Supplementary information (ESI) for Dalton Trans. This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Derek Gates' _publ_contact_author_address ; Chemistry Department University of British Columbia 2036 Main Mall Vancouver British Columbia, V6T 1Z3 CANADA ; _publ_contact_author_email DGATES@CHEM.UBC.CA _publ_section_title ; Chemical functionality of poly(methylenephosphine): phosphine-borane adducts and methylphosphonium ionomers ; loop_ _publ_author_name 'Derek Gates' 'Joshua I. Bates' 'Bastian Feldscher' 'Justin J. Kingsley' 'Kevin J. T. Noonan' 'Mandy Yam' # Attachment 'Dalton_Revised.cif' data_dg057 _database_code_depnum_ccdc_archive 'CCDC 668085' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H34 B P Si' _chemical_formula_sum 'C25 H34 B P Si' _chemical_formula_weight 404.39 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' Si Si 0.0817 0.0704 '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 10.128(5) _cell_length_b 10.750(5) _cell_length_c 12.890(5) _cell_angle_alpha 108.324(5) _cell_angle_beta 93.499(5) _cell_angle_gamma 117.089(5) _cell_volume 1151.0(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5485 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 28.0 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.889 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker X8 APEX 2' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23770 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.99 _reflns_number_total 5485 _reflns_number_gt 4637 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0473P)^2^+0.4144P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5485 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.03717(15) 0.18927(15) 0.23081(11) 0.0203(3) Uani 1 1 d . . . C2 C 0.13823(16) 0.21909(16) 0.32770(12) 0.0235(3) Uani 1 1 d . . . C3 C 0.0940(2) 0.1434(2) 0.41018(15) 0.0327(3) Uani 1 1 d . . . C4 C 0.29300(17) 0.32384(17) 0.35077(13) 0.0270(3) Uani 1 1 d . . . C5 C 0.35464(16) 0.39895(16) 0.28175(13) 0.0279(3) Uani 1 1 d . . . C6 C 0.5221(2) 0.5126(2) 0.30903(19) 0.0418(4) Uani 1 1 d . . . C7 C 0.25529(17) 0.36849(16) 0.18725(13) 0.0260(3) Uani 1 1 d . . . C8 C 0.09867(16) 0.26840(16) 0.16029(12) 0.0234(3) Uani 1 1 d . . . C9 C 0.01000(19) 0.2567(2) 0.05616(15) 0.0332(4) Uani 1 1 d . . . C10 C -0.25054(19) -0.03770(18) 0.04900(12) 0.0282(3) Uani 1 1 d . . . C11 C -0.27447(14) 0.13008(14) 0.26746(11) 0.0172(2) Uani 1 1 d . . . C12 C -0.23947(14) 0.26191(14) 0.22993(11) 0.0180(3) Uani 1 1 d . . . C13 C -0.11614(16) 0.40657(15) 0.29139(12) 0.0233(3) Uani 1 1 d . . . C14 C -0.08554(18) 0.52589(16) 0.25826(14) 0.0299(3) Uani 1 1 d . . . C15 C -0.17621(18) 0.50411(17) 0.16267(14) 0.0297(3) Uani 1 1 d . . . C16 C -0.29726(17) 0.36084(17) 0.09915(13) 0.0261(3) Uani 1 1 d . . . C17 C -0.32834(16) 0.24146(16) 0.13197(12) 0.0215(3) Uani 1 1 d . . . C18 C -0.44701(15) 0.01580(15) 0.23726(11) 0.0194(3) Uani 1 1 d . . . C19 C -0.55238(16) 0.06605(16) 0.23758(12) 0.0223(3) Uani 1 1 d . . . C20 C -0.70761(16) -0.03255(18) 0.21557(13) 0.0265(3) Uani 1 1 d . . . C21 C -0.76215(17) -0.18350(18) 0.19489(13) 0.0290(3) Uani 1 1 d . . . C22 C -0.65996(18) -0.23368(17) 0.19923(14) 0.0306(3) Uani 1 1 d . . . C23 C -0.50406(17) -0.13591(16) 0.21979(13) 0.0255(3) Uani 1 1 d . . . C24 C -0.3153(2) 0.3176(2) 0.48946(15) 0.0357(4) Uani 1 1 d . . . C25 C -0.2893(2) 0.0457(2) 0.48050(15) 0.0324(3) Uani 1 1 d . . . B1 B -0.1751(2) -0.1422(2) 0.21549(17) 0.0306(4) Uani 1 1 d . . . Si1 Si -0.22445(5) 0.20366(4) 0.43064(3) 0.02229(10) Uani 1 1 d . . . P1 P -0.16374(4) 0.03871(4) 0.19863(3) 0.01908(9) Uani 1 1 d . . . H1 H -0.0690(19) 0.2969(18) 0.4692(14) 0.026(4) Uiso 1 1 d . . . H1A H -0.060(2) -0.126(2) 0.2028(16) 0.045(5) Uiso 1 1 d . . . H1B H -0.197(2) -0.1488(19) 0.2975(15) 0.034(5) Uiso 1 1 d . . . H1C H -0.272(2) -0.238(2) 0.1420(15) 0.038(5) Uiso 1 1 d . . . H3A H -0.013(2) 0.092(2) 0.4079(15) 0.035(5) Uiso 1 1 d . . . H3B H 0.124(3) 0.070(3) 0.4009(19) 0.062(7) Uiso 1 1 d . . . H3C H 0.138(2) 0.214(2) 0.4817(19) 0.051(6) Uiso 1 1 d . . . H4 H 0.359(2) 0.345(2) 0.4172(16) 0.039(5) Uiso 1 1 d . . . H6A H 0.556(3) 0.533(3) 0.247(3) 0.091(9) Uiso 1 1 d . . . H6B H 0.544(3) 0.610(3) 0.363(2) 0.088(9) Uiso 1 1 d . . . H6C H 0.588(4) 0.486(3) 0.342(3) 0.102(10) Uiso 1 1 d . . . H7 H 0.296(2) 0.4182(19) 0.1373(15) 0.032(5) Uiso 1 1 d . . . H9A H -0.022(2) 0.161(2) -0.0073(18) 0.048(6) Uiso 1 1 d . . . H9B H -0.082(2) 0.262(2) 0.0678(16) 0.038(5) Uiso 1 1 d . . . H9C H 0.075(2) 0.337(2) 0.0350(18) 0.052(6) Uiso 1 1 d . . . H10A H -0.191(2) -0.073(2) 0.0085(16) 0.038(5) Uiso 1 1 d . . . H10B H -0.348(2) -0.124(2) 0.0392(16) 0.042(5) Uiso 1 1 d . . . H10C H -0.266(2) 0.030(2) 0.0245(16) 0.038(5) Uiso 1 1 d . . . H13 H -0.053(2) 0.4212(19) 0.3549(15) 0.028(4) Uiso 1 1 d . . . H14 H -0.004(2) 0.626(2) 0.3036(16) 0.039(5) Uiso 1 1 d . . . H15 H -0.156(2) 0.586(2) 0.1418(15) 0.037(5) Uiso 1 1 d . . . H16 H -0.3577(19) 0.3439(18) 0.0334(15) 0.027(4) Uiso 1 1 d . . . H17 H -0.4131(19) 0.1467(19) 0.0886(14) 0.023(4) Uiso 1 1 d . . . H19 H -0.5177(19) 0.1698(19) 0.2508(14) 0.026(4) Uiso 1 1 d . . . H20 H -0.777(2) 0.0022(19) 0.2136(15) 0.032(5) Uiso 1 1 d . . . H21 H -0.868(2) -0.247(2) 0.1781(15) 0.035(5) Uiso 1 1 d . . . H22 H -0.693(2) -0.335(2) 0.1899(16) 0.042(5) Uiso 1 1 d . . . H23 H -0.4397(19) -0.1711(19) 0.2230(14) 0.025(4) Uiso 1 1 d . . . H24A H -0.285(3) 0.394(3) 0.465(2) 0.069(7) Uiso 1 1 d . . . H24B H -0.284(2) 0.356(2) 0.568(2) 0.052(6) Uiso 1 1 d . . . H24C H -0.426(3) 0.259(2) 0.4692(18) 0.054(6) Uiso 1 1 d . . . H25A H -0.400(3) -0.014(3) 0.461(2) 0.064(7) Uiso 1 1 d . . . H25B H -0.261(3) 0.090(3) 0.558(2) 0.064(7) Uiso 1 1 d . . . H25C H -0.251(3) -0.022(3) 0.448(2) 0.064(7) 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 C1 0.0180(6) 0.0226(6) 0.0233(7) 0.0082(5) 0.0068(5) 0.0128(5) C2 0.0240(7) 0.0260(7) 0.0249(7) 0.0085(6) 0.0059(5) 0.0168(6) C3 0.0302(8) 0.0438(9) 0.0321(9) 0.0204(8) 0.0064(7) 0.0212(8) C4 0.0230(7) 0.0290(7) 0.0275(8) 0.0052(6) 0.0019(6) 0.0159(6) C5 0.0214(7) 0.0233(7) 0.0345(8) 0.0037(6) 0.0075(6) 0.0125(6) C6 0.0229(8) 0.0373(9) 0.0503(11) 0.0089(9) 0.0078(8) 0.0087(7) C7 0.0263(7) 0.0250(7) 0.0318(8) 0.0120(6) 0.0139(6) 0.0153(6) C8 0.0237(7) 0.0275(7) 0.0251(7) 0.0105(6) 0.0100(6) 0.0167(6) C9 0.0285(8) 0.0488(10) 0.0325(8) 0.0250(8) 0.0132(7) 0.0206(8) C10 0.0296(8) 0.0302(8) 0.0215(7) 0.0034(6) 0.0043(6) 0.0168(7) C11 0.0172(6) 0.0164(6) 0.0195(6) 0.0066(5) 0.0047(5) 0.0097(5) C12 0.0179(6) 0.0182(6) 0.0210(6) 0.0084(5) 0.0077(5) 0.0106(5) C13 0.0224(7) 0.0214(6) 0.0225(7) 0.0078(5) 0.0035(5) 0.0088(5) C14 0.0293(8) 0.0195(7) 0.0329(8) 0.0098(6) 0.0069(6) 0.0062(6) C15 0.0338(8) 0.0273(7) 0.0373(8) 0.0202(7) 0.0149(7) 0.0169(6) C16 0.0267(7) 0.0324(8) 0.0274(7) 0.0168(6) 0.0084(6) 0.0175(6) C17 0.0191(6) 0.0217(6) 0.0231(7) 0.0084(5) 0.0047(5) 0.0099(5) C18 0.0184(6) 0.0206(6) 0.0196(6) 0.0080(5) 0.0062(5) 0.0096(5) C19 0.0207(7) 0.0230(7) 0.0254(7) 0.0108(6) 0.0073(5) 0.0117(5) C20 0.0202(7) 0.0360(8) 0.0274(7) 0.0148(6) 0.0088(6) 0.0153(6) C21 0.0192(7) 0.0314(8) 0.0282(8) 0.0126(6) 0.0067(6) 0.0054(6) C22 0.0284(8) 0.0205(7) 0.0366(8) 0.0112(6) 0.0099(6) 0.0071(6) C23 0.0252(7) 0.0218(7) 0.0311(8) 0.0101(6) 0.0080(6) 0.0130(6) C24 0.0494(11) 0.0388(9) 0.0273(8) 0.0093(7) 0.0138(8) 0.0304(9) C25 0.0425(10) 0.0388(9) 0.0289(8) 0.0209(7) 0.0149(7) 0.0245(8) B1 0.0307(9) 0.0263(8) 0.0432(10) 0.0156(8) 0.0124(8) 0.0188(7) Si1 0.0261(2) 0.0245(2) 0.01871(19) 0.00788(15) 0.00527(15) 0.01490(16) P1 0.01829(17) 0.01966(17) 0.02122(18) 0.00686(13) 0.00540(13) 0.01159(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.415(2) . ? C1 C8 1.4181(19) . ? C1 P1 1.8459(15) . ? C2 C4 1.392(2) . ? C2 C3 1.504(2) . ? C3 H3A 0.963(19) . ? C3 H3B 0.94(2) . ? C3 H3C 0.91(2) . ? C4 C5 1.376(2) . ? C4 H4 0.949(19) . ? C5 C7 1.379(2) . ? C5 C6 1.504(2) . ? C6 H6A 0.94(3) . ? C6 H6B 0.98(3) . ? C6 H6C 0.96(3) . ? C7 C8 1.392(2) . ? C7 H7 0.958(18) . ? C8 C9 1.506(2) . ? C9 H9A 0.99(2) . ? C9 H9B 0.982(19) . ? C9 H9C 0.95(2) . ? C10 P1 1.8185(17) . ? C10 H10A 0.95(2) . ? C10 H10B 0.96(2) . ? C10 H10C 0.94(2) . ? C11 C12 1.5370(18) . ? C11 C18 1.5413(18) . ? C11 P1 1.8937(14) . ? C11 Si1 1.9405(15) . ? C12 C13 1.3934(19) . ? C12 C17 1.3998(19) . ? C13 C14 1.386(2) . ? C13 H13 0.928(18) . ? C14 C15 1.379(2) . ? C14 H14 0.956(19) . ? C15 C16 1.382(2) . ? C15 H15 0.940(19) . ? C16 C17 1.384(2) . ? C16 H16 0.930(17) . ? C17 H17 0.935(16) . ? C18 C23 1.393(2) . ? C18 C19 1.3981(19) . ? C19 C20 1.384(2) . ? C19 H19 0.955(17) . ? C20 C21 1.380(2) . ? C20 H20 0.938(18) . ? C21 C22 1.373(2) . ? C21 H21 0.934(18) . ? C22 C23 1.389(2) . ? C22 H22 0.943(19) . ? C23 H23 0.895(17) . ? C24 Si1 1.8570(18) . ? C24 H24A 0.90(3) . ? C24 H24B 0.94(2) . ? C24 H24C 0.97(2) . ? C25 Si1 1.8573(18) . ? C25 H25A 0.97(2) . ? C25 H25B 0.92(3) . ? C25 H25C 0.97(2) . ? B1 P1 1.9771(19) . ? B1 H1A 1.13(2) . ? B1 H1B 1.110(18) . ? B1 H1C 1.129(18) . ? Si1 H1 1.373(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C8 118.10(13) . . ? C2 C1 P1 117.59(10) . . ? C8 C1 P1 124.13(11) . . ? C4 C2 C1 119.59(13) . . ? C4 C2 C3 115.01(13) . . ? C1 C2 C3 125.39(13) . . ? C2 C3 H3A 116.1(11) . . ? C2 C3 H3B 112.3(14) . . ? H3A C3 H3B 105.4(17) . . ? C2 C3 H3C 109.9(14) . . ? H3A C3 H3C 104.4(17) . . ? H3B C3 H3C 108.2(19) . . ? C5 C4 C2 122.87(14) . . ? C5 C4 H4 118.3(11) . . ? C2 C4 H4 118.8(11) . . ? C4 C5 C7 117.06(14) . . ? C4 C5 C6 121.85(15) . . ? C7 C5 C6 121.07(16) . . ? C5 C6 H6A 113.8(18) . . ? C5 C6 H6B 110.1(16) . . ? H6A C6 H6B 104(2) . . ? C5 C6 H6C 114.3(18) . . ? H6A C6 H6C 107(3) . . ? H6B C6 H6C 106(2) . . ? C5 C7 C8 123.33(14) . . ? C5 C7 H7 118.5(11) . . ? C8 C7 H7 118.1(11) . . ? C7 C8 C1 119.00(13) . . ? C7 C8 C9 114.79(13) . . ? C1 C8 C9 126.21(13) . . ? C8 C9 H9A 111.2(12) . . ? C8 C9 H9B 112.5(11) . . ? H9A C9 H9B 107.6(16) . . ? C8 C9 H9C 108.1(13) . . ? H9A C9 H9C 107.5(17) . . ? H9B C9 H9C 109.7(16) . . ? P1 C10 H10A 108.1(11) . . ? P1 C10 H10B 103.7(12) . . ? H10A C10 H10B 108.5(16) . . ? P1 C10 H10C 114.3(12) . . ? H10A C10 H10C 112.7(16) . . ? H10B C10 H10C 109.1(16) . . ? C12 C11 C18 112.40(11) . . ? C12 C11 P1 106.61(9) . . ? C18 C11 P1 111.99(9) . . ? C12 C11 Si1 109.97(9) . . ? C18 C11 Si1 101.91(8) . . ? P1 C11 Si1 114.07(7) . . ? C13 C12 C17 117.22(12) . . ? C13 C12 C11 121.21(12) . . ? C17 C12 C11 121.57(11) . . ? C14 C13 C12 121.22(14) . . ? C14 C13 H13 120.4(10) . . ? C12 C13 H13 118.4(10) . . ? C15 C14 C13 120.68(14) . . ? C15 C14 H14 118.8(11) . . ? C13 C14 H14 120.4(11) . . ? C14 C15 C16 119.06(14) . . ? C14 C15 H15 120.1(11) . . ? C16 C15 H15 120.9(11) . . ? C15 C16 C17 120.45(14) . . ? C15 C16 H16 120.0(10) . . ? C17 C16 H16 119.5(10) . . ? C16 C17 C12 121.34(13) . . ? C16 C17 H17 118.4(10) . . ? C12 C17 H17 120.3(10) . . ? C23 C18 C19 117.20(13) . . ? C23 C18 C11 122.57(12) . . ? C19 C18 C11 119.93(12) . . ? C20 C19 C18 121.38(14) . . ? C20 C19 H19 118.8(10) . . ? C18 C19 H19 119.8(10) . . ? C21 C20 C19 120.43(14) . . ? C21 C20 H20 119.2(11) . . ? C19 C20 H20 120.4(11) . . ? C22 C21 C20 119.05(14) . . ? C22 C21 H21 122.8(11) . . ? C20 C21 H21 118.1(11) . . ? C21 C22 C23 120.87(14) . . ? C21 C22 H22 121.4(12) . . ? C23 C22 H22 117.7(12) . . ? C22 C23 C18 120.96(14) . . ? C22 C23 H23 119.2(11) . . ? C18 C23 H23 119.9(11) . . ? Si1 C24 H24A 109.1(16) . . ? Si1 C24 H24B 108.1(13) . . ? H24A C24 H24B 111(2) . . ? Si1 C24 H24C 113.3(13) . . ? H24A C24 H24C 109(2) . . ? H24B C24 H24C 107.0(18) . . ? Si1 C25 H25A 110.7(14) . . ? Si1 C25 H25B 106.3(15) . . ? H25A C25 H25B 105.9(19) . . ? Si1 C25 H25C 112.4(14) . . ? H25A C25 H25C 107.4(19) . . ? H25B C25 H25C 114(2) . . ? P1 B1 H1A 100.4(10) . . ? P1 B1 H1B 112.9(9) . . ? H1A B1 H1B 114.9(13) . . ? P1 B1 H1C 102.4(9) . . ? H1A B1 H1C 112.7(14) . . ? H1B B1 H1C 112.2(13) . . ? C24 Si1 C25 108.76(9) . . ? C24 Si1 C11 110.17(7) . . ? C25 Si1 C11 111.69(7) . . ? C24 Si1 H1 107.8(7) . . ? C25 Si1 H1 110.1(7) . . ? C11 Si1 H1 108.2(7) . . ? C10 P1 C1 110.20(7) . . ? C10 P1 C11 103.74(7) . . ? C1 P1 C11 107.81(7) . . ? C10 P1 B1 100.69(8) . . ? C1 P1 B1 110.63(8) . . ? C11 P1 B1 122.91(7) . . ? 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 C1 C2 C4 0.0(2) . . . . ? P1 C1 C2 C4 175.34(10) . . . . ? C8 C1 C2 C3 -178.49(14) . . . . ? P1 C1 C2 C3 -3.18(19) . . . . ? C1 C2 C4 C5 -1.5(2) . . . . ? C3 C2 C4 C5 177.20(14) . . . . ? C2 C4 C5 C7 1.1(2) . . . . ? C2 C4 C5 C6 179.53(15) . . . . ? C4 C5 C7 C8 0.7(2) . . . . ? C6 C5 C7 C8 -177.72(14) . . . . ? C5 C7 C8 C1 -2.1(2) . . . . ? C5 C7 C8 C9 177.44(14) . . . . ? C2 C1 C8 C7 1.67(19) . . . . ? P1 C1 C8 C7 -173.32(10) . . . . ? C2 C1 C8 C9 -177.81(14) . . . . ? P1 C1 C8 C9 7.2(2) . . . . ? C18 C11 C12 C13 147.41(12) . . . . ? P1 C11 C12 C13 -89.53(14) . . . . ? Si1 C11 C12 C13 34.62(15) . . . . ? C18 C11 C12 C17 -33.59(17) . . . . ? P1 C11 C12 C17 89.48(14) . . . . ? Si1 C11 C12 C17 -146.38(11) . . . . ? C17 C12 C13 C14 1.7(2) . . . . ? C11 C12 C13 C14 -179.27(13) . . . . ? C12 C13 C14 C15 -0.5(2) . . . . ? C13 C14 C15 C16 -0.9(2) . . . . ? C14 C15 C16 C17 0.9(2) . . . . ? C15 C16 C17 C12 0.3(2) . . . . ? C13 C12 C17 C16 -1.6(2) . . . . ? C11 C12 C17 C16 179.36(12) . . . . ? C12 C11 C18 C23 153.45(13) . . . . ? P1 C11 C18 C23 33.46(16) . . . . ? Si1 C11 C18 C23 -88.87(13) . . . . ? C12 C11 C18 C19 -33.00(16) . . . . ? P1 C11 C18 C19 -153.00(11) . . . . ? Si1 C11 C18 C19 84.68(13) . . . . ? C23 C18 C19 C20 -3.3(2) . . . . ? C11 C18 C19 C20 -177.21(12) . . . . ? C18 C19 C20 C21 1.4(2) . . . . ? C19 C20 C21 C22 1.6(2) . . . . ? C20 C21 C22 C23 -2.5(2) . . . . ? C21 C22 C23 C18 0.4(2) . . . . ? C19 C18 C23 C22 2.5(2) . . . . ? C11 C18 C23 C22 176.17(13) . . . . ? C12 C11 Si1 C24 51.13(12) . . . . ? C18 C11 Si1 C24 -68.28(11) . . . . ? P1 C11 Si1 C24 170.84(8) . . . . ? C12 C11 Si1 C25 172.12(9) . . . . ? C18 C11 Si1 C25 52.71(11) . . . . ? P1 C11 Si1 C25 -68.18(10) . . . . ? C2 C1 P1 C10 -155.28(11) . . . . ? C8 C1 P1 C10 19.73(14) . . . . ? C2 C1 P1 C11 92.14(11) . . . . ? C8 C1 P1 C11 -92.85(12) . . . . ? C2 C1 P1 B1 -44.81(13) . . . . ? C8 C1 P1 B1 130.20(12) . . . . ? C12 C11 P1 C10 -65.06(10) . . . . ? C18 C11 P1 C10 58.26(11) . . . . ? Si1 C11 P1 C10 173.36(7) . . . . ? C12 C11 P1 C1 51.81(10) . . . . ? C18 C11 P1 C1 175.13(9) . . . . ? Si1 C11 P1 C1 -69.77(8) . . . . ? C12 C11 P1 B1 -177.75(9) . . . . ? C18 C11 P1 B1 -54.43(12) . . . . ? Si1 C11 P1 B1 60.67(10) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.438 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.045 #===END data_dg061 _database_code_depnum_ccdc_archive 'CCDC 668086' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 B P' _chemical_formula_sum 'C23 H28 B P' _chemical_formula_weight 346.23 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 8.342(5) _cell_length_b 13.896(5) _cell_length_c 16.931(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 99.909(5) _cell_angle_gamma 90.000(5) _cell_volume 1933.4(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2889 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 23.6 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.684 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker X8 APEX 2' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26106 _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 23.63 _reflns_number_total 2889 _reflns_number_gt 2021 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0973P)^2^+3.6733P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2889 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1095 _refine_ls_R_factor_gt 0.0732 _refine_ls_wR_factor_ref 0.2219 _refine_ls_wR_factor_gt 0.1898 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0975(5) 0.0230(3) 0.2753(2) 0.0394(11) Uani 1 1 d . . . C2 C -0.2327(5) 0.0436(3) 0.3106(3) 0.0437(12) Uani 1 1 d . . . C3 C -0.3614(7) 0.1117(5) 0.2775(3) 0.0700(17) Uani 1 1 d . . . H3A H -0.3129 0.1745 0.2698 0.105 Uiso 1 1 calc R . . H3B H -0.4385 0.1185 0.3148 0.105 Uiso 1 1 calc R . . H3C H -0.4188 0.0877 0.2259 0.105 Uiso 1 1 calc R . . C4 C -0.2468(6) -0.0031(4) 0.3821(3) 0.0506(13) Uani 1 1 d . . . H4 H -0.3391 0.0102 0.4062 0.061 Uiso 1 1 calc R . . C5 C -0.1356(6) -0.0661(4) 0.4184(3) 0.0500(13) Uani 1 1 d . . . C6 C -0.1572(7) -0.1157(4) 0.4941(3) 0.0689(17) Uani 1 1 d . . . H6A H -0.1770 -0.1844 0.4834 0.103 Uiso 1 1 calc R . . H6B H -0.2501 -0.0877 0.5142 0.103 Uiso 1 1 calc R . . H6C H -0.0585 -0.1078 0.5343 0.103 Uiso 1 1 calc R . . C7 C -0.0025(7) -0.0821(4) 0.3851(3) 0.0532(13) Uani 1 1 d . . . H7 H 0.0782 -0.1251 0.4111 0.064 Uiso 1 1 calc R . . C8 C 0.0212(6) -0.0389(3) 0.3152(3) 0.0492(12) Uani 1 1 d . . . C9 C 0.1828(8) -0.0601(5) 0.2920(4) 0.081(2) Uani 1 1 d . . . H9A H 0.2653 -0.0168 0.3211 0.121 Uiso 1 1 calc R . . H9B H 0.1758 -0.0504 0.2342 0.121 Uiso 1 1 calc R . . H9C H 0.2132 -0.1270 0.3056 0.121 Uiso 1 1 calc R . . C10 C -0.0246(7) -0.0269(4) 0.1197(3) 0.0644(15) Uani 1 1 d . . . H10A H 0.0924 -0.0238 0.1189 0.097 Uiso 1 1 calc R . . H10B H -0.0848 -0.0229 0.0648 0.097 Uiso 1 1 calc R . . H10C H -0.0503 -0.0879 0.1439 0.097 Uiso 1 1 calc R . . C11 C 0.0963(5) 0.1513(3) 0.1952(2) 0.0372(11) Uani 1 1 d . . . H11 H 0.1896 0.1097 0.2196 0.045 Uiso 1 1 calc R . . C12 C 0.1394(5) 0.1878(3) 0.1175(2) 0.0379(11) Uani 1 1 d . . . C13 C 0.2737(6) 0.1509(4) 0.0927(3) 0.0475(12) Uani 1 1 d . . . H13 H 0.3374 0.1035 0.1242 0.057 Uiso 1 1 calc R . . C14 C 0.3176(6) 0.1823(4) 0.0221(3) 0.0570(14) Uani 1 1 d . . . H14 H 0.4105 0.1556 0.0048 0.068 Uiso 1 1 calc R . . C15 C 0.2304(7) 0.2500(4) -0.0219(3) 0.0566(14) Uani 1 1 d . . . H15 H 0.2615 0.2713 -0.0704 0.068 Uiso 1 1 calc R . . C16 C 0.0977(6) 0.2882(4) 0.0023(3) 0.0576(14) Uani 1 1 d . . . H16 H 0.0360 0.3366 -0.0289 0.069 Uiso 1 1 calc R . . C17 C 0.0525(6) 0.2566(4) 0.0724(3) 0.0484(12) Uani 1 1 d . . . H17 H -0.0408 0.2833 0.0893 0.058 Uiso 1 1 calc R . . C18 C 0.0816(5) 0.2267(3) 0.2566(2) 0.0345(10) Uani 1 1 d . . . C19 C 0.2024(6) 0.2333(3) 0.3229(2) 0.0429(11) Uani 1 1 d . . . H19 H 0.2904 0.1890 0.3291 0.052 Uiso 1 1 calc R . . C20 C 0.1984(6) 0.3021(4) 0.3796(2) 0.0481(13) Uani 1 1 d . . . H20 H 0.2834 0.3052 0.4247 0.058 Uiso 1 1 calc R . . C21 C 0.0760(6) 0.3655(4) 0.3725(3) 0.0495(13) Uani 1 1 d . . . H21 H 0.0742 0.4138 0.4121 0.059 Uiso 1 1 calc R . . C22 C -0.0459(6) 0.3599(4) 0.3079(3) 0.0536(13) Uani 1 1 d . . . H22 H -0.1331 0.4047 0.3026 0.064 Uiso 1 1 calc R . . C23 C -0.0448(6) 0.2909(3) 0.2507(3) 0.0459(12) Uani 1 1 d . . . H23 H -0.1319 0.2874 0.2065 0.055 Uiso 1 1 calc R . . B1 B -0.2603(8) 0.1208(6) 0.1116(4) 0.0667(19) Uani 1 1 d . . . H1A H -0.290(3) 0.183(2) 0.1329(15) 0.100 Uiso 1 1 calc R . . H1B H -0.352(3) 0.076(2) 0.109(2) 0.100 Uiso 1 1 calc R . . H1C H -0.2348(19) 0.130(3) 0.0574(18) 0.100 Uiso 1 1 calc R . . P1 P -0.08194(15) 0.07161(9) 0.17750(6) 0.0429(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 C1 0.047(3) 0.045(3) 0.029(2) -0.007(2) 0.014(2) -0.010(2) C2 0.040(3) 0.055(3) 0.037(3) -0.011(2) 0.008(2) -0.007(2) C3 0.057(3) 0.110(5) 0.047(3) -0.004(3) 0.020(3) 0.010(3) C4 0.049(3) 0.074(4) 0.034(3) -0.014(2) 0.020(2) -0.021(3) C5 0.063(3) 0.051(3) 0.036(3) -0.002(2) 0.008(2) -0.019(3) C6 0.095(4) 0.079(4) 0.034(3) 0.003(3) 0.016(3) -0.037(4) C7 0.074(4) 0.046(3) 0.041(3) 0.008(2) 0.015(3) -0.002(3) C8 0.064(3) 0.046(3) 0.040(3) 0.003(2) 0.015(2) 0.009(3) C9 0.086(4) 0.099(5) 0.063(4) 0.025(3) 0.030(3) 0.047(4) C10 0.084(4) 0.073(4) 0.041(3) -0.015(3) 0.023(3) -0.015(3) C11 0.036(2) 0.051(3) 0.025(2) 0.0027(19) 0.0077(18) 0.002(2) C12 0.035(2) 0.054(3) 0.025(2) -0.001(2) 0.0055(18) -0.005(2) C13 0.044(3) 0.066(3) 0.034(2) -0.004(2) 0.011(2) 0.003(2) C14 0.051(3) 0.084(4) 0.042(3) -0.011(3) 0.024(2) -0.005(3) C15 0.063(3) 0.079(4) 0.029(3) 0.004(3) 0.013(2) -0.014(3) C16 0.056(3) 0.080(4) 0.037(3) 0.016(3) 0.009(2) -0.008(3) C17 0.040(3) 0.069(3) 0.037(3) 0.010(2) 0.011(2) -0.002(3) C18 0.039(2) 0.042(2) 0.024(2) 0.0060(18) 0.0113(18) -0.002(2) C19 0.047(3) 0.054(3) 0.028(2) 0.005(2) 0.008(2) 0.003(2) C20 0.063(3) 0.063(3) 0.019(2) 0.001(2) 0.008(2) -0.005(3) C21 0.073(4) 0.052(3) 0.029(2) 0.001(2) 0.026(2) -0.007(3) C22 0.059(3) 0.055(3) 0.049(3) 0.005(2) 0.018(3) 0.013(3) C23 0.047(3) 0.057(3) 0.032(2) 0.002(2) 0.003(2) 0.008(2) B1 0.056(4) 0.086(5) 0.059(4) 0.029(4) 0.013(3) 0.001(4) P1 0.0471(8) 0.0578(8) 0.0251(6) 0.0003(5) 0.0097(5) -0.0053(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.394(6) . ? C1 C8 1.395(7) . ? C1 P1 1.814(4) . ? C2 C4 1.397(7) . ? C2 C3 1.469(7) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.344(7) . ? C4 H4 0.9500 . ? C5 C7 1.348(7) . ? C5 C6 1.493(6) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.372(6) . ? C7 H7 0.9500 . ? C8 C9 1.496(7) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 P1 1.795(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C18 1.496(6) . ? C11 C12 1.510(6) . ? C11 P1 1.837(4) . ? C11 H11 1.0000 . ? C12 C17 1.353(6) . ? C12 C13 1.362(6) . ? C13 C14 1.379(6) . ? C13 H13 0.9500 . ? C14 C15 1.335(7) . ? C14 H14 0.9500 . ? C15 C16 1.353(7) . ? C15 H15 0.9500 . ? C16 C17 1.378(6) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.372(6) . ? C18 C19 1.376(6) . ? C19 C20 1.359(6) . ? C19 H19 0.9500 . ? C20 C21 1.338(7) . ? C20 H20 0.9500 . ? C21 C22 1.362(7) . ? C21 H21 0.9500 . ? C22 C23 1.364(7) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? B1 P1 1.831(6) . ? B1 H1A 0.9850 . ? B1 H1B 0.9850 . ? B1 H1C 0.9850 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C8 118.6(4) . . ? C2 C1 P1 120.4(4) . . ? C8 C1 P1 121.0(3) . . ? C1 C2 C4 118.1(5) . . ? C1 C2 C3 124.1(4) . . ? C4 C2 C3 117.7(4) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C2 123.0(4) . . ? C5 C4 H4 118.5 . . ? C2 C4 H4 118.5 . . ? C4 C5 C7 118.0(4) . . ? C4 C5 C6 121.2(5) . . ? C7 C5 C6 120.8(5) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 C8 122.7(5) . . ? C5 C7 H7 118.6 . . ? C8 C7 H7 118.6 . . ? C7 C8 C1 119.4(5) . . ? C7 C8 C9 114.2(5) . . ? C1 C8 C9 126.2(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? P1 C10 H10A 109.5 . . ? P1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? P1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C18 C11 C12 115.6(4) . . ? C18 C11 P1 112.0(3) . . ? C12 C11 P1 111.6(3) . . ? C18 C11 H11 105.6 . . ? C12 C11 H11 105.6 . . ? P1 C11 H11 105.6 . . ? C17 C12 C13 118.8(4) . . ? C17 C12 C11 122.9(4) . . ? C13 C12 C11 118.3(4) . . ? C12 C13 C14 120.1(5) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 120.4(5) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.2(5) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 119.6(5) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C12 C17 C16 120.8(5) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C23 C18 C19 117.5(4) . . ? C23 C18 C11 123.9(4) . . ? C19 C18 C11 118.6(4) . . ? C20 C19 C18 121.3(5) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C21 C20 C19 120.7(5) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C22 119.1(5) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C21 C22 C23 121.1(5) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C22 C23 C18 120.2(4) . . ? C22 C23 H23 119.9 . . ? C18 C23 H23 119.9 . . ? P1 B1 H1A 109.5 . . ? P1 B1 H1B 109.5 . . ? H1A B1 H1B 109.5 . . ? P1 B1 H1C 109.5 . . ? H1A B1 H1C 109.5 . . ? H1B B1 H1C 109.5 . . ? C10 P1 C1 106.3(2) . . ? C10 P1 B1 102.6(3) . . ? C1 P1 B1 121.1(3) . . ? C10 P1 C11 105.4(2) . . ? C1 P1 C11 105.02(19) . . ? B1 P1 C11 115.1(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 C1 C2 C4 -3.6(7) . . . . ? P1 C1 C2 C4 173.7(3) . . . . ? C8 C1 C2 C3 176.3(5) . . . . ? P1 C1 C2 C3 -6.4(7) . . . . ? C1 C2 C4 C5 0.6(7) . . . . ? C3 C2 C4 C5 -179.2(5) . . . . ? C2 C4 C5 C7 2.1(7) . . . . ? C2 C4 C5 C6 -178.9(4) . . . . ? C4 C5 C7 C8 -1.8(8) . . . . ? C6 C5 C7 C8 179.2(5) . . . . ? C5 C7 C8 C1 -1.3(8) . . . . ? C5 C7 C8 C9 175.2(5) . . . . ? C2 C1 C8 C7 3.9(7) . . . . ? P1 C1 C8 C7 -173.4(4) . . . . ? C2 C1 C8 C9 -172.1(5) . . . . ? P1 C1 C8 C9 10.6(7) . . . . ? C18 C11 C12 C17 -54.8(6) . . . . ? P1 C11 C12 C17 74.7(5) . . . . ? C18 C11 C12 C13 123.9(5) . . . . ? P1 C11 C12 C13 -106.6(4) . . . . ? C17 C12 C13 C14 -1.2(7) . . . . ? C11 C12 C13 C14 -179.9(4) . . . . ? C12 C13 C14 C15 0.9(8) . . . . ? C13 C14 C15 C16 -0.1(8) . . . . ? C14 C15 C16 C17 -0.4(8) . . . . ? C13 C12 C17 C16 0.6(7) . . . . ? C11 C12 C17 C16 179.3(4) . . . . ? C15 C16 C17 C12 0.1(8) . . . . ? C12 C11 C18 C23 72.3(5) . . . . ? P1 C11 C18 C23 -57.0(5) . . . . ? C12 C11 C18 C19 -106.9(4) . . . . ? P1 C11 C18 C19 123.8(4) . . . . ? C23 C18 C19 C20 -1.2(6) . . . . ? C11 C18 C19 C20 178.0(4) . . . . ? C18 C19 C20 C21 0.1(7) . . . . ? C19 C20 C21 C22 0.5(7) . . . . ? C20 C21 C22 C23 0.0(7) . . . . ? C21 C22 C23 C18 -1.2(7) . . . . ? C19 C18 C23 C22 1.7(6) . . . . ? C11 C18 C23 C22 -177.5(4) . . . . ? C2 C1 P1 C10 -132.5(4) . . . . ? C8 C1 P1 C10 44.7(4) . . . . ? C2 C1 P1 B1 -16.4(5) . . . . ? C8 C1 P1 B1 160.9(4) . . . . ? C2 C1 P1 C11 116.1(4) . . . . ? C8 C1 P1 C11 -66.7(4) . . . . ? C18 C11 P1 C10 -168.2(3) . . . . ? C12 C11 P1 C10 60.5(4) . . . . ? C18 C11 P1 C1 -56.2(3) . . . . ? C12 C11 P1 C1 172.5(3) . . . . ? C18 C11 P1 B1 79.6(4) . . . . ? C12 C11 P1 B1 -51.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 23.63 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.846 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.069 #===END data_dg072 _database_code_depnum_ccdc_archive 'CCDC 668087' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 P, C F3 O3 S' _chemical_formula_sum 'C25 H28 F3 O3 P S' _chemical_formula_weight 496.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.118(5) _cell_length_b 17.583(5) _cell_length_c 13.314(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 98.166(5) _cell_angle_gamma 90.000(5) _cell_volume 2344.6(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5623 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.9 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.842 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker X8 APEX 2' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40481 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.93 _reflns_number_total 5623 _reflns_number_gt 3960 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0430P)^2^+1.3944P] 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 5623 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.96557(19) 0.10407(11) 0.59291(13) 0.0204(4) Uani 1 1 d . . . C2 C 1.08250(19) 0.05898(11) 0.61434(14) 0.0224(4) Uani 1 1 d . . . C3 C 1.0947(2) -0.01288(13) 0.67657(18) 0.0362(5) Uani 1 1 d . . . H3A H 1.1854 -0.0332 0.6798 0.054 Uiso 1 1 calc R . . H3B H 1.0304 -0.0505 0.6451 0.054 Uiso 1 1 calc R . . H3C H 1.0764 -0.0017 0.7453 0.054 Uiso 1 1 calc R . . C4 C 1.1961(2) 0.08245(12) 0.57589(15) 0.0256(4) Uani 1 1 d . . . H4 H 1.2746 0.0525 0.5904 0.031 Uiso 1 1 calc R . . C5 C 1.2010(2) 0.14721(12) 0.51753(15) 0.0261(4) Uani 1 1 d . . . C6 C 1.3281(2) 0.17104(14) 0.48000(18) 0.0367(5) Uani 1 1 d . . . H6A H 1.3814 0.2022 0.5318 0.055 Uiso 1 1 calc R . . H6B H 1.3066 0.2007 0.4175 0.055 Uiso 1 1 calc R . . H6C H 1.3791 0.1258 0.4663 0.055 Uiso 1 1 calc R . . C7 C 1.0861(2) 0.19004(12) 0.49670(14) 0.0259(4) Uani 1 1 d . . . H7 H 1.0873 0.2344 0.4561 0.031 Uiso 1 1 calc R . . C8 C 0.9689(2) 0.17048(11) 0.53306(14) 0.0220(4) Uani 1 1 d . . . C9 C 0.8513(2) 0.22259(13) 0.50261(16) 0.0310(5) Uani 1 1 d . . . H9A H 0.8836 0.2728 0.4851 0.046 Uiso 1 1 calc R . . H9B H 0.7997 0.2276 0.5592 0.046 Uiso 1 1 calc R . . H9C H 0.7943 0.2012 0.4437 0.046 Uiso 1 1 calc R . . C10 C 0.6701(2) 0.08731(14) 0.54842(16) 0.0351(5) Uani 1 1 d . . . H10A H 0.6953 0.0670 0.4853 0.053 Uiso 1 1 calc R . . H10B H 0.6378 0.1396 0.5372 0.053 Uiso 1 1 calc R . . H10C H 0.5993 0.0558 0.5699 0.053 Uiso 1 1 calc R . . C11 C 0.8041(2) -0.00428(12) 0.70475(18) 0.0325(5) Uani 1 1 d . . . H11A H 0.7140 -0.0120 0.7219 0.049 Uiso 1 1 calc R . . H11B H 0.8690 -0.0062 0.7668 0.049 Uiso 1 1 calc R . . H11C H 0.8244 -0.0443 0.6581 0.049 Uiso 1 1 calc R . . C12 C 0.79873(19) 0.16215(11) 0.74041(14) 0.0217(4) Uani 1 1 d . . . H12 H 0.8386 0.2087 0.7138 0.026 Uiso 1 1 calc R . . C13 C 0.65467(19) 0.18232(11) 0.74756(14) 0.0218(4) Uani 1 1 d . . . C14 C 0.6134(2) 0.25699(12) 0.72708(15) 0.0273(5) Uani 1 1 d . . . H14 H 0.6757 0.2940 0.7112 0.033 Uiso 1 1 calc R . . C15 C 0.4814(2) 0.27751(13) 0.72979(16) 0.0332(5) Uani 1 1 d . . . H15 H 0.4543 0.3287 0.7165 0.040 Uiso 1 1 calc R . . C16 C 0.3896(2) 0.22456(13) 0.75152(16) 0.0330(5) Uani 1 1 d . . . H16 H 0.2992 0.2388 0.7524 0.040 Uiso 1 1 calc R . . C17 C 0.4297(2) 0.15085(13) 0.77199(16) 0.0324(5) Uani 1 1 d . . . H17 H 0.3669 0.1142 0.7879 0.039 Uiso 1 1 calc R . . C18 C 0.5603(2) 0.12952(12) 0.76969(15) 0.0270(5) Uani 1 1 d . . . H18 H 0.5863 0.0782 0.7834 0.032 Uiso 1 1 calc R . . C19 C 0.8893(2) 0.14193(11) 0.83862(14) 0.0226(4) Uani 1 1 d . . . C20 C 0.8427(2) 0.11069(13) 0.92208(16) 0.0315(5) Uani 1 1 d . . . H20 H 0.7499 0.1016 0.9206 0.038 Uiso 1 1 calc R . . C21 C 0.9312(3) 0.09249(14) 1.00811(17) 0.0402(6) Uani 1 1 d . . . H21 H 0.8983 0.0715 1.0655 0.048 Uiso 1 1 calc R . . C22 C 1.0656(3) 0.10446(14) 1.01131(18) 0.0425(6) Uani 1 1 d . . . H22 H 1.1258 0.0912 1.0701 0.051 Uiso 1 1 calc R . . C23 C 1.1125(2) 0.13588(14) 0.92858(18) 0.0381(6) Uani 1 1 d . . . H23 H 1.2055 0.1444 0.9304 0.046 Uiso 1 1 calc R . . C24 C 1.0253(2) 0.15510(12) 0.84296(16) 0.0306(5) Uani 1 1 d . . . H24 H 1.0586 0.1775 0.7866 0.037 Uiso 1 1 calc R . . C25 C 1.0472(2) 0.42501(14) 0.62493(17) 0.0358(5) Uani 1 1 d . . . O1 O 0.91087(18) 0.34045(10) 0.72666(13) 0.0486(5) Uani 1 1 d . . . O2 O 1.15020(18) 0.34449(10) 0.77733(15) 0.0536(5) Uani 1 1 d . . . O3 O 1.01636(16) 0.45210(9) 0.80894(11) 0.0344(4) Uani 1 1 d . . . F1 F 1.14838(16) 0.47333(9) 0.63002(11) 0.0575(4) Uani 1 1 d . . . F2 F 1.06626(19) 0.37235(10) 0.55830(12) 0.0672(5) Uani 1 1 d . . . F3 F 0.93776(17) 0.46338(10) 0.58713(11) 0.0635(5) Uani 1 1 d . . . P1 P 0.81303(5) 0.08660(3) 0.64542(4) 0.02157(13) Uani 1 1 d . . . S1 S 1.02887(5) 0.38545(3) 0.74865(4) 0.02671(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 C1 0.0192(10) 0.0249(10) 0.0171(9) -0.0016(7) 0.0027(7) 0.0010(8) C2 0.0224(10) 0.0231(10) 0.0214(9) -0.0012(8) 0.0022(8) 0.0025(8) C3 0.0290(12) 0.0339(13) 0.0460(13) 0.0129(10) 0.0059(10) 0.0108(10) C4 0.0191(10) 0.0289(11) 0.0286(10) -0.0051(9) 0.0026(8) 0.0057(9) C5 0.0243(11) 0.0306(12) 0.0240(10) -0.0062(8) 0.0056(8) -0.0019(9) C6 0.0281(12) 0.0445(14) 0.0392(13) -0.0009(11) 0.0110(10) -0.0033(11) C7 0.0306(11) 0.0264(11) 0.0215(9) 0.0006(8) 0.0063(8) -0.0010(9) C8 0.0227(10) 0.0255(10) 0.0176(9) -0.0026(8) 0.0020(7) 0.0033(8) C9 0.0311(12) 0.0326(12) 0.0293(11) 0.0069(9) 0.0045(9) 0.0081(10) C10 0.0232(11) 0.0501(15) 0.0309(11) -0.0102(10) 0.0000(9) -0.0006(10) C11 0.0329(12) 0.0227(11) 0.0447(13) -0.0024(10) 0.0157(10) -0.0040(10) C12 0.0224(10) 0.0181(10) 0.0257(10) -0.0020(8) 0.0075(8) -0.0017(8) C13 0.0228(10) 0.0231(10) 0.0207(9) -0.0043(8) 0.0071(8) 0.0013(8) C14 0.0319(12) 0.0234(11) 0.0275(10) -0.0013(8) 0.0075(8) -0.0003(9) C15 0.0389(13) 0.0304(12) 0.0304(11) -0.0008(9) 0.0055(10) 0.0125(10) C16 0.0253(11) 0.0454(14) 0.0285(11) -0.0067(10) 0.0045(9) 0.0084(10) C17 0.0258(12) 0.0377(13) 0.0359(12) -0.0066(10) 0.0119(9) -0.0035(10) C18 0.0266(11) 0.0224(11) 0.0339(11) -0.0031(8) 0.0104(9) 0.0007(9) C19 0.0265(11) 0.0188(10) 0.0232(9) -0.0042(8) 0.0050(8) -0.0006(8) C20 0.0330(12) 0.0329(12) 0.0296(11) 0.0008(9) 0.0081(9) -0.0039(10) C21 0.0537(16) 0.0397(14) 0.0269(11) 0.0057(10) 0.0051(10) -0.0055(12) C22 0.0497(16) 0.0385(14) 0.0342(12) -0.0001(10) -0.0112(11) -0.0028(12) C23 0.0294(12) 0.0403(14) 0.0421(13) -0.0099(11) -0.0030(10) -0.0084(11) C24 0.0295(12) 0.0328(12) 0.0295(11) -0.0073(9) 0.0041(9) -0.0108(10) C25 0.0394(14) 0.0376(13) 0.0326(12) -0.0058(10) 0.0124(10) -0.0076(11) O1 0.0464(11) 0.0514(11) 0.0502(10) -0.0040(8) 0.0142(8) -0.0242(9) O2 0.0458(11) 0.0447(11) 0.0689(12) 0.0074(9) 0.0033(9) 0.0225(9) O3 0.0404(9) 0.0311(9) 0.0320(8) -0.0020(7) 0.0062(7) 0.0045(7) F1 0.0664(11) 0.0576(10) 0.0530(9) 0.0009(7) 0.0242(8) -0.0311(8) F2 0.0928(13) 0.0639(11) 0.0539(9) -0.0259(8) 0.0413(9) -0.0197(10) F3 0.0664(11) 0.0822(12) 0.0391(8) 0.0194(8) -0.0023(7) 0.0133(10) P1 0.0183(3) 0.0246(3) 0.0224(2) -0.0035(2) 0.00460(19) 0.0000(2) S1 0.0256(3) 0.0228(3) 0.0325(3) 0.0019(2) 0.0068(2) 0.0006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C8 1.417(3) . ? C1 C2 1.419(3) . ? C1 P1 1.809(2) . ? C2 C4 1.386(3) . ? C2 C3 1.506(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.383(3) . ? C4 H4 0.9500 . ? C5 C7 1.380(3) . ? C5 C6 1.504(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.386(3) . ? C7 H7 0.9500 . ? C8 C9 1.511(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 P1 1.797(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 P1 1.790(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.516(3) . ? C12 C19 1.528(3) . ? C12 P1 1.854(2) . ? C12 H12 1.0000 . ? C13 C18 1.393(3) . ? C13 C14 1.393(3) . ? C14 C15 1.389(3) . ? C14 H14 0.9500 . ? C15 C16 1.375(3) . ? C15 H15 0.9500 . ? C16 C17 1.374(3) . ? C16 H16 0.9500 . ? C17 C18 1.378(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.381(3) . ? C19 C24 1.389(3) . ? C20 C21 1.387(3) . ? C20 H20 0.9500 . ? C21 C22 1.371(4) . ? C21 H21 0.9500 . ? C22 C23 1.376(3) . ? C22 H22 0.9500 . ? C23 C24 1.381(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 F2 1.315(3) . ? C25 F1 1.325(3) . ? C25 F3 1.333(3) . ? C25 S1 1.822(2) . ? O1 S1 1.4275(18) . ? O2 S1 1.4278(18) . ? O3 S1 1.4362(16) . ? 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 C1 C2 119.21(18) . . ? C8 C1 P1 116.54(14) . . ? C2 C1 P1 124.07(15) . . ? C4 C2 C1 118.08(18) . . ? C4 C2 C3 116.44(18) . . ? C1 C2 C3 125.47(18) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C2 123.42(19) . . ? C5 C4 H4 118.3 . . ? C2 C4 H4 118.3 . . ? C7 C5 C4 117.72(19) . . ? C7 C5 C6 121.1(2) . . ? C4 C5 C6 121.12(19) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 C8 122.19(19) . . ? C5 C7 H7 118.9 . . ? C8 C7 H7 118.9 . . ? C7 C8 C1 119.38(18) . . ? C7 C8 C9 115.83(18) . . ? C1 C8 C9 124.78(18) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? P1 C10 H10A 109.5 . . ? P1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? P1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? P1 C11 H11A 109.5 . . ? P1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? P1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C19 117.75(16) . . ? C13 C12 P1 112.29(13) . . ? C19 C12 P1 108.76(13) . . ? C13 C12 H12 105.7 . . ? C19 C12 H12 105.7 . . ? P1 C12 H12 105.7 . . ? C18 C13 C14 118.30(19) . . ? C18 C13 C12 123.47(18) . . ? C14 C13 C12 118.18(18) . . ? C15 C14 C13 120.2(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 120.7(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 119.4(2) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 120.6(2) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C17 C18 C13 120.8(2) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? C20 C19 C24 118.84(19) . . ? C20 C19 C12 123.32(19) . . ? C24 C19 C12 117.84(18) . . ? C19 C20 C21 120.1(2) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 120.8(2) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C23 119.4(2) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C22 C23 C24 120.5(2) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C19 120.4(2) . . ? C23 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? F2 C25 F1 107.45(19) . . ? F2 C25 F3 107.2(2) . . ? F1 C25 F3 106.8(2) . . ? F2 C25 S1 112.62(17) . . ? F1 C25 S1 112.08(16) . . ? F3 C25 S1 110.41(16) . . ? C11 P1 C10 103.74(11) . . ? C11 P1 C1 114.92(10) . . ? C10 P1 C1 111.39(10) . . ? C11 P1 C12 108.96(10) . . ? C10 P1 C12 110.64(10) . . ? C1 P1 C12 107.19(9) . . ? O1 S1 O2 115.95(12) . . ? O1 S1 O3 115.42(11) . . ? O2 S1 O3 113.76(11) . . ? O1 S1 C25 102.47(11) . . ? O2 S1 C25 103.90(12) . . ? O3 S1 C25 102.84(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C1 C2 C4 0.4(3) . . . . ? P1 C1 C2 C4 -174.60(14) . . . . ? C8 C1 C2 C3 179.99(19) . . . . ? P1 C1 C2 C3 5.0(3) . . . . ? C1 C2 C4 C5 -0.3(3) . . . . ? C3 C2 C4 C5 -179.90(19) . . . . ? C2 C4 C5 C7 -0.3(3) . . . . ? C2 C4 C5 C6 178.43(19) . . . . ? C4 C5 C7 C8 0.7(3) . . . . ? C6 C5 C7 C8 -177.99(19) . . . . ? C5 C7 C8 C1 -0.6(3) . . . . ? C5 C7 C8 C9 -179.31(18) . . . . ? C2 C1 C8 C7 0.0(3) . . . . ? P1 C1 C8 C7 175.38(14) . . . . ? C2 C1 C8 C9 178.61(18) . . . . ? P1 C1 C8 C9 -6.0(3) . . . . ? C19 C12 C13 C18 -70.5(2) . . . . ? P1 C12 C13 C18 57.0(2) . . . . ? C19 C12 C13 C14 112.1(2) . . . . ? P1 C12 C13 C14 -120.42(17) . . . . ? C18 C13 C14 C15 0.5(3) . . . . ? C12 C13 C14 C15 178.11(17) . . . . ? C13 C14 C15 C16 -0.7(3) . . . . ? C14 C15 C16 C17 0.8(3) . . . . ? C15 C16 C17 C18 -0.8(3) . . . . ? C16 C17 C18 C13 0.6(3) . . . . ? C14 C13 C18 C17 -0.5(3) . . . . ? C12 C13 C18 C17 -177.93(18) . . . . ? C13 C12 C19 C20 27.8(3) . . . . ? P1 C12 C19 C20 -101.4(2) . . . . ? C13 C12 C19 C24 -152.94(18) . . . . ? P1 C12 C19 C24 77.9(2) . . . . ? C24 C19 C20 C21 -0.4(3) . . . . ? C12 C19 C20 C21 178.8(2) . . . . ? C19 C20 C21 C22 -0.6(4) . . . . ? C20 C21 C22 C23 0.9(4) . . . . ? C21 C22 C23 C24 -0.1(4) . . . . ? C22 C23 C24 C19 -1.0(3) . . . . ? C20 C19 C24 C23 1.2(3) . . . . ? C12 C19 C24 C23 -178.07(19) . . . . ? C8 C1 P1 C11 171.37(14) . . . . ? C2 C1 P1 C11 -13.5(2) . . . . ? C8 C1 P1 C10 53.78(18) . . . . ? C2 C1 P1 C10 -131.09(17) . . . . ? C8 C1 P1 C12 -67.39(16) . . . . ? C2 C1 P1 C12 107.75(17) . . . . ? C13 C12 P1 C11 -86.64(16) . . . . ? C19 C12 P1 C11 45.48(16) . . . . ? C13 C12 P1 C10 26.80(17) . . . . ? C19 C12 P1 C10 158.92(14) . . . . ? C13 C12 P1 C1 148.43(14) . . . . ? C19 C12 P1 C1 -79.45(15) . . . . ? F2 C25 S1 O1 -62.7(2) . . . . ? F1 C25 S1 O1 175.97(17) . . . . ? F3 C25 S1 O1 57.03(19) . . . . ? F2 C25 S1 O2 58.4(2) . . . . ? F1 C25 S1 O2 -62.9(2) . . . . ? F3 C25 S1 O2 178.12(17) . . . . ? F2 C25 S1 O3 177.19(17) . . . . ? F1 C25 S1 O3 55.88(19) . . . . ? F3 C25 S1 O3 -63.06(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.395 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.056