C4 123.3(5) . . ? C13 C12 C11 127.9(6) . . ? C13 C12 S1 112.1(5) . . ? C11 C12 S1 119.9(7) . . ? C12 C13 C14 113.0(7) . . ? C12 C13 C1 123.1(7) . . ? C14 C13 C1 123.8(9) . . ? C15 C14 C19 119.0(5) . . ? C15 C14 C13 130.7(7) . . ? C19 C14 C13 110.1(8) . . ? C16 C15 C14 119.1(8) . . ? C15 C16 C17 119.6(10) . . ? C18 C17 C16 121.8(7) . . ? C17 C18 C19 118.9(8) . . ? C18 C19 C14 121.1(9) . . ? C18 C19 S1 126.3(8) . . ? C14 C19 S1 112.6(5) . . ? C33 C32 C31 129.2(8) . . ? C33 C32 S2 111.0(8) . . ? C31 C32 S2 119.7(5) . . ? C32 C33 C34 113.4(8) . . ? C32 C33 C5 125.6(9) . . ? C34 C33 C5 120.8(6) . . ? C35 C34 C39 120.2(10) . . ? C35 C34 C33 127.9(8) . . ? C39 C34 C33 111.8(6) . . ? C36 C35 C34 118.3(9) . . ? C35 C36 C37 122.4(8) . . ? C36 C37 C38 119.2(11) . . ? C39 C38 C37 119.6(8) . . ? C38 C39 C34 120.3(7) . . ? C38 C39 S2 128.6(6) . . ? C34 C39 S2 111.0(8) . . ? C19 S1 C12 92.0(5) . . ? C39 S2 C32 92.8(5) . . ? _database_code_depnum_ccdc_archive 'CCDC 961260' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6.56GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 10.052(2) _cell_length_b 14.932(3) _cell_length_c 10.789(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.39(3) _cell_angle_gamma 90.00 _cell_volume 1545.4(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2294 _cell_measurement_theta_min 2.3181 _cell_measurement_theta_max 29.3887 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.013 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.329 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.24565 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 4424 _diffrn_reflns_av_R_equivalents 0.0921 _diffrn_reflns_av_sigmaI/netI 0.0849 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 22.60 _reflns_number_total 801 _reflns_number_gt 620 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.357 _diffrn_reflns_theta_full 22.60 _diffrn_measured_fraction_theta_full 0.357 _refine_diff_density_max 0.279 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.060 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0339P)^2^+1.4145P] 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 801 _refine_ls_number_parameters 137 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.261 _refine_ls_restrained_S_all 1.218 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.5431(11) 0.1661(4) 0.8066(10) 0.0151(17) Uiso 1 1 d D . . C2 C 0.4798(10) 0.2481(4) 0.8407(8) 0.0139(17) Uiso 1 1 d D . . C3 C 0.5526(11) 0.2650(4) 0.9872(9) 0.019(3) Uiso 1 1 d D . . C4 C 0.6685(9) 0.1959(4) 1.0236(8) 0.0139(17) Uiso 1 1 d D . . C5 C 0.6495(11) 0.1381(4) 0.9054(9) 0.0122(17) Uiso 1 1 d D . . C11 C 0.6820(12) 0.2189(4) 0.5969(11) 0.0188(18) Uiso 1 1 d D . . H11A H 0.6963 0.2553 0.6731 0.028 Uiso 1 1 calc R . . H11B H 0.6687 0.2567 0.5222 0.028 Uiso 1 1 calc R . . H11C H 0.7620 0.1814 0.6062 0.028 Uiso 1 1 calc R . . C12 C 0.5565(10) 0.1619(4) 0.5800(9) 0.0130(18) Uiso 1 1 d D . . C13 C 0.5010(10) 0.1319(4) 0.6727(9) 0.0123(17) Uiso 1 1 d D . . C14 C 0.3897(10) 0.0675(4) 0.6239(9) 0.0131(18) Uiso 1 1 d D . . C15 C 0.3198(11) 0.0131(4) 0.6903(10) 0.0205(19) Uiso 1 1 d D . . H15 H 0.3421 0.0151 0.7804 0.025 Uiso 1 1 calc R . . C16 C 0.2163(12) -0.0439(4) 0.6177(10) 0.027(2) Uiso 1 1 d D . . H16 H 0.1702 -0.0815 0.6599 0.032 Uiso 1 1 calc R . . C17 C 0.1808(11) -0.0453(4) 0.4832(9) 0.0189(19) Uiso 1 1 d D . . H17 H 0.1043 -0.0789 0.4365 0.023 Uiso 1 1 calc R . . C18 C 0.2549(11) 0.0010(4) 0.4184(10) 0.0150(18) Uiso 1 1 d D . . H18 H 0.2360 -0.0048 0.3289 0.018 Uiso 1 1 calc R . . C19 C 0.3605(9) 0.0575(4) 0.4897(8) 0.0136(17) Uiso 1 1 d D . . C31 C 0.6123(11) -0.0716(4) 0.9252(10) 0.0184(18) Uiso 1 1 d D . . H31A H 0.5426 -0.0303 0.9343 0.028 Uiso 1 1 calc R . . H31B H 0.6458 -0.1064 1.0032 0.028 Uiso 1 1 calc R . . H31C H 0.5725 -0.1107 0.8530 0.028 Uiso 1 1 calc R . . C32 C 0.7297(9) -0.0212(4) 0.9023(9) 0.0163(18) Uiso 1 1 d D . . C33 C 0.7485(10) 0.0690(4) 0.8978(9) 0.0146(18) Uiso 1 1 d D . . C34 C 0.8744(10) 0.0925(4) 0.8689(9) 0.0152(18) Uiso 1 1 d D . . C35 C 0.9218(13) 0.1783(4) 0.8514(10) 0.0156(19) Uiso 1 1 d D . . H35 H 0.8736 0.2291 0.8635 0.019 Uiso 1 1 calc R . . C36 C 1.0412(12) 0.1852(4) 0.8159(10) 0.017(2) Uiso 1 1 d D . . H36 H 1.0725 0.2419 0.8020 0.021 Uiso 1 1 calc R . . C37 C 1.1171(11) 0.1109(4) 0.7999(10) 0.023(2) Uiso 1 1 d D . . H37 H 1.1977 0.1182 0.7755 0.028 Uiso 1 1 calc R . . C38 C 1.0735(12) 0.0269(4) 0.8200(10) 0.019(2) Uiso 1 1 d D . . H38 H 1.1252 -0.0231 0.8112 0.023 Uiso 1 1 calc R . . C39 C 0.9515(11) 0.0169(4) 0.8535(9) 0.0147(18) Uiso 1 1 d D . . F1 F 0.4920(7) 0.3194(2) 0.7695(6) 0.0243(11) Uiso 1 1 d D . . F2 F 0.3397(7) 0.2400(2) 0.8224(7) 0.0261(11) Uiso 1 1 d D . . F3 F 0.6034(7) 0.3498(2) 1.0052(7) 0.0222(11) Uiso 1 1 d D . . F4 F 0.4661(9) 0.2564(3) 1.0563(8) 0.0299(16) Uiso 1 1 d D . . F5 F 0.7950(7) 0.2365(2) 1.0551(6) 0.0237(11) Uiso 1 1 d D . . F6 F 0.6671(7) 0.1481(2) 1.1297(6) 0.0239(11) Uiso 1 1 d D . . S1 S 0.4715(4) 0.11817(10) 0.4282(3) 0.027(4) Uani 1 1 d D . . S2 S 0.8671(4) -0.07960(10) 0.8740(3) 0.030(4) Uani 1 1 d 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 S1 0.041(5) 0.0159(10) 0.017(4) -0.0003(11) -0.003(4) 0.0022(13) S2 0.038(5) 0.0142(10) 0.028(4) 0.0013(11) -0.002(4) 0.0003(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 C5 1.332(7) . ? C1 C13 1.470(11) . ? C1 C2 1.476(12) . ? C2 F1 1.340(9) . ? C2 F2 1.367(10) . ? C2 C3 1.551(10) . ? C3 F4 1.310(13) . ? C3 F3 1.357(7) . ? C3 C4 1.517(10) . ? C4 F5 1.356(9) . ? C4 F6 1.353(10) . ? C4 C5 1.504(10) . ? C5 C33 1.453(11) . ? C11 C12 1.487(11) . ? C12 C13 1.358(13) . ? C12 S1 1.733(7) . ? C13 C14 1.450(9) . ? C14 C19 1.396(11) . ? C14 C15 1.403(13) . ? C15 C16 1.390(8) . ? C16 C17 1.386(11) . ? C17 C18 1.355(13) . ? C18 C19 1.394(8) . ? C19 S1 1.716(11) . ? C31 C32 1.481(12) . ? C32 C33 1.362(8) . ? C32 S2 1.736(10) . ? C33 C34 1.434(12) . ? C34 C35 1.399(9) . ? C34 C39 1.408(10) . ? C35 C36 1.368(13) . ? C36 C37 1.387(11) . ? C37 C38 1.368(9) . ? C38 C39 1.387(13) . ? C39 S2 1.719(9) . ? 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 C5 C1 C13 127.1(9) . . ? C5 C1 C2 111.3(7) . . ? C13 C1 C2 121.0(5) . . ? F1 C2 F2 104.7(5) . . ? F1 C2 C1 113.3(10) . . ? F2 C2 C1 113.1(6) . . ? F1 C2 C3 111.0(5) . . ? F2 C2 C3 108.3(9) . . ? C1 C2 C3 106.4(5) . . ? F4 C3 F3 107.2(9) . . ? F4 C3 C4 112.0(8) . . ? F3 C3 C4 111.7(7) . . ? F4 C3 C2 111.9(8) . . ? F3 C3 C2 109.9(7) . . ? C4 C3 C2 104.2(7) . . ? F5 C4 F6 105.7(5) . . ? F5 C4 C5 109.9(9) . . ? F6 C4 C5 112.5(6) . . ? F5 C4 C3 110.5(5) . . ? F6 C4 C3 112.1(9) . . ? C5 C4 C3 106.1(5) . . ? C1 C5 C33 125.3(9) . . ? C1 C5 C4 111.5(7) . . ? C33 C5 C4 122.7(5) . . ? C13 C12 C11 128.2(8) . . ? C13 C12 S1 112.1(6) . . ? C11 C12 S1 119.5(8) . . ? C12 C13 C14 113.2(8) . . ? C12 C13 C1 123.2(7) . . ? C14 C13 C1 123.5(10) . . ? C19 C14 C15 119.1(6) . . ? C19 C14 C13 110.3(9) . . ? C15 C14 C13 130.4(8) . . ? C16 C15 C14 118.1(10) . . ? C17 C16 C15 121.0(11) . . ? C18 C17 C16 121.5(8) . . ? C17 C18 C19 118.0(10) . . ? C18 C19 C14 121.8(10) . . ? C18 C19 S1 125.5(9) . . ? C14 C19 S1 112.7(5) . . ? C33 C32 C31 129.4(9) . . ? C33 C32 S2 111.3(9) . . ? C31 C32 S2 119.3(5) . . ? C32 C33 C34 113.0(9) . . ? C32 C33 C5 126.5(10) . . ? C34 C33 C5 120.1(7) . . ? C35 C34 C39 119.8(11) . . ? C35 C34 C33 127.7(9) . . ? C39 C34 C33 112.4(7) . . ? C36 C35 C34 118.0(10) . . ? C35 C36 C37 122.4(9) . . ? C38 C37 C36 120.0(12) . . ? C37 C38 C39 119.4(10) . . ? C38 C39 C34 120.4(8) . . ? C38 C39 S2 129.2(6) . . ? C34 C39 S2 110.3(8) . . ? C19 S1 C12 91.6(5) . . ? C39 S2 C32 92.9(5) . . ? _database_code_depnum_ccdc_archive 'CCDC 961261' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_7.40GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 9.985(2) _cell_length_b 14.855(3) _cell_length_c 10.722(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.35(3) _cell_angle_gamma 90.00 _cell_volume 1517.9(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1072 _cell_measurement_theta_min 3.3521 _cell_measurement_theta_max 25.9836 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.050 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.08663 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 2902 _diffrn_reflns_av_R_equivalents 0.1450 _diffrn_reflns_av_sigmaI/netI 0.1164 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 22.32 _reflns_number_total 711 _reflns_number_gt 542 _reflns_threshold_expression >2sigma(I) _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.1171P)^2^+3.0025P] 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 711 _refine_ls_number_parameters 137 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.1027 _refine_ls_R_factor_gt 0.0780 _refine_ls_wR_factor_ref 0.2080 _refine_ls_wR_factor_gt 0.1827 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.083 _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 0.5421(18) 0.1662(6) 0.8081(13) 0.013(3) Uiso 1 1 d D . . C2 C 0.4768(13) 0.2498(5) 0.8422(10) 0.006(3) Uiso 1 1 d D . . C3 C 0.5527(15) 0.2663(6) 0.9900(13) 0.010(4) Uiso 1 1 d D . . C4 C 0.6703(12) 0.1970(5) 1.0261(10) 0.006(3) Uiso 1 1 d D . . C5 C 0.6499(15) 0.1383(6) 0.9095(12) 0.006(2) Uiso 1 1 d D . . C11 C 0.6880(18) 0.2187(7) 0.5998(17) 0.016(3) Uiso 1 1 d D . . H11A H 0.7021 0.2550 0.6767 0.025 Uiso 1 1 calc R . . H11B H 0.6771 0.2569 0.5252 0.025 Uiso 1 1 calc R . . H11C H 0.7677 0.1801 0.6100 0.025 Uiso 1 1 calc R . . C12 C 0.5588(14) 0.1625(6) 0.5801(11) 0.007(3) Uiso 1 1 d D . . C13 C 0.5016(14) 0.1314(6) 0.6730(12) 0.010(3) Uiso 1 1 d D . . C14 C 0.3880(14) 0.0672(6) 0.6259(12) 0.012(3) Uiso 1 1 d D . . C15 C 0.3168(16) 0.0119(6) 0.6913(14) 0.016(3) Uiso 1 1 d D . . H15 H 0.3391 0.0125 0.7819 0.019 Uiso 1 1 calc R . . C16 C 0.2126(18) -0.0433(6) 0.6162(14) 0.015(3) Uiso 1 1 d D . . H16 H 0.1638 -0.0801 0.6578 0.018 Uiso 1 1 calc R . . C17 C 0.1775(17) -0.0458(6) 0.4795(13) 0.010(3) Uiso 1 1 d D . . H17 H 0.1008 -0.0794 0.4315 0.012 Uiso 1 1 calc R . . C18 C 0.2559(16) 0.0010(6) 0.4169(15) 0.009(3) Uiso 1 1 d D . . H18 H 0.2402 -0.0052 0.3274 0.011 Uiso 1 1 calc R . . C19 C 0.3606(12) 0.0586(6) 0.4908(11) 0.006(3) Uiso 1 1 d D . . C31 C 0.6081(16) -0.0729(6) 0.9258(15) 0.014(3) Uiso 1 1 d D . . H31A H 0.5425 -0.0308 0.9426 0.021 Uiso 1 1 calc R . . H31B H 0.6416 -0.1124 0.9994 0.021 Uiso 1 1 calc R . . H31C H 0.5626 -0.1076 0.8494 0.021 Uiso 1 1 calc R . . C32 C 0.7287(12) -0.0229(6) 0.9042(13) 0.011(3) Uiso 1 1 d D . . C33 C 0.7500(14) 0.0681(5) 0.8990(13) 0.009(3) Uiso 1 1 d D . . C34 C 0.8773(14) 0.0925(5) 0.8712(13) 0.011(3) Uiso 1 1 d D . . C35 C 0.922(2) 0.1790(6) 0.8527(13) 0.008(3) Uiso 1 1 d D . . H35 H 0.8715 0.2295 0.8638 0.010 Uiso 1 1 calc R . . C36 C 1.0430(19) 0.1872(6) 0.8173(13) 0.007(3) Uiso 1 1 d D . . H36 H 1.0743 0.2442 0.8033 0.008 Uiso 1 1 calc R . . C37 C 1.1195(17) 0.1122(5) 0.8020(15) 0.019(3) Uiso 1 1 d D . . H37 H 1.2011 0.1198 0.7783 0.023 Uiso 1 1 calc R . . C38 C 1.0764(16) 0.0264(6) 0.8215(13) 0.009(3) Uiso 1 1 d D . . H38 H 1.1292 -0.0237 0.8135 0.011 Uiso 1 1 calc R . . C39 C 0.9517(14) 0.0167(5) 0.8535(12) 0.008(3) Uiso 1 1 d D . . F1 F 0.4933(12) 0.3202(3) 0.7710(9) 0.0163(17) Uiso 1 1 d D . . F2 F 0.3371(12) 0.2414(3) 0.8256(10) 0.0192(18) Uiso 1 1 d D . . F3 F 0.6042(12) 0.3515(3) 1.0072(10) 0.0149(17) Uiso 1 1 d D . . F4 F 0.4662(15) 0.2580(4) 1.0598(12) 0.022(2) Uiso 1 1 d D . . F5 F 0.7975(11) 0.2377(3) 1.0565(10) 0.0176(17) Uiso 1 1 d D . . F6 F 0.6699(11) 0.1491(3) 1.1333(9) 0.0162(17) Uiso 1 1 d D . . S1 S 0.4739(6) 0.11847(16) 0.4277(5) 0.033(6) Uani 1 1 d D . . S2 S 0.8669(6) -0.08102(16) 0.8743(5) 0.034(6) Uani 1 1 d 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 S1 0.062(8) 0.0093(15) 0.009(6) -0.0004(16) -0.018(7) -0.0009(19) S2 0.058(8) 0.0053(15) 0.021(5) 0.0039(15) -0.016(6) -0.0026(18) _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 C5 1.347(11) . ? C1 C13 1.476(12) . ? C1 C2 1.498(15) . ? C2 F1 1.333(11) . ? C2 F2 1.358(13) . ? C2 C3 1.558(12) . ? C3 F4 1.306(14) . ? C3 F3 1.358(11) . ? C3 C4 1.522(12) . ? C4 F6 1.353(12) . ? C4 F5 1.356(12) . ? C4 C5 1.488(12) . ? C5 C33 1.472(12) . ? C11 C12 1.498(13) . ? C12 C13 1.368(13) . ? C12 S1 1.729(9) . ? C13 C14 1.452(12) . ? C14 C19 1.397(12) . ? C14 C15 1.403(14) . ? C15 C16 1.380(11) . ? C16 C17 1.403(13) . ? C17 C18 1.364(14) . ? C18 C19 1.399(10) . ? C19 S1 1.728(13) . ? C31 C32 1.490(14) . ? C32 C33 1.372(10) . ? C32 S2 1.737(13) . ? C33 C34 1.436(14) . ? C34 C35 1.394(12) . ? C34 C39 1.393(12) . ? C35 C36 1.377(14) . ? C36 C37 1.388(13) . ? C37 C38 1.381(12) . ? C38 C39 1.393(14) . ? C39 S2 1.728(11) . ? 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 C5 C1 C13 127.2(12) . . ? C5 C1 C2 111.1(9) . . ? C13 C1 C2 121.1(8) . . ? F1 C2 F2 107.1(8) . . ? F1 C2 C1 111.9(12) . . ? F2 C2 C1 113.3(9) . . ? F1 C2 C3 110.7(8) . . ? F2 C2 C3 108.4(11) . . ? C1 C2 C3 105.2(8) . . ? F4 C3 F3 107.3(12) . . ? F4 C3 C4 112.5(11) . . ? F3 C3 C4 111.3(10) . . ? F4 C3 C2 111.3(11) . . ? F3 C3 C2 109.5(10) . . ? C4 C3 C2 104.9(9) . . ? F6 C4 F5 105.7(8) . . ? F6 C4 C5 111.8(8) . . ? F5 C4 C5 110.3(11) . . ? F6 C4 C3 112.0(11) . . ? F5 C4 C3 110.9(8) . . ? C5 C4 C3 106.3(8) . . ? C1 C5 C33 123.6(11) . . ? C1 C5 C4 112.0(10) . . ? C33 C5 C4 123.7(8) . . ? C13 C12 C11 127.9(10) . . ? C13 C12 S1 111.6(9) . . ? C11 C12 S1 120.2(11) . . ? C12 C13 C14 114.9(11) . . ? C12 C13 C1 123.0(11) . . ? C14 C13 C1 121.9(13) . . ? C19 C14 C15 119.5(9) . . ? C19 C14 C13 108.2(11) . . ? C15 C14 C13 132.1(11) . . ? C16 C15 C14 117.6(14) . . ? C15 C16 C17 122.4(15) . . ? C18 C17 C16 120.0(11) . . ? C17 C18 C19 118.4(14) . . ? C18 C19 C14 121.7(12) . . ? C18 C19 S1 124.0(12) . . ? C14 C19 S1 114.2(7) . . ? C33 C32 C31 129.8(11) . . ? C33 C32 S2 109.9(11) . . ? C31 C32 S2 120.3(8) . . ? C32 C33 C34 114.5(11) . . ? C32 C33 C5 125.3(13) . . ? C34 C33 C5 120.0(10) . . ? C35 C34 C39 121.3(14) . . ? C35 C34 C33 127.0(12) . . ? C39 C34 C33 111.4(9) . . ? C36 C35 C34 117.7(14) . . ? C35 C36 C37 121.4(13) . . ? C38 C37 C36 121.0(16) . . ? C37 C38 C39 118.3(13) . . ? C34 C39 C38 120.1(10) . . ? C34 C39 S2 111.1(10) . . ? C38 C39 S2 128.8(8) . . ? C19 S1 C12 91.0(7) . . ? C39 S2 C32 93.1(6) . . ? _diffrn_measured_fraction_theta_max 0.334 _diffrn_reflns_theta_full 22.32 _diffrn_measured_fraction_theta_full 0.334 _refine_diff_density_max 0.311 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 961262' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_8.90GPaBenzothiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2-methyl benzothiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common BenzothiopheneDTE _chemical_formula_moiety 'C23 H14 F6 S2' _chemical_formula_sum 'C23 H14 F6 S2' _chemical_formula_weight 468.46 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 9.894(2) _cell_length_b 14.736(3) _cell_length_c 10.588(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.21(3) _cell_angle_gamma 90.00 _cell_volume 1474.6(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1405 _cell_measurement_theta_min 3.3181 _cell_measurement_theta_max 25.6144 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.110 _exptl_crystal_density_meas ? _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.345 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.64152 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 4687 _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 25.25 _reflns_number_total 908 _reflns_number_gt 765 _reflns_threshold_expression >2sigma(I) _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0221P)^2^+1.6990P] 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 908 _refine_ls_number_parameters 137 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.290 _refine_ls_restrained_S_all 1.262 _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 0.5416(9) 0.1671(3) 0.8100(7) 0.0137(11) Uiso 1 1 d D . . C2 C 0.4780(8) 0.2506(3) 0.8445(6) 0.0123(11) Uiso 1 1 d D . . C3 C 0.5523(9) 0.2687(3) 0.9939(7) 0.0138(15) Uiso 1 1 d D . . C4 C 0.6714(8) 0.1973(3) 1.0296(6) 0.0117(11) Uiso 1 1 d D . . C5 C 0.6484(9) 0.1380(3) 0.9110(7) 0.0130(11) Uiso 1 1 d D . . C11 C 0.6897(10) 0.2185(3) 0.6031(8) 0.0176(11) Uiso 1 1 d D . . H11A H 0.7015 0.2562 0.6795 0.026 Uiso 1 1 calc R . . H11B H 0.6809 0.2560 0.5269 0.026 Uiso 1 1 calc R . . H11C H 0.7704 0.1795 0.6164 0.026 Uiso 1 1 calc R . . C12 C 0.5597(8) 0.1624(3) 0.5818(7) 0.0140(11) Uiso 1 1 d D . . C13 C 0.5009(8) 0.1323(3) 0.6743(7) 0.0101(10) Uiso 1 1 d D . . C14 C 0.3889(8) 0.0673(3) 0.6220(6) 0.0123(11) Uiso 1 1 d D . . C15 C 0.3164(9) 0.0120(3) 0.6868(7) 0.0173(12) Uiso 1 1 d D . . H15 H 0.3407 0.0117 0.7786 0.021 Uiso 1 1 calc R . . C16 C 0.2070(10) -0.0431(3) 0.6123(8) 0.0223(13) Uiso 1 1 d D . . H16 H 0.1561 -0.0791 0.6542 0.027 Uiso 1 1 calc R . . C17 C 0.1743(9) -0.0441(3) 0.4754(7) 0.0171(12) Uiso 1 1 d D . . H17 H 0.0951 -0.0758 0.4258 0.021 Uiso 1 1 calc R . . C18 C 0.2566(9) 0.0008(3) 0.4124(7) 0.0145(11) Uiso 1 1 d D . . H18 H 0.2423 -0.0068 0.3222 0.017 Uiso 1 1 calc R . . C19 C 0.3625(8) 0.0584(3) 0.4865(6) 0.0125(11) Uiso 1 1 d D . . C31 C 0.6078(9) -0.0739(3) 0.9242(8) 0.0195(12) Uiso 1 1 d D . . H31A H 0.5375 -0.0314 0.9327 0.029 Uiso 1 1 calc R . . H31B H 0.6400 -0.1093 1.0037 0.029 Uiso 1 1 calc R . . H31C H 0.5676 -0.1134 0.8506 0.029 Uiso 1 1 calc R . . C32 C 0.7288(8) -0.0241(3) 0.9022(7) 0.0151(11) Uiso 1 1 d D . . C33 C 0.7484(9) 0.0676(3) 0.9015(7) 0.0123(11) Uiso 1 1 d D . . C34 C 0.8758(8) 0.0913(3) 0.8737(7) 0.0131(11) Uiso 1 1 d D . . C35 C 0.9245(11) 0.1781(3) 0.8561(7) 0.0126(11) Uiso 1 1 d D . . H35 H 0.8746 0.2293 0.8679 0.015 Uiso 1 1 calc R . . C36 C 1.0462(10) 0.1866(3) 0.8214(7) 0.0140(12) Uiso 1 1 d D . . H36 H 1.0785 0.2443 0.8095 0.017 Uiso 1 1 calc R . . C37 C 1.1233(9) 0.1110(3) 0.8032(7) 0.0179(12) Uiso 1 1 d D . . H37 H 1.2050 0.1188 0.7779 0.021 Uiso 1 1 calc R . . C38 C 1.0787(10) 0.0243(3) 0.8228(7) 0.0154(12) Uiso 1 1 d D . . H38 H 1.1310 -0.0264 0.8138 0.018 Uiso 1 1 calc R . . C39 C 0.9534(9) 0.0154(3) 0.8564(7) 0.0140(12) Uiso 1 1 d D . . F1 F 0.4935(6) 0.32211(16) 0.7714(5) 0.0211(7) Uiso 1 1 d D . . F2 F 0.3357(6) 0.24334(16) 0.8280(4) 0.0208(7) Uiso 1 1 d D . . F3 F 0.6062(6) 0.35307(16) 1.0098(5) 0.0190(7) Uiso 1 1 d D . . F4 F 0.4650(7) 0.25899(19) 1.0646(6) 0.0237(10) Uiso 1 1 d D . . F5 F 0.7996(6) 0.23796(16) 1.0600(4) 0.0196(7) Uiso 1 1 d D . . F6 F 0.6699(6) 0.14973(16) 1.1392(4) 0.0195(7) Uiso 1 1 d D . . S1 S 0.4770(3) 0.11891(7) 0.4263(2) 0.020(2) Uani 1 1 d D . . S2 S 0.8672(3) -0.08281(7) 0.8734(2) 0.020(2) Uani 1 1 d 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 S1 0.027(3) 0.0129(6) 0.017(2) 0.0001(6) 0.001(3) 0.0004(8) S2 0.023(3) 0.0104(6) 0.024(2) 0.0014(6) 0.003(3) 0.0004(8) _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 C5 1.332(6) . ? C1 C13 1.466(9) . ? C1 C2 1.476(9) . ? C2 F1 1.343(7) . ? C2 F2 1.371(9) . ? C2 C3 1.558(7) . ? C3 F4 1.308(11) . ? C3 F3 1.343(6) . ? C3 C4 1.541(8) . ? C4 F5 1.353(8) . ? C4 F6 1.360(8) . ? C4 C5 1.491(8) . ? C5 C33 1.458(9) . ? C11 C12 1.489(10) . ? C12 C13 1.353(11) . ? C12 S1 1.730(5) . ? C13 C14 1.445(7) . ? C14 C19 1.386(9) . ? C14 C15 1.394(11) . ? C15 C16 1.395(7) . ? C16 C17 1.388(10) . ? C17 C18 1.366(12) . ? C18 C19 1.395(6) . ? C19 S1 1.707(9) . ? C31 C32 1.481(11) . ? C32 C33 1.365(6) . ? C32 S2 1.721(9) . ? C33 C34 1.420(11) . ? C34 C39 1.399(9) . ? C34 C35 1.399(8) . ? C35 C36 1.365(12) . ? C36 C37 1.396(9) . ? C37 C38 1.387(8) . ? C38 C39 1.393(12) . ? C39 S2 1.716(7) . ? 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 C5 C1 C13 126.7(7) . . ? C5 C1 C2 111.4(5) . . ? C13 C1 C2 121.4(4) . . ? F1 C2 F2 106.0(4) . . ? F1 C2 C1 112.5(8) . . ? F2 C2 C1 113.6(5) . . ? F1 C2 C3 110.5(4) . . ? F2 C2 C3 107.5(7) . . ? C1 C2 C3 106.7(4) . . ? F4 C3 F3 109.6(7) . . ? F4 C3 C2 111.7(6) . . ? F3 C3 C2 109.7(6) . . ? F4 C3 C4 111.8(6) . . ? F3 C3 C4 110.8(6) . . ? C2 C3 C4 103.2(6) . . ? F5 C4 F6 105.7(4) . . ? F5 C4 C5 111.0(7) . . ? F6 C4 C5 112.3(4) . . ? F5 C4 C3 110.5(4) . . ? F6 C4 C3 111.2(7) . . ? C5 C4 C3 106.2(4) . . ? C1 C5 C33 124.5(7) . . ? C1 C5 C4 112.0(6) . . ? C33 C5 C4 122.5(4) . . ? C13 C12 C11 127.5(5) . . ? C13 C12 S1 112.6(5) . . ? C11 C12 S1 119.6(7) . . ? C12 C13 C14 112.6(6) . . ? C12 C13 C1 122.9(6) . . ? C14 C13 C1 124.3(8) . . ? C19 C14 C15 119.1(5) . . ? C19 C14 C13 110.3(7) . . ? C15 C14 C13 130.3(6) . . ? C14 C15 C16 119.2(7) . . ? C17 C16 C15 119.9(9) . . ? C18 C17 C16 121.1(6) . . ? C17 C18 C19 118.5(7) . . ? C14 C19 C18 121.3(8) . . ? C14 C19 S1 113.2(4) . . ? C18 C19 S1 125.3(7) . . ? C33 C32 C31 127.9(7) . . ? C33 C32 S2 112.0(7) . . ? C31 C32 S2 120.1(4) . . ? C32 C33 C34 112.4(7) . . ? C32 C33 C5 127.1(8) . . ? C34 C33 C5 120.1(5) . . ? C39 C34 C35 119.3(9) . . ? C39 C34 C33 112.7(6) . . ? C35 C34 C33 127.9(7) . . ? C36 C35 C34 119.1(7) . . ? C35 C36 C37 121.7(7) . . ? C38 C37 C36 120.2(9) . . ? C39 C38 C37 118.1(7) . . ? C38 C39 C34 121.5(6) . . ? C38 C39 S2 127.9(5) . . ? C34 C39 S2 110.5(7) . . ? C19 S1 C12 91.0(4) . . ? C39 S2 C32 92.3(4) . . ? _diffrn_measured_fraction_theta_max 0.309 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.309 _refine_diff_density_max 0.350 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.049 ##END _database_code_depnum_ccdc_archive 'CCDC 961263' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_0.00GPaDimethylthiopheneDTE(NOTINCELL) _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety 'C17 H14 F6 S2' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' 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 20.5687(10) _cell_length_b 8.8331(2) _cell_length_c 11.4381(5) _cell_angle_alpha 90.00 _cell_angle_beta 122.177(6) _cell_angle_gamma 90.00 _cell_volume 1758.95(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 14951 _cell_measurement_theta_min 2.9082 _cell_measurement_theta_max 32.8908 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.359 _exptl_absorpt_correction_T_min 0.89224 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293 _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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3795 _diffrn_reflns_number 55042 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 32.97 _reflns_number_total 3177 _reflns_number_gt 2453 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.300 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.044 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0069(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3177 _refine_ls_number_parameters 154 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1293 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.960 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.32895(2) 0.96348(4) 0.06725(4) 0.05453(14) Uani 1 1 d D A . C1 C 0.46324(6) 0.59984(12) 0.19578(11) 0.0379(2) Uani 1 1 d D . . C2A C 0.4359(4) 0.4475(9) 0.1368(8) 0.0475(15) Uani 0.50 1 d PD A 1 C2B C 0.4358(5) 0.4333(9) 0.1630(8) 0.0508(16) Uani 0.50 1 d PD A 2 C3 C 0.5000 0.3379(2) 0.2500 0.0653(6) Uani 1 2 d SD . . C11 C 0.43775(9) 0.88206(18) 0.33880(14) 0.0558(3) Uani 1 1 d D A . H11A H 0.4522 0.7896 0.3909 0.084 Uiso 1 1 calc R . . H11B H 0.4028 0.9373 0.3541 0.084 Uiso 1 1 calc R . . H11C H 0.4828 0.9422 0.3679 0.084 Uiso 1 1 calc R . . C12 C 0.39964(7) 0.84627(14) 0.18820(12) 0.0414(2) Uani 1 1 d D . . C13 C 0.41001(6) 0.72538(13) 0.12461(11) 0.0375(2) Uani 1 1 d D A . C14 C 0.35939(7) 0.73014(16) -0.02306(12) 0.0447(3) Uani 1 1 d D . . H14 H 0.3591 0.6565 -0.0815 0.054 Uiso 1 1 calc R A . C15 C 0.31232(7) 0.85154(17) -0.06899(13) 0.0488(3) Uani 1 1 d D A . C16 C 0.25141(9) 0.8909(3) -0.21554(16) 0.0699(5) Uani 1 1 d . . . H16A H 0.2584 0.9936 -0.2344 0.105 Uiso 1 1 calc R A . H16B H 0.2016 0.8804 -0.2281 0.105 Uiso 1 1 calc R . . H16C H 0.2554 0.8240 -0.2776 0.105 Uiso 1 1 calc R . . F1A F 0.4368(2) 0.4221(4) 0.0206(4) 0.0778(9) Uani 0.50 1 d PD A 1 F2A F 0.36401(14) 0.4143(3) 0.1033(3) 0.0777(8) Uani 0.50 1 d PD A 1 F1B F 0.4021(2) 0.4036(4) 0.0281(3) 0.0832(11) Uani 0.50 1 d PD A 2 F2B F 0.38253(16) 0.4066(3) 0.1952(4) 0.0862(8) Uani 0.50 1 d PD A 2 F3A F 0.53503(16) 0.2904(4) 0.1723(3) 0.0893(8) Uani 0.50 1 d PD A -1 F3B F 0.49330(18) 0.2142(3) 0.2980(3) 0.0914(9) Uani 0.50 1 d PD 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 0.0506(2) 0.0525(2) 0.0574(2) 0.01275(14) 0.02667(17) 0.01647(14) C1 0.0385(5) 0.0345(5) 0.0343(5) -0.0023(4) 0.0150(4) -0.0017(4) C2A 0.0396(18) 0.0360(18) 0.050(3) 0.0018(16) 0.0122(17) 0.0026(14) C2B 0.055(2) 0.039(2) 0.047(3) -0.0081(19) 0.020(2) -0.0133(17) C3 0.0813(15) 0.0329(8) 0.0624(12) 0.000 0.0253(11) 0.000 C11 0.0630(8) 0.0564(8) 0.0439(6) -0.0056(6) 0.0258(6) 0.0085(6) C12 0.0399(5) 0.0414(6) 0.0396(5) 0.0031(4) 0.0188(4) 0.0038(4) C13 0.0321(5) 0.0383(5) 0.0335(5) 0.0006(4) 0.0117(4) -0.0005(4) C14 0.0378(5) 0.0511(7) 0.0336(5) 0.0003(5) 0.0111(4) -0.0028(5) C15 0.0359(5) 0.0595(8) 0.0415(6) 0.0120(5) 0.0141(5) 0.0009(5) C16 0.0472(7) 0.0923(13) 0.0484(8) 0.0250(8) 0.0107(6) 0.0084(8) F1A 0.109(3) 0.0556(14) 0.0524(12) -0.0185(10) 0.0318(18) 0.0014(17) F2A 0.0500(11) 0.0498(11) 0.1060(19) -0.0115(14) 0.0232(14) -0.0142(9) F1B 0.093(2) 0.0511(13) 0.0483(13) -0.0183(10) -0.0009(15) -0.0038(15) F2B 0.0745(18) 0.0598(13) 0.138(3) -0.0083(18) 0.066(2) -0.0193(13) F3A 0.0819(17) 0.0898(19) 0.0887(17) -0.0288(15) 0.0405(14) 0.0150(14) F3B 0.0948(19) 0.0429(10) 0.100(2) 0.0126(10) 0.0275(17) -0.0166(12) _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 C15 1.7192(16) . ? S1 C12 1.7197(12) . ? C1 C1 1.352(2) 2_655 ? C1 C13 1.4636(15) . ? C1 C2A 1.476(8) . ? C1 C2B 1.548(8) . ? C2A F1A 1.358(9) . ? C2A F2A 1.347(8) . ? C2A C3 1.592(6) . ? C2B F1B 1.338(9) . ? C2B F2B 1.350(10) . ? C2B C3 1.430(7) . ? C3 F3B 1.263(3) 2_655 ? C3 F3B 1.263(3) . ? C3 C2B 1.430(7) 2_655 ? C3 F3A 1.473(3) . ? C3 F3A 1.473(3) 2_655 ? C3 C2A 1.592(6) 2_655 ? C11 C12 1.4978(17) . ? C12 C13 1.3712(17) . ? C13 C14 1.4373(15) . ? C14 C15 1.3497(19) . ? C15 C16 1.5046(17) . ? 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 C15 S1 C12 93.31(6) . . ? C1 C1 C13 130.57(6) 2_655 . ? C1 C1 C2A 112.8(2) 2_655 . ? C13 C1 C2A 116.5(3) . . ? C1 C1 C2B 107.9(3) 2_655 . ? C13 C1 C2B 121.1(3) . . ? F1A C2A F2A 105.7(6) . . ? F1A C2A C1 113.4(6) . . ? F2A C2A C1 115.0(5) . . ? F1A C2A C3 104.9(5) . . ? F2A C2A C3 114.0(6) . . ? C1 C2A C3 103.5(5) . . ? F1B C2B F2B 106.4(6) . . ? F1B C2B C3 114.0(6) . . ? F2B C2B C3 106.8(5) . . ? F1B C2B C1 111.4(5) . . ? F2B C2B C1 110.1(6) . . ? C3 C2B C1 108.0(5) . . ? F3B C3 F3B 60.2(3) 2_655 . ? F3B C3 C2B 122.6(4) 2_655 2_655 ? F3B C3 C2B 118.8(4) . 2_655 ? F3B C3 C2B 118.8(4) 2_655 . ? F3B C3 C2B 122.6(4) . . ? C2B C3 C2B 107.8(7) 2_655 . ? F3B C3 F3A 102.6(3) . . ? C2B C3 F3A 91.2(4) 2_655 . ? C2B C3 F3A 108.4(4) . . ? F3B C3 F3A 102.6(3) 2_655 2_655 ? C2B C3 F3A 108.4(4) 2_655 2_655 ? C2B C3 F3A 91.2(4) . 2_655 ? F3A C3 F3A 146.9(3) . 2_655 ? F3B C3 C2A 130.1(3) 2_655 2_655 ? F3B C3 C2A 114.1(3) . 2_655 ? C2B C3 C2A 105.41(19) . 2_655 ? F3A C3 C2A 101.8(3) . 2_655 ? F3A C3 C2A 98.2(3) 2_655 2_655 ? F3B C3 C2A 114.1(3) 2_655 . ? F3B C3 C2A 130.1(3) . . ? C2B C3 C2A 105.41(19) 2_655 . ? F3A C3 C2A 98.2(3) . . ? F3A C3 C2A 101.8(3) 2_655 . ? C2A C3 C2A 105.1(6) 2_655 . ? C13 C12 C11 129.82(11) . . ? C13 C12 S1 110.23(9) . . ? C11 C12 S1 119.91(10) . . ? C12 C13 C14 112.37(10) . . ? C12 C13 C1 125.22(10) . . ? C14 C13 C1 122.34(11) . . ? C15 C14 C13 113.65(12) . . ? C14 C15 C16 128.06(15) . . ? C14 C15 S1 110.42(9) . . ? C16 C15 S1 121.50(13) . . ? 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 C1 C1 C2A F1A -100.4(4) 2_655 . . . ? C13 C1 C2A F1A 75.9(5) . . . . ? C2B C1 C2A F1A -169(3) . . . . ? C1 C1 C2A F2A 137.8(4) 2_655 . . . ? C13 C1 C2A F2A -45.9(7) . . . . ? C2B C1 C2A F2A 70(3) . . . . ? C1 C1 C2A C3 12.8(6) 2_655 . . . ? C13 C1 C2A C3 -171.0(2) . . . . ? C2B C1 C2A C3 -55(2) . . . . ? C1 C1 C2B F1B -131.4(5) 2_655 . . . ? C13 C1 C2B F1B 55.1(7) . . . . ? C2A C1 C2B F1B -16(2) . . . . ? C1 C1 C2B F2B 110.8(5) 2_655 . . . ? C13 C1 C2B F2B -62.7(6) . . . . ? C2A C1 C2B F2B -133(3) . . . . ? C1 C1 C2B C3 -5.5(6) 2_655 . . . ? C13 C1 C2B C3 -179.0(3) . . . . ? C2A C1 C2B C3 110(3) . . . . ? F1B C2B C3 F3B -19.0(8) . . . 2_655 ? F2B C2B C3 F3B 98.3(6) . . . 2_655 ? C1 C2B C3 F3B -143.3(4) . . . 2_655 ? F1B C2B C3 F3B -90.2(7) . . . . ? F2B C2B C3 F3B 27.1(7) . . . . ? C1 C2B C3 F3B 145.5(4) . . . . ? F1B C2B C3 C2B 126.2(8) . . . 2_655 ? F2B C2B C3 C2B -116.5(7) . . . 2_655 ? C1 C2B C3 C2B 1.9(2) . . . 2_655 ? F1B C2B C3 F3A 28.8(7) . . . . ? F2B C2B C3 F3A 146.0(4) . . . . ? C1 C2B C3 F3A -95.6(5) . . . . ? F1B C2B C3 F3A -124.0(6) . . . 2_655 ? F2B C2B C3 F3A -6.8(5) . . . 2_655 ? C1 C2B C3 F3A 111.6(5) . . . 2_655 ? F1B C2B C3 C2A 137.1(5) . . . 2_655 ? F2B C2B C3 C2A -105.6(5) . . . 2_655 ? C1 C2B C3 C2A 12.8(9) . . . 2_655 ? F1B C2B C3 C2A 47(3) . . . . ? F2B C2B C3 C2A 165(4) . . . . ? C1 C2B C3 C2A -77(3) . . . . ? F1A C2A C3 F3B -33.6(6) . . . 2_655 ? F2A C2A C3 F3B 81.7(6) . . . 2_655 ? C1 C2A C3 F3B -152.7(4) . . . 2_655 ? F1A C2A C3 F3B -103.9(5) . . . . ? F2A C2A C3 F3B 11.3(8) . . . . ? C1 C2A C3 F3B 136.9(4) . . . . ? F1A C2A C3 C2B 103.7(5) . . . 2_655 ? F2A C2A C3 C2B -141.0(5) . . . 2_655 ? C1 C2A C3 C2B -15.4(8) . . . 2_655 ? F1A C2A C3 C2B -152(4) . . . . ? F2A C2A C3 C2B -37(3) . . . . ? C1 C2A C3 C2B 89(3) . . . . ? F1A C2A C3 F3A 10.2(5) . . . . ? F2A C2A C3 F3A 125.4(6) . . . . ? C1 C2A C3 F3A -108.9(4) . . . . ? F1A C2A C3 F3A -143.2(5) . . . 2_655 ? F2A C2A C3 F3A -28.0(6) . . . 2_655 ? C1 C2A C3 F3A 97.6(4) . . . 2_655 ? F1A C2A C3 C2A 114.8(6) . . . 2_655 ? F2A C2A C3 C2A -129.9(7) . . . 2_655 ? C1 C2A C3 C2A -4.31(19) . . . 2_655 ? C15 S1 C12 C13 0.32(10) . . . . ? C15 S1 C12 C11 -177.69(12) . . . . ? C11 C12 C13 C14 177.49(14) . . . . ? S1 C12 C13 C14 -0.26(14) . . . . ? C11 C12 C13 C1 0.4(2) . . . . ? S1 C12 C13 C1 -177.39(9) . . . . ? C1 C1 C13 C12 -43.8(2) 2_655 . . . ? C2A C1 C13 C12 140.7(4) . . . . ? C2B C1 C13 C12 128.0(4) . . . . ? C1 C1 C13 C14 139.32(17) 2_655 . . . ? C2A C1 C13 C14 -36.1(4) . . . . ? C2B C1 C13 C14 -48.8(4) . . . . ? C12 C13 C14 C15 0.04(16) . . . . ? C1 C13 C14 C15 177.27(11) . . . . ? C13 C14 C15 C16 -178.63(14) . . . . ? C13 C14 C15 S1 0.19(15) . . . . ? C12 S1 C15 C14 -0.29(11) . . . . ? C12 S1 C15 C16 178.62(13) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961264' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_0.00GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety 'C17 H14 F6 S2' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 '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' _symmetry_space_group_name_Hall '-C 2yc' 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 19.69(6) _cell_length_b 8.8311(18) _cell_length_c 11.460(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.72(5) _cell_angle_gamma 90.00 _cell_volume 1779(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 502 _cell_measurement_theta_min 2.8512 _cell_measurement_theta_max 28.9161 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 2544 _diffrn_reflns_av_R_equivalents 0.0720 _diffrn_reflns_av_sigmaI/netI 0.0769 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 28.58 _reflns_number_total 506 _reflns_number_gt 336 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.203 _diffrn_reflns_theta_full 28.58 _diffrn_measured_fraction_theta_full 0.203 _refine_diff_density_max 0.348 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.044 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 506 _refine_ls_number_parameters 75 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1296 _refine_ls_R_factor_gt 0.0895 _refine_ls_wR_factor_ref 0.2454 _refine_ls_wR_factor_gt 0.2160 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.3301(5) 0.9635(3) 0.0687(5) 0.065(8) Uani 1 1 d D A . C1 C 0.4649(6) 0.5991(7) 0.1971(7) 0.041(2) Uiso 1 1 d D . . C2A C 0.4389(12) 0.4456(14) 0.1370(14) 0.055(8) Uiso 0.50 1 d PD A 1 C2B C 0.4361(11) 0.4373(17) 0.1614(19) 0.069(10) Uiso 0.50 1 d PD A 2 C3 C 0.5000 0.3437(14) 0.2500 0.059(4) Uiso 1 2 d SD . . C11 C 0.4325(16) 0.8802(10) 0.3338(16) 0.060(3) Uiso 1 1 d D A . H11A H 0.4338 0.7888 0.3800 0.090 Uiso 1 1 calc R . . H11B H 0.4021 0.9545 0.3498 0.090 Uiso 1 1 calc R . . H11C H 0.4833 0.9181 0.3635 0.090 Uiso 1 1 calc R . . C12 C 0.3977(12) 0.8467(9) 0.1858(13) 0.050(2) Uiso 1 1 d D . . C13 C 0.4115(12) 0.7236(9) 0.1262(12) 0.049(2) Uiso 1 1 d D A . C14 C 0.3608(16) 0.7322(10) -0.0216(16) 0.052(2) Uiso 1 1 d D . . H14 H 0.3600 0.6560 -0.0783 0.063 Uiso 1 1 calc R A . C15 C 0.3197(15) 0.8510(11) -0.0618(15) 0.062(3) Uiso 1 1 d D A . C16 C 0.251(2) 0.8926(15) -0.215(2) 0.093(4) Uiso 1 1 d . . . H16A H 0.2544 0.9976 -0.2333 0.140 Uiso 1 1 calc R A . H16B H 0.2018 0.8728 -0.2197 0.140 Uiso 1 1 calc R . . H16C H 0.2580 0.8309 -0.2775 0.140 Uiso 1 1 calc R . . F1A F 0.440(2) 0.4226(12) 0.022(2) 0.055(3) Uiso 0.50 1 d PD A 1 F2A F 0.3652(17) 0.4144(15) 0.1027(19) 0.081(5) Uiso 0.50 1 d PD A 1 F1B F 0.406(2) 0.4011(13) 0.036(2) 0.070(4) Uiso 0.50 1 d PD A 2 F2B F 0.377(2) 0.4065(14) 0.188(2) 0.089(4) Uiso 0.50 1 d PD A 2 F3A F 0.5369(19) 0.2890(16) 0.172(2) 0.094(5) Uiso 0.50 1 d PD A -1 F3B F 0.491(2) 0.2158(14) 0.295(2) 0.086(4) Uiso 0.50 1 d PD 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 0.06(2) 0.0630(18) 0.079(9) 0.016(2) 0.038(14) 0.019(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 S1 C15 1.728(9) . ? S1 C12 1.740(16) . ? C1 C1 1.37(2) 2_655 ? C1 C13 1.485(15) . ? C1 C2A 1.502(13) . ? C1 C2B 1.523(17) . ? C2A F1A 1.344(17) . ? C2A F2A 1.35(2) . ? C2A C3 1.591(12) . ? C2B F1B 1.327(18) . ? C2B F2B 1.36(2) . ? C2B C3 1.465(12) . ? C3 F3B 1.283(11) 2_655 ? C3 F3B 1.283(11) . ? C3 F3A 1.461(12) 2_655 ? C3 F3A 1.461(12) . ? C3 C2B 1.465(12) 2_655 ? C3 C2A 1.591(12) 2_655 ? C11 C12 1.545(19) . ? C12 C13 1.375(11) . ? C13 C14 1.53(2) . ? C14 C15 1.28(2) . ? C15 C16 1.70(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 C15 S1 C12 94.6(7) . . ? C1 C1 C13 132.0(7) 2_655 . ? C1 C1 C2A 113.9(7) 2_655 . ? C13 C1 C2A 114.0(10) . . ? C1 C1 C2B 110.1(6) 2_655 . ? C13 C1 C2B 117.5(10) . . ? F1A C2A F2A 100.1(19) . . ? F1A C2A C1 115.7(15) . . ? F2A C2A C1 114.6(14) . . ? F1A C2A C3 111.8(17) . . ? F2A C2A C3 116.2(16) . . ? C1 C2A C3 99.3(11) . . ? F1B C2B F2B 101.2(16) . . ? F1B C2B C3 115.9(19) . . ? F2B C2B C3 107(2) . . ? F1B C2B C1 116.5(16) . . ? F2B C2B C1 112.3(16) . . ? C3 C2B C1 104.1(12) . . ? F3B C3 F3B 56.7(13) 2_655 . ? F3B C3 F3A 98.3(13) 2_655 2_655 ? F3B C3 F3A 98.3(13) . . ? F3A C3 F3A 141.4(15) 2_655 . ? F3B C3 C2B 123.0(18) 2_655 2_655 ? F3B C3 C2B 116.6(16) . 2_655 ? F3A C3 C2B 105.7(15) 2_655 2_655 ? F3A C3 C2B 95.8(16) . 2_655 ? F3B C3 C2B 116.6(16) 2_655 . ? F3B C3 C2B 123.0(18) . . ? F3A C3 C2B 95.8(16) 2_655 . ? F3A C3 C2B 105.7(15) . . ? C2B C3 C2B 111.3(16) 2_655 . ? F3B C3 C2A 129.4(18) 2_655 2_655 ? F3B C3 C2A 111.2(14) . 2_655 ? F3A C3 C2A 95.3(13) 2_655 2_655 ? F3A C3 C2A 106.4(15) . 2_655 ? C2B C3 C2A 110.1(13) . 2_655 ? F3B C3 C2A 111.2(14) 2_655 . ? F3B C3 C2A 129.4(18) . . ? F3A C3 C2A 106.4(15) 2_655 . ? F3A C3 C2A 95.3(13) . . ? C2B C3 C2A 110.1(12) 2_655 . ? C2A C3 C2A 111.1(14) 2_655 . ? C13 C12 C11 127.4(13) . . ? C13 C12 S1 109.8(10) . . ? C11 C12 S1 122.8(8) . . ? C12 C13 C1 124.3(11) . . ? C12 C13 C14 109.5(12) . . ? C1 C13 C14 126.2(7) . . ? C15 C14 C13 115.5(9) . . ? C14 C15 C16 128.9(11) . . ? C14 C15 S1 110.5(13) . . ? C16 C15 S1 119.8(11) . . ? _database_code_depnum_ccdc_archive 'CCDC 961265' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_0.71GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety 'C17 H14 F6 S2' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 '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' _symmetry_space_group_name_Hall '-C 2yc' 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 19.672(29) _cell_length_b 8.6717(8) _cell_length_c 11.0787(9) _cell_angle_alpha 90.00 _cell_angle_beta 120.594(13) _cell_angle_gamma 90.00 _cell_volume 1626.8(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 708 _cell_measurement_theta_min 1.8056 _cell_measurement_theta_max 29.1712 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 2588 _diffrn_reflns_av_R_equivalents 0.0903 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.34 _diffrn_reflns_theta_max 25.83 _reflns_number_total 434 _reflns_number_gt 336 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.252 _diffrn_reflns_theta_full 25.83 _diffrn_measured_fraction_theta_full 0.252 _refine_diff_density_max 0.360 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.050 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 434 _refine_ls_number_parameters 74 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0766 _refine_ls_wR_factor_ref 0.1996 _refine_ls_wR_factor_gt 0.1825 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.3258(4) 0.9691(2) 0.0595(5) 0.045(6) Uani 1 1 d D A . C1 C 0.4628(6) 0.5982(7) 0.1946(7) 0.029(2) Uiso 1 1 d D . . C2A C 0.4360(12) 0.4410(14) 0.1300(14) 0.042(7) Uiso 0.50 1 d PD A 1 C2B C 0.4327(10) 0.4314(16) 0.1567(17) 0.040(7) Uiso 0.50 1 d PD A 2 C3 C 0.5000 0.3345(13) 0.2500 0.040(3) Uiso 1 2 d SD . . C11 C 0.4355(16) 0.8890(9) 0.3371(16) 0.042(2) Uiso 1 1 d D A . H11A H 0.4386 0.7970 0.3879 0.063 Uiso 1 1 calc R . . H11B H 0.4037 0.9642 0.3496 0.063 Uiso 1 1 calc R . . H11C H 0.4875 0.9297 0.3717 0.063 Uiso 1 1 calc R . . C12 C 0.3988(11) 0.8520(8) 0.1848(12) 0.0321(19) Uiso 1 1 d D . . C13 C 0.4083(12) 0.7245(8) 0.1203(12) 0.035(2) Uiso 1 1 d D A . C14 C 0.3592(15) 0.7284(9) -0.0279(16) 0.036(2) Uiso 1 1 d D . . H14 H 0.3603 0.6528 -0.0864 0.043 Uiso 1 1 calc R A . C15 C 0.3113(13) 0.8506(9) -0.0756(14) 0.039(2) Uiso 1 1 d D A . C16 C 0.2462(19) 0.8867(12) -0.2267(19) 0.063(3) Uiso 1 1 d . . . H16A H 0.2571 0.9840 -0.2548 0.094 Uiso 1 1 calc R A . H16B H 0.1961 0.8917 -0.2317 0.094 Uiso 1 1 calc R . . H16C H 0.2448 0.8071 -0.2882 0.094 Uiso 1 1 calc R . . F1A F 0.4421(17) 0.4205(9) 0.0163(18) 0.031(2) Uiso 0.50 1 d PD A 1 F2A F 0.3619(17) 0.4076(13) 0.0955(18) 0.058(4) Uiso 0.50 1 d PD A 1 F1B F 0.4063(19) 0.3961(12) 0.025(2) 0.052(4) Uiso 0.50 1 d PD A 2 F2B F 0.3720(18) 0.4011(12) 0.179(2) 0.063(3) Uiso 0.50 1 d PD A 2 F3A F 0.5381(16) 0.2753(13) 0.1740(19) 0.062(3) Uiso 0.50 1 d PD A -1 F3B F 0.4890(19) 0.2072(12) 0.296(2) 0.063(3) Uiso 0.50 1 d PD 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 0.046(19) 0.0420(14) 0.044(7) 0.0125(16) 0.021(11) 0.014(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 S1 C15 1.715(8) . ? S1 C12 1.729(15) . ? C1 C1 1.348(19) 2_655 ? C1 C13 1.459(14) . ? C1 C2A 1.505(13) . ? C1 C2B 1.538(16) . ? C2A F2A 1.336(19) . ? C2A F1A 1.337(17) . ? C2A C3 1.581(11) . ? C2B F1B 1.308(17) . ? C2B F2B 1.360(19) . ? C2B C3 1.461(11) . ? C3 F3B 1.279(10) 2_655 ? C3 F3B 1.279(10) . ? C3 C2B 1.461(12) 2_655 ? C3 F3A 1.475(12) . ? C3 F3A 1.475(12) 2_655 ? C3 C2A 1.581(11) 2_655 ? C11 C12 1.494(17) . ? C12 C13 1.379(10) . ? C13 C14 1.42(2) . ? C14 C15 1.33(2) . ? C15 C16 1.54(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 C15 S1 C12 92.9(6) . . ? C1 C1 C13 131.2(7) 2_655 . ? C1 C1 C2A 112.9(7) 2_655 . ? C13 C1 C2A 115.7(9) . . ? C1 C1 C2B 109.7(6) 2_655 . ? C13 C1 C2B 118.8(10) . . ? C2A C1 C2B 12.9(10) . . ? F2A C2A F1A 108.1(17) . . ? F2A C2A C1 113.5(13) . . ? F1A C2A C1 113.0(13) . . ? F2A C2A C3 113.6(14) . . ? F1A C2A C3 107.4(14) . . ? C1 C2A C3 101.1(11) . . ? F1B C2B F2B 105.4(16) . . ? F1B C2B C3 110.9(17) . . ? F2B C2B C3 109.0(16) . . ? F1B C2B C1 113.8(14) . . ? F2B C2B C1 112.6(13) . . ? C3 C2B C1 105.2(12) . . ? F3B C3 F3B 60.7(13) 2_655 . ? F3B C3 C2B 120.1(16) 2_655 2_655 ? F3B C3 C2B 119.3(14) . 2_655 ? F3B C3 C2B 119.3(14) 2_655 . ? F3B C3 C2B 120.1(16) . . ? C2B C3 C2B 109.8(14) 2_655 . ? F3B C3 F3A 99.5(12) . . ? C2B C3 F3A 93.6(13) 2_655 . ? C2B C3 F3A 109.7(12) . . ? F3B C3 F3A 99.5(12) 2_655 2_655 ? C2B C3 F3A 109.7(12) 2_655 2_655 ? C2B C3 F3A 93.6(13) . 2_655 ? F3A C3 F3A 139.2(13) . 2_655 ? F3B C3 C2A 127.9(16) 2_655 2_655 ? F3B C3 C2A 113.1(12) . 2_655 ? C2B C3 C2A 107.9(11) . 2_655 ? F3A C3 C2A 105.4(13) . 2_655 ? F3A C3 C2A 98.2(11) 2_655 2_655 ? F3B C3 C2A 113.1(12) 2_655 . ? F3B C3 C2A 127.9(16) . . ? C2B C3 C2A 107.9(11) 2_655 . ? F3A C3 C2A 98.2(11) . . ? F3A C3 C2A 105.4(13) 2_655 . ? C2A C3 C2A 108.6(13) 2_655 . ? C13 C12 C11 130.0(12) . . ? C13 C12 S1 109.3(10) . . ? C11 C12 S1 120.4(8) . . ? C12 C13 C14 112.8(12) . . ? C12 C13 C1 124.4(11) . . ? C14 C13 C1 122.8(7) . . ? C15 C14 C13 113.9(7) . . ? C14 C15 C16 128.5(9) . . ? C14 C15 S1 111.1(11) . . ? C16 C15 S1 120.3(10) . . ? 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 C1 C1 C2A F2A 137.7(13) 2_655 . . . ? C13 C1 C2A F2A -48.0(16) . . . . ? C2B C1 C2A F2A 59(4) . . . . ? C1 C1 C2A F1A -98.8(18) 2_655 . . . ? C13 C1 C2A F1A 76(2) . . . . ? C2B C1 C2A F1A -177(5) . . . . ? C1 C1 C2A C3 15.7(16) 2_655 . . . ? C13 C1 C2A C3 -170.0(9) . . . . ? C2B C1 C2A C3 -63(3) . . . . ? C1 C1 C2B F1B -126.3(19) 2_655 . . . ? C13 C1 C2B F1B 59(2) . . . . ? C2A C1 C2B F1B -20(3) . . . . ? C1 C1 C2B F2B 113.9(16) 2_655 . . . ? C13 C1 C2B F2B -60.4(18) . . . . ? C2A C1 C2B F2B -140(4) . . . . ? C1 C1 C2B C3 -4.7(16) 2_655 . . . ? C13 C1 C2B C3 -179.0(9) . . . . ? C2A C1 C2B C3 102(4) . . . . ? F1B C2B C3 F3B -20(2) . . . 2_655 ? F2B C2B C3 F3B 96.0(17) . . . 2_655 ? C1 C2B C3 F3B -143.0(14) . . . 2_655 ? F1B C2B C3 F3B -91(2) . . . . ? F2B C2B C3 F3B 24.8(17) . . . . ? C1 C2B C3 F3B 145.8(10) . . . . ? F1B C2B C3 C2B 125(2) . . . 2_655 ? F2B C2B C3 C2B -119.4(16) . . . 2_655 ? C1 C2B C3 C2B 1.6(5) . . . 2_655 ? F1B C2B C3 F3A 23(2) . . . . ? F2B C2B C3 F3A 139.0(14) . . . . ? C1 C2B C3 F3A -100.0(14) . . . . ? F1B C2B C3 F3A -122.5(18) . . . 2_655 ? F2B C2B C3 F3A -6.9(14) . . . 2_655 ? C1 C2B C3 F3A 114.1(13) . . . 2_655 ? F1B C2B C3 C2A 137.7(16) . . . 2_655 ? F2B C2B C3 C2A -106.7(12) . . . 2_655 ? C1 C2B C3 C2A 14.3(15) . . . 2_655 ? F1B C2B C3 C2A 42(4) . . . . ? F2B C2B C3 C2A 158(5) . . . . ? C1 C2B C3 C2A -81(4) . . . . ? F2A C2A C3 F3B 84.8(17) . . . 2_655 ? F1A C2A C3 F3B -35(2) . . . 2_655 ? C1 C2A C3 F3B -153.3(14) . . . 2_655 ? F2A C2A C3 F3B 14.8(16) . . . . ? F1A C2A C3 F3B -104.7(16) . . . . ? C1 C2A C3 F3B 136.7(11) . . . . ? F2A C2A C3 C2B -139.9(14) . . . 2_655 ? F1A C2A C3 C2B 100.6(15) . . . 2_655 ? C1 C2A C3 C2B -18.0(15) . . . 2_655 ? F2A C2A C3 C2B -39(4) . . . . ? F1A C2A C3 C2B -158(5) . . . . ? C1 C2A C3 C2B 83(4) . . . . ? F2A C2A C3 F3A 123.6(13) . . . . ? F1A C2A C3 F3A 4.1(17) . . . . ? C1 C2A C3 F3A -114.5(13) . . . . ? F2A C2A C3 F3A -22.8(14) . . . 2_655 ? F1A C2A C3 F3A -142.3(14) . . . 2_655 ? C1 C2A C3 F3A 99.2(13) . . . 2_655 ? F2A C2A C3 C2A -127.1(14) . . . 2_655 ? F1A C2A C3 C2A 113.4(17) . . . 2_655 ? C1 C2A C3 C2A -5.2(6) . . . 2_655 ? C15 S1 C12 C13 -1.6(11) . . . . ? C15 S1 C12 C11 -176.2(12) . . . . ? C11 C12 C13 C14 176.5(15) . . . . ? S1 C12 C13 C14 2.6(17) . . . . ? C11 C12 C13 C1 -4(3) . . . . ? S1 C12 C13 C1 -177.5(11) . . . . ? C1 C1 C13 C12 -40(2) 2_655 . . . ? C2A C1 C13 C12 146.5(16) . . . . ? C2B C1 C13 C12 132.4(16) . . . . ? C1 C1 C13 C14 139.4(16) 2_655 . . . ? C2A C1 C13 C14 -33.6(19) . . . . ? C2B C1 C13 C14 -47.7(18) . . . . ? C12 C13 C14 C15 -3(2) . . . . ? C1 C13 C14 C15 177.5(13) . . . . ? C13 C14 C15 C16 -174.9(15) . . . . ? C13 C14 C15 S1 1.3(19) . . . . ? C12 S1 C15 C14 0.2(13) . . . . ? C12 S1 C15 C16 176.7(13) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961266' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1.02GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety 'C17 H14 F6 S2' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 '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' _symmetry_space_group_name_Hall '-C 2yc' 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 19.3247(61) _cell_length_b 8.6243(6) _cell_length_c 10.9544(7) _cell_angle_alpha 90.00 _cell_angle_beta 120.113(14) _cell_angle_gamma 90.00 _cell_volume 1579.3(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 700 _cell_measurement_theta_min 4.3389 _cell_measurement_theta_max 25.2722 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.313 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 2656 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.44 _diffrn_reflns_theta_max 25.93 _reflns_number_total 444 _reflns_number_gt 364 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.275 _diffrn_reflns_theta_full 25.93 _diffrn_measured_fraction_theta_full 0.275 _refine_diff_density_max 0.436 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.055 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 444 _refine_ls_number_parameters 74 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.1906 _refine_ls_wR_factor_gt 0.1772 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.3249(4) 0.9711(2) 0.0573(4) 0.044(5) Uani 1 1 d D A . C1 C 0.4625(6) 0.5970(6) 0.1938(6) 0.0250(19) Uiso 1 1 d D . . C2A C 0.4362(12) 0.4393(13) 0.1288(14) 0.036(6) Uiso 0.50 1 d PD A 1 C2B C 0.4335(10) 0.4302(15) 0.1551(15) 0.030(5) Uiso 0.50 1 d PD A 2 C3 C 0.5000 0.3314(11) 0.2500 0.035(3) Uiso 1 2 d SD . . C11 C 0.4309(15) 0.8929(9) 0.3332(14) 0.037(2) Uiso 1 1 d D A . H11A H 0.4276 0.8045 0.3833 0.056 Uiso 1 1 calc R . . H11B H 0.4015 0.9775 0.3420 0.056 Uiso 1 1 calc R . . H11C H 0.4859 0.9225 0.3721 0.056 Uiso 1 1 calc R . . C12 C 0.3967(11) 0.8531(8) 0.1825(11) 0.0312(18) Uiso 1 1 d D . . C13 C 0.4073(12) 0.7246(8) 0.1189(11) 0.0300(19) Uiso 1 1 d D A . C14 C 0.3553(14) 0.7273(8) -0.0324(14) 0.0316(19) Uiso 1 1 d D . . H14 H 0.3547 0.6489 -0.0913 0.038 Uiso 1 1 calc R A . C15 C 0.3088(14) 0.8503(9) -0.0798(13) 0.036(2) Uiso 1 1 d D A . C16 C 0.2441(17) 0.8846(11) -0.2311(16) 0.053(3) Uiso 1 1 d . . . H16A H 0.2565 0.9798 -0.2616 0.079 Uiso 1 1 calc R A . H16B H 0.1934 0.8943 -0.2357 0.079 Uiso 1 1 calc R . . H16C H 0.2418 0.8015 -0.2914 0.079 Uiso 1 1 calc R . . F1A F 0.4435(16) 0.4197(9) 0.0151(15) 0.027(2) Uiso 0.50 1 d PD A 1 F2A F 0.3615(16) 0.4047(13) 0.0964(17) 0.053(3) Uiso 0.50 1 d PD A 1 F1B F 0.4075(18) 0.3949(11) 0.0226(18) 0.044(3) Uiso 0.50 1 d PD A 2 F2B F 0.3722(17) 0.4006(12) 0.177(2) 0.064(3) Uiso 0.50 1 d PD A 2 F3A F 0.5406(14) 0.2719(13) 0.1760(17) 0.056(3) Uiso 0.50 1 d PD A -1 F3B F 0.4876(17) 0.2055(11) 0.2974(17) 0.055(3) Uiso 0.50 1 d PD 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 0.056(16) 0.0368(13) 0.044(4) 0.0096(13) 0.028(8) 0.009(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 C12 1.713(14) . ? S1 C15 1.723(8) . ? C1 C1 1.352(19) 2_655 ? C1 C13 1.463(14) . ? C1 C2A 1.500(12) . ? C1 C2B 1.524(15) . ? C2A F2A 1.337(19) . ? C2A F1A 1.332(16) . ? C2A C3 1.584(12) . ? C2B F1B 1.312(16) . ? C2B F2B 1.346(19) . ? C2B C3 1.456(12) . ? C3 F3B 1.277(10) 2_655 ? C3 F3B 1.277(10) . ? C3 C2B 1.456(12) 2_655 ? C3 F3A 1.475(12) 2_655 ? C3 F3A 1.475(12) . ? C3 C2A 1.584(12) 2_655 ? C11 C12 1.478(14) . ? C12 C13 1.379(10) . ? C13 C14 1.44(2) . ? C14 C15 1.32(2) . ? C15 C16 1.52(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 C12 S1 C15 93.3(6) . . ? C1 C1 C13 131.1(6) 2_655 . ? C1 C1 C2A 112.7(7) 2_655 . ? C13 C1 C2A 115.9(9) . . ? C1 C1 C2B 109.3(6) 2_655 . ? C13 C1 C2B 119.4(10) . . ? F2A C2A F1A 109.3(16) . . ? F2A C2A C1 113.0(13) . . ? F1A C2A C1 113.0(13) . . ? F2A C2A C3 112.0(14) . . ? F1A C2A C3 107.8(13) . . ? C1 C2A C3 101.5(10) . . ? F1B C2B F2B 105.8(16) . . ? F1B C2B C3 111.4(14) . . ? F2B C2B C3 107.6(15) . . ? F1B C2B C1 114.2(13) . . ? F2B C2B C1 111.3(12) . . ? C3 C2B C1 106.5(12) . . ? F3B C3 F3B 63.5(13) 2_655 . ? F3B C3 C2B 120.7(15) 2_655 2_655 ? F3B C3 C2B 119.1(12) . 2_655 ? F3B C3 C2B 119.1(12) 2_655 . ? F3B C3 C2B 120.7(15) . . ? C2B C3 C2B 108.3(14) 2_655 . ? F3B C3 F3A 100.8(12) 2_655 2_655 ? C2B C3 F3A 109.5(10) 2_655 2_655 ? C2B C3 F3A 94.2(12) . 2_655 ? F3B C3 F3A 100.8(12) . . ? C2B C3 F3A 94.2(12) 2_655 . ? C2B C3 F3A 109.5(10) . . ? F3A C3 F3A 139.3(12) 2_655 . ? F3B C3 C2A 128.0(14) 2_655 2_655 ? F3B C3 C2A 112.6(10) . 2_655 ? C2B C3 C2A 106.9(11) . 2_655 ? F3A C3 C2A 98.5(10) 2_655 2_655 ? F3A C3 C2A 105.1(12) . 2_655 ? F3B C3 C2A 112.6(10) 2_655 . ? F3B C3 C2A 128.0(15) . . ? C2B C3 C2A 106.9(11) 2_655 . ? F3A C3 C2A 105.1(12) 2_655 . ? F3A C3 C2A 98.5(10) . . ? C2A C3 C2A 108.0(13) 2_655 . ? C13 C12 C11 130.9(11) . . ? C13 C12 S1 109.8(8) . . ? C11 C12 S1 119.0(8) . . ? C12 C13 C14 111.9(11) . . ? C12 C13 C1 124.9(10) . . ? C14 C13 C1 123.2(7) . . ? C15 C14 C13 114.2(7) . . ? C14 C15 C16 127.7(8) . . ? C14 C15 S1 110.8(11) . . ? C16 C15 S1 121.4(10) . . ? 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 C1 C1 C2A F2A 136.2(12) 2_655 . . . ? C13 C1 C2A F2A -49.5(16) . . . . ? C2B C1 C2A F2A 60(4) . . . . ? C1 C1 C2A F1A -99.0(16) 2_655 . . . ? C13 C1 C2A F1A 75.2(19) . . . . ? C2B C1 C2A F1A -176(5) . . . . ? C1 C1 C2A C3 16.2(15) 2_655 . . . ? C13 C1 C2A C3 -169.6(9) . . . . ? C2B C1 C2A C3 -60(3) . . . . ? C1 C1 C2B F1B -126.5(17) 2_655 . . . ? C13 C1 C2B F1B 59(2) . . . . ? C2A C1 C2B F1B -18(4) . . . . ? C1 C1 C2B F2B 113.8(14) 2_655 . . . ? C13 C1 C2B F2B -61.0(17) . . . . ? C2A C1 C2B F2B -138(4) . . . . ? C1 C1 C2B C3 -3.1(15) 2_655 . . . ? C13 C1 C2B C3 -178.0(8) . . . . ? C2A C1 C2B C3 105(4) . . . . ? F1B C2B C3 F3B -17(2) . . . 2_655 ? F2B C2B C3 F3B 98.7(16) . . . 2_655 ? C1 C2B C3 F3B -141.9(13) . . . 2_655 ? F1B C2B C3 F3B -91.5(18) . . . . ? F2B C2B C3 F3B 24.0(15) . . . . ? C1 C2B C3 F3B 143.4(10) . . . . ? F1B C2B C3 C2B 126.2(19) . . . 2_655 ? F2B C2B C3 C2B -118.3(14) . . . 2_655 ? C1 C2B C3 C2B 1.1(5) . . . 2_655 ? F1B C2B C3 F3A -121.7(16) . . . 2_655 ? F2B C2B C3 F3A -6.2(12) . . . 2_655 ? C1 C2B C3 F3A 113.2(12) . . . 2_655 ? F1B C2B C3 F3A 25(2) . . . . ? F2B C2B C3 F3A 140.2(13) . . . . ? C1 C2B C3 F3A -100.4(13) . . . . ? F1B C2B C3 C2A 138.1(16) . . . 2_655 ? F2B C2B C3 C2A -106.4(12) . . . 2_655 ? C1 C2B C3 C2A 13.0(14) . . . 2_655 ? F1B C2B C3 C2A 41(4) . . . . ? F2B C2B C3 C2A 157(5) . . . . ? C1 C2B C3 C2A -84(4) . . . . ? F2A C2A C3 F3B 87.1(16) . . . 2_655 ? F1A C2A C3 F3B -33(2) . . . 2_655 ? C1 C2A C3 F3B -152.1(14) . . . 2_655 ? F2A C2A C3 F3B 13.8(16) . . . . ? F1A C2A C3 F3B -106.4(16) . . . . ? C1 C2A C3 F3B 134.6(11) . . . . ? F2A C2A C3 C2B -138.1(13) . . . 2_655 ? F1A C2A C3 C2B 101.6(15) . . . 2_655 ? C1 C2A C3 C2B -17.3(14) . . . 2_655 ? F2A C2A C3 C2B -40(4) . . . . ? F1A C2A C3 C2B -160(5) . . . . ? C1 C2A C3 C2B 81(4) . . . . ? F2A C2A C3 F3A -21.8(13) . . . 2_655 ? F1A C2A C3 F3A -142.0(14) . . . 2_655 ? C1 C2A C3 F3A 99.0(13) . . . 2_655 ? F2A C2A C3 F3A 124.8(12) . . . . ? F1A C2A C3 F3A 4.5(16) . . . . ? C1 C2A C3 F3A -114.4(13) . . . . ? F2A C2A C3 C2A -126.2(13) . . . 2_655 ? F1A C2A C3 C2A 113.6(16) . . . 2_655 ? C1 C2A C3 C2A -5.4(6) . . . 2_655 ? C15 S1 C12 C13 0.0(12) . . . . ? C15 S1 C12 C11 -175.0(12) . . . . ? C11 C12 C13 C14 174.1(17) . . . . ? S1 C12 C13 C14 -0.2(16) . . . . ? C11 C12 C13 C1 -4(3) . . . . ? S1 C12 C13 C1 -178.3(11) . . . . ? C1 C1 C13 C12 -40(2) 2_655 . . . ? C2A C1 C13 C12 146.9(15) . . . . ? C2B C1 C13 C12 133.4(16) . . . . ? C1 C1 C13 C14 141.9(15) 2_655 . . . ? C2A C1 C13 C14 -31.1(19) . . . . ? C2B C1 C13 C14 -44.5(18) . . . . ? C12 C13 C14 C15 0(2) . . . . ? C1 C13 C14 C15 178.5(13) . . . . ? C13 C14 C15 C16 -176.1(15) . . . . ? C13 C14 C15 S1 0(2) . . . . ? C12 S1 C15 C14 0.2(14) . . . . ? C12 S1 C15 C16 176.3(13) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961267' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2.52GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety 'C17 H14 F6 S2' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 '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' _symmetry_space_group_name_Hall '-C 2yc' 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 18.4265(46) _cell_length_b 8.4721(6) _cell_length_c 10.6330(7) _cell_angle_alpha 90.00 _cell_angle_beta 118.512(15) _cell_angle_gamma 90.00 _cell_volume 1458.6(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 699 _cell_measurement_theta_min 2.9697 _cell_measurement_theta_max 28.6911 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.339 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 2070 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.53 _diffrn_reflns_theta_max 25.95 _reflns_number_total 398 _reflns_number_gt 338 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.266 _diffrn_reflns_theta_full 25.95 _diffrn_measured_fraction_theta_full 0.266 _refine_diff_density_max 0.399 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.054 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 398 _refine_ls_number_parameters 74 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.1505 _refine_ls_wR_factor_gt 0.1441 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.3225(4) 0.9782(2) 0.0524(4) 0.035(5) Uani 1 1 d D A . C1 C 0.4622(7) 0.5948(6) 0.1929(7) 0.0185(18) Uiso 1 1 d D . . C2A C 0.4370(12) 0.4346(13) 0.1266(14) 0.022(6) Uiso 0.50 1 d PD A 1 C2B C 0.4324(11) 0.4252(15) 0.1531(16) 0.028(6) Uiso 0.50 1 d PD A 2 C3 C 0.5000 0.3235(11) 0.2500 0.024(3) Uiso 1 2 d SD . . C11 C 0.4320(14) 0.8974(9) 0.3366(14) 0.033(2) Uiso 1 1 d D A . H11A H 0.4280 0.8075 0.3879 0.049 Uiso 1 1 calc R . . H11B H 0.4025 0.9845 0.3485 0.049 Uiso 1 1 calc R . . H11C H 0.4890 0.9257 0.3731 0.049 Uiso 1 1 calc R . . C12 C 0.3951(11) 0.8576(8) 0.1803(12) 0.0246(18) Uiso 1 1 d D . . C13 C 0.4058(12) 0.7249(8) 0.1167(12) 0.0252(19) Uiso 1 1 d D A . C14 C 0.3547(15) 0.7248(8) -0.0348(16) 0.028(2) Uiso 1 1 d D . . H14 H 0.3555 0.6439 -0.0933 0.034 Uiso 1 1 calc R A . C15 C 0.3048(13) 0.8529(9) -0.0864(14) 0.030(2) Uiso 1 1 d D A . C16 C 0.2432(17) 0.8848(10) -0.2360(17) 0.045(3) Uiso 1 1 d . . . H16A H 0.2504 0.9903 -0.2610 0.068 Uiso 1 1 calc R A . H16B H 0.1887 0.8736 -0.2467 0.068 Uiso 1 1 calc R . . H16C H 0.2504 0.8112 -0.2978 0.068 Uiso 1 1 calc R . . F1A F 0.4483(16) 0.4172(9) 0.0109(16) 0.022(2) Uiso 0.50 1 d PD A 1 F2A F 0.3585(16) 0.3973(12) 0.0867(17) 0.041(3) Uiso 0.50 1 d PD A 1 F1B F 0.4136(17) 0.3923(11) 0.0191(18) 0.035(3) Uiso 0.50 1 d PD A 2 F2B F 0.3638(16) 0.3940(12) 0.1647(18) 0.048(3) Uiso 0.50 1 d PD A 2 F3A F 0.5452(14) 0.2633(12) 0.1797(17) 0.043(3) Uiso 0.50 1 d PD A -1 F3B F 0.4817(17) 0.1997(11) 0.2975(18) 0.043(3) Uiso 0.50 1 d PD 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 0.044(15) 0.0317(12) 0.037(5) 0.0118(14) 0.025(9) 0.012(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 C12 1.72(2) . ? S1 C15 1.719(10) . ? C1 C1 1.34(3) 2_655 ? C1 C13 1.465(16) . ? C1 C2A 1.497(12) . ? C1 C2B 1.524(15) . ? C2A F2A 1.34(2) . ? C2A F1A 1.351(16) . ? C2A C3 1.582(17) . ? C2B F1B 1.325(17) . ? C2B F2B 1.35(2) . ? C2B C3 1.460(17) . ? C3 F3B 1.277(10) 2_655 ? C3 F3B 1.277(10) . ? C3 F3A 1.452(14) 2_655 ? C3 F3A 1.452(14) . ? C3 C2B 1.460(17) 2_655 ? C3 C2A 1.582(17) 2_655 ? C11 C12 1.503(19) . ? C12 C13 1.373(10) . ? C13 C14 1.43(3) . ? C14 C15 1.36(2) . ? C15 C16 1.47(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 C12 S1 C15 94.0(8) . . ? C1 C1 C13 131.0(7) 2_655 . ? C1 C1 C2A 112.4(8) 2_655 . ? C13 C1 C2A 116.3(11) . . ? C1 C1 C2B 109.4(6) 2_655 . ? C13 C1 C2B 119.3(11) . . ? F2A C2A F1A 107.5(17) . . ? F2A C2A C1 114.1(12) . . ? F1A C2A C1 112.3(12) . . ? F2A C2A C3 112.1(14) . . ? F1A C2A C3 108.6(13) . . ? C1 C2A C3 102.1(12) . . ? F1B C2B F2B 106.3(17) . . ? F1B C2B C3 109.4(16) . . ? F2B C2B C3 109.9(16) . . ? F1B C2B C1 111.8(13) . . ? F2B C2B C1 112.7(12) . . ? C3 C2B C1 106.7(13) . . ? F3B C3 F3B 69.6(13) 2_655 . ? F3B C3 F3A 103.9(12) 2_655 2_655 ? F3B C3 F3A 103.9(12) . . ? F3A C3 F3A 138.9(12) 2_655 . ? F3B C3 C2B 117.8(15) 2_655 2_655 ? F3B C3 C2B 120.2(13) . 2_655 ? F3A C3 C2B 110.5(11) 2_655 2_655 ? F3A C3 C2B 93.7(13) . 2_655 ? F3B C3 C2B 120.2(13) 2_655 . ? F3B C3 C2B 117.8(15) . . ? F3A C3 C2B 93.7(13) 2_655 . ? F3A C3 C2B 110.5(11) . . ? C2B C3 C2B 107.6(15) 2_655 . ? F3B C3 C2A 126.1(15) 2_655 2_655 ? F3B C3 C2A 112.9(11) . 2_655 ? F3A C3 C2A 99.0(10) 2_655 2_655 ? F3A C3 C2A 105.2(13) . 2_655 ? C2B C3 C2A 106.0(13) . 2_655 ? F3B C3 C2A 112.9(11) 2_655 . ? F3B C3 C2A 126.1(15) . . ? F3A C3 C2A 105.2(13) 2_655 . ? F3A C3 C2A 99.0(10) . . ? C2B C3 C2A 106.0(13) 2_655 . ? C2A C3 C2A 106.9(14) 2_655 . ? C13 C12 C11 129.3(12) . . ? C13 C12 S1 109.7(10) . . ? C11 C12 S1 120.8(9) . . ? C12 C13 C14 112.6(11) . . ? C12 C13 C1 125.0(11) . . ? C14 C13 C1 122.3(8) . . ? C15 C14 C13 114.2(9) . . ? C14 C15 C16 127.4(9) . . ? C14 C15 S1 109.4(12) . . ? C16 C15 S1 123.2(10) . . ? 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 C1 C1 C2A F2A 138.3(13) 2_655 . . . ? C13 C1 C2A F2A -47.5(16) . . . . ? C2B C1 C2A F2A 59(4) . . . . ? C1 C1 C2A F1A -99.0(17) 2_655 . . . ? C13 C1 C2A F1A 75.2(19) . . . . ? C2B C1 C2A F1A -178(4) . . . . ? C1 C1 C2A C3 17.1(15) 2_655 . . . ? C13 C1 C2A C3 -168.7(8) . . . . ? C2B C1 C2A C3 -62(3) . . . . ? C1 C1 C2B F1B -122.8(17) 2_655 . . . ? C13 C1 C2B F1B 63(2) . . . . ? C2A C1 C2B F1B -17(3) . . . . ? C1 C1 C2B F2B 117.4(15) 2_655 . . . ? C13 C1 C2B F2B -56.9(17) . . . . ? C2A C1 C2B F2B -137(4) . . . . ? C1 C1 C2B C3 -3.3(16) 2_655 . . . ? C13 C1 C2B C3 -177.6(8) . . . . ? C2A C1 C2B C3 103(4) . . . . ? F1B C2B C3 F3B -16(2) . . . 2_655 ? F2B C2B C3 F3B 99.9(17) . . . 2_655 ? C1 C2B C3 F3B -137.6(13) . . . 2_655 ? F1B C2B C3 F3B -97.9(17) . . . . ? F2B C2B C3 F3B 18.4(15) . . . . ? C1 C2B C3 F3B 141.0(10) . . . . ? F1B C2B C3 F3A -124.9(16) . . . 2_655 ? F2B C2B C3 F3A -8.5(13) . . . 2_655 ? C1 C2B C3 F3A 114.0(13) . . . 2_655 ? F1B C2B C3 F3A 21.2(18) . . . . ? F2B C2B C3 F3A 137.6(14) . . . . ? C1 C2B C3 F3A -99.9(14) . . . . ? F1B C2B C3 C2B 122.3(19) . . . 2_655 ? F2B C2B C3 C2B -121.4(15) . . . 2_655 ? C1 C2B C3 C2B 1.1(5) . . . 2_655 ? F1B C2B C3 C2A 134.7(15) . . . 2_655 ? F2B C2B C3 C2A -109.0(12) . . . 2_655 ? C1 C2B C3 C2A 13.5(14) . . . 2_655 ? F1B C2B C3 C2A 38(4) . . . . ? F2B C2B C3 C2A 155(4) . . . . ? C1 C2B C3 C2A -83(4) . . . . ? F2A C2A C3 F3B 88.9(16) . . . 2_655 ? F1A C2A C3 F3B -29.7(19) . . . 2_655 ? C1 C2A C3 F3B -148.5(13) . . . 2_655 ? F2A C2A C3 F3B 8.2(15) . . . . ? F1A C2A C3 F3B -110.5(15) . . . . ? C1 C2A C3 F3B 130.8(12) . . . . ? F2A C2A C3 F3A -23.7(12) . . . 2_655 ? F1A C2A C3 F3A -142.3(13) . . . 2_655 ? C1 C2A C3 F3A 98.9(13) . . . 2_655 ? F2A C2A C3 F3A 122.8(13) . . . . ? F1A C2A C3 F3A 4.1(16) . . . . ? C1 C2A C3 F3A -114.7(13) . . . . ? F2A C2A C3 C2B -140.7(13) . . . 2_655 ? F1A C2A C3 C2B 100.7(15) . . . 2_655 ? C1 C2A C3 C2B -18.1(13) . . . 2_655 ? F2A C2A C3 C2B -41(4) . . . . ? F1A C2A C3 C2B -160(5) . . . . ? C1 C2A C3 C2B 81(4) . . . . ? F2A C2A C3 C2A -128.3(13) . . . 2_655 ? F1A C2A C3 C2A 113.1(16) . . . 2_655 ? C1 C2A C3 C2A -5.7(5) . . . 2_655 ? C15 S1 C12 C13 0.6(11) . . . . ? C15 S1 C12 C11 -174.8(12) . . . . ? C11 C12 C13 C14 175.0(14) . . . . ? S1 C12 C13 C14 0.2(16) . . . . ? C11 C12 C13 C1 -4(2) . . . . ? S1 C12 C13 C1 -179.2(10) . . . . ? C1 C1 C13 C12 -37(2) 2_655 . . . ? C2A C1 C13 C12 149.8(15) . . . . ? C2B C1 C13 C12 135.6(16) . . . . ? C1 C1 C13 C14 143.3(15) 2_655 . . . ? C2A C1 C13 C14 -29.5(17) . . . . ? C2B C1 C13 C14 -43.7(17) . . . . ? C12 C13 C14 C15 -1(2) . . . . ? C1 C13 C14 C15 178.3(12) . . . . ? C13 C14 C15 C16 -177.6(14) . . . . ? C13 C14 C15 S1 1.5(17) . . . . ? C12 S1 C15 C14 -1.2(12) . . . . ? C12 S1 C15 C16 178.0(14) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961268' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3.64GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety 'C17 H14 F6 S2' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 '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' _symmetry_space_group_name_Hall '-C 2yc' 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 18.0508(11) _cell_length_b 8.3848(8) _cell_length_c 10.551(23) _cell_angle_alpha 90.00 _cell_angle_beta 118.132(23) _cell_angle_gamma 90.00 _cell_volume 1408.2(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 786 _cell_measurement_theta_min 2.1079 _cell_measurement_theta_max 27.8447 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.351 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 1296 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0898 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 28.06 _reflns_number_total 476 _reflns_number_gt 353 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.254 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.254 _refine_diff_density_max 0.482 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.075 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 476 _refine_ls_number_parameters 74 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1193 _refine_ls_R_factor_gt 0.0982 _refine_ls_wR_factor_ref 0.2507 _refine_ls_wR_factor_gt 0.2321 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.3220(5) 0.9830(2) 0.0529(5) 0.041(5) Uani 1 1 d D A . C1 C 0.4610(7) 0.5933(7) 0.1927(7) 0.0171(19) Uiso 1 1 d D . . C2A C 0.4373(13) 0.4323(14) 0.1239(13) 0.022(5) Uiso 0.50 1 d PD A 1 C2B C 0.4312(11) 0.4215(15) 0.1545(15) 0.018(4) Uiso 0.50 1 d PD A 2 C3 C 0.5000 0.3193(11) 0.2500 0.024(3) Uiso 1 2 d SD . . C11 C 0.4299(17) 0.8985(10) 0.3369(15) 0.029(2) Uiso 1 1 d D A . H11A H 0.4322 0.8036 0.3895 0.043 Uiso 1 1 calc R . . H11B H 0.3946 0.9759 0.3492 0.043 Uiso 1 1 calc R . . H11C H 0.4855 0.9414 0.3722 0.043 Uiso 1 1 calc R . . C12 C 0.3950(12) 0.8595(8) 0.1822(12) 0.0219(19) Uiso 1 1 d D . . C13 C 0.4044(13) 0.7249(8) 0.1162(12) 0.0189(19) Uiso 1 1 d D A . C14 C 0.3517(17) 0.7258(9) -0.0359(16) 0.025(2) Uiso 1 1 d D . . H14 H 0.3519 0.6439 -0.0952 0.030 Uiso 1 1 calc R A . C15 C 0.3016(15) 0.8545(10) -0.0865(14) 0.031(2) Uiso 1 1 d D A . C16 C 0.233(2) 0.8890(13) -0.243(2) 0.051(3) Uiso 1 1 d . . . H16A H 0.2458 0.9872 -0.2755 0.077 Uiso 1 1 calc R A . H16B H 0.1793 0.8976 -0.2459 0.077 Uiso 1 1 calc R . . H16C H 0.2317 0.8035 -0.3047 0.077 Uiso 1 1 calc R . . F1A F 0.452(2) 0.4186(11) 0.010(2) 0.024(3) Uiso 0.50 1 d PD A 1 F2A F 0.3552(18) 0.3920(14) 0.0750(19) 0.045(4) Uiso 0.50 1 d PD A 1 F1B F 0.418(2) 0.3872(13) 0.022(2) 0.034(3) Uiso 0.50 1 d PD A 2 F2B F 0.3607(18) 0.3894(13) 0.162(2) 0.046(3) Uiso 0.50 1 d PD A 2 F3A F 0.5482(16) 0.2645(15) 0.181(2) 0.048(3) Uiso 0.50 1 d PD A -1 F3B F 0.482(2) 0.1943(12) 0.298(2) 0.043(3) Uiso 0.50 1 d PD 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 0.063(17) 0.0312(12) 0.046(5) 0.0173(14) 0.040(9) 0.016(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 C15 1.718(9) . ? S1 C12 1.725(15) . ? C1 C1 1.36(2) 2_655 ? C1 C13 1.461(14) . ? C1 C2A 1.497(12) . ? C1 C2B 1.524(15) . ? C2A F1A 1.352(16) . ? C2A F2A 1.36(2) . ? C2A C3 1.590(12) . ? C2B F1B 1.334(15) . ? C2B F2B 1.341(19) . ? C2B C3 1.453(12) . ? C3 F3B 1.267(11) . ? C3 F3B 1.267(11) 2_655 ? C3 F3A 1.451(13) 2_655 ? C3 F3A 1.451(13) . ? C3 C2B 1.453(12) 2_655 ? C3 C2A 1.590(12) 2_655 ? C11 C12 1.483(16) . ? C12 C13 1.378(11) . ? C13 C14 1.43(2) . ? C14 C15 1.35(2) . ? C15 C16 1.56(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 C15 S1 C12 94.3(6) . . ? C1 C1 C13 130.8(7) 2_655 . ? C1 C1 C2A 111.8(8) 2_655 . ? C13 C1 C2A 116.6(9) . . ? C1 C1 C2B 108.9(6) 2_655 . ? C13 C1 C2B 120.0(10) . . ? F1A C2A F2A 106.1(18) . . ? F1A C2A C1 112.1(13) . . ? F2A C2A C1 114.7(13) . . ? F1A C2A C3 109.4(15) . . ? F2A C2A C3 112.8(14) . . ? C1 C2A C3 101.8(10) . . ? F1B C2B F2B 108.3(18) . . ? F1B C2B C3 105.9(16) . . ? F2B C2B C3 111.3(15) . . ? F1B C2B C1 110.4(13) . . ? F2B C2B C1 113.6(12) . . ? C3 C2B C1 107.1(12) . . ? F3B C3 F3B 68.3(15) . 2_655 ? F3B C3 F3A 105.2(14) 2_655 2_655 ? F3B C3 F3A 105.2(14) . . ? F3A C3 F3A 143.1(13) 2_655 . ? F3B C3 C2B 120.4(13) . 2_655 ? F3B C3 C2B 118.0(16) 2_655 2_655 ? F3A C3 C2B 110.9(11) 2_655 2_655 ? F3A C3 C2B 91.0(12) . 2_655 ? F3B C3 C2B 118.0(16) . . ? F3B C3 C2B 120.4(13) 2_655 . ? F3A C3 C2B 91.0(12) 2_655 . ? F3A C3 C2B 110.9(11) . . ? C2B C3 C2B 107.7(14) 2_655 . ? F3B C3 C2A 112.0(11) . 2_655 ? F3B C3 C2A 127.7(16) 2_655 2_655 ? F3A C3 C2A 97.2(11) 2_655 2_655 ? F3A C3 C2A 104.6(13) . 2_655 ? C2B C3 C2A 105.5(11) . 2_655 ? F3B C3 C2A 127.7(16) . . ? F3B C3 C2A 112.0(11) 2_655 . ? F3A C3 C2A 104.6(13) 2_655 . ? F3A C3 C2A 97.2(11) . . ? C2B C3 C2A 105.5(11) 2_655 . ? C2A C3 C2A 106.9(12) 2_655 . ? C13 C12 C11 130.3(12) . . ? C13 C12 S1 108.8(9) . . ? C11 C12 S1 120.5(8) . . ? C12 C13 C14 112.8(11) . . ? C12 C13 C1 124.1(11) . . ? C14 C13 C1 123.1(7) . . ? C15 C14 C13 114.6(8) . . ? C14 C15 C16 128.3(10) . . ? C14 C15 S1 109.3(12) . . ? C16 C15 S1 122.3(10) . . ? 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 C1 C1 C2A F1A -96.4(18) 2_655 . . . ? C13 C1 C2A F1A 75(2) . . . . ? C2B C1 C2A F1A -178(4) . . . . ? C1 C1 C2A F2A 142.5(13) 2_655 . . . ? C13 C1 C2A F2A -46.3(16) . . . . ? C2B C1 C2A F2A 61(3) . . . . ? C1 C1 C2A C3 20.5(16) 2_655 . . . ? C13 C1 C2A C3 -168.3(9) . . . . ? C2B C1 C2A C3 -61(3) . . . . ? C1 C1 C2B F1B -118.3(19) 2_655 . . . ? C13 C1 C2B F1B 66(2) . . . . ? C2A C1 C2B F1B -15(3) . . . . ? C1 C1 C2B F2B 119.9(15) 2_655 . . . ? C13 C1 C2B F2B -55.4(18) . . . . ? C2A C1 C2B F2B -136(3) . . . . ? C1 C1 C2B C3 -3.5(16) 2_655 . . . ? C13 C1 C2B C3 -178.8(8) . . . . ? C2A C1 C2B C3 100(4) . . . . ? F1B C2B C3 F3B -100.5(17) . . . . ? F2B C2B C3 F3B 17.0(16) . . . . ? C1 C2B C3 F3B 141.8(11) . . . . ? F1B C2B C3 F3B -20(2) . . . 2_655 ? F2B C2B C3 F3B 97.1(18) . . . 2_655 ? C1 C2B C3 F3B -138.2(15) . . . 2_655 ? F1B C2B C3 F3A -128.7(16) . . . 2_655 ? F2B C2B C3 F3A -11.2(13) . . . 2_655 ? C1 C2B C3 F3A 113.5(13) . . . 2_655 ? F1B C2B C3 F3A 20.9(19) . . . . ? F2B C2B C3 F3A 138.4(14) . . . . ? C1 C2B C3 F3A -96.9(14) . . . . ? F1B C2B C3 C2B 119.0(18) . . . 2_655 ? F2B C2B C3 C2B -123.5(15) . . . 2_655 ? C1 C2B C3 C2B 1.2(5) . . . 2_655 ? F1B C2B C3 C2A 133.5(15) . . . 2_655 ? F2B C2B C3 C2A -109.0(12) . . . 2_655 ? C1 C2B C3 C2A 15.7(13) . . . 2_655 ? F1B C2B C3 C2A 36(3) . . . . ? F2B C2B C3 C2A 153(4) . . . . ? C1 C2B C3 C2A -82(3) . . . . ? F1A C2A C3 F3B -111.3(17) . . . . ? F2A C2A C3 F3B 6.6(16) . . . . ? C1 C2A C3 F3B 129.9(13) . . . . ? F1A C2A C3 F3B -32(2) . . . 2_655 ? F2A C2A C3 F3B 85.5(18) . . . 2_655 ? C1 C2A C3 F3B -151.1(15) . . . 2_655 ? F1A C2A C3 F3A -145.7(15) . . . 2_655 ? F2A C2A C3 F3A -27.8(13) . . . 2_655 ? C1 C2A C3 F3A 95.5(14) . . . 2_655 ? F1A C2A C3 F3A 4.3(17) . . . . ? F2A C2A C3 F3A 122.1(13) . . . . ? C1 C2A C3 F3A -114.5(14) . . . . ? F1A C2A C3 C2B 97.3(16) . . . 2_655 ? F2A C2A C3 C2B -144.8(14) . . . 2_655 ? C1 C2A C3 C2B -21.5(14) . . . 2_655 ? F1A C2A C3 C2B -161(4) . . . . ? F2A C2A C3 C2B -44(3) . . . . ? C1 C2A C3 C2B 80(3) . . . . ? F1A C2A C3 C2A 111.9(18) . . . 2_655 ? F2A C2A C3 C2A -130.2(14) . . . 2_655 ? C1 C2A C3 C2A -6.8(6) . . . 2_655 ? C15 S1 C12 C13 1.8(13) . . . . ? C15 S1 C12 C11 -172.2(14) . . . . ? C11 C12 C13 C14 172.6(17) . . . . ? S1 C12 C13 C14 -0.7(18) . . . . ? C11 C12 C13 C1 -6(3) . . . . ? S1 C12 C13 C1 -179.7(11) . . . . ? C1 C1 C13 C12 -38(2) 2_655 . . . ? C2A C1 C13 C12 152.7(16) . . . . ? C2B C1 C13 C12 136.0(16) . . . . ? C1 C1 C13 C14 143.0(16) 2_655 . . . ? C2A C1 C13 C14 -26(2) . . . . ? C2B C1 C13 C14 -42.9(19) . . . . ? C12 C13 C14 C15 -1(2) . . . . ? C1 C13 C14 C15 177.7(14) . . . . ? C13 C14 C15 C16 -175.7(17) . . . . ? C13 C14 C15 S1 3(2) . . . . ? C12 S1 C15 C14 -2.6(15) . . . . ? C12 S1 C15 C16 175.9(15) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961269' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4.15GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety 'C17 H14 F6 S2' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 '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' _symmetry_space_group_name_Hall '-C 2yc' 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 17.874(8) _cell_length_b 8.3360(7) _cell_length_c 10.524(13) _cell_angle_alpha 90.00 _cell_angle_beta 117.9(2) _cell_angle_gamma 90.00 _cell_volume 1386.9(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 724 _cell_measurement_theta_min 2.6647 _cell_measurement_theta_max 28.2743 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.900 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.357 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 1864 _diffrn_reflns_av_R_equivalents 0.0851 _diffrn_reflns_av_sigmaI/netI 0.0759 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.50 _diffrn_reflns_theta_max 25.50 _reflns_number_total 426 _reflns_number_gt 374 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.299 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.299 _refine_diff_density_max 0.512 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.072 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 426 _refine_ls_number_parameters 74 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1031 _refine_ls_R_factor_gt 0.0934 _refine_ls_wR_factor_ref 0.1994 _refine_ls_wR_factor_gt 0.1927 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.3212(5) 0.9855(3) 0.0536(5) 0.038(5) Uani 1 1 d D A . C1 C 0.4613(7) 0.5930(7) 0.1929(7) 0.0168(19) Uiso 1 1 d D . . C2A C 0.4376(13) 0.4306(13) 0.1243(14) 0.018(5) Uiso 0.50 1 d PD A 1 C2B C 0.4305(11) 0.4195(16) 0.1550(17) 0.031(6) Uiso 0.50 1 d PD A 2 C3 C 0.5000 0.3172(11) 0.2500 0.022(3) Uiso 1 2 d SD . . C11 C 0.4295(18) 0.8983(10) 0.3376(17) 0.029(2) Uiso 1 1 d D A . H11A H 0.4231 0.8070 0.3873 0.044 Uiso 1 1 calc R . . H11B H 0.3997 0.9882 0.3494 0.044 Uiso 1 1 calc R . . H11C H 0.4885 0.9243 0.3765 0.044 Uiso 1 1 calc R . . C12 C 0.3943(13) 0.8604(9) 0.1824(13) 0.022(2) Uiso 1 1 d D . . C13 C 0.4047(13) 0.7255(8) 0.1171(13) 0.0198(19) Uiso 1 1 d D A . C14 C 0.3547(18) 0.7257(10) -0.0325(18) 0.029(2) Uiso 1 1 d D . . H14 H 0.3561 0.6435 -0.0911 0.035 Uiso 1 1 calc R A . C15 C 0.3040(16) 0.8569(10) -0.0844(16) 0.033(2) Uiso 1 1 d D A . C16 C 0.240(2) 0.8914(13) -0.237(2) 0.055(3) Uiso 1 1 d . . . H16A H 0.2537 0.9918 -0.2668 0.083 Uiso 1 1 calc R A . H16B H 0.1848 0.8972 -0.2449 0.083 Uiso 1 1 calc R . . H16C H 0.2418 0.8072 -0.2986 0.083 Uiso 1 1 calc R . . F1A F 0.4527(19) 0.4167(11) 0.011(2) 0.025(3) Uiso 0.50 1 d PD A 1 F2A F 0.3552(17) 0.3912(13) 0.0726(19) 0.042(3) Uiso 0.50 1 d PD A 1 F1B F 0.411(2) 0.3850(12) 0.020(2) 0.036(3) Uiso 0.50 1 d PD A 2 F2B F 0.3602(18) 0.3877(13) 0.165(2) 0.044(3) Uiso 0.50 1 d PD A 2 F3A F 0.5508(16) 0.2643(14) 0.183(2) 0.047(3) Uiso 0.50 1 d PD A -1 F3B F 0.483(2) 0.1900(12) 0.297(2) 0.042(3) Uiso 0.50 1 d PD 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 0.050(16) 0.0312(12) 0.040(6) 0.0184(14) 0.029(10) 0.016(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 C15 1.714(9) . ? S1 C12 1.725(15) . ? C1 C1 1.34(2) 2_655 ? C1 C13 1.457(14) . ? C1 C2A 1.499(12) . ? C1 C2B 1.533(15) . ? C2A F2A 1.35(2) . ? C2A F1A 1.350(16) . ? C2A C3 1.583(12) . ? C2B F1B 1.328(16) . ? C2B F2B 1.338(19) . ? C2B C3 1.452(12) . ? C3 F3B 1.268(10) 2_655 ? C3 F3B 1.268(10) . ? C3 C2B 1.452(12) 2_655 ? C3 F3A 1.454(12) 2_655 ? C3 F3A 1.454(12) . ? C3 C2A 1.583(12) 2_655 ? C11 C12 1.484(18) . ? C12 C13 1.375(10) . ? C13 C14 1.40(2) . ? C14 C15 1.36(2) . ? C15 C16 1.50(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 C15 S1 C12 93.3(7) . . ? C1 C1 C13 130.6(7) 2_655 . ? C1 C1 C2A 111.8(8) 2_655 . ? C13 C1 C2A 117.0(9) . . ? C1 C1 C2B 109.1(6) 2_655 . ? C13 C1 C2B 119.9(10) . . ? F2A C2A F1A 104.7(17) . . ? F2A C2A C1 115.0(12) . . ? F1A C2A C1 112.1(13) . . ? F2A C2A C3 113.6(13) . . ? F1A C2A C3 109.6(14) . . ? C1 C2A C3 102.0(10) . . ? F1B C2B F2B 104.8(17) . . ? F1B C2B C3 108.9(16) . . ? F2B C2B C3 111.2(16) . . ? F1B C2B C1 111.5(14) . . ? F2B C2B C1 113.8(13) . . ? C3 C2B C1 106.7(12) . . ? F3B C3 F3B 66.5(14) 2_655 . ? F3B C3 C2B 118.2(17) 2_655 2_655 ? F3B C3 C2B 120.6(14) . 2_655 ? F3B C3 C2B 120.6(14) 2_655 . ? F3B C3 C2B 118.2(17) . . ? C2B C3 C2B 108.1(14) 2_655 . ? F3B C3 F3A 104.9(13) 2_655 2_655 ? C2B C3 F3A 111.8(12) 2_655 2_655 ? C2B C3 F3A 89.1(13) . 2_655 ? F3B C3 F3A 104.9(13) . . ? C2B C3 F3A 89.1(13) 2_655 . ? C2B C3 F3A 111.8(12) . . ? F3A C3 F3A 144.7(12) 2_655 . ? F3B C3 C2A 128.3(16) 2_655 2_655 ? F3B C3 C2A 112.3(12) . 2_655 ? C2B C3 C2A 105.4(11) . 2_655 ? F3A C3 C2A 97.6(10) 2_655 2_655 ? F3A C3 C2A 103.3(13) . 2_655 ? F3B C3 C2A 112.3(12) 2_655 . ? F3B C3 C2A 128.3(16) . . ? C2B C3 C2A 105.4(11) 2_655 . ? F3A C3 C2A 103.3(12) 2_655 . ? F3A C3 C2A 97.6(10) . . ? C2A C3 C2A 106.7(13) 2_655 . ? C13 C12 C11 129.6(12) . . ? C13 C12 S1 109.4(10) . . ? C11 C12 S1 120.7(9) . . ? C12 C13 C14 113.3(12) . . ? C12 C13 C1 124.6(11) . . ? C14 C13 C1 122.1(7) . . ? C15 C14 C13 114.0(8) . . ? C14 C15 C16 127.8(10) . . ? C14 C15 S1 109.9(12) . . ? C16 C15 S1 122.3(11) . . ? 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 C1 C1 C2A F2A 143.5(13) 2_655 . . . ? C13 C1 C2A F2A -44.6(16) . . . . ? C2B C1 C2A F2A 61(3) . . . . ? C1 C1 C2A F1A -97.1(18) 2_655 . . . ? C13 C1 C2A F1A 75(2) . . . . ? C2B C1 C2A F1A -180(4) . . . . ? C1 C1 C2A C3 20.1(15) 2_655 . . . ? C13 C1 C2A C3 -168.0(9) . . . . ? C2B C1 C2A C3 -63(3) . . . . ? C1 C1 C2B F1B -123.5(18) 2_655 . . . ? C13 C1 C2B F1B 62(2) . . . . ? C2A C1 C2B F1B -21(3) . . . . ? C1 C1 C2B F2B 118.2(16) 2_655 . . . ? C13 C1 C2B F2B -55.9(19) . . . . ? C2A C1 C2B F2B -139(3) . . . . ? C1 C1 C2B C3 -4.8(17) 2_655 . . . ? C13 C1 C2B C3 -178.9(9) . . . . ? C2A C1 C2B C3 98(3) . . . . ? F1B C2B C3 F3B -18(2) . . . 2_655 ? F2B C2B C3 F3B 96.6(18) . . . 2_655 ? C1 C2B C3 F3B -138.8(14) . . . 2_655 ? F1B C2B C3 F3B -96.4(18) . . . . ? F2B C2B C3 F3B 18.6(17) . . . . ? C1 C2B C3 F3B 143.2(11) . . . . ? F1B C2B C3 C2B 122(2) . . . 2_655 ? F2B C2B C3 C2B -123.0(17) . . . 2_655 ? C1 C2B C3 C2B 1.6(6) . . . 2_655 ? F1B C2B C3 F3A -125.2(17) . . . 2_655 ? F2B C2B C3 F3A -10.2(14) . . . 2_655 ? C1 C2B C3 F3A 114.4(13) . . . 2_655 ? F1B C2B C3 F3A 26(2) . . . . ? F2B C2B C3 F3A 140.5(15) . . . . ? C1 C2B C3 F3A -94.9(15) . . . . ? F1B C2B C3 C2A 137.1(16) . . . 2_655 ? F2B C2B C3 C2A -107.9(13) . . . 2_655 ? C1 C2B C3 C2A 16.7(14) . . . 2_655 ? F1B C2B C3 C2A 40(3) . . . . ? F2B C2B C3 C2A 155(4) . . . . ? C1 C2B C3 C2A -80(3) . . . . ? F2A C2A C3 F3B 83.7(17) . . . 2_655 ? F1A C2A C3 F3B -33(2) . . . 2_655 ? C1 C2A C3 F3B -151.9(15) . . . 2_655 ? F2A C2A C3 F3B 6.8(16) . . . . ? F1A C2A C3 F3B -110.0(16) . . . . ? C1 C2A C3 F3B 131.1(12) . . . . ? F2A C2A C3 C2B -146.3(14) . . . 2_655 ? F1A C2A C3 C2B 97.0(16) . . . 2_655 ? C1 C2A C3 C2B -21.9(14) . . . 2_655 ? F2A C2A C3 C2B -44(3) . . . . ? F1A C2A C3 C2B -161(4) . . . . ? C1 C2A C3 C2B 81(3) . . . . ? F2A C2A C3 F3A -28.7(13) . . . 2_655 ? F1A C2A C3 F3A -145.5(15) . . . 2_655 ? C1 C2A C3 F3A 95.6(13) . . . 2_655 ? F2A C2A C3 F3A 122.6(13) . . . . ? F1A C2A C3 F3A 5.8(18) . . . . ? C1 C2A C3 F3A -113.1(13) . . . . ? F2A C2A C3 C2A -131.0(14) . . . 2_655 ? F1A C2A C3 C2A 112.2(18) . . . 2_655 ? C1 C2A C3 C2A -6.7(6) . . . 2_655 ? C15 S1 C12 C13 0.9(13) . . . . ? C15 S1 C12 C11 -173.6(14) . . . . ? C11 C12 C13 C14 174.0(17) . . . . ? S1 C12 C13 C14 0.2(18) . . . . ? C11 C12 C13 C1 -6(3) . . . . ? S1 C12 C13 C1 -179.6(11) . . . . ? C1 C1 C13 C12 -38(2) 2_655 . . . ? C2A C1 C13 C12 152.0(16) . . . . ? C2B C1 C13 C12 134.7(17) . . . . ? C1 C1 C13 C14 142.4(16) 2_655 . . . ? C2A C1 C13 C14 -27.7(19) . . . . ? C2B C1 C13 C14 -45.0(19) . . . . ? C12 C13 C14 C15 -1(2) . . . . ? C1 C13 C14 C15 178.3(14) . . . . ? C13 C14 C15 C16 -177.1(18) . . . . ? C13 C14 C15 S1 2(2) . . . . ? C12 S1 C15 C14 -1.7(14) . . . . ? C12 S1 C15 C16 177.5(17) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961270' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5.70GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety '2(C17 H14 F6 S2)' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.506(2) _cell_length_b 16.364(3) _cell_length_c 15.514(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.95(3) _cell_angle_gamma 90.00 _cell_volume 2634.7(9) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2028 _cell_measurement_theta_min 3.4486 _cell_measurement_theta_max 25.5380 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.999 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.375 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 8389 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.13 _reflns_number_total 1452 _reflns_number_gt 1125 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.281 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.281 _refine_diff_density_max 0.559 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.069 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 1452 _refine_ls_number_parameters 229 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.2025 _refine_ls_wR_factor_gt 0.1779 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.026 _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 0.0137(6) 0.4153(3) 0.2146(10) 0.0102(16) Uiso 1 1 d D . . C2 C 0.0149(6) 0.3292(4) 0.1807(10) 0.0160(17) Uiso 1 1 d D . . C3 C -0.0139(6) 0.2779(4) 0.2611(10) 0.0114(16) Uiso 1 1 d D . . C4 C -0.0743(7) 0.3373(5) 0.3135(11) 0.0174(19) Uiso 1 1 d D . . C5 C -0.0225(6) 0.4192(4) 0.2933(11) 0.0108(16) Uiso 1 1 d D . . C11 C -0.1493(7) 0.5739(4) 0.1834(14) 0.0165(18) Uiso 1 1 d D . . H11A H -0.1986 0.5256 0.1901 0.025 Uiso 1 1 calc R . . H11B H -0.2013 0.6119 0.1460 0.025 Uiso 1 1 calc R . . H11C H -0.1228 0.5986 0.2395 0.025 Uiso 1 1 calc R . . C12 C -0.0330(6) 0.5517(4) 0.1438(12) 0.0135(16) Uiso 1 1 d D . . C13 C 0.0409(6) 0.4819(4) 0.1580(11) 0.0129(17) Uiso 1 1 d D . . C14 C 0.1434(6) 0.4792(4) 0.1083(12) 0.0128(16) Uiso 1 1 d D . . H14 H 0.2021 0.4363 0.1116 0.015 Uiso 1 1 calc R . . C15 C 0.1478(6) 0.5449(4) 0.0556(11) 0.0140(16) Uiso 1 1 d D . . C16 C 0.2354(7) 0.5590(4) -0.0099(13) 0.0195(18) Uiso 1 1 d D . . H16A H 0.3076 0.5224 0.0014 0.029 Uiso 1 1 calc R . . H16B H 0.2657 0.6144 -0.0057 0.029 Uiso 1 1 calc R . . H16C H 0.1895 0.5492 -0.0674 0.029 Uiso 1 1 calc R . . C31 C 0.1760(6) 0.5685(4) 0.3258(14) 0.0164(17) Uiso 1 1 d D . . H31A H 0.2354 0.5260 0.3475 0.025 Uiso 1 1 calc R . . H31B H 0.2112 0.6206 0.3455 0.025 Uiso 1 1 calc R . . H31C H 0.1614 0.5673 0.2631 0.025 Uiso 1 1 calc R . . C32 C 0.0518(6) 0.5555(4) 0.3585(12) 0.0131(16) Uiso 1 1 d D . . C33 C -0.0286(6) 0.4886(4) 0.3509(12) 0.0116(16) Uiso 1 1 d D . . C34 C -0.1261(6) 0.4944(4) 0.4056(12) 0.0126(16) Uiso 1 1 d D . . H34 H -0.1854 0.4530 0.4099 0.015 Uiso 1 1 calc R . . C35 C -0.1242(6) 0.5646(4) 0.4499(12) 0.0131(16) Uiso 1 1 d D . . C36 C -0.2076(7) 0.5915(4) 0.5134(14) 0.0232(19) Uiso 1 1 d D . . H36A H -0.2685 0.5492 0.5203 0.035 Uiso 1 1 calc R . . H36B H -0.2529 0.6403 0.4924 0.035 Uiso 1 1 calc R . . H36C H -0.1553 0.6023 0.5687 0.035 Uiso 1 1 calc R . . C51 C 0.4825(6) 0.8285(4) 0.2902(11) 0.0099(16) Uiso 1 1 d D . . C52 C 0.4707(6) 0.9141(4) 0.3224(10) 0.0160(17) Uiso 1 1 d D . . C53 C 0.4915(6) 0.9681(4) 0.2439(10) 0.0138(17) Uiso 1 1 d D . . C54 C 0.5649(7) 0.9124(5) 0.1937(12) 0.022(2) Uiso 1 1 d D . . C55 C 0.5202(6) 0.8278(4) 0.2112(12) 0.0094(16) Uiso 1 1 d D . . C61 C 0.6574(7) 0.6721(4) 0.3078(14) 0.0172(18) Uiso 1 1 d D . . H61A H 0.6293 0.6522 0.2498 0.026 Uiso 1 1 calc R . . H61B H 0.7101 0.6315 0.3409 0.026 Uiso 1 1 calc R . . H61C H 0.7064 0.7213 0.3052 0.026 Uiso 1 1 calc R . . C62 C 0.5432(7) 0.6896(4) 0.3507(12) 0.0149(17) Uiso 1 1 d D . . C63 C 0.4657(6) 0.7588(4) 0.3455(13) 0.0134(17) Uiso 1 1 d D . . C64 C 0.3720(6) 0.7548(4) 0.4020(12) 0.0146(17) Uiso 1 1 d D . . H64 H 0.3127 0.7961 0.4066 0.018 Uiso 1 1 calc R . . C65 C 0.3776(7) 0.6856(4) 0.4478(12) 0.0178(18) Uiso 1 1 d D . . C66 C 0.2954(8) 0.6594(5) 0.5138(13) 0.028(2) Uiso 1 1 d D . . H66A H 0.3464 0.6587 0.5708 0.041 Uiso 1 1 calc R . . H66B H 0.2619 0.6057 0.4994 0.041 Uiso 1 1 calc R . . H66C H 0.2253 0.6971 0.5133 0.041 Uiso 1 1 calc R . . C81 C 0.3332(7) 0.6781(5) 0.1621(15) 0.0173(18) Uiso 1 1 d D . . H81A H 0.3415 0.6855 0.2241 0.026 Uiso 1 1 calc R . . H81B H 0.3079 0.6228 0.1476 0.026 Uiso 1 1 calc R . . H81C H 0.2691 0.7149 0.1334 0.026 Uiso 1 1 calc R . . C82 C 0.4588(6) 0.6952(4) 0.1331(12) 0.0121(16) Uiso 1 1 d D . . C83 C 0.5359(6) 0.7628(4) 0.1523(13) 0.0125(16) Uiso 1 1 d D . . C84 C 0.6403(6) 0.7640(4) 0.1028(12) 0.0117(16) Uiso 1 1 d D . . H84 H 0.6992 0.8067 0.1061 0.014 Uiso 1 1 calc R . . C85 C 0.6462(6) 0.6991(4) 0.0518(12) 0.0132(16) Uiso 1 1 d D . . C86 C 0.7408(7) 0.6844(4) -0.0077(13) 0.0187(18) Uiso 1 1 d D . . H86A H 0.7013 0.6949 -0.0667 0.028 Uiso 1 1 calc R . . H86B H 0.7693 0.6286 -0.0025 0.028 Uiso 1 1 calc R . . H86C H 0.8134 0.7201 0.0074 0.028 Uiso 1 1 calc R . . F1 F 0.1284(4) 0.3071(2) 0.1585(9) 0.0243(12) Uiso 1 1 d D . . F2 F -0.0750(4) 0.3148(3) 0.1106(10) 0.0338(14) Uiso 1 1 d D . . F3 F 0.0975(4) 0.2509(3) 0.3041(9) 0.0348(14) Uiso 1 1 d D . . F4 F -0.0875(4) 0.2132(3) 0.2379(10) 0.0334(13) Uiso 1 1 d D . . F5 F -0.0488(5) 0.3161(3) 0.3983(10) 0.0317(15) Uiso 1 1 d D . . F6 F -0.2047(4) 0.3363(2) 0.2936(9) 0.0207(11) Uiso 1 1 d D . . F7 F 0.5594(4) 0.9333(3) 0.3920(9) 0.0304(13) Uiso 1 1 d D . . F8 F 0.3544(4) 0.9297(2) 0.3455(9) 0.0263(12) Uiso 1 1 d D . . F9 F 0.5567(4) 1.0362(2) 0.2696(9) 0.0245(12) Uiso 1 1 d D . . F10 F 0.3782(4) 0.9881(3) 0.1974(9) 0.0282(12) Uiso 1 1 d D . . F11 F 0.6941(4) 0.9178(2) 0.2207(9) 0.0203(11) Uiso 1 1 d D . . F12 F 0.5447(5) 0.9324(3) 0.1052(10) 0.0295(14) Uiso 1 1 d D . . S1 S 0.02613(16) 0.61239(10) 0.0689(4) 0.014(4) Uani 1 1 d D . . S2 S -0.00142(17) 0.62642(9) 0.4255(4) 0.014(5) Uani 1 1 d D . . S3 S 0.49576(17) 0.62206(10) 0.4236(4) 0.020(5) Uani 1 1 d D . . S4 S 0.52129(16) 0.63292(10) 0.0614(4) 0.014(4) Uani 1 1 d 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 S1 0.0144(8) 0.0156(8) 0.012(14) 0.0013(19) 0.005(2) -0.0023(6) S2 0.0171(9) 0.0127(9) 0.011(14) -0.0032(17) 0.001(2) 0.0005(6) S3 0.0181(9) 0.0156(9) 0.027(15) 0.0014(18) 0.004(2) -0.0024(6) S4 0.0154(9) 0.0136(8) 0.014(14) -0.0019(18) 0.006(2) 0.0000(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 C1 C5 1.335(16) . ? C1 C13 1.454(12) . ? C1 C2 1.506(10) . ? C2 F1 1.341(9) . ? C2 F2 1.345(14) . ? C2 C3 1.571(16) . ? C3 F4 1.327(8) . ? C3 F3 1.329(10) . ? C3 C4 1.473(14) . ? C4 F5 1.345(17) . ? C4 F6 1.357(8) . ? C4 C5 1.498(10) . ? C5 C33 1.453(14) . ? C11 C12 1.496(12) . ? C12 C13 1.379(9) . ? C12 S1 1.716(13) . ? C13 C14 1.419(13) . ? C14 C15 1.357(14) . ? C15 C16 1.491(16) . ? C15 S1 1.726(7) . ? C31 C32 1.488(11) . ? C32 C33 1.376(8) . ? C32 S2 1.709(12) . ? C33 C34 1.431(14) . ? C34 C35 1.339(13) . ? C35 C36 1.484(15) . ? C35 S2 1.726(7) . ? C51 C55 1.345(14) . ? C51 C63 1.456(17) . ? C51 C52 1.498(10) . ? C52 F7 1.349(14) . ? C52 F8 1.349(9) . ? C52 C53 1.547(16) . ? C53 F10 1.333(11) . ? C53 F9 1.337(9) . ? C53 C54 1.490(14) . ? C54 F11 1.360(9) . ? C54 F12 1.395(17) . ? C54 C55 1.500(11) . ? C55 C83 1.429(18) . ? C61 C62 1.487(13) . ? C62 C63 1.390(8) . ? C62 S3 1.710(13) . ? C63 C64 1.417(15) . ? C64 C65 1.332(13) . ? C65 C66 1.501(15) . ? C65 S3 1.706(8) . ? C81 C82 1.485(11) . ? C82 C83 1.377(9) . ? C82 S4 1.713(13) . ? C83 C84 1.433(14) . ? C84 C85 1.331(13) . ? C85 C86 1.478(15) . ? C85 S4 1.726(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 C5 C1 C13 128.9(8) . . ? C5 C1 C2 112.5(8) . . ? C13 C1 C2 118.5(11) . . ? F1 C2 F2 106.6(11) . . ? F1 C2 C1 113.4(6) . . ? F2 C2 C1 113.8(7) . . ? F1 C2 C3 110.4(8) . . ? F2 C2 C3 110.5(7) . . ? C1 C2 C3 102.1(9) . . ? F4 C3 F3 107.6(6) . . ? F4 C3 C4 113.2(7) . . ? F3 C3 C4 111.3(12) . . ? F4 C3 C2 112.7(12) . . ? F3 C3 C2 108.2(7) . . ? C4 C3 C2 103.8(8) . . ? F5 C4 F6 105.1(10) . . ? F5 C4 C3 109.4(9) . . ? F6 C4 C3 111.9(9) . . ? F5 C4 C5 114.3(11) . . ? F6 C4 C5 110.4(8) . . ? C3 C4 C5 105.8(9) . . ? C1 C5 C33 130.1(8) . . ? C1 C5 C4 108.3(9) . . ? C33 C5 C4 121.2(12) . . ? C13 C12 C11 127.6(11) . . ? C13 C12 S1 109.5(8) . . ? C11 C12 S1 122.8(7) . . ? C12 C13 C14 113.2(9) . . ? C12 C13 C1 123.9(9) . . ? C14 C13 C1 122.8(6) . . ? C15 C14 C13 113.7(6) . . ? C14 C15 C16 128.0(7) . . ? C14 C15 S1 109.9(7) . . ? C16 C15 S1 122.0(7) . . ? C33 C32 C31 130.1(9) . . ? C33 C32 S2 109.8(8) . . ? C31 C32 S2 119.8(7) . . ? C32 C33 C34 112.5(9) . . ? C32 C33 C5 126.2(10) . . ? C34 C33 C5 121.3(6) . . ? C35 C34 C33 114.0(7) . . ? C34 C35 C36 129.2(7) . . ? C34 C35 S2 110.0(8) . . ? C36 C35 S2 120.7(6) . . ? C55 C51 C63 127.7(9) . . ? C55 C51 C52 111.3(9) . . ? C63 C51 C52 120.8(14) . . ? F7 C52 F8 106.5(11) . . ? F7 C52 C51 113.7(7) . . ? F8 C52 C51 113.0(6) . . ? F7 C52 C53 109.4(7) . . ? F8 C52 C53 110.2(8) . . ? C51 C52 C53 104.0(10) . . ? F10 C53 F9 109.3(6) . . ? F10 C53 C54 111.0(11) . . ? F9 C53 C54 112.5(7) . . ? F10 C53 C52 110.0(7) . . ? F9 C53 C52 111.8(11) . . ? C54 C53 C52 102.1(8) . . ? F11 C54 F12 106.2(10) . . ? F11 C54 C53 111.9(10) . . ? F12 C54 C53 111.1(10) . . ? F11 C54 C55 109.3(8) . . ? F12 C54 C55 112.9(11) . . ? C53 C54 C55 105.5(9) . . ? C51 C55 C83 132.0(9) . . ? C51 C55 C54 107.5(10) . . ? C83 C55 C54 120.1(13) . . ? C63 C62 C61 129.6(10) . . ? C63 C62 S3 109.6(9) . . ? C61 C62 S3 120.6(6) . . ? C62 C63 C64 112.6(10) . . ? C62 C63 C51 123.2(11) . . ? C64 C63 C51 124.1(7) . . ? C65 C64 C63 113.1(7) . . ? C64 C65 C66 128.6(7) . . ? C64 C65 S3 111.9(9) . . ? C66 C65 S3 119.5(6) . . ? C83 C82 C81 127.4(10) . . ? C83 C82 S4 110.2(8) . . ? C81 C82 S4 122.2(7) . . ? C82 C83 C55 127.9(10) . . ? C82 C83 C84 111.6(10) . . ? C55 C83 C84 120.5(6) . . ? C85 C84 C83 114.7(7) . . ? C84 C85 C86 126.8(7) . . ? C84 C85 S4 110.0(8) . . ? C86 C85 S4 123.1(7) . . ? C12 S1 C15 93.6(5) . . ? C32 S2 C35 93.5(4) . . ? C65 S3 C62 92.8(5) . . ? C82 S4 C85 93.2(5) . . ? 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 C5 C1 C2 F1 -125.0(11) . . . . ? C13 C1 C2 F1 59.5(13) . . . . ? C5 C1 C2 F2 112.9(11) . . . . ? C13 C1 C2 F2 -62.6(10) . . . . ? C5 C1 C2 C3 -6.2(8) . . . . ? C13 C1 C2 C3 178.3(6) . . . . ? F1 C2 C3 F4 -95.6(8) . . . . ? F2 C2 C3 F4 22.0(7) . . . . ? C1 C2 C3 F4 143.4(6) . . . . ? F1 C2 C3 F3 23.2(11) . . . . ? F2 C2 C3 F3 140.9(8) . . . . ? C1 C2 C3 F3 -97.7(8) . . . . ? F1 C2 C3 C4 141.5(9) . . . . ? F2 C2 C3 C4 -100.8(8) . . . . ? C1 C2 C3 C4 20.6(8) . . . . ? F4 C3 C4 F5 86.6(12) . . . . ? F3 C3 C4 F5 -34.7(9) . . . . ? C2 C3 C4 F5 -150.9(6) . . . . ? F4 C3 C4 F6 -29.5(17) . . . . ? F3 C3 C4 F6 -150.8(10) . . . . ? C2 C3 C4 F6 93.1(10) . . . . ? F4 C3 C4 C5 -149.8(11) . . . . ? F3 C3 C4 C5 88.9(12) . . . . ? C2 C3 C4 C5 -27.3(11) . . . . ? C13 C1 C5 C33 -9.5(15) . . . . ? C2 C1 C5 C33 175.6(8) . . . . ? C13 C1 C5 C4 164.1(8) . . . . ? C2 C1 C5 C4 -10.8(10) . . . . ? F5 C4 C5 C1 145.2(8) . . . . ? F6 C4 C5 C1 -96.6(12) . . . . ? C3 C4 C5 C1 24.7(12) . . . . ? F5 C4 C5 C33 -40.5(11) . . . . ? F6 C4 C5 C33 77.7(15) . . . . ? C3 C4 C5 C33 -161.0(9) . . . . ? C11 C12 C13 C14 178.7(13) . . . . ? S1 C12 C13 C14 0.1(15) . . . . ? C11 C12 C13 C1 2(2) . . . . ? S1 C12 C13 C1 -176.9(10) . . . . ? C5 C1 C13 C12 -42.6(17) . . . . ? C2 C1 C13 C12 132.1(13) . . . . ? C5 C1 C13 C14 140.6(11) . . . . ? C2 C1 C13 C14 -44.7(14) . . . . ? C12 C13 C14 C15 -1.0(16) . . . . ? C1 C13 C14 C15 176.1(11) . . . . ? C13 C14 C15 C16 -174.9(12) . . . . ? C13 C14 C15 S1 1.4(14) . . . . ? C31 C32 C33 C34 168.8(15) . . . . ? S2 C32 C33 C34 -4.6(15) . . . . ? C31 C32 C33 C5 -13(3) . . . . ? S2 C32 C33 C5 173.7(10) . . . . ? C1 C5 C33 C32 -32.2(18) . . . . ? C4 C5 C33 C32 154.9(13) . . . . ? C1 C5 C33 C34 146.0(11) . . . . ? C4 C5 C33 C34 -26.8(15) . . . . ? C32 C33 C34 C35 3.1(16) . . . . ? C5 C33 C34 C35 -175.4(12) . . . . ? C33 C34 C35 C36 -178.6(12) . . . . ? C33 C34 C35 S2 0.0(14) . . . . ? C55 C51 C52 F7 -112.1(10) . . . . ? C63 C51 C52 F7 62.5(10) . . . . ? C55 C51 C52 F8 126.3(11) . . . . ? C63 C51 C52 F8 -59.1(14) . . . . ? C55 C51 C52 C53 6.8(8) . . . . ? C63 C51 C52 C53 -178.6(7) . . . . ? F7 C52 C53 F10 -143.3(8) . . . . ? F8 C52 C53 F10 -26.5(11) . . . . ? C51 C52 C53 F10 95.0(8) . . . . ? F7 C52 C53 F9 -21.7(7) . . . . ? F8 C52 C53 F9 95.1(8) . . . . ? C51 C52 C53 F9 -143.4(6) . . . . ? F7 C52 C53 C54 98.8(7) . . . . ? F8 C52 C53 C54 -144.4(9) . . . . ? C51 C52 C53 C54 -22.9(8) . . . . ? F10 C53 C54 F11 154.4(10) . . . . ? F9 C53 C54 F11 31.6(16) . . . . ? C52 C53 C54 F11 -88.4(10) . . . . ? F10 C53 C54 F12 36.0(9) . . . . ? F9 C53 C54 F12 -86.9(12) . . . . ? C52 C53 C54 F12 153.2(7) . . . . ? F10 C53 C54 C55 -86.8(12) . . . . ? F9 C53 C54 C55 150.4(11) . . . . ? C52 C53 C54 C55 30.4(11) . . . . ? C63 C51 C55 C83 10.8(15) . . . . ? C52 C51 C55 C83 -175.1(9) . . . . ? C63 C51 C55 C54 -161.6(9) . . . . ? C52 C51 C55 C54 12.6(9) . . . . ? F11 C54 C55 C51 92.6(11) . . . . ? F12 C54 C55 C51 -149.4(7) . . . . ? C53 C54 C55 C51 -27.9(12) . . . . ? F11 C54 C55 C83 -80.9(15) . . . . ? F12 C54 C55 C83 37.1(11) . . . . ? C53 C54 C55 C83 158.7(10) . . . . ? C61 C62 C63 C64 -175.1(14) . . . . ? S3 C62 C63 C64 0.9(15) . . . . ? C61 C62 C63 C51 3(2) . . . . ? S3 C62 C63 C51 179.0(11) . . . . ? C55 C51 C63 C62 34.9(18) . . . . ? C52 C51 C63 C62 -138.7(13) . . . . ? C55 C51 C63 C64 -147.2(11) . . . . ? C52 C51 C63 C64 39.1(15) . . . . ? C62 C63 C64 C65 -0.2(16) . . . . ? C51 C63 C64 C65 -178.2(13) . . . . ? C63 C64 C65 C66 179.9(12) . . . . ? C63 C64 C65 S3 -0.6(14) . . . . ? C81 C82 C83 C55 7(3) . . . . ? S4 C82 C83 C55 -177.8(12) . . . . ? C81 C82 C83 C84 -171.5(14) . . . . ? S4 C82 C83 C84 3.7(15) . . . . ? C51 C55 C83 C82 39(2) . . . . ? C54 C55 C83 C82 -149.0(14) . . . . ? C51 C55 C83 C84 -142.2(11) . . . . ? C54 C55 C83 C84 29.3(16) . . . . ? C82 C83 C84 C85 -2.8(17) . . . . ? C55 C83 C84 C85 178.6(13) . . . . ? C83 C84 C85 C86 178.5(12) . . . . ? C83 C84 C85 S4 0.5(14) . . . . ? C13 C12 S1 C15 0.5(11) . . . . ? C11 C12 S1 C15 -178.1(12) . . . . ? C14 C15 S1 C12 -1.1(10) . . . . ? C16 C15 S1 C12 175.4(10) . . . . ? C33 C32 S2 C35 4.0(12) . . . . ? C31 C32 S2 C35 -170.2(12) . . . . ? C34 C35 S2 C32 -2.3(11) . . . . ? C36 C35 S2 C32 176.5(11) . . . . ? C64 C65 S3 C62 1.0(11) . . . . ? C66 C65 S3 C62 -179.5(11) . . . . ? C63 C62 S3 C65 -1.1(11) . . . . ? C61 C62 S3 C65 175.3(12) . . . . ? C83 C82 S4 C85 -3.0(12) . . . . ? C81 C82 S4 C85 172.5(13) . . . . ? C84 C85 S4 C82 1.4(11) . . . . ? C86 C85 S4 C82 -176.7(11) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961271' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6.70GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety '2(C17 H14 F6 S2)' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.4886(10) _cell_length_b 16.3135(16) _cell_length_c 15.5602(96) _cell_angle_alpha 90.00 _cell_angle_beta 99.0816(16) _cell_angle_gamma 90.00 _cell_volume 2629.1(15) _cell_formula_units_Z 8 _cell_measurement_reflns_used 889 _cell_measurement_theta_min 2.7331 _cell_measurement_theta_max 28.0684 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.003 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 5726 _diffrn_reflns_av_R_equivalents 0.0971 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.62 _reflns_number_total 1536 _reflns_number_gt 1212 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.282 _diffrn_reflns_theta_full 25.62 _diffrn_measured_fraction_theta_full 0.282 _refine_diff_density_max 0.463 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.068 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 1536 _refine_ls_number_parameters 224 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1851 _refine_ls_wR_factor_gt 0.1714 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.026 _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 0.0136(7) 0.4148(4) 0.2148(10) 0.0147(17) Uiso 1 1 d D . . C2 C 0.0135(6) 0.3279(4) 0.1811(10) 0.0160(16) Uiso 1 1 d D . . C3 C -0.0150(6) 0.2772(4) 0.2622(10) 0.0152(16) Uiso 1 1 d D . . C4 C -0.0765(6) 0.3368(4) 0.3142(11) 0.0190(18) Uiso 1 1 d D . . C5 C -0.0222(6) 0.4190(4) 0.2930(11) 0.0134(16) Uiso 1 1 d D . . C11 C -0.1498(6) 0.5736(4) 0.1832(13) 0.0190(17) Uiso 1 1 d D . . H11A H -0.1950 0.5244 0.1941 0.029 Uiso 1 1 calc R . . H11B H -0.2057 0.6081 0.1440 0.029 Uiso 1 1 calc R . . H11C H -0.1233 0.6021 0.2370 0.029 Uiso 1 1 calc R . . C12 C -0.0328(6) 0.5517(4) 0.1432(11) 0.0149(15) Uiso 1 1 d D . . C13 C 0.0412(6) 0.4816(4) 0.1582(10) 0.0166(16) Uiso 1 1 d D . . C14 C 0.1428(6) 0.4790(3) 0.1080(11) 0.0140(15) Uiso 1 1 d D . . H14 H 0.2016 0.4360 0.1109 0.017 Uiso 1 1 calc R . . C15 C 0.1464(6) 0.5450(4) 0.0551(11) 0.0180(16) Uiso 1 1 d D . . C16 C 0.2358(6) 0.5596(4) -0.0087(13) 0.0190(17) Uiso 1 1 d D . . H16A H 0.3070 0.5220 0.0022 0.028 Uiso 1 1 calc R . . H16B H 0.2676 0.6148 -0.0029 0.028 Uiso 1 1 calc R . . H16C H 0.1904 0.5513 -0.0666 0.028 Uiso 1 1 calc R . . C31 C 0.1784(6) 0.5669(4) 0.3262(13) 0.0200(17) Uiso 1 1 d D . . H31A H 0.2367 0.5240 0.3492 0.030 Uiso 1 1 calc R . . H31B H 0.2144 0.6190 0.3456 0.030 Uiso 1 1 calc R . . H31C H 0.1655 0.5650 0.2637 0.030 Uiso 1 1 calc R . . C32 C 0.0528(5) 0.5555(3) 0.3571(11) 0.0137(15) Uiso 1 1 d D . . C33 C -0.0287(6) 0.4885(3) 0.3497(11) 0.0139(15) Uiso 1 1 d D . . C34 C -0.1253(6) 0.4946(4) 0.4044(12) 0.0161(16) Uiso 1 1 d D . . H34 H -0.1858 0.4536 0.4081 0.019 Uiso 1 1 calc R . . C35 C -0.1213(6) 0.5656(4) 0.4507(11) 0.0171(16) Uiso 1 1 d D . . C36 C -0.2065(7) 0.5923(4) 0.5155(14) 0.0272(19) Uiso 1 1 d D . . H36A H -0.2665 0.5494 0.5226 0.041 Uiso 1 1 calc R . . H36B H -0.2531 0.6408 0.4944 0.041 Uiso 1 1 calc R . . H36C H -0.1540 0.6038 0.5705 0.041 Uiso 1 1 calc R . . C51 C 0.4834(7) 0.8288(4) 0.2914(12) 0.0142(17) Uiso 1 1 d D . . C52 C 0.4702(6) 0.9151(4) 0.3232(10) 0.0175(17) Uiso 1 1 d D . . C53 C 0.4926(6) 0.9683(4) 0.2451(10) 0.0165(16) Uiso 1 1 d D . . C54 C 0.5660(7) 0.9127(5) 0.1946(11) 0.0211(19) Uiso 1 1 d D . . C55 C 0.5188(7) 0.8281(4) 0.2119(12) 0.0144(17) Uiso 1 1 d D . . C61 C 0.6586(6) 0.6727(4) 0.3066(13) 0.0211(18) Uiso 1 1 d D . . H61A H 0.6323 0.6437 0.2530 0.032 Uiso 1 1 calc R . . H61B H 0.7194 0.6401 0.3446 0.032 Uiso 1 1 calc R . . H61C H 0.6982 0.7237 0.2946 0.032 Uiso 1 1 calc R . . C62 C 0.5434(6) 0.6894(3) 0.3491(11) 0.0148(15) Uiso 1 1 d D . . C63 C 0.4659(6) 0.7586(4) 0.3461(12) 0.0144(15) Uiso 1 1 d D . . C64 C 0.3731(6) 0.7541(4) 0.4031(11) 0.0163(16) Uiso 1 1 d D . . H64 H 0.3139 0.7956 0.4083 0.020 Uiso 1 1 calc R . . C65 C 0.3794(6) 0.6839(4) 0.4489(11) 0.0190(17) Uiso 1 1 d D . . C66 C 0.2962(7) 0.6572(4) 0.5143(13) 0.029(2) Uiso 1 1 d D . . H66A H 0.3467 0.6568 0.5714 0.044 Uiso 1 1 calc R . . H66B H 0.2634 0.6032 0.5000 0.044 Uiso 1 1 calc R . . H66C H 0.2254 0.6947 0.5133 0.044 Uiso 1 1 calc R . . C81 C 0.3312(6) 0.6788(4) 0.1607(13) 0.0198(17) Uiso 1 1 d D . . H81A H 0.3401 0.6820 0.2229 0.030 Uiso 1 1 calc R . . H81B H 0.3015 0.6251 0.1418 0.030 Uiso 1 1 calc R . . H81C H 0.2699 0.7190 0.1351 0.030 Uiso 1 1 calc R . . C82 C 0.4589(6) 0.6948(4) 0.1329(11) 0.0148(15) Uiso 1 1 d D . . C83 C 0.5361(6) 0.7629(4) 0.1519(13) 0.0163(16) Uiso 1 1 d D . . C84 C 0.6398(6) 0.7643(4) 0.1026(12) 0.0145(15) Uiso 1 1 d D . . H84 H 0.6982 0.8075 0.1052 0.017 Uiso 1 1 calc R . . C85 C 0.6461(6) 0.6985(4) 0.0521(11) 0.0154(16) Uiso 1 1 d D . . C86 C 0.7404(6) 0.6842(4) -0.0087(13) 0.0217(17) Uiso 1 1 d D . . H86A H 0.6978 0.6905 -0.0676 0.032 Uiso 1 1 calc R . . H86B H 0.7747 0.6297 -0.0005 0.032 Uiso 1 1 calc R . . H86C H 0.8096 0.7232 0.0030 0.032 Uiso 1 1 calc R . . F1 F 0.1276(4) 0.3062(2) 0.1584(9) 0.0259(11) Uiso 1 1 d D . . F2 F -0.0769(4) 0.3139(3) 0.1097(9) 0.0339(13) Uiso 1 1 d D . . F3 F 0.0977(4) 0.2508(3) 0.3065(9) 0.0338(12) Uiso 1 1 d D . . F4 F -0.0888(4) 0.2118(3) 0.2377(9) 0.0344(12) Uiso 1 1 d D . . F5 F -0.0510(4) 0.3155(3) 0.3983(10) 0.0331(14) Uiso 1 1 d D . . F6 F -0.2059(3) 0.3362(2) 0.2918(8) 0.0227(11) Uiso 1 1 d D . . F7 F 0.5608(4) 0.9339(2) 0.3940(9) 0.0324(12) Uiso 1 1 d D . . F8 F 0.3547(4) 0.9303(2) 0.3464(9) 0.0283(12) Uiso 1 1 d D . . F9 F 0.5565(4) 1.0375(2) 0.2691(9) 0.0280(11) Uiso 1 1 d D . . F10 F 0.3780(4) 0.9885(2) 0.1975(9) 0.0279(11) Uiso 1 1 d D . . F11 F 0.6944(3) 0.9177(2) 0.2223(9) 0.0231(10) Uiso 1 1 d D . . F12 F 0.5470(4) 0.9329(3) 0.1073(10) 0.0307(13) Uiso 1 1 d D . . S1 S 0.02597(15) 0.61310(10) 0.0689(4) 0.0168(5) Uiso 1 1 d D . . S2 S 0.00025(15) 0.62697(9) 0.4252(4) 0.016(4) Uani 1 1 d D . . S3 S 0.49694(15) 0.62109(9) 0.4222(4) 0.015(4) Uani 1 1 d D . . S4 S 0.52080(15) 0.63210(9) 0.0606(4) 0.014(4) Uani 1 1 d 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 S2 0.0189(8) 0.0156(8) 0.013(13) -0.0033(17) 0.003(2) 0.0001(6) S3 0.0189(8) 0.0185(8) 0.009(14) 0.0002(18) 0.003(2) -0.0008(6) S4 0.0172(8) 0.0166(8) 0.011(13) -0.0002(18) 0.0058(19) -0.0005(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 C1 C5 1.331(16) . ? C1 C13 1.458(11) . ? C1 C2 1.510(9) . ? C2 F1 1.347(9) . ? C2 F2 1.362(13) . ? C2 C3 1.576(16) . ? C3 F4 1.337(8) . ? C3 F3 1.342(10) . ? C3 C4 1.477(14) . ? C4 F5 1.340(17) . ? C4 F6 1.346(8) . ? C4 C5 1.513(10) . ? C5 C33 1.445(14) . ? C11 C12 1.504(13) . ? C12 C13 1.381(8) . ? C12 S1 1.716(13) . ? C13 C14 1.418(13) . ? C14 C15 1.358(13) . ? C15 C16 1.489(15) . ? C15 S1 1.721(7) . ? C31 C32 1.484(12) . ? C32 C33 1.381(7) . ? C32 S2 1.724(12) . ? C33 C34 1.426(14) . ? C34 C35 1.361(13) . ? C35 C36 1.513(16) . ? C35 S2 1.717(8) . ? C51 C55 1.348(14) . ? C51 C63 1.456(17) . ? C51 C52 1.506(10) . ? C52 F8 1.340(10) . ? C52 F7 1.370(13) . ? C52 C53 1.541(16) . ? C53 F9 1.335(8) . ? C53 F10 1.349(10) . ? C53 C54 1.492(14) . ? C54 F11 1.350(8) . ? C54 F12 1.381(17) . ? C54 C55 1.505(10) . ? C55 C83 1.445(19) . ? C61 C62 1.491(13) . ? C62 C63 1.387(8) . ? C62 S3 1.717(12) . ? C63 C64 1.419(15) . ? C64 C65 1.345(12) . ? C65 C66 1.506(15) . ? C65 S3 1.705(8) . ? C81 C82 1.494(11) . ? C82 C83 1.379(8) . ? C82 S4 1.722(13) . ? C83 C84 1.427(14) . ? C84 C85 1.337(13) . ? C85 C86 1.492(15) . ? C85 S4 1.724(7) . ? 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 C5 C1 C13 128.7(8) . . ? C5 C1 C2 112.3(9) . . ? C13 C1 C2 118.8(11) . . ? F1 C2 F2 105.9(10) . . ? F1 C2 C1 112.7(6) . . ? F2 C2 C1 113.7(7) . . ? F1 C2 C3 111.1(7) . . ? F2 C2 C3 111.7(7) . . ? C1 C2 C3 101.9(9) . . ? F4 C3 F3 108.3(6) . . ? F4 C3 C4 113.4(7) . . ? F3 C3 C4 110.8(11) . . ? F4 C3 C2 111.5(11) . . ? F3 C3 C2 108.5(7) . . ? C4 C3 C2 104.3(7) . . ? F5 C4 F6 106.8(10) . . ? F5 C4 C3 109.1(9) . . ? F6 C4 C3 111.3(9) . . ? F5 C4 C5 114.7(10) . . ? F6 C4 C5 110.4(7) . . ? C3 C4 C5 104.6(9) . . ? C1 C5 C33 130.2(9) . . ? C1 C5 C4 108.9(9) . . ? C33 C5 C4 120.4(12) . . ? C13 C12 C11 126.9(10) . . ? C13 C12 S1 110.2(8) . . ? C11 C12 S1 122.9(6) . . ? C12 C13 C14 112.5(9) . . ? C12 C13 C1 124.1(9) . . ? C14 C13 C1 123.3(6) . . ? C15 C14 C13 113.9(6) . . ? C14 C15 C16 127.7(7) . . ? C14 C15 S1 110.2(8) . . ? C16 C15 S1 122.1(6) . . ? C33 C32 C31 129.9(9) . . ? C33 C32 S2 109.4(8) . . ? C31 C32 S2 120.1(6) . . ? C32 C33 C34 112.6(9) . . ? C32 C33 C5 125.7(10) . . ? C34 C33 C5 121.7(6) . . ? C35 C34 C33 114.2(7) . . ? C34 C35 C36 128.8(7) . . ? C34 C35 S2 109.6(8) . . ? C36 C35 S2 121.6(6) . . ? C55 C51 C63 127.5(9) . . ? C55 C51 C52 111.3(10) . . ? C63 C51 C52 121.1(14) . . ? F8 C52 F7 106.5(11) . . ? F8 C52 C51 113.2(6) . . ? F7 C52 C51 112.7(7) . . ? F8 C52 C53 111.4(7) . . ? F7 C52 C53 109.6(7) . . ? C51 C52 C53 103.5(11) . . ? F9 C53 F10 108.1(5) . . ? F9 C53 C54 112.5(7) . . ? F10 C53 C54 110.4(11) . . ? F9 C53 C52 112.8(11) . . ? F10 C53 C52 109.7(7) . . ? C54 C53 C52 103.2(8) . . ? F11 C54 F12 106.4(10) . . ? F11 C54 C53 111.5(10) . . ? F12 C54 C53 111.5(9) . . ? F11 C54 C55 109.7(8) . . ? F12 C54 C55 113.2(11) . . ? C53 C54 C55 104.5(10) . . ? C51 C55 C83 132.8(9) . . ? C51 C55 C54 107.6(11) . . ? C83 C55 C54 118.8(14) . . ? C63 C62 C61 130.2(10) . . ? C63 C62 S3 108.9(9) . . ? C61 C62 S3 120.7(6) . . ? C62 C63 C64 113.2(10) . . ? C62 C63 C51 122.2(11) . . ? C64 C63 C51 124.6(7) . . ? C65 C64 C63 113.2(7) . . ? C64 C65 C66 128.3(7) . . ? C64 C65 S3 111.1(9) . . ? C66 C65 S3 120.6(6) . . ? C83 C82 C81 127.0(10) . . ? C83 C82 S4 110.4(8) . . ? C81 C82 S4 122.2(7) . . ? C82 C83 C84 111.7(10) . . ? C82 C83 C55 127.0(11) . . ? C84 C83 C55 121.3(7) . . ? C85 C84 C83 114.5(6) . . ? C84 C85 C86 126.7(7) . . ? C84 C85 S4 110.5(8) . . ? C86 C85 S4 122.7(7) . . ? C12 S1 C15 93.2(5) . . ? C35 S2 C32 93.9(4) . . ? C65 S3 C62 93.6(5) . . ? C82 S4 C85 92.7(5) . . ? 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 C5 C1 C2 F1 -125.6(11) . . . . ? C13 C1 C2 F1 59.0(12) . . . . ? C5 C1 C2 F2 113.8(10) . . . . ? C13 C1 C2 F2 -61.6(10) . . . . ? C5 C1 C2 C3 -6.5(8) . . . . ? C13 C1 C2 C3 178.1(6) . . . . ? F1 C2 C3 F4 -95.5(8) . . . . ? F2 C2 C3 F4 22.6(7) . . . . ? C1 C2 C3 F4 144.3(5) . . . . ? F1 C2 C3 F3 23.7(10) . . . . ? F2 C2 C3 F3 141.7(8) . . . . ? C1 C2 C3 F3 -96.5(8) . . . . ? F1 C2 C3 C4 141.8(8) . . . . ? F2 C2 C3 C4 -100.1(7) . . . . ? C1 C2 C3 C4 21.6(7) . . . . ? F4 C3 C4 F5 87.3(11) . . . . ? F3 C3 C4 F5 -34.7(9) . . . . ? C2 C3 C4 F5 -151.3(6) . . . . ? F4 C3 C4 F6 -30.3(16) . . . . ? F3 C3 C4 F6 -152.3(9) . . . . ? C2 C3 C4 F6 91.1(10) . . . . ? F4 C3 C4 C5 -149.5(11) . . . . ? F3 C3 C4 C5 88.5(11) . . . . ? C2 C3 C4 C5 -28.1(10) . . . . ? C13 C1 C5 C33 -8.7(15) . . . . ? C2 C1 C5 C33 176.4(7) . . . . ? C13 C1 C5 C4 163.7(7) . . . . ? C2 C1 C5 C4 -11.2(10) . . . . ? F5 C4 C5 C1 145.0(8) . . . . ? F6 C4 C5 C1 -94.4(12) . . . . ? C3 C4 C5 C1 25.4(11) . . . . ? F5 C4 C5 C33 -41.8(10) . . . . ? F6 C4 C5 C33 78.9(14) . . . . ? C3 C4 C5 C33 -161.3(9) . . . . ? C11 C12 C13 C14 178.2(11) . . . . ? S1 C12 C13 C14 -0.8(13) . . . . ? C11 C12 C13 C1 2(2) . . . . ? S1 C12 C13 C1 -176.9(9) . . . . ? C5 C1 C13 C12 -43.3(16) . . . . ? C2 C1 C13 C12 131.3(12) . . . . ? C5 C1 C13 C14 141.1(11) . . . . ? C2 C1 C13 C14 -44.4(13) . . . . ? C12 C13 C14 C15 -0.5(15) . . . . ? C1 C13 C14 C15 175.6(10) . . . . ? C13 C14 C15 C16 -176.8(11) . . . . ? C13 C14 C15 S1 1.6(13) . . . . ? C31 C32 C33 C34 166.8(14) . . . . ? S2 C32 C33 C34 -4.4(13) . . . . ? C31 C32 C33 C5 -14(2) . . . . ? S2 C32 C33 C5 174.8(10) . . . . ? C1 C5 C33 C32 -33.0(17) . . . . ? C4 C5 C33 C32 155.4(12) . . . . ? C1 C5 C33 C34 146.2(11) . . . . ? C4 C5 C33 C34 -25.5(14) . . . . ? C32 C33 C34 C35 2.1(15) . . . . ? C5 C33 C34 C35 -177.2(11) . . . . ? C33 C34 C35 C36 -179.1(11) . . . . ? C33 C34 C35 S2 1.4(13) . . . . ? C55 C51 C52 F8 125.5(11) . . . . ? C63 C51 C52 F8 -57.8(13) . . . . ? C55 C51 C52 F7 -113.6(10) . . . . ? C63 C51 C52 F7 63.1(10) . . . . ? C55 C51 C52 C53 4.8(8) . . . . ? C63 C51 C52 C53 -178.6(6) . . . . ? F8 C52 C53 F9 94.2(8) . . . . ? F7 C52 C53 F9 -23.4(8) . . . . ? C51 C52 C53 F9 -143.8(6) . . . . ? F8 C52 C53 F10 -26.4(11) . . . . ? F7 C52 C53 F10 -144.0(8) . . . . ? C51 C52 C53 F10 95.6(8) . . . . ? F8 C52 C53 C54 -144.1(8) . . . . ? F7 C52 C53 C54 98.3(7) . . . . ? C51 C52 C53 C54 -22.1(7) . . . . ? F9 C53 C54 F11 34.1(15) . . . . ? F10 C53 C54 F11 154.9(9) . . . . ? C52 C53 C54 F11 -87.8(10) . . . . ? F9 C53 C54 F12 -84.7(11) . . . . ? F10 C53 C54 F12 36.2(9) . . . . ? C52 C53 C54 F12 153.4(6) . . . . ? F9 C53 C54 C55 152.6(11) . . . . ? F10 C53 C54 C55 -86.6(11) . . . . ? C52 C53 C54 C55 30.7(10) . . . . ? C63 C51 C55 C83 8.1(15) . . . . ? C52 C51 C55 C83 -175.6(8) . . . . ? C63 C51 C55 C54 -161.6(8) . . . . ? C52 C51 C55 C54 14.8(9) . . . . ? F11 C54 C55 C51 90.6(12) . . . . ? F12 C54 C55 C51 -150.7(7) . . . . ? C53 C54 C55 C51 -29.1(11) . . . . ? F11 C54 C55 C83 -80.8(15) . . . . ? F12 C54 C55 C83 37.9(10) . . . . ? C53 C54 C55 C83 159.5(9) . . . . ? C61 C62 C63 C64 -173.6(12) . . . . ? S3 C62 C63 C64 0.5(13) . . . . ? C61 C62 C63 C51 4(2) . . . . ? S3 C62 C63 C51 178.5(10) . . . . ? C55 C51 C63 C62 35.7(17) . . . . ? C52 C51 C63 C62 -140.4(12) . . . . ? C55 C51 C63 C64 -146.5(11) . . . . ? C52 C51 C63 C64 37.5(14) . . . . ? C62 C63 C64 C65 0.3(15) . . . . ? C51 C63 C64 C65 -177.7(12) . . . . ? C63 C64 C65 C66 -179.2(11) . . . . ? C63 C64 C65 S3 -1.0(13) . . . . ? C81 C82 C83 C84 -169.7(13) . . . . ? S4 C82 C83 C84 3.6(14) . . . . ? C81 C82 C83 C55 9(2) . . . . ? S4 C82 C83 C55 -177.8(12) . . . . ? C51 C55 C83 C82 40.8(19) . . . . ? C54 C55 C83 C82 -150.5(13) . . . . ? C51 C55 C83 C84 -140.8(11) . . . . ? C54 C55 C83 C84 28.0(15) . . . . ? C82 C83 C84 C85 -3.5(16) . . . . ? C55 C83 C84 C85 177.8(12) . . . . ? C83 C84 C85 C86 177.8(11) . . . . ? C83 C84 C85 S4 1.7(13) . . . . ? C13 C12 S1 C15 1.5(10) . . . . ? C11 C12 S1 C15 -177.6(11) . . . . ? C14 C15 S1 C12 -1.8(10) . . . . ? C16 C15 S1 C12 176.7(9) . . . . ? C34 C35 S2 C32 -3.3(10) . . . . ? C36 C35 S2 C32 177.0(10) . . . . ? C33 C32 S2 C35 4.5(11) . . . . ? C31 C32 S2 C35 -167.7(11) . . . . ? C64 C65 S3 C62 1.1(10) . . . . ? C66 C65 S3 C62 179.4(10) . . . . ? C63 C62 S3 C65 -0.9(10) . . . . ? C61 C62 S3 C65 173.9(10) . . . . ? C83 C82 S4 C85 -2.3(11) . . . . ? C81 C82 S4 C85 171.4(11) . . . . ? C84 C85 S4 C82 0.3(10) . . . . ? C86 C85 S4 C82 -175.9(10) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961272' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_7.40GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety '2(C17 H14 F6 S2)' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.4663(8) _cell_length_b 16.2590(12) _cell_length_c 15.4270(72) _cell_angle_alpha 90.00 _cell_angle_beta 99.409(12) _cell_angle_gamma 90.00 _cell_volume 2589.9(11) _cell_formula_units_Z 8 _cell_measurement_reflns_used 862 _cell_measurement_theta_min 2.7365 _cell_measurement_theta_max 28.0611 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.033 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.382 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 7408 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 25.63 _reflns_number_total 1557 _reflns_number_gt 1303 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.290 _diffrn_reflns_theta_full 25.63 _diffrn_measured_fraction_theta_full 0.290 _refine_diff_density_max 0.497 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.067 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 1557 _refine_ls_number_parameters 229 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1752 _refine_ls_wR_factor_gt 0.1650 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.043 _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 0.0134(5) 0.4147(3) 0.2148(9) 0.0096(13) Uiso 1 1 d D . . C2 C 0.0132(5) 0.3279(3) 0.1795(9) 0.0151(14) Uiso 1 1 d D . . C3 C -0.0159(5) 0.2762(3) 0.2604(9) 0.0120(13) Uiso 1 1 d D . . C4 C -0.0768(6) 0.3363(4) 0.3144(10) 0.0147(15) Uiso 1 1 d D . . C5 C -0.0229(5) 0.4183(3) 0.2934(10) 0.0097(13) Uiso 1 1 d D . . C11 C -0.1497(6) 0.5741(3) 0.1826(12) 0.0166(14) Uiso 1 1 d D . . H11A H -0.1966 0.5250 0.1917 0.025 Uiso 1 1 calc R . . H11B H -0.2044 0.6102 0.1436 0.025 Uiso 1 1 calc R . . H11C H -0.1229 0.6012 0.2378 0.025 Uiso 1 1 calc R . . C12 C -0.0331(5) 0.5522(3) 0.1430(10) 0.0123(13) Uiso 1 1 d D . . C13 C 0.0404(5) 0.4814(3) 0.1575(10) 0.0135(14) Uiso 1 1 d D . . C14 C 0.1424(5) 0.4786(3) 0.1077(10) 0.0121(13) Uiso 1 1 d D . . H14 H 0.2012 0.4354 0.1108 0.015 Uiso 1 1 calc R . . C15 C 0.1463(5) 0.5449(3) 0.0549(10) 0.0133(13) Uiso 1 1 d D . . C16 C 0.2345(6) 0.5597(3) -0.0107(12) 0.0176(14) Uiso 1 1 d D . . H16A H 0.3061 0.5221 -0.0001 0.026 Uiso 1 1 calc R . . H16B H 0.2663 0.6152 -0.0051 0.026 Uiso 1 1 calc R . . H16C H 0.1878 0.5514 -0.0689 0.026 Uiso 1 1 calc R . . C31 C 0.1794(5) 0.5665(4) 0.3266(12) 0.0168(14) Uiso 1 1 d D . . H31A H 0.2381 0.5236 0.3499 0.025 Uiso 1 1 calc R . . H31B H 0.2159 0.6190 0.3455 0.025 Uiso 1 1 calc R . . H31C H 0.1650 0.5640 0.2636 0.025 Uiso 1 1 calc R . . C32 C 0.0541(5) 0.5556(3) 0.3588(11) 0.0128(13) Uiso 1 1 d D . . C33 C -0.0281(5) 0.4884(3) 0.3514(10) 0.0117(13) Uiso 1 1 d D . . C34 C -0.1244(5) 0.4949(3) 0.4066(11) 0.0158(14) Uiso 1 1 d D . . H34 H -0.1836 0.4533 0.4120 0.019 Uiso 1 1 calc R . . C35 C -0.1219(5) 0.5665(3) 0.4501(10) 0.0139(13) Uiso 1 1 d D . . C36 C -0.2054(6) 0.5941(4) 0.5141(12) 0.0210(15) Uiso 1 1 d D . . H36A H -0.2664 0.5516 0.5214 0.032 Uiso 1 1 calc R . . H36B H -0.2513 0.6430 0.4925 0.032 Uiso 1 1 calc R . . H36C H -0.1524 0.6055 0.5697 0.032 Uiso 1 1 calc R . . C51 C 0.4826(5) 0.8288(3) 0.2903(10) 0.0093(13) Uiso 1 1 d D . . C52 C 0.4708(5) 0.9154(3) 0.3232(9) 0.0153(14) Uiso 1 1 d D . . C53 C 0.4929(5) 0.9689(3) 0.2446(10) 0.0128(13) Uiso 1 1 d D . . C54 C 0.5664(6) 0.9133(4) 0.1933(11) 0.0181(16) Uiso 1 1 d D . . C55 C 0.5194(5) 0.8285(3) 0.2107(10) 0.0091(13) Uiso 1 1 d D . . C61 C 0.6588(6) 0.6725(3) 0.3063(12) 0.0171(15) Uiso 1 1 d D . . H61A H 0.6310 0.6452 0.2513 0.026 Uiso 1 1 calc R . . H61B H 0.7189 0.6380 0.3435 0.026 Uiso 1 1 calc R . . H61C H 0.7001 0.7234 0.2961 0.026 Uiso 1 1 calc R . . C62 C 0.5441(5) 0.6892(3) 0.3499(10) 0.0130(13) Uiso 1 1 d D . . C63 C 0.4662(5) 0.7585(3) 0.3460(11) 0.0129(13) Uiso 1 1 d D . . C64 C 0.3739(5) 0.7538(3) 0.4037(10) 0.0148(13) Uiso 1 1 d D . . H64 H 0.3150 0.7956 0.4092 0.018 Uiso 1 1 calc R . . C65 C 0.3797(5) 0.6837(3) 0.4493(11) 0.0169(14) Uiso 1 1 d D . . C66 C 0.2982(6) 0.6552(4) 0.5152(12) 0.0251(16) Uiso 1 1 d D . . H66A H 0.3502 0.6536 0.5725 0.038 Uiso 1 1 calc R . . H66B H 0.2650 0.6013 0.4995 0.038 Uiso 1 1 calc R . . H66C H 0.2274 0.6927 0.5156 0.038 Uiso 1 1 calc R . . C81 C 0.3305(5) 0.6788(4) 0.1605(12) 0.0157(14) Uiso 1 1 d D . . H81A H 0.3396 0.6838 0.2232 0.024 Uiso 1 1 calc R . . H81B H 0.3018 0.6243 0.1432 0.024 Uiso 1 1 calc R . . H81C H 0.2682 0.7181 0.1332 0.024 Uiso 1 1 calc R . . C82 C 0.4577(5) 0.6947(3) 0.1323(11) 0.0125(13) Uiso 1 1 d D . . C83 C 0.5351(5) 0.7630(3) 0.1515(11) 0.0125(13) Uiso 1 1 d D . . C84 C 0.6398(5) 0.7641(3) 0.1026(10) 0.0123(13) Uiso 1 1 d D . . H84 H 0.6992 0.8070 0.1065 0.015 Uiso 1 1 calc R . . C85 C 0.6460(5) 0.6985(3) 0.0506(10) 0.0120(13) Uiso 1 1 d D . . C86 C 0.7408(6) 0.6836(3) -0.0088(11) 0.0183(14) Uiso 1 1 d D . . H86A H 0.7001 0.6921 -0.0685 0.027 Uiso 1 1 calc R . . H86B H 0.7719 0.6280 -0.0017 0.027 Uiso 1 1 calc R . . H86C H 0.8123 0.7210 0.0053 0.027 Uiso 1 1 calc R . . F1 F 0.1267(3) 0.3053(2) 0.1576(7) 0.0205(9) Uiso 1 1 d D . . F2 F -0.0784(4) 0.3132(2) 0.1091(8) 0.0296(11) Uiso 1 1 d D . . F3 F 0.0972(3) 0.2503(2) 0.3062(8) 0.0300(10) Uiso 1 1 d D . . F4 F -0.0894(3) 0.2108(2) 0.2364(8) 0.0278(10) Uiso 1 1 d D . . F5 F -0.0517(4) 0.3144(3) 0.4003(9) 0.0295(11) Uiso 1 1 d D . . F6 F -0.2075(3) 0.33593(19) 0.2906(7) 0.0190(9) Uiso 1 1 d D . . F7 F 0.5620(4) 0.9347(2) 0.3939(8) 0.0295(11) Uiso 1 1 d D . . F8 F 0.3558(3) 0.9312(2) 0.3474(8) 0.0245(10) Uiso 1 1 d D . . F9 F 0.5567(3) 1.0382(2) 0.2690(7) 0.0241(9) Uiso 1 1 d D . . F10 F 0.3784(3) 0.9888(2) 0.1957(8) 0.0248(10) Uiso 1 1 d D . . F11 F 0.6957(3) 0.91765(19) 0.2235(7) 0.0195(9) Uiso 1 1 d D . . F12 F 0.5480(4) 0.9336(2) 0.1046(9) 0.0264(11) Uiso 1 1 d D . . S1 S 0.02589(13) 0.61353(8) 0.0689(3) 0.016(4) Uani 1 1 d D . . S2 S 0.00150(14) 0.62749(8) 0.4253(4) 0.021(4) Uani 1 1 d D . . S3 S 0.49812(14) 0.62043(8) 0.4228(4) 0.025(4) Uani 1 1 d D . . S4 S 0.52032(13) 0.63167(8) 0.0605(3) 0.019(4) Uani 1 1 d 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 S1 0.0125(7) 0.0148(7) 0.019(12) 0.0041(15) -0.0001(17) -0.0002(5) S2 0.0156(7) 0.0123(7) 0.033(12) -0.0018(14) 0.0023(18) 0.0001(5) S3 0.0157(7) 0.0146(7) 0.043(12) 0.0021(15) 0.0016(18) -0.0019(5) S4 0.0135(7) 0.0129(7) 0.029(11) -0.0032(15) 0.0006(17) -0.0011(5) _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 C5 1.329(15) . ? C1 C13 1.456(11) . ? C1 C2 1.512(9) . ? C2 F1 1.339(8) . ? C2 F2 1.347(13) . ? C2 C3 1.575(15) . ? C3 F4 1.328(7) . ? C3 F3 1.343(9) . ? C3 C4 1.494(12) . ? C4 F5 1.354(16) . ? C4 F6 1.358(7) . ? C4 C5 1.504(9) . ? C5 C33 1.456(13) . ? C11 C12 1.494(11) . ? C12 C13 1.382(7) . ? C12 S1 1.708(11) . ? C13 C14 1.415(12) . ? C14 C15 1.356(12) . ? C15 C16 1.497(14) . ? C15 S1 1.723(6) . ? C31 C32 1.487(10) . ? C32 C33 1.384(7) . ? C32 S2 1.704(11) . ? C33 C34 1.427(13) . ? C34 C35 1.341(12) . ? C35 C36 1.492(14) . ? C35 S2 1.721(7) . ? C51 C55 1.346(13) . ? C51 C63 1.457(15) . ? C51 C52 1.509(9) . ? C52 F8 1.342(8) . ? C52 F7 1.363(13) . ? C52 C53 1.540(15) . ? C53 F9 1.333(7) . ? C53 F10 1.346(10) . ? C53 C54 1.494(12) . ? C54 F11 1.359(8) . ? C54 F12 1.390(16) . ? C54 C55 1.503(9) . ? C55 C83 1.430(16) . ? C61 C62 1.493(12) . ? C62 C63 1.386(7) . ? C62 S3 1.710(11) . ? C63 C64 1.419(14) . ? C64 C65 1.336(12) . ? C65 C66 1.503(14) . ? C65 S3 1.711(7) . ? C81 C82 1.489(10) . ? C82 C83 1.378(8) . ? C82 S4 1.715(11) . ? C83 C84 1.428(13) . ? C84 C85 1.342(12) . ? C85 C86 1.477(13) . ? C85 S4 1.732(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C1 C13 129.3(7) . . ? C5 C1 C2 112.7(7) . . ? C13 C1 C2 117.7(10) . . ? F1 C2 F2 106.9(10) . . ? F1 C2 C1 113.4(5) . . ? F2 C2 C1 114.5(6) . . ? F1 C2 C3 110.4(7) . . ? F2 C2 C3 109.9(6) . . ? C1 C2 C3 101.7(9) . . ? F4 C3 F3 108.5(5) . . ? F4 C3 C4 113.4(6) . . ? F3 C3 C4 109.3(10) . . ? F4 C3 C2 112.6(10) . . ? F3 C3 C2 108.4(6) . . ? C4 C3 C2 104.4(7) . . ? F5 C4 F6 106.8(9) . . ? F5 C4 C3 110.0(8) . . ? F6 C4 C3 110.5(8) . . ? F5 C4 C5 115.1(9) . . ? F6 C4 C5 110.0(7) . . ? C3 C4 C5 104.5(8) . . ? C1 C5 C33 129.8(7) . . ? C1 C5 C4 109.3(8) . . ? C33 C5 C4 120.6(11) . . ? C13 C12 C11 127.1(9) . . ? C13 C12 S1 110.0(7) . . ? C11 C12 S1 122.9(6) . . ? C12 C13 C14 112.8(8) . . ? C12 C13 C1 124.1(8) . . ? C14 C13 C1 123.0(5) . . ? C15 C14 C13 113.6(5) . . ? C14 C15 C16 128.0(6) . . ? C14 C15 S1 110.2(7) . . ? C16 C15 S1 121.7(6) . . ? C33 C32 C31 129.5(8) . . ? C33 C32 S2 109.5(7) . . ? C31 C32 S2 120.6(6) . . ? C32 C33 C34 112.5(8) . . ? C32 C33 C5 125.7(9) . . ? C34 C33 C5 121.8(6) . . ? C35 C34 C33 113.9(6) . . ? C34 C35 C36 128.8(7) . . ? C34 C35 S2 110.1(7) . . ? C36 C35 S2 121.1(5) . . ? C55 C51 C63 127.8(8) . . ? C55 C51 C52 111.2(8) . . ? C63 C51 C52 120.7(12) . . ? F8 C52 F7 106.0(10) . . ? F8 C52 C51 113.4(5) . . ? F7 C52 C51 113.5(6) . . ? F8 C52 C53 111.6(7) . . ? F7 C52 C53 108.9(6) . . ? C51 C52 C53 103.3(9) . . ? F9 C53 F10 108.3(5) . . ? F9 C53 C54 112.5(6) . . ? F10 C53 C54 109.7(10) . . ? F9 C53 C52 112.8(10) . . ? F10 C53 C52 110.0(6) . . ? C54 C53 C52 103.4(7) . . ? F11 C54 F12 107.2(9) . . ? F11 C54 C53 110.9(9) . . ? F12 C54 C53 112.1(8) . . ? F11 C54 C55 108.9(7) . . ? F12 C54 C55 113.4(10) . . ? C53 C54 C55 104.4(8) . . ? C51 C55 C83 131.8(8) . . ? C51 C55 C54 108.1(9) . . ? C83 C55 C54 119.6(12) . . ? C63 C62 C61 129.7(9) . . ? C63 C62 S3 109.5(8) . . ? C61 C62 S3 120.7(5) . . ? C62 C63 C64 112.7(9) . . ? C62 C63 C51 122.6(10) . . ? C64 C63 C51 124.7(6) . . ? C65 C64 C63 113.5(6) . . ? C64 C65 C66 129.6(6) . . ? C64 C65 S3 111.1(8) . . ? C66 C65 S3 119.3(5) . . ? C83 C82 C81 126.8(9) . . ? C83 C82 S4 110.3(7) . . ? C81 C82 S4 122.6(6) . . ? C82 C83 C84 111.8(9) . . ? C82 C83 C55 127.8(9) . . ? C84 C83 C55 120.4(6) . . ? C85 C84 C83 114.9(6) . . ? C84 C85 C86 127.2(6) . . ? C84 C85 S4 109.5(7) . . ? C86 C85 S4 123.3(6) . . ? C12 S1 C15 93.3(4) . . ? C32 S2 C35 93.8(4) . . ? C62 S3 C65 93.2(4) . . ? C82 S4 C85 93.3(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 C5 C1 C2 F1 -125.1(10) . . . . ? C13 C1 C2 F1 60.3(11) . . . . ? C5 C1 C2 F2 111.8(10) . . . . ? C13 C1 C2 F2 -62.8(9) . . . . ? C5 C1 C2 C3 -6.7(7) . . . . ? C13 C1 C2 C3 178.8(5) . . . . ? F1 C2 C3 F4 -94.9(7) . . . . ? F2 C2 C3 F4 22.8(6) . . . . ? C1 C2 C3 F4 144.4(5) . . . . ? F1 C2 C3 F3 25.2(9) . . . . ? F2 C2 C3 F3 142.8(7) . . . . ? C1 C2 C3 F3 -95.5(7) . . . . ? F1 C2 C3 C4 141.6(7) . . . . ? F2 C2 C3 C4 -100.7(6) . . . . ? C1 C2 C3 C4 21.0(6) . . . . ? F4 C3 C4 F5 85.8(10) . . . . ? F3 C3 C4 F5 -35.4(7) . . . . ? C2 C3 C4 F5 -151.2(5) . . . . ? F4 C3 C4 F6 -31.9(14) . . . . ? F3 C3 C4 F6 -153.1(8) . . . . ? C2 C3 C4 F6 91.1(9) . . . . ? F4 C3 C4 C5 -150.1(10) . . . . ? F3 C3 C4 C5 88.7(10) . . . . ? C2 C3 C4 C5 -27.2(9) . . . . ? C13 C1 C5 C33 -10.2(13) . . . . ? C2 C1 C5 C33 175.9(7) . . . . ? C13 C1 C5 C4 163.2(7) . . . . ? C2 C1 C5 C4 -10.6(9) . . . . ? F5 C4 C5 C1 145.1(7) . . . . ? F6 C4 C5 C1 -94.3(10) . . . . ? C3 C4 C5 C1 24.3(10) . . . . ? F5 C4 C5 C33 -40.8(9) . . . . ? F6 C4 C5 C33 79.9(13) . . . . ? C3 C4 C5 C33 -161.5(8) . . . . ? C11 C12 C13 C14 178.2(11) . . . . ? S1 C12 C13 C14 -0.3(13) . . . . ? C11 C12 C13 C1 0.8(19) . . . . ? S1 C12 C13 C1 -177.8(8) . . . . ? C5 C1 C13 C12 -41.7(15) . . . . ? C2 C1 C13 C12 131.9(11) . . . . ? C5 C1 C13 C14 141.2(10) . . . . ? C2 C1 C13 C14 -45.3(12) . . . . ? C12 C13 C14 C15 -1.0(14) . . . . ? C1 C13 C14 C15 176.4(10) . . . . ? C13 C14 C15 C16 -175.5(10) . . . . ? C13 C14 C15 S1 1.8(12) . . . . ? C31 C32 C33 C34 167.4(13) . . . . ? S2 C32 C33 C34 -5.3(13) . . . . ? C31 C32 C33 C5 -14(2) . . . . ? S2 C32 C33 C5 173.4(9) . . . . ? C1 C5 C33 C32 -31.8(16) . . . . ? C4 C5 C33 C32 155.4(11) . . . . ? C1 C5 C33 C34 146.7(9) . . . . ? C4 C5 C33 C34 -26.1(14) . . . . ? C32 C33 C34 C35 4.1(15) . . . . ? C5 C33 C34 C35 -174.6(11) . . . . ? C33 C34 C35 C36 -178.8(11) . . . . ? C33 C34 C35 S2 -0.9(13) . . . . ? C55 C51 C52 F8 127.0(10) . . . . ? C63 C51 C52 F8 -58.3(12) . . . . ? C55 C51 C52 F7 -111.9(9) . . . . ? C63 C51 C52 F7 62.8(9) . . . . ? C55 C51 C52 C53 5.9(7) . . . . ? C63 C51 C52 C53 -179.3(6) . . . . ? F8 C52 C53 F9 93.2(7) . . . . ? F7 C52 C53 F9 -23.5(6) . . . . ? C51 C52 C53 F9 -144.5(5) . . . . ? F8 C52 C53 F10 -27.8(10) . . . . ? F7 C52 C53 F10 -144.5(7) . . . . ? C51 C52 C53 F10 94.5(7) . . . . ? F8 C52 C53 C54 -144.9(8) . . . . ? F7 C52 C53 C54 98.3(7) . . . . ? C51 C52 C53 C54 -22.7(7) . . . . ? F9 C53 C54 F11 35.5(14) . . . . ? F10 C53 C54 F11 156.1(8) . . . . ? C52 C53 C54 F11 -86.6(9) . . . . ? F9 C53 C54 F12 -84.3(10) . . . . ? F10 C53 C54 F12 36.3(7) . . . . ? C52 C53 C54 F12 153.6(6) . . . . ? F9 C53 C54 C55 152.6(10) . . . . ? F10 C53 C54 C55 -86.8(10) . . . . ? C52 C53 C54 C55 30.5(10) . . . . ? C63 C51 C55 C83 10.3(13) . . . . ? C52 C51 C55 C83 -175.4(7) . . . . ? C63 C51 C55 C54 -160.7(7) . . . . ? C52 C51 C55 C54 13.6(8) . . . . ? F11 C54 C55 C51 90.3(10) . . . . ? F12 C54 C55 C51 -150.6(6) . . . . ? C53 C54 C55 C51 -28.2(10) . . . . ? F11 C54 C55 C83 -82.1(13) . . . . ? F12 C54 C55 C83 37.1(9) . . . . ? C53 C54 C55 C83 159.4(9) . . . . ? C61 C62 C63 C64 -174.3(12) . . . . ? S3 C62 C63 C64 1.2(13) . . . . ? C61 C62 C63 C51 4(2) . . . . ? S3 C62 C63 C51 179.2(10) . . . . ? C55 C51 C63 C62 34.5(16) . . . . ? C52 C51 C63 C62 -139.2(11) . . . . ? C55 C51 C63 C64 -147.7(10) . . . . ? C52 C51 C63 C64 38.5(13) . . . . ? C62 C63 C64 C65 -0.6(14) . . . . ? C51 C63 C64 C65 -178.6(11) . . . . ? C63 C64 C65 C66 -179.0(11) . . . . ? C63 C64 C65 S3 -0.3(13) . . . . ? C81 C82 C83 C84 -170.7(12) . . . . ? S4 C82 C83 C84 3.4(13) . . . . ? C81 C82 C83 C55 8(2) . . . . ? S4 C82 C83 C55 -177.5(11) . . . . ? C51 C55 C83 C82 39.6(18) . . . . ? C54 C55 C83 C82 -150.3(12) . . . . ? C51 C55 C83 C84 -141.5(10) . . . . ? C54 C55 C83 C84 28.7(14) . . . . ? C82 C83 C84 C85 -2.2(15) . . . . ? C55 C83 C84 C85 178.7(11) . . . . ? C83 C84 C85 C86 178.4(10) . . . . ? C83 C84 C85 S4 -0.1(13) . . . . ? C13 C12 S1 C15 1.2(9) . . . . ? C11 C12 S1 C15 -177.5(10) . . . . ? C14 C15 S1 C12 -1.7(9) . . . . ? C16 C15 S1 C12 175.8(9) . . . . ? C33 C32 S2 C35 4.2(10) . . . . ? C31 C32 S2 C35 -169.4(11) . . . . ? C34 C35 S2 C32 -1.9(10) . . . . ? C36 C35 S2 C32 176.2(10) . . . . ? C63 C62 S3 C65 -1.2(10) . . . . ? C61 C62 S3 C65 174.8(10) . . . . ? C64 C65 S3 C62 0.9(10) . . . . ? C66 C65 S3 C62 179.8(9) . . . . ? C83 C82 S4 C85 -3.0(10) . . . . ? C81 C82 S4 C85 171.4(11) . . . . ? C84 C85 S4 C82 1.8(9) . . . . ? C86 C85 S4 C82 -176.8(10) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961273' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_8.55GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety '2(C17 H14 F6 S2)' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.4211(7) _cell_length_b 16.1206(12) _cell_length_c 15.1690(68) _cell_angle_alpha 90.00 _cell_angle_beta 99.830(11) _cell_angle_gamma 90.00 _cell_volume 2509.3(11) _cell_formula_units_Z 8 _cell_measurement_reflns_used 688 _cell_measurement_theta_min 2.1237 _cell_measurement_theta_max 28.6401 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.099 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.394 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 5197 _diffrn_reflns_av_R_equivalents 0.1016 _diffrn_reflns_av_sigmaI/netI 0.0858 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 25.68 _reflns_number_total 1349 _reflns_number_gt 1024 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.258 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.258 _refine_diff_density_max 0.404 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.062 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 1349 _refine_ls_number_parameters 229 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1699 _refine_ls_wR_factor_gt 0.1546 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.036 _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 0.0125(6) 0.4135(3) 0.2128(11) 0.0095(15) Uiso 1 1 d D . . C2 C 0.0104(6) 0.3261(3) 0.1777(11) 0.0148(16) Uiso 1 1 d D . . C3 C -0.0172(5) 0.2746(3) 0.2604(11) 0.0098(15) Uiso 1 1 d D . . C4 C -0.0791(7) 0.3353(5) 0.3130(12) 0.019(2) Uiso 1 1 d D . . C5 C -0.0232(6) 0.4171(3) 0.2926(11) 0.0088(14) Uiso 1 1 d D . . C11 C -0.1503(6) 0.5743(4) 0.1821(14) 0.0130(15) Uiso 1 1 d D . . H11A H -0.1929 0.5242 0.1955 0.020 Uiso 1 1 calc R . . H11B H -0.2092 0.6067 0.1401 0.020 Uiso 1 1 calc R . . H11C H -0.1245 0.6056 0.2361 0.020 Uiso 1 1 calc R . . C12 C -0.0334(6) 0.5531(3) 0.1427(12) 0.0121(15) Uiso 1 1 d D . . C13 C 0.0397(6) 0.4815(3) 0.1558(12) 0.0156(16) Uiso 1 1 d D . . C14 C 0.1414(6) 0.4789(3) 0.1056(12) 0.0115(15) Uiso 1 1 d D . . H14 H 0.2010 0.4356 0.1092 0.014 Uiso 1 1 calc R . . C15 C 0.1441(6) 0.5451(4) 0.0518(12) 0.0152(16) Uiso 1 1 d D . . C16 C 0.2347(6) 0.5597(4) -0.0119(13) 0.0157(16) Uiso 1 1 d D . . H16A H 0.2990 0.5165 -0.0058 0.024 Uiso 1 1 calc R . . H16B H 0.2770 0.6124 0.0007 0.024 Uiso 1 1 calc R . . H16C H 0.1869 0.5598 -0.0720 0.024 Uiso 1 1 calc R . . C31 C 0.1827(6) 0.5654(4) 0.3258(14) 0.0159(16) Uiso 1 1 d D . . H31A H 0.2440 0.5252 0.3546 0.024 Uiso 1 1 calc R . . H31B H 0.2158 0.6202 0.3399 0.024 Uiso 1 1 calc R . . H31C H 0.1695 0.5572 0.2622 0.024 Uiso 1 1 calc R . . C32 C 0.0557(6) 0.5551(3) 0.3584(13) 0.0136(15) Uiso 1 1 d D . . C33 C -0.0270(6) 0.4883(3) 0.3508(12) 0.0100(14) Uiso 1 1 d D . . C34 C -0.1235(6) 0.4954(3) 0.4067(13) 0.0121(15) Uiso 1 1 d D . . H34 H -0.1843 0.4542 0.4114 0.014 Uiso 1 1 calc R . . C35 C -0.1184(6) 0.5680(3) 0.4525(12) 0.0138(15) Uiso 1 1 d D . . C36 C -0.2021(7) 0.5977(4) 0.5158(15) 0.0218(18) Uiso 1 1 d D . . H36A H -0.2641 0.5554 0.5235 0.033 Uiso 1 1 calc R . . H36B H -0.2473 0.6469 0.4924 0.033 Uiso 1 1 calc R . . H36C H -0.1490 0.6099 0.5725 0.033 Uiso 1 1 calc R . . C51 C 0.4839(6) 0.8300(3) 0.2919(11) 0.0111(15) Uiso 1 1 d D . . C52 C 0.4731(6) 0.9172(3) 0.3245(11) 0.0124(15) Uiso 1 1 d D . . C53 C 0.4937(5) 0.9707(4) 0.2437(11) 0.0116(15) Uiso 1 1 d D . . C54 C 0.5684(6) 0.9140(5) 0.1934(12) 0.0187(19) Uiso 1 1 d D . . C55 C 0.5195(6) 0.8296(3) 0.2107(11) 0.0090(15) Uiso 1 1 d D . . C61 C 0.6605(7) 0.6725(4) 0.3049(14) 0.0165(17) Uiso 1 1 d D . . H61A H 0.6317 0.6456 0.2485 0.025 Uiso 1 1 calc R . . H61B H 0.7219 0.6376 0.3421 0.025 Uiso 1 1 calc R . . H61C H 0.7013 0.7243 0.2951 0.025 Uiso 1 1 calc R . . C62 C 0.5449(6) 0.6884(3) 0.3508(13) 0.0137(15) Uiso 1 1 d D . . C63 C 0.4667(6) 0.7581(3) 0.3479(13) 0.0131(15) Uiso 1 1 d D . . C64 C 0.3755(6) 0.7528(4) 0.4063(12) 0.0175(16) Uiso 1 1 d D . . H64 H 0.3157 0.7944 0.4119 0.021 Uiso 1 1 calc R . . C65 C 0.3832(6) 0.6818(4) 0.4530(12) 0.0154(16) Uiso 1 1 d D . . C66 C 0.3029(7) 0.6512(4) 0.5193(14) 0.0256(19) Uiso 1 1 d D . . H66A H 0.3537 0.6533 0.5784 0.038 Uiso 1 1 calc R . . H66B H 0.2765 0.5950 0.5052 0.038 Uiso 1 1 calc R . . H66C H 0.2272 0.6856 0.5169 0.038 Uiso 1 1 calc R . . C81 C 0.3286(6) 0.6797(4) 0.1596(15) 0.0136(16) Uiso 1 1 d D . . H81A H 0.3334 0.6974 0.2205 0.020 Uiso 1 1 calc R . . H81B H 0.3080 0.6216 0.1551 0.020 Uiso 1 1 calc R . . H81C H 0.2620 0.7105 0.1218 0.020 Uiso 1 1 calc R . . C82 C 0.4568(6) 0.6944(3) 0.1305(13) 0.0125(15) Uiso 1 1 d D . . C83 C 0.5348(6) 0.7627(3) 0.1521(13) 0.0121(15) Uiso 1 1 d D . . C84 C 0.6385(6) 0.7640(3) 0.1015(12) 0.0097(14) Uiso 1 1 d D . . H84 H 0.6973 0.8077 0.1046 0.012 Uiso 1 1 calc R . . C85 C 0.6450(6) 0.6981(3) 0.0493(12) 0.0137(15) Uiso 1 1 d D . . C86 C 0.7425(6) 0.6826(4) -0.0095(13) 0.0152(15) Uiso 1 1 d D . . H86A H 0.7024 0.6899 -0.0709 0.023 Uiso 1 1 calc R . . H86B H 0.7748 0.6269 -0.0007 0.023 Uiso 1 1 calc R . . H86C H 0.8134 0.7210 0.0050 0.023 Uiso 1 1 calc R . . F1 F 0.1255(4) 0.3034(2) 0.1567(9) 0.0197(10) Uiso 1 1 d D . . F2 F -0.0811(4) 0.3108(2) 0.1054(9) 0.0256(11) Uiso 1 1 d D . . F3 F 0.0967(4) 0.2493(2) 0.3074(9) 0.0260(11) Uiso 1 1 d D . . F4 F -0.0916(4) 0.2085(2) 0.2366(10) 0.0269(11) Uiso 1 1 d D . . F5 F -0.0568(4) 0.3131(3) 0.4007(10) 0.0252(13) Uiso 1 1 d D . . F6 F -0.2108(3) 0.3361(2) 0.2882(9) 0.0178(10) Uiso 1 1 d D . . F7 F 0.5652(4) 0.9368(2) 0.3965(9) 0.0253(11) Uiso 1 1 d D . . F8 F 0.3570(4) 0.9334(2) 0.3478(9) 0.0226(10) Uiso 1 1 d D . . F9 F 0.5577(4) 1.0404(2) 0.2683(9) 0.0222(10) Uiso 1 1 d D . . F10 F 0.3786(4) 0.9900(2) 0.1934(9) 0.0220(10) Uiso 1 1 d D . . F11 F 0.6985(3) 0.9172(2) 0.2262(9) 0.0186(10) Uiso 1 1 d D . . F12 F 0.5521(4) 0.9348(2) 0.1038(10) 0.0229(12) Uiso 1 1 d D . . S1 S 0.02562(15) 0.61504(9) 0.0679(4) 0.024(5) Uani 1 1 d D . . S2 S 0.00423(16) 0.62892(8) 0.4250(4) 0.017(5) Uani 1 1 d D . . S3 S 0.50074(16) 0.61843(9) 0.4233(4) 0.028(5) Uani 1 1 d D . . S4 S 0.51938(16) 0.63027(9) 0.0591(4) 0.019(5) Uani 1 1 d 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 S1 0.0107(8) 0.0151(8) 0.045(16) 0.002(2) 0.003(3) 0.0003(6) S2 0.0133(8) 0.0128(8) 0.023(16) -0.0041(18) 0.001(3) 0.0000(6) S3 0.0145(9) 0.0146(8) 0.056(17) 0.003(2) 0.005(3) -0.0003(6) S4 0.0122(8) 0.0139(8) 0.030(16) -0.0026(18) 0.003(3) -0.0001(5) _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 C5 1.326(19) . ? C1 C13 1.454(12) . ? C1 C2 1.505(9) . ? C2 F1 1.343(8) . ? C2 F2 1.347(15) . ? C2 C3 1.570(17) . ? C3 F4 1.331(8) . ? C3 F3 1.340(11) . ? C3 C4 1.479(14) . ? C4 F5 1.358(19) . ? C4 F6 1.359(8) . ? C4 C5 1.496(10) . ? C5 C33 1.451(14) . ? C11 C12 1.485(12) . ? C12 C13 1.379(8) . ? C12 S1 1.703(14) . ? C13 C14 1.407(13) . ? C14 C15 1.345(14) . ? C15 C16 1.481(16) . ? C15 S1 1.720(6) . ? C31 C32 1.498(11) . ? C32 C33 1.372(7) . ? C32 S2 1.706(13) . ? C33 C34 1.426(14) . ? C34 C35 1.357(13) . ? C35 C36 1.482(16) . ? C35 S2 1.718(7) . ? C51 C55 1.345(16) . ? C51 C63 1.465(17) . ? C51 C52 1.501(10) . ? C52 F8 1.343(8) . ? C52 F7 1.363(15) . ? C52 C53 1.542(17) . ? C53 F9 1.328(8) . ? C53 F10 1.344(11) . ? C53 C54 1.492(13) . ? C54 F11 1.363(9) . ? C54 F12 1.381(19) . ? C54 C55 1.492(10) . ? C55 C83 1.422(18) . ? C61 C62 1.512(13) . ? C62 C63 1.384(8) . ? C62 S3 1.692(14) . ? C63 C64 1.408(15) . ? C64 C65 1.341(13) . ? C65 C66 1.497(16) . ? C65 S3 1.713(8) . ? C81 C82 1.495(10) . ? C82 C83 1.375(9) . ? C82 S4 1.705(14) . ? C83 C84 1.429(14) . ? C84 C85 1.333(14) . ? C85 C86 1.483(15) . ? C85 S4 1.731(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 C5 C1 C13 128.5(8) . . ? C5 C1 C2 112.0(8) . . ? C13 C1 C2 119.2(11) . . ? F1 C2 F2 107.1(11) . . ? F1 C2 C1 112.3(5) . . ? F2 C2 C1 115.1(7) . . ? F1 C2 C3 109.8(8) . . ? F2 C2 C3 110.6(7) . . ? C1 C2 C3 101.9(10) . . ? F4 C3 F3 108.7(6) . . ? F4 C3 C4 112.8(6) . . ? F3 C3 C4 110.1(12) . . ? F4 C3 C2 112.7(12) . . ? F3 C3 C2 108.6(7) . . ? C4 C3 C2 103.8(8) . . ? F5 C4 F6 105.6(10) . . ? F5 C4 C3 109.7(10) . . ? F6 C4 C3 111.7(10) . . ? F5 C4 C5 115.3(11) . . ? F6 C4 C5 110.2(8) . . ? C3 C4 C5 104.5(9) . . ? C1 C5 C33 129.1(8) . . ? C1 C5 C4 109.2(9) . . ? C33 C5 C4 121.3(12) . . ? C13 C12 C11 127.3(10) . . ? C13 C12 S1 109.5(8) . . ? C11 C12 S1 123.2(6) . . ? C12 C13 C14 113.3(9) . . ? C12 C13 C1 123.9(9) . . ? C14 C13 C1 122.8(6) . . ? C15 C14 C13 113.6(6) . . ? C14 C15 C16 127.1(7) . . ? C14 C15 S1 110.1(8) . . ? C16 C15 S1 122.7(7) . . ? C33 C32 C31 129.6(9) . . ? C33 C32 S2 109.9(8) . . ? C31 C32 S2 120.2(6) . . ? C32 C33 C34 112.5(9) . . ? C32 C33 C5 126.1(10) . . ? C34 C33 C5 121.4(6) . . ? C35 C34 C33 113.8(7) . . ? C34 C35 C36 129.3(7) . . ? C34 C35 S2 109.5(8) . . ? C36 C35 S2 121.1(6) . . ? C55 C51 C63 127.3(9) . . ? C55 C51 C52 110.7(9) . . ? C63 C51 C52 121.8(13) . . ? F8 C52 F7 106.6(11) . . ? F8 C52 C51 113.0(5) . . ? F7 C52 C51 113.5(7) . . ? F8 C52 C53 110.8(8) . . ? F7 C52 C53 109.4(7) . . ? C51 C52 C53 103.6(10) . . ? F9 C53 F10 108.7(6) . . ? F9 C53 C54 112.5(6) . . ? F10 C53 C54 110.1(11) . . ? F9 C53 C52 112.4(12) . . ? F10 C53 C52 110.4(7) . . ? C54 C53 C52 102.6(8) . . ? F11 C54 F12 107.3(10) . . ? F11 C54 C55 108.5(8) . . ? F12 C54 C55 114.0(11) . . ? F11 C54 C53 111.3(10) . . ? F12 C54 C53 111.5(9) . . ? C55 C54 C53 104.2(9) . . ? C51 C55 C83 130.8(9) . . ? C51 C55 C54 108.2(10) . . ? C83 C55 C54 120.2(12) . . ? C63 C62 C61 129.3(10) . . ? C63 C62 S3 109.7(9) . . ? C61 C62 S3 120.8(6) . . ? C62 C63 C64 112.8(10) . . ? C62 C63 C51 122.0(11) . . ? C64 C63 C51 125.1(6) . . ? C65 C64 C63 113.4(7) . . ? C64 C65 C66 130.2(7) . . ? C64 C65 S3 110.6(9) . . ? C66 C65 S3 119.1(6) . . ? C83 C82 C81 125.3(10) . . ? C83 C82 S4 111.2(8) . . ? C81 C82 S4 123.3(7) . . ? C82 C83 C55 129.1(10) . . ? C82 C83 C84 110.7(11) . . ? C55 C83 C84 120.0(6) . . ? C85 C84 C83 115.3(6) . . ? C84 C85 C86 126.9(6) . . ? C84 C85 S4 109.7(7) . . ? C86 C85 S4 123.4(7) . . ? C12 S1 C15 93.4(5) . . ? C32 S2 C35 93.8(5) . . ? C62 S3 C65 93.4(5) . . ? C82 S4 C85 92.8(5) . . ? 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 C5 C1 C2 F1 -124.5(11) . . . . ? C13 C1 C2 F1 60.9(13) . . . . ? C5 C1 C2 F2 112.5(11) . . . . ? C13 C1 C2 F2 -62.1(10) . . . . ? C5 C1 C2 C3 -7.2(8) . . . . ? C13 C1 C2 C3 178.2(6) . . . . ? F1 C2 C3 F4 -95.9(8) . . . . ? F2 C2 C3 F4 22.1(7) . . . . ? C1 C2 C3 F4 144.9(5) . . . . ? F1 C2 C3 F3 24.6(10) . . . . ? F2 C2 C3 F3 142.6(7) . . . . ? C1 C2 C3 F3 -94.6(8) . . . . ? F1 C2 C3 C4 141.7(8) . . . . ? F2 C2 C3 C4 -100.3(7) . . . . ? C1 C2 C3 C4 22.5(7) . . . . ? F4 C3 C4 F5 84.5(12) . . . . ? F3 C3 C4 F5 -37.1(8) . . . . ? C2 C3 C4 F5 -153.2(6) . . . . ? F4 C3 C4 F6 -32.3(16) . . . . ? F3 C3 C4 F6 -153.9(9) . . . . ? C2 C3 C4 F6 90.0(10) . . . . ? F4 C3 C4 C5 -151.4(12) . . . . ? F3 C3 C4 C5 87.0(11) . . . . ? C2 C3 C4 C5 -29.1(10) . . . . ? C13 C1 C5 C33 -9.8(14) . . . . ? C2 C1 C5 C33 176.3(8) . . . . ? C13 C1 C5 C4 162.7(8) . . . . ? C2 C1 C5 C4 -11.3(10) . . . . ? F5 C4 C5 C1 146.7(8) . . . . ? F6 C4 C5 C1 -93.9(12) . . . . ? C3 C4 C5 C1 26.2(12) . . . . ? F5 C4 C5 C33 -40.2(10) . . . . ? F6 C4 C5 C33 79.2(15) . . . . ? C3 C4 C5 C33 -160.7(9) . . . . ? C11 C12 C13 C14 177.3(13) . . . . ? S1 C12 C13 C14 0.4(15) . . . . ? C11 C12 C13 C1 0(2) . . . . ? S1 C12 C13 C1 -177.4(10) . . . . ? C5 C1 C13 C12 -41.4(18) . . . . ? C2 C1 C13 C12 132.2(13) . . . . ? C5 C1 C13 C14 141.1(12) . . . . ? C2 C1 C13 C14 -45.3(14) . . . . ? C12 C13 C14 C15 -2.7(17) . . . . ? C1 C13 C14 C15 175.1(12) . . . . ? C13 C14 C15 C16 -177.4(12) . . . . ? C13 C14 C15 S1 3.7(14) . . . . ? C31 C32 C33 C34 167.3(16) . . . . ? S2 C32 C33 C34 -5.8(15) . . . . ? C31 C32 C33 C5 -14(3) . . . . ? S2 C32 C33 C5 173.3(10) . . . . ? C1 C5 C33 C32 -32.4(18) . . . . ? C4 C5 C33 C32 155.9(13) . . . . ? C1 C5 C33 C34 146.6(11) . . . . ? C4 C5 C33 C34 -25.1(15) . . . . ? C32 C33 C34 C35 3.1(16) . . . . ? C5 C33 C34 C35 -176.1(12) . . . . ? C33 C34 C35 C36 179.6(12) . . . . ? C33 C34 C35 S2 1.1(14) . . . . ? C55 C51 C52 F8 126.0(11) . . . . ? C63 C51 C52 F8 -58.4(14) . . . . ? C55 C51 C52 F7 -112.4(10) . . . . ? C63 C51 C52 F7 63.2(10) . . . . ? C55 C51 C52 C53 6.1(8) . . . . ? C63 C51 C52 C53 -178.3(7) . . . . ? F8 C52 C53 F9 93.8(8) . . . . ? F7 C52 C53 F9 -23.5(6) . . . . ? C51 C52 C53 F9 -144.8(5) . . . . ? F8 C52 C53 F10 -27.7(10) . . . . ? F7 C52 C53 F10 -145.0(7) . . . . ? C51 C52 C53 F10 93.7(8) . . . . ? F8 C52 C53 C54 -145.1(9) . . . . ? F7 C52 C53 C54 97.6(7) . . . . ? C51 C52 C53 C54 -23.7(7) . . . . ? F9 C53 C54 F11 36.3(15) . . . . ? F10 C53 C54 F11 157.7(9) . . . . ? C52 C53 C54 F11 -84.7(10) . . . . ? F9 C53 C54 F12 -83.5(12) . . . . ? F10 C53 C54 F12 37.9(8) . . . . ? C52 C53 C54 F12 155.5(6) . . . . ? F9 C53 C54 C55 153.1(12) . . . . ? F10 C53 C54 C55 -85.5(11) . . . . ? C52 C53 C54 C55 32.1(11) . . . . ? C63 C51 C55 C83 8.6(14) . . . . ? C52 C51 C55 C83 -176.1(9) . . . . ? C63 C51 C55 C54 -160.8(8) . . . . ? C52 C51 C55 C54 14.6(9) . . . . ? F11 C54 C55 C51 88.7(11) . . . . ? F12 C54 C55 C51 -151.8(7) . . . . ? C53 C54 C55 C51 -30.0(11) . . . . ? F11 C54 C55 C83 -82.0(15) . . . . ? F12 C54 C55 C83 37.5(11) . . . . ? C53 C54 C55 C83 159.3(10) . . . . ? C61 C62 C63 C64 -174.4(13) . . . . ? S3 C62 C63 C64 1.3(15) . . . . ? C61 C62 C63 C51 3(2) . . . . ? S3 C62 C63 C51 178.9(11) . . . . ? C55 C51 C63 C62 35.4(18) . . . . ? C52 C51 C63 C62 -139.4(13) . . . . ? C55 C51 C63 C64 -147.4(11) . . . . ? C52 C51 C63 C64 37.8(16) . . . . ? C62 C63 C64 C65 0.3(16) . . . . ? C51 C63 C64 C65 -177.1(13) . . . . ? C63 C64 C65 C66 -178.2(12) . . . . ? C63 C64 C65 S3 -1.8(14) . . . . ? C81 C82 C83 C55 6(3) . . . . ? S4 C82 C83 C55 -178.4(13) . . . . ? C81 C82 C83 C84 -170.1(14) . . . . ? S4 C82 C83 C84 5.7(15) . . . . ? C51 C55 C83 C82 42(2) . . . . ? C54 C55 C83 C82 -149.4(15) . . . . ? C51 C55 C83 C84 -142.1(11) . . . . ? C54 C55 C83 C84 26.2(17) . . . . ? C82 C83 C84 C85 -4.3(17) . . . . ? C55 C83 C84 C85 179.4(13) . . . . ? C83 C84 C85 C86 -179.4(12) . . . . ? C83 C84 C85 S4 0.8(15) . . . . ? C13 C12 S1 C15 1.5(12) . . . . ? C11 C12 S1 C15 -175.6(12) . . . . ? C14 C15 S1 C12 -3.0(11) . . . . ? C16 C15 S1 C12 178.0(11) . . . . ? C33 C32 S2 C35 5.5(12) . . . . ? C31 C32 S2 C35 -168.3(13) . . . . ? C34 C35 S2 C32 -3.8(11) . . . . ? C36 C35 S2 C32 177.6(11) . . . . ? C63 C62 S3 C65 -2.0(11) . . . . ? C61 C62 S3 C65 174.2(12) . . . . ? C64 C65 S3 C62 2.2(11) . . . . ? C66 C65 S3 C62 179.1(11) . . . . ? C83 C82 S4 C85 -4.6(12) . . . . ? C81 C82 S4 C85 171.3(13) . . . . ? C84 C85 S4 C82 2.1(11) . . . . ? C86 C85 S4 C82 -177.7(12) . . . . ? C63 C62 S3 C65 -1.2(10) . . . . ? C61 C62 S3 C65 174.8(10) . . . . ? C64 C65 S3 C62 0.9(10) . . . . ? C66 C65 S3 C62 179.8(9) . . . . ? C83 C82 S4 C85 -3.0(10) . . . . ? C81 C82 S4 C85 171.4(11) . . . . ? C84 C85 S4 C82 1.8(9) . . . . ? C86 C85 S4 C82 -176.8(10) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961274' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9.50GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety '2(C17 H14 F6 S2)' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.377(2) _cell_length_b 16.060(3) _cell_length_c 15.031(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.45(3) _cell_angle_gamma 90.00 _cell_volume 2463.5(9) _cell_formula_units_Z 8 _cell_measurement_reflns_used 1925 _cell_measurement_theta_min 3.5355 _cell_measurement_theta_max 25.9484 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 7068 _diffrn_reflns_av_R_equivalents 0.1037 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.25 _reflns_number_total 1356 _reflns_number_gt 969 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.277 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.277 _refine_diff_density_max 0.502 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.088 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 1356 _refine_ls_number_parameters 209 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.1158 _refine_ls_R_factor_gt 0.0824 _refine_ls_wR_factor_ref 0.2172 _refine_ls_wR_factor_gt 0.1875 _refine_ls_goodness_of_fit_ref 1.437 _refine_ls_restrained_S_all 1.403 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.0107(8) 0.4122(4) 0.2130(12) 0.011(2) Uiso 1 1 d D . . C2 C 0.0097(8) 0.3255(4) 0.1784(11) 0.016(2) Uiso 1 1 d D . . C3 C -0.0156(7) 0.2741(4) 0.2623(12) 0.011(2) Uiso 1 1 d D . . C4 C -0.0813(8) 0.3347(5) 0.3119(13) 0.016(2) Uiso 1 1 d D . . C5 C -0.0246(8) 0.4169(4) 0.2936(12) 0.010(2) Uiso 1 1 d D . . C11 C -0.1515(9) 0.5743(5) 0.1828(17) 0.019(2) Uiso 1 1 d D . . H11A H -0.1996 0.5245 0.1901 0.028 Uiso 1 1 calc R . . H11B H -0.2070 0.6124 0.1441 0.028 Uiso 1 1 calc R . . H11C H -0.1225 0.5997 0.2408 0.028 Uiso 1 1 calc R . . C12 C -0.0354(8) 0.5530(4) 0.1412(14) 0.014(2) Uiso 1 1 d D . . C13 C 0.0385(8) 0.4809(4) 0.1558(13) 0.017(2) Uiso 1 1 d D . . C14 C 0.1402(7) 0.4790(4) 0.1047(14) 0.0102(19) Uiso 1 1 d D . . H14 H 0.1996 0.4352 0.1081 0.012 Uiso 1 1 calc R . . C15 C 0.1442(8) 0.5452(4) 0.0510(13) 0.015(2) Uiso 1 1 d D . . C16 C 0.2336(8) 0.5604(5) -0.0148(15) 0.017(2) Uiso 1 1 d D . . H16A H 0.2952 0.5155 -0.0117 0.026 Uiso 1 1 calc R . . H16B H 0.2799 0.6118 -0.0001 0.026 Uiso 1 1 calc R . . H16C H 0.1831 0.5638 -0.0749 0.026 Uiso 1 1 calc R . . C31 C 0.1846(8) 0.5642(5) 0.3263(16) 0.016(2) Uiso 1 1 d D . . H31A H 0.2447 0.5232 0.3561 0.024 Uiso 1 1 calc R . . H31B H 0.2191 0.6189 0.3416 0.024 Uiso 1 1 calc R . . H31C H 0.1727 0.5565 0.2620 0.024 Uiso 1 1 calc R . . C32 C 0.0565(8) 0.5551(4) 0.3562(14) 0.016(2) Uiso 1 1 d D . . C33 C -0.0264(8) 0.4883(4) 0.3519(13) 0.012(2) Uiso 1 1 d D . . C34 C -0.1236(8) 0.4963(4) 0.4078(15) 0.014(2) Uiso 1 1 d D . . H34 H -0.1843 0.4549 0.4135 0.017 Uiso 1 1 calc R . . C35 C -0.1182(8) 0.5691(4) 0.4508(14) 0.016(2) Uiso 1 1 d D . . C36 C -0.2008(9) 0.5988(5) 0.5160(16) 0.020(2) Uiso 1 1 d D . . H36A H -0.2640 0.5568 0.5231 0.029 Uiso 1 1 calc R . . H36B H -0.2454 0.6489 0.4933 0.029 Uiso 1 1 calc R . . H36C H -0.1461 0.6098 0.5735 0.029 Uiso 1 1 calc R . . C51 C 0.4845(7) 0.8311(4) 0.2941(13) 0.009(2) Uiso 1 1 d D . . C52 C 0.4747(8) 0.9181(4) 0.3259(12) 0.016(2) Uiso 1 1 d D . . C53 C 0.4942(7) 0.9704(5) 0.2439(12) 0.015(2) Uiso 1 1 d D . . C54 C 0.5696(8) 0.9152(6) 0.1926(13) 0.022(3) Uiso 1 1 d D . . C55 C 0.5199(8) 0.8296(4) 0.2124(13) 0.013(2) Uiso 1 1 d D . . C61 C 0.6591(9) 0.6718(5) 0.3009(16) 0.019(2) Uiso 1 1 d D . . H61A H 0.6272 0.6434 0.2451 0.028 Uiso 1 1 calc R . . H61B H 0.7238 0.6380 0.3380 0.028 Uiso 1 1 calc R . . H61C H 0.6977 0.7239 0.2884 0.028 Uiso 1 1 calc R . . C62 C 0.5465(8) 0.6879(4) 0.3501(14) 0.014(2) Uiso 1 1 d D . . C63 C 0.4674(9) 0.7585(4) 0.3488(16) 0.016(2) Uiso 1 1 d D . . C64 C 0.3757(8) 0.7523(4) 0.4063(14) 0.013(2) Uiso 1 1 d D . . H64 H 0.3154 0.7938 0.4125 0.016 Uiso 1 1 calc R . . C65 C 0.3845(8) 0.6796(5) 0.4516(14) 0.018(2) Uiso 1 1 d D . . C66 C 0.3035(9) 0.6493(5) 0.5188(15) 0.023(2) Uiso 1 1 d D . . H66A H 0.3559 0.6496 0.5784 0.035 Uiso 1 1 calc R . . H66B H 0.2739 0.5936 0.5034 0.035 Uiso 1 1 calc R . . H66C H 0.2292 0.6852 0.5173 0.035 Uiso 1 1 calc R . . C81 C 0.3266(8) 0.6802(5) 0.1572(17) 0.014(2) Uiso 1 1 d D . . H81A H 0.3302 0.6991 0.2182 0.020 Uiso 1 1 calc R . . H81B H 0.3066 0.6218 0.1535 0.020 Uiso 1 1 calc R . . H81C H 0.2598 0.7104 0.1175 0.020 Uiso 1 1 calc R . . C82 C 0.4552(8) 0.6947(4) 0.1300(15) 0.015(2) Uiso 1 1 d D . . C83 C 0.5326(8) 0.7628(4) 0.1508(16) 0.013(2) Uiso 1 1 d D . . C84 C 0.6388(8) 0.7638(4) 0.1025(15) 0.016(2) Uiso 1 1 d D . . H84 H 0.6998 0.8068 0.1081 0.020 Uiso 1 1 calc R . . C85 C 0.6441(8) 0.6977(4) 0.0483(15) 0.017(2) Uiso 1 1 d D . . C86 C 0.7411(8) 0.6830(5) -0.0114(15) 0.017(2) Uiso 1 1 d D . . H86A H 0.6985 0.6871 -0.0735 0.026 Uiso 1 1 calc R . . H86B H 0.7783 0.6285 -0.0001 0.026 Uiso 1 1 calc R . . H86C H 0.8093 0.7240 0.0009 0.026 Uiso 1 1 calc R . . F1 F 0.1250(5) 0.3020(3) 0.1559(11) 0.0209(13) Uiso 1 1 d D . . F2 F -0.0821(5) 0.3096(3) 0.1061(10) 0.0247(14) Uiso 1 1 d D . . F3 F 0.0969(5) 0.2486(3) 0.3079(10) 0.0266(14) Uiso 1 1 d D . . F4 F -0.0914(5) 0.2070(3) 0.2379(11) 0.0252(14) Uiso 1 1 d D . . F5 F -0.0569(5) 0.3120(3) 0.4011(11) 0.0244(16) Uiso 1 1 d D . . F6 F -0.2123(4) 0.3363(3) 0.2866(10) 0.0191(13) Uiso 1 1 d D . . F7 F 0.5675(5) 0.9378(3) 0.3965(10) 0.0241(15) Uiso 1 1 d D . . F8 F 0.3586(5) 0.9347(3) 0.3499(11) 0.0247(14) Uiso 1 1 d D . . F9 F 0.5609(5) 1.0416(3) 0.2727(10) 0.0234(14) Uiso 1 1 d D . . F10 F 0.3798(5) 0.9906(3) 0.1950(10) 0.0247(14) Uiso 1 1 d D . . F11 F 0.7003(4) 0.9162(3) 0.2269(10) 0.0195(13) Uiso 1 1 d D . . F12 F 0.5536(5) 0.9354(3) 0.1026(11) 0.0247(16) Uiso 1 1 d D . . S1 S 0.0252(2) 0.61597(11) 0.0673(5) 0.0144(7) Uiso 1 1 d D . . S2 S 0.0054(2) 0.62940(11) 0.4245(5) 0.0152(7) Uiso 1 1 d D . . S3 S 0.5021(2) 0.61749(11) 0.4224(5) 0.0157(7) Uiso 1 1 d D . . S4 S 0.5190(2) 0.62977(11) 0.0593(5) 0.0147(7) Uiso 1 1 d D . . _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 C5 1.329(17) . ? C1 C13 1.461(12) . ? C1 C2 1.485(10) . ? C2 F2 1.334(15) . ? C2 F1 1.355(9) . ? C2 C3 1.569(16) . ? C3 F3 1.308(12) . ? C3 F4 1.344(9) . ? C3 C4 1.468(14) . ? C4 F6 1.343(10) . ? C4 F5 1.368(18) . ? C4 C5 1.492(11) . ? C5 C33 1.446(15) . ? C11 C12 1.494(13) . ? C12 C13 1.384(9) . ? C12 S1 1.705(13) . ? C13 C14 1.413(13) . ? C14 C15 1.341(14) . ? C15 C16 1.494(16) . ? C15 S1 1.728(7) . ? C31 C32 1.485(12) . ? C32 C33 1.369(9) . ? C32 S2 1.719(13) . ? C33 C34 1.430(14) . ? C34 C35 1.332(13) . ? C35 C36 1.492(16) . ? C35 S2 1.710(8) . ? C51 C55 1.344(14) . ? C51 C63 1.457(18) . ? C51 C52 1.486(11) . ? C52 F7 1.335(15) . ? C52 F8 1.345(10) . ? C52 C53 1.534(16) . ? C53 F10 1.319(12) . ? C53 F9 1.366(10) . ? C53 C54 1.487(14) . ? C54 F11 1.361(11) . ? C54 F12 1.372(18) . ? C54 C55 1.516(12) . ? C55 C83 1.44(2) . ? C61 C62 1.513(14) . ? C62 C63 1.398(9) . ? C62 S3 1.689(13) . ? C63 C64 1.400(15) . ? C64 C65 1.346(13) . ? C65 C66 1.508(16) . ? C65 S3 1.695(9) . ? C81 C82 1.483(11) . ? C82 C83 1.359(10) . ? C82 S4 1.706(13) . ? C83 C84 1.425(14) . ? C84 C85 1.346(14) . ? C85 C86 1.482(15) . ? C85 S4 1.727(7) . ? 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 C5 C1 C13 127.5(9) . . ? C5 C1 C2 112.8(9) . . ? C13 C1 C2 119.4(12) . . ? F2 C2 F1 106.0(11) . . ? F2 C2 C1 115.1(9) . . ? F1 C2 C1 113.5(7) . . ? F2 C2 C3 110.8(8) . . ? F1 C2 C3 109.8(9) . . ? C1 C2 C3 101.7(10) . . ? F3 C3 F4 108.4(7) . . ? F3 C3 C4 113.2(13) . . ? F4 C3 C4 111.5(7) . . ? F3 C3 C2 108.9(8) . . ? F4 C3 C2 112.2(12) . . ? C4 C3 C2 102.7(8) . . ? F6 C4 F5 106.3(11) . . ? F6 C4 C3 114.0(10) . . ? F5 C4 C3 107.5(10) . . ? F6 C4 C5 110.1(9) . . ? F5 C4 C5 114.1(12) . . ? C3 C4 C5 105.0(9) . . ? C1 C5 C33 129.4(9) . . ? C1 C5 C4 107.5(10) . . ? C33 C5 C4 122.7(12) . . ? C13 C12 C11 126.2(11) . . ? C13 C12 S1 109.9(8) . . ? C11 C12 S1 123.9(7) . . ? C12 C13 C14 112.3(10) . . ? C12 C13 C1 124.2(9) . . ? C14 C13 C1 123.3(7) . . ? C15 C14 C13 114.7(7) . . ? C14 C15 C16 128.3(8) . . ? C14 C15 S1 109.6(8) . . ? C16 C15 S1 122.1(7) . . ? C33 C32 C31 130.7(9) . . ? C33 C32 S2 108.2(8) . . ? C31 C32 S2 120.1(8) . . ? C32 C33 C34 114.0(10) . . ? C32 C33 C5 124.9(11) . . ? C34 C33 C5 121.0(7) . . ? C35 C34 C33 113.1(8) . . ? C34 C35 C36 128.4(8) . . ? C34 C35 S2 110.6(9) . . ? C36 C35 S2 121.0(7) . . ? C55 C51 C63 125.7(10) . . ? C55 C51 C52 110.9(10) . . ? C63 C51 C52 123.3(15) . . ? F7 C52 F8 107.0(12) . . ? F7 C52 C51 113.3(9) . . ? F8 C52 C51 112.9(7) . . ? F7 C52 C53 109.1(8) . . ? F8 C52 C53 111.2(9) . . ? C51 C52 C53 103.2(11) . . ? F10 C53 F9 108.9(7) . . ? F10 C53 C54 111.3(12) . . ? F9 C53 C54 112.3(7) . . ? F10 C53 C52 110.2(8) . . ? F9 C53 C52 109.7(12) . . ? C54 C53 C52 104.4(9) . . ? F11 C54 F12 107.7(11) . . ? F11 C54 C53 112.2(11) . . ? F12 C54 C53 113.0(10) . . ? F11 C54 C55 106.7(9) . . ? F12 C54 C55 115.0(12) . . ? C53 C54 C55 102.0(10) . . ? C51 C55 C83 132.3(10) . . ? C51 C55 C54 108.8(11) . . ? C83 C55 C54 118.4(14) . . ? C63 C62 C61 129.4(11) . . ? C63 C62 S3 108.8(10) . . ? C61 C62 S3 121.7(7) . . ? C62 C63 C64 113.5(11) . . ? C62 C63 C51 121.7(12) . . ? C64 C63 C51 124.8(8) . . ? C65 C64 C63 112.4(8) . . ? C64 C65 C66 128.6(8) . . ? C64 C65 S3 111.5(9) . . ? C66 C65 S3 119.9(7) . . ? C83 C82 C81 125.9(11) . . ? C83 C82 S4 110.8(8) . . ? C81 C82 S4 123.1(9) . . ? C82 C83 C84 111.8(11) . . ? C82 C83 C55 128.9(11) . . ? C84 C83 C55 119.3(8) . . ? C85 C84 C83 114.9(8) . . ? C84 C85 C86 126.8(8) . . ? C84 C85 S4 109.0(8) . . ? C86 C85 S4 124.2(8) . . ? C12 S1 C15 93.4(5) . . ? C35 S2 C32 94.0(5) . . ? C65 S3 C62 93.8(5) . . ? C82 S4 C85 93.3(5) . . ? 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 C5 C1 C2 F2 112.2(12) . . . . ? C13 C1 C2 F2 -63.2(12) . . . . ? C5 C1 C2 F1 -125.5(13) . . . . ? C13 C1 C2 F1 59.1(15) . . . . ? C5 C1 C2 C3 -7.7(11) . . . . ? C13 C1 C2 C3 176.9(8) . . . . ? F2 C2 C3 F3 141.3(8) . . . . ? F1 C2 C3 F3 24.6(12) . . . . ? C1 C2 C3 F3 -95.8(9) . . . . ? F2 C2 C3 F4 21.4(8) . . . . ? F1 C2 C3 F4 -95.3(9) . . . . ? C1 C2 C3 F4 144.2(7) . . . . ? F2 C2 C3 C4 -98.5(8) . . . . ? F1 C2 C3 C4 144.8(9) . . . . ? C1 C2 C3 C4 24.4(9) . . . . ? F3 C3 C4 F6 -154.1(10) . . . . ? F4 C3 C4 F6 -31.6(18) . . . . ? C2 C3 C4 F6 88.7(12) . . . . ? F3 C3 C4 F5 -36.5(10) . . . . ? F4 C3 C4 F5 86.0(12) . . . . ? C2 C3 C4 F5 -153.6(7) . . . . ? F3 C3 C4 C5 85.4(13) . . . . ? F4 C3 C4 C5 -152.1(13) . . . . ? C2 C3 C4 C5 -31.8(12) . . . . ? C13 C1 C5 C33 -10.2(18) . . . . ? C2 C1 C5 C33 174.9(10) . . . . ? C13 C1 C5 C4 162.7(10) . . . . ? C2 C1 C5 C4 -12.2(12) . . . . ? F6 C4 C5 C1 -94.6(13) . . . . ? F5 C4 C5 C1 146.0(9) . . . . ? C3 C4 C5 C1 28.6(13) . . . . ? F6 C4 C5 C33 78.9(17) . . . . ? F5 C4 C5 C33 -40.6(13) . . . . ? C3 C4 C5 C33 -158.0(11) . . . . ? C11 C12 C13 C14 178.7(16) . . . . ? S1 C12 C13 C14 -1.2(17) . . . . ? C11 C12 C13 C1 2(3) . . . . ? S1 C12 C13 C1 -177.8(11) . . . . ? C5 C1 C13 C12 -42(2) . . . . ? C2 C1 C13 C12 132.2(15) . . . . ? C5 C1 C13 C14 141.3(14) . . . . ? C2 C1 C13 C14 -44.1(17) . . . . ? C12 C13 C14 C15 -1.5(19) . . . . ? C1 C13 C14 C15 175.1(13) . . . . ? C13 C14 C15 C16 -176.4(14) . . . . ? C13 C14 C15 S1 3.4(16) . . . . ? C31 C32 C33 C34 164.9(19) . . . . ? S2 C32 C33 C34 -3.6(17) . . . . ? C31 C32 C33 C5 -19(3) . . . . ? S2 C32 C33 C5 173.0(12) . . . . ? C1 C5 C33 C32 -30(2) . . . . ? C4 C5 C33 C32 158.3(14) . . . . ? C1 C5 C33 C34 146.6(13) . . . . ? C4 C5 C33 C34 -25.3(18) . . . . ? C32 C33 C34 C35 3(2) . . . . ? C5 C33 C34 C35 -174.2(14) . . . . ? C33 C34 C35 C36 -178.4(14) . . . . ? C33 C34 C35 S2 -0.1(17) . . . . ? C55 C51 C52 F7 -111.3(12) . . . . ? C63 C51 C52 F7 64.3(12) . . . . ? C55 C51 C52 F8 126.8(13) . . . . ? C63 C51 C52 F8 -57.5(16) . . . . ? C55 C51 C52 C53 6.6(10) . . . . ? C63 C51 C52 C53 -177.8(9) . . . . ? F7 C52 C53 F10 -144.1(8) . . . . ? F8 C52 C53 F10 -26.3(12) . . . . ? C51 C52 C53 F10 95.1(9) . . . . ? F7 C52 C53 F9 -24.3(8) . . . . ? F8 C52 C53 F9 93.5(9) . . . . ? C51 C52 C53 F9 -145.1(7) . . . . ? F7 C52 C53 C54 96.3(8) . . . . ? F8 C52 C53 C54 -145.9(10) . . . . ? C51 C52 C53 C54 -24.5(9) . . . . ? F10 C53 C54 F11 159.1(10) . . . . ? F9 C53 C54 F11 36.7(17) . . . . ? C52 C53 C54 F11 -82.0(11) . . . . ? F10 C53 C54 F12 37.0(11) . . . . ? F9 C53 C54 F12 -85.3(13) . . . . ? C52 C53 C54 F12 155.9(8) . . . . ? F10 C53 C54 C55 -87.0(12) . . . . ? F9 C53 C54 C55 150.6(12) . . . . ? C52 C53 C54 C55 31.9(12) . . . . ? C63 C51 C55 C83 10.0(18) . . . . ? C52 C51 C55 C83 -174.5(11) . . . . ? C63 C51 C55 C54 -161.5(10) . . . . ? C52 C51 C55 C54 14.0(11) . . . . ? F11 C54 C55 C51 88.7(12) . . . . ? F12 C54 C55 C51 -151.9(8) . . . . ? C53 C54 C55 C51 -29.2(13) . . . . ? F11 C54 C55 C83 -84.2(15) . . . . ? F12 C54 C55 C83 35.3(13) . . . . ? C53 C54 C55 C83 157.9(11) . . . . ? C61 C62 C63 C64 -177.4(15) . . . . ? S3 C62 C63 C64 0.2(18) . . . . ? C61 C62 C63 C51 1(3) . . . . ? S3 C62 C63 C51 178.5(13) . . . . ? C55 C51 C63 C62 35(2) . . . . ? C52 C51 C63 C62 -139.9(15) . . . . ? C55 C51 C63 C64 -146.8(14) . . . . ? C52 C51 C63 C64 38.2(19) . . . . ? C62 C63 C64 C65 0.8(19) . . . . ? C51 C63 C64 C65 -177.4(16) . . . . ? C63 C64 C65 C66 -179.6(14) . . . . ? C63 C64 C65 S3 -1.4(16) . . . . ? C81 C82 C83 C84 -170.5(18) . . . . ? S4 C82 C83 C84 4.5(19) . . . . ? C81 C82 C83 C55 10(3) . . . . ? S4 C82 C83 C55 -175.4(15) . . . . ? C51 C55 C83 C82 39(3) . . . . ? C54 C55 C83 C82 -150.1(17) . . . . ? C51 C55 C83 C84 -140.8(14) . . . . ? C54 C55 C83 C84 30.0(19) . . . . ? C82 C83 C84 C85 -1(2) . . . . ? C55 C83 C84 C85 178.5(15) . . . . ? C83 C84 C85 C86 178.4(14) . . . . ? C83 C84 C85 S4 -2.3(17) . . . . ? C13 C12 S1 C15 2.6(13) . . . . ? C11 C12 S1 C15 -177.2(15) . . . . ? C14 C15 S1 C12 -3.4(12) . . . . ? C16 C15 S1 C12 176.3(12) . . . . ? C34 C35 S2 C32 -1.7(14) . . . . ? C36 C35 S2 C32 176.8(12) . . . . ? C33 C32 S2 C35 3.0(14) . . . . ? C31 C32 S2 C35 -166.9(16) . . . . ? C66 C65 S3 C62 179.7(13) . . . . ? C63 C62 S3 C65 -0.9(13) . . . . ? C61 C62 S3 C65 177.0(14) . . . . ? C81 C82 S4 C85 170.2(16) . . . . ? C84 C85 S4 C82 4.1(13) . . . . ? C86 C85 S4 C82 -176.5(14) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 961275' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9.80GPaDimethylthiopheneDTE _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-Bis(2,5-dimethylthiophen-3-yl)' perfluorocyclopentene ; _chemical_name_common DimethylthiopheneDTE _chemical_formula_moiety '2(C17 H14 F6 S2)' _chemical_formula_sum 'C17 H14 F6 S2' _chemical_formula_weight 396.42 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0165 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1188 0.1164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.3834(5) _cell_length_b 16.0279(8) _cell_length_c 15.0219(45) _cell_angle_alpha 90.00 _cell_angle_beta 100.443(7) _cell_angle_gamma 90.00 _cell_volume 2458.6(7) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2092 _cell_measurement_theta_min 3.5444 _cell_measurement_theta_max 25.6867 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.402 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_monochromator Synchrotron _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method \w _diffrn_reflns_number 7870 _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.58 _reflns_number_total 1359 _reflns_number_gt 1060 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.269 _diffrn_reflns_theta_full 25.58 _diffrn_measured_fraction_theta_full 0.269 _refine_diff_density_max 0.468 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.054 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^)+(0.0538P)^2^+1.4525P] 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 1359 _refine_ls_number_parameters 229 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1281 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.0107(5) 0.4124(3) 0.2123(10) 0.0088(13) Uiso 1 1 d D . . C2 C 0.0100(5) 0.3249(3) 0.1776(10) 0.0111(13) Uiso 1 1 d D . . C3 C -0.0176(5) 0.2740(3) 0.2608(10) 0.0096(13) Uiso 1 1 d D . . C4 C -0.0800(6) 0.3344(4) 0.3129(11) 0.0171(17) Uiso 1 1 d D . . C5 C -0.0236(5) 0.4165(3) 0.2943(10) 0.0084(13) Uiso 1 1 d D . . C11 C -0.1507(6) 0.5739(3) 0.1845(13) 0.0134(14) Uiso 1 1 d D . . H11A H -0.1898 0.5232 0.2009 0.020 Uiso 1 1 calc R . . H11B H -0.2133 0.6041 0.1414 0.020 Uiso 1 1 calc R . . H11C H -0.1242 0.6075 0.2375 0.020 Uiso 1 1 calc R . . C12 C -0.0339(6) 0.5535(3) 0.1435(11) 0.0115(13) Uiso 1 1 d D . . C13 C 0.0390(6) 0.4811(3) 0.1559(10) 0.0135(14) Uiso 1 1 d D . . C14 C 0.1407(5) 0.4780(3) 0.1050(11) 0.0112(13) Uiso 1 1 d D . . H14 H 0.1990 0.4337 0.1072 0.013 Uiso 1 1 calc R . . C15 C 0.1445(6) 0.5459(3) 0.0529(11) 0.0133(14) Uiso 1 1 d D . . C16 C 0.2335(6) 0.5605(3) -0.0132(12) 0.0149(14) Uiso 1 1 d D . . H16A H 0.2992 0.5177 -0.0066 0.022 Uiso 1 1 calc R . . H16B H 0.2749 0.6140 -0.0018 0.022 Uiso 1 1 calc R . . H16C H 0.1838 0.5593 -0.0736 0.022 Uiso 1 1 calc R . . C31 C 0.1847(6) 0.5642(4) 0.3251(13) 0.0146(14) Uiso 1 1 d D . . H31A H 0.2453 0.5226 0.3530 0.022 Uiso 1 1 calc R . . H31B H 0.2204 0.6187 0.3405 0.022 Uiso 1 1 calc R . . H31C H 0.1697 0.5573 0.2606 0.022 Uiso 1 1 calc R . . C32 C 0.0574(6) 0.5551(3) 0.3584(12) 0.0127(14) Uiso 1 1 d D . . C33 C -0.0259(5) 0.4878(3) 0.3517(11) 0.0115(13) Uiso 1 1 d D . . C34 C -0.1230(5) 0.4959(3) 0.4063(11) 0.0128(14) Uiso 1 1 d D . . H34 H -0.1841 0.4545 0.4111 0.015 Uiso 1 1 calc R . . C35 C -0.1186(6) 0.5693(3) 0.4508(11) 0.0152(14) Uiso 1 1 d D . . C36 C -0.2006(6) 0.5999(4) 0.5163(13) 0.0181(15) Uiso 1 1 d D . . H36A H -0.2584 0.5562 0.5282 0.027 Uiso 1 1 calc R . . H36B H -0.2512 0.6471 0.4909 0.027 Uiso 1 1 calc R . . H36C H -0.1448 0.6160 0.5717 0.027 Uiso 1 1 calc R . . C51 C 0.4841(5) 0.8309(3) 0.2933(10) 0.0077(13) Uiso 1 1 d D . . C52 C 0.4758(5) 0.9179(3) 0.3266(10) 0.0132(14) Uiso 1 1 d D . . C53 C 0.4956(5) 0.9713(3) 0.2448(10) 0.0106(14) Uiso 1 1 d D . . C54 C 0.5693(6) 0.9144(4) 0.1938(11) 0.0184(17) Uiso 1 1 d D . . C55 C 0.5191(5) 0.8295(3) 0.2116(10) 0.0082(13) Uiso 1 1 d D . . C61 C 0.6606(6) 0.6730(3) 0.3042(12) 0.0145(14) Uiso 1 1 d D . . H61A H 0.6316 0.6437 0.2484 0.022 Uiso 1 1 calc R . . H61B H 0.7250 0.6401 0.3428 0.022 Uiso 1 1 calc R . . H61C H 0.6985 0.7254 0.2918 0.022 Uiso 1 1 calc R . . C62 C 0.5461(6) 0.6883(3) 0.3503(11) 0.0133(14) Uiso 1 1 d D . . C63 C 0.4677(6) 0.7585(3) 0.3484(12) 0.0131(14) Uiso 1 1 d D . . C64 C 0.3756(6) 0.7520(3) 0.4062(11) 0.0143(14) Uiso 1 1 d D . . H64 H 0.3155 0.7936 0.4127 0.017 Uiso 1 1 calc R . . C65 C 0.3841(6) 0.6798(3) 0.4505(11) 0.0148(14) Uiso 1 1 d D . . C66 C 0.3037(6) 0.6482(4) 0.5179(12) 0.0210(16) Uiso 1 1 d D . . H66A H 0.3555 0.6500 0.5777 0.031 Uiso 1 1 calc R . . H66B H 0.2769 0.5918 0.5032 0.031 Uiso 1 1 calc R . . H66C H 0.2277 0.6828 0.5157 0.031 Uiso 1 1 calc R . . C81 C 0.3270(6) 0.6805(3) 0.1593(13) 0.0123(14) Uiso 1 1 d D . . H81A H 0.3314 0.6998 0.2203 0.019 Uiso 1 1 calc R . . H81B H 0.3068 0.6220 0.1561 0.019 Uiso 1 1 calc R . . H81C H 0.2599 0.7106 0.1197 0.019 Uiso 1 1 calc R . . C82 C 0.4549(6) 0.6945(3) 0.1311(12) 0.0115(14) Uiso 1 1 d D . . C83 C 0.5331(6) 0.7633(3) 0.1508(12) 0.0105(13) Uiso 1 1 d D . . C84 C 0.6390(6) 0.7644(3) 0.1016(11) 0.0130(14) Uiso 1 1 d D . . H84 H 0.6987 0.8081 0.1054 0.016 Uiso 1 1 calc R . . C85 C 0.6446(6) 0.6976(3) 0.0498(11) 0.0117(13) Uiso 1 1 d D . . C86 C 0.7413(6) 0.6819(3) -0.0099(12) 0.0148(14) Uiso 1 1 d D . . H86A H 0.7003 0.6900 -0.0719 0.022 Uiso 1 1 calc R . . H86B H 0.7729 0.6256 -0.0017 0.022 Uiso 1 1 calc R . . H86C H 0.8134 0.7199 0.0052 0.022 Uiso 1 1 calc R . . F1 F 0.1249(3) 0.30228(19) 0.1548(8) 0.0173(9) Uiso 1 1 d D . . F2 F -0.0833(4) 0.3093(2) 0.1036(8) 0.0231(10) Uiso 1 1 d D . . F3 F 0.0965(4) 0.2482(2) 0.3090(8) 0.0249(10) Uiso 1 1 d D . . F4 F -0.0928(4) 0.2070(2) 0.2367(8) 0.0219(9) Uiso 1 1 d D . . F5 F -0.0590(4) 0.3118(2) 0.4018(9) 0.0241(11) Uiso 1 1 d D . . F6 F -0.2128(3) 0.33600(19) 0.2851(7) 0.0164(9) Uiso 1 1 d D . . F7 F 0.5682(4) 0.9382(2) 0.3987(8) 0.0233(10) Uiso 1 1 d D . . F8 F 0.3585(3) 0.9349(2) 0.3494(8) 0.0204(9) Uiso 1 1 d D . . F9 F 0.5602(3) 1.0421(2) 0.2699(8) 0.0206(9) Uiso 1 1 d D . . F10 F 0.3792(3) 0.9908(2) 0.1934(8) 0.0211(9) Uiso 1 1 d D . . F11 F 0.7004(3) 0.91648(19) 0.2277(7) 0.0160(8) Uiso 1 1 d D . . F12 F 0.5550(4) 0.9356(2) 0.1034(9) 0.0216(11) Uiso 1 1 d D . . S1 S 0.02547(14) 0.61627(8) 0.0686(3) 0.016(4) Uani 1 1 d D . . S2 S 0.00577(15) 0.62969(8) 0.4245(4) 0.019(4) Uani 1 1 d D . . S3 S 0.50230(15) 0.61718(8) 0.4224(4) 0.023(4) Uani 1 1 d D . . S4 S 0.51897(14) 0.62970(8) 0.0599(4) 0.019(4) Uani 1 1 d 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 S1 0.0115(7) 0.0119(7) 0.024(13) 0.0043(17) 0.002(2) 0.0004(5) S2 0.0147(8) 0.0106(7) 0.033(13) -0.0033(16) 0.005(2) 0.0009(5) S3 0.0163(8) 0.0121(7) 0.043(13) 0.0011(17) 0.009(2) -0.0006(5) S4 0.0124(8) 0.0114(7) 0.034(13) -0.0040(16) 0.005(2) -0.0007(5) _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 C5 1.344(16) . ? C1 C13 1.451(11) . ? C1 C2 1.497(9) . ? C2 F1 1.349(7) . ? C2 F2 1.359(13) . ? C2 C3 1.562(15) . ? C3 F3 1.337(10) . ? C3 F4 1.338(7) . ? C3 C4 1.468(12) . ? C4 F5 1.363(16) . ? C4 F6 1.367(8) . ? C4 C5 1.488(9) . ? C5 C33 1.434(13) . ? C11 C12 1.493(11) . ? C12 C13 1.379(7) . ? C12 S1 1.706(12) . ? C13 C14 1.412(12) . ? C14 C15 1.345(12) . ? C15 C16 1.492(14) . ? C15 S1 1.721(6) . ? C31 C32 1.503(10) . ? C32 C33 1.374(7) . ? C32 S2 1.702(11) . ? C33 C34 1.417(12) . ? C34 C35 1.349(12) . ? C35 C36 1.496(14) . ? C35 S2 1.717(6) . ? C51 C55 1.341(13) . ? C51 C63 1.454(14) . ? C51 C52 1.489(9) . ? C52 F8 1.351(8) . ? C52 F7 1.350(13) . ? C52 C53 1.542(15) . ? C53 F9 1.337(7) . ? C53 F10 1.348(10) . ? C53 C54 1.489(12) . ? C54 F11 1.365(8) . ? C54 F12 1.380(17) . ? C54 C55 1.500(9) . ? C55 C83 1.425(16) . ? C61 C62 1.501(11) . ? C62 C63 1.386(7) . ? C62 S3 1.690(12) . ? C63 C64 1.407(13) . ? C64 C65 1.330(11) . ? C65 C66 1.511(14) . ? C65 S3 1.697(7) . ? C81 C82 1.483(9) . ? C82 C83 1.368(8) . ? C82 S4 1.710(12) . ? C83 C84 1.432(12) . ? C84 C85 1.331(12) . ? C85 C86 1.485(13) . ? C85 S4 1.726(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C1 C13 127.9(7) . . ? C5 C1 C2 112.3(7) . . ? C13 C1 C2 119.7(10) . . ? F1 C2 F2 106.0(9) . . ? F1 C2 C1 113.1(4) . . ? F2 C2 C1 114.5(6) . . ? F1 C2 C3 111.2(7) . . ? F2 C2 C3 110.5(6) . . ? C1 C2 C3 101.6(9) . . ? F3 C3 F4 108.4(5) . . ? F3 C3 C4 110.4(10) . . ? F4 C3 C4 112.3(6) . . ? F3 C3 C2 108.8(6) . . ? F4 C3 C2 112.7(10) . . ? C4 C3 C2 104.2(7) . . ? F5 C4 F6 106.1(8) . . ? F5 C4 C3 109.9(8) . . ? F6 C4 C3 111.7(9) . . ? F5 C4 C5 114.8(10) . . ? F6 C4 C5 109.7(7) . . ? C3 C4 C5 104.9(8) . . ? C1 C5 C33 128.7(7) . . ? C1 C5 C4 107.9(9) . . ? C33 C5 C4 122.9(11) . . ? C13 C12 C11 126.6(9) . . ? C13 C12 S1 109.3(7) . . ? C11 C12 S1 124.1(6) . . ? C12 C13 C14 113.7(8) . . ? C12 C13 C1 123.5(8) . . ? C14 C13 C1 122.7(5) . . ? C15 C14 C13 113.0(6) . . ? C14 C15 C16 126.9(6) . . ? C14 C15 S1 110.6(7) . . ? C16 C15 S1 122.4(6) . . ? C33 C32 C31 129.2(8) . . ? C33 C32 S2 109.5(7) . . ? C31 C32 S2 120.9(5) . . ? C32 C33 C34 112.9(8) . . ? C32 C33 C5 126.2(9) . . ? C34 C33 C5 120.8(6) . . ? C35 C34 C33 113.8(6) . . ? C34 C35 C36 129.8(6) . . ? C34 C35 S2 109.7(7) . . ? C36 C35 S2 120.5(5) . . ? C55 C51 C63 125.9(8) . . ? C55 C51 C52 111.4(8) . . ? C63 C51 C52 122.4(12) . . ? F8 C52 F7 106.8(10) . . ? F8 C52 C51 112.6(5) . . ? F7 C52 C51 114.8(7) . . ? F8 C52 C53 110.2(7) . . ? F7 C52 C53 109.1(6) . . ? C51 C52 C53 103.2(9) . . ? F9 C53 F10 108.5(5) . . ? F9 C53 C54 112.7(5) . . ? F10 C53 C54 109.8(10) . . ? F9 C53 C52 112.3(10) . . ? F10 C53 C52 110.5(6) . . ? C54 C53 C52 103.0(7) . . ? F11 C54 F12 106.4(8) . . ? F11 C54 C53 111.4(9) . . ? F12 C54 C53 112.5(8) . . ? F11 C54 C55 108.1(7) . . ? F12 C54 C55 114.8(10) . . ? C53 C54 C55 103.7(8) . . ? C51 C55 C83 132.5(8) . . ? C51 C55 C54 108.0(9) . . ? C83 C55 C54 118.9(11) . . ? C63 C62 C61 129.4(9) . . ? C63 C62 S3 109.6(8) . . ? C61 C62 S3 120.9(5) . . ? C62 C63 C64 112.9(9) . . ? C62 C63 C51 122.0(10) . . ? C64 C63 C51 125.0(6) . . ? C65 C64 C63 112.5(6) . . ? C64 C65 C66 129.2(6) . . ? C64 C65 S3 112.0(8) . . ? C66 C65 S3 118.8(5) . . ? C83 C82 C81 126.0(9) . . ? C83 C82 S4 110.0(7) . . ? C81 C82 S4 123.8(6) . . ? C82 C83 C55 127.8(9) . . ? C82 C83 C84 112.3(9) . . ? C55 C83 C84 119.9(6) . . ? C85 C84 C83 114.2(6) . . ? C84 C85 C86 126.5(6) . . ? C84 C85 S4 110.0(7) . . ? C86 C85 S4 123.4(6) . . ? C12 S1 C15 93.3(4) . . ? C32 S2 C35 93.9(4) . . ? C62 S3 C65 93.0(4) . . ? C82 S4 C85 93.3(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 C5 C1 C2 F1 -125.2(10) . . . . ? C13 C1 C2 F1 58.2(12) . . . . ? C5 C1 C2 F2 113.3(9) . . . . ? C13 C1 C2 F2 -63.4(8) . . . . ? C5 C1 C2 C3 -5.9(7) . . . . ? C13 C1 C2 C3 177.5(6) . . . . ? F1 C2 C3 F3 25.1(9) . . . . ? F2 C2 C3 F3 142.6(7) . . . . ? C1 C2 C3 F3 -95.5(7) . . . . ? F1 C2 C3 F4 -95.1(7) . . . . ? F2 C2 C3 F4 22.4(6) . . . . ? C1 C2 C3 F4 144.3(5) . . . . ? F1 C2 C3 C4 142.9(8) . . . . ? F2 C2 C3 C4 -99.7(7) . . . . ? C1 C2 C3 C4 22.3(7) . . . . ? F3 C3 C4 F5 -37.4(7) . . . . ? F4 C3 C4 F5 83.7(10) . . . . ? C2 C3 C4 F5 -154.0(6) . . . . ? F3 C3 C4 F6 -154.8(8) . . . . ? F4 C3 C4 F6 -33.7(15) . . . . ? C2 C3 C4 F6 88.6(9) . . . . ? F3 C3 C4 C5 86.5(10) . . . . ? F4 C3 C4 C5 -152.4(10) . . . . ? C2 C3 C4 C5 -30.1(10) . . . . ? C13 C1 C5 C33 -8.2(13) . . . . ? C2 C1 C5 C33 175.4(7) . . . . ? C13 C1 C5 C4 163.4(7) . . . . ? C2 C1 C5 C4 -12.9(9) . . . . ? F5 C4 C5 C1 148.3(7) . . . . ? F6 C4 C5 C1 -92.4(10) . . . . ? C3 C4 C5 C1 27.6(11) . . . . ? F5 C4 C5 C33 -39.5(10) . . . . ? F6 C4 C5 C33 79.8(14) . . . . ? C3 C4 C5 C33 -160.2(9) . . . . ? C11 C12 C13 C14 177.3(12) . . . . ? S1 C12 C13 C14 0.1(14) . . . . ? C11 C12 C13 C1 0(2) . . . . ? S1 C12 C13 C1 -177.1(9) . . . . ? C5 C1 C13 C12 -42.4(16) . . . . ? C2 C1 C13 C12 133.7(12) . . . . ? C5 C1 C13 C14 140.7(11) . . . . ? C2 C1 C13 C14 -43.3(13) . . . . ? C12 C13 C14 C15 -1.3(15) . . . . ? C1 C13 C14 C15 175.9(11) . . . . ? C13 C14 C15 C16 -175.9(11) . . . . ? C13 C14 C15 S1 1.9(13) . . . . ? C31 C32 C33 C34 168.2(14) . . . . ? S2 C32 C33 C34 -4.9(14) . . . . ? C31 C32 C33 C5 -14(2) . . . . ? S2 C32 C33 C5 172.8(10) . . . . ? C1 C5 C33 C32 -32.5(16) . . . . ? C4 C5 C33 C32 157.0(12) . . . . ? C1 C5 C33 C34 145.0(10) . . . . ? C4 C5 C33 C34 -25.5(15) . . . . ? C32 C33 C34 C35 2.9(16) . . . . ? C5 C33 C34 C35 -174.9(11) . . . . ? C33 C34 C35 C36 -177.9(12) . . . . ? C33 C34 C35 S2 0.5(14) . . . . ? C55 C51 C52 F8 125.6(10) . . . . ? C63 C51 C52 F8 -59.7(12) . . . . ? C55 C51 C52 F7 -111.8(9) . . . . ? C63 C51 C52 F7 62.9(9) . . . . ? C55 C51 C52 C53 6.8(7) . . . . ? C63 C51 C52 C53 -178.5(6) . . . . ? F8 C52 C53 F9 93.6(7) . . . . ? F7 C52 C53 F9 -23.4(6) . . . . ? C51 C52 C53 F9 -145.9(5) . . . . ? F8 C52 C53 F10 -27.6(10) . . . . ? F7 C52 C53 F10 -144.6(7) . . . . ? C51 C52 C53 F10 92.9(7) . . . . ? F8 C52 C53 C54 -144.8(8) . . . . ? F7 C52 C53 C54 98.1(7) . . . . ? C51 C52 C53 C54 -24.3(7) . . . . ? F9 C53 C54 F11 37.5(14) . . . . ? F10 C53 C54 F11 158.5(8) . . . . ? C52 C53 C54 F11 -83.8(9) . . . . ? F9 C53 C54 F12 -81.9(11) . . . . ? F10 C53 C54 F12 39.1(8) . . . . ? C52 C53 C54 F12 156.8(6) . . . . ? F9 C53 C54 C55 153.5(10) . . . . ? F10 C53 C54 C55 -85.5(10) . . . . ? C52 C53 C54 C55 32.2(10) . . . . ? C63 C51 C55 C83 9.4(13) . . . . ? C52 C51 C55 C83 -176.2(8) . . . . ? C63 C51 C55 C54 -160.6(7) . . . . ? C52 C51 C55 C54 13.9(8) . . . . ? F11 C54 C55 C51 88.7(10) . . . . ? F12 C54 C55 C51 -152.7(6) . . . . ? C53 C54 C55 C51 -29.6(10) . . . . ? F11 C54 C55 C83 -82.8(13) . . . . ? F12 C54 C55 C83 35.8(9) . . . . ? C53 C54 C55 C83 158.9(9) . . . . ? C61 C62 C63 C64 -175.3(12) . . . . ? S3 C62 C63 C64 0.5(14) . . . . ? C61 C62 C63 C51 3(2) . . . . ? S3 C62 C63 C51 179.0(10) . . . . ? C55 C51 C63 C62 35.1(17) . . . . ? C52 C51 C63 C62 -138.8(12) . . . . ? C55 C51 C63 C64 -146.6(10) . . . . ? C52 C51 C63 C64 39.5(14) . . . . ? C62 C63 C64 C65 0.2(15) . . . . ? C51 C63 C64 C65 -178.3(12) . . . . ? C63 C64 C65 C66 -179.7(11) . . . . ? C63 C64 C65 S3 -0.8(13) . . . . ? C81 C82 C83 C55 9(2) . . . . ? S4 C82 C83 C55 -175.8(11) . . . . ? C81 C82 C83 C84 -170.3(13) . . . . ? S4 C82 C83 C84 4.4(14) . . . . ? C51 C55 C83 C82 39.4(19) . . . . ? C54 C55 C83 C82 -151.5(13) . . . . ? C51 C55 C83 C84 -140.8(10) . . . . ? C54 C55 C83 C84 28.2(15) . . . . ? C82 C83 C84 C85 -2.8(16) . . . . ? C55 C83 C84 C85 177.4(11) . . . . ? C83 C84 C85 C86 178.8(11) . . . . ? C83 C84 C85 S4 -0.2(14) . . . . ? C13 C12 S1 C15 0.8(10) . . . . ? C11 C12 S1 C15 -176.5(11) . . . . ? C14 C15 S1 C12 -1.6(10) . . . . ? C16 C15 S1 C12 176.3(10) . . . . ? C33 C32 S2 C35 4.4(11) . . . . ? C31 C32 S2 C35 -169.4(12) . . . . ? C34 C35 S2 C32 -2.8(11) . . . . ? C36 C35 S2 C32 175.7(10) . . . . ? C63 C62 S3 C65 -0.8(11) . . . . ? C61 C62 S3 C65 175.4(11) . . . . ? C64 C65 S3 C62 0.9(10) . . . . ? C66 C65 S3 C62 179.9(10) . . . . ? C83 C82 S4 C85 -3.9(11) . . . . ? C81 C82 S4 C85 170.9(12) . . . . ? C84 C85 S4 C82 2.3(10) . . . . ? C86 C85 S4 C82 -176.7(11) . . . . ? ##END _database_code_depnum_ccdc_archive 'CCDC 961276'