Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jean-Marc Denis' 'Henrietta Forintos' 'Annie-Claude Gaumont' 'Pierre-Jean Madec' 'Helga Szelke' 'Pham Thi-Nhan' 'Loic Toupet' _publ_contact_author_name 'Dr Jean-Marc Denis' _publ_contact_author_address ; Institut de Chimie Université de Rennes 1 Campus de Beaulieu RENNES Cedex 35042 FRANCE ; _publ_contact_author_email JEAN-MARC.DENIS@UNIV-RENNES1.FR _publ_requested_journal 'Chemical Communications' _publ_section_title ; B(C6F5)3-Catalysed Formation Of B-P Bonds by Dehydro-Coupling of Phosphine-Boranes; Access to Inorganic Material ; data_jmd2110 _database_code_CSD 196369 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H10 B2 F15 P S' _chemical_formula_weight 619.93 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6926(4) _cell_length_b 10.6562(5) _cell_length_c 12.3789(7) _cell_angle_alpha 64.353(2) _cell_angle_beta 86.081(2) _cell_angle_gamma 84.137(3) _cell_volume 1146.16(10) _cell_formula_units_Z 2 _cell_measurement_temperature 110(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5270 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0654 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.61 _reflns_number_total 5270 _reflns_number_gt 3970 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0572P)^2^+0.6570P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5270 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.84408(6) 0.20509(7) 0.93170(6) 0.02780(17) Uani 1 1 d . . . P1 P 0.65299(6) 0.28528(7) 0.71184(6) 0.02479(17) Uani 1 1 d . . . H1 H 0.575(3) 0.400(3) 0.673(3) 0.034 Uiso 1 1 d . . . H2 H 0.778(3) 0.326(3) 0.667(3) 0.034 Uiso 1 1 d . . . F1 F 0.37760(15) 0.18123(16) 0.79716(13) 0.0310(3) Uani 1 1 d . . . F2 F 0.10619(15) 0.25163(17) 0.75715(15) 0.0365(4) Uani 1 1 d . . . F3 F 0.00890(15) 0.34255(18) 0.53208(17) 0.0412(4) Uani 1 1 d . . . F4 F 0.18867(16) 0.35473(18) 0.34879(14) 0.0384(4) Uani 1 1 d . . . F5 F 0.45540(15) 0.27845(17) 0.38649(13) 0.0317(4) Uani 1 1 d . . . F6 F 0.64563(16) 0.44315(15) 0.44224(13) 0.0311(3) Uani 1 1 d . . . F7 F 0.8154(2) 0.50263(17) 0.24893(15) 0.0435(4) Uani 1 1 d . . . F8 F 0.96707(17) 0.29437(18) 0.21182(14) 0.0394(4) Uani 1 1 d . . . F9 F 0.94014(16) 0.02269(17) 0.37101(14) 0.0349(4) Uani 1 1 d . . . F10 F 0.77218(16) -0.03982(15) 0.56058(13) 0.0305(3) Uani 1 1 d . . . F11 F 0.39908(15) -0.05412(15) 0.67954(13) 0.0299(3) Uani 1 1 d . . . F12 F 0.42609(16) -0.31381(15) 0.84865(14) 0.0348(4) Uani 1 1 d . . . F13 F 0.64776(18) -0.40417(16) 0.99607(15) 0.0407(4) Uani 1 1 d . . . F14 F 0.84631(16) -0.22609(17) 0.96437(15) 0.0397(4) Uani 1 1 d . . . F15 F 0.82713(14) 0.03240(16) 0.78732(14) 0.0312(4) Uani 1 1 d . . . C1 C 0.4320(2) 0.2264(2) 0.5941(2) 0.0230(5) Uani 1 1 d . . . C2 C 0.3352(3) 0.2245(3) 0.6834(2) 0.0249(5) Uani 1 1 d . . . C3 C 0.1949(3) 0.2609(3) 0.6656(2) 0.0270(5) Uani 1 1 d . . . C4 C 0.1453(2) 0.3054(3) 0.5524(3) 0.0297(6) Uani 1 1 d . . . C5 C 0.2363(3) 0.3123(3) 0.4604(2) 0.0276(5) Uani 1 1 d . . . C6 C 0.3759(2) 0.2722(3) 0.4826(2) 0.0252(5) Uani 1 1 d . . . C7 C 0.7013(2) 0.1990(3) 0.5143(2) 0.0233(5) Uani 1 1 d . . . C8 C 0.7195(3) 0.3346(3) 0.4291(2) 0.0256(5) Uani 1 1 d . . . C9 C 0.8054(3) 0.3691(3) 0.3280(2) 0.0292(6) Uani 1 1 d . . . C10 C 0.8824(3) 0.2635(3) 0.3098(2) 0.0296(6) Uani 1 1 d . . . C11 C 0.8689(2) 0.1269(3) 0.3898(2) 0.0274(5) Uani 1 1 d . . . C12 C 0.7806(2) 0.0976(2) 0.4890(2) 0.0241(5) Uani 1 1 d . . . C13 C 0.6081(2) 0.0063(2) 0.7294(2) 0.0236(5) Uani 1 1 d . . . C14 C 0.5118(2) -0.0902(3) 0.7489(2) 0.0241(5) Uani 1 1 d . . . C15 C 0.5238(3) -0.2267(3) 0.8355(2) 0.0272(5) Uani 1 1 d . . . C16 C 0.6357(3) -0.2728(3) 0.9090(2) 0.0298(6) Uani 1 1 d . . . C17 C 0.7354(3) -0.1831(3) 0.8928(2) 0.0297(6) Uani 1 1 d . . . C18 C 0.7214(2) -0.0491(3) 0.8035(2) 0.0257(5) Uani 1 1 d . . . C19 C 0.8365(3) 0.1006(3) 1.0906(2) 0.0359(6) Uani 1 1 d . . . H19A H 0.8281 0.0111 1.1057 0.043 Uiso 1 1 calc R . . H19B H 0.7629 0.1322 1.1229 0.043 Uiso 1 1 calc R . . H19C H 0.9148 0.1061 1.1230 0.043 Uiso 1 1 calc R . . C20 C 0.8603(3) 0.3742(3) 0.9234(3) 0.0402(7) Uani 1 1 d . . . H20A H 0.8651 0.4366 0.8460 0.048 Uiso 1 1 calc R . . H20B H 0.9380 0.3727 0.9600 0.048 Uiso 1 1 calc R . . H20C H 0.7861 0.3988 0.9599 0.048 Uiso 1 1 calc R . . B1 B 0.5949(3) 0.1693(3) 0.6294(2) 0.0227(5) Uani 1 1 d . . . B2 B 0.6537(3) 0.2156(3) 0.8873(3) 0.0311(6) Uani 1 1 d . . . H3 H 0.593(3) 0.294(3) 0.912(3) 0.034 Uiso 1 1 d . . . H4 H 0.621(3) 0.106(3) 0.936(3) 0.034 Uiso 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 0.0230(3) 0.0352(3) 0.0255(3) -0.0131(3) -0.0012(2) -0.0029(2) P1 0.0233(3) 0.0276(3) 0.0246(3) -0.0118(3) -0.0014(2) -0.0038(2) F1 0.0264(7) 0.0417(9) 0.0240(7) -0.0133(7) 0.0001(6) -0.0028(6) F2 0.0248(8) 0.0431(9) 0.0404(9) -0.0179(8) 0.0084(7) -0.0046(6) F3 0.0188(7) 0.0466(10) 0.0552(11) -0.0189(9) -0.0088(7) 0.0022(7) F4 0.0329(8) 0.0453(9) 0.0328(9) -0.0115(7) -0.0140(7) -0.0001(7) F5 0.0278(8) 0.0437(9) 0.0242(7) -0.0149(7) -0.0018(6) -0.0023(6) F6 0.0379(8) 0.0238(7) 0.0296(8) -0.0105(6) 0.0023(6) -0.0006(6) F7 0.0630(11) 0.0303(8) 0.0321(9) -0.0079(7) 0.0121(8) -0.0163(8) F8 0.0383(9) 0.0535(10) 0.0297(8) -0.0203(8) 0.0127(7) -0.0158(8) F9 0.0306(8) 0.0417(9) 0.0365(9) -0.0228(7) 0.0026(6) 0.0042(7) F10 0.0360(8) 0.0237(7) 0.0299(8) -0.0109(6) 0.0028(6) 0.0000(6) F11 0.0278(8) 0.0298(8) 0.0321(8) -0.0116(6) -0.0070(6) -0.0062(6) F12 0.0371(9) 0.0266(8) 0.0388(9) -0.0114(7) 0.0047(7) -0.0101(6) F13 0.0472(10) 0.0262(8) 0.0350(9) -0.0020(7) 0.0016(7) 0.0029(7) F14 0.0303(8) 0.0428(9) 0.0346(9) -0.0068(7) -0.0106(7) 0.0079(7) F15 0.0198(7) 0.0349(8) 0.0363(8) -0.0122(7) -0.0042(6) -0.0026(6) C1 0.0214(11) 0.0200(11) 0.0266(12) -0.0086(10) -0.0011(9) -0.0033(9) C2 0.0245(12) 0.0254(12) 0.0236(12) -0.0087(10) -0.0027(9) -0.0037(9) C3 0.0213(11) 0.0268(12) 0.0328(13) -0.0127(11) 0.0051(10) -0.0063(9) C4 0.0176(11) 0.0256(12) 0.0430(15) -0.0115(11) -0.0056(10) -0.0008(9) C5 0.0262(12) 0.0245(12) 0.0289(13) -0.0076(10) -0.0082(10) -0.0017(10) C6 0.0242(12) 0.0260(12) 0.0247(12) -0.0100(10) -0.0021(9) -0.0028(9) C7 0.0192(11) 0.0281(12) 0.0246(12) -0.0130(10) -0.0017(9) -0.0027(9) C8 0.0258(12) 0.0252(12) 0.0276(13) -0.0129(10) -0.0012(10) -0.0017(9) C9 0.0320(13) 0.0289(13) 0.0255(13) -0.0091(11) 0.0003(10) -0.0099(10) C10 0.0269(12) 0.0419(15) 0.0218(12) -0.0144(11) 0.0053(10) -0.0117(11) C11 0.0200(11) 0.0360(14) 0.0319(13) -0.0202(12) -0.0024(10) -0.0003(10) C12 0.0212(11) 0.0253(12) 0.0256(12) -0.0100(10) -0.0022(9) -0.0035(9) C13 0.0221(11) 0.0247(12) 0.0233(12) -0.0099(10) -0.0006(9) -0.0009(9) C14 0.0213(11) 0.0280(12) 0.0237(12) -0.0120(10) -0.0016(9) 0.0004(9) C15 0.0282(12) 0.0248(12) 0.0284(13) -0.0117(10) 0.0053(10) -0.0048(10) C16 0.0353(14) 0.0211(12) 0.0241(12) -0.0029(10) 0.0013(11) 0.0037(10) C17 0.0235(12) 0.0338(14) 0.0270(13) -0.0098(11) -0.0057(10) 0.0061(10) C18 0.0205(11) 0.0296(13) 0.0267(12) -0.0121(10) 0.0008(9) -0.0021(9) C19 0.0319(14) 0.0394(15) 0.0286(14) -0.0062(12) -0.0047(11) -0.0045(12) C20 0.0354(15) 0.0331(15) 0.0456(17) -0.0087(13) -0.0161(13) -0.0029(12) B1 0.0207(12) 0.0239(13) 0.0234(13) -0.0097(11) -0.0023(10) -0.0021(10) B2 0.0246(14) 0.0420(17) 0.0283(15) -0.0157(14) -0.0027(12) -0.0052(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C20 1.783(3) . ? S1 C19 1.793(3) . ? S1 B2 1.940(3) . ? P1 B2 1.968(3) . ? P1 B1 2.049(3) . ? P1 H1 1.29(3) . ? P1 H2 1.34(3) . ? F1 C2 1.358(3) . ? F2 C3 1.350(3) . ? F3 C4 1.350(3) . ? F4 C5 1.353(3) . ? F5 C6 1.353(3) . ? F6 C8 1.362(3) . ? F7 C9 1.342(3) . ? F8 C10 1.352(3) . ? F9 C11 1.345(3) . ? F10 C12 1.351(3) . ? F11 C14 1.355(3) . ? F12 C15 1.347(3) . ? F13 C16 1.347(3) . ? F14 C17 1.352(3) . ? F15 C18 1.359(3) . ? C1 C6 1.380(3) . ? C1 C2 1.395(3) . ? C1 B1 1.650(3) . ? C2 C3 1.381(3) . ? C3 C4 1.374(4) . ? C4 C5 1.373(4) . ? C5 C6 1.386(3) . ? C7 C8 1.392(3) . ? C7 C12 1.396(3) . ? C7 B1 1.634(4) . ? C8 C9 1.384(4) . ? C9 C10 1.378(4) . ? C10 C11 1.375(4) . ? C11 C12 1.384(4) . ? C13 C14 1.391(3) . ? C13 C18 1.390(3) . ? C13 B1 1.638(4) . ? C14 C15 1.382(3) . ? C15 C16 1.374(4) . ? C16 C17 1.372(4) . ? C17 C18 1.377(4) . ? C19 H19A 0.9000 . ? C19 H19B 0.9000 . ? C19 H19C 0.9000 . ? C20 H20A 0.9000 . ? C20 H20B 0.9000 . ? C20 H20C 0.9000 . ? B2 H3 1.12(3) . ? B2 H4 1.13(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 S1 C19 101.67(15) . . ? C20 S1 B2 103.34(14) . . ? C19 S1 B2 102.41(13) . . ? B2 P1 B1 122.69(13) . . ? B2 P1 H1 106.4(14) . . ? B1 P1 H1 107.1(14) . . ? B2 P1 H2 109.0(13) . . ? B1 P1 H2 106.7(13) . . ? H1 P1 H2 103.3(18) . . ? C6 C1 C2 113.8(2) . . ? C6 C1 B1 126.5(2) . . ? C2 C1 B1 119.6(2) . . ? F1 C2 C3 116.1(2) . . ? F1 C2 C1 119.4(2) . . ? C3 C2 C1 124.4(2) . . ? F2 C3 C4 119.8(2) . . ? F2 C3 C2 121.3(2) . . ? C4 C3 C2 119.0(2) . . ? F3 C4 C5 120.5(2) . . ? F3 C4 C3 120.3(2) . . ? C5 C4 C3 119.2(2) . . ? F4 C5 C4 119.8(2) . . ? F4 C5 C6 120.2(2) . . ? C4 C5 C6 120.0(2) . . ? F5 C6 C1 121.3(2) . . ? F5 C6 C5 115.1(2) . . ? C1 C6 C5 123.6(2) . . ? C8 C7 C12 113.1(2) . . ? C8 C7 B1 121.1(2) . . ? C12 C7 B1 125.8(2) . . ? F6 C8 C9 116.2(2) . . ? F6 C8 C7 118.8(2) . . ? C9 C8 C7 124.9(2) . . ? F7 C9 C10 120.0(2) . . ? F7 C9 C8 121.2(2) . . ? C10 C9 C8 118.8(2) . . ? F8 C10 C11 120.5(2) . . ? F8 C10 C9 120.0(2) . . ? C11 C10 C9 119.5(2) . . ? F9 C11 C10 120.1(2) . . ? F9 C11 C12 120.4(2) . . ? C10 C11 C12 119.5(2) . . ? F10 C12 C11 114.9(2) . . ? F10 C12 C7 120.9(2) . . ? C11 C12 C7 124.1(2) . . ? C14 C13 C18 113.4(2) . . ? C14 C13 B1 125.0(2) . . ? C18 C13 B1 121.6(2) . . ? F11 C14 C15 115.5(2) . . ? F11 C14 C13 120.5(2) . . ? C15 C14 C13 124.0(2) . . ? F12 C15 C16 120.0(2) . . ? F12 C15 C14 120.5(2) . . ? C16 C15 C14 119.5(2) . . ? F13 C16 C17 120.3(2) . . ? F13 C16 C15 120.6(2) . . ? C17 C16 C15 119.2(2) . . ? F14 C17 C16 120.2(2) . . ? F14 C17 C18 120.3(2) . . ? C16 C17 C18 119.5(2) . . ? F15 C18 C17 116.8(2) . . ? F15 C18 C13 118.8(2) . . ? C17 C18 C13 124.4(2) . . ? S1 C19 H19A 109.5 . . ? S1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? S1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? S1 C20 H20A 109.5 . . ? S1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? S1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C7 B1 C13 113.0(2) . . ? C7 B1 C1 114.4(2) . . ? C13 B1 C1 111.61(19) . . ? C7 B1 P1 106.30(16) . . ? C13 B1 P1 106.34(16) . . ? C1 B1 P1 104.36(16) . . ? S1 B2 P1 107.43(15) . . ? S1 B2 H3 107.4(16) . . ? P1 B2 H3 108.4(15) . . ? S1 B2 H4 105.5(15) . . ? P1 B2 H4 112.7(16) . . ? H3 B2 H4 115(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 F1 179.9(2) . . . . ? B1 C1 C2 F1 2.8(3) . . . . ? C6 C1 C2 C3 1.6(4) . . . . ? B1 C1 C2 C3 -175.5(2) . . . . ? F1 C2 C3 F2 -0.9(3) . . . . ? C1 C2 C3 F2 177.5(2) . . . . ? F1 C2 C3 C4 -179.9(2) . . . . ? C1 C2 C3 C4 -1.5(4) . . . . ? F2 C3 C4 F3 1.4(4) . . . . ? C2 C3 C4 F3 -179.6(2) . . . . ? F2 C3 C4 C5 -179.0(2) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? F3 C4 C5 F4 -0.9(4) . . . . ? C3 C4 C5 F4 179.4(2) . . . . ? F3 C4 C5 C6 -179.2(2) . . . . ? C3 C4 C5 C6 1.1(4) . . . . ? C2 C1 C6 F5 -179.0(2) . . . . ? B1 C1 C6 F5 -2.2(4) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? B1 C1 C6 C5 176.6(2) . . . . ? F4 C5 C6 F5 -0.5(3) . . . . ? C4 C5 C6 F5 177.8(2) . . . . ? F4 C5 C6 C1 -179.3(2) . . . . ? C4 C5 C6 C1 -1.0(4) . . . . ? C12 C7 C8 F6 178.7(2) . . . . ? B1 C7 C8 F6 -0.8(3) . . . . ? C12 C7 C8 C9 0.6(4) . . . . ? B1 C7 C8 C9 -178.8(2) . . . . ? F6 C8 C9 F7 0.7(4) . . . . ? C7 C8 C9 F7 178.8(2) . . . . ? F6 C8 C9 C10 -179.8(2) . . . . ? C7 C8 C9 C10 -1.7(4) . . . . ? F7 C9 C10 F8 -0.5(4) . . . . ? C8 C9 C10 F8 180.0(2) . . . . ? F7 C9 C10 C11 -178.4(2) . . . . ? C8 C9 C10 C11 2.1(4) . . . . ? F8 C10 C11 F9 0.0(4) . . . . ? C9 C10 C11 F9 177.9(2) . . . . ? F8 C10 C11 C12 -179.4(2) . . . . ? C9 C10 C11 C12 -1.5(4) . . . . ? F9 C11 C12 F10 -0.9(3) . . . . ? C10 C11 C12 F10 178.5(2) . . . . ? F9 C11 C12 C7 -178.9(2) . . . . ? C10 C11 C12 C7 0.5(4) . . . . ? C8 C7 C12 F10 -177.9(2) . . . . ? B1 C7 C12 F10 1.5(4) . . . . ? C8 C7 C12 C11 0.0(4) . . . . ? B1 C7 C12 C11 179.4(2) . . . . ? C18 C13 C14 F11 -176.6(2) . . . . ? B1 C13 C14 F11 2.7(4) . . . . ? C18 C13 C14 C15 2.0(4) . . . . ? B1 C13 C14 C15 -178.7(2) . . . . ? F11 C14 C15 F12 -1.3(3) . . . . ? C13 C14 C15 F12 -179.9(2) . . . . ? F11 C14 C15 C16 179.3(2) . . . . ? C13 C14 C15 C16 0.6(4) . . . . ? F12 C15 C16 F13 -1.2(4) . . . . ? C14 C15 C16 F13 178.3(2) . . . . ? F12 C15 C16 C17 178.9(2) . . . . ? C14 C15 C16 C17 -1.7(4) . . . . ? F13 C16 C17 F14 -0.1(4) . . . . ? C15 C16 C17 F14 179.8(2) . . . . ? F13 C16 C17 C18 -179.9(2) . . . . ? C15 C16 C17 C18 0.0(4) . . . . ? F14 C17 C18 F15 3.8(4) . . . . ? C16 C17 C18 F15 -176.4(2) . . . . ? F14 C17 C18 C13 -176.9(2) . . . . ? C16 C17 C18 C13 2.9(4) . . . . ? C14 C13 C18 F15 175.5(2) . . . . ? B1 C13 C18 F15 -3.8(4) . . . . ? C14 C13 C18 C17 -3.8(4) . . . . ? B1 C13 C18 C17 176.9(2) . . . . ? C8 C7 B1 C13 -170.5(2) . . . . ? C12 C7 B1 C13 10.1(3) . . . . ? C8 C7 B1 C1 60.4(3) . . . . ? C12 C7 B1 C1 -119.0(3) . . . . ? C8 C7 B1 P1 -54.2(3) . . . . ? C12 C7 B1 P1 126.4(2) . . . . ? C14 C13 B1 C7 -106.4(3) . . . . ? C18 C13 B1 C7 72.9(3) . . . . ? C14 C13 B1 C1 24.1(3) . . . . ? C18 C13 B1 C1 -156.6(2) . . . . ? C14 C13 B1 P1 137.3(2) . . . . ? C18 C13 B1 P1 -43.4(3) . . . . ? C6 C1 B1 C7 12.1(3) . . . . ? C2 C1 B1 C7 -171.2(2) . . . . ? C6 C1 B1 C13 -117.8(3) . . . . ? C2 C1 B1 C13 58.9(3) . . . . ? C6 C1 B1 P1 127.8(2) . . . . ? C2 C1 B1 P1 -55.5(2) . . . . ? B2 P1 B1 C7 -140.53(17) . . . . ? B2 P1 B1 C13 -19.9(2) . . . . ? B2 P1 B1 C1 98.24(18) . . . . ? C20 S1 B2 P1 88.87(18) . . . . ? C19 S1 B2 P1 -165.77(15) . . . . ? B1 P1 B2 S1 116.84(15) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.328 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.076 data_ph _database_code_CSD 189751 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H7 B F15 P' _chemical_formula_weight 622.08 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 8.070(5) _cell_length_b 11.337(9) _cell_length_c 12.992(9) _cell_angle_alpha 86.66(9) _cell_angle_beta 77.22(7) _cell_angle_gamma 87.560(8) _cell_volume 1156.7(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.786 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4389 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 24.97 _reflns_number_total 4070 _reflns_number_gt 2495 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0327P)^2^+0.2136P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0043(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4070 _refine_ls_number_parameters 377 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0989 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 P1 P 0.14378(10) -0.19513(7) 0.19069(7) 0.0498(2) Uani 1 1 d . . . H1 H 0.217(3) -0.211(2) 0.0894(19) 0.050 Uiso 1 1 d . . . H2 H 0.014(3) -0.263(2) 0.2084(18) 0.050 Uiso 1 1 d . . . F1 F -0.0461(2) -0.27153(17) 0.39772(15) 0.0754(6) Uani 1 1 d . . . F2 F -0.1344(3) -0.38169(19) 0.58673(16) 0.0916(7) Uani 1 1 d . . . F3 F 0.1079(3) -0.46711(17) 0.69121(15) 0.0876(7) Uani 1 1 d . . . F4 F 0.4401(3) -0.43276(15) 0.60371(13) 0.0714(6) Uani 1 1 d . . . F5 F 0.5308(2) -0.31903(14) 0.41450(13) 0.0585(5) Uani 1 1 d . . . F6 F 0.2100(2) -0.44451(14) 0.20790(13) 0.0586(5) Uani 1 1 d . . . F7 F 0.3972(2) -0.62091(14) 0.11083(14) 0.0681(5) Uani 1 1 d . . . F8 F 0.7422(2) -0.60683(15) 0.05371(14) 0.0733(6) Uani 1 1 d . . . F9 F 0.8932(2) -0.41314(16) 0.09954(14) 0.0689(5) Uani 1 1 d . . . F10 F 0.71101(19) -0.24059(14) 0.20262(13) 0.0596(5) Uani 1 1 d . . . F11 F 0.5167(2) -0.09478(14) 0.09689(12) 0.0617(5) Uani 1 1 d . . . F12 F 0.6209(3) 0.12509(15) 0.09556(14) 0.0810(6) Uani 1 1 d . . . F13 F 0.5548(3) 0.24439(14) 0.27485(15) 0.0824(6) Uani 1 1 d . . . F14 F 0.3802(3) 0.13770(16) 0.45772(15) 0.0932(7) Uani 1 1 d . . . F15 F 0.2752(3) -0.07822(15) 0.46219(14) 0.0795(6) Uani 1 1 d . . . C1 C 0.0684(4) -0.0436(3) 0.1918(2) 0.0493(8) Uani 1 1 d . . . C2 C 0.1215(5) 0.0310(3) 0.1040(3) 0.0739(10) Uani 1 1 d . . . H2A H 0.1874 0.0008 0.0426 0.089 Uiso 1 1 calc R . . C3 C 0.0778(5) 0.1499(3) 0.1065(3) 0.0929(13) Uani 1 1 d . . . H3 H 0.1135 0.1997 0.0469 0.111 Uiso 1 1 calc R . . C4 C -0.0180(5) 0.1939(3) 0.1967(4) 0.0897(12) Uani 1 1 d . . . H4 H -0.0466 0.2742 0.1991 0.108 Uiso 1 1 calc R . . C5 C -0.0721(5) 0.1205(3) 0.2836(3) 0.0880(13) Uani 1 1 d . . . H5 H -0.1381 0.1512 0.3448 0.106 Uiso 1 1 calc R . . C6 C -0.0302(4) 0.0022(3) 0.2817(3) 0.0695(10) Uani 1 1 d . . . H6 H -0.0684 -0.0472 0.3413 0.083 Uiso 1 1 calc R . . C7 C 0.2484(4) -0.2948(2) 0.3942(2) 0.0429(7) Uani 1 1 d . . . C8 C 0.0819(4) -0.3126(3) 0.4439(3) 0.0541(8) Uani 1 1 d . . . C9 C 0.0314(4) -0.3688(3) 0.5435(3) 0.0595(9) Uani 1 1 d . . . C10 C 0.1535(5) -0.4107(3) 0.5952(2) 0.0601(9) Uani 1 1 d . . . C11 C 0.3206(5) -0.3938(3) 0.5517(2) 0.0524(8) Uani 1 1 d . . . C12 C 0.3639(4) -0.3367(2) 0.4535(2) 0.0461(7) Uani 1 1 d . . . C13 C 0.4488(3) -0.3323(2) 0.2090(2) 0.0389(7) Uani 1 1 d . . . C14 C 0.3808(4) -0.4340(2) 0.1831(2) 0.0428(7) Uani 1 1 d . . . C15 C 0.4743(4) -0.5259(2) 0.1329(2) 0.0465(7) Uani 1 1 d . . . C16 C 0.6476(4) -0.5190(3) 0.1049(2) 0.0501(8) Uani 1 1 d . . . C17 C 0.7234(4) -0.4207(3) 0.1275(2) 0.0476(7) Uani 1 1 d . . . C18 C 0.6247(4) -0.3320(2) 0.1793(2) 0.0449(7) Uani 1 1 d . . . C19 C 0.3982(3) -0.1019(2) 0.2806(2) 0.0399(7) Uani 1 1 d . . . C20 C 0.4847(4) -0.0415(2) 0.1904(2) 0.0459(7) Uani 1 1 d . . . C21 C 0.5378(4) 0.0719(3) 0.1864(2) 0.0537(8) Uani 1 1 d . . . C22 C 0.5041(4) 0.1331(3) 0.2768(3) 0.0580(9) Uani 1 1 d . . . C23 C 0.4167(4) 0.0797(3) 0.3682(3) 0.0571(8) Uani 1 1 d . . . C24 C 0.3658(4) -0.0350(3) 0.3687(2) 0.0507(8) Uani 1 1 d . . . B1 B 0.3234(4) -0.2332(3) 0.2771(3) 0.0415(8) 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 0.0466(5) 0.0492(5) 0.0565(5) -0.0115(4) -0.0163(4) 0.0024(4) F1 0.0456(11) 0.0933(15) 0.0805(14) 0.0138(11) -0.0048(10) -0.0001(10) F2 0.0681(14) 0.1027(16) 0.0871(15) 0.0117(12) 0.0164(12) -0.0113(12) F3 0.1187(18) 0.0757(13) 0.0578(12) 0.0140(10) -0.0003(12) -0.0064(12) F4 0.1013(15) 0.0611(12) 0.0585(12) -0.0091(9) -0.0327(11) 0.0105(11) F5 0.0557(12) 0.0641(11) 0.0589(11) -0.0071(9) -0.0184(9) -0.0029(9) F6 0.0477(11) 0.0516(10) 0.0769(12) -0.0074(9) -0.0119(9) -0.0113(8) F7 0.0848(13) 0.0413(10) 0.0833(13) -0.0143(9) -0.0249(11) -0.0098(9) F8 0.0812(14) 0.0600(11) 0.0757(13) -0.0240(10) -0.0097(11) 0.0208(10) F9 0.0434(11) 0.0792(13) 0.0790(13) -0.0154(10) -0.0010(9) 0.0072(9) F10 0.0407(10) 0.0567(11) 0.0835(13) -0.0188(9) -0.0130(9) -0.0064(8) F11 0.0895(13) 0.0506(10) 0.0435(10) -0.0092(8) -0.0072(9) -0.0139(9) F12 0.1153(17) 0.0573(12) 0.0646(13) -0.0008(10) -0.0026(12) -0.0296(12) F13 0.1217(17) 0.0413(11) 0.0882(15) -0.0107(10) -0.0264(13) -0.0179(11) F14 0.150(2) 0.0623(13) 0.0660(13) -0.0322(10) -0.0120(13) -0.0061(13) F15 0.1176(17) 0.0601(12) 0.0501(11) -0.0137(9) 0.0095(11) -0.0140(11) C1 0.0458(18) 0.0527(19) 0.051(2) -0.0069(16) -0.0144(15) 0.0060(15) C2 0.081(3) 0.070(2) 0.064(2) -0.008(2) -0.003(2) 0.018(2) C3 0.109(3) 0.068(3) 0.092(3) 0.018(2) -0.009(3) 0.014(2) C4 0.109(3) 0.059(2) 0.103(3) -0.008(2) -0.028(3) 0.018(2) C5 0.115(3) 0.072(3) 0.073(3) -0.018(2) -0.013(2) 0.033(3) C6 0.082(3) 0.064(2) 0.057(2) -0.0056(18) -0.0076(19) 0.019(2) C7 0.0464(19) 0.0339(16) 0.0472(18) -0.0095(13) -0.0056(15) -0.0021(14) C8 0.050(2) 0.0487(19) 0.062(2) -0.0003(16) -0.0111(18) 0.0031(16) C9 0.054(2) 0.051(2) 0.064(2) -0.0015(17) 0.0085(19) -0.0071(17) C10 0.087(3) 0.0439(19) 0.045(2) -0.0027(15) -0.003(2) -0.0035(19) C11 0.071(2) 0.0395(18) 0.049(2) -0.0116(15) -0.0165(19) 0.0039(17) C12 0.048(2) 0.0414(17) 0.0475(19) -0.0126(15) -0.0054(16) -0.0015(15) C13 0.0415(18) 0.0372(16) 0.0393(16) -0.0018(12) -0.0111(13) -0.0017(13) C14 0.0395(18) 0.0413(17) 0.0464(18) -0.0014(14) -0.0069(14) -0.0034(14) C15 0.061(2) 0.0338(17) 0.0478(18) -0.0037(14) -0.0173(16) -0.0024(15) C16 0.064(2) 0.0415(18) 0.0445(18) -0.0086(14) -0.0111(16) 0.0115(16) C17 0.0425(19) 0.054(2) 0.0434(18) -0.0043(15) -0.0041(15) 0.0049(15) C18 0.0457(19) 0.0452(18) 0.0462(17) -0.0072(14) -0.0129(15) -0.0064(15) C19 0.0433(17) 0.0378(16) 0.0404(17) -0.0081(13) -0.0117(14) 0.0018(13) C20 0.0537(19) 0.0437(17) 0.0417(18) -0.0137(14) -0.0103(15) -0.0025(15) C21 0.061(2) 0.0491(19) 0.051(2) 0.0024(16) -0.0100(17) -0.0138(16) C22 0.076(2) 0.0352(18) 0.067(2) -0.0102(17) -0.0224(19) -0.0080(16) C23 0.075(2) 0.0447(19) 0.054(2) -0.0202(16) -0.0149(18) 0.0012(17) C24 0.059(2) 0.0475(19) 0.0432(19) -0.0073(15) -0.0051(16) -0.0023(16) B1 0.0354(19) 0.0429(19) 0.048(2) -0.0084(15) -0.0116(16) 0.0003(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 P1 C1 1.798(3) . ? P1 B1 2.039(3) . ? P1 H1 1.34(2) . ? P1 H2 1.30(2) . ? F1 C8 1.358(3) . ? F2 C9 1.343(4) . ? F3 C10 1.351(4) . ? F4 C11 1.341(4) . ? F5 C12 1.349(3) . ? F6 C14 1.353(3) . ? F7 C15 1.342(3) . ? F8 C16 1.343(3) . ? F9 C17 1.343(3) . ? F10 C18 1.358(3) . ? F11 C20 1.357(3) . ? F12 C21 1.344(3) . ? F13 C22 1.340(3) . ? F14 C23 1.339(3) . ? F15 C24 1.348(3) . ? C1 C6 1.376(4) . ? C1 C2 1.379(4) . ? C2 C3 1.379(5) . ? C2 H2A 0.9300 . ? C3 C4 1.362(5) . ? C3 H3 0.9300 . ? C4 C5 1.364(5) . ? C4 H4 0.9300 . ? C5 C6 1.370(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.374(4) . ? C7 C12 1.388(4) . ? C7 B1 1.635(4) . ? C8 C9 1.392(4) . ? C9 C10 1.365(5) . ? C10 C11 1.359(4) . ? C11 C12 1.376(4) . ? C13 C18 1.387(4) . ? C13 C14 1.387(4) . ? C13 B1 1.641(4) . ? C14 C15 1.370(4) . ? C15 C16 1.369(4) . ? C16 C17 1.371(4) . ? C17 C18 1.367(4) . ? C19 C24 1.380(4) . ? C19 C20 1.384(4) . ? C19 B1 1.637(4) . ? C20 C21 1.367(4) . ? C21 C22 1.368(4) . ? C22 C23 1.363(4) . ? C23 C24 1.379(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 C1 P1 B1 114.58(14) . . ? C1 P1 H1 104.3(10) . . ? B1 P1 H1 107.4(10) . . ? C1 P1 H2 108.6(10) . . ? B1 P1 H2 117.1(10) . . ? H1 P1 H2 103.5(14) . . ? C6 C1 C2 119.0(3) . . ? C6 C1 P1 121.1(3) . . ? C2 C1 P1 119.7(3) . . ? C1 C2 C3 120.6(3) . . ? C1 C2 H2A 119.7 . . ? C3 C2 H2A 119.7 . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.2(4) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.7(4) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 120.0(4) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C8 C7 C12 113.6(3) . . ? C8 C7 B1 128.5(3) . . ? C12 C7 B1 117.9(3) . . ? F1 C8 C7 120.4(3) . . ? F1 C8 C9 115.6(3) . . ? C7 C8 C9 124.0(3) . . ? F2 C9 C10 121.2(3) . . ? F2 C9 C8 120.1(3) . . ? C10 C9 C8 118.7(3) . . ? F3 C10 C11 119.7(3) . . ? F3 C10 C9 119.8(3) . . ? C11 C10 C9 120.4(3) . . ? F4 C11 C10 120.3(3) . . ? F4 C11 C12 121.1(3) . . ? C10 C11 C12 118.6(3) . . ? F5 C12 C11 116.7(3) . . ? F5 C12 C7 118.6(3) . . ? C11 C12 C7 124.7(3) . . ? C18 C13 C14 113.1(3) . . ? C18 C13 B1 127.0(2) . . ? C14 C13 B1 119.7(2) . . ? F6 C14 C15 116.6(3) . . ? F6 C14 C13 118.7(2) . . ? C15 C14 C13 124.7(3) . . ? F7 C15 C16 120.5(3) . . ? F7 C15 C14 120.5(3) . . ? C16 C15 C14 119.0(3) . . ? F8 C16 C15 120.3(3) . . ? F8 C16 C17 120.3(3) . . ? C15 C16 C17 119.5(3) . . ? F9 C17 C18 120.9(3) . . ? F9 C17 C16 119.7(3) . . ? C18 C17 C16 119.4(3) . . ? F10 C18 C17 115.3(3) . . ? F10 C18 C13 120.3(3) . . ? C17 C18 C13 124.4(3) . . ? C24 C19 C20 113.2(3) . . ? C24 C19 B1 124.5(3) . . ? C20 C19 B1 122.0(2) . . ? F11 C20 C21 115.8(3) . . ? F11 C20 C19 119.3(2) . . ? C21 C20 C19 124.9(3) . . ? F12 C21 C20 121.5(3) . . ? F12 C21 C22 119.3(3) . . ? C20 C21 C22 119.2(3) . . ? F13 C22 C23 120.7(3) . . ? F13 C22 C21 120.3(3) . . ? C23 C22 C21 119.0(3) . . ? F14 C23 C22 120.4(3) . . ? F14 C23 C24 119.8(3) . . ? C22 C23 C24 119.8(3) . . ? F15 C24 C19 121.0(3) . . ? F15 C24 C23 115.1(3) . . ? C19 C24 C23 123.9(3) . . ? C7 B1 C19 113.4(2) . . ? C7 B1 C13 106.9(2) . . ? C19 B1 C13 117.9(2) . . ? C7 B1 P1 114.0(2) . . ? C19 B1 P1 100.82(19) . . ? C13 B1 P1 103.64(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 B1 P1 C1 C6 -69.5(3) . . . . ? B1 P1 C1 C2 105.0(3) . . . . ? C6 C1 C2 C3 0.6(5) . . . . ? P1 C1 C2 C3 -174.0(3) . . . . ? C1 C2 C3 C4 0.3(6) . . . . ? C2 C3 C4 C5 -0.8(7) . . . . ? C3 C4 C5 C6 0.4(7) . . . . ? C4 C5 C6 C1 0.5(6) . . . . ? C2 C1 C6 C5 -0.9(5) . . . . ? P1 C1 C6 C5 173.6(3) . . . . ? C12 C7 C8 F1 177.0(2) . . . . ? B1 C7 C8 F1 -3.6(4) . . . . ? C12 C7 C8 C9 -0.9(4) . . . . ? B1 C7 C8 C9 178.5(3) . . . . ? F1 C8 C9 F2 1.4(4) . . . . ? C7 C8 C9 F2 179.4(3) . . . . ? F1 C8 C9 C10 -179.0(3) . . . . ? C7 C8 C9 C10 -1.0(5) . . . . ? F2 C9 C10 F3 0.6(5) . . . . ? C8 C9 C10 F3 -179.0(3) . . . . ? F2 C9 C10 C11 -178.0(3) . . . . ? C8 C9 C10 C11 2.4(5) . . . . ? F3 C10 C11 F4 -0.1(4) . . . . ? C9 C10 C11 F4 178.5(3) . . . . ? F3 C10 C11 C12 179.6(2) . . . . ? C9 C10 C11 C12 -1.8(4) . . . . ? F4 C11 C12 F5 -2.0(4) . . . . ? C10 C11 C12 F5 178.3(3) . . . . ? F4 C11 C12 C7 179.4(2) . . . . ? C10 C11 C12 C7 -0.3(4) . . . . ? C8 C7 C12 F5 -177.0(2) . . . . ? B1 C7 C12 F5 3.6(4) . . . . ? C8 C7 C12 C11 1.6(4) . . . . ? B1 C7 C12 C11 -177.9(3) . . . . ? C18 C13 C14 F6 -179.8(2) . . . . ? B1 C13 C14 F6 4.9(4) . . . . ? C18 C13 C14 C15 -0.2(4) . . . . ? B1 C13 C14 C15 -175.5(3) . . . . ? F6 C14 C15 F7 -0.3(4) . . . . ? C13 C14 C15 F7 -179.9(3) . . . . ? F6 C14 C15 C16 179.2(2) . . . . ? C13 C14 C15 C16 -0.4(4) . . . . ? F7 C15 C16 F8 0.8(4) . . . . ? C14 C15 C16 F8 -178.7(2) . . . . ? F7 C15 C16 C17 179.5(2) . . . . ? C14 C15 C16 C17 0.0(4) . . . . ? F8 C16 C17 F9 -0.9(4) . . . . ? C15 C16 C17 F9 -179.6(3) . . . . ? F8 C16 C17 C18 179.8(2) . . . . ? C15 C16 C17 C18 1.1(4) . . . . ? F9 C17 C18 F10 -2.2(4) . . . . ? C16 C17 C18 F10 177.1(3) . . . . ? F9 C17 C18 C13 178.8(3) . . . . ? C16 C17 C18 C13 -1.9(4) . . . . ? C14 C13 C18 F10 -177.5(2) . . . . ? B1 C13 C18 F10 -2.7(4) . . . . ? C14 C13 C18 C17 1.4(4) . . . . ? B1 C13 C18 C17 176.2(3) . . . . ? C24 C19 C20 F11 -176.5(2) . . . . ? B1 C19 C20 F11 -3.6(4) . . . . ? C24 C19 C20 C21 1.4(4) . . . . ? B1 C19 C20 C21 174.3(3) . . . . ? F11 C20 C21 F12 -1.9(4) . . . . ? C19 C20 C21 F12 -179.8(3) . . . . ? F11 C20 C21 C22 177.4(3) . . . . ? C19 C20 C21 C22 -0.5(5) . . . . ? F12 C21 C22 F13 -0.6(5) . . . . ? C20 C21 C22 F13 -179.9(3) . . . . ? F12 C21 C22 C23 178.6(3) . . . . ? C20 C21 C22 C23 -0.7(5) . . . . ? F13 C22 C23 F14 0.0(5) . . . . ? C21 C22 C23 F14 -179.3(3) . . . . ? F13 C22 C23 C24 -179.9(3) . . . . ? C21 C22 C23 C24 0.8(5) . . . . ? C20 C19 C24 F15 176.7(3) . . . . ? B1 C19 C24 F15 4.0(4) . . . . ? C20 C19 C24 C23 -1.2(4) . . . . ? B1 C19 C24 C23 -173.9(3) . . . . ? F14 C23 C24 F15 2.2(4) . . . . ? C22 C23 C24 F15 -177.8(3) . . . . ? F14 C23 C24 C19 -179.7(3) . . . . ? C22 C23 C24 C19 0.2(5) . . . . ? C8 C7 B1 C19 107.6(3) . . . . ? C12 C7 B1 C19 -73.0(3) . . . . ? C8 C7 B1 C13 -120.8(3) . . . . ? C12 C7 B1 C13 58.5(3) . . . . ? C8 C7 B1 P1 -7.0(4) . . . . ? C12 C7 B1 P1 172.4(2) . . . . ? C24 C19 B1 C7 -15.6(4) . . . . ? C20 C19 B1 C7 172.4(2) . . . . ? C24 C19 B1 C13 -141.5(3) . . . . ? C20 C19 B1 C13 46.5(4) . . . . ? C24 C19 B1 P1 106.7(3) . . . . ? C20 C19 B1 P1 -65.4(3) . . . . ? C18 C13 B1 C7 -108.5(3) . . . . ? C14 C13 B1 C7 66.0(3) . . . . ? C18 C13 B1 C19 20.5(4) . . . . ? C14 C13 B1 C19 -165.0(2) . . . . ? C18 C13 B1 P1 130.8(3) . . . . ? C14 C13 B1 P1 -54.7(3) . . . . ? C1 P1 B1 C7 99.3(2) . . . . ? C1 P1 B1 C19 -22.5(2) . . . . ? C1 P1 B1 C13 -144.95(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.196 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.042 data_jmd _database_code_CSD 189752 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H12 B2 F30 S2' _chemical_formula_weight 1148.24 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' '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' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.7574(7) _cell_length_b 11.8948(5) _cell_length_c 20.2990(9) _cell_angle_alpha 90.00 _cell_angle_beta 110.101(2) _cell_angle_gamma 90.00 _cell_volume 4026.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.894 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4604 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4604 _reflns_number_gt 3119 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0978P)^2^+16.0484P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0002(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4604 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1124 _refine_ls_R_factor_gt 0.0724 _refine_ls_wR_factor_ref 0.2138 _refine_ls_wR_factor_gt 0.1795 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.80954(6) 0.01319(10) 0.10737(6) 0.0439(3) Uani 1 1 d . . . F1 F 0.73391(16) -0.0845(2) 0.20132(13) 0.0525(7) Uani 1 1 d . . . F2 F 0.68226(19) -0.2726(3) 0.24406(15) 0.0670(9) Uani 1 1 d . . . F3 F 0.57801(19) -0.4133(2) 0.14860(18) 0.0670(9) Uani 1 1 d . . . F4 F 0.53090(18) -0.3626(2) 0.00955(16) 0.0569(7) Uani 1 1 d . . . F5 F 0.57904(15) -0.1767(2) -0.03387(12) 0.0461(6) Uani 1 1 d . . . F6 F 0.54851(15) -0.00494(19) 0.11527(13) 0.0434(6) Uani 1 1 d . . . F7 F 0.50388(16) 0.1593(2) 0.18145(14) 0.0492(7) Uani 1 1 d . . . F8 F 0.57480(17) 0.3645(2) 0.19756(14) 0.0525(7) Uani 1 1 d . . . F9 F 0.69588(16) 0.4003(2) 0.14484(14) 0.0510(7) Uani 1 1 d . . . F10 F 0.74612(14) 0.2332(2) 0.08259(14) 0.0466(6) Uani 1 1 d . . . F11 F 0.58097(14) 0.1861(2) -0.02983(12) 0.0413(6) Uani 1 1 d . . . F12 F 0.54374(15) 0.2101(2) -0.16561(12) 0.0460(6) Uani 1 1 d . . . F13 F 0.59616(17) 0.0594(2) -0.24155(12) 0.0507(7) Uani 1 1 d . . . F14 F 0.69287(17) -0.1125(2) -0.17485(14) 0.0539(7) Uani 1 1 d . . . F15 F 0.73584(15) -0.1355(2) -0.03585(13) 0.0464(6) Uani 1 1 d . . . C1 C 0.8523(3) -0.1252(4) 0.1205(3) 0.0521(11) Uani 1 1 d . . . H1A H 0.8357 -0.1644 0.1545 0.063 Uiso 1 1 calc R . . H1B H 0.9098 -0.1196 0.1372 0.063 Uiso 1 1 calc R . . H1C H 0.8345 -0.1656 0.0769 0.063 Uiso 1 1 calc R . . C2 C 0.8511(3) 0.0634(4) 0.0429(3) 0.0510(11) Uani 1 1 d . . . H2A H 0.8334 0.1390 0.0298 0.061 Uiso 1 1 calc R . . H2B H 0.8334 0.0159 0.0022 0.061 Uiso 1 1 calc R . . H2C H 0.9086 0.0619 0.0626 0.061 Uiso 1 1 calc R . . C3 C 0.6611(2) -0.1214(3) 0.0808(2) 0.0373(9) Uani 1 1 d . . . C4 C 0.6843(3) -0.1527(4) 0.1519(2) 0.0436(10) Uani 1 1 d . . . C5 C 0.6580(3) -0.2490(4) 0.1747(3) 0.0506(11) Uani 1 1 d . . . C6 C 0.6067(3) -0.3203(4) 0.1279(3) 0.0501(11) Uani 1 1 d . . . C7 C 0.5826(3) -0.2947(4) 0.0577(3) 0.0444(10) Uani 1 1 d . . . C8 C 0.6095(3) -0.1963(4) 0.0362(2) 0.0395(9) Uani 1 1 d . . . C9 C 0.6547(2) 0.1022(3) 0.0999(2) 0.0365(9) Uani 1 1 d . . . C10 C 0.5911(2) 0.0917(3) 0.1247(2) 0.0358(9) Uani 1 1 d . . . C11 C 0.5652(3) 0.1767(4) 0.1584(2) 0.0399(9) Uani 1 1 d . . . C12 C 0.6010(3) 0.2802(4) 0.1663(2) 0.0420(10) Uani 1 1 d . . . C13 C 0.6620(3) 0.2976(3) 0.1400(2) 0.0406(9) Uani 1 1 d . . . C14 C 0.6870(2) 0.2100(4) 0.1090(2) 0.0396(9) Uani 1 1 d . . . C15 C 0.6630(2) 0.0239(3) -0.0237(2) 0.0350(8) Uani 1 1 d . . . C16 C 0.6134(2) 0.1104(3) -0.0617(2) 0.0336(8) Uani 1 1 d . . . C17 C 0.5917(2) 0.1245(3) -0.1337(2) 0.0362(9) Uani 1 1 d . . . C18 C 0.6178(3) 0.0496(4) -0.1721(2) 0.0404(9) Uani 1 1 d . . . C19 C 0.6668(3) -0.0376(4) -0.1379(2) 0.0399(9) Uani 1 1 d . . . C20 C 0.6884(2) -0.0468(3) -0.0659(2) 0.0383(9) Uani 1 1 d . . . B1 B 0.6850(3) 0.0023(4) 0.0596(2) 0.0357(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 0.0377(6) 0.0477(6) 0.0455(6) 0.0022(5) 0.0134(4) -0.0022(5) F1 0.0525(15) 0.0588(17) 0.0409(13) 0.0082(12) 0.0091(12) -0.0067(13) F2 0.0721(19) 0.0699(19) 0.0550(17) 0.0313(15) 0.0168(15) -0.0003(16) F3 0.071(2) 0.0431(15) 0.092(2) 0.0258(15) 0.0342(17) -0.0024(14) F4 0.0615(17) 0.0415(14) 0.0733(19) -0.0068(13) 0.0304(15) -0.0113(13) F5 0.0529(14) 0.0448(14) 0.0404(13) -0.0024(11) 0.0158(11) -0.0091(11) F6 0.0454(13) 0.0410(13) 0.0499(14) -0.0044(11) 0.0241(11) -0.0127(11) F7 0.0578(16) 0.0501(14) 0.0525(15) -0.0017(12) 0.0353(13) -0.0073(12) F8 0.0684(18) 0.0440(14) 0.0537(15) -0.0076(12) 0.0318(13) -0.0033(13) F9 0.0579(16) 0.0400(14) 0.0600(16) -0.0067(12) 0.0266(13) -0.0152(12) F10 0.0446(14) 0.0453(14) 0.0579(15) 0.0008(12) 0.0278(12) -0.0094(11) F11 0.0446(13) 0.0425(13) 0.0372(12) -0.0014(10) 0.0146(10) 0.0062(10) F12 0.0539(15) 0.0453(14) 0.0375(13) 0.0081(11) 0.0140(11) 0.0091(11) F13 0.0663(17) 0.0567(16) 0.0332(13) 0.0028(11) 0.0222(12) 0.0031(13) F14 0.0704(18) 0.0519(15) 0.0504(15) -0.0008(12) 0.0347(14) 0.0107(14) F15 0.0513(14) 0.0415(13) 0.0511(15) 0.0073(11) 0.0234(12) 0.0093(11) C1 0.048(3) 0.053(3) 0.055(3) 0.007(2) 0.018(2) 0.006(2) C2 0.039(2) 0.057(3) 0.063(3) 0.004(2) 0.025(2) -0.005(2) C3 0.034(2) 0.035(2) 0.043(2) 0.0060(17) 0.0147(17) 0.0022(16) C4 0.041(2) 0.044(2) 0.046(2) 0.0063(19) 0.0138(19) 0.0002(19) C5 0.048(3) 0.052(3) 0.052(3) 0.018(2) 0.016(2) 0.005(2) C6 0.051(3) 0.038(2) 0.067(3) 0.018(2) 0.027(2) 0.006(2) C7 0.043(2) 0.035(2) 0.060(3) -0.001(2) 0.023(2) -0.0050(18) C8 0.043(2) 0.038(2) 0.040(2) 0.0061(17) 0.0187(18) 0.0043(18) C9 0.038(2) 0.039(2) 0.034(2) 0.0015(16) 0.0130(16) -0.0056(17) C10 0.041(2) 0.035(2) 0.0312(19) 0.0026(16) 0.0123(16) -0.0062(17) C11 0.044(2) 0.046(2) 0.034(2) 0.0037(18) 0.0203(17) -0.0055(19) C12 0.051(2) 0.041(2) 0.036(2) -0.0026(18) 0.0177(18) 0.0002(19) C13 0.047(2) 0.035(2) 0.040(2) -0.0011(17) 0.0149(18) -0.0087(18) C14 0.036(2) 0.042(2) 0.040(2) 0.0031(18) 0.0129(17) -0.0085(18) C15 0.035(2) 0.034(2) 0.037(2) 0.0040(16) 0.0142(16) -0.0039(16) C16 0.0337(19) 0.0324(19) 0.036(2) -0.0015(16) 0.0138(16) -0.0041(16) C17 0.037(2) 0.035(2) 0.038(2) 0.0048(17) 0.0137(17) -0.0009(16) C18 0.046(2) 0.045(2) 0.033(2) 0.0050(18) 0.0171(17) -0.0064(19) C19 0.044(2) 0.038(2) 0.044(2) -0.0013(18) 0.0236(19) 0.0006(18) C20 0.037(2) 0.036(2) 0.044(2) 0.0056(18) 0.0170(17) 0.0002(17) B1 0.035(2) 0.039(2) 0.033(2) 0.0043(18) 0.0123(17) -0.0035(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.794(5) . ? S1 C2 1.810(5) . ? S1 B1 2.091(5) . ? F1 C4 1.355(5) . ? F2 C5 1.353(5) . ? F3 C6 1.345(5) . ? F4 C7 1.355(5) . ? F5 C8 1.358(5) . ? F6 C10 1.353(4) . ? F7 C11 1.342(5) . ? F8 C12 1.352(5) . ? F9 C13 1.350(5) . ? F10 C14 1.361(5) . ? F11 C16 1.348(4) . ? F12 C17 1.342(4) . ? F13 C18 1.333(5) . ? F14 C19 1.345(5) . ? F15 C20 1.357(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C8 1.372(6) . ? C3 C4 1.408(6) . ? C3 B1 1.630(6) . ? C4 C5 1.375(6) . ? C5 C6 1.363(7) . ? C6 C7 1.373(7) . ? C7 C8 1.389(6) . ? C9 C14 1.391(6) . ? C9 C10 1.391(6) . ? C9 B1 1.636(6) . ? C10 C11 1.384(6) . ? C11 C12 1.369(6) . ? C12 C13 1.379(6) . ? C13 C14 1.368(6) . ? C15 C20 1.382(6) . ? C15 C16 1.401(5) . ? C15 B1 1.619(6) . ? C16 C17 1.388(6) . ? C17 C18 1.366(6) . ? C18 C19 1.378(6) . ? C19 C20 1.382(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C2 98.8(2) . . ? C1 S1 B1 109.8(2) . . ? C2 S1 B1 108.3(2) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C8 C3 C4 113.4(4) . . ? C8 C3 B1 126.0(4) . . ? C4 C3 B1 119.9(4) . . ? F1 C4 C5 117.3(4) . . ? F1 C4 C3 119.2(4) . . ? C5 C4 C3 123.5(4) . . ? F2 C5 C6 119.6(4) . . ? F2 C5 C4 120.0(4) . . ? C6 C5 C4 120.4(4) . . ? F3 C6 C5 121.9(4) . . ? F3 C6 C7 119.4(5) . . ? C5 C6 C7 118.7(4) . . ? F4 C7 C6 120.6(4) . . ? F4 C7 C8 119.8(4) . . ? C6 C7 C8 119.6(4) . . ? F5 C8 C3 121.0(4) . . ? F5 C8 C7 114.7(4) . . ? C3 C8 C7 124.3(4) . . ? C14 C9 C10 112.6(4) . . ? C14 C9 B1 122.9(4) . . ? C10 C9 B1 124.3(3) . . ? F6 C10 C11 115.3(3) . . ? F6 C10 C9 120.6(4) . . ? C11 C10 C9 124.1(4) . . ? F7 C11 C12 119.8(4) . . ? F7 C11 C10 120.4(4) . . ? C12 C11 C10 119.8(4) . . ? F8 C12 C11 120.1(4) . . ? F8 C12 C13 120.9(4) . . ? C11 C12 C13 118.9(4) . . ? F9 C13 C14 121.1(4) . . ? F9 C13 C12 119.8(4) . . ? C14 C13 C12 119.1(4) . . ? F10 C14 C13 116.2(4) . . ? F10 C14 C9 118.3(4) . . ? C13 C14 C9 125.4(4) . . ? C20 C15 C16 112.5(4) . . ? C20 C15 B1 122.5(4) . . ? C16 C15 B1 124.9(4) . . ? F11 C16 C17 114.5(3) . . ? F11 C16 C15 121.2(3) . . ? C17 C16 C15 124.3(4) . . ? F12 C17 C18 120.2(4) . . ? F12 C17 C16 120.0(4) . . ? C18 C17 C16 119.8(4) . . ? F13 C18 C17 121.0(4) . . ? F13 C18 C19 120.1(4) . . ? C17 C18 C19 118.9(4) . . ? F14 C19 C18 119.8(4) . . ? F14 C19 C20 120.9(4) . . ? C18 C19 C20 119.3(4) . . ? F15 C20 C19 116.1(4) . . ? F15 C20 C15 118.6(4) . . ? C19 C20 C15 125.2(4) . . ? C15 B1 C3 115.3(3) . . ? C15 B1 C9 113.9(3) . . ? C3 B1 C9 111.3(3) . . ? C15 B1 S1 108.2(3) . . ? C3 B1 S1 105.3(3) . . ? C9 B1 S1 101.6(3) . . ? 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 C8 C3 C4 F1 -178.7(4) . . . . ? B1 C3 C4 F1 -7.4(6) . . . . ? C8 C3 C4 C5 0.2(6) . . . . ? B1 C3 C4 C5 171.4(4) . . . . ? F1 C4 C5 F2 -0.3(7) . . . . ? C3 C4 C5 F2 -179.2(4) . . . . ? F1 C4 C5 C6 178.7(4) . . . . ? C3 C4 C5 C6 -0.2(7) . . . . ? F2 C5 C6 F3 1.1(7) . . . . ? C4 C5 C6 F3 -177.9(4) . . . . ? F2 C5 C6 C7 179.8(4) . . . . ? C4 C5 C6 C7 0.8(7) . . . . ? F3 C6 C7 F4 -0.5(7) . . . . ? C5 C6 C7 F4 -179.2(4) . . . . ? F3 C6 C7 C8 177.4(4) . . . . ? C5 C6 C7 C8 -1.4(7) . . . . ? C4 C3 C8 F5 177.6(4) . . . . ? B1 C3 C8 F5 7.0(6) . . . . ? C4 C3 C8 C7 -0.8(6) . . . . ? B1 C3 C8 C7 -171.4(4) . . . . ? F4 C7 C8 F5 0.8(6) . . . . ? C6 C7 C8 F5 -177.1(4) . . . . ? F4 C7 C8 C3 179.3(4) . . . . ? C6 C7 C8 C3 1.5(7) . . . . ? C14 C9 C10 F6 174.9(3) . . . . ? B1 C9 C10 F6 -1.2(6) . . . . ? C14 C9 C10 C11 -3.4(6) . . . . ? B1 C9 C10 C11 -179.5(4) . . . . ? F6 C10 C11 F7 2.4(6) . . . . ? C9 C10 C11 F7 -179.2(4) . . . . ? F6 C10 C11 C12 -175.7(4) . . . . ? C9 C10 C11 C12 2.7(6) . . . . ? F7 C11 C12 F8 0.3(6) . . . . ? C10 C11 C12 F8 178.4(4) . . . . ? F7 C11 C12 C13 -177.7(4) . . . . ? C10 C11 C12 C13 0.4(6) . . . . ? F8 C12 C13 F9 -0.6(6) . . . . ? C11 C12 C13 F9 177.4(4) . . . . ? F8 C12 C13 C14 179.7(4) . . . . ? C11 C12 C13 C14 -2.3(6) . . . . ? F9 C13 C14 F10 -1.3(6) . . . . ? C12 C13 C14 F10 178.4(4) . . . . ? F9 C13 C14 C9 -178.3(4) . . . . ? C12 C13 C14 C9 1.4(7) . . . . ? C10 C9 C14 F10 -175.6(3) . . . . ? B1 C9 C14 F10 0.5(6) . . . . ? C10 C9 C14 C13 1.4(6) . . . . ? B1 C9 C14 C13 177.5(4) . . . . ? C20 C15 C16 F11 178.2(3) . . . . ? B1 C15 C16 F11 1.6(6) . . . . ? C20 C15 C16 C17 0.1(6) . . . . ? B1 C15 C16 C17 -176.5(4) . . . . ? F11 C16 C17 F12 1.6(5) . . . . ? C15 C16 C17 F12 179.9(3) . . . . ? F11 C16 C17 C18 -176.9(3) . . . . ? C15 C16 C17 C18 1.4(6) . . . . ? F12 C17 C18 F13 -0.3(6) . . . . ? C16 C17 C18 F13 178.3(4) . . . . ? F12 C17 C18 C19 -179.9(4) . . . . ? C16 C17 C18 C19 -1.3(6) . . . . ? F13 C18 C19 F14 0.1(6) . . . . ? C17 C18 C19 F14 179.7(4) . . . . ? F13 C18 C19 C20 -179.7(4) . . . . ? C17 C18 C19 C20 -0.1(6) . . . . ? F14 C19 C20 F15 -0.6(6) . . . . ? C18 C19 C20 F15 179.1(4) . . . . ? F14 C19 C20 C15 -178.1(4) . . . . ? C18 C19 C20 C15 1.7(7) . . . . ? C16 C15 C20 F15 -179.0(3) . . . . ? B1 C15 C20 F15 -2.3(6) . . . . ? C16 C15 C20 C19 -1.6(6) . . . . ? B1 C15 C20 C19 175.1(4) . . . . ? C20 C15 B1 C3 -54.3(5) . . . . ? C16 C15 B1 C3 122.0(4) . . . . ? C20 C15 B1 C9 175.3(4) . . . . ? C16 C15 B1 C9 -8.4(5) . . . . ? C20 C15 B1 S1 63.2(4) . . . . ? C16 C15 B1 S1 -120.5(4) . . . . ? C8 C3 B1 C15 -15.9(6) . . . . ? C4 C3 B1 C15 174.1(4) . . . . ? C8 C3 B1 C9 115.8(4) . . . . ? C4 C3 B1 C9 -54.3(5) . . . . ? C8 C3 B1 S1 -135.0(4) . . . . ? C4 C3 B1 S1 54.9(4) . . . . ? C14 C9 B1 C15 -68.1(5) . . . . ? C10 C9 B1 C15 107.6(4) . . . . ? C14 C9 B1 C3 159.6(4) . . . . ? C10 C9 B1 C3 -24.7(5) . . . . ? C14 C9 B1 S1 48.0(4) . . . . ? C10 C9 B1 S1 -136.3(4) . . . . ? C1 S1 B1 C15 -98.6(3) . . . . ? C2 S1 B1 C15 8.3(4) . . . . ? C1 S1 B1 C3 25.2(3) . . . . ? C2 S1 B1 C3 132.1(3) . . . . ? C1 S1 B1 C9 141.3(3) . . . . ? C2 S1 B1 C9 -111.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.827 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.089