# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global #============================================================================== _audit_creation_date 11-11-2003 _audit_creation_method ? _audit_update_record ; ? ; _journal_coden_Cambridge 182 loop_ _publ_author_name 'Guenter Helmchen' 'Christian Korff' _publ_contact_author_name 'Prof Guenter Helmchen' _publ_contact_author_address ; Organisch-Chemisches Institut der Ruprechts-Karls-University Heidelberg Im Neuenheimer Feld 270 Heidelberg D-69120 GERMANY ; _publ_contact_author_email EN4@IX.URZ.UNI-HEIDELBERG.DE _publ_requested_journal 'Chemical Communications' _publ_section_title ; Preparation of chiral triarylphosphines by Pd-catalysed asymmetric P-C cross-coupling ; data_985cko8 _database_code_depnum_ccdc_archive 'CCDC 227101' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tert-butyl 2-[biphenyl-2-yl(phenyl)phosphorothioyl]benzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H27 O2 P S' _chemical_formula_weight 470.54 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' 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 Hexagonal _symmetry_space_group_name_H-M P6(5) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' _cell_length_a 10.9348(4) _cell_length_b 10.9348(4) _cell_length_c 35.379(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3663.5(3) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8608 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.30 _exptl_crystal_description 'hexagonal column' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9383 _exptl_absorpt_correction_T_max 0.9527 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50418 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.30 _reflns_number_total 6079 _reflns_number_gt 5949 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0486P)^2^+0.1641P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(3) _refine_ls_number_reflns 6079 _refine_ls_number_parameters 406 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0658 _refine_ls_wR_factor_gt 0.0654 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.53390(3) 0.69763(3) 0.096977(8) 0.01676(6) Uani 1 1 d . . . S1 S 0.59438(3) 0.55648(3) 0.100454(9) 0.02450(7) Uani 1 1 d . . . O1 O 0.42950(9) 0.90964(9) 0.09754(2) 0.02114(16) Uani 1 1 d . . . O2 O 0.23075(10) 0.84006(10) 0.06342(2) 0.02359(18) Uani 1 1 d . . . C1 C 0.68581(12) 0.86950(12) 0.10770(3) 0.0196(2) Uani 1 1 d . . . C2 C 0.76564(14) 0.88536(13) 0.14004(4) 0.0238(2) Uani 1 1 d . . . C3 C 0.88751(14) 1.01374(14) 0.14767(4) 0.0267(3) Uani 1 1 d . . . C4 C 0.93355(13) 1.12426(14) 0.12203(4) 0.0269(3) Uani 1 1 d . . . C5 C 0.85758(14) 1.10776(14) 0.08927(4) 0.0266(3) Uani 1 1 d . . . C6 C 0.73347(13) 0.98151(13) 0.08212(4) 0.0225(2) Uani 1 1 d . . . C7 C 0.39040(12) 0.65433(12) 0.13062(3) 0.0173(2) Uani 1 1 d . . . C8 C 0.42659(13) 0.72487(13) 0.16548(3) 0.0219(2) Uani 1 1 d . . . C9 C 0.32767(15) 0.69100(14) 0.19401(4) 0.0254(2) Uani 1 1 d . . . C10 C 0.18968(15) 0.58524(14) 0.18799(4) 0.0269(3) Uani 1 1 d . . . C11 C 0.15075(13) 0.51712(13) 0.15330(4) 0.0244(2) Uani 1 1 d . . . C12 C 0.24839(13) 0.54935(12) 0.12406(3) 0.0191(2) Uani 1 1 d . . . C13 C 0.19186(12) 0.47656(12) 0.08700(3) 0.0198(2) Uani 1 1 d . . . C14 C 0.08778(14) 0.49403(13) 0.06885(4) 0.0272(3) Uani 1 1 d . . . C15 C 0.03643(16) 0.43404(15) 0.03373(4) 0.0346(3) Uani 1 1 d . . . C16 C 0.08471(17) 0.35283(17) 0.01668(4) 0.0376(3) Uani 1 1 d . . . C17 C 0.18297(16) 0.32932(17) 0.03495(4) 0.0358(3) Uani 1 1 d . . . C18 C 0.23686(14) 0.39128(13) 0.07004(4) 0.0252(2) Uani 1 1 d . . . C19 C 0.47535(12) 0.71443(12) 0.04964(3) 0.0178(2) Uani 1 1 d . . . C20 C 0.39296(12) 0.77682(12) 0.04110(3) 0.0182(2) Uani 1 1 d . . . C21 C 0.34957(13) 0.77624(13) 0.00396(3) 0.0225(2) Uani 1 1 d . . . C22 C 0.39070(14) 0.71804(14) -0.02501(4) 0.0261(3) Uani 1 1 d . . . C23 C 0.47193(14) 0.65730(14) -0.01676(4) 0.0259(3) Uani 1 1 d . . . C24 C 0.51245(14) 0.65399(13) 0.02027(4) 0.0227(2) Uani 1 1 d . . . C25 C 0.35473(12) 0.84941(11) 0.07085(3) 0.0178(2) Uani 1 1 d . . . C26 C 0.17428(14) 0.91021(15) 0.08823(4) 0.0255(3) Uani 1 1 d . . . C27 C 0.27572(19) 1.06853(16) 0.08914(5) 0.0370(3) Uani 1 1 d . . . C28 C 0.03866(19) 0.8764(2) 0.06777(5) 0.0445(4) Uani 1 1 d . . . C29 C 0.14352(17) 0.84388(17) 0.12733(4) 0.0310(3) Uani 1 1 d . . . H2 H 0.7380(17) 0.8067(19) 0.1570(5) 0.027(4) Uiso 1 1 d . . . H3 H 0.936(2) 1.018(2) 0.1703(6) 0.047(5) Uiso 1 1 d . . . H4 H 1.0116(18) 1.2093(18) 0.1268(5) 0.023(4) Uiso 1 1 d . . . H5 H 0.8880(17) 1.1826(18) 0.0713(5) 0.022(4) Uiso 1 1 d . . . H6 H 0.6810(18) 0.9684(17) 0.0601(5) 0.024(4) Uiso 1 1 d . . . H8 H 0.5213(17) 0.8006(17) 0.1696(4) 0.021(4) Uiso 1 1 d . . . H9 H 0.3554(18) 0.7442(18) 0.2180(5) 0.025(4) Uiso 1 1 d . . . H10 H 0.1181(18) 0.5609(17) 0.2071(5) 0.024(4) Uiso 1 1 d . . . H11 H 0.0566(18) 0.4478(18) 0.1494(5) 0.023(4) Uiso 1 1 d . . . H14 H 0.060(2) 0.553(2) 0.0817(6) 0.043(5) Uiso 1 1 d . . . H15 H -0.0303(19) 0.4480(19) 0.0215(5) 0.030(4) Uiso 1 1 d . . . H16 H 0.050(2) 0.314(2) -0.0070(6) 0.033(4) Uiso 1 1 d . . . H17 H 0.214(2) 0.268(2) 0.0221(6) 0.050(6) Uiso 1 1 d . . . H18 H 0.304(2) 0.3780(19) 0.0825(5) 0.033(4) Uiso 1 1 d . . . H21 H 0.2972(18) 0.8164(18) -0.0004(5) 0.028(4) Uiso 1 1 d . . . H22 H 0.3627(17) 0.7190(16) -0.0491(5) 0.022(4) Uiso 1 1 d . . . H23 H 0.4960(19) 0.6136(19) -0.0365(5) 0.028(4) Uiso 1 1 d . . . H24 H 0.5670(17) 0.6110(17) 0.0259(4) 0.020(4) Uiso 1 1 d . . . H27A H 0.3598(19) 1.0925(19) 0.1056(5) 0.030(4) Uiso 1 1 d . . . H27B H 0.312(2) 1.105(2) 0.0644(6) 0.042(5) Uiso 1 1 d . . . H27C H 0.227(2) 1.116(2) 0.1000(6) 0.046(5) Uiso 1 1 d . . . H28A H -0.028(2) 0.772(2) 0.0670(6) 0.043(5) Uiso 1 1 d . . . H28B H 0.059(3) 0.915(3) 0.0412(9) 0.067(7) Uiso 1 1 d . . . H28C H -0.011(2) 0.914(2) 0.0823(6) 0.040(5) Uiso 1 1 d . . . H29A H 0.229(2) 0.865(2) 0.1404(6) 0.034(5) Uiso 1 1 d . . . H29B H 0.086(2) 0.741(3) 0.1250(6) 0.049(6) Uiso 1 1 d . . . H29C H 0.090(2) 0.8844(19) 0.1418(5) 0.033(4) 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 P1 0.01717(13) 0.01498(12) 0.01916(13) 0.00171(10) 0.00253(10) 0.00881(11) S1 0.02599(15) 0.02048(14) 0.03247(16) 0.00110(11) 0.00050(11) 0.01571(11) O1 0.0216(4) 0.0222(4) 0.0206(4) -0.0033(3) -0.0016(3) 0.0117(3) O2 0.0261(4) 0.0296(4) 0.0225(4) -0.0078(3) -0.0040(3) 0.0195(4) C1 0.0180(5) 0.0162(5) 0.0254(6) 0.0017(4) 0.0041(4) 0.0092(4) C2 0.0217(6) 0.0192(5) 0.0289(6) 0.0020(5) 0.0006(5) 0.0090(5) C3 0.0223(6) 0.0241(6) 0.0314(7) -0.0015(5) -0.0010(5) 0.0099(5) C4 0.0184(6) 0.0184(6) 0.0381(7) -0.0009(5) 0.0056(5) 0.0050(5) C5 0.0252(6) 0.0199(6) 0.0331(7) 0.0070(5) 0.0113(5) 0.0100(5) C6 0.0213(5) 0.0213(6) 0.0271(6) 0.0054(4) 0.0063(5) 0.0123(5) C7 0.0201(5) 0.0147(5) 0.0177(5) 0.0030(4) 0.0031(4) 0.0090(4) C8 0.0220(6) 0.0187(5) 0.0227(6) -0.0006(4) 0.0004(4) 0.0085(5) C9 0.0326(7) 0.0226(6) 0.0191(5) -0.0015(4) 0.0036(5) 0.0122(5) C10 0.0285(6) 0.0251(6) 0.0238(6) 0.0005(5) 0.0101(5) 0.0108(5) C11 0.0211(6) 0.0182(5) 0.0283(6) -0.0013(4) 0.0058(5) 0.0056(5) C12 0.0229(6) 0.0150(5) 0.0196(5) -0.0004(4) 0.0018(4) 0.0096(4) C13 0.0183(5) 0.0157(5) 0.0195(5) 0.0021(4) 0.0030(4) 0.0042(4) C14 0.0238(6) 0.0187(5) 0.0336(7) 0.0023(5) -0.0023(5) 0.0065(5) C15 0.0295(7) 0.0282(7) 0.0310(7) 0.0080(5) -0.0065(5) 0.0031(6) C16 0.0319(7) 0.0406(8) 0.0193(6) -0.0008(6) 0.0007(5) 0.0023(6) C17 0.0297(7) 0.0379(8) 0.0297(7) -0.0117(6) 0.0077(6) 0.0093(6) C18 0.0227(6) 0.0226(6) 0.0263(6) -0.0027(5) 0.0032(5) 0.0084(5) C19 0.0185(5) 0.0159(5) 0.0172(5) 0.0027(4) 0.0048(4) 0.0072(4) C20 0.0186(5) 0.0159(5) 0.0180(5) -0.0001(4) 0.0022(4) 0.0070(4) C21 0.0226(6) 0.0240(6) 0.0199(5) 0.0004(4) 0.0002(4) 0.0110(5) C22 0.0270(6) 0.0270(6) 0.0171(5) -0.0017(4) 0.0026(5) 0.0081(5) C23 0.0297(6) 0.0228(6) 0.0205(6) -0.0027(4) 0.0089(5) 0.0097(5) C24 0.0265(6) 0.0198(5) 0.0232(6) 0.0023(4) 0.0078(5) 0.0126(5) C25 0.0205(5) 0.0153(5) 0.0190(5) 0.0014(4) 0.0020(4) 0.0100(4) C26 0.0282(6) 0.0340(6) 0.0249(6) -0.0094(5) -0.0044(5) 0.0235(5) C27 0.0504(9) 0.0324(7) 0.0414(8) -0.0026(6) 0.0019(7) 0.0306(7) C28 0.0420(9) 0.0743(13) 0.0393(8) -0.0232(9) -0.0158(7) 0.0456(10) C29 0.0340(7) 0.0361(7) 0.0287(6) -0.0047(5) 0.0038(5) 0.0218(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 P1 C1 1.8202(12) . ? P1 C7 1.8331(12) . ? P1 C19 1.8346(12) . ? P1 S1 1.9635(4) . ? O1 C25 1.2064(14) . ? O2 C25 1.3338(15) . ? O2 C26 1.4879(14) . ? C1 C2 1.3964(18) . ? C1 C6 1.3973(16) . ? C2 C3 1.3960(18) . ? C2 H2 0.964(18) . ? C3 C4 1.389(2) . ? C3 H3 0.95(2) . ? C4 C5 1.384(2) . ? C4 H4 0.910(17) . ? C5 C6 1.3921(18) . ? C5 H5 0.955(17) . ? C6 H6 0.936(17) . ? C7 C8 1.4025(17) . ? C7 C12 1.4144(16) . ? C8 C9 1.3877(17) . ? C8 H8 0.960(16) . ? C9 C10 1.384(2) . ? C9 H9 0.988(18) . ? C10 C11 1.3874(19) . ? C10 H10 0.965(17) . ? C11 C12 1.3995(17) . ? C11 H11 0.935(17) . ? C12 C13 1.4974(16) . ? C13 C18 1.3894(17) . ? C13 C14 1.4005(18) . ? C14 C15 1.386(2) . ? C14 H14 0.96(2) . ? C15 C16 1.378(3) . ? C15 H15 0.924(19) . ? C16 C17 1.384(3) . ? C16 H16 0.93(2) . ? C17 C18 1.3958(19) . ? C17 H17 1.00(2) . ? C18 H18 0.927(19) . ? C19 C24 1.3963(16) . ? C19 C20 1.4083(16) . ? C20 C21 1.3957(17) . ? C20 C25 1.4981(15) . ? C21 C22 1.3944(18) . ? C21 H21 0.892(19) . ? C22 C23 1.380(2) . ? C22 H22 0.907(18) . ? C23 C24 1.3890(19) . ? C23 H23 0.955(18) . ? C24 H24 0.948(16) . ? C26 C27 1.519(2) . ? C26 C29 1.520(2) . ? C26 C28 1.5205(19) . ? C27 H27A 1.006(19) . ? C27 H27B 0.96(2) . ? C27 H27C 0.99(2) . ? C28 H28A 1.01(2) . ? C28 H28B 1.01(3) . ? C28 H28C 0.98(2) . ? C29 H29A 0.96(2) . ? C29 H29B 0.98(2) . ? C29 H29C 1.026(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C7 110.66(5) . . ? C1 P1 C19 105.71(5) . . ? C7 P1 C19 108.79(5) . . ? C1 P1 S1 107.84(4) . . ? C7 P1 S1 109.73(4) . . ? C19 P1 S1 114.05(4) . . ? C25 O2 C26 120.80(9) . . ? C2 C1 C6 119.06(11) . . ? C2 C1 P1 119.34(9) . . ? C6 C1 P1 121.20(10) . . ? C3 C2 C1 120.43(12) . . ? C3 C2 H2 119.5(10) . . ? C1 C2 H2 120.1(10) . . ? C4 C3 C2 119.82(13) . . ? C4 C3 H3 123.7(14) . . ? C2 C3 H3 116.5(14) . . ? C5 C4 C3 120.04(12) . . ? C5 C4 H4 119.0(11) . . ? C3 C4 H4 120.9(11) . . ? C4 C5 C6 120.36(12) . . ? C4 C5 H5 121.1(10) . . ? C6 C5 H5 118.5(10) . . ? C5 C6 C1 120.20(12) . . ? C5 C6 H6 121.5(10) . . ? C1 C6 H6 118.3(11) . . ? C8 C7 C12 118.96(11) . . ? C8 C7 P1 117.33(9) . . ? C12 C7 P1 123.62(9) . . ? C9 C8 C7 121.66(11) . . ? C9 C8 H8 118.7(10) . . ? C7 C8 H8 119.6(10) . . ? C10 C9 C8 119.33(12) . . ? C10 C9 H9 120.7(10) . . ? C8 C9 H9 120.0(10) . . ? C9 C10 C11 119.91(12) . . ? C9 C10 H10 121.2(10) . . ? C11 C10 H10 118.8(10) . . ? C10 C11 C12 121.88(12) . . ? C10 C11 H11 119.1(10) . . ? C12 C11 H11 119.1(10) . . ? C11 C12 C7 118.21(11) . . ? C11 C12 C13 116.95(11) . . ? C7 C12 C13 124.69(10) . . ? C18 C13 C14 118.57(12) . . ? C18 C13 C12 122.96(11) . . ? C14 C13 C12 118.46(11) . . ? C15 C14 C13 120.73(14) . . ? C15 C14 H14 123.5(13) . . ? C13 C14 H14 115.6(13) . . ? C16 C15 C14 120.14(15) . . ? C16 C15 H15 119.3(11) . . ? C14 C15 H15 120.5(11) . . ? C15 C16 C17 119.89(14) . . ? C15 C16 H16 118.8(11) . . ? C17 C16 H16 121.3(11) . . ? C16 C17 C18 120.26(14) . . ? C16 C17 H17 117.8(13) . . ? C18 C17 H17 121.9(13) . . ? C13 C18 C17 120.30(13) . . ? C13 C18 H18 118.3(11) . . ? C17 C18 H18 121.4(11) . . ? C24 C19 C20 118.50(11) . . ? C24 C19 P1 115.69(9) . . ? C20 C19 P1 125.76(8) . . ? C21 C20 C19 119.88(10) . . ? C21 C20 C25 118.65(10) . . ? C19 C20 C25 121.42(10) . . ? C22 C21 C20 120.50(12) . . ? C22 C21 H21 122.0(12) . . ? C20 C21 H21 117.4(12) . . ? C23 C22 C21 119.74(12) . . ? C23 C22 H22 120.4(11) . . ? C21 C22 H22 119.9(11) . . ? C22 C23 C24 120.16(11) . . ? C22 C23 H23 119.4(11) . . ? C24 C23 H23 120.3(11) . . ? C23 C24 C19 121.17(12) . . ? C23 C24 H24 120.1(10) . . ? C19 C24 H24 118.8(10) . . ? O1 C25 O2 125.56(10) . . ? O1 C25 C20 123.14(10) . . ? O2 C25 C20 111.29(10) . . ? O2 C26 C27 110.20(11) . . ? O2 C26 C29 109.93(10) . . ? C27 C26 C29 112.70(12) . . ? O2 C26 C28 101.51(10) . . ? C27 C26 C28 110.77(13) . . ? C29 C26 C28 111.17(13) . . ? C26 C27 H27A 111.1(10) . . ? C26 C27 H27B 111.7(12) . . ? H27A C27 H27B 106.7(16) . . ? C26 C27 H27C 109.1(13) . . ? H27A C27 H27C 107.5(16) . . ? H27B C27 H27C 110.6(17) . . ? C26 C28 H28A 110.8(12) . . ? C26 C28 H28B 111.1(16) . . ? H28A C28 H28B 109(2) . . ? C26 C28 H28C 109.2(12) . . ? H28A C28 H28C 104.8(16) . . ? H28B C28 H28C 111.3(19) . . ? C26 C29 H29A 111.4(12) . . ? C26 C29 H29B 109.4(12) . . ? H29A C29 H29B 107.7(16) . . ? C26 C29 H29C 106.6(11) . . ? H29A C29 H29C 110.5(16) . . ? H29B C29 H29C 111.3(16) . . ? 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 C7 P1 C1 C2 70.55(11) . . . . ? C19 P1 C1 C2 -171.83(10) . . . . ? S1 P1 C1 C2 -49.48(10) . . . . ? C7 P1 C1 C6 -116.74(10) . . . . ? C19 P1 C1 C6 0.88(11) . . . . ? S1 P1 C1 C6 123.24(9) . . . . ? C6 C1 C2 C3 3.22(18) . . . . ? P1 C1 C2 C3 176.10(10) . . . . ? C1 C2 C3 C4 -3.2(2) . . . . ? C2 C3 C4 C5 0.9(2) . . . . ? C3 C4 C5 C6 1.1(2) . . . . ? C4 C5 C6 C1 -1.06(19) . . . . ? C2 C1 C6 C5 -1.12(18) . . . . ? P1 C1 C6 C5 -173.86(10) . . . . ? C1 P1 C7 C8 -21.40(11) . . . . ? C19 P1 C7 C8 -137.12(9) . . . . ? S1 P1 C7 C8 97.48(9) . . . . ? C1 P1 C7 C12 162.15(9) . . . . ? C19 P1 C7 C12 46.43(11) . . . . ? S1 P1 C7 C12 -78.97(10) . . . . ? C12 C7 C8 C9 2.14(18) . . . . ? P1 C7 C8 C9 -174.49(10) . . . . ? C7 C8 C9 C10 -0.2(2) . . . . ? C8 C9 C10 C11 -1.8(2) . . . . ? C9 C10 C11 C12 1.8(2) . . . . ? C10 C11 C12 C7 0.21(19) . . . . ? C10 C11 C12 C13 -175.57(12) . . . . ? C8 C7 C12 C11 -2.12(17) . . . . ? P1 C7 C12 C11 174.27(9) . . . . ? C8 C7 C12 C13 173.30(11) . . . . ? P1 C7 C12 C13 -10.31(16) . . . . ? C11 C12 C13 C18 -121.00(13) . . . . ? C7 C12 C13 C18 63.52(16) . . . . ? C11 C12 C13 C14 58.25(15) . . . . ? C7 C12 C13 C14 -117.22(13) . . . . ? C18 C13 C14 C15 -3.56(18) . . . . ? C12 C13 C14 C15 177.15(11) . . . . ? C13 C14 C15 C16 1.8(2) . . . . ? C14 C15 C16 C17 1.0(2) . . . . ? C15 C16 C17 C18 -2.1(2) . . . . ? C14 C13 C18 C17 2.50(18) . . . . ? C12 C13 C18 C17 -178.24(12) . . . . ? C16 C17 C18 C13 0.3(2) . . . . ? C1 P1 C19 C24 103.01(10) . . . . ? C7 P1 C19 C24 -138.12(9) . . . . ? S1 P1 C19 C24 -15.28(10) . . . . ? C1 P1 C19 C20 -79.74(11) . . . . ? C7 P1 C19 C20 39.12(12) . . . . ? S1 P1 C19 C20 161.96(9) . . . . ? C24 C19 C20 C21 0.46(17) . . . . ? P1 C19 C20 C21 -176.71(9) . . . . ? C24 C19 C20 C25 -177.19(11) . . . . ? P1 C19 C20 C25 5.63(16) . . . . ? C19 C20 C21 C22 -1.94(18) . . . . ? C25 C20 C21 C22 175.78(11) . . . . ? C20 C21 C22 C23 1.67(19) . . . . ? C21 C22 C23 C24 0.07(19) . . . . ? C22 C23 C24 C19 -1.6(2) . . . . ? C20 C19 C24 C23 1.29(18) . . . . ? P1 C19 C24 C23 178.74(10) . . . . ? C26 O2 C25 O1 1.76(17) . . . . ? C26 O2 C25 C20 -177.19(10) . . . . ? C21 C20 C25 O1 -146.56(12) . . . . ? C19 C20 C25 O1 31.12(17) . . . . ? C21 C20 C25 O2 32.42(15) . . . . ? C19 C20 C25 O2 -149.90(11) . . . . ? C25 O2 C26 C27 59.98(15) . . . . ? C25 O2 C26 C29 -64.82(15) . . . . ? C25 O2 C26 C28 177.41(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.275 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.040 #===END data_992ck9 _database_code_depnum_ccdc_archive 'CCDC 227102' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tert-butyl 2-[biphenyl-2-yl(phenyl)phosphorothioyl]benzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H27 O2 P S' _chemical_formula_weight 470.54 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' 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 Hexagonal _symmetry_space_group_name_H-M P6(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 10.9341(3) _cell_length_b 10.9341(3) _cell_length_c 35.377(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3662.8(3) _cell_formula_units_Z 6 _cell_measurement_temperature 373(2) _cell_measurement_reflns_used 9726 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.21 _exptl_crystal_description 'hexagonal pyramid' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9323 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 373(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50489 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.27 _reflns_number_total 6067 _reflns_number_gt 5730 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0408P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_number_reflns 6067 _refine_ls_number_parameters 406 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0605 _refine_ls_wR_factor_gt 0.0601 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _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 0.46615(3) 0.16380(3) 0.109031(9) 0.01750(7) Uani 1 1 d . . . S1 S 0.40562(4) -0.03789(3) 0.112475(10) 0.02539(8) Uani 1 1 d . . . O1 O 0.57046(9) 0.48018(9) 0.10954(3) 0.02178(18) Uani 1 1 d . . . O2 O 0.76926(10) 0.60936(9) 0.07547(3) 0.0246(2) Uani 1 1 d . . . C1 C 0.31393(13) 0.18361(13) 0.11972(4) 0.0202(2) Uani 1 1 d . . . C2 C 0.26637(14) 0.24792(13) 0.09420(4) 0.0235(3) Uani 1 1 d . . . C3 C 0.14232(15) 0.25000(15) 0.10133(4) 0.0274(3) Uani 1 1 d . . . C4 C 0.06665(15) 0.19065(15) 0.13406(4) 0.0275(3) Uani 1 1 d . . . C5 C 0.11279(15) 0.12646(15) 0.15960(4) 0.0279(3) Uani 1 1 d . . . C6 C 0.23418(15) 0.11993(14) 0.15207(4) 0.0245(3) Uani 1 1 d . . . C7 C 0.60974(13) 0.26401(13) 0.14270(3) 0.0183(2) Uani 1 1 d . . . C8 C 0.57352(14) 0.29832(14) 0.17753(4) 0.0225(3) Uani 1 1 d . . . C9 C 0.67229(16) 0.36329(15) 0.20600(4) 0.0260(3) Uani 1 1 d . . . C10 C 0.81036(16) 0.39549(15) 0.20002(4) 0.0274(3) Uani 1 1 d . . . C11 C 0.84908(15) 0.36635(15) 0.16534(4) 0.0252(3) Uani 1 1 d . . . C12 C 0.75148(14) 0.30065(13) 0.13611(4) 0.0203(2) Uani 1 1 d . . . C13 C 0.80803(13) 0.28445(14) 0.09898(4) 0.0208(3) Uani 1 1 d . . . C14 C 0.76348(15) 0.15461(15) 0.08201(4) 0.0263(3) Uani 1 1 d . . . C15 C 0.81705(17) 0.1466(2) 0.04700(4) 0.0374(4) Uani 1 1 d . . . C16 C 0.91540(17) 0.2681(2) 0.02882(4) 0.0386(4) Uani 1 1 d . . . C17 C 0.96312(17) 0.3972(2) 0.04579(5) 0.0355(4) Uani 1 1 d . . . C18 C 0.91223(15) 0.40608(16) 0.08088(4) 0.0285(3) Uani 1 1 d . . . C19 C 0.52480(13) 0.23914(13) 0.06166(3) 0.0185(2) Uani 1 1 d . . . C20 C 0.60707(13) 0.38379(13) 0.05314(3) 0.0189(2) Uani 1 1 d . . . C21 C 0.65024(14) 0.42640(15) 0.01603(4) 0.0229(3) Uani 1 1 d . . . C22 C 0.60923(15) 0.32710(16) -0.01289(4) 0.0270(3) Uani 1 1 d . . . C23 C 0.52833(15) 0.18541(16) -0.00473(4) 0.0264(3) Uani 1 1 d . . . C24 C 0.48774(15) 0.14175(15) 0.03232(4) 0.0230(3) Uani 1 1 d . . . C25 C 0.64515(13) 0.49454(13) 0.08288(3) 0.0189(2) Uani 1 1 d . . . C26 C 0.82555(15) 0.73592(13) 0.10021(4) 0.0270(3) Uani 1 1 d . . . C27 C 0.85629(18) 0.70034(17) 0.13932(4) 0.0321(3) Uani 1 1 d . . . C28 C 0.9614(2) 0.83779(18) 0.07973(6) 0.0456(5) Uani 1 1 d . . . C29 C 0.7246(2) 0.79302(17) 0.10110(5) 0.0381(4) Uani 1 1 d . . . H2 H 0.3180(16) 0.2881(15) 0.0720(4) 0.020(4) Uiso 1 1 d . . . H3 H 0.1120(16) 0.2956(16) 0.0830(4) 0.022(4) Uiso 1 1 d . . . H4 H -0.0110(17) 0.1960(17) 0.1388(4) 0.022(4) Uiso 1 1 d . . . H5 H 0.065(2) 0.083(2) 0.1819(6) 0.047(5) Uiso 1 1 d . . . H6 H 0.2598(16) 0.0695(17) 0.1685(5) 0.025(4) Uiso 1 1 d . . . H8 H 0.4783(16) 0.2790(15) 0.1812(4) 0.019(4) Uiso 1 1 d . . . H9 H 0.6456(17) 0.3861(17) 0.2305(5) 0.025(4) Uiso 1 1 d . . . H10 H 0.8840(17) 0.4440(16) 0.2192(4) 0.024(4) Uiso 1 1 d . . . H11 H 0.9438(16) 0.3923(15) 0.1618(4) 0.018(4) Uiso 1 1 d . . . H14 H 0.698(2) 0.0750(19) 0.0945(5) 0.038(5) Uiso 1 1 d . . . H15 H 0.788(2) 0.057(2) 0.0350(5) 0.048(5) Uiso 1 1 d . . . H16 H 0.9521(18) 0.2670(17) 0.0051(5) 0.031(4) Uiso 1 1 d . . . H17 H 1.0293(18) 0.4780(19) 0.0341(5) 0.031(4) Uiso 1 1 d . . . H18 H 0.9422(18) 0.494(2) 0.0936(5) 0.038(5) Uiso 1 1 d . . . H21 H 0.7060(17) 0.5199(18) 0.0115(5) 0.025(4) Uiso 1 1 d . . . H22 H 0.6387(17) 0.3563(17) -0.0372(5) 0.025(4) Uiso 1 1 d . . . H23 H 0.5014(17) 0.1157(17) -0.0249(5) 0.024(4) Uiso 1 1 d . . . H24 H 0.4308(17) 0.0409(17) 0.0379(4) 0.027(4) Uiso 1 1 d . . . H27A H 0.7722(19) 0.6360(19) 0.1530(5) 0.030(4) Uiso 1 1 d . . . H27B H 0.9100(19) 0.7942(19) 0.1537(5) 0.034(4) Uiso 1 1 d . . . H27C H 0.913(2) 0.654(2) 0.1369(5) 0.043(5) Uiso 1 1 d . . . H28A H 1.0101(19) 0.925(2) 0.0933(5) 0.037(5) Uiso 1 1 d . . . H28B H 1.029(2) 0.798(2) 0.0787(6) 0.044(5) Uiso 1 1 d . . . H28C H 0.940(3) 0.854(3) 0.0525(8) 0.076(7) Uiso 1 1 d . . . H29A H 0.6367(19) 0.7331(18) 0.1175(5) 0.032(4) Uiso 1 1 d . . . H29B H 0.689(2) 0.792(2) 0.0765(6) 0.044(5) Uiso 1 1 d . . . H29C H 0.774(2) 0.888(2) 0.1117(5) 0.040(5) 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 P1 0.01799(15) 0.01499(14) 0.02002(14) -0.00101(12) -0.00276(12) 0.00862(12) S1 0.02692(16) 0.01565(14) 0.03364(18) 0.00054(12) -0.00037(13) 0.01067(13) O1 0.0224(4) 0.0211(4) 0.0214(4) -0.0019(4) 0.0016(4) 0.0105(4) O2 0.0264(5) 0.0173(4) 0.0239(5) -0.0036(4) 0.0039(4) 0.0064(4) C1 0.0181(6) 0.0158(6) 0.0266(6) -0.0033(5) -0.0042(5) 0.0085(5) C2 0.0227(6) 0.0194(6) 0.0272(7) -0.0017(5) -0.0073(5) 0.0096(5) C3 0.0254(7) 0.0256(7) 0.0339(8) -0.0047(6) -0.0119(6) 0.0148(6) C4 0.0179(6) 0.0269(7) 0.0397(8) -0.0075(6) -0.0060(6) 0.0128(6) C5 0.0238(7) 0.0272(7) 0.0316(8) -0.0005(6) 0.0017(6) 0.0121(6) C6 0.0230(7) 0.0226(6) 0.0299(7) 0.0011(5) -0.0017(5) 0.0130(6) C7 0.0207(6) 0.0179(6) 0.0188(6) -0.0001(5) -0.0036(5) 0.0115(5) C8 0.0230(7) 0.0244(6) 0.0225(6) -0.0004(5) -0.0001(5) 0.0137(5) C9 0.0337(7) 0.0311(7) 0.0197(6) -0.0045(5) -0.0031(5) 0.0210(6) C10 0.0296(7) 0.0328(8) 0.0234(7) -0.0091(6) -0.0107(6) 0.0183(6) C11 0.0220(7) 0.0282(7) 0.0296(7) -0.0068(6) -0.0060(5) 0.0157(6) C12 0.0250(6) 0.0192(6) 0.0208(6) -0.0019(5) -0.0023(5) 0.0142(5) C13 0.0192(6) 0.0274(6) 0.0209(6) -0.0013(5) -0.0038(5) 0.0154(5) C14 0.0230(7) 0.0302(7) 0.0272(7) -0.0053(6) -0.0039(6) 0.0144(6) C15 0.0310(8) 0.0508(10) 0.0323(8) -0.0208(7) -0.0096(6) 0.0219(8) C16 0.0318(8) 0.0699(12) 0.0203(7) -0.0008(7) -0.0005(6) 0.0300(8) C17 0.0293(8) 0.0527(10) 0.0324(8) 0.0144(7) 0.0060(6) 0.0264(8) C18 0.0248(7) 0.0308(7) 0.0351(8) 0.0038(6) 0.0007(6) 0.0178(6) C19 0.0185(6) 0.0211(6) 0.0181(6) -0.0023(5) -0.0046(5) 0.0117(5) C20 0.0195(6) 0.0219(6) 0.0189(6) -0.0023(5) -0.0026(5) 0.0130(5) C21 0.0227(6) 0.0252(7) 0.0214(6) 0.0000(5) -0.0004(5) 0.0124(6) C22 0.0273(7) 0.0393(8) 0.0183(6) -0.0040(6) -0.0023(5) 0.0196(6) C23 0.0302(7) 0.0335(7) 0.0216(7) -0.0122(6) -0.0099(6) 0.0205(6) C24 0.0257(7) 0.0220(6) 0.0243(6) -0.0051(5) -0.0080(5) 0.0142(6) C25 0.0211(6) 0.0166(6) 0.0205(6) 0.0002(5) -0.0021(5) 0.0105(5) C26 0.0297(7) 0.0155(6) 0.0263(7) -0.0060(5) 0.0035(5) 0.0042(5) C27 0.0352(8) 0.0275(7) 0.0293(7) -0.0089(6) -0.0034(6) 0.0125(7) C28 0.0437(10) 0.0244(8) 0.0424(10) -0.0089(7) 0.0144(8) -0.0027(7) C29 0.0515(10) 0.0230(7) 0.0414(10) -0.0056(6) -0.0022(8) 0.0199(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.8223(13) . ? P1 C7 1.8341(13) . ? P1 C19 1.8358(13) . ? P1 S1 1.9638(4) . ? O1 C25 1.2053(15) . ? O2 C25 1.3352(16) . ? O2 C26 1.4860(15) . ? C1 C2 1.3949(18) . ? C1 C6 1.3955(19) . ? C2 C3 1.391(2) . ? C2 H2 0.938(15) . ? C3 C4 1.382(2) . ? C3 H3 0.973(16) . ? C4 C5 1.385(2) . ? C4 H4 0.896(16) . ? C5 C6 1.390(2) . ? C5 H5 0.94(2) . ? C6 H6 0.935(16) . ? C7 C8 1.4015(18) . ? C7 C12 1.4127(18) . ? C8 C9 1.3851(19) . ? C8 H8 0.962(15) . ? C9 C10 1.384(2) . ? C9 H9 0.984(17) . ? C10 C11 1.386(2) . ? C10 H10 0.982(16) . ? C11 C12 1.3990(19) . ? C11 H11 0.936(15) . ? C12 C13 1.4996(18) . ? C13 C14 1.3862(19) . ? C13 C18 1.401(2) . ? C14 C15 1.391(2) . ? C14 H14 0.919(18) . ? C15 C16 1.381(3) . ? C15 H15 0.97(2) . ? C16 C17 1.375(3) . ? C16 H16 0.931(18) . ? C17 C18 1.383(2) . ? C17 H17 0.914(18) . ? C18 H18 0.963(19) . ? C19 C24 1.3943(18) . ? C19 C20 1.4067(18) . ? C20 C21 1.3940(18) . ? C20 C25 1.4975(17) . ? C21 C22 1.393(2) . ? C21 H21 0.906(17) . ? C22 C23 1.377(2) . ? C22 H22 0.919(17) . ? C23 C24 1.389(2) . ? C23 H23 0.975(16) . ? C24 H24 0.978(16) . ? C26 C29 1.516(2) . ? C26 C27 1.519(2) . ? C26 C28 1.522(2) . ? C27 H27A 0.963(19) . ? C27 H27B 1.027(18) . ? C27 H27C 0.99(2) . ? C28 H28A 0.960(19) . ? C28 H28B 1.03(2) . ? C28 H28C 1.03(3) . ? C29 H29A 1.030(18) . ? C29 H29B 0.95(2) . ? C29 H29C 0.970(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C7 110.74(6) . . ? C1 P1 C19 105.72(6) . . ? C7 P1 C19 108.79(6) . . ? C1 P1 S1 107.79(4) . . ? C7 P1 S1 109.74(4) . . ? C19 P1 S1 113.99(4) . . ? C25 O2 C26 120.86(10) . . ? C2 C1 C6 119.00(12) . . ? C2 C1 P1 121.23(10) . . ? C6 C1 P1 119.39(10) . . ? C3 C2 C1 120.21(13) . . ? C3 C2 H2 120.5(9) . . ? C1 C2 H2 119.2(9) . . ? C4 C3 C2 120.27(13) . . ? C4 C3 H3 121.6(9) . . ? C2 C3 H3 118.2(9) . . ? C3 C4 C5 120.03(13) . . ? C3 C4 H4 119.5(10) . . ? C5 C4 H4 120.5(10) . . ? C4 C5 C6 120.01(14) . . ? C4 C5 H5 123.6(13) . . ? C6 C5 H5 116.4(13) . . ? C5 C6 C1 120.40(13) . . ? C5 C6 H6 119.1(10) . . ? C1 C6 H6 120.4(10) . . ? C8 C7 C12 119.06(11) . . ? C8 C7 P1 117.31(10) . . ? C12 C7 P1 123.53(9) . . ? C9 C8 C7 121.64(12) . . ? C9 C8 H8 119.7(9) . . ? C7 C8 H8 118.6(9) . . ? C10 C9 C8 119.39(13) . . ? C10 C9 H9 119.6(9) . . ? C8 C9 H9 121.0(9) . . ? C9 C10 C11 119.77(13) . . ? C9 C10 H10 121.8(9) . . ? C11 C10 H10 118.4(9) . . ? C10 C11 C12 122.00(13) . . ? C10 C11 H11 118.0(9) . . ? C12 C11 H11 120.0(9) . . ? C11 C12 C7 118.09(12) . . ? C11 C12 C13 117.02(12) . . ? C7 C12 C13 124.72(11) . . ? C14 C13 C18 118.48(13) . . ? C14 C13 C12 123.09(12) . . ? C18 C13 C12 118.43(12) . . ? C13 C14 C15 120.42(15) . . ? C13 C14 H14 118.0(11) . . ? C15 C14 H14 121.6(11) . . ? C16 C15 C14 120.28(15) . . ? C16 C15 H15 118.4(12) . . ? C14 C15 H15 121.3(12) . . ? C17 C16 C15 119.85(15) . . ? C17 C16 H16 117.5(10) . . ? C15 C16 H16 122.7(10) . . ? C16 C17 C18 120.30(16) . . ? C16 C17 H17 120.3(11) . . ? C18 C17 H17 119.4(11) . . ? C17 C18 C13 120.57(15) . . ? C17 C18 H18 122.9(11) . . ? C13 C18 H18 116.5(11) . . ? C24 C19 C20 118.52(12) . . ? C24 C19 P1 115.72(10) . . ? C20 C19 P1 125.71(9) . . ? C21 C20 C19 119.79(11) . . ? C21 C20 C25 118.72(11) . . ? C19 C20 C25 121.44(11) . . ? C22 C21 C20 120.53(13) . . ? C22 C21 H21 121.4(11) . . ? C20 C21 H21 118.0(11) . . ? C23 C22 C21 119.90(13) . . ? C23 C22 H22 120.2(10) . . ? C21 C22 H22 119.8(10) . . ? C22 C23 C24 119.96(12) . . ? C22 C23 H23 120.0(9) . . ? C24 C23 H23 120.0(9) . . ? C23 C24 C19 121.26(13) . . ? C23 C24 H24 119.5(9) . . ? C19 C24 H24 119.2(9) . . ? O1 C25 O2 125.45(11) . . ? O1 C25 C20 123.23(11) . . ? O2 C25 C20 111.30(10) . . ? O2 C26 C29 110.35(12) . . ? O2 C26 C27 109.85(11) . . ? C29 C26 C27 112.74(13) . . ? O2 C26 C28 101.49(11) . . ? C29 C26 C28 110.69(14) . . ? C27 C26 C28 111.16(14) . . ? C26 C27 H27A 113.1(10) . . ? C26 C27 H27B 106.5(10) . . ? H27A C27 H27B 110.0(14) . . ? C26 C27 H27C 109.3(10) . . ? H27A C27 H27C 106.5(14) . . ? H27B C27 H27C 111.5(15) . . ? C26 C28 H28A 110.1(11) . . ? C26 C28 H28B 110.5(11) . . ? H28A C28 H28B 106.5(15) . . ? C26 C28 H28C 110.4(15) . . ? H28A C28 H28C 110.7(18) . . ? H28B C28 H28C 108.5(18) . . ? C26 C29 H29A 112.9(9) . . ? C26 C29 H29B 110.7(12) . . ? H29A C29 H29B 105.4(15) . . ? C26 C29 H29C 108.2(11) . . ? H29A C29 H29C 107.9(14) . . ? H29B C29 H29C 111.7(16) . . ? 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 C7 P1 C1 C2 116.68(11) . . . . ? C19 P1 C1 C2 -0.99(12) . . . . ? S1 P1 C1 C2 -123.26(10) . . . . ? C7 P1 C1 C6 -70.38(11) . . . . ? C19 P1 C1 C6 171.95(10) . . . . ? S1 P1 C1 C6 49.68(11) . . . . ? C6 C1 C2 C3 0.94(19) . . . . ? P1 C1 C2 C3 173.90(10) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? C2 C3 C4 C5 -1.2(2) . . . . ? C3 C4 C5 C6 -0.9(2) . . . . ? C4 C5 C6 C1 3.0(2) . . . . ? C2 C1 C6 C5 -3.04(19) . . . . ? P1 C1 C6 C5 -176.13(11) . . . . ? C1 P1 C7 C8 21.37(12) . . . . ? C19 P1 C7 C8 137.15(10) . . . . ? S1 P1 C7 C8 -97.52(10) . . . . ? C1 P1 C7 C12 -162.28(10) . . . . ? C19 P1 C7 C12 -46.50(12) . . . . ? S1 P1 C7 C12 78.84(11) . . . . ? C12 C7 C8 C9 -1.99(19) . . . . ? P1 C7 C8 C9 174.53(10) . . . . ? C7 C8 C9 C10 0.1(2) . . . . ? C8 C9 C10 C11 1.9(2) . . . . ? C9 C10 C11 C12 -2.0(2) . . . . ? C10 C11 C12 C7 0.1(2) . . . . ? C10 C11 C12 C13 175.58(13) . . . . ? C8 C7 C12 C11 1.85(18) . . . . ? P1 C7 C12 C11 -174.44(10) . . . . ? C8 C7 C12 C13 -173.22(12) . . . . ? P1 C7 C12 C13 10.49(18) . . . . ? C11 C12 C13 C14 121.07(14) . . . . ? C7 C12 C13 C14 -63.81(18) . . . . ? C11 C12 C13 C18 -57.99(16) . . . . ? C7 C12 C13 C18 117.13(14) . . . . ? C18 C13 C14 C15 -2.8(2) . . . . ? C12 C13 C14 C15 178.19(12) . . . . ? C13 C14 C15 C16 0.1(2) . . . . ? C14 C15 C16 C17 1.6(2) . . . . ? C15 C16 C17 C18 -0.5(2) . . . . ? C16 C17 C18 C13 -2.2(2) . . . . ? C14 C13 C18 C17 3.8(2) . . . . ? C12 C13 C18 C17 -177.08(12) . . . . ? C1 P1 C19 C24 -102.91(10) . . . . ? C7 P1 C19 C24 138.12(10) . . . . ? S1 P1 C19 C24 15.30(11) . . . . ? C1 P1 C19 C20 79.77(12) . . . . ? C7 P1 C19 C20 -39.20(12) . . . . ? S1 P1 C19 C20 -162.01(10) . . . . ? C24 C19 C20 C21 -0.43(18) . . . . ? P1 C19 C20 C21 176.82(10) . . . . ? C24 C19 C20 C25 177.12(12) . . . . ? P1 C19 C20 C25 -5.63(17) . . . . ? C19 C20 C21 C22 1.83(19) . . . . ? C25 C20 C21 C22 -175.79(12) . . . . ? C20 C21 C22 C23 -1.6(2) . . . . ? C21 C22 C23 C24 0.0(2) . . . . ? C22 C23 C24 C19 1.4(2) . . . . ? C20 C19 C24 C23 -1.18(19) . . . . ? P1 C19 C24 C23 -178.70(11) . . . . ? C26 O2 C25 O1 -1.79(18) . . . . ? C26 O2 C25 C20 177.13(11) . . . . ? C21 C20 C25 O1 146.42(12) . . . . ? C19 C20 C25 O1 -31.15(18) . . . . ? C21 C20 C25 O2 -32.53(16) . . . . ? C19 C20 C25 O2 149.90(11) . . . . ? C25 O2 C26 C29 -60.02(16) . . . . ? C25 O2 C26 C27 64.88(16) . . . . ? C25 O2 C26 C28 -177.41(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.316 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.038 #===END data_cko1 _database_code_depnum_ccdc_archive 'CCDC 227103' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R)-tert-butyl 2-(phenyl[2-trifluoromethyl)phenyl]phosphorothioyl)benzoat ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 F3 O2 P S' _chemical_formula_weight 462.45 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.9795(9) _cell_length_b 14.313(1) _cell_length_c 18.102(2) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 2326.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9357 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18072 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 24.76 _reflns_number_total 3972 _reflns_number_gt 3834 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0265P)^2^+2.0470P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(11) _refine_ls_number_reflns 3972 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.267 _refine_ls_restrained_S_all 1.267 _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 P1 P 0.30284(9) 0.72522(6) 0.78529(5) 0.0115(2) Uani 1 1 d . . . S1 S 0.15081(10) 0.78882(7) 0.84423(5) 0.0196(2) Uani 1 1 d . . . C1 C 0.3619(4) 0.7930(2) 0.70432(18) 0.0145(7) Uani 1 1 d . . . C2 C 0.3324(4) 0.8890(2) 0.7078(2) 0.0187(8) Uani 1 1 d . . . H2 H 0.2894 0.9147 0.7512 0.022 Uiso 1 1 calc R . . C3 C 0.3649(4) 0.9466(3) 0.6491(2) 0.0207(8) Uani 1 1 d . . . H3 H 0.3439 1.0115 0.6522 0.025 Uiso 1 1 calc R . . C4 C 0.4284(4) 0.9100(3) 0.5853(2) 0.0237(9) Uani 1 1 d . . . H4 H 0.4521 0.9500 0.5451 0.028 Uiso 1 1 calc R . . C5 C 0.4571(5) 0.8156(3) 0.5804(2) 0.0216(9) Uani 1 1 d . . . H5 H 0.4982 0.7907 0.5363 0.026 Uiso 1 1 calc R . . C6 C 0.4261(4) 0.7562(2) 0.63988(18) 0.0133(8) Uani 1 1 d . . . C7 C 0.4682(4) 0.6549(2) 0.63358(19) 0.0138(8) Uani 1 1 d . . . O7 O 0.5102(3) 0.60996(17) 0.68577(13) 0.0188(6) Uani 1 1 d . . . O8 O 0.4505(3) 0.62428(17) 0.56479(13) 0.0226(6) Uani 1 1 d . . . C8 C 0.4964(5) 0.5276(3) 0.5443(2) 0.0263(10) Uani 1 1 d . . . C9 C 0.4662(7) 0.5255(3) 0.4618(2) 0.0487(14) Uani 1 1 d . . . H9A H 0.3613 0.5404 0.4527 0.073 Uiso 1 1 calc R . . H9B H 0.4885 0.4632 0.4424 0.073 Uiso 1 1 calc R . . H9C H 0.5294 0.5718 0.4370 0.073 Uiso 1 1 calc R . . C10 C 0.3996(5) 0.4581(3) 0.5848(3) 0.0368(12) Uani 1 1 d . . . H10A H 0.4252 0.4585 0.6374 0.055 Uiso 1 1 calc R . . H10B H 0.4162 0.3954 0.5646 0.055 Uiso 1 1 calc R . . H10C H 0.2947 0.4752 0.5787 0.055 Uiso 1 1 calc R . . C11 C 0.6600(5) 0.5151(3) 0.5607(3) 0.0363(11) Uani 1 1 d . . . H11A H 0.7167 0.5657 0.5375 0.054 Uiso 1 1 calc R . . H11B H 0.6938 0.4549 0.5409 0.054 Uiso 1 1 calc R . . H11C H 0.6758 0.5164 0.6142 0.054 Uiso 1 1 calc R . . C12 C 0.2315(4) 0.6099(2) 0.75889(18) 0.0121(8) Uani 1 1 d . . . C13 C 0.2973(4) 0.5339(2) 0.7950(2) 0.0184(8) Uani 1 1 d . . . H13 H 0.3832 0.5445 0.8244 0.022 Uiso 1 1 calc R . . C14 C 0.2423(4) 0.4440(2) 0.7895(2) 0.0201(9) Uani 1 1 d . . . H14 H 0.2907 0.3941 0.8144 0.024 Uiso 1 1 calc R . . C15 C 0.1167(4) 0.4271(3) 0.7477(2) 0.0205(9) Uani 1 1 d . . . H15 H 0.0755 0.3660 0.7451 0.025 Uiso 1 1 calc R . . C16 C 0.0513(4) 0.5004(3) 0.7096(2) 0.0201(8) Uani 1 1 d . . . H16 H -0.0329 0.4886 0.6792 0.024 Uiso 1 1 calc R . . C17 C 0.1073(4) 0.5916(2) 0.7149(2) 0.0163(8) Uani 1 1 d . . . C18 C 0.0203(4) 0.6610(3) 0.6702(2) 0.0226(9) Uani 1 1 d . . . F1 F -0.1185(3) 0.6728(2) 0.69639(17) 0.0496(8) Uani 1 1 d . . . F2 F 0.0024(4) 0.63318(18) 0.60083(14) 0.0526(8) Uani 1 1 d . . . F3 F 0.0781(2) 0.74632(14) 0.66731(13) 0.0302(6) Uani 1 1 d . . . C19 C 0.4685(4) 0.7081(2) 0.84160(19) 0.0146(7) Uani 1 1 d . . . C20 C 0.4474(4) 0.6845(2) 0.9161(2) 0.0179(8) Uani 1 1 d . . . H20 H 0.3497 0.6742 0.9346 0.021 Uiso 1 1 calc R . . C21 C 0.5684(5) 0.6762(3) 0.9625(2) 0.0249(10) Uani 1 1 d . . . H21 H 0.5539 0.6587 1.0126 0.030 Uiso 1 1 calc R . . C22 C 0.7106(5) 0.6931(2) 0.9366(2) 0.0248(10) Uani 1 1 d . . . H22 H 0.7932 0.6882 0.9692 0.030 Uiso 1 1 calc R . . C23 C 0.7333(4) 0.7171(3) 0.8635(2) 0.0235(9) Uani 1 1 d . . . H23 H 0.8312 0.7284 0.8458 0.028 Uiso 1 1 calc R . . C24 C 0.6118(4) 0.7246(2) 0.8160(2) 0.0178(8) Uani 1 1 d . . . H24 H 0.6271 0.7411 0.7657 0.021 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 0.0139(4) 0.0088(4) 0.0119(4) -0.0012(4) -0.0004(4) 0.0018(4) S1 0.0194(5) 0.0197(5) 0.0196(5) -0.0038(4) 0.0033(4) 0.0065(4) C1 0.0142(17) 0.0143(18) 0.0151(17) -0.0011(15) -0.0084(15) -0.0021(15) C2 0.018(2) 0.0177(19) 0.021(2) -0.0025(16) -0.0008(16) 0.0004(15) C3 0.0177(19) 0.0150(19) 0.029(2) 0.0073(17) -0.0068(18) -0.0034(16) C4 0.027(2) 0.023(2) 0.021(2) 0.0129(17) -0.0109(18) -0.0062(18) C5 0.034(2) 0.018(2) 0.0128(19) 0.0006(15) -0.0014(17) -0.0029(17) C6 0.0152(18) 0.0140(18) 0.0108(18) -0.0006(13) -0.0036(14) -0.0004(14) C7 0.0121(18) 0.0145(18) 0.0148(19) -0.0045(15) 0.0050(15) -0.0021(15) O7 0.0277(15) 0.0147(13) 0.0139(13) 0.0026(10) 0.0011(11) 0.0026(11) O8 0.0354(17) 0.0176(14) 0.0146(13) -0.0042(11) -0.0031(12) 0.0012(13) C8 0.037(3) 0.020(2) 0.021(2) -0.0112(17) 0.0017(19) 0.0048(18) C9 0.085(4) 0.035(3) 0.027(2) -0.017(2) -0.003(3) 0.007(3) C10 0.050(3) 0.017(2) 0.043(3) -0.010(2) 0.009(2) -0.006(2) C11 0.041(3) 0.031(3) 0.036(3) -0.011(2) 0.015(2) 0.007(2) C12 0.0165(19) 0.0100(18) 0.0099(18) -0.0039(13) 0.0038(14) -0.0020(14) C13 0.0210(19) 0.0181(19) 0.0162(19) -0.0041(15) -0.0016(17) 0.0012(16) C14 0.026(2) 0.0139(19) 0.021(2) 0.0008(17) 0.0025(17) -0.0023(15) C15 0.023(2) 0.0128(19) 0.026(2) -0.0016(16) 0.0020(17) -0.0101(15) C16 0.017(2) 0.024(2) 0.0187(19) -0.0038(17) -0.0038(17) -0.0065(16) C17 0.020(2) 0.0180(19) 0.0113(18) 0.0004(15) 0.0014(15) -0.0039(14) C18 0.020(2) 0.029(2) 0.019(2) -0.0054(17) -0.0076(17) -0.0048(17) F1 0.0161(13) 0.0561(18) 0.077(2) 0.0283(16) 0.0055(13) 0.0078(12) F2 0.096(2) 0.0337(15) 0.0284(14) -0.0049(12) -0.0298(15) 0.0101(16) F3 0.0300(13) 0.0185(12) 0.0423(15) 0.0088(10) -0.0199(11) -0.0017(10) C19 0.0201(19) 0.0048(16) 0.0189(18) -0.0076(15) -0.0040(15) 0.0008(14) C20 0.025(2) 0.0112(18) 0.0178(19) 0.0001(15) -0.0038(17) 0.0019(15) C21 0.040(3) 0.021(2) 0.0143(19) -0.0019(16) -0.0137(19) 0.0033(19) C22 0.033(2) 0.0112(19) 0.030(2) -0.0018(16) -0.025(2) 0.0022(17) C23 0.021(2) 0.0114(19) 0.038(2) 0.0014(18) -0.0094(17) -0.0007(16) C24 0.0182(19) 0.0096(18) 0.025(2) -0.0012(16) -0.0048(15) -0.0007(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 C19 1.820(3) . ? P1 C12 1.833(3) . ? P1 C1 1.836(4) . ? P1 S1 1.9572(12) . ? C1 C2 1.401(5) . ? C1 C6 1.404(5) . ? C2 C3 1.375(5) . ? C3 C4 1.391(6) . ? C4 C5 1.378(5) . ? C5 C6 1.400(5) . ? C6 C7 1.502(5) . ? C7 O7 1.203(4) . ? C7 O8 1.330(4) . ? O8 C8 1.491(4) . ? C8 C11 1.509(6) . ? C8 C10 1.511(6) . ? C8 C9 1.517(6) . ? C12 C17 1.396(5) . ? C12 C13 1.400(5) . ? C13 C14 1.381(5) . ? C14 C15 1.380(5) . ? C15 C16 1.386(5) . ? C16 C17 1.402(5) . ? C17 C18 1.501(5) . ? C18 F2 1.326(4) . ? C18 F3 1.328(4) . ? C18 F1 1.344(5) . ? C19 C24 1.388(5) . ? C19 C20 1.403(5) . ? C20 C21 1.378(5) . ? C21 C22 1.382(6) . ? C22 C23 1.382(6) . ? C23 C24 1.394(5) . ? 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 C19 P1 C12 108.06(16) . . ? C19 P1 C1 106.41(16) . . ? C12 P1 C1 111.60(15) . . ? C19 P1 S1 109.11(12) . . ? C12 P1 S1 108.48(12) . . ? C1 P1 S1 113.02(12) . . ? C2 C1 C6 118.9(3) . . ? C2 C1 P1 115.3(3) . . ? C6 C1 P1 125.7(3) . . ? C3 C2 C1 120.9(4) . . ? C2 C3 C4 120.1(3) . . ? C5 C4 C3 120.0(4) . . ? C4 C5 C6 120.6(4) . . ? C5 C6 C1 119.5(3) . . ? C5 C6 C7 118.5(3) . . ? C1 C6 C7 121.9(3) . . ? O7 C7 O8 126.6(3) . . ? O7 C7 C6 122.4(3) . . ? O8 C7 C6 111.0(3) . . ? C7 O8 C8 120.4(3) . . ? O8 C8 C11 109.3(3) . . ? O8 C8 C10 109.3(3) . . ? C11 C8 C10 112.7(4) . . ? O8 C8 C9 102.3(3) . . ? C11 C8 C9 111.4(4) . . ? C10 C8 C9 111.2(4) . . ? C17 C12 C13 117.2(3) . . ? C17 C12 P1 126.7(3) . . ? C13 C12 P1 115.5(3) . . ? C14 C13 C12 122.7(4) . . ? C15 C14 C13 119.7(4) . . ? C14 C15 C16 119.1(3) . . ? C15 C16 C17 121.3(3) . . ? C12 C17 C16 120.1(3) . . ? C12 C17 C18 126.8(3) . . ? C16 C17 C18 113.1(3) . . ? F2 C18 F3 106.7(3) . . ? F2 C18 F1 105.0(3) . . ? F3 C18 F1 105.1(3) . . ? F2 C18 C17 112.0(3) . . ? F3 C18 C17 115.2(3) . . ? F1 C18 C17 112.0(3) . . ? C24 C19 C20 119.2(3) . . ? C24 C19 P1 123.2(3) . . ? C20 C19 P1 117.4(3) . . ? C21 C20 C19 120.0(4) . . ? C20 C21 C22 120.5(4) . . ? C21 C22 C23 120.3(3) . . ? C22 C23 C24 119.7(4) . . ? C19 C24 C23 120.4(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.76 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.404 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.062 #===END