# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Shigehiro Yamaguchi' _publ_contact_author_email yamaguchi@chem.nagoya-u.ac.jp _publ_section_title ; Intense Fluorescence of 1-Aryl-2,3,4,5-tetraphenylphosphole Oxides in the Crystalline State ; loop_ _publ_author_name 'Aiko Fukuzawa' 'Yasunori Ichihashi' 'Shigehiro Yamaguchi' # Attachment '- cmpd2rev.CIF' data_cmpd2rev_ _database_code_depnum_ccdc_archive 'CCDC 767155' #TrackingRef '- cmpd2rev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-mesityl-2,3,4,5-tetraphenyl-1H-phosphole-1-oxide ; _chemical_name_common 1-mesityl-2,3,4,5-tetraphenyl-1H-phosphole-1-oxide _chemical_melting_point 192 _chemical_formula_moiety ? _chemical_formula_sum 'C37 H31 O P' _chemical_formula_weight 522.59 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 10.1486(8) _cell_length_b 16.5262(11) _cell_length_c 17.1966(14) _cell_angle_alpha 90 _cell_angle_beta 97.0498(14) _cell_angle_gamma 90 _cell_volume 2862.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 95(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9816 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 95(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating-anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23470 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4931 _reflns_number_gt 4423 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_cell_refinement 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_data_reduction 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0371P)^2^+1.6500P] 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 4931 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.02406(6) 0.09726(3) 0.27675(3) 0.01566(15) Uani 1 1 d . . . C1 C -0.0434(2) -0.00159(12) 0.25058(13) 0.0160(5) Uani 1 1 d . . . C2 C -0.1200(2) 0.00299(13) 0.18031(13) 0.0165(5) Uani 1 1 d . . . C3 C -0.1243(2) 0.08593(13) 0.14306(12) 0.0168(5) Uani 1 1 d . . . C4 C -0.0466(2) 0.14152(13) 0.18446(13) 0.0173(5) Uani 1 1 d . . . O1 O -0.02663(15) 0.13586(9) 0.34494(9) 0.0207(4) Uani 1 1 d . . . C5 C -0.0110(2) -0.07308(13) 0.30051(13) 0.0175(5) Uani 1 1 d . . . C6 C -0.0046(2) -0.06670(14) 0.38181(13) 0.0217(5) Uani 1 1 d . . . H1 H -0.0186 -0.0156 0.4047 0.026 Uiso 1 1 calc R . . C7 C 0.0221(2) -0.13389(14) 0.42976(14) 0.0262(6) Uani 1 1 d . . . H2 H 0.0256 -0.1286 0.4850 0.031 Uiso 1 1 calc R . . C8 C 0.0434(2) -0.20850(14) 0.39703(15) 0.0295(6) Uani 1 1 d . . . H3 H 0.0594 -0.2548 0.4296 0.035 Uiso 1 1 calc R . . C9 C 0.0415(2) -0.21553(14) 0.31667(15) 0.0274(6) Uani 1 1 d . . . H4 H 0.0584 -0.2665 0.2943 0.033 Uiso 1 1 calc R . . C10 C 0.0151(2) -0.14886(13) 0.26893(14) 0.0222(5) Uani 1 1 d . . . H5 H 0.0145 -0.1544 0.2139 0.027 Uiso 1 1 calc R . . C11 C -0.1885(2) -0.06858(12) 0.14136(12) 0.0167(5) Uani 1 1 d . . . C12 C -0.2705(2) -0.11590(13) 0.18258(13) 0.0191(5) Uani 1 1 d . . . H6 H -0.2935 -0.0976 0.2315 0.023 Uiso 1 1 calc R . . C13 C -0.3185(2) -0.18929(14) 0.15255(14) 0.0225(5) Uani 1 1 d . . . H7 H -0.3740 -0.2212 0.1810 0.027 Uiso 1 1 calc R . . C14 C -0.2859(2) -0.21650(14) 0.08112(14) 0.0250(5) Uani 1 1 d . . . H8 H -0.3161 -0.2678 0.0614 0.030 Uiso 1 1 calc R . . C15 C -0.2087(2) -0.16815(14) 0.03877(14) 0.0244(5) Uani 1 1 d . . . H9 H -0.1887 -0.1857 -0.0110 0.029 Uiso 1 1 calc R . . C16 C -0.1604(2) -0.09443(13) 0.06831(13) 0.0202(5) Uani 1 1 d . . . H10 H -0.1082 -0.0616 0.0386 0.024 Uiso 1 1 calc R . . C17 C -0.2047(2) 0.10186(12) 0.06661(13) 0.0175(5) Uani 1 1 d . . . C18 C -0.3385(2) 0.08007(13) 0.05232(14) 0.0208(5) Uani 1 1 d . . . H11 H -0.3788 0.0520 0.0915 0.025 Uiso 1 1 calc R . . C19 C -0.4133(2) 0.09898(14) -0.01843(14) 0.0238(5) Uani 1 1 d . . . H12 H -0.5047 0.0850 -0.0269 0.029 Uiso 1 1 calc R . . C20 C -0.3550(2) 0.13819(14) -0.07666(14) 0.0270(6) Uani 1 1 d . . . H13 H -0.4061 0.1508 -0.1252 0.032 Uiso 1 1 calc R . . C21 C -0.2216(2) 0.15896(14) -0.06388(14) 0.0246(5) Uani 1 1 d . . . H14 H -0.1809 0.1852 -0.1039 0.029 Uiso 1 1 calc R . . C22 C -0.1478(2) 0.14144(13) 0.00725(13) 0.0197(5) Uani 1 1 d . . . H15 H -0.0569 0.1566 0.0158 0.024 Uiso 1 1 calc R . . C23 C -0.0329(2) 0.22859(13) 0.16742(13) 0.0186(5) Uani 1 1 d . . . C24 C -0.1434(2) 0.27711(13) 0.14416(13) 0.0210(5) Uani 1 1 d . . . H16 H -0.2299 0.2542 0.1395 0.025 Uiso 1 1 calc R . . C25 C -0.1281(2) 0.35839(13) 0.12782(13) 0.0237(5) Uani 1 1 d . . . H17 H -0.2041 0.3908 0.1122 0.028 Uiso 1 1 calc R . . C26 C -0.0033(3) 0.39251(14) 0.13406(14) 0.0282(6) Uani 1 1 d . . . H18 H 0.0067 0.4480 0.1217 0.034 Uiso 1 1 calc R . . C27 C 0.1072(3) 0.34588(14) 0.15825(16) 0.0324(6) Uani 1 1 d . . . H19 H 0.1932 0.3694 0.1630 0.039 Uiso 1 1 calc R . . C28 C 0.0924(2) 0.26445(14) 0.17554(14) 0.0260(6) Uani 1 1 d . . . H20 H 0.1684 0.2329 0.1931 0.031 Uiso 1 1 calc R . . C29 C 0.2048(2) 0.09197(12) 0.28416(13) 0.0165(5) Uani 1 1 d . . . C30 C 0.2824(2) 0.11429(13) 0.35461(13) 0.0197(5) Uani 1 1 d . . . C31 C 0.4205(2) 0.11637(14) 0.35701(14) 0.0243(5) Uani 1 1 d . . . H21 H 0.4722 0.1338 0.4038 0.029 Uiso 1 1 calc R . . C32 C 0.4851(2) 0.09407(13) 0.29392(14) 0.0232(5) Uani 1 1 d . . . C33 C 0.4079(2) 0.06837(13) 0.22666(14) 0.0226(5) Uani 1 1 d . . . H22 H 0.4508 0.0505 0.1836 0.027 Uiso 1 1 calc R . . C34 C 0.2698(2) 0.06758(12) 0.21953(13) 0.0189(5) Uani 1 1 d . . . C35 C 0.6344(2) 0.09723(16) 0.29882(17) 0.0347(6) Uani 1 1 d . . . H23 H 0.6669 0.0478 0.2762 0.052 Uiso 1 1 calc R . . H24 H 0.6727 0.1017 0.3538 0.052 Uiso 1 1 calc R . . H25 H 0.6607 0.1443 0.2697 0.052 Uiso 1 1 calc R . . C36 C 0.1980(2) 0.04003(15) 0.14182(14) 0.0272(6) Uani 1 1 d . . . H26 H 0.2631 0.0250 0.1067 0.041 Uiso 1 1 calc R . . H27 H 0.1421 0.0841 0.1183 0.041 Uiso 1 1 calc R . . H28 H 0.1423 -0.0069 0.1501 0.041 Uiso 1 1 calc R . . C37 C 0.2273(3) 0.13419(16) 0.43024(14) 0.0300(6) Uani 1 1 d . . . H29 H 0.2996 0.1520 0.4695 0.045 Uiso 1 1 calc R . . H30 H 0.1853 0.0859 0.4494 0.045 Uiso 1 1 calc R . . H31 H 0.1613 0.1775 0.4208 0.045 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 0.0155(3) 0.0143(3) 0.0171(3) -0.0009(2) 0.0016(2) 0.0004(2) C1 0.0142(11) 0.0162(11) 0.0182(12) -0.0016(9) 0.0044(9) -0.0001(9) C2 0.0143(12) 0.0161(11) 0.0202(12) -0.0005(9) 0.0063(9) 0.0007(9) C3 0.0157(12) 0.0177(11) 0.0177(11) 0.0011(9) 0.0052(9) 0.0016(9) C4 0.0150(12) 0.0172(11) 0.0197(12) -0.0001(9) 0.0027(9) 0.0027(9) O1 0.0205(9) 0.0211(8) 0.0209(8) -0.0034(6) 0.0041(7) 0.0023(6) C5 0.0128(12) 0.0180(11) 0.0210(12) 0.0012(9) 0.0001(9) -0.0021(9) C6 0.0206(13) 0.0207(12) 0.0237(12) 0.0007(9) 0.0022(10) 0.0011(9) C7 0.0243(14) 0.0322(14) 0.0224(13) 0.0075(10) 0.0035(10) 0.0038(10) C8 0.0253(14) 0.0221(13) 0.0388(15) 0.0118(11) -0.0057(12) -0.0004(10) C9 0.0263(14) 0.0192(12) 0.0340(15) -0.0003(10) -0.0068(11) 0.0024(10) C10 0.0220(13) 0.0208(12) 0.0227(13) 0.0001(9) -0.0015(10) 0.0010(10) C11 0.0148(11) 0.0153(11) 0.0188(12) 0.0023(9) -0.0027(9) 0.0010(9) C12 0.0171(12) 0.0221(12) 0.0176(11) 0.0035(9) -0.0002(9) -0.0009(9) C13 0.0174(12) 0.0233(12) 0.0254(13) 0.0073(10) -0.0028(10) -0.0046(9) C14 0.0236(13) 0.0192(12) 0.0299(14) 0.0006(10) -0.0058(11) -0.0034(10) C15 0.0261(14) 0.0254(13) 0.0210(12) -0.0055(10) 0.0009(10) -0.0014(10) C16 0.0198(12) 0.0207(12) 0.0199(12) 0.0012(9) 0.0023(10) -0.0027(9) C17 0.0187(12) 0.0142(11) 0.0194(11) -0.0008(9) 0.0014(9) 0.0014(9) C18 0.0205(13) 0.0192(12) 0.0227(12) 0.0006(9) 0.0025(10) 0.0004(9) C19 0.0172(12) 0.0248(12) 0.0281(13) -0.0008(10) -0.0026(10) 0.0009(10) C20 0.0289(14) 0.0286(13) 0.0214(13) 0.0015(10) -0.0052(11) 0.0061(11) C21 0.0311(14) 0.0243(12) 0.0185(12) 0.0026(10) 0.0039(11) 0.0021(10) C22 0.0173(12) 0.0189(11) 0.0230(12) -0.0009(9) 0.0027(10) 0.0009(9) C23 0.0246(13) 0.0146(11) 0.0164(11) -0.0012(9) 0.0019(10) -0.0005(9) C24 0.0221(13) 0.0224(12) 0.0183(12) 0.0001(9) 0.0018(10) 0.0037(10) C25 0.0319(14) 0.0212(12) 0.0177(12) 0.0007(9) 0.0019(10) 0.0086(10) C26 0.0429(16) 0.0125(11) 0.0286(14) 0.0012(10) 0.0023(12) -0.0012(11) C27 0.0306(15) 0.0188(13) 0.0468(17) 0.0018(11) 0.0002(13) -0.0066(11) C28 0.0227(13) 0.0197(12) 0.0343(14) 0.0010(10) -0.0012(11) 0.0004(10) C29 0.0178(12) 0.0117(10) 0.0201(11) 0.0023(9) 0.0025(9) 0.0005(9) C30 0.0212(13) 0.0165(11) 0.0212(12) 0.0012(9) 0.0014(10) 0.0008(9) C31 0.0209(13) 0.0223(12) 0.0282(13) 0.0016(10) -0.0025(10) -0.0017(10) C32 0.0178(13) 0.0147(11) 0.0367(14) 0.0032(10) 0.0017(10) 0.0009(9) C33 0.0214(13) 0.0177(11) 0.0299(13) 0.0039(10) 0.0083(10) 0.0015(9) C34 0.0215(13) 0.0118(10) 0.0235(12) 0.0007(9) 0.0027(10) 0.0004(9) C35 0.0164(13) 0.0342(15) 0.0529(18) -0.0023(13) 0.0024(12) -0.0006(11) C36 0.0226(13) 0.0357(14) 0.0244(13) -0.0072(11) 0.0069(11) 0.0003(11) C37 0.0276(14) 0.0406(15) 0.0211(13) -0.0051(11) -0.0006(11) -0.0052(11) _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 1.4815(16) . ? P1 C1 1.807(2) . ? P1 C4 1.814(2) . ? P1 C29 1.825(2) . ? C1 C2 1.356(3) . ? C1 C5 1.474(3) . ? C2 C11 1.489(3) . ? C2 C3 1.511(3) . ? C3 C4 1.355(3) . ? C3 C17 1.483(3) . ? C4 C23 1.478(3) . ? C5 C6 1.396(3) . ? C5 C10 1.403(3) . ? C6 C7 1.390(3) . ? C6 H1 0.9500 . ? C7 C8 1.384(3) . ? C7 H2 0.9500 . ? C8 C9 1.384(4) . ? C8 H3 0.9500 . ? C9 C10 1.381(3) . ? C9 H4 0.9500 . ? C10 H5 0.9500 . ? C11 C16 1.389(3) . ? C11 C12 1.397(3) . ? C12 C13 1.383(3) . ? C12 H6 0.9500 . ? C13 C14 1.386(3) . ? C13 H7 0.9500 . ? C14 C15 1.387(3) . ? C14 H8 0.9500 . ? C15 C16 1.386(3) . ? C15 H9 0.9500 . ? C16 H10 0.9500 . ? C17 C22 1.396(3) . ? C17 C18 1.397(3) . ? C18 C19 1.388(3) . ? C18 H11 0.9500 . ? C19 C20 1.385(3) . ? C19 H12 0.9500 . ? C20 C21 1.388(3) . ? C20 H13 0.9500 . ? C21 C22 1.384(3) . ? C21 H14 0.9500 . ? C22 H15 0.9500 . ? C23 C28 1.394(3) . ? C23 C24 1.397(3) . ? C24 C25 1.385(3) . ? C24 H16 0.9500 . ? C25 C26 1.379(3) . ? C25 H17 0.9500 . ? C26 C27 1.382(4) . ? C26 H18 0.9500 . ? C27 C28 1.390(3) . ? C27 H19 0.9500 . ? C28 H20 0.9500 . ? C29 C30 1.411(3) . ? C29 C34 1.419(3) . ? C30 C31 1.398(3) . ? C30 C37 1.514(3) . ? C31 C32 1.384(3) . ? C31 H21 0.9500 . ? C32 C33 1.382(3) . ? C32 C35 1.508(3) . ? C33 C34 1.392(3) . ? C33 H22 0.9500 . ? C34 C36 1.512(3) . ? C35 H23 0.9800 . ? C35 H24 0.9800 . ? C35 H25 0.9800 . ? C36 H26 0.9800 . ? C36 H27 0.9800 . ? C36 H28 0.9800 . ? C37 H29 0.9800 . ? C37 H30 0.9800 . ? C37 H31 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C1 115.38(10) . . ? O1 P1 C4 112.37(9) . . ? C1 P1 C4 92.84(10) . . ? O1 P1 C29 114.14(10) . . ? C1 P1 C29 108.74(10) . . ? C4 P1 C29 111.50(10) . . ? C2 C1 C5 128.79(19) . . ? C2 C1 P1 109.25(16) . . ? C5 C1 P1 121.93(16) . . ? C1 C2 C11 122.77(19) . . ? C1 C2 C3 114.33(19) . . ? C11 C2 C3 122.83(19) . . ? C4 C3 C17 124.53(19) . . ? C4 C3 C2 114.06(19) . . ? C17 C3 C2 121.39(18) . . ? C3 C4 C23 128.2(2) . . ? C3 C4 P1 109.18(16) . . ? C23 C4 P1 121.97(16) . . ? C6 C5 C10 117.9(2) . . ? C6 C5 C1 120.19(19) . . ? C10 C5 C1 121.9(2) . . ? C7 C6 C5 121.1(2) . . ? C7 C6 H1 119.5 . . ? C5 C6 H1 119.5 . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H2 120.0 . . ? C6 C7 H2 120.0 . . ? C7 C8 C9 119.8(2) . . ? C7 C8 H3 120.1 . . ? C9 C8 H3 120.1 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H4 119.8 . . ? C8 C9 H4 119.8 . . ? C9 C10 C5 120.9(2) . . ? C9 C10 H5 119.5 . . ? C5 C10 H5 119.5 . . ? C16 C11 C12 119.2(2) . . ? C16 C11 C2 120.98(19) . . ? C12 C11 C2 119.40(19) . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H6 119.8 . . ? C11 C12 H6 119.8 . . ? C12 C13 C14 120.3(2) . . ? C12 C13 H7 119.9 . . ? C14 C13 H7 119.9 . . ? C13 C14 C15 119.4(2) . . ? C13 C14 H8 120.3 . . ? C15 C14 H8 120.3 . . ? C16 C15 C14 120.7(2) . . ? C16 C15 H9 119.6 . . ? C14 C15 H9 119.6 . . ? C15 C16 C11 119.9(2) . . ? C15 C16 H10 120.0 . . ? C11 C16 H10 120.0 . . ? C22 C17 C18 118.2(2) . . ? C22 C17 C3 120.0(2) . . ? C18 C17 C3 121.8(2) . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H11 119.6 . . ? C17 C18 H11 119.6 . . ? C20 C19 C18 120.2(2) . . ? C20 C19 H12 119.9 . . ? C18 C19 H12 119.9 . . ? C19 C20 C21 119.8(2) . . ? C19 C20 H13 120.1 . . ? C21 C20 H13 120.1 . . ? C22 C21 C20 120.0(2) . . ? C22 C21 H14 120.0 . . ? C20 C21 H14 120.0 . . ? C21 C22 C17 121.1(2) . . ? C21 C22 H15 119.4 . . ? C17 C22 H15 119.4 . . ? C28 C23 C24 118.4(2) . . ? C28 C23 C4 120.0(2) . . ? C24 C23 C4 121.6(2) . . ? C25 C24 C23 120.6(2) . . ? C25 C24 H16 119.7 . . ? C23 C24 H16 119.7 . . ? C26 C25 C24 120.4(2) . . ? C26 C25 H17 119.8 . . ? C24 C25 H17 119.8 . . ? C25 C26 C27 120.0(2) . . ? C25 C26 H18 120.0 . . ? C27 C26 H18 120.0 . . ? C26 C27 C28 119.9(2) . . ? C26 C27 H19 120.0 . . ? C28 C27 H19 120.0 . . ? C27 C28 C23 120.8(2) . . ? C27 C28 H20 119.6 . . ? C23 C28 H20 119.6 . . ? C30 C29 C34 118.8(2) . . ? C30 C29 P1 119.87(17) . . ? C34 C29 P1 121.27(17) . . ? C31 C30 C29 119.0(2) . . ? C31 C30 C37 116.4(2) . . ? C29 C30 C37 124.6(2) . . ? C32 C31 C30 122.7(2) . . ? C32 C31 H21 118.7 . . ? C30 C31 H21 118.7 . . ? C33 C32 C31 117.6(2) . . ? C33 C32 C35 121.3(2) . . ? C31 C32 C35 121.0(2) . . ? C32 C33 C34 122.5(2) . . ? C32 C33 H22 118.7 . . ? C34 C33 H22 118.7 . . ? C33 C34 C29 119.2(2) . . ? C33 C34 C36 116.9(2) . . ? C29 C34 C36 123.9(2) . . ? C32 C35 H23 109.5 . . ? C32 C35 H24 109.5 . . ? H23 C35 H24 109.5 . . ? C32 C35 H25 109.5 . . ? H23 C35 H25 109.5 . . ? H24 C35 H25 109.5 . . ? C34 C36 H26 109.5 . . ? C34 C36 H27 109.5 . . ? H26 C36 H27 109.5 . . ? C34 C36 H28 109.5 . . ? H26 C36 H28 109.5 . . ? H27 C36 H28 109.5 . . ? C30 C37 H29 109.5 . . ? C30 C37 H30 109.5 . . ? H29 C37 H30 109.5 . . ? C30 C37 H31 109.5 . . ? H29 C37 H31 109.5 . . ? H30 C37 H31 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 O1 P1 C1 C2 112.26(16) . . . . ? C4 P1 C1 C2 -4.18(17) . . . . ? C29 P1 C1 C2 -118.03(16) . . . . ? O1 P1 C1 C5 -69.5(2) . . . . ? C4 P1 C1 C5 174.04(18) . . . . ? C29 P1 C1 C5 60.2(2) . . . . ? C5 C1 C2 C11 0.9(4) . . . . ? P1 C1 C2 C11 178.93(17) . . . . ? C5 C1 C2 C3 -176.2(2) . . . . ? P1 C1 C2 C3 1.9(2) . . . . ? C1 C2 C3 C4 2.5(3) . . . . ? C11 C2 C3 C4 -174.5(2) . . . . ? C1 C2 C3 C17 -179.22(19) . . . . ? C11 C2 C3 C17 3.7(3) . . . . ? C17 C3 C4 C23 5.4(4) . . . . ? C2 C3 C4 C23 -176.4(2) . . . . ? C17 C3 C4 P1 176.29(17) . . . . ? C2 C3 C4 P1 -5.5(2) . . . . ? O1 P1 C4 C3 -113.38(16) . . . . ? C1 P1 C4 C3 5.60(17) . . . . ? C29 P1 C4 C3 117.02(16) . . . . ? O1 P1 C4 C23 58.2(2) . . . . ? C1 P1 C4 C23 177.16(18) . . . . ? C29 P1 C4 C23 -71.4(2) . . . . ? C2 C1 C5 C6 -141.1(2) . . . . ? P1 C1 C5 C6 41.0(3) . . . . ? C2 C1 C5 C10 39.3(3) . . . . ? P1 C1 C5 C10 -138.54(19) . . . . ? C10 C5 C6 C7 -2.3(3) . . . . ? C1 C5 C6 C7 178.1(2) . . . . ? C5 C6 C7 C8 0.4(4) . . . . ? C6 C7 C8 C9 1.6(4) . . . . ? C7 C8 C9 C10 -1.6(4) . . . . ? C8 C9 C10 C5 -0.4(4) . . . . ? C6 C5 C10 C9 2.3(3) . . . . ? C1 C5 C10 C9 -178.1(2) . . . . ? C1 C2 C11 C16 -119.1(2) . . . . ? C3 C2 C11 C16 57.7(3) . . . . ? C1 C2 C11 C12 53.4(3) . . . . ? C3 C2 C11 C12 -129.8(2) . . . . ? C16 C11 C12 C13 2.8(3) . . . . ? C2 C11 C12 C13 -169.9(2) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 C15 -2.3(3) . . . . ? C13 C14 C15 C16 2.1(3) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C12 C11 C16 C15 -2.9(3) . . . . ? C2 C11 C16 C15 169.6(2) . . . . ? C4 C3 C17 C22 47.4(3) . . . . ? C2 C3 C17 C22 -130.7(2) . . . . ? C4 C3 C17 C18 -131.0(2) . . . . ? C2 C3 C17 C18 51.0(3) . . . . ? C22 C17 C18 C19 -1.4(3) . . . . ? C3 C17 C18 C19 177.0(2) . . . . ? C17 C18 C19 C20 1.5(3) . . . . ? C18 C19 C20 C21 -0.4(4) . . . . ? C19 C20 C21 C22 -0.9(3) . . . . ? C20 C21 C22 C17 1.0(3) . . . . ? C18 C17 C22 C21 0.2(3) . . . . ? C3 C17 C22 C21 -178.3(2) . . . . ? C3 C4 C23 C28 -136.9(2) . . . . ? P1 C4 C23 C28 53.3(3) . . . . ? C3 C4 C23 C24 44.1(3) . . . . ? P1 C4 C23 C24 -125.7(2) . . . . ? C28 C23 C24 C25 1.5(3) . . . . ? C4 C23 C24 C25 -179.4(2) . . . . ? C23 C24 C25 C26 0.2(3) . . . . ? C24 C25 C26 C27 -1.3(4) . . . . ? C25 C26 C27 C28 0.6(4) . . . . ? C26 C27 C28 C23 1.2(4) . . . . ? C24 C23 C28 C27 -2.2(4) . . . . ? C4 C23 C28 C27 178.7(2) . . . . ? O1 P1 C29 C30 7.6(2) . . . . ? C1 P1 C29 C30 -122.81(17) . . . . ? C4 P1 C29 C30 136.24(17) . . . . ? O1 P1 C29 C34 -170.87(16) . . . . ? C1 P1 C29 C34 58.74(19) . . . . ? C4 P1 C29 C34 -42.2(2) . . . . ? C34 C29 C30 C31 3.8(3) . . . . ? P1 C29 C30 C31 -174.66(16) . . . . ? C34 C29 C30 C37 -174.2(2) . . . . ? P1 C29 C30 C37 7.3(3) . . . . ? C29 C30 C31 C32 -2.8(3) . . . . ? C37 C30 C31 C32 175.4(2) . . . . ? C30 C31 C32 C33 -0.5(3) . . . . ? C30 C31 C32 C35 180.0(2) . . . . ? C31 C32 C33 C34 2.8(3) . . . . ? C35 C32 C33 C34 -177.7(2) . . . . ? C32 C33 C34 C29 -1.7(3) . . . . ? C32 C33 C34 C36 178.4(2) . . . . ? C30 C29 C34 C33 -1.7(3) . . . . ? P1 C29 C34 C33 176.78(16) . . . . ? C30 C29 C34 C36 178.2(2) . . . . ? P1 C29 C34 C36 -3.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.245 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.047 data_cmpd3rev _database_code_depnum_ccdc_archive 'CCDC 767156' #TrackingRef '- cmpd3rev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,4,5-tetraphenyl-1-(2',4',6'-triisopropylphenyl)-1H-phosphole-1-oxide ; _chemical_name_common ;2,3,4,5-tetraphenyl-1-(2',4',6'-triisopropylphenyl)-1H- phosphole-1-oxide ; _chemical_melting_point 210 _chemical_formula_moiety ? _chemical_formula_sum 'C43 H43 O P' _chemical_formula_weight 606.74 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.153(3) _cell_length_b 10.506(4) _cell_length_c 35.335(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3398.1(19) _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 block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9832 _exptl_absorpt_correction_T_max 0.9943 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotation-anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28731 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5979 _reflns_number_gt 5813 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_cell_refinement 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_data_reduction 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0287P)^2^+0.9561P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(7) _refine_ls_number_reflns 5979 _refine_ls_number_parameters 413 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.85590(4) 0.40990(4) 0.376531(12) 0.01286(10) Uani 1 1 d . . . C1 C 0.75379(18) 0.33597(16) 0.41462(5) 0.0141(3) Uani 1 1 d . . . C2 C 0.74709(18) 0.41828(16) 0.44421(4) 0.0134(3) Uani 1 1 d . . . C3 C 0.80522(18) 0.54945(16) 0.43556(5) 0.0135(4) Uani 1 1 d . . . C4 C 0.85459(18) 0.56520(15) 0.39953(4) 0.0140(3) Uani 1 1 d . . . O1 O 1.00890(12) 0.36432(11) 0.37335(3) 0.0176(3) Uani 1 1 d . . . C5 C 0.68450(18) 0.21039(16) 0.41027(4) 0.0140(4) Uani 1 1 d . . . C6 C 0.75308(18) 0.11414(16) 0.38951(4) 0.0161(4) Uani 1 1 d . . . H1 H 0.8492 0.1271 0.3802 0.019 Uiso 1 1 calc R . . C7 C 0.68223(19) -0.00016(16) 0.38241(5) 0.0182(4) Uani 1 1 d . . . H2 H 0.7310 -0.0658 0.3689 0.022 Uiso 1 1 calc R . . C8 C 0.5404(2) -0.01853(16) 0.39501(5) 0.0194(4) Uani 1 1 d . . . H3 H 0.4907 -0.0956 0.3893 0.023 Uiso 1 1 calc R . . C9 C 0.47112(19) 0.07532(17) 0.41588(5) 0.0193(4) Uani 1 1 d . . . H4 H 0.3746 0.0620 0.4249 0.023 Uiso 1 1 calc R . . C10 C 0.54267(19) 0.18871(16) 0.42361(5) 0.0170(4) Uani 1 1 d . . . H5 H 0.4949 0.2524 0.4381 0.020 Uiso 1 1 calc R . . C11 C 0.68967(17) 0.38401(16) 0.48225(4) 0.0127(3) Uani 1 1 d . . . C12 C 0.73705(19) 0.27189(17) 0.49955(5) 0.0164(4) Uani 1 1 d . . . H6 H 0.8049 0.2185 0.4868 0.020 Uiso 1 1 calc R . . C13 C 0.68592(19) 0.23770(17) 0.53513(5) 0.0177(4) Uani 1 1 d . . . H7 H 0.7183 0.1608 0.5465 0.021 Uiso 1 1 calc R . . C14 C 0.58769(18) 0.31535(17) 0.55420(5) 0.0179(4) Uani 1 1 d . . . H8 H 0.5539 0.2926 0.5787 0.022 Uiso 1 1 calc R . . C15 C 0.53932(18) 0.42666(17) 0.53705(5) 0.0174(4) Uani 1 1 d . . . H9 H 0.4713 0.4797 0.5498 0.021 Uiso 1 1 calc R . . C16 C 0.58920(18) 0.46102(16) 0.50155(5) 0.0154(4) Uani 1 1 d . . . H10 H 0.5551 0.5374 0.4902 0.019 Uiso 1 1 calc R . . C17 C 0.80342(17) 0.65210(16) 0.46458(5) 0.0137(3) Uani 1 1 d . . . C18 C 0.86255(18) 0.63348(17) 0.50067(5) 0.0167(4) Uani 1 1 d . . . H11 H 0.9075 0.5547 0.5069 0.020 Uiso 1 1 calc R . . C19 C 0.8556(2) 0.72967(18) 0.52739(5) 0.0203(4) Uani 1 1 d . . . H12 H 0.8958 0.7164 0.5519 0.024 Uiso 1 1 calc R . . C20 C 0.79031(19) 0.84527(18) 0.51873(5) 0.0216(4) Uani 1 1 d . . . H13 H 0.7847 0.9105 0.5373 0.026 Uiso 1 1 calc R . . C21 C 0.73323(19) 0.86511(17) 0.48275(5) 0.0204(4) Uani 1 1 d . . . H14 H 0.6898 0.9445 0.4765 0.024 Uiso 1 1 calc R . . C22 C 0.73982(19) 0.76850(16) 0.45598(5) 0.0175(4) Uani 1 1 d . . . H15 H 0.7003 0.7823 0.4315 0.021 Uiso 1 1 calc R . . C23 C 0.93394(18) 0.67459(15) 0.38309(5) 0.0150(4) Uani 1 1 d . . . C24 C 1.03436(19) 0.74465(17) 0.40431(5) 0.0185(4) Uani 1 1 d . . . H16 H 1.0525 0.7219 0.4299 0.022 Uiso 1 1 calc R . . C25 C 1.10784(19) 0.84697(17) 0.38847(5) 0.0225(4) Uani 1 1 d . . . H17 H 1.1761 0.8935 0.4033 0.027 Uiso 1 1 calc R . . C26 C 1.0826(2) 0.88199(17) 0.35120(5) 0.0237(4) Uani 1 1 d . . . H18 H 1.1316 0.9533 0.3406 0.028 Uiso 1 1 calc R . . C27 C 0.9850(2) 0.81186(18) 0.32954(5) 0.0222(4) Uani 1 1 d . . . H19 H 0.9679 0.8349 0.3039 0.027 Uiso 1 1 calc R . . C28 C 0.91233(19) 0.70848(17) 0.34503(5) 0.0179(4) Uani 1 1 d . . . H20 H 0.8473 0.6601 0.3298 0.021 Uiso 1 1 calc R . . C29 C 0.75386(18) 0.40442(16) 0.33193(4) 0.0139(3) Uani 1 1 d . . . C30 C 0.61576(18) 0.46380(16) 0.32858(5) 0.0146(4) Uani 1 1 d . . . C31 C 0.55249(19) 0.47726(16) 0.29292(5) 0.0165(4) Uani 1 1 d . . . H21 H 0.4605 0.5186 0.2909 0.020 Uiso 1 1 calc R . . C32 C 0.61944(18) 0.43223(16) 0.26024(4) 0.0163(4) Uani 1 1 d . . . C33 C 0.74954(19) 0.36696(17) 0.26429(5) 0.0169(4) Uani 1 1 d . . . H22 H 0.7941 0.3325 0.2423 0.020 Uiso 1 1 calc R . . C34 C 0.81887(18) 0.34905(16) 0.29913(5) 0.0154(4) Uani 1 1 d . . . C35 C 0.52701(19) 0.50955(17) 0.36253(5) 0.0171(4) Uani 1 1 d . . . H23 H 0.5855 0.4921 0.3859 0.021 Uiso 1 1 calc R . . C36 C 0.4958(2) 0.65267(18) 0.36121(5) 0.0247(4) Uani 1 1 d . . . H24 H 0.5883 0.6996 0.3607 0.037 Uiso 1 1 calc R . . H25 H 0.4398 0.6774 0.3837 0.037 Uiso 1 1 calc R . . H26 H 0.4394 0.6726 0.3384 0.037 Uiso 1 1 calc R . . C37 C 0.38320(19) 0.43535(18) 0.36573(5) 0.0234(4) Uani 1 1 d . . . H27 H 0.3214 0.4543 0.3438 0.035 Uiso 1 1 calc R . . H28 H 0.3323 0.4604 0.3890 0.035 Uiso 1 1 calc R . . H29 H 0.4040 0.3439 0.3665 0.035 Uiso 1 1 calc R . . C38 C 0.5507(2) 0.45010(18) 0.22132(5) 0.0200(4) Uani 1 1 d . . . H30 H 0.6152 0.4070 0.2024 0.024 Uiso 1 1 calc R . . C39 C 0.40055(19) 0.3874(2) 0.21916(5) 0.0248(4) Uani 1 1 d . . . H31 H 0.4094 0.2969 0.2255 0.037 Uiso 1 1 calc R . . H32 H 0.3616 0.3961 0.1935 0.037 Uiso 1 1 calc R . . H33 H 0.3343 0.4288 0.2371 0.037 Uiso 1 1 calc R . . C40 C 0.5413(2) 0.5905(2) 0.21049(5) 0.0322(5) Uani 1 1 d . . . H34 H 0.5024 0.5982 0.1847 0.048 Uiso 1 1 calc R . . H35 H 0.6389 0.6286 0.2116 0.048 Uiso 1 1 calc R . . H36 H 0.4764 0.6348 0.2282 0.048 Uiso 1 1 calc R . . C41 C 0.96015(19) 0.27121(17) 0.29898(5) 0.0178(4) Uani 1 1 d . . . H37 H 0.9798 0.2440 0.3256 0.021 Uiso 1 1 calc R . . C42 C 0.9486(2) 0.15080(18) 0.27484(5) 0.0255(4) Uani 1 1 d . . . H38 H 0.9371 0.1745 0.2482 0.038 Uiso 1 1 calc R . . H39 H 0.8638 0.1009 0.2830 0.038 Uiso 1 1 calc R . . H40 H 1.0375 0.0998 0.2779 0.038 Uiso 1 1 calc R . . C43 C 1.08766(19) 0.35492(18) 0.28640(5) 0.0222(4) Uani 1 1 d . . . H41 H 1.0716 0.3831 0.2603 0.033 Uiso 1 1 calc R . . H42 H 1.1787 0.3060 0.2878 0.033 Uiso 1 1 calc R . . H43 H 1.0945 0.4293 0.3030 0.033 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 0.0135(2) 0.0139(2) 0.0111(2) 0.00041(17) -0.00008(17) -0.00063(18) C1 0.0119(8) 0.0160(9) 0.0143(8) 0.0029(7) 0.0003(7) 0.0029(7) C2 0.0115(7) 0.0140(8) 0.0148(8) 0.0010(7) -0.0013(7) 0.0017(7) C3 0.0111(8) 0.0151(9) 0.0142(8) 0.0028(7) -0.0015(7) 0.0014(7) C4 0.0131(8) 0.0155(8) 0.0136(8) 0.0003(7) -0.0038(7) 0.0006(7) O1 0.0151(6) 0.0220(6) 0.0158(6) 0.0014(5) -0.0002(5) 0.0023(5) C5 0.0178(8) 0.0147(9) 0.0095(8) 0.0036(7) -0.0012(7) 0.0004(7) C6 0.0162(8) 0.0193(9) 0.0128(8) 0.0004(7) -0.0003(7) 0.0007(7) C7 0.0262(9) 0.0155(9) 0.0128(9) -0.0021(7) -0.0021(7) 0.0029(7) C8 0.0251(9) 0.0142(9) 0.0189(9) 0.0009(7) -0.0049(8) -0.0040(8) C9 0.0170(9) 0.0201(9) 0.0209(9) 0.0042(8) 0.0014(7) -0.0020(8) C10 0.0195(9) 0.0155(9) 0.0160(9) 0.0000(7) 0.0015(7) 0.0016(8) C11 0.0125(8) 0.0147(9) 0.0109(8) -0.0012(7) -0.0016(6) -0.0034(7) C12 0.0158(8) 0.0174(9) 0.0160(8) -0.0013(7) -0.0001(7) 0.0003(7) C13 0.0201(9) 0.0161(9) 0.0170(9) 0.0035(7) -0.0026(7) -0.0020(7) C14 0.0178(9) 0.0238(10) 0.0122(8) 0.0011(7) 0.0002(7) -0.0067(8) C15 0.0150(8) 0.0200(9) 0.0171(8) -0.0045(8) 0.0031(7) -0.0033(8) C16 0.0135(8) 0.0140(9) 0.0188(9) 0.0009(7) -0.0018(7) -0.0023(7) C17 0.0121(8) 0.0155(9) 0.0135(8) 0.0007(7) 0.0019(7) -0.0036(7) C18 0.0135(8) 0.0192(9) 0.0175(8) 0.0009(7) 0.0014(7) -0.0022(7) C19 0.0193(9) 0.0283(10) 0.0134(8) -0.0030(7) 0.0002(7) -0.0059(8) C20 0.0216(9) 0.0209(10) 0.0222(10) -0.0103(8) 0.0068(7) -0.0081(8) C21 0.0187(9) 0.0151(9) 0.0273(10) -0.0011(8) 0.0047(8) -0.0013(7) C22 0.0154(8) 0.0189(9) 0.0181(9) 0.0030(7) -0.0004(7) -0.0039(8) C23 0.0149(8) 0.0144(8) 0.0156(9) 0.0005(7) 0.0027(7) 0.0017(7) C24 0.0181(9) 0.0217(10) 0.0156(9) 0.0019(7) 0.0001(7) -0.0011(8) C25 0.0202(9) 0.0213(10) 0.0262(10) -0.0046(8) 0.0036(7) -0.0079(8) C26 0.0269(10) 0.0189(10) 0.0253(10) 0.0028(8) 0.0098(8) -0.0027(8) C27 0.0264(10) 0.0236(10) 0.0167(9) 0.0051(8) 0.0045(8) 0.0004(8) C28 0.0210(9) 0.0192(9) 0.0135(8) -0.0009(7) 0.0005(7) -0.0002(7) C29 0.0175(8) 0.0132(8) 0.0112(8) -0.0009(7) -0.0012(6) -0.0018(7) C30 0.0161(9) 0.0134(8) 0.0143(8) -0.0015(7) 0.0003(7) -0.0021(7) C31 0.0132(8) 0.0170(9) 0.0193(9) -0.0010(7) -0.0007(7) 0.0015(7) C32 0.0167(9) 0.0178(9) 0.0144(8) 0.0003(7) -0.0007(7) -0.0039(7) C33 0.0186(9) 0.0189(9) 0.0131(8) -0.0022(7) 0.0019(7) -0.0032(8) C34 0.0155(8) 0.0154(9) 0.0152(8) -0.0002(7) 0.0016(7) -0.0030(7) C35 0.0153(8) 0.0212(9) 0.0149(8) -0.0017(7) -0.0016(7) 0.0019(7) C36 0.0260(10) 0.0232(10) 0.0248(10) -0.0050(8) 0.0048(8) 0.0027(8) C37 0.0199(9) 0.0294(11) 0.0208(9) -0.0028(8) 0.0035(7) -0.0028(8) C38 0.0195(9) 0.0266(10) 0.0140(9) -0.0020(7) -0.0001(7) -0.0009(8) C39 0.0240(10) 0.0329(11) 0.0176(9) 0.0017(8) -0.0064(7) -0.0053(9) C40 0.0460(12) 0.0289(11) 0.0216(10) 0.0055(9) -0.0130(9) -0.0104(10) C41 0.0187(9) 0.0202(9) 0.0144(8) -0.0002(7) 0.0007(7) 0.0026(8) C42 0.0302(10) 0.0200(10) 0.0262(10) -0.0036(8) 0.0021(8) 0.0044(9) C43 0.0190(9) 0.0268(10) 0.0208(9) 0.0014(8) 0.0010(7) 0.0024(8) _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 1.4843(12) . ? P1 C1 1.8134(17) . ? P1 C4 1.8229(17) . ? P1 C29 1.8327(17) . ? C1 C2 1.358(2) . ? C1 C5 1.472(2) . ? C2 C11 1.488(2) . ? C2 C3 1.509(2) . ? C3 C4 1.361(2) . ? C3 C17 1.488(2) . ? C4 C23 1.478(2) . ? C5 C6 1.398(2) . ? C5 C10 1.400(2) . ? C6 C7 1.388(2) . ? C6 H1 0.9500 . ? C7 C8 1.386(3) . ? C7 H2 0.9500 . ? C8 C9 1.385(3) . ? C8 H3 0.9500 . ? C9 C10 1.387(2) . ? C9 H4 0.9500 . ? C10 H5 0.9500 . ? C11 C12 1.396(2) . ? C11 C16 1.402(2) . ? C12 C13 1.389(2) . ? C12 H6 0.9500 . ? C13 C14 1.389(3) . ? C13 H7 0.9500 . ? C14 C15 1.390(3) . ? C14 H8 0.9500 . ? C15 C16 1.383(2) . ? C15 H9 0.9500 . ? C16 H10 0.9500 . ? C17 C22 1.388(2) . ? C17 C18 1.399(2) . ? C18 C19 1.384(2) . ? C18 H11 0.9500 . ? C19 C20 1.388(3) . ? C19 H12 0.9500 . ? C20 C21 1.390(3) . ? C20 H13 0.9500 . ? C21 C22 1.389(2) . ? C21 H14 0.9500 . ? C22 H15 0.9500 . ? C23 C24 1.396(2) . ? C23 C28 1.405(2) . ? C24 C25 1.386(2) . ? C24 H16 0.9500 . ? C25 C26 1.387(3) . ? C25 H17 0.9500 . ? C26 C27 1.388(3) . ? C26 H18 0.9500 . ? C27 C28 1.386(2) . ? C27 H19 0.9500 . ? C28 H20 0.9500 . ? C29 C30 1.415(2) . ? C29 C34 1.427(2) . ? C30 C31 1.394(2) . ? C30 C35 1.526(2) . ? C31 C32 1.390(2) . ? C31 H21 0.9500 . ? C32 C33 1.382(2) . ? C32 C38 1.524(2) . ? C33 C34 1.398(2) . ? C33 H22 0.9500 . ? C34 C41 1.530(2) . ? C35 C36 1.531(3) . ? C35 C37 1.534(2) . ? C35 H23 1.0000 . ? C36 H24 0.9800 . ? C36 H25 0.9800 . ? C36 H26 0.9800 . ? C37 H27 0.9800 . ? C37 H28 0.9800 . ? C37 H29 0.9800 . ? C38 C39 1.526(3) . ? C38 C40 1.527(3) . ? C38 H30 1.0000 . ? C39 H31 0.9800 . ? C39 H32 0.9800 . ? C39 H33 0.9800 . ? C40 H34 0.9800 . ? C40 H35 0.9800 . ? C40 H36 0.9800 . ? C41 C43 1.528(3) . ? C41 C42 1.529(2) . ? C41 H37 1.0000 . ? C42 H38 0.9800 . ? C42 H39 0.9800 . ? C42 H40 0.9800 . ? C43 H41 0.9800 . ? C43 H42 0.9800 . ? C43 H43 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C1 113.85(7) . . ? O1 P1 C4 109.19(7) . . ? C1 P1 C4 92.81(8) . . ? O1 P1 C29 113.92(7) . . ? C1 P1 C29 111.23(8) . . ? C4 P1 C29 114.09(8) . . ? C2 C1 C5 129.18(15) . . ? C2 C1 P1 108.78(13) . . ? C5 C1 P1 121.90(12) . . ? C1 C2 C11 123.88(15) . . ? C1 C2 C3 114.19(14) . . ? C11 C2 C3 121.93(14) . . ? C4 C3 C17 124.07(15) . . ? C4 C3 C2 114.69(14) . . ? C17 C3 C2 121.22(14) . . ? C3 C4 C23 128.70(15) . . ? C3 C4 P1 108.08(12) . . ? C23 C4 P1 121.15(12) . . ? C6 C5 C10 118.38(16) . . ? C6 C5 C1 120.64(15) . . ? C10 C5 C1 120.68(15) . . ? C7 C6 C5 120.73(16) . . ? C7 C6 H1 119.6 . . ? C5 C6 H1 119.6 . . ? C8 C7 C6 120.01(16) . . ? C8 C7 H2 120.0 . . ? C6 C7 H2 120.0 . . ? C9 C8 C7 120.06(17) . . ? C9 C8 H3 120.0 . . ? C7 C8 H3 120.0 . . ? C8 C9 C10 120.01(16) . . ? C8 C9 H4 120.0 . . ? C10 C9 H4 120.0 . . ? C9 C10 C5 120.76(16) . . ? C9 C10 H5 119.6 . . ? C5 C10 H5 119.6 . . ? C12 C11 C16 118.54(15) . . ? C12 C11 C2 119.34(15) . . ? C16 C11 C2 122.12(15) . . ? C13 C12 C11 120.65(16) . . ? C13 C12 H6 119.7 . . ? C11 C12 H6 119.7 . . ? C14 C13 C12 120.37(16) . . ? C14 C13 H7 119.8 . . ? C12 C13 H7 119.8 . . ? C13 C14 C15 119.28(16) . . ? C13 C14 H8 120.4 . . ? C15 C14 H8 120.4 . . ? C16 C15 C14 120.67(16) . . ? C16 C15 H9 119.7 . . ? C14 C15 H9 119.7 . . ? C15 C16 C11 120.48(16) . . ? C15 C16 H10 119.8 . . ? C11 C16 H10 119.8 . . ? C22 C17 C18 119.01(16) . . ? C22 C17 C3 119.48(15) . . ? C18 C17 C3 121.50(15) . . ? C19 C18 C17 120.10(17) . . ? C19 C18 H11 119.9 . . ? C17 C18 H11 119.9 . . ? C18 C19 C20 120.55(16) . . ? C18 C19 H12 119.7 . . ? C20 C19 H12 119.7 . . ? C19 C20 C21 119.65(16) . . ? C19 C20 H13 120.2 . . ? C21 C20 H13 120.2 . . ? C22 C21 C20 119.80(17) . . ? C22 C21 H14 120.1 . . ? C20 C21 H14 120.1 . . ? C17 C22 C21 120.87(16) . . ? C17 C22 H15 119.6 . . ? C21 C22 H15 119.6 . . ? C24 C23 C28 118.24(15) . . ? C24 C23 C4 121.48(15) . . ? C28 C23 C4 120.26(15) . . ? C25 C24 C23 120.77(16) . . ? C25 C24 H16 119.6 . . ? C23 C24 H16 119.6 . . ? C24 C25 C26 120.56(17) . . ? C24 C25 H17 119.7 . . ? C26 C25 H17 119.7 . . ? C25 C26 C27 119.35(17) . . ? C25 C26 H18 120.3 . . ? C27 C26 H18 120.3 . . ? C28 C27 C26 120.46(17) . . ? C28 C27 H19 119.8 . . ? C26 C27 H19 119.8 . . ? C27 C28 C23 120.58(16) . . ? C27 C28 H20 119.7 . . ? C23 C28 H20 119.7 . . ? C30 C29 C34 118.96(14) . . ? C30 C29 P1 120.91(12) . . ? C34 C29 P1 119.92(13) . . ? C31 C30 C29 119.46(15) . . ? C31 C30 C35 117.22(15) . . ? C29 C30 C35 123.26(14) . . ? C32 C31 C30 122.22(16) . . ? C32 C31 H21 118.9 . . ? C30 C31 H21 118.9 . . ? C33 C32 C31 117.56(15) . . ? C33 C32 C38 120.70(15) . . ? C31 C32 C38 121.72(16) . . ? C32 C33 C34 123.34(15) . . ? C32 C33 H22 118.3 . . ? C34 C33 H22 118.3 . . ? C33 C34 C29 118.12(16) . . ? C33 C34 C41 116.92(14) . . ? C29 C34 C41 124.97(15) . . ? C30 C35 C36 112.61(15) . . ? C30 C35 C37 110.77(14) . . ? C36 C35 C37 109.96(15) . . ? C30 C35 H23 107.8 . . ? C36 C35 H23 107.8 . . ? C37 C35 H23 107.8 . . ? C35 C36 H24 109.5 . . ? C35 C36 H25 109.5 . . ? H24 C36 H25 109.5 . . ? C35 C36 H26 109.5 . . ? H24 C36 H26 109.5 . . ? H25 C36 H26 109.5 . . ? C35 C37 H27 109.5 . . ? C35 C37 H28 109.5 . . ? H27 C37 H28 109.5 . . ? C35 C37 H29 109.5 . . ? H27 C37 H29 109.5 . . ? H28 C37 H29 109.5 . . ? C32 C38 C39 111.32(14) . . ? C32 C38 C40 111.63(14) . . ? C39 C38 C40 110.72(16) . . ? C32 C38 H30 107.7 . . ? C39 C38 H30 107.7 . . ? C40 C38 H30 107.7 . . ? C38 C39 H31 109.5 . . ? C38 C39 H32 109.5 . . ? H31 C39 H32 109.5 . . ? C38 C39 H33 109.5 . . ? H31 C39 H33 109.5 . . ? H32 C39 H33 109.5 . . ? C38 C40 H34 109.5 . . ? C38 C40 H35 109.5 . . ? H34 C40 H35 109.5 . . ? C38 C40 H36 109.5 . . ? H34 C40 H36 109.5 . . ? H35 C40 H36 109.5 . . ? C43 C41 C42 111.52(15) . . ? C43 C41 C34 109.82(14) . . ? C42 C41 C34 112.68(15) . . ? C43 C41 H37 107.5 . . ? C42 C41 H37 107.5 . . ? C34 C41 H37 107.5 . . ? C41 C42 H38 109.5 . . ? C41 C42 H39 109.5 . . ? H38 C42 H39 109.5 . . ? C41 C42 H40 109.5 . . ? H38 C42 H40 109.5 . . ? H39 C42 H40 109.5 . . ? C41 C43 H41 109.5 . . ? C41 C43 H42 109.5 . . ? H41 C43 H42 109.5 . . ? C41 C43 H43 109.5 . . ? H41 C43 H43 109.5 . . ? H42 C43 H43 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 O1 P1 C1 C2 101.74(12) . . . . ? C4 P1 C1 C2 -10.69(13) . . . . ? C29 P1 C1 C2 -127.91(12) . . . . ? O1 P1 C1 C5 -82.29(15) . . . . ? C4 P1 C1 C5 165.28(14) . . . . ? C29 P1 C1 C5 48.06(15) . . . . ? C5 C1 C2 C11 13.1(3) . . . . ? P1 C1 C2 C11 -171.33(13) . . . . ? C5 C1 C2 C3 -167.65(16) . . . . ? P1 C1 C2 C3 7.93(17) . . . . ? C1 C2 C3 C4 0.3(2) . . . . ? C11 C2 C3 C4 179.58(15) . . . . ? C1 C2 C3 C17 178.82(15) . . . . ? C11 C2 C3 C17 -1.9(2) . . . . ? C17 C3 C4 C23 9.7(3) . . . . ? C2 C3 C4 C23 -171.80(16) . . . . ? C17 C3 C4 P1 173.24(13) . . . . ? C2 C3 C4 P1 -8.28(17) . . . . ? O1 P1 C4 C3 -105.70(12) . . . . ? C1 P1 C4 C3 10.77(13) . . . . ? C29 P1 C4 C3 125.55(12) . . . . ? O1 P1 C4 C23 59.30(15) . . . . ? C1 P1 C4 C23 175.77(14) . . . . ? C29 P1 C4 C23 -69.45(15) . . . . ? C2 C1 C5 C6 -147.54(18) . . . . ? P1 C1 C5 C6 37.4(2) . . . . ? C2 C1 C5 C10 38.8(3) . . . . ? P1 C1 C5 C10 -136.31(14) . . . . ? C10 C5 C6 C7 -0.2(2) . . . . ? C1 C5 C6 C7 -173.99(15) . . . . ? C5 C6 C7 C8 1.8(2) . . . . ? C6 C7 C8 C9 -2.3(3) . . . . ? C7 C8 C9 C10 1.1(3) . . . . ? C8 C9 C10 C5 0.6(3) . . . . ? C6 C5 C10 C9 -1.0(2) . . . . ? C1 C5 C10 C9 172.79(15) . . . . ? C1 C2 C11 C12 47.7(2) . . . . ? C3 C2 C11 C12 -131.56(17) . . . . ? C1 C2 C11 C16 -132.52(18) . . . . ? C3 C2 C11 C16 48.3(2) . . . . ? C16 C11 C12 C13 -0.1(2) . . . . ? C2 C11 C12 C13 179.68(15) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C13 C14 C15 C16 -0.7(3) . . . . ? C14 C15 C16 C11 0.0(3) . . . . ? C12 C11 C16 C15 0.5(2) . . . . ? C2 C11 C16 C15 -179.37(15) . . . . ? C4 C3 C17 C22 51.6(2) . . . . ? C2 C3 C17 C22 -126.82(17) . . . . ? C4 C3 C17 C18 -129.42(18) . . . . ? C2 C3 C17 C18 52.2(2) . . . . ? C22 C17 C18 C19 0.8(2) . . . . ? C3 C17 C18 C19 -178.22(15) . . . . ? C17 C18 C19 C20 -0.1(3) . . . . ? C18 C19 C20 C21 -0.9(3) . . . . ? C19 C20 C21 C22 1.0(3) . . . . ? C18 C17 C22 C21 -0.6(2) . . . . ? C3 C17 C22 C21 178.42(15) . . . . ? C20 C21 C22 C17 -0.3(3) . . . . ? C3 C4 C23 C24 34.9(3) . . . . ? P1 C4 C23 C24 -126.77(15) . . . . ? C3 C4 C23 C28 -146.83(18) . . . . ? P1 C4 C23 C28 51.5(2) . . . . ? C28 C23 C24 C25 1.7(3) . . . . ? C4 C23 C24 C25 180.00(16) . . . . ? C23 C24 C25 C26 0.2(3) . . . . ? C24 C25 C26 C27 -1.3(3) . . . . ? C25 C26 C27 C28 0.6(3) . . . . ? C26 C27 C28 C23 1.3(3) . . . . ? C24 C23 C28 C27 -2.4(3) . . . . ? C4 C23 C28 C27 179.22(16) . . . . ? O1 P1 C29 C30 -169.32(12) . . . . ? C1 P1 C29 C30 60.37(16) . . . . ? C4 P1 C29 C30 -43.00(16) . . . . ? O1 P1 C29 C34 5.37(16) . . . . ? C1 P1 C29 C34 -124.94(13) . . . . ? C4 P1 C29 C34 131.69(13) . . . . ? C34 C29 C30 C31 -5.8(2) . . . . ? P1 C29 C30 C31 168.93(13) . . . . ? C34 C29 C30 C35 171.27(16) . . . . ? P1 C29 C30 C35 -14.0(2) . . . . ? C29 C30 C31 C32 1.1(3) . . . . ? C35 C30 C31 C32 -176.16(16) . . . . ? C30 C31 C32 C33 3.2(3) . . . . ? C30 C31 C32 C38 -178.64(16) . . . . ? C31 C32 C33 C34 -2.7(3) . . . . ? C38 C32 C33 C34 179.07(16) . . . . ? C32 C33 C34 C29 -1.9(3) . . . . ? C32 C33 C34 C41 178.27(16) . . . . ? C30 C29 C34 C33 6.2(2) . . . . ? P1 C29 C34 C33 -168.61(13) . . . . ? C30 C29 C34 C41 -174.05(15) . . . . ? P1 C29 C34 C41 11.2(2) . . . . ? C31 C30 C35 C36 -62.4(2) . . . . ? C29 C30 C35 C36 120.46(18) . . . . ? C31 C30 C35 C37 61.2(2) . . . . ? C29 C30 C35 C37 -115.94(18) . . . . ? C33 C32 C38 C39 118.43(19) . . . . ? C31 C32 C38 C39 -59.7(2) . . . . ? C33 C32 C38 C40 -117.27(19) . . . . ? C31 C32 C38 C40 64.6(2) . . . . ? C33 C34 C41 C43 80.37(19) . . . . ? C29 C34 C41 C43 -99.40(19) . . . . ? C33 C34 C41 C42 -44.6(2) . . . . ? C29 C34 C41 C42 135.62(17) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.257 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.033 # Attachment 'cmpd4.CIF' data_unkwnwa _database_code_depnum_ccdc_archive 'CCDC 767157' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4'-methoxyphenyl)-2,3,4,5-tetraphenyl-1H-phosphole-1-oxide ; _chemical_name_common 1-(4'-methoxyphenyl)-2,3,4,5-tetraphenyl-1H-phosphole-1-oxide _chemical_melting_point 270 _chemical_formula_moiety ? _chemical_formula_sum 'C35 H27 O2 P' _chemical_formula_weight 510.54 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' _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 10.234(3) _cell_length_b 10.522(2) _cell_length_c 14.911(5) _cell_angle_alpha 70.376(11) _cell_angle_beta 89.627(14) _cell_angle_gamma 63.750(10) _cell_volume 1337.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9737 _exptl_absorpt_correction_T_max 0.9737 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating-anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9049 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4624 _reflns_number_gt 3637 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_cell_refinement 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_data_reduction 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4624 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.09167(5) 0.28584(5) 0.83869(3) 0.01808(14) Uani 1 1 d . . . C1 C -0.0670(2) 0.45932(19) 0.76154(13) 0.0194(4) Uani 1 1 d . . . C2 C -0.02038(19) 0.53998(19) 0.69017(13) 0.0186(4) Uani 1 1 d . . . C3 C 0.14438(19) 0.46381(19) 0.69244(13) 0.0181(4) Uani 1 1 d . . . C4 C 0.22009(19) 0.33008(19) 0.76787(13) 0.0181(4) Uani 1 1 d . . . O1 O 0.10665(14) 0.26784(13) 0.94181(9) 0.0224(3) Uani 1 1 d . . . C5 C 0.09997(19) 0.11813(19) 0.82610(13) 0.0180(4) Uani 1 1 d . . . C6 C 0.1073(2) 0.0912(2) 0.74048(14) 0.0258(5) Uani 1 1 d . . . H1 H 0.1069 0.1655 0.6824 0.031 Uiso 1 1 calc R . . C7 C 0.1152(2) -0.0426(2) 0.73933(14) 0.0290(5) Uani 1 1 d . . . H2 H 0.1205 -0.0601 0.6806 0.035 Uiso 1 1 calc R . . C8 C 0.1154(2) -0.1525(2) 0.82425(13) 0.0200(4) Uani 1 1 d . . . C9 C 0.1095(2) -0.1277(2) 0.90953(13) 0.0207(4) Uani 1 1 d . . . H3 H 0.1099 -0.2019 0.9676 0.025 Uiso 1 1 calc R . . C10 C 0.1031(2) 0.0066(2) 0.91006(13) 0.0200(4) Uani 1 1 d . . . H4 H 0.1009 0.0225 0.9692 0.024 Uiso 1 1 calc R . . O2 O 0.12362(15) -0.28114(14) 0.81630(9) 0.0282(3) Uani 1 1 d . . . C11 C 0.1245(2) -0.3959(2) 0.90368(14) 0.0295(5) Uani 1 1 d . . . H5 H 0.2108 -0.4319 0.9514 0.044 Uiso 1 1 calc R . . H6 H 0.1292 -0.4818 0.8891 0.044 Uiso 1 1 calc R . . H7 H 0.0341 -0.3517 0.9298 0.044 Uiso 1 1 calc R . . C12 C -0.2134(2) 0.5098(2) 0.79279(13) 0.0215(4) Uani 1 1 d . . . C13 C -0.2717(2) 0.4079(2) 0.82725(14) 0.0245(4) Uani 1 1 d . . . H8 H -0.2206 0.3080 0.8262 0.029 Uiso 1 1 calc R . . C14 C -0.4037(2) 0.4523(2) 0.86290(15) 0.0310(5) Uani 1 1 d . . . H9 H -0.4424 0.3825 0.8864 0.037 Uiso 1 1 calc R . . C15 C -0.4790(2) 0.5969(2) 0.86445(16) 0.0356(5) Uani 1 1 d . . . H10 H -0.5696 0.6268 0.8886 0.043 Uiso 1 1 calc R . . C16 C -0.4224(2) 0.6985(2) 0.83077(16) 0.0358(5) Uani 1 1 d . . . H11 H -0.4742 0.7982 0.8319 0.043 Uiso 1 1 calc R . . C17 C -0.2908(2) 0.6550(2) 0.79558(15) 0.0307(5) Uani 1 1 d . . . H12 H -0.2525 0.7254 0.7729 0.037 Uiso 1 1 calc R . . C18 C -0.11610(19) 0.69418(19) 0.61683(13) 0.0192(4) Uani 1 1 d . . . C19 C -0.2434(2) 0.7233(2) 0.56234(14) 0.0257(4) Uani 1 1 d . . . H13 H -0.2702 0.6444 0.5730 0.031 Uiso 1 1 calc R . . C20 C -0.3308(2) 0.8661(2) 0.49314(15) 0.0330(5) Uani 1 1 d . . . H14 H -0.4171 0.8847 0.4562 0.040 Uiso 1 1 calc R . . C21 C -0.2935(2) 0.9821(2) 0.47723(15) 0.0319(5) Uani 1 1 d . . . H15 H -0.3532 1.0798 0.4289 0.038 Uiso 1 1 calc R . . C22 C -0.1691(2) 0.9556(2) 0.53179(14) 0.0277(5) Uani 1 1 d . . . H16 H -0.1441 1.0357 0.5216 0.033 Uiso 1 1 calc R . . C23 C -0.0807(2) 0.8127(2) 0.60122(13) 0.0220(4) Uani 1 1 d . . . H17 H 0.0047 0.7953 0.6385 0.026 Uiso 1 1 calc R . . C24 C 0.21562(19) 0.53585(19) 0.61980(13) 0.0202(4) Uani 1 1 d . . . C25 C 0.1730(2) 0.5824(2) 0.52140(14) 0.0266(5) Uani 1 1 d . . . H18 H 0.0939 0.5713 0.4984 0.032 Uiso 1 1 calc R . . C26 C 0.2461(2) 0.6456(2) 0.45608(16) 0.0373(6) Uani 1 1 d . . . H19 H 0.2174 0.6766 0.3886 0.045 Uiso 1 1 calc R . . C27 C 0.3604(3) 0.6630(2) 0.48974(18) 0.0406(6) Uani 1 1 d . . . H20 H 0.4105 0.7055 0.4452 0.049 Uiso 1 1 calc R . . C28 C 0.4021(2) 0.6190(2) 0.58759(17) 0.0354(5) Uani 1 1 d . . . H21 H 0.4799 0.6325 0.6101 0.042 Uiso 1 1 calc R . . C29 C 0.3310(2) 0.55537(19) 0.65280(15) 0.0256(5) Uani 1 1 d . . . H22 H 0.3603 0.5248 0.7201 0.031 Uiso 1 1 calc R . . C30 C 0.3804(2) 0.22327(19) 0.79022(13) 0.0196(4) Uani 1 1 d . . . C31 C 0.4580(2) 0.1789(2) 0.71976(15) 0.0276(5) Uani 1 1 d . . . H23 H 0.4080 0.2195 0.6554 0.033 Uiso 1 1 calc R . . C32 C 0.6077(2) 0.0759(2) 0.74285(17) 0.0373(5) Uani 1 1 d . . . H24 H 0.6595 0.0463 0.6943 0.045 Uiso 1 1 calc R . . C33 C 0.6811(2) 0.0167(2) 0.83565(17) 0.0396(6) Uani 1 1 d . . . H25 H 0.7836 -0.0536 0.8512 0.047 Uiso 1 1 calc R . . C34 C 0.6057(2) 0.0595(2) 0.90641(17) 0.0383(6) Uani 1 1 d . . . H26 H 0.6566 0.0187 0.9705 0.046 Uiso 1 1 calc R . . C35 C 0.4559(2) 0.1620(2) 0.88392(15) 0.0285(5) Uani 1 1 d . . . H27 H 0.4045 0.1905 0.9329 0.034 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 0.0199(3) 0.0154(3) 0.0202(3) -0.0058(2) 0.00692(19) -0.0098(2) C1 0.0203(10) 0.0160(9) 0.0242(10) -0.0079(8) 0.0054(8) -0.0100(8) C2 0.0201(10) 0.0155(9) 0.0230(10) -0.0095(8) 0.0053(8) -0.0090(8) C3 0.0190(10) 0.0164(9) 0.0221(10) -0.0093(8) 0.0060(8) -0.0095(8) C4 0.0199(10) 0.0166(9) 0.0203(10) -0.0070(8) 0.0051(8) -0.0106(8) O1 0.0305(7) 0.0213(7) 0.0213(7) -0.0098(6) 0.0097(6) -0.0156(6) C5 0.0136(9) 0.0166(9) 0.0227(10) -0.0061(8) 0.0047(7) -0.0071(7) C6 0.0384(12) 0.0243(11) 0.0183(10) -0.0038(8) 0.0069(9) -0.0205(9) C7 0.0473(13) 0.0314(11) 0.0207(11) -0.0139(9) 0.0110(9) -0.0258(10) C8 0.0222(10) 0.0193(10) 0.0241(10) -0.0107(8) 0.0058(8) -0.0124(8) C9 0.0238(10) 0.0177(10) 0.0201(10) -0.0045(8) 0.0064(8) -0.0112(8) C10 0.0241(10) 0.0193(10) 0.0194(10) -0.0094(8) 0.0064(8) -0.0109(8) O2 0.0485(9) 0.0249(7) 0.0248(8) -0.0139(6) 0.0138(7) -0.0253(7) C11 0.0465(13) 0.0204(10) 0.0301(12) -0.0106(9) 0.0127(10) -0.0219(10) C12 0.0203(10) 0.0204(10) 0.0218(10) -0.0049(8) 0.0048(8) -0.0098(8) C13 0.0222(10) 0.0198(10) 0.0286(11) -0.0056(8) 0.0046(8) -0.0098(9) C14 0.0245(11) 0.0349(12) 0.0334(12) -0.0043(9) 0.0064(9) -0.0197(10) C15 0.0195(11) 0.0383(13) 0.0389(13) -0.0079(10) 0.0117(9) -0.0099(10) C16 0.0278(12) 0.0258(11) 0.0474(14) -0.0135(10) 0.0165(10) -0.0072(10) C17 0.0299(12) 0.0250(11) 0.0411(13) -0.0136(9) 0.0171(10) -0.0153(9) C18 0.0198(10) 0.0175(10) 0.0194(10) -0.0078(8) 0.0074(8) -0.0072(8) C19 0.0237(10) 0.0220(10) 0.0315(12) -0.0137(9) 0.0056(9) -0.0080(9) C20 0.0271(11) 0.0327(12) 0.0307(12) -0.0168(10) -0.0028(9) -0.0033(10) C21 0.0338(12) 0.0204(11) 0.0239(11) -0.0043(8) 0.0040(9) -0.0008(9) C22 0.0279(11) 0.0182(10) 0.0322(12) -0.0070(9) 0.0134(9) -0.0087(9) C23 0.0197(10) 0.0203(10) 0.0248(10) -0.0072(8) 0.0085(8) -0.0093(8) C24 0.0198(10) 0.0110(9) 0.0247(10) -0.0047(8) 0.0096(8) -0.0044(8) C25 0.0281(11) 0.0174(10) 0.0265(11) -0.0062(8) 0.0096(9) -0.0055(9) C26 0.0443(14) 0.0179(11) 0.0282(12) -0.0020(9) 0.0182(10) -0.0015(10) C27 0.0374(13) 0.0176(11) 0.0546(16) -0.0049(10) 0.0306(12) -0.0091(10) C28 0.0249(11) 0.0192(11) 0.0557(16) -0.0077(10) 0.0166(10) -0.0096(9) C29 0.0219(10) 0.0148(10) 0.0367(12) -0.0059(8) 0.0096(9) -0.0084(8) C30 0.0198(10) 0.0140(9) 0.0245(10) -0.0030(8) 0.0053(8) -0.0104(8) C31 0.0279(11) 0.0202(10) 0.0267(11) -0.0041(8) 0.0072(9) -0.0079(9) C32 0.0267(12) 0.0262(11) 0.0441(14) -0.0059(10) 0.0169(10) -0.0051(9) C33 0.0198(11) 0.0241(11) 0.0534(16) 0.0041(10) 0.0042(10) -0.0058(9) C34 0.0289(12) 0.0372(13) 0.0350(13) 0.0029(10) -0.0027(10) -0.0156(10) C35 0.0272(11) 0.0283(11) 0.0252(11) -0.0025(9) 0.0041(9) -0.0143(9) _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 1.4851(14) . ? P1 C5 1.8017(18) . ? P1 C4 1.8032(18) . ? P1 C1 1.8123(19) . ? C1 C2 1.351(2) . ? C1 C12 1.482(2) . ? C2 C18 1.485(2) . ? C2 C3 1.508(2) . ? C3 C4 1.352(2) . ? C3 C24 1.485(2) . ? C4 C30 1.480(2) . ? C5 C10 1.388(2) . ? C5 C6 1.392(3) . ? C6 C7 1.381(3) . ? C6 H1 0.9500 . ? C7 C8 1.398(3) . ? C7 H2 0.9500 . ? C8 O2 1.364(2) . ? C8 C9 1.377(3) . ? C9 C10 1.388(2) . ? C9 H3 0.9500 . ? C10 H4 0.9500 . ? O2 C11 1.445(2) . ? C11 H5 0.9800 . ? C11 H6 0.9800 . ? C11 H7 0.9800 . ? C12 C17 1.391(3) . ? C12 C13 1.400(2) . ? C13 C14 1.387(3) . ? C13 H8 0.9500 . ? C14 C15 1.376(3) . ? C14 H9 0.9500 . ? C15 C16 1.383(3) . ? C15 H10 0.9500 . ? C16 C17 1.380(3) . ? C16 H11 0.9500 . ? C17 H12 0.9500 . ? C18 C19 1.395(3) . ? C18 C23 1.395(2) . ? C19 C20 1.380(3) . ? C19 H13 0.9500 . ? C20 C21 1.382(3) . ? C20 H14 0.9500 . ? C21 C22 1.381(3) . ? C21 H15 0.9500 . ? C22 C23 1.383(3) . ? C22 H16 0.9500 . ? C23 H17 0.9500 . ? C24 C25 1.385(3) . ? C24 C29 1.403(3) . ? C25 C26 1.394(3) . ? C25 H18 0.9500 . ? C26 C27 1.383(3) . ? C26 H19 0.9500 . ? C27 C28 1.380(3) . ? C27 H20 0.9500 . ? C28 C29 1.381(3) . ? C28 H21 0.9500 . ? C29 H22 0.9500 . ? C30 C35 1.390(3) . ? C30 C31 1.394(3) . ? C31 C32 1.389(3) . ? C31 H23 0.9500 . ? C32 C33 1.374(3) . ? C32 H24 0.9500 . ? C33 C34 1.383(3) . ? C33 H25 0.9500 . ? C34 C35 1.389(3) . ? C34 H26 0.9500 . ? C35 H27 0.9500 . ? 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 C5 111.18(8) . . ? O1 P1 C4 118.30(8) . . ? C5 P1 C4 106.55(8) . . ? O1 P1 C1 114.25(8) . . ? C5 P1 C1 112.30(8) . . ? C4 P1 C1 92.97(8) . . ? C2 C1 C12 128.82(16) . . ? C2 C1 P1 109.10(13) . . ? C12 C1 P1 120.47(13) . . ? C1 C2 C18 125.32(16) . . ? C1 C2 C3 114.25(16) . . ? C18 C2 C3 120.36(15) . . ? C4 C3 C24 123.74(16) . . ? C4 C3 C2 114.39(16) . . ? C24 C3 C2 121.80(15) . . ? C3 C4 C30 128.75(16) . . ? C3 C4 P1 109.24(13) . . ? C30 C4 P1 121.85(13) . . ? C10 C5 C6 118.50(16) . . ? C10 C5 P1 116.16(14) . . ? C6 C5 P1 125.31(14) . . ? C7 C6 C5 120.46(17) . . ? C7 C6 H1 119.8 . . ? C5 C6 H1 119.8 . . ? C6 C7 C8 120.26(18) . . ? C6 C7 H2 119.9 . . ? C8 C7 H2 119.9 . . ? O2 C8 C9 124.04(16) . . ? O2 C8 C7 116.20(16) . . ? C9 C8 C7 119.76(16) . . ? C8 C9 C10 119.51(16) . . ? C8 C9 H3 120.2 . . ? C10 C9 H3 120.2 . . ? C9 C10 C5 121.49(17) . . ? C9 C10 H4 119.3 . . ? C5 C10 H4 119.3 . . ? C8 O2 C11 116.73(14) . . ? O2 C11 H5 109.5 . . ? O2 C11 H6 109.5 . . ? H5 C11 H6 109.5 . . ? O2 C11 H7 109.5 . . ? H5 C11 H7 109.5 . . ? H6 C11 H7 109.5 . . ? C17 C12 C13 118.39(17) . . ? C17 C12 C1 121.04(16) . . ? C13 C12 C1 120.40(16) . . ? C14 C13 C12 120.21(17) . . ? C14 C13 H8 119.9 . . ? C12 C13 H8 119.9 . . ? C15 C14 C13 120.46(18) . . ? C15 C14 H9 119.8 . . ? C13 C14 H9 119.8 . . ? C14 C15 C16 119.86(19) . . ? C14 C15 H10 120.1 . . ? C16 C15 H10 120.1 . . ? C17 C16 C15 120.07(19) . . ? C17 C16 H11 120.0 . . ? C15 C16 H11 120.0 . . ? C16 C17 C12 121.01(18) . . ? C16 C17 H12 119.5 . . ? C12 C17 H12 119.5 . . ? C19 C18 C23 118.71(17) . . ? C19 C18 C2 120.59(16) . . ? C23 C18 C2 120.70(16) . . ? C20 C19 C18 120.44(18) . . ? C20 C19 H13 119.8 . . ? C18 C19 H13 119.8 . . ? C19 C20 C21 120.36(19) . . ? C19 C20 H14 119.8 . . ? C21 C20 H14 119.8 . . ? C22 C21 C20 119.82(18) . . ? C22 C21 H15 120.1 . . ? C20 C21 H15 120.1 . . ? C21 C22 C23 120.19(18) . . ? C21 C22 H16 119.9 . . ? C23 C22 H16 119.9 . . ? C22 C23 C18 120.45(18) . . ? C22 C23 H17 119.8 . . ? C18 C23 H17 119.8 . . ? C25 C24 C29 119.35(17) . . ? C25 C24 C3 122.29(17) . . ? C29 C24 C3 118.36(17) . . ? C24 C25 C26 120.17(19) . . ? C24 C25 H18 119.9 . . ? C26 C25 H18 119.9 . . ? C27 C26 C25 119.8(2) . . ? C27 C26 H19 120.1 . . ? C25 C26 H19 120.1 . . ? C28 C27 C26 120.44(19) . . ? C28 C27 H20 119.8 . . ? C26 C27 H20 119.8 . . ? C27 C28 C29 120.1(2) . . ? C27 C28 H21 119.9 . . ? C29 C28 H21 119.9 . . ? C28 C29 C24 120.1(2) . . ? C28 C29 H22 119.9 . . ? C24 C29 H22 119.9 . . ? C35 C30 C31 118.67(18) . . ? C35 C30 C4 119.79(17) . . ? C31 C30 C4 121.51(17) . . ? C32 C31 C30 120.5(2) . . ? C32 C31 H23 119.7 . . ? C30 C31 H23 119.7 . . ? C33 C32 C31 120.2(2) . . ? C33 C32 H24 119.9 . . ? C31 C32 H24 119.9 . . ? C32 C33 C34 119.9(2) . . ? C32 C33 H25 120.0 . . ? C34 C33 H25 120.0 . . ? C33 C34 C35 120.1(2) . . ? C33 C34 H26 119.9 . . ? C35 C34 H26 119.9 . . ? C34 C35 C30 120.5(2) . . ? C34 C35 H27 119.8 . . ? C30 C35 H27 119.8 . . ? 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 O1 P1 C1 C2 122.42(13) . . . . ? C5 P1 C1 C2 -109.77(13) . . . . ? C4 P1 C1 C2 -0.53(14) . . . . ? O1 P1 C1 C12 -44.36(16) . . . . ? C5 P1 C1 C12 83.45(16) . . . . ? C4 P1 C1 C12 -167.31(14) . . . . ? C12 C1 C2 C18 -9.7(3) . . . . ? P1 C1 C2 C18 -175.09(14) . . . . ? C12 C1 C2 C3 167.16(17) . . . . ? P1 C1 C2 C3 1.81(19) . . . . ? C1 C2 C3 C4 -2.7(2) . . . . ? C18 C2 C3 C4 174.33(16) . . . . ? C1 C2 C3 C24 -179.82(16) . . . . ? C18 C2 C3 C24 -2.8(3) . . . . ? C24 C3 C4 C30 -5.6(3) . . . . ? C2 C3 C4 C30 177.40(16) . . . . ? C24 C3 C4 P1 179.18(14) . . . . ? C2 C3 C4 P1 2.16(19) . . . . ? O1 P1 C4 C3 -120.65(13) . . . . ? C5 P1 C4 C3 113.33(14) . . . . ? C1 P1 C4 C3 -0.99(14) . . . . ? O1 P1 C4 C30 63.71(17) . . . . ? C5 P1 C4 C30 -62.31(16) . . . . ? C1 P1 C4 C30 -176.62(15) . . . . ? O1 P1 C5 C10 6.41(16) . . . . ? C4 P1 C5 C10 136.61(14) . . . . ? C1 P1 C5 C10 -123.01(14) . . . . ? O1 P1 C5 C6 -171.78(15) . . . . ? C4 P1 C5 C6 -41.58(18) . . . . ? C1 P1 C5 C6 58.81(18) . . . . ? C10 C5 C6 C7 1.0(3) . . . . ? P1 C5 C6 C7 179.16(15) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? C6 C7 C8 O2 -179.94(17) . . . . ? C6 C7 C8 C9 -0.8(3) . . . . ? O2 C8 C9 C10 179.23(17) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C8 C9 C10 C5 1.1(3) . . . . ? C6 C5 C10 C9 -1.7(3) . . . . ? P1 C5 C10 C9 -179.99(14) . . . . ? C9 C8 O2 C11 0.7(3) . . . . ? C7 C8 O2 C11 179.77(17) . . . . ? C2 C1 C12 C17 -38.7(3) . . . . ? P1 C1 C12 C17 125.16(18) . . . . ? C2 C1 C12 C13 146.2(2) . . . . ? P1 C1 C12 C13 -49.9(2) . . . . ? C17 C12 C13 C14 0.1(3) . . . . ? C1 C12 C13 C14 175.37(18) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C14 C15 C16 C17 0.1(4) . . . . ? C15 C16 C17 C12 0.3(3) . . . . ? C13 C12 C17 C16 -0.4(3) . . . . ? C1 C12 C17 C16 -175.63(19) . . . . ? C1 C2 C18 C19 -52.2(3) . . . . ? C3 C2 C18 C19 131.05(18) . . . . ? C1 C2 C18 C23 127.6(2) . . . . ? C3 C2 C18 C23 -49.1(2) . . . . ? C23 C18 C19 C20 1.2(3) . . . . ? C2 C18 C19 C20 -178.93(17) . . . . ? C18 C19 C20 C21 -0.2(3) . . . . ? C19 C20 C21 C22 -0.9(3) . . . . ? C20 C21 C22 C23 1.0(3) . . . . ? C21 C22 C23 C18 0.0(3) . . . . ? C19 C18 C23 C22 -1.1(3) . . . . ? C2 C18 C23 C22 179.03(17) . . . . ? C4 C3 C24 C25 128.2(2) . . . . ? C2 C3 C24 C25 -55.0(2) . . . . ? C4 C3 C24 C29 -51.1(3) . . . . ? C2 C3 C24 C29 125.71(18) . . . . ? C29 C24 C25 C26 1.1(3) . . . . ? C3 C24 C25 C26 -178.18(17) . . . . ? C24 C25 C26 C27 -0.6(3) . . . . ? C25 C26 C27 C28 -0.4(3) . . . . ? C26 C27 C28 C29 0.8(3) . . . . ? C27 C28 C29 C24 -0.3(3) . . . . ? C25 C24 C29 C28 -0.7(3) . . . . ? C3 C24 C29 C28 178.65(16) . . . . ? C3 C4 C30 C35 135.0(2) . . . . ? P1 C4 C30 C35 -50.3(2) . . . . ? C3 C4 C30 C31 -46.7(3) . . . . ? P1 C4 C30 C31 128.03(16) . . . . ? C35 C30 C31 C32 -0.2(3) . . . . ? C4 C30 C31 C32 -178.54(17) . . . . ? C30 C31 C32 C33 -0.1(3) . . . . ? C31 C32 C33 C34 0.1(3) . . . . ? C32 C33 C34 C35 0.1(3) . . . . ? C33 C34 C35 C30 -0.4(3) . . . . ? C31 C30 C35 C34 0.4(3) . . . . ? C4 C30 C35 C34 178.83(17) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.252 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.046 # Attachment 'cmpd5.CIF' data_ichi-5 _database_code_depnum_ccdc_archive 'CCDC 767158' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-trifluoromethyl)phenyl-2,3,4,5-tetraphenyl-1H-phosphole-1-oxide ; _chemical_name_common ;1-(4-trifluoromethyl)phenyl-2,3,4,5-tetraphenyl-1H-phosphole- 1-oxide ; _chemical_melting_point 283 _chemical_formula_moiety ? _chemical_formula_sum 'C35 H24 F3 O P' _chemical_formula_weight 548.51 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.2429(16) _cell_length_b 21.249(5) _cell_length_c 20.413(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.4377(14) _cell_angle_gamma 90.00 _cell_volume 2685.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 84(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9632 _exptl_absorpt_correction_T_max 0.9985 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 84(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating-anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17965 _diffrn_reflns_av_R_equivalents 0.0790 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4724 _reflns_number_gt 3292 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_cell_refinement 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_data_reduction 'CrystalClear 1.3.5 (Rigaku Corp)' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0582P)^2^+4.5398P] 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 4724 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1138 _refine_ls_R_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.1761 _refine_ls_wR_factor_gt 0.1535 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.40192(16) 0.21972(5) 0.95088(5) 0.0157(3) Uani 1 1 d . . . C1 C 0.3712(6) 0.18562(18) 1.03089(18) 0.0167(9) Uani 1 1 d . . . C2 C 0.2429(6) 0.22403(18) 1.06123(18) 0.0162(8) Uani 1 1 d . . . C3 C 0.1700(6) 0.28267(18) 1.02245(18) 0.0161(8) Uani 1 1 d . . . C4 C 0.2475(6) 0.28814(18) 0.96415(18) 0.0158(8) Uani 1 1 d . . . O1 O 0.6212(4) 0.22797(12) 0.93140(12) 0.0192(6) Uani 1 1 d . . . C5 C 0.2297(6) 0.17305(17) 0.89095(18) 0.0150(8) Uani 1 1 d . . . C6 C 0.0278(6) 0.15224(18) 0.90297(18) 0.0182(9) Uani 1 1 d . . . H1 H -0.0237 0.1628 0.9434 0.022 Uiso 1 1 calc R . . C7 C -0.0992(6) 0.11629(18) 0.85679(18) 0.0181(9) Uani 1 1 d . . . H2 H -0.2363 0.1016 0.8656 0.022 Uiso 1 1 calc R . . C8 C -0.0241(6) 0.10164(18) 0.79695(18) 0.0168(9) Uani 1 1 d . . . C9 C 0.1742(6) 0.12297(19) 0.78365(19) 0.0209(9) Uani 1 1 d . . . H3 H 0.2234 0.1133 0.7427 0.025 Uiso 1 1 calc R . . C10 C 0.3023(6) 0.15893(18) 0.83081(18) 0.0173(9) Uani 1 1 d . . . H4 H 0.4391 0.1738 0.8219 0.021 Uiso 1 1 calc R . . C11 C -0.1623(6) 0.0609(2) 0.74866(19) 0.0218(9) Uani 1 1 d . . . F1 F -0.3707(4) 0.07471(13) 0.74461(12) 0.0367(7) Uani 1 1 d . . . F2 F -0.1067(4) 0.06412(12) 0.68770(11) 0.0318(6) Uani 1 1 d . . . F3 F -0.1444(4) -0.00047(11) 0.76578(12) 0.0379(7) Uani 1 1 d . . . C12 C 0.4787(6) 0.12584(18) 1.05248(18) 0.0178(9) Uani 1 1 d . . . C13 C 0.6145(6) 0.09789(19) 1.0113(2) 0.0223(9) Uani 1 1 d . . . H5 H 0.6323 0.1174 0.9705 0.027 Uiso 1 1 calc R . . C14 C 0.7234(7) 0.04244(19) 1.0288(2) 0.0271(10) Uani 1 1 d . . . H6 H 0.8152 0.0246 1.0001 0.033 Uiso 1 1 calc R . . C15 C 0.6999(7) 0.0129(2) 1.0877(2) 0.0294(11) Uani 1 1 d . . . H7 H 0.7764 -0.0248 1.1002 0.035 Uiso 1 1 calc R . . C16 C 0.5620(8) 0.0394(2) 1.1280(2) 0.0343(12) Uani 1 1 d . . . H8 H 0.5427 0.0188 1.1681 0.041 Uiso 1 1 calc R . . C17 C 0.4519(7) 0.0946(2) 1.1118(2) 0.0284(10) Uani 1 1 d . . . H9 H 0.3583 0.1116 1.1405 0.034 Uiso 1 1 calc R . . C18 C 0.1827(6) 0.21722(18) 1.12969(18) 0.0158(8) Uani 1 1 d . . . C19 C 0.0053(7) 0.1811(2) 1.1416(2) 0.0251(10) Uani 1 1 d . . . H10 H -0.0772 0.1593 1.1062 0.030 Uiso 1 1 calc R . . C20 C -0.0506(7) 0.1769(2) 1.2054(2) 0.0302(11) Uani 1 1 d . . . H11 H -0.1714 0.1522 1.2135 0.036 Uiso 1 1 calc R . . C21 C 0.0688(8) 0.20836(19) 1.2565(2) 0.0297(11) Uani 1 1 d . . . H12 H 0.0288 0.2058 1.2998 0.036 Uiso 1 1 calc R . . C22 C 0.2466(8) 0.2438(2) 1.2455(2) 0.0342(12) Uani 1 1 d . . . H13 H 0.3293 0.2650 1.2812 0.041 Uiso 1 1 calc R . . C23 C 0.3040(7) 0.24827(19) 1.1817(2) 0.0264(10) Uani 1 1 d . . . H14 H 0.4259 0.2726 1.1739 0.032 Uiso 1 1 calc R . . C24 C 0.0260(6) 0.33118(18) 1.04691(18) 0.0155(8) Uani 1 1 d . . . C25 C -0.1737(6) 0.31428(19) 1.06555(18) 0.0177(9) Uani 1 1 d . . . H15 H -0.2155 0.2713 1.0655 0.021 Uiso 1 1 calc R . . C26 C -0.3117(6) 0.36068(19) 1.08425(18) 0.0198(9) Uani 1 1 d . . . H16 H -0.4472 0.3490 1.0970 0.024 Uiso 1 1 calc R . . C27 C -0.2535(7) 0.42355(19) 1.08440(19) 0.0217(9) Uani 1 1 d . . . H17 H -0.3491 0.4550 1.0966 0.026 Uiso 1 1 calc R . . C28 C -0.0533(7) 0.44014(18) 1.06646(19) 0.0204(9) Uani 1 1 d . . . H18 H -0.0108 0.4831 1.0672 0.024 Uiso 1 1 calc R . . C29 C 0.0847(6) 0.39429(18) 1.04753(18) 0.0189(9) Uani 1 1 d . . . H19 H 0.2203 0.4061 1.0349 0.023 Uiso 1 1 calc R . . C30 C 0.2115(6) 0.33839(18) 0.91421(18) 0.0184(9) Uani 1 1 d . . . C31 C 0.0083(7) 0.3498(2) 0.8800(2) 0.0252(10) Uani 1 1 d . . . H20 H -0.1115 0.3255 0.8895 0.030 Uiso 1 1 calc R . . C32 C -0.0218(8) 0.3964(2) 0.8320(2) 0.0309(11) Uani 1 1 d . . . H21 H -0.1609 0.4032 0.8081 0.037 Uiso 1 1 calc R . . C33 C 0.1520(8) 0.4330(2) 0.8189(2) 0.0327(11) Uani 1 1 d . . . H22 H 0.1310 0.4660 0.7874 0.039 Uiso 1 1 calc R . . C34 C 0.3565(8) 0.42129(19) 0.8521(2) 0.0295(11) Uani 1 1 d . . . H23 H 0.4763 0.4453 0.8418 0.035 Uiso 1 1 calc R . . C35 C 0.3869(7) 0.37495(18) 0.8998(2) 0.0232(9) Uani 1 1 d . . . H24 H 0.5268 0.3678 0.9230 0.028 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 0.0174(5) 0.0191(6) 0.0109(5) -0.0005(4) 0.0028(4) 0.0009(4) C1 0.021(2) 0.021(2) 0.0083(19) -0.0001(16) -0.0001(16) 0.0005(16) C2 0.017(2) 0.021(2) 0.0102(19) -0.0006(17) 0.0017(15) -0.0024(16) C3 0.0143(19) 0.021(2) 0.0125(19) -0.0034(17) 0.0004(15) -0.0028(16) C4 0.018(2) 0.020(2) 0.0093(19) -0.0008(16) 0.0021(15) 0.0005(16) O1 0.0159(14) 0.0273(16) 0.0154(14) -0.0028(12) 0.0057(11) -0.0014(12) C5 0.018(2) 0.017(2) 0.0108(19) -0.0005(16) 0.0028(16) 0.0020(16) C6 0.021(2) 0.025(2) 0.0084(19) -0.0007(17) 0.0047(16) 0.0017(17) C7 0.016(2) 0.024(2) 0.015(2) 0.0048(17) 0.0038(16) -0.0029(16) C8 0.020(2) 0.019(2) 0.0113(19) -0.0005(16) 0.0007(16) 0.0065(16) C9 0.022(2) 0.031(2) 0.011(2) -0.0020(18) 0.0061(16) 0.0047(18) C10 0.018(2) 0.022(2) 0.0114(19) -0.0019(17) 0.0028(16) -0.0005(16) C11 0.024(2) 0.030(3) 0.014(2) -0.0019(18) 0.0084(17) 0.0008(18) F1 0.0158(13) 0.0597(18) 0.0339(15) -0.0245(13) 0.0008(11) -0.0004(12) F2 0.0319(15) 0.0508(16) 0.0134(12) -0.0078(12) 0.0053(10) -0.0074(12) F3 0.0547(19) 0.0275(15) 0.0298(15) -0.0034(12) -0.0003(13) -0.0087(13) C12 0.020(2) 0.021(2) 0.012(2) -0.0023(17) -0.0014(16) 0.0032(17) C13 0.023(2) 0.026(2) 0.018(2) 0.0029(18) 0.0038(17) 0.0029(18) C14 0.030(3) 0.024(2) 0.027(2) 0.000(2) 0.004(2) 0.0068(19) C15 0.040(3) 0.021(2) 0.025(2) -0.002(2) -0.004(2) 0.008(2) C16 0.055(3) 0.033(3) 0.015(2) 0.003(2) 0.004(2) 0.011(2) C17 0.039(3) 0.027(2) 0.020(2) 0.0025(19) 0.006(2) 0.012(2) C18 0.019(2) 0.019(2) 0.0091(19) 0.0005(16) 0.0033(15) 0.0032(16) C19 0.020(2) 0.039(3) 0.016(2) -0.002(2) 0.0012(17) -0.0029(19) C20 0.024(2) 0.048(3) 0.021(2) 0.013(2) 0.0087(19) 0.000(2) C21 0.052(3) 0.026(2) 0.014(2) 0.0041(19) 0.016(2) 0.010(2) C22 0.065(4) 0.027(3) 0.012(2) -0.0036(19) 0.007(2) -0.009(2) C23 0.040(3) 0.021(2) 0.019(2) 0.0011(19) 0.006(2) -0.0072(19) C24 0.017(2) 0.019(2) 0.0106(19) -0.0002(16) 0.0004(15) 0.0021(16) C25 0.020(2) 0.022(2) 0.012(2) -0.0008(17) 0.0042(16) -0.0021(17) C26 0.020(2) 0.026(2) 0.013(2) 0.0012(18) 0.0026(16) 0.0009(17) C27 0.027(2) 0.022(2) 0.017(2) -0.0040(18) 0.0045(18) 0.0064(18) C28 0.028(2) 0.014(2) 0.018(2) -0.0019(17) 0.0038(18) 0.0012(17) C29 0.019(2) 0.026(2) 0.012(2) -0.0007(18) 0.0049(16) 0.0001(17) C30 0.022(2) 0.023(2) 0.0111(19) -0.0035(17) 0.0042(16) 0.0060(17) C31 0.028(2) 0.032(2) 0.015(2) 0.0037(19) 0.0016(18) 0.0053(19) C32 0.046(3) 0.027(3) 0.017(2) 0.003(2) -0.004(2) 0.009(2) C33 0.062(3) 0.022(2) 0.016(2) 0.0030(19) 0.009(2) 0.007(2) C34 0.051(3) 0.021(2) 0.022(2) 0.0003(19) 0.023(2) 0.005(2) C35 0.031(2) 0.023(2) 0.017(2) -0.0040(19) 0.0065(18) 0.0000(18) _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 1.485(3) . ? P1 C4 1.784(4) . ? P1 C5 1.816(4) . ? P1 C1 1.819(4) . ? C1 C2 1.349(5) . ? C1 C12 1.477(5) . ? C2 C18 1.500(5) . ? C2 C3 1.514(5) . ? C3 C4 1.346(5) . ? C3 C24 1.496(5) . ? C4 C30 1.473(5) . ? C5 C6 1.387(5) . ? C5 C10 1.395(5) . ? C6 C7 1.381(5) . ? C6 H1 0.9500 . ? C7 C8 1.399(5) . ? C7 H2 0.9500 . ? C8 C9 1.378(5) . ? C8 C11 1.499(5) . ? C9 C10 1.397(5) . ? C9 H3 0.9500 . ? C10 H4 0.9500 . ? C11 F1 1.326(4) . ? C11 F2 1.336(4) . ? C11 F3 1.351(5) . ? C12 C13 1.402(5) . ? C12 C17 1.409(6) . ? C13 C14 1.384(6) . ? C13 H5 0.9500 . ? C14 C15 1.380(6) . ? C14 H6 0.9500 . ? C15 C16 1.386(6) . ? C15 H7 0.9500 . ? C16 C17 1.379(6) . ? C16 H8 0.9500 . ? C17 H9 0.9500 . ? C18 C23 1.388(6) . ? C18 C19 1.394(5) . ? C19 C20 1.394(6) . ? C19 H10 0.9500 . ? C20 C21 1.376(6) . ? C20 H11 0.9500 . ? C21 C22 1.384(6) . ? C21 H12 0.9500 . ? C22 C23 1.398(6) . ? C22 H13 0.9500 . ? C23 H14 0.9500 . ? C24 C29 1.390(5) . ? C24 C25 1.397(5) . ? C25 C26 1.394(5) . ? C25 H15 0.9500 . ? C26 C27 1.384(6) . ? C26 H16 0.9500 . ? C27 C28 1.393(6) . ? C27 H17 0.9500 . ? C28 C29 1.388(5) . ? C28 H18 0.9500 . ? C29 H19 0.9500 . ? C30 C31 1.388(6) . ? C30 C35 1.404(6) . ? C31 C32 1.389(6) . ? C31 H20 0.9500 . ? C32 C33 1.388(6) . ? C32 H21 0.9500 . ? C33 C34 1.388(7) . ? C33 H22 0.9500 . ? C34 C35 1.382(6) . ? C34 H23 0.9500 . ? C35 H24 0.9500 . ? 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 C4 118.66(17) . . ? O1 P1 C5 111.73(16) . . ? C4 P1 C5 105.23(18) . . ? O1 P1 C1 119.70(17) . . ? C4 P1 C1 93.81(17) . . ? C5 P1 C1 105.39(18) . . ? C2 C1 C12 131.1(4) . . ? C2 C1 P1 108.0(3) . . ? C12 C1 P1 120.9(3) . . ? C1 C2 C18 127.2(4) . . ? C1 C2 C3 114.4(3) . . ? C18 C2 C3 118.2(3) . . ? C4 C3 C24 122.4(3) . . ? C4 C3 C2 114.5(3) . . ? C24 C3 C2 123.0(3) . . ? C3 C4 C30 129.4(4) . . ? C3 C4 P1 109.1(3) . . ? C30 C4 P1 121.5(3) . . ? C6 C5 C10 119.5(4) . . ? C6 C5 P1 121.8(3) . . ? C10 C5 P1 118.6(3) . . ? C7 C6 C5 120.7(3) . . ? C7 C6 H1 119.7 . . ? C5 C6 H1 119.7 . . ? C6 C7 C8 119.4(4) . . ? C6 C7 H2 120.3 . . ? C8 C7 H2 120.3 . . ? C9 C8 C7 120.7(4) . . ? C9 C8 C11 121.1(3) . . ? C7 C8 C11 118.3(3) . . ? C8 C9 C10 119.5(4) . . ? C8 C9 H3 120.2 . . ? C10 C9 H3 120.2 . . ? C5 C10 C9 120.1(4) . . ? C5 C10 H4 119.9 . . ? C9 C10 H4 119.9 . . ? F1 C11 F2 107.5(3) . . ? F1 C11 F3 106.1(3) . . ? F2 C11 F3 105.5(3) . . ? F1 C11 C8 112.9(3) . . ? F2 C11 C8 112.7(3) . . ? F3 C11 C8 111.5(3) . . ? C13 C12 C17 117.7(4) . . ? C13 C12 C1 118.2(3) . . ? C17 C12 C1 124.2(3) . . ? C14 C13 C12 121.4(4) . . ? C14 C13 H5 119.3 . . ? C12 C13 H5 119.3 . . ? C15 C14 C13 120.6(4) . . ? C15 C14 H6 119.7 . . ? C13 C14 H6 119.7 . . ? C14 C15 C16 118.4(4) . . ? C14 C15 H7 120.8 . . ? C16 C15 H7 120.8 . . ? C17 C16 C15 122.2(4) . . ? C17 C16 H8 118.9 . . ? C15 C16 H8 118.9 . . ? C16 C17 C12 119.7(4) . . ? C16 C17 H9 120.1 . . ? C12 C17 H9 120.1 . . ? C23 C18 C19 119.7(4) . . ? C23 C18 C2 119.3(4) . . ? C19 C18 C2 121.0(3) . . ? C20 C19 C18 119.9(4) . . ? C20 C19 H10 120.1 . . ? C18 C19 H10 120.1 . . ? C21 C20 C19 120.1(4) . . ? C21 C20 H11 120.0 . . ? C19 C20 H11 120.0 . . ? C20 C21 C22 120.6(4) . . ? C20 C21 H12 119.7 . . ? C22 C21 H12 119.7 . . ? C21 C22 C23 119.8(4) . . ? C21 C22 H13 120.1 . . ? C23 C22 H13 120.1 . . ? C18 C23 C22 120.0(4) . . ? C18 C23 H14 120.0 . . ? C22 C23 H14 120.0 . . ? C29 C24 C25 119.3(3) . . ? C29 C24 C3 119.9(3) . . ? C25 C24 C3 120.7(3) . . ? C26 C25 C24 119.8(4) . . ? C26 C25 H15 120.1 . . ? C24 C25 H15 120.1 . . ? C27 C26 C25 120.8(4) . . ? C27 C26 H16 119.6 . . ? C25 C26 H16 119.6 . . ? C26 C27 C28 119.2(4) . . ? C26 C27 H17 120.4 . . ? C28 C27 H17 120.4 . . ? C29 C28 C27 120.4(4) . . ? C29 C28 H18 119.8 . . ? C27 C28 H18 119.8 . . ? C28 C29 C24 120.5(4) . . ? C28 C29 H19 119.8 . . ? C24 C29 H19 119.8 . . ? C31 C30 C35 119.0(4) . . ? C31 C30 C4 121.5(4) . . ? C35 C30 C4 119.5(4) . . ? C30 C31 C32 120.8(4) . . ? C30 C31 H20 119.6 . . ? C32 C31 H20 119.6 . . ? C33 C32 C31 119.8(4) . . ? C33 C32 H21 120.1 . . ? C31 C32 H21 120.1 . . ? C34 C33 C32 120.0(4) . . ? C34 C33 H22 120.0 . . ? C32 C33 H22 120.0 . . ? C35 C34 C33 120.3(4) . . ? C35 C34 H23 119.8 . . ? C33 C34 H23 119.8 . . ? C34 C35 C30 120.2(4) . . ? C34 C35 H24 119.9 . . ? C30 C35 H24 119.9 . . ? 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 O1 P1 C1 C2 129.2(3) . . . . ? C4 P1 C1 C2 2.9(3) . . . . ? C5 P1 C1 C2 -104.0(3) . . . . ? O1 P1 C1 C12 -50.7(4) . . . . ? C4 P1 C1 C12 -176.9(3) . . . . ? C5 P1 C1 C12 76.1(3) . . . . ? C12 C1 C2 C18 3.7(7) . . . . ? P1 C1 C2 C18 -176.2(3) . . . . ? C12 C1 C2 C3 178.2(4) . . . . ? P1 C1 C2 C3 -1.6(4) . . . . ? C1 C2 C3 C4 -1.1(5) . . . . ? C18 C2 C3 C4 174.0(3) . . . . ? C1 C2 C3 C24 179.6(3) . . . . ? C18 C2 C3 C24 -5.3(5) . . . . ? C24 C3 C4 C30 -0.5(6) . . . . ? C2 C3 C4 C30 -179.8(4) . . . . ? C24 C3 C4 P1 -177.4(3) . . . . ? C2 C3 C4 P1 3.3(4) . . . . ? O1 P1 C4 C3 -130.6(3) . . . . ? C5 P1 C4 C3 103.5(3) . . . . ? C1 P1 C4 C3 -3.5(3) . . . . ? O1 P1 C4 C30 52.2(4) . . . . ? C5 P1 C4 C30 -73.7(3) . . . . ? C1 P1 C4 C30 179.3(3) . . . . ? O1 P1 C5 C6 171.3(3) . . . . ? C4 P1 C5 C6 -58.6(4) . . . . ? C1 P1 C5 C6 39.8(4) . . . . ? O1 P1 C5 C10 -9.8(4) . . . . ? C4 P1 C5 C10 120.2(3) . . . . ? C1 P1 C5 C10 -141.4(3) . . . . ? C10 C5 C6 C7 1.8(6) . . . . ? P1 C5 C6 C7 -179.4(3) . . . . ? C5 C6 C7 C8 -1.0(6) . . . . ? C6 C7 C8 C9 -0.3(6) . . . . ? C6 C7 C8 C11 178.1(4) . . . . ? C7 C8 C9 C10 0.8(6) . . . . ? C11 C8 C9 C10 -177.6(4) . . . . ? C6 C5 C10 C9 -1.3(6) . . . . ? P1 C5 C10 C9 179.8(3) . . . . ? C8 C9 C10 C5 0.1(6) . . . . ? C9 C8 C11 F1 -141.0(4) . . . . ? C7 C8 C11 F1 40.6(5) . . . . ? C9 C8 C11 F2 -18.9(5) . . . . ? C7 C8 C11 F2 162.7(3) . . . . ? C9 C8 C11 F3 99.6(4) . . . . ? C7 C8 C11 F3 -78.8(4) . . . . ? C2 C1 C12 C13 -176.3(4) . . . . ? P1 C1 C12 C13 3.5(5) . . . . ? C2 C1 C12 C17 4.3(7) . . . . ? P1 C1 C12 C17 -175.9(3) . . . . ? C17 C12 C13 C14 -1.7(6) . . . . ? C1 C12 C13 C14 178.9(4) . . . . ? C12 C13 C14 C15 0.3(7) . . . . ? C13 C14 C15 C16 1.1(7) . . . . ? C14 C15 C16 C17 -1.3(7) . . . . ? C15 C16 C17 C12 -0.1(7) . . . . ? C13 C12 C17 C16 1.6(6) . . . . ? C1 C12 C17 C16 -179.1(4) . . . . ? C1 C2 C18 C23 93.7(5) . . . . ? C3 C2 C18 C23 -80.7(5) . . . . ? C1 C2 C18 C19 -87.3(5) . . . . ? C3 C2 C18 C19 98.3(4) . . . . ? C23 C18 C19 C20 0.7(6) . . . . ? C2 C18 C19 C20 -178.3(4) . . . . ? C18 C19 C20 C21 0.0(7) . . . . ? C19 C20 C21 C22 -0.8(7) . . . . ? C20 C21 C22 C23 0.8(7) . . . . ? C19 C18 C23 C22 -0.7(6) . . . . ? C2 C18 C23 C22 178.3(4) . . . . ? C21 C22 C23 C18 0.0(7) . . . . ? C4 C3 C24 C29 -50.3(5) . . . . ? C2 C3 C24 C29 128.9(4) . . . . ? C4 C3 C24 C25 125.8(4) . . . . ? C2 C3 C24 C25 -55.0(5) . . . . ? C29 C24 C25 C26 0.2(6) . . . . ? C3 C24 C25 C26 -176.0(3) . . . . ? C24 C25 C26 C27 0.2(6) . . . . ? C25 C26 C27 C28 -0.9(6) . . . . ? C26 C27 C28 C29 1.1(6) . . . . ? C27 C28 C29 C24 -0.7(6) . . . . ? C25 C24 C29 C28 0.0(6) . . . . ? C3 C24 C29 C28 176.2(4) . . . . ? C3 C4 C30 C31 -64.8(6) . . . . ? P1 C4 C30 C31 111.8(4) . . . . ? C3 C4 C30 C35 116.4(5) . . . . ? P1 C4 C30 C35 -67.0(5) . . . . ? C35 C30 C31 C32 0.3(6) . . . . ? C4 C30 C31 C32 -178.5(4) . . . . ? C30 C31 C32 C33 -1.4(6) . . . . ? C31 C32 C33 C34 2.5(6) . . . . ? C32 C33 C34 C35 -2.5(6) . . . . ? C33 C34 C35 C30 1.4(6) . . . . ? C31 C30 C35 C34 -0.3(6) . . . . ? C4 C30 C35 C34 178.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.335 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.082