# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_try _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 F3 I O5' _chemical_formula_weight 408.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7331(12) _cell_length_b 11.849(2) _cell_length_c 15.250(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.274(8) _cell_angle_gamma 90.00 _cell_volume 1365.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8079 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 36.09 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.985 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 2.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2712 _exptl_absorpt_correction_T_max 0.4474 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 71720 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 33.14 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.987 _reflns_number_total 5126 _reflns_number_gt 4491 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5126 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.323 _refine_diff_density_min -1.115 _refine_diff_density_rms 0.116 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 0.1167(3) 0.31228(18) 0.01769(13) 0.0209(4) Uani 1 1 d . . . H11 H 0.019(4) 0.368(3) 0.002(2) 0.021(7) Uiso 1 1 d . . . C2 C 0.2801(4) 0.5417(3) 0.2285(2) 0.0415(7) Uani 1 1 d . . . H2A H 0.2353 0.6163 0.2070 0.062 Uiso 1 1 calc R . . H2B H 0.4088 0.5397 0.2346 0.062 Uiso 1 1 calc R . . H2C H 0.2510 0.5268 0.2869 0.062 Uiso 1 1 calc R . . C3 C 0.2231(3) 0.14626(18) 0.00522(12) 0.0188(3) Uani 1 1 d . . . H13 H 0.209(3) 0.072(2) -0.0194(17) 0.013(6) Uiso 1 1 d . . . C4 C 0.1489(3) 0.2706(2) 0.11485(13) 0.0217(4) Uani 1 1 d . . . H14 H 0.038(4) 0.256(3) 0.125(2) 0.031(8) Uiso 1 1 d . . . C5 C 0.1517(3) 0.0584(2) 0.14314(13) 0.0226(4) Uani 1 1 d . . . C6 C 0.2479(3) 0.3503(2) 0.18505(14) 0.0256(4) Uani 1 1 d . . . C7 C 0.2965(3) 0.33992(18) -0.00651(13) 0.0188(3) Uani 1 1 d . . . H17 H 0.379(3) 0.374(2) 0.0433(18) 0.012(6) Uiso 1 1 d . . . C8 C 0.2425(3) 0.15619(19) 0.10824(13) 0.0202(4) Uani 1 1 d . . . H18 H 0.369(4) 0.151(3) 0.137(2) 0.025(7) Uiso 1 1 d . . . C9 C 0.3570(2) 0.22008(18) -0.02822(12) 0.0185(3) Uani 1 1 d . . . H19 H 0.349(4) 0.207(2) -0.0922(19) 0.017(6) Uiso 1 1 d . . . C10 C 0.1980(4) -0.1183(2) 0.21500(17) 0.0319(5) Uani 1 1 d . . . H310 H 0.128(5) -0.168(3) 0.168(2) 0.033(9) Uiso 1 1 d . . . H210 H 0.296(5) -0.162(3) 0.236(3) 0.040(10) Uiso 1 1 d . . . H110 H 0.137(5) -0.100(3) 0.255(3) 0.045(10) Uiso 1 1 d . . . C11 C 0.2771(3) 0.4198(2) -0.08440(15) 0.0266(4) Uani 1 1 d . . . O1 O 0.1987(2) 0.45599(17) 0.16455(13) 0.0333(4) Uani 1 1 d . . . O2 O -0.0066(2) 0.04930(17) 0.13444(13) 0.0316(4) Uani 1 1 d . . . O3 O 0.2692(2) -0.01743(16) 0.18185(11) 0.0271(3) Uani 1 1 d . . . O4 O 0.3558(3) 0.32158(18) 0.25016(12) 0.0413(5) Uani 1 1 d . . . O5 O 0.06447(19) 0.20934(15) -0.03006(10) 0.0231(3) Uani 1 1 d . . . F1 F 0.2214(3) 0.52144(14) -0.06340(11) 0.0398(4) Uani 1 1 d . . . F2 F 0.4311(2) 0.43625(15) -0.10909(11) 0.0374(4) Uani 1 1 d . . . F3 F 0.1611(2) 0.38393(15) -0.15681(9) 0.0363(4) Uani 1 1 d . . . I1 I 0.629125(16) 0.181621(12) 0.026129(9) 0.02268(5) 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 0.0128(8) 0.0311(10) 0.0173(8) -0.0094(7) -0.0002(6) 0.0049(7) C2 0.0299(12) 0.0508(16) 0.0465(15) -0.0334(13) 0.0142(11) -0.0104(11) C3 0.0127(8) 0.0287(9) 0.0137(7) -0.0061(6) 0.0003(6) 0.0037(6) C4 0.0127(8) 0.0379(11) 0.0152(8) -0.0108(7) 0.0050(6) -0.0033(7) C5 0.0165(8) 0.0371(11) 0.0140(7) -0.0036(7) 0.0026(6) -0.0017(7) C6 0.0214(9) 0.0430(12) 0.0150(8) -0.0113(8) 0.0095(7) -0.0099(9) C7 0.0148(8) 0.0277(9) 0.0129(7) -0.0022(6) 0.0006(6) 0.0060(6) C8 0.0117(8) 0.0346(10) 0.0140(7) -0.0032(7) 0.0023(6) -0.0019(7) C9 0.0145(8) 0.0277(9) 0.0125(7) -0.0014(6) 0.0013(6) 0.0060(6) C10 0.0327(12) 0.0381(12) 0.0220(10) 0.0029(9) -0.0007(9) -0.0068(10) C11 0.0283(11) 0.0319(10) 0.0188(9) 0.0015(8) 0.0031(8) 0.0087(8) O1 0.0244(8) 0.0404(9) 0.0339(9) -0.0227(8) 0.0033(7) 0.0006(7) O2 0.0165(7) 0.0425(9) 0.0367(9) -0.0017(8) 0.0073(6) -0.0046(7) O3 0.0195(7) 0.0398(9) 0.0208(7) 0.0032(6) 0.0012(6) -0.0027(6) O4 0.0517(13) 0.0510(12) 0.0160(7) -0.0023(7) -0.0043(8) -0.0184(9) O5 0.0124(6) 0.0345(8) 0.0193(6) -0.0107(6) -0.0039(5) 0.0050(5) F1 0.0508(10) 0.0323(8) 0.0351(8) 0.0029(6) 0.0068(7) 0.0170(7) F2 0.0370(8) 0.0465(9) 0.0318(8) 0.0126(7) 0.0142(6) 0.0067(7) F3 0.0396(8) 0.0474(9) 0.0166(6) 0.0034(6) -0.0061(6) 0.0124(7) I1 0.01242(7) 0.03044(8) 0.02581(7) 0.00166(5) 0.00549(5) 0.00539(4) _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 O5 1.434(2) . ? C1 C4 1.531(3) . ? C1 C7 1.547(3) . ? C2 O1 1.455(3) . ? C3 O5 1.440(2) . ? C3 C9 1.524(3) . ? C3 C8 1.551(3) . ? C4 C6 1.508(3) . ? C4 C8 1.550(3) . ? C5 O2 1.207(3) . ? C5 O3 1.324(3) . ? C5 C8 1.509(3) . ? C6 O4 1.202(3) . ? C6 O1 1.327(3) . ? C7 C11 1.501(3) . ? C7 C9 1.553(3) . ? C9 I1 2.1407(18) . ? C10 O3 1.451(3) . ? C11 F3 1.336(3) . ? C11 F2 1.337(3) . ? C11 F1 1.341(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 O5 C1 C4 100.81(17) . . ? O5 C1 C7 103.26(15) . . ? C4 C1 C7 109.25(15) . . ? O5 C3 C9 99.35(17) . . ? O5 C3 C8 103.31(15) . . ? C9 C3 C8 111.69(16) . . ? C6 C4 C1 116.0(2) . . ? C6 C4 C8 114.82(18) . . ? C1 C4 C8 101.59(15) . . ? O2 C5 O3 124.9(2) . . ? O2 C5 C8 124.5(2) . . ? O3 C5 C8 110.57(18) . . ? O4 C6 O1 125.1(2) . . ? O4 C6 C4 124.6(2) . . ? O1 C6 C4 110.26(19) . . ? C11 C7 C1 112.25(17) . . ? C11 C7 C9 113.07(17) . . ? C1 C7 C9 100.60(17) . . ? C5 C8 C3 110.31(17) . . ? C5 C8 C4 112.97(18) . . ? C3 C8 C4 100.75(16) . . ? C3 C9 C7 101.35(16) . . ? C3 C9 I1 115.47(13) . . ? C7 C9 I1 115.34(13) . . ? F3 C11 F2 107.16(19) . . ? F3 C11 F1 106.85(18) . . ? F2 C11 F1 106.7(2) . . ? F3 C11 C7 112.9(2) . . ? F2 C11 C7 111.70(18) . . ? F1 C11 C7 111.12(18) . . ? C6 O1 C2 116.1(2) . . ? C5 O3 C10 116.00(19) . . ? C1 O5 C3 97.25(14) . . ? _database_code_depnum_ccdc_archive 'CCDC 951078' ####################################################################### # # 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_p-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 F10 O2 S2' _chemical_formula_weight 540.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.337(3) _cell_length_b 10.385(5) _cell_length_c 15.832(8) _cell_angle_alpha 96.304(11) _cell_angle_beta 90.560(11) _cell_angle_gamma 99.260(11) _cell_volume 1021.7(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1276 _cell_measurement_theta_min 3.54 _cell_measurement_theta_max 20.71 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.118 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.369 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6780 _exptl_absorpt_correction_T_max 0.7446 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4875 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 20.81 _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 0.947 _reflns_number_total 2028 _reflns_number_gt 1593 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+12.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2028 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.2060 _refine_ls_wR_factor_gt 0.1952 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.557 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.100 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 0.7601(4) 0.5864(2) 0.11510(15) 0.0368(7) Uani 1 1 d . . . S1A S 0.2474(4) 0.5383(2) 0.38138(14) 0.0341(7) Uani 1 1 d . . . C1 C 0.8457(14) 0.7606(8) 0.1227(5) 0.024(2) Uani 1 1 d . . . C1A C 0.3250(14) 0.7107(8) 0.3736(5) 0.027(2) Uani 1 1 d . . . C2 C 0.7009(17) 0.8402(10) 0.1672(6) 0.042(3) Uani 1 1 d . . . H2A H 0.5731 0.7997 0.1878 0.050 Uiso 1 1 calc R . . C2A C 0.1664(17) 0.7738(10) 0.3313(6) 0.041(3) Uani 1 1 d . . . H2AA H 0.0371 0.7249 0.3100 0.049 Uiso 1 1 calc R . . C3A C 0.2109(17) 0.9001(12) 0.3241(6) 0.050(3) Uani 1 1 d . . . H3AA H 0.1108 0.9404 0.2982 0.060 Uiso 1 1 calc R . . C3 C 0.7528(18) 0.9710(11) 0.1780(6) 0.051(3) Uani 1 1 d . . . H3A H 0.6610 1.0210 0.2067 0.061 Uiso 1 1 calc R . . C4 C 0.9432(15) 1.0336(10) 0.1467(5) 0.036(3) Uani 1 1 d . . . C4A C 0.4062(15) 0.9757(10) 0.3549(5) 0.034(2) Uani 1 1 d . . . C5A C 0.4499(19) 1.1167(11) 0.3477(7) 0.053(3) Uani 1 1 d . . . H5AA H 0.3484 1.1580 0.3234 0.063 Uiso 1 1 calc R . . C5 C 1.0049(19) 1.1783(10) 0.1603(7) 0.052(3) Uani 1 1 d . . . H5A H 0.9152 1.2300 0.1888 0.062 Uiso 1 1 calc R . . C6 C 1.194(2) 1.2343(10) 0.1307(7) 0.051(3) Uani 1 1 d . . . H6A H 1.2342 1.3250 0.1392 0.061 Uiso 1 1 calc R . . C6A C 0.644(2) 1.1870(10) 0.3775(7) 0.051(3) Uani 1 1 d . . . H6AA H 0.6758 1.2763 0.3724 0.061 Uiso 1 1 calc R . . C7A C 0.789(2) 1.1254(12) 0.4148(7) 0.054(3) Uani 1 1 d . . . H7AA H 0.9195 1.1752 0.4341 0.065 Uiso 1 1 calc R . . C7 C 1.327(2) 1.1575(11) 0.0877(7) 0.054(3) Uani 1 1 d . . . H7A H 1.4548 1.1979 0.0671 0.064 Uiso 1 1 calc R . . C8 C 1.2753(17) 1.0245(11) 0.0751(6) 0.049(3) Uani 1 1 d . . . H8A H 1.3684 0.9754 0.0464 0.058 Uiso 1 1 calc R . . C8A C 0.7548(17) 0.9955(11) 0.4251(6) 0.049(3) Uani 1 1 d . . . H8AA H 0.8571 0.9576 0.4516 0.059 Uiso 1 1 calc R . . C9A C 0.5610(17) 0.9212(9) 0.3946(6) 0.037(3) Uani 1 1 d . . . C9 C 1.0887(15) 0.9623(9) 0.1040(5) 0.031(2) Uani 1 1 d . . . C10 C 1.0284(16) 0.8203(10) 0.0937(5) 0.034(3) Uani 1 1 d . . . C10A C 0.5136(15) 0.7806(10) 0.4034(6) 0.036(2) Uani 1 1 d . . . O1A O 0.6701(11) 0.7361(8) 0.4413(5) 0.048(2) Uani 1 1 d . . . H1OA H 0.642(13) 0.655(9) 0.453(5) 0.02(3) Uiso 1 1 d . . . O1 O 1.1750(14) 0.7620(11) 0.0521(6) 0.053(3) Uani 1 1 d . . . H101 H 1.159(15) 0.705(8) 0.050(6) -0.01(3) Uiso 1 1 d . . . F1A F 0.1772(9) 0.3859(5) 0.3897(4) 0.0529(16) Uani 1 1 d . . . F1 F 0.6876(10) 0.4310(5) 0.1075(4) 0.0557(17) Uani 1 1 d . . . F2A F 0.0132(8) 0.5558(6) 0.4074(4) 0.0508(16) Uani 1 1 d . . . F2 F 0.7037(10) 0.5901(6) 0.2121(3) 0.0558(17) Uani 1 1 d . . . F3A F 0.1736(10) 0.5077(5) 0.2849(3) 0.0569(17) Uani 1 1 d . . . F3 F 0.5223(8) 0.5976(5) 0.0901(4) 0.0534(17) Uani 1 1 d . . . F4A F 0.4764(9) 0.5040(5) 0.3566(3) 0.0431(15) Uani 1 1 d . . . F4 F 0.8133(9) 0.5665(5) 0.0168(3) 0.0425(15) Uani 1 1 d . . . F5 F 0.9934(8) 0.5589(5) 0.1383(3) 0.0439(15) Uani 1 1 d . . . F5A F 0.3179(8) 0.5533(5) 0.4799(3) 0.0384(14) 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 S1 0.0347(17) 0.0348(16) 0.0379(16) 0.0025(11) -0.0031(11) -0.0021(11) S1A 0.0357(17) 0.0352(15) 0.0326(15) 0.0076(11) 0.0008(11) 0.0070(11) C1 0.021(6) 0.028(5) 0.020(5) 0.001(4) -0.002(4) 0.003(4) C1A 0.027(6) 0.032(5) 0.023(5) 0.010(4) 0.008(4) 0.005(5) C2 0.056(8) 0.030(7) 0.036(6) -0.004(5) -0.015(5) -0.001(5) C2A 0.048(7) 0.037(7) 0.038(6) 0.008(5) 0.015(5) 0.006(5) C3A 0.047(8) 0.074(9) 0.041(7) 0.019(6) 0.005(5) 0.034(7) C3 0.047(8) 0.068(9) 0.039(6) -0.004(6) 0.003(5) 0.023(6) C4 0.026(6) 0.057(7) 0.025(5) 0.005(5) -0.003(4) 0.005(5) C4A 0.028(6) 0.047(7) 0.022(5) -0.010(4) 0.009(4) -0.001(5) C5A 0.063(9) 0.052(8) 0.045(7) -0.004(5) 0.025(6) 0.021(6) C5 0.070(9) 0.045(7) 0.044(7) 0.017(5) -0.005(6) 0.009(6) C6 0.070(9) 0.031(6) 0.049(7) 0.013(5) -0.011(6) -0.003(6) C6A 0.071(9) 0.019(6) 0.058(7) -0.008(5) 0.025(6) 0.001(6) C7A 0.065(9) 0.047(8) 0.047(7) -0.001(6) 0.013(6) 0.004(7) C7 0.070(9) 0.037(7) 0.049(7) 0.005(5) -0.004(6) -0.005(6) C8 0.041(8) 0.064(9) 0.043(7) 0.008(5) 0.006(5) 0.015(6) C8A 0.042(8) 0.057(8) 0.044(7) -0.004(5) 0.011(5) -0.003(6) C9A 0.050(8) 0.041(7) 0.026(6) 0.009(4) 0.015(5) 0.025(6) C9 0.035(7) 0.043(7) 0.019(5) 0.002(4) 0.004(4) 0.015(5) C10 0.036(7) 0.049(7) 0.021(5) -0.002(5) 0.000(5) 0.021(6) C10A 0.025(7) 0.052(7) 0.036(6) 0.017(5) 0.005(5) 0.016(5) O1A 0.044(5) 0.042(5) 0.060(5) 0.011(4) -0.001(4) 0.007(4) O1 0.049(6) 0.042(7) 0.066(6) -0.001(5) 0.006(4) 0.005(5) F1A 0.058(4) 0.025(3) 0.073(4) 0.013(3) 0.005(3) -0.004(3) F1 0.065(4) 0.033(3) 0.063(4) -0.004(3) -0.001(3) -0.008(3) F2A 0.027(4) 0.063(4) 0.067(4) 0.022(3) 0.003(3) 0.010(3) F2 0.069(5) 0.052(4) 0.040(3) 0.011(3) 0.014(3) -0.013(3) F3A 0.077(5) 0.050(4) 0.039(4) -0.003(3) -0.018(3) 0.005(3) F3 0.027(3) 0.055(4) 0.072(4) -0.008(3) -0.008(3) -0.002(3) F4A 0.047(4) 0.040(3) 0.048(3) 0.011(3) 0.017(3) 0.021(3) F4 0.048(4) 0.044(3) 0.034(3) -0.004(2) -0.004(2) 0.005(3) F5 0.045(4) 0.039(3) 0.049(3) 0.009(3) -0.013(3) 0.009(3) F5A 0.042(4) 0.047(3) 0.029(3) 0.015(2) 0.002(2) 0.008(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 F2 1.579(6) . ? S1 F3 1.580(6) . ? S1 F4 1.594(6) . ? S1 F1 1.596(6) . ? S1 F5 1.597(6) . ? S1 C1 1.793(9) . ? S1A F3A 1.576(6) . ? S1A F2A 1.577(6) . ? S1A F4A 1.592(6) . ? S1A F1A 1.594(6) . ? S1A F5A 1.603(5) . ? S1A C1A 1.797(9) . ? C1 C10 1.334(13) . ? C1 C2 1.466(13) . ? C1A C10A 1.346(13) . ? C1A C2A 1.478(14) . ? C2 C3 1.337(14) . ? C2A C3A 1.314(14) . ? C3A C4A 1.406(14) . ? C3 C4 1.398(14) . ? C4 C9 1.406(13) . ? C4 C5 1.482(14) . ? C4A C9A 1.386(14) . ? C4A C5A 1.464(14) . ? C5A C6A 1.374(16) . ? C5 C6 1.355(15) . ? C6 C7 1.386(15) . ? C6A C7A 1.368(16) . ? C7A C8A 1.359(15) . ? C7 C8 1.359(14) . ? C8 C9 1.362(14) . ? C8A C9A 1.393(14) . ? C9A C10A 1.465(13) . ? C9 C10 1.453(13) . ? C10 O1 1.330(13) . ? C10A O1A 1.324(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 F2 S1 F3 91.1(3) . . ? F2 S1 F4 174.0(3) . . ? F3 S1 F4 89.6(3) . . ? F2 S1 F1 87.6(3) . . ? F3 S1 F1 87.8(3) . . ? F4 S1 F1 86.5(3) . . ? F2 S1 F5 89.4(3) . . ? F3 S1 F5 174.0(3) . . ? F4 S1 F5 89.3(3) . . ? F1 S1 F5 86.3(3) . . ? F2 S1 C1 93.1(3) . . ? F3 S1 C1 93.0(4) . . ? F4 S1 C1 92.8(3) . . ? F1 S1 C1 179.0(4) . . ? F5 S1 C1 93.0(3) . . ? F3A S1A F2A 90.7(3) . . ? F3A S1A F4A 89.4(3) . . ? F2A S1A F4A 173.6(3) . . ? F3A S1A F1A 87.7(3) . . ? F2A S1A F1A 86.9(3) . . ? F4A S1A F1A 86.7(3) . . ? F3A S1A F5A 174.0(3) . . ? F2A S1A F5A 89.7(3) . . ? F4A S1A F5A 89.6(3) . . ? F1A S1A F5A 86.4(3) . . ? F3A S1A C1A 93.0(4) . . ? F2A S1A C1A 92.5(4) . . ? F4A S1A C1A 93.8(4) . . ? F1A S1A C1A 179.1(4) . . ? F5A S1A C1A 92.9(3) . . ? C10 C1 C2 119.2(8) . . ? C10 C1 S1 125.4(7) . . ? C2 C1 S1 115.3(7) . . ? C10A C1A C2A 120.8(8) . . ? C10A C1A S1A 123.7(7) . . ? C2A C1A S1A 115.5(7) . . ? C3 C2 C1 119.9(10) . . ? C3A C2A C1A 118.9(10) . . ? C2A C3A C4A 121.5(10) . . ? C2 C3 C4 120.9(10) . . ? C3 C4 C9 121.7(9) . . ? C3 C4 C5 121.3(10) . . ? C9 C4 C5 117.0(9) . . ? C9A C4A C3A 121.9(10) . . ? C9A C4A C5A 117.7(9) . . ? C3A C4A C5A 120.4(10) . . ? C6A C5A C4A 118.7(11) . . ? C6 C5 C4 119.1(10) . . ? C5 C6 C7 120.5(10) . . ? C7A C6A C5A 119.9(10) . . ? C8A C7A C6A 123.8(11) . . ? C8 C7 C6 121.5(11) . . ? C7 C8 C9 120.7(10) . . ? C7A C8A C9A 117.7(11) . . ? C4A C9A C8A 122.1(10) . . ? C4A C9A C10A 117.3(9) . . ? C8A C9A C10A 120.6(9) . . ? C8 C9 C4 121.1(9) . . ? C8 C9 C10 122.8(9) . . ? C4 C9 C10 116.1(9) . . ? C1 C10 O1 126.3(9) . . ? C1 C10 C9 122.2(8) . . ? O1 C10 C9 111.6(9) . . ? O1A C10A C1A 126.9(9) . . ? O1A C10A C9A 113.5(9) . . ? C1A C10A C9A 119.5(8) . . ? _database_code_depnum_ccdc_archive 'CCDC 951079' ####################################################################### # # 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_try _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 F5 O S' _chemical_formula_weight 246.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.367(3) _cell_length_b 9.325(2) _cell_length_c 7.9104(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.640(13) _cell_angle_gamma 90.00 _cell_volume 906.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9762 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 28.24 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.405 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8546 _exptl_absorpt_correction_T_max 0.9118 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 49354 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 27.08 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.08 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 1982 _reflns_number_gt 1799 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.3500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1982 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.311 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.074 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 0.78324(11) 1.09116(14) 0.14961(17) 0.0184(3) Uani 1 1 d . . . C2 C 0.67788(11) 1.11406(16) 0.18956(18) 0.0205(3) Uani 1 1 d . . . H1C2 H 0.6371(16) 1.041(2) 0.213(3) 0.033(5) Uiso 1 1 d . . . C3 C 0.64163(11) 1.25400(15) 0.19042(17) 0.0209(3) Uani 1 1 d . . . C4 C 0.70666(11) 1.36754(15) 0.15108(17) 0.0208(3) Uani 1 1 d . . . C5 C 0.81149(11) 1.34383(16) 0.11074(18) 0.0224(3) Uani 1 1 d . . . H1C5 H 0.8556(16) 1.420(2) 0.085(2) 0.031(5) Uiso 1 1 d . . . C6 C 0.85039(11) 1.20400(16) 0.11044(19) 0.0214(3) Uani 1 1 d . . . H1C6 H 0.9194(14) 1.1852(19) 0.085(2) 0.021(4) Uiso 1 1 d . . . C7 C 0.53400(12) 1.31153(18) 0.2304(2) 0.0276(3) Uani 1 1 d . . . H2C7 H 0.4721(15) 1.278(2) 0.153(2) 0.028(5) Uiso 1 1 d . . . H1C7 H 0.5150(15) 1.288(2) 0.347(3) 0.033(5) Uiso 1 1 d . . . C8 C 0.64420(12) 1.50464(17) 0.1588(2) 0.0268(3) Uani 1 1 d . . . H2C8 H 0.6820(17) 1.573(2) 0.238(3) 0.039(5) Uiso 1 1 d . . . H1C8 H 0.6300(15) 1.550(2) 0.048(2) 0.027(5) Uiso 1 1 d . . . O1 O 0.54337(10) 1.46410(14) 0.21843(19) 0.0434(3) Uani 1 1 d . . . S1 S 0.83480(3) 0.91069(4) 0.15332(4) 0.02280(14) Uani 1 1 d . . . F1 F 0.88041(8) 0.75145(10) 0.15726(13) 0.0359(3) Uani 1 1 d . . . F2 F 0.78932(9) 0.87629(10) 0.32951(12) 0.0329(2) Uani 1 1 d . . . F3 F 0.72514(7) 0.84965(10) 0.05364(12) 0.0302(2) Uani 1 1 d . . . F4 F 0.94801(7) 0.95718(11) 0.25400(13) 0.0350(3) Uani 1 1 d . . . F5 F 0.88340(8) 0.93054(10) -0.02291(12) 0.0313(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 0.0188(6) 0.0198(6) 0.0166(6) 0.0012(5) 0.0017(5) 0.0017(5) C2 0.0172(6) 0.0250(7) 0.0195(7) 0.0036(5) 0.0035(5) -0.0025(5) C3 0.0168(6) 0.0295(7) 0.0164(6) 0.0015(5) 0.0023(5) 0.0034(5) C4 0.0222(6) 0.0230(7) 0.0166(6) -0.0001(5) -0.0004(5) 0.0030(5) C5 0.0194(6) 0.0238(7) 0.0236(7) 0.0031(5) 0.0016(5) -0.0021(5) C6 0.0155(6) 0.0265(7) 0.0225(7) 0.0022(5) 0.0040(5) 0.0001(5) C7 0.0219(7) 0.0348(8) 0.0271(8) 0.0034(6) 0.0067(6) 0.0068(6) C8 0.0256(7) 0.0262(7) 0.0283(8) -0.0004(6) 0.0021(6) 0.0057(6) O1 0.0321(6) 0.0340(7) 0.0675(9) 0.0022(6) 0.0208(6) 0.0120(5) S1 0.0247(2) 0.0212(2) 0.0224(2) 0.00068(12) 0.00221(14) 0.00339(12) F1 0.0451(6) 0.0227(5) 0.0395(6) -0.0005(4) 0.0029(4) 0.0104(4) F2 0.0488(6) 0.0263(5) 0.0245(5) 0.0076(4) 0.0089(4) 0.0051(4) F3 0.0312(5) 0.0245(5) 0.0340(5) -0.0042(4) 0.0003(4) -0.0037(3) F4 0.0257(5) 0.0321(5) 0.0440(6) -0.0015(4) -0.0090(4) 0.0078(4) F5 0.0340(5) 0.0321(5) 0.0302(5) -0.0009(4) 0.0136(4) 0.0072(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3922(19) . ? C1 C6 1.3973(19) . ? C1 S1 1.7986(14) . ? C2 C3 1.380(2) . ? C3 C4 1.387(2) . ? C3 C7 1.5023(19) . ? C4 C5 1.388(2) . ? C4 C8 1.499(2) . ? C5 C6 1.390(2) . ? C7 O1 1.431(2) . ? C8 O1 1.434(2) . ? S1 F1 1.5875(10) . ? S1 F4 1.5890(10) . ? S1 F5 1.5914(10) . ? S1 F3 1.5930(10) . ? S1 F2 1.5947(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 C2 C1 C6 122.05(13) . . ? C2 C1 S1 118.63(11) . . ? C6 C1 S1 119.31(11) . . ? C3 C2 C1 117.34(12) . . ? C2 C3 C4 121.58(12) . . ? C2 C3 C7 129.42(13) . . ? C4 C3 C7 109.01(13) . . ? C3 C4 C5 120.75(13) . . ? C3 C4 C8 109.10(12) . . ? C5 C4 C8 130.14(13) . . ? C6 C5 C4 118.85(13) . . ? C5 C6 C1 119.43(12) . . ? O1 C7 C3 105.10(12) . . ? O1 C8 C4 105.10(12) . . ? C7 O1 C8 111.34(11) . . ? F1 S1 F4 87.41(6) . . ? F1 S1 F5 87.51(5) . . ? F4 S1 F5 90.41(6) . . ? F1 S1 F3 87.46(5) . . ? F4 S1 F3 174.86(5) . . ? F5 S1 F3 89.66(6) . . ? F1 S1 F2 87.43(5) . . ? F4 S1 F2 89.78(6) . . ? F5 S1 F2 174.92(5) . . ? F3 S1 F2 89.69(6) . . ? F1 S1 C1 179.81(7) . . ? F4 S1 C1 92.47(6) . . ? F5 S1 C1 92.64(6) . . ? F3 S1 C1 92.66(6) . . ? F2 S1 C1 92.42(6) . . ? _database_code_depnum_ccdc_archive 'CCDC 951080'