# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Wade, Casey' 'Zhao, Haiyan' 'Gabbai, F.' _publ_contact_author_name 'Gabbai, F.' _publ_contact_author_email francois@tamu.edu _publ_section_title ; Stabilization of zwitterionic aryltrifluoroborates against hydrolysis ; # Attachment '- N-BF3 cif.cif' data_xl _database_code_depnum_ccdc_archive 'CCDC 782715' #TrackingRef '- N-BF3 cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H13 B F3 N' _chemical_formula_weight 203.02 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' B B 0.0013 0.0007 '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' _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 7.0647(2) _cell_length_b 13.0809(3) _cell_length_c 10.1994(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.3490(10) _cell_angle_gamma 90.00 _cell_volume 938.45(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3520 _cell_measurement_theta_min 5.077 _cell_measurement_theta_max 54.313 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9940 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 32.21 _reflns_number_total 3254 _reflns_number_gt 2466 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX _computing_cell_refinement APEX _computing_data_reduction APEX _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0563P)^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 3254 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 F1 F 0.39345(8) 0.13888(4) 0.84042(5) 0.02031(14) Uani 1 1 d . . . F2 F 0.17848(9) 0.01490(4) 0.78598(6) 0.02530(15) Uani 1 1 d . . . F3 F 0.39909(8) 0.05591(5) 0.64522(5) 0.02247(14) Uani 1 1 d . . . N1 N 0.28224(11) 0.34923(6) 0.68337(7) 0.01230(15) Uani 1 1 d . . . C1 C 0.12947(12) 0.27915(6) 0.61936(8) 0.01185(16) Uani 1 1 d . . . C2 C 0.12521(12) 0.17439(7) 0.65199(8) 0.01267(16) Uani 1 1 d . . . C3 C -0.03094(13) 0.12105(7) 0.59017(9) 0.01663(18) Uani 1 1 d . . . H3A H -0.0422 0.0521 0.6100 0.020 Uiso 1 1 calc R . . C4 C -0.16963(13) 0.16381(8) 0.50164(9) 0.01852(19) Uani 1 1 d . . . H4A H -0.2702 0.1244 0.4644 0.022 Uiso 1 1 calc R . . C5 C -0.15582(13) 0.26564(7) 0.46984(9) 0.01901(19) Uani 1 1 d . . . H5A H -0.2453 0.2955 0.4089 0.023 Uiso 1 1 calc R . . C6 C -0.00700(13) 0.32337(7) 0.52957(9) 0.01626(18) Uani 1 1 d . . . H6A H 0.0016 0.3924 0.5094 0.020 Uiso 1 1 calc R . . C7 C 0.26236(14) 0.35514(7) 0.82904(8) 0.01644(18) Uani 1 1 d . . . H7A H 0.3588 0.3994 0.8701 0.025 Uiso 1 1 calc R . . H7B H 0.2765 0.2881 0.8669 0.025 Uiso 1 1 calc R . . H7C H 0.1391 0.3817 0.8430 0.025 Uiso 1 1 calc R . . C8 C 0.47741(12) 0.31295(7) 0.65683(8) 0.01589(18) Uani 1 1 d . . . H8A H 0.5715 0.3584 0.6982 0.024 Uiso 1 1 calc R . . H8B H 0.4871 0.3120 0.5636 0.024 Uiso 1 1 calc R . . H8C H 0.4980 0.2453 0.6918 0.024 Uiso 1 1 calc R . . C9 C 0.26671(14) 0.45772(7) 0.63376(9) 0.01689(18) Uani 1 1 d . . . H9A H 0.3668 0.4981 0.6778 0.025 Uiso 1 1 calc R . . H9B H 0.1459 0.4856 0.6513 0.025 Uiso 1 1 calc R . . H9C H 0.2775 0.4586 0.5406 0.025 Uiso 1 1 calc R . . B1 B 0.27676(15) 0.09666(8) 0.73373(10) 0.0158(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 F1 0.0257(3) 0.0179(3) 0.0159(2) 0.0001(2) -0.0062(2) 0.0037(2) F2 0.0276(3) 0.0176(3) 0.0302(3) 0.0105(2) -0.0002(2) -0.0019(2) F3 0.0243(3) 0.0243(3) 0.0188(3) -0.0018(2) 0.0014(2) 0.0099(2) N1 0.0124(3) 0.0124(3) 0.0119(3) 0.0000(3) -0.0003(2) -0.0007(3) C1 0.0105(4) 0.0129(4) 0.0121(3) -0.0014(3) 0.0006(3) -0.0006(3) C2 0.0131(4) 0.0130(4) 0.0121(3) -0.0004(3) 0.0021(3) -0.0001(3) C3 0.0180(4) 0.0146(4) 0.0174(4) -0.0003(3) 0.0019(3) -0.0032(4) C4 0.0135(4) 0.0211(4) 0.0206(4) -0.0034(3) -0.0006(3) -0.0039(4) C5 0.0132(4) 0.0220(5) 0.0209(4) -0.0009(4) -0.0037(3) 0.0023(4) C6 0.0152(4) 0.0137(4) 0.0191(4) 0.0003(3) -0.0020(3) 0.0020(3) C7 0.0220(5) 0.0158(4) 0.0116(3) -0.0016(3) 0.0020(3) 0.0000(4) C8 0.0112(4) 0.0198(4) 0.0166(4) -0.0003(3) 0.0007(3) 0.0002(3) C9 0.0197(5) 0.0113(4) 0.0192(4) 0.0022(3) -0.0011(3) -0.0027(4) B1 0.0191(5) 0.0131(4) 0.0149(4) 0.0008(3) 0.0000(3) 0.0013(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 F1 B1 1.4148(11) . ? F2 B1 1.4067(12) . ? F3 B1 1.4112(12) . ? N1 C8 1.5064(12) . ? N1 C9 1.5072(11) . ? N1 C7 1.5074(10) . ? N1 C1 1.5166(11) . ? C1 C6 1.3921(12) . ? C1 C2 1.4111(12) . ? C2 C3 1.4041(12) . ? C2 B1 1.6458(13) . ? C3 C4 1.3868(13) . ? C3 H3A 0.9300 . ? C4 C5 1.3766(14) . ? C4 H4A 0.9300 . ? C5 C6 1.3883(13) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? 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 C8 N1 C9 105.99(7) . . ? C8 N1 C7 111.36(7) . . ? C9 N1 C7 105.78(7) . . ? C8 N1 C1 111.03(6) . . ? C9 N1 C1 113.46(7) . . ? C7 N1 C1 109.11(7) . . ? C6 C1 C2 122.00(8) . . ? C6 C1 N1 116.96(7) . . ? C2 C1 N1 121.03(7) . . ? C3 C2 C1 114.19(8) . . ? C3 C2 B1 111.55(8) . . ? C1 C2 B1 133.80(8) . . ? C4 C3 C2 124.74(8) . . ? C4 C3 H3A 117.6 . . ? C2 C3 H3A 117.6 . . ? C5 C4 C3 118.84(8) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 C6 119.36(8) . . ? C4 C5 H5A 120.3 . . ? C6 C5 H5A 120.3 . . ? C5 C6 C1 120.82(9) . . ? C5 C6 H6A 119.6 . . ? C1 C6 H6A 119.6 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? F2 B1 F3 107.97(8) . . ? F2 B1 F1 106.15(7) . . ? F3 B1 F1 106.97(8) . . ? F2 B1 C2 109.93(8) . . ? F3 B1 C2 108.52(7) . . ? F1 B1 C2 116.96(7) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 32.21 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.380 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.048 # Attachment '- P-BF3 cif.cif' data_sad _database_code_depnum_ccdc_archive 'CCDC 782716' #TrackingRef '- P-BF3 cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 B F3 P' _chemical_formula_weight 344.11 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' B B 0.0013 0.0007 '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' P P 0.1023 0.0942 '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 11.6184(6) _cell_length_b 12.0740(6) _cell_length_c 12.6108(7) _cell_angle_alpha 108.737(3) _cell_angle_beta 94.921(4) _cell_angle_gamma 90.944(3) _cell_volume 1667.30(15) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5515 _cell_measurement_theta_min 4.675 _cell_measurement_theta_max 47.325 _exptl_crystal_description block _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.624754 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27166 _diffrn_reflns_av_R_equivalents 0.0758 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5847 _reflns_number_gt 4340 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker APEX' _computing_data_reduction 'Bruker APEX' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0300P)^2^+8.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5847 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0981 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.2021 _refine_ls_wR_factor_gt 0.1870 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 P1 P 1.20505(11) 0.98143(10) 0.21386(11) 0.0334(3) Uani 1 1 d . . . P2 P 0.69773(11) 0.32062(10) 0.22952(11) 0.0343(3) Uani 1 1 d . . . F1 F 1.4440(2) 1.0565(2) 0.1827(3) 0.0452(8) Uani 1 1 d . . . F2 F 1.5675(3) 0.9767(3) 0.2830(3) 0.0502(8) Uani 1 1 d . . . F3 F 1.5681(3) 0.9195(3) 0.0937(3) 0.0512(8) Uani 1 1 d . . . F4 F 0.9541(3) 0.2527(3) 0.2392(3) 0.0559(9) Uani 1 1 d . . . F5 F 0.9368(3) 0.2041(2) 0.0504(3) 0.0509(8) Uani 1 1 d . . . F6 F 1.0853(3) 0.3237(3) 0.1513(3) 0.0626(10) Uani 1 1 d . . . C1 C 1.2827(4) 0.8473(4) 0.1772(4) 0.0316(10) Uani 1 1 d . . . C2 C 1.4025(4) 0.8456(4) 0.1677(4) 0.0364(11) Uani 1 1 d . . . C3 C 1.4493(4) 0.7328(4) 0.1379(5) 0.0413(12) Uani 1 1 d . . . H3A H 1.5284 0.7271 0.1321 0.050 Uiso 1 1 calc R . . C4 C 1.3818(4) 0.6316(4) 0.1171(5) 0.0410(12) Uani 1 1 d . . . H4A H 1.4162 0.5597 0.0990 0.049 Uiso 1 1 calc R . . C5 C 1.2654(4) 0.6359(4) 0.1230(5) 0.0399(12) Uani 1 1 d . . . H5A H 1.2202 0.5671 0.1068 0.048 Uiso 1 1 calc R . . C6 C 1.2147(4) 0.7434(4) 0.1534(4) 0.0347(11) Uani 1 1 d . . . H6A H 1.1353 0.7467 0.1580 0.042 Uiso 1 1 calc R . . C7 C 1.1943(4) 1.0446(4) 0.1032(4) 0.0379(12) Uani 1 1 d . . . H7A H 1.1528 1.1152 0.1261 0.057 Uiso 1 1 calc R . . H7B H 1.1538 0.9901 0.0370 0.057 Uiso 1 1 calc R . . H7C H 1.2704 1.0623 0.0872 0.057 Uiso 1 1 calc R . . C8 C 1.2679(4) 1.0849(4) 0.3419(4) 0.0350(11) Uani 1 1 d . . . C9 C 1.3463(4) 1.0525(5) 0.4147(5) 0.0415(12) Uani 1 1 d . . . H9A H 1.3707 0.9762 0.3947 0.050 Uiso 1 1 calc R . . C10 C 1.3881(5) 1.1325(5) 0.5163(5) 0.0448(13) Uani 1 1 d . . . H10A H 1.4399 1.1098 0.5650 0.054 Uiso 1 1 calc R . . C11 C 1.3536(6) 1.2453(5) 0.5459(5) 0.0558(15) Uani 1 1 d . . . H11A H 1.3834 1.2998 0.6138 0.067 Uiso 1 1 calc R . . C12 C 1.2744(6) 1.2782(5) 0.4747(5) 0.0630(18) Uani 1 1 d . . . H12A H 1.2501 1.3546 0.4957 0.076 Uiso 1 1 calc R . . C13 C 1.2315(5) 1.1998(5) 0.3739(5) 0.0522(15) Uani 1 1 d . . . H13A H 1.1781 1.2227 0.3266 0.063 Uiso 1 1 calc R . . C14 C 1.0609(4) 0.9495(4) 0.2418(4) 0.0356(11) Uani 1 1 d . . . C15 C 1.0443(5) 0.9251(4) 0.3409(5) 0.0432(13) Uani 1 1 d . . . H15A H 1.1080 0.9240 0.3904 0.052 Uiso 1 1 calc R . . C16 C 0.9352(5) 0.9027(5) 0.3663(5) 0.0468(13) Uani 1 1 d . . . H16A H 0.9258 0.8840 0.4311 0.056 Uiso 1 1 calc R . . C17 C 0.8395(5) 0.9080(4) 0.2950(5) 0.0460(13) Uani 1 1 d . . . H17A H 0.7655 0.8957 0.3131 0.055 Uiso 1 1 calc R . . C18 C 0.8548(5) 0.9317(4) 0.1970(5) 0.0449(13) Uani 1 1 d . . . H18A H 0.7908 0.9338 0.1483 0.054 Uiso 1 1 calc R . . C19 C 0.9643(4) 0.9523(4) 0.1705(5) 0.0397(12) Uani 1 1 d . . . H19A H 0.9732 0.9681 0.1041 0.048 Uiso 1 1 calc R . . C20 C 0.7777(4) 0.4253(4) 0.1848(4) 0.0336(11) Uani 1 1 d . . . C21 C 0.8916(4) 0.4104(4) 0.1576(4) 0.0356(11) Uani 1 1 d . . . C22 C 0.9438(4) 0.5003(4) 0.1282(4) 0.0400(12) Uani 1 1 d . . . H22A H 1.0202 0.4939 0.1111 0.048 Uiso 1 1 calc R . . C23 C 0.8857(5) 0.5990(4) 0.1236(5) 0.0430(13) Uani 1 1 d . . . H23A H 0.9233 0.6567 0.1034 0.052 Uiso 1 1 calc R . . C24 C 0.7730(4) 0.6109(4) 0.1489(5) 0.0422(13) Uani 1 1 d . . . H24A H 0.7338 0.6764 0.1454 0.051 Uiso 1 1 calc R . . C25 C 0.7181(4) 0.5248(4) 0.1797(4) 0.0372(11) Uani 1 1 d . . . H25A H 0.6418 0.5325 0.1970 0.045 Uiso 1 1 calc R . . C26 C 0.6987(5) 0.1757(4) 0.1333(5) 0.0430(13) Uani 1 1 d . . . H26A H 0.6557 0.1232 0.1602 0.065 Uiso 1 1 calc R . . H26B H 0.7770 0.1521 0.1271 0.065 Uiso 1 1 calc R . . H26C H 0.6638 0.1738 0.0609 0.065 Uiso 1 1 calc R . . C27 C 0.7537(4) 0.3242(4) 0.3675(4) 0.0372(12) Uani 1 1 d . . . C28 C 0.7111(5) 0.2400(5) 0.4114(5) 0.0518(15) Uani 1 1 d . . . H28A H 0.6560 0.1825 0.3691 0.062 Uiso 1 1 calc R . . C29 C 0.7530(6) 0.2445(5) 0.5185(5) 0.0572(16) Uani 1 1 d . . . H29A H 0.7256 0.1894 0.5487 0.069 Uiso 1 1 calc R . . C30 C 0.8341(5) 0.3287(5) 0.5810(5) 0.0532(15) Uani 1 1 d . . . H30A H 0.8620 0.3292 0.6526 0.064 Uiso 1 1 calc R . . C31 C 0.8747(5) 0.4121(5) 0.5399(5) 0.0449(13) Uani 1 1 d . . . H31A H 0.9290 0.4697 0.5834 0.054 Uiso 1 1 calc R . . C32 C 0.8341(4) 0.4100(5) 0.4325(5) 0.0416(12) Uani 1 1 d . . . H32A H 0.8611 0.4667 0.4041 0.050 Uiso 1 1 calc R . . C33 C 0.5492(4) 0.3606(4) 0.2391(4) 0.0349(11) Uani 1 1 d . . . C34 C 0.4653(4) 0.3073(4) 0.1522(4) 0.0365(11) Uani 1 1 d . . . H34A H 0.4849 0.2500 0.0880 0.044 Uiso 1 1 calc R . . C35 C 0.3519(4) 0.3394(4) 0.1611(5) 0.0384(12) Uani 1 1 d . . . H35A H 0.2950 0.3030 0.1033 0.046 Uiso 1 1 calc R . . C36 C 0.3235(4) 0.4261(4) 0.2564(5) 0.0411(12) Uani 1 1 d . . . H36A H 0.2473 0.4480 0.2621 0.049 Uiso 1 1 calc R . . C37 C 0.4063(5) 0.4794(5) 0.3418(5) 0.0440(13) Uani 1 1 d . . . H37A H 0.3864 0.5381 0.4051 0.053 Uiso 1 1 calc R . . C38 C 0.5197(4) 0.4469(4) 0.3351(5) 0.0399(12) Uani 1 1 d . . . H38A H 0.5757 0.4823 0.3942 0.048 Uiso 1 1 calc R . . B1 B 1.4971(5) 0.9510(5) 0.1827(5) 0.0375(13) Uani 1 1 d . . . B2 B 0.9698(5) 0.2954(5) 0.1514(5) 0.0384(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0360(7) 0.0211(6) 0.0434(8) 0.0114(5) -0.0002(6) 0.0060(5) P2 0.0345(7) 0.0223(6) 0.0462(8) 0.0111(5) 0.0036(6) 0.0049(5) F1 0.0450(17) 0.0268(14) 0.068(2) 0.0217(14) 0.0017(15) 0.0036(12) F2 0.0479(18) 0.0406(17) 0.060(2) 0.0184(15) -0.0108(15) -0.0037(14) F3 0.0509(19) 0.0341(16) 0.066(2) 0.0104(15) 0.0156(16) 0.0009(14) F4 0.063(2) 0.0448(18) 0.065(2) 0.0228(16) 0.0087(17) 0.0237(16) F5 0.0536(19) 0.0321(16) 0.058(2) 0.0031(14) 0.0008(15) 0.0136(14) F6 0.0353(17) 0.0408(18) 0.108(3) 0.0193(18) 0.0042(18) 0.0081(14) C1 0.035(3) 0.022(2) 0.037(3) 0.010(2) 0.002(2) 0.0061(19) C2 0.041(3) 0.026(2) 0.045(3) 0.015(2) -0.003(2) 0.005(2) C3 0.034(3) 0.030(3) 0.062(4) 0.018(2) 0.007(2) 0.009(2) C4 0.043(3) 0.023(2) 0.059(3) 0.015(2) 0.004(2) 0.011(2) C5 0.043(3) 0.020(2) 0.056(3) 0.011(2) 0.005(2) 0.004(2) C6 0.035(3) 0.029(2) 0.043(3) 0.014(2) 0.002(2) 0.005(2) C7 0.041(3) 0.028(2) 0.045(3) 0.013(2) 0.002(2) 0.007(2) C8 0.036(3) 0.027(2) 0.044(3) 0.014(2) 0.002(2) 0.006(2) C9 0.042(3) 0.034(3) 0.049(3) 0.016(2) -0.001(2) 0.004(2) C10 0.045(3) 0.040(3) 0.047(3) 0.013(3) -0.003(2) 0.007(2) C11 0.069(4) 0.041(3) 0.049(4) 0.007(3) -0.005(3) -0.001(3) C12 0.096(5) 0.029(3) 0.052(4) 0.001(3) -0.011(3) 0.014(3) C13 0.069(4) 0.033(3) 0.053(4) 0.014(3) -0.007(3) 0.011(3) C14 0.040(3) 0.021(2) 0.046(3) 0.011(2) 0.004(2) 0.009(2) C15 0.044(3) 0.037(3) 0.048(3) 0.013(2) 0.001(2) 0.005(2) C16 0.053(3) 0.039(3) 0.048(3) 0.013(3) 0.009(3) 0.001(2) C17 0.042(3) 0.030(3) 0.061(4) 0.006(3) 0.012(3) 0.002(2) C18 0.040(3) 0.028(3) 0.069(4) 0.020(3) -0.003(3) 0.006(2) C19 0.042(3) 0.027(2) 0.049(3) 0.011(2) 0.001(2) 0.008(2) C20 0.034(3) 0.024(2) 0.039(3) 0.006(2) 0.000(2) 0.0005(19) C21 0.037(3) 0.026(2) 0.041(3) 0.008(2) 0.000(2) -0.001(2) C22 0.037(3) 0.032(3) 0.049(3) 0.010(2) 0.002(2) 0.004(2) C23 0.044(3) 0.028(3) 0.057(3) 0.014(2) 0.006(3) 0.000(2) C24 0.044(3) 0.023(2) 0.060(4) 0.013(2) 0.006(3) 0.007(2) C25 0.037(3) 0.025(2) 0.048(3) 0.008(2) 0.006(2) 0.004(2) C26 0.045(3) 0.025(2) 0.056(3) 0.007(2) 0.007(3) 0.003(2) C27 0.035(3) 0.026(2) 0.051(3) 0.014(2) 0.005(2) 0.012(2) C28 0.054(3) 0.036(3) 0.068(4) 0.020(3) 0.007(3) 0.003(3) C29 0.069(4) 0.050(3) 0.062(4) 0.032(3) 0.005(3) 0.013(3) C30 0.052(3) 0.061(4) 0.052(4) 0.026(3) 0.003(3) 0.016(3) C31 0.037(3) 0.050(3) 0.046(3) 0.013(3) 0.004(2) 0.010(2) C32 0.039(3) 0.037(3) 0.050(3) 0.015(2) 0.005(2) 0.008(2) C33 0.036(3) 0.024(2) 0.046(3) 0.012(2) 0.008(2) 0.004(2) C34 0.043(3) 0.024(2) 0.044(3) 0.012(2) 0.007(2) 0.005(2) C35 0.038(3) 0.029(2) 0.050(3) 0.016(2) -0.003(2) 0.000(2) C36 0.036(3) 0.035(3) 0.054(3) 0.016(2) 0.005(2) 0.006(2) C37 0.043(3) 0.037(3) 0.050(3) 0.011(2) 0.010(3) 0.010(2) C38 0.040(3) 0.031(3) 0.046(3) 0.010(2) 0.000(2) 0.004(2) B1 0.035(3) 0.028(3) 0.049(4) 0.014(3) -0.002(3) 0.003(2) B2 0.034(3) 0.030(3) 0.049(4) 0.011(3) 0.001(3) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C8 1.781(5) . ? P1 C7 1.789(5) . ? P1 C14 1.801(5) . ? P1 C1 1.813(5) . ? P2 C26 1.781(5) . ? P2 C27 1.791(5) . ? P2 C33 1.803(5) . ? P2 C20 1.813(5) . ? F1 B1 1.425(6) . ? F2 B1 1.389(7) . ? F3 B1 1.406(7) . ? F4 B2 1.387(7) . ? F5 B2 1.409(7) . ? F6 B2 1.379(6) . ? C1 C6 1.405(6) . ? C1 C2 1.407(7) . ? C2 C3 1.422(7) . ? C2 B1 1.621(7) . ? C3 C4 1.381(7) . ? C3 H3A 0.9300 . ? C4 C5 1.361(7) . ? C4 H4A 0.9300 . ? C5 C6 1.387(6) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.387(7) . ? C8 C13 1.398(7) . ? C9 C10 1.376(7) . ? C9 H9A 0.9300 . ? C10 C11 1.368(8) . ? C10 H10A 0.9300 . ? C11 C12 1.382(8) . ? C11 H11A 0.9300 . ? C12 C13 1.366(8) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C19 1.385(7) . ? C14 C15 1.401(7) . ? C15 C16 1.376(8) . ? C15 H15A 0.9300 . ? C16 C17 1.384(8) . ? C16 H16A 0.9300 . ? C17 C18 1.380(8) . ? C17 H17A 0.9300 . ? C18 C19 1.381(7) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C21 1.396(7) . ? C20 C25 1.413(7) . ? C21 C22 1.399(7) . ? C21 B2 1.656(7) . ? C22 C23 1.393(7) . ? C22 H22A 0.9300 . ? C23 C24 1.373(7) . ? C23 H23A 0.9300 . ? C24 C25 1.385(7) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C32 1.382(7) . ? C27 C28 1.406(7) . ? C28 C29 1.380(8) . ? C28 H28A 0.9300 . ? C29 C30 1.367(8) . ? C29 H29A 0.9300 . ? C30 C31 1.367(8) . ? C30 H30A 0.9300 . ? C31 C32 1.387(8) . ? C31 H31A 0.9300 . ? C32 H32A 0.9300 . ? C33 C34 1.382(7) . ? C33 C38 1.394(7) . ? C34 C35 1.382(7) . ? C34 H34A 0.9300 . ? C35 C36 1.385(7) . ? C35 H35A 0.9300 . ? C36 C37 1.363(7) . ? C36 H36A 0.9300 . ? C37 C38 1.383(7) . ? C37 H37A 0.9300 . ? C38 H38A 0.9300 . ? 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 C8 P1 C7 110.8(2) . . ? C8 P1 C14 105.0(2) . . ? C7 P1 C14 108.3(2) . . ? C8 P1 C1 111.4(2) . . ? C7 P1 C1 112.2(2) . . ? C14 P1 C1 108.8(2) . . ? C26 P2 C27 110.2(2) . . ? C26 P2 C33 107.8(2) . . ? C27 P2 C33 106.4(2) . . ? C26 P2 C20 112.2(2) . . ? C27 P2 C20 110.6(2) . . ? C33 P2 C20 109.4(2) . . ? C6 C1 C2 121.5(4) . . ? C6 C1 P1 115.7(4) . . ? C2 C1 P1 122.8(3) . . ? C1 C2 C3 115.4(4) . . ? C1 C2 B1 130.9(4) . . ? C3 C2 B1 113.8(4) . . ? C4 C3 C2 122.5(5) . . ? C4 C3 H3A 118.8 . . ? C2 C3 H3A 118.8 . . ? C5 C4 C3 120.7(4) . . ? C5 C4 H4A 119.6 . . ? C3 C4 H4A 119.6 . . ? C4 C5 C6 119.6(4) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C5 C6 C1 120.3(5) . . ? C5 C6 H6A 119.8 . . ? C1 C6 H6A 119.8 . . ? P1 C7 H7A 109.5 . . ? P1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? P1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 118.9(5) . . ? C9 C8 P1 121.6(4) . . ? C13 C8 P1 119.3(4) . . ? C10 C9 C8 120.5(5) . . ? C10 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? C11 C10 C9 120.2(5) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? C10 C11 C12 119.9(5) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C13 C12 C11 120.7(5) . . ? C13 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? C12 C13 C8 119.8(5) . . ? C12 C13 H13A 120.1 . . ? C8 C13 H13A 120.1 . . ? C19 C14 C15 118.2(5) . . ? C19 C14 P1 122.3(4) . . ? C15 C14 P1 119.5(4) . . ? C16 C15 C14 121.1(5) . . ? C16 C15 H15A 119.4 . . ? C14 C15 H15A 119.4 . . ? C15 C16 C17 119.9(5) . . ? C15 C16 H16A 120.1 . . ? C17 C16 H16A 120.1 . . ? C18 C17 C16 119.5(5) . . ? C18 C17 H17A 120.3 . . ? C16 C17 H17A 120.3 . . ? C17 C18 C19 120.7(5) . . ? C17 C18 H18A 119.6 . . ? C19 C18 H18A 119.6 . . ? C18 C19 C14 120.6(5) . . ? C18 C19 H19A 119.7 . . ? C14 C19 H19A 119.7 . . ? C21 C20 C25 121.2(4) . . ? C21 C20 P2 122.8(4) . . ? C25 C20 P2 116.0(4) . . ? C20 C21 C22 116.5(4) . . ? C20 C21 B2 126.9(4) . . ? C22 C21 B2 116.5(4) . . ? C23 C22 C21 122.5(5) . . ? C23 C22 H22A 118.7 . . ? C21 C22 H22A 118.7 . . ? C24 C23 C22 120.0(5) . . ? C24 C23 H23A 120.0 . . ? C22 C23 H23A 120.0 . . ? C23 C24 C25 119.5(5) . . ? C23 C24 H24A 120.2 . . ? C25 C24 H24A 120.2 . . ? C24 C25 C20 120.2(5) . . ? C24 C25 H25A 119.9 . . ? C20 C25 H25A 119.9 . . ? P2 C26 H26A 109.5 . . ? P2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? P2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C32 C27 C28 119.7(5) . . ? C32 C27 P2 121.5(4) . . ? C28 C27 P2 118.8(4) . . ? C29 C28 C27 118.5(6) . . ? C29 C28 H28A 120.7 . . ? C27 C28 H28A 120.7 . . ? C30 C29 C28 121.0(6) . . ? C30 C29 H29A 119.5 . . ? C28 C29 H29A 119.5 . . ? C29 C30 C31 120.9(6) . . ? C29 C30 H30A 119.5 . . ? C31 C30 H30A 119.5 . . ? C30 C31 C32 119.4(5) . . ? C30 C31 H31A 120.3 . . ? C32 C31 H31A 120.3 . . ? C27 C32 C31 120.4(5) . . ? C27 C32 H32A 119.8 . . ? C31 C32 H32A 119.8 . . ? C34 C33 C38 120.0(5) . . ? C34 C33 P2 120.7(4) . . ? C38 C33 P2 119.3(4) . . ? C33 C34 C35 119.9(5) . . ? C33 C34 H34A 120.1 . . ? C35 C34 H34A 120.1 . . ? C34 C35 C36 119.8(5) . . ? C34 C35 H35A 120.1 . . ? C36 C35 H35A 120.1 . . ? C37 C36 C35 120.5(5) . . ? C37 C36 H36A 119.7 . . ? C35 C36 H36A 119.7 . . ? C36 C37 C38 120.4(5) . . ? C36 C37 H37A 119.8 . . ? C38 C37 H37A 119.8 . . ? C37 C38 C33 119.5(5) . . ? C37 C38 H38A 120.3 . . ? C33 C38 H38A 120.3 . . ? F2 B1 F3 108.1(4) . . ? F2 B1 F1 106.8(4) . . ? F3 B1 F1 107.9(4) . . ? F2 B1 C2 112.0(4) . . ? F3 B1 C2 109.9(4) . . ? F1 B1 C2 112.0(4) . . ? F6 B2 F4 110.2(5) . . ? F6 B2 F5 107.2(5) . . ? F4 B2 F5 107.3(4) . . ? F6 B2 C21 110.2(4) . . ? F4 B2 C21 112.0(4) . . ? F5 B2 C21 109.8(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.780 _refine_diff_density_min -0.611 _refine_diff_density_rms 0.092 # Attachment '- S-BF3 cif.cif' data_h _database_code_depnum_ccdc_archive 'CCDC 782717' #TrackingRef '- S-BF3 cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 B F3 S' _chemical_formula_weight 206.03 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' B B 0.0013 0.0007 '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)/n 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 6.6172(5) _cell_length_b 12.6622(9) _cell_length_c 11.2891(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.9180(10) _cell_angle_gamma 90.00 _cell_volume 921.95(12) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5491 _cell_measurement_theta_min 4.904 _cell_measurement_theta_max 58.936 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9503 _exptl_absorpt_correction_T_max 0.9632 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9052 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.49 _reflns_number_total 1709 _reflns_number_gt 1555 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker APEX' _computing_data_reduction 'Bruker APEX' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+0.6710P] 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 1709 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0632 _refine_ls_wR_factor_gt 0.0619 _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 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 0.21634(6) 0.06436(3) 0.11841(3) 0.01608(11) Uani 1 1 d . . . F1 F 0.41397(14) -0.11975(7) -0.01102(8) 0.0221(2) Uani 1 1 d . . . F2 F 0.17497(13) -0.17209(7) 0.09472(8) 0.0242(2) Uani 1 1 d . . . F3 F 0.48081(15) -0.26223(7) 0.11454(8) 0.0290(2) Uani 1 1 d . . . C1 C 0.4343(2) 0.01759(11) 0.23086(13) 0.0158(3) Uani 1 1 d . . . C2 C 0.4971(2) -0.08613(11) 0.21504(13) 0.0160(3) Uani 1 1 d . . . C3 C 0.6574(2) -0.12419(12) 0.30818(14) 0.0189(3) Uani 1 1 d . . . H3A H 0.7059 -0.1942 0.3025 0.023 Uiso 1 1 calc R . . C4 C 0.7478(2) -0.06340(12) 0.40838(14) 0.0210(3) Uani 1 1 d . . . H4A H 0.8554 -0.0922 0.4700 0.025 Uiso 1 1 calc R . . C5 C 0.6812(2) 0.03928(12) 0.41857(14) 0.0222(3) Uani 1 1 d . . . H5A H 0.7445 0.0812 0.4866 0.027 Uiso 1 1 calc R . . C6 C 0.5224(2) 0.08081(12) 0.32973(14) 0.0204(3) Uani 1 1 d . . . H6A H 0.4747 0.1509 0.3361 0.025 Uiso 1 1 calc R . . C7 C 0.2347(2) 0.20567(11) 0.12082(14) 0.0206(3) Uani 1 1 d . . . H7A H 0.3450 0.2278 0.0810 0.031 Uiso 1 1 calc R . . H7B H 0.2668 0.2304 0.2052 0.031 Uiso 1 1 calc R . . H7C H 0.1025 0.2360 0.0776 0.031 Uiso 1 1 calc R . . C8 C 0.0087(2) 0.04393(13) 0.19477(15) 0.0231(3) Uani 1 1 d . . . H8A H -0.0177 -0.0319 0.1996 0.035 Uiso 1 1 calc R . . H8B H -0.1168 0.0791 0.1494 0.035 Uiso 1 1 calc R . . H8C H 0.0474 0.0735 0.2770 0.035 Uiso 1 1 calc R . . B1 B 0.3915(3) -0.16121(13) 0.10099(16) 0.0189(4) 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 0.01598(19) 0.01582(19) 0.01639(19) 0.00005(13) 0.00348(14) 0.00169(14) F1 0.0253(5) 0.0233(5) 0.0190(5) 0.0002(4) 0.0076(4) 0.0021(4) F2 0.0208(5) 0.0271(5) 0.0245(5) -0.0030(4) 0.0045(4) -0.0074(4) F3 0.0387(6) 0.0150(5) 0.0288(5) -0.0022(4) -0.0017(4) 0.0055(4) C1 0.0133(7) 0.0187(7) 0.0156(7) 0.0036(6) 0.0038(6) 0.0002(6) C2 0.0150(7) 0.0156(7) 0.0188(7) 0.0033(6) 0.0072(6) -0.0018(6) C3 0.0171(7) 0.0163(7) 0.0241(8) 0.0035(6) 0.0061(6) -0.0001(6) C4 0.0156(7) 0.0253(8) 0.0212(8) 0.0053(6) 0.0024(6) -0.0010(6) C5 0.0215(8) 0.0246(8) 0.0193(8) -0.0028(6) 0.0020(6) -0.0036(6) C6 0.0216(8) 0.0180(7) 0.0217(8) -0.0013(6) 0.0047(6) 0.0002(6) C7 0.0237(8) 0.0145(7) 0.0237(8) 0.0012(6) 0.0059(6) 0.0038(6) C8 0.0177(8) 0.0280(8) 0.0251(8) 0.0010(7) 0.0077(6) -0.0003(6) B1 0.0207(9) 0.0161(8) 0.0197(9) 0.0009(7) 0.0041(7) 0.0012(7) _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 C7 1.7932(15) . ? S1 C1 1.7955(14) . ? S1 C8 1.7963(15) . ? F1 B1 1.4074(19) . ? F2 B1 1.4253(19) . ? F3 B1 1.4030(19) . ? C1 C6 1.391(2) . ? C1 C2 1.401(2) . ? C2 C3 1.401(2) . ? C2 B1 1.627(2) . ? C3 C4 1.388(2) . ? C3 H3A 0.9500 . ? C4 C5 1.386(2) . ? C4 H4A 0.9500 . ? C5 C6 1.384(2) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C7 S1 C1 106.10(7) . . ? C7 S1 C8 101.12(7) . . ? C1 S1 C8 101.12(7) . . ? C6 C1 C2 123.95(14) . . ? C6 C1 S1 120.26(11) . . ? C2 C1 S1 115.69(11) . . ? C1 C2 C3 115.03(13) . . ? C1 C2 B1 124.15(13) . . ? C3 C2 B1 120.79(13) . . ? C4 C3 C2 122.47(14) . . ? C4 C3 H3A 118.8 . . ? C2 C3 H3A 118.8 . . ? C5 C4 C3 120.03(14) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C6 C5 C4 120.03(14) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C5 C6 C1 118.49(14) . . ? C5 C6 H6A 120.8 . . ? C1 C6 H6A 120.8 . . ? S1 C7 H7A 109.5 . . ? S1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? S1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? S1 C8 H8A 109.5 . . ? S1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? F3 B1 F1 108.15(13) . . ? F3 B1 F2 108.16(13) . . ? F1 B1 F2 107.36(12) . . ? F3 B1 C2 110.52(13) . . ? F1 B1 C2 112.33(12) . . ? F2 B1 C2 110.18(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.356 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.043