# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email gerhard.maas@chemie.uni-ulm.de _publ_contact_author_name 'Prof Gerhard Maas' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_address ; Division of Organic Chemistry I University of Ulm Albert-Einstein-Allee 11 Ulm D-89081 GERMANY ; _publ_contact_author_phone '+49 731 502 2790' _publ_contact_author_fax '+49 731 502 2803' #=========================================================================== # 4. TEXT #=========================================================================== _publ_section_abstract ; The structure of compound 3 in the paper has been determined by single crystal X-ray diffraction analysis. ; _publ_section_title ; Different thermal reactivity of a 1,2-thiaphospholo[a]phosphirane in free and complexed form ; #=========================================================================== # 3. TITLE AND AUTHOR LIST #=========================================================================== loop_ _publ_author_name _publ_author_address T.Jikyo ; Abteilung Organische Chemie Universitat Ulm Albert-Einstein-Allee 11 D-89081 Ulm Germany ; G.Maas ; Abteilung Organische Chemie Universitat Ulm Albert-Einstein-Allee 11 D-89081 Ulm Germany ; #============================================================================ # DATA for compound 5 in publication #============================================================================ data_jik020 _database_code_CSD 218743 _chemical_name_common ; 2,3a,8-triphenyl-3a,8-dihydro-1-thia-8a- phosphacyclopenta(a)indene P-(pentacarbonyl)tungsten ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3a,8-triphenyl-3a,8-dihydro-1-thia-8a-phosphacyclopenta[a]indene P-(pentacarbonyl)tungsten ; _chemical_melting_point '173-174 \%C' _chemical_formula_moiety (C28H21PS)xW(CO)5 _chemical_formula_sum 'C33 H21 O5 P S W' _chemical_formula_weight 744.38 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' W W -0.8490 6.8722 '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 2/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 8.8753(16) _cell_length_b 10.701(2) _cell_length_c 30.832(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.81(2) _cell_angle_gamma 90.00 _cell_volume 2924.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 4.116 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.1900 _exptl_absorpt_correction_T_max 0.6600 _diffrn_ambient_temperature 193(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 'IPDS (Stoe, Darmstadt)' _diffrn_measurement_method 'Phi scans, rotation mode' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20349 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 24.06 _reflns_number_total 4431 _reflns_number_gt 3209 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS software (Stoe, Darmstadt)' _computing_cell_refinement 'IPDS software (Stoe, Darmstadt)' _computing_data_reduction 'X-RED (Stoe, Darmstadt)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1998)' _computing_publication_material 'SHELX-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^)+(0.0448P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4431 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _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 W1 W 1.08877(3) 0.49018(2) 0.846140(10) 0.03418(11) Uani 1 1 d . . . S1 S 0.7762(2) 0.27699(14) 0.80984(6) 0.0331(4) Uani 1 1 d . . . P1 P 0.88753(19) 0.33997(14) 0.86703(6) 0.0262(4) Uani 1 1 d . . . O1 O 1.2682(9) 0.4894(6) 0.9373(2) 0.089(2) Uani 1 1 d . . . O2 O 0.9436(8) 0.7514(5) 0.8667(3) 0.099(3) Uani 1 1 d . . . O3 O 1.2865(12) 0.2718(7) 0.8109(4) 0.153(5) Uani 1 1 d . . . O4 O 0.9376(12) 0.5110(8) 0.7502(3) 0.147(4) Uani 1 1 d . . . O5 O 1.3318(7) 0.6692(7) 0.8106(3) 0.102(3) Uani 1 1 d . . . C1 C 0.7441(7) 0.1235(5) 0.8295(2) 0.0296(16) Uani 1 1 d . . . C2 C 0.8167(7) 0.0912(6) 0.8664(2) 0.0295(16) Uani 1 1 d . . . H2 H 0.797(7) 0.013(6) 0.877(2) 0.035(17) Uiso 1 1 d . . . C3 C 0.9163(7) 0.1786(5) 0.8927(2) 0.0255(14) Uani 1 1 d . . . C4 C 0.8520(7) 0.1941(5) 0.9376(2) 0.0283(15) Uani 1 1 d . . . C5 C 0.8709(8) 0.1065(6) 0.9703(2) 0.0377(18) Uani 1 1 d . . . H5 H 0.9334 0.0357 0.9664 0.045 Uiso 1 1 calc R . . C6 C 0.7988(8) 0.1215(7) 1.0090(3) 0.046(2) Uani 1 1 d . . . H6 H 0.8123 0.0615 1.0316 0.055 Uiso 1 1 calc R . . C7 C 0.7072(9) 0.2243(7) 1.0144(2) 0.0453(19) Uani 1 1 d . . . H7 H 0.6581 0.2347 1.0408 0.054 Uiso 1 1 calc R . . C8 C 0.6859(8) 0.3121(6) 0.9818(2) 0.0380(17) Uani 1 1 d . . . H8 H 0.6232 0.3827 0.9858 0.046 Uiso 1 1 calc R . . C9 C 0.7576(7) 0.2959(6) 0.9430(2) 0.0303(16) Uani 1 1 d . . . C10 C 0.7327(8) 0.3815(6) 0.9039(2) 0.0293(15) Uani 1 1 d . . . H10 H 0.655(6) 0.344(5) 0.891(2) 0.015(16) Uiso 1 1 d . . . C11 C 1.1993(9) 0.4868(7) 0.9053(3) 0.052(2) Uani 1 1 d . . . C12 C 0.9856(9) 0.6500(8) 0.8607(3) 0.057(2) Uani 1 1 d . . . C13 C 1.2107(11) 0.3453(8) 0.8244(3) 0.071(3) Uani 1 1 d . . . C14 C 0.9892(13) 0.5009(9) 0.7865(3) 0.084(3) Uani 1 1 d . . . C15 C 1.2454(9) 0.6018(7) 0.8253(3) 0.055(2) Uani 1 1 d . . . C16 C 0.6478(7) 0.0427(6) 0.8014(2) 0.0304(16) Uani 1 1 d . . . C17 C 0.6659(9) -0.0868(6) 0.8031(3) 0.045(2) Uani 1 1 d . . . H17 H 0.7401 -0.1228 0.8226 0.054 Uiso 1 1 calc R . . C18 C 0.5747(10) -0.1629(7) 0.7763(3) 0.052(2) Uani 1 1 d . . . H18 H 0.5892 -0.2508 0.7769 0.063 Uiso 1 1 calc R . . C19 C 0.4642(10) -0.1122(9) 0.7491(3) 0.056(2) Uani 1 1 d . . . H19 H 0.4000 -0.1650 0.7317 0.067 Uiso 1 1 calc R . . C20 C 0.4467(8) 0.0144(8) 0.7472(2) 0.050(2) Uani 1 1 d . . . H20 H 0.3716 0.0496 0.7279 0.060 Uiso 1 1 calc R . . C21 C 0.5376(8) 0.0916(7) 0.7731(2) 0.0389(18) Uani 1 1 d . . . H21 H 0.5242 0.1796 0.7714 0.047 Uiso 1 1 calc R . . C22 C 0.7177(8) 0.5202(6) 0.9143(2) 0.0382(17) Uani 1 1 d . . . C23 C 0.8077(11) 0.5756(7) 0.9471(3) 0.059(2) Uani 1 1 d . . . H23 H 0.8799 0.5265 0.9633 0.071 Uiso 1 1 calc R . . C24 C 0.7934(16) 0.7009(9) 0.9565(3) 0.086(4) Uani 1 1 d . . . H24 H 0.8567 0.7385 0.9785 0.104 Uiso 1 1 calc R . . C25 C 0.6869(15) 0.7709(9) 0.9337(4) 0.084(4) Uani 1 1 d . . . H25 H 0.6755 0.8570 0.9403 0.101 Uiso 1 1 calc R . . C26 C 0.5961(12) 0.7169(8) 0.9011(4) 0.078(4) Uani 1 1 d . . . H26 H 0.5216 0.7653 0.8856 0.094 Uiso 1 1 calc R . . C27 C 0.6148(9) 0.5924(7) 0.8913(3) 0.053(2) Uani 1 1 d . . . H27 H 0.5551 0.5560 0.8682 0.063 Uiso 1 1 calc R . . C28 C 1.0819(7) 0.1364(5) 0.8955(2) 0.0277(15) Uani 1 1 d . . . C29 C 1.1834(8) 0.1925(6) 0.9252(2) 0.0366(17) Uani 1 1 d . . . H29 H 1.1498 0.2545 0.9446 0.044 Uiso 1 1 calc R . . C30 C 1.3332(8) 0.1574(7) 0.9265(3) 0.046(2) Uani 1 1 d . . . H30 H 1.4025 0.1960 0.9468 0.055 Uiso 1 1 calc R . . C31 C 1.3840(8) 0.0672(7) 0.8988(3) 0.049(2) Uani 1 1 d . . . H31 H 1.4877 0.0452 0.8997 0.059 Uiso 1 1 calc R . . C32 C 1.2840(8) 0.0095(7) 0.8701(3) 0.0492(19) Uani 1 1 d . . . H32 H 1.3177 -0.0545 0.8515 0.059 Uiso 1 1 calc R . . C33 C 1.1331(8) 0.0449(6) 0.8680(2) 0.0363(17) Uani 1 1 d . . . H33 H 1.0645 0.0059 0.8477 0.044 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 W1 0.03311(15) 0.03298(15) 0.03635(19) 0.00908(15) 0.00075(11) -0.00336(14) S1 0.0467(10) 0.0343(8) 0.0173(10) 0.0049(7) -0.0079(8) -0.0023(7) P1 0.0305(9) 0.0294(8) 0.0181(10) 0.0033(7) -0.0044(8) -0.0013(7) O1 0.131(6) 0.075(4) 0.055(5) 0.001(4) -0.042(5) -0.029(4) O2 0.098(5) 0.040(3) 0.164(8) 0.028(4) 0.059(5) 0.020(3) O3 0.204(10) 0.065(4) 0.205(10) 0.029(5) 0.165(9) 0.038(5) O4 0.201(10) 0.145(8) 0.088(7) 0.065(6) -0.072(7) -0.118(7) O5 0.050(4) 0.099(5) 0.158(8) 0.071(5) 0.010(5) -0.012(4) C1 0.031(3) 0.032(3) 0.026(5) 0.003(3) -0.003(3) -0.003(3) C2 0.032(4) 0.031(3) 0.025(5) 0.005(3) -0.004(3) 0.001(3) C3 0.026(3) 0.033(3) 0.017(4) 0.007(3) -0.007(3) 0.000(3) C4 0.029(3) 0.036(3) 0.020(4) 0.008(3) -0.003(3) -0.006(3) C5 0.038(4) 0.046(4) 0.028(5) 0.011(3) -0.006(4) -0.002(3) C6 0.050(5) 0.059(4) 0.029(5) 0.017(4) 0.010(4) 0.000(4) C7 0.050(5) 0.061(5) 0.026(5) 0.003(4) 0.007(4) -0.007(4) C8 0.037(4) 0.048(4) 0.030(5) -0.001(3) 0.000(4) 0.004(3) C9 0.029(4) 0.037(3) 0.024(5) 0.003(3) -0.006(3) -0.009(3) C10 0.031(4) 0.038(4) 0.018(4) -0.001(3) -0.007(3) -0.002(3) C11 0.058(5) 0.039(4) 0.058(6) 0.010(4) -0.013(5) -0.020(4) C12 0.041(5) 0.061(5) 0.071(7) 0.024(4) 0.024(5) 0.009(4) C13 0.078(7) 0.054(5) 0.086(8) 0.023(5) 0.044(6) -0.004(5) C14 0.113(8) 0.088(7) 0.049(6) 0.037(6) -0.026(6) -0.066(6) C15 0.037(4) 0.048(4) 0.081(7) 0.028(4) 0.006(5) 0.001(3) C16 0.028(3) 0.048(4) 0.015(4) -0.001(3) -0.003(3) -0.006(3) C17 0.049(5) 0.046(4) 0.038(6) 0.004(3) -0.011(4) -0.008(3) C18 0.058(5) 0.049(4) 0.049(6) -0.008(4) 0.000(5) -0.025(4) C19 0.051(5) 0.082(6) 0.034(6) -0.008(4) -0.005(5) -0.032(4) C20 0.037(4) 0.086(6) 0.027(5) 0.001(4) -0.008(3) -0.011(4) C21 0.033(4) 0.057(4) 0.026(5) 0.005(3) -0.001(4) -0.008(3) C22 0.044(4) 0.036(4) 0.036(5) 0.007(3) 0.015(3) 0.001(3) C23 0.094(7) 0.051(5) 0.033(6) -0.002(4) 0.006(5) -0.013(4) C24 0.169(12) 0.054(6) 0.039(7) -0.016(5) 0.029(7) -0.032(7) C25 0.135(11) 0.044(5) 0.079(9) -0.003(6) 0.065(8) 0.003(6) C26 0.076(7) 0.054(6) 0.109(10) 0.023(6) 0.048(7) 0.025(5) C27 0.041(4) 0.050(5) 0.068(7) 0.018(4) 0.013(4) 0.006(4) C28 0.032(4) 0.033(3) 0.017(4) 0.009(3) -0.004(3) 0.002(3) C29 0.036(4) 0.045(4) 0.028(5) 0.006(3) -0.003(3) -0.002(3) C30 0.033(4) 0.061(5) 0.042(6) 0.014(4) -0.016(4) -0.005(3) C31 0.026(4) 0.064(5) 0.055(6) 0.020(4) -0.004(4) 0.004(4) C32 0.047(4) 0.048(4) 0.053(5) 0.008(4) 0.008(4) 0.020(4) C33 0.044(4) 0.040(4) 0.025(4) 0.003(3) -0.002(4) 0.000(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 W1 C15 1.965(7) . ? W1 C12 2.001(8) . ? W1 C14 2.004(11) . ? W1 C13 2.023(9) . ? W1 C11 2.028(10) . ? W1 P1 2.5103(16) . ? S1 C1 1.778(6) . ? S1 P1 2.090(3) . ? P1 C10 1.879(7) . ? P1 C3 1.911(6) . ? O1 C11 1.135(10) . ? O2 C12 1.165(9) . ? O3 C13 1.128(10) . ? O4 C14 1.193(12) . ? O5 C15 1.161(9) . ? C1 C2 1.326(10) . ? C1 C16 1.469(9) . ? C2 C3 1.497(9) . ? C3 C4 1.533(9) . ? C3 C28 1.537(8) . ? C4 C5 1.381(9) . ? C4 C9 1.389(9) . ? C5 C6 1.390(10) . ? C6 C7 1.383(10) . ? C7 C8 1.381(10) . ? C8 C9 1.395(9) . ? C9 C10 1.521(9) . ? C10 C22 1.526(9) . ? C16 C21 1.381(10) . ? C16 C17 1.396(10) . ? C17 C18 1.391(11) . ? C18 C19 1.371(12) . ? C19 C20 1.364(11) . ? C20 C21 1.382(10) . ? C22 C27 1.368(11) . ? C22 C23 1.391(11) . ? C23 C24 1.379(12) . ? C24 C25 1.372(17) . ? C25 C26 1.383(16) . ? C26 C27 1.379(12) . ? C28 C33 1.385(9) . ? C28 C29 1.390(10) . ? C29 C30 1.380(9) . ? C30 C31 1.379(11) . ? C31 C32 1.370(11) . ? C32 C33 1.390(10) . ? 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 C15 W1 C12 83.8(3) . . ? C15 W1 C14 87.2(4) . . ? C12 W1 C14 88.3(5) . . ? C15 W1 C13 87.7(3) . . ? C12 W1 C13 170.8(3) . . ? C14 W1 C13 87.7(5) . . ? C15 W1 C11 89.2(3) . . ? C12 W1 C11 91.1(4) . . ? C14 W1 C11 176.5(3) . . ? C13 W1 C11 92.3(4) . . ? C15 W1 P1 175.5(3) . . ? C12 W1 P1 98.7(2) . . ? C14 W1 P1 89.1(2) . . ? C13 W1 P1 89.6(2) . . ? C11 W1 P1 94.4(2) . . ? C1 S1 P1 95.0(3) . . ? C10 P1 C3 92.9(3) . . ? C10 P1 S1 104.9(2) . . ? C3 P1 S1 96.1(2) . . ? C10 P1 W1 123.7(2) . . ? C3 P1 W1 127.0(2) . . ? S1 P1 W1 107.64(8) . . ? C2 C1 C16 126.7(6) . . ? C2 C1 S1 117.0(5) . . ? C16 C1 S1 116.1(5) . . ? C1 C2 C3 123.4(6) . . ? C2 C3 C4 108.7(5) . . ? C2 C3 C28 112.6(5) . . ? C4 C3 C28 112.2(6) . . ? C2 C3 P1 106.1(4) . . ? C4 C3 P1 103.2(4) . . ? C28 C3 P1 113.4(4) . . ? C5 C4 C9 119.9(6) . . ? C5 C4 C3 123.3(6) . . ? C9 C4 C3 116.4(6) . . ? C4 C5 C6 120.2(7) . . ? C7 C6 C5 119.5(7) . . ? C8 C7 C6 121.0(7) . . ? C7 C8 C9 119.2(6) . . ? C4 C9 C8 120.2(6) . . ? C4 C9 C10 116.4(6) . . ? C8 C9 C10 123.4(6) . . ? C9 C10 C22 115.5(6) . . ? C9 C10 P1 104.7(4) . . ? C22 C10 P1 115.5(5) . . ? O1 C11 W1 175.6(7) . . ? O2 C12 W1 170.1(7) . . ? O3 C13 W1 174.2(7) . . ? O4 C14 W1 176.0(8) . . ? O5 C15 W1 175.6(8) . . ? C21 C16 C17 118.5(7) . . ? C21 C16 C1 121.6(6) . . ? C17 C16 C1 119.9(7) . . ? C18 C17 C16 119.7(8) . . ? C19 C18 C17 120.7(8) . . ? C20 C19 C18 119.7(8) . . ? C19 C20 C21 120.5(8) . . ? C16 C21 C20 120.9(7) . . ? C27 C22 C23 118.8(7) . . ? C27 C22 C10 120.2(7) . . ? C23 C22 C10 121.0(7) . . ? C24 C23 C22 120.7(10) . . ? C25 C24 C23 119.5(11) . . ? C24 C25 C26 120.4(9) . . ? C27 C26 C25 119.4(10) . . ? C22 C27 C26 121.1(10) . . ? C33 C28 C29 119.2(6) . . ? C33 C28 C3 121.0(6) . . ? C29 C28 C3 119.8(6) . . ? C30 C29 C28 119.5(7) . . ? C31 C30 C29 121.1(8) . . ? C32 C31 C30 119.7(7) . . ? C31 C32 C33 119.9(7) . . ? C28 C33 C32 120.6(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 S1 P1 C10 -81.4(3) . . . . ? C1 S1 P1 C3 13.2(3) . . . . ? C1 S1 P1 W1 145.3(2) . . . . ? C15 W1 P1 C10 -143(3) . . . . ? C12 W1 P1 C10 -19.1(4) . . . . ? C14 W1 P1 C10 -107.3(5) . . . . ? C13 W1 P1 C10 165.1(4) . . . . ? C11 W1 P1 C10 72.7(4) . . . . ? C15 W1 P1 C3 92(3) . . . . ? C12 W1 P1 C3 -144.4(4) . . . . ? C14 W1 P1 C3 127.4(4) . . . . ? C13 W1 P1 C3 39.7(4) . . . . ? C11 W1 P1 C3 -52.6(4) . . . . ? C15 W1 P1 S1 -20(3) . . . . ? C12 W1 P1 S1 103.3(3) . . . . ? C14 W1 P1 S1 15.1(4) . . . . ? C13 W1 P1 S1 -72.6(3) . . . . ? C11 W1 P1 S1 -164.9(2) . . . . ? P1 S1 C1 C2 -11.6(5) . . . . ? P1 S1 C1 C16 172.6(4) . . . . ? C16 C1 C2 C3 178.3(6) . . . . ? S1 C1 C2 C3 3.1(9) . . . . ? C1 C2 C3 C4 119.1(7) . . . . ? C1 C2 C3 C28 -115.9(7) . . . . ? C1 C2 C3 P1 8.6(8) . . . . ? C10 P1 C3 C2 91.9(5) . . . . ? S1 P1 C3 C2 -13.4(4) . . . . ? W1 P1 C3 C2 -131.0(3) . . . . ? C10 P1 C3 C4 -22.4(5) . . . . ? S1 P1 C3 C4 -127.7(4) . . . . ? W1 P1 C3 C4 114.8(4) . . . . ? C10 P1 C3 C28 -144.1(5) . . . . ? S1 P1 C3 C28 110.6(5) . . . . ? W1 P1 C3 C28 -6.9(6) . . . . ? C2 C3 C4 C5 78.5(8) . . . . ? C28 C3 C4 C5 -46.8(8) . . . . ? P1 C3 C4 C5 -169.2(6) . . . . ? C2 C3 C4 C9 -94.6(7) . . . . ? C28 C3 C4 C9 140.2(6) . . . . ? P1 C3 C4 C9 17.8(7) . . . . ? C9 C4 C5 C6 -1.7(11) . . . . ? C3 C4 C5 C6 -174.5(7) . . . . ? C4 C5 C6 C7 0.5(12) . . . . ? C5 C6 C7 C8 0.2(12) . . . . ? C6 C7 C8 C9 0.4(12) . . . . ? C5 C4 C9 C8 2.2(10) . . . . ? C3 C4 C9 C8 175.5(6) . . . . ? C5 C4 C9 C10 -174.8(6) . . . . ? C3 C4 C9 C10 -1.5(8) . . . . ? C7 C8 C9 C4 -1.6(11) . . . . ? C7 C8 C9 C10 175.3(7) . . . . ? C4 C9 C10 C22 -144.2(6) . . . . ? C8 C9 C10 C22 38.9(9) . . . . ? C4 C9 C10 P1 -16.0(7) . . . . ? C8 C9 C10 P1 167.1(6) . . . . ? C3 P1 C10 C9 21.9(5) . . . . ? S1 P1 C10 C9 119.0(4) . . . . ? W1 P1 C10 C9 -117.4(4) . . . . ? C3 P1 C10 C22 150.1(6) . . . . ? S1 P1 C10 C22 -112.8(5) . . . . ? W1 P1 C10 C22 10.8(7) . . . . ? C15 W1 C11 O1 -4(11) . . . . ? C12 W1 C11 O1 -88(11) . . . . ? C14 W1 C11 O1 -7(14) . . . . ? C13 W1 C11 O1 84(11) . . . . ? P1 W1 C11 O1 173(11) . . . . ? C15 W1 C12 O2 0(5) . . . . ? C14 W1 C12 O2 -87(5) . . . . ? C13 W1 C12 O2 -23(7) . . . . ? C11 W1 C12 O2 89(5) . . . . ? P1 W1 C12 O2 -176(5) . . . . ? C15 W1 C13 O3 -6(12) . . . . ? C12 W1 C13 O3 17(13) . . . . ? C14 W1 C13 O3 82(12) . . . . ? C11 W1 C13 O3 -95(12) . . . . ? P1 W1 C13 O3 171(12) . . . . ? C15 W1 C14 O4 9(17) . . . . ? C12 W1 C14 O4 93(17) . . . . ? C13 W1 C14 O4 -79(17) . . . . ? C11 W1 C14 O4 12(22) . . . . ? P1 W1 C14 O4 -169(17) . . . . ? C12 W1 C15 O5 -76(11) . . . . ? C14 W1 C15 O5 12(11) . . . . ? C13 W1 C15 O5 100(11) . . . . ? C11 W1 C15 O5 -167(11) . . . . ? P1 W1 C15 O5 48(12) . . . . ? C2 C1 C16 C21 156.7(7) . . . . ? S1 C1 C16 C21 -28.0(8) . . . . ? C2 C1 C16 C17 -22.7(10) . . . . ? S1 C1 C16 C17 152.5(5) . . . . ? C21 C16 C17 C18 0.7(11) . . . . ? C1 C16 C17 C18 -179.8(6) . . . . ? C16 C17 C18 C19 -2.0(12) . . . . ? C17 C18 C19 C20 2.3(12) . . . . ? C18 C19 C20 C21 -1.3(12) . . . . ? C17 C16 C21 C20 0.3(10) . . . . ? C1 C16 C21 C20 -179.2(6) . . . . ? C19 C20 C21 C16 0.0(11) . . . . ? C9 C10 C22 C27 -140.5(6) . . . . ? P1 C10 C22 C27 96.9(7) . . . . ? C9 C10 C22 C23 39.5(9) . . . . ? P1 C10 C22 C23 -83.2(7) . . . . ? C27 C22 C23 C24 0.2(11) . . . . ? C10 C22 C23 C24 -179.8(7) . . . . ? C22 C23 C24 C25 1.4(13) . . . . ? C23 C24 C25 C26 -1.0(15) . . . . ? C24 C25 C26 C27 -0.8(14) . . . . ? C23 C22 C27 C26 -2.0(10) . . . . ? C10 C22 C27 C26 177.9(7) . . . . ? C25 C26 C27 C22 2.4(12) . . . . ? C2 C3 C28 C33 14.0(8) . . . . ? C4 C3 C28 C33 137.1(6) . . . . ? P1 C3 C28 C33 -106.5(6) . . . . ? C2 C3 C28 C29 -167.4(6) . . . . ? C4 C3 C28 C29 -44.4(7) . . . . ? P1 C3 C28 C29 72.1(7) . . . . ? C33 C28 C29 C30 1.0(10) . . . . ? C3 C28 C29 C30 -177.7(6) . . . . ? C28 C29 C30 C31 -0.2(11) . . . . ? C29 C30 C31 C32 -1.2(11) . . . . ? C30 C31 C32 C33 2.0(11) . . . . ? C29 C28 C33 C32 -0.2(10) . . . . ? C3 C28 C33 C32 178.4(6) . . . . ? C31 C32 C33 C28 -1.3(11) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 24.06 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.936 _refine_diff_density_min -0.626 _refine_diff_density_rms 0.097 #============================================================================ # DATA for compound 3 in publication #============================================================================ data_jik018 _database_code_CSD 218744 _chemical_name_common ; 3,5,6,6-tetraphenyl-2-thia-1-phosphabicyclo(3.1.0)hex-3-ene P- (pentacarbonyl)tungsten ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5,6,6-tetraphenyl-2-thia-1-phosphabicyclo[3.1.0]hex-3-ene P-(pentacarbonyl)tungsten ; _chemical_melting_point '127 \%C' _chemical_formula_moiety 'C28H21PS x W(CO)5' _chemical_formula_sum 'C33 H21 O5 P S W' _chemical_formula_weight 744.38 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' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.159(3) _cell_length_b 11.268(3) _cell_length_c 13.387(4) _cell_angle_alpha 69.34(3) _cell_angle_beta 79.86(3) _cell_angle_gamma 69.31(3) _cell_volume 1470.9(7) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 4.092 _exptl_absorpt_correction_type DIFABS _exptl_absorpt_correction_T_min 0.53 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'IPDS (Stoe)' _diffrn_measurement_method 'Phi scans, rotation mode' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15692 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.95 _reflns_number_total 5352 _reflns_number_gt 4910 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS software (Stoe, Darmstadt)' _computing_cell_refinement 'IPDS software (Stoe, Darmstadt)' _computing_data_reduction 'X-RED (Stoe, Darmstadt)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1998)' _computing_publication_material 'SHELX-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^)+(0.0381P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5352 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0273 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0552 _refine_ls_wR_factor_gt 0.0542 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 W1 W 0.379831(10) -0.172057(12) 0.276053(9) 0.02345(5) Uani 1 1 d . . . P1 P 0.27051(7) 0.06268(8) 0.27319(6) 0.02175(16) Uani 1 1 d . . . S1 S 0.34307(7) 0.11518(8) 0.38007(6) 0.02569(16) Uani 1 1 d . . . O1 O 0.5418(3) -0.4681(3) 0.2866(2) 0.0515(7) Uani 1 1 d . . . O2 O 0.6260(2) -0.1171(3) 0.3158(2) 0.0432(6) Uani 1 1 d . . . O3 O 0.3308(4) -0.2628(3) 0.5288(2) 0.0655(9) Uani 1 1 d . . . O4 O 0.4405(3) -0.1115(3) 0.0244(2) 0.0496(7) Uani 1 1 d . . . O5 O 0.1235(3) -0.2295(3) 0.2644(3) 0.0548(8) Uani 1 1 d . . . C1 C 0.1988(3) 0.2404(3) 0.3978(2) 0.0244(6) Uani 1 1 d . . . C2 C 0.0975(3) 0.2581(3) 0.3472(2) 0.0246(6) Uani 1 1 d . . . H2 H 0.0171 0.3188 0.3608 0.029 Uiso 1 1 calc R . . C3 C 0.1054(3) 0.1872(3) 0.2712(2) 0.0220(6) Uani 1 1 d . . . C4 C 0.1951(3) 0.2228(3) 0.1678(2) 0.0230(6) Uani 1 1 d . . . C5 C 0.2037(3) 0.3171(3) 0.4656(2) 0.0249(6) Uani 1 1 d . . . C6 C 0.3022(3) 0.3727(4) 0.4486(3) 0.0326(7) Uani 1 1 d . . . H6 H 0.3679 0.3588 0.3943 0.039 Uiso 1 1 calc R . . C7 C 0.3050(3) 0.4483(4) 0.5104(3) 0.0358(8) Uani 1 1 d . . . H7 H 0.3719 0.4865 0.4978 0.043 Uiso 1 1 calc R . . C8 C 0.2097(3) 0.4679(3) 0.5905(3) 0.0348(8) Uani 1 1 d . . . H8 H 0.2112 0.5197 0.6327 0.042 Uiso 1 1 calc R . . C9 C 0.1125(3) 0.4118(4) 0.6089(3) 0.0335(8) Uani 1 1 d . . . H9 H 0.0478 0.4246 0.6641 0.040 Uiso 1 1 calc R . . C10 C 0.1094(3) 0.3372(3) 0.5471(2) 0.0286(7) Uani 1 1 d . . . H10 H 0.0423 0.2992 0.5603 0.034 Uiso 1 1 calc R . . C11 C -0.0184(3) 0.1639(3) 0.2657(2) 0.0251(6) Uani 1 1 d . . . C12 C -0.0501(3) 0.0556(4) 0.3395(3) 0.0322(7) Uani 1 1 d . . . H12 H 0.0091 -0.0086 0.3907 0.039 Uiso 1 1 calc R . . C13 C -0.1687(3) 0.0407(4) 0.3385(3) 0.0415(9) Uani 1 1 d . . . H13 H -0.1892 -0.0347 0.3882 0.050 Uiso 1 1 calc R . . C14 C -0.2568(3) 0.1353(4) 0.2656(3) 0.0444(9) Uani 1 1 d . . . H14 H -0.3380 0.1255 0.2659 0.053 Uiso 1 1 calc R . . C15 C -0.2260(3) 0.2436(4) 0.1926(3) 0.0441(9) Uani 1 1 d . . . H15 H -0.2858 0.3082 0.1419 0.053 Uiso 1 1 calc R . . C16 C -0.1071(3) 0.2586(4) 0.1931(3) 0.0359(8) Uani 1 1 d . . . H16 H -0.0869 0.3341 0.1433 0.043 Uiso 1 1 calc R . . C17 C 0.2344(3) 0.3429(3) 0.1485(2) 0.0247(6) Uani 1 1 d . . . C18 C 0.3627(3) 0.3369(4) 0.1387(2) 0.0313(7) Uani 1 1 d . . . H18 H 0.4284 0.2532 0.1480 0.038 Uiso 1 1 calc R . . C19 C 0.3951(3) 0.4526(4) 0.1154(3) 0.0380(8) Uani 1 1 d . . . H19 H 0.4828 0.4472 0.1101 0.046 Uiso 1 1 calc R . . C20 C 0.3008(4) 0.5752(4) 0.1000(3) 0.0415(9) Uani 1 1 d . . . H20 H 0.3235 0.6540 0.0841 0.050 Uiso 1 1 calc R . . C21 C 0.1726(4) 0.5829(4) 0.1079(3) 0.0401(8) Uani 1 1 d . . . H21 H 0.1075 0.6672 0.0962 0.048 Uiso 1 1 calc R . . C22 C 0.1398(3) 0.4681(3) 0.1328(3) 0.0312(7) Uani 1 1 d . . . H22 H 0.0518 0.4740 0.1394 0.037 Uiso 1 1 calc R . . C23 C 0.1786(3) 0.1983(3) 0.0674(2) 0.0259(6) Uani 1 1 d . . . C24 C 0.1347(3) 0.0967(4) 0.0682(3) 0.0306(7) Uani 1 1 d . . . H24 H 0.1068 0.0432 0.1342 0.037 Uiso 1 1 calc R . . C25 C 0.1308(3) 0.0716(4) -0.0254(3) 0.0377(8) Uani 1 1 d . . . H25 H 0.1040 -0.0008 -0.0224 0.045 Uiso 1 1 calc R . . C26 C 0.1660(3) 0.1521(5) -0.1229(3) 0.0449(10) Uani 1 1 d . . . H26 H 0.1611 0.1371 -0.1874 0.054 Uiso 1 1 calc R . . C27 C 0.2079(3) 0.2536(4) -0.1252(3) 0.0421(9) Uani 1 1 d . . . H27 H 0.2327 0.3087 -0.1919 0.050 Uiso 1 1 calc R . . C28 C 0.2147(3) 0.2772(4) -0.0318(2) 0.0337(8) Uani 1 1 d . . . H28 H 0.2444 0.3481 -0.0354 0.040 Uiso 1 1 calc R . . C29 C 0.4824(3) -0.3606(4) 0.2836(3) 0.0358(8) Uani 1 1 d . . . C30 C 0.5408(3) -0.1375(3) 0.2984(3) 0.0293(7) Uani 1 1 d . . . C31 C 0.3477(4) -0.2292(4) 0.4386(3) 0.0401(8) Uani 1 1 d . . . C32 C 0.4169(3) -0.1259(4) 0.1126(3) 0.0326(7) Uani 1 1 d . . . C33 C 0.2149(3) -0.2080(4) 0.2660(3) 0.0334(7) 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 W1 0.02299(7) 0.02057(8) 0.02713(7) -0.00860(5) -0.00104(4) -0.00640(5) P1 0.0215(3) 0.0208(4) 0.0219(3) -0.0072(3) -0.0032(3) -0.0040(3) S1 0.0258(3) 0.0252(4) 0.0254(4) -0.0096(3) -0.0067(3) -0.0034(3) O1 0.0519(16) 0.0282(16) 0.073(2) -0.0237(13) -0.0206(14) 0.0047(12) O2 0.0290(12) 0.0447(17) 0.0601(17) -0.0194(13) -0.0077(11) -0.0114(11) O3 0.117(3) 0.045(2) 0.0300(15) -0.0093(13) 0.0081(15) -0.0292(18) O4 0.0506(15) 0.065(2) 0.0306(14) -0.0187(12) 0.0067(11) -0.0166(13) O5 0.0395(14) 0.067(2) 0.079(2) -0.0414(17) 0.0099(13) -0.0292(14) C1 0.0289(14) 0.0231(17) 0.0191(13) -0.0057(11) 0.0005(11) -0.0075(11) C2 0.0265(14) 0.0227(17) 0.0215(14) -0.0069(12) 0.0014(11) -0.0059(11) C3 0.0218(13) 0.0206(16) 0.0223(14) -0.0076(11) -0.0008(10) -0.0045(11) C4 0.0201(12) 0.0253(17) 0.0221(14) -0.0068(11) -0.0030(10) -0.0053(11) C5 0.0310(15) 0.0208(16) 0.0195(13) -0.0042(11) -0.0067(11) -0.0040(11) C6 0.0397(17) 0.032(2) 0.0274(16) -0.0088(13) 0.0006(13) -0.0147(14) C7 0.0440(18) 0.030(2) 0.0372(18) -0.0085(14) -0.0074(14) -0.0151(14) C8 0.0454(18) 0.0237(19) 0.0353(17) -0.0149(14) -0.0158(14) 0.0011(14) C9 0.0328(16) 0.036(2) 0.0264(15) -0.0133(13) -0.0065(12) 0.0010(13) C10 0.0309(15) 0.0258(18) 0.0245(15) -0.0074(12) -0.0064(11) -0.0020(12) C11 0.0217(13) 0.0312(18) 0.0244(14) -0.0129(12) 0.0027(11) -0.0086(12) C12 0.0305(15) 0.0333(19) 0.0301(16) -0.0074(14) 0.0008(12) -0.0106(13) C13 0.0397(18) 0.040(2) 0.049(2) -0.0144(17) 0.0088(15) -0.0226(16) C14 0.0290(16) 0.057(3) 0.056(2) -0.0246(19) 0.0020(15) -0.0192(16) C15 0.0247(16) 0.054(3) 0.048(2) -0.0082(18) -0.0082(14) -0.0104(15) C16 0.0252(15) 0.040(2) 0.0348(17) -0.0026(15) -0.0036(12) -0.0095(13) C17 0.0248(14) 0.0285(17) 0.0179(13) -0.0050(11) -0.0006(10) -0.0078(12) C18 0.0272(15) 0.037(2) 0.0277(16) -0.0083(13) 0.0008(12) -0.0112(13) C19 0.0379(17) 0.046(2) 0.0348(18) -0.0096(16) 0.0015(14) -0.0239(16) C20 0.060(2) 0.036(2) 0.0380(19) -0.0103(16) 0.0038(16) -0.0308(18) C21 0.048(2) 0.028(2) 0.0387(19) -0.0072(15) 0.0002(15) -0.0101(15) C22 0.0318(15) 0.0264(18) 0.0329(16) -0.0082(13) -0.0023(12) -0.0071(13) C23 0.0195(13) 0.0314(18) 0.0255(15) -0.0112(12) -0.0032(11) -0.0034(11) C24 0.0231(14) 0.039(2) 0.0301(16) -0.0131(14) -0.0019(12) -0.0081(13) C25 0.0275(15) 0.054(3) 0.044(2) -0.0290(17) -0.0022(13) -0.0143(15) C26 0.0333(17) 0.076(3) 0.0340(18) -0.0316(19) -0.0039(14) -0.0116(17) C27 0.0426(19) 0.059(3) 0.0247(16) -0.0105(16) -0.0026(14) -0.0183(17) C28 0.0313(15) 0.043(2) 0.0243(15) -0.0071(14) -0.0023(12) -0.0116(14) C29 0.0361(17) 0.035(2) 0.0385(18) -0.0112(15) -0.0054(14) -0.0123(15) C30 0.0300(16) 0.0210(18) 0.0352(17) -0.0122(13) -0.0028(12) -0.0024(12) C31 0.055(2) 0.022(2) 0.041(2) -0.0094(15) 0.0009(16) -0.0116(15) C32 0.0278(15) 0.033(2) 0.0368(19) -0.0126(14) 0.0012(13) -0.0084(13) C33 0.0327(16) 0.032(2) 0.0410(18) -0.0187(15) 0.0026(13) -0.0123(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 W1 C29 2.001(4) . ? W1 C31 2.043(4) . ? W1 C30 2.058(3) . ? W1 C33 2.055(3) . ? W1 C32 2.063(4) . ? W1 P1 2.4800(12) . ? P1 C4 1.872(3) . ? P1 C3 1.878(3) . ? P1 S1 2.0968(12) . ? S1 C1 1.771(3) . ? O1 C29 1.148(5) . ? O2 C30 1.132(4) . ? O3 C31 1.134(5) . ? O4 C32 1.130(4) . ? O5 C33 1.133(4) . ? C1 C2 1.339(4) . ? C1 C5 1.476(4) . ? C2 C3 1.473(4) . ? C3 C11 1.513(4) . ? C3 C4 1.576(4) . ? C4 C17 1.491(5) . ? C4 C23 1.516(4) . ? C5 C6 1.397(5) . ? C5 C10 1.397(4) . ? C6 C7 1.391(5) . ? C7 C8 1.389(5) . ? C8 C9 1.384(5) . ? C9 C10 1.383(5) . ? C11 C16 1.387(4) . ? C11 C12 1.386(5) . ? C12 C13 1.394(5) . ? C13 C14 1.385(6) . ? C14 C15 1.378(6) . ? C15 C16 1.397(5) . ? C17 C18 1.393(4) . ? C17 C22 1.402(5) . ? C18 C19 1.391(5) . ? C19 C20 1.381(6) . ? C20 C21 1.389(5) . ? C21 C22 1.381(5) . ? C23 C24 1.393(5) . ? C23 C28 1.396(4) . ? C24 C25 1.388(5) . ? C25 C26 1.384(6) . ? C26 C27 1.369(6) . ? C27 C28 1.387(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 C29 W1 C31 90.49(15) . . ? C29 W1 C30 90.68(13) . . ? C31 W1 C30 87.28(15) . . ? C29 W1 C33 90.24(14) . . ? C31 W1 C33 88.34(15) . . ? C30 W1 C33 175.53(12) . . ? C29 W1 C32 86.23(15) . . ? C31 W1 C32 176.68(14) . . ? C30 W1 C32 93.23(13) . . ? C33 W1 C32 91.19(14) . . ? C29 W1 P1 174.54(10) . . ? C31 W1 P1 88.11(11) . . ? C30 W1 P1 83.98(10) . . ? C33 W1 P1 95.00(11) . . ? C32 W1 P1 95.20(11) . . ? C4 P1 C3 49.70(12) . . ? C4 P1 S1 106.12(11) . . ? C3 P1 S1 96.53(10) . . ? C4 P1 W1 134.54(10) . . ? C3 P1 W1 140.77(10) . . ? S1 P1 W1 113.07(5) . . ? C1 S1 P1 95.06(11) . . ? C2 C1 C5 126.5(3) . . ? C2 C1 S1 117.3(3) . . ? C5 C1 S1 116.1(2) . . ? C1 C2 C3 122.7(3) . . ? C2 C3 C11 114.0(2) . . ? C2 C3 C4 114.2(2) . . ? C11 C3 C4 121.1(2) . . ? C2 C3 P1 108.10(19) . . ? C11 C3 P1 125.7(2) . . ? C4 C3 P1 64.92(15) . . ? C17 C4 C23 114.8(2) . . ? C17 C4 C3 116.0(3) . . ? C23 C4 C3 120.0(2) . . ? C17 C4 P1 120.2(2) . . ? C23 C4 P1 111.6(2) . . ? C3 C4 P1 65.37(15) . . ? C6 C5 C10 118.5(3) . . ? C6 C5 C1 120.6(3) . . ? C10 C5 C1 121.0(3) . . ? C7 C6 C5 120.7(3) . . ? C8 C7 C6 119.8(3) . . ? C9 C8 C7 120.0(3) . . ? C8 C9 C10 120.2(3) . . ? C9 C10 C5 120.9(3) . . ? C16 C11 C12 119.2(3) . . ? C16 C11 C3 119.8(3) . . ? C12 C11 C3 120.7(3) . . ? C11 C12 C13 120.1(3) . . ? C14 C13 C12 120.4(3) . . ? C15 C14 C13 119.6(3) . . ? C14 C15 C16 120.1(3) . . ? C11 C16 C15 120.5(3) . . ? C18 C17 C22 118.4(3) . . ? C18 C17 C4 122.4(3) . . ? C22 C17 C4 119.1(3) . . ? C19 C18 C17 120.4(3) . . ? C20 C19 C18 120.5(3) . . ? C19 C20 C21 119.7(3) . . ? C22 C21 C20 120.1(3) . . ? C21 C22 C17 120.9(3) . . ? C24 C23 C28 117.3(3) . . ? C24 C23 C4 123.7(3) . . ? C28 C23 C4 118.9(3) . . ? C25 C24 C23 121.6(3) . . ? C26 C25 C24 120.0(4) . . ? C27 C26 C25 119.1(3) . . ? C26 C27 C28 121.1(3) . . ? C27 C28 C23 120.9(4) . . ? O1 C29 W1 179.1(3) . . ? O2 C30 W1 176.2(3) . . ? O3 C31 W1 179.0(4) . . ? O4 C32 W1 174.4(3) . . ? O5 C33 W1 177.5(3) . . ? 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 C29 W1 P1 C4 123.4(11) . . . . ? C31 W1 P1 C4 -161.51(17) . . . . ? C30 W1 P1 C4 111.03(16) . . . . ? C33 W1 P1 C4 -73.34(16) . . . . ? C32 W1 P1 C4 18.31(15) . . . . ? C29 W1 P1 C3 -159.9(11) . . . . ? C31 W1 P1 C3 -84.77(19) . . . . ? C30 W1 P1 C3 -172.24(17) . . . . ? C33 W1 P1 C3 3.39(17) . . . . ? C32 W1 P1 C3 95.05(17) . . . . ? C29 W1 P1 S1 -24.1(11) . . . . ? C31 W1 P1 S1 51.07(12) . . . . ? C30 W1 P1 S1 -36.40(10) . . . . ? C33 W1 P1 S1 139.23(10) . . . . ? C32 W1 P1 S1 -129.11(10) . . . . ? C4 P1 S1 C1 50.59(14) . . . . ? C3 P1 S1 C1 0.72(13) . . . . ? W1 P1 S1 C1 -152.95(10) . . . . ? P1 S1 C1 C2 2.3(2) . . . . ? P1 S1 C1 C5 -176.3(2) . . . . ? C5 C1 C2 C3 172.8(3) . . . . ? S1 C1 C2 C3 -5.8(4) . . . . ? C1 C2 C3 C11 150.8(3) . . . . ? C1 C2 C3 C4 -64.1(4) . . . . ? C1 C2 C3 P1 6.0(4) . . . . ? C4 P1 C3 C2 -108.9(3) . . . . ? S1 P1 C3 C2 -3.3(2) . . . . ? W1 P1 C3 C2 136.55(17) . . . . ? C4 P1 C3 C11 111.5(3) . . . . ? S1 P1 C3 C11 -142.9(2) . . . . ? W1 P1 C3 C11 -3.0(3) . . . . ? S1 P1 C3 C4 105.63(15) . . . . ? W1 P1 C3 C4 -114.54(17) . . . . ? C2 C3 C4 C17 -13.6(3) . . . . ? C11 C3 C4 C17 128.8(3) . . . . ? P1 C3 C4 C17 -113.1(2) . . . . ? C2 C3 C4 C23 -158.7(3) . . . . ? C11 C3 C4 C23 -16.4(4) . . . . ? P1 C3 C4 C23 101.7(3) . . . . ? C2 C3 C4 P1 99.5(2) . . . . ? C11 C3 C4 P1 -118.1(3) . . . . ? C3 P1 C4 C17 106.9(3) . . . . ? S1 P1 C4 C17 22.0(2) . . . . ? W1 P1 C4 C17 -126.9(2) . . . . ? C3 P1 C4 C23 -114.2(3) . . . . ? S1 P1 C4 C23 160.95(17) . . . . ? W1 P1 C4 C23 12.0(3) . . . . ? S1 P1 C4 C3 -84.84(15) . . . . ? W1 P1 C4 C3 126.19(15) . . . . ? C2 C1 C5 C6 -129.4(3) . . . . ? S1 C1 C5 C6 49.1(4) . . . . ? C2 C1 C5 C10 49.7(4) . . . . ? S1 C1 C5 C10 -131.8(3) . . . . ? C10 C5 C6 C7 -1.0(5) . . . . ? C1 C5 C6 C7 178.1(3) . . . . ? C5 C6 C7 C8 0.6(5) . . . . ? C6 C7 C8 C9 0.2(5) . . . . ? C7 C8 C9 C10 -0.5(5) . . . . ? C8 C9 C10 C5 0.0(5) . . . . ? C6 C5 C10 C9 0.7(4) . . . . ? C1 C5 C10 C9 -178.5(3) . . . . ? C2 C3 C11 C16 90.1(3) . . . . ? C4 C3 C11 C16 -52.4(4) . . . . ? P1 C3 C11 C16 -132.3(3) . . . . ? C2 C3 C11 C12 -83.4(4) . . . . ? C4 C3 C11 C12 134.1(3) . . . . ? P1 C3 C11 C12 54.2(4) . . . . ? C16 C11 C12 C13 1.6(5) . . . . ? C3 C11 C12 C13 175.2(3) . . . . ? C11 C12 C13 C14 -1.4(6) . . . . ? C12 C13 C14 C15 1.0(6) . . . . ? C13 C14 C15 C16 -0.7(6) . . . . ? C12 C11 C16 C15 -1.4(5) . . . . ? C3 C11 C16 C15 -175.0(3) . . . . ? C14 C15 C16 C11 0.9(6) . . . . ? C23 C4 C17 C18 -90.7(3) . . . . ? C3 C4 C17 C18 122.4(3) . . . . ? P1 C4 C17 C18 47.0(4) . . . . ? C23 C4 C17 C22 85.2(3) . . . . ? C3 C4 C17 C22 -61.7(4) . . . . ? P1 C4 C17 C22 -137.1(2) . . . . ? C22 C17 C18 C19 0.9(5) . . . . ? C4 C17 C18 C19 176.8(3) . . . . ? C17 C18 C19 C20 -1.0(5) . . . . ? C18 C19 C20 C21 0.0(5) . . . . ? C19 C20 C21 C22 1.0(6) . . . . ? C20 C21 C22 C17 -1.2(5) . . . . ? C18 C17 C22 C21 0.2(5) . . . . ? C4 C17 C22 C21 -175.8(3) . . . . ? C17 C4 C23 C24 -175.8(3) . . . . ? C3 C4 C23 C24 -30.3(4) . . . . ? P1 C4 C23 C24 42.9(3) . . . . ? C17 C4 C23 C28 7.3(4) . . . . ? C3 C4 C23 C28 152.8(3) . . . . ? P1 C4 C23 C28 -133.9(3) . . . . ? C28 C23 C24 C25 2.1(4) . . . . ? C4 C23 C24 C25 -174.8(3) . . . . ? C23 C24 C25 C26 -2.8(5) . . . . ? C24 C25 C26 C27 1.9(5) . . . . ? C25 C26 C27 C28 -0.4(6) . . . . ? C26 C27 C28 C23 -0.2(5) . . . . ? C24 C23 C28 C27 -0.6(5) . . . . ? C4 C23 C28 C27 176.4(3) . . . . ? C31 W1 C29 O1 -168(100) . . . . ? C30 W1 C29 O1 -81(20) . . . . ? C33 W1 C29 O1 104(20) . . . . ? C32 W1 C29 O1 13(20) . . . . ? P1 W1 C29 O1 -93(21) . . . . ? C29 W1 C30 O2 -119(5) . . . . ? C31 W1 C30 O2 -29(5) . . . . ? C33 W1 C30 O2 -17(6) . . . . ? C32 W1 C30 O2 155(5) . . . . ? P1 W1 C30 O2 60(5) . . . . ? C29 W1 C31 O3 -4(22) . . . . ? C30 W1 C31 O3 -94(22) . . . . ? C33 W1 C31 O3 87(22) . . . . ? C32 W1 C31 O3 5(24) . . . . ? P1 W1 C31 O3 -178(100) . . . . ? C29 W1 C32 O4 13(3) . . . . ? C31 W1 C32 O4 5(4) . . . . ? C30 W1 C32 O4 104(3) . . . . ? C33 W1 C32 O4 -77(3) . . . . ? P1 W1 C32 O4 -172(3) . . . . ? C29 W1 C33 O5 85(8) . . . . ? C31 W1 C33 O5 -5(8) . . . . ? C30 W1 C33 O5 -17(9) . . . . ? C32 W1 C33 O5 172(8) . . . . ? P1 W1 C33 O5 -93(8) . . . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 25.95 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.604 _refine_diff_density_min -1.123 _refine_diff_density_rms 0.112