# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Weaver, George' _publ_contact_author_name 'Weaver, George' _publ_contact_author_email g.w.weaver@lboro.ac.uk _publ_section_title ; Synthesis of Fluorinated Fused Benzofurans and Benzothiophenes: Smiles-type Rearrangement and Cyclisation of Perfluoro(het)aryl Ethers and Sulfides ; # Attachment '- Weaver.CIF' data_4 _database_code_depnum_ccdc_archive 'CCDC 794854' #TrackingRef '- Weaver.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H5 F4 N O' _chemical_formula_sum 'C11 H5 F4 N O' _chemical_formula_weight 243.16 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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I4(1)cd _symmetry_space_group_name_Hall 'I 4bw -2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x, -y, z+1/2' '-x+1/2, y+1/2, z' '-y, -x+1/2, z+3/4' 'y+1/2, x, z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' 'x+1/2, -y+1/2, z+1' '-x+1, y+1, z+1/2' '-y+1/2, -x+1, z+5/4' 'y+1, x+1/2, z+3/4' _cell_length_a 13.0912(7) _cell_length_b 13.0912(7) _cell_length_c 23.1759(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3971.9(4) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4965 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 25.79 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.914 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details 'SADABS v2007/2, Sheldrick, G.M., (2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12777 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0096 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 28.33 _reflns_number_total 1268 _reflns_number_gt 1158 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _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 and local programs' _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. Friedels merged. ; _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^)+(0.0442P)^2^+1.3858P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _chemical_absolute_configuration unk _refine_ls_number_reflns 1268 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.68224(15) 0.23057(14) 0.30734(8) 0.0341(4) Uani 1 1 d . . . C2 C 0.60879(18) 0.15503(16) 0.30150(10) 0.0432(5) Uani 1 1 d . . . F2 F 0.61597(15) 0.06914(11) 0.33182(8) 0.0701(5) Uani 1 1 d . . . C3 C 0.52715(19) 0.16931(19) 0.26459(11) 0.0477(5) Uani 1 1 d . . . F3 F 0.45742(15) 0.09736(14) 0.25863(9) 0.0776(6) Uani 1 1 d . . . N4 N 0.51384(16) 0.25167(15) 0.23350(9) 0.0477(4) Uani 1 1 d . . . C5 C 0.5829(2) 0.32392(18) 0.23851(11) 0.0487(5) Uani 1 1 d . . . F5 F 0.56767(17) 0.40772(13) 0.20702(9) 0.0827(6) Uani 1 1 d . . . C6 C 0.66617(18) 0.31727(16) 0.27374(10) 0.0412(4) Uani 1 1 d . . . F6 F 0.73321(13) 0.39436(11) 0.27461(7) 0.0635(5) Uani 1 1 d . . . C7 C 0.77286(16) 0.22009(15) 0.34506(9) 0.0374(4) Uani 1 1 d . . . C8 C 0.79262(17) 0.29540(18) 0.38647(10) 0.0429(5) Uani 1 1 d . . . O8 O 0.72185(14) 0.36921(15) 0.39340(9) 0.0604(5) Uani 1 1 d . . . H8 H 0.7380 0.4062 0.4216 0.091 Uiso 1 1 calc R . . C9 C 0.8825(2) 0.2898(2) 0.41899(11) 0.0523(6) Uani 1 1 d . . . H9 H 0.8971 0.3411 0.4468 0.063 Uiso 1 1 calc R . . C10 C 0.9498(2) 0.2107(2) 0.41098(13) 0.0589(6) Uani 1 1 d . . . H10 H 1.0108 0.2079 0.4331 0.071 Uiso 1 1 calc R . . C11 C 0.9298(2) 0.1356(2) 0.37118(15) 0.0652(8) Uani 1 1 d . . . H11 H 0.9767 0.0810 0.3659 0.078 Uiso 1 1 calc R . . C12 C 0.8406(2) 0.13962(18) 0.33859(12) 0.0540(6) Uani 1 1 d . . . H12 H 0.8261 0.0868 0.3117 0.065 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0412(10) 0.0323(9) 0.0287(8) -0.0053(7) -0.0006(7) -0.0018(7) C2 0.0532(12) 0.0318(9) 0.0446(11) -0.0019(8) -0.0071(10) -0.0048(9) F2 0.0871(11) 0.0408(7) 0.0823(11) 0.0187(8) -0.0297(10) -0.0220(8) C3 0.0504(13) 0.0414(11) 0.0513(12) -0.0072(9) -0.0093(10) -0.0106(9) F3 0.0713(11) 0.0591(10) 0.1024(14) 0.0053(9) -0.0352(9) -0.0288(8) N4 0.0493(10) 0.0455(9) 0.0483(10) -0.0061(9) -0.0147(9) -0.0018(8) C5 0.0558(13) 0.0409(11) 0.0494(12) 0.0063(10) -0.0129(10) -0.0037(9) F5 0.0944(13) 0.0606(9) 0.0931(13) 0.0337(10) -0.0461(11) -0.0148(9) C6 0.0469(11) 0.0362(10) 0.0405(10) 0.0021(8) -0.0052(8) -0.0077(8) F6 0.0654(10) 0.0527(8) 0.0725(10) 0.0218(7) -0.0213(8) -0.0262(7) C7 0.0432(11) 0.0359(10) 0.0333(9) 0.0017(7) -0.0031(8) -0.0034(7) C8 0.0420(11) 0.0487(11) 0.0381(10) -0.0065(9) -0.0041(9) -0.0044(9) O8 0.0484(9) 0.0668(11) 0.0661(12) -0.0358(10) -0.0140(8) 0.0064(8) C9 0.0502(13) 0.0628(15) 0.0439(12) -0.0064(11) -0.0127(10) -0.0053(11) C10 0.0534(13) 0.0685(16) 0.0548(14) 0.0082(12) -0.0202(11) 0.0016(12) C11 0.0655(16) 0.0543(14) 0.0758(19) 0.0075(14) -0.0177(14) 0.0170(12) C12 0.0662(15) 0.0424(12) 0.0534(13) -0.0015(10) -0.0130(12) 0.0067(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 C2 1.386(3) . ? C1 C6 1.393(3) . ? C1 C7 1.480(3) . ? C2 F2 1.329(3) . ? C2 C3 1.382(3) . ? C3 N4 1.308(3) . ? C3 F3 1.319(3) . ? N4 C5 1.313(3) . ? C5 F5 1.333(3) . ? C5 C6 1.365(3) . ? C6 F6 1.338(2) . ? C7 C12 1.385(3) . ? C7 C8 1.400(3) . ? C8 O8 1.348(3) . ? C8 C9 1.400(3) . ? C9 C10 1.372(4) . ? C10 C11 1.374(4) . ? C11 C12 1.392(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 114.97(19) . . ? C2 C1 C7 123.21(18) . . ? C6 C1 C7 121.80(18) . . ? F2 C2 C3 119.76(19) . . ? F2 C2 C1 120.2(2) . . ? C3 C2 C1 120.0(2) . . ? N4 C3 F3 116.0(2) . . ? N4 C3 C2 123.7(2) . . ? F3 C3 C2 120.2(2) . . ? C3 N4 C5 116.9(2) . . ? N4 C5 F5 116.2(2) . . ? N4 C5 C6 123.8(2) . . ? F5 C5 C6 119.9(2) . . ? F6 C6 C5 119.03(19) . . ? F6 C6 C1 120.49(19) . . ? C5 C6 C1 120.47(19) . . ? C12 C7 C8 119.4(2) . . ? C12 C7 C1 121.31(19) . . ? C8 C7 C1 119.20(18) . . ? O8 C8 C9 123.5(2) . . ? O8 C8 C7 117.35(19) . . ? C9 C8 C7 119.2(2) . . ? C10 C9 C8 120.4(2) . . ? C9 C10 C11 120.6(2) . . ? C10 C11 C12 119.8(3) . . ? C7 C12 C11 120.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F2 -179.5(2) . . . . ? C7 C1 C2 F2 2.0(3) . . . . ? C6 C1 C2 C3 -0.3(3) . . . . ? C7 C1 C2 C3 -178.7(2) . . . . ? F2 C2 C3 N4 179.5(2) . . . . ? C1 C2 C3 N4 0.3(4) . . . . ? F2 C2 C3 F3 -1.2(4) . . . . ? C1 C2 C3 F3 179.6(2) . . . . ? F3 C3 N4 C5 -179.5(2) . . . . ? C2 C3 N4 C5 -0.2(4) . . . . ? C3 N4 C5 F5 -179.3(3) . . . . ? C3 N4 C5 C6 0.2(4) . . . . ? N4 C5 C6 F6 178.4(3) . . . . ? F5 C5 C6 F6 -2.1(4) . . . . ? N4 C5 C6 C1 -0.2(4) . . . . ? F5 C5 C6 C1 179.3(2) . . . . ? C2 C1 C6 F6 -178.4(2) . . . . ? C7 C1 C6 F6 0.1(3) . . . . ? C2 C1 C6 C5 0.2(3) . . . . ? C7 C1 C6 C5 178.7(2) . . . . ? C2 C1 C7 C12 56.6(3) . . . . ? C6 C1 C7 C12 -121.8(2) . . . . ? C2 C1 C7 C8 -126.1(2) . . . . ? C6 C1 C7 C8 55.5(3) . . . . ? C12 C7 C8 O8 -176.5(2) . . . . ? C1 C7 C8 O8 6.2(3) . . . . ? C12 C7 C8 C9 2.4(4) . . . . ? C1 C7 C8 C9 -175.0(2) . . . . ? O8 C8 C9 C10 177.9(3) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C8 C7 C12 C11 -2.7(4) . . . . ? C1 C7 C12 C11 174.6(2) . . . . ? C10 C11 C12 C7 1.4(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O8 H8 N4 0.84 2.02 2.846(3) 167.8 8 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.156 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.030 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 794855' #TrackingRef '- Weaver.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H12 Br3 F2 N S3, 0.5(C7 H8)' _chemical_formula_sum 'C26.50 H16 Br3 F2 N S3' _chemical_formula_weight 722.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0016(12) _cell_length_b 10.9436(19) _cell_length_c 17.466(3) _cell_angle_alpha 92.675(3) _cell_angle_beta 99.643(3) _cell_angle_gamma 90.003(3) _cell_volume 1317.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3439 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.38 _exptl_crystal_description lath _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 706 _exptl_absorpt_coefficient_mu 4.861 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.153 _exptl_absorpt_correction_T_max 0.793 _exptl_absorpt_process_details 'TWINABS v2007/5, Sheldrick, G.M., (2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14248 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.87 _reflns_number_total 8971 _reflns_number_gt 6373 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _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 and local programs' _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. Two domain non- merohedral twin. BASF = 0.1256(6). 180 deg rotn about real axis 1 0 0. ; _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^)+(0.1034P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8971 _refine_ls_number_parameters 354 _refine_ls_number_restraints 63 _refine_ls_R_factor_all 0.0837 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1632 _refine_ls_wR_factor_gt 0.1496 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.035 _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 N1 N 0.3675(5) 0.4993(3) 0.1765(2) 0.0254(8) Uani 1 1 d . . . C2 C 0.4436(6) 0.6012(4) 0.2145(3) 0.0243(9) Uani 1 1 d . . . C3 C 0.5457(6) 0.5990(4) 0.2896(3) 0.0252(9) Uani 1 1 d . . . F3 F 0.6100(4) 0.7083(2) 0.32357(16) 0.0360(7) Uani 1 1 d . . . C4 C 0.5744(6) 0.4928(4) 0.3292(3) 0.0240(9) Uani 1 1 d . . . C5 C 0.4892(6) 0.3869(4) 0.2896(3) 0.0230(9) Uani 1 1 d . . . C6 C 0.3926(6) 0.3989(4) 0.2144(3) 0.0262(10) Uani 1 1 d . . . F6 F 0.3139(4) 0.2984(2) 0.17469(17) 0.0379(7) Uani 1 1 d . . . S1 S 0.41519(17) 0.74393(11) 0.17100(7) 0.0316(3) Uani 1 1 d . . . C7 C 0.2924(6) 0.6981(4) 0.0776(3) 0.0282(10) Uani 1 1 d . . . C8 C 0.0924(7) 0.6844(4) 0.0595(3) 0.0300(10) Uani 1 1 d . . . Br1 Br -0.06375(8) 0.70915(7) 0.13773(4) 0.05478(19) Uani 1 1 d . . . S2 S 0.69405(17) 0.48036(12) 0.42513(7) 0.0310(3) Uani 1 1 d . . . C9 C 0.0003(7) 0.6513(5) -0.0151(3) 0.0407(13) Uani 1 1 d . . . H9 H -0.1368 0.6434 -0.0264 0.049 Uiso 1 1 calc R . . C10 C 0.1095(9) 0.6303(6) -0.0724(3) 0.0484(14) Uani 1 1 d . . . H10 H 0.0480 0.6053 -0.1234 0.058 Uiso 1 1 calc R . . C11 C 0.3060(9) 0.6448(7) -0.0569(4) 0.0586(17) Uani 1 1 d . . . H11 H 0.3804 0.6309 -0.0972 0.070 Uiso 1 1 calc R . . C12 C 0.3966(8) 0.6797(6) 0.0174(3) 0.0494(15) Uani 1 1 d . . . H12 H 0.5331 0.6913 0.0273 0.059 Uiso 1 1 calc R . . C13 C 0.8481(6) 0.6120(4) 0.4444(3) 0.0275(10) Uani 1 1 d . . . C14 C 1.0061(7) 0.6287(4) 0.4079(3) 0.0280(10) Uani 1 1 d . . . Br2 Br 1.05953(7) 0.51625(5) 0.32835(3) 0.04277(16) Uani 1 1 d . . . S3 S 0.47775(17) 0.24892(10) 0.33723(7) 0.0293(3) Uani 1 1 d . . . C15 C 1.1286(7) 0.7285(5) 0.4270(3) 0.0397(13) Uani 1 1 d . . . H15 H 1.2352 0.7399 0.4007 0.048 Uiso 1 1 calc R . . C16 C 1.0934(9) 0.8106(5) 0.4844(4) 0.0538(17) Uani 1 1 d . . . H16 H 1.1763 0.8798 0.4978 0.065 Uiso 1 1 calc R . . C17 C 0.9394(9) 0.7949(5) 0.5233(4) 0.0519(16) Uani 1 1 d . . . H17 H 0.9190 0.8511 0.5642 0.062 Uiso 1 1 calc R . . C18 C 0.8145(8) 0.6958(5) 0.5017(3) 0.0406(13) Uani 1 1 d . . . H18 H 0.7054 0.6859 0.5267 0.049 Uiso 1 1 calc R . . C19 C 0.6692(6) 0.1618(4) 0.3081(3) 0.0226(9) Uani 1 1 d . . . C20 C 0.6860(6) 0.0421(4) 0.3298(3) 0.0270(10) Uani 1 1 d . . . Br3 Br 0.50944(8) -0.02126(4) 0.38981(3) 0.04023(16) Uani 1 1 d . . . C21 C 0.8340(7) -0.0333(4) 0.3106(3) 0.0334(11) Uani 1 1 d . . . H21 H 0.8439 -0.1153 0.3265 0.040 Uiso 1 1 calc R . . C22 C 0.9647(7) 0.0126(4) 0.2686(3) 0.0358(12) Uani 1 1 d . . . H22 H 1.0657 -0.0378 0.2552 0.043 Uiso 1 1 calc R . . C23 C 0.9493(7) 0.1334(4) 0.2457(3) 0.0330(11) Uani 1 1 d . . . H23 H 1.0402 0.1653 0.2170 0.040 Uiso 1 1 calc R . . C24 C 0.8010(7) 0.2067(4) 0.2649(3) 0.0296(10) Uani 1 1 d . . . H24 H 0.7895 0.2882 0.2485 0.036 Uiso 1 1 calc R . . C25 C 0.407(2) 1.0075(11) 0.0348(8) 0.054(3) Uani 0.50 1 d PDU A -1 C26 C 0.364(3) 0.992(2) -0.0454(10) 0.061(5) Uani 0.50 1 d PDU A -1 H26 H 0.2329 0.9973 -0.0695 0.073 Uiso 0.50 1 calc PR A -1 C27 C 0.503(3) 0.9683(14) -0.0930(10) 0.071(4) Uani 0.50 1 d PDU A -1 H27 H 0.4680 0.9593 -0.1479 0.085 Uiso 0.50 1 calc PR A -1 C28 C 0.694(3) 0.959(2) -0.0565(11) 0.073(5) Uani 0.50 1 d PDU A -1 H28 H 0.7938 0.9424 -0.0863 0.088 Uiso 0.50 1 calc PR A -1 C29 C 0.737(2) 0.9725(16) 0.0214(11) 0.079(4) Uani 0.50 1 d PDU A -1 H29 H 0.8682 0.9656 0.0458 0.094 Uiso 0.50 1 calc PR A -1 C30 C 0.596(3) 0.997(3) 0.0675(12) 0.067(6) Uani 0.50 1 d PDU A -1 H30 H 0.6329 1.0055 0.1224 0.080 Uiso 0.50 1 calc PR A -1 C31 C 0.256(3) 1.032(2) 0.0859(14) 0.093(7) Uani 0.50 1 d PDU A -1 H31A H 0.3190 1.0390 0.1405 0.140 Uiso 0.50 1 calc PR A -1 H31B H 0.1625 0.9635 0.0789 0.140 Uiso 0.50 1 calc PR A -1 H31C H 0.1882 1.1076 0.0717 0.140 Uiso 0.50 1 calc PR 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 N1 0.024(2) 0.0273(19) 0.024(2) 0.0019(16) 0.0021(15) 0.0003(15) C2 0.016(2) 0.029(2) 0.028(2) 0.0064(18) 0.0021(17) 0.0008(17) C3 0.020(2) 0.022(2) 0.034(3) 0.0013(18) 0.0051(19) -0.0026(17) F3 0.0430(17) 0.0245(14) 0.0343(16) 0.0006(12) -0.0111(13) -0.0077(11) C4 0.017(2) 0.028(2) 0.029(2) 0.0042(18) 0.0070(18) 0.0004(17) C5 0.017(2) 0.023(2) 0.031(2) 0.0048(18) 0.0089(17) 0.0020(16) C6 0.023(2) 0.029(2) 0.026(2) -0.0054(19) 0.0071(18) -0.0037(17) F6 0.0450(17) 0.0285(14) 0.0369(17) -0.0049(12) -0.0005(13) -0.0089(12) S1 0.0309(6) 0.0283(6) 0.0328(6) 0.0064(5) -0.0045(5) -0.0032(5) C7 0.024(2) 0.033(2) 0.027(2) 0.0027(19) 0.0006(18) -0.0002(18) C8 0.025(2) 0.035(3) 0.032(3) 0.012(2) 0.006(2) 0.0036(19) Br1 0.0307(3) 0.0909(5) 0.0435(3) -0.0086(3) 0.0119(2) 0.0000(3) S2 0.0275(6) 0.0389(7) 0.0265(6) 0.0083(5) 0.0026(5) -0.0057(5) C9 0.026(3) 0.063(4) 0.032(3) 0.005(3) 0.000(2) -0.002(2) C10 0.051(4) 0.067(4) 0.025(3) 0.002(3) 0.002(2) 0.000(3) C11 0.048(4) 0.094(5) 0.039(3) 0.006(3) 0.019(3) 0.007(3) C12 0.025(3) 0.086(5) 0.038(3) 0.011(3) 0.005(2) -0.002(3) C13 0.026(2) 0.031(2) 0.024(2) 0.0030(19) -0.0011(19) -0.0004(18) C14 0.025(2) 0.030(2) 0.028(2) 0.0037(19) 0.0011(19) -0.0002(18) Br2 0.0314(3) 0.0541(3) 0.0460(3) -0.0041(3) 0.0174(2) 0.0000(2) S3 0.0282(6) 0.0265(6) 0.0365(7) 0.0052(5) 0.0141(5) -0.0006(5) C15 0.030(3) 0.041(3) 0.045(3) 0.015(2) -0.008(2) -0.004(2) C16 0.065(4) 0.038(3) 0.048(4) 0.005(3) -0.024(3) -0.020(3) C17 0.071(4) 0.040(3) 0.037(3) -0.011(3) -0.011(3) 0.006(3) C18 0.045(3) 0.048(3) 0.026(3) -0.002(2) 0.000(2) 0.009(2) C19 0.020(2) 0.023(2) 0.023(2) -0.0015(17) 0.0006(17) -0.0028(16) C20 0.026(2) 0.026(2) 0.028(2) 0.0040(19) 0.0011(19) -0.0038(18) Br3 0.0441(3) 0.0295(3) 0.0509(3) 0.0101(2) 0.0170(3) -0.0076(2) C21 0.029(3) 0.023(2) 0.046(3) -0.003(2) 0.001(2) -0.0025(18) C22 0.025(2) 0.036(3) 0.046(3) -0.004(2) 0.004(2) 0.003(2) C23 0.027(2) 0.031(2) 0.043(3) -0.001(2) 0.011(2) -0.005(2) C24 0.028(2) 0.025(2) 0.036(3) 0.001(2) 0.009(2) -0.0037(18) C25 0.069(7) 0.026(6) 0.059(7) -0.005(5) -0.009(6) -0.002(6) C26 0.069(9) 0.036(8) 0.064(9) -0.002(10) -0.024(7) -0.004(9) C27 0.103(11) 0.045(8) 0.061(9) 0.008(7) 0.001(7) -0.016(8) C28 0.087(10) 0.053(10) 0.085(9) -0.003(10) 0.031(9) -0.013(9) C29 0.063(8) 0.074(11) 0.092(9) 0.003(9) -0.008(7) -0.006(8) C30 0.071(9) 0.070(14) 0.053(9) 0.014(10) -0.013(6) -0.011(10) C31 0.111(12) 0.037(9) 0.143(16) -0.003(12) 0.058(12) 0.001(9) _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 N1 C6 1.307(6) . ? N1 C2 1.334(6) . ? C2 C3 1.385(6) . ? C2 S1 1.766(4) . ? C3 F3 1.353(5) . ? C3 C4 1.377(6) . ? C4 C5 1.402(6) . ? C4 S2 1.755(5) . ? C5 C6 1.384(6) . ? C5 S3 1.766(4) . ? C6 F6 1.339(5) . ? S1 C7 1.762(5) . ? C7 C12 1.385(7) . ? C7 C8 1.390(6) . ? C8 C9 1.385(7) . ? C8 Br1 1.898(5) . ? S2 C13 1.785(5) . ? C9 C10 1.369(7) . ? C10 C11 1.364(8) . ? C11 C12 1.382(8) . ? C13 C18 1.375(7) . ? C13 C14 1.382(6) . ? C14 C15 1.382(7) . ? C14 Br2 1.897(5) . ? S3 C19 1.774(4) . ? C15 C16 1.369(9) . ? C16 C17 1.382(9) . ? C17 C18 1.391(8) . ? C19 C20 1.380(6) . ? C19 C24 1.388(6) . ? C20 C21 1.399(6) . ? C20 Br3 1.900(4) . ? C21 C22 1.374(7) . ? C22 C23 1.398(7) . ? C23 C24 1.388(6) . ? C25 C30 1.36(2) . ? C25 C26 1.384(19) . ? C25 C31 1.51(2) . ? C26 C27 1.40(3) . ? C27 C28 1.39(2) . ? C28 C29 1.34(2) . ? C29 C30 1.39(2) . ? 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 C6 N1 C2 116.2(4) . . ? N1 C2 C3 121.4(4) . . ? N1 C2 S1 120.9(3) . . ? C3 C2 S1 117.7(3) . . ? F3 C3 C4 121.2(4) . . ? F3 C3 C2 116.3(4) . . ? C4 C3 C2 122.4(4) . . ? C3 C4 C5 115.8(4) . . ? C3 C4 S2 126.2(3) . . ? C5 C4 S2 117.9(3) . . ? C6 C5 C4 117.1(4) . . ? C6 C5 S3 120.9(3) . . ? C4 C5 S3 121.5(3) . . ? N1 C6 F6 114.7(4) . . ? N1 C6 C5 127.1(4) . . ? F6 C6 C5 118.2(4) . . ? C7 S1 C2 100.5(2) . . ? C12 C7 C8 117.1(5) . . ? C12 C7 S1 119.4(4) . . ? C8 C7 S1 123.4(4) . . ? C9 C8 C7 121.9(4) . . ? C9 C8 Br1 117.8(4) . . ? C7 C8 Br1 120.4(4) . . ? C4 S2 C13 105.0(2) . . ? C10 C9 C8 119.1(5) . . ? C11 C10 C9 120.6(6) . . ? C10 C11 C12 120.0(5) . . ? C11 C12 C7 121.4(5) . . ? C18 C13 C14 119.1(4) . . ? C18 C13 S2 118.1(4) . . ? C14 C13 S2 122.7(3) . . ? C15 C14 C13 121.4(5) . . ? C15 C14 Br2 117.7(4) . . ? C13 C14 Br2 120.9(3) . . ? C5 S3 C19 103.2(2) . . ? C16 C15 C14 118.7(5) . . ? C15 C16 C17 121.3(5) . . ? C16 C17 C18 119.2(5) . . ? C13 C18 C17 120.4(5) . . ? C20 C19 C24 118.6(4) . . ? C20 C19 S3 117.4(3) . . ? C24 C19 S3 124.0(3) . . ? C19 C20 C21 121.6(4) . . ? C19 C20 Br3 119.6(3) . . ? C21 C20 Br3 118.8(3) . . ? C22 C21 C20 119.2(5) . . ? C21 C22 C23 120.1(5) . . ? C24 C23 C22 119.9(4) . . ? C23 C24 C19 120.6(4) . . ? C30 C25 C26 116.3(19) . . ? C30 C25 C31 119.8(16) . . ? C26 C25 C31 123.9(17) . . ? C25 C26 C27 124.2(18) . . ? C28 C27 C26 117.0(17) . . ? C29 C28 C27 119(2) . . ? C28 C29 C30 122(2) . . ? C25 C30 C29 120.7(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 1.0(6) . . . . ? C6 N1 C2 S1 -178.4(3) . . . . ? N1 C2 C3 F3 -177.6(4) . . . . ? S1 C2 C3 F3 1.8(5) . . . . ? N1 C2 C3 C4 -0.2(7) . . . . ? S1 C2 C3 C4 179.3(3) . . . . ? F3 C3 C4 C5 175.6(4) . . . . ? C2 C3 C4 C5 -1.7(6) . . . . ? F3 C3 C4 S2 -0.4(6) . . . . ? C2 C3 C4 S2 -177.7(3) . . . . ? C3 C4 C5 C6 2.5(6) . . . . ? S2 C4 C5 C6 178.9(3) . . . . ? C3 C4 C5 S3 -169.5(3) . . . . ? S2 C4 C5 S3 6.9(5) . . . . ? C2 N1 C6 F6 179.8(4) . . . . ? C2 N1 C6 C5 0.0(7) . . . . ? C4 C5 C6 N1 -1.9(7) . . . . ? S3 C5 C6 N1 170.2(4) . . . . ? C4 C5 C6 F6 178.4(4) . . . . ? S3 C5 C6 F6 -9.6(6) . . . . ? N1 C2 S1 C7 -3.8(4) . . . . ? C3 C2 S1 C7 176.8(4) . . . . ? C2 S1 C7 C12 -96.8(5) . . . . ? C2 S1 C7 C8 86.2(4) . . . . ? C12 C7 C8 C9 1.3(7) . . . . ? S1 C7 C8 C9 178.3(4) . . . . ? C12 C7 C8 Br1 -179.4(4) . . . . ? S1 C7 C8 Br1 -2.4(6) . . . . ? C3 C4 S2 C13 -22.9(4) . . . . ? C5 C4 S2 C13 161.1(3) . . . . ? C7 C8 C9 C10 0.7(8) . . . . ? Br1 C8 C9 C10 -178.6(4) . . . . ? C8 C9 C10 C11 -1.7(9) . . . . ? C9 C10 C11 C12 0.7(10) . . . . ? C10 C11 C12 C7 1.4(10) . . . . ? C8 C7 C12 C11 -2.3(9) . . . . ? S1 C7 C12 C11 -179.4(5) . . . . ? C4 S2 C13 C18 116.6(4) . . . . ? C4 S2 C13 C14 -67.7(4) . . . . ? C18 C13 C14 C15 -0.9(7) . . . . ? S2 C13 C14 C15 -176.6(4) . . . . ? C18 C13 C14 Br2 -179.9(4) . . . . ? S2 C13 C14 Br2 4.4(6) . . . . ? C6 C5 S3 C19 87.0(4) . . . . ? C4 C5 S3 C19 -101.3(4) . . . . ? C13 C14 C15 C16 1.2(7) . . . . ? Br2 C14 C15 C16 -179.7(4) . . . . ? C14 C15 C16 C17 0.3(8) . . . . ? C15 C16 C17 C18 -2.1(9) . . . . ? C14 C13 C18 C17 -0.9(7) . . . . ? S2 C13 C18 C17 174.9(4) . . . . ? C16 C17 C18 C13 2.4(8) . . . . ? C5 S3 C19 C20 -173.6(4) . . . . ? C5 S3 C19 C24 6.2(4) . . . . ? C24 C19 C20 C21 1.2(7) . . . . ? S3 C19 C20 C21 -179.0(4) . . . . ? C24 C19 C20 Br3 179.3(3) . . . . ? S3 C19 C20 Br3 -0.9(5) . . . . ? C19 C20 C21 C22 -0.5(7) . . . . ? Br3 C20 C21 C22 -178.7(4) . . . . ? C20 C21 C22 C23 0.1(7) . . . . ? C21 C22 C23 C24 -0.4(7) . . . . ? C22 C23 C24 C19 1.1(7) . . . . ? C20 C19 C24 C23 -1.5(7) . . . . ? S3 C19 C24 C23 178.7(4) . . . . ? C30 C25 C26 C27 -1(4) . . . . ? C31 C25 C26 C27 -179.3(18) . . . . ? C25 C26 C27 C28 1(3) . . . . ? C26 C27 C28 C29 0(3) . . . . ? C27 C28 C29 C30 0(3) . . . . ? C26 C25 C30 C29 1(4) . . . . ? C31 C25 C30 C29 179(2) . . . . ? C28 C29 C30 C25 0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 28.87 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 1.031 _refine_diff_density_min -0.878 _refine_diff_density_rms 0.167 #===END data_8 _database_code_depnum_ccdc_archive 'CCDC 794856' #TrackingRef '- Weaver.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H4 F3 N S' _chemical_formula_sum 'C11 H4 F3 N S' _chemical_formula_weight 239.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2230(8) _cell_length_b 7.9584(9) _cell_length_c 9.1866(10) _cell_angle_alpha 100.979(2) _cell_angle_beta 97.143(2) _cell_angle_gamma 113.863(2) _cell_volume 462.01(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2860 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 26.93 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.362 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.849 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details 'TWINABS v2007/5, Sheldrick, G.M., (2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7449 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.08 _reflns_number_total 3593 _reflns_number_gt 3172 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _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 and local programs' _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. Non-merohedrally twinned with a 180 degree rotation relating the two components about reciprocal axis 0 0 1. Ratio of components was 62.15:37.85(7)%. ; _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^)+(0.0467P)^2^+0.1159P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3593 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.30418(5) 0.25106(5) 0.92937(4) 0.02511(10) Uani 1 1 d . . . C2 C 0.28484(19) 0.20442(19) 1.10501(15) 0.0215(3) Uani 1 1 d . . . C3 C 0.2995(2) 0.32815(19) 1.23902(16) 0.0246(3) Uani 1 1 d . . . F3 F 0.33273(13) 0.50808(11) 1.24488(10) 0.0348(2) Uani 1 1 d . . . C4 C 0.2781(2) 0.2600(2) 1.36502(16) 0.0267(3) Uani 1 1 d . . . F4 F 0.28771(14) 0.37427(13) 1.49616(10) 0.0375(2) Uani 1 1 d . . . N5 N 0.24641(18) 0.08544(17) 1.36810(13) 0.0273(3) Uani 1 1 d . . . C6 C 0.2334(2) -0.02883(19) 1.24080(16) 0.0237(3) Uani 1 1 d . . . F6 F 0.20183(14) -0.20500(12) 1.24751(10) 0.0336(2) Uani 1 1 d . . . C7 C 0.24900(19) 0.01659(18) 1.10301(15) 0.0204(3) Uani 1 1 d . . . C8 C 0.23457(19) -0.09414(18) 0.95362(15) 0.0208(3) Uani 1 1 d . . . C9 C 0.1961(2) -0.28496(19) 0.90387(16) 0.0250(3) Uani 1 1 d . . . H9 H 0.1770 -0.3623 0.9730 0.030 Uiso 1 1 calc R . . C10 C 0.1863(2) -0.3598(2) 0.75254(17) 0.0304(3) Uani 1 1 d . . . H10 H 0.1596 -0.4895 0.7179 0.036 Uiso 1 1 calc R . . C11 C 0.2149(2) -0.2477(2) 0.65055(17) 0.0317(3) Uani 1 1 d . . . H11 H 0.2082 -0.3020 0.5474 0.038 Uiso 1 1 calc R . . C12 C 0.2529(2) -0.0589(2) 0.69643(16) 0.0287(3) Uani 1 1 d . . . H12 H 0.2725 0.0173 0.6265 0.034 Uiso 1 1 calc R . . C13 C 0.26171(19) 0.01646(19) 0.84829(15) 0.0227(3) 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 0.02776(18) 0.02347(17) 0.02612(18) 0.01108(13) 0.00667(13) 0.01108(13) C2 0.0182(6) 0.0232(6) 0.0248(7) 0.0085(5) 0.0048(5) 0.0098(5) C3 0.0218(6) 0.0214(6) 0.0302(7) 0.0041(5) 0.0051(5) 0.0106(5) F3 0.0387(5) 0.0214(4) 0.0435(5) 0.0036(4) 0.0087(4) 0.0147(4) C4 0.0217(7) 0.0325(8) 0.0227(7) -0.0008(6) 0.0043(5) 0.0126(6) F4 0.0394(5) 0.0418(5) 0.0273(5) -0.0036(4) 0.0089(4) 0.0193(4) N5 0.0279(6) 0.0355(7) 0.0226(6) 0.0091(5) 0.0082(5) 0.0165(5) C6 0.0232(6) 0.0261(7) 0.0260(7) 0.0100(6) 0.0070(5) 0.0132(5) F6 0.0492(5) 0.0300(4) 0.0332(5) 0.0174(4) 0.0149(4) 0.0231(4) C7 0.0183(6) 0.0219(6) 0.0223(6) 0.0066(5) 0.0051(5) 0.0096(5) C8 0.0178(6) 0.0238(6) 0.0217(6) 0.0065(5) 0.0051(5) 0.0098(5) C9 0.0223(7) 0.0258(7) 0.0286(7) 0.0063(6) 0.0069(5) 0.0124(5) C10 0.0261(7) 0.0293(7) 0.0340(8) 0.0001(6) 0.0066(6) 0.0141(6) C11 0.0273(7) 0.0430(9) 0.0220(7) 0.0004(6) 0.0050(6) 0.0166(7) C12 0.0245(7) 0.0411(8) 0.0225(7) 0.0111(6) 0.0069(5) 0.0150(6) C13 0.0186(6) 0.0265(7) 0.0245(7) 0.0080(5) 0.0050(5) 0.0107(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 S1 C2 1.7329(14) . ? S1 C13 1.7564(14) . ? C2 C3 1.3849(19) . ? C2 C7 1.4060(17) . ? C3 F3 1.3417(15) . ? C3 C4 1.369(2) . ? C4 N5 1.3197(19) . ? C4 F4 1.3396(16) . ? N5 C6 1.3047(18) . ? C6 F6 1.3413(15) . ? C6 C7 1.3866(18) . ? C7 C8 1.4492(18) . ? C8 C9 1.3981(18) . ? C8 C13 1.4077(18) . ? C9 C10 1.385(2) . ? C10 C11 1.391(2) . ? C11 C12 1.381(2) . ? C12 C13 1.3923(19) . ? 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 S1 C13 90.90(6) . . ? C3 C2 C7 119.57(12) . . ? C3 C2 S1 127.54(11) . . ? C7 C2 S1 112.89(10) . . ? F3 C3 C4 121.26(12) . . ? F3 C3 C2 121.16(13) . . ? C4 C3 C2 117.58(13) . . ? N5 C4 F4 115.98(13) . . ? N5 C4 C3 124.65(13) . . ? F4 C4 C3 119.37(13) . . ? C6 N5 C4 116.84(12) . . ? N5 C6 F6 115.49(12) . . ? N5 C6 C7 125.83(12) . . ? F6 C6 C7 118.68(12) . . ? C6 C7 C2 115.52(12) . . ? C6 C7 C8 132.09(12) . . ? C2 C7 C8 112.39(11) . . ? C9 C8 C13 119.03(12) . . ? C9 C8 C7 130.08(12) . . ? C13 C8 C7 110.89(11) . . ? C10 C9 C8 119.14(13) . . ? C9 C10 C11 120.91(14) . . ? C12 C11 C10 121.21(13) . . ? C11 C12 C13 118.03(13) . . ? C12 C13 C8 121.68(13) . . ? C12 C13 S1 125.39(11) . . ? C8 C13 S1 112.93(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 C13 S1 C2 C3 -179.08(13) . . . . ? C13 S1 C2 C7 0.52(10) . . . . ? C7 C2 C3 F3 -179.72(11) . . . . ? S1 C2 C3 F3 -0.14(19) . . . . ? C7 C2 C3 C4 0.06(19) . . . . ? S1 C2 C3 C4 179.64(10) . . . . ? F3 C3 C4 N5 -179.59(12) . . . . ? C2 C3 C4 N5 0.6(2) . . . . ? F3 C3 C4 F4 0.92(19) . . . . ? C2 C3 C4 F4 -178.86(11) . . . . ? F4 C4 N5 C6 178.98(12) . . . . ? C3 C4 N5 C6 -0.5(2) . . . . ? C4 N5 C6 F6 179.80(11) . . . . ? C4 N5 C6 C7 -0.3(2) . . . . ? N5 C6 C7 C2 0.9(2) . . . . ? F6 C6 C7 C2 -179.18(11) . . . . ? N5 C6 C7 C8 -178.81(13) . . . . ? F6 C6 C7 C8 1.1(2) . . . . ? C3 C2 C7 C6 -0.76(18) . . . . ? S1 C2 C7 C6 179.60(9) . . . . ? C3 C2 C7 C8 179.04(11) . . . . ? S1 C2 C7 C8 -0.60(14) . . . . ? C6 C7 C8 C9 1.3(2) . . . . ? C2 C7 C8 C9 -178.46(13) . . . . ? C6 C7 C8 C13 -179.89(13) . . . . ? C2 C7 C8 C13 0.36(15) . . . . ? C13 C8 C9 C10 0.16(19) . . . . ? C7 C8 C9 C10 178.90(13) . . . . ? C8 C9 C10 C11 0.3(2) . . . . ? C9 C10 C11 C12 -0.3(2) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? C11 C12 C13 C8 0.5(2) . . . . ? C11 C12 C13 S1 -179.01(10) . . . . ? C9 C8 C13 C12 -0.54(19) . . . . ? C7 C8 C13 C12 -179.51(11) . . . . ? C9 C8 C13 S1 179.00(10) . . . . ? C7 C8 C13 S1 0.03(14) . . . . ? C2 S1 C13 C12 179.21(12) . . . . ? C2 S1 C13 C8 -0.31(10) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.08 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.366 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.053 #===END data_22 _database_code_depnum_ccdc_archive 'CCDC 794857' #TrackingRef '- Weaver.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H8 F2 O2' _chemical_formula_sum 'C18 H8 F2 O2' _chemical_formula_weight 294.24 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _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 6.198(2) _cell_length_b 6.525(2) _cell_length_c 15.416(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.211(4) _cell_angle_gamma 90.00 _cell_volume 618.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 519 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 23.55 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.992 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details 'SADABS v2008/1, Sheldrick, G.M., (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6942 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4 _diffrn_reflns_number 2656 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 22.99 _reflns_number_total 907 _reflns_number_gt 588 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _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 and local programs' _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^)+(0.1905P)^2^+0.7738P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.8(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 907 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1365 _refine_ls_R_factor_gt 0.0949 _refine_ls_wR_factor_ref 0.2902 _refine_ls_wR_factor_gt 0.2480 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 O1 O 0.3000(7) 0.2143(7) 0.6197(3) 0.0524(15) Uani 1 1 d . . . C2 C 0.4431(10) 0.3776(10) 0.6368(4) 0.0476(18) Uani 1 1 d . . . C3 C 0.4151(11) 0.5308(11) 0.6944(4) 0.054(2) Uani 1 1 d . . . H3 H 0.2932 0.5348 0.7261 0.065 Uiso 1 1 calc R . . C4 C 0.5743(13) 0.6798(10) 0.7040(4) 0.060(2) Uani 1 1 d . . . H4 H 0.5616 0.7901 0.7432 0.072 Uiso 1 1 calc R . . C5 C 0.7529(11) 0.6731(11) 0.6577(5) 0.057(2) Uani 1 1 d . . . H5 H 0.8597 0.7781 0.6661 0.068 Uiso 1 1 calc R . . C6 C 0.7772(10) 0.5174(10) 0.6002(4) 0.0504(19) Uani 1 1 d . . . H6 H 0.8990 0.5124 0.5685 0.061 Uiso 1 1 calc R . . C7 C 0.6180(10) 0.3677(9) 0.5899(4) 0.0480(19) Uani 1 1 d . . . C8 C 0.5862(9) 0.1777(9) 0.5372(4) 0.0428(17) Uani 1 1 d . . . C9 C 0.6941(9) 0.0819(10) 0.4779(4) 0.0454(18) Uani 1 1 d . . . F1 F 0.8815(5) 0.1611(6) 0.4546(2) 0.0546(14) Uani 1 1 d . . . C10 C 0.3932(10) 0.0946(9) 0.5589(4) 0.0442(18) 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 O1 0.056(3) 0.044(3) 0.059(3) -0.006(2) 0.012(2) -0.004(2) C2 0.048(4) 0.036(4) 0.056(4) 0.007(3) -0.009(3) -0.007(3) C3 0.056(4) 0.056(5) 0.048(4) 0.008(3) 0.002(3) 0.009(3) C4 0.091(5) 0.042(4) 0.041(4) -0.008(3) -0.016(4) 0.016(4) C5 0.054(4) 0.040(4) 0.069(5) 0.008(3) -0.019(3) -0.012(3) C6 0.051(4) 0.050(4) 0.048(4) 0.013(3) 0.000(3) 0.003(3) C7 0.062(4) 0.035(4) 0.042(4) 0.002(3) -0.010(3) 0.010(3) C8 0.042(3) 0.035(4) 0.047(4) 0.004(3) -0.009(3) -0.003(3) C9 0.032(3) 0.042(4) 0.062(4) 0.016(3) 0.006(3) -0.008(3) F1 0.046(2) 0.045(2) 0.074(3) 0.0042(18) 0.0130(17) -0.0054(16) C10 0.054(4) 0.040(4) 0.040(3) 0.003(3) 0.006(3) 0.017(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 O1 C2 1.391(7) . ? O1 C10 1.400(7) . ? C2 C3 1.362(9) . ? C2 C7 1.378(9) . ? C3 C4 1.380(10) . ? C4 C5 1.391(11) . ? C5 C6 1.368(10) . ? C6 C7 1.384(9) . ? C7 C8 1.481(9) . ? C8 C9 1.352(8) . ? C8 C10 1.391(8) . ? C9 F1 1.360(6) . ? C9 C10 1.366(9) 3_656 ? C10 C9 1.366(9) 3_656 ? 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 O1 C10 104.3(5) . . ? C3 C2 C7 123.3(6) . . ? C3 C2 O1 123.8(6) . . ? C7 C2 O1 112.9(6) . . ? C2 C3 C4 116.0(6) . . ? C3 C4 C5 121.8(6) . . ? C6 C5 C4 121.0(6) . . ? C5 C6 C7 117.6(6) . . ? C2 C7 C6 120.2(6) . . ? C2 C7 C8 105.5(6) . . ? C6 C7 C8 134.3(6) . . ? C9 C8 C10 119.7(5) . . ? C9 C8 C7 135.6(6) . . ? C10 C8 C7 104.7(5) . . ? C8 C9 F1 121.0(6) . . ? C8 C9 C10 117.8(5) . 3_656 ? F1 C9 C10 121.2(6) . 3_656 ? C9 C10 C8 122.5(5) 3_656 . ? C9 C10 O1 125.0(5) 3_656 . ? C8 C10 O1 112.5(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 C10 O1 C2 C3 -179.0(5) . . . . ? C10 O1 C2 C7 0.6(6) . . . . ? C7 C2 C3 C4 -0.1(9) . . . . ? O1 C2 C3 C4 179.4(6) . . . . ? C2 C3 C4 C5 -0.2(9) . . . . ? C3 C4 C5 C6 0.2(9) . . . . ? C4 C5 C6 C7 0.0(9) . . . . ? C3 C2 C7 C6 0.4(9) . . . . ? O1 C2 C7 C6 -179.2(5) . . . . ? C3 C2 C7 C8 179.1(5) . . . . ? O1 C2 C7 C8 -0.4(7) . . . . ? C5 C6 C7 C2 -0.3(9) . . . . ? C5 C6 C7 C8 -178.6(6) . . . . ? C2 C7 C8 C9 178.9(7) . . . . ? C6 C7 C8 C9 -2.6(12) . . . . ? C2 C7 C8 C10 0.1(6) . . . . ? C6 C7 C8 C10 178.6(6) . . . . ? C10 C8 C9 F1 179.0(5) . . . . ? C7 C8 C9 F1 0.4(10) . . . . ? C10 C8 C9 C10 0.2(9) . . . 3_656 ? C7 C8 C9 C10 -178.4(6) . . . 3_656 ? C9 C8 C10 C9 -0.2(10) . . . 3_656 ? C7 C8 C10 C9 178.8(5) . . . 3_656 ? C9 C8 C10 O1 -178.8(5) . . . . ? C7 C8 C10 O1 0.2(6) . . . . ? C2 O1 C10 C9 -179.0(6) . . . 3_656 ? C2 O1 C10 C8 -0.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 22.99 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.974 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.094 #===END data_32A _database_code_depnum_ccdc_archive 'CCDC 794858' #TrackingRef '- Weaver.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H8 Br F3 S2' _chemical_formula_sum 'C18 H8 Br F3 S2' _chemical_formula_weight 425.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 _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 9.8845(5) _cell_length_b 15.6680(8) _cell_length_c 10.3729(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.2845(8) _cell_angle_gamma 90.00 _cell_volume 1605.18(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4354 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.23 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.84 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.760 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 2.848 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.196 _exptl_absorpt_correction_T_max 0.756 _exptl_absorpt_process_details 'SADABS v2007/4, Sheldrick, G.M., (2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16379 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.33 _reflns_number_total 3987 _reflns_number_gt 3119 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _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 and local programs' _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^)+(0.0469P)^2^+1.0699P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3987 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.07087(7) 0.35737(4) -0.17917(6) 0.03459(16) Uani 1 1 d . . . C2 C 0.0421(2) 0.31497(15) -0.0634(2) 0.0281(5) Uani 1 1 d . . . C3 C 0.1206(3) 0.36081(15) 0.0264(2) 0.0304(5) Uani 1 1 d . . . F3 F 0.11589(18) 0.44650(9) 0.02806(17) 0.0415(4) Uani 1 1 d . . . C4 C 0.2036(2) 0.31831(16) 0.1134(2) 0.0307(5) Uani 1 1 d . . . F4 F 0.27767(17) 0.36392(10) 0.20027(16) 0.0435(4) Uani 1 1 d . . . C5 C 0.2123(2) 0.22925(16) 0.1153(2) 0.0295(5) Uani 1 1 d . . . C6 C 0.1324(2) 0.18516(15) 0.0256(2) 0.0290(5) Uani 1 1 d . . . F6 F 0.13844(16) 0.09898(9) 0.02502(15) 0.0385(4) Uani 1 1 d . . . C7 C 0.0471(2) 0.22507(15) -0.0657(2) 0.0272(5) Uani 1 1 d . . . C8 C -0.0438(2) 0.18994(16) -0.1653(2) 0.0301(5) Uani 1 1 d . . . C9 C -0.0674(3) 0.10431(18) -0.1997(3) 0.0371(6) Uani 1 1 d . . . H9 H -0.0198 0.0595 -0.1559 0.045 Uiso 1 1 calc R . . C10 C -0.1612(3) 0.0865(2) -0.2984(3) 0.0451(7) Uani 1 1 d . . . H10 H -0.1784 0.0288 -0.3220 0.054 Uiso 1 1 calc R . . C11 C -0.2306(3) 0.1512(2) -0.3636(3) 0.0485(8) Uani 1 1 d . . . H11 H -0.2948 0.1370 -0.4308 0.058 Uiso 1 1 calc R . . C12 C -0.2084(3) 0.2356(2) -0.3330(3) 0.0421(7) Uani 1 1 d . . . H12 H -0.2558 0.2797 -0.3785 0.051 Uiso 1 1 calc R . . C13 C -0.1141(3) 0.25460(17) -0.2334(2) 0.0324(5) Uani 1 1 d . . . S14 S 0.31736(7) 0.17667(5) 0.23138(6) 0.03536(16) Uani 1 1 d . . . C15 C 0.4499(2) 0.14001(16) 0.1346(2) 0.0266(5) Uani 1 1 d . . . C16 C 0.4673(2) 0.16500(16) 0.0079(2) 0.0303(5) Uani 1 1 d . . . H16 H 0.4087 0.2066 -0.0308 0.036 Uiso 1 1 calc R . . C17 C 0.5696(3) 0.12962(18) -0.0625(3) 0.0365(6) Uani 1 1 d . . . H17 H 0.5808 0.1473 -0.1490 0.044 Uiso 1 1 calc R . . C18 C 0.6554(3) 0.06888(18) -0.0077(3) 0.0408(6) Uani 1 1 d . . . H18 H 0.7231 0.0434 -0.0576 0.049 Uiso 1 1 calc R . . C19 C 0.6428(3) 0.04524(18) 0.1191(3) 0.0395(6) Uani 1 1 d . . . H19 H 0.7032 0.0047 0.1581 0.047 Uiso 1 1 calc R . . C20 C 0.5409(3) 0.08131(17) 0.1893(2) 0.0314(5) Uani 1 1 d . . . Br1 Br 0.52356(3) 0.04808(2) 0.36293(3) 0.05105(12) 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 0.0342(3) 0.0340(3) 0.0356(3) 0.0032(3) 0.0014(3) 0.0058(3) C2 0.0246(11) 0.0284(12) 0.0316(12) 0.0003(10) 0.0052(9) 0.0037(9) C3 0.0324(13) 0.0234(12) 0.0360(13) -0.0029(10) 0.0077(10) 0.0007(10) F3 0.0506(10) 0.0234(8) 0.0506(10) -0.0021(6) 0.0022(8) -0.0012(7) C4 0.0286(12) 0.0315(13) 0.0322(12) -0.0083(10) 0.0027(10) -0.0043(10) F4 0.0463(9) 0.0392(9) 0.0443(9) -0.0108(7) -0.0074(7) -0.0052(7) C5 0.0278(12) 0.0317(13) 0.0293(12) -0.0009(10) 0.0035(10) 0.0037(10) C6 0.0284(12) 0.0239(12) 0.0352(13) -0.0010(10) 0.0078(10) 0.0032(10) F6 0.0458(9) 0.0232(7) 0.0464(9) -0.0021(6) 0.0010(7) 0.0046(6) C7 0.0235(11) 0.0282(12) 0.0302(12) -0.0039(9) 0.0070(9) 0.0013(9) C8 0.0268(12) 0.0335(13) 0.0305(12) -0.0057(10) 0.0094(10) -0.0031(10) C9 0.0361(14) 0.0388(15) 0.0373(14) -0.0097(11) 0.0116(11) -0.0088(12) C10 0.0425(16) 0.0518(17) 0.0419(16) -0.0174(14) 0.0135(13) -0.0161(14) C11 0.0347(15) 0.076(2) 0.0354(15) -0.0154(15) 0.0051(12) -0.0159(15) C12 0.0322(14) 0.062(2) 0.0325(14) -0.0014(13) 0.0035(11) -0.0004(13) C13 0.0277(12) 0.0395(14) 0.0303(12) -0.0015(11) 0.0061(10) -0.0014(11) S14 0.0364(3) 0.0451(4) 0.0249(3) 0.0012(3) 0.0045(2) 0.0096(3) C15 0.0245(11) 0.0301(12) 0.0251(11) -0.0002(9) -0.0001(9) -0.0008(9) C16 0.0291(12) 0.0346(14) 0.0271(12) 0.0053(10) -0.0013(10) 0.0035(10) C17 0.0360(14) 0.0434(15) 0.0307(13) 0.0022(11) 0.0084(11) -0.0015(12) C18 0.0324(14) 0.0409(15) 0.0499(17) 0.0026(13) 0.0129(12) 0.0024(12) C19 0.0274(13) 0.0374(15) 0.0537(17) 0.0095(12) 0.0017(12) 0.0031(11) C20 0.0299(12) 0.0340(13) 0.0299(12) 0.0094(10) -0.0025(10) -0.0034(10) Br1 0.0505(2) 0.0657(2) 0.03647(17) 0.02294(14) -0.00458(13) -0.00021(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.739(2) . ? S1 C13 1.753(3) . ? C2 C3 1.388(3) . ? C2 C7 1.410(3) . ? C3 F3 1.344(3) . ? C3 C4 1.369(4) . ? C4 F4 1.344(3) . ? C4 C5 1.398(4) . ? C5 C6 1.381(3) . ? C5 S14 1.763(3) . ? C6 F6 1.352(3) . ? C6 C7 1.392(3) . ? C7 C8 1.450(3) . ? C8 C13 1.403(4) . ? C8 C9 1.405(4) . ? C9 C10 1.382(4) . ? C10 C11 1.385(5) . ? C11 C12 1.375(4) . ? C12 C13 1.396(4) . ? S14 C15 1.777(2) . ? C15 C16 1.389(3) . ? C15 C20 1.391(3) . ? C16 C17 1.387(4) . ? C17 C18 1.382(4) . ? C18 C19 1.377(4) . ? C19 C20 1.386(4) . ? C20 Br1 1.889(2) . ? 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 S1 C13 90.71(12) . . ? C3 C2 C7 120.6(2) . . ? C3 C2 S1 126.30(19) . . ? C7 C2 S1 113.08(19) . . ? F3 C3 C4 119.9(2) . . ? F3 C3 C2 120.4(2) . . ? C4 C3 C2 119.7(2) . . ? F4 C4 C3 118.7(2) . . ? F4 C4 C5 119.3(2) . . ? C3 C4 C5 122.0(2) . . ? C6 C5 C4 117.2(2) . . ? C6 C5 S14 122.12(19) . . ? C4 C5 S14 120.69(19) . . ? F6 C6 C5 118.6(2) . . ? F6 C6 C7 118.1(2) . . ? C5 C6 C7 123.3(2) . . ? C6 C7 C2 117.3(2) . . ? C6 C7 C8 131.0(2) . . ? C2 C7 C8 111.7(2) . . ? C13 C8 C9 119.2(2) . . ? C13 C8 C7 111.4(2) . . ? C9 C8 C7 129.4(2) . . ? C10 C9 C8 118.7(3) . . ? C9 C10 C11 121.2(3) . . ? C12 C11 C10 121.3(3) . . ? C11 C12 C13 118.1(3) . . ? C12 C13 C8 121.4(3) . . ? C12 C13 S1 125.5(2) . . ? C8 C13 S1 113.08(19) . . ? C5 S14 C15 101.11(11) . . ? C16 C15 C20 118.0(2) . . ? C16 C15 S14 124.44(19) . . ? C20 C15 S14 117.55(18) . . ? C17 C16 C15 120.4(2) . . ? C18 C17 C16 120.5(2) . . ? C19 C18 C17 120.1(3) . . ? C18 C19 C20 119.1(2) . . ? C19 C20 C15 121.8(2) . . ? C19 C20 Br1 118.90(19) . . ? C15 C20 Br1 119.28(19) . . ? 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 C13 S1 C2 C3 -178.9(2) . . . . ? C13 S1 C2 C7 0.00(19) . . . . ? C7 C2 C3 F3 179.8(2) . . . . ? S1 C2 C3 F3 -1.4(3) . . . . ? C7 C2 C3 C4 0.1(4) . . . . ? S1 C2 C3 C4 178.86(19) . . . . ? F3 C3 C4 F4 0.9(4) . . . . ? C2 C3 C4 F4 -179.4(2) . . . . ? F3 C3 C4 C5 -179.8(2) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? F4 C4 C5 C6 178.9(2) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? F4 C4 C5 S14 0.8(3) . . . . ? C3 C4 C5 S14 -178.5(2) . . . . ? C4 C5 C6 F6 -180.0(2) . . . . ? S14 C5 C6 F6 -1.9(3) . . . . ? C4 C5 C6 C7 1.0(4) . . . . ? S14 C5 C6 C7 178.99(18) . . . . ? F6 C6 C7 C2 180.0(2) . . . . ? C5 C6 C7 C2 -1.0(4) . . . . ? F6 C6 C7 C8 1.5(4) . . . . ? C5 C6 C7 C8 -179.4(2) . . . . ? C3 C2 C7 C6 0.4(3) . . . . ? S1 C2 C7 C6 -178.50(17) . . . . ? C3 C2 C7 C8 179.2(2) . . . . ? S1 C2 C7 C8 0.2(3) . . . . ? C6 C7 C8 C13 178.1(2) . . . . ? C2 C7 C8 C13 -0.4(3) . . . . ? C6 C7 C8 C9 -2.3(4) . . . . ? C2 C7 C8 C9 179.2(2) . . . . ? C13 C8 C9 C10 -1.1(4) . . . . ? C7 C8 C9 C10 179.3(2) . . . . ? C8 C9 C10 C11 0.5(4) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C10 C11 C12 C13 -0.4(4) . . . . ? C11 C12 C13 C8 -0.3(4) . . . . ? C11 C12 C13 S1 -180.0(2) . . . . ? C9 C8 C13 C12 1.0(4) . . . . ? C7 C8 C13 C12 -179.3(2) . . . . ? C9 C8 C13 S1 -179.26(18) . . . . ? C7 C8 C13 S1 0.4(3) . . . . ? C2 S1 C13 C12 179.5(2) . . . . ? C2 S1 C13 C8 -0.23(19) . . . . ? C6 C5 S14 C15 73.9(2) . . . . ? C4 C5 S14 C15 -108.1(2) . . . . ? C5 S14 C15 C16 10.7(2) . . . . ? C5 S14 C15 C20 -168.3(2) . . . . ? C20 C15 C16 C17 2.4(4) . . . . ? S14 C15 C16 C17 -176.6(2) . . . . ? C15 C16 C17 C18 0.2(4) . . . . ? C16 C17 C18 C19 -2.3(4) . . . . ? C17 C18 C19 C20 1.8(4) . . . . ? C18 C19 C20 C15 0.8(4) . . . . ? C18 C19 C20 Br1 179.6(2) . . . . ? C16 C15 C20 C19 -2.9(4) . . . . ? S14 C15 C20 C19 176.2(2) . . . . ? C16 C15 C20 Br1 178.28(19) . . . . ? S14 C15 C20 Br1 -2.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.023 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.073 #===END data_32B _database_code_depnum_ccdc_archive 'CCDC 794859' #TrackingRef '- Weaver.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H8 Br F3 S2' _chemical_formula_sum 'C18 H8 Br F3 S2' _chemical_formula_weight 425.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 _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 15.1514(9) _cell_length_b 12.9717(8) _cell_length_c 8.1916(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.5221(9) _cell_angle_gamma 90.00 _cell_volume 1565.34(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5922 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 30.34 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 2.921 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.234 _exptl_absorpt_correction_T_max 0.918 _exptl_absorpt_process_details 'SADABS v2007/4, Sheldrick, G.M., (2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 18058 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 30.57 _reflns_number_total 4770 _reflns_number_gt 3675 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _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 and local programs' _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^)+(0.0585P)^2^+0.1754P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _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 4770 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.02240(4) 0.74095(4) 0.51513(7) 0.02830(12) Uani 1 1 d . . . C2 C 0.07209(13) 0.66199(15) 0.5743(2) 0.0225(4) Uani 1 1 d . . . C3 C 0.15565(15) 0.67712(17) 0.5371(3) 0.0290(4) Uani 1 1 d . . . F3 F 0.16915(11) 0.76007(11) 0.4464(2) 0.0435(4) Uani 1 1 d . . . C4 C 0.22437(14) 0.60809(18) 0.5911(3) 0.0282(4) Uani 1 1 d . . . F4 F 0.30484(9) 0.62483(12) 0.55325(18) 0.0426(4) Uani 1 1 d . . . C5 C 0.21311(13) 0.52069(16) 0.6851(2) 0.0241(4) Uani 1 1 d . . . C6 C 0.12878(13) 0.50741(15) 0.7214(2) 0.0216(4) Uani 1 1 d . . . F6 F 0.11560(8) 0.42503(9) 0.81236(16) 0.0292(3) Uani 1 1 d . . . C7 C 0.05701(13) 0.57604(14) 0.6688(2) 0.0202(4) Uani 1 1 d . . . C8 C -0.03448(13) 0.57451(15) 0.6939(2) 0.0218(4) Uani 1 1 d . . . C9 C -0.07593(14) 0.50440(17) 0.7822(3) 0.0280(4) Uani 1 1 d . . . H9 H -0.0441 0.4473 0.8339 0.034 Uiso 1 1 calc R . . C10 C -0.16462(16) 0.5209(2) 0.7916(3) 0.0357(5) Uani 1 1 d . . . H10 H -0.1927 0.4739 0.8489 0.043 Uiso 1 1 calc R . . C11 C -0.21289(15) 0.6072(2) 0.7163(3) 0.0373(5) Uani 1 1 d . . . H11 H -0.2722 0.6173 0.7259 0.045 Uiso 1 1 calc R . . C12 C -0.17413(15) 0.67715(18) 0.6284(3) 0.0319(5) Uani 1 1 d . . . H12 H -0.2066 0.7341 0.5774 0.038 Uiso 1 1 calc R . . C13 C -0.08447(14) 0.66042(15) 0.6176(2) 0.0238(4) Uani 1 1 d . . . S14 S 0.29935(4) 0.42727(4) 0.74593(7) 0.02808(12) Uani 1 1 d . . . C15 C 0.35533(12) 0.47196(15) 0.9489(2) 0.0218(4) Uani 1 1 d . . . C16 C 0.34503(14) 0.57065(16) 1.0080(3) 0.0268(4) Uani 1 1 d . . . H16 H 0.3052 0.6166 0.9410 0.032 Uiso 1 1 calc R . . C17 C 0.39358(16) 0.60129(18) 1.1660(3) 0.0317(5) Uani 1 1 d . . . H17 H 0.3849 0.6669 1.2053 0.038 Uiso 1 1 calc R . . C18 C 0.45487(16) 0.53462(18) 1.2653(3) 0.0337(5) Uani 1 1 d . . . H18 H 0.4883 0.5560 1.3699 0.040 Uiso 1 1 calc R . . C19 C 0.46611(16) 0.43641(18) 1.2087(3) 0.0314(5) Uani 1 1 d . . . H19 H 0.5073 0.3914 1.2747 0.038 Uiso 1 1 calc R . . C20 C 0.41580(13) 0.40526(16) 1.0531(3) 0.0240(4) Uani 1 1 d . . . Br1 Br 0.429846(15) 0.268511(17) 0.98197(3) 0.03465(9) 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 0.0305(3) 0.0229(2) 0.0283(3) 0.00407(19) 0.0003(2) 0.0052(2) C2 0.0237(9) 0.0213(9) 0.0200(8) -0.0010(7) -0.0001(7) 0.0007(7) C3 0.0323(11) 0.0286(11) 0.0257(10) 0.0057(8) 0.0058(8) -0.0060(8) F3 0.0404(8) 0.0402(8) 0.0503(9) 0.0225(7) 0.0114(7) -0.0045(6) C4 0.0227(9) 0.0349(11) 0.0281(10) -0.0008(8) 0.0078(8) -0.0043(8) F4 0.0251(7) 0.0538(9) 0.0513(8) 0.0112(7) 0.0138(6) -0.0032(6) C5 0.0209(9) 0.0248(10) 0.0243(9) -0.0019(7) 0.0008(7) 0.0007(7) C6 0.0232(9) 0.0190(9) 0.0207(9) -0.0003(7) 0.0013(7) -0.0014(7) F6 0.0277(6) 0.0215(6) 0.0379(7) 0.0088(5) 0.0067(5) 0.0026(5) C7 0.0218(9) 0.0192(9) 0.0181(8) -0.0030(6) 0.0018(7) 0.0005(7) C8 0.0206(9) 0.0230(9) 0.0202(9) -0.0051(7) 0.0017(7) 0.0003(7) C9 0.0261(10) 0.0273(10) 0.0301(10) -0.0012(8) 0.0053(8) -0.0013(8) C10 0.0282(11) 0.0438(14) 0.0380(12) -0.0021(10) 0.0138(9) -0.0048(10) C11 0.0219(10) 0.0483(14) 0.0411(13) -0.0117(11) 0.0064(9) 0.0031(10) C12 0.0259(10) 0.0340(12) 0.0318(11) -0.0098(9) -0.0010(8) 0.0074(9) C13 0.0246(9) 0.0229(9) 0.0210(9) -0.0052(7) -0.0004(7) 0.0015(7) S14 0.0223(2) 0.0296(3) 0.0292(3) -0.00713(19) -0.00035(19) 0.00565(19) C15 0.0157(8) 0.0253(10) 0.0243(9) -0.0014(7) 0.0044(7) -0.0014(7) C16 0.0236(9) 0.0268(10) 0.0294(10) -0.0024(8) 0.0051(8) 0.0017(8) C17 0.0332(11) 0.0296(11) 0.0325(11) -0.0082(9) 0.0078(9) -0.0042(9) C18 0.0347(11) 0.0388(12) 0.0250(10) -0.0003(9) 0.0019(9) -0.0107(10) C19 0.0284(11) 0.0331(11) 0.0304(11) 0.0074(9) 0.0023(9) -0.0063(9) C20 0.0202(9) 0.0235(9) 0.0291(10) 0.0019(7) 0.0073(8) -0.0035(7) Br1 0.03239(13) 0.02395(13) 0.04513(16) 0.00249(9) 0.00403(10) 0.00244(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 S1 C2 1.735(2) . ? S1 C13 1.746(2) . ? C2 C3 1.384(3) . ? C2 C7 1.406(3) . ? C3 F3 1.350(2) . ? C3 C4 1.366(3) . ? C4 F4 1.344(2) . ? C4 C5 1.403(3) . ? C5 C6 1.389(3) . ? C5 S14 1.766(2) . ? C6 F6 1.344(2) . ? C6 C7 1.393(3) . ? C7 C8 1.449(3) . ? C8 C9 1.399(3) . ? C8 C13 1.409(3) . ? C9 C10 1.381(3) . ? C10 C11 1.400(4) . ? C11 C12 1.373(4) . ? C12 C13 1.399(3) . ? S14 C15 1.7776(19) . ? C15 C16 1.390(3) . ? C15 C20 1.397(3) . ? C16 C17 1.389(3) . ? C17 C18 1.385(3) . ? C18 C19 1.380(3) . ? C19 C20 1.383(3) . ? C20 Br1 1.895(2) . ? 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 S1 C13 90.82(10) . . ? C3 C2 C7 120.57(18) . . ? C3 C2 S1 126.32(16) . . ? C7 C2 S1 113.10(15) . . ? F3 C3 C4 119.9(2) . . ? F3 C3 C2 119.90(19) . . ? C4 C3 C2 120.18(19) . . ? F4 C4 C3 118.9(2) . . ? F4 C4 C5 119.37(19) . . ? C3 C4 C5 121.75(19) . . ? C6 C5 C4 116.98(18) . . ? C6 C5 S14 120.76(16) . . ? C4 C5 S14 122.16(16) . . ? F6 C6 C5 118.73(17) . . ? F6 C6 C7 118.24(17) . . ? C5 C6 C7 123.03(18) . . ? C6 C7 C2 117.48(18) . . ? C6 C7 C8 130.60(18) . . ? C2 C7 C8 111.92(17) . . ? C9 C8 C13 118.94(19) . . ? C9 C8 C7 130.00(19) . . ? C13 C8 C7 111.04(18) . . ? C10 C9 C8 119.3(2) . . ? C9 C10 C11 120.9(2) . . ? C12 C11 C10 121.1(2) . . ? C11 C12 C13 118.1(2) . . ? C12 C13 C8 121.6(2) . . ? C12 C13 S1 125.28(17) . . ? C8 C13 S1 113.11(15) . . ? C5 S14 C15 101.52(9) . . ? C16 C15 C20 117.94(18) . . ? C16 C15 S14 123.92(16) . . ? C20 C15 S14 118.10(15) . . ? C17 C16 C15 120.7(2) . . ? C18 C17 C16 120.3(2) . . ? C19 C18 C17 119.8(2) . . ? C18 C19 C20 119.6(2) . . ? C19 C20 C15 121.6(2) . . ? C19 C20 Br1 118.65(16) . . ? C15 C20 Br1 119.77(15) . . ? 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 C13 S1 C2 C3 -179.62(19) . . . . ? C13 S1 C2 C7 0.38(15) . . . . ? C7 C2 C3 F3 -179.95(18) . . . . ? S1 C2 C3 F3 0.1(3) . . . . ? C7 C2 C3 C4 0.4(3) . . . . ? S1 C2 C3 C4 -179.62(17) . . . . ? F3 C3 C4 F4 0.4(3) . . . . ? C2 C3 C4 F4 -179.93(18) . . . . ? F3 C3 C4 C5 -179.75(19) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? F4 C4 C5 C6 179.69(18) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? F4 C4 C5 S14 -3.7(3) . . . . ? C3 C4 C5 S14 176.47(17) . . . . ? C4 C5 C6 F6 -179.46(17) . . . . ? S14 C5 C6 F6 3.9(3) . . . . ? C4 C5 C6 C7 0.1(3) . . . . ? S14 C5 C6 C7 -176.59(15) . . . . ? F6 C6 C7 C2 179.75(16) . . . . ? C5 C6 C7 C2 0.2(3) . . . . ? F6 C6 C7 C8 -0.7(3) . . . . ? C5 C6 C7 C8 179.75(19) . . . . ? C3 C2 C7 C6 -0.4(3) . . . . ? S1 C2 C7 C6 179.57(14) . . . . ? C3 C2 C7 C8 179.93(18) . . . . ? S1 C2 C7 C8 -0.1(2) . . . . ? C6 C7 C8 C9 1.7(3) . . . . ? C2 C7 C8 C9 -178.7(2) . . . . ? C6 C7 C8 C13 -179.96(19) . . . . ? C2 C7 C8 C13 -0.4(2) . . . . ? C13 C8 C9 C10 0.3(3) . . . . ? C7 C8 C9 C10 178.5(2) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C9 C10 C11 C12 1.1(4) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C11 C12 C13 C8 0.1(3) . . . . ? C11 C12 C13 S1 -178.89(16) . . . . ? C9 C8 C13 C12 0.1(3) . . . . ? C7 C8 C13 C12 -178.43(17) . . . . ? C9 C8 C13 S1 179.22(15) . . . . ? C7 C8 C13 S1 0.7(2) . . . . ? C2 S1 C13 C12 178.45(18) . . . . ? C2 S1 C13 C8 -0.61(15) . . . . ? C6 C5 S14 C15 -89.99(17) . . . . ? C4 C5 S14 C15 93.50(18) . . . . ? C5 S14 C15 C16 -16.2(2) . . . . ? C5 S14 C15 C20 166.23(15) . . . . ? C20 C15 C16 C17 -0.1(3) . . . . ? S14 C15 C16 C17 -177.67(16) . . . . ? C15 C16 C17 C18 1.7(3) . . . . ? C16 C17 C18 C19 -1.6(3) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? C18 C19 C20 C15 1.9(3) . . . . ? C18 C19 C20 Br1 -177.96(16) . . . . ? C16 C15 C20 C19 -1.7(3) . . . . ? S14 C15 C20 C19 176.00(16) . . . . ? C16 C15 C20 Br1 178.10(15) . . . . ? S14 C15 C20 Br1 -4.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.57 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.564 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.091 #===END data_34 _database_code_depnum_ccdc_archive 'CCDC 794860' #TrackingRef '- Weaver.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H8 F2 S2' _chemical_formula_sum 'C18 H8 F2 S2' _chemical_formula_weight 326.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _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 7.823(2) _cell_length_b 3.9110(12) _cell_length_c 21.623(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.499(4) _cell_angle_gamma 90.00 _cell_volume 660.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1598 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.39 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.417 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.800 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'SADABS v2007/4, Sheldrick, G.M., (2007)' _exptl_special_details ; These crystals were very thin and also flexible. ; _diffrn_ambient_temperature 150(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 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4059 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.43 _reflns_number_total 1347 _reflns_number_gt 1022 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _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 and local programs' _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^)+(0.0684P)^2^+0.3261P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1347 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1285 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.38688(10) 0.2393(3) 0.12981(4) 0.0243(3) Uani 1 1 d . . . C2 C 0.5973(4) 0.3851(9) 0.14468(16) 0.0225(7) Uani 1 1 d . . . C3 C 0.6568(4) 0.5374(9) 0.19978(16) 0.0269(8) Uani 1 1 d . . . H3 H 0.5832 0.5700 0.2331 0.032 Uiso 1 1 calc R . . C4 C 0.8274(5) 0.6405(9) 0.20463(18) 0.0292(8) Uani 1 1 d . . . H4 H 0.8712 0.7426 0.2419 0.035 Uiso 1 1 calc R . . C5 C 0.9340(4) 0.5956(10) 0.15559(17) 0.0286(8) Uani 1 1 d . . . H5 H 1.0492 0.6721 0.1595 0.034 Uiso 1 1 calc R . . C6 C 0.8753(4) 0.4414(9) 0.10117(17) 0.0257(8) Uani 1 1 d . . . H6 H 0.9500 0.4094 0.0682 0.031 Uiso 1 1 calc R . . C7 C 0.7043(4) 0.3323(8) 0.09515(16) 0.0210(8) Uani 1 1 d . . . C8 C 0.6130(4) 0.1636(8) 0.04356(16) 0.0207(7) Uani 1 1 d . . . C9 C 0.4396(4) 0.0981(9) 0.05644(15) 0.0210(7) Uani 1 1 d . . . C10 C 0.3322(4) -0.0607(9) 0.01331(16) 0.0224(7) Uani 1 1 d . . . F10 F 0.1674(2) -0.1202(5) 0.02845(9) 0.0279(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 S1 0.0141(4) 0.0321(5) 0.0270(5) -0.0013(4) 0.0046(3) -0.0008(4) C2 0.0123(15) 0.0248(18) 0.0305(18) 0.0045(15) 0.0016(13) 0.0011(13) C3 0.0234(19) 0.027(2) 0.0299(19) 0.0004(15) 0.0024(15) 0.0021(15) C4 0.0272(19) 0.025(2) 0.035(2) 0.0003(15) -0.0050(15) -0.0001(15) C5 0.0148(17) 0.0287(19) 0.042(2) 0.0015(17) -0.0029(15) -0.0010(15) C6 0.0151(17) 0.0258(19) 0.036(2) 0.0051(16) 0.0020(14) 0.0015(14) C7 0.0152(16) 0.0184(19) 0.0293(18) 0.0033(13) 0.0009(13) 0.0026(12) C8 0.0107(15) 0.0211(19) 0.0303(18) 0.0054(13) 0.0008(13) 0.0006(12) C9 0.0130(16) 0.0245(17) 0.0257(17) 0.0030(14) 0.0033(13) 0.0017(13) C10 0.0078(14) 0.0283(19) 0.0314(19) 0.0058(15) 0.0040(13) -0.0008(13) F10 0.0088(9) 0.0407(13) 0.0347(12) 0.0006(9) 0.0054(8) -0.0027(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 S1 C9 1.746(3) . ? S1 C2 1.758(3) . ? C2 C3 1.394(5) . ? C2 C7 1.403(5) . ? C3 C4 1.394(5) . ? C4 C5 1.388(5) . ? C5 C6 1.383(5) . ? C6 C7 1.405(5) . ? C7 C8 1.456(5) . ? C8 C10 1.380(5) 3_655 ? C8 C9 1.420(4) . ? C9 C10 1.376(5) . ? C10 F10 1.364(4) . ? C10 C8 1.380(5) 3_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 S1 C2 90.72(16) . . ? C3 C2 C7 121.8(3) . . ? C3 C2 S1 124.8(3) . . ? C7 C2 S1 113.4(3) . . ? C2 C3 C4 118.1(3) . . ? C5 C4 C3 120.7(3) . . ? C6 C5 C4 121.1(3) . . ? C5 C6 C7 119.4(3) . . ? C2 C7 C6 118.8(3) . . ? C2 C7 C8 111.3(3) . . ? C6 C7 C8 129.9(3) . . ? C10 C8 C9 117.3(3) 3_655 . ? C10 C8 C7 130.8(3) 3_655 . ? C9 C8 C7 111.9(3) . . ? C10 C9 C8 120.6(3) . . ? C10 C9 S1 126.7(3) . . ? C8 C9 S1 112.7(2) . . ? F10 C10 C9 118.0(3) . . ? F10 C10 C8 119.9(3) . 3_655 ? C9 C10 C8 122.1(3) . 3_655 ? 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 C9 S1 C2 C3 -178.9(3) . . . . ? C9 S1 C2 C7 0.7(3) . . . . ? C7 C2 C3 C4 0.5(5) . . . . ? S1 C2 C3 C4 -179.9(3) . . . . ? C2 C3 C4 C5 0.7(5) . . . . ? C3 C4 C5 C6 -1.4(6) . . . . ? C4 C5 C6 C7 0.8(5) . . . . ? C3 C2 C7 C6 -1.0(5) . . . . ? S1 C2 C7 C6 179.3(3) . . . . ? C3 C2 C7 C8 178.9(3) . . . . ? S1 C2 C7 C8 -0.8(4) . . . . ? C5 C6 C7 C2 0.3(5) . . . . ? C5 C6 C7 C8 -179.5(3) . . . . ? C2 C7 C8 C10 -179.2(3) . . . 3_655 ? C6 C7 C8 C10 0.7(6) . . . 3_655 ? C2 C7 C8 C9 0.4(4) . . . . ? C6 C7 C8 C9 -179.8(3) . . . . ? C10 C8 C9 C10 -0.3(6) 3_655 . . . ? C7 C8 C9 C10 -179.9(3) . . . . ? C10 C8 C9 S1 179.8(3) 3_655 . . . ? C7 C8 C9 S1 0.2(4) . . . . ? C2 S1 C9 C10 179.6(3) . . . . ? C2 S1 C9 C8 -0.5(3) . . . . ? C8 C9 C10 F10 179.4(3) . . . . ? S1 C9 C10 F10 -0.7(5) . . . . ? C8 C9 C10 C8 0.3(6) . . . 3_655 ? S1 C9 C10 C8 -179.8(3) . . . 3_655 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.501 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.087 #===END