# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_section_title ; Facile synthesis of luminescent benzo-1,2-dihydrophosphinines from a phosphaalkene ; _publ_contact_author_name 'Kim M Baines' _publ_contact_author_address ;Department of Chemistry University of Western Ontario London, ON N6A 5B7 ; _publ_contact_author_email kbaines2@uwo.ca loop_ _publ_author_name _publ_author_address K.Baines ;Department of Chemistry University of Western Ontario London, ON N6A 5B7 ; L.Pavelka ;Department of Chemistry University of Western Ontario London, ON N6A 5B7 ; data_07089 _database_code_depnum_ccdc_archive 'CCDC 842629' #TrackingRef '6998_web_deposit_cif_file_0_LauraPavelka_1314899584.07089.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H27 P S' _exptl_crystal_recrystallization_method 'diff hexanes into Et2O/C6H6' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour colourless _diffrn_ambient_temperature 150(2) _chemical_formula_weight 450.55 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.307(2) _cell_length_b 11.822(2) _cell_length_c 20.330(4) _cell_angle_alpha 87.82(3) _cell_angle_beta 76.16(3) _cell_angle_gamma 62.43(3) _cell_volume 2330.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20638 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 30.03 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9208 _exptl_absorpt_correction_T_max 0.9359 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scan, and \w scanes with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16932 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 30.03 _reflns_number_total 13308 _reflns_number_gt 12159 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0586P)^2^+1.4729P] 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 13308 _refine_ls_number_parameters 593 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1286 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.23322(4) 0.54320(4) 0.41490(2) 0.02070(10) Uani 1 1 d . . . S1 S 0.13735(5) 0.63183(5) 0.50587(2) 0.02957(11) Uani 1 1 d . . . C1 C 0.12138(18) 0.52030(17) 0.37364(9) 0.0225(3) Uani 1 1 d . . . H1 H 0.0411 0.5221 0.4002 0.027 Uiso 1 1 calc R . . C2 C 0.14948(17) 0.50064(16) 0.30580(9) 0.0205(3) Uani 1 1 d . . . C3 C 0.27659(17) 0.49505(16) 0.26054(9) 0.0210(3) Uani 1 1 d . . . C4 C 0.34128(17) 0.56022(16) 0.28094(9) 0.0202(3) Uani 1 1 d . . . C5 C 0.28909(17) 0.63446(16) 0.34992(9) 0.0211(3) Uani 1 1 d . . . H5 H 0.3688 0.6356 0.3604 0.025 Uiso 1 1 calc R . . C6 C 0.38213(18) 0.38804(17) 0.41747(9) 0.0215(3) Uani 1 1 d . . . C7 C 0.3655(2) 0.27606(19) 0.42599(10) 0.0280(4) Uani 1 1 d . . . C8 C 0.4751(2) 0.16178(19) 0.43542(10) 0.0284(4) Uani 1 1 d . . . H8 H 0.4641 0.0883 0.4392 0.034 Uiso 1 1 calc R . . C9 C 0.59929(19) 0.15304(18) 0.43934(9) 0.0253(4) Uani 1 1 d . . . C10 C 0.61379(18) 0.26372(17) 0.43193(9) 0.0239(4) Uani 1 1 d . . . H10 H 0.6967 0.2598 0.4343 0.029 Uiso 1 1 calc R . . C11 C 0.50925(17) 0.38000(17) 0.42110(9) 0.0212(3) Uani 1 1 d . . . C12 C 0.2318(3) 0.2722(3) 0.42956(17) 0.0557(8) Uani 1 1 d . . . H12A H 0.2164 0.2771 0.3849 0.084 Uiso 1 1 calc R . . H12B H 0.1568 0.3433 0.4591 0.084 Uiso 1 1 calc R . . H12C H 0.2378 0.1936 0.4470 0.084 Uiso 1 1 calc R . . C13 C 0.7117(2) 0.02988(19) 0.45422(12) 0.0355(5) Uani 1 1 d . . . H13A H 0.7165 -0.0409 0.4300 0.053 Uiso 1 1 calc R . . H13B H 0.6919 0.0206 0.5021 0.053 Uiso 1 1 calc R . . H13C H 0.7982 0.0313 0.4400 0.053 Uiso 1 1 calc R . . C14 C 0.54043(19) 0.49211(18) 0.41657(10) 0.0254(4) Uani 1 1 d . . . H14A H 0.6191 0.4711 0.4342 0.038 Uiso 1 1 calc R . . H14B H 0.4623 0.5659 0.4427 0.038 Uiso 1 1 calc R . . H14C H 0.5596 0.5103 0.3699 0.038 Uiso 1 1 calc R . . C15 C 0.04767(17) 0.48859(16) 0.27524(9) 0.0216(3) Uani 1 1 d . . . C16 C -0.02330(19) 0.42352(18) 0.30748(10) 0.0260(4) Uani 1 1 d . . . H16 H -0.0003 0.3802 0.3453 0.031 Uiso 1 1 calc R . . C17 C -0.1278(2) 0.4232(2) 0.28334(11) 0.0318(4) Uani 1 1 d . . . H17 H -0.1737 0.3785 0.3047 0.038 Uiso 1 1 calc R . . C18 C -0.1644(2) 0.4887(2) 0.22784(12) 0.0342(5) Uani 1 1 d . . . H18 H -0.2363 0.4900 0.2126 0.041 Uiso 1 1 calc R . . C19 C -0.0938(2) 0.5524(2) 0.19484(11) 0.0331(4) Uani 1 1 d . . . H19 H -0.1179 0.5962 0.1573 0.040 Uiso 1 1 calc R . . C20 C 0.0132(2) 0.55079(18) 0.21802(10) 0.0267(4) Uani 1 1 d . . . H20 H 0.0621 0.5917 0.1950 0.032 Uiso 1 1 calc R . . C21 C 0.33371(19) 0.42633(18) 0.19680(10) 0.0259(4) Uani 1 1 d . . . H21 H 0.2937 0.3805 0.1836 0.031 Uiso 1 1 calc R . . C22 C 0.4488(2) 0.42499(18) 0.15276(10) 0.0281(4) Uani 1 1 d . . . H22 H 0.4860 0.3781 0.1106 0.034 Uiso 1 1 calc R . . C23 C 0.50805(19) 0.49387(18) 0.17190(10) 0.0273(4) Uani 1 1 d . . . H23 H 0.5833 0.4959 0.1419 0.033 Uiso 1 1 calc R . . C24 C 0.45529(18) 0.55979(17) 0.23569(9) 0.0235(3) Uani 1 1 d . . . H24 H 0.4968 0.6045 0.2484 0.028 Uiso 1 1 calc R . . C25 C 0.18168(18) 0.77405(17) 0.35208(9) 0.0231(3) Uani 1 1 d . . . C26 C 0.1676(2) 0.86194(19) 0.40136(11) 0.0313(4) Uani 1 1 d . . . H26 H 0.2159 0.8329 0.4348 0.038 Uiso 1 1 calc R . . C27 C 0.0821(2) 0.9924(2) 0.40084(12) 0.0361(5) Uani 1 1 d . . . H27 H 0.0745 1.0502 0.4334 0.043 Uiso 1 1 calc R . . C28 C 0.0086(2) 1.03610(19) 0.35201(12) 0.0356(5) Uani 1 1 d . . . H28 H -0.0475 1.1233 0.3512 0.043 Uiso 1 1 calc R . . C29 C 0.0187(2) 0.9495(2) 0.30417(12) 0.0371(5) Uani 1 1 d . . . H29 H -0.0322 0.9788 0.2718 0.045 Uiso 1 1 calc R . . C30 C 0.1046(2) 0.81926(19) 0.30441(10) 0.0297(4) Uani 1 1 d . . . H30 H 0.1103 0.7619 0.2722 0.036 Uiso 1 1 calc R . . P51 P 0.56187(5) -0.06736(4) 0.15111(3) 0.02490(11) Uani 1 1 d . . . S51 S 0.5164(3) -0.2067(3) 0.15900(16) 0.0200(5) Uani 0.4950(16) 1 d P A 1 S51A S 0.5004(4) -0.2021(4) 0.1647(2) 0.0564(13) Uani 0.4950(16) 1 d P A 1 C51 C 0.7402(2) -0.13585(18) 0.10658(10) 0.0286(4) Uani 1 1 d . A . H51 H 0.7738 -0.2031 0.0736 0.034 Uiso 1 1 calc R . . C52 C 0.8291(2) -0.09675(18) 0.11760(10) 0.0273(4) Uani 1 1 d . . . C53 C 0.7802(2) 0.02100(17) 0.16194(10) 0.0267(4) Uani 1 1 d . A . C54 C 0.65587(18) 0.06923(16) 0.21347(9) 0.0221(3) Uani 1 1 d . . . C55 C 0.56515(19) 0.00353(16) 0.23038(9) 0.0226(3) Uani 1 1 d . A . H55 H 0.4711 0.0709 0.2498 0.027 Uiso 1 1 calc R . . C56 C 0.45056(19) 0.07113(17) 0.11272(9) 0.0241(4) Uani 1 1 d . A . C57 C 0.3068(2) 0.13289(18) 0.14468(11) 0.0293(4) Uani 1 1 d . . . C58 C 0.2171(2) 0.23773(19) 0.11781(12) 0.0354(5) Uani 1 1 d . A . H58 H 0.1236 0.2762 0.1394 0.043 Uiso 1 1 calc R . . C59 C 0.2608(2) 0.28691(19) 0.06075(12) 0.0368(5) Uani 1 1 d . . . C60 C 0.3983(3) 0.2282(2) 0.02902(11) 0.0355(5) Uani 1 1 d . A . H60 H 0.4286 0.2613 -0.0098 0.043 Uiso 1 1 calc R . . C61 C 0.4970(2) 0.11855(19) 0.05267(10) 0.0295(4) Uani 1 1 d . . . C62 C 0.2408(2) 0.0918(2) 0.20879(14) 0.0465(6) Uani 1 1 d . A . H62A H 0.1426 0.1336 0.2151 0.070 Uiso 1 1 calc R . . H62B H 0.2626 0.1151 0.2473 0.070 Uiso 1 1 calc R . . H62C H 0.2754 0.0007 0.2045 0.070 Uiso 1 1 calc R . . C63 C 0.1605(3) 0.4047(2) 0.03339(14) 0.0476(6) Uani 1 1 d . A . H63A H 0.1393 0.4802 0.0599 0.071 Uiso 1 1 calc R . . H63B H 0.0773 0.3992 0.0362 0.071 Uiso 1 1 calc R . . H63C H 0.2015 0.4089 -0.0132 0.071 Uiso 1 1 calc R . . C64 C 0.6424(2) 0.0617(2) 0.00925(11) 0.0358(5) Uani 1 1 d . A . H64A H 0.6996 0.0737 0.0334 0.054 Uiso 1 1 calc R . . H64B H 0.6440 0.1032 -0.0322 0.054 Uiso 1 1 calc R . . H64C H 0.6764 -0.0282 -0.0011 0.054 Uiso 1 1 calc R . . C65 C 0.9788(2) -0.17146(18) 0.08415(11) 0.0316(4) Uani 1 1 d . A . C66 C 1.0230(2) -0.2166(2) 0.01553(12) 0.0391(5) Uani 1 1 d . . . H66 H 0.9591 -0.1970 -0.0101 0.047 Uiso 1 1 calc R A . C67 C 1.1623(3) -0.2906(2) -0.01404(13) 0.0474(6) Uani 1 1 d . A . H67 H 1.1918 -0.3200 -0.0598 0.057 Uiso 1 1 calc R . . C68 C 1.2575(3) -0.3208(2) 0.02399(14) 0.0487(6) Uani 1 1 d . . . H68 H 1.3507 -0.3721 0.0040 0.058 Uiso 1 1 calc R A . C69 C 1.2153(3) -0.2751(2) 0.09190(14) 0.0448(6) Uani 1 1 d . A . H69 H 1.2797 -0.2947 0.1173 0.054 Uiso 1 1 calc R . . C70 C 1.0775(2) -0.2009(2) 0.12101(12) 0.0359(5) Uani 1 1 d . . . H70 H 1.0492 -0.1695 0.1663 0.043 Uiso 1 1 calc R A . C71 C 0.8587(2) 0.08626(19) 0.15238(11) 0.0311(4) Uani 1 1 d . . . H71 H 0.9393 0.0563 0.1177 0.037 Uiso 1 1 calc R A . C72 C 0.8182(2) 0.19461(18) 0.19372(11) 0.0298(4) Uani 1 1 d . A . H72 H 0.8708 0.2375 0.1866 0.036 Uiso 1 1 calc R . . C73 C 0.6994(2) 0.23894(18) 0.24561(10) 0.0272(4) Uani 1 1 d . . . H73 H 0.6737 0.3102 0.2744 0.033 Uiso 1 1 calc R A . C74 C 0.61854(19) 0.17766(17) 0.25495(9) 0.0249(4) Uani 1 1 d . A . H74 H 0.5378 0.2094 0.2895 0.030 Uiso 1 1 calc R . . C75 C 0.60273(19) -0.09153(17) 0.28400(9) 0.0230(3) Uani 1 1 d . . . C76 C 0.5021(2) -0.11912(19) 0.32456(10) 0.0300(4) Uani 1 1 d . A . H76 H 0.4137 -0.0809 0.3178 0.036 Uiso 1 1 calc R . . C77 C 0.5334(2) -0.2034(2) 0.37490(11) 0.0351(5) Uani 1 1 d . . . H77 H 0.4656 -0.2210 0.4015 0.042 Uiso 1 1 calc R A . C78 C 0.6644(2) -0.26140(19) 0.38577(10) 0.0337(4) Uani 1 1 d . A . H78 H 0.6853 -0.3183 0.4192 0.040 Uiso 1 1 calc R . . C79 C 0.7636(2) -0.23334(18) 0.34622(10) 0.0307(4) Uani 1 1 d . . . H79 H 0.8516 -0.2710 0.3534 0.037 Uiso 1 1 calc R A . C80 C 0.7332(2) -0.14923(17) 0.29565(10) 0.0264(4) Uani 1 1 d . A . H80 H 0.8012 -0.1315 0.2694 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0191(2) 0.0273(2) 0.0186(2) 0.00238(17) -0.00554(16) -0.01277(18) S1 0.0249(2) 0.0426(3) 0.0209(2) -0.00315(19) -0.00278(17) -0.0166(2) C1 0.0201(8) 0.0276(8) 0.0235(8) 0.0043(7) -0.0066(6) -0.0139(7) C2 0.0200(8) 0.0201(7) 0.0234(8) 0.0026(6) -0.0069(6) -0.0104(6) C3 0.0204(8) 0.0207(8) 0.0218(8) 0.0025(6) -0.0050(6) -0.0097(7) C4 0.0201(8) 0.0197(7) 0.0210(8) 0.0032(6) -0.0060(6) -0.0093(6) C5 0.0206(8) 0.0236(8) 0.0220(8) 0.0018(6) -0.0065(6) -0.0123(7) C6 0.0231(8) 0.0281(8) 0.0170(8) 0.0043(7) -0.0065(6) -0.0145(7) C7 0.0286(9) 0.0348(10) 0.0304(10) 0.0120(8) -0.0125(8) -0.0211(8) C8 0.0360(10) 0.0287(9) 0.0288(10) 0.0079(8) -0.0116(8) -0.0206(8) C9 0.0269(9) 0.0263(9) 0.0211(9) -0.0013(7) -0.0046(7) -0.0116(7) C10 0.0208(8) 0.0268(8) 0.0239(9) -0.0005(7) -0.0058(7) -0.0107(7) C11 0.0213(8) 0.0252(8) 0.0185(8) -0.0013(6) -0.0040(6) -0.0123(7) C12 0.0475(14) 0.0518(14) 0.100(2) 0.0490(15) -0.0451(15) -0.0401(12) C13 0.0307(10) 0.0272(9) 0.0443(13) 0.0033(9) -0.0093(9) -0.0101(8) C14 0.0237(8) 0.0265(9) 0.0309(10) 0.0030(7) -0.0105(7) -0.0141(7) C15 0.0207(8) 0.0228(8) 0.0223(8) -0.0007(7) -0.0063(6) -0.0104(7) C16 0.0246(9) 0.0278(9) 0.0289(10) 0.0014(7) -0.0077(7) -0.0143(7) C17 0.0244(9) 0.0349(10) 0.0405(11) -0.0051(9) -0.0067(8) -0.0176(8) C18 0.0244(9) 0.0350(10) 0.0440(12) -0.0078(9) -0.0150(8) -0.0106(8) C19 0.0339(10) 0.0303(10) 0.0349(11) 0.0000(8) -0.0191(9) -0.0095(8) C20 0.0289(9) 0.0267(9) 0.0270(9) 0.0022(7) -0.0109(7) -0.0131(8) C21 0.0282(9) 0.0256(8) 0.0258(9) -0.0012(7) -0.0060(7) -0.0141(7) C22 0.0277(9) 0.0278(9) 0.0233(9) -0.0032(7) -0.0004(7) -0.0110(8) C23 0.0231(9) 0.0291(9) 0.0267(9) 0.0027(7) -0.0010(7) -0.0120(7) C24 0.0220(8) 0.0243(8) 0.0255(9) 0.0032(7) -0.0044(7) -0.0126(7) C25 0.0213(8) 0.0237(8) 0.0251(9) -0.0005(7) -0.0021(7) -0.0126(7) C26 0.0309(10) 0.0306(10) 0.0345(11) -0.0034(8) -0.0092(8) -0.0152(8) C27 0.0328(10) 0.0282(10) 0.0441(12) -0.0089(9) -0.0038(9) -0.0136(8) C28 0.0312(10) 0.0230(9) 0.0424(12) 0.0006(8) 0.0004(9) -0.0087(8) C29 0.0382(11) 0.0292(10) 0.0368(12) 0.0059(9) -0.0126(9) -0.0086(9) C30 0.0337(10) 0.0265(9) 0.0282(10) 0.0025(8) -0.0100(8) -0.0125(8) P51 0.0318(2) 0.0212(2) 0.0254(2) 0.00313(18) -0.01276(19) -0.01291(19) S51 0.0244(6) 0.0225(9) 0.0184(7) 0.0038(6) -0.0022(5) -0.0168(6) S51A 0.107(3) 0.0375(17) 0.059(2) 0.0210(14) -0.0525(19) -0.0476(19) C51 0.0335(10) 0.0226(8) 0.0254(9) -0.0022(7) -0.0108(8) -0.0078(8) C52 0.0314(10) 0.0252(9) 0.0225(9) 0.0012(7) -0.0020(7) -0.0132(8) C53 0.0354(10) 0.0222(8) 0.0218(9) 0.0022(7) -0.0033(7) -0.0148(8) C54 0.0268(9) 0.0194(8) 0.0203(8) 0.0039(6) -0.0079(7) -0.0101(7) C55 0.0257(8) 0.0201(8) 0.0227(8) 0.0010(7) -0.0075(7) -0.0106(7) C56 0.0292(9) 0.0239(8) 0.0251(9) 0.0025(7) -0.0101(7) -0.0159(7) C57 0.0309(10) 0.0267(9) 0.0334(10) 0.0005(8) -0.0107(8) -0.0147(8) C58 0.0372(11) 0.0252(9) 0.0439(12) -0.0003(9) -0.0174(9) -0.0109(8) C59 0.0502(13) 0.0241(9) 0.0401(12) -0.0006(8) -0.0220(10) -0.0153(9) C60 0.0635(14) 0.0329(10) 0.0269(10) 0.0103(8) -0.0202(10) -0.0327(11) C61 0.0452(11) 0.0282(9) 0.0254(9) 0.0013(7) -0.0094(8) -0.0251(9) C62 0.0343(12) 0.0475(13) 0.0506(15) 0.0066(11) 0.0013(10) -0.0191(10) C63 0.0596(15) 0.0295(11) 0.0508(15) 0.0048(10) -0.0264(12) -0.0125(11) C64 0.0421(12) 0.0420(11) 0.0316(11) 0.0100(9) -0.0111(9) -0.0262(10) C65 0.0341(10) 0.0228(9) 0.0326(10) -0.0013(8) 0.0040(8) -0.0145(8) C66 0.0417(12) 0.0358(11) 0.0309(11) -0.0048(9) 0.0018(9) -0.0154(10) C67 0.0477(14) 0.0421(12) 0.0313(12) -0.0014(10) 0.0092(10) -0.0124(11) C68 0.0412(13) 0.0390(12) 0.0484(15) 0.0083(11) 0.0043(11) -0.0122(10) C69 0.0415(13) 0.0353(11) 0.0521(15) 0.0111(11) -0.0093(11) -0.0153(10) C70 0.0407(12) 0.0332(10) 0.0327(11) 0.0067(9) -0.0066(9) -0.0180(9) C71 0.0357(10) 0.0276(9) 0.0289(10) 0.0006(8) -0.0015(8) -0.0169(8) C72 0.0370(10) 0.0242(9) 0.0330(10) 0.0053(8) -0.0090(8) -0.0184(8) C73 0.0326(10) 0.0213(8) 0.0289(10) -0.0008(7) -0.0107(8) -0.0119(7) C74 0.0266(9) 0.0233(8) 0.0229(9) -0.0012(7) -0.0055(7) -0.0102(7) C75 0.0299(9) 0.0209(8) 0.0194(8) 0.0005(6) -0.0053(7) -0.0133(7) C76 0.0340(10) 0.0335(10) 0.0283(10) 0.0053(8) -0.0078(8) -0.0207(9) C77 0.0483(12) 0.0376(11) 0.0274(10) 0.0056(8) -0.0053(9) -0.0289(10) C78 0.0549(13) 0.0250(9) 0.0228(9) 0.0044(7) -0.0115(9) -0.0192(9) C79 0.0378(11) 0.0248(9) 0.0250(9) 0.0018(7) -0.0111(8) -0.0093(8) C80 0.0286(9) 0.0244(8) 0.0235(9) 0.0009(7) -0.0047(7) -0.0110(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.7937(18) . ? P1 C6 1.838(2) . ? P1 C5 1.8526(19) . ? P1 S1 1.9571(11) . ? C1 C2 1.343(3) . ? C1 H1 0.9300 . ? C2 C3 1.484(2) . ? C2 C15 1.494(2) . ? C3 C21 1.396(3) . ? C3 C4 1.411(2) . ? C4 C24 1.391(2) . ? C4 C5 1.518(2) . ? C5 C25 1.525(3) . ? C5 H5 0.9800 . ? C6 C11 1.416(2) . ? C6 C7 1.420(3) . ? C7 C8 1.393(3) . ? C7 C12 1.518(3) . ? C8 C9 1.381(3) . ? C8 H8 0.9300 . ? C9 C10 1.390(3) . ? C9 C13 1.505(3) . ? C10 C11 1.390(3) . ? C10 H10 0.9300 . ? C11 C14 1.516(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C20 1.390(3) . ? C15 C16 1.395(3) . ? C16 C17 1.385(3) . ? C16 H16 0.9300 . ? C17 C18 1.380(3) . ? C17 H17 0.9300 . ? C18 C19 1.384(3) . ? C18 H18 0.9300 . ? C19 C20 1.392(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.386(3) . ? C21 H21 0.9300 . ? C22 C23 1.384(3) . ? C22 H22 0.9300 . ? C23 C24 1.386(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.385(3) . ? C25 C26 1.399(3) . ? C26 C27 1.392(3) . ? C26 H26 0.9300 . ? C27 C28 1.378(3) . ? C27 H27 0.9300 . ? C28 C29 1.386(3) . ? C28 H28 0.9300 . ? C29 C30 1.390(3) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? P51 C51 1.792(2) . ? P51 C56 1.827(2) . ? P51 C55 1.8603(19) . ? P51 S51 1.930(3) . ? P51 S51A 1.999(4) . ? C51 C52 1.348(3) . ? C51 H51 0.9300 . ? C52 C53 1.483(3) . ? C52 C65 1.490(3) . ? C53 C71 1.401(3) . ? C53 C54 1.413(3) . ? C54 C74 1.394(2) . ? C54 C55 1.524(2) . ? C55 C75 1.523(3) . ? C55 H55 0.9800 . ? C56 C61 1.412(3) . ? C56 C57 1.424(3) . ? C57 C58 1.384(3) . ? C57 C62 1.522(3) . ? C58 C59 1.367(3) . ? C58 H58 0.9300 . ? C59 C60 1.367(3) . ? C59 C63 1.521(3) . ? C60 C61 1.424(3) . ? C60 H60 0.9300 . ? C61 C64 1.505(3) . ? C62 H62A 0.9600 . ? C62 H62B 0.9600 . ? C62 H62C 0.9600 . ? C63 H63A 0.9600 . ? C63 H63B 0.9600 . ? C63 H63C 0.9600 . ? C64 H64A 0.9600 . ? C64 H64B 0.9600 . ? C64 H64C 0.9600 . ? C65 C70 1.395(3) . ? C65 C66 1.399(3) . ? C66 C67 1.385(3) . ? C66 H66 0.9300 . ? C67 C68 1.380(4) . ? C67 H67 0.9300 . ? C68 C69 1.389(4) . ? C68 H68 0.9300 . ? C69 C70 1.371(3) . ? C69 H69 0.9300 . ? C70 H70 0.9300 . ? C71 C72 1.382(3) . ? C71 H71 0.9300 . ? C72 C73 1.379(3) . ? C72 H72 0.9300 . ? C73 C74 1.385(3) . ? C73 H73 0.9300 . ? C74 H74 0.9300 . ? C75 C80 1.386(3) . ? C75 C76 1.398(3) . ? C76 C77 1.391(3) . ? C76 H76 0.9300 . ? C77 C78 1.385(3) . ? C77 H77 0.9300 . ? C78 C79 1.381(3) . ? C78 H78 0.9300 . ? C79 C80 1.392(3) . ? C79 H79 0.9300 . ? C80 H80 0.9300 . ? 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 C6 109.67(8) . . ? C1 P1 C5 97.63(8) . . ? C6 P1 C5 109.03(8) . . ? C1 P1 S1 112.37(7) . . ? C6 P1 S1 111.34(7) . . ? C5 P1 S1 115.96(6) . . ? C2 C1 P1 122.36(13) . . ? C2 C1 H1 118.8 . . ? P1 C1 H1 118.8 . . ? C1 C2 C3 121.62(16) . . ? C1 C2 C15 119.00(15) . . ? C3 C2 C15 119.35(15) . . ? C21 C3 C4 118.79(16) . . ? C21 C3 C2 120.72(15) . . ? C4 C3 C2 120.49(15) . . ? C24 C4 C3 119.12(16) . . ? C24 C4 C5 118.24(15) . . ? C3 C4 C5 122.62(15) . . ? C4 C5 C25 114.47(15) . . ? C4 C5 P1 108.77(11) . . ? C25 C5 P1 113.82(12) . . ? C4 C5 H5 106.4 . . ? C25 C5 H5 106.4 . . ? P1 C5 H5 106.4 . . ? C11 C6 C7 118.27(17) . . ? C11 C6 P1 121.16(13) . . ? C7 C6 P1 119.92(13) . . ? C8 C7 C6 119.42(17) . . ? C8 C7 C12 116.07(17) . . ? C6 C7 C12 124.42(19) . . ? C9 C8 C7 122.72(17) . . ? C9 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? C8 C9 C10 117.37(18) . . ? C8 C9 C13 121.04(17) . . ? C10 C9 C13 121.53(17) . . ? C11 C10 C9 122.61(17) . . ? C11 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C10 C11 C6 119.57(16) . . ? C10 C11 C14 115.78(15) . . ? C6 C11 C14 124.61(16) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 118.82(17) . . ? C20 C15 C2 120.95(16) . . ? C16 C15 C2 119.99(17) . . ? C17 C16 C15 120.28(19) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 120.51(19) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 119.86(18) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C20 119.9(2) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C15 C20 C19 120.63(19) . . ? C15 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C3 121.33(17) . . ? C22 C21 H21 119.3 . . ? C3 C21 H21 119.3 . . ? C23 C22 C21 119.54(17) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 120.03(17) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C4 121.10(17) . . ? C23 C24 H24 119.5 . . ? C4 C24 H24 119.5 . . ? C30 C25 C26 118.52(18) . . ? C30 C25 C5 122.81(16) . . ? C26 C25 C5 118.51(17) . . ? C27 C26 C25 120.7(2) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C28 C27 C26 119.99(19) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C29 119.78(19) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C28 C29 C30 120.3(2) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C25 C30 C29 120.65(19) . . ? C25 C30 H30 119.7 . . ? C29 C30 H30 119.7 . . ? C51 P51 C56 113.27(10) . . ? C51 P51 C55 100.43(9) . . ? C56 P51 C55 103.77(9) . . ? C51 P51 S51 105.97(10) . . ? C56 P51 S51 115.14(12) . . ? C55 P51 S51 117.55(12) . . ? C51 P51 S51A 110.56(14) . . ? C56 P51 S51A 113.18(15) . . ? C55 P51 S51A 114.89(14) . . ? S51 P51 S51A 4.69(18) . . ? C52 C51 P51 124.57(14) . . ? C52 C51 H51 117.7 . . ? P51 C51 H51 117.7 . . ? C51 C52 C53 121.13(18) . . ? C51 C52 C65 119.85(17) . . ? C53 C52 C65 119.01(17) . . ? C71 C53 C54 119.18(17) . . ? C71 C53 C52 119.29(17) . . ? C54 C53 C52 121.53(17) . . ? C74 C54 C53 118.57(16) . . ? C74 C54 C55 117.46(16) . . ? C53 C54 C55 123.79(15) . . ? C75 C55 C54 113.18(15) . . ? C75 C55 P51 113.19(12) . . ? C54 C55 P51 110.12(12) . . ? C75 C55 H55 106.6 . . ? C54 C55 H55 106.6 . . ? P51 C55 H55 106.6 . . ? C61 C56 C57 118.02(18) . . ? C61 C56 P51 124.42(15) . . ? C57 C56 P51 117.54(15) . . ? C58 C57 C56 120.3(2) . . ? C58 C57 C62 115.4(2) . . ? C56 C57 C62 124.28(19) . . ? C59 C58 C57 122.4(2) . . ? C59 C58 H58 118.8 . . ? C57 C58 H58 118.8 . . ? C58 C59 C60 118.1(2) . . ? C58 C59 C63 121.4(2) . . ? C60 C59 C63 120.5(2) . . ? C59 C60 C61 123.0(2) . . ? C59 C60 H60 118.5 . . ? C61 C60 H60 118.5 . . ? C56 C61 C60 118.15(19) . . ? C56 C61 C64 125.99(19) . . ? C60 C61 C64 115.84(19) . . ? C57 C62 H62A 109.5 . . ? C57 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C57 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C59 C63 H63A 109.5 . . ? C59 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? C59 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? C61 C64 H64A 109.5 . . ? C61 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C61 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C70 C65 C66 118.7(2) . . ? C70 C65 C52 120.78(19) . . ? C66 C65 C52 120.5(2) . . ? C67 C66 C65 119.8(2) . . ? C67 C66 H66 120.1 . . ? C65 C66 H66 120.1 . . ? C68 C67 C66 120.3(2) . . ? C68 C67 H67 119.8 . . ? C66 C67 H67 119.8 . . ? C67 C68 C69 120.5(2) . . ? C67 C68 H68 119.7 . . ? C69 C68 H68 119.7 . . ? C70 C69 C68 119.1(3) . . ? C70 C69 H69 120.4 . . ? C68 C69 H69 120.4 . . ? C69 C70 C65 121.5(2) . . ? C69 C70 H70 119.2 . . ? C65 C70 H70 119.2 . . ? C72 C71 C53 120.94(18) . . ? C72 C71 H71 119.5 . . ? C53 C71 H71 119.5 . . ? C73 C72 C71 119.84(18) . . ? C73 C72 H72 120.1 . . ? C71 C72 H72 120.1 . . ? C72 C73 C74 120.16(17) . . ? C72 C73 H73 119.9 . . ? C74 C73 H73 119.9 . . ? C73 C74 C54 121.25(17) . . ? C73 C74 H74 119.4 . . ? C54 C74 H74 119.4 . . ? C80 C75 C76 118.39(18) . . ? C80 C75 C55 122.08(16) . . ? C76 C75 C55 119.50(17) . . ? C77 C76 C75 120.4(2) . . ? C77 C76 H76 119.8 . . ? C75 C76 H76 119.8 . . ? C78 C77 C76 120.71(19) . . ? C78 C77 H77 119.6 . . ? C76 C77 H77 119.6 . . ? C79 C78 C77 119.0(2) . . ? C79 C78 H78 120.5 . . ? C77 C78 H78 120.5 . . ? C78 C79 C80 120.7(2) . . ? C78 C79 H79 119.7 . . ? C80 C79 H79 119.7 . . ? C75 C80 C79 120.82(18) . . ? C75 C80 H80 119.6 . . ? C79 C80 H80 119.6 . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.964 _refine_diff_density_min -0.719 _refine_diff_density_rms 0.063 # Attachment '6999_web_deposit_cif_file_1_LauraPavelka_1314899584.07145.cif' data_07145 _database_code_depnum_ccdc_archive 'CCDC 842630' #TrackingRef '6999_web_deposit_cif_file_1_LauraPavelka_1314899584.07145.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H29 O P S' _exptl_crystal_recrystallization_method 'diff hexanes into Et2O/C6H6' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour colourless _diffrn_ambient_temperature 150(2) _chemical_formula_weight 480.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.163(2) _cell_length_b 14.137(3) _cell_length_c 17.859(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.19(3) _cell_angle_gamma 90.00 _cell_volume 2508.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14684 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 27.48 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.325 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9094 _exptl_absorpt_correction_T_max 0.9383 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scan, and \w scanes with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19121 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6004 _reflns_number_gt 9363 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.7592P] 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 5762 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.56896(5) 0.81245(3) 0.17938(3) 0.03273(14) Uani 1 1 d . . . S1 S 0.56152(5) 0.90992(4) 0.25614(3) 0.04725(16) Uani 1 1 d . . . C1 C 0.62905(17) 0.86398(13) 0.10147(10) 0.0337(4) Uani 1 1 d . . . H1 H 0.6165 0.9284 0.0922 0.040 Uiso 1 1 calc R . . C2 C 0.69160(17) 0.81310(13) 0.05591(10) 0.0318(4) Uani 1 1 d . . . C3 C 0.69318(16) 0.70811(13) 0.06075(10) 0.0302(4) Uani 1 1 d . . . C4 C 0.69153(16) 0.66159(13) 0.13000(10) 0.0313(4) Uani 1 1 d . . . C5 C 0.69762(17) 0.71709(13) 0.20353(10) 0.0333(4) Uani 1 1 d . . . H5 H 0.6689 0.6748 0.2405 0.040 Uiso 1 1 calc R . . C6 C 0.41300(17) 0.74580(13) 0.14922(10) 0.0325(4) Uani 1 1 d . . . C7 C 0.37303(18) 0.68698(15) 0.20447(10) 0.0372(4) Uani 1 1 d . . . C8 C 0.2599(2) 0.63073(15) 0.18310(12) 0.0429(5) Uani 1 1 d . . . H8 H 0.2368 0.5903 0.2194 0.051 Uiso 1 1 calc R . . C9 C 0.17975(19) 0.63193(14) 0.11037(12) 0.0411(5) Uani 1 1 d . . . C10 C 0.21671(18) 0.69255(14) 0.05783(11) 0.0379(4) Uani 1 1 d . . . H10 H 0.1625 0.6957 0.0089 0.045 Uiso 1 1 calc R . . C11 C 0.33100(17) 0.74909(13) 0.07445(10) 0.0325(4) Uani 1 1 d . . . C12 C 0.4417(2) 0.68190(18) 0.28866(11) 0.0527(6) Uani 1 1 d . . . H12A H 0.3749 0.6833 0.3195 0.079 Uiso 1 1 calc R . . H12B H 0.5011 0.7350 0.3015 0.079 Uiso 1 1 calc R . . H12C H 0.4924 0.6243 0.2982 0.079 Uiso 1 1 calc R . . C13 C 0.0571(2) 0.57012(17) 0.08953(14) 0.0562(6) Uani 1 1 d . . . H13A H 0.0809 0.5116 0.0685 0.084 Uiso 1 1 calc R . . H13B H -0.0103 0.6019 0.0522 0.084 Uiso 1 1 calc R . . H13C H 0.0224 0.5574 0.1345 0.084 Uiso 1 1 calc R . . C14 C 0.35675(19) 0.81093(16) 0.01011(11) 0.0439(5) Uani 1 1 d . . . H14A H 0.4268 0.7835 -0.0115 0.066 Uiso 1 1 calc R . . H14B H 0.3840 0.8728 0.0297 0.066 Uiso 1 1 calc R . . H14C H 0.2759 0.8159 -0.0288 0.066 Uiso 1 1 calc R . . C15 C 0.75431(17) 0.86016(13) -0.00226(10) 0.0326(4) Uani 1 1 d . . . C16 C 0.68341(19) 0.92478(14) -0.05445(11) 0.0381(4) Uani 1 1 d . . . H16 H 0.5942 0.9380 -0.0535 0.046 Uiso 1 1 calc R . . C17 C 0.74217(19) 0.96930(15) -0.10726(11) 0.0424(5) Uani 1 1 d . . . H17 H 0.6922 1.0115 -0.1420 0.051 Uiso 1 1 calc R . . C18 C 0.87544(19) 0.95184(13) -0.10912(11) 0.0374(4) Uani 1 1 d . . . C19 C 0.9489(2) 0.88970(15) -0.05669(13) 0.0453(5) Uani 1 1 d . . . H19 H 1.0393 0.8788 -0.0564 0.054 Uiso 1 1 calc R . . C20 C 0.88798(19) 0.84381(15) -0.00486(12) 0.0446(5) Uani 1 1 d . . . H20 H 0.9377 0.8008 0.0292 0.054 Uiso 1 1 calc R . . C21 C 0.68428(17) 0.65445(13) -0.00599(11) 0.0346(4) Uani 1 1 d . . . H21 H 0.6857 0.6848 -0.0520 0.041 Uiso 1 1 calc R . . C22 C 0.67336(18) 0.55685(14) -0.00450(11) 0.0383(4) Uani 1 1 d . . . H22 H 0.6662 0.5220 -0.0494 0.046 Uiso 1 1 calc R . . C23 C 0.67309(19) 0.51163(14) 0.06388(11) 0.0400(5) Uani 1 1 d . . . H23 H 0.6662 0.4461 0.0652 0.048 Uiso 1 1 calc R . . C24 C 0.68301(18) 0.56345(13) 0.13065(11) 0.0363(4) Uani 1 1 d . . . H24 H 0.6840 0.5322 0.1766 0.044 Uiso 1 1 calc R . . C25 C 0.83516(19) 0.75590(14) 0.24079(10) 0.0372(4) Uani 1 1 d . . . C26 C 0.8552(2) 0.78686(18) 0.31640(12) 0.0576(6) Uani 1 1 d . . . H26 H 0.7857 0.7825 0.3427 0.069 Uiso 1 1 calc R . . C27 C 0.9785(3) 0.82424(19) 0.35253(15) 0.0736(9) Uani 1 1 d . . . H27 H 0.9907 0.8450 0.4029 0.088 Uiso 1 1 calc R . . C28 C 1.0823(3) 0.83094(17) 0.31492(17) 0.0691(8) Uani 1 1 d . . . H28 H 1.1644 0.8566 0.3395 0.083 Uiso 1 1 calc R . . C29 C 1.0646(2) 0.79946(15) 0.24044(14) 0.0529(6) Uani 1 1 d . . . H29 H 1.1349 0.8033 0.2147 0.064 Uiso 1 1 calc R . . C30 C 0.94127(19) 0.76197(13) 0.20388(12) 0.0397(5) Uani 1 1 d . . . H30 H 0.9301 0.7406 0.1537 0.048 Uiso 1 1 calc R . . O31 O 0.92454(14) 0.99806(10) -0.16452(8) 0.0501(4) Uani 1 1 d . . . C31 C 1.0595(2) 0.97815(16) -0.17043(14) 0.0533(6) Uani 1 1 d . . . H31A H 1.1195 0.9927 -0.1227 0.080 Uiso 1 1 calc R . . H31B H 1.0823 1.0160 -0.2105 0.080 Uiso 1 1 calc R . . H31C H 1.0674 0.9124 -0.1821 0.080 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0283(2) 0.0371(3) 0.0310(2) -0.0032(2) 0.00218(19) 0.0071(2) S1 0.0465(3) 0.0499(3) 0.0405(3) -0.0144(2) -0.0020(2) 0.0143(2) C1 0.0276(9) 0.0320(10) 0.0392(10) 0.0024(8) 0.0017(8) 0.0044(7) C2 0.0225(8) 0.0327(10) 0.0379(9) 0.0008(8) 0.0014(7) 0.0011(7) C3 0.0211(8) 0.0348(10) 0.0336(9) -0.0017(7) 0.0033(7) 0.0017(7) C4 0.0212(8) 0.0358(10) 0.0358(9) -0.0015(8) 0.0034(7) 0.0037(7) C5 0.0301(9) 0.0367(10) 0.0326(9) 0.0020(8) 0.0054(7) 0.0059(8) C6 0.0289(9) 0.0387(10) 0.0302(9) -0.0020(8) 0.0066(7) 0.0089(8) C7 0.0320(10) 0.0488(12) 0.0315(9) 0.0021(8) 0.0082(8) 0.0088(8) C8 0.0374(11) 0.0478(12) 0.0457(11) 0.0083(10) 0.0142(9) 0.0037(9) C9 0.0341(10) 0.0406(11) 0.0486(12) -0.0067(9) 0.0092(9) 0.0037(9) C10 0.0323(10) 0.0453(11) 0.0339(10) -0.0066(9) 0.0022(8) 0.0063(8) C11 0.0260(9) 0.0411(10) 0.0297(9) -0.0026(8) 0.0042(7) 0.0096(8) C12 0.0472(13) 0.0770(17) 0.0336(11) 0.0106(11) 0.0081(9) 0.0042(11) C13 0.0470(13) 0.0504(13) 0.0701(15) -0.0095(12) 0.0096(11) -0.0081(10) C14 0.0313(10) 0.0632(14) 0.0341(10) 0.0073(10) 0.0002(8) 0.0039(9) C15 0.0283(9) 0.0303(10) 0.0382(10) -0.0014(8) 0.0047(7) -0.0002(7) C16 0.0291(9) 0.0442(11) 0.0407(10) 0.0037(9) 0.0064(8) 0.0064(8) C17 0.0368(11) 0.0479(12) 0.0418(11) 0.0102(9) 0.0069(9) 0.0097(9) C18 0.0367(10) 0.0337(10) 0.0429(10) 0.0023(8) 0.0108(8) -0.0012(8) C19 0.0294(10) 0.0441(12) 0.0644(14) 0.0121(10) 0.0147(9) 0.0046(8) C20 0.0320(10) 0.0433(12) 0.0589(13) 0.0163(10) 0.0104(9) 0.0087(9) C21 0.0289(9) 0.0389(11) 0.0359(10) -0.0006(8) 0.0069(8) 0.0009(8) C22 0.0336(10) 0.0374(11) 0.0425(11) -0.0085(8) 0.0048(8) 0.0026(8) C23 0.0359(10) 0.0307(10) 0.0506(12) -0.0026(9) 0.0027(9) 0.0016(8) C24 0.0300(9) 0.0353(10) 0.0420(10) 0.0056(8) 0.0037(8) 0.0039(8) C25 0.0354(10) 0.0355(10) 0.0354(10) -0.0030(8) -0.0045(8) 0.0113(8) C26 0.0526(14) 0.0740(16) 0.0382(11) -0.0095(11) -0.0088(10) 0.0286(12) C27 0.0719(18) 0.0697(17) 0.0577(15) -0.0257(13) -0.0352(14) 0.0329(14) C28 0.0544(15) 0.0401(13) 0.0886(19) -0.0129(12) -0.0394(14) 0.0073(11) C29 0.0359(11) 0.0361(11) 0.0767(16) 0.0006(11) -0.0109(10) 0.0003(9) C30 0.0340(10) 0.0337(10) 0.0466(11) -0.0046(9) -0.0022(8) 0.0039(8) O31 0.0466(9) 0.0494(9) 0.0597(9) 0.0167(7) 0.0239(7) 0.0063(7) C31 0.0493(13) 0.0469(13) 0.0716(15) 0.0088(11) 0.0308(11) 0.0027(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 P1 C1 1.7885(19) . ? P1 C6 1.8248(19) . ? P1 C5 1.8642(18) . ? P1 S1 1.9563(7) . ? C1 C2 1.342(3) . ? C1 H1 0.9300 . ? C2 C15 1.486(3) . ? C2 C3 1.487(3) . ? C3 C21 1.400(2) . ? C3 C4 1.404(3) . ? C4 C24 1.390(3) . ? C4 C5 1.520(2) . ? C5 C25 1.518(3) . ? C5 H5 0.9800 . ? C6 C7 1.414(3) . ? C6 C11 1.418(2) . ? C7 C8 1.384(3) . ? C7 C12 1.520(3) . ? C8 C9 1.380(3) . ? C8 H8 0.9300 . ? C9 C10 1.380(3) . ? C9 C13 1.503(3) . ? C10 C11 1.389(3) . ? C10 H10 0.9300 . ? C11 C14 1.510(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C20 1.389(3) . ? C15 C16 1.392(3) . ? C16 C17 1.371(3) . ? C16 H16 0.9300 . ? C17 C18 1.384(3) . ? C17 H17 0.9300 . ? C18 O31 1.365(2) . ? C18 C19 1.382(3) . ? C19 C20 1.380(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.385(3) . ? C21 H21 0.9300 . ? C22 C23 1.379(3) . ? C22 H22 0.9300 . ? C23 C24 1.385(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.380(3) . ? C25 C26 1.393(3) . ? C26 C27 1.387(4) . ? C26 H26 0.9300 . ? C27 C28 1.369(4) . ? C27 H27 0.9300 . ? C28 C29 1.378(4) . ? C28 H28 0.9300 . ? C29 C30 1.390(3) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? O31 C31 1.426(2) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C6 113.50(8) . . ? C1 P1 C5 97.84(9) . . ? C6 P1 C5 102.59(8) . . ? C1 P1 S1 109.17(7) . . ? C6 P1 S1 114.26(6) . . ? C5 P1 S1 118.45(6) . . ? C2 C1 P1 122.45(15) . . ? C2 C1 H1 118.8 . . ? P1 C1 H1 118.8 . . ? C1 C2 C15 120.79(16) . . ? C1 C2 C3 120.03(17) . . ? C15 C2 C3 119.13(16) . . ? C21 C3 C4 119.05(17) . . ? C21 C3 C2 119.58(16) . . ? C4 C3 C2 121.13(16) . . ? C24 C4 C3 119.16(17) . . ? C24 C4 C5 119.95(17) . . ? C3 C4 C5 120.89(16) . . ? C25 C5 C4 115.53(15) . . ? C25 C5 P1 112.09(13) . . ? C4 C5 P1 105.96(11) . . ? C25 C5 H5 107.6 . . ? C4 C5 H5 107.6 . . ? P1 C5 H5 107.6 . . ? C7 C6 C11 118.57(17) . . ? C7 C6 P1 117.22(13) . . ? C11 C6 P1 124.22(14) . . ? C8 C7 C6 119.34(17) . . ? C8 C7 C12 115.27(18) . . ? C6 C7 C12 125.35(18) . . ? C9 C8 C7 122.91(19) . . ? C9 C8 H8 118.5 . . ? C7 C8 H8 118.5 . . ? C8 C9 C10 117.16(18) . . ? C8 C9 C13 121.3(2) . . ? C10 C9 C13 121.54(19) . . ? C9 C10 C11 123.17(17) . . ? C9 C10 H10 118.4 . . ? C11 C10 H10 118.4 . . ? C10 C11 C6 118.76(17) . . ? C10 C11 C14 116.22(16) . . ? C6 C11 C14 125.02(17) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 117.29(17) . . ? C20 C15 C2 121.06(16) . . ? C16 C15 C2 121.60(16) . . ? C17 C16 C15 121.51(18) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C18 120.34(18) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? O31 C18 C19 124.55(18) . . ? O31 C18 C17 116.19(17) . . ? C19 C18 C17 119.25(18) . . ? C20 C19 C18 119.89(18) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C15 121.68(18) . . ? C19 C20 H20 119.2 . . ? C15 C20 H20 119.2 . . ? C22 C21 C3 120.97(18) . . ? C22 C21 H21 119.5 . . ? C3 C21 H21 119.5 . . ? C23 C22 C21 119.61(18) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 120.26(18) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C4 120.93(18) . . ? C23 C24 H24 119.5 . . ? C4 C24 H24 119.5 . . ? C30 C25 C26 118.32(19) . . ? C30 C25 C5 123.58(16) . . ? C26 C25 C5 118.10(19) . . ? C27 C26 C25 120.2(2) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C28 C27 C26 120.8(2) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C27 C28 C29 119.6(2) . . ? C27 C28 H28 120.2 . . ? C29 C28 H28 120.2 . . ? C28 C29 C30 119.9(2) . . ? C28 C29 H29 120.1 . . ? C30 C29 H29 120.1 . . ? C25 C30 C29 121.1(2) . . ? C25 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? C18 O31 C31 117.63(16) . . ? O31 C31 H31A 109.5 . . ? O31 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O31 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.206 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.050 # Attachment '7000_web_deposit_cif_file_2_LauraPavelka_1314899584.07231.cif' data_07231 _database_code_depnum_ccdc_archive 'CCDC 842631' #TrackingRef '7000_web_deposit_cif_file_2_LauraPavelka_1314899584.07231.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H26 F3 P S' _exptl_crystal_recrystallization_method 'diff hexanes into Et2O/C6H6' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour colourless _diffrn_ambient_temperature 150(2) _chemical_formula_weight 518.55 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.684(2) _cell_length_b 10.885(2) _cell_length_c 13.114(3) _cell_angle_alpha 69.32(3) _cell_angle_beta 74.49(3) _cell_angle_gamma 74.93(3) _cell_volume 1351.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8797 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 27.48 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.125 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9278 _exptl_absorpt_correction_T_max 0.9733 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scan, and \w scanes with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10114 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 27.65 _reflns_number_total 6195 _reflns_number_gt 5542 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.1069P)^2^+0.1512P] 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 6195 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.2005 _refine_ls_wR_factor_gt 0.1745 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.22470(6) -0.12721(6) 0.36808(5) 0.0464(2) Uani 1 1 d . . . S1 S 0.13514(8) -0.21681(8) 0.51623(6) 0.0660(3) Uani 1 1 d . . . F1 F -0.3058(5) 0.5108(5) -0.0618(4) 0.249(3) Uani 1 1 d . . . F2 F -0.2905(4) 0.6038(4) 0.0381(5) 0.238(3) Uani 1 1 d . . . F3 F -0.4024(3) 0.4646(5) 0.0923(5) 0.238(3) Uani 1 1 d . . . C1 C 0.1164(2) 0.0154(3) 0.3010(2) 0.0498(6) Uani 1 1 d . . . H1 H 0.0508 0.0600 0.3451 0.060 Uiso 1 1 calc R . . C2 C 0.1240(2) 0.0631(3) 0.1891(2) 0.0524(6) Uani 1 1 d . . . C3 C 0.2283(2) 0.0023(3) 0.1124(2) 0.0494(6) Uani 1 1 d . . . C4 C 0.2959(2) -0.1290(2) 0.1484(2) 0.0472(6) Uani 1 1 d . . . C5 C 0.2651(3) -0.2212(2) 0.2664(2) 0.0489(6) Uani 1 1 d . . . H5 H 0.3461 -0.2864 0.2803 0.059 Uiso 1 1 calc R . . C6 C 0.3804(2) -0.0836(3) 0.36523(19) 0.0492(6) Uani 1 1 d . . . C7 C 0.4867(3) -0.1882(3) 0.3954(2) 0.0642(7) Uani 1 1 d . . . C8 C 0.6068(3) -0.1609(4) 0.3928(2) 0.0728(9) Uani 1 1 d . . . H8 H 0.6758 -0.2316 0.4117 0.087 Uiso 1 1 calc R . . C9 C 0.6274(3) -0.0335(4) 0.3635(2) 0.0711(9) Uani 1 1 d . . . C10 C 0.5241(3) 0.0683(3) 0.3401(2) 0.0677(8) Uani 1 1 d . . . H10 H 0.5366 0.1554 0.3229 0.081 Uiso 1 1 calc R . . C11 C 0.3982(3) 0.0477(3) 0.3409(2) 0.0583(7) Uani 1 1 d . . . C12 C 0.4792(4) -0.3356(3) 0.4356(4) 0.1041(13) Uani 1 1 d . . . H12A H 0.5154 -0.3723 0.3750 0.156 Uiso 1 1 calc R . . H12B H 0.3887 -0.3461 0.4636 0.156 Uiso 1 1 calc R . . H12C H 0.5289 -0.3816 0.4937 0.156 Uiso 1 1 calc R . . C13 C 0.7600(3) -0.0039(5) 0.3573(3) 0.1052(14) Uani 1 1 d . . . H13A H 0.7933 -0.0593 0.4232 0.158 Uiso 1 1 calc R . . H13B H 0.7505 0.0883 0.3515 0.158 Uiso 1 1 calc R . . H13C H 0.8207 -0.0220 0.2934 0.158 Uiso 1 1 calc R . . C14 C 0.2930(4) 0.1689(3) 0.3214(3) 0.0903(11) Uani 1 1 d . . . H14A H 0.2697 0.1867 0.2511 0.136 Uiso 1 1 calc R . . H14B H 0.3249 0.2438 0.3210 0.136 Uiso 1 1 calc R . . H14C H 0.2167 0.1543 0.3796 0.136 Uiso 1 1 calc R . . C15 C 0.0218(3) 0.1772(3) 0.1445(2) 0.0524(6) Uani 1 1 d . . . C16 C -0.0103(3) 0.2914(3) 0.1778(3) 0.0706(8) Uani 1 1 d . . . H16 H 0.0365 0.2988 0.2252 0.085 Uiso 1 1 calc R . . C17 C -0.1102(4) 0.3930(3) 0.1413(3) 0.0874(11) Uani 1 1 d . . . H17 H -0.1308 0.4689 0.1642 0.105 Uiso 1 1 calc R . . C18 C -0.1803(3) 0.3838(3) 0.0714(3) 0.0749(9) Uani 1 1 d . . . C19 C -0.1493(3) 0.2716(4) 0.0386(3) 0.0789(9) Uani 1 1 d . . . H19 H -0.1975 0.2640 -0.0076 0.095 Uiso 1 1 calc R . . C20 C -0.0494(3) 0.1717(3) 0.0726(3) 0.0698(8) Uani 1 1 d . . . H20 H -0.0280 0.0978 0.0471 0.084 Uiso 1 1 calc R . . C21 C 0.2614(3) 0.0760(3) 0.0003(2) 0.0608(7) Uani 1 1 d . . . H21 H 0.2174 0.1635 -0.0248 0.073 Uiso 1 1 calc R . . C22 C 0.3574(3) 0.0220(4) -0.0733(2) 0.0677(8) Uani 1 1 d . . . H22 H 0.3784 0.0729 -0.1472 0.081 Uiso 1 1 calc R . . C23 C 0.4223(3) -0.1076(3) -0.0375(2) 0.0683(8) Uani 1 1 d . . . H23 H 0.4861 -0.1452 -0.0873 0.082 Uiso 1 1 calc R . . C24 C 0.3927(3) -0.1820(3) 0.0725(2) 0.0574(7) Uani 1 1 d . . . H24 H 0.4383 -0.2690 0.0965 0.069 Uiso 1 1 calc R . . C25 C 0.1580(3) -0.3001(3) 0.2844(2) 0.0531(6) Uani 1 1 d . . . C26 C 0.1704(4) -0.4314(3) 0.3510(3) 0.0743(9) Uani 1 1 d . . . H26 H 0.2450 -0.4712 0.3826 0.089 Uiso 1 1 calc R . . C27 C 0.0734(4) -0.5043(3) 0.3713(3) 0.0885(11) Uani 1 1 d . . . H27 H 0.0833 -0.5925 0.4166 0.106 Uiso 1 1 calc R . . C28 C -0.0364(4) -0.4488(4) 0.3258(3) 0.0861(11) Uani 1 1 d . . . H28 H -0.1015 -0.4984 0.3400 0.103 Uiso 1 1 calc R . . C29 C -0.0499(4) -0.3181(4) 0.2585(3) 0.0793(9) Uani 1 1 d . . . H29 H -0.1245 -0.2790 0.2269 0.095 Uiso 1 1 calc R . . C30 C 0.0474(3) -0.2451(3) 0.2378(2) 0.0657(8) Uani 1 1 d . . . H30 H 0.0377 -0.1572 0.1917 0.079 Uiso 1 1 calc R . . C31 C -0.2916(5) 0.4905(6) 0.0359(5) 0.1152(15) 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 P1 0.0480(4) 0.0495(4) 0.0439(3) -0.0153(3) -0.0062(3) -0.0140(3) S1 0.0806(5) 0.0706(5) 0.0490(4) -0.0185(3) 0.0059(3) -0.0359(4) F1 0.265(5) 0.235(5) 0.224(5) -0.076(4) -0.169(4) 0.126(4) F2 0.192(4) 0.100(2) 0.477(8) -0.111(4) -0.216(5) 0.071(2) F3 0.077(2) 0.204(4) 0.332(6) 0.007(4) -0.054(3) 0.034(2) C1 0.0464(14) 0.0532(15) 0.0540(14) -0.0258(12) -0.0081(11) -0.0045(11) C2 0.0499(14) 0.0530(15) 0.0521(14) -0.0185(12) -0.0031(12) -0.0095(12) C3 0.0463(13) 0.0510(15) 0.0496(13) -0.0175(11) -0.0018(11) -0.0114(12) C4 0.0429(13) 0.0522(15) 0.0499(13) -0.0207(11) -0.0047(11) -0.0115(11) C5 0.0480(14) 0.0468(14) 0.0517(14) -0.0184(11) -0.0082(11) -0.0052(11) C6 0.0527(14) 0.0529(15) 0.0416(12) -0.0115(10) -0.0065(11) -0.0161(12) C7 0.0587(17) 0.071(2) 0.0606(16) -0.0118(14) -0.0176(14) -0.0137(15) C8 0.0571(18) 0.099(3) 0.0645(18) -0.0249(17) -0.0152(14) -0.0141(17) C9 0.0609(18) 0.113(3) 0.0532(16) -0.0397(17) -0.0024(14) -0.0286(19) C10 0.085(2) 0.077(2) 0.0528(16) -0.0297(15) 0.0057(15) -0.0394(18) C11 0.0650(17) 0.0568(17) 0.0545(15) -0.0189(12) -0.0018(13) -0.0211(14) C12 0.094(3) 0.063(2) 0.140(3) 0.004(2) -0.052(2) -0.0074(19) C13 0.074(2) 0.173(4) 0.097(3) -0.063(3) -0.0021(19) -0.056(3) C14 0.099(3) 0.061(2) 0.126(3) -0.031(2) -0.037(2) -0.0190(19) C15 0.0497(14) 0.0499(15) 0.0501(14) -0.0134(11) -0.0056(11) -0.0031(12) C16 0.078(2) 0.0658(19) 0.081(2) -0.0353(16) -0.0395(17) 0.0090(16) C17 0.091(2) 0.071(2) 0.121(3) -0.054(2) -0.050(2) 0.0172(19) C18 0.0629(19) 0.071(2) 0.092(2) -0.0266(17) -0.0309(17) 0.0055(16) C19 0.0641(19) 0.088(2) 0.100(2) -0.040(2) -0.0353(18) -0.0037(18) C20 0.0686(19) 0.069(2) 0.086(2) -0.0380(16) -0.0244(16) -0.0066(16) C21 0.0622(17) 0.0637(18) 0.0509(15) -0.0135(13) -0.0055(13) -0.0136(14) C22 0.0660(18) 0.092(2) 0.0462(15) -0.0215(15) 0.0015(13) -0.0277(17) C23 0.0630(18) 0.091(2) 0.0572(16) -0.0402(16) 0.0050(14) -0.0178(17) C24 0.0531(15) 0.0622(17) 0.0611(16) -0.0322(13) -0.0044(13) -0.0054(13) C25 0.0656(17) 0.0476(15) 0.0505(14) -0.0232(12) -0.0016(13) -0.0161(12) C26 0.099(2) 0.0506(17) 0.0755(19) -0.0185(14) -0.0143(17) -0.0218(16) C27 0.134(3) 0.059(2) 0.085(2) -0.0197(17) -0.020(2) -0.043(2) C28 0.112(3) 0.089(3) 0.077(2) -0.0358(19) 0.005(2) -0.060(2) C29 0.084(2) 0.088(2) 0.081(2) -0.0270(18) -0.0137(17) -0.0405(19) C30 0.073(2) 0.0599(18) 0.0686(18) -0.0139(14) -0.0138(15) -0.0278(15) C31 0.089(3) 0.117(4) 0.151(4) -0.044(3) -0.070(3) 0.014(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 P1 C1 1.780(3) . ? P1 C6 1.832(3) . ? P1 C5 1.853(3) . ? P1 S1 1.9477(12) . ? F1 C31 1.265(6) . ? F2 C31 1.246(6) . ? F3 C31 1.260(6) . ? C1 C2 1.361(3) . ? C1 H1 0.9300 . ? C2 C3 1.476(3) . ? C2 C15 1.484(4) . ? C3 C4 1.399(4) . ? C3 C21 1.402(4) . ? C4 C24 1.392(3) . ? C4 C5 1.520(3) . ? C5 C25 1.525(4) . ? C5 H5 0.9800 . ? C6 C11 1.403(4) . ? C6 C7 1.411(4) . ? C7 C8 1.380(4) . ? C7 C12 1.519(5) . ? C8 C9 1.362(5) . ? C8 H8 0.9300 . ? C9 C10 1.358(5) . ? C9 C13 1.508(4) . ? C10 C11 1.417(4) . ? C10 H10 0.9300 . ? C11 C14 1.488(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C20 1.385(4) . ? C15 C16 1.391(4) . ? C16 C17 1.370(4) . ? C16 H16 0.9300 . ? C17 C18 1.372(4) . ? C17 H17 0.9300 . ? C18 C19 1.367(5) . ? C18 C31 1.475(5) . ? C19 C20 1.353(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.374(4) . ? C21 H21 0.9300 . ? C22 C23 1.375(4) . ? C22 H22 0.9300 . ? C23 C24 1.378(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.374(4) . ? C25 C26 1.380(4) . ? C26 C27 1.381(5) . ? C26 H26 0.9300 . ? C27 C28 1.358(5) . ? C27 H27 0.9300 . ? C28 C29 1.378(5) . ? C28 H28 0.9300 . ? C29 C30 1.382(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? 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 C6 111.08(12) . . ? C1 P1 C5 99.35(12) . . ? C6 P1 C5 105.61(12) . . ? C1 P1 S1 110.54(9) . . ? C6 P1 S1 114.05(9) . . ? C5 P1 S1 115.21(9) . . ? C2 C1 P1 123.83(19) . . ? C2 C1 H1 118.1 . . ? P1 C1 H1 118.1 . . ? C1 C2 C3 121.8(2) . . ? C1 C2 C15 118.3(2) . . ? C3 C2 C15 119.8(2) . . ? C4 C3 C21 118.3(2) . . ? C4 C3 C2 121.6(2) . . ? C21 C3 C2 120.1(2) . . ? C24 C4 C3 119.3(2) . . ? C24 C4 C5 117.3(2) . . ? C3 C4 C5 123.4(2) . . ? C4 C5 C25 113.6(2) . . ? C4 C5 P1 110.69(17) . . ? C25 C5 P1 111.43(16) . . ? C4 C5 H5 106.9 . . ? C25 C5 H5 106.9 . . ? P1 C5 H5 106.9 . . ? C11 C6 C7 117.7(3) . . ? C11 C6 P1 123.9(2) . . ? C7 C6 P1 118.4(2) . . ? C8 C7 C6 120.7(3) . . ? C8 C7 C12 114.9(3) . . ? C6 C7 C12 124.4(3) . . ? C9 C8 C7 122.0(3) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C10 C9 C8 118.1(3) . . ? C10 C9 C13 120.0(3) . . ? C8 C9 C13 121.9(4) . . ? C9 C10 C11 122.9(3) . . ? C9 C10 H10 118.6 . . ? C11 C10 H10 118.6 . . ? C6 C11 C10 118.4(3) . . ? C6 C11 C14 125.3(3) . . ? C10 C11 C14 116.2(3) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 117.6(3) . . ? C20 C15 C2 121.5(2) . . ? C16 C15 C2 120.9(3) . . ? C17 C16 C15 120.5(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 120.5(3) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C19 C18 C17 119.2(3) . . ? C19 C18 C31 120.2(4) . . ? C17 C18 C31 120.6(3) . . ? C20 C19 C18 120.8(3) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C15 121.4(3) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 119.3 . . ? C22 C21 C3 121.5(3) . . ? C22 C21 H21 119.2 . . ? C3 C21 H21 119.2 . . ? C21 C22 C23 119.8(3) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C22 C23 C24 119.9(2) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C4 121.2(3) . . ? C23 C24 H24 119.4 . . ? C4 C24 H24 119.4 . . ? C30 C25 C26 118.0(3) . . ? C30 C25 C5 122.6(2) . . ? C26 C25 C5 119.5(3) . . ? C25 C26 C27 120.8(3) . . ? C25 C26 H26 119.6 . . ? C27 C26 H26 119.6 . . ? C28 C27 C26 120.9(3) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C27 C28 C29 119.1(3) . . ? C27 C28 H28 120.5 . . ? C29 C28 H28 120.5 . . ? C28 C29 C30 120.1(3) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C25 C30 C29 121.1(3) . . ? C25 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? F2 C31 F3 105.1(5) . . ? F2 C31 F1 103.8(6) . . ? F3 C31 F1 101.7(5) . . ? F2 C31 C18 116.7(4) . . ? F3 C31 C18 113.1(5) . . ? F1 C31 C18 114.8(5) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.65 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.517 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.051