# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '- all.cif' # Name and address of author for correspondence _publ_contact_author_name 'Hatcher, L.E.' _publ_contact_author_address ; Department of Chemistry University of Bath Bath UK ; _publ_contact_author_email p.r.raithby@bath.ac.uk _publ_contact_author_fax '+44 (0) 1225 383183' _publ_contact_author_phone '+44 (0) 1225 386231' _publ_requested_category FO loop_ _publ_author_name 'Amanda Jarvis' 'Hazel Sparkes' 'Sarah Tallentire' 'Lauren Hatcher' 'Mark Warren' 'Paul Raithby' 'David Allan' 'Adrian Whitwood' 'Martin Cockett' 'Simon Duckett' 'Johnathan Clark' 'Ian Fairlamb' data_ijf0909m _database_code_depnum_ccdc_archive 'CCDC 874829' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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 9.4829(7) _cell_length_b 17.0177(13) _cell_length_c 14.5741(11) _cell_angle_alpha 90.00 _cell_angle_beta 101.8810(10) _cell_angle_gamma 90.00 _cell_volume 2301.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 9550 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 28.27 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.841 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_process_details 'SADABS v2.10 (Sheldrick)' _diffrn_ambient_temperature 110(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 23431 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5718 _reflns_number_gt 4934 _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, 1997)' _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^)+(0.0556P)^2^+0.7477P] 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 5718 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.96010(14) 0.05394(8) 0.22191(10) 0.0269(3) Uani 1 1 d . . . H1 H 1.0157 0.0256 0.2730 0.032 Uiso 1 1 calc R . . C2 C 1.00608(15) 0.05911(8) 0.13740(10) 0.0300(3) Uani 1 1 d . . . H2 H 1.0929 0.0339 0.1310 0.036 Uiso 1 1 calc R . . C3 C 0.92666(16) 0.10061(9) 0.06233(10) 0.0311(3) Uani 1 1 d . . . H3 H 0.9594 0.1038 0.0051 0.037 Uiso 1 1 calc R . . C4 C 0.79913(16) 0.13750(9) 0.07092(10) 0.0330(3) Uani 1 1 d . . . H4 H 0.7444 0.1660 0.0197 0.040 Uiso 1 1 calc R . . C5 C 0.75243(15) 0.13227(8) 0.15512(10) 0.0298(3) Uani 1 1 d . . . H5 H 0.6652 0.1574 0.1609 0.036 Uiso 1 1 calc R . . C6 C 0.83151(14) 0.09064(8) 0.23162(9) 0.0240(3) Uani 1 1 d . . . C7 C 0.77573(14) 0.08757(8) 0.31824(10) 0.0248(3) Uani 1 1 d . . . H7 H 0.6842 0.1110 0.3160 0.030 Uiso 1 1 calc R . . C8 C 0.83926(14) 0.05546(8) 0.39998(9) 0.0241(3) Uani 1 1 d . . . H8 H 0.9278 0.0285 0.4030 0.029 Uiso 1 1 calc R . . C9 C 0.77967(14) 0.05946(7) 0.48609(9) 0.0233(3) Uani 1 1 d . . . C10 C 0.62612(14) 0.08129(8) 0.47932(9) 0.0251(3) Uani 1 1 d . . . H10 H 0.5624 0.0844 0.4199 0.030 Uiso 1 1 calc R . . C11 C 0.57881(13) 0.09641(7) 0.55735(9) 0.0228(2) Uani 1 1 d . . . H11 H 0.6481 0.0931 0.6145 0.027 Uiso 1 1 calc R . . C12 C 0.43145(13) 0.11764(7) 0.56509(9) 0.0217(2) Uani 1 1 d . . . C13 C 0.32546(15) 0.13228(8) 0.48426(9) 0.0268(3) Uani 1 1 d . . . H13 H 0.3502 0.1288 0.4245 0.032 Uiso 1 1 calc R . . C14 C 0.18531(14) 0.15172(8) 0.48984(10) 0.0286(3) Uani 1 1 d . . . H14 H 0.1157 0.1618 0.4342 0.034 Uiso 1 1 calc R . . C15 C 0.14666(14) 0.15645(8) 0.57593(10) 0.0282(3) Uani 1 1 d . . . H15 H 0.0506 0.1696 0.5796 0.034 Uiso 1 1 calc R . . C16 C 0.24908(14) 0.14181(8) 0.65743(9) 0.0243(3) Uani 1 1 d . . . H16 H 0.2220 0.1445 0.7166 0.029 Uiso 1 1 calc R . . C17 C 0.39108(13) 0.12317(7) 0.65322(9) 0.0200(2) Uani 1 1 d . . . C18 C 0.66759(13) 0.16825(7) 0.76793(8) 0.0208(2) Uani 1 1 d . . . C19 C 0.64491(14) 0.24564(8) 0.73619(9) 0.0242(3) Uani 1 1 d . . . H19 H 0.5501 0.2638 0.7110 0.029 Uiso 1 1 calc R . . C20 C 0.76199(16) 0.29570(8) 0.74176(10) 0.0295(3) Uani 1 1 d . . . H20 H 0.7470 0.3486 0.7214 0.035 Uiso 1 1 calc R . . C21 C 0.90090(16) 0.26885(9) 0.77693(11) 0.0343(3) Uani 1 1 d . . . H21 H 0.9805 0.3033 0.7795 0.041 Uiso 1 1 calc R . . C22 C 0.92391(15) 0.19253(10) 0.80816(11) 0.0356(3) Uani 1 1 d . . . H22 H 1.0190 0.1745 0.8325 0.043 Uiso 1 1 calc R . . C23 C 0.80722(15) 0.14209(9) 0.80384(10) 0.0289(3) Uani 1 1 d . . . H23 H 0.8229 0.0895 0.8255 0.035 Uiso 1 1 calc R . . C24 C 0.43012(13) 0.12566(7) 0.85597(9) 0.0218(2) Uani 1 1 d . . . C25 C 0.39873(15) 0.20391(8) 0.87356(10) 0.0269(3) Uani 1 1 d . . . H25 H 0.4260 0.2448 0.8364 0.032 Uiso 1 1 calc R . . C26 C 0.32765(16) 0.22172(9) 0.94538(10) 0.0312(3) Uani 1 1 d . . . H26 H 0.3067 0.2749 0.9574 0.037 Uiso 1 1 calc R . . C27 C 0.28730(16) 0.16202(10) 0.99945(10) 0.0333(3) Uani 1 1 d . . . H27 H 0.2385 0.1743 1.0484 0.040 Uiso 1 1 calc R . . C28 C 0.31797(17) 0.08453(10) 0.98228(11) 0.0355(3) Uani 1 1 d . . . H28 H 0.2903 0.0438 1.0195 0.043 Uiso 1 1 calc R . . C29 C 0.38923(15) 0.06618(8) 0.91071(10) 0.0285(3) Uani 1 1 d . . . H29 H 0.4101 0.0129 0.8991 0.034 Uiso 1 1 calc R . . O1 O 0.85753(10) 0.04568(6) 0.56237(7) 0.0308(2) Uani 1 1 d . . . P1 P 0.51887(3) 0.099318(18) 0.76105(2) 0.01890(9) Uani 1 1 d . . . S1 S 0.58347(4) -0.010288(18) 0.76819(2) 0.02511(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0268(6) 0.0260(6) 0.0280(7) 0.0019(5) 0.0060(5) 0.0035(5) C2 0.0291(7) 0.0302(7) 0.0332(7) 0.0000(6) 0.0123(6) 0.0039(5) C3 0.0355(7) 0.0329(7) 0.0274(7) 0.0012(5) 0.0121(6) -0.0007(6) C4 0.0345(7) 0.0345(7) 0.0297(7) 0.0064(6) 0.0057(6) 0.0045(6) C5 0.0270(7) 0.0306(7) 0.0319(7) 0.0027(6) 0.0065(5) 0.0049(5) C6 0.0242(6) 0.0230(6) 0.0253(6) -0.0006(5) 0.0060(5) -0.0005(5) C7 0.0221(6) 0.0246(6) 0.0286(7) -0.0012(5) 0.0075(5) 0.0006(5) C8 0.0209(6) 0.0239(6) 0.0282(6) -0.0020(5) 0.0063(5) 0.0003(5) C9 0.0238(6) 0.0204(6) 0.0256(6) -0.0006(5) 0.0048(5) -0.0004(5) C10 0.0220(6) 0.0291(6) 0.0234(6) 0.0006(5) 0.0033(5) 0.0001(5) C11 0.0204(6) 0.0249(6) 0.0221(6) 0.0001(5) 0.0022(5) -0.0007(5) C12 0.0214(6) 0.0204(6) 0.0231(6) 0.0005(5) 0.0042(5) 0.0002(4) C13 0.0269(6) 0.0293(7) 0.0229(6) 0.0015(5) 0.0024(5) 0.0006(5) C14 0.0229(6) 0.0309(7) 0.0283(7) 0.0026(5) -0.0028(5) 0.0007(5) C15 0.0190(6) 0.0285(7) 0.0359(7) 0.0006(5) 0.0028(5) 0.0011(5) C16 0.0205(6) 0.0251(6) 0.0280(6) 0.0001(5) 0.0065(5) -0.0008(5) C17 0.0202(6) 0.0172(5) 0.0216(6) 0.0002(4) 0.0023(4) -0.0006(4) C18 0.0208(6) 0.0240(6) 0.0178(5) -0.0010(4) 0.0047(4) -0.0029(4) C19 0.0249(6) 0.0254(6) 0.0231(6) 0.0001(5) 0.0063(5) -0.0031(5) C20 0.0362(7) 0.0265(7) 0.0270(7) -0.0007(5) 0.0091(6) -0.0092(6) C21 0.0294(7) 0.0414(8) 0.0333(7) -0.0059(6) 0.0093(6) -0.0151(6) C22 0.0207(6) 0.0465(9) 0.0379(8) -0.0026(7) 0.0021(6) -0.0041(6) C23 0.0236(6) 0.0316(7) 0.0299(7) 0.0023(5) 0.0017(5) -0.0006(5) C24 0.0208(6) 0.0237(6) 0.0211(6) 0.0002(5) 0.0047(5) -0.0022(5) C25 0.0309(7) 0.0243(6) 0.0279(6) -0.0020(5) 0.0118(5) -0.0038(5) C26 0.0334(7) 0.0306(7) 0.0315(7) -0.0062(6) 0.0114(6) -0.0022(6) C27 0.0338(7) 0.0447(8) 0.0243(6) -0.0021(6) 0.0126(6) -0.0019(6) C28 0.0394(8) 0.0398(8) 0.0306(7) 0.0093(6) 0.0146(6) -0.0016(6) C29 0.0327(7) 0.0265(7) 0.0272(7) 0.0044(5) 0.0087(5) -0.0010(5) O1 0.0264(5) 0.0387(6) 0.0267(5) 0.0022(4) 0.0043(4) 0.0043(4) P1 0.01904(15) 0.01810(15) 0.01949(16) 0.00090(11) 0.00380(11) -0.00027(11) S1 0.02653(17) 0.01933(16) 0.02847(17) 0.00123(12) 0.00337(13) 0.00285(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 C1 C2 1.3913(19) . ? C1 C6 1.4029(18) . ? C1 H1 0.9500 . ? C2 C3 1.387(2) . ? C2 H2 0.9500 . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 C6 1.4012(19) . ? C5 H5 0.9500 . ? C6 C7 1.4667(18) . ? C7 C8 1.3360(19) . ? C7 H7 0.9500 . ? C8 C9 1.4802(18) . ? C8 H8 0.9500 . ? C9 O1 1.2239(16) . ? C9 C10 1.4862(18) . ? C10 C11 1.3307(18) . ? C10 H10 0.9500 . ? C11 C12 1.4700(17) . ? C11 H11 0.9500 . ? C12 C13 1.4044(18) . ? C12 C17 1.4169(17) . ? C13 C14 1.3881(19) . ? C13 H13 0.9500 . ? C14 C15 1.380(2) . ? C14 H14 0.9500 . ? C15 C16 1.3932(19) . ? C15 H15 0.9500 . ? C16 C17 1.3970(17) . ? C16 H16 0.9500 . ? C17 P1 1.8219(12) . ? C18 C23 1.3929(18) . ? C18 C19 1.3978(18) . ? C18 P1 1.8212(13) . ? C19 C20 1.3884(18) . ? C19 H19 0.9500 . ? C20 C21 1.389(2) . ? C20 H20 0.9500 . ? C21 C22 1.379(2) . ? C21 H21 0.9500 . ? C22 C23 1.392(2) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C29 1.3923(18) . ? C24 C25 1.3997(18) . ? C24 P1 1.8173(13) . ? C25 C26 1.3901(18) . ? C25 H25 0.9500 . ? C26 C27 1.387(2) . ? C26 H26 0.9500 . ? C27 C28 1.384(2) . ? C27 H27 0.9500 . ? C28 C29 1.390(2) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? P1 S1 1.9593(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 C2 C1 C6 119.90(13) . . ? C2 C1 H1 120.1 . . ? C6 C1 H1 120.1 . . ? C3 C2 C1 120.82(13) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 119.99(13) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.42(13) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.27(13) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 118.60(12) . . ? C5 C6 C7 118.30(12) . . ? C1 C6 C7 123.10(12) . . ? C8 C7 C6 127.28(12) . . ? C8 C7 H7 116.4 . . ? C6 C7 H7 116.4 . . ? C7 C8 C9 123.81(12) . . ? C7 C8 H8 118.1 . . ? C9 C8 H8 118.1 . . ? O1 C9 C8 119.81(12) . . ? O1 C9 C10 120.52(12) . . ? C8 C9 C10 119.67(11) . . ? C11 C10 C9 119.32(12) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 127.31(12) . . ? C10 C11 H11 116.3 . . ? C12 C11 H11 116.3 . . ? C13 C12 C17 117.92(11) . . ? C13 C12 C11 120.44(12) . . ? C17 C12 C11 121.63(11) . . ? C14 C13 C12 121.44(12) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C15 C14 C13 120.26(12) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.71(12) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 120.82(12) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C12 119.85(11) . . ? C16 C17 P1 119.26(9) . . ? C12 C17 P1 120.75(9) . . ? C23 C18 C19 119.67(12) . . ? C23 C18 P1 118.70(10) . . ? C19 C18 P1 121.61(10) . . ? C20 C19 C18 119.47(13) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C19 C20 C21 120.40(13) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C20 120.36(13) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 119.72(14) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C22 C23 C18 120.36(13) . . ? C22 C23 H23 119.8 . . ? C18 C23 H23 119.8 . . ? C29 C24 C25 119.47(12) . . ? C29 C24 P1 118.95(10) . . ? C25 C24 P1 121.56(10) . . ? C26 C25 C24 119.98(13) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C27 C26 C25 120.10(14) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C28 C27 C26 120.14(13) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C28 C29 120.16(14) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C28 C29 C24 120.16(13) . . ? C28 C29 H29 119.9 . . ? C24 C29 H29 119.9 . . ? C24 P1 C18 105.90(6) . . ? C24 P1 C17 105.76(6) . . ? C18 P1 C17 105.90(6) . . ? C24 P1 S1 112.53(4) . . ? C18 P1 S1 112.34(4) . . ? C17 P1 S1 113.77(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.4(2) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C3 C4 C5 C6 0.1(2) . . . . ? C4 C5 C6 C1 0.1(2) . . . . ? C4 C5 C6 C7 -179.98(13) . . . . ? C2 C1 C6 C5 -0.3(2) . . . . ? C2 C1 C6 C7 179.75(13) . . . . ? C5 C6 C7 C8 -175.41(14) . . . . ? C1 C6 C7 C8 4.5(2) . . . . ? C6 C7 C8 C9 175.84(12) . . . . ? C7 C8 C9 O1 -162.76(13) . . . . ? C7 C8 C9 C10 16.40(19) . . . . ? O1 C9 C10 C11 9.3(2) . . . . ? C8 C9 C10 C11 -169.87(12) . . . . ? C9 C10 C11 C12 -179.03(12) . . . . ? C10 C11 C12 C13 -6.9(2) . . . . ? C10 C11 C12 C17 172.35(13) . . . . ? C17 C12 C13 C14 0.1(2) . . . . ? C11 C12 C13 C14 179.41(12) . . . . ? C12 C13 C14 C15 -0.6(2) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C14 C15 C16 C17 0.7(2) . . . . ? C15 C16 C17 C12 -1.11(19) . . . . ? C15 C16 C17 P1 -176.72(10) . . . . ? C13 C12 C17 C16 0.72(18) . . . . ? C11 C12 C17 C16 -178.58(12) . . . . ? C13 C12 C17 P1 176.26(10) . . . . ? C11 C12 C17 P1 -3.04(17) . . . . ? C23 C18 C19 C20 -0.63(19) . . . . ? P1 C18 C19 C20 -179.14(10) . . . . ? C18 C19 C20 C21 1.2(2) . . . . ? C19 C20 C21 C22 -1.1(2) . . . . ? C20 C21 C22 C23 0.4(2) . . . . ? C21 C22 C23 C18 0.2(2) . . . . ? C19 C18 C23 C22 -0.1(2) . . . . ? P1 C18 C23 C22 178.50(11) . . . . ? C29 C24 C25 C26 0.2(2) . . . . ? P1 C24 C25 C26 178.47(11) . . . . ? C24 C25 C26 C27 -0.2(2) . . . . ? C25 C26 C27 C28 0.2(2) . . . . ? C26 C27 C28 C29 -0.1(2) . . . . ? C27 C28 C29 C24 0.0(2) . . . . ? C25 C24 C29 C28 -0.1(2) . . . . ? P1 C24 C29 C28 -178.40(11) . . . . ? C29 C24 P1 C18 -136.26(11) . . . . ? C25 C24 P1 C18 45.46(12) . . . . ? C29 C24 P1 C17 111.63(11) . . . . ? C25 C24 P1 C17 -66.66(12) . . . . ? C29 C24 P1 S1 -13.15(12) . . . . ? C25 C24 P1 S1 168.56(10) . . . . ? C23 C18 P1 C24 104.74(11) . . . . ? C19 C18 P1 C24 -76.74(11) . . . . ? C23 C18 P1 C17 -143.25(10) . . . . ? C19 C18 P1 C17 35.28(12) . . . . ? C23 C18 P1 S1 -18.48(12) . . . . ? C19 C18 P1 S1 160.04(9) . . . . ? C16 C17 P1 C24 -11.12(12) . . . . ? C12 C17 P1 C24 173.31(10) . . . . ? C16 C17 P1 C18 -123.23(10) . . . . ? C12 C17 P1 C18 61.20(11) . . . . ? C16 C17 P1 S1 112.89(10) . . . . ? C12 C17 P1 S1 -62.67(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.435 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.053 ### END data_ijf0911m _database_code_depnum_ccdc_archive 'CCDC 874830' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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 9.3900(7) _cell_length_b 17.1409(14) _cell_length_c 14.6595(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.038(2) _cell_angle_gamma 90.00 _cell_volume 2307.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 7433 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 28.01 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.940 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details 'SADABS v2.03;(Sheldrick)' _diffrn_ambient_temperature 110(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 23321 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5737 _reflns_number_gt 4646 _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. Mixture of uncyclised and cyclised compounds with a refined ratio of 0.689:0.311(3). ADP of pairs of disordered atom constrained to be equal as follows: C1 C1A, C2 C2A, C3 C3A, C4 C4A, C5 C5A, C6 C6A, C12A C12, C13A C13, C14 C14A, C15A C15, C16A C16, C17A C17 Same distance restraint on C7-C6 & C7A-C6A; C7-C8 & C7A-C8A Rigid bond restraint on C9-C8; C8A-C9A-C10A ISotropic ADP restrain on C8A C7A C9 C9A C10A O1 O1A ; _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^)+(0.0528P)^2^+1.1333P] 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 5737 _refine_ls_number_parameters 368 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7456(4) 0.1317(3) 0.1548(2) 0.0343(6) Uani 0.689(3) 1 d P A 1 H1 H 0.6572 0.1567 0.1599 0.041 Uiso 0.689(3) 1 calc PR A 1 C2 C 0.7929(8) 0.1364(5) 0.0716(3) 0.0410(7) Uani 0.689(3) 1 d P A 1 H2 H 0.7377 0.1646 0.0205 0.049 Uiso 0.689(3) 1 calc PR A 1 C3 C 0.9215(11) 0.0996(8) 0.0633(5) 0.0415(8) Uani 0.689(3) 1 d P A 1 H3 H 0.9545 0.1024 0.0064 0.050 Uiso 0.689(3) 1 calc PR A 1 C4 C 1.0011(8) 0.0592(7) 0.1382(6) 0.0414(8) Uani 0.689(3) 1 d P A 1 H4 H 1.0889 0.0340 0.1323 0.050 Uiso 0.689(3) 1 calc PR A 1 C5 C 0.9548(4) 0.0546(4) 0.2221(5) 0.0368(7) Uani 0.689(3) 1 d P A 1 H5 H 1.0113 0.0268 0.2731 0.044 Uiso 0.689(3) 1 calc PR A 1 C6 C 0.8251(3) 0.0910(3) 0.2317(2) 0.0289(6) Uani 0.689(3) 1 d PD A 1 C6A C 0.8635(9) 0.0851(7) 0.2471(6) 0.0289(6) Uani 0.311(3) 1 d PGD A 2 C5A C 0.9879(11) 0.0503(10) 0.2282(11) 0.0368(7) Uani 0.311(3) 1 d PG A 2 H5A H 1.0502 0.0208 0.2751 0.044 Uiso 0.311(3) 1 calc PR A 2 C4A C 1.0212(19) 0.0588(16) 0.1407(14) 0.0414(8) Uani 0.311(3) 1 d PG A 2 H4A H 1.1063 0.0350 0.1277 0.050 Uiso 0.311(3) 1 calc PR A 2 C3A C 0.930(2) 0.1020(18) 0.0721(10) 0.0415(8) Uani 0.311(3) 1 d PG A 2 H3A H 0.9529 0.1077 0.0123 0.050 Uiso 0.311(3) 1 calc PR A 2 C2A C 0.806(2) 0.1367(12) 0.0910(7) 0.0410(7) Uani 0.311(3) 1 d PG A 2 H2A H 0.7435 0.1662 0.0441 0.049 Uiso 0.311(3) 1 calc PR A 2 C1A C 0.7724(10) 0.1283(7) 0.1785(6) 0.0343(6) Uani 0.311(3) 1 d PG A 2 H1A H 0.6874 0.1520 0.1915 0.041 Uiso 0.311(3) 1 calc PR A 2 C7 C 0.7733(3) 0.08691(15) 0.31922(17) 0.0256(5) Uani 0.689(3) 1 d PD A 1 H7 H 0.6808 0.1100 0.3176 0.031 Uiso 0.689(3) 1 calc PR A 1 C7A C 0.8386(12) 0.0705(6) 0.3464(9) 0.073(3) Uani 0.311(3) 1 d PDU A 2 H7A H 0.9154 0.0512 0.3937 0.087 Uiso 0.311(3) 1 calc PR A 2 C8 C 0.8389(3) 0.05466(14) 0.40318(16) 0.0284(5) Uani 0.689(3) 1 d PDU A 1 H8 H 0.9279 0.0276 0.4055 0.034 Uiso 0.689(3) 1 calc PR A 1 C8A C 0.7234(11) 0.0834(5) 0.3630(8) 0.077(2) Uani 0.311(3) 1 d PDU A 2 H8A H 0.6438 0.1046 0.3192 0.092 Uiso 0.311(3) 1 calc PR A 2 C9 C 0.7859(4) 0.05815(19) 0.4864(2) 0.0318(6) Uani 0.689(3) 1 d PU A 1 C9A C 0.7166(15) 0.0591(5) 0.4774(8) 0.055(2) Uani 0.311(3) 1 d PU A 2 C10 C 0.6319(4) 0.07963(16) 0.47914(18) 0.0342(6) Uani 0.689(3) 1 d P A 1 H10 H 0.5672 0.0816 0.4200 0.041 Uiso 0.689(3) 1 calc PR A 1 C10A C 0.5516(8) 0.0454(3) 0.4655(4) 0.0383(14) Uani 0.311(3) 1 d PU . 2 H10A H 0.4936 0.0837 0.4213 0.046 Uiso 0.311(3) 1 calc PR A 2 C11 C 0.5840(3) 0.09640(13) 0.55688(16) 0.0314(5) Uani 0.689(3) 1 d P A 1 H11 H 0.6546 0.0951 0.6137 0.038 Uiso 0.689(3) 1 calc PR A 1 C11A C 0.4993(6) 0.0410(3) 0.5585(3) 0.0274(11) Uani 0.311(3) 1 d P . 2 H11A H 0.5841 0.0422 0.6126 0.033 Uiso 0.311(3) 1 calc PR A 2 C12 C 0.4339(3) 0.11673(15) 0.56410(17) 0.0299(5) Uani 0.689(3) 1 d P A 1 C12A C 0.3811(7) 0.0954(4) 0.5752(4) 0.0299(5) Uani 0.311(3) 1 d P A 2 C13 C 0.3279(3) 0.13117(19) 0.4836(2) 0.0360(6) Uani 0.689(3) 1 d P A 1 H13 H 0.3542 0.1284 0.4245 0.043 Uiso 0.689(3) 1 calc PR A 1 C13A C 0.2727(9) 0.1220(5) 0.4980(5) 0.0360(6) Uani 0.311(3) 1 d P A 2 H13A H 0.2831 0.1102 0.4365 0.043 Uiso 0.311(3) 1 calc PR A 2 C14 C 0.1865(5) 0.1493(2) 0.4874(3) 0.0395(8) Uani 0.689(3) 1 d P A 1 H14 H 0.1171 0.1593 0.4316 0.047 Uiso 0.689(3) 1 calc PR A 1 C14A C 0.1570(12) 0.1633(7) 0.5101(7) 0.0395(8) Uani 0.311(3) 1 d P A 2 H14A H 0.0886 0.1809 0.4570 0.047 Uiso 0.311(3) 1 calc PR A 2 C15 C 0.1455(3) 0.15308(19) 0.5726(2) 0.0403(7) Uani 0.689(3) 1 d P A 1 H15 H 0.0475 0.1648 0.5753 0.048 Uiso 0.689(3) 1 calc PR A 1 C15A C 0.1348(9) 0.1807(5) 0.5975(6) 0.0403(7) Uani 0.311(3) 1 d P A 2 H15A H 0.0498 0.2079 0.6050 0.048 Uiso 0.311(3) 1 calc PR A 2 C16 C 0.2481(5) 0.1396(2) 0.6545(3) 0.0333(7) Uani 0.689(3) 1 d P A 1 H16 H 0.2189 0.1425 0.7127 0.040 Uiso 0.689(3) 1 calc PR A 1 C16A C 0.2402(14) 0.1575(6) 0.6761(7) 0.0333(7) Uani 0.311(3) 1 d P A 2 H16A H 0.2298 0.1697 0.7376 0.040 Uiso 0.311(3) 1 calc PR A 2 C17 C 0.3932(4) 0.1220(4) 0.6531(5) 0.0262(8) Uani 0.689(3) 1 d P A 1 C17A C 0.3588(13) 0.1164(9) 0.6605(12) 0.0262(8) Uani 0.311(3) 1 d P A 2 C18 C 0.66430(17) 0.16575(9) 0.76692(10) 0.0285(3) Uani 1 1 d . A . C19 C 0.6413(2) 0.24251(10) 0.73516(11) 0.0341(3) Uani 1 1 d . . . H19 H 0.5457 0.2602 0.7088 0.041 Uiso 1 1 calc R . . C20 C 0.7592(2) 0.29278(10) 0.74238(13) 0.0413(4) Uani 1 1 d . . . H20 H 0.7439 0.3452 0.7217 0.050 Uiso 1 1 calc R . . C21 C 0.8983(2) 0.26690(12) 0.77944(15) 0.0490(5) Uani 1 1 d . . . H21 H 0.9784 0.3016 0.7836 0.059 Uiso 1 1 calc R . . C22 C 0.9222(2) 0.19109(13) 0.81053(15) 0.0508(5) Uani 1 1 d . . . H22 H 1.0182 0.1736 0.8360 0.061 Uiso 1 1 calc R . . C23 C 0.80519(19) 0.14057(11) 0.80441(13) 0.0388(4) Uani 1 1 d . . . H23 H 0.8214 0.0884 0.8260 0.047 Uiso 1 1 calc R . . C24 C 0.42761(17) 0.12483(9) 0.85717(11) 0.0307(3) Uani 1 1 d . A . C25 C 0.3996(2) 0.20272(10) 0.87517(13) 0.0395(4) Uani 1 1 d . . . H25 H 0.4287 0.2430 0.8385 0.047 Uiso 1 1 calc R . . C26 C 0.3293(2) 0.22121(11) 0.94672(14) 0.0450(4) Uani 1 1 d . . . H26 H 0.3104 0.2742 0.9589 0.054 Uiso 1 1 calc R . . C27 C 0.2867(2) 0.16275(12) 1.00032(13) 0.0438(4) Uani 1 1 d . . . H27 H 0.2387 0.1756 1.0493 0.053 Uiso 1 1 calc R . . C28 C 0.3139(2) 0.08575(12) 0.98257(13) 0.0461(5) Uani 1 1 d . . . H28 H 0.2845 0.0457 1.0194 0.055 Uiso 1 1 calc R . . C29 C 0.3840(2) 0.06660(11) 0.91128(12) 0.0395(4) Uani 1 1 d . . . H29 H 0.4024 0.0134 0.8994 0.047 Uiso 1 1 calc R . . O1 O 0.8634(3) 0.04482(14) 0.56181(16) 0.0406(5) Uani 0.689(3) 1 d PU A 1 O1A O 0.7935(9) 0.0593(5) 0.5519(9) 0.090(3) Uani 0.311(3) 1 d PU A 2 P1 P 0.51495(4) 0.09727(2) 0.76214(3) 0.02779(11) Uani 1 1 d . . . S1 S 0.58192(5) -0.01120(2) 0.77201(3) 0.03907(12) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0279(17) 0.0426(11) 0.028(2) 0.0058(15) -0.0046(12) 0.0049(11) C2 0.0401(16) 0.0482(11) 0.0316(19) 0.008(2) 0.0004(18) 0.0042(11) C3 0.0412(15) 0.0468(13) 0.0373(15) 0.0017(15) 0.0101(14) -0.0018(12) C4 0.032(2) 0.0411(10) 0.0508(12) 0.0012(9) 0.0087(15) 0.0025(18) C5 0.028(2) 0.0347(12) 0.0422(14) 0.0053(9) -0.0052(18) 0.0041(17) C6 0.0213(18) 0.0308(11) 0.0298(15) 0.0013(11) -0.0057(12) -0.0018(15) C6A 0.0213(18) 0.0308(11) 0.0298(15) 0.0013(11) -0.0057(12) -0.0018(15) C5A 0.028(2) 0.0347(12) 0.0422(14) 0.0053(9) -0.0052(18) 0.0041(17) C4A 0.032(2) 0.0411(10) 0.0508(12) 0.0012(9) 0.0087(15) 0.0025(18) C3A 0.0412(15) 0.0468(13) 0.0373(15) 0.0017(15) 0.0101(14) -0.0018(12) C2A 0.0401(16) 0.0482(11) 0.0316(19) 0.008(2) 0.0004(18) 0.0042(11) C1A 0.0279(17) 0.0426(11) 0.028(2) 0.0058(15) -0.0046(12) 0.0049(11) C7 0.0257(13) 0.0246(11) 0.0251(11) 0.0001(9) 0.0024(10) 0.0008(10) C7A 0.051(5) 0.053(5) 0.119(8) -0.036(5) 0.029(6) -0.012(4) C8 0.0374(13) 0.0224(10) 0.0214(11) 0.0002(9) -0.0030(10) 0.0002(9) C8A 0.077(5) 0.064(5) 0.088(5) -0.004(4) 0.013(5) -0.008(4) C9 0.0320(16) 0.0255(12) 0.0349(15) -0.0005(10) -0.0002(14) 0.0017(13) C9A 0.069(5) 0.041(4) 0.072(5) -0.029(4) 0.050(5) -0.021(5) C10 0.0372(15) 0.0365(15) 0.0264(12) 0.0028(10) 0.0009(11) -0.0012(13) C10A 0.067(4) 0.019(2) 0.037(3) -0.007(2) 0.029(3) -0.008(3) C11 0.0347(12) 0.0307(11) 0.0269(11) 0.0005(9) 0.0022(9) -0.0027(9) C11A 0.046(3) 0.018(2) 0.022(2) -0.0043(17) 0.015(2) -0.0022(19) C12 0.0379(16) 0.0247(13) 0.0256(10) 0.0003(9) 0.0032(10) 0.0004(9) C12A 0.0379(16) 0.0247(13) 0.0256(10) 0.0003(9) 0.0032(10) 0.0004(9) C13 0.040(2) 0.0384(13) 0.0256(12) -0.0012(10) -0.0010(11) 0.0012(14) C13A 0.040(2) 0.0384(13) 0.0256(12) -0.0012(10) -0.0010(11) 0.0012(14) C14 0.041(2) 0.042(2) 0.030(2) 0.0004(13) -0.0078(13) -0.0006(15) C14A 0.041(2) 0.042(2) 0.030(2) 0.0004(13) -0.0078(13) -0.0006(15) C15 0.0296(11) 0.040(2) 0.047(2) 0.0013(13) -0.0018(12) 0.0039(13) C15A 0.0296(11) 0.040(2) 0.047(2) 0.0013(13) -0.0018(12) 0.0039(13) C16 0.0301(10) 0.037(2) 0.032(2) 0.0001(13) 0.0030(14) -0.0012(14) C16A 0.0301(10) 0.037(2) 0.032(2) 0.0001(13) 0.0030(14) -0.0012(14) C17 0.022(2) 0.0205(12) 0.0322(14) -0.0019(9) -0.0033(17) -0.0037(16) C17A 0.022(2) 0.0205(12) 0.0322(14) -0.0019(9) -0.0033(17) -0.0037(16) C18 0.0352(8) 0.0291(7) 0.0217(7) 0.0002(6) 0.0073(6) -0.0009(6) C19 0.0426(9) 0.0301(8) 0.0300(8) 0.0013(6) 0.0084(7) -0.0005(7) C20 0.0574(11) 0.0318(8) 0.0372(9) 0.0005(7) 0.0155(8) -0.0078(8) C21 0.0504(11) 0.0487(11) 0.0513(11) -0.0038(9) 0.0185(9) -0.0176(9) C22 0.0344(9) 0.0565(12) 0.0600(13) 0.0034(10) 0.0062(9) -0.0065(9) C23 0.0371(9) 0.0369(9) 0.0411(9) 0.0051(7) 0.0050(7) -0.0009(7) C24 0.0300(8) 0.0293(8) 0.0311(8) 0.0021(6) 0.0022(6) -0.0033(6) C25 0.0453(10) 0.0297(8) 0.0485(10) 0.0010(7) 0.0216(8) -0.0035(7) C26 0.0487(11) 0.0388(10) 0.0526(11) -0.0033(8) 0.0223(9) 0.0001(8) C27 0.0412(10) 0.0575(12) 0.0347(9) 0.0010(8) 0.0124(8) -0.0035(8) C28 0.0557(12) 0.0481(11) 0.0351(9) 0.0115(8) 0.0107(8) -0.0062(9) C29 0.0493(10) 0.0331(9) 0.0344(9) 0.0064(7) 0.0045(8) -0.0024(8) O1 0.0460(14) 0.0433(11) 0.0290(9) 0.0038(8) -0.0006(10) 0.0026(11) O1A 0.062(5) 0.090(5) 0.134(7) -0.070(5) 0.054(6) -0.032(4) P1 0.0317(2) 0.02251(19) 0.02625(19) -0.00064(14) -0.00071(15) 0.00074(15) S1 0.0372(2) 0.0237(2) 0.0511(3) 0.00025(17) -0.00272(19) 0.00326(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 C1 C2 1.385(4) . ? C1 C6 1.401(3) . ? C1 H1 0.9500 . ? C2 C3 1.390(4) . ? C2 H2 0.9500 . ? C3 C4 1.379(4) . ? C3 H3 0.9500 . ? C4 C5 1.389(4) . ? C4 H4 0.9500 . ? C5 C6 1.401(4) . ? C5 H5 0.9500 . ? C6 C7 1.466(4) . ? C6A C5A 1.3900 . ? C6A C1A 1.3900 . ? C6A C7A 1.542(13) . ? C5A C4A 1.3900 . ? C5A H5A 0.9500 . ? C4A C3A 1.3900 . ? C4A H4A 0.9500 . ? C3A C2A 1.3900 . ? C3A H3A 0.9500 . ? C2A C1A 1.3900 . ? C2A H2A 0.9500 . ? C1A H1A 0.9500 . ? C7 C8 1.373(3) . ? C7 H7 0.9500 . ? C7A C8A 1.178(11) . ? C7A H7A 0.9500 . ? C8 C9 1.412(5) . ? C8 H8 0.9500 . ? C8A C9A 1.742(16) . ? C8A H8A 0.9500 . ? C9 O1 1.211(4) . ? C9 C10 1.475(4) . ? C9A O1A 1.177(15) . ? C9A C10A 1.540(13) . ? C10 C11 1.340(4) . ? C10 H10 0.9500 . ? C10A C11A 1.544(7) . ? C10A C11A 1.574(7) 3_656 ? C10A H10A 1.0000 . ? C11 C12 1.478(4) . ? C11 H11 0.9500 . ? C11A C12A 1.507(8) . ? C11A C10A 1.574(7) 3_656 ? C11A H11A 1.0000 . ? C12 C13 1.398(4) . ? C12 C17 1.437(6) . ? C12A C17A 1.358(17) . ? C12A C13A 1.430(10) . ? C13 C14 1.376(5) . ? C13 H13 0.9500 . ? C13A C14A 1.339(11) . ? C13A H13A 0.9500 . ? C14 C15 1.383(5) . ? C14 H14 0.9500 . ? C14A C15A 1.373(11) . ? C14A H14A 0.9500 . ? C15 C16 1.393(5) . ? C15 H15 0.9500 . ? C15A C16A 1.411(15) . ? C15A H15A 0.9500 . ? C16 C17 1.400(6) . ? C16 H16 0.9500 . ? C16A C17A 1.376(17) . ? C16A H16A 0.9500 . ? C17 P1 1.811(6) . ? C17A P1 1.889(16) . ? C18 C23 1.391(2) . ? C18 C19 1.397(2) . ? C18 P1 1.8189(16) . ? C19 C20 1.389(2) . ? C19 H19 0.9500 . ? C20 C21 1.379(3) . ? C20 H20 0.9500 . ? C21 C22 1.380(3) . ? C21 H21 0.9500 . ? C22 C23 1.387(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C29 1.389(2) . ? C24 C25 1.396(2) . ? C24 P1 1.8200(17) . ? C25 C26 1.388(3) . ? C25 H25 0.9500 . ? C26 C27 1.383(3) . ? C26 H26 0.9500 . ? C27 C28 1.379(3) . ? C27 H27 0.9500 . ? C28 C29 1.386(3) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? P1 S1 1.9585(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.4(2) . . ? C2 C1 H1 119.3 . . ? C6 C1 H1 119.3 . . ? C1 C2 C3 119.7(2) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 119.6(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 121.0(3) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 118.0(2) . . ? C1 C6 C7 120.6(3) . . ? C5 C6 C7 121.4(3) . . ? C5A C6A C1A 120.0 . . ? C5A C6A C7A 114.7(9) . . ? C1A C6A C7A 125.3(9) . . ? C6A C5A C4A 120.0 . . ? C6A C5A H5A 120.0 . . ? C4A C5A H5A 120.0 . . ? C3A C4A C5A 120.0 . . ? C3A C4A H4A 120.0 . . ? C5A C4A H4A 120.0 . . ? C4A C3A C2A 120.0 . . ? C4A C3A H3A 120.0 . . ? C2A C3A H3A 120.0 . . ? C1A C2A C3A 120.0 . . ? C1A C2A H2A 120.0 . . ? C3A C2A H2A 120.0 . . ? C2A C1A C6A 120.0 . . ? C2A C1A H1A 120.0 . . ? C6A C1A H1A 120.0 . . ? C8 C7 C6 129.4(3) . . ? C8 C7 H7 115.3 . . ? C6 C7 H7 115.3 . . ? C8A C7A C6A 119.4(14) . . ? C8A C7A H7A 120.3 . . ? C6A C7A H7A 120.3 . . ? C7 C8 C9 125.8(3) . . ? C7 C8 H8 117.1 . . ? C9 C8 H8 117.1 . . ? C7A C8A C9A 111.9(12) . . ? C7A C8A H8A 124.0 . . ? C9A C8A H8A 124.0 . . ? O1 C9 C8 121.9(3) . . ? O1 C9 C10 120.4(3) . . ? C8 C9 C10 117.7(3) . . ? O1A C9A C10A 120.8(8) . . ? O1A C9A C8A 139.0(10) . . ? C10A C9A C8A 99.5(9) . . ? C11 C10 C9 119.3(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C9A C10A C11A 113.9(6) . . ? C9A C10A C11A 114.8(5) . 3_656 ? C11A C10A C11A 90.8(4) . 3_656 ? C9A C10A H10A 111.9 . . ? C11A C10A H10A 111.9 . . ? C11A C10A H10A 111.9 3_656 . ? C10 C11 C12 127.3(2) . . ? C10 C11 H11 116.4 . . ? C12 C11 H11 116.4 . . ? C12A C11A C10A 119.6(5) . . ? C12A C11A C10A 114.8(5) . 3_656 ? C10A C11A C10A 89.2(4) . 3_656 ? C12A C11A H11A 110.5 . . ? C10A C11A H11A 110.5 . . ? C10A C11A H11A 110.5 3_656 . ? C13 C12 C17 118.6(3) . . ? C13 C12 C11 120.2(2) . . ? C17 C12 C11 121.2(3) . . ? C17A C12A C13A 115.0(9) . . ? C17A C12A C11A 125.0(8) . . ? C13A C12A C11A 119.7(5) . . ? C14 C13 C12 121.9(3) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C14A C13A C12A 121.8(8) . . ? C14A C13A H13A 119.1 . . ? C12A C13A H13A 119.1 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C13A C14A C15A 121.6(9) . . ? C13A C14A H14A 119.2 . . ? C15A C14A H14A 119.2 . . ? C14 C15 C16 119.8(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C14A C15A C16A 118.9(8) . . ? C14A C15A H15A 120.5 . . ? C16A C15A H15A 120.5 . . ? C15 C16 C17 121.6(4) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C17A C16A C15A 117.6(10) . . ? C17A C16A H16A 121.2 . . ? C15A C16A H16A 121.2 . . ? C16 C17 C12 118.0(5) . . ? C16 C17 P1 118.4(4) . . ? C12 C17 P1 123.3(3) . . ? C12A C17A C16A 125.1(13) . . ? C12A C17A P1 115.9(9) . . ? C16A C17A P1 118.6(11) . . ? C23 C18 C19 119.47(15) . . ? C23 C18 P1 118.49(12) . . ? C19 C18 P1 122.03(13) . . ? C20 C19 C18 119.55(17) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C21 C20 C19 120.31(17) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.53(18) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C21 C22 C23 119.67(19) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C22 C23 C18 120.46(17) . . ? C22 C23 H23 119.8 . . ? C18 C23 H23 119.8 . . ? C29 C24 C25 119.33(16) . . ? C29 C24 P1 118.96(13) . . ? C25 C24 P1 121.68(12) . . ? C26 C25 C24 119.94(16) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C27 C26 C25 120.24(18) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C28 C27 C26 119.94(18) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C29 120.32(17) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C28 C29 C24 120.23(17) . . ? C28 C29 H29 119.9 . . ? C24 C29 H29 119.9 . . ? C17 P1 C18 102.88(13) . . ? C17 P1 C24 108.22(17) . . ? C18 P1 C24 105.66(7) . . ? C17 P1 C17A 11.4(4) . . ? C18 P1 C17A 112.6(4) . . ? C24 P1 C17A 99.2(4) . . ? C17 P1 S1 114.9(2) . . ? C18 P1 S1 112.13(6) . . ? C24 P1 S1 112.26(6) . . ? C17A P1 S1 114.0(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.4(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C2 C1 C6 C5 -0.1(4) . . . . ? C2 C1 C6 C7 179.8(5) . . . . ? C4 C5 C6 C1 -0.3(4) . . . . ? C4 C5 C6 C7 179.8(6) . . . . ? C1A C6A C5A C4A 0.0 . . . . ? C7A C6A C5A C4A 179.4(12) . . . . ? C6A C5A C4A C3A 0.0 . . . . ? C5A C4A C3A C2A 0.0 . . . . ? C4A C3A C2A C1A 0.0 . . . . ? C3A C2A C1A C6A 0.0 . . . . ? C5A C6A C1A C2A 0.0 . . . . ? C7A C6A C1A C2A -179.3(13) . . . . ? C1 C6 C7 C8 -175.4(3) . . . . ? C5 C6 C7 C8 4.5(6) . . . . ? C5A C6A C7A C8A -164.6(11) . . . . ? C1A C6A C7A C8A 14.8(15) . . . . ? C6 C7 C8 C9 175.2(3) . . . . ? C6A C7A C8A C9A 177.5(8) . . . . ? C7 C8 C9 O1 -162.6(3) . . . . ? C7 C8 C9 C10 16.8(5) . . . . ? C7A C8A C9A O1A 34.8(17) . . . . ? C7A C8A C9A C10A -155.3(8) . . . . ? O1 C9 C10 C11 10.5(5) . . . . ? C8 C9 C10 C11 -168.8(3) . . . . ? O1A C9A C10A C11A 5.9(12) . . . . ? C8A C9A C10A C11A -166.5(5) . . . . ? O1A C9A C10A C11A -97.0(9) . . . 3_656 ? C8A C9A C10A C11A 90.7(7) . . . 3_656 ? C9 C10 C11 C12 -178.1(3) . . . . ? C9A C10A C11A C12A 124.0(6) . . . . ? C11A C10A C11A C12A -118.3(6) 3_656 . . . ? C9A C10A C11A C10A -117.7(7) . . . 3_656 ? C11A C10A C11A C10A 0.0 3_656 . . 3_656 ? C10 C11 C12 C13 -9.3(4) . . . . ? C10 C11 C12 C17 170.6(3) . . . . ? C10A C11A C12A C17A -156.8(8) . . . . ? C10A C11A C12A C17A 99.0(9) 3_656 . . . ? C10A C11A C12A C13A 30.1(8) . . . . ? C10A C11A C12A C13A -74.1(7) 3_656 . . . ? C17 C12 C13 C14 -0.7(5) . . . . ? C11 C12 C13 C14 179.2(3) . . . . ? C17A C12A C13A C14A -1.2(13) . . . . ? C11A C12A C13A C14A 172.6(9) . . . . ? C12 C13 C14 C15 -0.5(6) . . . . ? C12A C13A C14A C15A -1.4(16) . . . . ? C13 C14 C15 C16 1.0(6) . . . . ? C13A C14A C15A C16A 2.9(16) . . . . ? C14 C15 C16 C17 -0.2(6) . . . . ? C14A C15A C16A C17A -1.7(16) . . . . ? C15 C16 C17 C12 -1.0(7) . . . . ? C15 C16 C17 P1 -174.8(3) . . . . ? C13 C12 C17 C16 1.4(6) . . . . ? C11 C12 C17 C16 -178.5(4) . . . . ? C13 C12 C17 P1 174.9(3) . . . . ? C11 C12 C17 P1 -5.0(5) . . . . ? C13A C12A C17A C16A 2.5(16) . . . . ? C11A C12A C17A C16A -170.9(10) . . . . ? C13A C12A C17A P1 -169.9(6) . . . . ? C11A C12A C17A P1 16.7(12) . . . . ? C15A C16A C17A C12A -1.0(18) . . . . ? C15A C16A C17A P1 171.1(8) . . . . ? C23 C18 C19 C20 -0.7(2) . . . . ? P1 C18 C19 C20 178.61(12) . . . . ? C18 C19 C20 C21 0.9(3) . . . . ? C19 C20 C21 C22 -0.6(3) . . . . ? C20 C21 C22 C23 0.0(3) . . . . ? C21 C22 C23 C18 0.2(3) . . . . ? C19 C18 C23 C22 0.1(3) . . . . ? P1 C18 C23 C22 -179.17(15) . . . . ? C29 C24 C25 C26 0.2(3) . . . . ? P1 C24 C25 C26 178.27(15) . . . . ? C24 C25 C26 C27 0.0(3) . . . . ? C25 C26 C27 C28 -0.1(3) . . . . ? C26 C27 C28 C29 0.1(3) . . . . ? C27 C28 C29 C24 0.1(3) . . . . ? C25 C24 C29 C28 -0.2(3) . . . . ? P1 C24 C29 C28 -178.35(14) . . . . ? C16 C17 P1 C18 -125.6(4) . . . . ? C12 C17 P1 C18 61.0(4) . . . . ? C16 C17 P1 C24 -14.1(5) . . . . ? C12 C17 P1 C24 172.5(3) . . . . ? C16 C17 P1 C17A 24(3) . . . . ? C12 C17 P1 C17A -149(4) . . . . ? C16 C17 P1 S1 112.3(4) . . . . ? C12 C17 P1 S1 -61.2(4) . . . . ? C23 C18 P1 C17 -143.4(2) . . . . ? C19 C18 P1 C17 37.3(2) . . . . ? C23 C18 P1 C24 103.16(14) . . . . ? C19 C18 P1 C24 -76.15(14) . . . . ? C23 C18 P1 C17A -149.6(5) . . . . ? C19 C18 P1 C17A 31.1(5) . . . . ? C23 C18 P1 S1 -19.44(14) . . . . ? C19 C18 P1 S1 161.26(12) . . . . ? C29 C24 P1 C17 112.2(2) . . . . ? C25 C24 P1 C17 -65.9(2) . . . . ? C29 C24 P1 C18 -138.18(14) . . . . ? C25 C24 P1 C18 43.73(16) . . . . ? C29 C24 P1 C17A 105.1(5) . . . . ? C25 C24 P1 C17A -73.0(5) . . . . ? C29 C24 P1 S1 -15.67(15) . . . . ? C25 C24 P1 S1 166.24(13) . . . . ? C12A C17A P1 C17 42(3) . . . . ? C16A C17A P1 C17 -131(4) . . . . ? C12A C17A P1 C18 74.1(10) . . . . ? C16A C17A P1 C18 -98.8(10) . . . . ? C12A C17A P1 C24 -174.6(8) . . . . ? C16A C17A P1 C24 12.5(11) . . . . ? C12A C17A P1 S1 -55.1(9) . . . . ? C16A C17A P1 S1 132.0(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.496 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.047 ### END data_ijf0902 _database_code_depnum_ccdc_archive 'CCDC 874831' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C58 H46 O2 P2 S2' _chemical_formula_moiety 'C58 H46 O2 P2 S2' _chemical_formula_weight 901.0 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' 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 9.39010(10) _cell_length_b 17.15340(10) _cell_length_c 14.8607(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.3283(10) _cell_angle_gamma 90.00 _cell_volume 2338.45(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11626 _cell_measurement_theta_min 3.9815 _cell_measurement_theta_max 70.4366 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' _exptl_crystal_description shard _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 2.014 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.191 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD are detector' _diffrn_measurement_method 'Phi & Omega scans' _diffrn_detector_area_resol_mean 8.2707 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21056 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.99 _diffrn_reflns_theta_max 70.46 _reflns_number_total 4254 _reflns_number_gt 3679 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Structure solved as a disordered mixture of the discrete C29H23OPS compound and the dimerised C58H46O2P2S2 adduct in 19:81 ratio (by occupancy) repectivly . Anisotropic displacement factors between the following atom pairs were modelled as identical; C1a C1b, C2a C2b, C3a C3b, C4a C4b,C5a C5b, C6a C6b,C7a C7b. Atoms C1b, C2b, C3b, C4b, C5b, C6b constrained to form a regular hexagon with d=1.39 . ; _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^)+(0.0488P)^2^+1.3514P] 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 4254 _refine_ls_number_parameters 392 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.023 _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 C1A C 0.7208(4) 0.1336(3) 1.3116(3) 0.0468(8) Uani 0.809(3) 1 d P A 1 H1A H 0.7984 0.1588 1.2942 0.056 Uiso 0.809(3) 1 calc PR A 1 C2A C 0.6989(8) 0.1442(6) 1.3998(3) 0.0511(8) Uani 0.809(3) 1 d P A 1 H2A H 0.7614 0.1760 1.4410 0.061 Uiso 0.809(3) 1 calc PR A 1 C3A C 0.5834(9) 0.1071(6) 1.4269(4) 0.0474(7) Uani 0.809(3) 1 d P A 1 H3A H 0.5684 0.1136 1.4863 0.057 Uiso 0.809(3) 1 calc PR A 1 C4A C 0.4914(6) 0.0607(4) 1.3649(3) 0.0466(8) Uani 0.809(3) 1 d P A 1 H4A H 0.4135 0.0360 1.3825 0.056 Uiso 0.809(3) 1 calc PR A 1 C5A C 0.5135(3) 0.0503(2) 1.2761(2) 0.0429(7) Uani 0.809(3) 1 d P A 1 H5A H 0.4498 0.0190 1.2349 0.051 Uiso 0.809(3) 1 calc PR A 1 C6A C 0.6295(3) 0.0861(2) 1.2479(2) 0.0393(7) Uani 0.809(3) 1 d P A 1 C7A C 0.6533(3) 0.07152(16) 1.1526(2) 0.0402(6) Uani 0.809(3) 1 d P A 1 H7A H 0.5777 0.0495 1.1094 0.048 Uiso 0.809(3) 1 calc PR A 1 C8A C 0.7754(2) 0.08834(8) 1.12729(11) 0.0398(6) Uani 0.809(3) 1 d P A 1 H8A H 0.8484 0.1129 1.1700 0.048 Uiso 0.809(3) 1 calc PR A 1 C9A C 0.8051(2) 0.07066(8) 1.03438(11) 0.0368(7) Uani 0.809(3) 1 d PR A 1 C10A C 0.9611(2) 0.04901(8) 1.03575(11) 0.0319(6) Uani 0.809(3) 1 d PR . 1 H10A H 1.0293 0.0838 1.0760 0.038 Uiso 0.809(3) 1 calc PR A 1 C11A C 1.0006(2) 0.04008(12) 0.94118(15) 0.0281(5) Uani 0.809(3) 1 d P . 1 H11A H 0.9134 0.0447 0.8916 0.034 Uiso 0.809(3) 1 calc PR A 1 C12A C 1.1228(3) 0.08941(15) 0.9209(2) 0.0284(5) Uani 0.809(3) 1 d P A 1 C13A C 1.2380(4) 0.1108(2) 0.9926(2) 0.0385(6) Uani 0.809(3) 1 d P A 1 H13A H 1.2317 0.0997 1.0529 0.046 Uiso 0.809(3) 1 calc PR A 1 C14A C 1.3616(6) 0.1481(3) 0.9769(4) 0.0478(11) Uani 0.809(3) 1 d P A 1 H14A H 1.4360 0.1623 1.0261 0.057 Uiso 0.809(3) 1 calc PR A 1 C15A C 1.3734(3) 0.1639(2) 0.8877(3) 0.0491(10) Uani 0.809(3) 1 d P A 1 H15A H 1.4574 0.1871 0.8764 0.059 Uiso 0.809(3) 1 calc PR A 1 C16A C 1.2612(3) 0.14526(18) 0.8161(2) 0.0346(7) Uani 0.809(3) 1 d P A 1 H16A H 1.2696 0.1568 0.7563 0.042 Uiso 0.809(3) 1 calc PR A 1 C17A C 1.1334(5) 0.1091(2) 0.8303(3) 0.0255(8) Uani 0.809(3) 1 d P A 1 C1B C 0.754(2) 0.1362(15) 1.3315(12) 0.0468(8) Uani 0.191(3) 1 d PGD A 2 H1B H 0.8411 0.1607 1.3272 0.056 Uiso 0.191(3) 1 calc PR A 2 C2B C 0.703(3) 0.141(2) 1.4125(13) 0.0511(8) Uani 0.191(3) 1 d PG A 2 H2B H 0.7559 0.1691 1.4624 0.061 Uiso 0.191(3) 1 calc PR A 2 C3B C 0.574(4) 0.105(3) 1.4189(15) 0.0474(7) Uani 0.191(3) 1 d PG A 2 H3B H 0.5397 0.1081 1.4731 0.057 Uiso 0.191(3) 1 calc PR A 2 C4B C 0.495(3) 0.0631(19) 1.3444(16) 0.0466(8) Uani 0.191(3) 1 d PG A 2 H4B H 0.4087 0.0386 1.3487 0.056 Uiso 0.191(3) 1 calc PR A 2 C5B C 0.5464(15) 0.0580(11) 1.2634(13) 0.0429(7) Uani 0.191(3) 1 d PGD A 2 H5B H 0.4939 0.0301 1.2135 0.051 Uiso 0.191(3) 1 calc PR A 2 C6B C 0.6760(13) 0.0946(10) 1.2570(11) 0.0393(7) Uani 0.191(3) 1 d PG A 2 C7B C 0.7216(14) 0.0930(7) 1.1774(10) 0.0402(6) Uani 0.191(3) 1 d PD A 2 H7B H 0.8071 0.1207 1.1784 0.048 Uiso 0.191(3) 1 calc PR A 2 C8B C 0.6636(13) 0.0574(6) 1.0939(9) 0.041(3) Uani 0.191(3) 1 d P A 2 H8B H 0.5776 0.0299 1.0919 0.050 Uiso 0.191(3) 1 calc PR A 2 C9B C 0.7134(19) 0.0565(7) 1.0150(12) 0.051(4) Uani 0.191(3) 1 d P A 2 C10B C 0.867(2) 0.0774(13) 1.0202(11) 0.079(7) Uani 0.191(3) 1 d P A 2 H10B H 0.9349 0.0795 1.0759 0.095 Uiso 0.191(3) 1 calc PR A 2 C11B C 0.9024(12) 0.0923(8) 0.9440(8) 0.049(3) Uani 0.191(3) 1 d P A 2 H11B H 0.8300 0.0917 0.8904 0.059 Uiso 0.191(3) 1 calc PR A 2 C12B C 1.0559(15) 0.1106(8) 0.9371(7) 0.039(3) Uani 0.191(3) 1 d P A 2 C13B C 1.1612(17) 0.1290(7) 1.0176(9) 0.048(3) Uani 0.191(3) 1 d P A 2 H13B H 1.1357 0.1297 1.0747 0.057 Uiso 0.191(3) 1 calc PR A 2 C14B C 1.2995(19) 0.1455(8) 1.0108(11) 0.041(3) Uani 0.191(3) 1 d P A 2 H14B H 1.3660 0.1585 1.0646 0.049 Uiso 0.191(3) 1 calc PR A 2 C15B C 1.346(2) 0.1445(11) 0.9337(14) 0.041(5) Uani 0.191(3) 1 d P A 2 H15B H 1.4436 0.1534 0.9325 0.049 Uiso 0.191(3) 1 calc PR A 2 C16B C 1.235(2) 0.1284(9) 0.8489(11) 0.042(4) Uani 0.191(3) 1 d P A 2 H16B H 1.2587 0.1311 0.7912 0.050 Uiso 0.191(3) 1 calc PR A 2 C17B C 1.101(2) 0.1099(11) 0.8576(14) 0.031(4) Uani 0.191(3) 1 d P A 2 C18 C 0.84009(19) 0.15711(10) 0.73338(12) 0.0309(4) Uani 1 1 d . A . C19 C 0.8670(2) 0.23232(11) 0.76749(14) 0.0388(4) Uani 1 1 d . . . H19 H 0.9613 0.2475 0.7950 0.047 Uiso 1 1 calc R . . C20 C 0.7529(3) 0.28457(12) 0.76044(15) 0.0478(5) Uani 1 1 d . . . H20 H 0.7709 0.3351 0.7825 0.057 Uiso 1 1 calc R . . C21 C 0.6132(3) 0.26194(14) 0.72098(17) 0.0532(6) Uani 1 1 d . . . H21 H 0.5371 0.2974 0.7165 0.064 Uiso 1 1 calc R . . C22 C 0.5847(2) 0.18746(15) 0.68811(18) 0.0563(6) Uani 1 1 d . . . H22 H 0.4897 0.1725 0.6620 0.068 Uiso 1 1 calc R . . C23 C 0.6984(2) 0.13473(12) 0.69408(15) 0.0435(5) Uani 1 1 d . . . H23 H 0.6796 0.0843 0.6717 0.052 Uiso 1 1 calc R . . C24 C 1.06553(19) 0.11570(11) 0.63584(14) 0.0361(4) Uani 1 1 d . A . C25 C 1.0782(2) 0.19363(12) 0.61066(16) 0.0480(5) Uani 1 1 d . . . H25 H 1.0386 0.2328 0.6410 0.058 Uiso 1 1 calc R . . C26 C 1.1492(2) 0.21300(14) 0.54104(17) 0.0519(6) Uani 1 1 d . . . H26 H 1.1578 0.2649 0.5249 0.062 Uiso 1 1 calc R . . C27 C 1.2071(2) 0.15455(14) 0.49568(16) 0.0500(5) Uani 1 1 d . . . H27 H 1.2553 0.1671 0.4491 0.060 Uiso 1 1 calc R . . C28 C 1.1933(2) 0.07769(14) 0.51939(16) 0.0512(5) Uani 1 1 d . . . H28 H 1.2315 0.0387 0.4881 0.061 Uiso 1 1 calc R . . C29 C 1.1235(2) 0.05790(12) 0.58919(15) 0.0442(5) Uani 1 1 d . . . H29 H 1.1155 0.0058 0.6048 0.053 Uiso 1 1 calc R . . O1A O 0.7105(3) 0.07015(17) 0.9645(2) 0.0545(7) Uani 0.809(3) 1 d P A 1 O1B O 0.6347(15) 0.0428(5) 0.9394(7) 0.066(3) Uani 0.191(3) 1 d P A 2 P1 P 0.98643(5) 0.08757(3) 0.73259(3) 0.03129(13) Uani 1 1 d . . . S2 S 0.91643(5) -0.02025(3) 0.72129(4) 0.04195(15) Uani 1 1 d . A . 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 C1A 0.036(2) 0.0450(13) 0.064(2) 0.0031(19) 0.0216(16) 0.0054(18) C2A 0.0427(12) 0.0474(15) 0.064(2) -0.0061(19) 0.0133(16) 0.0007(11) C3A 0.0466(16) 0.0517(14) 0.0464(16) -0.0042(14) 0.0157(14) 0.0038(12) C4A 0.0452(12) 0.0546(14) 0.045(3) -0.002(2) 0.0218(16) -0.0037(10) C5A 0.0375(16) 0.0480(15) 0.0485(19) 0.0008(12) 0.0211(13) -0.0002(13) C6A 0.0314(18) 0.0387(14) 0.0515(15) 0.0078(10) 0.0176(16) 0.0122(15) C7A 0.0335(15) 0.0392(15) 0.0498(19) 0.0098(13) 0.0128(14) 0.0089(11) C8A 0.0354(13) 0.0324(12) 0.0520(16) 0.0024(11) 0.0099(12) 0.0049(10) C9A 0.0343(19) 0.0340(15) 0.0463(19) 0.0096(12) 0.0176(15) 0.0100(14) C10A 0.0313(13) 0.0293(11) 0.0376(13) 0.0060(9) 0.0129(11) 0.0067(10) C11A 0.0288(11) 0.0262(11) 0.0313(11) 0.0046(8) 0.0106(9) 0.0029(9) C12A 0.0261(13) 0.0295(12) 0.0308(16) 0.0082(11) 0.0088(11) 0.0048(10) C13A 0.0321(16) 0.0485(18) 0.0335(15) 0.0108(13) 0.0041(13) -0.0013(16) C14A 0.030(2) 0.065(2) 0.041(3) 0.010(2) -0.008(2) -0.0114(17) C15A 0.0307(15) 0.065(2) 0.050(2) 0.0167(16) 0.0041(14) -0.0116(12) C16A 0.0250(14) 0.0447(17) 0.0348(18) 0.0108(13) 0.0079(12) -0.0051(12) C17A 0.021(2) 0.0301(13) 0.026(2) 0.0083(14) 0.0060(14) -0.0019(14) C1B 0.036(2) 0.0450(13) 0.064(2) 0.0031(19) 0.0216(16) 0.0054(18) C2B 0.0427(12) 0.0474(15) 0.064(2) -0.0061(19) 0.0133(16) 0.0007(11) C3B 0.0466(16) 0.0517(14) 0.0464(16) -0.0042(14) 0.0157(14) 0.0038(12) C4B 0.0452(12) 0.0546(14) 0.045(3) -0.002(2) 0.0218(16) -0.0037(10) C5B 0.0375(16) 0.0480(15) 0.0485(19) 0.0008(12) 0.0211(13) -0.0002(13) C6B 0.0314(18) 0.0387(14) 0.0515(15) 0.0078(10) 0.0176(16) 0.0122(15) C7B 0.0335(15) 0.0392(15) 0.0498(19) 0.0098(13) 0.0128(14) 0.0089(11) C8B 0.051(7) 0.033(6) 0.034(7) 0.006(5) -0.007(6) -0.004(5) C9B 0.063(9) 0.030(6) 0.049(9) 0.018(6) -0.015(8) -0.029(6) C10B 0.068(12) 0.144(17) 0.034(7) -0.028(9) 0.028(8) -0.064(12) C11B 0.038(6) 0.073(8) 0.035(6) 0.004(5) 0.006(5) -0.002(5) C12B 0.039(6) 0.051(7) 0.023(6) 0.004(5) -0.002(5) 0.001(6) C13B 0.057(8) 0.040(6) 0.039(7) 0.003(5) -0.005(6) 0.000(6) C14B 0.032(8) 0.037(7) 0.053(9) -0.007(6) 0.005(7) -0.003(6) C15B 0.022(7) 0.045(8) 0.045(14) -0.020(10) -0.018(9) -0.001(5) C16B 0.053(11) 0.039(7) 0.045(9) 0.011(6) 0.035(8) 0.007(6) C17B 0.025(8) 0.031(6) 0.042(13) 0.002(7) 0.018(7) -0.011(5) C18 0.0331(9) 0.0323(9) 0.0273(9) 0.0020(7) 0.0067(7) 0.0033(7) C19 0.0434(10) 0.0369(10) 0.0374(11) -0.0040(8) 0.0115(8) -0.0006(8) C20 0.0601(13) 0.0367(11) 0.0519(13) -0.0047(9) 0.0236(11) 0.0073(10) C21 0.0530(13) 0.0508(13) 0.0601(14) 0.0056(11) 0.0215(11) 0.0214(11) C22 0.0344(11) 0.0649(15) 0.0674(16) -0.0003(12) 0.0056(10) 0.0109(10) C23 0.0366(10) 0.0418(11) 0.0497(12) -0.0057(9) 0.0036(9) 0.0035(9) C24 0.0320(9) 0.0336(9) 0.0425(11) -0.0005(8) 0.0073(8) 0.0048(8) C25 0.0532(12) 0.0365(11) 0.0614(14) 0.0034(10) 0.0280(11) 0.0090(9) C26 0.0534(13) 0.0443(12) 0.0648(15) 0.0086(10) 0.0277(11) 0.0051(10) C27 0.0470(12) 0.0601(14) 0.0466(13) 0.0031(10) 0.0186(10) 0.0072(10) C28 0.0550(13) 0.0549(13) 0.0468(13) -0.0091(10) 0.0178(10) 0.0089(10) C29 0.0478(11) 0.0368(10) 0.0464(12) -0.0040(9) 0.0065(9) 0.0048(9) O1A 0.0386(13) 0.0744(19) 0.0521(17) 0.0193(15) 0.0135(13) 0.0178(12) O1B 0.082(8) 0.040(5) 0.056(6) -0.009(4) -0.029(6) -0.003(5) P1 0.0297(2) 0.0268(2) 0.0351(3) 0.00206(18) 0.00176(18) 0.00132(18) S2 0.0379(3) 0.0283(2) 0.0564(3) -0.0011(2) 0.0029(2) -0.00193(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A C2A 1.382(4) . ? C1A C6A 1.396(4) . ? C1A H1A 0.9300 . ? C2A C3A 1.389(4) . ? C2A H2A 0.9300 . ? C3A C4A 1.374(4) . ? C3A H3A 0.9300 . ? C4A C5A 1.390(4) . ? C4A H4A 0.9300 . ? C5A C6A 1.391(4) . ? C5A H5A 0.9300 . ? C6A C7A 1.500(5) . ? C7A C8A 1.313(4) . ? C7A H7A 0.9300 . ? C8A C9A 1.4971 . ? C8A H8A 0.9300 . ? C9A O1A 1.214(3) . ? C9A C10A 1.5064 . ? C10A C11A 1.536(3) . ? C10A C11A 1.591(2) 3_757 ? C10A H10A 0.9800 . ? C11A C12A 1.507(3) . ? C11A C10A 1.591(2) 3_757 ? C11A H11A 0.9800 . ? C12A C13A 1.396(4) . ? C12A C17A 1.411(4) . ? C13A C14A 1.388(6) . ? C13A H13A 0.9300 . ? C14A C15A 1.380(5) . ? C14A H14A 0.9300 . ? C15A C16A 1.365(5) . ? C15A H15A 0.9300 . ? C16A C17A 1.407(4) . ? C16A H16A 0.9300 . ? C17A P1 1.815(5) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B H1B 0.9300 . ? C2B C3B 1.3900 . ? C2B H2B 0.9300 . ? C3B C4B 1.3900 . ? C3B H3B 0.9300 . ? C4B C5B 1.3900 . ? C4B H4B 0.9300 . ? C5B C6B 1.3900 . ? C5B H5B 0.9300 . ? C6B C7B 1.34(2) . ? C7B C8B 1.385(18) . ? C7B H7B 0.9300 . ? C8B C9B 1.35(2) . ? C8B H8B 0.9300 . ? C9B O1B 1.228(18) . ? C9B C10B 1.48(2) . ? C10B C11B 1.270(18) . ? C10B H10B 0.9300 . ? C11B C12B 1.500(17) . ? C11B H11B 0.9300 . ? C12B C17B 1.34(2) . ? C12B C13B 1.415(15) . ? C13B C14B 1.35(2) . ? C13B H13B 0.9300 . ? C14B C15B 1.31(3) . ? C14B H14B 0.9300 . ? C15B C16B 1.48(3) . ? C15B H15B 0.9300 . ? C16B C17B 1.338(19) . ? C16B H16B 0.9300 . ? C17B P1 1.97(2) . ? C18 C23 1.388(3) . ? C18 C19 1.389(3) . ? C18 P1 1.8216(18) . ? C19 C20 1.383(3) . ? C19 H19 0.9300 . ? C20 C21 1.374(3) . ? C20 H20 0.9300 . ? C21 C22 1.373(3) . ? C21 H21 0.9300 . ? C22 C23 1.387(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C29 1.386(3) . ? C24 C25 1.400(3) . ? C24 P1 1.819(2) . ? C25 C26 1.385(3) . ? C25 H25 0.9300 . ? C26 C27 1.383(3) . ? C26 H26 0.9300 . ? C27 C28 1.378(3) . ? C27 H27 0.9300 . ? C28 C29 1.383(3) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? P1 S2 1.9579(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A C1A C6A 121.7(3) . . ? C2A C1A H1A 119.1 . . ? C6A C1A H1A 119.1 . . ? C1A C2A C3A 119.9(3) . . ? C1A C2A H2A 120.0 . . ? C3A C2A H2A 120.0 . . ? C4A C3A C2A 119.2(3) . . ? C4A C3A H3A 120.4 . . ? C2A C3A H3A 120.4 . . ? C3A C4A C5A 120.7(2) . . ? C3A C4A H4A 119.6 . . ? C5A C4A H4A 119.6 . . ? C4A C5A C6A 121.0(3) . . ? C4A C5A H5A 119.5 . . ? C6A C5A H5A 119.5 . . ? C5A C6A C1A 117.4(2) . . ? C5A C6A C7A 119.6(3) . . ? C1A C6A C7A 123.0(3) . . ? C8A C7A C6A 123.3(3) . . ? C8A C7A H7A 118.4 . . ? C6A C7A H7A 118.4 . . ? C7A C8A C9A 124.49(18) . . ? C7A C8A H8A 117.8 . . ? C9A C8A H8A 117.8 . . ? O1A C9A C8A 122.96(13) . . ? O1A C9A C10A 122.77(13) . . ? C8A C9A C10A 114.2 . . ? C9A C10A C11A 115.85(10) . . ? C9A C10A C11A 114.49(10) . 3_757 ? C11A C10A C11A 90.78(13) . 3_757 ? C9A C10A H10A 111.4 . . ? C11A C10A H10A 111.4 . . ? C11A C10A H10A 111.4 3_757 . ? C12A C11A C10A 118.0(2) . . ? C12A C11A C10A 115.81(17) . 3_757 ? C10A C11A C10A 89.22(13) . 3_757 ? C12A C11A H11A 110.7 . . ? C10A C11A H11A 110.7 . . ? C10A C11A H11A 110.7 3_757 . ? C13A C12A C17A 117.7(3) . . ? C13A C12A C11A 119.6(3) . . ? C17A C12A C11A 122.5(3) . . ? C14A C13A C12A 122.1(3) . . ? C14A C13A H13A 119.0 . . ? C12A C13A H13A 119.0 . . ? C15A C14A C13A 119.6(3) . . ? C15A C14A H14A 120.2 . . ? C13A C14A H14A 120.2 . . ? C16A C15A C14A 119.7(3) . . ? C16A C15A H15A 120.1 . . ? C14A C15A H15A 120.1 . . ? C15A C16A C17A 121.8(3) . . ? C15A C16A H16A 119.1 . . ? C17A C16A H16A 119.1 . . ? C16A C17A C12A 119.0(3) . . ? C16A C17A P1 119.8(3) . . ? C12A C17A P1 121.2(3) . . ? C2B C1B C6B 120.0 . . ? C2B C1B H1B 120.0 . . ? C6B C1B H1B 120.0 . . ? C3B C2B C1B 120.0 . . ? C3B C2B H2B 120.0 . . ? C1B C2B H2B 120.0 . . ? C2B C3B C4B 120.0 . . ? C2B C3B H3B 120.0 . . ? C4B C3B H3B 120.0 . . ? C5B C4B C3B 120.0 . . ? C5B C4B H4B 120.0 . . ? C3B C4B H4B 120.0 . . ? C6B C5B C4B 120.0 . . ? C6B C5B H5B 120.0 . . ? C4B C5B H5B 120.0 . . ? C7B C6B C5B 120.0(2) . . ? C7B C6B C1B 119.9(2) . . ? C5B C6B C1B 120.0 . . ? C6B C7B C8B 131.3(10) . . ? C6B C7B H7B 114.3 . . ? C8B C7B H7B 114.3 . . ? C9B C8B C7B 129.7(12) . . ? C9B C8B H8B 115.1 . . ? C7B C8B H8B 115.1 . . ? O1B C9B C8B 122.9(15) . . ? O1B C9B C10B 119.1(17) . . ? C8B C9B C10B 117.9(12) . . ? C11B C10B C9B 116.0(15) . . ? C11B C10B H10B 122.0 . . ? C9B C10B H10B 122.0 . . ? C10B C11B C12B 122.5(12) . . ? C10B C11B H11B 118.7 . . ? C12B C11B H11B 118.7 . . ? C17B C12B C13B 117.1(15) . . ? C17B C12B C11B 123.1(12) . . ? C13B C12B C11B 119.9(12) . . ? C14B C13B C12B 119.5(14) . . ? C14B C13B H13B 120.3 . . ? C12B C13B H13B 120.3 . . ? C15B C14B C13B 124.6(14) . . ? C15B C14B H14B 117.7 . . ? C13B C14B H14B 117.7 . . ? C14B C15B C16B 116.1(15) . . ? C14B C15B H15B 121.9 . . ? C16B C15B H15B 121.9 . . ? C17B C16B C15B 118.0(16) . . ? C17B C16B H16B 121.0 . . ? C15B C16B H16B 121.0 . . ? C12B C17B C16B 124.4(17) . . ? C12B C17B P1 128.6(13) . . ? C16B C17B P1 106.9(13) . . ? C23 C18 C19 119.56(17) . . ? C23 C18 P1 118.22(14) . . ? C19 C18 P1 122.13(14) . . ? C20 C19 C18 119.77(19) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C21 C20 C19 120.2(2) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 120.7(2) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 119.7(2) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C22 C23 C18 120.1(2) . . ? C22 C23 H23 119.9 . . ? C18 C23 H23 119.9 . . ? C29 C24 C25 118.97(19) . . ? C29 C24 P1 118.42(15) . . ? C25 C24 P1 122.48(15) . . ? C26 C25 C24 120.70(19) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C27 C26 C25 119.5(2) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C28 C27 C26 120.1(2) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C29 120.8(2) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C28 C29 C24 120.0(2) . . ? C28 C29 H29 120.0 . . ? C24 C29 H29 120.0 . . ? C17A P1 C24 102.09(15) . . ? C17A P1 C18 107.88(14) . . ? C24 P1 C18 105.50(8) . . ? C17A P1 S2 116.42(14) . . ? C24 P1 S2 111.66(7) . . ? C18 P1 S2 112.29(6) . . ? C24 P1 C17B 117.5(5) . . ? C18 P1 C17B 97.2(5) . . ? S2 P1 C17B 111.6(6) . . ? 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 C6A C1A C2A C3A -0.1(4) . . . . ? C1A C2A C3A C4A -0.5(4) . . . . ? C2A C3A C4A C5A 0.4(4) . . . . ? C3A C4A C5A C6A 0.4(4) . . . . ? C4A C5A C6A C1A -1.0(4) . . . . ? C4A C5A C6A C7A 178.0(4) . . . . ? C2A C1A C6A C5A 0.9(4) . . . . ? C2A C1A C6A C7A -178.0(5) . . . . ? C5A C6A C7A C8A -164.5(3) . . . . ? C1A C6A C7A C8A 14.4(4) . . . . ? C6A C7A C8A C9A 176.6(2) . . . . ? C7A C8A C9A O1A 31.7(2) . . . . ? C7A C8A C9A C10A -144.98(15) . . . . ? O1A C9A C10A C11A 10.45(19) . . . . ? C8A C9A C10A C11A -172.88(11) . . . . ? O1A C9A C10A C11A -93.3(2) . . . 3_757 ? C8A C9A C10A C11A 83.39(11) . . . 3_757 ? C9A C10A C11A C12A 123.06(17) . . . . ? C11A C10A C11A C12A -119.1(2) 3_757 . . . ? C9A C10A C11A C10A -117.86(11) . . . 3_757 ? C11A C10A C11A C10A 0.0 3_757 . . 3_757 ? C10A C11A C12A C13A 31.0(3) . . . . ? C10A C11A C12A C13A -72.9(3) 3_757 . . . ? C10A C11A C12A C17A -155.2(3) . . . . ? C10A C11A C12A C17A 100.9(3) 3_757 . . . ? C17A C12A C13A C14A -1.9(5) . . . . ? C11A C12A C13A C14A 172.2(3) . . . . ? C12A C13A C14A C15A -1.0(7) . . . . ? C13A C14A C15A C16A 2.4(7) . . . . ? C14A C15A C16A C17A -0.9(6) . . . . ? C15A C16A C17A C12A -2.0(5) . . . . ? C15A C16A C17A P1 178.8(3) . . . . ? C13A C12A C17A C16A 3.3(5) . . . . ? C11A C12A C17A C16A -170.6(3) . . . . ? C13A C12A C17A P1 -177.5(2) . . . . ? C11A C12A C17A P1 8.6(4) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C2B C3B C4B C5B 0.0 . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C7B -177(2) . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C7B 177(2) . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C5B C6B C7B C8B -3(2) . . . . ? C1B C6B C7B C8B -179.2(15) . . . . ? C6B C7B C8B C9B -179.4(15) . . . . ? C7B C8B C9B O1B -158.4(12) . . . . ? C7B C8B C9B C10B 18(2) . . . . ? O1B C9B C10B C11B 11(3) . . . . ? C8B C9B C10B C11B -165.4(15) . . . . ? C9B C10B C11B C12B -177.0(14) . . . . ? C10B C11B C12B C17B 165.1(19) . . . . ? C10B C11B C12B C13B -14(2) . . . . ? C17B C12B C13B C14B 1(2) . . . . ? C11B C12B C13B C14B 180.0(12) . . . . ? C12B C13B C14B C15B -1(2) . . . . ? C13B C14B C15B C16B 4(2) . . . . ? C14B C15B C16B C17B -5(2) . . . . ? C13B C12B C17B C16B -3(3) . . . . ? C11B C12B C17B C16B 177.8(16) . . . . ? C13B C12B C17B P1 -179.7(12) . . . . ? C11B C12B C17B P1 1(2) . . . . ? C15B C16B C17B C12B 5(3) . . . . ? C15B C16B C17B P1 -177.3(11) . . . . ? C23 C18 C19 C20 -1.2(3) . . . . ? P1 C18 C19 C20 175.36(15) . . . . ? C18 C19 C20 C21 0.9(3) . . . . ? C19 C20 C21 C22 0.0(4) . . . . ? C20 C21 C22 C23 -0.6(4) . . . . ? C21 C22 C23 C18 0.2(4) . . . . ? C19 C18 C23 C22 0.7(3) . . . . ? P1 C18 C23 C22 -176.05(18) . . . . ? C29 C24 C25 C26 -0.8(3) . . . . ? P1 C24 C25 C26 175.01(18) . . . . ? C24 C25 C26 C27 0.4(4) . . . . ? C25 C26 C27 C28 0.4(4) . . . . ? C26 C27 C28 C29 -0.8(4) . . . . ? C27 C28 C29 C24 0.4(3) . . . . ? C25 C24 C29 C28 0.4(3) . . . . ? P1 C24 C29 C28 -175.60(17) . . . . ? C16A C17A P1 C24 4.8(3) . . . . ? C12A C17A P1 C24 -174.4(3) . . . . ? C16A C17A P1 C18 -106.1(3) . . . . ? C12A C17A P1 C18 74.7(3) . . . . ? C16A C17A P1 S2 126.7(3) . . . . ? C12A C17A P1 S2 -52.6(3) . . . . ? C16A C17A P1 C17B -157(3) . . . . ? C12A C17A P1 C17B 24(2) . . . . ? C29 C24 P1 C17A 98.9(2) . . . . ? C25 C24 P1 C17A -76.9(2) . . . . ? C29 C24 P1 C18 -148.40(16) . . . . ? C25 C24 P1 C18 35.75(19) . . . . ? C29 C24 P1 S2 -26.15(17) . . . . ? C25 C24 P1 S2 158.00(16) . . . . ? C29 C24 P1 C17B 104.7(6) . . . . ? C25 C24 P1 C17B -71.2(6) . . . . ? C23 C18 P1 C17A -152.6(2) . . . . ? C19 C18 P1 C17A 30.8(2) . . . . ? C23 C18 P1 C24 98.87(17) . . . . ? C19 C18 P1 C24 -77.75(17) . . . . ? C23 C18 P1 S2 -22.97(17) . . . . ? C19 C18 P1 S2 160.40(14) . . . . ? C23 C18 P1 C17B -140.0(6) . . . . ? C19 C18 P1 C17B 43.4(6) . . . . ? C12B C17B P1 C17A -175(4) . . . . ? C16B C17B P1 C17A 7.5(13) . . . . ? C12B C17B P1 C24 164.3(15) . . . . ? C16B C17B P1 C24 -12.9(15) . . . . ? C12B C17B P1 C18 52.6(17) . . . . ? C16B C17B P1 C18 -124.6(12) . . . . ? C12B C17B P1 S2 -64.9(18) . . . . ? C16B C17B P1 S2 117.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 70.46 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.400 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.041 _audit_creation_date ; 'Thu Jan 29 14:58:21 2009' ; _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 35.00 88.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 13.7937 45.0000 150.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 2 omega -10.00 48.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 13.7937 -77.0000 60.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 3 omega 35.00 88.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 13.7937 45.0000 270.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 4 omega -38.00 20.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -13.7937 -77.0000 240.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 5 omega -72.00 -14.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 77.0000 210.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 6 omega -178.00 -90.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 0.0000 210.0000 0.0000 0.0000 88 #__ type_ start__ end____ width___ exp.time_ 7 omega -72.00 -19.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 45.0000 210.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 8 omega -121.00 -68.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 45.0000 150.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 9 omega -72.00 -14.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 77.0000 330.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 10 omega 21.00 80.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 100.0000 -77.0000 240.0000 0.0000 0.0000 59 #__ type_ start__ end____ width___ exp.time_ 11 omega 75.00 128.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 100.0000 -45.0000 210.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 12 omega 74.00 128.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 100.0000 82.0000 107.0000 0.0000 0.0000 54 #__ type_ start__ end____ width___ exp.time_ 13 omega -178.00 -6.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 0.0000 180.0000 0.0000 0.0000 172 #__ type_ start__ end____ width___ exp.time_ 14 omega -178.00 -6.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 0.0000 0.0000 0.0000 0.0000 172 #__ type_ start__ end____ width___ exp.time_ 15 omega -178.00 -6.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 0.0000 330.0000 0.0000 0.0000 172 #__ type_ start__ end____ width___ exp.time_ 16 omega -178.00 -49.00 1.0000 23.1000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 0.0000 150.0000 0.0000 0.0000 129 ; ### END data_ijsf1114 _database_code_depnum_ccdc_archive 'CCDC 874832' #TrackingRef '- all.cif' _audit_creation_date 2011-11-01 _audit_creation_method ; Olex2 1.1 (compiled 2011.09.07 svn.r1971, GUI svn.r3853) ; _chemical_name_systematic ; ? ; _chemical_formula_sum 'C58 H46 O2 P2 S2' _chemical_formula_moiety 'C58 H46 O2 P2 S2' _chemical_formula_weight 901.0 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' 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 11.9199(2) _cell_length_b 14.3119(4) _cell_length_c 13.7279(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.026(2) _cell_angle_gamma 90.00 _cell_volume 2290.54(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4435 _cell_measurement_temperature 110.00(10) _cell_measurement_theta_max 31.6527 _cell_measurement_theta_min 2.8398 _space_group_crystal_system monoclinic _symmetry_space_group_name_H-M P2(1)/n _space_group_name_Hall '-P 2yn' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_recrystallization_method 'CD2Cl2, acetone' _exptl_crystal_size_max 0.2505 _exptl_crystal_size_mid 0.1012 _exptl_crystal_size_min 0.076 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_unetI/netI 0.0498 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 12391 _diffrn_reflns_theta_full 29.51 _diffrn_reflns_theta_max 31.74 _diffrn_reflns_theta_min 2.85 _diffrn_ambient_temperature 110.00(10) _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.9958 _diffrn_measured_fraction_theta_max 0.886 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -89.00 5.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - -24.0022 -77.0000 -180.0000 94 #__ type_ start__ end____ width___ exp.time_ 2 omega -48.00 45.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - -24.0022 77.0000 -60.0000 93 #__ type_ start__ end____ width___ exp.time_ 3 omega 15.00 56.00 1.0000 120.0000 omega____ theta____ kappa____ phi______ frames - 25.5647 -77.0000 -30.0000 41 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0244170000 _diffrn_orient_matrix_UB_12 0.0408279000 _diffrn_orient_matrix_UB_13 -0.0249116000 _diffrn_orient_matrix_UB_21 -0.0150747000 _diffrn_orient_matrix_UB_22 0.0157533000 _diffrn_orient_matrix_UB_23 0.0446067000 _diffrn_orient_matrix_UB_31 0.0535271000 _diffrn_orient_matrix_UB_32 0.0231074000 _diffrn_orient_matrix_UB_33 0.0136667000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5498 _reflns_number_total 6896 _reflns_odcompleteness_completeness 99.58 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 29.51 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.448 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.063 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 297 _refine_ls_number_reflns 6896 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0462 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+1.5380P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0991 _refine_ls_wR_factor_ref 0.1077 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.89009(12) 0.00284(10) 0.73464(11) 0.0142(3) Uani 1 1 d . . . C2 C 0.90464(14) -0.03882(12) 0.64596(12) 0.0197(3) Uani 1 1 d . . . H2 H 0.8653 -0.0141 0.5840 0.024 Uiso 1 1 calc R . . C3 C 0.97583(15) -0.11580(12) 0.64736(13) 0.0228(3) Uani 1 1 d . . . H3 H 0.9870 -0.1424 0.5867 0.027 Uiso 1 1 calc R . . C4 C 1.03045(14) -0.15357(11) 0.73753(13) 0.0199(3) Uani 1 1 d . . . H4 H 1.0788 -0.2065 0.7389 0.024 Uiso 1 1 calc R . . C5 C 1.01461(13) -0.11417(11) 0.82585(12) 0.0168(3) Uani 1 1 d . . . H5 H 1.0510 -0.1418 0.8872 0.020 Uiso 1 1 calc R . . C6 C 0.94647(12) -0.03480(10) 0.82701(11) 0.0137(3) Uani 1 1 d . . . C7 C 0.94252(12) 0.00995(10) 0.92553(11) 0.0131(3) Uani 1 1 d . . . H7 H 0.8824(16) 0.0542(13) 0.9190(14) 0.015(4) Uiso 1 1 d . . . C8 C 1.05936(12) 0.05391(11) 0.98414(11) 0.0138(3) Uani 1 1 d . . . H8 H 1.0493(15) 0.1207(13) 0.9945(14) 0.016(5) Uiso 1 1 d . . . C9 C 1.15929(13) 0.04005(11) 0.93309(12) 0.0157(3) Uani 1 1 d . . . C10 C 1.15446(13) 0.09808(11) 0.84355(12) 0.0173(3) Uani 1 1 d . . . H10 H 1.1065 0.1518 0.8346 0.021 Uiso 1 1 calc R . . C11 C 1.21485(13) 0.07800(12) 0.77466(12) 0.0187(3) Uani 1 1 d . . . H11 H 1.2587 0.0221 0.7835 0.022 Uiso 1 1 calc R . . C12 C 1.21972(13) 0.13444(12) 0.68657(12) 0.0182(3) Uani 1 1 d . . . C13 C 1.14750(15) 0.21074(12) 0.65785(13) 0.0225(3) Uani 1 1 d . . . H13 H 1.0880 0.2240 0.6923 0.027 Uiso 1 1 calc R . . C14 C 1.16183(17) 0.26717(13) 0.57970(14) 0.0267(4) Uani 1 1 d . . . H14 H 1.1129 0.3195 0.5616 0.032 Uiso 1 1 calc R . . C15 C 1.24675(16) 0.24815(13) 0.52750(13) 0.0261(4) Uani 1 1 d . . . H15 H 1.2572 0.2877 0.4745 0.031 Uiso 1 1 calc R . . C16 C 1.31640(16) 0.17075(14) 0.55335(14) 0.0292(4) Uani 1 1 d . . . H16 H 1.3737 0.1564 0.5168 0.035 Uiso 1 1 calc R . . C17 C 1.30319(15) 0.11456(14) 0.63150(14) 0.0263(4) Uani 1 1 d . . . H17 H 1.3514 0.0616 0.6483 0.032 Uiso 1 1 calc R . . C18 C 0.73680(13) 0.12368(11) 0.59779(12) 0.0178(3) Uani 1 1 d . . . C19 C 0.62781(15) 0.09354(13) 0.55197(13) 0.0234(4) Uani 1 1 d . . . H19 H 0.5810 0.0619 0.5896 0.028 Uiso 1 1 calc R . . C20 C 0.58719(16) 0.10993(14) 0.45048(14) 0.0287(4) Uani 1 1 d . . . H20 H 0.5123 0.0899 0.4194 0.034 Uiso 1 1 calc R . . C21 C 0.65423(17) 0.15448(14) 0.39546(14) 0.0295(4) Uani 1 1 d . . . H21 H 0.6267 0.1635 0.3260 0.035 Uiso 1 1 calc R . . C22 C 0.76205(17) 0.18649(16) 0.44060(15) 0.0331(4) Uani 1 1 d . . . H22 H 0.8079 0.2186 0.4025 0.040 Uiso 1 1 calc R . . C23 C 0.80319(15) 0.17175(14) 0.54151(14) 0.0283(4) Uani 1 1 d . . . H23 H 0.8769 0.1944 0.5725 0.034 Uiso 1 1 calc R . . C24 C 0.67721(12) 0.06224(11) 0.78167(11) 0.0145(3) Uani 1 1 d . . . C25 C 0.60786(13) 0.12760(12) 0.81583(12) 0.0185(3) Uani 1 1 d . . . H25 H 0.6215 0.1925 0.8094 0.022 Uiso 1 1 calc R . . C26 C 0.51876(14) 0.09803(12) 0.85934(13) 0.0215(3) Uani 1 1 d . . . H26 H 0.4714 0.1427 0.8824 0.026 Uiso 1 1 calc R . . C27 C 0.49866(14) 0.00311(12) 0.86915(13) 0.0212(3) Uani 1 1 d . . . H27 H 0.4387 -0.0170 0.9002 0.025 Uiso 1 1 calc R . . C28 C 0.56602(14) -0.06194(12) 0.83375(13) 0.0206(3) Uani 1 1 d . . . H28 H 0.5515 -0.1267 0.8397 0.025 Uiso 1 1 calc R . . C29 C 0.65517(13) -0.03299(11) 0.78936(12) 0.0175(3) Uani 1 1 d . . . H29 H 0.7008 -0.0779 0.7644 0.021 Uiso 1 1 calc R . . O1 O 1.23561(10) -0.01625(9) 0.96250(9) 0.0217(3) Uani 1 1 d . . . P1 P 0.79555(3) 0.10365(3) 0.72899(3) 0.01377(9) Uani 1 1 d . . . S1 S 0.86859(3) 0.21750(3) 0.79262(3) 0.01829(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0118(6) 0.0151(7) 0.0158(7) -0.0009(6) 0.0034(5) -0.0001(5) C2 0.0198(7) 0.0244(8) 0.0141(7) -0.0019(6) 0.0015(6) 0.0026(6) C3 0.0244(8) 0.0255(8) 0.0191(8) -0.0082(7) 0.0056(6) 0.0030(7) C4 0.0193(7) 0.0175(7) 0.0231(8) -0.0030(6) 0.0050(6) 0.0036(6) C5 0.0156(7) 0.0156(7) 0.0190(7) 0.0002(6) 0.0034(6) 0.0012(5) C6 0.0119(6) 0.0148(7) 0.0148(7) -0.0008(6) 0.0036(5) -0.0024(5) C7 0.0118(6) 0.0145(7) 0.0128(7) 0.0015(6) 0.0022(5) 0.0000(5) C8 0.0139(6) 0.0146(7) 0.0130(7) 0.0009(6) 0.0028(5) -0.0007(5) C9 0.0137(7) 0.0174(7) 0.0156(7) -0.0002(6) 0.0026(5) -0.0033(5) C10 0.0155(7) 0.0181(7) 0.0189(7) 0.0031(6) 0.0047(6) -0.0008(6) C11 0.0161(7) 0.0206(7) 0.0195(8) 0.0021(6) 0.0040(6) 0.0002(6) C12 0.0184(7) 0.0209(8) 0.0161(7) 0.0011(6) 0.0055(6) -0.0019(6) C13 0.0238(8) 0.0253(9) 0.0202(8) 0.0015(7) 0.0086(7) 0.0020(7) C14 0.0344(10) 0.0232(8) 0.0226(9) 0.0030(7) 0.0063(7) 0.0032(7) C15 0.0308(9) 0.0296(9) 0.0185(8) 0.0047(7) 0.0064(7) -0.0087(7) C16 0.0257(9) 0.0409(11) 0.0248(9) 0.0028(8) 0.0138(7) 0.0019(8) C17 0.0249(8) 0.0325(9) 0.0234(9) 0.0037(8) 0.0096(7) 0.0067(7) C18 0.0178(7) 0.0192(7) 0.0163(7) 0.0023(6) 0.0037(6) 0.0048(6) C19 0.0218(8) 0.0283(9) 0.0192(8) 0.0027(7) 0.0020(6) -0.0015(7) C20 0.0255(9) 0.0352(10) 0.0216(9) -0.0007(8) -0.0039(7) 0.0023(8) C21 0.0347(10) 0.0365(10) 0.0155(8) 0.0040(8) 0.0009(7) 0.0116(8) C22 0.0308(10) 0.0461(12) 0.0243(9) 0.0141(9) 0.0104(8) 0.0052(9) C23 0.0205(8) 0.0410(11) 0.0233(9) 0.0083(8) 0.0044(7) 0.0006(7) C24 0.0128(6) 0.0176(7) 0.0129(7) 0.0008(6) 0.0019(5) 0.0000(5) C25 0.0164(7) 0.0182(7) 0.0210(8) 0.0006(6) 0.0040(6) 0.0014(6) C26 0.0173(7) 0.0247(8) 0.0240(8) -0.0005(7) 0.0077(6) 0.0038(6) C27 0.0152(7) 0.0285(9) 0.0204(8) 0.0032(7) 0.0049(6) -0.0030(6) C28 0.0181(7) 0.0199(8) 0.0237(8) 0.0029(7) 0.0037(6) -0.0027(6) C29 0.0166(7) 0.0164(7) 0.0195(8) -0.0004(6) 0.0037(6) 0.0006(6) O1 0.0159(5) 0.0277(6) 0.0219(6) 0.0050(5) 0.0046(5) 0.0029(5) P1 0.01250(17) 0.01507(18) 0.01381(18) 0.00162(15) 0.00291(14) 0.00118(14) S1 0.01848(18) 0.01455(18) 0.0224(2) 0.00014(15) 0.00551(15) -0.00140(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.398(2) . ? C1 C6 1.412(2) . ? C1 P1 1.8223(15) . ? C2 H2 0.9500 . ? C2 C3 1.388(2) . ? C3 H3 0.9500 . ? C3 C4 1.383(2) . ? C4 H4 0.9500 . ? C4 C5 1.385(2) . ? C5 H5 0.9500 . ? C5 C6 1.398(2) . ? C6 C7 1.506(2) . ? C7 H7 0.946(18) . ? C7 C8 1.544(2) 3_757 ? C7 C8 1.586(2) . ? C8 C7 1.544(2) 3_757 ? C8 H8 0.978(19) . ? C8 C9 1.516(2) . ? C9 C10 1.475(2) . ? C9 O1 1.2194(19) . ? C10 H10 0.9500 . ? C10 C11 1.334(2) . ? C11 H11 0.9500 . ? C11 C12 1.465(2) . ? C12 C13 1.396(2) . ? C12 C17 1.399(2) . ? C13 H13 0.9500 . ? C13 C14 1.382(2) . ? C14 H14 0.9500 . ? C14 C15 1.384(3) . ? C15 H15 0.9500 . ? C15 C16 1.385(3) . ? C16 H16 0.9500 . ? C16 C17 1.376(3) . ? C17 H17 0.9500 . ? C18 C19 1.389(2) . ? C18 C23 1.397(2) . ? C18 P1 1.8141(16) . ? C19 H19 0.9500 . ? C19 C20 1.396(2) . ? C20 H20 0.9500 . ? C20 C21 1.366(3) . ? C21 H21 0.9500 . ? C21 C22 1.383(3) . ? C22 H22 0.9500 . ? C22 C23 1.386(3) . ? C23 H23 0.9500 . ? C24 C25 1.393(2) . ? C24 C29 1.396(2) . ? C24 P1 1.8136(15) . ? C25 H25 0.9500 . ? C25 C26 1.389(2) . ? C26 H26 0.9500 . ? C26 C27 1.391(2) . ? C27 H27 0.9500 . ? C27 C28 1.382(2) . ? C28 H28 0.9500 . ? C28 C29 1.394(2) . ? C29 H29 0.9500 . ? P1 S1 1.9644(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.79(14) . . ? C2 C1 P1 119.22(12) . . ? C6 C1 P1 120.97(11) . . ? C1 C2 H2 119.6 . . ? C3 C2 C1 120.84(15) . . ? C3 C2 H2 119.6 . . ? C2 C3 H3 120.2 . . ? C4 C3 C2 119.66(15) . . ? C4 C3 H3 120.2 . . ? C3 C4 H4 120.0 . . ? C3 C4 C5 119.98(15) . . ? C5 C4 H4 120.0 . . ? C4 C5 H5 119.1 . . ? C4 C5 C6 121.74(15) . . ? C6 C5 H5 119.1 . . ? C1 C6 C7 123.09(13) . . ? C5 C6 C1 117.93(14) . . ? C5 C6 C7 118.86(13) . . ? C6 C7 H7 111.4(11) . . ? C6 C7 C8 115.84(12) . . ? C6 C7 C8 118.54(13) . 3_757 ? C8 C7 H7 110.5(11) . . ? C8 C7 H7 109.5(11) 3_757 . ? C8 C7 C8 89.17(11) 3_757 . ? C7 C8 C7 90.83(11) 3_757 . ? C7 C8 H8 116.0(11) 3_757 . ? C7 C8 H8 109.9(11) . . ? C9 C8 C7 115.98(12) . 3_757 ? C9 C8 C7 113.90(12) . . ? C9 C8 H8 109.2(11) . . ? C10 C9 C8 114.44(13) . . ? O1 C9 C8 122.50(14) . . ? O1 C9 C10 123.03(14) . . ? C9 C10 H10 118.8 . . ? C11 C10 C9 122.45(15) . . ? C11 C10 H10 118.8 . . ? C10 C11 H11 117.0 . . ? C10 C11 C12 125.90(15) . . ? C12 C11 H11 117.0 . . ? C13 C12 C11 122.43(15) . . ? C13 C12 C17 118.23(15) . . ? C17 C12 C11 119.27(15) . . ? C12 C13 H13 119.7 . . ? C14 C13 C12 120.53(16) . . ? C14 C13 H13 119.7 . . ? C13 C14 H14 119.7 . . ? C13 C14 C15 120.61(17) . . ? C15 C14 H14 119.7 . . ? C14 C15 H15 120.4 . . ? C14 C15 C16 119.25(16) . . ? C16 C15 H15 120.4 . . ? C15 C16 H16 119.8 . . ? C17 C16 C15 120.48(17) . . ? C17 C16 H16 119.8 . . ? C12 C17 H17 119.6 . . ? C16 C17 C12 120.83(17) . . ? C16 C17 H17 119.6 . . ? C19 C18 C23 119.12(16) . . ? C19 C18 P1 122.12(13) . . ? C23 C18 P1 118.75(13) . . ? C18 C19 H19 120.1 . . ? C18 C19 C20 119.80(17) . . ? C20 C19 H19 120.1 . . ? C19 C20 H20 119.7 . . ? C21 C20 C19 120.59(17) . . ? C21 C20 H20 119.7 . . ? C20 C21 H21 119.9 . . ? C20 C21 C22 120.17(17) . . ? C22 C21 H21 119.9 . . ? C21 C22 H22 120.0 . . ? C21 C22 C23 119.98(18) . . ? C23 C22 H22 120.0 . . ? C18 C23 H23 119.8 . . ? C22 C23 C18 120.30(17) . . ? C22 C23 H23 119.8 . . ? C25 C24 C29 119.73(14) . . ? C25 C24 P1 118.70(12) . . ? C29 C24 P1 121.56(12) . . ? C24 C25 H25 120.0 . . ? C26 C25 C24 120.06(15) . . ? C26 C25 H25 120.0 . . ? C25 C26 H26 119.9 . . ? C25 C26 C27 120.13(15) . . ? C27 C26 H26 119.9 . . ? C26 C27 H27 120.0 . . ? C28 C27 C26 119.96(15) . . ? C28 C27 H27 120.0 . . ? C27 C28 H28 119.8 . . ? C27 C28 C29 120.35(15) . . ? C29 C28 H28 119.8 . . ? C24 C29 H29 120.1 . . ? C28 C29 C24 119.73(15) . . ? C28 C29 H29 120.1 . . ? C1 P1 S1 115.15(5) . . ? C18 P1 C1 105.95(7) . . ? C18 P1 S1 110.73(6) . . ? C24 P1 C1 104.46(7) . . ? C24 P1 C18 106.03(7) . . ? C24 P1 S1 113.78(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 C1 C2 C3 C4 1.9(3) . . . . ? C1 C6 C7 C8 144.88(14) . . . 3_757 ? C1 C6 C7 C8 -110.93(16) . . . . ? C2 C1 C6 C5 -0.7(2) . . . . ? C2 C1 C6 C7 175.26(14) . . . . ? C2 C1 P1 C18 1.53(14) . . . . ? C2 C1 P1 C24 113.26(13) . . . . ? C2 C1 P1 S1 -121.22(12) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 -1.7(2) . . . . ? C4 C5 C6 C1 2.2(2) . . . . ? C4 C5 C6 C7 -173.93(14) . . . . ? C5 C6 C7 C8 65.01(18) . . . . ? C5 C6 C7 C8 -39.18(19) . . . 3_757 ? C6 C1 C2 C3 -1.3(2) . . . . ? C6 C1 P1 C18 -177.02(12) . . . . ? C6 C1 P1 C24 -65.29(13) . . . . ? C6 C1 P1 S1 60.24(13) . . . . ? C6 C7 C8 C7 -121.59(15) . . . 3_757 ? C6 C7 C8 C9 -2.53(18) . . . . ? C7 C8 C9 C10 176.41(13) 3_757 . . . ? C7 C8 C9 C10 72.90(17) . . . . ? C7 C8 C9 O1 -105.33(17) . . . . ? C7 C8 C9 O1 -1.8(2) 3_757 . . . ? C8 C7 C8 C7 0.0 3_757 . . 3_757 ? C8 C7 C8 C9 119.06(15) 3_757 . . . ? C8 C9 C10 C11 -160.99(15) . . . . ? C9 C10 C11 C12 -176.53(15) . . . . ? C10 C11 C12 C13 -9.1(3) . . . . ? C10 C11 C12 C17 167.68(17) . . . . ? C11 C12 C13 C14 174.08(16) . . . . ? C11 C12 C17 C16 -174.62(17) . . . . ? C12 C13 C14 C15 1.1(3) . . . . ? C13 C12 C17 C16 2.3(3) . . . . ? C13 C14 C15 C16 1.1(3) . . . . ? C14 C15 C16 C17 -1.5(3) . . . . ? C15 C16 C17 C12 -0.2(3) . . . . ? C17 C12 C13 C14 -2.7(3) . . . . ? C18 C19 C20 C21 0.7(3) . . . . ? C19 C18 C23 C22 -2.0(3) . . . . ? C19 C18 P1 C1 99.83(15) . . . . ? C19 C18 P1 C24 -10.80(16) . . . . ? C19 C18 P1 S1 -134.67(13) . . . . ? C19 C20 C21 C22 -2.0(3) . . . . ? C20 C21 C22 C23 1.3(3) . . . . ? C21 C22 C23 C18 0.8(3) . . . . ? C23 C18 C19 C20 1.3(3) . . . . ? C23 C18 P1 C1 -80.76(15) . . . . ? C23 C18 P1 C24 168.61(14) . . . . ? C23 C18 P1 S1 44.74(15) . . . . ? C24 C25 C26 C27 0.2(3) . . . . ? C25 C24 C29 C28 -1.8(2) . . . . ? C25 C24 P1 C1 160.90(12) . . . . ? C25 C24 P1 C18 -87.42(14) . . . . ? C25 C24 P1 S1 34.52(14) . . . . ? C25 C26 C27 C28 -1.3(3) . . . . ? C26 C27 C28 C29 0.9(3) . . . . ? C27 C28 C29 C24 0.7(2) . . . . ? C29 C24 C25 C26 1.4(2) . . . . ? C29 C24 P1 C1 -18.52(15) . . . . ? C29 C24 P1 C18 93.16(14) . . . . ? C29 C24 P1 S1 -144.90(12) . . . . ? O1 C9 C10 C11 17.2(2) . . . . ? P1 C1 C2 C3 -179.91(13) . . . . ? P1 C1 C6 C5 177.82(11) . . . . ? P1 C1 C6 C7 -6.2(2) . . . . ? P1 C18 C19 C20 -179.33(14) . . . . ? P1 C18 C23 C22 178.57(16) . . . . ? P1 C24 C25 C26 -178.02(13) . . . . ? P1 C24 C29 C28 177.58(12) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 2 -15 -13 0.0506 2.0000 -14.9834 -12.9894 -0.3370 -0.8456 -0.4167 -2 15 13 0.0506 -2.0000 14.9834 12.9894 0.3370 0.8456 0.4167 -17 -2 6 0.1310 -17.0017 -2.0053 6.0273 0.1831 0.4936 -0.8740 17 3 -5 0.1107 17.0018 3.0042 -5.0284 -0.1672 -0.4333 0.9108 1 -15 13 0.0380 1.0127 -14.9977 12.9859 -0.9606 0.3277 -0.1149 -1 15 -13 0.0380 -1.0127 14.9977 -12.9859 0.9606 -0.3277 0.1149 -2 -15 -12 0.0610 -2.0008 -14.9847 -11.9826 -0.2644 -0.7404 -0.6171 15 8 -1 0.0943 15.0012 7.9986 -1.0290 -0.0141 -0.1460 0.9737 5 -14 -14 0.0541 5.0001 -13.9829 -13.9943 -0.3444 -0.9199 -0.2467 1 12 -16 0.0362 0.9876 12.0015 -15.9865 0.8641 -0.5389 0.1117 2 -10 16 0.0429 2.0126 -10.0021 15.9805 -0.8556 0.5249 0.0950 -12 -1 -11 0.1262 -12.0090 -0.9958 -10.9652 0.5257 -0.3238 -0.8157 2 -20 2 0.0457 2.0095 -19.9885 1.9956 -0.9149 -0.2562 -0.3270 -2 20 -2 0.0518 -2.0095 19.9885 -1.9956 0.9149 0.2562 0.3270 -14 9 -3 0.1227 -14.0095 8.9934 -2.9703 0.7832 0.2204 -0.5827 1 -4 -19 0.0487 0.9924 -3.9871 -18.9822 0.2859 -0.9245 -0.2984 -14 -12 2 0.1221 -13.9988 -11.9965 2.0263 -0.1985 0.1124 -0.9988 ### END data_0h _database_code_depnum_ccdc_archive 'CCDC 874833' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.517 _cell_length_b 17.083 _cell_length_c 14.581 _cell_angle_alpha 90.00 _cell_angle_beta 101.96 _cell_angle_gamma 90.00 _cell_volume 2319.1 _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3621 _cell_measurement_theta_min 3.0831 _cell_measurement_theta_max 32.4797 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.29 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98755 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 14600 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.1375 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.0831 _diffrn_reflns_theta_max 32.4797 _reflns_number_total 7634 _reflns_number_gt 3962 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0447504000 _diffrn_orient_matrix_UB_12 -0.0007363000 _diffrn_orient_matrix_UB_13 0.0453000000 _diffrn_orient_matrix_UB_21 -0.0533897000 _diffrn_orient_matrix_UB_22 0.0215704000 _diffrn_orient_matrix_UB_23 0.0168445000 _diffrn_orient_matrix_UB_31 -0.0337997000 _diffrn_orient_matrix_UB_32 -0.0349907000 _diffrn_orient_matrix_UB_33 0.0094313000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement '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^)+(0.0375P)^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 7634 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1106 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 0.857 _refine_ls_restrained_S_all 0.857 _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 S1 S 0.41517(4) -0.01093(2) 0.73218(3) 0.03232(12) Uani 1 1 d . . . P1 P 0.47885(4) 0.09835(2) 0.73953(3) 0.02315(10) Uani 1 1 d . . . O1 O 0.14208(12) 0.04560(6) 0.93873(9) 0.0389(3) Uani 1 1 d . . . C18 C 0.56684(15) 0.12478(8) 0.64473(12) 0.0253(3) Uani 1 1 d . . . C6 C 0.16825(16) 0.09166(8) 1.26869(13) 0.0276(4) Uani 1 1 d . . . C17 C 0.60556(15) 0.12198(7) 0.84704(12) 0.0232(3) Uani 1 1 d . . . C7 C 0.22292(16) 0.08847(8) 1.18248(13) 0.0287(4) Uani 1 1 d . . . H7 H 0.3143 0.1117 1.1850 0.034 Uiso 1 1 calc R . . C12 C 0.56687(15) 0.11684(8) 0.93533(12) 0.0241(3) Uani 1 1 d . . . C10 C 0.37182(16) 0.08291(9) 1.02065(13) 0.0302(4) Uani 1 1 d . . . H10 H 0.4346 0.0882 1.0801 0.036 Uiso 1 1 calc R . . C11 C 0.41992(15) 0.09554(8) 0.94345(12) 0.0268(3) Uani 1 1 d . . . H11 H 0.3517 0.0903 0.8862 0.032 Uiso 1 1 calc R . . C5 C 0.04009(17) 0.05535(8) 1.27868(13) 0.0328(4) Uani 1 1 d . . . H5 H -0.0155 0.0270 1.2278 0.039 Uiso 1 1 calc R . . C9 C 0.21923(16) 0.06044(8) 1.01457(13) 0.0269(4) Uani 1 1 d . . . C29 C 0.35262(17) 0.24363(8) 0.76453(12) 0.0297(4) Uani 1 1 d . . . H29 H 0.4470 0.2618 0.7898 0.036 Uiso 1 1 calc R . . C24 C 0.33042(16) 0.16680(8) 0.73293(12) 0.0248(3) Uani 1 1 d . . . C16 C 0.74750(16) 0.14057(8) 0.84311(13) 0.0288(4) Uani 1 1 d . . . H16 H 0.7747 0.1432 0.7841 0.035 Uiso 1 1 calc R . . C8 C 0.16065(16) 0.05702(8) 1.10082(13) 0.0277(4) Uani 1 1 d . . . H8 H 0.0721 0.0304 1.0976 0.033 Uiso 1 1 calc R . . C23 C 0.59656(18) 0.20236(9) 0.62607(13) 0.0338(4) Uani 1 1 d . . . H23 H 0.5684 0.2432 0.6626 0.041 Uiso 1 1 calc R . . C15 C 0.84884(16) 0.15516(9) 0.92429(14) 0.0340(4) Uani 1 1 d . . . H15 H 0.9446 0.1681 0.9206 0.041 Uiso 1 1 calc R . . C3 C 0.07317(19) 0.10139(9) 1.43756(14) 0.0401(4) Uani 1 1 d . . . H3 H 0.0407 0.1044 1.4948 0.048 Uiso 1 1 calc R . . C13 C 0.67181(16) 0.13166(9) 1.01547(13) 0.0326(4) Uani 1 1 d . . . H13 H 0.6471 0.1285 1.0752 0.039 Uiso 1 1 calc R . . C27 C 0.09918(19) 0.26685(11) 0.72390(14) 0.0444(5) Uani 1 1 d . . . H27 H 0.0199 0.3012 0.7211 0.053 Uiso 1 1 calc R . . C14 C 0.81088(17) 0.15087(9) 1.01010(14) 0.0352(4) Uani 1 1 d . . . H14 H 0.8803 0.1611 1.0657 0.042 Uiso 1 1 calc R . . C19 C 0.60927(18) 0.06628(9) 0.59072(14) 0.0368(4) Uani 1 1 d . . . H19 H 0.5897 0.0131 0.6027 0.044 Uiso 1 1 calc R . . C4 C -0.00528(18) 0.06089(9) 1.36260(14) 0.0380(4) Uani 1 1 d . . . H4 H -0.0924 0.0362 1.3686 0.046 Uiso 1 1 calc R . . C21 C 0.70851(19) 0.16131(11) 0.50179(14) 0.0440(5) Uani 1 1 d . . . H21 H 0.7572 0.1738 0.4530 0.053 Uiso 1 1 calc R . . C20 C 0.6798(2) 0.08428(11) 0.51945(15) 0.0463(5) Uani 1 1 d . . . H20 H 0.7084 0.0437 0.4828 0.056 Uiso 1 1 calc R . . C1 C 0.24609(18) 0.13247(9) 1.34564(14) 0.0365(4) Uani 1 1 d . . . H1 H 0.3334 0.1573 1.3404 0.044 Uiso 1 1 calc R . . C25 C 0.19204(17) 0.14088(9) 0.69775(14) 0.0365(4) Uani 1 1 d . . . H25 H 0.1763 0.0884 0.6766 0.044 Uiso 1 1 calc R . . C22 C 0.66662(19) 0.22016(10) 0.55490(14) 0.0413(5) Uani 1 1 d . . . H22 H 0.6861 0.2732 0.5424 0.050 Uiso 1 1 calc R . . C28 C 0.23633(19) 0.29334(9) 0.75890(13) 0.0374(4) Uani 1 1 d . . . H28 H 0.2513 0.3461 0.7793 0.045 Uiso 1 1 calc R . . C2 C 0.19974(19) 0.13768(10) 1.42897(15) 0.0428(5) Uani 1 1 d . . . H2 H 0.2544 0.1660 1.4802 0.051 Uiso 1 1 calc R . . C26 C 0.07599(18) 0.19113(11) 0.69307(15) 0.0460(5) Uani 1 1 d . . . H26 H -0.0189 0.1732 0.6687 0.055 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 S1 0.0342(2) 0.02415(19) 0.0370(3) -0.00222(18) 0.0036(2) -0.00443(16) P1 0.02258(19) 0.02226(18) 0.0243(2) -0.00158(17) 0.00401(17) 0.00048(15) O1 0.0288(6) 0.0549(7) 0.0320(8) -0.0025(6) 0.0037(6) -0.0086(5) C18 0.0250(8) 0.0286(8) 0.0226(10) -0.0012(7) 0.0054(7) 0.0024(6) C6 0.0263(8) 0.0257(7) 0.0315(11) -0.0003(7) 0.0073(7) -0.0002(6) C17 0.0213(7) 0.0198(7) 0.0278(10) -0.0011(6) 0.0032(7) 0.0013(5) C7 0.0228(7) 0.0294(8) 0.0345(11) 0.0014(7) 0.0074(7) -0.0028(6) C12 0.0223(7) 0.0236(7) 0.0253(10) -0.0009(7) 0.0026(7) 0.0013(6) C10 0.0236(8) 0.0401(9) 0.0257(10) -0.0024(8) 0.0023(7) -0.0026(6) C11 0.0223(7) 0.0309(8) 0.0254(10) -0.0014(7) 0.0011(7) -0.0002(6) C5 0.0307(9) 0.0328(8) 0.0352(12) -0.0042(8) 0.0077(8) -0.0052(7) C9 0.0253(8) 0.0254(7) 0.0293(11) 0.0005(7) 0.0043(7) 0.0014(6) C29 0.0293(8) 0.0326(8) 0.0273(10) -0.0002(7) 0.0058(7) 0.0032(6) C24 0.0250(8) 0.0288(7) 0.0209(9) 0.0006(7) 0.0051(7) 0.0039(6) C16 0.0238(8) 0.0299(8) 0.0338(11) 0.0008(7) 0.0088(8) 0.0010(6) C8 0.0229(8) 0.0299(8) 0.0308(11) 0.0012(7) 0.0071(7) -0.0014(6) C23 0.0401(10) 0.0295(8) 0.0347(12) 0.0011(8) 0.0142(9) 0.0051(7) C15 0.0186(8) 0.0366(9) 0.0452(13) 0.0001(8) 0.0030(8) -0.0032(6) C3 0.0476(11) 0.0428(10) 0.0335(12) -0.0023(9) 0.0169(9) -0.0018(8) C13 0.0300(9) 0.0390(9) 0.0280(11) -0.0022(8) 0.0042(8) -0.0010(7) C27 0.0386(10) 0.0551(11) 0.0415(13) 0.0087(9) 0.0131(10) 0.0239(8) C14 0.0257(8) 0.0397(9) 0.0358(12) -0.0040(8) -0.0040(8) -0.0033(7) C19 0.0441(10) 0.0335(9) 0.0347(12) -0.0060(8) 0.0131(9) -0.0006(7) C4 0.0357(9) 0.0407(9) 0.0407(13) -0.0021(9) 0.0153(9) -0.0071(7) C21 0.0448(11) 0.0605(12) 0.0308(12) 0.0045(10) 0.0178(10) 0.0015(9) C20 0.0551(12) 0.0518(11) 0.0381(13) -0.0138(10) 0.0234(11) 0.0017(9) C1 0.0320(9) 0.0378(9) 0.0402(13) -0.0039(9) 0.0082(9) -0.0086(7) C25 0.0286(9) 0.0398(9) 0.0385(12) -0.0029(8) 0.0012(8) 0.0014(7) C22 0.0448(11) 0.0405(9) 0.0422(13) 0.0099(9) 0.0172(10) 0.0025(8) C28 0.0471(11) 0.0334(8) 0.0335(12) 0.0006(8) 0.0125(9) 0.0153(8) C2 0.0458(11) 0.0467(10) 0.0357(13) -0.0118(9) 0.0077(10) -0.0087(8) C26 0.0245(9) 0.0644(12) 0.0462(14) 0.0029(10) 0.0008(9) 0.0070(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 S1 P1 1.9589(5) . ? P1 C17 1.8140(16) . ? P1 C18 1.8155(16) . ? P1 C24 1.8210(14) . ? O1 C9 1.221(2) . ? C18 C19 1.383(2) . ? C18 C23 1.394(2) . ? C6 C1 1.396(2) . ? C6 C5 1.403(2) . ? C6 C7 1.458(2) . ? C17 C16 1.4003(19) . ? C17 C12 1.413(2) . ? C7 C8 1.329(2) . ? C7 H7 0.9500 . ? C12 C13 1.394(2) . ? C12 C11 1.4735(19) . ? C10 C11 1.318(2) . ? C10 C9 1.487(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C5 C4 1.383(2) . ? C5 H5 0.9500 . ? C9 C8 1.479(2) . ? C29 C28 1.384(2) . ? C29 C24 1.392(2) . ? C29 H29 0.9500 . ? C24 C25 1.383(2) . ? C16 C15 1.386(2) . ? C16 H16 0.9500 . ? C8 H8 0.9500 . ? C23 C22 1.379(2) . ? C23 H23 0.9500 . ? C15 C14 1.374(3) . ? C15 H15 0.9500 . ? C3 C4 1.376(2) . ? C3 C2 1.383(2) . ? C3 H3 0.9500 . ? C13 C14 1.381(2) . ? C13 H13 0.9500 . ? C27 C26 1.372(2) . ? C27 C28 1.376(2) . ? C27 H27 0.9500 . ? C14 H14 0.9500 . ? C19 C20 1.384(2) . ? C19 H19 0.9500 . ? C4 H4 0.9500 . ? C21 C22 1.377(2) . ? C21 C20 1.379(2) . ? C21 H21 0.9500 . ? C20 H20 0.9500 . ? C1 C2 1.379(2) . ? C1 H1 0.9500 . ? C25 C26 1.389(2) . ? C25 H25 0.9500 . ? C22 H22 0.9500 . ? C28 H28 0.9500 . ? C2 H2 0.9500 . ? C26 H26 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 C17 P1 C18 105.88(7) . . ? C17 P1 C24 105.80(7) . . ? C18 P1 C24 105.98(7) . . ? C17 P1 S1 113.71(5) . . ? C18 P1 S1 112.44(5) . . ? C24 P1 S1 112.41(5) . . ? C19 C18 C23 118.74(15) . . ? C19 C18 P1 119.27(12) . . ? C23 C18 P1 121.97(12) . . ? C1 C6 C5 117.74(16) . . ? C1 C6 C7 119.14(14) . . ? C5 C6 C7 123.13(16) . . ? C16 C17 C12 119.14(15) . . ? C16 C17 P1 119.29(13) . . ? C12 C17 P1 121.42(11) . . ? C8 C7 C6 127.97(14) . . ? C8 C7 H7 116.0 . . ? C6 C7 H7 116.0 . . ? C13 C12 C17 118.41(14) . . ? C13 C12 C11 120.30(16) . . ? C17 C12 C11 121.29(15) . . ? C11 C10 C9 119.94(16) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 127.77(16) . . ? C10 C11 H11 116.1 . . ? C12 C11 H11 116.1 . . ? C4 C5 C6 119.96(17) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? O1 C9 C8 120.02(14) . . ? O1 C9 C10 120.29(16) . . ? C8 C9 C10 119.68(15) . . ? C28 C29 C24 119.61(16) . . ? C28 C29 H29 120.2 . . ? C24 C29 H29 120.2 . . ? C25 C24 C29 119.47(14) . . ? C25 C24 P1 118.85(11) . . ? C29 C24 P1 121.66(12) . . ? C15 C16 C17 120.83(17) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C7 C8 C9 124.71(14) . . ? C7 C8 H8 117.6 . . ? C9 C8 H8 117.6 . . ? C22 C23 C18 120.40(15) . . ? C22 C23 H23 119.8 . . ? C18 C23 H23 119.8 . . ? C14 C15 C16 120.02(15) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C4 C3 C2 119.53(18) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C14 C13 C12 121.60(17) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C26 C27 C28 120.49(15) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C15 C14 C13 120.00(17) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C18 C19 C20 120.75(15) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C3 C4 C5 121.33(16) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C22 C21 C20 119.99(17) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C20 C19 119.86(17) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C2 C1 C6 121.81(16) . . ? C2 C1 H1 119.1 . . ? C6 C1 H1 119.1 . . ? C24 C25 C26 120.43(16) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C22 C23 120.24(16) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C27 C28 C29 120.38(16) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C1 C2 C3 119.63(18) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C27 C26 C25 119.61(17) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 P1 C18 C19 110.85(13) . . . . ? C24 P1 C18 C19 -137.07(13) . . . . ? S1 P1 C18 C19 -13.88(15) . . . . ? C17 P1 C18 C23 -67.42(15) . . . . ? C24 P1 C18 C23 44.66(15) . . . . ? S1 P1 C18 C23 167.84(12) . . . . ? C18 P1 C17 C16 -11.31(12) . . . . ? C24 P1 C17 C16 -123.51(11) . . . . ? S1 P1 C17 C16 112.63(10) . . . . ? C18 P1 C17 C12 173.08(11) . . . . ? C24 P1 C17 C12 60.87(12) . . . . ? S1 P1 C17 C12 -62.98(12) . . . . ? C1 C6 C7 C8 -175.51(16) . . . . ? C5 C6 C7 C8 4.6(2) . . . . ? C16 C17 C12 C13 0.9(2) . . . . ? P1 C17 C12 C13 176.50(10) . . . . ? C16 C17 C12 C11 -178.45(12) . . . . ? P1 C17 C12 C11 -2.83(18) . . . . ? C9 C10 C11 C12 -178.94(13) . . . . ? C13 C12 C11 C10 -4.8(2) . . . . ? C17 C12 C11 C10 174.49(15) . . . . ? C1 C6 C5 C4 0.2(2) . . . . ? C7 C6 C5 C4 -179.96(14) . . . . ? C11 C10 C9 O1 7.7(2) . . . . ? C11 C10 C9 C8 -171.58(14) . . . . ? C28 C29 C24 C25 -1.1(3) . . . . ? C28 C29 C24 P1 -179.39(13) . . . . ? C17 P1 C24 C25 -142.83(14) . . . . ? C18 P1 C24 C25 105.03(14) . . . . ? S1 P1 C24 C25 -18.17(16) . . . . ? C17 P1 C24 C29 35.52(15) . . . . ? C18 P1 C24 C29 -76.62(15) . . . . ? S1 P1 C24 C29 160.18(12) . . . . ? C12 C17 C16 C15 -1.1(2) . . . . ? P1 C17 C16 C15 -176.82(11) . . . . ? C6 C7 C8 C9 176.02(14) . . . . ? O1 C9 C8 C7 -163.94(15) . . . . ? C10 C9 C8 C7 15.4(2) . . . . ? C19 C18 C23 C22 0.2(3) . . . . ? P1 C18 C23 C22 178.44(14) . . . . ? C17 C16 C15 C14 0.5(2) . . . . ? C17 C12 C13 C14 -0.1(2) . . . . ? C11 C12 C13 C14 179.25(13) . . . . ? C16 C15 C14 C13 0.3(2) . . . . ? C12 C13 C14 C15 -0.5(2) . . . . ? C23 C18 C19 C20 0.0(3) . . . . ? P1 C18 C19 C20 -178.37(15) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C6 C5 C4 C3 -0.2(3) . . . . ? C22 C21 C20 C19 -0.2(3) . . . . ? C18 C19 C20 C21 0.0(3) . . . . ? C5 C6 C1 C2 -0.2(2) . . . . ? C7 C6 C1 C2 179.88(15) . . . . ? C29 C24 C25 C26 0.6(3) . . . . ? P1 C24 C25 C26 178.96(15) . . . . ? C20 C21 C22 C23 0.3(3) . . . . ? C18 C23 C22 C21 -0.3(3) . . . . ? C26 C27 C28 C29 -0.8(3) . . . . ? C24 C29 C28 C27 1.2(3) . . . . ? C6 C1 C2 C3 0.3(3) . . . . ? C4 C3 C2 C1 -0.3(3) . . . . ? C28 C27 C26 C25 0.3(3) . . . . ? C24 C25 C26 C27 -0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.320 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.052 ### END data_2h _database_code_depnum_ccdc_archive 'CCDC 874834' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.3791(2) _cell_length_b 17.2497(3) _cell_length_c 14.7021(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.069(2) _cell_angle_gamma 90.00 _cell_volume 2326.03(9) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 26951 _cell_measurement_theta_min 3.0606 _cell_measurement_theta_max 29.9909 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.29 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98755 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_reflns_number 17523 _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_sigmaI/netI 0.1573 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.0606 _diffrn_reflns_theta_max 29.9909 _diffrn_orient_matrix_UB_11 0.0447504000 _diffrn_orient_matrix_UB_12 -0.0007363000 _diffrn_orient_matrix_UB_13 0.0453000000 _diffrn_orient_matrix_UB_21 -0.0533897000 _diffrn_orient_matrix_UB_22 0.0215704000 _diffrn_orient_matrix_UB_23 0.0168445000 _diffrn_orient_matrix_UB_31 -0.0337997000 _diffrn_orient_matrix_UB_32 -0.0349907000 _diffrn_orient_matrix_UB_33 0.0094313000 _reflns_number_total 6786 _reflns_number_gt 3069 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement '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^)+(0.0510P)^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 6786 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1263 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 0.866 _refine_ls_restrained_S_all 0.865 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91711(7) -0.01223(3) 0.22575(5) 0.04950(19) Uani 1 1 d . A . P1 P 0.98516(6) 0.09527(3) 0.23747(4) 0.03423(15) Uani 1 1 d . . . O1 O 0.6308(5) 0.0445(3) 0.4394(4) 0.0475(13) Uani 0.494(5) 1 d P A 1 C1 C 1.0708(2) 0.12308(11) 0.14276(15) 0.0355(5) Uani 1 1 d . A . C2 C 1.1183(3) 0.06646(13) 0.08949(17) 0.0498(6) Uani 1 1 d . . . H2 H 1.1029 0.0134 0.1019 0.060 Uiso 1 1 calc R A . C3 C 1.1875(3) 0.08569(16) 0.01882(18) 0.0591(7) Uani 1 1 d . A . H3 H 1.2195 0.0461 -0.0171 0.071 Uiso 1 1 calc R . . C4 C 1.2103(3) 0.16180(16) 0.00029(18) 0.0569(7) Uani 1 1 d . . . H4 H 1.2581 0.1748 -0.0486 0.068 Uiso 1 1 calc R A . C5 C 1.1646(3) 0.21969(15) 0.0520(2) 0.0620(8) Uani 1 1 d . A . H5 H 1.1807 0.2725 0.0389 0.074 Uiso 1 1 calc R . . C6 C 1.0947(3) 0.20051(12) 0.12323(19) 0.0537(7) Uani 1 1 d . . . H6 H 1.0629 0.2404 0.1589 0.064 Uiso 1 1 calc R A . C7 C 0.8374(2) 0.16358(11) 0.23404(14) 0.0335(5) Uani 1 1 d . A . C8 C 0.6967(3) 0.13974(14) 0.19658(17) 0.0508(6) Uani 1 1 d . . . H8 H 0.6796 0.0879 0.1751 0.061 Uiso 1 1 calc R A . C9 C 0.5809(3) 0.18998(17) 0.1899(2) 0.0700(8) Uani 1 1 d . A . H9 H 0.4847 0.1728 0.1641 0.084 Uiso 1 1 calc R . . C10 C 0.6049(3) 0.26511(16) 0.2207(2) 0.0630(8) Uani 1 1 d . . . H10 H 0.5254 0.3001 0.2159 0.076 Uiso 1 1 calc R A . C11 C 0.7438(3) 0.28928(13) 0.25822(17) 0.0535(7) Uani 1 1 d . A . H11 H 0.7603 0.3413 0.2790 0.064 Uiso 1 1 calc R . . C12 C 0.8599(3) 0.23902(12) 0.26624(15) 0.0418(5) Uani 1 1 d . . . H12 H 0.9555 0.2561 0.2939 0.050 Uiso 1 1 calc R A . C13 C 1.1043(11) 0.1193(5) 0.3524(6) 0.0268(19) Uani 0.494(5) 1 d PD A 1 C14 C 1.2484(10) 0.1358(4) 0.3483(5) 0.039(2) Uani 0.494(5) 1 d PD A 1 H14 H 1.2764 0.1377 0.2898 0.046 Uiso 0.494(5) 1 calc PR A 1 C15 C 1.3504(8) 0.1494(4) 0.4292(6) 0.0444(18) Uani 0.494(5) 1 d PD A 1 H15 H 1.4488 0.1603 0.4268 0.053 Uiso 0.494(5) 1 calc PR A 1 C16 C 1.3079(9) 0.1468(5) 0.5141(7) 0.0419(19) Uani 0.494(5) 1 d PD A 1 H16 H 1.3772 0.1574 0.5698 0.050 Uiso 0.494(5) 1 calc PR A 1 C17 C 1.1666(8) 0.1291(4) 0.5185(4) 0.0389(16) Uani 0.494(5) 1 d PD A 1 H17 H 1.1407 0.1258 0.5775 0.047 Uiso 0.494(5) 1 calc PR A 1 C18 C 1.0599(6) 0.1159(3) 0.4378(4) 0.0322(13) Uani 0.494(5) 1 d PD A 1 C19 C 0.9103(5) 0.0960(2) 0.4444(3) 0.0349(12) Uani 0.494(5) 1 d P A 1 H19 H 0.8401 0.0941 0.3876 0.042 Uiso 0.494(5) 1 calc PR A 1 C20 C 0.8623(8) 0.0804(4) 0.5214(4) 0.0365(16) Uani 0.494(5) 1 d P A 1 H20 H 0.9274 0.0832 0.5802 0.044 Uiso 0.494(5) 1 calc PR A 1 C21 C 0.7085(9) 0.0588(5) 0.5157(5) 0.0352(17) Uani 0.494(5) 1 d P A 1 C22 C 0.6679(9) 0.0555(4) 0.5943(4) 0.0345(19) Uani 0.494(5) 1 d P A 1 H22 H 0.5831 0.0249 0.5920 0.041 Uiso 0.494(5) 1 calc PR A 1 C23 C 0.7222(8) 0.0876(4) 0.6826(4) 0.0265(11) Uani 0.494(5) 1 d P A 1 H23 H 0.8147 0.1120 0.6898 0.032 Uiso 0.494(5) 1 calc PR A 1 C24 C 0.6603(3) 0.08913(14) 0.76200(19) 0.0548(7) Uani 1 1 d . . . C25 C 0.5327(3) 0.05363(14) 0.7756(2) 0.0583(7) Uani 1 1 d . A . H25 H 0.4733 0.0254 0.7263 0.070 Uiso 1 1 calc R . . C26 C 0.4927(3) 0.05941(14) 0.8606(2) 0.0584(7) Uani 1 1 d . . . H26 H 0.4064 0.0347 0.8699 0.070 Uiso 1 1 calc R A . C27 C 0.5772(3) 0.10069(15) 0.93149(19) 0.0557(7) Uani 1 1 d . A . H27 H 0.5492 0.1048 0.9898 0.067 Uiso 1 1 calc R . . C28 C 0.7023(3) 0.13614(15) 0.9185(2) 0.0608(7) Uani 1 1 d . . . H28 H 0.7604 0.1648 0.9679 0.073 Uiso 1 1 calc R A . C29 C 0.7438(3) 0.13055(14) 0.8350(2) 0.0609(7) Uani 1 1 d . A . H29 H 0.8307 0.1553 0.8268 0.073 Uiso 1 1 calc R . . O1A O 0.7047(8) 0.0603(5) 0.4530(7) 0.098(3) Uani 0.506(5) 1 d P A 2 C13A C 1.1337(12) 0.1152(5) 0.3344(7) 0.029(2) Uani 0.506(5) 1 d PD A 2 C14A C 1.2577(10) 0.1553(5) 0.3243(6) 0.044(2) Uani 0.506(5) 1 d PD A 2 H14A H 1.2699 0.1678 0.2635 0.053 Uiso 0.506(5) 1 calc PR A 2 C15A C 1.3634(8) 0.1776(4) 0.3993(6) 0.062(2) Uani 0.506(5) 1 d PD A 2 H15A H 1.4469 0.2049 0.3897 0.075 Uiso 0.506(5) 1 calc PR A 2 C16A C 1.3487(10) 0.1603(6) 0.4880(6) 0.056(3) Uani 0.506(5) 1 d PD A 2 H16A H 1.4214 0.1755 0.5402 0.067 Uiso 0.506(5) 1 calc PR A 2 C17A C 1.2270(9) 0.1207(4) 0.4999(5) 0.0472(18) Uani 0.506(5) 1 d PD A 2 H17A H 1.2159 0.1096 0.5614 0.057 Uiso 0.506(5) 1 calc PR A 2 C18A C 1.1175(6) 0.0958(3) 0.4242(4) 0.0325(12) Uani 0.506(5) 1 d PD A 2 C19A C 1.0008(5) 0.0410(2) 0.4419(3) 0.0350(13) Uani 0.506(5) 1 d P . 2 H19A H 0.9154 0.0419 0.3882 0.042 Uiso 0.506(5) 1 calc PR A 2 C20A C 0.9493(7) 0.0457(3) 0.5333(4) 0.0474(15) Uani 0.506(5) 1 d P . 2 H20A H 1.0089 0.0834 0.5772 0.057 Uiso 0.506(5) 1 calc PR A 2 C21A C 0.7866(14) 0.0603(6) 0.5237(8) 0.070(4) Uani 0.506(5) 1 d P A 2 C22A C 0.7701(10) 0.0835(4) 0.6431(8) 0.091(3) Uani 0.506(5) 1 d P A 2 H22A H 0.8407 0.1044 0.6930 0.109 Uiso 0.506(5) 1 calc PR A 2 C23A C 0.6521(11) 0.0660(5) 0.6413(12) 0.102(5) Uani 0.506(5) 1 d P A 2 H23A H 0.5767 0.0464 0.5935 0.122 Uiso 0.506(5) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0443(4) 0.0314(3) 0.0665(4) -0.0011(3) -0.0028(3) -0.0040(3) P1 0.0354(3) 0.0294(3) 0.0342(3) 0.0015(2) -0.0011(2) 0.0003(2) O1 0.049(3) 0.059(2) 0.029(2) -0.0096(16) -0.005(2) -0.005(2) C1 0.0325(12) 0.0349(10) 0.0374(13) 0.0008(9) 0.0035(9) 0.0054(9) C2 0.0598(17) 0.0431(12) 0.0455(15) -0.0083(11) 0.0091(12) 0.0019(12) C3 0.0645(19) 0.0665(16) 0.0495(17) -0.0153(13) 0.0191(14) 0.0071(15) C4 0.0541(17) 0.0739(17) 0.0467(17) 0.0011(13) 0.0194(13) 0.0041(14) C5 0.067(2) 0.0535(14) 0.075(2) 0.0078(14) 0.0371(16) -0.0006(14) C6 0.0609(18) 0.0392(12) 0.0695(19) 0.0021(12) 0.0328(14) 0.0058(12) C7 0.0413(13) 0.0359(10) 0.0240(11) 0.0020(9) 0.0084(9) 0.0031(10) C8 0.0414(15) 0.0525(13) 0.0568(17) -0.0097(12) 0.0063(12) 0.0023(12) C9 0.0426(16) 0.0824(19) 0.082(2) -0.0122(17) 0.0073(15) 0.0109(15) C10 0.0588(19) 0.0670(17) 0.067(2) 0.0021(14) 0.0222(15) 0.0276(15) C11 0.071(2) 0.0425(12) 0.0510(17) -0.0023(11) 0.0216(14) 0.0137(14) C12 0.0486(15) 0.0436(12) 0.0346(13) -0.0030(10) 0.0120(11) 0.0037(11) C13 0.031(4) 0.024(3) 0.025(4) -0.002(3) 0.003(3) 0.000(3) C14 0.039(4) 0.043(4) 0.033(4) -0.002(3) 0.007(3) 0.004(3) C15 0.032(3) 0.057(4) 0.041(5) -0.004(4) -0.001(3) -0.004(3) C16 0.031(5) 0.053(4) 0.039(4) -0.003(3) 0.001(3) -0.004(3) C17 0.043(4) 0.048(3) 0.025(3) -0.001(2) 0.005(3) -0.011(3) C18 0.036(3) 0.034(3) 0.026(3) 0.000(2) 0.007(2) 0.002(2) C19 0.042(3) 0.041(2) 0.021(2) 0.0000(18) 0.0034(17) 0.000(2) C20 0.039(4) 0.047(4) 0.022(3) -0.004(2) 0.005(2) -0.004(3) C21 0.035(4) 0.029(3) 0.036(4) 0.001(2) -0.006(3) 0.000(3) C22 0.048(5) 0.029(2) 0.023(3) -0.001(2) -0.002(2) -0.008(3) C23 0.021(3) 0.035(3) 0.026(3) 0.005(2) 0.009(2) -0.001(3) C24 0.069(2) 0.0455(13) 0.0558(18) 0.0112(13) 0.0258(15) 0.0217(14) C25 0.0606(19) 0.0474(14) 0.0616(19) -0.0037(12) 0.0002(15) 0.0043(13) C26 0.0506(17) 0.0606(15) 0.067(2) -0.0010(14) 0.0193(15) -0.0034(13) C27 0.0518(17) 0.0626(15) 0.0565(17) -0.0015(13) 0.0200(13) 0.0025(14) C28 0.0530(18) 0.0617(16) 0.070(2) -0.0086(14) 0.0172(15) -0.0078(14) C29 0.0577(18) 0.0532(14) 0.078(2) 0.0026(14) 0.0278(16) -0.0004(14) O1A 0.065(5) 0.105(5) 0.131(7) 0.062(5) 0.034(6) 0.038(4) C13A 0.032(5) 0.031(3) 0.028(4) 0.005(2) 0.013(3) 0.003(3) C14A 0.031(3) 0.056(5) 0.044(5) 0.012(3) 0.004(3) -0.004(3) C15A 0.038(4) 0.067(5) 0.076(6) 0.017(4) -0.002(3) -0.012(3) C16A 0.038(5) 0.067(5) 0.051(7) 0.005(4) -0.013(4) -0.011(4) C17A 0.047(5) 0.062(4) 0.030(4) 0.014(3) 0.002(3) -0.001(4) C18A 0.032(3) 0.029(2) 0.036(3) 0.009(2) 0.007(2) 0.007(2) C19A 0.043(3) 0.030(2) 0.037(3) 0.0039(17) 0.018(2) 0.0048(19) C20A 0.068(4) 0.029(2) 0.056(3) 0.003(2) 0.036(3) 0.005(3) C21A 0.094(9) 0.049(5) 0.084(8) 0.033(5) 0.059(8) 0.038(7) C22A 0.074(6) 0.036(3) 0.145(10) 0.016(5) -0.017(6) 0.002(4) C23A 0.036(4) 0.048(6) 0.231(17) 0.063(9) 0.050(10) 0.019(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9568(7) . ? P1 C13A 1.805(12) . ? P1 C1 1.811(2) . ? P1 C7 1.812(2) . ? P1 C13 1.867(10) . ? O1 C21 1.228(10) . ? C1 C2 1.383(3) . ? C1 C6 1.394(3) . ? C2 C3 1.376(3) . ? C3 C4 1.367(3) . ? C4 C5 1.377(3) . ? C5 C6 1.387(3) . ? C7 C8 1.382(3) . ? C7 C12 1.386(3) . ? C8 C9 1.377(3) . ? C9 C10 1.376(4) . ? C10 C11 1.370(4) . ? C11 C12 1.377(3) . ? C13 C14 1.395(9) . ? C13 C18 1.403(8) . ? C14 C15 1.382(9) . ? C15 C16 1.388(9) . ? C16 C17 1.375(8) . ? C17 C18 1.402(7) . ? C18 C19 1.467(7) . ? C19 C20 1.330(7) . ? C20 C21 1.475(9) . ? C21 C22 1.292(10) . ? C22 C23 1.404(10) . ? C23 C24 1.409(7) . ? C24 C29 1.387(4) . ? C24 C25 1.395(4) . ? C24 C23A 1.804(17) . ? C25 C26 1.381(4) . ? C26 C27 1.370(4) . ? C27 C28 1.371(3) . ? C28 C29 1.368(3) . ? O1A C21A 1.157(12) . ? C13A C14A 1.387(9) . ? C13A C18A 1.401(9) . ? C14A C15A 1.375(9) . ? C15A C16A 1.373(9) . ? C16A C17A 1.373(9) . ? C17A C18A 1.414(8) . ? C18A C19A 1.509(7) . ? C19A C20A 1.522(6) . ? C19A C20A 1.587(7) 3_756 ? C20A C21A 1.524(11) . ? C20A C19A 1.587(7) 3_756 ? C21A C22A 1.839(16) . ? C22A C23A 1.142(12) . ? 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 C13A P1 C1 99.4(3) . . ? C13A P1 C7 111.0(3) . . ? C1 P1 C7 105.42(9) . . ? C13A P1 C13 13.2(4) . . ? C1 P1 C13 111.1(3) . . ? C7 P1 C13 101.0(3) . . ? C13A P1 S1 115.7(3) . . ? C1 P1 S1 111.85(7) . . ? C7 P1 S1 112.35(7) . . ? C13 P1 S1 114.3(3) . . ? C2 C1 C6 118.4(2) . . ? C2 C1 P1 119.71(17) . . ? C6 C1 P1 121.89(17) . . ? C3 C2 C1 121.1(2) . . ? C4 C3 C2 120.0(2) . . ? C3 C4 C5 120.5(2) . . ? C4 C5 C6 119.7(2) . . ? C5 C6 C1 120.4(2) . . ? C8 C7 C12 118.7(2) . . ? C8 C7 P1 118.61(16) . . ? C12 C7 P1 122.69(17) . . ? C9 C8 C7 121.0(2) . . ? C10 C9 C8 119.8(3) . . ? C11 C10 C9 119.7(2) . . ? C10 C11 C12 120.7(2) . . ? C11 C12 C7 120.0(2) . . ? C14 C13 C18 121.3(8) . . ? C14 C13 P1 114.0(6) . . ? C18 C13 P1 124.5(7) . . ? C15 C14 C13 120.0(7) . . ? C14 C15 C16 119.5(6) . . ? C17 C16 C15 120.7(7) . . ? C16 C17 C18 121.4(6) . . ? C17 C18 C13 117.2(6) . . ? C17 C18 C19 120.3(5) . . ? C13 C18 C19 122.4(6) . . ? C20 C19 C18 127.1(5) . . ? C19 C20 C21 120.3(6) . . ? O1 C21 C22 125.4(7) . . ? O1 C21 C20 119.2(7) . . ? C22 C21 C20 115.4(7) . . ? C21 C22 C23 133.7(7) . . ? C22 C23 C24 129.8(6) . . ? C29 C24 C25 118.6(3) . . ? C29 C24 C23 112.7(4) . . ? C25 C24 C23 128.7(4) . . ? C29 C24 C23A 140.8(4) . . ? C25 C24 C23A 100.5(4) . . ? C23 C24 C23A 28.5(4) . . ? C26 C25 C24 120.1(3) . . ? C27 C26 C25 120.2(3) . . ? C26 C27 C28 120.1(3) . . ? C29 C28 C27 120.4(3) . . ? C28 C29 C24 120.7(3) . . ? C14A C13A C18A 118.6(9) . . ? C14A C13A P1 122.4(7) . . ? C18A C13A P1 118.7(6) . . ? C15A C14A C13A 122.2(8) . . ? C16A C15A C14A 120.2(7) . . ? C15A C16A C17A 118.7(7) . . ? C16A C17A C18A 122.5(6) . . ? C13A C18A C17A 117.7(7) . . ? C13A C18A C19A 122.5(6) . . ? C17A C18A C19A 119.2(5) . . ? C18A C19A C20A 119.6(4) . . ? C18A C19A C20A 116.1(4) . 3_756 ? C20A C19A C20A 88.8(3) . 3_756 ? C19A C20A C21A 115.1(5) . . ? C19A C20A C19A 91.2(3) . 3_756 ? C21A C20A C19A 114.7(5) . 3_756 ? O1A C21A C20A 123.2(9) . . ? O1A C21A C22A 133.3(10) . . ? C20A C21A C22A 103.3(8) . . ? C23A C22A C21A 101.2(13) . . ? C22A C23A C24 94.4(14) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.315 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.047 ### END data_4h _database_code_depnum_ccdc_archive 'CCDC 874835' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.3700(2) _cell_length_b 17.2807(3) _cell_length_c 14.7363(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.134(2) _cell_angle_gamma 90.00 _cell_volume 2332.79(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 27338 _cell_measurement_theta_min 3.0621 _cell_measurement_theta_max 30.4381 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96819 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_av_unetI/netI 0.1635 _diffrn_reflns_number 17895 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.1101 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.0621 _diffrn_reflns_theta_max 30.4381 _reflns_number_total 7057 _reflns_number_gt 3052 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0447596000 _diffrn_orient_matrix_UB_12 -0.0007115000 _diffrn_orient_matrix_UB_13 0.0453162000 _diffrn_orient_matrix_UB_21 -0.0534208000 _diffrn_orient_matrix_UB_22 0.0215623000 _diffrn_orient_matrix_UB_23 0.0168847000 _diffrn_orient_matrix_UB_31 -0.0338270000 _diffrn_orient_matrix_UB_32 -0.0349963000 _diffrn_orient_matrix_UB_33 0.0094405000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement '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^)+(0.0413P)^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 7057 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1230 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 0.840 _refine_ls_restrained_S_all 0.840 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91755(6) -0.01310(3) 0.22413(4) 0.05172(17) Uani 1 1 d . A . P1 P 0.98627(6) 0.09416(3) 0.23666(3) 0.03561(13) Uani 1 1 d . . . O1 O 0.6281(6) 0.0434(3) 0.4415(4) 0.0493(14) Uani 0.405(4) 1 d P A 1 C1 C 1.0712(2) 0.12232(10) 0.14175(13) 0.0377(4) Uani 1 1 d . A . C2 C 1.1200(2) 0.06566(11) 0.08929(15) 0.0512(6) Uani 1 1 d . . . H2 H 1.1057 0.0126 0.1019 0.061 Uiso 1 1 calc R A . C3 C 1.1892(3) 0.08573(14) 0.01892(15) 0.0622(6) Uani 1 1 d . A . H3 H 1.2222 0.0463 -0.0166 0.075 Uiso 1 1 calc R . . C4 C 1.2108(3) 0.16134(14) -0.00035(16) 0.0615(6) Uani 1 1 d . . . H4 H 1.2588 0.1744 -0.0490 0.074 Uiso 1 1 calc R A . C5 C 1.1629(3) 0.21885(13) 0.05070(17) 0.0650(7) Uani 1 1 d . A . H5 H 1.1778 0.2716 0.0372 0.078 Uiso 1 1 calc R . . C6 C 1.0932(2) 0.19983(11) 0.12157(16) 0.0570(6) Uani 1 1 d . . . H6 H 1.0602 0.2396 0.1566 0.068 Uiso 1 1 calc R A . C7 C 0.8383(2) 0.16257(10) 0.23420(12) 0.0345(4) Uani 1 1 d . A . C8 C 0.6978(2) 0.13914(12) 0.19590(15) 0.0532(6) Uani 1 1 d . . . H8 H 0.6806 0.0875 0.1742 0.064 Uiso 1 1 calc R A . C9 C 0.5815(3) 0.18960(15) 0.18870(18) 0.0741(7) Uani 1 1 d . A . H9 H 0.4851 0.1729 0.1622 0.089 Uiso 1 1 calc R . . C10 C 0.6070(3) 0.26440(14) 0.22033(17) 0.0660(7) Uani 1 1 d . . . H10 H 0.5278 0.2995 0.2155 0.079 Uiso 1 1 calc R A . C11 C 0.7458(3) 0.28847(11) 0.25864(15) 0.0544(6) Uani 1 1 d . A . H11 H 0.7626 0.3403 0.2797 0.065 Uiso 1 1 calc R . . C12 C 0.8613(2) 0.23768(10) 0.26668(13) 0.0435(5) Uani 1 1 d . . . H12 H 0.9571 0.2543 0.2946 0.052 Uiso 1 1 calc R A . C13 C 1.1047(11) 0.1181(5) 0.3537(6) 0.0243(19) Uani 0.405(4) 1 d PD A 1 C14 C 1.2492(9) 0.1336(4) 0.3501(5) 0.0370(19) Uani 0.405(4) 1 d PD A 1 H14 H 1.2777 0.1347 0.2920 0.044 Uiso 0.405(4) 1 calc PR A 1 C15 C 1.3511(8) 0.1473(4) 0.4307(6) 0.044(2) Uani 0.405(4) 1 d PD A 1 H15 H 1.4500 0.1573 0.4287 0.053 Uiso 0.405(4) 1 calc PR A 1 C16 C 1.3067(9) 0.1462(5) 0.5147(7) 0.043(2) Uani 0.405(4) 1 d PD A 1 H16 H 1.3757 0.1574 0.5702 0.052 Uiso 0.405(4) 1 calc PR A 1 C17 C 1.1655(8) 0.1293(4) 0.5192(4) 0.0382(16) Uani 0.405(4) 1 d PD A 1 H17 H 1.1393 0.1270 0.5780 0.046 Uiso 0.405(4) 1 calc PR A 1 C18 C 1.0587(6) 0.1152(3) 0.4383(4) 0.0313(13) Uani 0.405(4) 1 d PD A 1 C19 C 0.9082(5) 0.0954(2) 0.4452(3) 0.0352(13) Uani 0.405(4) 1 d P A 1 H19 H 0.8380 0.0931 0.3884 0.042 Uiso 0.405(4) 1 calc PR A 1 C20 C 0.8597(8) 0.0804(4) 0.5219(4) 0.0363(18) Uani 0.405(4) 1 d P A 1 H20 H 0.9246 0.0837 0.5807 0.044 Uiso 0.405(4) 1 calc PR A 1 C21 C 0.7041(8) 0.0586(5) 0.5162(7) 0.042(2) Uani 0.405(4) 1 d P A 1 C22 C 0.6687(8) 0.0551(3) 0.5920(4) 0.0319(16) Uani 0.405(4) 1 d P A 1 H22 H 0.5863 0.0228 0.5907 0.038 Uiso 0.405(4) 1 calc PR A 1 C23 C 0.7230(7) 0.0887(4) 0.6820(4) 0.0258(12) Uani 0.405(4) 1 d P A 1 H23 H 0.8148 0.1140 0.6902 0.031 Uiso 0.405(4) 1 calc PR A 1 C24 C 0.6570(3) 0.08862(13) 0.75927(17) 0.0607(7) Uani 1 1 d . . . C25 C 0.5307(3) 0.05309(12) 0.77471(18) 0.0640(7) Uani 1 1 d . A . H25 H 0.4704 0.0245 0.7263 0.077 Uiso 1 1 calc R . . C26 C 0.4930(3) 0.05931(13) 0.86007(18) 0.0624(6) Uani 1 1 d . . . H26 H 0.4076 0.0344 0.8705 0.075 Uiso 1 1 calc R A . C27 C 0.5781(3) 0.10112(13) 0.92936(16) 0.0594(6) Uani 1 1 d . A . H27 H 0.5516 0.1057 0.9879 0.071 Uiso 1 1 calc R . . C28 C 0.7018(3) 0.13650(13) 0.91445(18) 0.0639(6) Uani 1 1 d . . . H28 H 0.7608 0.1656 0.9629 0.077 Uiso 1 1 calc R A . C29 C 0.7412(3) 0.13042(13) 0.83101(19) 0.0660(7) Uani 1 1 d . A . H29 H 0.8276 0.1552 0.8219 0.079 Uiso 1 1 calc R . . O1A O 0.7058(6) 0.0618(3) 0.4535(5) 0.098(2) Uani 0.595(4) 1 d P A 2 C13A C 1.1333(9) 0.1143(4) 0.3329(5) 0.0318(15) Uani 0.595(4) 1 d PD A 2 C14A C 1.2581(7) 0.1542(3) 0.3231(4) 0.0444(14) Uani 0.595(4) 1 d PD A 2 H14A H 1.2699 0.1668 0.2624 0.053 Uiso 0.595(4) 1 calc PR A 2 C15A C 1.3658(6) 0.1762(3) 0.3981(4) 0.0622(16) Uani 0.595(4) 1 d PD A 2 H15A H 1.4497 0.2032 0.3886 0.075 Uiso 0.595(4) 1 calc PR A 2 C16A C 1.3500(7) 0.1587(4) 0.4858(5) 0.060(2) Uani 0.595(4) 1 d PD A 2 H16A H 1.4227 0.1742 0.5377 0.072 Uiso 0.595(4) 1 calc PR A 2 C17A C 1.2289(7) 0.1186(3) 0.4993(4) 0.0478(13) Uani 0.595(4) 1 d PD A 2 H17A H 1.2194 0.1072 0.5608 0.057 Uiso 0.595(4) 1 calc PR A 2 C18A C 1.1191(4) 0.0942(2) 0.4243(3) 0.0322(8) Uani 0.595(4) 1 d PD A 2 C19A C 1.0011(4) 0.04104(15) 0.4419(2) 0.0334(9) Uani 0.595(4) 1 d P . 2 H19A H 0.9152 0.0427 0.3886 0.040 Uiso 0.595(4) 1 calc PR A 2 C20A C 0.9505(5) 0.04601(19) 0.5341(2) 0.0463(11) Uani 0.595(4) 1 d P . 2 H20A H 1.0113 0.0832 0.5779 0.056 Uiso 0.595(4) 1 calc PR A 2 C21A C 0.7875(11) 0.0608(4) 0.5258(5) 0.074(3) Uani 0.595(4) 1 d P A 2 C22A C 0.7699(7) 0.0839(3) 0.6386(5) 0.0831(19) Uani 0.595(4) 1 d P A 2 H22A H 0.8436 0.1061 0.6856 0.100 Uiso 0.595(4) 1 calc PR A 2 C23A C 0.6532(7) 0.0675(3) 0.6460(7) 0.086(3) Uani 0.595(4) 1 d P A 2 H23A H 0.5750 0.0473 0.6004 0.104 Uiso 0.595(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0454(3) 0.0327(2) 0.0703(4) -0.0009(2) -0.0033(3) -0.0045(2) P1 0.0360(3) 0.0305(2) 0.0360(3) 0.0019(2) -0.0021(2) 0.0006(2) O1 0.045(3) 0.057(2) 0.039(2) -0.0096(18) -0.008(2) -0.010(2) C1 0.0330(11) 0.0370(9) 0.0425(12) -0.0001(8) 0.0063(9) 0.0057(8) C2 0.0569(15) 0.0455(11) 0.0499(14) -0.0088(10) 0.0079(11) 0.0015(11) C3 0.0689(17) 0.0723(15) 0.0488(15) -0.0160(12) 0.0201(12) 0.0080(13) C4 0.0596(16) 0.0769(15) 0.0524(15) -0.0010(12) 0.0220(12) 0.0029(13) C5 0.0671(17) 0.0566(13) 0.0812(19) 0.0074(12) 0.0386(14) 0.0007(12) C6 0.0619(16) 0.0422(11) 0.0763(17) 0.0021(11) 0.0361(13) 0.0077(11) C7 0.0402(12) 0.0382(9) 0.0254(10) 0.0010(8) 0.0071(8) 0.0035(9) C8 0.0415(13) 0.0533(12) 0.0615(15) -0.0116(10) 0.0036(11) 0.0053(11) C9 0.0426(15) 0.0881(18) 0.087(2) -0.0147(15) 0.0036(13) 0.0140(14) C10 0.0609(18) 0.0675(15) 0.0739(18) 0.0022(13) 0.0242(14) 0.0273(13) C11 0.0705(18) 0.0435(11) 0.0542(15) -0.0022(10) 0.0242(12) 0.0137(12) C12 0.0484(13) 0.0455(11) 0.0376(12) -0.0035(9) 0.0109(9) 0.0030(10) C13 0.027(4) 0.024(3) 0.020(4) -0.006(3) -0.001(3) 0.001(3) C14 0.037(4) 0.037(4) 0.035(4) 0.000(3) 0.004(3) 0.005(3) C15 0.024(3) 0.057(4) 0.046(6) -0.006(4) -0.004(4) -0.003(3) C16 0.031(5) 0.055(5) 0.042(5) -0.009(3) 0.002(3) -0.010(3) C17 0.041(4) 0.045(3) 0.026(3) 0.000(2) 0.001(3) -0.005(3) C18 0.034(3) 0.031(3) 0.027(3) -0.003(2) 0.001(2) 0.002(2) C19 0.037(3) 0.039(2) 0.028(3) -0.004(2) 0.0054(19) -0.005(2) C20 0.033(4) 0.051(4) 0.021(3) -0.007(3) -0.001(3) -0.005(3) C21 0.027(4) 0.032(3) 0.059(5) -0.007(3) -0.009(4) -0.004(3) C22 0.047(4) 0.028(2) 0.016(3) -0.001(2) -0.004(2) -0.008(3) C23 0.015(3) 0.034(3) 0.030(3) 0.000(2) 0.010(2) -0.007(3) C24 0.0800(19) 0.0471(12) 0.0625(17) 0.0133(12) 0.0323(14) 0.0257(13) C25 0.0677(18) 0.0540(14) 0.0640(17) -0.0041(11) -0.0001(14) 0.0066(13) C26 0.0494(15) 0.0669(14) 0.0738(19) -0.0021(13) 0.0196(13) -0.0038(12) C27 0.0543(15) 0.0692(14) 0.0590(15) -0.0045(12) 0.0217(12) 0.0032(13) C28 0.0511(16) 0.0650(14) 0.0772(19) -0.0094(13) 0.0174(13) -0.0051(12) C29 0.0643(17) 0.0582(13) 0.086(2) 0.0002(13) 0.0389(15) 0.0021(12) O1A 0.070(4) 0.105(4) 0.132(5) 0.062(3) 0.050(5) 0.034(3) C13A 0.037(3) 0.033(2) 0.028(3) 0.0079(19) 0.012(2) 0.006(2) C14A 0.032(2) 0.057(3) 0.042(3) 0.014(2) 0.002(2) -0.006(2) C15A 0.043(3) 0.069(3) 0.068(4) 0.018(2) -0.004(2) -0.015(2) C16A 0.037(4) 0.080(4) 0.053(5) 0.005(3) -0.014(3) -0.007(3) C17A 0.051(4) 0.059(3) 0.030(3) 0.010(2) 0.003(2) 0.002(3) C18A 0.034(2) 0.0286(18) 0.034(2) 0.0059(16) 0.0071(17) 0.0043(17) C19A 0.045(2) 0.0302(15) 0.0291(17) 0.0025(12) 0.0168(14) 0.0034(14) C20A 0.071(3) 0.0324(17) 0.044(2) 0.0044(15) 0.030(2) 0.0103(19) C21A 0.114(8) 0.052(4) 0.077(5) 0.042(4) 0.065(6) 0.048(5) C22A 0.067(4) 0.044(2) 0.126(6) 0.006(3) -0.008(4) 0.006(3) C23A 0.039(3) 0.052(4) 0.181(10) 0.055(5) 0.050(6) 0.019(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9581(6) . ? P1 C13A 1.792(9) . ? P1 C1 1.8148(19) . ? P1 C7 1.8167(18) . ? P1 C13 1.890(10) . ? O1 C21 1.207(11) . ? C1 C2 1.383(3) . ? C1 C6 1.397(2) . ? C2 C3 1.378(3) . ? C3 C4 1.361(3) . ? C4 C5 1.377(3) . ? C5 C6 1.383(3) . ? C7 C8 1.380(3) . ? C7 C12 1.385(2) . ? C8 C9 1.382(3) . ? C9 C10 1.378(3) . ? C10 C11 1.369(3) . ? C11 C12 1.379(3) . ? C13 C14 1.392(10) . ? C13 C18 1.402(8) . ? C14 C15 1.378(9) . ? C15 C16 1.386(10) . ? C16 C17 1.371(8) . ? C17 C18 1.408(7) . ? C18 C19 1.475(7) . ? C19 C20 1.329(8) . ? C20 C21 1.491(10) . ? C21 C22 1.233(11) . ? C22 C23 1.440(9) . ? C23 C24 1.404(7) . ? C24 C29 1.382(3) . ? C24 C25 1.394(3) . ? C24 C23A 1.701(10) . ? C25 C26 1.380(3) . ? C26 C27 1.363(3) . ? C27 C28 1.368(3) . ? C28 C29 1.360(3) . ? O1A C21A 1.174(9) . ? C13A C14A 1.390(7) . ? C13A C18A 1.423(6) . ? C14A C15A 1.384(7) . ? C15A C16A 1.366(7) . ? C16A C17A 1.379(7) . ? C17A C18A 1.408(6) . ? C18A C19A 1.501(5) . ? C19A C20A 1.533(4) . ? C19A C20A 1.590(5) 3_756 ? C20A C21A 1.528(9) . ? C20A C19A 1.590(5) 3_756 ? C21A C22A 1.751(10) . ? C22A C23A 1.157(8) . ? 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 C13A P1 C1 99.8(2) . . ? C13A P1 C7 110.2(2) . . ? C1 P1 C7 105.45(8) . . ? C13A P1 C13 13.8(3) . . ? C1 P1 C13 112.1(3) . . ? C7 P1 C13 100.1(3) . . ? C13A P1 S1 116.2(2) . . ? C1 P1 S1 111.71(6) . . ? C7 P1 S1 112.32(6) . . ? C13 P1 S1 114.3(3) . . ? C2 C1 C6 118.60(19) . . ? C2 C1 P1 119.39(15) . . ? C6 C1 P1 121.97(15) . . ? C3 C2 C1 120.37(19) . . ? C4 C3 C2 120.8(2) . . ? C3 C4 C5 119.9(2) . . ? C4 C5 C6 120.0(2) . . ? C5 C6 C1 120.21(19) . . ? C8 C7 C12 118.84(18) . . ? C8 C7 P1 118.42(14) . . ? C12 C7 P1 122.72(15) . . ? C7 C8 C9 121.01(19) . . ? C10 C9 C8 119.2(2) . . ? C11 C10 C9 120.4(2) . . ? C10 C11 C12 120.15(19) . . ? C11 C12 C7 120.3(2) . . ? C14 C13 C18 121.6(8) . . ? C14 C13 P1 113.4(6) . . ? C18 C13 P1 124.9(6) . . ? C15 C14 C13 120.2(7) . . ? C14 C15 C16 118.9(6) . . ? C17 C16 C15 121.4(7) . . ? C16 C17 C18 121.1(7) . . ? C13 C18 C17 116.8(6) . . ? C13 C18 C19 123.1(6) . . ? C17 C18 C19 120.1(5) . . ? C20 C19 C18 127.3(5) . . ? C19 C20 C21 120.4(6) . . ? O1 C21 C22 126.6(7) . . ? O1 C21 C20 119.3(9) . . ? C22 C21 C20 114.1(7) . . ? C21 C22 C23 134.9(7) . . ? C24 C23 C22 128.0(6) . . ? C29 C24 C25 118.2(2) . . ? C29 C24 C23 110.0(3) . . ? C25 C24 C23 131.7(4) . . ? C29 C24 C23A 138.9(3) . . ? C25 C24 C23A 102.8(3) . . ? C23 C24 C23A 29.2(3) . . ? C26 C25 C24 120.2(2) . . ? C27 C26 C25 120.2(2) . . ? C26 C27 C28 119.9(2) . . ? C29 C28 C27 120.7(2) . . ? C28 C29 C24 120.8(2) . . ? C14A C13A C18A 117.9(6) . . ? C14A C13A P1 122.5(5) . . ? C18A C13A P1 119.5(5) . . ? C15A C14A C13A 122.8(6) . . ? C16A C15A C14A 119.2(5) . . ? C15A C16A C17A 120.3(6) . . ? C16A C17A C18A 121.7(5) . . ? C17A C18A C13A 118.1(5) . . ? C17A C18A C19A 119.4(4) . . ? C13A C18A C19A 122.1(4) . . ? C18A C19A C20A 119.7(3) . . ? C18A C19A C20A 115.6(3) . 3_756 ? C20A C19A C20A 89.0(2) . 3_756 ? C21A C20A C19A 115.4(4) . . ? C21A C20A C19A 114.2(3) . 3_756 ? C19A C20A C19A 91.0(2) . 3_756 ? O1A C21A C20A 121.7(6) . . ? O1A C21A C22A 133.2(8) . . ? C20A C21A C22A 104.7(6) . . ? C23A C22A C21A 108.3(9) . . ? C22A C23A C24 102.4(9) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.231 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.041 ### END data_6h _database_code_depnum_ccdc_archive 'CCDC 874836' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.3726(2) _cell_length_b 17.2873(3) _cell_length_c 14.7499(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.167(2) _cell_angle_gamma 90.00 _cell_volume 2336.20(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 27338 _cell_measurement_theta_min 3.0621 _cell_measurement_theta_max 30.4381 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97339 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 18304 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.1649 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.0621 _diffrn_reflns_theta_max 30.4381 _reflns_number_total 7058 _reflns_number_gt 3041 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0447596000 _diffrn_orient_matrix_UB_12 -0.0007115000 _diffrn_orient_matrix_UB_13 0.0453162000 _diffrn_orient_matrix_UB_21 -0.0534208000 _diffrn_orient_matrix_UB_22 0.0215623000 _diffrn_orient_matrix_UB_23 0.0168847000 _diffrn_orient_matrix_UB_31 -0.0338270000 _diffrn_orient_matrix_UB_32 -0.0349963000 _diffrn_orient_matrix_UB_33 0.0094405000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement '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^)+(0.0415P)^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 7058 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1268 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 0.844 _refine_ls_restrained_S_all 0.844 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91767(6) -0.01359(3) 0.22358(4) 0.05238(17) Uani 1 1 d . A . P1 P 0.98655(6) 0.09364(3) 0.23633(3) 0.03608(13) Uani 1 1 d . . . O1 O 0.6271(6) 0.0431(3) 0.4416(4) 0.0503(15) Uani 0.370(4) 1 d P A 1 C1 C 1.0711(2) 0.12163(10) 0.14136(13) 0.0383(4) Uani 1 1 d . A . C2 C 1.1203(2) 0.06537(11) 0.08910(15) 0.0521(6) Uani 1 1 d . . . H2 H 1.1061 0.0124 0.1017 0.063 Uiso 1 1 calc R A . C3 C 1.1896(3) 0.08492(14) 0.01908(15) 0.0632(6) Uani 1 1 d . A . H3 H 1.2230 0.0454 -0.0161 0.076 Uiso 1 1 calc R . . C4 C 1.2109(3) 0.16069(14) -0.00046(15) 0.0611(6) Uani 1 1 d . . . H4 H 1.2595 0.1736 -0.0488 0.073 Uiso 1 1 calc R A . C5 C 1.1620(3) 0.21841(13) 0.04975(17) 0.0654(7) Uani 1 1 d . A . H5 H 1.1764 0.2712 0.0361 0.079 Uiso 1 1 calc R . . C6 C 1.0917(3) 0.19900(11) 0.12053(16) 0.0586(6) Uani 1 1 d . . . H6 H 1.0573 0.2387 0.1550 0.070 Uiso 1 1 calc R A . C7 C 0.8391(2) 0.16225(10) 0.23423(12) 0.0348(4) Uani 1 1 d . A . C8 C 0.6982(2) 0.13905(12) 0.19567(15) 0.0542(6) Uani 1 1 d . . . H8 H 0.6809 0.0875 0.1738 0.065 Uiso 1 1 calc R A . C9 C 0.5822(3) 0.18956(15) 0.18837(18) 0.0754(8) Uani 1 1 d . A . H9 H 0.4859 0.1729 0.1617 0.091 Uiso 1 1 calc R . . C10 C 0.6073(3) 0.26400(14) 0.21998(17) 0.0672(7) Uani 1 1 d . . . H10 H 0.5281 0.2992 0.2149 0.081 Uiso 1 1 calc R A . C11 C 0.7463(3) 0.28787(12) 0.25887(15) 0.0563(6) Uani 1 1 d . A . H11 H 0.7630 0.3396 0.2803 0.068 Uiso 1 1 calc R . . C12 C 0.8622(2) 0.23698(10) 0.26701(13) 0.0441(5) Uani 1 1 d . . . H12 H 0.9579 0.2535 0.2952 0.053 Uiso 1 1 calc R A . C13 C 1.1028(12) 0.1177(5) 0.3540(7) 0.026(2) Uani 0.370(4) 1 d PD A 1 C14 C 1.2478(10) 0.1334(4) 0.3508(5) 0.037(2) Uani 0.370(4) 1 d PD A 1 H14 H 1.2763 0.1346 0.2927 0.045 Uiso 0.370(4) 1 calc PR A 1 C15 C 1.3504(9) 0.1475(4) 0.4316(6) 0.045(2) Uani 0.370(4) 1 d PD A 1 H15 H 1.4492 0.1575 0.4293 0.054 Uiso 0.370(4) 1 calc PR A 1 C16 C 1.3069(9) 0.1467(5) 0.5150(6) 0.040(2) Uani 0.370(4) 1 d PD A 1 H16 H 1.3756 0.1582 0.5705 0.048 Uiso 0.370(4) 1 calc PR A 1 C17 C 1.1650(8) 0.1294(4) 0.5188(5) 0.0379(16) Uani 0.370(4) 1 d PD A 1 H17 H 1.1386 0.1273 0.5775 0.045 Uiso 0.370(4) 1 calc PR A 1 C18 C 1.0585(7) 0.1149(3) 0.4388(4) 0.0316(14) Uani 0.370(4) 1 d PD A 1 C19 C 0.9070(5) 0.0950(3) 0.4454(3) 0.0356(14) Uani 0.370(4) 1 d P A 1 H19 H 0.8372 0.0922 0.3885 0.043 Uiso 0.370(4) 1 calc PR A 1 C20 C 0.8578(9) 0.0806(5) 0.5223(5) 0.037(2) Uani 0.370(4) 1 d P A 1 H20 H 0.9221 0.0846 0.5812 0.044 Uiso 0.370(4) 1 calc PR A 1 C21 C 0.7034(9) 0.0584(5) 0.5162(7) 0.043(2) Uani 0.370(4) 1 d P A 1 C22 C 0.6695(9) 0.0556(3) 0.5918(4) 0.0303(16) Uani 0.370(4) 1 d P A 1 H22 H 0.5869 0.0234 0.5903 0.036 Uiso 0.370(4) 1 calc PR A 1 C23 C 0.7223(8) 0.0884(4) 0.6825(5) 0.0253(13) Uani 0.370(4) 1 d P A 1 H23 H 0.8147 0.1132 0.6918 0.030 Uiso 0.370(4) 1 calc PR A 1 C24 C 0.6551(3) 0.08850(13) 0.75828(17) 0.0630(7) Uani 1 1 d . . . C25 C 0.5296(3) 0.05274(12) 0.77450(18) 0.0651(7) Uani 1 1 d . A . H25 H 0.4694 0.0237 0.7266 0.078 Uiso 1 1 calc R . . C26 C 0.4925(3) 0.05932(13) 0.85993(18) 0.0643(6) Uani 1 1 d . . . H26 H 0.4071 0.0346 0.8708 0.077 Uiso 1 1 calc R A . C27 C 0.5783(3) 0.10132(13) 0.92873(16) 0.0602(6) Uani 1 1 d . A . H27 H 0.5527 0.1059 0.9875 0.072 Uiso 1 1 calc R . . C28 C 0.7013(3) 0.13688(13) 0.91303(18) 0.0649(6) Uani 1 1 d . . . H28 H 0.7603 0.1664 0.9610 0.078 Uiso 1 1 calc R A . C29 C 0.7399(3) 0.13048(13) 0.82955(19) 0.0672(7) Uani 1 1 d . A . H29 H 0.8262 0.1551 0.8201 0.081 Uiso 1 1 calc R . . O1A O 0.7051(5) 0.0623(3) 0.4539(4) 0.0970(19) Uani 0.630(4) 1 d P A 2 C13A C 1.1337(8) 0.1138(3) 0.3334(5) 0.0298(13) Uani 0.630(4) 1 d PD A 2 C14A C 1.2581(6) 0.1535(3) 0.3225(4) 0.0437(13) Uani 0.630(4) 1 d PD A 2 H14A H 1.2692 0.1660 0.2616 0.052 Uiso 0.630(4) 1 calc PR A 2 C15A C 1.3666(5) 0.1752(3) 0.3973(4) 0.0621(15) Uani 0.630(4) 1 d PD A 2 H15A H 1.4504 0.2023 0.3878 0.075 Uiso 0.630(4) 1 calc PR A 2 C16A C 1.3515(7) 0.1574(4) 0.4846(4) 0.0627(19) Uani 0.630(4) 1 d PD A 2 H16A H 1.4252 0.1722 0.5363 0.075 Uiso 0.630(4) 1 calc PR A 2 C17A C 1.2301(6) 0.1180(3) 0.4989(3) 0.0484(12) Uani 0.630(4) 1 d PD A 2 H17A H 1.2210 0.1070 0.5606 0.058 Uiso 0.630(4) 1 calc PR A 2 C18A C 1.1191(4) 0.0936(2) 0.4241(3) 0.0321(8) Uani 0.630(4) 1 d PD A 2 C19A C 1.0007(3) 0.04085(15) 0.44187(19) 0.0351(9) Uani 0.630(4) 1 d P . 2 H19A H 0.9148 0.0425 0.3886 0.042 Uiso 0.630(4) 1 calc PR A 2 C20A C 0.9505(5) 0.04630(18) 0.5341(2) 0.0467(10) Uani 0.630(4) 1 d P . 2 H20A H 1.0115 0.0836 0.5777 0.056 Uiso 0.630(4) 1 calc PR A 2 C21A C 0.7878(10) 0.0610(4) 0.5261(5) 0.075(3) Uani 0.630(4) 1 d P A 2 C22A C 0.7702(6) 0.0844(3) 0.6374(5) 0.0838(18) Uani 0.630(4) 1 d P A 2 H22A H 0.8440 0.1073 0.6837 0.101 Uiso 0.630(4) 1 calc PR A 2 C23A C 0.6526(7) 0.0676(3) 0.6466(7) 0.086(3) Uani 0.630(4) 1 d P A 2 H23A H 0.5744 0.0469 0.6015 0.104 Uiso 0.630(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0460(3) 0.0330(2) 0.0713(4) -0.0011(2) -0.0031(3) -0.0044(2) P1 0.0362(3) 0.0312(2) 0.0368(3) 0.0022(2) -0.0017(2) 0.0006(2) O1 0.046(3) 0.056(2) 0.041(3) -0.010(2) -0.009(3) -0.011(3) C1 0.0340(11) 0.0380(9) 0.0422(12) 0.0005(8) 0.0063(9) 0.0059(9) C2 0.0574(15) 0.0443(10) 0.0525(14) -0.0081(10) 0.0066(11) 0.0024(11) C3 0.0708(17) 0.0721(15) 0.0498(15) -0.0168(12) 0.0197(12) 0.0082(13) C4 0.0583(16) 0.0800(15) 0.0498(15) -0.0006(12) 0.0218(11) 0.0039(13) C5 0.0680(18) 0.0561(13) 0.0823(19) 0.0088(12) 0.0385(14) 0.0036(12) C6 0.0666(16) 0.0406(11) 0.0795(17) 0.0031(11) 0.0401(13) 0.0092(11) C7 0.0405(12) 0.0386(9) 0.0251(10) 0.0003(8) 0.0063(8) 0.0039(9) C8 0.0431(14) 0.0539(12) 0.0621(15) -0.0123(10) 0.0034(11) 0.0041(11) C9 0.0449(15) 0.0859(17) 0.091(2) -0.0157(15) 0.0034(13) 0.0168(14) C10 0.0616(18) 0.0690(15) 0.0753(18) 0.0039(13) 0.0243(14) 0.0290(13) C11 0.0730(18) 0.0452(11) 0.0565(15) -0.0038(10) 0.0268(13) 0.0146(12) C12 0.0488(13) 0.0477(11) 0.0369(12) -0.0032(9) 0.0115(9) 0.0010(10) C13 0.028(5) 0.025(3) 0.024(5) -0.004(3) 0.002(3) 0.001(3) C14 0.040(5) 0.042(4) 0.030(5) 0.003(3) 0.006(3) 0.007(4) C15 0.028(4) 0.059(5) 0.045(6) -0.006(5) 0.001(4) -0.008(3) C16 0.023(5) 0.056(5) 0.038(5) -0.010(3) 0.001(3) -0.009(3) C17 0.033(4) 0.048(3) 0.030(4) -0.001(3) 0.001(3) -0.005(3) C18 0.036(4) 0.029(3) 0.029(3) -0.002(2) 0.004(3) 0.005(3) C19 0.037(3) 0.043(3) 0.028(3) -0.003(2) 0.009(2) -0.001(3) C20 0.039(5) 0.045(5) 0.021(4) -0.007(3) -0.005(3) -0.005(3) C21 0.026(4) 0.033(3) 0.062(6) -0.006(4) -0.010(4) -0.002(4) C22 0.041(5) 0.029(3) 0.018(3) -0.001(2) -0.002(3) -0.007(3) C23 0.015(3) 0.031(3) 0.032(3) 0.002(3) 0.011(2) -0.004(3) C24 0.085(2) 0.0494(12) 0.0624(17) 0.0145(12) 0.0344(15) 0.0288(14) C25 0.0678(18) 0.0545(14) 0.0679(18) -0.0027(12) 0.0026(14) 0.0053(13) C26 0.0513(16) 0.0694(15) 0.0754(19) -0.0026(13) 0.0209(13) -0.0045(12) C27 0.0561(16) 0.0713(14) 0.0575(15) -0.0006(12) 0.0219(12) 0.0043(13) C28 0.0522(16) 0.0668(14) 0.0781(19) -0.0104(13) 0.0190(13) -0.0043(12) C29 0.0653(18) 0.0603(14) 0.086(2) -0.0002(14) 0.0378(15) 0.0038(13) O1A 0.069(4) 0.108(3) 0.126(4) 0.060(3) 0.048(4) 0.037(3) C13A 0.032(3) 0.031(2) 0.028(3) 0.0066(17) 0.011(2) 0.0042(18) C14A 0.034(2) 0.058(3) 0.036(3) 0.014(2) 0.002(2) -0.006(2) C15A 0.041(3) 0.077(3) 0.062(4) 0.020(2) -0.002(2) -0.014(2) C16A 0.037(3) 0.089(4) 0.054(5) 0.007(3) -0.009(3) -0.006(3) C17A 0.047(4) 0.061(3) 0.033(3) 0.011(2) 0.000(2) 0.003(3) C18A 0.034(2) 0.0309(17) 0.031(2) 0.0057(15) 0.0059(16) 0.0048(16) C19A 0.049(2) 0.0312(14) 0.0295(17) 0.0037(12) 0.0173(14) 0.0030(14) C20A 0.074(3) 0.0308(15) 0.044(2) 0.0054(14) 0.0315(19) 0.0094(18) C21A 0.117(8) 0.051(4) 0.078(5) 0.042(4) 0.066(6) 0.044(5) C22A 0.069(4) 0.043(2) 0.127(6) 0.007(3) -0.009(4) 0.004(3) C23A 0.043(3) 0.055(3) 0.172(9) 0.054(5) 0.047(5) 0.018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9589(6) . ? P1 C13A 1.800(8) . ? P1 C1 1.8147(19) . ? P1 C7 1.8167(18) . ? P1 C13 1.891(11) . ? O1 C21 1.208(12) . ? C1 C2 1.379(3) . ? C1 C6 1.395(2) . ? C2 C3 1.373(3) . ? C3 C4 1.365(3) . ? C4 C5 1.377(3) . ? C5 C6 1.388(3) . ? C7 C12 1.380(2) . ? C7 C8 1.383(3) . ? C8 C9 1.381(3) . ? C9 C10 1.372(3) . ? C10 C11 1.371(3) . ? C11 C12 1.383(3) . ? C13 C14 1.397(10) . ? C13 C18 1.398(9) . ? C14 C15 1.386(10) . ? C15 C16 1.375(10) . ? C16 C17 1.376(8) . ? C17 C18 1.399(8) . ? C18 C19 1.484(8) . ? C19 C20 1.335(9) . ? C20 C21 1.481(11) . ? C21 C22 1.223(12) . ? C22 C23 1.441(10) . ? C23 C24 1.395(8) . ? C24 C29 1.383(3) . ? C24 C25 1.393(3) . ? C24 C23A 1.682(10) . ? C25 C26 1.381(3) . ? C26 C27 1.364(3) . ? C27 C28 1.369(3) . ? C28 C29 1.359(3) . ? O1A C21A 1.178(9) . ? C13A C14A 1.391(7) . ? C13A C18A 1.417(6) . ? C14A C15A 1.386(6) . ? C15A C16A 1.360(7) . ? C16A C17A 1.379(7) . ? C17A C18A 1.412(6) . ? C18A C19A 1.502(5) . ? C19A C20A 1.533(4) . ? C19A C20A 1.592(4) 3_756 ? C20A C21A 1.526(8) . ? C20A C19A 1.592(4) 3_756 ? C21A C22A 1.733(10) . ? C22A C23A 1.175(7) . ? 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 C13A P1 C1 100.14(18) . . ? C13A P1 C7 109.84(18) . . ? C1 P1 C7 105.51(8) . . ? C13A P1 C13 14.3(3) . . ? C1 P1 C13 112.9(3) . . ? C7 P1 C13 99.3(3) . . ? C13A P1 S1 116.21(19) . . ? C1 P1 S1 111.53(6) . . ? C7 P1 S1 112.46(7) . . ? C13 P1 S1 114.2(3) . . ? C2 C1 C6 118.37(19) . . ? C2 C1 P1 119.68(15) . . ? C6 C1 P1 121.92(15) . . ? C3 C2 C1 120.91(19) . . ? C4 C3 C2 120.6(2) . . ? C3 C4 C5 120.1(2) . . ? C4 C5 C6 119.6(2) . . ? C5 C6 C1 120.46(19) . . ? C12 C7 C8 118.76(18) . . ? C12 C7 P1 122.86(15) . . ? C8 C7 P1 118.35(14) . . ? C9 C8 C7 121.10(19) . . ? C10 C9 C8 119.4(2) . . ? C11 C10 C9 120.3(2) . . ? C10 C11 C12 120.3(2) . . ? C7 C12 C11 120.2(2) . . ? C14 C13 C18 120.8(9) . . ? C14 C13 P1 112.8(6) . . ? C18 C13 P1 126.2(7) . . ? C15 C14 C13 120.5(8) . . ? C16 C15 C14 119.0(7) . . ? C15 C16 C17 120.7(7) . . ? C16 C17 C18 121.9(7) . . ? C13 C18 C17 117.0(7) . . ? C13 C18 C19 122.3(6) . . ? C17 C18 C19 120.6(5) . . ? C20 C19 C18 127.3(5) . . ? C19 C20 C21 120.3(7) . . ? O1 C21 C22 127.1(8) . . ? O1 C21 C20 119.7(10) . . ? C22 C21 C20 113.1(8) . . ? C21 C22 C23 136.6(8) . . ? C24 C23 C22 128.3(7) . . ? C29 C24 C25 118.3(2) . . ? C29 C24 C23 109.0(4) . . ? C25 C24 C23 132.7(4) . . ? C29 C24 C23A 138.1(3) . . ? C25 C24 C23A 103.6(3) . . ? C23 C24 C23A 29.5(3) . . ? C26 C25 C24 120.3(2) . . ? C27 C26 C25 120.0(2) . . ? C26 C27 C28 119.9(2) . . ? C29 C28 C27 120.8(2) . . ? C28 C29 C24 120.7(2) . . ? C14A C13A C18A 118.7(6) . . ? C14A C13A P1 121.6(5) . . ? C18A C13A P1 119.5(4) . . ? C15A C14A C13A 122.2(5) . . ? C16A C15A C14A 119.2(5) . . ? C15A C16A C17A 120.7(5) . . ? C16A C17A C18A 121.5(4) . . ? C17A C18A C13A 117.6(4) . . ? C17A C18A C19A 119.6(3) . . ? C13A C18A C19A 122.4(4) . . ? C18A C19A C20A 119.6(3) . . ? C18A C19A C20A 115.2(3) . 3_756 ? C20A C19A C20A 89.3(2) . 3_756 ? C21A C20A C19A 115.5(3) . . ? C21A C20A C19A 114.2(3) . 3_756 ? C19A C20A C19A 90.7(2) . 3_756 ? O1A C21A C20A 122.0(6) . . ? O1A C21A C22A 132.5(7) . . ? C20A C21A C22A 105.0(6) . . ? C23A C22A C21A 109.3(8) . . ? C22A C23A C24 103.9(9) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.250 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.041 ### END data_8h _database_code_depnum_ccdc_archive 'CCDC 874837' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.3734(2) _cell_length_b 17.2887(3) _cell_length_c 14.7596(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.190(2) _cell_angle_gamma 90.00 _cell_volume 2337.92(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 27338 _cell_measurement_theta_min 3.0621 _cell_measurement_theta_max 30.4381 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97693 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 18322 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.1655 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.0621 _diffrn_reflns_theta_max 30.4381 _reflns_number_total 7062 _reflns_number_gt 3066 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0447596000 _diffrn_orient_matrix_UB_12 -0.0007115000 _diffrn_orient_matrix_UB_13 0.0453162000 _diffrn_orient_matrix_UB_21 -0.0534208000 _diffrn_orient_matrix_UB_22 0.0215623000 _diffrn_orient_matrix_UB_23 0.0168847000 _diffrn_orient_matrix_UB_31 -0.0338270000 _diffrn_orient_matrix_UB_32 -0.0349963000 _diffrn_orient_matrix_UB_33 0.0094405000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement '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^)+(0.0449P)^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 7062 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1276 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 0.849 _refine_ls_restrained_S_all 0.850 _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 S1 S 0.91767(6) -0.01393(3) 0.22331(4) 0.05269(18) Uani 1 1 d . A . P1 P 0.98679(6) 0.09325(3) 0.23610(4) 0.03634(14) Uani 1 1 d . . . O1 O 0.6270(6) 0.0432(3) 0.4420(5) 0.0499(16) Uani 0.350(4) 1 d P A 1 C1 C 1.0709(2) 0.12128(10) 0.14115(13) 0.0386(5) Uani 1 1 d . A . C2 C 1.1212(2) 0.06486(11) 0.08923(15) 0.0524(6) Uani 1 1 d . . . H2 H 1.1078 0.0118 0.1021 0.063 Uiso 1 1 calc R A . C3 C 1.1903(3) 0.08457(14) 0.01932(16) 0.0632(7) Uani 1 1 d . A . H3 H 1.2243 0.0451 -0.0157 0.076 Uiso 1 1 calc R . . C4 C 1.2106(3) 0.16064(14) -0.00047(16) 0.0623(6) Uani 1 1 d . . . H4 H 1.2591 0.1738 -0.0488 0.075 Uiso 1 1 calc R A . C5 C 1.1610(3) 0.21794(13) 0.04944(18) 0.0658(7) Uani 1 1 d . A . H5 H 1.1745 0.2707 0.0354 0.079 Uiso 1 1 calc R . . C6 C 1.0913(3) 0.19877(11) 0.12021(17) 0.0590(6) Uani 1 1 d . . . H6 H 1.0572 0.2385 0.1547 0.071 Uiso 1 1 calc R A . C7 C 0.8392(2) 0.16201(10) 0.23408(12) 0.0357(4) Uani 1 1 d . A . C8 C 0.6983(2) 0.13894(12) 0.19537(15) 0.0542(6) Uani 1 1 d . . . H8 H 0.6809 0.0874 0.1735 0.065 Uiso 1 1 calc R A . C9 C 0.5824(3) 0.18959(15) 0.18798(19) 0.0760(8) Uani 1 1 d . A . H9 H 0.4860 0.1732 0.1610 0.091 Uiso 1 1 calc R . . C10 C 0.6082(3) 0.26409(14) 0.22024(18) 0.0678(7) Uani 1 1 d . . . H10 H 0.5292 0.2993 0.2156 0.081 Uiso 1 1 calc R A . C11 C 0.7470(3) 0.28763(12) 0.25893(16) 0.0572(6) Uani 1 1 d . A . H11 H 0.7640 0.3393 0.2802 0.069 Uiso 1 1 calc R . . C12 C 0.8625(2) 0.23670(10) 0.26723(13) 0.0441(5) Uani 1 1 d . . . H12 H 0.9581 0.2530 0.2958 0.053 Uiso 1 1 calc R A . C13 C 1.1019(12) 0.1165(5) 0.3545(7) 0.025(2) Uani 0.350(4) 1 d PD A 1 C14 C 1.2463(10) 0.1319(4) 0.3511(6) 0.036(2) Uani 0.350(4) 1 d PD A 1 H14 H 1.2748 0.1326 0.2931 0.044 Uiso 0.350(4) 1 calc PR A 1 C15 C 1.3493(10) 0.1464(5) 0.4320(7) 0.049(3) Uani 0.350(4) 1 d PD A 1 H15 H 1.4482 0.1563 0.4297 0.059 Uiso 0.350(4) 1 calc PR A 1 C16 C 1.3060(10) 0.1460(5) 0.5151(7) 0.041(2) Uani 0.350(4) 1 d PD A 1 H16 H 1.3750 0.1574 0.5705 0.050 Uiso 0.350(4) 1 calc PR A 1 C17 C 1.1644(9) 0.1295(4) 0.5193(5) 0.0395(18) Uani 0.350(4) 1 d PD A 1 H17 H 1.1377 0.1281 0.5779 0.047 Uiso 0.350(4) 1 calc PR A 1 C18 C 1.0580(8) 0.1146(3) 0.4389(4) 0.0321(15) Uani 0.350(4) 1 d PD A 1 C19 C 0.9063(6) 0.0954(3) 0.4452(4) 0.0345(15) Uani 0.350(4) 1 d P A 1 H19 H 0.8363 0.0933 0.3884 0.041 Uiso 0.350(4) 1 calc PR A 1 C20 C 0.8571(10) 0.0807(6) 0.5223(5) 0.038(2) Uani 0.350(4) 1 d P A 1 H20 H 0.9214 0.0846 0.5812 0.045 Uiso 0.350(4) 1 calc PR A 1 C21 C 0.7017(10) 0.0583(6) 0.5160(8) 0.044(3) Uani 0.350(4) 1 d P A 1 C22 C 0.6694(9) 0.0555(3) 0.5908(4) 0.0315(17) Uani 0.350(4) 1 d P A 1 H22 H 0.5875 0.0229 0.5897 0.038 Uiso 0.350(4) 1 calc PR A 1 C23 C 0.7230(8) 0.0891(4) 0.6828(5) 0.0230(13) Uani 0.350(4) 1 d P A 1 H23 H 0.8152 0.1141 0.6927 0.028 Uiso 0.350(4) 1 calc PR A 1 C24 C 0.6533(3) 0.08820(13) 0.75729(18) 0.0643(7) Uani 1 1 d . . . C25 C 0.5284(3) 0.05254(13) 0.77415(19) 0.0662(7) Uani 1 1 d . A . H25 H 0.4677 0.0234 0.7265 0.079 Uiso 1 1 calc R . . C26 C 0.4923(3) 0.05924(13) 0.85976(19) 0.0649(7) Uani 1 1 d . . . H26 H 0.4072 0.0345 0.8710 0.078 Uiso 1 1 calc R A . C27 C 0.5785(3) 0.10135(13) 0.92813(17) 0.0605(6) Uani 1 1 d . A . H27 H 0.5534 0.1059 0.9870 0.073 Uiso 1 1 calc R . . C28 C 0.7007(3) 0.13693(13) 0.91222(19) 0.0655(7) Uani 1 1 d . . . H28 H 0.7599 0.1665 0.9600 0.079 Uiso 1 1 calc R A . C29 C 0.7386(3) 0.13049(13) 0.8284(2) 0.0685(7) Uani 1 1 d . A . H29 H 0.8246 0.1553 0.8186 0.082 Uiso 1 1 calc R . . O1A O 0.7061(6) 0.0628(3) 0.4550(4) 0.0984(19) Uani 0.650(4) 1 d P A 2 C13A C 1.1335(7) 0.1140(3) 0.3333(4) 0.0294(12) Uani 0.650(4) 1 d PD A 2 C14A C 1.2586(5) 0.1529(2) 0.3227(3) 0.0429(12) Uani 0.650(4) 1 d PD A 2 H14A H 1.2698 0.1653 0.2619 0.052 Uiso 0.650(4) 1 calc PR A 2 C15A C 1.3680(5) 0.1744(3) 0.3973(4) 0.0632(15) Uani 0.650(4) 1 d PD A 2 H15A H 1.4529 0.2003 0.3877 0.076 Uiso 0.650(4) 1 calc PR A 2 C16A C 1.3511(7) 0.1576(4) 0.4846(4) 0.0630(19) Uani 0.650(4) 1 d PD A 2 H16A H 1.4233 0.1737 0.5365 0.076 Uiso 0.650(4) 1 calc PR A 2 C17A C 1.2303(6) 0.1175(3) 0.4987(3) 0.0502(12) Uani 0.650(4) 1 d PD A 2 H17A H 1.2218 0.1057 0.5602 0.060 Uiso 0.650(4) 1 calc PR A 2 C18A C 1.1196(4) 0.09375(19) 0.4241(3) 0.0325(8) Uani 0.650(4) 1 d PD A 2 C19A C 1.0007(3) 0.04099(15) 0.44166(19) 0.0357(9) Uani 0.650(4) 1 d P . 2 H19A H 0.9146 0.0429 0.3885 0.043 Uiso 0.650(4) 1 calc PR A 2 C20A C 0.9511(5) 0.04649(17) 0.5341(2) 0.0466(10) Uani 0.650(4) 1 d P . 2 H20A H 1.0126 0.0836 0.5776 0.056 Uiso 0.650(4) 1 calc PR A 2 C21A C 0.7888(10) 0.0616(4) 0.5269(5) 0.077(3) Uani 0.650(4) 1 d P A 2 C22A C 0.7705(6) 0.0842(2) 0.6366(5) 0.0783(16) Uani 0.650(4) 1 d P A 2 H22A H 0.8448 0.1068 0.6828 0.094 Uiso 0.650(4) 1 calc PR A 2 C23A C 0.6527(6) 0.0678(3) 0.6471(6) 0.081(2) Uani 0.650(4) 1 d P A 2 H23A H 0.5741 0.0474 0.6021 0.097 Uiso 0.650(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0464(4) 0.0336(2) 0.0714(4) -0.0011(3) -0.0028(3) -0.0044(2) P1 0.0362(3) 0.0313(2) 0.0373(3) 0.0023(2) -0.0017(2) 0.0005(2) O1 0.045(4) 0.053(3) 0.045(3) -0.011(2) -0.007(3) -0.012(3) C1 0.0328(11) 0.0397(10) 0.0429(12) 0.0001(9) 0.0069(9) 0.0060(9) C2 0.0583(16) 0.0455(11) 0.0522(15) -0.0092(10) 0.0089(12) 0.0011(11) C3 0.0691(18) 0.0729(15) 0.0512(16) -0.0161(12) 0.0206(13) 0.0079(14) C4 0.0593(17) 0.0813(16) 0.0513(16) 0.0005(13) 0.0228(12) 0.0037(14) C5 0.0691(18) 0.0574(13) 0.082(2) 0.0090(13) 0.0404(15) 0.0034(12) C6 0.0656(17) 0.0429(11) 0.0787(18) 0.0024(11) 0.0385(13) 0.0090(11) C7 0.0416(12) 0.0385(9) 0.0266(10) 0.0006(8) 0.0065(8) 0.0039(9) C8 0.0424(14) 0.0539(12) 0.0626(16) -0.0119(11) 0.0024(11) 0.0055(11) C9 0.0433(15) 0.0887(18) 0.091(2) -0.0135(16) 0.0033(14) 0.0172(14) C10 0.0614(18) 0.0716(16) 0.0747(19) 0.0033(13) 0.0239(14) 0.0291(14) C11 0.0732(19) 0.0447(11) 0.0584(16) -0.0030(10) 0.0244(13) 0.0141(13) C12 0.0494(13) 0.0470(11) 0.0367(12) -0.0031(9) 0.0106(9) 0.0021(10) C13 0.027(5) 0.023(3) 0.027(6) -0.003(3) 0.010(3) -0.002(3) C14 0.044(5) 0.039(4) 0.026(5) 0.003(3) 0.009(4) 0.003(4) C15 0.022(4) 0.064(6) 0.060(8) -0.014(6) 0.006(5) -0.008(4) C16 0.026(5) 0.053(5) 0.043(6) -0.009(4) 0.002(4) -0.011(4) C17 0.041(5) 0.040(3) 0.033(4) -0.004(3) -0.001(3) 0.000(3) C18 0.033(4) 0.033(3) 0.029(3) -0.001(2) 0.004(3) 0.004(3) C19 0.036(3) 0.041(3) 0.026(3) -0.003(2) 0.006(2) -0.003(3) C20 0.040(5) 0.046(5) 0.021(4) -0.006(3) -0.008(3) 0.000(4) C21 0.025(4) 0.033(4) 0.064(7) -0.001(4) -0.012(5) -0.002(4) C22 0.044(5) 0.030(3) 0.015(3) 0.000(2) -0.005(3) -0.011(3) C23 0.010(3) 0.027(3) 0.033(4) 0.000(3) 0.007(2) -0.003(3) C24 0.086(2) 0.0480(13) 0.0674(18) 0.0152(12) 0.0353(15) 0.0291(14) C25 0.0701(19) 0.0557(14) 0.0679(19) -0.0031(12) 0.0037(15) 0.0068(13) C26 0.0524(16) 0.0670(15) 0.079(2) -0.0034(13) 0.0209(14) -0.0045(13) C27 0.0536(16) 0.0735(15) 0.0589(16) -0.0022(12) 0.0224(12) 0.0027(13) C28 0.0530(16) 0.0676(15) 0.078(2) -0.0114(13) 0.0180(14) -0.0055(13) C29 0.0651(18) 0.0614(14) 0.090(2) 0.0018(14) 0.0411(16) 0.0043(13) O1A 0.074(4) 0.107(3) 0.127(5) 0.063(3) 0.051(4) 0.036(3) C13A 0.027(3) 0.034(2) 0.029(3) 0.0089(17) 0.0093(19) 0.0028(17) C14A 0.033(2) 0.056(3) 0.039(3) 0.0170(19) 0.0055(19) -0.0042(19) C15A 0.042(3) 0.076(3) 0.065(4) 0.016(2) -0.003(2) -0.014(2) C16A 0.040(3) 0.083(4) 0.057(5) 0.006(3) -0.011(3) -0.011(3) C17A 0.053(4) 0.062(3) 0.031(2) 0.009(2) -0.002(2) 0.003(3) C18A 0.034(2) 0.0318(17) 0.032(2) 0.0075(15) 0.0074(16) 0.0035(16) C19A 0.051(2) 0.0325(14) 0.0288(17) 0.0036(12) 0.0190(14) 0.0019(14) C20A 0.072(3) 0.0316(15) 0.044(2) 0.0057(14) 0.0314(19) 0.0097(17) C21A 0.120(8) 0.053(4) 0.078(5) 0.040(4) 0.066(6) 0.046(5) C22A 0.063(3) 0.047(2) 0.115(5) 0.003(3) -0.004(3) 0.010(2) C23A 0.043(3) 0.056(3) 0.155(8) 0.048(4) 0.044(5) 0.020(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9589(6) . ? P1 C13A 1.801(7) . ? P1 C1 1.813(2) . ? P1 C7 1.8192(19) . ? P1 C13 1.894(12) . ? O1 C21 1.195(13) . ? C1 C2 1.383(3) . ? C1 C6 1.397(2) . ? C2 C3 1.372(3) . ? C3 C4 1.369(3) . ? C4 C5 1.373(3) . ? C5 C6 1.384(3) . ? C7 C12 1.382(2) . ? C7 C8 1.383(3) . ? C8 C9 1.382(3) . ? C9 C10 1.377(3) . ? C10 C11 1.367(3) . ? C11 C12 1.381(3) . ? C13 C14 1.391(10) . ? C13 C18 1.392(9) . ? C14 C15 1.390(10) . ? C15 C16 1.371(12) . ? C16 C17 1.372(9) . ? C17 C18 1.403(8) . ? C18 C19 1.483(8) . ? C19 C20 1.339(9) . ? C20 C21 1.491(12) . ? C21 C22 1.206(13) . ? C22 C23 1.464(10) . ? C23 C24 1.393(8) . ? C24 C29 1.386(4) . ? C24 C25 1.391(3) . ? C24 C23A 1.663(9) . ? C25 C26 1.380(3) . ? C26 C27 1.363(3) . ? C27 C28 1.364(3) . ? C28 C29 1.362(3) . ? O1A C21A 1.174(9) . ? C13A C14A 1.389(6) . ? C13A C18A 1.419(6) . ? C14A C15A 1.387(6) . ? C15A C16A 1.362(7) . ? C16A C17A 1.381(7) . ? C17A C18A 1.405(5) . ? C18A C19A 1.504(4) . ? C19A C20A 1.535(4) . ? C19A C20A 1.597(4) 3_756 ? C20A C21A 1.524(8) . ? C20A C19A 1.597(4) 3_756 ? C21A C22A 1.709(9) . ? C22A C23A 1.181(7) . ? 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 C13A P1 C1 100.29(17) . . ? C13A P1 C7 109.44(17) . . ? C1 P1 C7 105.42(8) . . ? C13A P1 C13 14.5(3) . . ? C1 P1 C13 113.6(3) . . ? C7 P1 C13 99.2(3) . . ? C13A P1 S1 116.53(18) . . ? C1 P1 S1 111.55(6) . . ? C7 P1 S1 112.44(7) . . ? C13 P1 S1 113.7(3) . . ? C2 C1 C6 118.4(2) . . ? C2 C1 P1 119.63(15) . . ? C6 C1 P1 121.97(15) . . ? C3 C2 C1 120.8(2) . . ? C4 C3 C2 120.5(2) . . ? C3 C4 C5 120.0(2) . . ? C4 C5 C6 120.0(2) . . ? C5 C6 C1 120.3(2) . . ? C12 C7 C8 118.77(18) . . ? C12 C7 P1 122.85(16) . . ? C8 C7 P1 118.36(14) . . ? C9 C8 C7 121.1(2) . . ? C10 C9 C8 119.2(2) . . ? C11 C10 C9 120.3(2) . . ? C10 C11 C12 120.4(2) . . ? C11 C12 C7 120.2(2) . . ? C14 C13 C18 120.7(9) . . ? C14 C13 P1 112.1(6) . . ? C18 C13 P1 127.0(7) . . ? C15 C14 C13 120.6(8) . . ? C16 C15 C14 118.9(8) . . ? C15 C16 C17 120.9(8) . . ? C16 C17 C18 121.4(8) . . ? C13 C18 C17 117.5(8) . . ? C13 C18 C19 122.0(7) . . ? C17 C18 C19 120.5(6) . . ? C20 C19 C18 127.1(6) . . ? C19 C20 C21 120.2(8) . . ? O1 C21 C22 128.0(9) . . ? O1 C21 C20 119.4(10) . . ? C22 C21 C20 112.6(9) . . ? C21 C22 C23 136.9(8) . . ? C24 C23 C22 127.0(7) . . ? C29 C24 C25 118.1(2) . . ? C29 C24 C23 107.5(4) . . ? C25 C24 C23 134.3(4) . . ? C29 C24 C23A 137.3(3) . . ? C25 C24 C23A 104.6(3) . . ? C23 C24 C23A 30.1(3) . . ? C26 C25 C24 120.3(2) . . ? C27 C26 C25 120.0(2) . . ? C26 C27 C28 120.1(2) . . ? C29 C28 C27 120.6(2) . . ? C28 C29 C24 120.8(2) . . ? C14A C13A C18A 118.3(5) . . ? C14A C13A P1 121.9(4) . . ? C18A C13A P1 119.8(4) . . ? C15A C14A C13A 122.7(5) . . ? C16A C15A C14A 118.7(5) . . ? C15A C16A C17A 120.8(5) . . ? C16A C17A C18A 121.5(4) . . ? C17A C18A C13A 117.9(4) . . ? C17A C18A C19A 119.6(3) . . ? C13A C18A C19A 122.1(4) . . ? C18A C19A C20A 119.3(3) . . ? C18A C19A C20A 115.3(3) . 3_756 ? C20A C19A C20A 89.1(2) . 3_756 ? C21A C20A C19A 115.7(3) . . ? C21A C20A C19A 114.1(3) . 3_756 ? C19A C20A C19A 90.9(2) . 3_756 ? O1A C21A C20A 121.7(6) . . ? O1A C21A C22A 132.2(7) . . ? C20A C21A C22A 105.7(6) . . ? C23A C22A C21A 110.7(8) . . ? C22A C23A C24 105.5(8) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.247 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.042 ### END data_10h _database_code_depnum_ccdc_archive 'CCDC 874838' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.3741(2) _cell_length_b 17.2885(3) _cell_length_c 14.7653(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.202(2) _cell_angle_gamma 90.00 _cell_volume 2338.87(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 27338 _cell_measurement_theta_min 3.0621 _cell_measurement_theta_max 30.4381 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97761 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 18246 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.1655 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.0621 _diffrn_reflns_theta_max 30.4381 _reflns_number_total 7060 _reflns_number_gt 3030 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0447596000 _diffrn_orient_matrix_UB_12 -0.0007115000 _diffrn_orient_matrix_UB_13 0.0453162000 _diffrn_orient_matrix_UB_21 -0.0534208000 _diffrn_orient_matrix_UB_22 0.0215623000 _diffrn_orient_matrix_UB_23 0.0168847000 _diffrn_orient_matrix_UB_31 -0.0338270000 _diffrn_orient_matrix_UB_32 -0.0349963000 _diffrn_orient_matrix_UB_33 0.0094405000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement '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^)+(0.0446P)^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 7060 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 0.853 _refine_ls_restrained_S_all 0.853 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91769(6) -0.01424(3) 0.22311(4) 0.05278(18) Uani 1 1 d . A . P1 P 0.98686(6) 0.09296(3) 0.23593(4) 0.03648(14) Uani 1 1 d . . . O1 O 0.6266(7) 0.0429(4) 0.4418(5) 0.0529(18) Uani 0.337(4) 1 d P A 1 C1 C 1.0709(2) 0.12095(10) 0.14096(13) 0.0386(5) Uani 1 1 d . A . C2 C 1.1210(2) 0.06466(12) 0.08926(16) 0.0525(6) Uani 1 1 d . . . H2 H 1.1072 0.0117 0.1020 0.063 Uiso 1 1 calc R A . C3 C 1.1907(3) 0.08430(14) 0.01948(16) 0.0641(7) Uani 1 1 d . A . H3 H 1.2255 0.0448 -0.0151 0.077 Uiso 1 1 calc R . . C4 C 1.2105(3) 0.16032(15) -0.00057(16) 0.0631(7) Uani 1 1 d . . . H4 H 1.2589 0.1734 -0.0489 0.076 Uiso 1 1 calc R A . C5 C 1.1605(3) 0.21768(13) 0.04895(18) 0.0660(7) Uani 1 1 d . A . H5 H 1.1736 0.2705 0.0347 0.079 Uiso 1 1 calc R . . C6 C 1.0908(3) 0.19841(11) 0.11977(17) 0.0583(6) Uani 1 1 d . . . H6 H 1.0563 0.2381 0.1541 0.070 Uiso 1 1 calc R A . C7 C 0.8397(2) 0.16174(10) 0.23416(12) 0.0354(4) Uani 1 1 d . A . C8 C 0.6985(2) 0.13866(12) 0.19547(16) 0.0550(6) Uani 1 1 d . . . H8 H 0.6812 0.0872 0.1735 0.066 Uiso 1 1 calc R A . C9 C 0.5824(3) 0.18914(15) 0.18825(18) 0.0750(8) Uani 1 1 d . A . H9 H 0.4860 0.1726 0.1619 0.090 Uiso 1 1 calc R . . C10 C 0.6086(3) 0.26392(14) 0.21994(18) 0.0674(7) Uani 1 1 d . . . H10 H 0.5299 0.2994 0.2147 0.081 Uiso 1 1 calc R A . C11 C 0.7476(3) 0.28734(12) 0.25891(15) 0.0561(6) Uani 1 1 d . A . H11 H 0.7648 0.3390 0.2804 0.067 Uiso 1 1 calc R . . C12 C 0.8629(2) 0.23628(11) 0.26713(14) 0.0447(5) Uani 1 1 d . . . H12 H 0.9586 0.2526 0.2956 0.054 Uiso 1 1 calc R A . C13 C 1.1022(13) 0.1172(6) 0.3539(8) 0.026(2) Uani 0.337(4) 1 d PD A 1 C14 C 1.2465(11) 0.1328(5) 0.3515(6) 0.038(2) Uani 0.337(4) 1 d PD A 1 H14 H 1.2752 0.1337 0.2935 0.045 Uiso 0.337(4) 1 calc PR A 1 C15 C 1.3495(10) 0.1469(5) 0.4317(7) 0.045(3) Uani 0.337(4) 1 d PD A 1 H15 H 1.4483 0.1568 0.4292 0.054 Uiso 0.337(4) 1 calc PR A 1 C16 C 1.3066(10) 0.1464(5) 0.5147(7) 0.041(2) Uani 0.337(4) 1 d PD A 1 H16 H 1.3757 0.1578 0.5701 0.049 Uiso 0.337(4) 1 calc PR A 1 C17 C 1.1652(9) 0.1296(4) 0.5192(5) 0.0380(18) Uani 0.337(4) 1 d PD A 1 H17 H 1.1389 0.1283 0.5778 0.046 Uiso 0.337(4) 1 calc PR A 1 C18 C 1.0584(8) 0.1144(3) 0.4387(4) 0.0311(16) Uani 0.337(4) 1 d PD A 1 C19 C 0.9061(6) 0.0951(3) 0.4451(4) 0.0348(16) Uani 0.337(4) 1 d P A 1 H19 H 0.8365 0.0926 0.3882 0.042 Uiso 0.337(4) 1 calc PR A 1 C20 C 0.8555(11) 0.0807(5) 0.5223(5) 0.035(2) Uani 0.337(4) 1 d P A 1 H20 H 0.9197 0.0851 0.5812 0.042 Uiso 0.337(4) 1 calc PR A 1 C21 C 0.7011(10) 0.0580(6) 0.5170(9) 0.049(3) Uani 0.337(4) 1 d P A 1 C22 C 0.6696(9) 0.0553(4) 0.5917(5) 0.0286(16) Uani 0.337(4) 1 d P A 1 H22 H 0.5882 0.0225 0.5913 0.034 Uiso 0.337(4) 1 calc PR A 1 C23 C 0.7236(8) 0.0890(4) 0.6820(5) 0.0251(14) Uani 0.337(4) 1 d P A 1 H23 H 0.8156 0.1143 0.6917 0.030 Uiso 0.337(4) 1 calc PR A 1 C24 C 0.6530(3) 0.08799(14) 0.75684(18) 0.0655(7) Uani 1 1 d . . . C25 C 0.5278(3) 0.05216(13) 0.77425(19) 0.0667(7) Uani 1 1 d . A . H25 H 0.4671 0.0228 0.7269 0.080 Uiso 1 1 calc R . . C26 C 0.4923(3) 0.05929(13) 0.85965(19) 0.0659(7) Uani 1 1 d . . . H26 H 0.4073 0.0345 0.8710 0.079 Uiso 1 1 calc R A . C27 C 0.5782(3) 0.10158(13) 0.92810(17) 0.0611(6) Uani 1 1 d . A . H27 H 0.5531 0.1063 0.9869 0.073 Uiso 1 1 calc R . . C28 C 0.7005(3) 0.13722(13) 0.91160(19) 0.0649(7) Uani 1 1 d . . . H28 H 0.7599 0.1670 0.9591 0.078 Uiso 1 1 calc R A . C29 C 0.7378(3) 0.13046(13) 0.8277(2) 0.0684(7) Uani 1 1 d . A . H29 H 0.8235 0.1553 0.8177 0.082 Uiso 1 1 calc R . . O1A O 0.7065(6) 0.0632(3) 0.4559(4) 0.098(2) Uani 0.663(4) 1 d P A 2 C13A C 1.1340(7) 0.1129(3) 0.3334(4) 0.0305(13) Uani 0.663(4) 1 d PD A 2 C14A C 1.2587(5) 0.1520(3) 0.3222(3) 0.0435(12) Uani 0.663(4) 1 d PD A 2 H14A H 1.2694 0.1643 0.2613 0.052 Uiso 0.663(4) 1 calc PR A 2 C15A C 1.3679(5) 0.1737(3) 0.3965(4) 0.0633(15) Uani 0.663(4) 1 d PD A 2 H15A H 1.4522 0.2002 0.3867 0.076 Uiso 0.663(4) 1 calc PR A 2 C16A C 1.3520(7) 0.1563(4) 0.4840(4) 0.064(2) Uani 0.663(4) 1 d PD A 2 H16A H 1.4255 0.1714 0.5356 0.077 Uiso 0.663(4) 1 calc PR A 2 C17A C 1.2313(6) 0.1171(3) 0.4983(3) 0.0498(12) Uani 0.663(4) 1 d PD A 2 H17A H 1.2227 0.1060 0.5599 0.060 Uiso 0.663(4) 1 calc PR A 2 C18A C 1.1197(4) 0.09292(19) 0.4239(3) 0.0337(8) Uani 0.663(4) 1 d PD A 2 C19A C 1.0005(3) 0.04124(14) 0.44149(19) 0.0336(8) Uani 0.663(4) 1 d P . 2 H19A H 0.9142 0.0435 0.3885 0.040 Uiso 0.663(4) 1 calc PR A 2 C20A C 0.9519(5) 0.04666(17) 0.5343(2) 0.0450(10) Uani 0.663(4) 1 d P . 2 H20A H 1.0137 0.0838 0.5776 0.054 Uiso 0.663(4) 1 calc PR A 2 C21A C 0.7896(10) 0.0615(4) 0.5272(5) 0.078(3) Uani 0.663(4) 1 d P A 2 C22A C 0.7717(6) 0.0844(2) 0.6362(4) 0.0761(15) Uani 0.663(4) 1 d P A 2 H22A H 0.8466 0.1071 0.6818 0.091 Uiso 0.663(4) 1 calc PR A 2 C23A C 0.6535(6) 0.0683(3) 0.6482(6) 0.082(2) Uani 0.663(4) 1 d P A 2 H23A H 0.5746 0.0479 0.6034 0.098 Uiso 0.663(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0466(4) 0.0339(2) 0.0712(4) -0.0007(3) -0.0026(3) -0.0043(2) P1 0.0361(3) 0.0314(2) 0.0378(3) 0.0027(2) -0.0016(2) 0.0008(2) O1 0.049(4) 0.057(3) 0.044(3) -0.009(2) -0.011(3) -0.011(3) C1 0.0315(11) 0.0406(10) 0.0425(12) 0.0001(9) 0.0055(9) 0.0058(9) C2 0.0573(16) 0.0449(11) 0.0545(15) -0.0080(10) 0.0102(12) 0.0017(11) C3 0.0708(18) 0.0737(16) 0.0519(16) -0.0165(13) 0.0224(13) 0.0099(14) C4 0.0592(17) 0.0813(16) 0.0534(16) 0.0020(13) 0.0222(12) 0.0039(14) C5 0.0700(19) 0.0548(13) 0.084(2) 0.0098(13) 0.0410(15) 0.0053(13) C6 0.0665(17) 0.0398(11) 0.0790(18) 0.0019(11) 0.0391(14) 0.0082(11) C7 0.0405(12) 0.0408(10) 0.0245(10) 0.0008(8) 0.0056(8) 0.0046(9) C8 0.0437(14) 0.0549(12) 0.0631(16) -0.0103(11) 0.0041(11) 0.0050(11) C9 0.0432(15) 0.0877(18) 0.089(2) -0.0129(16) 0.0035(14) 0.0153(14) C10 0.0622(19) 0.0685(16) 0.0761(19) 0.0043(13) 0.0246(15) 0.0290(14) C11 0.0705(18) 0.0447(11) 0.0584(16) -0.0037(10) 0.0257(13) 0.0138(13) C12 0.0514(14) 0.0457(11) 0.0378(12) -0.0038(9) 0.0110(10) 0.0015(10) C13 0.029(5) 0.022(3) 0.027(6) -0.006(3) 0.003(3) 0.003(3) C14 0.046(6) 0.042(5) 0.027(5) 0.002(3) 0.013(4) 0.004(4) C15 0.019(4) 0.069(6) 0.044(7) -0.005(6) 0.000(5) -0.002(4) C16 0.021(5) 0.052(5) 0.045(6) -0.008(4) 0.000(4) -0.011(4) C17 0.035(5) 0.044(4) 0.032(4) -0.003(3) 0.000(3) -0.007(3) C18 0.036(4) 0.028(3) 0.026(3) 0.000(2) -0.001(3) 0.006(3) C19 0.038(4) 0.040(3) 0.027(3) -0.002(2) 0.008(2) 0.000(3) C20 0.042(5) 0.038(5) 0.019(4) -0.006(3) -0.009(3) -0.004(4) C21 0.021(4) 0.030(4) 0.084(9) -0.008(5) -0.015(5) -0.004(4) C22 0.041(5) 0.029(3) 0.013(3) -0.003(2) -0.001(3) -0.010(3) C23 0.009(3) 0.035(3) 0.035(4) -0.001(3) 0.014(3) -0.006(3) C24 0.089(2) 0.0508(13) 0.0655(18) 0.0147(13) 0.0353(16) 0.0308(14) C25 0.0688(19) 0.0576(14) 0.0697(19) -0.0007(13) 0.0056(15) 0.0067(14) C26 0.0525(17) 0.0704(15) 0.079(2) -0.0012(14) 0.0226(14) -0.0046(13) C27 0.0562(16) 0.0721(15) 0.0594(16) -0.0026(13) 0.0225(13) 0.0028(13) C28 0.0537(17) 0.0651(15) 0.078(2) -0.0103(13) 0.0183(14) -0.0036(13) C29 0.0676(19) 0.0600(14) 0.089(2) 0.0014(14) 0.0430(16) 0.0041(13) O1A 0.073(4) 0.107(3) 0.127(5) 0.060(3) 0.050(4) 0.037(3) C13A 0.031(3) 0.034(2) 0.028(3) 0.0081(17) 0.0093(19) 0.0039(18) C14A 0.032(2) 0.063(3) 0.035(3) 0.0139(19) 0.0044(18) -0.0065(19) C15A 0.043(3) 0.078(3) 0.063(4) 0.017(2) -0.003(2) -0.016(2) C16A 0.041(4) 0.087(4) 0.055(5) 0.012(3) -0.012(3) -0.010(3) C17A 0.050(4) 0.062(3) 0.034(2) 0.0108(19) 0.002(2) 0.004(3) C18A 0.033(2) 0.0320(17) 0.035(2) 0.0073(15) 0.0061(16) 0.0058(16) C19A 0.046(2) 0.0304(14) 0.0292(16) 0.0040(11) 0.0179(13) 0.0023(13) C20A 0.070(3) 0.0291(15) 0.044(2) 0.0057(13) 0.0314(18) 0.0080(17) C21A 0.124(8) 0.053(4) 0.078(5) 0.042(3) 0.066(6) 0.043(5) C22A 0.064(3) 0.042(2) 0.114(5) 0.004(3) -0.002(3) 0.007(2) C23A 0.043(3) 0.057(3) 0.156(8) 0.049(4) 0.045(5) 0.021(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9594(6) . ? P1 C13A 1.804(7) . ? P1 C1 1.813(2) . ? P1 C7 1.8177(19) . ? P1 C13 1.893(12) . ? O1 C21 1.209(14) . ? C1 C2 1.379(3) . ? C1 C6 1.397(3) . ? C2 C3 1.374(3) . ? C3 C4 1.368(3) . ? C4 C5 1.372(3) . ? C5 C6 1.386(3) . ? C7 C12 1.378(2) . ? C7 C8 1.385(3) . ? C8 C9 1.381(3) . ? C9 C10 1.379(3) . ? C10 C11 1.370(3) . ? C11 C12 1.380(3) . ? C13 C14 1.387(11) . ? C13 C18 1.398(10) . ? C14 C15 1.382(10) . ? C15 C16 1.369(12) . ? C16 C17 1.371(9) . ? C17 C18 1.408(8) . ? C18 C19 1.489(9) . ? C19 C20 1.347(10) . ? C20 C21 1.485(12) . ? C21 C22 1.201(14) . ? C22 C23 1.446(10) . ? C23 C24 1.403(8) . ? C24 C29 1.384(4) . ? C24 C25 1.398(3) . ? C24 C23A 1.641(9) . ? C25 C26 1.376(3) . ? C26 C27 1.364(3) . ? C27 C28 1.368(3) . ? C28 C29 1.361(3) . ? O1A C21A 1.170(9) . ? C13A C14A 1.391(6) . ? C13A C18A 1.414(6) . ? C14A C15A 1.384(6) . ? C15A C16A 1.365(7) . ? C16A C17A 1.373(7) . ? C17A C18A 1.410(5) . ? C18A C19A 1.496(4) . ? C19A C20A 1.535(4) . ? C19A C20A 1.603(4) 3_756 ? C20A C21A 1.525(8) . ? C20A C19A 1.603(4) 3_756 ? C21A C22A 1.699(9) . ? C22A C23A 1.191(7) . ? 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 C13A P1 C1 100.49(18) . . ? C13A P1 C7 109.66(17) . . ? C1 P1 C7 105.48(8) . . ? C13A P1 C13 14.4(3) . . ? C1 P1 C13 113.3(3) . . ? C7 P1 C13 98.8(3) . . ? C13A P1 S1 116.08(19) . . ? C1 P1 S1 111.52(6) . . ? C7 P1 S1 112.50(7) . . ? C13 P1 S1 114.3(3) . . ? C2 C1 C6 118.4(2) . . ? C2 C1 P1 119.61(15) . . ? C6 C1 P1 121.97(15) . . ? C3 C2 C1 120.8(2) . . ? C4 C3 C2 120.5(2) . . ? C3 C4 C5 120.1(2) . . ? C4 C5 C6 119.8(2) . . ? C5 C6 C1 120.4(2) . . ? C12 C7 C8 118.75(19) . . ? C12 C7 P1 122.94(16) . . ? C8 C7 P1 118.29(14) . . ? C9 C8 C7 121.2(2) . . ? C10 C9 C8 119.0(2) . . ? C11 C10 C9 120.3(2) . . ? C10 C11 C12 120.4(2) . . ? C7 C12 C11 120.3(2) . . ? C14 C13 C18 120.2(10) . . ? C14 C13 P1 112.9(7) . . ? C18 C13 P1 126.7(8) . . ? C15 C14 C13 121.3(8) . . ? C16 C15 C14 118.8(8) . . ? C15 C16 C17 120.9(8) . . ? C16 C17 C18 121.4(8) . . ? C13 C18 C17 117.2(8) . . ? C13 C18 C19 122.2(7) . . ? C17 C18 C19 120.6(6) . . ? C20 C19 C18 127.5(6) . . ? C19 C20 C21 121.2(8) . . ? C22 C21 O1 128.9(9) . . ? C22 C21 C20 112.8(9) . . ? O1 C21 C20 118.2(11) . . ? C21 C22 C23 136.5(8) . . ? C24 C23 C22 126.2(7) . . ? C29 C24 C25 117.8(2) . . ? C29 C24 C23 107.3(4) . . ? C25 C24 C23 134.8(4) . . ? C29 C24 C23A 136.9(3) . . ? C25 C24 C23A 105.3(3) . . ? C23 C24 C23A 29.9(3) . . ? C26 C25 C24 120.3(3) . . ? C27 C26 C25 120.5(3) . . ? C26 C27 C28 119.7(2) . . ? C29 C28 C27 120.6(2) . . ? C28 C29 C24 121.1(3) . . ? C14A C13A C18A 118.8(5) . . ? C14A C13A P1 121.2(4) . . ? C18A C13A P1 119.9(4) . . ? C15A C14A C13A 122.5(5) . . ? C16A C15A C14A 118.6(5) . . ? C15A C16A C17A 120.9(5) . . ? C16A C17A C18A 121.8(4) . . ? C17A C18A C13A 117.4(4) . . ? C17A C18A C19A 120.0(3) . . ? C13A C18A C19A 122.2(4) . . ? C18A C19A C20A 119.4(3) . . ? C18A C19A C20A 115.0(3) . 3_756 ? C20A C19A C20A 88.8(2) . 3_756 ? C21A C20A C19A 115.4(3) . . ? C21A C20A C19A 113.7(3) . 3_756 ? C19A C20A C19A 91.2(2) . 3_756 ? O1A C21A C20A 122.0(6) . . ? O1A C21A C22A 131.8(7) . . ? C20A C21A C22A 105.8(6) . . ? C23A C22A C21A 111.6(7) . . ? C22A C23A C24 107.0(8) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.220 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.042 ### END data_12h _database_code_depnum_ccdc_archive 'CCDC 874839' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.3749(2) _cell_length_b 17.2881(3) _cell_length_c 14.7691(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.220(2) _cell_angle_gamma 90.00 _cell_volume 2339.45(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 27338 _cell_measurement_theta_min 3.0621 _cell_measurement_theta_max 30.4381 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97177 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 18324 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.1665 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.0621 _diffrn_reflns_theta_max 30.4381 _reflns_number_total 7058 _reflns_number_gt 3056 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0447596000 _diffrn_orient_matrix_UB_12 -0.0007115000 _diffrn_orient_matrix_UB_13 0.0453162000 _diffrn_orient_matrix_UB_21 -0.0534208000 _diffrn_orient_matrix_UB_22 0.0215623000 _diffrn_orient_matrix_UB_23 0.0168847000 _diffrn_orient_matrix_UB_31 -0.0338270000 _diffrn_orient_matrix_UB_32 -0.0349963000 _diffrn_orient_matrix_UB_33 0.0094405000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement '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^)+(0.0438P)^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 7058 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1308 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 0.833 _refine_ls_restrained_S_all 0.833 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91765(6) -0.01445(3) 0.22301(4) 0.05283(17) Uani 1 1 d . A . P1 P 0.98692(6) 0.09274(3) 0.23579(3) 0.03677(14) Uani 1 1 d . . . O1 O 0.6267(7) 0.0429(4) 0.4419(5) 0.0514(17) Uani 0.325(3) 1 d P A 1 C1 C 1.0706(2) 0.12081(10) 0.14094(13) 0.0391(5) Uani 1 1 d . A . C2 C 1.1214(2) 0.06446(11) 0.08930(15) 0.0536(6) Uani 1 1 d . . . H2 H 1.1084 0.0114 0.1024 0.064 Uiso 1 1 calc R A . C3 C 1.1907(3) 0.08415(14) 0.01932(16) 0.0654(7) Uani 1 1 d . A . H3 H 1.2250 0.0447 -0.0155 0.078 Uiso 1 1 calc R . . C4 C 1.2106(3) 0.16020(14) -0.00052(16) 0.0635(6) Uani 1 1 d . . . H4 H 1.2595 0.1734 -0.0485 0.076 Uiso 1 1 calc R A . C5 C 1.1599(3) 0.21730(13) 0.04878(17) 0.0667(7) Uani 1 1 d . A . H5 H 1.1726 0.2701 0.0344 0.080 Uiso 1 1 calc R . . C6 C 1.0904(3) 0.19827(11) 0.11946(16) 0.0585(6) Uani 1 1 d . . . H6 H 1.0559 0.2381 0.1537 0.070 Uiso 1 1 calc R A . C7 C 0.8396(2) 0.16138(10) 0.23424(12) 0.0356(4) Uani 1 1 d . A . C8 C 0.6985(2) 0.13859(12) 0.19523(15) 0.0553(6) Uani 1 1 d . . . H8 H 0.6811 0.0872 0.1729 0.066 Uiso 1 1 calc R A . C9 C 0.5828(3) 0.18904(15) 0.18808(18) 0.0760(8) Uani 1 1 d . A . H9 H 0.4863 0.1725 0.1616 0.091 Uiso 1 1 calc R . . C10 C 0.6090(3) 0.26408(14) 0.22000(17) 0.0679(7) Uani 1 1 d . . . H10 H 0.5304 0.2996 0.2147 0.081 Uiso 1 1 calc R A . C11 C 0.7480(3) 0.28725(12) 0.25925(15) 0.0574(6) Uani 1 1 d . A . H11 H 0.7653 0.3388 0.2810 0.069 Uiso 1 1 calc R . . C12 C 0.8630(2) 0.23617(10) 0.26733(13) 0.0441(5) Uani 1 1 d . . . H12 H 0.9588 0.2524 0.2958 0.053 Uiso 1 1 calc R A . C13 C 1.1038(13) 0.1163(5) 0.3542(7) 0.022(2) Uani 0.325(3) 1 d PD A 1 C14 C 1.2472(11) 0.1320(5) 0.3514(6) 0.040(2) Uani 0.325(3) 1 d PD A 1 H14 H 1.2762 0.1329 0.2935 0.048 Uiso 0.325(3) 1 calc PR A 1 C15 C 1.3490(9) 0.1465(5) 0.4322(7) 0.041(2) Uani 0.325(3) 1 d PD A 1 H15 H 1.4478 0.1566 0.4300 0.049 Uiso 0.325(3) 1 calc PR A 1 C16 C 1.3060(10) 0.1464(5) 0.5159(7) 0.040(2) Uani 0.325(3) 1 d PD A 1 H16 H 1.3746 0.1582 0.5714 0.048 Uiso 0.325(3) 1 calc PR A 1 C17 C 1.1652(9) 0.1294(4) 0.5193(5) 0.0391(19) Uani 0.325(3) 1 d PD A 1 H17 H 1.1384 0.1282 0.5778 0.047 Uiso 0.325(3) 1 calc PR A 1 C18 C 1.0583(8) 0.1136(4) 0.4393(4) 0.0313(16) Uani 0.325(3) 1 d PD A 1 C19 C 0.9070(6) 0.0950(3) 0.4453(4) 0.0359(16) Uani 0.325(3) 1 d P A 1 H19 H 0.8375 0.0932 0.3882 0.043 Uiso 0.325(3) 1 calc PR A 1 C20 C 0.8552(11) 0.0801(6) 0.5231(6) 0.038(3) Uani 0.325(3) 1 d P A 1 H20 H 0.9186 0.0836 0.5823 0.046 Uiso 0.325(3) 1 calc PR A 1 C21 C 0.7007(10) 0.0585(6) 0.5155(9) 0.047(3) Uani 0.325(3) 1 d P A 1 C22 C 0.6685(9) 0.0551(4) 0.5906(4) 0.0294(17) Uani 0.325(3) 1 d P A 1 H22 H 0.5873 0.0221 0.5898 0.035 Uiso 0.325(3) 1 calc PR A 1 C23 C 0.7230(8) 0.0892(4) 0.6826(5) 0.0253(14) Uani 0.325(3) 1 d P A 1 H23 H 0.8151 0.1144 0.6928 0.030 Uiso 0.325(3) 1 calc PR A 1 C24 C 0.6519(3) 0.08773(13) 0.75601(18) 0.0662(7) Uani 1 1 d . . . C25 C 0.5269(3) 0.05194(13) 0.77421(18) 0.0667(7) Uani 1 1 d . A . H25 H 0.4658 0.0224 0.7272 0.080 Uiso 1 1 calc R . . C26 C 0.4923(3) 0.05926(13) 0.85961(19) 0.0673(7) Uani 1 1 d . . . H26 H 0.4074 0.0346 0.8713 0.081 Uiso 1 1 calc R A . C27 C 0.5784(3) 0.10160(13) 0.92782(17) 0.0609(6) Uani 1 1 d . A . H27 H 0.5536 0.1063 0.9867 0.073 Uiso 1 1 calc R . . C28 C 0.7009(3) 0.13737(13) 0.91123(18) 0.0659(7) Uani 1 1 d . . . H28 H 0.7607 0.1670 0.9587 0.079 Uiso 1 1 calc R A . C29 C 0.7371(3) 0.13058(13) 0.8268(2) 0.0705(7) Uani 1 1 d . A . H29 H 0.8223 0.1557 0.8163 0.085 Uiso 1 1 calc R . . O1A O 0.7062(5) 0.0631(3) 0.4555(4) 0.0985(19) Uani 0.675(3) 1 d P A 2 C13A C 1.1333(7) 0.1129(3) 0.3325(4) 0.0338(13) Uani 0.675(3) 1 d PD A 2 C14A C 1.2582(5) 0.1520(2) 0.3222(3) 0.0437(11) Uani 0.675(3) 1 d PD A 2 H14A H 1.2691 0.1646 0.2614 0.052 Uiso 0.675(3) 1 calc PR A 2 C15A C 1.3681(5) 0.1735(2) 0.3967(3) 0.0643(14) Uani 0.675(3) 1 d PD A 2 H15A H 1.4526 0.1999 0.3872 0.077 Uiso 0.675(3) 1 calc PR A 2 C16A C 1.3515(7) 0.1558(4) 0.4840(4) 0.0633(18) Uani 0.675(3) 1 d PD A 2 H16A H 1.4245 0.1709 0.5360 0.076 Uiso 0.675(3) 1 calc PR A 2 C17A C 1.2313(6) 0.1166(3) 0.4974(3) 0.0512(11) Uani 0.675(3) 1 d PD A 2 H17A H 1.2229 0.1049 0.5589 0.061 Uiso 0.675(3) 1 calc PR A 2 C18A C 1.1198(4) 0.09308(19) 0.4236(2) 0.0344(7) Uani 0.675(3) 1 d PD A 2 C19A C 1.0004(3) 0.04095(13) 0.44174(18) 0.0351(8) Uani 0.675(3) 1 d P . 2 H19A H 0.9139 0.0432 0.3890 0.042 Uiso 0.675(3) 1 calc PR A 2 C20A C 0.9522(5) 0.04713(16) 0.5345(2) 0.0456(9) Uani 0.675(3) 1 d P . 2 H20A H 1.0138 0.0844 0.5778 0.055 Uiso 0.675(3) 1 calc PR A 2 C21A C 0.7888(10) 0.0617(4) 0.5265(5) 0.077(3) Uani 0.675(3) 1 d P A 2 C22A C 0.7716(5) 0.0845(2) 0.6356(4) 0.0774(15) Uani 0.675(3) 1 d P A 2 H22A H 0.8466 0.1074 0.6811 0.093 Uiso 0.675(3) 1 calc PR A 2 C23A C 0.6538(6) 0.0682(3) 0.6478(5) 0.0754(19) Uani 0.675(3) 1 d P A 2 H23A H 0.5752 0.0476 0.6029 0.090 Uiso 0.675(3) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0463(3) 0.0339(2) 0.0716(4) -0.0007(2) -0.0025(3) -0.0042(2) P1 0.0366(3) 0.0319(2) 0.0377(3) 0.0027(2) -0.0012(2) 0.0006(2) O1 0.041(4) 0.061(3) 0.044(3) -0.011(2) -0.008(3) -0.011(3) C1 0.0333(11) 0.0410(9) 0.0424(12) 0.0007(8) 0.0067(9) 0.0047(9) C2 0.0596(15) 0.0457(11) 0.0536(15) -0.0076(10) 0.0076(11) 0.0013(11) C3 0.0754(18) 0.0733(15) 0.0512(15) -0.0145(12) 0.0218(13) 0.0128(14) C4 0.0592(16) 0.0830(16) 0.0528(16) 0.0026(13) 0.0223(12) 0.0043(13) C5 0.0703(18) 0.0555(13) 0.085(2) 0.0104(12) 0.0421(14) 0.0062(12) C6 0.0676(16) 0.0413(11) 0.0777(17) 0.0047(11) 0.0406(13) 0.0097(11) C7 0.0398(12) 0.0405(9) 0.0263(10) -0.0005(8) 0.0062(8) 0.0037(9) C8 0.0435(14) 0.0552(12) 0.0637(16) -0.0106(11) 0.0031(11) 0.0061(11) C9 0.0439(15) 0.0881(18) 0.092(2) -0.0112(15) 0.0049(13) 0.0153(14) C10 0.0623(18) 0.0700(16) 0.0750(18) 0.0053(13) 0.0226(14) 0.0296(14) C11 0.0747(18) 0.0459(11) 0.0567(15) -0.0041(10) 0.0252(13) 0.0150(12) C12 0.0505(13) 0.0455(10) 0.0374(12) -0.0043(9) 0.0117(9) 0.0011(10) C13 0.026(5) 0.019(3) 0.020(5) -0.004(3) -0.001(3) -0.001(3) C14 0.052(6) 0.039(4) 0.029(5) 0.005(3) 0.009(4) 0.007(4) C15 0.021(4) 0.056(5) 0.045(7) -0.005(5) 0.005(5) -0.008(4) C16 0.033(6) 0.046(5) 0.040(6) -0.008(4) 0.002(4) -0.011(4) C17 0.040(5) 0.044(4) 0.030(4) -0.003(3) -0.001(3) -0.003(4) C18 0.033(4) 0.035(3) 0.025(3) -0.001(2) 0.005(3) 0.007(3) C19 0.037(4) 0.048(3) 0.025(3) -0.001(3) 0.012(2) -0.003(3) C20 0.040(6) 0.042(5) 0.024(4) -0.010(4) -0.015(4) -0.002(4) C21 0.020(4) 0.029(4) 0.081(9) -0.008(4) -0.014(5) 0.001(4) C22 0.041(5) 0.033(3) 0.010(3) -0.002(2) -0.004(3) -0.010(3) C23 0.008(3) 0.031(3) 0.038(4) -0.003(3) 0.008(3) -0.006(3) C24 0.091(2) 0.0504(13) 0.0656(18) 0.0132(12) 0.0355(15) 0.0315(14) C25 0.0691(19) 0.0587(14) 0.0682(18) -0.0008(12) 0.0057(14) 0.0070(13) C26 0.0549(17) 0.0729(15) 0.078(2) -0.0035(14) 0.0227(14) -0.0032(13) C27 0.0555(16) 0.0734(15) 0.0583(16) -0.0020(12) 0.0224(12) 0.0037(13) C28 0.0524(16) 0.0669(14) 0.080(2) -0.0113(13) 0.0187(13) -0.0035(12) C29 0.0681(19) 0.0639(14) 0.092(2) 0.0031(14) 0.0442(16) 0.0063(13) O1A 0.071(3) 0.114(3) 0.122(4) 0.061(3) 0.047(4) 0.036(2) C13A 0.034(3) 0.039(2) 0.030(3) 0.0098(17) 0.0112(19) 0.0026(18) C14A 0.032(2) 0.060(3) 0.038(3) 0.0137(18) 0.0037(18) -0.0057(18) C15A 0.040(2) 0.078(3) 0.069(3) 0.019(2) -0.001(2) -0.014(2) C16A 0.044(3) 0.088(4) 0.048(4) 0.012(3) -0.012(3) -0.010(3) C17A 0.051(3) 0.064(3) 0.035(2) 0.0100(19) 0.000(2) 0.002(2) C18A 0.034(2) 0.0344(17) 0.035(2) 0.0073(15) 0.0075(15) 0.0035(15) C19A 0.048(2) 0.0311(13) 0.0301(16) 0.0037(11) 0.0176(13) 0.0029(13) C20A 0.071(3) 0.0296(14) 0.0441(19) 0.0062(13) 0.0298(17) 0.0092(16) C21A 0.118(8) 0.055(4) 0.077(5) 0.040(3) 0.061(5) 0.049(5) C22A 0.061(3) 0.046(2) 0.118(5) 0.004(3) 0.001(3) 0.009(2) C23A 0.045(3) 0.053(3) 0.136(6) 0.041(4) 0.036(4) 0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9595(6) . ? P1 C13A 1.793(7) . ? P1 C1 1.811(2) . ? P1 C7 1.8175(19) . ? P1 C13 1.901(11) . ? O1 C21 1.190(14) . ? C1 C2 1.383(3) . ? C1 C6 1.398(2) . ? C2 C3 1.375(3) . ? C3 C4 1.368(3) . ? C4 C5 1.370(3) . ? C5 C6 1.382(3) . ? C7 C12 1.383(2) . ? C7 C8 1.383(3) . ? C8 C9 1.379(3) . ? C9 C10 1.384(3) . ? C10 C11 1.369(3) . ? C11 C12 1.379(3) . ? C13 C14 1.381(11) . ? C13 C18 1.411(10) . ? C14 C15 1.384(10) . ? C15 C16 1.380(11) . ? C16 C17 1.363(10) . ? C17 C18 1.405(8) . ? C18 C19 1.476(9) . ? C19 C20 1.363(11) . ? C20 C21 1.477(13) . ? C21 C22 1.210(14) . ? C22 C23 1.470(10) . ? C23 C24 1.388(8) . ? C24 C29 1.388(3) . ? C24 C25 1.400(3) . ? C24 C23A 1.637(8) . ? C25 C26 1.373(3) . ? C26 C27 1.363(3) . ? C27 C28 1.371(3) . ? C28 C29 1.365(3) . ? O1A C21A 1.164(8) . ? C13A C14A 1.387(6) . ? C13A C18A 1.420(5) . ? C14A C15A 1.390(6) . ? C15A C16A 1.366(6) . ? C16A C17A 1.365(7) . ? C17A C18A 1.401(5) . ? C18A C19A 1.504(4) . ? C19A C20A 1.535(4) . ? C19A C20A 1.604(4) 3_756 ? C20A C21A 1.532(8) . ? C20A C19A 1.604(4) 3_756 ? C21A C22A 1.699(9) . ? C22A C23A 1.190(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13A P1 C1 100.38(18) . . ? C13A P1 C7 109.57(17) . . ? C1 P1 C7 105.54(8) . . ? C13A P1 C13 14.2(3) . . ? C1 P1 C13 113.2(3) . . ? C7 P1 C13 99.2(3) . . ? C13A P1 S1 116.27(19) . . ? C1 P1 S1 111.59(6) . . ? C7 P1 S1 112.38(7) . . ? C13 P1 S1 114.0(3) . . ? C2 C1 C6 118.16(19) . . ? C2 C1 P1 119.62(15) . . ? C6 C1 P1 122.18(15) . . ? C3 C2 C1 120.9(2) . . ? C4 C3 C2 120.4(2) . . ? C3 C4 C5 120.0(2) . . ? C4 C5 C6 120.1(2) . . ? C5 C6 C1 120.40(19) . . ? C12 C7 C8 118.65(18) . . ? C12 C7 P1 122.86(15) . . ? C8 C7 P1 118.44(14) . . ? C9 C8 C7 121.3(2) . . ? C8 C9 C10 119.1(2) . . ? C11 C10 C9 120.2(2) . . ? C10 C11 C12 120.4(2) . . ? C11 C12 C7 120.4(2) . . ? C14 C13 C18 120.9(9) . . ? C14 C13 P1 113.0(7) . . ? C18 C13 P1 126.0(7) . . ? C13 C14 C15 120.5(8) . . ? C16 C15 C14 119.6(8) . . ? C17 C16 C15 120.1(8) . . ? C16 C17 C18 122.4(7) . . ? C17 C18 C13 116.5(8) . . ? C17 C18 C19 121.0(6) . . ? C13 C18 C19 122.4(7) . . ? C20 C19 C18 127.6(6) . . ? C19 C20 C21 120.2(8) . . ? O1 C21 C22 128.0(9) . . ? O1 C21 C20 119.9(12) . . ? C22 C21 C20 111.9(9) . . ? C21 C22 C23 136.3(8) . . ? C24 C23 C22 125.8(7) . . ? C23 C24 C29 106.5(4) . . ? C23 C24 C25 135.9(4) . . ? C29 C24 C25 117.6(2) . . ? C23 C24 C23A 30.1(3) . . ? C29 C24 C23A 136.2(3) . . ? C25 C24 C23A 106.2(3) . . ? C26 C25 C24 120.4(2) . . ? C27 C26 C25 120.7(2) . . ? C26 C27 C28 119.8(2) . . ? C29 C28 C27 120.3(2) . . ? C28 C29 C24 121.3(2) . . ? C14A C13A C18A 117.9(5) . . ? C14A C13A P1 121.9(4) . . ? C18A C13A P1 120.1(4) . . ? C13A C14A C15A 123.0(5) . . ? C16A C15A C14A 118.3(4) . . ? C17A C16A C15A 120.7(5) . . ? C16A C17A C18A 122.2(4) . . ? C17A C18A C13A 117.8(4) . . ? C17A C18A C19A 119.7(3) . . ? C13A C18A C19A 122.1(4) . . ? C18A C19A C20A 119.2(3) . . ? C18A C19A C20A 115.2(3) . 3_756 ? C20A C19A C20A 89.5(2) . 3_756 ? C21A C20A C19A 114.9(3) . . ? C21A C20A C19A 113.5(3) . 3_756 ? C19A C20A C19A 90.5(2) . 3_756 ? O1A C21A C20A 122.5(6) . . ? O1A C21A C22A 132.1(7) . . ? C20A C21A C22A 105.0(5) . . ? C23A C22A C21A 111.5(7) . . ? C22A C23A C24 107.5(7) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.218 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.041 ### END data_14h _database_code_depnum_ccdc_archive 'CCDC 874840' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.3761(2) _cell_length_b 17.2872(2) _cell_length_c 14.7712(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.226(2) _cell_angle_gamma 90.00 _cell_volume 2339.91(7) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 34683 _cell_measurement_theta_min 3.0594 _cell_measurement_theta_max 30.4392 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97529 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 55684 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.1655 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.0594 _diffrn_reflns_theta_max 30.4392 _reflns_number_total 7075 _reflns_number_gt 3736 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0447346000 _diffrn_orient_matrix_UB_12 -0.0007367000 _diffrn_orient_matrix_UB_13 0.0452913000 _diffrn_orient_matrix_UB_21 -0.0533844000 _diffrn_orient_matrix_UB_22 0.0215673000 _diffrn_orient_matrix_UB_23 0.0168256000 _diffrn_orient_matrix_UB_31 -0.0338005000 _diffrn_orient_matrix_UB_32 -0.0349866000 _diffrn_orient_matrix_UB_33 0.0094210000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement '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^)+(0.0699P)^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 7075 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1439 _refine_ls_wR_factor_gt 0.1319 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91759(6) -0.01477(3) 0.22278(4) 0.05274(18) Uani 1 1 d . A . P1 P 0.98704(6) 0.09241(3) 0.23552(4) 0.03655(14) Uani 1 1 d . . . O1 O 0.6263(7) 0.0435(3) 0.4423(5) 0.0530(16) Uani 0.320(3) 1 d P A 1 C1 C 1.0704(2) 0.12041(10) 0.14070(14) 0.0401(4) Uani 1 1 d . A . C2 C 1.1219(3) 0.06376(12) 0.08941(16) 0.0539(6) Uani 1 1 d . . . H2 H 1.1091 0.0108 0.1027 0.065 Uiso 1 1 calc R A . C3 C 1.1914(3) 0.08333(15) 0.01956(17) 0.0645(7) Uani 1 1 d . A . H3 H 1.2263 0.0439 -0.0149 0.077 Uiso 1 1 calc R . . C4 C 1.2108(3) 0.15961(15) -0.00067(17) 0.0637(6) Uani 1 1 d . . . H4 H 1.2600 0.1727 -0.0485 0.076 Uiso 1 1 calc R A . C5 C 1.1590(3) 0.21722(14) 0.04820(19) 0.0660(7) Uani 1 1 d . A . H5 H 1.1707 0.2700 0.0332 0.079 Uiso 1 1 calc R . . C6 C 1.0899(3) 0.19801(12) 0.11930(18) 0.0593(6) Uani 1 1 d . . . H6 H 1.0556 0.2378 0.1537 0.071 Uiso 1 1 calc R A . C7 C 0.8397(2) 0.16113(10) 0.23390(12) 0.0361(4) Uani 1 1 d . A . C8 C 0.6987(2) 0.13821(13) 0.19499(16) 0.0550(6) Uani 1 1 d . . . H8 H 0.6808 0.0868 0.1726 0.066 Uiso 1 1 calc R A . C9 C 0.5833(3) 0.18930(16) 0.1883(2) 0.0753(8) Uani 1 1 d . A . H9 H 0.4867 0.1730 0.1621 0.090 Uiso 1 1 calc R . . C10 C 0.6094(3) 0.26359(15) 0.21975(19) 0.0678(7) Uani 1 1 d . . . H10 H 0.5307 0.2991 0.2143 0.081 Uiso 1 1 calc R A . C11 C 0.7485(3) 0.28694(12) 0.25910(16) 0.0582(6) Uani 1 1 d . A . H11 H 0.7657 0.3386 0.2808 0.070 Uiso 1 1 calc R . . C12 C 0.8639(2) 0.23579(11) 0.26740(14) 0.0455(5) Uani 1 1 d . . . H12 H 0.9597 0.2519 0.2961 0.055 Uiso 1 1 calc R A . C13 C 1.1039(12) 0.1159(5) 0.3549(7) 0.025(2) Uani 0.320(3) 1 d PD A 1 C14 C 1.2478(10) 0.1319(4) 0.3520(6) 0.039(2) Uani 0.320(3) 1 d PD A 1 H14 H 1.2772 0.1328 0.2942 0.046 Uiso 0.320(3) 1 calc PR A 1 C15 C 1.3488(9) 0.1466(5) 0.4331(7) 0.050(2) Uani 0.320(3) 1 d PD A 1 H15 H 1.4475 0.1571 0.4310 0.060 Uiso 0.320(3) 1 calc PR A 1 C16 C 1.3071(10) 0.1461(5) 0.5159(6) 0.0413(19) Uani 0.320(3) 1 d PD A 1 H16 H 1.3758 0.1574 0.5715 0.050 Uiso 0.320(3) 1 calc PR A 1 C17 C 1.1657(9) 0.1292(4) 0.5186(5) 0.0414(18) Uani 0.320(3) 1 d PD A 1 H17 H 1.1385 0.1282 0.5770 0.050 Uiso 0.320(3) 1 calc PR A 1 C18 C 1.0587(8) 0.1133(4) 0.4384(4) 0.0336(15) Uani 0.320(3) 1 d PD A 1 C19 C 0.9065(7) 0.0944(3) 0.4459(4) 0.0387(15) Uani 0.320(3) 1 d P A 1 H19 H 0.8368 0.0924 0.3890 0.046 Uiso 0.320(3) 1 calc PR A 1 C20 C 0.8534(10) 0.0795(5) 0.5236(5) 0.038(2) Uani 0.320(3) 1 d P A 1 H20 H 0.9169 0.0830 0.5828 0.046 Uiso 0.320(3) 1 calc PR A 1 C21 C 0.7015(9) 0.0582(5) 0.5171(8) 0.046(3) Uani 0.320(3) 1 d P A 1 C22 C 0.6680(8) 0.0556(3) 0.5913(4) 0.0302(14) Uani 0.320(3) 1 d P A 1 H22 H 0.5844 0.0243 0.5904 0.036 Uiso 0.320(3) 1 calc PR A 1 C23 C 0.7254(7) 0.0892(4) 0.6822(4) 0.0240(12) Uani 0.320(3) 1 d P A 1 H23 H 0.8183 0.1135 0.6926 0.029 Uiso 0.320(3) 1 calc PR A 1 C24 C 0.6510(3) 0.08762(14) 0.75556(19) 0.0684(8) Uani 1 1 d . . . C25 C 0.5264(3) 0.05193(14) 0.7741(2) 0.0683(7) Uani 1 1 d . A . H25 H 0.4651 0.0224 0.7272 0.082 Uiso 1 1 calc R . . C26 C 0.4921(3) 0.05928(15) 0.8598(2) 0.0670(7) Uani 1 1 d . . . H26 H 0.4076 0.0345 0.8718 0.080 Uiso 1 1 calc R A . C27 C 0.5784(3) 0.10181(14) 0.92757(18) 0.0619(6) Uani 1 1 d . A . H27 H 0.5543 0.1065 0.9867 0.074 Uiso 1 1 calc R . . C28 C 0.7002(3) 0.13784(14) 0.91019(19) 0.0662(7) Uani 1 1 d . . . H28 H 0.7597 0.1680 0.9573 0.079 Uiso 1 1 calc R A . C29 C 0.7366(3) 0.13074(14) 0.8262(2) 0.0709(8) Uani 1 1 d . A . H29 H 0.8219 0.1557 0.8156 0.085 Uiso 1 1 calc R . . O1A O 0.7072(5) 0.0638(3) 0.4563(4) 0.0959(17) Uani 0.680(3) 1 d P A 2 C13A C 1.1332(6) 0.1127(3) 0.3325(4) 0.0321(11) Uani 0.680(3) 1 d PD A 2 C14A C 1.2589(5) 0.1515(2) 0.3218(3) 0.0438(10) Uani 0.680(3) 1 d PD A 2 H14A H 1.2695 0.1641 0.2610 0.053 Uiso 0.680(3) 1 calc PR A 2 C15A C 1.3685(5) 0.1724(2) 0.3956(3) 0.0624(13) Uani 0.680(3) 1 d PD A 2 H15A H 1.4532 0.1984 0.3858 0.075 Uiso 0.680(3) 1 calc PR A 2 C16A C 1.3524(6) 0.1549(3) 0.4833(4) 0.0636(16) Uani 0.680(3) 1 d PD A 2 H16A H 1.4259 0.1700 0.5349 0.076 Uiso 0.680(3) 1 calc PR A 2 C17A C 1.2329(6) 0.1162(3) 0.4975(3) 0.0519(10) Uani 0.680(3) 1 d PD A 2 H17A H 1.2246 0.1047 0.5591 0.062 Uiso 0.680(3) 1 calc PR A 2 C18A C 1.1207(4) 0.09277(17) 0.4229(2) 0.0332(7) Uani 0.680(3) 1 d PD A 2 C19A C 1.0003(3) 0.04067(13) 0.44163(19) 0.0354(7) Uani 0.680(3) 1 d P . 2 H19A H 0.9134 0.0431 0.3891 0.042 Uiso 0.680(3) 1 calc PR A 2 C20A C 0.9531(4) 0.04676(16) 0.5349(2) 0.0462(9) Uani 0.680(3) 1 d P . 2 H20A H 1.0153 0.0839 0.5780 0.055 Uiso 0.680(3) 1 calc PR A 2 C21A C 0.7900(10) 0.0621(4) 0.5275(5) 0.079(2) Uani 0.680(3) 1 d P A 2 C22A C 0.7728(5) 0.0852(2) 0.6341(4) 0.0708(13) Uani 0.680(3) 1 d P A 2 H22A H 0.8484 0.1088 0.6785 0.085 Uiso 0.680(3) 1 calc PR A 2 C23A C 0.6546(6) 0.0689(3) 0.6496(5) 0.0717(16) Uani 0.680(3) 1 d P A 2 H23A H 0.5754 0.0480 0.6054 0.086 Uiso 0.680(3) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0469(3) 0.0340(2) 0.0707(4) -0.0009(2) -0.0023(3) -0.0044(2) P1 0.0362(3) 0.0316(2) 0.0379(3) 0.0025(2) -0.00117(19) 0.0006(2) O1 0.043(3) 0.060(3) 0.049(3) -0.008(2) -0.006(3) -0.012(3) C1 0.0352(10) 0.0404(9) 0.0438(11) 0.0004(8) 0.0061(8) 0.0054(8) C2 0.0587(15) 0.0466(11) 0.0545(14) -0.0078(10) 0.0081(11) 0.0028(11) C3 0.0720(17) 0.0743(16) 0.0496(15) -0.0150(12) 0.0183(12) 0.0103(14) C4 0.0582(16) 0.0840(17) 0.0534(15) 0.0021(13) 0.0223(12) 0.0040(13) C5 0.0698(17) 0.0544(13) 0.084(2) 0.0102(12) 0.0401(14) 0.0050(12) C6 0.0679(16) 0.0399(10) 0.0809(18) 0.0038(11) 0.0401(14) 0.0105(11) C7 0.0402(11) 0.0406(9) 0.0273(9) 0.0000(7) 0.0066(8) 0.0032(8) C8 0.0423(13) 0.0570(12) 0.0623(15) -0.0102(11) 0.0032(11) 0.0046(10) C9 0.0444(14) 0.0843(18) 0.092(2) -0.0099(16) 0.0040(13) 0.0150(13) C10 0.0637(17) 0.0681(15) 0.0755(18) 0.0026(13) 0.0236(14) 0.0294(13) C11 0.0749(17) 0.0444(11) 0.0608(16) -0.0053(10) 0.0268(13) 0.0138(12) C12 0.0523(13) 0.0452(10) 0.0403(12) -0.0035(9) 0.0128(9) 0.0017(10) C13 0.031(5) 0.023(3) 0.020(5) -0.003(3) 0.001(3) -0.002(3) C14 0.044(5) 0.042(4) 0.030(5) 0.005(3) 0.008(4) 0.006(4) C15 0.023(4) 0.081(7) 0.043(6) -0.004(6) 0.001(4) -0.006(4) C16 0.035(5) 0.050(4) 0.034(5) -0.002(3) -0.002(3) -0.009(4) C17 0.041(5) 0.044(4) 0.032(4) 0.003(3) -0.007(3) -0.010(3) C18 0.033(4) 0.037(3) 0.028(3) 0.000(2) 0.002(3) 0.001(3) C19 0.037(3) 0.048(3) 0.032(3) -0.003(3) 0.008(2) -0.005(3) C20 0.046(5) 0.041(4) 0.019(3) -0.006(3) -0.012(3) -0.004(4) C21 0.018(3) 0.032(3) 0.081(8) -0.004(4) -0.007(4) -0.005(3) C22 0.040(4) 0.032(3) 0.015(3) 0.000(2) -0.002(3) -0.009(3) C23 0.010(3) 0.029(3) 0.033(3) -0.001(2) 0.006(2) -0.004(2) C24 0.094(2) 0.0512(13) 0.0689(18) 0.0163(12) 0.0365(16) 0.0348(14) C25 0.0699(18) 0.0610(15) 0.0712(19) -0.0009(13) 0.0083(14) 0.0049(13) C26 0.0548(15) 0.0713(15) 0.079(2) -0.0010(14) 0.0236(14) -0.0037(13) C27 0.0557(15) 0.0753(16) 0.0591(16) -0.0022(12) 0.0216(12) 0.0046(13) C28 0.0548(15) 0.0673(15) 0.078(2) -0.0103(13) 0.0181(13) -0.0032(12) C29 0.0687(18) 0.0612(14) 0.095(2) 0.0019(14) 0.0454(16) 0.0049(13) O1A 0.066(3) 0.113(3) 0.122(4) 0.065(3) 0.050(3) 0.038(2) C13A 0.033(3) 0.0363(19) 0.028(3) 0.0084(15) 0.0081(17) 0.0020(15) C14A 0.0326(18) 0.061(3) 0.036(2) 0.0150(17) 0.0044(16) -0.0042(17) C15A 0.037(2) 0.085(3) 0.060(3) 0.015(2) -0.0014(19) -0.014(2) C16A 0.045(3) 0.091(3) 0.046(4) 0.017(3) -0.011(3) -0.016(2) C17A 0.049(3) 0.068(3) 0.034(2) 0.0097(18) -0.0011(19) 0.003(2) C18A 0.0324(17) 0.0337(15) 0.0343(18) 0.0057(13) 0.0085(13) 0.0041(14) C19A 0.0475(17) 0.0302(12) 0.0334(15) 0.0030(10) 0.0199(12) 0.0031(12) C20A 0.074(3) 0.0302(14) 0.0433(18) 0.0073(12) 0.0332(16) 0.0102(15) C21A 0.112(7) 0.055(4) 0.090(5) 0.046(3) 0.070(5) 0.045(4) C22A 0.060(3) 0.0428(19) 0.104(4) 0.006(2) 0.005(3) 0.0093(19) C23A 0.045(2) 0.057(3) 0.122(5) 0.035(3) 0.037(3) 0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9597(7) . ? P1 C13A 1.795(6) . ? P1 C1 1.808(2) . ? P1 C7 1.8183(19) . ? P1 C13 1.912(11) . ? O1 C21 1.205(12) . ? C1 C2 1.386(3) . ? C1 C6 1.399(3) . ? C2 C3 1.374(3) . ? C3 C4 1.372(3) . ? C4 C5 1.377(3) . ? C5 C6 1.386(3) . ? C7 C12 1.384(3) . ? C7 C8 1.384(3) . ? C8 C9 1.383(3) . ? C9 C10 1.370(3) . ? C10 C11 1.372(4) . ? C11 C12 1.382(3) . ? C13 C14 1.387(11) . ? C13 C18 1.388(9) . ? C14 C15 1.385(10) . ? C15 C16 1.361(11) . ? C16 C17 1.366(10) . ? C17 C18 1.408(8) . ? C18 C19 1.491(9) . ? C19 C20 1.368(10) . ? C20 C21 1.454(11) . ? C21 C22 1.203(13) . ? C22 C23 1.458(9) . ? C23 C24 1.408(7) . ? C24 C29 1.390(4) . ? C24 C25 1.398(4) . ? C24 C23A 1.606(7) . ? C25 C26 1.377(4) . ? C26 C27 1.361(3) . ? C27 C28 1.372(3) . ? C28 C29 1.360(4) . ? O1A C21A 1.167(8) . ? C13A C14A 1.394(6) . ? C13A C18A 1.408(5) . ? C14A C15A 1.378(6) . ? C15A C16A 1.369(6) . ? C16A C17A 1.360(7) . ? C17A C18A 1.412(5) . ? C18A C19A 1.515(4) . ? C19A C20A 1.537(4) . ? C19A C20A 1.591(4) 3_756 ? C20A C21A 1.533(8) . ? C20A C19A 1.591(4) 3_756 ? C21A C22A 1.666(8) . ? C22A C23A 1.212(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13A P1 C1 100.59(16) . . ? C13A P1 C7 109.42(16) . . ? C1 P1 C7 105.46(8) . . ? C13A P1 C13 14.3(3) . . ? C1 P1 C13 113.6(3) . . ? C7 P1 C13 99.2(3) . . ? C13A P1 S1 116.30(17) . . ? C1 P1 S1 111.60(7) . . ? C7 P1 S1 112.36(7) . . ? C13 P1 S1 113.8(3) . . ? C2 C1 C6 118.4(2) . . ? C2 C1 P1 119.48(16) . . ? C6 C1 P1 122.04(16) . . ? C3 C2 C1 120.8(2) . . ? C4 C3 C2 120.4(2) . . ? C3 C4 C5 120.2(2) . . ? C4 C5 C6 119.8(2) . . ? C5 C6 C1 120.4(2) . . ? C12 C7 C8 119.03(19) . . ? C12 C7 P1 122.58(16) . . ? C8 C7 P1 118.36(14) . . ? C9 C8 C7 120.7(2) . . ? C10 C9 C8 119.6(2) . . ? C9 C10 C11 120.3(2) . . ? C10 C11 C12 120.4(2) . . ? C11 C12 C7 120.0(2) . . ? C14 C13 C18 121.1(9) . . ? C14 C13 P1 112.7(6) . . ? C18 C13 P1 126.1(7) . . ? C15 C14 C13 120.1(8) . . ? C16 C15 C14 120.2(8) . . ? C15 C16 C17 119.5(8) . . ? C16 C17 C18 122.7(8) . . ? C13 C18 C17 116.3(8) . . ? C13 C18 C19 123.4(7) . . ? C17 C18 C19 120.2(6) . . ? C20 C19 C18 128.9(6) . . ? C19 C20 C21 121.1(7) . . ? C22 C21 O1 127.7(8) . . ? C22 C21 C20 113.0(8) . . ? O1 C21 C20 119.2(10) . . ? C21 C22 C23 135.0(7) . . ? C24 C23 C22 123.7(7) . . ? C29 C24 C25 117.5(2) . . ? C29 C24 C23 105.4(4) . . ? C25 C24 C23 136.9(4) . . ? C29 C24 C23A 135.4(3) . . ? C25 C24 C23A 107.0(3) . . ? C23 C24 C23A 30.4(2) . . ? C26 C25 C24 120.5(3) . . ? C27 C26 C25 120.5(3) . . ? C26 C27 C28 119.7(2) . . ? C29 C28 C27 120.6(3) . . ? C28 C29 C24 121.1(3) . . ? C14A C13A C18A 117.8(5) . . ? C14A C13A P1 121.6(4) . . ? C18A C13A P1 120.4(4) . . ? C15A C14A C13A 122.9(4) . . ? C16A C15A C14A 118.5(4) . . ? C17A C16A C15A 121.0(4) . . ? C16A C17A C18A 121.5(4) . . ? C13A C18A C17A 118.2(4) . . ? C13A C18A C19A 122.2(3) . . ? C17A C18A C19A 119.3(3) . . ? C18A C19A C20A 119.3(3) . . ? C18A C19A C20A 115.0(2) . 3_756 ? C20A C19A C20A 89.3(2) . 3_756 ? C21A C20A C19A 114.8(3) . . ? C21A C20A C19A 113.8(3) . 3_756 ? C19A C20A C19A 90.7(2) . 3_756 ? O1A C21A C20A 122.1(5) . . ? O1A C21A C22A 131.8(6) . . ? C20A C21A C22A 105.6(5) . . ? C23A C22A C21A 113.5(6) . . ? C22A C23A C24 110.2(7) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.294 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.043 ### END data_18h _database_code_depnum_ccdc_archive 'CCDC 874841' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.3781(2) _cell_length_b 17.2875(2) _cell_length_c 14.7775(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.232(2) _cell_angle_gamma 90.00 _cell_volume 2341.40(7) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 34683 _cell_measurement_theta_min 3.0594 _cell_measurement_theta_max 30.4392 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97715 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 19733 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.1662 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.0594 _diffrn_reflns_theta_max 30.4392 _reflns_number_total 7072 _reflns_number_gt 3055 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0447346000 _diffrn_orient_matrix_UB_12 -0.0007367000 _diffrn_orient_matrix_UB_13 0.0452913000 _diffrn_orient_matrix_UB_21 -0.0533844000 _diffrn_orient_matrix_UB_22 0.0215673000 _diffrn_orient_matrix_UB_23 0.0168256000 _diffrn_orient_matrix_UB_31 -0.0338005000 _diffrn_orient_matrix_UB_32 -0.0349866000 _diffrn_orient_matrix_UB_33 0.0094210000 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement '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^)+(0.0456P)^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 7072 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1301 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 0.852 _refine_ls_restrained_S_all 0.852 _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 S1 S 0.91756(6) -0.01490(3) 0.22272(4) 0.05318(18) Uani 1 1 d . A . P1 P 0.98698(6) 0.09227(3) 0.23547(4) 0.03700(14) Uani 1 1 d . . . O1 O 0.6265(7) 0.0431(4) 0.4422(5) 0.0520(18) Uani 0.307(4) 1 d P A 1 C1 C 1.0703(2) 0.12046(10) 0.14052(14) 0.0395(5) Uani 1 1 d . A . C2 C 1.1219(2) 0.06370(11) 0.08958(16) 0.0535(6) Uani 1 1 d . . . H2 H 1.1093 0.0107 0.1030 0.064 Uiso 1 1 calc R A . C3 C 1.1914(3) 0.08369(14) 0.01952(16) 0.0648(7) Uani 1 1 d . A . H3 H 1.2263 0.0443 -0.0150 0.078 Uiso 1 1 calc R . . C4 C 1.2105(3) 0.15971(14) -0.00083(17) 0.0638(6) Uani 1 1 d . . . H4 H 1.2595 0.1729 -0.0487 0.077 Uiso 1 1 calc R A . C5 C 1.1587(3) 0.21677(13) 0.04795(18) 0.0662(7) Uani 1 1 d . A . H5 H 1.1705 0.2695 0.0331 0.079 Uiso 1 1 calc R . . C6 C 1.0894(3) 0.19782(11) 0.11872(17) 0.0584(6) Uani 1 1 d . . . H6 H 1.0546 0.2377 0.1527 0.070 Uiso 1 1 calc R A . C7 C 0.8400(2) 0.16088(10) 0.23403(12) 0.0360(4) Uani 1 1 d . A . C8 C 0.6990(2) 0.13817(12) 0.19485(16) 0.0563(6) Uani 1 1 d . . . H8 H 0.6810 0.0869 0.1723 0.068 Uiso 1 1 calc R A . C9 C 0.5837(3) 0.18935(15) 0.18816(19) 0.0766(8) Uani 1 1 d . A . H9 H 0.4871 0.1731 0.1617 0.092 Uiso 1 1 calc R . . C10 C 0.6098(3) 0.26369(14) 0.21990(18) 0.0670(7) Uani 1 1 d . . . H10 H 0.5311 0.2992 0.2145 0.080 Uiso 1 1 calc R A . C11 C 0.7485(3) 0.28680(12) 0.25926(16) 0.0588(6) Uani 1 1 d . A . H11 H 0.7659 0.3383 0.2811 0.071 Uiso 1 1 calc R . . C12 C 0.8634(2) 0.23563(10) 0.26737(14) 0.0450(5) Uani 1 1 d . . . H12 H 0.9592 0.2518 0.2960 0.054 Uiso 1 1 calc R A . C13 C 1.1032(13) 0.1162(5) 0.3553(7) 0.021(2) Uani 0.307(4) 1 d PD A 1 C14 C 1.2467(11) 0.1319(5) 0.3518(6) 0.036(2) Uani 0.307(4) 1 d PD A 1 H14 H 1.2753 0.1328 0.2939 0.044 Uiso 0.307(4) 1 calc PR A 1 C15 C 1.3486(10) 0.1464(5) 0.4325(7) 0.046(3) Uani 0.307(4) 1 d PD A 1 H15 H 1.4473 0.1567 0.4303 0.055 Uiso 0.307(4) 1 calc PR A 1 C16 C 1.3063(11) 0.1458(5) 0.5156(7) 0.040(2) Uani 0.307(4) 1 d PD A 1 H16 H 1.3752 0.1568 0.5710 0.048 Uiso 0.307(4) 1 calc PR A 1 C17 C 1.1653(10) 0.1293(4) 0.5189(6) 0.041(2) Uani 0.307(4) 1 d PD A 1 H17 H 1.1384 0.1285 0.5773 0.049 Uiso 0.307(4) 1 calc PR A 1 C18 C 1.0585(8) 0.1135(4) 0.4389(5) 0.0319(17) Uani 0.307(4) 1 d PD A 1 C19 C 0.9062(7) 0.0941(4) 0.4453(4) 0.0389(18) Uani 0.307(4) 1 d P A 1 H19 H 0.8370 0.0915 0.3882 0.047 Uiso 0.307(4) 1 calc PR A 1 C20 C 0.8535(12) 0.0795(7) 0.5234(6) 0.040(3) Uani 0.307(4) 1 d P A 1 H20 H 0.9169 0.0832 0.5826 0.048 Uiso 0.307(4) 1 calc PR A 1 C21 C 0.7011(11) 0.0583(6) 0.5164(9) 0.045(3) Uani 0.307(4) 1 d P A 1 C22 C 0.6690(10) 0.0554(4) 0.5899(5) 0.0303(17) Uani 0.307(4) 1 d P A 1 H22 H 0.5872 0.0227 0.5891 0.036 Uiso 0.307(4) 1 calc PR A 1 C23 C 0.7241(8) 0.0897(4) 0.6828(5) 0.0221(14) Uani 0.307(4) 1 d P A 1 H23 H 0.8162 0.1149 0.6935 0.027 Uiso 0.307(4) 1 calc PR A 1 C24 C 0.6507(3) 0.08778(14) 0.75542(18) 0.0666(7) Uani 1 1 d . . . C25 C 0.5264(3) 0.05187(13) 0.77381(19) 0.0686(7) Uani 1 1 d . A . H25 H 0.4652 0.0222 0.7270 0.082 Uiso 1 1 calc R . . C26 C 0.4923(3) 0.05930(14) 0.85951(19) 0.0675(7) Uani 1 1 d . . . H26 H 0.4077 0.0346 0.8715 0.081 Uiso 1 1 calc R A . C27 C 0.5789(3) 0.10188(13) 0.92750(17) 0.0619(6) Uani 1 1 d . A . H27 H 0.5552 0.1064 0.9867 0.074 Uiso 1 1 calc R . . C28 C 0.7001(3) 0.13798(13) 0.90999(19) 0.0669(7) Uani 1 1 d . . . H28 H 0.7596 0.1683 0.9569 0.080 Uiso 1 1 calc R A . C29 C 0.7359(3) 0.13072(13) 0.8259(2) 0.0698(7) Uani 1 1 d . A . H29 H 0.8211 0.1556 0.8152 0.084 Uiso 1 1 calc R . . O1A O 0.7067(5) 0.0639(3) 0.4568(4) 0.0971(18) Uani 0.693(4) 1 d P A 2 C13A C 1.1336(6) 0.1126(3) 0.3321(4) 0.0316(12) Uani 0.693(4) 1 d PD A 2 C14A C 1.2592(5) 0.1513(2) 0.3217(3) 0.0437(11) Uani 0.693(4) 1 d PD A 2 H14A H 1.2702 0.1637 0.2610 0.052 Uiso 0.693(4) 1 calc PR A 2 C15A C 1.3684(5) 0.1723(2) 0.3957(3) 0.0636(14) Uani 0.693(4) 1 d PD A 2 H15A H 1.4530 0.1984 0.3860 0.076 Uiso 0.693(4) 1 calc PR A 2 C16A C 1.3526(7) 0.1548(4) 0.4832(4) 0.0654(19) Uani 0.693(4) 1 d PD A 2 H16A H 1.4262 0.1698 0.5349 0.078 Uiso 0.693(4) 1 calc PR A 2 C17A C 1.2322(6) 0.1161(3) 0.4974(3) 0.0519(11) Uani 0.693(4) 1 d PD A 2 H17A H 1.2238 0.1046 0.5589 0.062 Uiso 0.693(4) 1 calc PR A 2 C18A C 1.1203(4) 0.09284(18) 0.4230(2) 0.0329(7) Uani 0.693(4) 1 d PD A 2 C19A C 1.0005(3) 0.04080(13) 0.44164(18) 0.0346(8) Uani 0.693(4) 1 d P . 2 H19A H 0.9136 0.0431 0.3891 0.042 Uiso 0.693(4) 1 calc PR A 2 C20A C 0.9529(4) 0.04690(15) 0.5345(2) 0.0456(9) Uani 0.693(4) 1 d P . 2 H20A H 1.0154 0.0839 0.5776 0.055 Uiso 0.693(4) 1 calc PR A 2 C21A C 0.7911(10) 0.0625(4) 0.5274(5) 0.080(3) Uani 0.693(4) 1 d P A 2 C22A C 0.7718(5) 0.0850(2) 0.6342(4) 0.0731(13) Uani 0.693(4) 1 d P A 2 H22A H 0.8469 0.1084 0.6791 0.088 Uiso 0.693(4) 1 calc PR A 2 C23A C 0.6539(6) 0.0687(3) 0.6489(5) 0.0723(17) Uani 0.693(4) 1 d P A 2 H23A H 0.5749 0.0479 0.6047 0.087 Uiso 0.693(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0472(3) 0.0347(2) 0.0711(4) -0.0010(3) -0.0021(3) -0.0042(2) P1 0.0369(3) 0.0322(2) 0.0379(3) 0.0026(2) -0.0011(2) 0.0007(2) O1 0.041(4) 0.057(3) 0.049(4) -0.009(3) -0.009(3) -0.009(3) C1 0.0342(11) 0.0406(9) 0.0427(12) 0.0009(9) 0.0063(9) 0.0065(9) C2 0.0565(15) 0.0460(11) 0.0563(16) -0.0074(10) 0.0080(12) 0.0014(11) C3 0.0716(17) 0.0745(15) 0.0520(16) -0.0165(13) 0.0212(13) 0.0105(14) C4 0.0595(16) 0.0841(17) 0.0525(16) 0.0018(13) 0.0226(12) 0.0044(14) C5 0.0712(18) 0.0554(13) 0.083(2) 0.0104(13) 0.0423(15) 0.0058(12) C6 0.0676(16) 0.0415(11) 0.0768(18) 0.0038(11) 0.0397(13) 0.0118(11) C7 0.0413(11) 0.0402(10) 0.0264(10) -0.0003(8) 0.0071(8) 0.0032(9) C8 0.0431(13) 0.0567(12) 0.0648(16) -0.0110(11) 0.0018(11) 0.0055(11) C9 0.0451(14) 0.0857(18) 0.094(2) -0.0113(16) 0.0039(14) 0.0160(14) C10 0.0623(17) 0.0696(16) 0.0734(19) 0.0044(13) 0.0237(14) 0.0278(13) C11 0.0769(18) 0.0443(11) 0.0604(16) -0.0042(11) 0.0259(13) 0.0150(12) C12 0.0529(13) 0.0446(11) 0.0389(12) -0.0033(9) 0.0126(10) 0.0022(10) C13 0.029(5) 0.021(3) 0.013(5) -0.006(3) 0.005(3) -0.002(3) C14 0.041(6) 0.042(5) 0.027(5) 0.005(4) 0.010(4) 0.004(4) C15 0.023(4) 0.069(6) 0.044(8) 0.001(6) 0.001(5) -0.009(4) C16 0.032(6) 0.045(5) 0.039(6) -0.002(4) -0.002(4) -0.007(4) C17 0.042(5) 0.045(4) 0.030(5) -0.001(3) -0.003(4) -0.008(4) C18 0.035(4) 0.035(4) 0.025(4) -0.002(3) 0.008(3) 0.006(3) C19 0.039(4) 0.053(4) 0.025(3) -0.007(3) 0.008(3) -0.004(3) C20 0.041(6) 0.049(6) 0.020(5) -0.013(4) -0.013(4) 0.002(5) C21 0.019(4) 0.031(4) 0.075(9) -0.002(5) -0.012(5) 0.002(4) C22 0.043(5) 0.030(3) 0.015(4) -0.003(3) -0.002(3) -0.010(3) C23 0.007(3) 0.026(3) 0.033(4) -0.001(3) 0.005(3) -0.006(3) C24 0.091(2) 0.0520(13) 0.0657(18) 0.0161(13) 0.0366(16) 0.0349(14) C25 0.0696(18) 0.0632(15) 0.0693(19) -0.0022(13) 0.0066(15) 0.0072(14) C26 0.0551(16) 0.0741(15) 0.077(2) -0.0017(14) 0.0229(14) -0.0041(13) C27 0.0569(15) 0.0746(15) 0.0590(16) -0.0024(13) 0.0232(13) 0.0035(13) C28 0.0558(16) 0.0682(14) 0.079(2) -0.0117(13) 0.0198(14) -0.0026(13) C29 0.0690(18) 0.0610(14) 0.091(2) 0.0017(15) 0.0433(16) 0.0048(13) O1A 0.067(3) 0.114(3) 0.122(4) 0.063(3) 0.046(4) 0.037(2) C13A 0.032(3) 0.037(2) 0.028(3) 0.0087(17) 0.0120(18) 0.0043(16) C14A 0.033(2) 0.060(3) 0.037(3) 0.0158(18) 0.0050(18) -0.0041(18) C15A 0.037(2) 0.085(3) 0.063(3) 0.020(2) -0.002(2) -0.013(2) C16A 0.045(3) 0.090(4) 0.051(5) 0.015(3) -0.012(3) -0.014(3) C17A 0.050(3) 0.068(3) 0.033(2) 0.0115(19) 0.000(2) 0.003(2) C18A 0.0353(19) 0.0330(16) 0.0313(19) 0.0068(14) 0.0091(15) 0.0038(15) C19A 0.0465(18) 0.0316(13) 0.0307(16) 0.0024(11) 0.0194(13) 0.0026(12) C20A 0.072(3) 0.0315(14) 0.0429(19) 0.0064(13) 0.0322(17) 0.0082(16) C21A 0.114(8) 0.061(4) 0.082(5) 0.043(3) 0.062(5) 0.053(5) C22A 0.064(3) 0.0423(19) 0.107(4) 0.003(2) 0.006(3) 0.010(2) C23A 0.041(3) 0.055(3) 0.129(6) 0.034(3) 0.036(4) 0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9596(6) . ? P1 C13A 1.794(6) . ? P1 C1 1.812(2) . ? P1 C7 1.8150(19) . ? P1 C13 1.917(11) . ? O1 C21 1.197(15) . ? C1 C2 1.385(3) . ? C1 C6 1.396(2) . ? C2 C3 1.379(3) . ? C3 C4 1.368(3) . ? C4 C5 1.370(3) . ? C5 C6 1.383(3) . ? C7 C8 1.384(3) . ? C7 C12 1.384(2) . ? C8 C9 1.384(3) . ? C9 C10 1.372(3) . ? C10 C11 1.368(3) . ? C11 C12 1.380(3) . ? C13 C14 1.384(11) . ? C13 C18 1.388(9) . ? C14 C15 1.384(11) . ? C15 C16 1.367(12) . ? C16 C17 1.363(10) . ? C17 C18 1.405(9) . ? C18 C19 1.489(9) . ? C19 C20 1.372(12) . ? C20 C21 1.458(14) . ? C21 C22 1.189(15) . ? C22 C23 1.484(10) . ? C23 C24 1.392(8) . ? C24 C29 1.386(4) . ? C24 C25 1.398(3) . ? C24 C23A 1.614(7) . ? C25 C26 1.377(3) . ? C26 C27 1.366(3) . ? C27 C28 1.368(3) . ? C28 C29 1.360(3) . ? O1A C21A 1.169(8) . ? C13A C14A 1.390(6) . ? C13A C18A 1.418(5) . ? C14A C15A 1.379(6) . ? C15A C16A 1.367(6) . ? C16A C17A 1.367(7) . ? C17A C18A 1.408(5) . ? C18A C19A 1.509(4) . ? C19A C20A 1.534(4) . ? C19A C20A 1.596(4) 3_756 ? C20A C21A 1.523(8) . ? C20A C19A 1.596(4) 3_756 ? C21A C22A 1.671(9) . ? C22A C23A 1.204(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13A P1 C1 100.36(16) . . ? C13A P1 C7 109.46(16) . . ? C1 P1 C7 105.44(8) . . ? C13A P1 C13 14.8(3) . . ? C1 P1 C13 113.8(3) . . ? C7 P1 C13 98.7(3) . . ? C13A P1 S1 116.41(17) . . ? C1 P1 S1 111.65(6) . . ? C7 P1 S1 112.38(7) . . ? C13 P1 S1 113.9(3) . . ? C2 C1 C6 118.5(2) . . ? C2 C1 P1 119.22(15) . . ? C6 C1 P1 122.27(15) . . ? C3 C2 C1 120.4(2) . . ? C4 C3 C2 120.7(2) . . ? C3 C4 C5 119.9(2) . . ? C4 C5 C6 120.2(2) . . ? C5 C6 C1 120.4(2) . . ? C8 C7 C12 118.64(18) . . ? C8 C7 P1 118.41(14) . . ? C12 C7 P1 122.91(15) . . ? C7 C8 C9 120.8(2) . . ? C10 C9 C8 119.7(2) . . ? C11 C10 C9 120.2(2) . . ? C10 C11 C12 120.3(2) . . ? C11 C12 C7 120.4(2) . . ? C14 C13 C18 121.3(9) . . ? C14 C13 P1 112.0(6) . . ? C18 C13 P1 126.5(7) . . ? C13 C14 C15 120.2(8) . . ? C16 C15 C14 119.6(8) . . ? C17 C16 C15 120.1(8) . . ? C16 C17 C18 122.3(8) . . ? C13 C18 C17 116.5(8) . . ? C13 C18 C19 122.6(7) . . ? C17 C18 C19 120.9(6) . . ? C20 C19 C18 128.0(6) . . ? C19 C20 C21 120.6(9) . . ? C22 C21 O1 128.0(10) . . ? C22 C21 C20 112.3(10) . . ? O1 C21 C20 119.6(12) . . ? C21 C22 C23 136.3(9) . . ? C24 C23 C22 124.8(7) . . ? C29 C24 C23 105.4(4) . . ? C29 C24 C25 117.6(2) . . ? C23 C24 C25 136.8(4) . . ? C29 C24 C23A 135.6(3) . . ? C23 C24 C23A 30.6(3) . . ? C25 C24 C23A 106.7(3) . . ? C26 C25 C24 120.2(3) . . ? C27 C26 C25 120.6(3) . . ? C26 C27 C28 119.7(2) . . ? C29 C28 C27 120.4(2) . . ? C28 C29 C24 121.4(3) . . ? C14A C13A C18A 117.9(5) . . ? C14A C13A P1 122.1(4) . . ? C18A C13A P1 120.0(4) . . ? C15A C14A C13A 122.9(4) . . ? C16A C15A C14A 118.8(4) . . ? C17A C16A C15A 120.8(5) . . ? C16A C17A C18A 121.6(4) . . ? C17A C18A C13A 118.0(4) . . ? C17A C18A C19A 119.2(3) . . ? C13A C18A C19A 122.4(3) . . ? C18A C19A C20A 119.4(2) . . ? C18A C19A C20A 115.2(2) . 3_756 ? C20A C19A C20A 89.2(2) . 3_756 ? C21A C20A C19A 115.1(3) . . ? C21A C20A C19A 114.0(3) . 3_756 ? C19A C20A C19A 90.8(2) . 3_756 ? O1A C21A C20A 122.8(6) . . ? O1A C21A C22A 130.5(7) . . ? C20A C21A C22A 106.4(5) . . ? C23A C22A C21A 113.8(7) . . ? C22A C23A C24 109.7(7) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.247 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.041 ### END data_140K _database_code_depnum_ccdc_archive 'CCDC 874842' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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 9.4946(2) _cell_length_b 17.0479(4) _cell_length_c 14.5784(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.951(2) _cell_angle_gamma 90.00 _cell_volume 2308.56(10) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 3557 _cell_measurement_theta_min 2.8506 _cell_measurement_theta_max 29.1369 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98288 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 11979 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.1125 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.8506 _diffrn_reflns_theta_max 29.1369 _reflns_number_total 5420 _reflns_number_gt 3806 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0023202000 _diffrn_orient_matrix_UB_12 -0.0229406000 _diffrn_orient_matrix_UB_13 -0.0408788000 _diffrn_orient_matrix_UB_21 0.0756164000 _diffrn_orient_matrix_UB_22 0.0040344000 _diffrn_orient_matrix_UB_23 0.0053274000 _diffrn_orient_matrix_UB_31 0.0103891000 _diffrn_orient_matrix_UB_32 -0.0344637000 _diffrn_orient_matrix_UB_33 0.0278382000 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement '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^)+(0.0476P)^2^+0.2395P] 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 5420 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1122 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.41597(6) -0.01057(3) 0.23186(4) 0.02693(15) Uani 1 1 d . . . P1 P 0.48019(5) 0.09878(3) 0.23915(4) 0.01922(14) Uani 1 1 d . . . O1 O 0.14238(15) 0.04572(10) 0.43815(10) 0.0341(4) Uani 1 1 d . . . C1 C 0.5688(2) 0.12520(12) 0.14437(13) 0.0209(4) Uani 1 1 d . . . C2 C 0.5993(2) 0.20325(13) 0.12649(15) 0.0283(5) Uani 1 1 d . . . H2 H 0.5715 0.2441 0.1634 0.034 Uiso 1 1 calc R . . C3 C 0.6700(2) 0.22097(14) 0.05494(16) 0.0335(5) Uani 1 1 d . . . H3 H 0.6905 0.2740 0.0427 0.040 Uiso 1 1 calc R . . C4 C 0.7108(2) 0.16176(16) 0.00136(16) 0.0360(6) Uani 1 1 d . . . H4 H 0.7593 0.1741 -0.0476 0.043 Uiso 1 1 calc R . . C5 C 0.6810(2) 0.08450(16) 0.01889(17) 0.0391(6) Uani 1 1 d . . . H5 H 0.7093 0.0438 -0.0180 0.047 Uiso 1 1 calc R . . C6 C 0.6100(2) 0.06619(14) 0.09017(15) 0.0297(5) Uani 1 1 d . . . H6 H 0.5896 0.0130 0.1019 0.036 Uiso 1 1 calc R . . C7 C 0.33209(19) 0.16779(12) 0.23251(13) 0.0202(4) Uani 1 1 d . . . C8 C 0.3539(2) 0.24452(13) 0.26439(14) 0.0246(5) Uani 1 1 d . . . H8 H 0.4484 0.2626 0.2901 0.030 Uiso 1 1 calc R . . C9 C 0.2377(2) 0.29463(14) 0.25871(15) 0.0314(5) Uani 1 1 d . . . H9 H 0.2528 0.3475 0.2790 0.038 Uiso 1 1 calc R . . C10 C 0.0992(2) 0.26779(15) 0.22347(16) 0.0359(6) Uani 1 1 d . . . H10 H 0.0197 0.3021 0.2209 0.043 Uiso 1 1 calc R . . C11 C 0.0763(2) 0.19185(16) 0.19226(17) 0.0390(6) Uani 1 1 d . . . H11 H -0.0187 0.1739 0.1676 0.047 Uiso 1 1 calc R . . C12 C 0.1929(2) 0.14147(14) 0.19695(15) 0.0307(5) Uani 1 1 d . . . H12 H 0.1773 0.0889 0.1758 0.037 Uiso 1 1 calc R . . C13 C 0.60800(19) 0.12261(12) 0.34705(13) 0.0197(4) Uani 1 1 d . . . C14 C 0.7495(2) 0.14139(12) 0.34287(15) 0.0247(5) Uani 1 1 d . . . H14 H 0.7765 0.1442 0.2838 0.030 Uiso 1 1 calc R . . C15 C 0.8512(2) 0.15595(13) 0.42423(16) 0.0297(5) Uani 1 1 d . . . H15 H 0.9471 0.1691 0.4207 0.036 Uiso 1 1 calc R . . C16 C 0.8125(2) 0.15130(14) 0.50994(16) 0.0307(5) Uani 1 1 d . . . H16 H 0.8820 0.1614 0.5656 0.037 Uiso 1 1 calc R . . C17 C 0.6738(2) 0.13206(13) 0.51557(15) 0.0276(5) Uani 1 1 d . . . H17 H 0.6493 0.1289 0.5754 0.033 Uiso 1 1 calc R . . C18 C 0.5680(2) 0.11708(12) 0.43519(14) 0.0222(5) Uani 1 1 d . . . C19 C 0.4205(2) 0.09572(12) 0.44314(14) 0.0239(5) Uani 1 1 d . . . H19 H 0.3517 0.0913 0.3859 0.029 Uiso 1 1 calc R . . C20 C 0.3726(2) 0.08192(13) 0.52086(15) 0.0270(5) Uani 1 1 d . . . H20 H 0.4358 0.0860 0.5804 0.032 Uiso 1 1 calc R . . C21 C 0.2197(2) 0.06006(12) 0.51421(15) 0.0247(5) Uani 1 1 d . . . C22 C 0.1610(2) 0.05631(13) 0.60011(14) 0.0257(5) Uani 1 1 d . . . H22 H 0.0725 0.0294 0.5968 0.031 Uiso 1 1 calc R . . C23 C 0.2232(2) 0.08797(13) 0.68195(15) 0.0253(5) Uani 1 1 d . . . H23 H 0.3146 0.1114 0.6844 0.030 Uiso 1 1 calc R . . C24 C 0.1687(2) 0.09121(13) 0.76849(14) 0.0241(5) Uani 1 1 d . . . C25 C 0.2468(2) 0.13232(14) 0.84543(16) 0.0317(5) Uani 1 1 d . . . H25 H 0.3341 0.1574 0.8401 0.038 Uiso 1 1 calc R . . C26 C 0.2007(2) 0.13746(15) 0.92869(16) 0.0357(6) Uani 1 1 d . . . H26 H 0.2555 0.1659 0.9799 0.043 Uiso 1 1 calc R . . C27 C 0.0734(2) 0.10084(14) 0.93757(16) 0.0338(5) Uani 1 1 d . . . H27 H 0.0409 0.1040 0.9949 0.041 Uiso 1 1 calc R . . C28 C -0.0055(2) 0.05985(14) 0.86242(16) 0.0316(5) Uani 1 1 d . . . H28 H -0.0925 0.0348 0.8685 0.038 Uiso 1 1 calc R . . C29 C 0.0402(2) 0.05463(13) 0.77842(15) 0.0287(5) Uani 1 1 d . . . H29 H -0.0155 0.0263 0.7274 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 S1 0.0281(3) 0.0199(3) 0.0316(3) -0.0017(2) 0.0033(2) -0.0036(2) P1 0.0189(3) 0.0190(3) 0.0197(3) -0.0015(2) 0.0039(2) 0.0003(2) O1 0.0273(8) 0.0469(11) 0.0269(8) -0.0026(7) 0.0030(7) -0.0052(7) C1 0.0190(10) 0.0246(12) 0.0190(10) 0.0004(9) 0.0040(8) 0.0032(8) C2 0.0322(12) 0.0257(12) 0.0297(12) 0.0004(10) 0.0128(10) 0.0039(9) C3 0.0353(12) 0.0314(14) 0.0364(13) 0.0065(11) 0.0132(11) 0.0010(10) C4 0.0341(12) 0.0506(17) 0.0256(12) 0.0019(11) 0.0117(10) 0.0005(11) C5 0.0432(14) 0.0456(17) 0.0319(13) -0.0129(12) 0.0156(11) 0.0029(12) C6 0.0357(12) 0.0261(13) 0.0285(11) -0.0054(10) 0.0095(10) 0.0008(10) C7 0.0194(10) 0.0258(12) 0.0160(9) 0.0019(8) 0.0053(8) 0.0037(8) C8 0.0267(10) 0.0261(12) 0.0220(10) -0.0012(9) 0.0069(9) 0.0039(9) C9 0.0392(13) 0.0300(13) 0.0265(11) 0.0007(10) 0.0104(10) 0.0126(10) C10 0.0315(13) 0.0410(16) 0.0369(13) 0.0062(11) 0.0113(11) 0.0165(11) C11 0.0192(11) 0.0540(18) 0.0418(14) 0.0036(13) 0.0014(10) 0.0072(11) C12 0.0247(11) 0.0351(14) 0.0303(12) -0.0048(10) 0.0011(9) 0.0012(9) C13 0.0180(10) 0.0169(10) 0.0226(10) -0.0004(8) 0.0008(8) 0.0001(8) C14 0.0222(10) 0.0235(12) 0.0297(11) -0.0001(9) 0.0086(9) 0.0016(8) C15 0.0157(10) 0.0309(13) 0.0409(13) -0.0012(10) 0.0022(9) -0.0018(9) C16 0.0241(11) 0.0344(14) 0.0290(12) -0.0045(10) -0.0047(9) -0.0006(9) C17 0.0277(11) 0.0314(13) 0.0223(11) -0.0006(9) 0.0016(9) -0.0003(9) C18 0.0215(10) 0.0202(11) 0.0240(10) 0.0005(9) 0.0028(9) 0.0028(8) C19 0.0221(10) 0.0264(12) 0.0224(10) -0.0004(9) 0.0026(8) 0.0010(9) C20 0.0228(10) 0.0332(13) 0.0237(11) -0.0016(9) 0.0021(9) -0.0011(9) C21 0.0244(10) 0.0212(12) 0.0279(11) 0.0008(9) 0.0041(9) 0.0021(8) C22 0.0209(10) 0.0268(13) 0.0304(11) 0.0013(10) 0.0074(9) -0.0011(9) C23 0.0218(10) 0.0233(12) 0.0316(11) 0.0029(9) 0.0076(9) -0.0015(8) C24 0.0230(10) 0.0236(12) 0.0261(11) 0.0017(9) 0.0061(9) 0.0024(8) C25 0.0270(11) 0.0342(14) 0.0341(12) -0.0048(11) 0.0066(10) -0.0063(10) C26 0.0390(13) 0.0388(15) 0.0283(12) -0.0080(11) 0.0047(10) -0.0063(11) C27 0.0399(13) 0.0349(14) 0.0292(12) -0.0014(11) 0.0134(11) 0.0002(11) C28 0.0306(12) 0.0325(14) 0.0347(12) 0.0014(10) 0.0136(10) -0.0043(10) C29 0.0278(11) 0.0276(13) 0.0309(12) -0.0005(10) 0.0062(10) -0.0041(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 S1 P1 1.9573(8) . ? P1 C1 1.817(2) . ? P1 C7 1.821(2) . ? P1 C13 1.8225(19) . ? O1 C21 1.221(2) . ? C1 C6 1.385(3) . ? C1 C2 1.398(3) . ? C2 C3 1.386(3) . ? C2 H2 0.9500 . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(4) . ? C4 H4 0.9500 . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.390(3) . ? C7 C8 1.389(3) . ? C8 C9 1.384(3) . ? C8 H8 0.9500 . ? C9 C10 1.386(3) . ? C9 H9 0.9500 . ? C10 C11 1.375(4) . ? C10 H10 0.9500 . ? C11 C12 1.392(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.394(3) . ? C13 C18 1.416(3) . ? C14 C15 1.388(3) . ? C14 H14 0.9500 . ? C15 C16 1.375(3) . ? C15 H15 0.9500 . ? C16 C17 1.376(3) . ? C16 H16 0.9500 . ? C17 C18 1.400(3) . ? C17 H17 0.9500 . ? C18 C19 1.475(3) . ? C19 C20 1.326(3) . ? C19 H19 0.9500 . ? C20 C21 1.483(3) . ? C20 H20 0.9500 . ? C21 C22 1.473(3) . ? C22 C23 1.331(3) . ? C22 H22 0.9500 . ? C23 C24 1.460(3) . ? C23 H23 0.9500 . ? C24 C25 1.398(3) . ? C24 C29 1.405(3) . ? C25 C26 1.376(3) . ? C25 H25 0.9500 . ? C26 C27 1.389(3) . ? C26 H26 0.9500 . ? C27 C28 1.382(3) . ? C27 H27 0.9500 . ? C28 C29 1.384(3) . ? C28 H28 0.9500 . ? C29 H29 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 C1 P1 C7 105.86(9) . . ? C1 P1 C13 105.71(9) . . ? C7 P1 C13 105.71(9) . . ? C1 P1 S1 112.52(7) . . ? C7 P1 S1 112.59(7) . . ? C13 P1 S1 113.79(7) . . ? C6 C1 C2 119.4(2) . . ? C6 C1 P1 118.94(17) . . ? C2 C1 P1 121.62(16) . . ? C3 C2 C1 120.0(2) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.0(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 120.2(2) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C12 C7 C8 119.52(19) . . ? C12 C7 P1 118.38(16) . . ? C8 C7 P1 122.07(15) . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.1(2) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.5(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.7(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C7 C12 C11 120.3(2) . . ? C7 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C18 119.78(17) . . ? C14 C13 P1 119.25(15) . . ? C18 C13 P1 120.83(14) . . ? C15 C14 C13 120.6(2) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 119.79(19) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 120.44(19) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C18 121.6(2) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C17 C18 C13 117.79(18) . . ? C17 C18 C19 120.53(19) . . ? C13 C18 C19 121.68(17) . . ? C20 C19 C18 127.59(19) . . ? C20 C19 H19 116.2 . . ? C18 C19 H19 116.2 . . ? C19 C20 C21 119.54(19) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? O1 C21 C22 120.09(18) . . ? O1 C21 C20 120.39(19) . . ? C22 C21 C20 119.51(18) . . ? C23 C22 C21 124.67(19) . . ? C23 C22 H22 117.7 . . ? C21 C22 H22 117.7 . . ? C22 C23 C24 128.26(19) . . ? C22 C23 H23 115.9 . . ? C24 C23 H23 115.9 . . ? C25 C24 C29 117.9(2) . . ? C25 C24 C23 119.22(18) . . ? C29 C24 C23 122.89(19) . . ? C26 C25 C24 121.8(2) . . ? C26 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? C25 C26 C27 119.7(2) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C28 C27 C26 119.5(2) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C27 C28 C29 121.1(2) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C28 C29 C24 120.0(2) . . ? C28 C29 H29 120.0 . . ? C24 C29 H29 120.0 . . ? 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 C6 -136.78(16) . . . . ? C13 P1 C1 C6 111.36(17) . . . . ? S1 P1 C1 C6 -13.41(18) . . . . ? C7 P1 C1 C2 44.83(18) . . . . ? C13 P1 C1 C2 -67.03(18) . . . . ? S1 P1 C1 C2 168.20(14) . . . . ? C6 C1 C2 C3 0.1(3) . . . . ? P1 C1 C2 C3 178.49(16) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? P1 C1 C6 C5 -178.39(16) . . . . ? C4 C5 C6 C1 -0.1(3) . . . . ? C1 P1 C7 C12 105.10(17) . . . . ? C13 P1 C7 C12 -143.03(16) . . . . ? S1 P1 C7 C12 -18.22(18) . . . . ? C1 P1 C7 C8 -76.92(18) . . . . ? C13 P1 C7 C8 34.94(19) . . . . ? S1 P1 C7 C8 159.75(15) . . . . ? C12 C7 C8 C9 -1.4(3) . . . . ? P1 C7 C8 C9 -179.36(16) . . . . ? C7 C8 C9 C10 1.7(3) . . . . ? C8 C9 C10 C11 -1.2(3) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C8 C7 C12 C11 0.8(3) . . . . ? P1 C7 C12 C11 178.79(18) . . . . ? C10 C11 C12 C7 -0.4(3) . . . . ? C1 P1 C13 C14 -11.03(19) . . . . ? C7 P1 C13 C14 -123.00(17) . . . . ? S1 P1 C13 C14 112.95(16) . . . . ? C1 P1 C13 C18 173.28(16) . . . . ? C7 P1 C13 C18 61.32(18) . . . . ? S1 P1 C13 C18 -62.74(17) . . . . ? C18 C13 C14 C15 -1.0(3) . . . . ? P1 C13 C14 C15 -176.75(17) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C15 C16 C17 C18 -0.3(3) . . . . ? C16 C17 C18 C13 -0.2(3) . . . . ? C16 C17 C18 C19 179.3(2) . . . . ? C14 C13 C18 C17 0.9(3) . . . . ? P1 C13 C18 C17 176.53(16) . . . . ? C14 C13 C18 C19 -178.66(19) . . . . ? P1 C13 C18 C19 -3.0(3) . . . . ? C17 C18 C19 C20 -5.9(3) . . . . ? C13 C18 C19 C20 173.6(2) . . . . ? C18 C19 C20 C21 -179.2(2) . . . . ? C19 C20 C21 O1 8.7(3) . . . . ? C19 C20 C21 C22 -170.9(2) . . . . ? O1 C21 C22 C23 -163.3(2) . . . . ? C20 C21 C22 C23 16.2(3) . . . . ? C21 C22 C23 C24 175.90(19) . . . . ? C22 C23 C24 C25 -175.5(2) . . . . ? C22 C23 C24 C29 4.5(3) . . . . ? C29 C24 C25 C26 -0.1(3) . . . . ? C23 C24 C25 C26 179.9(2) . . . . ? C24 C25 C26 C27 0.2(4) . . . . ? C25 C26 C27 C28 -0.2(4) . . . . ? C26 C27 C28 C29 0.0(3) . . . . ? C27 C28 C29 C24 0.1(3) . . . . ? C25 C24 C29 C28 -0.1(3) . . . . ? C23 C24 C29 C28 179.92(19) . . . . ? _diffrn_measured_fraction_theta_max 0.869 _diffrn_reflns_theta_full 29.20 _diffrn_measured_fraction_theta_full 0.869 _refine_diff_density_max 0.389 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.056 ### END data_150K _database_code_depnum_ccdc_archive 'CCDC 874843' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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 9.4645(2) _cell_length_b 17.0968(4) _cell_length_c 14.5914(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.008(3) _cell_angle_gamma 90.00 _cell_volume 2309.41(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3751 _cell_measurement_theta_min 3.0877 _cell_measurement_theta_max 29.1545 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98924 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 11446 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0893 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.0877 _diffrn_reflns_theta_max 29.1545 _reflns_number_total 5404 _reflns_number_gt 3944 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0586713000 _diffrn_orient_matrix_UB_12 0.0129162000 _diffrn_orient_matrix_UB_13 -0.0352344000 _diffrn_orient_matrix_UB_21 0.0191826000 _diffrn_orient_matrix_UB_22 0.0394177000 _diffrn_orient_matrix_UB_23 0.0115292000 _diffrn_orient_matrix_UB_31 0.0453680000 _diffrn_orient_matrix_UB_32 0.0000347000 _diffrn_orient_matrix_UB_33 -0.0331102000 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement '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^)+(0.0330P)^2^+0.9412P] 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 5404 _refine_ls_number_parameters 338 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91622(5) -0.01070(3) 0.23072(4) 0.03335(14) Uani 1 1 d . A . P1 P 0.98123(5) 0.09830(3) 0.23880(3) 0.02345(12) Uani 1 1 d . . . O1 O 0.6406(2) 0.04511(12) 0.43831(13) 0.0383(5) Uani 0.886(4) 1 d P A 1 C1 C 0.83231(19) 0.16673(11) 0.23271(13) 0.0247(4) Uani 1 1 d . A . C2 C 0.6928(2) 0.14120(13) 0.19660(15) 0.0366(5) Uani 1 1 d . . . H2 H 0.6767 0.0889 0.1751 0.044 Uiso 1 1 calc R A . C3 C 0.5768(2) 0.19134(15) 0.19162(17) 0.0466(6) Uani 1 1 d . A . H3 H 0.4814 0.1734 0.1672 0.056 Uiso 1 1 calc R . . C4 C 0.5999(2) 0.26722(14) 0.22214(16) 0.0443(6) Uani 1 1 d . . . H4 H 0.5202 0.3017 0.2184 0.053 Uiso 1 1 calc R A . C5 C 0.7379(2) 0.29354(13) 0.25813(15) 0.0382(5) Uani 1 1 d . A . H5 H 0.7529 0.3462 0.2787 0.046 Uiso 1 1 calc R . . C6 C 0.8544(2) 0.24388(11) 0.26450(14) 0.0302(4) Uani 1 1 d . . . H6 H 0.9493 0.2620 0.2904 0.036 Uiso 1 1 calc R A . C7 C 1.06915(19) 0.12493(11) 0.14401(13) 0.0257(4) Uani 1 1 d . A . C8 C 1.0987(2) 0.20271(12) 0.12593(15) 0.0340(5) Uani 1 1 d . . . H8 H 1.0704 0.2433 0.1628 0.041 Uiso 1 1 calc R A . C9 C 1.1691(2) 0.22085(13) 0.05434(16) 0.0401(5) Uani 1 1 d . A . H9 H 1.1886 0.2739 0.0420 0.048 Uiso 1 1 calc R . . C10 C 1.2108(2) 0.16227(14) 0.00108(15) 0.0422(5) Uani 1 1 d . . . H10 H 1.2595 0.1748 -0.0477 0.051 Uiso 1 1 calc R A . C11 C 1.1820(2) 0.08531(14) 0.01858(16) 0.0442(6) Uani 1 1 d . A . H11 H 1.2106 0.0449 -0.0184 0.053 Uiso 1 1 calc R . . C12 C 1.1116(2) 0.06678(12) 0.08976(15) 0.0360(5) Uani 1 1 d . . . H12 H 1.0923 0.0136 0.1015 0.043 Uiso 1 1 calc R A . C13 C 1.1058(3) 0.12251(16) 0.34723(19) 0.0233(7) Uani 0.886(4) 1 d PD A 1 C14 C 1.2488(3) 0.14048(17) 0.3440(2) 0.0294(7) Uani 0.886(4) 1 d PD A 1 H14 H 1.2764 0.1430 0.2851 0.035 Uiso 0.886(4) 1 calc PR A 1 C15 C 1.3514(3) 0.15477(17) 0.4254(2) 0.0350(6) Uani 0.886(4) 1 d PD A 1 H15 H 1.4479 0.1675 0.4221 0.042 Uiso 0.886(4) 1 calc PR A 1 C16 C 1.3118(3) 0.15022(19) 0.5108(2) 0.0353(7) Uani 0.886(4) 1 d PD A 1 H16 H 1.3812 0.1599 0.5667 0.042 Uiso 0.886(4) 1 calc PR A 1 C17 C 1.1722(3) 0.13170(15) 0.51557(17) 0.0312(6) Uani 0.886(4) 1 d PD A 1 H17 H 1.1468 0.1288 0.5751 0.037 Uiso 0.886(4) 1 calc PR A 1 C18 C 1.0670(3) 0.11700(14) 0.43525(15) 0.0245(5) Uani 0.886(4) 1 d PD A 1 C19 C 0.9189(2) 0.09607(12) 0.44302(15) 0.0273(5) Uani 0.886(4) 1 d P A 1 H19 H 0.8495 0.0927 0.3859 0.033 Uiso 0.886(4) 1 calc PR A 1 C20 C 0.8714(3) 0.08138(14) 0.52054(16) 0.0297(6) Uani 0.886(4) 1 d P A 1 H20 H 0.9352 0.0849 0.5800 0.036 Uiso 0.886(4) 1 calc PR A 1 C21 C 0.7181(3) 0.05944(13) 0.5139(2) 0.0270(6) Uani 0.886(4) 1 d P A 1 C22 C 0.6599(2) 0.05566(13) 0.5985(2) 0.0265(5) Uani 0.886(4) 1 d P A 1 H22 H 0.5710 0.0289 0.5952 0.032 Uiso 0.886(4) 1 calc PR A 1 C23 C 0.7242(3) 0.08783(14) 0.68206(19) 0.0264(5) Uani 0.886(4) 1 d P A 1 H23 H 0.8161 0.1112 0.6850 0.032 Uiso 0.886(4) 1 calc PR A 1 C24 C 0.6678(2) 0.09043(12) 0.76731(15) 0.0317(4) Uani 1 1 d . . . C25 C 0.5392(2) 0.05440(12) 0.77766(15) 0.0356(5) Uani 1 1 d . A . H25 H 0.4828 0.0261 0.7269 0.043 Uiso 1 1 calc R . . C26 C 0.4941(2) 0.05998(13) 0.86177(16) 0.0390(5) Uani 1 1 d . . . H26 H 0.4068 0.0354 0.8683 0.047 Uiso 1 1 calc R A . C27 C 0.5743(2) 0.10077(13) 0.93604(16) 0.0397(5) Uani 1 1 d . A . H27 H 0.5427 0.1041 0.9936 0.048 Uiso 1 1 calc R . . C28 C 0.7012(2) 0.13699(14) 0.92645(16) 0.0438(6) Uani 1 1 d . . . H28 H 0.7568 0.1655 0.9773 0.053 Uiso 1 1 calc R A . C29 C 0.7468(2) 0.13159(13) 0.84289(16) 0.0388(5) Uani 1 1 d . A . H29 H 0.8341 0.1566 0.8369 0.047 Uiso 1 1 calc R . . C19A C 1.0011(17) 0.0422(9) 0.4419(12) 0.024(4) Uiso 0.114(4) 1 d P . 2 H19A H 0.9167 0.0441 0.3878 0.029 Uiso 0.114(4) 1 calc PR A 2 C20A C 0.950(2) 0.0443(11) 0.5355(13) 0.030(4) Uiso 0.114(4) 1 d P . 2 H20A H 1.0112 0.0810 0.5803 0.035 Uiso 0.114(4) 1 calc PR A 2 C22A C 0.755(5) 0.079(3) 0.639(4) 0.116(16) Uiso 0.114(4) 1 d P A 2 H22A H 0.8287 0.0968 0.6892 0.139 Uiso 0.114(4) 1 calc PR A 2 O1A O 0.703(3) 0.0595(16) 0.450(2) 0.080(9) Uiso 0.114(4) 1 d P A 2 C21A C 0.788(3) 0.0650(14) 0.5251(17) 0.034(6) Uiso 0.114(4) 1 d P A 2 C23A C 0.671(3) 0.0701(15) 0.646(2) 0.035(6) Uiso 0.114(4) 1 d P A 2 H23A H 0.5918 0.0522 0.5993 0.043 Uiso 0.114(4) 1 calc PR A 2 C13A C 1.1411(19) 0.1158(11) 0.3389(11) 0.002(4) Uiso 0.114(4) 1 d PD A 2 C14A C 1.260(2) 0.1565(11) 0.3244(13) 0.018(6) Uiso 0.114(4) 1 d PD A 2 H14A H 1.2727 0.1682 0.2629 0.021 Uiso 0.114(4) 1 calc PR A 2 C15A C 1.363(2) 0.1800(12) 0.4030(13) 0.031(6) Uiso 0.114(4) 1 d PD A 2 H15A H 1.4480 0.2066 0.3960 0.037 Uiso 0.114(4) 1 calc PR A 2 C16A C 1.338(2) 0.1642(13) 0.4896(14) 0.020(6) Uiso 0.114(4) 1 d PD A 2 H16A H 1.4030 0.1844 0.5429 0.024 Uiso 0.114(4) 1 calc PR A 2 C17A C 1.2240(19) 0.1209(10) 0.5030(11) 0.016(4) Uiso 0.114(4) 1 d PD A 2 H17A H 1.2164 0.1069 0.5647 0.019 Uiso 0.114(4) 1 calc PR A 2 C18A C 1.1170(18) 0.0964(10) 0.4263(10) 0.021(4) Uiso 0.114(4) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0344(3) 0.0221(2) 0.0404(3) -0.0011(2) 0.0007(2) -0.0042(2) P1 0.0252(2) 0.0205(2) 0.0230(3) -0.0005(2) 0.00129(19) -0.0001(2) O1 0.0355(11) 0.0463(11) 0.0301(11) -0.0029(8) 0.0003(9) -0.0061(9) C1 0.0276(9) 0.0269(9) 0.0195(9) -0.0001(8) 0.0045(8) 0.0023(8) C2 0.0334(11) 0.0362(11) 0.0377(13) -0.0038(10) 0.0018(9) -0.0004(9) C3 0.0279(11) 0.0591(16) 0.0502(15) 0.0005(12) 0.0022(10) 0.0058(11) C4 0.0409(13) 0.0497(14) 0.0437(14) 0.0058(11) 0.0121(11) 0.0203(11) C5 0.0505(13) 0.0325(11) 0.0333(12) 0.0008(9) 0.0124(10) 0.0137(10) C6 0.0347(10) 0.0284(10) 0.0277(11) -0.0017(8) 0.0067(9) 0.0023(9) C7 0.0257(9) 0.0266(10) 0.0242(10) -0.0011(8) 0.0041(8) 0.0015(8) C8 0.0399(11) 0.0291(10) 0.0364(12) -0.0009(9) 0.0156(10) 0.0043(9) C9 0.0444(12) 0.0372(12) 0.0421(14) 0.0083(10) 0.0168(11) 0.0029(10) C10 0.0407(12) 0.0582(15) 0.0306(12) 0.0008(11) 0.0141(10) 0.0019(11) C11 0.0510(13) 0.0474(14) 0.0374(13) -0.0137(11) 0.0167(11) 0.0024(11) C12 0.0431(12) 0.0312(11) 0.0343(12) -0.0070(9) 0.0095(10) -0.0004(10) C13 0.0204(14) 0.0194(12) 0.0294(14) -0.0019(9) 0.0033(11) 0.0039(11) C14 0.0279(15) 0.0293(14) 0.0317(16) 0.0013(13) 0.0077(11) 0.0007(11) C15 0.0193(11) 0.0368(16) 0.0459(19) 0.0008(14) 0.0001(11) -0.0040(11) C16 0.0320(16) 0.0402(17) 0.0290(16) -0.0001(13) -0.0042(13) -0.0027(13) C17 0.0303(14) 0.0358(14) 0.0261(13) -0.0004(10) 0.0027(11) 0.0032(12) C18 0.0251(12) 0.0238(12) 0.0232(12) -0.0008(9) 0.0017(9) 0.0028(10) C19 0.0267(11) 0.0289(12) 0.0245(12) 0.0000(9) 0.0011(9) 0.0019(9) C20 0.0238(12) 0.0398(14) 0.0234(12) -0.0015(10) -0.0003(9) -0.0010(11) C21 0.0249(13) 0.0236(12) 0.0298(15) -0.0019(10) -0.0002(11) -0.0011(10) C22 0.0262(12) 0.0261(12) 0.0252(14) 0.0004(11) 0.0011(10) -0.0015(9) C23 0.0257(12) 0.0239(11) 0.0281(14) 0.0000(10) 0.0019(12) -0.0018(10) C24 0.0344(10) 0.0280(10) 0.0335(12) 0.0026(9) 0.0089(9) 0.0037(9) C25 0.0370(11) 0.0322(11) 0.0355(13) -0.0032(9) 0.0027(10) -0.0033(9) C26 0.0360(11) 0.0397(12) 0.0430(14) -0.0005(10) 0.0123(10) -0.0040(10) C27 0.0450(12) 0.0424(13) 0.0342(12) -0.0030(10) 0.0141(10) 0.0004(11) C28 0.0449(13) 0.0458(13) 0.0389(14) -0.0115(11) 0.0044(10) -0.0069(11) C29 0.0343(11) 0.0390(12) 0.0433(14) -0.0032(10) 0.0089(10) -0.0067(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9583(7) . ? P1 C13 1.814(3) . ? P1 C7 1.8143(19) . ? P1 C1 1.8196(18) . ? P1 C13A 1.895(18) . ? O1 C21 1.216(4) . ? C1 C2 1.387(3) . ? C1 C6 1.399(3) . ? C2 C3 1.383(3) . ? C3 C4 1.374(3) . ? C4 C5 1.378(3) . ? C5 C6 1.380(3) . ? C7 C12 1.382(3) . ? C7 C8 1.395(3) . ? C8 C9 1.386(3) . ? C9 C10 1.375(3) . ? C10 C11 1.378(3) . ? C11 C12 1.382(3) . ? C13 C14 1.398(4) . ? C13 C18 1.411(3) . ? C14 C15 1.391(3) . ? C15 C16 1.377(4) . ? C16 C17 1.373(4) . ? C17 C18 1.394(3) . ? C18 C19 1.473(3) . ? C19 C20 1.325(3) . ? C20 C21 1.482(3) . ? C21 C22 1.455(4) . ? C22 C23 1.360(4) . ? C23 C24 1.453(3) . ? C24 C29 1.388(3) . ? C24 C25 1.400(3) . ? C24 C23A 1.81(3) . ? C25 C26 1.384(3) . ? C26 C27 1.376(3) . ? C27 C28 1.384(3) . ? C28 C29 1.378(3) . ? C19A C18A 1.49(2) . ? C19A C20A 1.54(2) . ? C19A C20A 1.56(2) 3_756 ? C20A C21A 1.55(3) . ? C20A C19A 1.56(2) 3_756 ? C22A C23A 0.84(5) . ? C22A C21A 1.77(6) . ? O1A C21A 1.22(3) . ? C13A C14A 1.381(16) . ? C13A C18A 1.382(15) . ? C14A C15A 1.396(16) . ? C15A C16A 1.360(16) . ? C16A C17A 1.355(16) . ? C17A C18A 1.407(15) . ? 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 C13 P1 C7 106.84(11) . . ? C13 P1 C1 104.62(12) . . ? C7 P1 C1 105.96(8) . . ? C13 P1 C13A 12.0(5) . . ? C7 P1 C13A 97.4(5) . . ? C1 P1 C13A 115.0(5) . . ? C13 P1 S1 114.13(9) . . ? C7 P1 S1 112.40(7) . . ? C1 P1 S1 112.23(6) . . ? C13A P1 S1 112.8(5) . . ? C2 C1 C6 119.18(17) . . ? C2 C1 P1 118.89(15) . . ? C6 C1 P1 121.92(14) . . ? C3 C2 C1 120.5(2) . . ? C4 C3 C2 119.8(2) . . ? C3 C4 C5 120.4(2) . . ? C4 C5 C6 120.4(2) . . ? C5 C6 C1 119.69(19) . . ? C12 C7 C8 118.94(18) . . ? C12 C7 P1 119.37(15) . . ? C8 C7 P1 121.67(14) . . ? C9 C8 C7 120.15(19) . . ? C10 C9 C8 120.2(2) . . ? C9 C10 C11 119.9(2) . . ? C10 C11 C12 120.2(2) . . ? C7 C12 C11 120.6(2) . . ? C14 C13 C18 118.9(2) . . ? C14 C13 P1 118.6(2) . . ? C18 C13 P1 122.2(2) . . ? C15 C14 C13 121.2(3) . . ? C16 C15 C14 119.3(3) . . ? C17 C16 C15 120.3(2) . . ? C16 C17 C18 121.7(2) . . ? C17 C18 C13 118.5(2) . . ? C17 C18 C19 120.3(2) . . ? C13 C18 C19 121.2(2) . . ? C20 C19 C18 127.5(2) . . ? C19 C20 C21 119.6(2) . . ? O1 C21 C22 119.8(3) . . ? O1 C21 C20 120.6(2) . . ? C22 C21 C20 119.6(2) . . ? C23 C22 C21 124.4(2) . . ? C22 C23 C24 127.2(3) . . ? C29 C24 C25 118.29(19) . . ? C29 C24 C23 117.6(2) . . ? C25 C24 C23 124.1(2) . . ? C29 C24 C23A 139.4(9) . . ? C25 C24 C23A 102.2(9) . . ? C23 C24 C23A 22.1(9) . . ? C26 C25 C24 120.0(2) . . ? C27 C26 C25 120.8(2) . . ? C26 C27 C28 119.7(2) . . ? C29 C28 C27 119.8(2) . . ? C28 C29 C24 121.4(2) . . ? C18A C19A C20A 119.8(14) . . ? C18A C19A C20A 115.2(13) . 3_756 ? C20A C19A C20A 88.2(13) . 3_756 ? C19A C20A C21A 113.9(16) . . ? C19A C20A C19A 91.8(13) . 3_756 ? C21A C20A C19A 118.7(15) . 3_756 ? C23A C22A C21A 117(7) . . ? O1A C21A C20A 122(2) . . ? O1A C21A C22A 130(3) . . ? C20A C21A C22A 108(2) . . ? C22A C23A C24 107(6) . . ? C14A C13A C18A 124.0(15) . . ? C14A C13A P1 120.6(12) . . ? C18A C13A P1 114.5(12) . . ? C13A C14A C15A 118.0(16) . . ? C16A C15A C14A 118.8(17) . . ? C17A C16A C15A 122.6(17) . . ? C16A C17A C18A 120.8(15) . . ? C13A C18A C17A 115.6(14) . . ? C13A C18A C19A 123.9(14) . . ? C17A C18A C19A 119.7(14) . . ? _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 29.22 _diffrn_measured_fraction_theta_full 0.865 _refine_diff_density_max 0.424 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.051 ### END data_160K _database_code_depnum_ccdc_archive 'CCDC 874844' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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 9.4512(2) _cell_length_b 17.1319(4) _cell_length_c 14.6123(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.013(3) _cell_angle_gamma 90.00 _cell_volume 2314.17(11) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 3400 _cell_measurement_theta_min 3.0824 _cell_measurement_theta_max 29.1628 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97669 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 11495 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.1078 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.0824 _diffrn_reflns_theta_max 29.1628 _reflns_number_total 5404 _reflns_number_gt 3743 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0587993000 _diffrn_orient_matrix_UB_12 0.0128702000 _diffrn_orient_matrix_UB_13 0.0351884000 _diffrn_orient_matrix_UB_21 -0.0191323000 _diffrn_orient_matrix_UB_22 0.0393530000 _diffrn_orient_matrix_UB_23 -0.0115610000 _diffrn_orient_matrix_UB_31 -0.0454165000 _diffrn_orient_matrix_UB_32 0.0000796000 _diffrn_orient_matrix_UB_33 0.0330271000 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement '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^)+(0.0321P)^2^+0.9188P] 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 5404 _refine_ls_number_parameters 392 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0865 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91624(6) -0.01090(3) 0.22993(4) 0.03820(16) Uani 1 1 d . A . P1 P 0.98161(6) 0.09790(3) 0.23862(4) 0.02702(14) Uani 1 1 d . . . O1 O 0.6395(3) 0.0452(2) 0.4388(2) 0.0428(8) Uani 0.831(4) 1 d P A 1 C1 C 1.0694(2) 0.12488(12) 0.14392(14) 0.0287(5) Uani 1 1 d . A . C2 C 1.1120(2) 0.06692(14) 0.08980(16) 0.0403(6) Uani 1 1 d . . . H2 H 1.0929 0.0138 0.1016 0.048 Uiso 1 1 calc R A . C3 C 1.1822(3) 0.08551(16) 0.01849(18) 0.0505(7) Uani 1 1 d . A . H3 H 1.2112 0.0452 -0.0184 0.061 Uiso 1 1 calc R . . C4 C 1.2103(3) 0.16242(16) 0.00088(17) 0.0465(6) Uani 1 1 d . . . H4 H 1.2589 0.1751 -0.0479 0.056 Uiso 1 1 calc R A . C5 C 1.1678(3) 0.22068(15) 0.05404(18) 0.0455(6) Uani 1 1 d . A . H5 H 1.1866 0.2737 0.0416 0.055 Uiso 1 1 calc R . . C6 C 1.0978(2) 0.20242(13) 0.12571(17) 0.0388(6) Uani 1 1 d . . . H6 H 1.0691 0.2429 0.1624 0.047 Uiso 1 1 calc R A . C7 C 0.8329(2) 0.16627(12) 0.23299(14) 0.0272(4) Uani 1 1 d . A . C8 C 0.6935(2) 0.14112(14) 0.19661(17) 0.0403(6) Uani 1 1 d . . . H8 H 0.6775 0.0889 0.1750 0.048 Uiso 1 1 calc R A . C9 C 0.5775(3) 0.19098(16) 0.19131(19) 0.0516(7) Uani 1 1 d . A . H9 H 0.4821 0.1730 0.1666 0.062 Uiso 1 1 calc R . . C10 C 0.6002(3) 0.26652(16) 0.22186(18) 0.0499(7) Uani 1 1 d . . . H10 H 0.5204 0.3010 0.2180 0.060 Uiso 1 1 calc R A . C11 C 0.7382(3) 0.29257(14) 0.25812(17) 0.0428(6) Uani 1 1 d . A . H11 H 0.7532 0.3451 0.2788 0.051 Uiso 1 1 calc R . . C12 C 0.8550(2) 0.24306(12) 0.26473(15) 0.0334(5) Uani 1 1 d . . . H12 H 0.9499 0.2611 0.2907 0.040 Uiso 1 1 calc R A . C13 C 1.1062(3) 0.1220(2) 0.3472(2) 0.0254(8) Uani 0.831(4) 1 d PD A 1 C14 C 1.2490(5) 0.1396(3) 0.3444(4) 0.0332(12) Uani 0.831(4) 1 d PD A 1 H14 H 1.2768 0.1416 0.2856 0.040 Uiso 0.831(4) 1 calc PR A 1 C15 C 1.3517(5) 0.1540(3) 0.4251(4) 0.0390(10) Uani 0.831(4) 1 d PD A 1 H15 H 1.4485 0.1663 0.4218 0.047 Uiso 0.831(4) 1 calc PR A 1 C16 C 1.3110(7) 0.1504(5) 0.5104(4) 0.0397(13) Uani 0.831(4) 1 d PD A 1 H16 H 1.3803 0.1609 0.5662 0.048 Uiso 0.831(4) 1 calc PR A 1 C17 C 1.1717(5) 0.1318(3) 0.5156(3) 0.0355(10) Uani 0.831(4) 1 d PD A 1 H17 H 1.1464 0.1290 0.5751 0.043 Uiso 0.831(4) 1 calc PR A 1 C18 C 1.0664(3) 0.11684(19) 0.4353(2) 0.0273(7) Uani 0.831(4) 1 d PD A 1 C19 C 0.9179(3) 0.09592(15) 0.44342(18) 0.0315(7) Uani 0.831(4) 1 d P A 1 H19 H 0.8483 0.0927 0.3864 0.038 Uiso 0.831(4) 1 calc PR A 1 C20 C 0.8702(4) 0.08111(19) 0.5206(2) 0.0327(8) Uani 0.831(4) 1 d P A 1 H20 H 0.9344 0.0844 0.5799 0.039 Uiso 0.831(4) 1 calc PR A 1 C21 C 0.7164(5) 0.0594(3) 0.5145(3) 0.0310(10) Uani 0.831(4) 1 d P A 1 C22 C 0.6599(5) 0.0556(2) 0.5978(2) 0.0300(9) Uani 0.831(4) 1 d P A 1 H22 H 0.5712 0.0285 0.5945 0.036 Uiso 0.831(4) 1 calc PR A 1 C23 C 0.7235(6) 0.0877(3) 0.6817(3) 0.0291(8) Uani 0.831(4) 1 d P A 1 H23 H 0.8155 0.1112 0.6848 0.035 Uiso 0.831(4) 1 calc PR A 1 C24 C 0.6673(2) 0.09025(13) 0.76647(17) 0.0369(5) Uani 1 1 d . . . C25 C 0.5388(2) 0.05435(13) 0.77740(18) 0.0408(6) Uani 1 1 d . A . H25 H 0.4821 0.0260 0.7269 0.049 Uiso 1 1 calc R . . C26 C 0.4940(3) 0.05999(14) 0.86153(18) 0.0443(6) Uani 1 1 d . . . H26 H 0.4068 0.0354 0.8683 0.053 Uiso 1 1 calc R A . C27 C 0.5746(3) 0.10087(14) 0.93538(17) 0.0437(6) Uani 1 1 d . A . H27 H 0.5433 0.1044 0.9929 0.052 Uiso 1 1 calc R . . C28 C 0.7015(3) 0.13678(15) 0.92521(18) 0.0485(6) Uani 1 1 d . . . H28 H 0.7575 0.1653 0.9758 0.058 Uiso 1 1 calc R A . C29 C 0.7466(3) 0.13121(14) 0.84171(18) 0.0445(6) Uani 1 1 d . A . H29 H 0.8341 0.1560 0.8356 0.053 Uiso 1 1 calc R . . C19A C 1.0028(13) 0.0405(7) 0.4426(8) 0.026(3) Uani 0.169(4) 1 d P . 2 H19A H 0.9195 0.0405 0.3877 0.031 Uiso 0.169(4) 1 calc PR A 2 C20A C 0.9473(18) 0.0442(7) 0.5325(10) 0.032(3) Uani 0.169(4) 1 d P . 2 H20A H 1.0043 0.0822 0.5775 0.038 Uiso 0.169(4) 1 calc PR A 2 C22A C 0.766(4) 0.0821(19) 0.648(3) 0.112(14) Uani 0.169(4) 1 d P A 2 H22A H 0.8356 0.1023 0.6988 0.134 Uiso 0.169(4) 1 calc PR A 2 O1A O 0.707(3) 0.0595(15) 0.448(2) 0.108(10) Uani 0.169(4) 1 d P A 2 C21A C 0.783(3) 0.0587(15) 0.520(2) 0.055(9) Uani 0.169(4) 1 d P A 2 C23A C 0.668(3) 0.0679(13) 0.645(3) 0.054(8) Uani 0.169(4) 1 d P A 2 H23A H 0.5955 0.0484 0.5956 0.065 Uiso 0.169(4) 1 calc PR A 2 C13A C 1.138(2) 0.1167(14) 0.3364(14) 0.0254(8) Uani 0.17 1 d PD A 2 C14A C 1.258(2) 0.1591(12) 0.3243(15) 0.020(4) Uani 0.169(4) 1 d PD A 2 H14A H 1.2694 0.1722 0.2631 0.024 Uiso 0.169(4) 1 calc PR A 2 C15A C 1.361(2) 0.1822(12) 0.4015(16) 0.046(6) Uani 0.169(4) 1 d PD A 2 H15A H 1.4427 0.2116 0.3940 0.056 Uiso 0.169(4) 1 calc PR A 2 C16A C 1.342(3) 0.162(2) 0.4889(17) 0.044(8) Uani 0.169(4) 1 d PD A 2 H16A H 1.4126 0.1772 0.5419 0.053 Uiso 0.169(4) 1 calc PR A 2 C17A C 1.225(2) 0.1201(11) 0.5026(11) 0.027(4) Uani 0.169(4) 1 d PD A 2 H17A H 1.2153 0.1074 0.5643 0.033 Uiso 0.169(4) 1 calc PR A 2 C18A C 1.1177(15) 0.0956(8) 0.4248(11) 0.027(4) Uani 0.169(4) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0392(3) 0.0239(3) 0.0474(4) -0.0016(3) -0.0004(3) -0.0043(2) P1 0.0301(3) 0.0225(3) 0.0261(3) -0.0006(2) 0.0003(2) -0.0003(2) O1 0.0416(16) 0.0528(15) 0.0305(14) -0.0040(11) -0.0001(12) -0.0053(13) C1 0.0295(11) 0.0300(11) 0.0253(11) -0.0009(9) 0.0026(9) 0.0025(9) C2 0.0494(14) 0.0348(12) 0.0364(14) -0.0076(11) 0.0083(11) -0.0007(11) C3 0.0600(16) 0.0528(16) 0.0415(16) -0.0145(13) 0.0169(13) 0.0043(13) C4 0.0463(14) 0.0630(17) 0.0331(14) 0.0010(12) 0.0152(11) 0.0032(13) C5 0.0494(14) 0.0406(14) 0.0505(17) 0.0071(12) 0.0194(12) 0.0001(12) C6 0.0455(13) 0.0313(12) 0.0439(15) -0.0004(11) 0.0194(11) 0.0053(11) C7 0.0306(10) 0.0295(11) 0.0216(11) 0.0018(9) 0.0059(9) 0.0021(9) C8 0.0361(12) 0.0400(13) 0.0423(15) -0.0051(11) 0.0023(11) 0.0012(11) C9 0.0328(12) 0.0619(18) 0.0572(18) -0.0018(14) 0.0031(12) 0.0062(13) C10 0.0454(15) 0.0549(17) 0.0511(17) 0.0065(13) 0.0142(13) 0.0229(13) C11 0.0578(15) 0.0346(12) 0.0383(15) 0.0006(11) 0.0156(12) 0.0127(12) C12 0.0405(12) 0.0306(11) 0.0292(12) -0.0030(9) 0.0073(10) 0.0022(10) C13 0.026(2) 0.0211(12) 0.0276(16) -0.0006(11) 0.0020(12) 0.0018(14) C14 0.034(2) 0.030(3) 0.034(2) 0.0023(18) 0.0047(16) -0.0010(18) C15 0.0252(17) 0.040(3) 0.050(3) -0.001(2) 0.0018(19) -0.0010(18) C16 0.034(3) 0.044(3) 0.035(2) -0.004(2) -0.005(2) -0.004(2) C17 0.037(2) 0.038(2) 0.0290(19) -0.0016(15) 0.0006(16) 0.0035(18) C18 0.0291(18) 0.0250(18) 0.0256(15) 0.0005(13) 0.0005(13) 0.0022(13) C19 0.0335(14) 0.0328(14) 0.0266(14) 0.0003(12) 0.0024(11) 0.0025(12) C20 0.0313(17) 0.039(2) 0.0273(16) -0.0034(14) 0.0043(14) -0.0013(16) C21 0.030(2) 0.0232(17) 0.038(2) -0.0008(15) 0.003(2) 0.0031(18) C22 0.0349(18) 0.0269(17) 0.0247(19) -0.0010(16) -0.0018(18) -0.0025(13) C23 0.026(2) 0.0270(19) 0.032(2) -0.0022(14) 0.0013(16) -0.0014(17) C24 0.0418(12) 0.0302(12) 0.0398(14) 0.0038(10) 0.0112(11) 0.0071(10) C25 0.0440(13) 0.0331(12) 0.0427(15) -0.0025(11) 0.0035(11) -0.0012(11) C26 0.0402(13) 0.0443(14) 0.0498(16) -0.0008(12) 0.0124(12) -0.0039(12) C27 0.0479(14) 0.0470(14) 0.0377(14) -0.0033(12) 0.0122(11) 0.0003(12) C28 0.0476(14) 0.0523(16) 0.0438(16) -0.0114(13) 0.0051(12) -0.0063(12) C29 0.0392(13) 0.0441(14) 0.0505(16) -0.0056(12) 0.0100(12) -0.0067(11) C19A 0.041(7) 0.022(6) 0.019(6) 0.000(5) 0.018(5) 0.006(5) C20A 0.055(9) 0.007(5) 0.040(8) 0.005(5) 0.024(7) 0.012(6) C22A 0.12(3) 0.024(12) 0.18(4) 0.019(19) 0.00(3) 0.002(17) O1A 0.088(19) 0.091(16) 0.16(2) 0.082(16) 0.06(2) 0.044(13) C21A 0.067(18) 0.047(13) 0.072(17) 0.051(11) 0.063(17) 0.044(15) C23A 0.037(12) 0.036(13) 0.08(3) 0.008(15) 0.000(19) -0.021(9) C13A 0.026(2) 0.0211(12) 0.0276(16) -0.0006(11) 0.0020(12) 0.0018(14) C14A 0.007(6) 0.022(10) 0.030(11) 0.003(7) 0.003(6) -0.004(6) C15A 0.038(10) 0.033(12) 0.060(16) 0.003(9) -0.010(9) -0.008(9) C16A 0.021(11) 0.056(18) 0.05(2) 0.001(15) -0.005(12) 0.004(10) C17A 0.035(13) 0.022(8) 0.021(8) -0.001(6) -0.004(8) 0.011(10) C18A 0.021(8) 0.007(6) 0.054(10) -0.004(6) 0.011(7) 0.003(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 S1 P1 1.9595(7) . ? P1 C13 1.816(4) . ? P1 C1 1.815(2) . ? P1 C7 1.818(2) . ? P1 C13A 1.86(2) . ? O1 C21 1.215(6) . ? C1 C2 1.381(3) . ? C1 C6 1.392(3) . ? C2 C3 1.384(3) . ? C3 C4 1.379(4) . ? C4 C5 1.375(3) . ? C5 C6 1.386(3) . ? C7 C8 1.383(3) . ? C7 C12 1.396(3) . ? C8 C9 1.380(3) . ? C9 C10 1.371(4) . ? C10 C11 1.376(3) . ? C11 C12 1.380(3) . ? C13 C14 1.392(5) . ? C13 C18 1.417(4) . ? C14 C15 1.384(5) . ? C15 C16 1.380(6) . ? C16 C17 1.372(6) . ? C17 C18 1.395(5) . ? C18 C19 1.477(4) . ? C19 C20 1.323(4) . ? C20 C21 1.485(5) . ? C21 C22 1.428(6) . ? C22 C23 1.364(6) . ? C23 C24 1.446(4) . ? C24 C29 1.386(3) . ? C24 C25 1.400(3) . ? C24 C23A 1.82(4) . ? C25 C26 1.384(3) . ? C26 C27 1.376(3) . ? C27 C28 1.383(3) . ? C28 C29 1.377(3) . ? C19A C18A 1.501(18) . ? C19A C20A 1.515(16) . ? C19A C20A 1.546(17) 3_756 ? C20A C21A 1.54(3) . ? C20A C19A 1.546(17) 3_756 ? C22A C23A 0.95(4) . ? C22A C21A 1.95(5) . ? O1A C21A 1.16(4) . ? C13A C18A 1.392(16) . ? C13A C14A 1.389(16) . ? C14A C15A 1.384(16) . ? C15A C16A 1.371(16) . ? C16A C17A 1.364(17) . ? C17A C18A 1.420(15) . ? 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 C13 P1 C1 106.99(11) . . ? C13 P1 C7 104.32(13) . . ? C1 P1 C7 105.85(9) . . ? C13 P1 C13A 11.7(6) . . ? C1 P1 C13A 97.3(6) . . ? C7 P1 C13A 114.0(7) . . ? C13 P1 S1 114.31(14) . . ? C1 P1 S1 112.38(7) . . ? C7 P1 S1 112.30(7) . . ? C13A P1 S1 113.9(7) . . ? C2 C1 C6 119.1(2) . . ? C2 C1 P1 119.18(17) . . ? C6 C1 P1 121.71(16) . . ? C1 C2 C3 120.6(2) . . ? C4 C3 C2 120.1(2) . . ? C5 C4 C3 119.9(2) . . ? C4 C5 C6 120.3(2) . . ? C5 C6 C1 120.1(2) . . ? C8 C7 C12 119.09(19) . . ? C8 C7 P1 118.83(16) . . ? C12 C7 P1 122.08(16) . . ? C9 C8 C7 120.7(2) . . ? C10 C9 C8 119.8(2) . . ? C9 C10 C11 120.2(2) . . ? C10 C11 C12 120.5(2) . . ? C11 C12 C7 119.6(2) . . ? C14 C13 C18 118.8(3) . . ? C14 C13 P1 118.7(3) . . ? C18 C13 P1 122.2(2) . . ? C15 C14 C13 121.8(4) . . ? C16 C15 C14 118.9(4) . . ? C17 C16 C15 120.7(4) . . ? C16 C17 C18 121.4(4) . . ? C17 C18 C13 118.3(3) . . ? C17 C18 C19 120.0(3) . . ? C13 C18 C19 121.6(3) . . ? C20 C19 C18 127.8(3) . . ? C19 C20 C21 120.0(3) . . ? O1 C21 C22 120.5(4) . . ? O1 C21 C20 119.7(4) . . ? C22 C21 C20 119.7(4) . . ? C23 C22 C21 125.0(4) . . ? C22 C23 C24 127.6(4) . . ? C29 C24 C25 118.1(2) . . ? C29 C24 C23 117.4(3) . . ? C25 C24 C23 124.5(3) . . ? C29 C24 C23A 140.3(8) . . ? C25 C24 C23A 101.5(8) . . ? C23 C24 C23A 23.1(8) . . ? C26 C25 C24 120.2(2) . . ? C27 C26 C25 120.7(2) . . ? C26 C27 C28 119.5(2) . . ? C29 C28 C27 120.0(2) . . ? C28 C29 C24 121.5(2) . . ? C18A C19A C20A 121.2(11) . . ? C18A C19A C20A 115.7(10) . 3_756 ? C20A C19A C20A 88.7(9) . 3_756 ? C19A C20A C21A 115.4(14) . . ? C19A C20A C19A 91.3(9) . 3_756 ? C21A C20A C19A 115.3(13) . 3_756 ? C23A C22A C21A 100(5) . . ? O1A C21A C20A 122(2) . . ? O1A C21A C22A 136(3) . . ? C20A C21A C22A 102(2) . . ? C22A C23A C24 96(5) . . ? C18A C13A C14A 121.7(17) . . ? C18A C13A P1 115.5(13) . . ? C14A C13A P1 122.2(14) . . ? C15A C14A C13A 120.0(16) . . ? C16A C15A C14A 118.7(17) . . ? C17A C16A C15A 122.4(19) . . ? C16A C17A C18A 120.1(16) . . ? C13A C18A C17A 117.0(14) . . ? C13A C18A C19A 124.5(14) . . ? C17A C18A C19A 117.9(14) . . ? _diffrn_measured_fraction_theta_max 0.862 _diffrn_reflns_theta_full 29.23 _diffrn_measured_fraction_theta_full 0.862 _refine_diff_density_max 0.385 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.051 ### END data_170K _database_code_depnum_ccdc_archive 'CCDC 874845' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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 9.407(5) _cell_length_b 17.207(5) _cell_length_c 14.659(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 102.087(5) _cell_angle_gamma 90.000(5) _cell_volume 2320.2(16) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 2633 _cell_measurement_theta_min 3.0992 _cell_measurement_theta_max 29.2253 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72409 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 11659 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.1691 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.0992 _diffrn_reflns_theta_max 29.2253 _reflns_number_total 5423 _reflns_number_gt 3173 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0104734000 _diffrn_orient_matrix_UB_12 0.0280809000 _diffrn_orient_matrix_UB_13 -0.0362237000 _diffrn_orient_matrix_UB_21 0.0665615000 _diffrn_orient_matrix_UB_22 -0.0113558000 _diffrn_orient_matrix_UB_23 -0.0115460000 _diffrn_orient_matrix_UB_31 -0.0374674000 _diffrn_orient_matrix_UB_32 -0.0279898000 _diffrn_orient_matrix_UB_33 -0.0316398000 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement '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^)+(0.0580P)^2^+0.0132P] 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 5423 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1331 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3348(3) 0.16471(15) 0.23381(18) 0.0330(6) Uani 1 1 d . A . C2 C 0.1939(3) 0.14101(17) 0.1961(2) 0.0463(8) Uani 1 1 d . . . H2 H 0.1773 0.0892 0.1739 0.056 Uiso 1 1 calc R . . C3 C 0.0786(4) 0.1903(2) 0.1900(3) 0.0616(10) Uani 1 1 d . . . H3 H -0.0172 0.1727 0.1646 0.074 Uiso 1 1 calc R . . C4 C 0.1022(4) 0.2660(2) 0.2212(2) 0.0573(9) Uani 1 1 d . . . H4 H 0.0224 0.3007 0.2168 0.069 Uiso 1 1 calc R . . C5 C 0.2399(4) 0.29107(17) 0.2582(2) 0.0499(8) Uani 1 1 d . . . H5 H 0.2552 0.3433 0.2791 0.060 Uiso 1 1 calc R . . C6 C 0.3577(3) 0.24141(15) 0.26574(19) 0.0388(7) Uani 1 1 d . . . H6 H 0.4530 0.2592 0.2923 0.047 Uiso 1 1 calc R . . C7 C 0.5702(3) 0.12428(15) 0.14329(19) 0.0349(7) Uani 1 1 d . A . C8 C 0.5970(3) 0.20149(17) 0.1245(2) 0.0486(8) Uani 1 1 d . . . H8 H 0.5673 0.2416 0.1609 0.058 Uiso 1 1 calc R . . C9 C 0.6663(4) 0.22028(18) 0.0533(3) 0.0564(9) Uani 1 1 d . . . H9 H 0.6835 0.2732 0.0406 0.068 Uiso 1 1 calc R . . C10 C 0.7106(4) 0.1625(2) 0.0009(2) 0.0557(9) Uani 1 1 d . . . H10 H 0.7590 0.1755 -0.0478 0.067 Uiso 1 1 calc R . . C11 C 0.6849(4) 0.0860(2) 0.0188(2) 0.0559(9) Uani 1 1 d . . . H11 H 0.7154 0.0462 -0.0177 0.067 Uiso 1 1 calc R . . C12 C 0.6150(3) 0.06664(17) 0.0894(2) 0.0463(8) Uani 1 1 d . . . H12 H 0.5975 0.0136 0.1012 0.056 Uiso 1 1 calc R . . C13 C 0.6055(11) 0.1212(5) 0.3504(6) 0.027(2) Uani 0.655(6) 1 d PD A 1 C14 C 0.7488(10) 0.1385(5) 0.3470(6) 0.038(2) Uani 0.655(6) 1 d PD A 1 H14 H 0.7764 0.1410 0.2883 0.046 Uiso 0.655(6) 1 calc PR A 1 C15 C 0.8524(8) 0.1522(4) 0.4284(6) 0.0433(17) Uani 0.655(6) 1 d PD A 1 H15 H 0.9502 0.1638 0.4258 0.052 Uiso 0.655(6) 1 calc PR A 1 C16 C 0.8099(9) 0.1484(5) 0.5135(6) 0.042(2) Uani 0.655(6) 1 d PD A 1 H16 H 0.8791 0.1578 0.5697 0.051 Uiso 0.655(6) 1 calc PR A 1 C17 C 0.6696(9) 0.1314(5) 0.5170(5) 0.042(2) Uani 0.655(6) 1 d PD A 1 H17 H 0.6432 0.1294 0.5760 0.051 Uiso 0.655(6) 1 calc PR A 1 C18 C 0.5634(6) 0.1168(3) 0.4370(4) 0.0308(14) Uani 0.655(6) 1 d PD A 1 C19 C 0.4155(5) 0.0957(2) 0.4437(3) 0.0362(14) Uani 0.655(6) 1 d P A 1 H19 H 0.3464 0.0922 0.3864 0.043 Uiso 0.655(6) 1 calc PR A 1 C20 C 0.3656(8) 0.0807(4) 0.5218(4) 0.0366(14) Uani 0.655(6) 1 d P A 1 H20 H 0.4294 0.0842 0.5812 0.044 Uiso 0.655(6) 1 calc PR A 1 C21 C 0.2138(10) 0.0592(5) 0.5150(7) 0.035(2) Uani 0.655(6) 1 d P A 1 C22 C 0.1636(7) 0.0557(4) 0.5969(4) 0.0299(15) Uani 0.655(6) 1 d P A 1 H22 H 0.0755 0.0281 0.5944 0.036 Uiso 0.655(6) 1 calc PR A 1 C23 C 0.2260(8) 0.0874(4) 0.6807(4) 0.0290(14) Uani 0.655(6) 1 d P A 1 H23 H 0.3192 0.1102 0.6855 0.035 Uiso 0.655(6) 1 calc PR A 1 C24 C 0.1637(4) 0.08978(17) 0.7647(2) 0.0464(8) Uani 1 1 d . . . C25 C 0.0367(4) 0.05411(17) 0.7764(2) 0.0512(9) Uani 1 1 d . A . H25 H -0.0209 0.0257 0.7265 0.061 Uiso 1 1 calc R . . C26 C -0.0063(4) 0.05991(18) 0.8611(3) 0.0551(9) Uani 1 1 d . . . H26 H -0.0936 0.0355 0.8688 0.066 Uiso 1 1 calc R A . C27 C 0.0758(4) 0.10051(18) 0.9337(2) 0.0530(8) Uani 1 1 d . A . H27 H 0.0461 0.1041 0.9916 0.064 Uiso 1 1 calc R . . C28 C 0.2020(4) 0.13620(19) 0.9222(3) 0.0571(9) Uani 1 1 d . . . H28 H 0.2590 0.1646 0.9724 0.068 Uiso 1 1 calc R A . C29 C 0.2462(4) 0.13118(18) 0.8387(3) 0.0540(9) Uani 1 1 d . A . H29 H 0.3333 0.1561 0.8315 0.065 Uiso 1 1 calc R . . O1 O 0.1350(6) 0.0459(4) 0.4381(5) 0.0506(15) Uani 0.655(6) 1 d P A 1 P1 P 0.48343(8) 0.09667(4) 0.23822(5) 0.0331(2) Uani 1 1 d . . . S1 S 0.41672(9) -0.01137(4) 0.22770(6) 0.0463(3) Uani 1 1 d . A . C19A C 0.5017(9) 0.0404(4) 0.4418(5) 0.032(3) Uani 0.345(6) 1 d P . 2 H19A H 0.4173 0.0408 0.3875 0.038 Uiso 0.345(6) 1 calc PR A 2 C20A C 0.4479(15) 0.0455(5) 0.5332(6) 0.043(3) Uani 0.345(6) 1 d P . 2 H20A H 0.5050 0.0839 0.5774 0.052 Uiso 0.345(6) 1 calc PR A 2 C22A C 0.264(3) 0.0819(10) 0.6402(16) 0.096(6) Uani 0.345(6) 1 d P A 2 H22A H 0.3407 0.1024 0.6868 0.115 Uiso 0.345(6) 1 calc PR A 2 C21A C 0.281(2) 0.0581(12) 0.5210(15) 0.061(7) Uani 0.345(6) 1 d P A 2 O1A O 0.2007(18) 0.0567(12) 0.4510(17) 0.109(7) Uani 0.345(6) 1 d P A 2 C23A C 0.155(3) 0.0697(14) 0.651(3) 0.176(19) Uani 0.345(6) 1 d P A 2 H23A H 0.0730 0.0517 0.6065 0.211 Uiso 0.345(6) 1 calc PR A 2 C13A C 0.634(2) 0.1153(10) 0.3343(11) 0.024(4) Uani 0.345(6) 1 d PD A 2 C14A C 0.7565(17) 0.1561(10) 0.3227(10) 0.036(4) Uani 0.345(6) 1 d PD A 2 H14A H 0.7680 0.1684 0.2615 0.043 Uiso 0.345(6) 1 calc PR A 2 C15A C 0.8625(16) 0.1794(8) 0.3989(11) 0.059(5) Uani 0.345(6) 1 d PD A 2 H15A H 0.9460 0.2071 0.3905 0.071 Uiso 0.345(6) 1 calc PR A 2 C16A C 0.8429(18) 0.1610(10) 0.4872(11) 0.047(4) Uani 0.345(6) 1 d PD A 2 H16A H 0.9140 0.1768 0.5399 0.056 Uiso 0.345(6) 1 calc PR A 2 C17A C 0.7242(17) 0.1207(8) 0.5006(9) 0.043(4) Uani 0.345(6) 1 d PD A 2 H17A H 0.7142 0.1092 0.5624 0.052 Uiso 0.345(6) 1 calc PR A 2 C18A C 0.6165(13) 0.0960(6) 0.4249(8) 0.029(3) Uani 0.345(6) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0451(17) 0.0359(14) 0.0190(14) -0.0001(11) 0.0086(12) -0.0021(13) C2 0.049(2) 0.0476(17) 0.042(2) -0.0084(14) 0.0075(15) 0.0035(16) C3 0.043(2) 0.075(2) 0.065(3) -0.0092(19) 0.0060(18) 0.0087(19) C4 0.058(2) 0.064(2) 0.053(2) 0.0019(17) 0.0199(18) 0.0239(18) C5 0.072(2) 0.0439(17) 0.0375(19) -0.0005(14) 0.0191(17) 0.0110(18) C6 0.0493(18) 0.0422(16) 0.0258(16) -0.0010(12) 0.0099(14) 0.0036(14) C7 0.0363(16) 0.0362(15) 0.0312(16) -0.0011(12) 0.0047(13) 0.0050(12) C8 0.061(2) 0.0389(16) 0.053(2) -0.0013(15) 0.0282(17) 0.0019(15) C9 0.069(2) 0.0463(18) 0.063(2) 0.0047(17) 0.0324(19) 0.0001(17) C10 0.060(2) 0.074(2) 0.036(2) -0.0019(17) 0.0159(17) 0.0022(19) C11 0.074(2) 0.060(2) 0.037(2) -0.0151(16) 0.0202(18) 0.0069(18) C12 0.061(2) 0.0433(17) 0.0341(19) -0.0067(14) 0.0081(16) 0.0036(15) C13 0.030(4) 0.025(3) 0.026(5) -0.003(3) 0.002(3) 0.005(3) C14 0.040(4) 0.043(4) 0.031(4) 0.002(3) 0.006(3) 0.003(3) C15 0.030(3) 0.060(5) 0.037(5) -0.005(4) 0.001(3) -0.001(3) C16 0.045(5) 0.053(5) 0.026(5) -0.004(3) 0.002(3) 0.000(4) C17 0.054(5) 0.044(4) 0.027(4) -0.003(3) 0.002(3) -0.002(3) C18 0.037(4) 0.031(3) 0.023(3) -0.003(2) 0.003(2) 0.002(2) C19 0.044(3) 0.039(3) 0.023(2) -0.0035(19) 0.002(2) 0.000(2) C20 0.037(4) 0.046(4) 0.025(3) -0.006(2) 0.003(3) 0.002(3) C21 0.033(4) 0.026(3) 0.041(4) -0.003(3) -0.008(4) 0.007(3) C22 0.033(4) 0.032(3) 0.022(3) 0.000(2) 0.000(2) -0.006(3) C23 0.032(4) 0.036(3) 0.022(3) 0.003(2) 0.014(2) 0.002(3) C24 0.062(2) 0.0384(17) 0.044(2) 0.0072(15) 0.0236(18) 0.0105(16) C25 0.057(2) 0.0432(18) 0.050(2) -0.0024(15) 0.0028(18) 0.0016(16) C26 0.053(2) 0.059(2) 0.057(2) -0.0011(17) 0.0177(18) -0.0054(17) C27 0.056(2) 0.062(2) 0.042(2) -0.0045(16) 0.0129(17) -0.0001(18) C28 0.058(2) 0.063(2) 0.050(2) -0.0132(17) 0.0088(18) -0.0062(18) C29 0.053(2) 0.0500(18) 0.060(2) -0.0035(17) 0.0164(18) -0.0056(16) O1 0.054(4) 0.061(2) 0.029(2) -0.0087(19) -0.008(3) 0.001(3) P1 0.0413(4) 0.0297(4) 0.0253(4) 0.0004(3) 0.0003(3) -0.0009(3) S1 0.0497(5) 0.0316(4) 0.0524(5) -0.0008(3) -0.0011(4) -0.0043(3) C19A 0.052(6) 0.029(4) 0.018(4) 0.003(3) 0.015(4) 0.001(4) C20A 0.085(8) 0.024(4) 0.030(5) 0.004(4) 0.034(5) 0.004(5) C22A 0.119(18) 0.058(9) 0.098(17) 0.015(11) -0.003(13) 0.028(10) C21A 0.072(16) 0.055(10) 0.073(14) 0.038(8) 0.051(14) 0.032(12) O1A 0.078(12) 0.133(13) 0.110(13) 0.066(11) 0.006(13) 0.048(10) C23A 0.089(16) 0.091(17) 0.40(5) 0.17(3) 0.18(3) 0.070(13) C13A 0.040(10) 0.027(6) 0.011(5) -0.001(4) 0.020(5) 0.004(6) C14A 0.030(6) 0.052(9) 0.026(7) 0.008(6) 0.006(5) -0.001(6) C15A 0.047(7) 0.074(11) 0.047(10) 0.018(6) -0.010(6) -0.012(7) C16A 0.052(9) 0.064(9) 0.019(9) 0.002(7) -0.004(7) -0.006(7) C17A 0.063(12) 0.041(7) 0.019(6) 0.005(5) -0.005(7) 0.000(8) C18A 0.043(7) 0.019(5) 0.024(6) -0.003(4) 0.006(5) 0.008(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.386(4) . ? C1 C6 1.402(4) . ? C1 P1 1.814(3) . ? C2 C3 1.365(4) . ? C2 H2 0.9500 . ? C3 C4 1.384(5) . ? C3 H3 0.9500 . ? C4 C5 1.365(5) . ? C4 H4 0.9500 . ? C5 C6 1.385(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.387(4) . ? C7 C8 1.391(4) . ? C7 P1 1.818(3) . ? C8 C9 1.380(4) . ? C8 H8 0.9500 . ? C9 C10 1.373(4) . ? C9 H9 0.9500 . ? C10 C11 1.374(5) . ? C10 H10 0.9500 . ? C11 C12 1.378(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.392(8) . ? C13 C18 1.408(8) . ? C13 P1 1.847(9) . ? C14 C15 1.394(8) . ? C14 H14 0.9500 . ? C15 C16 1.388(9) . ? C15 H15 0.9500 . ? C16 C17 1.364(9) . ? C16 H16 0.9500 . ? C17 C18 1.395(8) . ? C17 H17 0.9500 . ? C18 C19 1.461(7) . ? C19 C20 1.350(7) . ? C19 H19 0.9500 . ? C20 C21 1.458(10) . ? C20 H20 0.9500 . ? C21 O1 1.235(12) . ? C21 C22 1.380(11) . ? C22 C23 1.360(10) . ? C22 H22 0.9500 . ? C23 C24 1.470(7) . ? C23 H23 0.9500 . ? C24 C25 1.385(5) . ? C24 C29 1.390(4) . ? C24 C23A 1.69(4) . ? C25 C26 1.388(5) . ? C25 H25 0.9500 . ? C26 C27 1.368(4) . ? C26 H26 0.9500 . ? C27 C28 1.378(5) . ? C27 H27 0.9500 . ? C28 C29 1.375(5) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? P1 C13A 1.807(19) . ? P1 S1 1.9578(11) . ? C19A C18A 1.502(14) . ? C19A C20A 1.530(11) . ? C19A C20A 1.571(13) 3_656 ? C19A H19A 1.0000 . ? C20A C21A 1.55(2) . ? C20A C19A 1.571(13) 3_656 ? C20A H20A 1.0000 . ? C22A C23A 1.09(3) . ? C22A C21A 1.84(3) . ? C22A H22A 0.9500 . ? C21A O1A 1.14(2) . ? C23A H23A 0.9500 . ? C13A C14A 1.387(13) . ? C13A C18A 1.412(13) . ? C14A C15A 1.391(13) . ? C14A H14A 0.9500 . ? C15A C16A 1.381(13) . ? C15A H15A 0.9500 . ? C16A C17A 1.363(14) . ? C16A H16A 0.9500 . ? C17A C18A 1.403(13) . ? C17A H17A 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 C2 C1 C6 118.5(3) . . ? C2 C1 P1 119.3(2) . . ? C6 C1 P1 122.2(2) . . ? C3 C2 C1 121.6(3) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 119.6(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 119.4(3) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? C12 C7 C8 118.7(3) . . ? C12 C7 P1 119.2(2) . . ? C8 C7 P1 122.0(2) . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.4(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 120.3(3) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? C14 C13 C18 120.1(7) . . ? C14 C13 P1 116.3(6) . . ? C18 C13 P1 123.4(6) . . ? C13 C14 C15 120.9(7) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 118.7(7) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C17 C16 C15 120.4(7) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 122.4(7) . . ? C16 C17 H17 118.8 . . ? C18 C17 H17 118.8 . . ? C17 C18 C13 117.4(6) . . ? C17 C18 C19 120.8(5) . . ? C13 C18 C19 121.7(6) . . ? C20 C19 C18 127.6(5) . . ? C20 C19 H19 116.2 . . ? C18 C19 H19 116.2 . . ? C19 C20 C21 120.0(6) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? O1 C21 C22 122.5(7) . . ? O1 C21 C20 120.1(8) . . ? C22 C21 C20 117.4(7) . . ? C23 C22 C21 127.4(8) . . ? C23 C22 H22 116.3 . . ? C21 C22 H22 116.3 . . ? C22 C23 C24 126.6(7) . . ? C22 C23 H23 116.7 . . ? C24 C23 H23 116.7 . . ? C25 C24 C29 119.0(3) . . ? C25 C24 C23 126.6(4) . . ? C29 C24 C23 114.3(4) . . ? C25 C24 C23A 99.5(9) . . ? C29 C24 C23A 141.3(9) . . ? C23 C24 C23A 27.6(8) . . ? C24 C25 C26 120.0(3) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C27 C26 C25 120.6(3) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C26 C27 C28 119.6(3) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C29 C28 C27 120.6(3) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C24 120.2(3) . . ? C28 C29 H29 119.9 . . ? C24 C29 H29 119.9 . . ? C13A P1 C1 112.8(5) . . ? C13A P1 C7 98.3(5) . . ? C1 P1 C7 105.68(12) . . ? C13A P1 C13 12.8(6) . . ? C1 P1 C13 102.4(3) . . ? C7 P1 C13 109.1(3) . . ? C13A P1 S1 114.6(5) . . ? C1 P1 S1 112.22(10) . . ? C7 P1 S1 112.08(9) . . ? C13 P1 S1 114.6(3) . . ? C18A C19A C20A 119.3(7) . . ? C18A C19A C20A 116.5(8) . 3_656 ? C20A C19A C20A 89.4(7) . 3_656 ? C18A C19A H19A 110.0 . . ? C20A C19A H19A 110.0 . . ? C20A C19A H19A 110.0 3_656 . ? C19A C20A C21A 114.7(10) . . ? C19A C20A C19A 90.6(7) . 3_656 ? C21A C20A C19A 113.9(9) . 3_656 ? C19A C20A H20A 112.0 . . ? C21A C20A H20A 112.0 . . ? C19A C20A H20A 112.0 3_656 . ? C23A C22A C21A 112(4) . . ? C23A C22A H22A 124.2 . . ? C21A C22A H22A 124.2 . . ? O1A C21A C20A 124.4(19) . . ? O1A C21A C22A 133(2) . . ? C20A C21A C22A 102.1(15) . . ? C22A C23A C24 105(4) . . ? C22A C23A H23A 127.7 . . ? C24 C23A H23A 127.7 . . ? C14A C13A C18A 119.9(14) . . ? C14A C13A P1 122.0(11) . . ? C18A C13A P1 117.6(11) . . ? C13A C14A C15A 121.3(13) . . ? C13A C14A H14A 119.3 . . ? C15A C14A H14A 119.3 . . ? C16A C15A C14A 118.2(12) . . ? C16A C15A H15A 120.9 . . ? C14A C15A H15A 120.9 . . ? C17A C16A C15A 121.8(13) . . ? C17A C16A H16A 119.1 . . ? C15A C16A H16A 119.1 . . ? C16A C17A C18A 121.1(12) . . ? C16A C17A H17A 119.4 . . ? C18A C17A H17A 119.4 . . ? C17A C18A C13A 117.6(12) . . ? C17A C18A C19A 119.2(10) . . ? C13A C18A C19A 122.4(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.3(4) . . . . ? P1 C1 C2 C3 -179.1(3) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C2 C3 C4 C5 -0.4(5) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? C4 C5 C6 C1 0.7(5) . . . . ? C2 C1 C6 C5 -0.4(4) . . . . ? P1 C1 C6 C5 178.3(2) . . . . ? C12 C7 C8 C9 0.2(4) . . . . ? P1 C7 C8 C9 178.4(3) . . . . ? C7 C8 C9 C10 -0.5(5) . . . . ? C8 C9 C10 C11 0.5(5) . . . . ? C9 C10 C11 C12 -0.1(5) . . . . ? C10 C11 C12 C7 -0.1(5) . . . . ? C8 C7 C12 C11 0.1(4) . . . . ? P1 C7 C12 C11 -178.1(2) . . . . ? C18 C13 C14 C15 -0.4(4) . . . . ? P1 C13 C14 C15 -175.2(6) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C14 C15 C16 C17 0.2(8) . . . . ? C15 C16 C17 C18 0.3(10) . . . . ? C16 C17 C18 C13 -0.8(10) . . . . ? C16 C17 C18 C19 177.5(6) . . . . ? C14 C13 C18 C17 0.9(7) . . . . ? P1 C13 C18 C17 175.3(6) . . . . ? C14 C13 C18 C19 -177.5(5) . . . . ? P1 C13 C18 C19 -3.0(9) . . . . ? C17 C18 C19 C20 -6.6(9) . . . . ? C13 C18 C19 C20 171.7(6) . . . . ? C18 C19 C20 C21 -179.0(6) . . . . ? C19 C20 C21 O1 8.4(11) . . . . ? C19 C20 C21 C22 -170.7(6) . . . . ? O1 C21 C22 C23 -161.8(8) . . . . ? C20 C21 C22 C23 17.2(11) . . . . ? C21 C22 C23 C24 173.4(7) . . . . ? C22 C23 C24 C25 6.4(9) . . . . ? C22 C23 C24 C29 -175.2(6) . . . . ? C22 C23 C24 C23A -5.6(16) . . . . ? C29 C24 C25 C26 -0.1(4) . . . . ? C23 C24 C25 C26 178.2(4) . . . . ? C23A C24 C25 C26 -176.2(7) . . . . ? C24 C25 C26 C27 -0.2(5) . . . . ? C25 C26 C27 C28 0.3(5) . . . . ? C26 C27 C28 C29 -0.2(5) . . . . ? C27 C28 C29 C24 -0.1(5) . . . . ? C25 C24 C29 C28 0.2(4) . . . . ? C23 C24 C29 C28 -178.3(4) . . . . ? C23A C24 C29 C28 174.0(11) . . . . ? C2 C1 P1 C13A -151.0(6) . . . . ? C6 C1 P1 C13A 30.3(6) . . . . ? C2 C1 P1 C7 102.7(2) . . . . ? C6 C1 P1 C7 -76.0(2) . . . . ? C2 C1 P1 C13 -143.2(3) . . . . ? C6 C1 P1 C13 38.1(4) . . . . ? C2 C1 P1 S1 -19.8(3) . . . . ? C6 C1 P1 S1 161.5(2) . . . . ? C12 C7 P1 C13A 104.6(6) . . . . ? C8 C7 P1 C13A -73.6(6) . . . . ? C12 C7 P1 C1 -138.9(2) . . . . ? C8 C7 P1 C1 43.0(3) . . . . ? C12 C7 P1 C13 111.7(4) . . . . ? C8 C7 P1 C13 -66.5(4) . . . . ? C12 C7 P1 S1 -16.3(3) . . . . ? C8 C7 P1 S1 165.5(2) . . . . ? C14 C13 P1 C13A 20(3) . . . . ? C18 C13 P1 C13A -155(4) . . . . ? C14 C13 P1 C1 -125.7(4) . . . . ? C18 C13 P1 C1 59.7(7) . . . . ? C14 C13 P1 C7 -14.0(5) . . . . ? C18 C13 P1 C7 171.3(5) . . . . ? C14 C13 P1 S1 112.5(4) . . . . ? C18 C13 P1 S1 -62.1(7) . . . . ? C18A C19A C20A C21A 122.8(11) . . . . ? C20A C19A C20A C21A -116.8(11) 3_656 . . . ? C18A C19A C20A C19A -120.3(9) . . . 3_656 ? C20A C19A C20A C19A 0.0 3_656 . . 3_656 ? C19A C20A C21A O1A 7(3) . . . . ? C19A C20A C21A O1A -96(2) 3_656 . . . ? C19A C20A C21A C22A -168.4(9) . . . . ? C19A C20A C21A C22A 89.1(13) 3_656 . . . ? C23A C22A C21A O1A 28(3) . . . . ? C23A C22A C21A C20A -156.7(18) . . . . ? C21A C22A C23A C24 176.6(10) . . . . ? C25 C24 C23A C22A -165.3(16) . . . . ? C29 C24 C23A C22A 20(2) . . . . ? C23 C24 C23A C22A 4.9(13) . . . . ? C1 P1 C13A C14A -98.5(7) . . . . ? C7 P1 C13A C14A 12.5(7) . . . . ? C13 P1 C13A C14A -136(4) . . . . ? S1 P1 C13A C14A 131.5(6) . . . . ? C1 P1 C13A C18A 73.2(11) . . . . ? C7 P1 C13A C18A -175.8(9) . . . . ? C13 P1 C13A C18A 36(3) . . . . ? S1 P1 C13A C18A -56.8(11) . . . . ? C18A C13A C14A C15A -0.5(5) . . . . ? P1 C13A C14A C15A 171.0(12) . . . . ? C13A C14A C15A C16A -0.2(5) . . . . ? C14A C15A C16A C17A 0.4(12) . . . . ? C15A C16A C17A C18A 0.2(15) . . . . ? C16A C17A C18A C13A -0.9(14) . . . . ? C16A C17A C18A C19A 169.5(11) . . . . ? C14A C13A C18A C17A 1.1(11) . . . . ? P1 C13A C18A C17A -170.8(11) . . . . ? C14A C13A C18A C19A -168.9(9) . . . . ? P1 C13A C18A C19A 19.2(14) . . . . ? C20A C19A C18A C17A 34.0(13) . . . . ? C20A C19A C18A C17A -71.4(11) 3_656 . . . ? C20A C19A C18A C13A -156.1(10) . . . . ? C20A C19A C18A C13A 98.5(11) 3_656 . . . ? _diffrn_measured_fraction_theta_max 0.858 _diffrn_reflns_theta_full 29.29 _diffrn_measured_fraction_theta_full 0.858 _refine_diff_density_max 0.423 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.060 ### END data_173K _database_code_depnum_ccdc_archive 'CCDC 874846' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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 9.3704(14) _cell_length_b 17.241(3) _cell_length_c 14.693(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.056(2) _cell_angle_gamma 90.00 _cell_volume 2321.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6349 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 31.6 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.703 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn724+' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 28.5714 _diffrn_reflns_number 30313 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 31.74 _reflns_number_total 8032 _reflns_number_gt 5766 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.015208 _diffrn_orient_matrix_UB_12 0.107948 _diffrn_orient_matrix_UB_13 0.004946 _diffrn_orient_matrix_UB_21 -0.038488 _diffrn_orient_matrix_UB_22 -0.007381 _diffrn_orient_matrix_UB_23 0.042760 _diffrn_orient_matrix_UB_31 0.047999 _diffrn_orient_matrix_UB_32 0.019325 _diffrn_orient_matrix_UB_33 0.046540 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement '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^)+(0.0728P)^2^+0.9845P] 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 8032 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1865 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.58282(6) -0.01194(3) 0.77381(4) 0.04864(16) Uani 1 1 d . A . P1 P 0.51469(5) 0.09572(3) 0.76226(3) 0.03370(13) Uani 1 1 d . . . O1 O 0.8700(4) 0.0443(2) 0.5589(2) 0.0480(8) Uani 0.537(4) 1 d P A 1 C1 C 0.42843(19) 0.12355(11) 0.85710(14) 0.0379(4) Uani 1 1 d . A . C21A C 0.7165(13) 0.0581(5) 0.4773(7) 0.080(3) Uani 0.463(4) 1 d P A 2 O1A O 0.7969(7) 0.0588(4) 0.5529(6) 0.101(3) Uani 0.463(4) 1 d P A 2 C23A C 0.8443(9) 0.0660(6) 0.3574(11) 0.104(5) Uani 0.463(4) 1 d P A 2 H23A H 0.9186 0.0446 0.4048 0.125 Uiso 0.463(4) 1 calc PR A 2 C22A C 0.7329(10) 0.0850(4) 0.3565(9) 0.097(4) Uani 0.463(4) 1 d P A 2 H22A H 0.6636 0.1086 0.3080 0.116 Uiso 0.463(4) 1 calc PR A 2 C20A C 0.5519(7) 0.0453(2) 0.4658(3) 0.0480(13) Uani 0.463(4) 1 d P . 2 H20A H 0.4940 0.0835 0.4216 0.058 Uiso 0.463(4) 1 calc PR A 2 C19A C 0.4991(5) 0.0408(2) 0.5583(3) 0.0343(9) Uani 0.463(4) 1 d P . 2 H19A H 0.5842 0.0418 0.6123 0.041 Uiso 0.463(4) 1 calc PR A 2 C2 C 0.3828(3) 0.06653(14) 0.91067(16) 0.0493(5) Uani 1 1 d . . . H2 H 0.3999 0.0135 0.8989 0.059 Uiso 1 1 calc R A . C3 C 0.3126(3) 0.08616(16) 0.98136(18) 0.0592(6) Uani 1 1 d . A . H3 H 0.2814 0.0465 1.0176 0.071 Uiso 1 1 calc R . . C4 C 0.2876(3) 0.16240(17) 0.99952(18) 0.0563(6) Uani 1 1 d . . . H4 H 0.2389 0.1754 1.0480 0.068 Uiso 1 1 calc R A . C5 C 0.3333(3) 0.22016(15) 0.9472(2) 0.0599(6) Uani 1 1 d . A . H5 H 0.3167 0.2730 0.9600 0.072 Uiso 1 1 calc R . . C6 C 0.4033(3) 0.20115(13) 0.87604(19) 0.0533(6) Uani 1 1 d . . . H6 H 0.4343 0.2410 0.8400 0.064 Uiso 1 1 calc R A . C7 C 0.6634(2) 0.16418(11) 0.76608(12) 0.0343(4) Uani 1 1 d . A . C8 C 0.8045(2) 0.13945(14) 0.80378(17) 0.0498(5) Uani 1 1 d . . . H8 H 0.8212 0.0877 0.8255 0.060 Uiso 1 1 calc R A . C9 C 0.9212(3) 0.19007(18) 0.8099(2) 0.0680(8) Uani 1 1 d . A . H9 H 1.0176 0.1729 0.8350 0.082 Uiso 1 1 calc R . . C10 C 0.8968(3) 0.26506(16) 0.7795(2) 0.0619(7) Uani 1 1 d . . . H10 H 0.9767 0.2998 0.7845 0.074 Uiso 1 1 calc R A . C11 C 0.7574(3) 0.29052(14) 0.74163(16) 0.0508(5) Uani 1 1 d . A . H11 H 0.7417 0.3426 0.7209 0.061 Uiso 1 1 calc R . . C12 C 0.6400(2) 0.23994(12) 0.73381(14) 0.0413(4) Uani 1 1 d . . . H12 H 0.5443 0.2570 0.7065 0.050 Uiso 1 1 calc R A . C13 C 0.3945(8) 0.1185(3) 0.6476(5) 0.0301(12) Uani 0.537(4) 1 d PD A 1 C14 C 0.2507(5) 0.1355(3) 0.6510(4) 0.0380(10) Uani 0.537(4) 1 d PD A 1 H14 H 0.2221 0.1375 0.7093 0.046 Uiso 0.537(4) 1 calc PR A 1 C15 C 0.1477(4) 0.1496(3) 0.5688(4) 0.0441(10) Uani 0.537(4) 1 d PD A 1 H15 H 0.0494 0.1610 0.5713 0.053 Uiso 0.537(4) 1 calc PR A 1 C16 C 0.1890(6) 0.1470(3) 0.4850(4) 0.0440(11) Uani 0.537(4) 1 d PD A 1 H16 H 0.1197 0.1569 0.4291 0.053 Uiso 0.537(4) 1 calc PR A 1 C17 C 0.3325(5) 0.1299(3) 0.4816(3) 0.0416(9) Uani 0.537(4) 1 d PD A 1 H17 H 0.3598 0.1281 0.4229 0.050 Uiso 0.537(4) 1 calc PR A 1 C18 C 0.4378(4) 0.1152(2) 0.5621(2) 0.0338(7) Uani 0.537(4) 1 d PD A 1 C19 C 0.5894(4) 0.0958(2) 0.5551(2) 0.0345(7) Uani 0.537(4) 1 d P A 1 H19 H 0.6598 0.0945 0.6119 0.041 Uiso 0.537(4) 1 calc PR A 1 C20 C 0.6378(5) 0.0801(3) 0.4781(3) 0.0397(9) Uani 0.537(4) 1 d P A 1 H20 H 0.5730 0.0828 0.4192 0.048 Uiso 0.537(4) 1 calc PR A 1 C21 C 0.7908(5) 0.0585(3) 0.4840(3) 0.0383(9) Uani 0.537(4) 1 d P A 1 C22 C 0.8351(6) 0.0555(3) 0.4050(3) 0.0386(11) Uani 0.537(4) 1 d P A 1 H22 H 0.9228 0.0272 0.4078 0.046 Uiso 0.537(4) 1 calc PR A 1 C23 C 0.7762(5) 0.0863(3) 0.3184(3) 0.0315(8) Uani 0.537(4) 1 d P A 1 H23 H 0.6819 0.1086 0.3121 0.038 Uiso 0.537(4) 1 calc PR A 1 C24 C 0.8371(3) 0.08938(14) 0.23718(18) 0.0541(6) Uani 1 1 d . . . C25 C 0.9661(3) 0.05333(15) 0.22395(19) 0.0584(6) Uani 1 1 d . A . H25 H 1.0250 0.0250 0.2734 0.070 Uiso 1 1 calc R . . C26 C 1.0074(3) 0.05910(16) 0.1390(2) 0.0572(6) Uani 1 1 d . . . H26 H 1.0939 0.0343 0.1300 0.069 Uiso 1 1 calc R A . C27 C 0.9235(3) 0.10063(16) 0.06779(19) 0.0555(6) Uani 1 1 d . A . H27 H 0.9527 0.1049 0.0098 0.067 Uiso 1 1 calc R . . C28 C 0.7962(3) 0.13639(16) 0.0801(2) 0.0589(6) Uani 1 1 d . . . H28 H 0.7379 0.1649 0.0306 0.071 Uiso 1 1 calc R A . C29 C 0.7549(3) 0.13039(15) 0.1636(2) 0.0580(6) Uani 1 1 d . A . H29 H 0.6676 0.1550 0.1714 0.070 Uiso 1 1 calc R . . C13A C 0.3668(9) 0.1177(5) 0.6657(5) 0.0286(13) Uani 0.463(4) 1 d PD A 2 C14A C 0.2416(6) 0.1570(4) 0.6766(4) 0.0386(12) Uani 0.463(4) 1 d PD A 2 H14A H 0.2283 0.1688 0.7375 0.046 Uiso 0.463(4) 1 calc PR A 2 C15A C 0.1358(6) 0.1792(4) 0.6000(5) 0.0524(14) Uani 0.463(4) 1 d PD A 2 H15A H 0.0509 0.2060 0.6084 0.063 Uiso 0.463(4) 1 calc PR A 2 C16A C 0.1545(8) 0.1623(5) 0.5126(5) 0.0516(16) Uani 0.463(4) 1 d PD A 2 H16A H 0.0844 0.1796 0.4601 0.062 Uiso 0.463(4) 1 calc PR A 2 C17A C 0.2734(7) 0.1206(3) 0.4998(4) 0.0454(12) Uani 0.463(4) 1 d PD A 2 H17A H 0.2830 0.1086 0.4382 0.054 Uiso 0.463(4) 1 calc PR A 2 C18A C 0.3811(5) 0.0952(2) 0.5751(3) 0.0317(8) Uani 0.463(4) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0429(3) 0.0300(2) 0.0663(4) 0.0004(2) -0.0040(2) 0.00457(18) P1 0.0350(2) 0.0285(2) 0.0340(2) -0.00151(17) -0.00113(17) 0.00033(16) O1 0.0495(17) 0.0563(19) 0.0342(14) 0.0066(13) -0.0007(13) 0.0071(15) C1 0.0351(8) 0.0344(9) 0.0430(10) 0.0024(7) 0.0058(7) -0.0038(7) C21A 0.109(7) 0.061(4) 0.093(6) -0.049(4) 0.077(6) -0.049(5) O1A 0.069(4) 0.109(5) 0.145(6) -0.080(4) 0.063(4) -0.043(3) C23A 0.041(4) 0.069(6) 0.213(13) -0.079(8) 0.051(7) -0.022(4) C22A 0.075(5) 0.039(3) 0.149(10) -0.020(5) -0.038(6) 0.005(3) C20A 0.091(4) 0.0250(18) 0.039(2) -0.0062(16) 0.040(2) -0.011(2) C19A 0.052(2) 0.0262(17) 0.0294(17) -0.0019(13) 0.0179(15) -0.0028(15) C2 0.0594(12) 0.0433(11) 0.0443(11) 0.0087(9) 0.0083(9) -0.0046(9) C3 0.0686(15) 0.0640(16) 0.0472(13) 0.0134(11) 0.0167(11) -0.0082(12) C4 0.0522(12) 0.0703(17) 0.0504(13) 0.0024(12) 0.0201(10) -0.0016(11) C5 0.0655(15) 0.0490(13) 0.0747(17) -0.0020(12) 0.0365(13) 0.0026(11) C6 0.0585(13) 0.0382(11) 0.0727(16) 0.0004(10) 0.0359(12) -0.0034(9) C7 0.0382(8) 0.0376(9) 0.0276(8) 0.0004(6) 0.0078(6) -0.0027(7) C8 0.0386(9) 0.0514(12) 0.0571(13) 0.0098(10) 0.0049(9) -0.0024(8) C9 0.0404(11) 0.0723(18) 0.089(2) 0.0093(15) 0.0083(12) -0.0109(11) C10 0.0580(14) 0.0615(16) 0.0707(17) -0.0039(13) 0.0240(12) -0.0234(12) C11 0.0654(13) 0.0448(12) 0.0454(11) 0.0027(9) 0.0188(10) -0.0125(10) C12 0.0498(10) 0.0372(10) 0.0371(10) 0.0026(8) 0.0097(8) -0.0024(8) C13 0.034(3) 0.0257(17) 0.029(3) -0.0019(17) 0.0038(17) 0.0043(15) C14 0.0347(18) 0.041(3) 0.039(2) -0.0008(18) 0.0085(17) 0.0013(17) C15 0.0308(16) 0.051(3) 0.048(3) 0.003(2) 0.0020(18) 0.0056(17) C16 0.039(3) 0.051(3) 0.037(3) 0.002(2) -0.0034(19) 0.002(2) C17 0.043(2) 0.048(2) 0.031(2) 0.0010(16) 0.0008(16) 0.0044(18) C18 0.0355(17) 0.0318(18) 0.0313(17) -0.0008(13) 0.0004(14) 0.0000(14) C19 0.0351(15) 0.0367(17) 0.0305(15) 0.0016(12) 0.0039(12) 0.0012(12) C20 0.0401(18) 0.045(2) 0.0308(17) 0.0026(15) 0.0012(14) -0.0020(16) C21 0.0354(18) 0.0307(18) 0.044(2) 0.0010(16) -0.0023(17) 0.0016(15) C22 0.055(3) 0.0297(17) 0.0256(16) 0.0008(14) -0.0050(15) 0.0034(17) C23 0.0287(18) 0.0357(18) 0.0306(17) 0.0001(13) 0.0074(13) 0.0049(14) C24 0.0636(14) 0.0444(12) 0.0568(14) -0.0087(10) 0.0183(11) -0.0160(10) C25 0.0612(14) 0.0474(13) 0.0613(15) 0.0032(11) 0.0007(11) -0.0018(11) C26 0.0469(11) 0.0580(14) 0.0680(16) 0.0029(12) 0.0152(11) 0.0031(10) C27 0.0503(12) 0.0636(15) 0.0551(13) 0.0033(11) 0.0166(10) -0.0011(11) C28 0.0487(12) 0.0616(15) 0.0664(16) 0.0056(12) 0.0118(11) 0.0050(11) C29 0.0523(12) 0.0530(14) 0.0737(17) -0.0018(12) 0.0244(12) 0.0014(10) C13A 0.033(3) 0.032(2) 0.021(3) -0.0095(17) 0.0046(18) 0.0015(18) C14A 0.0293(19) 0.044(3) 0.042(3) -0.010(2) 0.0049(18) 0.0035(19) C15A 0.035(2) 0.053(3) 0.063(4) -0.010(3) -0.003(2) 0.007(2) C16A 0.048(4) 0.060(4) 0.039(4) -0.003(3) -0.010(3) 0.003(3) C17A 0.050(3) 0.053(3) 0.030(2) -0.005(2) 0.001(2) -0.005(3) C18A 0.037(2) 0.0280(19) 0.0306(19) -0.0013(14) 0.0080(15) -0.0035(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 S1 P1 1.9586(7) . ? P1 C13A 1.804(9) . ? P1 C1 1.815(2) . ? P1 C7 1.8178(19) . ? P1 C13 1.862(7) . ? O1 C21 1.218(5) . ? C1 C2 1.382(3) . ? C1 C6 1.397(3) . ? C21A O1A 1.205(13) . ? C21A C20A 1.531(11) . ? C21A C22A 1.872(16) . ? C23A C22A 1.092(11) . ? C23A C24 1.800(17) . ? C23A H23A 0.9500 . ? C22A H22A 0.9500 . ? C20A C19A 1.543(5) . ? C20A C19A 1.577(6) 3_656 ? C20A H20A 1.0000 . ? C19A C18A 1.510(6) . ? C19A C20A 1.577(6) 3_656 ? C19A H19A 1.0000 . ? C2 C3 1.383(4) . ? C2 H2 0.9500 . ? C3 C4 1.371(4) . ? C3 H3 0.9500 . ? C4 C5 1.380(4) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.390(3) . ? C7 C12 1.391(3) . ? C8 C9 1.387(3) . ? C8 H8 0.9500 . ? C9 C10 1.371(4) . ? C9 H9 0.9500 . ? C10 C11 1.380(4) . ? C10 H10 0.9500 . ? C11 C12 1.389(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.390(7) . ? C13 C18 1.400(6) . ? C14 C15 1.401(6) . ? C14 H14 0.9500 . ? C15 C16 1.367(7) . ? C15 H15 0.9500 . ? C16 C17 1.387(6) . ? C16 H16 0.9500 . ? C17 C18 1.396(5) . ? C17 H17 0.9500 . ? C18 C19 1.484(5) . ? C19 C20 1.331(6) . ? C19 H19 0.9500 . ? C20 C21 1.465(6) . ? C20 H20 0.9500 . ? C21 C22 1.313(7) . ? C22 C23 1.383(6) . ? C22 H22 0.9500 . ? C23 C24 1.427(5) . ? C23 H23 0.9500 . ? C24 C29 1.383(4) . ? C24 C25 1.409(4) . ? C25 C26 1.386(4) . ? C25 H25 0.9500 . ? C26 C27 1.371(4) . ? C26 H26 0.9500 . ? C27 C28 1.388(3) . ? C27 H27 0.9500 . ? C28 C29 1.366(4) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C13A C14A 1.393(8) . ? C13A C18A 1.419(7) . ? C14A C15A 1.390(7) . ? C14A H14A 0.9500 . ? C15A C16A 1.362(8) . ? C15A H15A 0.9500 . ? C16A C17A 1.372(8) . ? C16A H16A 0.9500 . ? C17A C18A 1.403(6) . ? C17A H17A 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 C13A P1 C1 99.0(2) . . ? C13A P1 C7 110.2(3) . . ? C1 P1 C7 105.42(9) . . ? C13A P1 C13 12.7(3) . . ? C1 P1 C13 110.90(19) . . ? C7 P1 C13 101.89(19) . . ? C13A P1 S1 116.8(2) . . ? C1 P1 S1 111.92(7) . . ? C7 P1 S1 112.26(7) . . ? C13 P1 S1 113.74(18) . . ? C2 C1 C6 118.9(2) . . ? C2 C1 P1 119.31(17) . . ? C6 C1 P1 121.80(16) . . ? O1A C21A C20A 121.7(6) . . ? O1A C21A C22A 135.4(8) . . ? C20A C21A C22A 102.2(8) . . ? C22A C23A C24 94.6(15) . . ? C22A C23A H23A 132.7 . . ? C24 C23A H23A 132.7 . . ? C23A C22A C21A 100.5(13) . . ? C23A C22A H22A 129.8 . . ? C21A C22A H22A 129.8 . . ? C21A C20A C19A 114.2(5) . . ? C21A C20A C19A 114.3(4) . 3_656 ? C19A C20A C19A 90.6(3) . 3_656 ? C21A C20A H20A 112.0 . . ? C19A C20A H20A 112.0 . . ? C19A C20A H20A 112.0 3_656 . ? C18A C19A C20A 119.5(4) . . ? C18A C19A C20A 115.0(4) . 3_656 ? C20A C19A C20A 89.4(3) . 3_656 ? C18A C19A H19A 110.4 . . ? C20A C19A H19A 110.4 . . ? C20A C19A H19A 110.4 3_656 . ? C1 C2 C3 120.4(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 120.6(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.9(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 120.1(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.2(2) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C8 C7 C12 119.51(18) . . ? C8 C7 P1 118.20(15) . . ? C12 C7 P1 122.29(15) . . ? C9 C8 C7 120.3(2) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 119.8(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.7(2) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C12 120.0(2) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C7 119.7(2) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? C14 C13 C18 120.3(6) . . ? C14 C13 P1 114.8(4) . . ? C18 C13 P1 124.7(4) . . ? C13 C14 C15 120.3(5) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 119.8(4) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 119.9(4) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C18 121.8(5) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C17 C18 C13 117.9(5) . . ? C17 C18 C19 119.9(4) . . ? C13 C18 C19 122.2(4) . . ? C20 C19 C18 127.3(3) . . ? C20 C19 H19 116.3 . . ? C18 C19 H19 116.3 . . ? C19 C20 C21 120.3(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? O1 C21 C22 123.1(5) . . ? O1 C21 C20 120.5(5) . . ? C22 C21 C20 116.4(4) . . ? C21 C22 C23 131.2(5) . . ? C21 C22 H22 114.4 . . ? C23 C22 H22 114.4 . . ? C22 C23 C24 129.1(4) . . ? C22 C23 H23 115.4 . . ? C24 C23 H23 115.4 . . ? C29 C24 C25 118.1(2) . . ? C29 C24 C23 114.7(3) . . ? C25 C24 C23 127.1(3) . . ? C29 C24 C23A 141.5(4) . . ? C25 C24 C23A 100.3(3) . . ? C23 C24 C23A 27.2(3) . . ? C26 C25 C24 120.1(2) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C27 C26 C25 120.1(2) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 120.3(2) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C29 C28 C27 119.7(2) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C28 C29 C24 121.7(2) . . ? C28 C29 H29 119.2 . . ? C24 C29 H29 119.2 . . ? C14A C13A C18A 119.2(7) . . ? C14A C13A P1 122.6(5) . . ? C18A C13A P1 118.2(5) . . ? C15A C14A C13A 121.1(6) . . ? C15A C14A H14A 119.5 . . ? C13A C14A H14A 119.5 . . ? C16A C15A C14A 119.6(5) . . ? C16A C15A H15A 120.2 . . ? C14A C15A H15A 120.2 . . ? C15A C16A C17A 120.6(6) . . ? C15A C16A H16A 119.7 . . ? C17A C16A H16A 119.7 . . ? C16A C17A C18A 121.7(5) . . ? C16A C17A H17A 119.2 . . ? C18A C17A H17A 119.2 . . ? C17A C18A C13A 117.5(5) . . ? C17A C18A C19A 119.7(4) . . ? C13A C18A C19A 122.6(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 C13A P1 C1 C2 106.4(3) . . . . ? C7 P1 C1 C2 -139.62(17) . . . . ? C13 P1 C1 C2 110.9(3) . . . . ? S1 P1 C1 C2 -17.31(18) . . . . ? C13A P1 C1 C6 -71.9(3) . . . . ? C7 P1 C1 C6 42.1(2) . . . . ? C13 P1 C1 C6 -67.4(3) . . . . ? S1 P1 C1 C6 164.40(17) . . . . ? C24 C23A C22A C21A 176.3(4) . . . . ? O1A C21A C22A C23A 37.2(13) . . . . ? C20A C21A C22A C23A -153.2(7) . . . . ? O1A C21A C20A C19A 4.9(10) . . . . ? C22A C21A C20A C19A -166.5(4) . . . . ? O1A C21A C20A C19A -97.6(8) . . . 3_656 ? C22A C21A C20A C19A 91.0(6) . . . 3_656 ? C21A C20A C19A C18A 124.1(5) . . . . ? C19A C20A C19A C18A -118.7(4) 3_656 . . . ? C21A C20A C19A C20A -117.1(6) . . . 3_656 ? C19A C20A C19A C20A 0.0 3_656 . . 3_656 ? C6 C1 C2 C3 0.5(3) . . . . ? P1 C1 C2 C3 -177.89(18) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? C3 C4 C5 C6 0.5(4) . . . . ? C4 C5 C6 C1 -0.3(4) . . . . ? C2 C1 C6 C5 -0.2(4) . . . . ? P1 C1 C6 C5 178.1(2) . . . . ? C13A P1 C7 C8 -151.3(3) . . . . ? C1 P1 C7 C8 102.83(18) . . . . ? C13 P1 C7 C8 -141.3(2) . . . . ? S1 P1 C7 C8 -19.26(18) . . . . ? C13A P1 C7 C12 29.5(3) . . . . ? C1 P1 C7 C12 -76.37(17) . . . . ? C13 P1 C7 C12 39.5(2) . . . . ? S1 P1 C7 C12 161.54(14) . . . . ? C12 C7 C8 C9 0.5(3) . . . . ? P1 C7 C8 C9 -178.7(2) . . . . ? C7 C8 C9 C10 0.7(4) . . . . ? C8 C9 C10 C11 -0.9(5) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C10 C11 C12 C7 1.4(3) . . . . ? C8 C7 C12 C11 -1.5(3) . . . . ? P1 C7 C12 C11 177.65(16) . . . . ? C13A P1 C13 C14 6.6(16) . . . . ? C1 P1 C13 C14 -13.9(3) . . . . ? C7 P1 C13 C14 -125.7(3) . . . . ? S1 P1 C13 C14 113.3(3) . . . . ? C13A P1 C13 C18 -170(2) . . . . ? C1 P1 C13 C18 169.7(4) . . . . ? C7 P1 C13 C18 57.9(4) . . . . ? S1 P1 C13 C18 -63.1(5) . . . . ? C18 C13 C14 C15 -0.1(3) . . . . ? P1 C13 C14 C15 -176.7(4) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? C14 C15 C16 C17 0.4(6) . . . . ? C15 C16 C17 C18 -0.1(7) . . . . ? C16 C17 C18 C13 -0.2(6) . . . . ? C16 C17 C18 C19 179.0(4) . . . . ? C14 C13 C18 C17 0.4(5) . . . . ? P1 C13 C18 C17 176.6(4) . . . . ? C14 C13 C18 C19 -178.8(4) . . . . ? P1 C13 C18 C19 -2.6(6) . . . . ? C17 C18 C19 C20 -9.7(6) . . . . ? C13 C18 C19 C20 169.5(4) . . . . ? C18 C19 C20 C21 -177.2(4) . . . . ? C19 C20 C21 O1 10.2(7) . . . . ? C19 C20 C21 C22 -170.0(4) . . . . ? O1 C21 C22 C23 -162.4(5) . . . . ? C20 C21 C22 C23 17.9(8) . . . . ? C21 C22 C23 C24 171.7(5) . . . . ? C22 C23 C24 C29 -174.7(5) . . . . ? C22 C23 C24 C25 7.8(7) . . . . ? C22 C23 C24 C23A -3.0(7) . . . . ? C22A C23A C24 C29 14.5(8) . . . . ? C22A C23A C24 C25 -169.0(6) . . . . ? C22A C23A C24 C23 2.3(7) . . . . ? C29 C24 C25 C26 -0.3(4) . . . . ? C23 C24 C25 C26 177.1(3) . . . . ? C23A C24 C25 C26 -177.9(3) . . . . ? C24 C25 C26 C27 0.7(4) . . . . ? C25 C26 C27 C28 -0.7(4) . . . . ? C26 C27 C28 C29 0.3(4) . . . . ? C27 C28 C29 C24 0.0(4) . . . . ? C25 C24 C29 C28 0.0(4) . . . . ? C23 C24 C29 C28 -177.8(3) . . . . ? C23A C24 C29 C28 176.1(4) . . . . ? C1 P1 C13A C14A 9.0(6) . . . . ? C7 P1 C13A C14A -101.2(6) . . . . ? C13 P1 C13A C14A -152(2) . . . . ? S1 P1 C13A C14A 129.2(5) . . . . ? C1 P1 C13A C18A -172.2(5) . . . . ? C7 P1 C13A C18A 77.6(6) . . . . ? C13 P1 C13A C18A 27.1(14) . . . . ? S1 P1 C13A C18A -52.0(6) . . . . ? C18A C13A C14A C15A -4.6(10) . . . . ? P1 C13A C14A C15A 174.2(6) . . . . ? C13A C14A C15A C16A 0.0(10) . . . . ? C14A C15A C16A C17A 3.0(11) . . . . ? C15A C16A C17A C18A -1.3(11) . . . . ? C16A C17A C18A C13A -3.3(9) . . . . ? C16A C17A C18A C19A 172.0(6) . . . . ? C14A C13A C18A C17A 6.1(9) . . . . ? P1 C13A C18A C17A -172.7(4) . . . . ? C14A C13A C18A C19A -169.0(5) . . . . ? P1 C13A C18A C19A 12.2(8) . . . . ? C20A C19A C18A C17A 31.3(6) . . . . ? C20A C19A C18A C17A -73.2(5) 3_656 . . . ? C20A C19A C18A C13A -153.6(5) . . . . ? C20A C19A C18A C13A 101.8(6) 3_656 . . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 31.74 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.516 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.069 ### END data_180K _database_code_depnum_ccdc_archive 'CCDC 874847' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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 9.3801(2) _cell_length_b 17.2580(2) _cell_length_c 14.7370(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.273(2) _cell_angle_gamma 90.00 _cell_volume 2331.13(7) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 34683 _cell_measurement_theta_min 3.0594 _cell_measurement_theta_max 30.4392 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97715 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 19733 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.1662 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.0594 _diffrn_reflns_theta_max 30.4392 _reflns_number_total 7072 _reflns_number_gt 3055 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0447346000 _diffrn_orient_matrix_UB_12 -0.0007367000 _diffrn_orient_matrix_UB_13 0.0452913000 _diffrn_orient_matrix_UB_21 -0.0533844000 _diffrn_orient_matrix_UB_22 0.0215673000 _diffrn_orient_matrix_UB_23 0.0168256000 _diffrn_orient_matrix_UB_31 -0.0338005000 _diffrn_orient_matrix_UB_32 -0.0349866000 _diffrn_orient_matrix_UB_33 0.0094210000 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement '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^)+(0.0505P)^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 7072 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1299 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 0.835 _refine_ls_restrained_S_all 0.835 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91756(6) -0.01490(3) 0.22272(4) 0.05298(18) Uani 1 1 d . A . P1 P 0.98698(6) 0.09228(3) 0.23548(4) 0.03685(14) Uani 1 1 d . . . O1 O 0.6266(7) 0.0432(4) 0.4422(5) 0.0520(18) Uani 0.308(4) 1 d P A 1 C1 C 1.0703(2) 0.12045(10) 0.14052(14) 0.0394(5) Uani 1 1 d . A . C2 C 1.1219(2) 0.06369(12) 0.08958(16) 0.0533(6) Uani 1 1 d . . . H2 H 1.1093 0.0106 0.1030 0.064 Uiso 1 1 calc R A . C3 C 1.1914(3) 0.08366(14) 0.01952(17) 0.0646(7) Uani 1 1 d . A . H3 H 1.2264 0.0442 -0.0150 0.078 Uiso 1 1 calc R . . C4 C 1.2105(3) 0.15971(15) -0.00084(17) 0.0636(7) Uani 1 1 d . . . H4 H 1.2597 0.1729 -0.0488 0.076 Uiso 1 1 calc R A . C5 C 1.1587(3) 0.21680(13) 0.04793(18) 0.0659(7) Uani 1 1 d . A . H5 H 1.1705 0.2696 0.0330 0.079 Uiso 1 1 calc R . . C6 C 1.0894(3) 0.19784(11) 0.11876(17) 0.0581(6) Uani 1 1 d . . . H6 H 1.0546 0.2377 0.1528 0.070 Uiso 1 1 calc R A . C7 C 0.8400(2) 0.16090(10) 0.23402(12) 0.0359(4) Uani 1 1 d . A . C8 C 0.6989(2) 0.13817(12) 0.19485(16) 0.0560(6) Uani 1 1 d . . . H8 H 0.6810 0.0868 0.1722 0.067 Uiso 1 1 calc R A . C9 C 0.5837(3) 0.18935(15) 0.18819(19) 0.0762(8) Uani 1 1 d . A . H9 H 0.4871 0.1730 0.1618 0.091 Uiso 1 1 calc R . . C10 C 0.6097(3) 0.26369(14) 0.21985(18) 0.0668(7) Uani 1 1 d . . . H10 H 0.5311 0.2993 0.2144 0.080 Uiso 1 1 calc R A . C11 C 0.7485(3) 0.28681(12) 0.25924(16) 0.0586(6) Uani 1 1 d . A . H11 H 0.7659 0.3384 0.2811 0.070 Uiso 1 1 calc R . . C12 C 0.8635(2) 0.23564(11) 0.26737(14) 0.0449(5) Uani 1 1 d . . . H12 H 0.9592 0.2519 0.2960 0.054 Uiso 1 1 calc R A . C13 C 1.1033(13) 0.1162(5) 0.3553(7) 0.021(2) Uani 0.308(4) 1 d PD A 1 C14 C 1.2468(11) 0.1319(5) 0.3518(6) 0.036(2) Uani 0.308(4) 1 d PD A 1 H14 H 1.2753 0.1328 0.2937 0.044 Uiso 0.308(4) 1 calc PR A 1 C15 C 1.3487(10) 0.1464(5) 0.4326(7) 0.046(3) Uani 0.308(4) 1 d PD A 1 H15 H 1.4474 0.1567 0.4304 0.056 Uiso 0.308(4) 1 calc PR A 1 C16 C 1.3064(11) 0.1458(5) 0.5156(7) 0.040(2) Uani 0.308(4) 1 d PD A 1 H16 H 1.3753 0.1569 0.5712 0.048 Uiso 0.308(4) 1 calc PR A 1 C17 C 1.1654(10) 0.1293(4) 0.5188(6) 0.041(2) Uani 0.308(4) 1 d PD A 1 H17 H 1.1386 0.1285 0.5775 0.049 Uiso 0.308(4) 1 calc PR A 1 C18 C 1.0585(8) 0.1134(4) 0.4389(5) 0.0321(17) Uani 0.308(4) 1 d PD A 1 C19 C 0.9062(7) 0.0941(4) 0.4453(4) 0.0389(18) Uani 0.308(4) 1 d P A 1 H19 H 0.8370 0.0916 0.3880 0.047 Uiso 0.308(4) 1 calc PR A 1 C20 C 0.8536(12) 0.0795(7) 0.5234(6) 0.039(3) Uani 0.308(4) 1 d P A 1 H20 H 0.9170 0.0832 0.5828 0.047 Uiso 0.308(4) 1 calc PR A 1 C21 C 0.7012(11) 0.0582(6) 0.5165(9) 0.045(3) Uani 0.308(4) 1 d P A 1 C22 C 0.6689(10) 0.0554(4) 0.5900(5) 0.0304(17) Uani 0.308(4) 1 d P A 1 H22 H 0.5868 0.0229 0.5891 0.036 Uiso 0.308(4) 1 calc PR A 1 C23 C 0.7242(8) 0.0897(4) 0.6827(5) 0.0220(14) Uani 0.308(4) 1 d P A 1 H23 H 0.8164 0.1148 0.6935 0.026 Uiso 0.308(4) 1 calc PR A 1 C24 C 0.6507(3) 0.08777(14) 0.75540(19) 0.0666(7) Uani 1 1 d . . . C25 C 0.5264(3) 0.05186(14) 0.7738(2) 0.0683(7) Uani 1 1 d . A . H25 H 0.4652 0.0222 0.7268 0.082 Uiso 1 1 calc R . . C26 C 0.4922(3) 0.05930(14) 0.8595(2) 0.0672(7) Uani 1 1 d . . . H26 H 0.4076 0.0346 0.8715 0.081 Uiso 1 1 calc R A . C27 C 0.5789(3) 0.10188(13) 0.92751(18) 0.0616(6) Uani 1 1 d . A . H27 H 0.5552 0.1065 0.9868 0.074 Uiso 1 1 calc R . . C28 C 0.7001(3) 0.13799(14) 0.90999(19) 0.0666(7) Uani 1 1 d . . . H28 H 0.7595 0.1684 0.9570 0.080 Uiso 1 1 calc R A . C29 C 0.7359(3) 0.13072(14) 0.8259(2) 0.0696(7) Uani 1 1 d . A . H29 H 0.8212 0.1556 0.8152 0.084 Uiso 1 1 calc R . . O1A O 0.7067(5) 0.0639(3) 0.4568(4) 0.0964(18) Uani 0.692(4) 1 d P A 2 C13A C 1.1336(6) 0.1126(3) 0.3321(4) 0.0315(12) Uani 0.692(4) 1 d PD A 2 C14A C 1.2592(5) 0.1513(2) 0.3217(3) 0.0435(11) Uani 0.692(4) 1 d PD A 2 H14A H 1.2701 0.1638 0.2608 0.052 Uiso 0.692(4) 1 calc PR A 2 C15A C 1.3684(5) 0.1723(2) 0.3957(3) 0.0633(14) Uani 0.692(4) 1 d PD A 2 H15A H 1.4530 0.1984 0.3859 0.076 Uiso 0.692(4) 1 calc PR A 2 C16A C 1.3526(7) 0.1548(4) 0.4832(4) 0.0651(19) Uani 0.692(4) 1 d PD A 2 H16A H 1.4263 0.1698 0.5351 0.078 Uiso 0.692(4) 1 calc PR A 2 C17A C 1.2323(6) 0.1161(3) 0.4974(3) 0.0517(11) Uani 0.692(4) 1 d PD A 2 H17A H 1.2240 0.1045 0.5590 0.062 Uiso 0.692(4) 1 calc PR A 2 C18A C 1.1203(4) 0.09281(18) 0.4230(2) 0.0327(7) Uani 0.692(4) 1 d PD A 2 C19A C 1.0004(3) 0.04079(13) 0.44164(19) 0.0345(8) Uani 0.692(4) 1 d P . 2 H19A H 0.9137 0.0431 0.3889 0.041 Uiso 0.692(4) 1 calc PR A 2 C20A C 0.9529(4) 0.04689(16) 0.5346(2) 0.0455(9) Uani 0.692(4) 1 d P . 2 H20A H 1.0154 0.0840 0.5778 0.055 Uiso 0.692(4) 1 calc PR A 2 C21A C 0.7911(10) 0.0625(4) 0.5275(5) 0.079(3) Uani 0.692(4) 1 d P A 2 C22A C 0.7719(5) 0.0850(2) 0.6341(4) 0.0725(13) Uani 0.692(4) 1 d P A 2 H22A H 0.8470 0.1085 0.6791 0.087 Uiso 0.692(4) 1 calc PR A 2 C23A C 0.6540(6) 0.0688(3) 0.6491(5) 0.0717(17) Uani 0.692(4) 1 d P A 2 H23A H 0.5749 0.0479 0.6046 0.086 Uiso 0.692(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0473(3) 0.0345(2) 0.0706(4) -0.0010(3) -0.0021(3) -0.0042(2) P1 0.0368(3) 0.0320(2) 0.0376(3) 0.0026(2) -0.0012(2) 0.0007(2) O1 0.041(4) 0.057(3) 0.049(4) -0.009(3) -0.009(3) -0.009(3) C1 0.0344(11) 0.0404(9) 0.0425(12) 0.0008(9) 0.0061(9) 0.0063(9) C2 0.0566(15) 0.0458(11) 0.0558(16) -0.0074(11) 0.0080(12) 0.0015(11) C3 0.0716(17) 0.0741(16) 0.0515(16) -0.0162(13) 0.0207(13) 0.0105(14) C4 0.0595(16) 0.0839(17) 0.0522(16) 0.0017(13) 0.0224(12) 0.0043(14) C5 0.0712(18) 0.0551(13) 0.083(2) 0.0103(13) 0.0421(15) 0.0058(12) C6 0.0676(16) 0.0412(11) 0.0763(18) 0.0038(11) 0.0395(13) 0.0116(11) C7 0.0413(11) 0.0401(10) 0.0262(10) -0.0003(8) 0.0071(8) 0.0032(9) C8 0.0431(13) 0.0565(12) 0.0641(16) -0.0108(11) 0.0018(11) 0.0054(11) C9 0.0451(14) 0.0853(18) 0.093(2) -0.0111(16) 0.0040(14) 0.0160(14) C10 0.0626(17) 0.0692(16) 0.0726(19) 0.0044(13) 0.0235(14) 0.0278(14) C11 0.0768(18) 0.0441(11) 0.0600(16) -0.0042(11) 0.0258(14) 0.0149(13) C12 0.0530(13) 0.0443(11) 0.0386(12) -0.0033(9) 0.0125(10) 0.0023(10) C13 0.029(5) 0.021(3) 0.013(5) -0.005(3) 0.005(3) -0.002(3) C14 0.041(6) 0.042(5) 0.027(5) 0.006(4) 0.010(4) 0.004(4) C15 0.023(4) 0.069(6) 0.044(8) 0.001(6) 0.001(5) -0.009(4) C16 0.032(6) 0.045(5) 0.038(6) -0.001(4) -0.002(4) -0.007(4) C17 0.043(5) 0.044(4) 0.030(5) -0.001(3) -0.004(4) -0.008(4) C18 0.036(4) 0.035(4) 0.026(4) -0.002(3) 0.008(3) 0.006(3) C19 0.039(4) 0.053(4) 0.025(3) -0.006(3) 0.008(3) -0.005(3) C20 0.042(6) 0.048(6) 0.020(5) -0.012(4) -0.013(4) 0.001(5) C21 0.020(4) 0.031(4) 0.074(9) -0.001(5) -0.012(5) 0.001(4) C22 0.043(5) 0.030(3) 0.015(4) -0.003(3) -0.002(3) -0.010(3) C23 0.008(3) 0.026(3) 0.033(4) -0.001(3) 0.005(3) -0.006(3) C24 0.091(2) 0.0518(13) 0.0655(19) 0.0161(13) 0.0364(16) 0.0349(15) C25 0.0697(18) 0.0629(15) 0.0689(19) -0.0021(13) 0.0068(15) 0.0070(14) C26 0.0551(16) 0.0736(16) 0.077(2) -0.0016(14) 0.0229(15) -0.0040(13) C27 0.0568(16) 0.0743(15) 0.0585(17) -0.0024(13) 0.0230(13) 0.0035(13) C28 0.0559(16) 0.0678(15) 0.079(2) -0.0114(13) 0.0196(14) -0.0026(13) C29 0.0691(18) 0.0608(14) 0.091(2) 0.0018(15) 0.0433(17) 0.0048(13) O1A 0.067(3) 0.113(3) 0.121(4) 0.062(3) 0.046(4) 0.037(2) C13A 0.033(3) 0.037(2) 0.028(3) 0.0085(17) 0.0117(18) 0.0042(16) C14A 0.033(2) 0.060(3) 0.036(3) 0.0156(18) 0.0050(18) -0.0041(18) C15A 0.037(2) 0.084(3) 0.062(3) 0.019(2) -0.002(2) -0.012(2) C16A 0.045(3) 0.090(4) 0.050(4) 0.016(3) -0.012(3) -0.015(3) C17A 0.050(3) 0.068(3) 0.033(2) 0.0113(19) 0.000(2) 0.003(2) C18A 0.0353(19) 0.0327(16) 0.0311(19) 0.0068(14) 0.0090(15) 0.0039(15) C19A 0.0466(18) 0.0313(13) 0.0306(16) 0.0024(11) 0.0195(13) 0.0026(12) C20A 0.072(3) 0.0312(14) 0.0425(19) 0.0065(13) 0.0322(17) 0.0084(16) C21A 0.113(7) 0.060(4) 0.083(5) 0.043(3) 0.062(5) 0.051(5) C22A 0.064(3) 0.0420(19) 0.106(4) 0.003(2) 0.006(3) 0.010(2) C23A 0.042(3) 0.055(3) 0.127(6) 0.034(3) 0.036(4) 0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9566(7) . ? P1 C13A 1.791(6) . ? P1 C1 1.808(2) . ? P1 C7 1.8141(19) . ? P1 C13 1.913(11) . ? O1 C21 1.196(14) . ? C1 C2 1.383(3) . ? C1 C6 1.394(3) . ? C2 C3 1.377(3) . ? C3 C4 1.367(3) . ? C4 C5 1.368(3) . ? C5 C6 1.381(3) . ? C7 C12 1.381(2) . ? C7 C8 1.383(3) . ? C8 C9 1.383(3) . ? C9 C10 1.369(3) . ? C10 C11 1.367(3) . ? C11 C12 1.379(3) . ? C13 C18 1.385(9) . ? C13 C14 1.384(11) . ? C14 C15 1.382(11) . ? C15 C16 1.363(12) . ? C16 C17 1.363(10) . ? C17 C18 1.402(9) . ? C18 C19 1.490(10) . ? C19 C20 1.370(12) . ? C20 C21 1.458(14) . ? C21 C22 1.187(15) . ? C22 C23 1.478(10) . ? C23 C24 1.392(8) . ? C24 C29 1.384(4) . ? C24 C25 1.397(4) . ? C24 C23A 1.608(7) . ? C25 C26 1.374(4) . ? C26 C27 1.363(3) . ? C27 C28 1.368(3) . ? C28 C29 1.357(3) . ? O1A C21A 1.167(8) . ? C13A C14A 1.390(6) . ? C13A C18A 1.414(5) . ? C14A C15A 1.376(6) . ? C15A C16A 1.364(6) . ? C16A C17A 1.366(7) . ? C17A C18A 1.406(5) . ? C18A C19A 1.509(4) . ? C19A C20A 1.531(4) . ? C19A C20A 1.593(4) 3_756 ? C20A C21A 1.523(8) . ? C20A C19A 1.593(4) 3_756 ? C21A C22A 1.666(9) . ? C22A C23A 1.205(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13A P1 C1 100.21(16) . . ? C13A P1 C7 109.55(16) . . ? C1 P1 C7 105.53(8) . . ? C13A P1 C13 14.8(3) . . ? C1 P1 C13 113.6(3) . . ? C7 P1 C13 98.8(3) . . ? C13A P1 S1 116.44(17) . . ? C1 P1 S1 111.69(6) . . ? C7 P1 S1 112.30(7) . . ? C13 P1 S1 113.9(3) . . ? C2 C1 C6 118.5(2) . . ? C2 C1 P1 119.24(15) . . ? C6 C1 P1 122.25(15) . . ? C3 C2 C1 120.4(2) . . ? C4 C3 C2 120.7(2) . . ? C3 C4 C5 119.9(2) . . ? C4 C5 C6 120.2(2) . . ? C5 C6 C1 120.3(2) . . ? C12 C7 C8 118.64(18) . . ? C12 C7 P1 122.83(16) . . ? C8 C7 P1 118.49(14) . . ? C7 C8 C9 120.8(2) . . ? C10 C9 C8 119.6(2) . . ? C11 C10 C9 120.2(2) . . ? C10 C11 C12 120.4(2) . . ? C11 C12 C7 120.3(2) . . ? C18 C13 C14 121.4(9) . . ? C18 C13 P1 126.3(7) . . ? C14 C13 P1 112.1(6) . . ? C13 C14 C15 120.2(8) . . ? C16 C15 C14 119.4(8) . . ? C17 C16 C15 120.2(8) . . ? C16 C17 C18 122.4(8) . . ? C13 C18 C17 116.3(8) . . ? C13 C18 C19 122.7(7) . . ? C17 C18 C19 120.9(6) . . ? C20 C19 C18 128.1(6) . . ? C19 C20 C21 120.7(9) . . ? C22 C21 O1 127.9(10) . . ? C22 C21 C20 112.5(10) . . ? O1 C21 C20 119.5(12) . . ? C21 C22 C23 136.0(9) . . ? C24 C23 C22 124.6(7) . . ? C29 C24 C23 105.3(4) . . ? C29 C24 C25 117.7(2) . . ? C23 C24 C25 136.9(4) . . ? C29 C24 C23A 135.5(3) . . ? C23 C24 C23A 30.6(3) . . ? C25 C24 C23A 106.8(3) . . ? C26 C25 C24 120.3(3) . . ? C27 C26 C25 120.5(3) . . ? C26 C27 C28 119.8(2) . . ? C29 C28 C27 120.5(2) . . ? C28 C29 C24 121.3(3) . . ? C14A C13A C18A 117.9(5) . . ? C14A C13A P1 122.1(4) . . ? C18A C13A P1 119.9(4) . . ? C15A C14A C13A 123.0(4) . . ? C16A C15A C14A 118.6(4) . . ? C15A C16A C17A 120.8(5) . . ? C16A C17A C18A 121.7(4) . . ? C17A C18A C13A 117.9(4) . . ? C17A C18A C19A 119.3(3) . . ? C13A C18A C19A 122.4(3) . . ? C18A C19A C20A 119.5(2) . . ? C18A C19A C20A 115.1(2) . 3_756 ? C20A C19A C20A 89.2(2) . 3_756 ? C21A C20A C19A 115.2(3) . . ? C21A C20A C19A 114.0(3) . 3_756 ? C19A C20A C19A 90.8(2) . 3_756 ? O1A C21A C20A 122.9(6) . . ? O1A C21A C22A 130.4(7) . . ? C20A C21A C22A 106.4(5) . . ? C23A C22A C21A 113.9(7) . . ? C22A C23A C24 109.8(7) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.251 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.041 ### END data_220K _database_code_depnum_ccdc_archive 'CCDC 874848' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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 9.406(5) _cell_length_b 17.312(5) _cell_length_c 14.818(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 102.305(5) _cell_angle_gamma 90.000(5) _cell_volume 2357.5(16) _cell_formula_units_Z 4 _cell_measurement_temperature 221(2) _cell_measurement_reflns_used 4999 _cell_measurement_theta_min 2.8081 _cell_measurement_theta_max 29.4966 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.63206 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 221(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.3795 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 18393 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.1464 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.8081 _diffrn_reflns_theta_max 29.4966 _reflns_number_total 5786 _reflns_number_gt 3246 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0167426000 _diffrn_orient_matrix_UB_12 0.0348632000 _diffrn_orient_matrix_UB_13 -0.0206317000 _diffrn_orient_matrix_UB_21 0.0210537000 _diffrn_orient_matrix_UB_22 -0.0214422000 _diffrn_orient_matrix_UB_23 -0.0358020000 _diffrn_orient_matrix_UB_31 -0.0723370000 _diffrn_orient_matrix_UB_32 0.0018504000 _diffrn_orient_matrix_UB_33 -0.0263176000 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement '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^)+(0.0503P)^2^+0.2027P] 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 5786 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1213 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1293 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91675(7) -0.01547(4) 0.22253(5) 0.0575(2) Uani 1 1 d . A . P1 P 0.98573(6) 0.09124(3) 0.23506(4) 0.04031(17) Uani 1 1 d . . . O1A O 0.7107(7) 0.0662(4) 0.4601(5) 0.098(2) Uani 0.695(5) 1 d P A 2 C1 C 1.0678(2) 0.11946(14) 0.13968(15) 0.0451(5) Uani 1 1 d . A . C2 C 1.1216(3) 0.06307(15) 0.09017(17) 0.0603(7) Uani 1 1 d . . . H2 H 1.1115 0.0107 0.1044 0.072 Uiso 1 1 calc R A . C3 C 1.1902(3) 0.08317(19) 0.01992(18) 0.0739(8) Uani 1 1 d . A . H3 H 1.2252 0.0442 -0.0138 0.089 Uiso 1 1 calc R . . C4 C 1.2077(3) 0.1584(2) -0.00109(18) 0.0728(8) Uani 1 1 d . . . H4 H 1.2563 0.1713 -0.0483 0.087 Uiso 1 1 calc R A . C5 C 1.1544(3) 0.21586(18) 0.0467(2) 0.0744(8) Uani 1 1 d . A . H5 H 1.1647 0.2680 0.0315 0.089 Uiso 1 1 calc R . . C6 C 1.0855(3) 0.19627(15) 0.11718(18) 0.0648(7) Uani 1 1 d . . . H6 H 1.0501 0.2355 0.1504 0.078 Uiso 1 1 calc R A . C7 C 0.8392(2) 0.15951(13) 0.23412(13) 0.0403(5) Uani 1 1 d . A . C8 C 0.6989(3) 0.13762(16) 0.19452(18) 0.0645(7) Uani 1 1 d . . . H8 H 0.6807 0.0872 0.1714 0.077 Uiso 1 1 calc R A . C9 C 0.5848(3) 0.1888(2) 0.1884(2) 0.0883(10) Uani 1 1 d . A . H9 H 0.4892 0.1731 0.1624 0.106 Uiso 1 1 calc R . . C10 C 0.6114(3) 0.2624(2) 0.2201(2) 0.0775(9) Uani 1 1 d . . . H10 H 0.5340 0.2977 0.2142 0.093 Uiso 1 1 calc R A . C11 C 0.7497(3) 0.28545(16) 0.26055(17) 0.0668(7) Uani 1 1 d . A . H11 H 0.7668 0.3361 0.2830 0.080 Uiso 1 1 calc R . . C12 C 0.8633(3) 0.23419(14) 0.26815(15) 0.0531(6) Uani 1 1 d . . . H12 H 0.9580 0.2498 0.2966 0.064 Uiso 1 1 calc R A . C13A C 1.1325(8) 0.1117(4) 0.3317(5) 0.0352(14) Uani 0.695(5) 1 d PD A 2 C14A C 1.2572(6) 0.1499(3) 0.3200(4) 0.0495(14) Uani 0.695(5) 1 d PD A 2 H14A H 1.2666 0.1624 0.2598 0.059 Uiso 0.695(5) 1 calc PR A 2 C15A C 1.3675(5) 0.1703(3) 0.3930(4) 0.0694(17) Uani 0.695(5) 1 d PD A 2 H15A H 1.4512 0.1956 0.3831 0.083 Uiso 0.695(5) 1 calc PR A 2 C16A C 1.3520(8) 0.1525(4) 0.4809(4) 0.066(2) Uani 0.695(5) 1 d PD A 2 H16A H 1.4255 0.1668 0.5317 0.079 Uiso 0.695(5) 1 calc PR A 2 C17A C 1.2327(6) 0.1147(3) 0.4958(3) 0.0544(13) Uani 0.695(5) 1 d PD A 2 H17A H 1.2250 0.1039 0.5568 0.065 Uiso 0.695(5) 1 calc PR A 2 C18A C 1.1209(4) 0.0913(2) 0.4225(3) 0.0372(9) Uani 0.695(5) 1 d PD A 2 C19A C 1.0014(3) 0.04018(17) 0.44169(19) 0.0369(9) Uani 0.695(5) 1 d P . 2 H19A H 0.9149 0.0433 0.3903 0.044 Uiso 0.695(5) 1 calc PR A 2 C20A C 0.9559(5) 0.0467(2) 0.5353(2) 0.0463(10) Uani 0.695(5) 1 d P . 2 H20A H 1.0210 0.0822 0.5774 0.056 Uiso 0.695(5) 1 calc PR A 2 C21A C 0.7985(10) 0.0657(4) 0.5313(5) 0.070(3) Uani 0.695(5) 1 d P A 2 C22A C 0.7729(5) 0.0855(2) 0.6311(4) 0.0674(13) Uani 0.695(5) 1 d P A 2 H22A H 0.8470 0.1092 0.6751 0.081 Uiso 0.695(5) 1 calc PR A 2 C23A C 0.6563(7) 0.0699(3) 0.6507(5) 0.0633(16) Uani 0.695(5) 1 d P A 2 H23A H 0.5780 0.0490 0.6074 0.076 Uiso 0.695(5) 1 calc PR A 2 C24 C 0.6468(4) 0.08734(17) 0.7531(2) 0.0713(8) Uani 1 1 d . . . C25 C 0.7331(3) 0.13082(18) 0.8224(2) 0.0788(9) Uani 1 1 d . A . H25 H 0.8163 0.1556 0.8109 0.095 Uiso 1 1 calc R . . C26 C 0.6991(3) 0.13827(18) 0.9077(2) 0.0768(8) Uani 1 1 d . . . H26 H 0.7587 0.1680 0.9538 0.092 Uiso 1 1 calc R A . C27 C 0.5779(3) 0.10216(18) 0.9255(2) 0.0707(8) Uani 1 1 d . A . H27 H 0.5544 0.1068 0.9838 0.085 Uiso 1 1 calc R . . C28 C 0.4928(3) 0.05988(17) 0.8584(2) 0.0731(8) Uani 1 1 d . . . H28 H 0.4098 0.0353 0.8706 0.088 Uiso 1 1 calc R A . C29 C 0.5249(3) 0.05197(17) 0.7726(2) 0.0731(8) Uani 1 1 d . A . H29 H 0.4637 0.0224 0.7270 0.088 Uiso 1 1 calc R . . C19 C 0.9052(8) 0.0936(5) 0.4448(5) 0.050(3) Uani 0.305(5) 1 d P A 1 H19 H 0.8348 0.0922 0.3893 0.060 Uiso 0.305(5) 1 calc PR A 1 O1 O 0.6291(10) 0.0435(5) 0.4413(6) 0.068(2) Uani 0.305(5) 1 d P A 1 C21 C 0.7025(16) 0.0583(7) 0.5151(12) 0.059(4) Uani 0.305(5) 1 d P A 1 C22 C 0.6669(11) 0.0565(4) 0.5912(6) 0.035(2) Uani 0.305(5) 1 d P A 1 H22 H 0.5833 0.0265 0.5904 0.042 Uiso 0.305(5) 1 calc PR A 1 C20 C 0.8600(16) 0.0792(10) 0.5206(8) 0.057(4) Uani 0.305(5) 1 d P A 1 H20 H 0.9252 0.0819 0.5782 0.069 Uiso 0.305(5) 1 calc PR A 1 C23 C 0.7255(10) 0.0903(5) 0.6809(6) 0.028(2) Uani 0.305(5) 1 d P A 1 H23 H 0.8169 0.1145 0.6916 0.034 Uiso 0.305(5) 1 calc PR A 1 C13 C 1.1028(16) 0.1147(7) 0.3545(8) 0.032(3) Uani 0.305(5) 1 d PD A 1 C14 C 1.2456(14) 0.1322(7) 0.3515(7) 0.046(3) Uani 0.305(5) 1 d PD A 1 H14 H 1.2735 0.1333 0.2942 0.056 Uiso 0.305(5) 1 calc PR A 1 C15 C 1.3478(13) 0.1480(7) 0.4316(8) 0.054(4) Uani 0.305(5) 1 d PD A 1 H15 H 1.4445 0.1597 0.4292 0.064 Uiso 0.305(5) 1 calc PR A 1 C16 C 1.3044(13) 0.1462(6) 0.5145(8) 0.049(3) Uani 0.305(5) 1 d PD A 1 H16 H 1.3723 0.1569 0.5695 0.059 Uiso 0.305(5) 1 calc PR A 1 C17 C 1.1634(12) 0.1289(6) 0.5181(6) 0.053(3) Uani 0.305(5) 1 d PD A 1 H17 H 1.1359 0.1283 0.5755 0.063 Uiso 0.305(5) 1 calc PR A 1 C18 C 1.0594(10) 0.1122(5) 0.4374(5) 0.035(2) Uani 0.305(5) 1 d PD A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0540(4) 0.0382(4) 0.0742(4) -0.0008(3) -0.0001(3) -0.0048(3) P1 0.0412(3) 0.0358(3) 0.0402(3) 0.0030(3) 0.0003(2) 0.0003(3) O1A 0.073(4) 0.115(4) 0.117(5) 0.054(4) 0.043(5) 0.034(3) C1 0.0420(12) 0.0441(14) 0.0485(12) 0.0013(11) 0.0082(10) 0.0084(11) C2 0.0699(17) 0.0503(15) 0.0605(15) -0.0089(13) 0.0135(14) 0.0060(14) C3 0.089(2) 0.079(2) 0.0604(17) -0.0160(16) 0.0313(16) 0.0124(18) C4 0.0721(19) 0.092(2) 0.0598(17) 0.0063(17) 0.0273(14) 0.0066(17) C5 0.083(2) 0.0616(18) 0.092(2) 0.0170(16) 0.0474(17) 0.0097(16) C6 0.0778(18) 0.0468(16) 0.0813(18) 0.0057(14) 0.0425(15) 0.0145(14) C7 0.0469(13) 0.0442(13) 0.0289(10) 0.0013(10) 0.0062(9) 0.0022(11) C8 0.0492(15) 0.0620(18) 0.0760(17) -0.0137(14) -0.0009(13) 0.0085(14) C9 0.0526(17) 0.094(3) 0.112(2) -0.011(2) 0.0022(16) 0.0173(18) C10 0.077(2) 0.077(2) 0.084(2) 0.0053(17) 0.0271(17) 0.0324(18) C11 0.086(2) 0.0533(16) 0.0669(17) -0.0088(14) 0.0306(16) 0.0154(16) C12 0.0602(15) 0.0524(16) 0.0474(13) -0.0056(12) 0.0130(11) 0.0022(13) C13A 0.043(4) 0.034(2) 0.031(3) 0.0103(19) 0.014(2) -0.001(2) C14A 0.039(2) 0.065(3) 0.042(3) 0.016(2) 0.005(2) -0.009(2) C15A 0.042(3) 0.095(4) 0.066(4) 0.023(3) 0.000(2) -0.018(2) C16A 0.049(4) 0.090(4) 0.050(5) 0.016(4) -0.011(4) -0.013(3) C17A 0.059(3) 0.064(4) 0.037(2) 0.011(2) 0.002(2) -0.002(3) C18A 0.035(2) 0.040(2) 0.039(2) 0.0046(18) 0.0111(18) 0.0071(18) C19A 0.048(2) 0.0321(18) 0.0335(16) 0.0077(13) 0.0163(14) 0.0049(15) C20A 0.064(3) 0.035(2) 0.0459(19) 0.0084(15) 0.0249(19) 0.0112(18) C21A 0.093(7) 0.057(4) 0.074(4) 0.033(3) 0.049(5) 0.043(5) C22A 0.062(3) 0.049(3) 0.091(3) 0.007(3) 0.016(3) 0.008(2) C23A 0.049(3) 0.053(3) 0.094(5) 0.024(3) 0.029(3) 0.012(2) C24 0.098(2) 0.0541(17) 0.0708(18) 0.0143(15) 0.0378(17) 0.0320(17) C25 0.077(2) 0.067(2) 0.107(2) 0.0034(19) 0.0530(19) 0.0076(16) C26 0.0646(18) 0.075(2) 0.093(2) -0.0175(17) 0.0227(17) -0.0014(16) C27 0.0646(17) 0.081(2) 0.0700(17) -0.0077(16) 0.0231(15) 0.0002(16) C28 0.0633(17) 0.078(2) 0.085(2) -0.0019(17) 0.0304(16) -0.0041(16) C29 0.0706(19) 0.071(2) 0.0776(19) -0.0009(16) 0.0147(16) 0.0030(16) C19 0.046(5) 0.066(6) 0.036(4) -0.005(4) 0.005(3) -0.010(4) O1 0.065(5) 0.069(5) 0.058(4) -0.009(3) -0.013(5) -0.017(4) C21 0.029(6) 0.035(5) 0.099(13) 0.012(7) -0.014(7) -0.007(5) C22 0.045(5) 0.039(5) 0.020(4) 0.002(4) 0.002(4) -0.014(4) C20 0.053(8) 0.086(10) 0.029(6) -0.012(6) 0.000(6) -0.018(7) C23 0.017(4) 0.033(4) 0.035(5) -0.003(4) 0.003(4) -0.012(4) C13 0.029(6) 0.040(5) 0.027(7) -0.002(5) 0.003(5) -0.004(4) C14 0.046(7) 0.052(7) 0.038(7) 0.002(5) 0.004(5) 0.003(5) C15 0.032(5) 0.085(9) 0.044(9) 0.006(8) 0.008(7) -0.007(5) C16 0.045(8) 0.056(7) 0.041(7) -0.014(5) -0.003(5) -0.006(6) C17 0.059(7) 0.061(6) 0.033(5) -0.003(4) 0.000(4) -0.008(5) C18 0.040(5) 0.038(5) 0.024(4) 0.002(3) 0.000(4) 0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9536(10) . ? P1 C13A 1.800(7) . ? P1 C7 1.814(2) . ? P1 C1 1.816(2) . ? P1 C13 1.918(13) . ? O1A C21A 1.193(9) . ? C1 C2 1.381(3) . ? C1 C6 1.390(3) . ? C2 C3 1.381(4) . ? C2 H2 0.9400 . ? C3 C4 1.358(4) . ? C3 H3 0.9400 . ? C4 C5 1.375(4) . ? C4 H4 0.9400 . ? C5 C6 1.384(3) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C7 C8 1.378(3) . ? C7 C12 1.389(3) . ? C8 C9 1.380(4) . ? C8 H8 0.9400 . ? C9 C10 1.362(4) . ? C9 H9 0.9400 . ? C10 C11 1.371(4) . ? C10 H10 0.9400 . ? C11 C12 1.375(3) . ? C11 H11 0.9400 . ? C12 H12 0.9400 . ? C13A C14A 1.390(7) . ? C13A C18A 1.418(6) . ? C14A C15A 1.375(7) . ? C14A H14A 0.9400 . ? C15A C16A 1.376(6) . ? C15A H15A 0.9400 . ? C16A C17A 1.357(8) . ? C16A H16A 0.9400 . ? C17A C18A 1.401(6) . ? C17A H17A 0.9400 . ? C18A C19A 1.504(5) . ? C19A C20A 1.540(4) . ? C19A C20A 1.576(5) 3_756 ? C19A H19A 0.9900 . ? C20A C21A 1.506(8) . ? C20A C19A 1.576(5) 3_756 ? C20A H20A 0.9900 . ? C21A C22A 1.586(9) . ? C22A C23A 1.222(7) . ? C22A H22A 0.9400 . ? C23A C24 1.568(7) . ? C23A H23A 0.9400 . ? C24 C29 1.384(4) . ? C24 C25 1.388(4) . ? C24 C23 1.426(10) . ? C25 C26 1.374(4) . ? C25 H25 0.9400 . ? C26 C27 1.374(4) . ? C26 H26 0.9400 . ? C27 C28 1.351(4) . ? C27 H27 0.9400 . ? C28 C29 1.373(4) . ? C28 H28 0.9400 . ? C29 H29 0.9400 . ? C19 C20 1.307(14) . ? C19 C18 1.512(11) . ? C19 H19 0.9400 . ? O1 C21 1.19(2) . ? C21 C22 1.244(19) . ? C21 C20 1.510(16) . ? C22 C23 1.449(13) . ? C22 H22 0.9400 . ? C20 H20 0.9400 . ? C23 H23 0.9400 . ? C13 C18 1.376(11) . ? C13 C14 1.387(13) . ? C14 C15 1.386(13) . ? C14 H14 0.9400 . ? C15 C16 1.376(13) . ? C15 H15 0.9400 . ? C16 C17 1.372(12) . ? C16 H16 0.9400 . ? C17 C18 1.403(10) . ? C17 H17 0.9400 . ? 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 C13A P1 C7 109.3(2) . . ? C13A P1 C1 100.7(2) . . ? C7 P1 C1 105.49(10) . . ? C13A P1 C13 14.5(4) . . ? C7 P1 C13 98.9(4) . . ? C1 P1 C13 113.9(4) . . ? C13A P1 S1 116.4(2) . . ? C7 P1 S1 112.27(8) . . ? C1 P1 S1 111.60(8) . . ? C13 P1 S1 113.7(4) . . ? C2 C1 C6 118.2(2) . . ? C2 C1 P1 119.23(19) . . ? C6 C1 P1 122.47(18) . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 120.9(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.5(3) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 121.0(2) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? C8 C7 C12 118.6(2) . . ? C8 C7 P1 118.77(18) . . ? C12 C7 P1 122.60(17) . . ? C7 C8 C9 120.8(3) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 119.7(3) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.7(3) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C12 119.8(3) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C7 120.5(2) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? C14A C13A C18A 118.3(5) . . ? C14A C13A P1 121.3(4) . . ? C18A C13A P1 120.4(4) . . ? C15A C14A C13A 122.6(5) . . ? C15A C14A H14A 118.7 . . ? C13A C14A H14A 118.7 . . ? C14A C15A C16A 118.2(5) . . ? C14A C15A H15A 120.9 . . ? C16A C15A H15A 120.9 . . ? C17A C16A C15A 121.3(5) . . ? C17A C16A H16A 119.3 . . ? C15A C16A H16A 119.3 . . ? C16A C17A C18A 121.6(4) . . ? C16A C17A H17A 119.2 . . ? C18A C17A H17A 119.2 . . ? C17A C18A C13A 117.8(5) . . ? C17A C18A C19A 119.4(4) . . ? C13A C18A C19A 122.5(4) . . ? C18A C19A C20A 119.3(3) . . ? C18A C19A C20A 115.9(3) . 3_756 ? C20A C19A C20A 89.0(2) . 3_756 ? C18A C19A H19A 110.4 . . ? C20A C19A H19A 110.4 . . ? C20A C19A H19A 110.4 3_756 . ? C21A C20A C19A 116.2(4) . . ? C21A C20A C19A 114.8(4) . 3_756 ? C19A C20A C19A 91.0(2) . 3_756 ? C21A C20A H20A 111.1 . . ? C19A C20A H20A 111.1 . . ? C19A C20A H20A 111.1 3_756 . ? O1A C21A C20A 121.7(6) . . ? O1A C21A C22A 127.5(7) . . ? C20A C21A C22A 110.7(6) . . ? C23A C22A C21A 119.7(8) . . ? C23A C22A H22A 120.2 . . ? C21A C22A H22A 120.2 . . ? C22A C23A C24 115.2(8) . . ? C22A C23A H23A 122.4 . . ? C24 C23A H23A 122.4 . . ? C29 C24 C25 117.7(3) . . ? C29 C24 C23 139.3(5) . . ? C25 C24 C23 102.8(4) . . ? C29 C24 C23A 109.8(4) . . ? C25 C24 C23A 132.5(4) . . ? C23 C24 C23A 30.1(3) . . ? C26 C25 C24 121.2(3) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C27 C26 C25 119.9(3) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C28 C27 C26 119.4(3) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C27 C28 C29 121.5(3) . . ? C27 C28 H28 119.2 . . ? C29 C28 H28 119.2 . . ? C28 C29 C24 120.3(3) . . ? C28 C29 H29 119.9 . . ? C24 C29 H29 119.9 . . ? C20 C19 C18 126.5(8) . . ? C20 C19 H19 116.7 . . ? C18 C19 H19 116.7 . . ? O1 C21 C22 127.7(12) . . ? O1 C21 C20 118.2(15) . . ? C22 C21 C20 114.1(12) . . ? C21 C22 C23 134.3(10) . . ? C21 C22 H22 112.9 . . ? C23 C22 H22 112.9 . . ? C19 C20 C21 119.6(11) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C24 C23 C22 121.2(9) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C18 C13 C14 120.6(10) . . ? C18 C13 P1 126.6(9) . . ? C14 C13 P1 112.7(8) . . ? C15 C14 C13 121.0(10) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C16 C15 C14 118.5(10) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C17 C16 C15 120.8(10) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 121.1(9) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C13 C18 C17 118.0(9) . . ? C13 C18 C19 122.9(8) . . ? C17 C18 C19 119.2(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13A P1 C1 C2 101.1(3) . . . . ? C7 P1 C1 C2 -145.21(18) . . . . ? C13 P1 C1 C2 107.4(5) . . . . ? S1 P1 C1 C2 -23.0(2) . . . . ? C13A P1 C1 C6 -75.5(3) . . . . ? C7 P1 C1 C6 38.2(2) . . . . ? C13 P1 C1 C6 -69.2(5) . . . . ? S1 P1 C1 C6 160.38(19) . . . . ? C6 C1 C2 C3 -0.4(4) . . . . ? P1 C1 C2 C3 -177.17(19) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C3 C4 C5 C6 1.2(4) . . . . ? C4 C5 C6 C1 -0.8(4) . . . . ? C2 C1 C6 C5 0.4(4) . . . . ? P1 C1 C6 C5 177.0(2) . . . . ? C13A P1 C7 C8 -152.8(3) . . . . ? C1 P1 C7 C8 99.6(2) . . . . ? C13 P1 C7 C8 -142.4(4) . . . . ? S1 P1 C7 C8 -22.1(2) . . . . ? C13A P1 C7 C12 30.0(3) . . . . ? C1 P1 C7 C12 -77.52(19) . . . . ? C13 P1 C7 C12 40.5(4) . . . . ? S1 P1 C7 C12 160.73(16) . . . . ? C12 C7 C8 C9 0.3(4) . . . . ? P1 C7 C8 C9 -177.0(2) . . . . ? C7 C8 C9 C10 1.3(5) . . . . ? C8 C9 C10 C11 -1.9(5) . . . . ? C9 C10 C11 C12 0.9(4) . . . . ? C10 C11 C12 C7 0.8(4) . . . . ? C8 C7 C12 C11 -1.4(3) . . . . ? P1 C7 C12 C11 175.79(17) . . . . ? C7 P1 C13A C14A -102.7(3) . . . . ? C1 P1 C13A C14A 8.1(3) . . . . ? C13 P1 C13A C14A -148(2) . . . . ? S1 P1 C13A C14A 128.8(3) . . . . ? C7 P1 C13A C18A 75.0(5) . . . . ? C1 P1 C13A C18A -174.2(4) . . . . ? C13 P1 C13A C18A 29.4(18) . . . . ? S1 P1 C13A C18A -53.4(5) . . . . ? C18A C13A C14A C15A -1.6(4) . . . . ? P1 C13A C14A C15A 176.2(4) . . . . ? C13A C14A C15A C16A -0.7(4) . . . . ? C14A C15A C16A C17A 1.2(8) . . . . ? C15A C16A C17A C18A 0.7(9) . . . . ? C16A C17A C18A C13A -3.0(7) . . . . ? C16A C17A C18A C19A 171.6(4) . . . . ? C14A C13A C18A C17A 3.4(6) . . . . ? P1 C13A C18A C17A -174.4(4) . . . . ? C14A C13A C18A C19A -171.1(3) . . . . ? P1 C13A C18A C19A 11.1(6) . . . . ? C17A C18A C19A C20A 30.8(5) . . . . ? C13A C18A C19A C20A -154.9(4) . . . . ? C17A C18A C19A C20A -73.6(4) . . . 3_756 ? C13A C18A C19A C20A 100.7(4) . . . 3_756 ? C18A C19A C20A C21A 122.2(5) . . . . ? C20A C19A C20A C21A -118.5(5) 3_756 . . . ? C18A C19A C20A C19A -119.4(3) . . . 3_756 ? C20A C19A C20A C19A 0.0 3_756 . . 3_756 ? C19A C20A C21A O1A 9.0(10) . . . . ? C19A C20A C21A O1A -95.5(8) 3_756 . . . ? C19A C20A C21A C22A -169.7(4) . . . . ? C19A C20A C21A C22A 85.8(6) 3_756 . . . ? O1A C21A C22A C23A 33.1(11) . . . . ? C20A C21A C22A C23A -148.3(5) . . . . ? C21A C22A C23A C24 176.3(4) . . . . ? C22A C23A C24 C29 -166.6(4) . . . . ? C22A C23A C24 C25 14.8(6) . . . . ? C22A C23A C24 C23 4.3(7) . . . . ? C29 C24 C25 C26 0.3(4) . . . . ? C23 C24 C25 C26 -175.9(4) . . . . ? C23A C24 C25 C26 178.7(3) . . . . ? C24 C25 C26 C27 0.1(5) . . . . ? C25 C26 C27 C28 -0.4(5) . . . . ? C26 C27 C28 C29 0.2(5) . . . . ? C27 C28 C29 C24 0.3(5) . . . . ? C25 C24 C29 C28 -0.5(4) . . . . ? C23 C24 C29 C28 173.8(6) . . . . ? C23A C24 C29 C28 -179.3(3) . . . . ? O1 C21 C22 C23 -161.0(12) . . . . ? C20 C21 C22 C23 21(2) . . . . ? C18 C19 C20 C21 -177.4(11) . . . . ? O1 C21 C20 C19 12(2) . . . . ? C22 C21 C20 C19 -170.4(13) . . . . ? C29 C24 C23 C22 10.1(11) . . . . ? C25 C24 C23 C22 -175.2(6) . . . . ? C23A C24 C23 C22 -3.2(5) . . . . ? C21 C22 C23 C24 170.2(12) . . . . ? C13A P1 C13 C18 -166(3) . . . . ? C7 P1 C13 C18 56.8(9) . . . . ? C1 P1 C13 C18 168.2(8) . . . . ? S1 P1 C13 C18 -62.4(10) . . . . ? C13A P1 C13 C14 10.8(18) . . . . ? C7 P1 C13 C14 -126.2(5) . . . . ? C1 P1 C13 C14 -14.8(6) . . . . ? S1 P1 C13 C14 114.6(5) . . . . ? C18 C13 C14 C15 -0.5(5) . . . . ? P1 C13 C14 C15 -177.7(8) . . . . ? C13 C14 C15 C16 -0.1(5) . . . . ? C14 C15 C16 C17 0.2(11) . . . . ? C15 C16 C17 C18 0.3(13) . . . . ? C14 C13 C18 C17 1.0(10) . . . . ? P1 C13 C18 C17 177.8(9) . . . . ? C14 C13 C18 C19 180.0(8) . . . . ? P1 C13 C18 C19 -3.2(13) . . . . ? C16 C17 C18 C13 -0.9(12) . . . . ? C16 C17 C18 C19 -179.9(9) . . . . ? C20 C19 C18 C13 169.5(12) . . . . ? C20 C19 C18 C17 -11.5(15) . . . . ? _diffrn_measured_fraction_theta_max 0.876 _diffrn_reflns_theta_full 29.56 _diffrn_measured_fraction_theta_full 0.876 _refine_diff_density_max 0.263 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.039 ### END data_ijf1027 _database_code_depnum_ccdc_archive 'CCDC 874849' #TrackingRef '- all.cif' _audit_creation_method 'WinGX routine CIF_UPDATE' __chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4598(10) _cell_length_b 16.9974(14) _cell_length_c 14.5643(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.853(9) _cell_angle_gamma 90.00 _cell_volume 2291.9(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4090 _cell_measurement_temperature 110.0 _cell_measurement_theta_max 24.9727 _cell_measurement_theta_min 3.0932 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.98417 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_unetI/netI 0.0418 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7539 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 3.10 _diffrn_ambient_temperature 110.0 _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -54.00 39.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 16.2440 -37.0000 -150.0000 93 #__ type_ start__ end____ width___ exp.time_ 2 omega -7.00 82.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 16.2440 77.0000 -30.0000 89 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0586888000 _diffrn_orient_matrix_UB_12 -0.0247995000 _diffrn_orient_matrix_UB_13 -0.0037697000 _diffrn_orient_matrix_UB_21 -0.0322822000 _diffrn_orient_matrix_UB_22 -0.0077496000 _diffrn_orient_matrix_UB_23 -0.0476419000 _diffrn_orient_matrix_UB_31 0.0369876000 _diffrn_orient_matrix_UB_32 0.0326706000 _diffrn_orient_matrix_UB_33 -0.0141465000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3423 _reflns_number_total 4017 _reflns_odcompleteness_completeness 98.28 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 25.01 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.335 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 4017 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0379 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0302P)^2^+1.1477P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0826 _refine_ls_wR_factor_ref 0.0887 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.10914(19) 0.12327(11) 0.84690(13) 0.0161(4) Uani 1 1 d . . . C2 C 1.2510(2) 0.14194(11) 0.84295(13) 0.0196(4) Uani 1 1 d . . . H2 H 1.2777 0.1448 0.7850 0.024 Uiso 1 1 calc R . . C3 C 1.3533(2) 0.15632(12) 0.92434(14) 0.0230(5) Uani 1 1 d . . . H3 H 1.4477 0.1689 0.9208 0.028 Uiso 1 1 calc R . . C4 C 1.3145(2) 0.15186(12) 1.01021(14) 0.0232(5) Uani 1 1 d . . . H4 H 1.3824 0.1620 1.0648 0.028 Uiso 1 1 calc R . . C5 C 1.1751(2) 0.13245(12) 1.01539(14) 0.0222(5) Uani 1 1 d . . . H5 H 1.1507 0.1290 1.0739 0.027 Uiso 1 1 calc R . . C6 C 1.0689(2) 0.11780(11) 0.93479(13) 0.0175(4) Uani 1 1 d . . . C7 C 0.9217(2) 0.09637(11) 0.94293(13) 0.0185(4) Uani 1 1 d . . . H7 H 0.8537 0.0931 0.8870 0.022 Uiso 1 1 calc R . . C8 C 0.8741(2) 0.08118(12) 1.02020(14) 0.0210(4) Uani 1 1 d . . . H8 H 0.9366 0.0841 1.0784 0.025 Uiso 1 1 calc R . . C9 C 0.7206(2) 0.05952(11) 1.01393(13) 0.0193(4) Uani 1 1 d . . . C10 C 0.6609(2) 0.05540(11) 1.09990(13) 0.0202(4) Uani 1 1 d . . . H10 H 0.5741 0.0289 1.0968 0.024 Uiso 1 1 calc R . . C11 C 0.7242(2) 0.08736(12) 1.18171(13) 0.0202(4) Uani 1 1 d . . . H11 H 0.8140 0.1104 1.1839 0.024 Uiso 1 1 calc R . . C12 C 0.6690(2) 0.09044(12) 1.26850(13) 0.0192(4) Uani 1 1 d . . . C13 C 0.7473(2) 0.13197(12) 1.34504(14) 0.0250(5) Uani 1 1 d . . . H13 H 0.8328 0.1567 1.3394 0.030 Uiso 1 1 calc R . . C14 C 0.7011(2) 0.13723(13) 1.42889(14) 0.0276(5) Uani 1 1 d . . . H14 H 0.7548 0.1653 1.4789 0.033 Uiso 1 1 calc R . . C15 C 0.5744(2) 0.10046(13) 1.43774(14) 0.0268(5) Uani 1 1 d . . . H15 H 0.5426 0.1034 1.4940 0.032 Uiso 1 1 calc R . . C16 C 0.4947(2) 0.05911(12) 1.36253(14) 0.0249(5) Uani 1 1 d . . . H16 H 0.4092 0.0346 1.3687 0.030 Uiso 1 1 calc R . . C17 C 0.5405(2) 0.05378(12) 1.27848(14) 0.0226(5) Uani 1 1 d . . . H17 H 0.4860 0.0258 1.2286 0.027 Uiso 1 1 calc R . . C18 C 0.83276(19) 0.16858(11) 0.73216(12) 0.0159(4) Uani 1 1 d . . . C19 C 0.8549(2) 0.24585(12) 0.76371(12) 0.0192(4) Uani 1 1 d . . . H19 H 0.9479 0.2637 0.7885 0.023 Uiso 1 1 calc R . . C20 C 0.7385(2) 0.29596(12) 0.75814(13) 0.0242(5) Uani 1 1 d . . . H20 H 0.7533 0.3479 0.7780 0.029 Uiso 1 1 calc R . . C21 C 0.5997(2) 0.26902(13) 0.72296(14) 0.0286(5) Uani 1 1 d . . . H21 H 0.5215 0.3027 0.7204 0.034 Uiso 1 1 calc R . . C22 C 0.5769(2) 0.19266(14) 0.69183(15) 0.0306(5) Uani 1 1 d . . . H22 H 0.4836 0.1749 0.6678 0.037 Uiso 1 1 calc R . . C23 C 0.6931(2) 0.14258(13) 0.69641(13) 0.0239(5) Uani 1 1 d . . . H23 H 0.6778 0.0910 0.6754 0.029 Uiso 1 1 calc R . . C24 C 1.07039(19) 0.12585(11) 0.64397(12) 0.0172(4) Uani 1 1 d . . . C25 C 1.1108(2) 0.06678(13) 0.58902(13) 0.0239(5) Uani 1 1 d . . . H25 H 1.0900 0.0146 0.6002 0.029 Uiso 1 1 calc R . . C26 C 1.1819(2) 0.08481(14) 0.51777(14) 0.0299(5) Uani 1 1 d . . . H26 H 1.2088 0.0448 0.4812 0.036 Uiso 1 1 calc R . . C27 C 1.2131(2) 0.16218(14) 0.50084(14) 0.0282(5) Uani 1 1 d . . . H27 H 1.2609 0.1743 0.4529 0.034 Uiso 1 1 calc R . . C28 C 1.1734(2) 0.22161(13) 0.55496(14) 0.0262(5) Uani 1 1 d . . . H28 H 1.1946 0.2737 0.5434 0.031 Uiso 1 1 calc R . . C29 C 1.1022(2) 0.20392(12) 0.62643(13) 0.0225(5) Uani 1 1 d . . . H29 H 1.0756 0.2441 0.6628 0.027 Uiso 1 1 calc R . . O1 O 0.64285(14) 0.04570(9) 0.93753(9) 0.0263(3) Uani 1 1 d . . . P1 P 0.98139(5) 0.09946(3) 0.73890(3) 0.01550(13) Uani 1 1 d . . . S1 S 0.91673(5) -0.01016(3) 0.73171(3) 0.02135(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0152(10) 0.0111(10) 0.0211(10) 0.0003(8) 0.0015(7) 0.0004(8) C2 0.0173(10) 0.0192(11) 0.0230(10) 0.0003(9) 0.0060(8) 0.0019(8) C3 0.0129(10) 0.0235(11) 0.0312(11) 0.0005(9) 0.0008(8) -0.0010(8) C4 0.0181(10) 0.0244(11) 0.0234(11) -0.0025(9) -0.0043(8) -0.0008(9) C5 0.0210(11) 0.0249(12) 0.0199(10) -0.0007(9) 0.0027(8) -0.0007(9) C6 0.0167(10) 0.0150(10) 0.0199(10) -0.0010(8) 0.0021(8) 0.0009(8) C7 0.0167(10) 0.0199(11) 0.0176(10) -0.0001(9) 0.0003(8) 0.0018(8) C8 0.0192(10) 0.0225(11) 0.0205(10) -0.0010(9) 0.0020(8) -0.0003(9) C9 0.0209(10) 0.0143(10) 0.0219(11) 0.0000(9) 0.0023(8) 0.0016(8) C10 0.0156(10) 0.0186(11) 0.0266(11) 0.0019(9) 0.0048(8) -0.0007(8) C11 0.0162(10) 0.0173(10) 0.0271(11) 0.0015(9) 0.0046(8) -0.0016(8) C12 0.0181(10) 0.0172(11) 0.0224(10) 0.0017(9) 0.0045(8) 0.0031(8) C13 0.0211(11) 0.0244(12) 0.0294(12) -0.0020(10) 0.0051(9) -0.0050(9) C14 0.0293(12) 0.0273(12) 0.0253(11) -0.0058(10) 0.0037(9) -0.0032(10) C15 0.0324(12) 0.0272(12) 0.0231(11) 0.0003(10) 0.0106(9) 0.0016(10) C16 0.0232(11) 0.0230(12) 0.0309(11) 0.0017(10) 0.0113(9) -0.0018(9) C17 0.0217(10) 0.0201(11) 0.0248(11) -0.0010(9) 0.0022(8) -0.0009(9) C18 0.0171(10) 0.0185(11) 0.0121(9) 0.0016(8) 0.0033(7) 0.0028(8) C19 0.0189(10) 0.0221(11) 0.0164(10) 0.0004(9) 0.0033(8) 0.0024(8) C20 0.0317(12) 0.0202(11) 0.0215(10) 0.0007(9) 0.0075(9) 0.0073(9) C21 0.0246(11) 0.0342(13) 0.0273(11) 0.0052(10) 0.0062(9) 0.0149(10) C22 0.0158(10) 0.0408(14) 0.0329(12) 0.0017(11) 0.0000(9) 0.0034(10) C23 0.0211(11) 0.0251(12) 0.0239(11) -0.0027(9) 0.0011(8) -0.0011(9) C24 0.0158(10) 0.0192(11) 0.0158(9) -0.0001(8) 0.0014(7) 0.0026(8) C25 0.0243(11) 0.0228(12) 0.0245(11) -0.0036(9) 0.0048(8) 0.0002(9) C26 0.0341(13) 0.0331(13) 0.0247(11) -0.0077(10) 0.0114(9) 0.0021(10) C27 0.0270(11) 0.0397(14) 0.0198(11) 0.0015(10) 0.0096(9) 0.0018(10) C28 0.0253(11) 0.0261(12) 0.0280(11) 0.0054(10) 0.0076(9) 0.0021(9) C29 0.0244(11) 0.0220(11) 0.0229(11) -0.0010(9) 0.0090(8) 0.0035(9) O1 0.0214(8) 0.0337(9) 0.0230(8) -0.0015(7) 0.0025(6) -0.0045(7) P1 0.0144(2) 0.0149(3) 0.0167(3) -0.0009(2) 0.00203(19) 0.0001(2) S1 0.0214(3) 0.0157(3) 0.0256(3) -0.0011(2) 0.0018(2) -0.0026(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.392(3) . ? C1 C6 1.411(3) . ? C1 P1 1.8214(18) . ? C2 H2 0.9300 . ? C2 C3 1.389(3) . ? C3 H3 0.9300 . ? C3 C4 1.376(3) . ? C4 H4 0.9300 . ? C4 C5 1.376(3) . ? C5 H5 0.9300 . ? C5 C6 1.402(3) . ? C6 C7 1.468(3) . ? C7 H7 0.9300 . ? C7 C8 1.321(3) . ? C8 H8 0.9300 . ? C8 C9 1.482(3) . ? C9 C10 1.477(3) . ? C9 O1 1.224(2) . ? C10 H10 0.9300 . ? C10 C11 1.334(3) . ? C11 H11 0.9300 . ? C11 C12 1.465(3) . ? C12 C13 1.397(3) . ? C12 C17 1.399(3) . ? C13 H13 0.9300 . ? C13 C14 1.382(3) . ? C14 H14 0.9300 . ? C14 C15 1.381(3) . ? C15 H15 0.9300 . ? C15 C16 1.387(3) . ? C16 H16 0.9300 . ? C16 C17 1.383(3) . ? C17 H17 0.9300 . ? C18 C19 1.393(3) . ? C18 C23 1.389(3) . ? C18 P1 1.8194(19) . ? C19 H19 0.9300 . ? C19 C20 1.382(3) . ? C20 H20 0.9300 . ? C20 C21 1.385(3) . ? C21 H21 0.9300 . ? C21 C22 1.377(3) . ? C22 H22 0.9300 . ? C22 C23 1.382(3) . ? C23 H23 0.9300 . ? C24 C25 1.386(3) . ? C24 C29 1.396(3) . ? C24 P1 1.8164(19) . ? C25 H25 0.9300 . ? C25 C26 1.382(3) . ? C26 H26 0.9300 . ? C26 C27 1.381(3) . ? C27 H27 0.9300 . ? C27 C28 1.380(3) . ? C28 H28 0.9300 . ? C28 C29 1.384(3) . ? C29 H29 0.9300 . ? P1 S1 1.9573(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.64(16) . . ? C2 C1 P1 119.30(14) . . ? C6 C1 P1 120.92(14) . . ? C1 C2 H2 119.6 . . ? C3 C2 C1 120.90(18) . . ? C3 C2 H2 119.6 . . ? C2 C3 H3 120.1 . . ? C4 C3 C2 119.76(18) . . ? C4 C3 H3 120.1 . . ? C3 C4 H4 120.0 . . ? C5 C4 C3 120.06(18) . . ? C5 C4 H4 120.0 . . ? C4 C5 H5 119.1 . . ? C4 C5 C6 121.77(18) . . ? C6 C5 H5 119.1 . . ? C1 C6 C7 121.79(16) . . ? C5 C6 C1 117.87(17) . . ? C5 C6 C7 120.33(17) . . ? C6 C7 H7 116.1 . . ? C8 C7 C6 127.78(17) . . ? C8 C7 H7 116.1 . . ? C7 C8 H8 120.1 . . ? C7 C8 C9 119.81(17) . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 119.96(16) . . ? O1 C9 C8 120.11(17) . . ? O1 C9 C10 119.92(18) . . ? C9 C10 H10 118.0 . . ? C11 C10 C9 123.94(18) . . ? C11 C10 H10 118.0 . . ? C10 C11 H11 116.2 . . ? C10 C11 C12 127.67(18) . . ? C12 C11 H11 116.2 . . ? C13 C12 C11 118.80(18) . . ? C13 C12 C17 118.16(18) . . ? C17 C12 C11 123.03(18) . . ? C12 C13 H13 119.2 . . ? C14 C13 C12 121.69(19) . . ? C14 C13 H13 119.2 . . ? C13 C14 H14 120.3 . . ? C15 C14 C13 119.44(19) . . ? C15 C14 H14 120.3 . . ? C14 C15 H15 120.1 . . ? C14 C15 C16 119.81(19) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 119.5 . . ? C17 C16 C15 120.93(19) . . ? C17 C16 H16 119.5 . . ? C12 C17 H17 120.0 . . ? C16 C17 C12 119.97(19) . . ? C16 C17 H17 120.0 . . ? C19 C18 P1 121.91(14) . . ? C23 C18 C19 119.40(18) . . ? C23 C18 P1 118.67(15) . . ? C18 C19 H19 120.1 . . ? C20 C19 C18 119.84(18) . . ? C20 C19 H19 120.1 . . ? C19 C20 H20 119.9 . . ? C19 C20 C21 120.1(2) . . ? C21 C20 H20 119.9 . . ? C20 C21 H21 119.8 . . ? C22 C21 C20 120.38(19) . . ? C22 C21 H21 119.8 . . ? C21 C22 H22 120.2 . . ? C21 C22 C23 119.7(2) . . ? C23 C22 H22 120.2 . . ? C18 C23 H23 119.7 . . ? C22 C23 C18 120.6(2) . . ? C22 C23 H23 119.7 . . ? C25 C24 C29 119.16(18) . . ? C25 C24 P1 119.13(15) . . ? C29 C24 P1 121.69(14) . . ? C24 C25 H25 119.7 . . ? C26 C25 C24 120.5(2) . . ? C26 C25 H25 119.7 . . ? C25 C26 H26 120.0 . . ? C27 C26 C25 120.0(2) . . ? C27 C26 H26 120.0 . . ? C26 C27 H27 119.9 . . ? C28 C27 C26 120.14(19) . . ? C28 C27 H27 119.9 . . ? C27 C28 H28 119.9 . . ? C27 C28 C29 120.1(2) . . ? C29 C28 H28 119.9 . . ? C24 C29 H29 120.0 . . ? C28 C29 C24 120.06(19) . . ? C28 C29 H29 120.0 . . ? C1 P1 S1 113.72(6) . . ? C18 P1 C1 105.75(8) . . ? C18 P1 S1 112.47(7) . . ? C24 P1 C1 105.87(8) . . ? C24 P1 C18 105.87(8) . . ? C24 P1 S1 112.52(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 0.2(3) . . . . ? C1 C6 C7 C8 172.2(2) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? C2 C1 C6 C7 -178.44(18) . . . . ? C2 C1 P1 C18 -123.14(16) . . . . ? C2 C1 P1 C24 -11.09(18) . . . . ? C2 C1 P1 S1 112.95(15) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C4 C5 C6 C7 179.31(19) . . . . ? C5 C6 C7 C8 -6.8(3) . . . . ? C6 C1 C2 C3 -0.9(3) . . . . ? C6 C1 P1 C18 61.23(17) . . . . ? C6 C1 P1 C24 173.28(15) . . . . ? C6 C1 P1 S1 -62.68(17) . . . . ? C6 C7 C8 C9 -179.30(19) . . . . ? C7 C8 C9 C10 -169.85(19) . . . . ? C7 C8 C9 O1 9.5(3) . . . . ? C8 C9 C10 C11 16.5(3) . . . . ? C9 C10 C11 C12 175.88(19) . . . . ? C10 C11 C12 C13 -175.3(2) . . . . ? C10 C11 C12 C17 4.5(3) . . . . ? C11 C12 C13 C14 179.92(19) . . . . ? C11 C12 C17 C16 -179.98(19) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? C13 C12 C17 C16 -0.2(3) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C15 C16 C17 C12 0.0(3) . . . . ? C17 C12 C13 C14 0.1(3) . . . . ? C18 C19 C20 C21 1.2(3) . . . . ? C19 C18 C23 C22 0.1(3) . . . . ? C19 C18 P1 C1 35.38(17) . . . . ? C19 C18 P1 C24 -76.67(16) . . . . ? C19 C18 P1 S1 160.07(13) . . . . ? C19 C20 C21 C22 -1.1(3) . . . . ? C20 C21 C22 C23 0.5(3) . . . . ? C21 C22 C23 C18 0.0(3) . . . . ? C23 C18 C19 C20 -0.8(3) . . . . ? C23 C18 P1 C1 -143.13(15) . . . . ? C23 C18 P1 C24 104.82(16) . . . . ? C23 C18 P1 S1 -18.44(16) . . . . ? C24 C25 C26 C27 0.0(3) . . . . ? C25 C24 C29 C28 0.0(3) . . . . ? C25 C24 P1 C1 111.92(16) . . . . ? C25 C24 P1 C18 -136.11(15) . . . . ? C25 C24 P1 S1 -12.88(17) . . . . ? C25 C26 C27 C28 0.0(3) . . . . ? C26 C27 C28 C29 0.0(3) . . . . ? C27 C28 C29 C24 0.0(3) . . . . ? C29 C24 C25 C26 0.1(3) . . . . ? C29 C24 P1 C1 -66.48(17) . . . . ? C29 C24 P1 C18 45.49(17) . . . . ? C29 C24 P1 S1 168.73(14) . . . . ? O1 C9 C10 C11 -162.9(2) . . . . ? P1 C1 C2 C3 -176.56(15) . . . . ? P1 C1 C6 C5 176.27(15) . . . . ? P1 C1 C6 C7 -2.8(3) . . . . ? P1 C18 C19 C20 -179.25(14) . . . . ? P1 C18 C23 C22 178.66(15) . . . . ? P1 C24 C25 C26 -178.38(15) . . . . ? P1 C24 C29 C28 178.36(15) . . . . ? ### END data_ijf1028 _database_code_depnum_ccdc_archive 'CCDC 874850' #TrackingRef '- all.cif' _audit_creation_method 'WinGX routine CIF_UPDATE' __chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4904(3) _cell_length_b 17.0028(5) _cell_length_c 14.5622(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.951(3) _cell_angle_gamma 90.00 _cell_volume 2298.89(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3828 _cell_measurement_temperature 110.0 _cell_measurement_theta_max 24.9623 _cell_measurement_theta_min 3.0910 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.99548 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_unetI/netI 0.0410 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7096 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 3.10 _diffrn_ambient_temperature 110.0 _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 28.00 73.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 16.2440 65.0000 176.0000 45 #__ type_ start__ end____ width___ exp.time_ 2 omega -38.00 89.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 16.2440 0.0000 0.0000 127 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0725600000 _diffrn_orient_matrix_UB_12 0.0100459000 _diffrn_orient_matrix_UB_13 -0.0195658000 _diffrn_orient_matrix_UB_21 0.0027090000 _diffrn_orient_matrix_UB_22 0.0297711000 _diffrn_orient_matrix_UB_23 0.0344534000 _diffrn_orient_matrix_UB_31 0.0238644000 _diffrn_orient_matrix_UB_32 0.0274223000 _diffrn_orient_matrix_UB_33 -0.0301577000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3425 _reflns_number_total 4020 _reflns_odcompleteness_completeness 98.09 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 25.01 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.332 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 4020 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0377 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+1.3200P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0836 _refine_ls_wR_factor_ref 0.0890 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C0AA C 0.6109(2) 0.06685(12) 0.58905(14) 0.0241(5) Uani 1 1 d . . . H0A H 0.5896 0.0136 0.6004 0.029 Uiso 1 1 calc R . . C1 C 0.6092(2) 0.12321(11) 0.84680(13) 0.0170(4) Uani 1 1 d . . . C2 C 0.7511(2) 0.14194(11) 0.84308(14) 0.0198(4) Uani 1 1 d . . . H2 H 0.7781 0.1448 0.7839 0.024 Uiso 1 1 calc R . . C3 C 0.8534(2) 0.15645(12) 0.92435(14) 0.0234(5) Uani 1 1 d . . . H3 H 0.9495 0.1695 0.9208 0.028 Uiso 1 1 calc R . . C4 C 0.8144(2) 0.15176(12) 1.01017(14) 0.0232(5) Uani 1 1 d . . . H4 H 0.8837 0.1618 1.0660 0.028 Uiso 1 1 calc R . . C5 C 0.6751(2) 0.13256(12) 1.01543(14) 0.0221(5) Uani 1 1 d . . . H5 H 0.6505 0.1292 1.0753 0.026 Uiso 1 1 calc R . . C6 C 0.5688(2) 0.11783(11) 0.93500(13) 0.0177(4) Uani 1 1 d . . . C7 C 0.4215(2) 0.09655(11) 0.94291(13) 0.0188(4) Uani 1 1 d . . . H7 H 0.3522 0.0935 0.8857 0.023 Uiso 1 1 calc R . . C8 C 0.3740(2) 0.08117(12) 1.02054(14) 0.0211(4) Uani 1 1 d . . . H8 H 0.4377 0.0839 1.0801 0.025 Uiso 1 1 calc R . . C9 C 0.2205(2) 0.05960(11) 1.01384(14) 0.0196(4) Uani 1 1 d . . . C10 C 0.1610(2) 0.05534(11) 1.09962(13) 0.0203(4) Uani 1 1 d . . . H10 H 0.0726 0.0282 1.0963 0.024 Uiso 1 1 calc R . . C11 C 0.2241(2) 0.08738(11) 1.18175(14) 0.0211(4) Uani 1 1 d . . . H11 H 0.3156 0.1109 1.1841 0.025 Uiso 1 1 calc R . . C12 C 0.1688(2) 0.09048(12) 1.26854(13) 0.0198(4) Uani 1 1 d . . . C13 C 0.2476(2) 0.13207(12) 1.34495(14) 0.0248(5) Uani 1 1 d . . . H13 H 0.3347 0.1573 1.3393 0.030 Uiso 1 1 calc R . . C14 C 0.2009(2) 0.13711(13) 1.42889(14) 0.0278(5) Uani 1 1 d . . . H14 H 0.2557 0.1656 1.4802 0.033 Uiso 1 1 calc R . . C15 C 0.0737(2) 0.10033(12) 1.43756(14) 0.0264(5) Uani 1 1 d . . . H15 H 0.0410 0.1035 1.4949 0.032 Uiso 1 1 calc R . . C16 C -0.0051(2) 0.05915(12) 1.36261(14) 0.0253(5) Uani 1 1 d . . . H16 H -0.0920 0.0340 1.3688 0.030 Uiso 1 1 calc R . . C17 C 0.0406(2) 0.05382(12) 1.27837(14) 0.0218(5) Uani 1 1 d . . . H17 H -0.0150 0.0253 1.2274 0.026 Uiso 1 1 calc R . . C18 C 0.3330(2) 0.16866(11) 0.73198(12) 0.0163(4) Uani 1 1 d . . . C19 C 0.3553(2) 0.24592(11) 0.76385(12) 0.0186(4) Uani 1 1 d . . . H19 H 0.4499 0.2642 0.7893 0.022 Uiso 1 1 calc R . . C20 C 0.2385(2) 0.29571(13) 0.75811(13) 0.0250(5) Uani 1 1 d . . . H20 H 0.2535 0.3487 0.7785 0.030 Uiso 1 1 calc R . . C21 C 0.0997(2) 0.26909(13) 0.72292(14) 0.0277(5) Uani 1 1 d . . . H21 H 0.0203 0.3036 0.7203 0.033 Uiso 1 1 calc R . . C22 C 0.0768(2) 0.19257(14) 0.69173(15) 0.0296(5) Uani 1 1 d . . . H22 H -0.0182 0.1743 0.6673 0.036 Uiso 1 1 calc R . . C23 C 0.1932(2) 0.14262(13) 0.69640(14) 0.0239(5) Uani 1 1 d . . . H23 H 0.1776 0.0899 0.6751 0.029 Uiso 1 1 calc R . . C24 C 0.57073(19) 0.12586(11) 0.64400(13) 0.0173(4) Uani 1 1 d . . . C25 C 0.6022(2) 0.20408(12) 0.62667(13) 0.0219(5) Uani 1 1 d . . . H25 H 0.5754 0.2451 0.6640 0.026 Uiso 1 1 calc R . . C26 C 0.6730(2) 0.22168(13) 0.55471(14) 0.0271(5) Uani 1 1 d . . . H26 H 0.6940 0.2748 0.5425 0.033 Uiso 1 1 calc R . . C27 C 0.7129(2) 0.16196(13) 0.50067(14) 0.0280(5) Uani 1 1 d . . . H27 H 0.7617 0.1742 0.4517 0.034 Uiso 1 1 calc R . . C29 C 0.6819(2) 0.08484(14) 0.51774(15) 0.0299(5) Uani 1 1 d . . . H29 H 0.7093 0.0440 0.4805 0.036 Uiso 1 1 calc R . . O1 O 0.14255(15) 0.04578(9) 0.93751(9) 0.0264(3) Uani 1 1 d . . . P3 P 0.48140(5) 0.09947(3) 0.73887(3) 0.01549(13) Uani 1 1 d . . . S1 S 0.41668(5) -0.01019(3) 0.73168(3) 0.02143(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C0AA 0.0271(12) 0.0212(11) 0.0237(11) -0.0045(9) 0.0050(9) -0.0006(9) C1 0.0176(10) 0.0113(9) 0.0209(10) 0.0006(8) 0.0011(8) 0.0007(8) C2 0.0183(10) 0.0188(10) 0.0228(10) -0.0006(9) 0.0055(8) 0.0009(8) C3 0.0151(10) 0.0208(11) 0.0329(12) -0.0018(9) 0.0016(8) -0.0017(9) C4 0.0185(11) 0.0233(11) 0.0237(11) -0.0026(9) -0.0051(8) -0.0016(9) C5 0.0228(11) 0.0232(11) 0.0195(10) -0.0003(9) 0.0026(8) 0.0002(9) C6 0.0166(10) 0.0154(10) 0.0207(10) -0.0005(8) 0.0029(8) 0.0017(8) C7 0.0160(10) 0.0188(10) 0.0199(10) 0.0003(9) -0.0003(8) 0.0014(8) C8 0.0208(11) 0.0231(11) 0.0187(10) -0.0021(9) 0.0025(8) -0.0012(9) C9 0.0196(10) 0.0150(10) 0.0234(11) 0.0014(9) 0.0025(8) 0.0009(8) C10 0.0166(10) 0.0188(10) 0.0252(11) 0.0015(9) 0.0035(8) -0.0009(8) C11 0.0164(10) 0.0175(10) 0.0295(11) 0.0020(9) 0.0049(8) -0.0011(8) C12 0.0199(10) 0.0177(10) 0.0219(10) 0.0018(9) 0.0044(8) 0.0034(8) C13 0.0197(11) 0.0238(11) 0.0309(12) -0.0025(10) 0.0050(9) -0.0036(9) C14 0.0314(12) 0.0271(12) 0.0242(11) -0.0050(10) 0.0039(9) -0.0032(10) C15 0.0318(12) 0.0259(12) 0.0236(11) 0.0009(10) 0.0105(9) 0.0006(10) C16 0.0242(11) 0.0239(11) 0.0299(12) 0.0012(10) 0.0108(9) -0.0030(9) C17 0.0215(11) 0.0194(11) 0.0233(11) -0.0023(9) 0.0019(8) -0.0030(9) C18 0.0178(10) 0.0181(10) 0.0127(9) 0.0017(8) 0.0027(7) 0.0028(8) C19 0.0189(10) 0.0210(11) 0.0158(9) 0.0006(8) 0.0035(8) 0.0012(8) C20 0.0324(12) 0.0225(11) 0.0211(10) 0.0014(9) 0.0081(9) 0.0079(10) C21 0.0238(12) 0.0346(13) 0.0253(11) 0.0050(10) 0.0068(9) 0.0129(10) C22 0.0148(11) 0.0400(14) 0.0319(12) 0.0008(11) -0.0003(9) 0.0029(10) C23 0.0210(11) 0.0242(11) 0.0249(11) -0.0013(9) 0.0009(8) -0.0011(9) C24 0.0143(10) 0.0196(10) 0.0171(9) -0.0008(9) 0.0010(7) 0.0020(8) C25 0.0244(11) 0.0211(11) 0.0212(10) 0.0007(9) 0.0069(8) 0.0039(9) C26 0.0273(12) 0.0257(12) 0.0291(12) 0.0055(10) 0.0075(9) 0.0008(10) C27 0.0266(12) 0.0393(14) 0.0197(11) 0.0008(10) 0.0087(9) 0.0024(10) C29 0.0351(13) 0.0320(13) 0.0249(11) -0.0081(10) 0.0114(10) 0.0025(11) O1 0.0217(8) 0.0340(9) 0.0223(8) -0.0004(7) 0.0017(6) -0.0034(7) P3 0.0148(3) 0.0142(3) 0.0168(3) -0.0006(2) 0.00195(19) 0.0000(2) S1 0.0220(3) 0.0156(3) 0.0254(3) -0.0008(2) 0.0018(2) -0.0031(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C0AA H0A 0.9500 . ? C0AA C24 1.385(3) . ? C0AA C29 1.384(3) . ? C1 C2 1.396(3) . ? C1 C6 1.417(3) . ? C1 P3 1.8205(19) . ? C2 H2 0.9500 . ? C2 C3 1.389(3) . ? C3 H3 0.9500 . ? C3 C4 1.377(3) . ? C4 H4 0.9500 . ? C4 C5 1.379(3) . ? C5 H5 0.9500 . ? C5 C6 1.401(3) . ? C6 C7 1.472(3) . ? C7 H7 0.9500 . ? C7 C8 1.327(3) . ? C8 H8 0.9500 . ? C8 C9 1.485(3) . ? C9 C10 1.476(3) . ? C9 O1 1.224(2) . ? C10 H10 0.9500 . ? C10 C11 1.338(3) . ? C11 H11 0.9500 . ? C11 C12 1.466(3) . ? C12 C13 1.397(3) . ? C12 C17 1.401(3) . ? C13 H13 0.9500 . ? C13 C14 1.386(3) . ? C14 H14 0.9500 . ? C14 C15 1.388(3) . ? C15 H15 0.9500 . ? C15 C16 1.379(3) . ? C16 H16 0.9500 . ? C16 C17 1.386(3) . ? C17 H17 0.9500 . ? C18 C19 1.395(3) . ? C18 C23 1.393(3) . ? C18 P3 1.8218(19) . ? C19 H19 0.9500 . ? C19 C20 1.384(3) . ? C20 H20 0.9500 . ? C20 C21 1.387(3) . ? C21 H21 0.9500 . ? C21 C22 1.380(3) . ? C22 H22 0.9500 . ? C22 C23 1.384(3) . ? C23 H23 0.9500 . ? C24 C25 1.398(3) . ? C24 P3 1.8203(19) . ? C25 H25 0.9500 . ? C25 C26 1.389(3) . ? C26 H26 0.9500 . ? C26 C27 1.385(3) . ? C27 H27 0.9500 . ? C27 C29 1.377(3) . ? C29 H29 0.9500 . ? P3 S1 1.9590(7) . ? 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 C24 C0AA H0A 119.7 . . ? C29 C0AA H0A 119.7 . . ? C29 C0AA C24 120.6(2) . . ? C2 C1 C6 119.59(17) . . ? C2 C1 P3 119.51(14) . . ? C6 C1 P3 120.78(14) . . ? C1 C2 H2 119.4 . . ? C3 C2 C1 121.17(18) . . ? C3 C2 H2 119.4 . . ? C2 C3 H3 120.3 . . ? C4 C3 C2 119.39(19) . . ? C4 C3 H3 120.3 . . ? C3 C4 H4 119.8 . . ? C3 C4 C5 120.34(18) . . ? C5 C4 H4 119.8 . . ? C4 C5 H5 119.1 . . ? C4 C5 C6 121.88(18) . . ? C6 C5 H5 119.1 . . ? C1 C6 C7 121.74(17) . . ? C5 C6 C1 117.62(17) . . ? C5 C6 C7 120.63(17) . . ? C6 C7 H7 116.2 . . ? C8 C7 C6 127.66(18) . . ? C8 C7 H7 116.2 . . ? C7 C8 H8 120.2 . . ? C7 C8 C9 119.61(18) . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 119.91(17) . . ? O1 C9 C8 120.48(18) . . ? O1 C9 C10 119.60(18) . . ? C9 C10 H10 118.0 . . ? C11 C10 C9 123.91(18) . . ? C11 C10 H10 118.0 . . ? C10 C11 H11 116.2 . . ? C10 C11 C12 127.70(19) . . ? C12 C11 H11 116.2 . . ? C13 C12 C11 118.48(18) . . ? C13 C12 C17 118.46(18) . . ? C17 C12 C11 123.07(18) . . ? C12 C13 H13 119.4 . . ? C14 C13 C12 121.17(19) . . ? C14 C13 H13 119.4 . . ? C13 C14 H14 120.2 . . ? C13 C14 C15 119.66(19) . . ? C15 C14 H14 120.2 . . ? C14 C15 H15 120.1 . . ? C16 C15 C14 119.72(19) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 119.5 . . ? C15 C16 C17 121.07(19) . . ? C17 C16 H16 119.5 . . ? C12 C17 H17 120.0 . . ? C16 C17 C12 119.92(19) . . ? C16 C17 H17 120.0 . . ? C19 C18 P3 121.84(14) . . ? C23 C18 C19 119.38(18) . . ? C23 C18 P3 118.76(15) . . ? C18 C19 H19 120.3 . . ? C20 C19 C18 119.45(18) . . ? C20 C19 H19 120.3 . . ? C19 C20 H20 119.7 . . ? C19 C20 C21 120.7(2) . . ? C21 C20 H20 119.7 . . ? C20 C21 H21 119.9 . . ? C22 C21 C20 120.2(2) . . ? C22 C21 H21 119.9 . . ? C21 C22 H22 120.3 . . ? C21 C22 C23 119.5(2) . . ? C23 C22 H22 120.3 . . ? C18 C23 H23 119.6 . . ? C22 C23 C18 120.8(2) . . ? C22 C23 H23 119.6 . . ? C0AA C24 C25 119.34(18) . . ? C0AA C24 P3 119.15(15) . . ? C25 C24 P3 121.49(15) . . ? C24 C25 H25 120.1 . . ? C26 C25 C24 119.75(19) . . ? C26 C25 H25 120.1 . . ? C25 C26 H26 119.9 . . ? C27 C26 C25 120.2(2) . . ? C27 C26 H26 119.9 . . ? C26 C27 H27 119.9 . . ? C29 C27 C26 120.12(19) . . ? C29 C27 H27 119.9 . . ? C0AA C29 H29 120.0 . . ? C27 C29 C0AA 120.1(2) . . ? C27 C29 H29 120.0 . . ? C1 P3 C18 105.87(9) . . ? C1 P3 S1 113.74(6) . . ? C18 P3 S1 112.42(7) . . ? C24 P3 C1 105.61(9) . . ? C24 P3 C18 105.97(8) . . ? C24 P3 S1 112.59(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C0AA C24 C25 C26 0.1(3) . . . . ? C0AA C24 P3 C1 111.95(16) . . . . ? C0AA C24 P3 C18 -136.01(16) . . . . ? C0AA C24 P3 S1 -12.73(17) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C1 C6 C7 C8 172.0(2) . . . . ? C2 C1 C6 C5 0.6(3) . . . . ? C2 C1 C6 C7 -178.61(18) . . . . ? C2 C1 P3 C18 -123.09(16) . . . . ? C2 C1 P3 C24 -10.98(18) . . . . ? C2 C1 P3 S1 112.99(15) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C4 C5 C6 C7 179.27(19) . . . . ? C5 C6 C7 C8 -7.2(3) . . . . ? C6 C1 C2 C3 -0.9(3) . . . . ? C6 C1 P3 C18 61.13(17) . . . . ? C6 C1 P3 C24 173.24(15) . . . . ? C6 C1 P3 S1 -62.80(17) . . . . ? C6 C7 C8 C9 -179.20(18) . . . . ? C7 C8 C9 C10 -169.83(19) . . . . ? C7 C8 C9 O1 9.7(3) . . . . ? C8 C9 C10 C11 16.7(3) . . . . ? C9 C10 C11 C12 175.77(18) . . . . ? C10 C11 C12 C13 -175.3(2) . . . . ? C10 C11 C12 C17 4.5(3) . . . . ? C11 C12 C13 C14 -179.99(19) . . . . ? C11 C12 C17 C16 179.93(19) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C13 C12 C17 C16 -0.2(3) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C14 C15 C16 C17 0.0(3) . . . . ? C15 C16 C17 C12 0.2(3) . . . . ? C17 C12 C13 C14 0.1(3) . . . . ? C18 C19 C20 C21 1.4(3) . . . . ? C19 C18 C23 C22 0.5(3) . . . . ? C19 C18 P3 C1 35.12(17) . . . . ? C19 C18 P3 C24 -76.74(17) . . . . ? C19 C18 P3 S1 159.87(13) . . . . ? C19 C20 C21 C22 -1.0(3) . . . . ? C20 C21 C22 C23 0.4(3) . . . . ? C21 C22 C23 C18 -0.1(3) . . . . ? C23 C18 C19 C20 -1.1(3) . . . . ? C23 C18 P3 C1 -142.94(15) . . . . ? C23 C18 P3 C24 105.20(16) . . . . ? C23 C18 P3 S1 -18.19(17) . . . . ? C24 C0AA C29 C27 -0.2(3) . . . . ? C24 C25 C26 C27 -0.4(3) . . . . ? C25 C24 P3 C1 -66.70(18) . . . . ? C25 C24 P3 C18 45.33(18) . . . . ? C25 C24 P3 S1 168.62(14) . . . . ? C25 C26 C27 C29 0.3(3) . . . . ? C26 C27 C29 C0AA -0.1(3) . . . . ? C29 C0AA C24 C25 0.1(3) . . . . ? C29 C0AA C24 P3 -178.55(16) . . . . ? O1 C9 C10 C11 -162.8(2) . . . . ? P3 C1 C2 C3 -176.69(15) . . . . ? P3 C1 C6 C5 176.37(15) . . . . ? P3 C1 C6 C7 -2.8(3) . . . . ? P3 C18 C19 C20 -179.12(14) . . . . ? P3 C18 C23 C22 178.57(15) . . . . ? P3 C24 C25 C26 178.78(15) . . . . ? ### END data_ijf1029 _database_code_depnum_ccdc_archive 'CCDC 874851' #TrackingRef '- all.cif' _audit_creation_method 'WinGX routine CIF_UPDATE' __chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3365(5) _cell_length_b 17.1396(6) _cell_length_c 14.7354(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.311(8) _cell_angle_gamma 90.00 _cell_volume 2303.8(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1670 _cell_measurement_temperature 110.0 _cell_measurement_theta_max 27.7628 _cell_measurement_theta_min 3.2569 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_preparation ? _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.88844 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_unetI/netI 0.0627 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4050 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 27.81 _diffrn_reflns_theta_min 3.26 _diffrn_ambient_temperature 110.0 _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.756 _diffrn_measured_fraction_theta_max 0.556 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -80.00 11.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -14.9940 -77.0000 120.0000 91 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0740166000 _diffrn_orient_matrix_UB_12 0.0123562000 _diffrn_orient_matrix_UB_13 -0.0131092000 _diffrn_orient_matrix_UB_21 0.0052972000 _diffrn_orient_matrix_UB_22 0.0173376000 _diffrn_orient_matrix_UB_23 0.0443671000 _diffrn_orient_matrix_UB_31 0.0231530000 _diffrn_orient_matrix_UB_32 0.0354757000 _diffrn_orient_matrix_UB_33 -0.0171698000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2330 _reflns_number_total 3037 _reflns_odcompleteness_completeness 65.33 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 25.01 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.403 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 344 _refine_ls_number_reflns 3037 _refine_ls_number_restraints 63 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0639 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+1.9471P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1349 _refine_ls_wR_factor_ref 0.1485 _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. The crystal contained a disordered mixture of the monomer and photo-dimer. The ratio of these compounds refined to 0.340:0.660(4). The ADP of the following pairs of atoms were constrained to be equal: O1 O1A, C1A C1, C2 C2A, C3A C3, C4A C4, C5A C5, C6A C6, C9A C9, C12A C12, C13A C13, C14A C14, C15A C15, C16A C16, C17A C17. The ADP of the following atoms were restrained to be isotropic C1 C1A C6 C6A C7 C7A C8 C8A O1 O1A Rigid bond restraints were applied to C10-C11, C7-C8 & C7A-C8A Two phenyl rings (C12-C17 & C12A-C17A) were constrained to be regular hexagons with a C-C bond length of 1.39 angstroms. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.611(2) 0.1162(12) 0.8511(19) 0.0257(17) Uani 0.340(4) 1 d PU A 1 C1A C 0.6346(10) 0.1115(6) 0.8312(8) 0.0257(17) Uani 0.660(4) 1 d PU A 2 C2 C 0.750(3) 0.1322(14) 0.848(2) 0.027(3) Uani 0.340(4) 1 d P A 1 H2 H 0.7790 0.1328 0.7896 0.033 Uiso 0.340(4) 1 calc PR A 1 C2A C 0.7612(14) 0.1505(6) 0.8198(9) 0.027(3) Uani 0.660(4) 1 d P A 2 H2A H 0.7707 0.1641 0.7589 0.033 Uiso 0.660(4) 1 calc PR A 2 C3 C 0.854(3) 0.1481(14) 0.931(2) 0.046(4) Uani 0.340(4) 1 d P A 1 H3 H 0.9533 0.1601 0.9312 0.056 Uiso 0.340(4) 1 calc PR A 1 C3A C 0.8722(11) 0.1700(6) 0.8935(8) 0.046(4) Uani 0.660(4) 1 d P A 2 H3A H 0.9587 0.1941 0.8828 0.056 Uiso 0.660(4) 1 calc PR A 2 C4 C 0.808(2) 0.1455(18) 1.003(3) 0.052(5) Uani 0.340(4) 1 d P A 1 H4 H 0.8775 0.1577 1.0582 0.062 Uiso 0.340(4) 1 calc PR A 1 C4A C 0.8580(11) 0.1541(8) 0.9857(16) 0.052(5) Uani 0.660(4) 1 d P A 2 H4A H 0.9297 0.1707 1.0380 0.062 Uiso 0.660(4) 1 calc PR A 2 C5 C 0.6686(15) 0.1275(9) 1.0157(19) 0.038(3) Uani 0.340(4) 1 d P A 1 H5 H 0.6443 0.1255 1.0751 0.045 Uiso 0.340(4) 1 calc PR A 1 C5A C 0.7383(8) 0.1147(4) 0.9953(9) 0.038(3) Uani 0.660(4) 1 d P A 2 H5A H 0.7312 0.1017 1.0568 0.045 Uiso 0.660(4) 1 calc PR A 2 C6 C 0.5659(14) 0.1124(6) 0.9317(13) 0.0233(15) Uani 0.340(4) 1 d PU A 1 C6A C 0.6229(7) 0.0906(3) 0.9240(6) 0.0233(15) Uani 0.660(4) 1 d PU A 2 C7 C 0.4063(16) 0.0942(7) 0.9467(13) 0.044(4) Uani 0.340(4) 1 d PU A 1 H7 H 0.3282 0.0994 0.8940 0.052 Uiso 0.340(4) 1 calc PR A 1 C7A C 0.5004(6) 0.0406(3) 0.9419(5) 0.0225(17) Uani 0.660(4) 1 d PU . 2 H7A H 0.4119 0.0452 0.8903 0.027 Uiso 0.660(4) 1 calc PR A 2 C8 C 0.371(3) 0.0732(13) 1.023(2) 0.061(6) Uani 0.340(4) 1 d PU A 1 H8 H 0.4417 0.0685 1.0798 0.073 Uiso 0.340(4) 1 calc PR A 1 C8A C 0.4595(8) 0.0475(3) 1.0352(6) 0.0309(18) Uani 0.660(4) 1 d PU . 2 H8A H 0.5286 0.0830 1.0772 0.037 Uiso 0.660(4) 1 calc PR A 2 C9 C 0.215(2) 0.0569(9) 1.016(2) 0.041(3) Uani 0.340(4) 1 d P A 1 C9A C 0.3034(12) 0.0687(5) 1.0340(9) 0.041(3) Uani 0.660(4) 1 d P A 2 C10 C 0.162(2) 0.0548(9) 1.0919(17) 0.035(9) Uani 0.340(4) 1 d PU A 1 H10A H 0.0734 0.0263 1.0866 0.042 Uiso 0.340(4) 1 calc PR A 1 C10A C 0.2728(9) 0.0865(4) 1.1321(9) 0.041(4) Uani 0.660(4) 1 d P A 2 H10 H 0.3472 0.1104 1.1776 0.049 Uiso 0.660(4) 1 calc PR A 2 C11 C 0.2200(19) 0.0903(7) 1.1855(13) 0.020(5) Uani 0.340(4) 1 d PU A 1 H11A H 0.3081 0.1194 1.1913 0.024 Uiso 0.340(4) 1 calc PR A 1 C11A C 0.1528(12) 0.0701(5) 1.1522(12) 0.043(4) Uani 0.660(4) 1 d P A 2 H11 H 0.0751 0.0473 1.1079 0.052 Uiso 0.660(4) 1 calc PR A 2 C12 C 0.168(5) 0.087(2) 1.258(3) 0.048(4) Uani 0.340(4) 1 d PG A 1 C17 C 0.032(5) 0.057(3) 1.266(3) 0.045(4) Uani 0.340(4) 1 d PG A 1 H17 H -0.0283 0.0314 1.2151 0.054 Uiso 0.340(4) 1 calc PR A 1 C16 C -0.015(4) 0.066(3) 1.349(4) 0.042(3) Uani 0.340(4) 1 d PG A 1 H16 H -0.1075 0.0455 1.3546 0.050 Uiso 0.340(4) 1 calc PR A 1 C15 C 0.073(5) 0.104(3) 1.424(3) 0.044(2) Uani 0.340(4) 1 d PG A 1 H15 H 0.0414 0.1093 1.4806 0.052 Uiso 0.340(4) 1 calc PR A 1 C14 C 0.209(5) 0.133(2) 1.416(3) 0.051(3) Uani 0.340(4) 1 d PG A 1 H14 H 0.2693 0.1591 1.4672 0.061 Uiso 0.340(4) 1 calc PR A 1 C13 C 0.256(3) 0.1248(18) 1.333(3) 0.047(3) Uani 0.340(4) 1 d PG A 1 H13 H 0.3485 0.1450 1.3277 0.056 Uiso 0.340(4) 1 calc PR A 1 C12A C 0.136(2) 0.0885(11) 1.2525(14) 0.048(4) Uani 0.660(4) 1 d PG A 2 C17A C 0.020(2) 0.0485(12) 1.2764(16) 0.045(4) Uani 0.660(4) 1 d PG A 2 H17A H -0.0407 0.0159 1.2322 0.054 Uiso 0.660(4) 1 calc PR A 2 C16A C -0.007(2) 0.0564(15) 1.3651(18) 0.042(3) Uani 0.660(4) 1 d PG A 2 H16A H -0.0868 0.0291 1.3814 0.050 Uiso 0.660(4) 1 calc PR A 2 C15A C 0.082(3) 0.1042(16) 1.4298(14) 0.044(2) Uani 0.660(4) 1 d PG A 2 H15A H 0.0628 0.1096 1.4904 0.052 Uiso 0.660(4) 1 calc PR A 2 C14A C 0.198(2) 0.1441(11) 1.4059(13) 0.051(3) Uani 0.660(4) 1 d PG A 2 H14A H 0.2584 0.1768 1.4502 0.061 Uiso 0.660(4) 1 calc PR A 2 C13A C 0.2250(15) 0.1363(8) 1.3173(14) 0.047(3) Uani 0.660(4) 1 d PG A 2 H13A H 0.3044 0.1635 1.3009 0.056 Uiso 0.660(4) 1 calc PR A 2 C18 C 0.3402(4) 0.15993(19) 0.7332(3) 0.0282(14) Uani 1 1 d . A . C19 C 0.3651(5) 0.2353(2) 0.7666(3) 0.0341(15) Uani 1 1 d . . . H19 H 0.4617 0.2515 0.7948 0.041 Uiso 1 1 calc R . . C20 C 0.2505(6) 0.2868(2) 0.7588(4) 0.0440(18) Uani 1 1 d . . . H20 H 0.2682 0.3389 0.7804 0.053 Uiso 1 1 calc R . . C21 C 0.1102(6) 0.2633(2) 0.7198(4) 0.0464(18) Uani 1 1 d . . . H21 H 0.0313 0.2991 0.7150 0.056 Uiso 1 1 calc R . . C22 C 0.0832(5) 0.1886(3) 0.6878(4) 0.0514(19) Uani 1 1 d . . . H22 H -0.0141 0.1724 0.6614 0.062 Uiso 1 1 calc R . . C23 C 0.1982(5) 0.1369(2) 0.6940(4) 0.0398(17) Uani 1 1 d . . . H23 H 0.1800 0.0852 0.6713 0.048 Uiso 1 1 calc R . . C24 C 0.5692(4) 0.1190(2) 0.6399(4) 0.0329(16) Uani 1 1 d . A . C25 C 0.5894(5) 0.1968(2) 0.6159(4) 0.048(2) Uani 1 1 d . . . H25 H 0.5538 0.2375 0.6488 0.057 Uiso 1 1 calc R . . C26 C 0.6591(6) 0.2155(3) 0.5462(5) 0.053(2) Uani 1 1 d . . . H26 H 0.6716 0.2687 0.5317 0.063 Uiso 1 1 calc R . . C27 C 0.7112(5) 0.1579(3) 0.4970(4) 0.0441(18) Uani 1 1 d . . . H27 H 0.7600 0.1709 0.4487 0.053 Uiso 1 1 calc R . . C28 C 0.6913(6) 0.0810(3) 0.5190(4) 0.050(2) Uani 1 1 d . . . H28 H 0.7263 0.0408 0.4850 0.060 Uiso 1 1 calc R . . C29 C 0.6221(5) 0.0616(2) 0.5887(4) 0.0392(19) Uani 1 1 d . . . H29 H 0.6099 0.0082 0.6025 0.047 Uiso 1 1 calc R . . O1 O 0.1384(13) 0.0426(6) 0.9355(9) 0.060(2) Uani 0.340(4) 1 d PU A 1 O1A O 0.2100(8) 0.0669(4) 0.9631(6) 0.060(2) Uani 0.660(4) 1 d PU A 2 P1 P 0.48758(11) 0.09101(5) 0.73442(9) 0.0297(4) Uani 1 1 d . . . S1 S 0.41771(12) -0.01687(5) 0.72265(10) 0.0425(5) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(2) 0.0261(17) 0.025(3) 0.0011(19) 0.0049(17) 0.0003(17) C1A 0.025(2) 0.0261(17) 0.025(3) 0.0011(19) 0.0049(17) 0.0003(17) C2 0.026(3) 0.032(6) 0.025(9) 0.017(3) 0.010(5) -0.004(3) C2A 0.026(3) 0.032(6) 0.025(9) 0.017(3) 0.010(5) -0.004(3) C3 0.024(4) 0.060(6) 0.051(11) 0.020(4) -0.002(6) -0.010(3) C3A 0.024(4) 0.060(6) 0.051(11) 0.020(4) -0.002(6) -0.010(3) C4 0.020(6) 0.062(5) 0.062(10) 0.005(5) -0.016(9) -0.014(5) C4A 0.020(6) 0.062(5) 0.062(10) 0.005(5) -0.016(9) -0.014(5) C5 0.023(4) 0.052(4) 0.036(7) 0.016(3) 0.000(6) -0.004(4) C5A 0.023(4) 0.052(4) 0.036(7) 0.016(3) 0.000(6) -0.004(4) C6 0.022(3) 0.023(2) 0.025(3) 0.006(2) 0.005(2) 0.0105(19) C6A 0.022(3) 0.023(2) 0.025(3) 0.006(2) 0.005(2) 0.0105(19) C7 0.041(5) 0.045(5) 0.043(5) 0.001(4) 0.007(4) 0.000(4) C7A 0.027(3) 0.019(2) 0.025(4) 0.003(2) 0.011(3) 0.004(2) C8 0.057(7) 0.066(7) 0.059(7) 0.000(5) 0.012(5) -0.009(5) C8A 0.037(3) 0.021(2) 0.038(4) 0.003(2) 0.016(3) 0.010(2) C9 0.034(4) 0.043(4) 0.047(8) 0.014(4) 0.013(7) 0.021(4) C9A 0.034(4) 0.043(4) 0.047(8) 0.014(4) 0.013(7) 0.021(4) C10 0.038(10) 0.033(7) 0.030(16) -0.007(8) -0.003(15) 0.001(6) C10A 0.039(4) 0.025(3) 0.053(10) 0.004(4) -0.002(6) 0.008(3) C11 0.019(7) 0.022(6) 0.021(14) -0.004(6) 0.010(9) -0.007(6) C11A 0.029(5) 0.032(5) 0.070(11) 0.012(5) 0.014(9) 0.001(4) C12 0.070(10) 0.043(3) 0.041(6) 0.014(3) 0.035(6) 0.036(5) C17 0.054(5) 0.047(5) 0.038(7) 0.006(4) 0.017(5) 0.006(3) C16 0.038(3) 0.042(7) 0.048(11) 0.008(5) 0.013(5) -0.003(4) C15 0.042(4) 0.050(2) 0.040(5) -0.006(3) 0.011(4) 0.008(3) C14 0.035(4) 0.041(6) 0.074(7) -0.005(4) 0.005(5) 0.003(4) C13 0.043(7) 0.033(5) 0.070(10) 0.015(5) 0.026(7) 0.024(4) C12A 0.070(10) 0.043(3) 0.041(6) 0.014(3) 0.035(6) 0.036(5) C17A 0.054(5) 0.047(5) 0.038(7) 0.006(4) 0.017(5) 0.006(3) C16A 0.038(3) 0.042(7) 0.048(11) 0.008(5) 0.013(5) -0.003(4) C15A 0.042(4) 0.050(2) 0.040(5) -0.006(3) 0.011(4) 0.008(3) C14A 0.035(4) 0.041(6) 0.074(7) -0.005(4) 0.005(5) 0.003(4) C13A 0.043(7) 0.033(5) 0.070(10) 0.015(5) 0.026(7) 0.024(4) C18 0.031(2) 0.0294(18) 0.024(3) 0.0015(17) 0.005(3) 0.0010(15) C19 0.043(2) 0.035(2) 0.027(4) -0.0026(18) 0.014(3) -0.0002(18) C20 0.063(3) 0.030(2) 0.044(4) -0.003(2) 0.024(3) 0.007(2) C21 0.050(3) 0.047(2) 0.047(5) 0.008(2) 0.022(3) 0.020(2) C22 0.033(2) 0.060(3) 0.060(5) -0.006(3) 0.007(3) 0.011(2) C23 0.035(2) 0.039(2) 0.043(4) -0.006(2) 0.002(3) 0.0023(18) C24 0.0272(19) 0.0319(19) 0.038(4) 0.0022(19) 0.004(3) 0.0069(16) C25 0.053(3) 0.030(2) 0.070(6) 0.004(2) 0.036(4) 0.0090(19) C26 0.056(3) 0.040(2) 0.071(6) 0.007(3) 0.031(4) 0.008(2) C27 0.038(2) 0.063(3) 0.038(5) 0.005(3) 0.023(3) 0.006(2) C28 0.058(3) 0.050(3) 0.042(5) -0.014(3) 0.010(4) 0.012(2) C29 0.043(3) 0.037(2) 0.035(5) -0.010(2) 0.003(3) 0.0034(19) O1 0.051(3) 0.063(3) 0.066(4) 0.016(3) 0.012(3) 0.007(2) O1A 0.051(3) 0.063(3) 0.066(4) 0.016(3) 0.012(3) 0.007(2) P1 0.0279(5) 0.0241(5) 0.0340(9) 0.0019(4) -0.0005(6) 0.0015(4) S1 0.0358(6) 0.0255(5) 0.0608(11) -0.0015(5) -0.0016(7) -0.0009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.34(4) . ? C1 C6 1.34(3) . ? C1 P1 1.90(2) . ? C1A C2A 1.399(16) . ? C1A C6A 1.441(15) . ? C1A P1 1.790(10) . ? C2 H2 0.9500 . ? C2 C3 1.42(3) . ? C2A H2A 0.9500 . ? C2A C3A 1.373(13) . ? C3 H3 0.9500 . ? C3 C4 1.23(6) . ? C3A H3A 0.9500 . ? C3A C4A 1.42(2) . ? C4 H4 0.9500 . ? C4 C5 1.38(3) . ? C4A H4A 0.9500 . ? C4A C5A 1.339(13) . ? C5 H5 0.9500 . ? C5 C6 1.42(2) . ? C5A H5A 0.9500 . ? C5A C6A 1.397(11) . ? C6 C7 1.58(2) . ? C6A C7A 1.496(10) . ? C7 H7 0.9500 . ? C7 C8 1.29(4) . ? C7A H7A 1.0000 . ? C7A C8A 1.507(11) . ? C7A C8A 1.576(7) 3_657 ? C8 H8 0.9500 . ? C8 C9 1.47(3) . ? C8A C7A 1.576(7) 3_657 ? C8A H8A 1.0000 . ? C8A C9A 1.498(12) . ? C9 C10 1.31(3) . ? C9 O1 1.27(3) . ? C9A C10A 1.562(17) . ? C9A O1A 1.211(12) . ? C10 H10A 0.9500 . ? C10 C11 1.50(2) . ? C10A H10 0.9500 . ? C10A C11A 1.250(18) . ? C11 H11A 0.9500 . ? C11 C12 1.27(5) . ? C11A H11 0.9500 . ? C11A C12A 1.55(3) . ? C12 C17 1.3900 . ? C12 C13 1.3900 . ? C17 H17 0.9500 . ? C17 C16 1.3900 . ? C16 H16 0.9500 . ? C16 C15 1.3900 . ? C15 H15 0.9500 . ? C15 C14 1.3900 . ? C14 H14 0.9500 . ? C14 C13 1.3900 . ? C13 H13 0.9500 . ? C12A C17A 1.3900 . ? C12A C13A 1.3900 . ? C17A H17A 0.9500 . ? C17A C16A 1.3900 . ? C16A H16A 0.9500 . ? C16A C15A 1.3900 . ? C15A H15A 0.9500 . ? C15A C14A 1.3900 . ? C14A H14A 0.9500 . ? C14A C13A 1.3900 . ? C13A H13A 0.9500 . ? C18 C19 1.385(5) . ? C18 C23 1.385(5) . ? C18 P1 1.811(4) . ? C19 H19 0.9500 . ? C19 C20 1.373(6) . ? C20 H20 0.9500 . ? C20 C21 1.374(7) . ? C21 H21 0.9500 . ? C21 C22 1.369(6) . ? C22 H22 0.9500 . ? C22 C23 1.380(6) . ? C23 H23 0.9500 . ? C24 C25 1.402(6) . ? C24 C29 1.393(7) . ? C24 P1 1.790(6) . ? C25 H25 0.9500 . ? C25 C26 1.365(8) . ? C26 H26 0.9500 . ? C26 C27 1.373(8) . ? C27 H27 0.9500 . ? C27 C28 1.379(7) . ? C28 H28 0.9500 . ? C28 C29 1.367(8) . ? C29 H29 0.9500 . ? P1 S1 1.9561(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 122(2) . . ? C2 C1 P1 115(2) . . ? C6 C1 P1 123.1(15) . . ? C2A C1A C6A 118.0(9) . . ? C2A C1A P1 121.5(10) . . ? C6A C1A P1 120.5(7) . . ? C1 C2 H2 120.1 . . ? C1 C2 C3 120(3) . . ? C3 C2 H2 120.1 . . ? C1A C2A H2A 118.8 . . ? C3A C2A C1A 122.4(12) . . ? C3A C2A H2A 118.8 . . ? C2 C3 H3 122.0 . . ? C4 C3 C2 116(3) . . ? C4 C3 H3 122.0 . . ? C2A C3A H3A 119.9 . . ? C2A C3A C4A 120.1(10) . . ? C4A C3A H3A 119.9 . . ? C3 C4 H4 115.2 . . ? C3 C4 C5 130(3) . . ? C5 C4 H4 115.2 . . ? C3A C4A H4A 121.7 . . ? C5A C4A C3A 116.6(14) . . ? C5A C4A H4A 121.7 . . ? C4 C5 H5 123.1 . . ? C4 C5 C6 114(3) . . ? C6 C5 H5 123.1 . . ? C4A C5A H5A 116.7 . . ? C4A C5A C6A 126.7(14) . . ? C6A C5A H5A 116.7 . . ? C1 C6 C5 118.9(16) . . ? C1 C6 C7 127.9(14) . . ? C5 C6 C7 113.3(18) . . ? C1A C6A C7A 121.7(6) . . ? C5A C6A C1A 116.0(8) . . ? C5A C6A C7A 122.2(8) . . ? C6 C7 H7 116.6 . . ? C8 C7 C6 126.7(16) . . ? C8 C7 H7 116.6 . . ? C6A C7A H7A 111.0 . . ? C6A C7A C8A 115.5(5) . 3_657 ? C6A C7A C8A 117.9(5) . . ? C8A C7A H7A 111.0 3_657 . ? C8A C7A H7A 111.0 . . ? C8A C7A C8A 88.6(6) . 3_657 ? C7 C8 H8 122.4 . . ? C7 C8 C9 115(2) . . ? C9 C8 H8 122.4 . . ? C7A C8A C7A 91.4(6) . 3_657 ? C7A C8A H8A 110.9 . . ? C7A C8A H8A 110.9 3_657 . ? C9A C8A C7A 116.4(7) . . ? C9A C8A C7A 114.9(6) . 3_657 ? C9A C8A H8A 110.9 . . ? C10 C9 C8 120(2) . . ? O1 C9 C8 117(3) . . ? O1 C9 C10 123(2) . . ? C8A C9A C10A 114.0(8) . . ? O1A C9A C8A 121.6(11) . . ? O1A C9A C10A 124.3(10) . . ? C9 C10 H10A 115.0 . . ? C9 C10 C11 130(2) . . ? C11 C10 H10A 115.0 . . ? C9A C10A H10 119.1 . . ? C11A C10A C9A 121.7(11) . . ? C11A C10A H10 119.1 . . ? C10 C11 H11A 115.5 . . ? C12 C11 C10 129(3) . . ? C12 C11 H11A 115.5 . . ? C10A C11A H11 121.4 . . ? C10A C11A C12A 117.2(15) . . ? C12A C11A H11 121.4 . . ? C11 C12 C17 128(3) . . ? C11 C12 C13 112(3) . . ? C17 C12 C13 120.0 . . ? C12 C17 H17 120.0 . . ? C12 C17 C16 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C16 H16 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 C16 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C14 H14 120.0 . . ? C15 C14 C13 120.0 . . ? C13 C14 H14 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 C12 120.00(5) . . ? C14 C13 H13 120.0 . . ? C17A C12A C11A 112.6(13) . . ? C17A C12A C13A 120.0 . . ? C13A C12A C11A 127.4(13) . . ? C12A C17A H17A 120.0 . . ? C12A C17A C16A 120.0 . . ? C16A C17A H17A 120.0 . . ? C17A C16A H16A 120.0 . . ? C17A C16A C15A 120.0 . . ? C15A C16A H16A 120.0 . . ? C16A C15A H15A 120.0 . . ? C16A C15A C14A 120.0 . . ? C14A C15A H15A 120.0 . . ? C15A C14A H14A 120.0 . . ? C13A C14A C15A 120.0 . . ? C13A C14A H14A 120.0 . . ? C12A C13A H13A 120.0 . . ? C14A C13A C12A 120.0 . . ? C14A C13A H13A 120.0 . . ? C19 C18 C23 119.2(4) . . ? C19 C18 P1 122.4(3) . . ? C23 C18 P1 118.4(3) . . ? C18 C19 H19 120.0 . . ? C20 C19 C18 120.1(4) . . ? C20 C19 H19 120.0 . . ? C19 C20 H20 119.9 . . ? C19 C20 C21 120.2(4) . . ? C21 C20 H20 119.9 . . ? C20 C21 H21 119.7 . . ? C22 C21 C20 120.5(4) . . ? C22 C21 H21 119.7 . . ? C21 C22 H22 120.2 . . ? C21 C22 C23 119.6(4) . . ? C23 C22 H22 120.2 . . ? C18 C23 H23 119.8 . . ? C22 C23 C18 120.5(4) . . ? C22 C23 H23 119.8 . . ? C25 C24 P1 123.7(4) . . ? C29 C24 C25 116.9(6) . . ? C29 C24 P1 119.4(4) . . ? C24 C25 H25 119.2 . . ? C26 C25 C24 121.7(5) . . ? C26 C25 H25 119.2 . . ? C25 C26 H26 119.8 . . ? C25 C26 C27 120.5(5) . . ? C27 C26 H26 119.8 . . ? C26 C27 H27 120.6 . . ? C26 C27 C28 118.8(7) . . ? C28 C27 H27 120.6 . . ? C27 C28 H28 119.4 . . ? C29 C28 C27 121.3(5) . . ? C29 C28 H28 119.4 . . ? C24 C29 H29 119.6 . . ? C28 C29 C24 120.9(5) . . ? C28 C29 H29 119.6 . . ? C1 P1 S1 114.9(7) . . ? C1A P1 C1 12.3(11) . . ? C1A P1 C18 109.4(3) . . ? C1A P1 S1 116.1(4) . . ? C18 P1 C1 99.9(7) . . ? C18 P1 S1 112.17(13) . . ? C24 P1 C1 111.5(9) . . ? C24 P1 C1A 100.7(4) . . ? C24 P1 C18 105.43(19) . . ? C24 P1 S1 111.96(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 1(4) . . . . ? C1 C6 C7 C8 163(2) . . . . ? C1A C2A C3A C4A -3(2) . . . . ? C1A C6A C7A C8A -155.7(6) . . . . ? C1A C6A C7A C8A 101.5(8) . . . 3_657 ? C2 C1 C6 C5 2(3) . . . . ? C2 C1 C6 C7 -180.0(18) . . . . ? C2 C1 P1 C1A 14(4) . . . . ? C2 C1 P1 C18 -126.8(17) . . . . ? C2 C1 P1 C24 -15.7(19) . . . . ? C2 C1 P1 S1 113.0(17) . . . . ? C2 C3 C4 C5 2(5) . . . . ? C2A C1A C6A C5A 2.6(12) . . . . ? C2A C1A C6A C7A -172.6(9) . . . . ? C2A C1A P1 C1 -143(5) . . . . ? C2A C1A P1 C18 -102.4(10) . . . . ? C2A C1A P1 C24 8.3(10) . . . . ? C2A C1A P1 S1 129.4(9) . . . . ? C2A C3A C4A C5A 5(2) . . . . ? C3 C4 C5 C6 -2(4) . . . . ? C3A C4A C5A C6A -3.1(19) . . . . ? C4 C5 C6 C1 0(2) . . . . ? C4 C5 C6 C7 -178.3(16) . . . . ? C4A C5A C6A C1A -0.7(14) . . . . ? C4A C5A C6A C7A 174.5(11) . . . . ? C5 C6 C7 C8 -19(2) . . . . ? C5A C6A C7A C8A -73.5(9) . . . 3_657 ? C5A C6A C7A C8A 29.3(8) . . . . ? C6 C1 C2 C3 -2(4) . . . . ? C6 C1 P1 C1A -161(6) . . . . ? C6 C1 P1 C18 58.4(17) . . . . ? C6 C1 P1 C24 169.4(14) . . . . ? C6 C1 P1 S1 -61.8(17) . . . . ? C6 C7 C8 C9 -177.5(14) . . . . ? C6A C1A C2A C3A -0.7(18) . . . . ? C6A C1A P1 C1 34(4) . . . . ? C6A C1A P1 C18 75.2(8) . . . . ? C6A C1A P1 C24 -174.1(6) . . . . ? C6A C1A P1 S1 -53.0(8) . . . . ? C6A C7A C8A C7A -118.3(5) . . . 3_657 ? C6A C7A C8A C9A 122.9(6) . . . . ? C7 C8 C9 C10 -162.6(17) . . . . ? C7 C8 C9 O1 20(3) . . . . ? C7A C8A C9A C10A -171.8(5) . . . . ? C7A C8A C9A C10A 83.1(9) 3_657 . . . ? C7A C8A C9A O1A 12.5(11) . . . . ? C7A C8A C9A O1A -92.6(10) 3_657 . . . ? C8 C9 C10 C11 22(3) . . . . ? C8A C7A C8A C7A 0.0 3_657 . . 3_657 ? C8A C7A C8A C9A -118.8(6) 3_657 . . . ? C8A C9A C10A C11A -146.4(8) . . . . ? C9 C10 C11 C12 -179(2) . . . . ? C9A C10A C11A C12A 178.4(9) . . . . ? C10 C11 C12 C17 -9(3) . . . . ? C10 C11 C12 C13 177.5(15) . . . . ? C10A C11A C12A C17A -162.3(7) . . . . ? C10A C11A C12A C13A 15.4(17) . . . . ? C11 C12 C17 C16 -173(4) . . . . ? C11 C12 C13 C14 174(3) . . . . ? C11A C12A C17A C16A 177.9(13) . . . . ? C11A C12A C13A C14A -177.6(16) . . . . ? C12 C17 C16 C15 0.0 . . . . ? C17 C12 C13 C14 0.0 . . . . ? C17 C16 C15 C14 0.0 . . . . ? C16 C15 C14 C13 0.0 . . . . ? C15 C14 C13 C12 0.0 . . . . ? C13 C12 C17 C16 0.0 . . . . ? C12A C17A C16A C15A 0.0 . . . . ? C17A C12A C13A C14A 0.0 . . . . ? C17A C16A C15A C14A 0.0 . . . . ? C16A C15A C14A C13A 0.0 . . . . ? C15A C14A C13A C12A 0.0 . . . . ? C13A C12A C17A C16A 0.0 . . . . ? C18 C19 C20 C21 1.4(9) . . . . ? C19 C18 C23 C22 0.4(8) . . . . ? C19 C18 P1 C1 38.8(9) . . . . ? C19 C18 P1 C1A 30.6(6) . . . . ? C19 C18 P1 C24 -76.9(4) . . . . ? C19 C18 P1 S1 161.0(4) . . . . ? C19 C20 C21 C22 -0.4(9) . . . . ? C20 C21 C22 C23 -0.6(9) . . . . ? C21 C22 C23 C18 0.7(9) . . . . ? C23 C18 C19 C20 -1.4(8) . . . . ? C23 C18 P1 C1 -143.8(9) . . . . ? C23 C18 P1 C1A -152.0(6) . . . . ? C23 C18 P1 C24 100.4(4) . . . . ? C23 C18 P1 S1 -21.7(5) . . . . ? C24 C25 C26 C27 0.3(7) . . . . ? C25 C24 C29 C28 0.5(6) . . . . ? C25 C24 P1 C1 -68.9(8) . . . . ? C25 C24 P1 C1A -75.2(5) . . . . ? C25 C24 P1 C18 38.6(4) . . . . ? C25 C24 P1 S1 160.8(3) . . . . ? C25 C26 C27 C28 0.3(7) . . . . ? C26 C27 C28 C29 -0.5(7) . . . . ? C27 C28 C29 C24 0.1(6) . . . . ? C29 C24 C25 C26 -0.7(6) . . . . ? C29 C24 P1 C1 108.3(7) . . . . ? C29 C24 P1 C1A 102.0(4) . . . . ? C29 C24 P1 C18 -144.2(3) . . . . ? C29 C24 P1 S1 -22.0(3) . . . . ? O1 C9 C10 C11 -160.8(14) . . . . ? O1A C9A C10A C11A 29.2(12) . . . . ? P1 C1 C2 C3 -177.0(19) . . . . ? P1 C1 C6 C5 176.0(12) . . . . ? P1 C1 C6 C7 -6(2) . . . . ? P1 C1A C2A C3A 176.9(11) . . . . ? P1 C1A C6A C5A -175.0(6) . . . . ? P1 C1A C6A C7A 9.7(10) . . . . ? P1 C18 C19 C20 175.9(4) . . . . ? P1 C18 C23 C22 -177.1(5) . . . . ? P1 C24 C25 C26 176.6(4) . . . . ? P1 C24 C29 C28 -176.9(3) . . . . ? ### END data_ijf1030 _database_code_depnum_ccdc_archive 'CCDC 874852' #TrackingRef '- all.cif' _audit_creation_method 'WinGX routine CIF_UPDATE' __chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3733(3) _cell_length_b 17.2097(5) _cell_length_c 14.8077(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.379(3) _cell_angle_gamma 90.00 _cell_volume 2333.12(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3877 _cell_measurement_temperature 110.0 _cell_measurement_theta_max 27.8130 _cell_measurement_theta_min 3.1049 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.93742 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_unetI/netI 0.0504 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9725 _diffrn_reflns_theta_full 27.87 _diffrn_reflns_theta_max 27.87 _diffrn_reflns_theta_min 3.11 _diffrn_ambient_temperature 110.0 _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -51.00 49.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - -20.9830 77.0000 -150.0000 100 #__ type_ start__ end____ width___ exp.time_ 2 omega -8.00 92.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - 22.2330 77.0000 -30.0000 100 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0563200000 _diffrn_orient_matrix_UB_12 0.0127822000 _diffrn_orient_matrix_UB_13 -0.0217269000 _diffrn_orient_matrix_UB_21 -0.0153520000 _diffrn_orient_matrix_UB_22 0.0391169000 _diffrn_orient_matrix_UB_23 0.0095858000 _diffrn_orient_matrix_UB_31 0.0509821000 _diffrn_orient_matrix_UB_32 -0.0023361000 _diffrn_orient_matrix_UB_33 0.0428848000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4260 _reflns_number_total 5517 _reflns_odcompleteness_completeness 97.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 28.02 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.604 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.058 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 362 _refine_ls_number_reflns 5517 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0640 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+2.7606P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1338 _refine_ls_wR_factor_ref 0.1463 _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. The crystal contained a disordered mixture of the monomer and photo-dimer. The ratio of these compounds refined to 0.293:0.707(3). The ADP of the following pairs of atoms were constrained to be equal: O1 O1A, C1A C1, C2 C2A, C3A C3, C8a C8, C9A C9, C12A C12, C14A C14, C15A C15, C16A C16, C17A C17. The ADP of the following atoms were restrained to be isotropic C11 C13 C13A The bond lengths of C10-C11 & C10A-C11A were restrained to be equal The bond lengths of C11-C12 & C11A-C12A were restrained to be equal Two phenyl rings (C12-C17 & C12A-C17A) were constrained to be regular hexagons with a C-C bond length of 1.39 angstroms. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.1030(14) 0.1142(9) 0.8533(9) 0.0213(8) Uani 0.293(3) 1 d P A 1 C1A C 1.1358(5) 0.1117(3) 0.8316(3) 0.0213(8) Uani 0.707(3) 1 d P A 2 C2 C 1.2450(13) 0.1323(7) 0.8473(9) 0.0315(9) Uani 0.293(3) 1 d P A 1 H2 H 1.2731 0.1337 0.7894 0.038 Uiso 0.293(3) 1 calc PR A 1 C2A C 1.2624(5) 0.1495(3) 0.8191(3) 0.0315(9) Uani 0.707(3) 1 d P A 2 H2A H 1.2722 0.1622 0.7583 0.038 Uiso 0.707(3) 1 calc PR A 2 C3 C 1.3487(13) 0.1489(9) 0.9327(11) 0.0448(11) Uani 0.293(3) 1 d P A 1 H3 H 1.4471 0.1612 0.9316 0.054 Uiso 0.293(3) 1 calc PR A 1 C3A C 1.3728(4) 0.1684(3) 0.8929(3) 0.0448(11) Uani 0.707(3) 1 d P A 2 H3A H 1.4586 0.1932 0.8828 0.054 Uiso 0.707(3) 1 calc PR A 2 C4 C 1.3066(13) 0.1470(7) 1.0115(9) 0.034(2) Uani 0.293(3) 1 d P A 1 H4 H 1.3754 0.1584 1.0670 0.041 Uiso 0.293(3) 1 calc PR A 1 C4A C 1.3590(6) 0.1514(3) 0.9811(4) 0.0476(14) Uani 0.707(3) 1 d P A 2 H4A H 1.4346 0.1656 1.0321 0.057 Uiso 0.707(3) 1 calc PR A 2 C5 C 1.1644(13) 0.1287(6) 1.0161(7) 0.036(2) Uani 0.293(3) 1 d P A 1 H5 H 1.1374 0.1276 1.0744 0.043 Uiso 0.293(3) 1 calc PR A 1 C5A C 1.2364(6) 0.1140(3) 0.9962(3) 0.0356(9) Uani 0.707(3) 1 d P A 2 H5A H 1.2279 0.1035 1.0578 0.043 Uiso 0.707(3) 1 calc PR A 2 C6 C 1.0609(11) 0.1119(7) 0.9361(6) 0.034(2) Uani 0.293(3) 1 d P A 1 C6A C 1.1233(4) 0.0911(2) 0.9224(3) 0.0227(7) Uani 0.707(3) 1 d P A 2 C7 C 0.9073(10) 0.0941(6) 0.9431(7) 0.039(2) Uani 0.293(3) 1 d P A 1 H7 H 0.8354 0.0934 0.8871 0.047 Uiso 0.293(3) 1 calc PR A 1 C7A C 1.0011(4) 0.04089(19) 0.9420(2) 0.0240(7) Uani 0.707(3) 1 d P . 2 H7A H 0.9131 0.0448 0.8904 0.029 Uiso 0.707(3) 1 calc PR A 2 C8 C 0.8618(13) 0.0789(6) 1.0215(7) 0.0311(8) Uani 0.293(3) 1 d P A 1 H8 H 0.9284 0.0823 1.0796 0.037 Uiso 0.293(3) 1 calc PR A 1 C8A C 0.9571(4) 0.0478(2) 1.0358(3) 0.0311(8) Uani 0.707(3) 1 d P . 2 H8A H 1.0248 0.0833 1.0783 0.037 Uiso 0.707(3) 1 calc PR A 2 C9 C 0.7095(12) 0.0571(7) 1.0172(9) 0.0414(11) Uani 0.293(3) 1 d P A 1 C9A C 0.8020(5) 0.0677(3) 1.0333(3) 0.0414(11) Uani 0.707(3) 1 d P A 2 C10 C 0.6641(10) 0.0563(5) 1.0936(6) 0.0269(19) Uani 0.293(3) 1 d PD A 1 H10 H 0.5760 0.0285 1.0917 0.032 Uiso 0.293(3) 1 calc PR A 1 C10A C 0.7745(5) 0.0869(2) 1.1291(3) 0.0433(10) Uani 0.707(3) 1 d PD A 2 H10A H 0.8496 0.1120 1.1726 0.052 Uiso 0.707(3) 1 calc PR A 2 C11 C 0.7255(10) 0.0903(5) 1.1783(5) 0.0191(16) Uani 0.293(3) 1 d PDU A 1 H11 H 0.8157 0.1161 1.1799 0.023 Uiso 0.293(3) 1 calc PR A 1 C11A C 0.6536(5) 0.0704(3) 1.1533(4) 0.0430(11) Uani 0.707(3) 1 d PD A 2 H11A H 0.5762 0.0478 1.1090 0.052 Uiso 0.707(3) 1 calc PR A 2 C12 C 0.6744(13) 0.0934(11) 1.2674(6) 0.0403(12) Uani 0.293(3) 1 d PGD A 1 C13 C 0.7528(14) 0.1361(9) 1.3413(7) 0.033(3) Uani 0.293(3) 1 d PGU A 1 H13 H 0.8408 0.1613 1.3363 0.040 Uiso 0.293(3) 1 calc PR A 1 C14 C 0.702(3) 0.1418(18) 1.4227(9) 0.0424(10) Uani 0.293(3) 1 d PG A 1 H14 H 0.7557 0.1709 1.4733 0.051 Uiso 0.293(3) 1 calc PR A 1 C15 C 0.573(3) 0.105(3) 1.4302(14) 0.0437(8) Uani 0.293(3) 1 d PG A 1 H15 H 0.5387 0.1088 1.4858 0.052 Uiso 0.293(3) 1 calc PR A 1 C16 C 0.495(3) 0.062(3) 1.3562(16) 0.0469(9) Uani 0.293(3) 1 d PG A 1 H16 H 0.4069 0.0370 1.3613 0.056 Uiso 0.293(3) 1 calc PR A 1 C17 C 0.546(2) 0.0565(16) 1.2748(12) 0.0433(11) Uani 0.293(3) 1 d PG A 1 H17 H 0.4920 0.0274 1.2242 0.052 Uiso 0.293(3) 1 calc PR A 1 C12A C 0.6315(4) 0.0858(4) 1.2491(2) 0.0403(12) Uani 0.707(3) 1 d PGD A 2 C13A C 0.7252(5) 0.1316(3) 1.3130(3) 0.0410(13) Uani 0.707(3) 1 d PGU A 2 H13A H 0.8060 0.1566 1.2962 0.049 Uiso 0.707(3) 1 calc PR A 2 C14A C 0.7005(10) 0.1408(7) 1.4017(4) 0.0424(10) Uani 0.707(3) 1 d PG A 2 H14A H 0.7645 0.1721 1.4454 0.051 Uiso 0.707(3) 1 calc PR A 2 C15A C 0.5823(14) 0.1043(11) 1.4264(5) 0.0437(8) Uani 0.707(3) 1 d PG A 2 H15A H 0.5654 0.1106 1.4870 0.052 Uiso 0.707(3) 1 calc PR A 2 C16A C 0.4886(13) 0.0585(10) 1.3624(6) 0.0469(9) Uani 0.707(3) 1 d PG A 2 H16A H 0.4078 0.0335 1.3793 0.056 Uiso 0.707(3) 1 calc PR A 2 C17A C 0.5133(7) 0.0492(6) 1.2738(5) 0.0433(11) Uani 0.707(3) 1 d PG A 2 H17A H 0.4493 0.0179 1.2301 0.052 Uiso 0.707(3) 1 calc PR A 2 C18 C 0.8401(3) 0.15936(15) 0.73343(16) 0.0272(5) Uani 1 1 d . A . C19 C 0.6980(3) 0.13627(17) 0.6944(2) 0.0387(6) Uani 1 1 d . . . H19 H 0.6793 0.0848 0.6718 0.046 Uiso 1 1 calc R . . C20 C 0.5834(3) 0.1885(2) 0.6884(2) 0.0517(8) Uani 1 1 d . . . H20 H 0.4863 0.1726 0.6622 0.062 Uiso 1 1 calc R . . C21 C 0.6102(3) 0.26307(19) 0.7201(2) 0.0490(8) Uani 1 1 d . . . H21 H 0.5316 0.2988 0.7152 0.059 Uiso 1 1 calc R . . C22 C 0.7505(3) 0.28651(17) 0.7593(2) 0.0424(7) Uani 1 1 d . . . H22 H 0.7681 0.3383 0.7810 0.051 Uiso 1 1 calc R . . C23 C 0.8662(3) 0.23484(16) 0.76698(18) 0.0337(6) Uani 1 1 d . . . H23 H 0.9626 0.2508 0.7950 0.040 Uiso 1 1 calc R . . C24 C 1.0689(3) 0.11844(16) 0.63795(19) 0.0323(6) Uani 1 1 d . A . C25 C 1.0863(3) 0.19620(17) 0.6154(2) 0.0461(8) Uani 1 1 d . . . H25 H 1.0496 0.2362 0.6484 0.055 Uiso 1 1 calc R . . C26 C 1.1571(3) 0.2155(2) 0.5451(2) 0.0488(8) Uani 1 1 d . . . H26 H 1.1688 0.2684 0.5300 0.059 Uiso 1 1 calc R . . C27 C 1.2104(3) 0.1568(2) 0.4970(2) 0.0443(7) Uani 1 1 d . . . H27 H 1.2595 0.1697 0.4492 0.053 Uiso 1 1 calc R . . C28 C 1.1925(3) 0.0802(2) 0.5185(2) 0.0470(8) Uani 1 1 d . . . H28 H 1.2281 0.0404 0.4848 0.056 Uiso 1 1 calc R . . C29 C 1.1226(3) 0.06076(17) 0.5890(2) 0.0392(6) Uani 1 1 d . . . H29 H 1.1116 0.0077 0.6038 0.047 Uiso 1 1 calc R . . O1 O 0.6305(9) 0.0442(6) 0.9400(7) 0.0598(10) Uani 0.293(3) 1 d P A 1 O1A O 0.7100(4) 0.0666(2) 0.9616(3) 0.0598(10) Uani 0.707(3) 1 d P A 2 P1 P 0.98744(7) 0.09027(4) 0.73408(5) 0.02752(16) Uani 1 1 d . . . S1 S 0.91759(7) -0.01743(4) 0.72213(6) 0.03913(19) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.019(2) 0.0265(14) 0.019(2) 0.0076(17) 0.0069(12) -0.0005(16) C1A 0.019(2) 0.0265(14) 0.019(2) 0.0076(17) 0.0069(12) -0.0005(16) C2 0.0252(16) 0.035(3) 0.035(3) 0.0134(18) 0.0083(16) -0.0037(15) C2A 0.0252(16) 0.035(3) 0.035(3) 0.0134(18) 0.0083(16) -0.0037(15) C3 0.0206(17) 0.063(3) 0.048(3) 0.018(2) -0.0002(17) -0.0092(17) C3A 0.0206(17) 0.063(3) 0.048(3) 0.018(2) -0.0002(17) -0.0092(17) C4 0.015(5) 0.044(6) 0.042(7) -0.001(5) 0.004(4) -0.007(5) C4A 0.024(3) 0.070(4) 0.042(3) 0.022(3) -0.009(2) -0.011(2) C5 0.034(6) 0.046(6) 0.027(5) -0.002(4) 0.004(4) -0.003(5) C5A 0.030(2) 0.048(3) 0.027(2) 0.0155(19) 0.0030(19) -0.001(2) C6 0.028(5) 0.048(6) 0.020(5) 0.000(4) -0.007(4) 0.002(4) C6A 0.0219(18) 0.0202(17) 0.0267(19) 0.0091(15) 0.0068(15) 0.0054(14) C7 0.038(5) 0.048(6) 0.031(5) -0.005(5) 0.008(4) 0.000(4) C7A 0.0331(17) 0.0191(16) 0.0226(17) 0.0045(13) 0.0123(13) 0.0030(13) C8 0.045(2) 0.0229(17) 0.0308(18) 0.0014(14) 0.0197(16) 0.0036(13) C8A 0.045(2) 0.0229(17) 0.0308(18) 0.0014(14) 0.0197(16) 0.0036(13) C9 0.040(2) 0.044(2) 0.049(3) 0.0205(19) 0.029(2) 0.019(2) C9A 0.040(2) 0.044(2) 0.049(3) 0.0205(19) 0.029(2) 0.019(2) C10 0.032(4) 0.024(4) 0.017(4) 0.002(4) -0.010(3) -0.004(3) C10A 0.040(2) 0.032(2) 0.056(3) 0.003(2) 0.008(2) 0.0070(17) C11 0.013(3) 0.022(3) 0.022(3) -0.003(3) 0.005(3) -0.006(3) C11A 0.031(2) 0.039(3) 0.061(4) 0.015(2) 0.014(2) 0.0091(19) C12 0.047(3) 0.039(2) 0.036(2) 0.005(2) 0.010(2) 0.020(3) C13 0.037(4) 0.033(4) 0.028(4) -0.002(4) 0.002(4) 0.003(3) C14 0.0403(16) 0.0454(19) 0.043(3) -0.009(3) 0.012(3) 0.0009(13) C15 0.040(2) 0.0515(19) 0.0434(19) -0.0046(16) 0.0165(13) 0.0048(18) C16 0.0400(18) 0.050(3) 0.054(2) -0.002(2) 0.0168(15) -0.0033(14) C17 0.035(4) 0.044(3) 0.051(2) 0.0001(17) 0.008(2) 0.001(3) C12A 0.047(3) 0.039(2) 0.036(2) 0.005(2) 0.010(2) 0.020(3) C13A 0.039(2) 0.043(3) 0.046(3) -0.004(3) 0.021(2) 0.002(2) C14A 0.0403(16) 0.0454(19) 0.043(3) -0.009(3) 0.012(3) 0.0009(13) C15A 0.040(2) 0.0515(19) 0.0434(19) -0.0046(16) 0.0165(13) 0.0048(18) C16A 0.0400(18) 0.050(3) 0.054(2) -0.002(2) 0.0168(15) -0.0033(14) C17A 0.035(4) 0.044(3) 0.051(2) 0.0001(17) 0.008(2) 0.001(3) C18 0.0306(12) 0.0302(13) 0.0206(12) 0.0003(10) 0.0053(9) 0.0018(10) C19 0.0320(13) 0.0369(15) 0.0443(17) -0.0061(13) 0.0017(11) 0.0039(11) C20 0.0316(14) 0.058(2) 0.063(2) -0.0028(18) 0.0052(14) 0.0101(14) C21 0.0494(17) 0.0477(19) 0.054(2) 0.0055(16) 0.0210(15) 0.0212(14) C22 0.0611(18) 0.0305(14) 0.0415(17) -0.0038(13) 0.0239(14) 0.0090(13) C23 0.0404(14) 0.0322(14) 0.0305(14) -0.0020(11) 0.0120(11) -0.0004(11) C24 0.0269(12) 0.0325(14) 0.0371(15) 0.0014(12) 0.0060(10) 0.0069(10) C25 0.0539(17) 0.0319(15) 0.062(2) 0.0055(15) 0.0335(16) 0.0103(13) C26 0.0526(18) 0.0416(18) 0.060(2) 0.0077(16) 0.0297(16) 0.0058(14) C27 0.0392(15) 0.056(2) 0.0402(17) 0.0017(15) 0.0151(13) 0.0069(13) C28 0.0514(17) 0.054(2) 0.0362(17) -0.0122(15) 0.0114(13) 0.0098(14) C29 0.0426(15) 0.0347(15) 0.0372(16) -0.0051(13) 0.0013(12) 0.0038(12) O1 0.0344(18) 0.079(3) 0.073(2) 0.031(2) 0.026(2) 0.0175(18) O1A 0.0344(18) 0.079(3) 0.073(2) 0.031(2) 0.026(2) 0.0175(18) P1 0.0264(3) 0.0242(3) 0.0290(3) 0.0027(3) -0.0007(2) 0.0016(2) S1 0.0340(3) 0.0248(3) 0.0540(5) -0.0006(3) -0.0009(3) -0.0013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.388(14) . ? C1 C6 1.367(14) . ? C1 P1 1.908(14) . ? C1A C2A 1.400(5) . ? C1A C6A 1.419(5) . ? C1A P1 1.815(5) . ? C2 H2 0.9500 . ? C2 C3 1.449(19) . ? C2A H2A 0.9500 . ? C2A C3A 1.373(6) . ? C3 H3 0.9500 . ? C3 C4 1.309(18) . ? C3A H3A 0.9500 . ? C3A C4A 1.372(7) . ? C4 H4 0.9500 . ? C4 C5 1.385(14) . ? C4A H4A 0.9500 . ? C4A C5A 1.377(6) . ? C5 H5 0.9500 . ? C5 C6 1.392(13) . ? C5A H5A 0.9500 . ? C5A C6A 1.407(6) . ? C6 C7 1.498(14) . ? C6A C7A 1.511(5) . ? C7 H7 0.9500 . ? C7 C8 1.345(13) . ? C7A H7A 1.0000 . ? C7A C8A 1.593(5) 3_757 ? C7A C8A 1.535(5) . ? C8 H8 0.9500 . ? C8 C9 1.464(15) . ? C8A C7A 1.593(5) 3_757 ? C8A H8A 1.0000 . ? C8A C9A 1.486(6) . ? C9 C10 1.292(15) . ? C9 O1 1.241(16) . ? C9A C10A 1.532(7) . ? C9A O1A 1.216(6) . ? C10 H10 0.9500 . ? C10 C11 1.392(10) . ? C10A H10A 0.9500 . ? C10A C11A 1.291(6) . ? C11 H11 0.9500 . ? C11 C12 1.497(6) . ? C11A H11A 0.9500 . ? C11A C12A 1.501(5) . ? C12 C13 1.3900 . ? C12 C17 1.3900 . ? C13 H13 0.9500 . ? C13 C14 1.3900 . ? C14 H14 0.9500 . ? C14 C15 1.3900 . ? C15 H15 0.9500 . ? C15 C16 1.3900 . ? C16 H16 0.9500 . ? C16 C17 1.3900 . ? C17 H17 0.9500 . ? C12A C13A 1.3900 . ? C12A C17A 1.3900 . ? C13A H13A 0.9500 . ? C13A C14A 1.3900 . ? C14A H14A 0.9500 . ? C14A C15A 1.3900 . ? C15A H15A 0.9500 . ? C15A C16A 1.3900 . ? C16A H16A 0.9500 . ? C16A C17A 1.3900 . ? C17A H17A 0.9500 . ? C18 C19 1.392(3) . ? C18 C23 1.393(4) . ? C18 P1 1.821(2) . ? C19 H19 0.9500 . ? C19 C20 1.389(4) . ? C20 H20 0.9500 . ? C20 C21 1.371(5) . ? C21 H21 0.9500 . ? C21 C22 1.379(5) . ? C22 H22 0.9500 . ? C22 C23 1.388(4) . ? C23 H23 0.9500 . ? C24 C25 1.397(4) . ? C24 C29 1.386(4) . ? C24 P1 1.819(3) . ? C25 H25 0.9500 . ? C25 C26 1.389(4) . ? C26 H26 0.9500 . ? C26 C27 1.388(4) . ? C27 H27 0.9500 . ? C27 C28 1.375(5) . ? C28 H28 0.9500 . ? C28 C29 1.387(4) . ? C29 H29 0.9500 . ? P1 S1 1.9610(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 P1 110.6(8) . . ? C6 C1 C2 122.0(12) . . ? C6 C1 P1 127.4(9) . . ? C2A C1A C6A 119.1(4) . . ? C2A C1A P1 121.0(3) . . ? C6A C1A P1 119.8(3) . . ? C1 C2 H2 121.3 . . ? C1 C2 C3 117.5(12) . . ? C3 C2 H2 121.3 . . ? C1A C2A H2A 119.3 . . ? C3A C2A C1A 121.3(4) . . ? C3A C2A H2A 119.3 . . ? C2 C3 H3 120.0 . . ? C4 C3 C2 119.9(11) . . ? C4 C3 H3 120.0 . . ? C2A C3A H3A 120.0 . . ? C4A C3A C2A 119.9(4) . . ? C4A C3A H3A 120.0 . . ? C3 C4 H4 119.1 . . ? C3 C4 C5 121.8(11) . . ? C5 C4 H4 119.1 . . ? C3A C4A H4A 119.8 . . ? C3A C4A C5A 120.4(5) . . ? C5A C4A H4A 119.8 . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.5(10) . . ? C6 C5 H5 119.8 . . ? C4A C5A H5A 119.3 . . ? C4A C5A C6A 121.4(4) . . ? C6A C5A H5A 119.3 . . ? C1 C6 C5 118.4(11) . . ? C1 C6 C7 122.4(9) . . ? C5 C6 C7 119.3(10) . . ? C1A C6A C7A 123.1(3) . . ? C5A C6A C1A 117.7(4) . . ? C5A C6A C7A 119.1(3) . . ? C6 C7 H7 117.0 . . ? C8 C7 C6 125.9(9) . . ? C8 C7 H7 117.0 . . ? C6A C7A H7A 110.4 . . ? C6A C7A C8A 119.4(3) . . ? C6A C7A C8A 115.1(3) . 3_757 ? C8A C7A H7A 110.4 . . ? C8A C7A H7A 110.4 3_757 . ? C8A C7A C8A 89.4(2) . 3_757 ? C7 C8 H8 120.1 . . ? C7 C8 C9 119.9(10) . . ? C9 C8 H8 120.1 . . ? C7A C8A C7A 90.6(2) . 3_757 ? C7A C8A H8A 111.1 3_757 . ? C7A C8A H8A 111.1 . . ? C9A C8A C7A 114.9(3) . 3_757 ? C9A C8A C7A 116.5(3) . . ? C9A C8A H8A 111.1 . . ? C10 C9 C8 117.7(11) . . ? O1 C9 C8 118.1(10) . . ? O1 C9 C10 124.1(10) . . ? C8A C9A C10A 112.6(4) . . ? O1A C9A C8A 121.7(4) . . ? O1A C9A C10A 125.7(4) . . ? C9 C10 H10 115.3 . . ? C9 C10 C11 129.4(10) . . ? C11 C10 H10 115.3 . . ? C9A C10A H10A 118.6 . . ? C11A C10A C9A 122.8(5) . . ? C11A C10A H10A 118.6 . . ? C10 C11 H11 114.3 . . ? C10 C11 C12 131.3(9) . . ? C12 C11 H11 114.3 . . ? C10A C11A H11A 119.0 . . ? C10A C11A C12A 122.0(6) . . ? C12A C11A H11A 119.0 . . ? C13 C12 C11 119.9(10) . . ? C13 C12 C17 120.0 . . ? C17 C12 C11 120.0(9) . . ? C12 C13 H13 120.0 . . ? C12 C13 C14 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 H14 120.0 . . ? C15 C14 C13 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 H15 120.0 . . ? C14 C15 C16 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 120.0 . . ? C17 C16 H16 120.0 . . ? C12 C17 H17 120.0 . . ? C16 C17 C12 120.0 . . ? C16 C17 H17 120.0 . . ? C13A C12A C11A 123.3(4) . . ? C13A C12A C17A 120.0 . . ? C17A C12A C11A 116.6(4) . . ? C12A C13A H13A 120.0 . . ? C12A C13A C14A 120.0 . . ? C14A C13A H13A 120.0 . . ? C13A C14A H14A 120.0 . . ? C13A C14A C15A 120.0 . . ? C15A C14A H14A 120.0 . . ? C14A C15A H15A 120.0 . . ? C16A C15A C14A 120.0 . . ? C16A C15A H15A 120.0 . . ? C15A C16A H16A 120.0 . . ? C15A C16A C17A 120.0 . . ? C17A C16A H16A 120.0 . . ? C12A C17A H17A 120.0 . . ? C16A C17A C12A 120.0 . . ? C16A C17A H17A 120.0 . . ? C19 C18 C23 119.6(2) . . ? C19 C18 P1 118.2(2) . . ? C23 C18 P1 122.14(19) . . ? C18 C19 H19 120.0 . . ? C20 C19 C18 120.0(3) . . ? C20 C19 H19 120.0 . . ? C19 C20 H20 119.9 . . ? C21 C20 C19 120.1(3) . . ? C21 C20 H20 119.9 . . ? C20 C21 H21 119.8 . . ? C20 C21 C22 120.4(3) . . ? C22 C21 H21 119.8 . . ? C21 C22 H22 119.8 . . ? C21 C22 C23 120.3(3) . . ? C23 C22 H22 119.8 . . ? C18 C23 H23 120.2 . . ? C22 C23 C18 119.6(3) . . ? C22 C23 H23 120.2 . . ? C25 C24 P1 122.2(2) . . ? C29 C24 C25 119.1(3) . . ? C29 C24 P1 118.6(2) . . ? C24 C25 H25 119.8 . . ? C26 C25 C24 120.5(3) . . ? C26 C25 H25 119.8 . . ? C25 C26 H26 120.2 . . ? C27 C26 C25 119.5(3) . . ? C27 C26 H26 120.2 . . ? C26 C27 H27 119.9 . . ? C28 C27 C26 120.2(3) . . ? C28 C27 H27 119.9 . . ? C27 C28 H28 119.8 . . ? C27 C28 C29 120.4(3) . . ? C29 C28 H28 119.8 . . ? C24 C29 C28 120.2(3) . . ? C24 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C1 P1 S1 113.5(4) . . ? C1A P1 C1 14.9(3) . . ? C1A P1 C18 108.78(16) . . ? C1A P1 C24 100.95(14) . . ? C1A P1 S1 116.63(16) . . ? C18 P1 C1 98.3(4) . . ? C18 P1 S1 112.25(9) . . ? C24 P1 C1 114.6(3) . . ? C24 P1 C18 105.47(11) . . ? C24 P1 S1 111.67(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 0(2) . . . . ? C1 C6 C7 C8 169.0(12) . . . . ? C1A C2A C3A C4A -1.1(8) . . . . ? C1A C6A C7A C8A 100.4(4) . . . 3_757 ? C1A C6A C7A C8A -155.0(4) . . . . ? C2 C1 C6 C5 0(2) . . . . ? C2 C1 C6 C7 178.7(12) . . . . ? C2 C1 P1 C1A 10.4(15) . . . . ? C2 C1 P1 C18 -125.5(10) . . . . ? C2 C1 P1 C24 -14.3(12) . . . . ? C2 C1 P1 S1 115.7(9) . . . . ? C2 C3 C4 C5 1(2) . . . . ? C2A C1A C6A C5A 3.8(6) . . . . ? C2A C1A C6A C7A -171.4(4) . . . . ? C2A C1A P1 C1 -150(2) . . . . ? C2A C1A P1 C18 -103.9(4) . . . . ? C2A C1A P1 C24 6.8(4) . . . . ? C2A C1A P1 S1 128.0(4) . . . . ? C2A C3A C4A C5A 1.4(8) . . . . ? C3 C4 C5 C6 -0.2(19) . . . . ? C3A C4A C5A C6A 1.0(8) . . . . ? C4 C5 C6 C1 -0.1(18) . . . . ? C4 C5 C6 C7 -178.7(10) . . . . ? C4A C5A C6A C1A -3.6(7) . . . . ? C4A C5A C6A C7A 171.8(4) . . . . ? C5 C6 C7 C8 -12.5(17) . . . . ? C5A C6A C7A C8A 29.9(5) . . . . ? C5A C6A C7A C8A -74.7(5) . . . 3_757 ? C6 C1 C2 C3 0(2) . . . . ? C6 C1 P1 C1A -167(3) . . . . ? C6 C1 P1 C18 56.9(13) . . . . ? C6 C1 P1 C24 168.2(11) . . . . ? C6 C1 P1 S1 -61.8(13) . . . . ? C6 C7 C8 C9 -175.9(10) . . . . ? C6A C1A C2A C3A -1.6(7) . . . . ? C6A C1A P1 C1 29(2) . . . . ? C6A C1A P1 C18 75.3(4) . . . . ? C6A C1A P1 C24 -174.0(3) . . . . ? C6A C1A P1 S1 -52.8(4) . . . . ? C6A C7A C8A C7A -118.8(4) . . . 3_757 ? C6A C7A C8A C9A 122.8(4) . . . . ? C7 C8 C9 C10 -168.2(10) . . . . ? C7 C8 C9 O1 8.6(16) . . . . ? C7A C8A C9A C10A 85.7(4) 3_757 . . . ? C7A C8A C9A C10A -170.2(3) . . . . ? C7A C8A C9A O1A -93.0(5) 3_757 . . . ? C7A C8A C9A O1A 11.1(6) . . . . ? C8 C9 C10 C11 17.1(16) . . . . ? C8A C7A C8A C7A 0.0 3_757 . . 3_757 ? C8A C7A C8A C9A -118.4(4) 3_757 . . . ? C8A C9A C10A C11A -146.4(4) . . . . ? C9 C10 C11 C12 177.4(13) . . . . ? C9A C10A C11A C12A 176.7(5) . . . . ? C10 C11 C12 C13 -175.8(11) . . . . ? C10 C11 C12 C17 1(2) . . . . ? C10A C11A C12A C13A 12.8(8) . . . . ? C10A C11A C12A C17A -164.9(6) . . . . ? C11 C12 C13 C14 177(2) . . . . ? C11 C12 C17 C16 -177(2) . . . . ? C11A C12A C13A C14A -177.6(8) . . . . ? C11A C12A C17A C16A 177.8(8) . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C12 C17 C16 0.0 . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C12 0.0 . . . . ? C17 C12 C13 C14 0.0 . . . . ? C12A C13A C14A C15A 0.0 . . . . ? C13A C12A C17A C16A 0.0 . . . . ? C13A C14A C15A C16A 0.0 . . . . ? C14A C15A C16A C17A 0.0 . . . . ? C15A C16A C17A C12A 0.0 . . . . ? C17A C12A C13A C14A 0.0 . . . . ? C18 C19 C20 C21 0.6(5) . . . . ? C19 C18 C23 C22 -1.3(4) . . . . ? C19 C18 P1 C1 -141.4(4) . . . . ? C19 C18 P1 C1A -152.3(2) . . . . ? C19 C18 P1 C24 100.1(2) . . . . ? C19 C18 P1 S1 -21.7(2) . . . . ? C19 C20 C21 C22 -0.8(5) . . . . ? C20 C21 C22 C23 -0.1(5) . . . . ? C21 C22 C23 C18 1.1(4) . . . . ? C23 C18 C19 C20 0.5(4) . . . . ? C23 C18 P1 C1 41.4(4) . . . . ? C23 C18 P1 C1A 30.5(3) . . . . ? C23 C18 P1 C24 -77.1(2) . . . . ? C23 C18 P1 S1 161.10(19) . . . . ? C24 C25 C26 C27 0.1(5) . . . . ? C25 C24 C29 C28 -0.1(4) . . . . ? C25 C24 P1 C1 -68.7(5) . . . . ? C25 C24 P1 C1A -75.0(3) . . . . ? C25 C24 P1 C18 38.2(3) . . . . ? C25 C24 P1 S1 160.4(2) . . . . ? C25 C26 C27 C28 0.5(5) . . . . ? C26 C27 C28 C29 -0.8(5) . . . . ? C27 C28 C29 C24 0.7(4) . . . . ? C29 C24 C25 C26 -0.2(5) . . . . ? C29 C24 P1 C1 107.6(5) . . . . ? C29 C24 P1 C1A 101.3(3) . . . . ? C29 C24 P1 C18 -145.5(2) . . . . ? C29 C24 P1 S1 -23.3(2) . . . . ? O1 C9 C10 C11 -159.4(11) . . . . ? O1A C9A C10A C11A 32.2(7) . . . . ? P1 C1 C2 C3 -177.6(10) . . . . ? P1 C1 C6 C5 177.5(10) . . . . ? P1 C1 C6 C7 -4.0(19) . . . . ? P1 C1A C2A C3A 177.6(4) . . . . ? P1 C1A C6A C5A -175.4(3) . . . . ? P1 C1A C6A C7A 9.4(6) . . . . ? P1 C18 C19 C20 -176.8(2) . . . . ? P1 C18 C23 C22 175.9(2) . . . . ? P1 C24 C25 C26 176.0(2) . . . . ? P1 C24 C29 C28 -176.5(2) . . . . ? ### END data_ijf1038 _database_code_depnum_ccdc_archive 'CCDC 874853' #TrackingRef '- all.cif' _audit_creation_method 'WinGX routine CIF_UPDATE' __chemical_name_systematic ; ? ; _chemical_formula_sum 'C29 H23 O P S' _chemical_formula_moiety 'C29 H23 O P S' _chemical_formula_weight 450.5 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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3833(3) _cell_length_b 17.1058(4) _cell_length_c 14.6168(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.040(3) _cell_angle_gamma 90.00 _cell_volume 2294.51(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4001 _cell_measurement_temperature 110.0 _cell_measurement_theta_max 27.4233 _cell_measurement_theta_min 3.0828 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92996 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_unetI/netI 0.0508 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 9051 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.09 _diffrn_ambient_temperature 110.0 _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -90.00 10.00 1.0000 43.5400 omega____ theta____ kappa____ phi______ frames - -20.1438 -77.0000 90.0000 100 #__ type_ start__ end____ width___ exp.time_ 2 omega -69.00 31.00 1.0000 43.5400 omega____ theta____ kappa____ phi______ frames - -20.1438 0.0000 -120.0000 100 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0401562000 _diffrn_orient_matrix_UB_12 0.0181148000 _diffrn_orient_matrix_UB_13 -0.0303107000 _diffrn_orient_matrix_UB_21 0.0656249000 _diffrn_orient_matrix_UB_22 -0.0061780000 _diffrn_orient_matrix_UB_23 0.0333458000 _diffrn_orient_matrix_UB_31 0.0085897000 _diffrn_orient_matrix_UB_32 -0.0367707000 _diffrn_orient_matrix_UB_33 -0.0206049000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3936 _reflns_number_total 5202 _reflns_odcompleteness_completeness 97.87 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 27.50 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.764 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.065 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 326 _refine_ls_number_reflns 5202 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0600 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+2.7000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1346 _refine_ls_wR_factor_ref 0.1517 _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. The crystal contained a disordered mixture of the monomer and photo-dimer. The ratio of these compounds refined to 0.752:0.248(2). The ADP of the following pairs of atoms were constrained to be equal: O1 O1A, C1A C1, C2 C2A, C3A C3, C4A C4, C6A C6, C7 C7A, C8 C8A, C9A C9, C10, C10A, C11 C11A, C12A C12, C13A C13, C14A C14, C15A C15, C16A C16, C17A C17. The ADP of the following atoms were restrained to be isotropic c9 C9A The bond lengths C10-C11 & C10A-C11A were restrained to be equal. The bond lengths C11-C12 & C11A-C12A were restrained to be equal. Two phenyl rings (C12-C17 & C12A-C17A) were constrained to be regular hexagons with a C-C bond length of 1.39 angstroms. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6080(5) 0.1211(5) 0.3461(6) 0.0229(11) Uani 0.752(2) 1 d P A 2 C1A C 0.645(2) 0.1184(17) 0.341(2) 0.0229(11) Uani 0.248(2) 1 d P A 1 C2 C 0.7520(7) 0.1404(3) 0.3442(4) 0.0309(11) Uani 0.752(2) 1 d P A 2 H2 H 0.7804 0.1441 0.2856 0.037 Uiso 0.752(2) 1 calc PR A 2 C2A C 0.761(3) 0.1601(12) 0.3239(16) 0.0309(11) Uani 0.248(2) 1 d P A 1 H2A H 0.7685 0.1735 0.2619 0.037 Uiso 0.248(2) 1 calc PR A 1 C3 C 0.8551(5) 0.1546(3) 0.4262(3) 0.0394(11) Uani 0.752(2) 1 d P A 2 H3 H 0.9526 0.1672 0.4232 0.047 Uiso 0.752(2) 1 calc PR A 2 C3A C 0.8673(18) 0.1822(10) 0.3991(12) 0.0394(11) Uani 0.248(2) 1 d P A 1 H3A H 0.9514 0.2095 0.3901 0.047 Uiso 0.248(2) 1 calc PR A 1 C4 C 0.8150(6) 0.1501(3) 0.5116(4) 0.0358(12) Uani 0.752(2) 1 d P A 2 H4 H 0.8848 0.1598 0.5676 0.043 Uiso 0.752(2) 1 calc PR A 2 C4A C 0.850(2) 0.1641(12) 0.4874(14) 0.0358(12) Uani 0.248(2) 1 d P A 1 H4A H 0.9191 0.1821 0.5400 0.043 Uiso 0.248(2) 1 calc PR A 1 C5 C 0.6742(6) 0.1316(3) 0.5156(3) 0.0340(11) Uani 0.752(2) 1 d P A 2 H5 H 0.6479 0.1293 0.5749 0.041 Uiso 0.752(2) 1 calc PR A 2 C5A C 0.7314(18) 0.1197(9) 0.5010(9) 0.026(3) Uani 0.248(2) 1 d P A 1 H5A H 0.7229 0.1068 0.5629 0.031 Uiso 0.248(2) 1 calc PR A 1 C6 C 0.5681(5) 0.1160(2) 0.4352(3) 0.0300(8) Uani 0.752(2) 1 d P A 2 C6A C 0.6237(15) 0.0936(8) 0.4244(9) 0.0300(8) Uani 0.248(2) 1 d P A 1 C7 C 0.4163(4) 0.0962(2) 0.4428(2) 0.0294(7) Uani 0.752(2) 1 d P A 2 H7 H 0.3449 0.0954 0.3862 0.035 Uiso 0.752(2) 1 calc PR A 2 C7A C 0.5009(12) 0.0410(6) 0.4414(7) 0.0294(7) Uani 0.248(2) 1 d P . 1 H7A H 0.4143 0.0445 0.3884 0.035 Uiso 0.248(2) 1 calc PR A 1 C8 C 0.3707(5) 0.0794(2) 0.5211(3) 0.0344(8) Uani 0.752(2) 1 d P A 2 H8 H 0.4353 0.0814 0.5804 0.041 Uiso 0.752(2) 1 calc PR A 2 C8A C 0.4545(14) 0.0441(7) 0.5368(8) 0.0344(8) Uani 0.248(2) 1 d P . 1 H8A H 0.5190 0.0803 0.5807 0.041 Uiso 0.248(2) 1 calc PR A 1 C9 C 0.2183(5) 0.0579(2) 0.5124(3) 0.0291(8) Uani 0.752(2) 1 d PU A 2 C9A C 0.2993(18) 0.0634(7) 0.5316(8) 0.0291(8) Uani 0.248(2) 1 d PU A 1 C10 C 0.1600(4) 0.0549(2) 0.5980(2) 0.0293(7) Uani 0.752(2) 1 d PD A 2 H10 H 0.0698 0.0288 0.5952 0.035 Uiso 0.752(2) 1 calc PR A 2 C10A C 0.2841(11) 0.0843(6) 0.6343(7) 0.0293(7) Uani 0.248(2) 1 d PD A 1 H10A H 0.3637 0.1056 0.6782 0.035 Uiso 0.248(2) 1 calc PR A 1 C11 C 0.2261(4) 0.0867(2) 0.6807(2) 0.0255(7) Uani 0.752(2) 1 d PD A 2 H11 H 0.3193 0.1092 0.6826 0.031 Uiso 0.752(2) 1 calc PR A 2 C11A C 0.1580(11) 0.0712(7) 0.6572(8) 0.0255(7) Uani 0.248(2) 1 d PD A 1 H11A H 0.0795 0.0528 0.6101 0.031 Uiso 0.248(2) 1 calc PR A 1 C12 C 0.1717(3) 0.0908(3) 0.7683(2) 0.0259(9) Uani 0.752(2) 1 d PGD A 2 C17 C 0.2528(5) 0.1316(3) 0.8438(2) 0.0307(9) Uani 0.752(2) 1 d PG A 2 H17 H 0.3407 0.1568 0.8381 0.037 Uiso 0.752(2) 1 calc PR A 2 C16 C 0.2053(8) 0.1354(4) 0.9276(2) 0.0364(11) Uani 0.752(2) 1 d PG A 2 H16 H 0.2608 0.1633 0.9792 0.044 Uiso 0.752(2) 1 calc PR A 2 C15 C 0.0768(10) 0.0985(5) 0.9360(4) 0.0353(13) Uani 0.752(2) 1 d PG A 2 H15 H 0.0443 0.1011 0.9933 0.042 Uiso 0.752(2) 1 calc PR A 2 C14 C -0.0043(7) 0.0577(5) 0.8606(5) 0.0356(11) Uani 0.752(2) 1 d PG A 2 H14 H -0.0922 0.0324 0.8663 0.043 Uiso 0.752(2) 1 calc PR A 2 C13 C 0.0431(4) 0.0538(4) 0.7767(4) 0.0320(10) Uani 0.752(2) 1 d PG A 2 H13 H -0.0123 0.0260 0.7252 0.038 Uiso 0.752(2) 1 calc PR A 2 C12A C 0.1319(14) 0.0838(13) 0.7527(7) 0.0259(9) Uani 0.248(2) 1 d PGD A 1 C17A C 0.2262(16) 0.1287(12) 0.8180(9) 0.0307(9) Uani 0.248(2) 1 d PG A 1 H17A H 0.3107 0.1510 0.8024 0.037 Uiso 0.248(2) 1 calc PR A 1 C16A C 0.197(3) 0.1410(14) 0.9063(9) 0.0364(11) Uani 0.248(2) 1 d PG A 1 H16A H 0.2613 0.1717 0.9509 0.044 Uiso 0.248(2) 1 calc PR A 1 C15A C 0.073(3) 0.1084(19) 0.9292(13) 0.0353(13) Uani 0.248(2) 1 d PG A 1 H15A H 0.0532 0.1168 0.9895 0.042 Uiso 0.248(2) 1 calc PR A 1 C14A C -0.021(3) 0.0635(19) 0.8639(17) 0.0356(11) Uani 0.248(2) 1 d PG A 1 H14A H -0.1055 0.0412 0.8796 0.043 Uiso 0.248(2) 1 calc PR A 1 C13A C 0.0083(17) 0.0512(14) 0.7757(14) 0.0320(10) Uani 0.248(2) 1 d PG A 1 H13A H -0.0561 0.0205 0.7311 0.038 Uiso 0.248(2) 1 calc PR A 1 C18 C 0.5724(3) 0.12473(15) 0.14270(17) 0.0266(5) Uani 1 1 d . A . C19 C 0.6156(3) 0.06672(17) 0.08867(19) 0.0349(6) Uani 1 1 d . . . H19 H 0.5970 0.0135 0.1005 0.042 Uiso 1 1 calc R . . C20 C 0.6857(4) 0.08580(19) 0.0173(2) 0.0416(7) Uani 1 1 d . . . H20 H 0.7149 0.0456 -0.0197 0.050 Uiso 1 1 calc R . . C21 C 0.7134(3) 0.16238(19) -0.0003(2) 0.0385(7) Uani 1 1 d . . . H21 H 0.7619 0.1751 -0.0493 0.046 Uiso 1 1 calc R . . C22 C 0.6708(3) 0.22110(18) 0.0533(2) 0.0391(7) Uani 1 1 d . . . H22 H 0.6898 0.2742 0.0410 0.047 Uiso 1 1 calc R . . C23 C 0.6003(3) 0.20249(16) 0.1249(2) 0.0348(6) Uani 1 1 d . . . H23 H 0.5712 0.2428 0.1618 0.042 Uiso 1 1 calc R . . C24 C 0.3352(3) 0.16595(15) 0.23268(16) 0.0241(5) Uani 1 1 d . A . C25 C 0.3582(3) 0.24260(15) 0.26474(17) 0.0292(6) Uani 1 1 d . . . H25 H 0.4539 0.2602 0.2914 0.035 Uiso 1 1 calc R . . C26 C 0.2411(3) 0.29299(16) 0.25753(19) 0.0359(6) Uani 1 1 d . . . H26 H 0.2566 0.3456 0.2781 0.043 Uiso 1 1 calc R . . C27 C 0.1011(4) 0.26682(19) 0.2203(2) 0.0423(7) Uani 1 1 d . . . H27 H 0.0210 0.3016 0.2160 0.051 Uiso 1 1 calc R . . C28 C 0.0770(3) 0.1909(2) 0.1897(2) 0.0446(8) Uani 1 1 d . . . H28 H -0.0191 0.1731 0.1646 0.053 Uiso 1 1 calc R . . C29 C 0.1949(3) 0.14046(16) 0.19587(19) 0.0333(6) Uani 1 1 d . . . H29 H 0.1791 0.0881 0.1747 0.040 Uiso 1 1 calc R . . O1 O 0.1379(4) 0.04423(18) 0.4364(2) 0.0423(7) Uani 0.752(2) 1 d P A 2 O1A O 0.2060(12) 0.0620(6) 0.4564(8) 0.0423(7) Uani 0.248(2) 1 d P A 1 P1 P 0.48476(7) 0.09727(4) 0.23791(4) 0.02363(17) Uani 1 1 d . . . S1 S 0.41764(8) -0.01124(4) 0.22819(5) 0.03444(19) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.013(3) 0.0219(14) 0.0299(17) 0.0030(12) -0.004(3) 0.000(3) C1A 0.013(3) 0.0219(14) 0.0299(17) 0.0030(12) -0.004(3) 0.000(3) C2 0.0208(18) 0.035(3) 0.036(3) -0.0026(19) 0.0036(19) 0.000(2) C2A 0.0208(18) 0.035(3) 0.036(3) -0.0026(19) 0.0036(19) 0.000(2) C3 0.0198(17) 0.048(3) 0.045(3) -0.008(2) -0.0050(19) -0.004(2) C3A 0.0198(17) 0.048(3) 0.045(3) -0.008(2) -0.0050(19) -0.004(2) C4 0.029(3) 0.040(3) 0.030(3) -0.004(2) -0.0114(19) 0.002(2) C4A 0.029(3) 0.040(3) 0.030(3) -0.004(2) -0.0114(19) 0.002(2) C5 0.040(3) 0.033(2) 0.025(2) -0.0006(17) -0.003(2) 0.001(2) C5A 0.021(8) 0.038(7) 0.014(5) -0.001(5) -0.005(5) 0.011(7) C6 0.035(3) 0.028(2) 0.0240(16) 0.0024(15) 0.0001(16) -0.0038(16) C6A 0.035(3) 0.028(2) 0.0240(16) 0.0024(15) 0.0001(16) -0.0038(16) C7 0.0293(18) 0.0331(17) 0.0247(15) -0.0022(13) 0.0033(14) 0.0023(14) C7A 0.0293(18) 0.0331(17) 0.0247(15) -0.0022(13) 0.0033(14) 0.0023(14) C8 0.032(2) 0.043(2) 0.0284(18) -0.0025(15) 0.0050(17) -0.0065(16) C8A 0.032(2) 0.043(2) 0.0284(18) -0.0025(15) 0.0050(17) -0.0065(16) C9 0.0294(16) 0.0280(13) 0.0248(14) -0.0004(11) -0.0061(13) -0.0019(14) C9A 0.0294(16) 0.0280(13) 0.0248(14) -0.0004(11) -0.0061(13) -0.0019(14) C10 0.0314(18) 0.0268(16) 0.0264(17) 0.0031(13) -0.0013(14) 0.0019(14) C10A 0.0314(18) 0.0268(16) 0.0264(17) 0.0031(13) -0.0013(14) 0.0019(14) C11 0.021(2) 0.0263(17) 0.0265(17) 0.0023(13) -0.0018(15) -0.0011(15) C11A 0.021(2) 0.0263(17) 0.0265(17) 0.0023(13) -0.0018(15) -0.0011(15) C12 0.016(2) 0.0302(19) 0.0274(18) -0.0006(17) -0.0042(17) 0.003(2) C17 0.024(2) 0.0412(17) 0.024(3) -0.004(2) -0.0023(18) -0.0033(17) C16 0.0332(19) 0.046(2) 0.028(2) -0.003(2) 0.001(2) -0.0018(16) C15 0.0365(17) 0.037(3) 0.0336(17) 0.0010(18) 0.0101(15) 0.002(2) C14 0.025(2) 0.036(2) 0.0456(18) -0.0025(14) 0.0084(15) 0.002(2) C13 0.018(3) 0.0336(16) 0.0409(16) -0.0017(12) -0.001(2) -0.001(2) C12A 0.016(2) 0.0302(19) 0.0274(18) -0.0006(17) -0.0042(17) 0.003(2) C17A 0.024(2) 0.0412(17) 0.024(3) -0.004(2) -0.0023(18) -0.0033(17) C16A 0.0332(19) 0.046(2) 0.028(2) -0.003(2) 0.001(2) -0.0018(16) C15A 0.0365(17) 0.037(3) 0.0336(17) 0.0010(18) 0.0101(15) 0.002(2) C14A 0.025(2) 0.036(2) 0.0456(18) -0.0025(14) 0.0084(15) 0.002(2) C13A 0.018(3) 0.0336(16) 0.0409(16) -0.0017(12) -0.001(2) -0.001(2) C18 0.0209(13) 0.0294(13) 0.0280(12) -0.0009(10) 0.0014(10) 0.0042(10) C19 0.0399(17) 0.0318(14) 0.0309(14) -0.0062(11) 0.0026(12) 0.0026(13) C20 0.0468(19) 0.0452(17) 0.0335(15) -0.0111(13) 0.0101(14) 0.0079(14) C21 0.0329(16) 0.0539(18) 0.0305(14) -0.0013(13) 0.0107(12) 0.0033(14) C22 0.0364(17) 0.0388(16) 0.0468(17) 0.0020(13) 0.0192(14) 0.0000(13) C23 0.0346(16) 0.0302(14) 0.0439(16) -0.0021(12) 0.0180(13) 0.0037(12) C24 0.0234(13) 0.0306(13) 0.0184(11) 0.0011(9) 0.0041(9) -0.0001(10) C25 0.0337(15) 0.0298(13) 0.0245(12) 0.0000(10) 0.0071(11) -0.0003(11) C26 0.0470(18) 0.0298(14) 0.0335(14) -0.0009(11) 0.0143(13) 0.0066(13) C27 0.0399(18) 0.0456(17) 0.0445(17) 0.0035(14) 0.0155(14) 0.0166(14) C28 0.0259(15) 0.0520(19) 0.0543(19) -0.0017(15) 0.0047(14) 0.0063(14) C29 0.0302(15) 0.0338(14) 0.0344(14) -0.0046(11) 0.0029(12) 0.0004(12) O1 0.045(2) 0.0433(17) 0.0303(15) -0.0049(12) -0.0102(14) -0.0040(15) O1A 0.045(2) 0.0433(17) 0.0303(15) -0.0049(12) -0.0102(14) -0.0040(15) P1 0.0219(3) 0.0231(3) 0.0230(3) 0.0009(2) -0.0019(2) -0.0010(3) S1 0.0277(4) 0.0246(3) 0.0462(4) 0.0001(3) -0.0033(3) -0.0030(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.397(7) . ? C1 C6 1.431(8) . ? C1 P1 1.800(8) . ? C1A C2A 1.37(3) . ? C1A C6A 1.35(3) . ? C1A P1 1.93(3) . ? C2 H2 0.9500 . ? C2 C3 1.396(8) . ? C2A H2A 0.9500 . ? C2A C3A 1.37(3) . ? C3 H3 0.9500 . ? C3 C4 1.379(7) . ? C3A H3A 0.9500 . ? C3A C4A 1.37(2) . ? C4 H4 0.9500 . ? C4 C5 1.371(7) . ? C4A H4A 0.9500 . ? C4A C5A 1.39(2) . ? C5 H5 0.9500 . ? C5 C6 1.398(6) . ? C5A H5A 0.9500 . ? C5A C6A 1.42(2) . ? C6 C7 1.490(5) . ? C6A C7A 1.522(17) . ? C7 H7 0.9500 . ? C7 C8 1.334(5) . ? C7A H7A 1.0000 . ? C7A C8A 1.546(15) . ? C7A C8A 1.530(16) 3_656 ? C8 H8 0.9500 . ? C8 C9 1.456(5) . ? C8A C7A 1.530(16) 3_656 ? C8A H8A 1.0000 . ? C8A C9A 1.480(19) . ? C9 C10 1.467(5) . ? C9 O1 1.228(5) . ? C9A C10A 1.578(16) . ? C9A O1A 1.254(15) . ? C10 H10 0.9500 . ? C10 C11 1.352(4) . ? C10A H10A 0.9500 . ? C10A C11A 1.315(9) . ? C11 H11 0.9500 . ? C11 C12 1.476(4) . ? C11A H11A 0.9500 . ? C11A C12A 1.483(9) . ? C12 C17 1.3900 . ? C12 C13 1.3900 . ? C17 H17 0.9500 . ? C17 C16 1.3900 . ? C16 H16 0.9500 . ? C16 C15 1.3900 . ? C15 H15 0.9500 . ? C15 C14 1.3900 . ? C14 H14 0.9500 . ? C14 C13 1.3900 . ? C13 H13 0.9500 . ? C12A C17A 1.3900 . ? C12A C13A 1.3900 . ? C17A H17A 0.9500 . ? C17A C16A 1.3900 . ? C16A H16A 0.9500 . ? C16A C15A 1.3900 . ? C15A H15A 0.9500 . ? C15A C14A 1.3900 . ? C14A H14A 0.9500 . ? C14A C13A 1.3900 . ? C13A H13A 0.9500 . ? C18 C19 1.380(4) . ? C18 C23 1.391(4) . ? C18 P1 1.820(3) . ? C19 H19 0.9500 . ? C19 C20 1.384(4) . ? C20 H20 0.9500 . ? C20 C21 1.370(4) . ? C21 H21 0.9500 . ? C21 C22 1.383(4) . ? C22 H22 0.9500 . ? C22 C23 1.387(4) . ? C23 H23 0.9500 . ? C24 C25 1.394(4) . ? C24 C29 1.384(4) . ? C24 P1 1.819(3) . ? C25 H25 0.9500 . ? C25 C26 1.383(4) . ? C26 H26 0.9500 . ? C26 C27 1.387(4) . ? C27 H27 0.9500 . ? C27 C28 1.377(5) . ? C28 H28 0.9500 . ? C28 C29 1.391(4) . ? C29 H29 0.9500 . ? P1 S1 1.9557(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.0(6) . . ? C2 C1 P1 118.9(5) . . ? C6 C1 P1 122.9(4) . . ? C2A C1A P1 119(2) . . ? C6A C1A C2A 127(2) . . ? C6A C1A P1 114.1(16) . . ? C1 C2 H2 119.2 . . ? C3 C2 C1 121.6(6) . . ? C3 C2 H2 119.2 . . ? C1A C2A H2A 121.0 . . ? C1A C2A C3A 118(2) . . ? C3A C2A H2A 121.0 . . ? C2 C3 H3 120.1 . . ? C4 C3 C2 119.8(5) . . ? C4 C3 H3 120.1 . . ? C2A C3A H3A 120.5 . . ? C4A C3A C2A 118.9(17) . . ? C4A C3A H3A 120.5 . . ? C3 C4 H4 120.0 . . ? C5 C4 C3 119.9(5) . . ? C5 C4 H4 120.0 . . ? C3A C4A H4A 119.5 . . ? C3A C4A C5A 120.9(17) . . ? C5A C4A H4A 119.5 . . ? C4 C5 H5 119.0 . . ? C4 C5 C6 122.1(5) . . ? C6 C5 H5 119.0 . . ? C4A C5A H5A 119.4 . . ? C4A C5A C6A 121.2(14) . . ? C6A C5A H5A 119.4 . . ? C1 C6 C7 121.1(4) . . ? C5 C6 C1 118.6(5) . . ? C5 C6 C7 120.3(4) . . ? C1A C6A C5A 113.6(16) . . ? C1A C6A C7A 126.5(16) . . ? C5A C6A C7A 119.9(12) . . ? C6 C7 H7 116.7 . . ? C8 C7 C6 126.6(3) . . ? C8 C7 H7 116.7 . . ? C6A C7A H7A 111.1 . . ? C6A C7A C8A 114.4(10) . 3_656 ? C6A C7A C8A 119.5(10) . . ? C8A C7A H7A 111.1 3_656 . ? C8A C7A H7A 111.1 . . ? C8A C7A C8A 87.7(9) 3_656 . ? C7 C8 H8 121.1 . . ? C7 C8 C9 117.7(3) . . ? C9 C8 H8 121.1 . . ? C7A C8A C7A 92.3(9) 3_656 . ? C7A C8A H8A 110.7 . . ? C7A C8A H8A 110.7 3_656 . ? C9A C8A C7A 114.9(10) . . ? C9A C8A C7A 116.5(10) . 3_656 ? C9A C8A H8A 110.7 . . ? C8 C9 C10 117.9(4) . . ? O1 C9 C8 122.2(4) . . ? O1 C9 C10 119.8(4) . . ? C8A C9A C10A 106.5(10) . . ? O1A C9A C8A 122.7(12) . . ? O1A C9A C10A 130.8(14) . . ? C9 C10 H10 117.8 . . ? C11 C10 C9 124.4(4) . . ? C11 C10 H10 117.8 . . ? C9A C10A H10A 121.0 . . ? C11A C10A C9A 117.9(11) . . ? C11A C10A H10A 121.0 . . ? C10 C11 H11 115.9 . . ? C10 C11 C12 128.2(3) . . ? C12 C11 H11 115.9 . . ? C10A C11A H11A 118.3 . . ? C10A C11A C12A 123.3(11) . . ? C12A C11A H11A 118.3 . . ? C17 C12 C11 118.8(3) . . ? C17 C12 C13 120.0 . . ? C13 C12 C11 121.2(3) . . ? C12 C17 H17 120.0 . . ? C12 C17 C16 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C16 H16 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 C16 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C14 H14 120.0 . . ? C13 C14 C15 120.0 . . ? C13 C14 H14 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 H13 120.0 . . ? C17A C12A C11A 121.4(12) . . ? C17A C12A C13A 120.0 . . ? C13A C12A C11A 118.6(12) . . ? C12A C17A H17A 120.0 . . ? C16A C17A C12A 120.0 . . ? C16A C17A H17A 120.0 . . ? C17A C16A H16A 120.0 . . ? C17A C16A C15A 120.0 . . ? C15A C16A H16A 120.0 . . ? C16A C15A H15A 120.0 . . ? C16A C15A C14A 120.0 . . ? C14A C15A H15A 120.0 . . ? C15A C14A H14A 120.0 . . ? C13A C14A C15A 120.0 . . ? C13A C14A H14A 120.0 . . ? C12A C13A H13A 120.0 . . ? C14A C13A C12A 120.0 . . ? C14A C13A H13A 120.0 . . ? C19 C18 C23 119.4(2) . . ? C19 C18 P1 119.0(2) . . ? C23 C18 P1 121.5(2) . . ? C18 C19 H19 119.9 . . ? C18 C19 C20 120.3(3) . . ? C20 C19 H19 119.9 . . ? C19 C20 H20 119.8 . . ? C21 C20 C19 120.4(3) . . ? C21 C20 H20 119.8 . . ? C20 C21 H21 120.0 . . ? C20 C21 C22 119.9(3) . . ? C22 C21 H21 120.0 . . ? C21 C22 H22 120.0 . . ? C21 C22 C23 120.0(3) . . ? C23 C22 H22 120.0 . . ? C18 C23 H23 120.0 . . ? C22 C23 C18 119.9(3) . . ? C22 C23 H23 120.0 . . ? C25 C24 P1 121.9(2) . . ? C29 C24 C25 119.7(2) . . ? C29 C24 P1 118.4(2) . . ? C24 C25 H25 120.2 . . ? C26 C25 C24 119.7(3) . . ? C26 C25 H25 120.2 . . ? C25 C26 H26 120.0 . . ? C25 C26 C27 120.1(3) . . ? C27 C26 H26 120.0 . . ? C26 C27 H27 119.7 . . ? C28 C27 C26 120.6(3) . . ? C28 C27 H27 119.7 . . ? C27 C28 H28 120.3 . . ? C27 C28 C29 119.3(3) . . ? C29 C28 H28 120.3 . . ? C24 C29 C28 120.6(3) . . ? C24 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C1 P1 C1A 10.9(8) . . ? C1 P1 C18 107.7(2) . . ? C1 P1 C24 103.8(2) . . ? C1 P1 S1 114.6(3) . . ? C1A P1 S1 115.0(9) . . ? C18 P1 C1A 98.3(8) . . ? C18 P1 S1 112.31(9) . . ? C24 P1 C1A 112.4(8) . . ? C24 P1 C18 105.60(11) . . ? C24 P1 S1 112.08(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 C1 C2 C3 C4 -0.5(8) . . . . ? C1 C6 C7 C8 170.3(5) . . . . ? C1A C2A C3A C4A -2(3) . . . . ? C1A C6A C7A C8A -155.7(17) . . . . ? C1A C6A C7A C8A 102.4(19) . . . 3_656 ? C2 C1 C6 C5 0.9(9) . . . . ? C2 C1 C6 C7 179.6(5) . . . . ? C2 C1 P1 C1A 19(5) . . . . ? C2 C1 P1 C18 -12.1(6) . . . . ? C2 C1 P1 C24 -123.7(5) . . . . ? C2 C1 P1 S1 113.7(6) . . . . ? C2 C3 C4 C5 0.2(8) . . . . ? C2A C1A C6A C5A 5(3) . . . . ? C2A C1A C6A C7A -174(2) . . . . ? C2A C1A P1 C1 -137(7) . . . . ? C2A C1A P1 C18 13(2) . . . . ? C2A C1A P1 C24 -98(2) . . . . ? C2A C1A P1 S1 132.4(19) . . . . ? C2A C3A C4A C5A 4(3) . . . . ? C3 C4 C5 C6 0.7(8) . . . . ? C3A C4A C5A C6A -2(3) . . . . ? C4 C5 C6 C1 -1.2(8) . . . . ? C4 C5 C6 C7 -180.0(5) . . . . ? C4A C5A C6A C1A -3(2) . . . . ? C4A C5A C6A C7A 176.2(15) . . . . ? C5 C6 C7 C8 -11.0(6) . . . . ? C5A C6A C7A C8A -76.2(14) . . . 3_656 ? C5A C6A C7A C8A 25.7(17) . . . . ? C6 C1 C2 C3 -0.1(9) . . . . ? C6 C1 P1 C1A -156(6) . . . . ? C6 C1 P1 C18 172.4(5) . . . . ? C6 C1 P1 C24 60.8(6) . . . . ? C6 C1 P1 S1 -61.8(6) . . . . ? C6 C7 C8 C9 -177.1(3) . . . . ? C6A C1A C2A C3A -2(4) . . . . ? C6A C1A P1 C1 39(5) . . . . ? C6A C1A P1 C18 -171.2(16) . . . . ? C6A C1A P1 C24 78.1(19) . . . . ? C6A C1A P1 S1 -51.8(19) . . . . ? C6A C7A C8A C7A -116.9(12) . . . 3_656 ? C6A C7A C8A C9A 122.4(12) . . . . ? C7 C8 C9 C10 -167.9(3) . . . . ? C7 C8 C9 O1 10.5(6) . . . . ? C7A C8A C9A C10A -166.1(9) . . . . ? C7A C8A C9A C10A 87.7(12) 3_656 . . . ? C7A C8A C9A O1A 13.7(19) . . . . ? C7A C8A C9A O1A -92.6(15) 3_656 . . . ? C8 C9 C10 C11 15.3(5) . . . . ? C8A C7A C8A C7A 0.0 3_656 . . 3_656 ? C8A C7A C8A C9A -120.7(12) 3_656 . . . ? C8A C9A C10A C11A -151.5(11) . . . . ? C9 C10 C11 C12 175.8(4) . . . . ? C9A C10A C11A C12A 176.3(13) . . . . ? C10 C11 C12 C17 -175.1(4) . . . . ? C10 C11 C12 C13 5.8(6) . . . . ? C10A C11A C12A C17A 17(2) . . . . ? C10A C11A C12A C13A -164.7(14) . . . . ? C11 C12 C17 C16 -179.0(5) . . . . ? C11 C12 C13 C14 179.0(5) . . . . ? C11A C12A C17A C16A 178.4(19) . . . . ? C11A C12A C13A C14A -178.4(18) . . . . ? C12 C17 C16 C15 0.0 . . . . ? C17 C12 C13 C14 0.0 . . . . ? C17 C16 C15 C14 0.0 . . . . ? C16 C15 C14 C13 0.0 . . . . ? C15 C14 C13 C12 0.0 . . . . ? C13 C12 C17 C16 0.0 . . . . ? C12A C17A C16A C15A 0.0 . . . . ? C17A C12A C13A C14A 0.0 . . . . ? C17A C16A C15A C14A 0.0 . . . . ? C16A C15A C14A C13A 0.0 . . . . ? C15A C14A C13A C12A 0.0 . . . . ? C13A C12A C17A C16A 0.0 . . . . ? C18 C19 C20 C21 0.2(5) . . . . ? C19 C18 C23 C22 0.1(4) . . . . ? C19 C18 P1 C1 111.6(3) . . . . ? C19 C18 P1 C1A 105.9(9) . . . . ? C19 C18 P1 C24 -137.9(2) . . . . ? C19 C18 P1 S1 -15.5(2) . . . . ? C19 C20 C21 C22 -0.1(5) . . . . ? C20 C21 C22 C23 0.1(5) . . . . ? C21 C22 C23 C18 -0.1(5) . . . . ? C23 C18 C19 C20 -0.1(4) . . . . ? C23 C18 P1 C1 -66.6(3) . . . . ? C23 C18 P1 C1A -72.3(9) . . . . ? C23 C18 P1 C24 43.8(3) . . . . ? C23 C18 P1 S1 166.3(2) . . . . ? C24 C25 C26 C27 1.3(4) . . . . ? C25 C24 C29 C28 0.7(4) . . . . ? C25 C24 P1 C1 36.7(3) . . . . ? C25 C24 P1 C1A 29.6(9) . . . . ? C25 C24 P1 C18 -76.5(2) . . . . ? C25 C24 P1 S1 160.94(18) . . . . ? C25 C26 C27 C28 -0.4(4) . . . . ? C26 C27 C28 C29 -0.4(5) . . . . ? C27 C28 C29 C24 0.2(4) . . . . ? C29 C24 C25 C26 -1.5(4) . . . . ? C29 C24 P1 C1 -143.1(3) . . . . ? C29 C24 P1 C1A -150.2(9) . . . . ? C29 C24 P1 C18 103.7(2) . . . . ? C29 C24 P1 S1 -18.9(2) . . . . ? O1 C9 C10 C11 -163.1(4) . . . . ? O1A C9A C10A C11A 29(2) . . . . ? P1 C1 C2 C3 -175.8(4) . . . . ? P1 C1 C6 C5 176.4(4) . . . . ? P1 C1 C6 C7 -4.8(8) . . . . ? P1 C1A C2A C3A 173.0(16) . . . . ? P1 C1A C6A C5A -170.8(13) . . . . ? P1 C1A C6A C7A 10(3) . . . . ? P1 C18 C19 C20 -178.4(2) . . . . ? P1 C18 C23 C22 178.3(2) . . . . ? P1 C24 C25 C26 178.74(19) . . . . ? P1 C24 C29 C28 -179.5(2) . . . . ? ### END