# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_address 'Viale Risorgimento 4 - 40136 Bologna' _publ_contact_author ; Dr. Andrea Mazzanti University of Bologna Department of Organic Chemistry A.Mangini Viale Risorgimento 4 40136 Bologna Italy ; _publ_contact_author_email andrea.mazzanti@unibo.it _publ_contact_author_fax '[039]051 209 3654' _publ_contact_author_phone '[039]051 209 3632' _publ_section_title ; Rotational barrier of biphenyls having heavy heteroatoms as ortho-substituents: experimental and theoretical determination of steric effects. ; _publ_contact_author_name 'Dr. Andrea Mazzanti' loop_ _publ_author_name L.Lunazzi 'Michele Mancinelli' 'Andrea Mazzanti' 'Susan Lepri' 'Renzo Ruzziconi' 'Manfred Schlosser' data_b5_f _database_code_depnum_ccdc_archive 'CCDC 849731' _audit_creation_date 12/11/2010 _audit_update_record 09/29/2011 _publ_section_references ? _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-(Dimethylisopropylsilyl)biphenyl-2-yl]diphenylphosphine ; _chemical_name_common 'compound 9' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H31 O0.47 P Si' _chemical_formula_weight 446.12 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' 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' O O 0.0106 0.0060 '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 12.3538(14) _cell_length_b 11.1227(12) _cell_length_c 18.446(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.7460(10) _cell_angle_gamma 90.00 _cell_volume 2533.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description stick _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 951 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9503 _exptl_absorpt_correction_T_max 0.9747 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD are a detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25500 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0145 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4987 _reflns_number_gt 4337 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0566P)^2^+1.0484P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4987 _refine_ls_number_parameters 294 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.045 _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 0.90857(3) 0.19519(4) 0.14167(2) 0.03916(13) Uani 1 1 d D . . O1 O 0.9580(2) 0.07946(15) 0.16425(14) 0.0552(11) Uani 0.471(5) 1 d PD A 1 Si2 Si 0.82831(4) 0.24810(5) 0.46678(3) 0.04910(15) Uani 1 1 d . . . C1 C 1.04242(12) 0.34743(14) 0.22520(8) 0.0358(3) Uani 1 1 d . . . C2 C 0.99026(12) 0.33062(14) 0.15696(8) 0.0348(3) Uani 1 1 d . A . C3 C 1.00450(14) 0.41704(16) 0.10323(9) 0.0429(4) Uani 1 1 d . . . H3 H 0.9696 0.4074 0.0582 0.051 Uiso 1 1 calc R A . C4 C 1.06928(15) 0.51670(16) 0.11551(9) 0.0464(4) Uani 1 1 d . A . H4 H 1.0779 0.5731 0.0789 0.056 Uiso 1 1 calc R . . C5 C 1.12099(14) 0.53230(16) 0.18194(10) 0.0468(4) Uani 1 1 d . . . H5 H 1.1654 0.5987 0.1902 0.056 Uiso 1 1 calc R A . C6 C 1.10671(14) 0.44862(17) 0.23657(9) 0.0453(4) Uani 1 1 d . A . H6 H 1.1408 0.4604 0.2817 0.054 Uiso 1 1 calc R . . C7 C 1.02707(13) 0.26226(15) 0.28691(8) 0.0383(4) Uani 1 1 d . A . C8 C 1.08499(15) 0.15565(17) 0.29240(10) 0.0492(4) Uani 1 1 d . . . H8 H 1.1339 0.1354 0.2570 0.059 Uiso 1 1 calc R A . C9 C 1.06996(18) 0.07950(19) 0.35049(11) 0.0617(5) Uani 1 1 d . A . H9 H 1.1099 0.0088 0.3547 0.074 Uiso 1 1 calc R . . C10 C 0.99567(18) 0.10830(19) 0.40233(11) 0.0595(5) Uani 1 1 d . . . H10 H 0.9856 0.0554 0.4406 0.071 Uiso 1 1 calc R A . C11 C 0.93540(15) 0.21430(17) 0.39901(9) 0.0452(4) Uani 1 1 d . A . C12 C 0.95401(14) 0.29040(16) 0.34026(9) 0.0416(4) Uani 1 1 d . . . H12 H 0.9161 0.3625 0.3368 0.050 Uiso 1 1 calc R A . C13 C 0.78141(14) 0.22927(16) 0.18419(9) 0.0424(4) Uani 1 1 d . A . C14 C 0.72987(17) 0.1338(2) 0.21734(11) 0.0595(5) Uani 1 1 d . . . H14 H 0.7611 0.0578 0.2165 0.071 Uiso 1 1 calc R A . C15 C 0.6337(2) 0.1497(3) 0.25130(13) 0.0795(7) Uani 1 1 d . A . H15 H 0.6001 0.0849 0.2732 0.095 Uiso 1 1 calc R . . C16 C 0.58773(19) 0.2605(3) 0.25278(14) 0.0830(8) Uani 1 1 d . . . H16 H 0.5227 0.2712 0.2761 0.100 Uiso 1 1 calc R A . C17 C 0.6362(2) 0.3575(3) 0.22013(16) 0.0838(8) Uani 1 1 d . A . H17 H 0.6037 0.4329 0.2209 0.101 Uiso 1 1 calc R . . C18 C 0.73457(17) 0.3413(2) 0.18586(13) 0.0642(6) Uani 1 1 d . . . H18 H 0.7683 0.4063 0.1642 0.077 Uiso 1 1 calc R A . C19 C 0.87555(14) 0.19517(15) 0.04454(9) 0.0395(4) Uani 1 1 d . A . C20 C 0.77453(16) 0.2223(2) 0.01397(11) 0.0561(5) Uani 1 1 d . . . H20 H 0.7207 0.2533 0.0428 0.067 Uiso 1 1 calc R A . C21 C 0.75334(18) 0.2036(2) -0.05951(12) 0.0680(6) Uani 1 1 d . A . H21 H 0.6850 0.2209 -0.0794 0.082 Uiso 1 1 calc R . . C22 C 0.8319(2) 0.1598(2) -0.10287(11) 0.0636(6) Uani 1 1 d . . . H22 H 0.8171 0.1478 -0.1521 0.076 Uiso 1 1 calc R A . C23 C 0.9326(2) 0.1337(2) -0.07381(11) 0.0625(5) Uani 1 1 d . A . H23 H 0.9863 0.1044 -0.1033 0.075 Uiso 1 1 calc R . . C24 C 0.95397(16) 0.15111(18) -0.00039(10) 0.0517(4) Uani 1 1 d . . . H24 H 1.0223 0.1328 0.0191 0.062 Uiso 1 1 calc R A . C25 C 0.89252(18) 0.26246(19) 0.56031(10) 0.0573(5) Uani 1 1 d . . . H25 H 0.9345 0.1891 0.5698 0.069 Uiso 1 1 calc R . . C26 C 0.8080(2) 0.2718(3) 0.61931(13) 0.0840(8) Uani 1 1 d . . . H26A H 0.8441 0.2748 0.6661 0.126 Uiso 1 1 calc R . . H26B H 0.7612 0.2030 0.6168 0.126 Uiso 1 1 calc R . . H26C H 0.7659 0.3436 0.6119 0.126 Uiso 1 1 calc R . . C27 C 0.9714(2) 0.3684(3) 0.56503(14) 0.0843(8) Uani 1 1 d . . . H27A H 0.9318 0.4424 0.5606 0.126 Uiso 1 1 calc R . . H27B H 1.0218 0.3627 0.5266 0.126 Uiso 1 1 calc R . . H27C H 1.0102 0.3665 0.6109 0.126 Uiso 1 1 calc R . . C28 C 0.7301(2) 0.1209(3) 0.46413(15) 0.0864(8) Uani 1 1 d . . . H28A H 0.7004 0.1119 0.4157 0.130 Uiso 1 1 calc R . . H28B H 0.6727 0.1371 0.4967 0.130 Uiso 1 1 calc R . . H28C H 0.7666 0.0481 0.4786 0.130 Uiso 1 1 calc R . . C29 C 0.75890(19) 0.3914(2) 0.44095(13) 0.0705(6) Uani 1 1 d . . . H29A H 0.8119 0.4534 0.4349 0.106 Uiso 1 1 calc R . . H29B H 0.7107 0.4142 0.4784 0.106 Uiso 1 1 calc R . . H29C H 0.7184 0.3802 0.3962 0.106 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0436(2) 0.0388(2) 0.0351(2) 0.00070(17) 0.00235(17) -0.00336(17) O1 0.066(2) 0.0494(18) 0.0495(17) 0.0007(12) -0.0022(13) 0.0038(13) Si2 0.0512(3) 0.0572(3) 0.0394(3) 0.0060(2) 0.0089(2) -0.0083(2) C1 0.0323(7) 0.0419(8) 0.0334(7) 0.0028(6) 0.0042(6) 0.0027(6) C2 0.0340(8) 0.0374(8) 0.0333(7) 0.0017(6) 0.0054(6) 0.0005(6) C3 0.0499(9) 0.0464(9) 0.0325(8) 0.0043(7) 0.0030(7) -0.0030(8) C4 0.0534(10) 0.0443(9) 0.0422(9) 0.0085(7) 0.0117(8) -0.0041(8) C5 0.0428(9) 0.0451(10) 0.0528(10) 0.0002(8) 0.0061(8) -0.0099(7) C6 0.0421(9) 0.0527(10) 0.0407(9) 0.0002(8) -0.0032(7) -0.0050(8) C7 0.0379(8) 0.0446(9) 0.0323(8) 0.0044(7) -0.0027(6) -0.0017(7) C8 0.0501(10) 0.0534(11) 0.0441(9) 0.0047(8) 0.0040(8) 0.0085(8) C9 0.0713(13) 0.0533(12) 0.0606(12) 0.0164(9) 0.0063(10) 0.0172(10) C10 0.0724(13) 0.0570(12) 0.0494(10) 0.0211(9) 0.0073(9) 0.0043(10) C11 0.0484(9) 0.0503(10) 0.0369(8) 0.0082(7) 0.0029(7) -0.0037(8) C12 0.0443(9) 0.0435(9) 0.0370(8) 0.0050(7) 0.0018(7) 0.0011(7) C13 0.0431(9) 0.0476(10) 0.0366(8) -0.0025(7) 0.0044(7) -0.0069(7) C14 0.0590(12) 0.0661(13) 0.0540(11) 0.0072(10) 0.0088(9) -0.0153(10) C15 0.0655(14) 0.107(2) 0.0671(14) 0.0016(14) 0.0203(12) -0.0257(15) C16 0.0516(12) 0.131(3) 0.0679(15) -0.0333(16) 0.0197(11) -0.0235(15) C17 0.0608(14) 0.0861(18) 0.105(2) -0.0394(16) 0.0066(13) 0.0108(13) C18 0.0571(12) 0.0539(12) 0.0824(15) -0.0088(11) 0.0141(11) -0.0024(10) C19 0.0443(9) 0.0377(8) 0.0364(8) -0.0003(6) 0.0005(7) -0.0050(7) C20 0.0469(10) 0.0742(13) 0.0469(10) 0.0008(9) -0.0006(8) 0.0024(9) C21 0.0579(12) 0.0921(17) 0.0531(12) 0.0071(11) -0.0149(10) -0.0082(12) C22 0.0855(15) 0.0671(13) 0.0377(9) -0.0009(9) -0.0054(10) -0.0173(12) C23 0.0809(14) 0.0643(13) 0.0429(10) -0.0055(9) 0.0129(10) 0.0039(11) C24 0.0521(10) 0.0588(11) 0.0442(9) -0.0017(8) 0.0025(8) 0.0058(9) C25 0.0702(13) 0.0614(12) 0.0407(10) 0.0089(9) 0.0054(9) -0.0011(10) C26 0.102(2) 0.104(2) 0.0476(12) -0.0039(12) 0.0198(12) -0.0128(16) C27 0.0839(17) 0.102(2) 0.0656(14) 0.0031(14) -0.0112(13) -0.0279(15) C28 0.0899(18) 0.0939(19) 0.0768(16) -0.0120(14) 0.0271(14) -0.0426(15) C29 0.0601(13) 0.0874(17) 0.0647(13) 0.0142(12) 0.0117(10) 0.0161(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 P1 O1 1.4790(10) . ? P1 C13 1.8171(18) . ? P1 C19 1.8252(17) . ? P1 C2 1.8302(16) . ? Si2 C28 1.864(2) . ? Si2 C29 1.865(2) . ? Si2 C25 1.884(2) . ? Si2 C11 1.8855(19) . ? C1 C6 1.390(2) . ? C1 C2 1.409(2) . ? C1 C7 1.497(2) . ? C2 C3 1.396(2) . ? C3 C4 1.382(2) . ? C3 H3 0.9300 . ? C4 C5 1.375(3) . ? C4 H4 0.9300 . ? C5 C6 1.387(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.387(2) . ? C7 C12 1.391(2) . ? C8 C9 1.383(3) . ? C8 H8 0.9300 . ? C9 C10 1.383(3) . ? C9 H9 0.9300 . ? C10 C11 1.395(3) . ? C10 H10 0.9300 . ? C11 C12 1.400(2) . ? C12 H12 0.9300 . ? C13 C18 1.375(3) . ? C13 C14 1.390(3) . ? C14 C15 1.371(3) . ? C14 H14 0.9300 . ? C15 C16 1.357(4) . ? C15 H15 0.9300 . ? C16 C17 1.381(4) . ? C16 H16 0.9300 . ? C17 C18 1.399(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C24 1.384(2) . ? C19 C20 1.387(3) . ? C20 C21 1.388(3) . ? C20 H20 0.9300 . ? C21 C22 1.366(3) . ? C21 H21 0.9300 . ? C22 C23 1.370(3) . ? C22 H22 0.9300 . ? C23 C24 1.386(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C27 1.530(3) . ? C25 C26 1.534(3) . ? C25 H25 0.9800 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C13 114.50(13) . . ? O1 P1 C19 110.75(12) . . ? C13 P1 C19 104.68(8) . . ? O1 P1 C2 116.88(13) . . ? C13 P1 C2 103.99(7) . . ? C19 P1 C2 104.90(7) . . ? C28 Si2 C29 110.38(13) . . ? C28 Si2 C25 110.13(11) . . ? C29 Si2 C25 109.82(11) . . ? C28 Si2 C11 107.49(10) . . ? C29 Si2 C11 109.12(9) . . ? C25 Si2 C11 109.86(9) . . ? C6 C1 C2 119.07(14) . . ? C6 C1 C7 118.86(14) . . ? C2 C1 C7 122.01(14) . . ? C3 C2 C1 118.61(15) . . ? C3 C2 P1 122.57(12) . . ? C1 C2 P1 118.81(11) . . ? C4 C3 C2 121.40(15) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C5 C4 C3 119.88(16) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 119.78(16) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 121.24(16) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? C8 C7 C12 119.02(15) . . ? C8 C7 C1 121.28(15) . . ? C12 C7 C1 119.69(14) . . ? C9 C8 C7 119.94(17) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.09(18) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 122.01(17) . . ? C9 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? C10 C11 C12 116.43(17) . . ? C10 C11 Si2 121.59(13) . . ? C12 C11 Si2 121.86(14) . . ? C7 C12 C11 122.48(16) . . ? C7 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C18 C13 C14 118.96(18) . . ? C18 C13 P1 124.66(14) . . ? C14 C13 P1 116.38(15) . . ? C15 C14 C13 121.2(2) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16 C15 C14 119.7(2) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.9(2) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C18 119.4(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C13 C18 C17 119.9(2) . . ? C13 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C24 C19 C20 118.12(16) . . ? C24 C19 P1 116.64(13) . . ? C20 C19 P1 124.78(14) . . ? C19 C20 C21 120.31(19) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C20 120.6(2) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 119.93(18) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 119.8(2) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C19 C24 C23 121.24(18) . . ? C19 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C27 C25 C26 110.7(2) . . ? C27 C25 Si2 111.55(14) . . ? C26 C25 Si2 112.26(17) . . ? C27 C25 H25 107.4 . . ? C26 C25 H25 107.4 . . ? Si2 C25 H25 107.4 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? Si2 C28 H28A 109.5 . . ? Si2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? Si2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? Si2 C29 H29A 109.5 . . ? Si2 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? Si2 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.5(2) . . . . ? C7 C1 C2 C3 176.92(15) . . . . ? C6 C1 C2 P1 178.44(12) . . . . ? C7 C1 C2 P1 -4.2(2) . . . . ? O1 P1 C2 C3 131.31(18) . . . . ? C13 P1 C2 C3 -101.43(14) . . . . ? C19 P1 C2 C3 8.23(16) . . . . ? O1 P1 C2 C1 -47.55(18) . . . . ? C13 P1 C2 C1 79.70(13) . . . . ? C19 P1 C2 C1 -170.63(12) . . . . ? C1 C2 C3 C4 0.9(2) . . . . ? P1 C2 C3 C4 -178.01(13) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C4 C5 C6 C1 1.2(3) . . . . ? C2 C1 C6 C5 -0.6(2) . . . . ? C7 C1 C6 C5 -178.03(16) . . . . ? C6 C1 C7 C8 -100.7(2) . . . . ? C2 C1 C7 C8 81.9(2) . . . . ? C6 C1 C7 C12 78.8(2) . . . . ? C2 C1 C7 C12 -98.62(19) . . . . ? C12 C7 C8 C9 -0.3(3) . . . . ? C1 C7 C8 C9 179.24(18) . . . . ? C7 C8 C9 C10 1.3(3) . . . . ? C8 C9 C10 C11 -1.2(3) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C9 C10 C11 Si2 176.20(17) . . . . ? C28 Si2 C11 C10 -56.2(2) . . . . ? C29 Si2 C11 C10 -175.92(17) . . . . ? C25 Si2 C11 C10 63.63(19) . . . . ? C28 Si2 C11 C12 119.79(18) . . . . ? C29 Si2 C11 C12 0.07(19) . . . . ? C25 Si2 C11 C12 -120.38(16) . . . . ? C8 C7 C12 C11 -0.9(3) . . . . ? C1 C7 C12 C11 179.54(16) . . . . ? C10 C11 C12 C7 1.1(3) . . . . ? Si2 C11 C12 C7 -175.14(13) . . . . ? O1 P1 C13 C18 163.4(2) . . . . ? C19 P1 C13 C18 -75.17(18) . . . . ? C2 P1 C13 C18 34.66(19) . . . . ? O1 P1 C13 C14 -16.2(2) . . . . ? C19 P1 C13 C14 105.21(15) . . . . ? C2 P1 C13 C14 -144.96(14) . . . . ? C18 C13 C14 C15 0.1(3) . . . . ? P1 C13 C14 C15 179.72(17) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C14 C15 C16 C17 0.4(4) . . . . ? C15 C16 C17 C18 -0.8(4) . . . . ? C14 C13 C18 C17 -0.4(3) . . . . ? P1 C13 C18 C17 179.95(18) . . . . ? C16 C17 C18 C13 0.8(4) . . . . ? O1 P1 C19 C24 -45.2(2) . . . . ? C13 P1 C19 C24 -169.12(14) . . . . ? C2 P1 C19 C24 81.72(15) . . . . ? O1 P1 C19 C20 126.8(2) . . . . ? C13 P1 C19 C20 2.94(18) . . . . ? C2 P1 C19 C20 -106.22(17) . . . . ? C24 C19 C20 C21 1.0(3) . . . . ? P1 C19 C20 C21 -170.93(17) . . . . ? C19 C20 C21 C22 -1.0(4) . . . . ? C20 C21 C22 C23 0.3(4) . . . . ? C21 C22 C23 C24 0.4(3) . . . . ? C20 C19 C24 C23 -0.4(3) . . . . ? P1 C19 C24 C23 172.21(16) . . . . ? C22 C23 C24 C19 -0.3(3) . . . . ? C28 Si2 C25 C27 -178.43(19) . . . . ? C29 Si2 C25 C27 -56.7(2) . . . . ? C11 Si2 C25 C27 63.36(19) . . . . ? C28 Si2 C25 C26 -53.5(2) . . . . ? C29 Si2 C25 C26 68.24(19) . . . . ? C11 Si2 C25 C26 -171.74(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.627 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.040 # Attachment '- compound10.cif' data_b5g _database_code_depnum_ccdc_archive 'CCDC 849732' _audit_creation_date 12/10/2010 _audit_update_record 09/29/2011 _publ_section_references ? _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-(Dimethylisopropylsilyl)biphenyl-2-yl]diphenylphosphine oxide ; _chemical_name_common 'compound 10' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H31 O P Si' _chemical_formula_weight 454.60 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' 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 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 12.3039(19) _cell_length_b 11.1280(17) _cell_length_c 18.544(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.632(2) _cell_angle_gamma 90.00 _cell_volume 2537.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description brick _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9257 _exptl_absorpt_correction_T_max 0.9660 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 28424 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.17 _reflns_number_total 6101 _reflns_number_gt 5050 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0481P)^2^+0.7135P] 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 6101 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.90332(3) 0.20003(3) 0.139889(17) 0.03241(9) Uani 1 1 d . . . Si1 Si 0.82469(4) 0.25168(4) 0.46754(2) 0.04624(12) Uani 1 1 d . . . O1 O 0.95421(9) 0.08413(9) 0.16157(5) 0.0438(2) Uani 1 1 d . . . C1 C 1.04011(10) 0.34595(12) 0.22647(7) 0.0336(3) Uani 1 1 d . . . C2 C 0.98898(10) 0.33049(11) 0.15812(7) 0.0322(3) Uani 1 1 d . . . C3 C 1.00524(12) 0.41695(13) 0.10516(7) 0.0396(3) Uani 1 1 d . . . H3 H 0.9707 0.4081 0.0602 0.048 Uiso 1 1 calc R . . C4 C 1.07149(12) 0.51571(13) 0.11783(8) 0.0439(3) Uani 1 1 d . . . H4 H 1.0814 0.5722 0.0817 0.053 Uiso 1 1 calc R . . C5 C 1.12244(12) 0.52966(14) 0.18417(8) 0.0455(3) Uani 1 1 d . . . H5 H 1.1678 0.5952 0.1929 0.055 Uiso 1 1 calc R . . C6 C 1.10617(12) 0.44597(14) 0.23811(8) 0.0434(3) Uani 1 1 d . . . H6 H 1.1402 0.4569 0.2831 0.052 Uiso 1 1 calc R . . C7 C 1.02302(11) 0.26101(12) 0.28785(7) 0.0358(3) Uani 1 1 d . . . C8 C 0.95037(11) 0.29139(13) 0.34096(7) 0.0391(3) Uani 1 1 d . . . H8 H 0.9139 0.3645 0.3376 0.047 Uiso 1 1 calc R . . C9 C 0.93026(12) 0.21545(14) 0.39952(8) 0.0424(3) Uani 1 1 d . . . C10 C 0.98849(15) 0.10790(15) 0.40253(9) 0.0539(4) Uani 1 1 d . . . H10 H 0.9770 0.0550 0.4404 0.065 Uiso 1 1 calc R . . C11 C 1.06267(15) 0.07739(15) 0.35103(9) 0.0553(4) Uani 1 1 d . . . H11 H 1.1014 0.0058 0.3552 0.066 Uiso 1 1 calc R . . C12 C 1.07933(12) 0.15315(14) 0.29346(8) 0.0453(3) Uani 1 1 d . . . H12 H 1.1283 0.1319 0.2584 0.054 Uiso 1 1 calc R . . C13 C 0.87109(11) 0.20065(12) 0.04408(7) 0.0345(3) Uani 1 1 d . . . C14 C 0.77089(13) 0.23277(16) 0.01397(9) 0.0502(4) Uani 1 1 d . . . H14 H 0.7183 0.2667 0.0427 0.060 Uiso 1 1 calc R . . C15 C 0.74892(15) 0.21446(19) -0.05884(9) 0.0628(5) Uani 1 1 d . . . H15 H 0.6815 0.2359 -0.0788 0.075 Uiso 1 1 calc R . . C16 C 0.82582(16) 0.16511(16) -0.10158(8) 0.0578(4) Uani 1 1 d . . . H16 H 0.8102 0.1529 -0.1504 0.069 Uiso 1 1 calc R . . C17 C 0.92589(16) 0.13346(15) -0.07302(8) 0.0543(4) Uani 1 1 d . . . H17 H 0.9782 0.1003 -0.1023 0.065 Uiso 1 1 calc R . . C18 C 0.94830(13) 0.15130(14) -0.00018(8) 0.0449(3) Uani 1 1 d . . . H18 H 1.0160 0.1299 0.0193 0.054 Uiso 1 1 calc R . . C19 C 0.77814(11) 0.22819(13) 0.18500(7) 0.0371(3) Uani 1 1 d . . . C20 C 0.72934(14) 0.34005(15) 0.18887(10) 0.0538(4) Uani 1 1 d . . . H20 H 0.7609 0.4061 0.1670 0.065 Uiso 1 1 calc R . . C21 C 0.63291(15) 0.35344(19) 0.22558(11) 0.0674(5) Uani 1 1 d . . . H21 H 0.5997 0.4283 0.2282 0.081 Uiso 1 1 calc R . . C22 C 0.58710(14) 0.2552(2) 0.25793(10) 0.0674(5) Uani 1 1 d . . . H22 H 0.5230 0.2643 0.2827 0.081 Uiso 1 1 calc R . . C23 C 0.63454(15) 0.1446(2) 0.25416(10) 0.0653(5) Uani 1 1 d . . . H23 H 0.6026 0.0788 0.2761 0.078 Uiso 1 1 calc R . . C24 C 0.72966(13) 0.13045(15) 0.21785(8) 0.0501(4) Uani 1 1 d . . . H24 H 0.7617 0.0550 0.2153 0.060 Uiso 1 1 calc R . . C25 C 0.75751(16) 0.39666(19) 0.44377(10) 0.0672(5) Uani 1 1 d . . . H25A H 0.7167 0.3878 0.3992 0.101 Uiso 1 1 calc R . . H25B H 0.8117 0.4578 0.4385 0.101 Uiso 1 1 calc R . . H25C H 0.7094 0.4191 0.4813 0.101 Uiso 1 1 calc R . . C26 C 0.72382(19) 0.1265(2) 0.46495(12) 0.0828(7) Uani 1 1 d . . . H26A H 0.6937 0.1183 0.4169 0.124 Uiso 1 1 calc R . . H26B H 0.6667 0.1437 0.4976 0.124 Uiso 1 1 calc R . . H26C H 0.7592 0.0529 0.4791 0.124 Uiso 1 1 calc R . . C27 C 0.89106(15) 0.26216(17) 0.56009(9) 0.0556(4) Uani 1 1 d . . . H27 H 0.9321 0.1877 0.5683 0.067 Uiso 1 1 calc R . . C28 C 0.97235(19) 0.3661(2) 0.56522(12) 0.0833(7) Uani 1 1 d . . . H28A H 0.9340 0.4411 0.5613 0.125 Uiso 1 1 calc R . . H28B H 1.0228 0.3598 0.5268 0.125 Uiso 1 1 calc R . . H28C H 1.0113 0.3627 0.6108 0.125 Uiso 1 1 calc R . . C29 C 0.8078(2) 0.2714(2) 0.61967(11) 0.0833(7) Uani 1 1 d . . . H29A H 0.8451 0.2744 0.6658 0.125 Uiso 1 1 calc R . . H29B H 0.7608 0.2026 0.6177 0.125 Uiso 1 1 calc R . . H29C H 0.7653 0.3431 0.6128 0.125 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.03705(18) 0.03054(17) 0.02975(16) -0.00011(12) 0.00285(12) -0.00018(13) Si1 0.0498(2) 0.0514(3) 0.0378(2) 0.00590(17) 0.00732(17) -0.00705(19) O1 0.0556(6) 0.0340(5) 0.0415(5) 0.0002(4) -0.0022(4) 0.0060(4) C1 0.0312(6) 0.0365(7) 0.0331(6) 0.0021(5) 0.0033(5) 0.0019(5) C2 0.0326(6) 0.0334(6) 0.0310(6) 0.0003(5) 0.0057(5) 0.0009(5) C3 0.0469(7) 0.0410(7) 0.0311(6) 0.0027(5) 0.0046(5) -0.0026(6) C4 0.0508(8) 0.0392(7) 0.0421(7) 0.0068(6) 0.0114(6) -0.0052(6) C5 0.0409(7) 0.0417(8) 0.0542(9) 0.0000(6) 0.0050(6) -0.0102(6) C6 0.0408(7) 0.0476(8) 0.0414(7) 0.0000(6) -0.0040(6) -0.0061(6) C7 0.0369(7) 0.0399(7) 0.0303(6) 0.0025(5) -0.0033(5) -0.0016(5) C8 0.0433(7) 0.0386(7) 0.0354(7) 0.0049(6) 0.0008(5) 0.0007(6) C9 0.0481(8) 0.0447(8) 0.0345(7) 0.0054(6) 0.0019(6) -0.0048(6) C10 0.0703(11) 0.0480(9) 0.0435(8) 0.0163(7) 0.0036(7) 0.0019(8) C11 0.0698(11) 0.0447(9) 0.0512(9) 0.0100(7) 0.0003(8) 0.0147(8) C12 0.0488(8) 0.0480(8) 0.0391(7) 0.0022(6) 0.0004(6) 0.0085(7) C13 0.0392(7) 0.0330(6) 0.0312(6) -0.0001(5) 0.0006(5) -0.0027(5) C14 0.0436(8) 0.0638(10) 0.0431(8) 0.0021(7) 0.0000(6) 0.0067(7) C15 0.0551(10) 0.0855(13) 0.0471(9) 0.0084(9) -0.0129(8) -0.0037(9) C16 0.0793(12) 0.0607(10) 0.0330(7) -0.0002(7) -0.0054(7) -0.0145(9) C17 0.0750(11) 0.0510(9) 0.0374(8) -0.0042(7) 0.0121(7) 0.0038(8) C18 0.0481(8) 0.0485(8) 0.0383(7) -0.0010(6) 0.0039(6) 0.0069(6) C19 0.0389(7) 0.0399(7) 0.0327(6) -0.0041(5) 0.0047(5) -0.0042(5) C20 0.0522(9) 0.0417(8) 0.0684(11) -0.0082(7) 0.0137(8) -0.0013(7) C21 0.0538(10) 0.0644(12) 0.0845(13) -0.0287(10) 0.0109(9) 0.0066(9) C22 0.0449(9) 0.0973(16) 0.0608(11) -0.0234(10) 0.0170(8) -0.0139(10) C23 0.0544(10) 0.0822(14) 0.0601(11) 0.0052(10) 0.0172(8) -0.0161(10) C24 0.0498(8) 0.0516(9) 0.0494(8) 0.0060(7) 0.0082(7) -0.0072(7) C25 0.0577(10) 0.0821(13) 0.0622(11) 0.0139(10) 0.0099(8) 0.0160(10) C26 0.0842(14) 0.0939(16) 0.0715(13) -0.0092(12) 0.0225(11) -0.0412(13) C27 0.0694(11) 0.0590(10) 0.0387(8) 0.0082(7) 0.0043(7) 0.0005(8) C28 0.0810(14) 0.1063(18) 0.0618(12) 0.0017(12) -0.0119(10) -0.0258(13) C29 0.0991(17) 0.1064(18) 0.0455(10) -0.0028(11) 0.0204(10) -0.0145(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 P1 O1 1.4842(10) . ? P1 C19 1.8011(14) . ? P1 C13 1.8093(13) . ? P1 C2 1.8201(13) . ? Si1 C25 1.860(2) . ? Si1 C26 1.866(2) . ? Si1 C9 1.8799(16) . ? Si1 C27 1.8831(18) . ? C1 C6 1.3915(19) . ? C1 C2 1.4094(18) . ? C1 C7 1.4989(18) . ? C2 C3 1.3933(18) . ? C3 C4 1.384(2) . ? C4 C5 1.374(2) . ? C5 C6 1.385(2) . ? C7 C12 1.388(2) . ? C7 C8 1.3904(19) . ? C8 C9 1.4036(19) . ? C9 C10 1.395(2) . ? C10 C11 1.382(2) . ? C11 C12 1.380(2) . ? C13 C14 1.386(2) . ? C13 C18 1.3864(19) . ? C14 C15 1.384(2) . ? C15 C16 1.367(3) . ? C16 C17 1.372(3) . ? C17 C18 1.385(2) . ? C19 C20 1.385(2) . ? C19 C24 1.389(2) . ? C20 C21 1.393(2) . ? C21 C22 1.375(3) . ? C22 C23 1.366(3) . ? C23 C24 1.376(2) . ? C27 C28 1.530(3) . ? C27 C29 1.531(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 O1 P1 C19 112.65(6) . . ? O1 P1 C13 110.38(6) . . ? C19 P1 C13 106.80(6) . . ? O1 P1 C2 113.91(6) . . ? C19 P1 C2 105.86(6) . . ? C13 P1 C2 106.79(6) . . ? C25 Si1 C26 110.54(11) . . ? C25 Si1 C9 109.75(8) . . ? C26 Si1 C9 107.12(9) . . ? C25 Si1 C27 109.90(9) . . ? C26 Si1 C27 109.92(9) . . ? C9 Si1 C27 109.56(8) . . ? C6 C1 C2 118.74(12) . . ? C6 C1 C7 118.73(12) . . ? C2 C1 C7 122.50(12) . . ? C3 C2 C1 118.70(12) . . ? C3 C2 P1 120.92(10) . . ? C1 C2 P1 120.37(9) . . ? C4 C3 C2 121.62(13) . . ? C5 C4 C3 119.55(13) . . ? C4 C5 C6 119.93(13) . . ? C5 C6 C1 121.44(13) . . ? C12 C7 C8 119.12(12) . . ? C12 C7 C1 121.44(12) . . ? C8 C7 C1 119.43(12) . . ? C7 C8 C9 122.19(13) . . ? C10 C9 C8 116.47(14) . . ? C10 C9 Si1 121.40(11) . . ? C8 C9 Si1 122.03(12) . . ? C11 C10 C9 122.11(14) . . ? C12 C11 C10 120.00(15) . . ? C11 C12 C7 120.08(14) . . ? C14 C13 C18 118.71(13) . . ? C14 C13 P1 124.35(11) . . ? C18 C13 P1 116.43(10) . . ? C15 C14 C13 120.12(15) . . ? C16 C15 C14 120.36(16) . . ? C15 C16 C17 120.51(15) . . ? C16 C17 C18 119.40(15) . . ? C17 C18 C13 120.88(15) . . ? C20 C19 C24 119.26(14) . . ? C20 C19 P1 123.94(11) . . ? C24 C19 P1 116.80(11) . . ? C19 C20 C21 119.88(16) . . ? C22 C21 C20 119.59(18) . . ? C23 C22 C21 120.88(16) . . ? C22 C23 C24 119.93(17) . . ? C23 C24 C19 120.46(17) . . ? C28 C27 C29 110.71(17) . . ? C28 C27 Si1 111.66(12) . . ? C29 C27 Si1 112.34(14) . . ? 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 C3 -0.97(19) . . . . ? C7 C1 C2 C3 176.89(12) . . . . ? C6 C1 C2 P1 179.14(10) . . . . ? C7 C1 C2 P1 -2.99(17) . . . . ? O1 P1 C2 C3 131.03(11) . . . . ? C19 P1 C2 C3 -104.65(11) . . . . ? C13 P1 C2 C3 8.91(12) . . . . ? O1 P1 C2 C1 -49.08(12) . . . . ? C19 P1 C2 C1 75.24(11) . . . . ? C13 P1 C2 C1 -171.21(10) . . . . ? C1 C2 C3 C4 1.1(2) . . . . ? P1 C2 C3 C4 -178.99(11) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 -0.8(2) . . . . ? C4 C5 C6 C1 1.0(2) . . . . ? C2 C1 C6 C5 -0.1(2) . . . . ? C7 C1 C6 C5 -178.01(13) . . . . ? C6 C1 C7 C12 -100.88(16) . . . . ? C2 C1 C7 C12 81.25(17) . . . . ? C6 C1 C7 C8 78.21(17) . . . . ? C2 C1 C7 C8 -99.65(16) . . . . ? C12 C7 C8 C9 -1.3(2) . . . . ? C1 C7 C8 C9 179.58(13) . . . . ? C7 C8 C9 C10 1.0(2) . . . . ? C7 C8 C9 Si1 -175.50(11) . . . . ? C25 Si1 C9 C10 -176.35(14) . . . . ? C26 Si1 C9 C10 -56.31(16) . . . . ? C27 Si1 C9 C10 62.89(15) . . . . ? C25 Si1 C9 C8 -0.02(16) . . . . ? C26 Si1 C9 C8 120.02(15) . . . . ? C27 Si1 C9 C8 -120.79(13) . . . . ? C8 C9 C10 C11 0.4(2) . . . . ? Si1 C9 C10 C11 176.90(14) . . . . ? C9 C10 C11 C12 -1.4(3) . . . . ? C10 C11 C12 C7 1.1(3) . . . . ? C8 C7 C12 C11 0.2(2) . . . . ? C1 C7 C12 C11 179.31(14) . . . . ? O1 P1 C13 C14 130.28(13) . . . . ? C19 P1 C13 C14 7.51(15) . . . . ? C2 P1 C13 C14 -105.40(13) . . . . ? O1 P1 C13 C18 -41.39(13) . . . . ? C19 P1 C13 C18 -164.17(11) . . . . ? C2 P1 C13 C18 82.92(12) . . . . ? C18 C13 C14 C15 0.6(2) . . . . ? P1 C13 C14 C15 -170.91(14) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C16 C17 C18 C13 0.0(2) . . . . ? C14 C13 C18 C17 -0.4(2) . . . . ? P1 C13 C18 C17 171.71(12) . . . . ? O1 P1 C19 C20 163.03(13) . . . . ? C13 P1 C19 C20 -75.62(14) . . . . ? C2 P1 C19 C20 37.92(15) . . . . ? O1 P1 C19 C24 -16.55(14) . . . . ? C13 P1 C19 C24 104.80(12) . . . . ? C2 P1 C19 C24 -141.65(12) . . . . ? C24 C19 C20 C21 0.2(2) . . . . ? P1 C19 C20 C21 -179.39(14) . . . . ? C19 C20 C21 C22 0.2(3) . . . . ? C20 C21 C22 C23 -0.4(3) . . . . ? C21 C22 C23 C24 0.3(3) . . . . ? C22 C23 C24 C19 0.1(3) . . . . ? C20 C19 C24 C23 -0.3(2) . . . . ? P1 C19 C24 C23 179.26(13) . . . . ? C25 Si1 C27 C28 -56.58(17) . . . . ? C26 Si1 C27 C28 -178.45(16) . . . . ? C9 Si1 C27 C28 64.10(16) . . . . ? C25 Si1 C27 C29 68.50(16) . . . . ? C26 Si1 C27 C29 -53.38(18) . . . . ? C9 Si1 C27 C29 -170.83(14) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.17 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.414 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.036