data_el01 _database_code_CSD 169046 _journal_coden_Cambridge 207 _publ_contact_author 'Professor J. S. Field' _publ_contact_author_address ; Professor J. S. Field, School of Chemical and Physical Sciences, University of Natal, Pietermaritzburg 3201, South Africa ; _publ_contact_author_email 'fieldj@nu.ac.za' loop_ _publ_author_name 'John S. Field' 'Raymond J. Haines' 'Elena I. Lakoba' 'M. Hal Sosabowski' _journal_name_full ' J. Chem Soc Perkin Transactions I' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,5'-bis(diphenylphosphino)-2,2'-bithiophene ; _chemical_name_common ? _chemical_melting_point '191 C' _chemical_formula_moiety '{P(C6H5)2}2(C8H4S2)' _chemical_formula_sum 'C32 H24 P2 S2' _chemical_formula_weight 534.57 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 2(1)/c' 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 8.954(2) _cell_length_b 19.678(3) _cell_length_c 8.877(2) _cell_angle_alpha 90.00 _cell_angle_beta 117.93(2) _cell_angle_gamma 90.00 _cell_volume 1381.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2 _cell_measurement_theta_max 12 _exptl_crystal_description 'needle' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_type 'Semi-empirical' _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _exptl_special_details ; ? ; _exptl_crystal_preparation ; Crystals grown from chloroform by slow evaporation ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Nonius CAD4' _diffrn_measurement_method 'omega-2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '60 minutes' _diffrn_standards_decay_% 0% _diffrn_reflns_number 2508 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 22.97 _reflns_number_total 1923 _reflns_number_gt 1652 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius CAD4' _computing_cell_refinement 'CELDIM, CAD4' _computing_data_reduction 'XCAD (McArdle, 2000)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OSCAIL (McArdle 2000)' _computing_publication_material 'ORTEP 3 (Farrugia, 2000)' _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^)+(0.0739P)^2^+0.6782P] 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 1923 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.32182(10) 0.67999(4) 0.05940(10) 0.0526(3) Uani 1 1 d . . . S1 S 0.47203(11) 0.54640(4) 0.26582(10) 0.0607(3) Uani 1 1 d . . . C1 C 0.3667(4) 0.62261(14) 0.2334(4) 0.0499(7) Uani 1 1 d . . . C2 C 0.3293(4) 0.63377(17) 0.3630(4) 0.0595(8) Uani 1 1 d . . . C3 C 0.3835(5) 0.58214(17) 0.4849(4) 0.0629(9) Uani 1 1 d . . . C4 C 0.4639(3) 0.53079(14) 0.4525(3) 0.0470(7) Uani 1 1 d . . . C5 C 0.5212(4) 0.67858(15) 0.0494(4) 0.0529(8) Uani 1 1 d . . . C6 C 0.6294(5) 0.7322(2) 0.1245(5) 0.0775(11) Uani 1 1 d . . . C7 C 0.7840(6) 0.7344(3) 0.1292(7) 0.0979(15) Uani 1 1 d . . . C8 C 0.8307(6) 0.6839(3) 0.0566(6) 0.0967(17) Uani 1 1 d . . . C9 C 0.7271(5) 0.6299(3) -0.0170(6) 0.0846(12) Uani 1 1 d . . . C10 C 0.5719(5) 0.6275(2) -0.0208(5) 0.0668(9) Uani 1 1 d . . . C11 C 0.1814(3) 0.63128(16) -0.1274(4) 0.0517(7) Uani 1 1 d . . . C12 C 0.1501(5) 0.6555(2) -0.2867(4) 0.0672(9) Uani 1 1 d . . . C13 C 0.0299(6) 0.6243(3) -0.4329(5) 0.0874(14) Uani 1 1 d . . . C14 C -0.0601(6) 0.5697(3) -0.4230(7) 0.1014(16) Uani 1 1 d . . . C15 C -0.0321(6) 0.5463(3) -0.2679(7) 0.1054(16) Uani 1 1 d . . . C16 C 0.0871(5) 0.5766(2) -0.1226(5) 0.0788(11) Uani 1 1 d . . . H1 H 0.263(4) 0.6742(17) 0.363(4) 0.067(9) Uiso 1 1 d . . . H2 H 0.358(5) 0.581(2) 0.573(5) 0.089(12) Uiso 1 1 d . . . H3 H 0.600(5) 0.764(2) 0.160(5) 0.075(13) Uiso 1 1 d . . . H4 H 0.857(6) 0.770(2) 0.177(5) 0.095(13) Uiso 1 1 d . . . H5 H 0.923(6) 0.686(2) 0.065(6) 0.091(14) Uiso 1 1 d . . . H6 H 0.761(5) 0.595(2) -0.056(5) 0.078(12) Uiso 1 1 d . . . H7 H 0.506(5) 0.5941(18) -0.060(5) 0.072(11) Uiso 1 1 d . . . H8 H 0.207(5) 0.6933(19) -0.293(5) 0.077(12) Uiso 1 1 d . . . H9 H 0.002(6) 0.641(2) -0.528(6) 0.104(16) Uiso 1 1 d . . . H10 H -0.149(6) 0.551(2) -0.525(7) 0.119(16) Uiso 1 1 d . . . H11 H -0.094(6) 0.504(3) -0.255(6) 0.130(17) Uiso 1 1 d . . . H12 H 0.112(5) 0.559(2) -0.019(6) 0.094(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0600(5) 0.0508(5) 0.0531(5) 0.0024(3) 0.0317(4) 0.0040(4) S1 0.0778(6) 0.0677(6) 0.0505(5) 0.0089(4) 0.0416(4) 0.0200(4) C1 0.0558(17) 0.0514(17) 0.0488(16) -0.0014(13) 0.0299(14) 0.0000(13) C2 0.077(2) 0.0571(19) 0.0570(19) -0.0009(15) 0.0419(17) 0.0123(16) C3 0.087(2) 0.069(2) 0.0517(18) 0.0006(16) 0.0477(18) 0.0124(18) C4 0.0466(15) 0.0593(17) 0.0383(15) -0.0026(12) 0.0226(13) -0.0039(13) C5 0.0591(18) 0.0544(18) 0.0494(17) 0.0045(13) 0.0289(15) -0.0040(14) C6 0.079(3) 0.075(3) 0.078(3) -0.010(2) 0.036(2) -0.016(2) C7 0.077(3) 0.118(4) 0.097(3) -0.010(3) 0.040(3) -0.040(3) C8 0.056(2) 0.152(5) 0.086(3) 0.020(3) 0.036(2) -0.009(3) C9 0.068(2) 0.110(3) 0.090(3) 0.006(3) 0.049(2) 0.010(3) C10 0.065(2) 0.070(2) 0.076(2) -0.0010(19) 0.0425(19) -0.0049(19) C11 0.0442(16) 0.0610(18) 0.0524(18) 0.0024(14) 0.0248(14) 0.0074(13) C12 0.071(2) 0.080(2) 0.056(2) 0.0074(18) 0.0337(18) 0.011(2) C13 0.083(3) 0.130(4) 0.048(2) 0.002(2) 0.030(2) 0.029(3) C14 0.063(3) 0.146(5) 0.081(3) -0.035(3) 0.022(2) -0.012(3) C15 0.083(3) 0.139(4) 0.083(3) -0.023(3) 0.030(3) -0.044(3) C16 0.072(2) 0.096(3) 0.063(2) -0.001(2) 0.027(2) -0.022(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.800(3) . ? P1 C11 1.816(3) . ? P1 C5 1.828(3) . ? S1 C4 1.720(3) . ? S1 C1 1.722(3) . ? C1 C2 1.358(4) . ? C2 C3 1.395(5) . ? C3 C4 1.347(4) . ? C4 C4 1.445(6) 3_666 ? C5 C10 1.368(5) . ? C5 C6 1.375(5) . ? C6 C7 1.366(6) . ? C7 C8 1.353(7) . ? C8 C9 1.360(7) . ? C9 C10 1.375(5) . ? C11 C16 1.381(5) . ? C11 C12 1.391(5) . ? C12 C13 1.382(6) . ? C13 C14 1.370(7) . ? C14 C15 1.360(7) . ? C15 C16 1.367(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C11 103.50(14) . . ? C1 P1 C5 101.61(13) . . ? C11 P1 C5 102.84(14) . . ? C4 S1 C1 92.83(14) . . ? C2 C1 S1 109.4(2) . . ? C2 C1 P1 125.5(2) . . ? S1 C1 P1 125.04(17) . . ? C1 C2 C3 113.9(3) . . ? C4 C3 C2 114.0(3) . . ? C3 C4 C4 129.9(3) . 3_666 ? C3 C4 S1 109.9(2) . . ? C4 C4 S1 120.2(3) 3_666 . ? C10 C5 C6 118.4(3) . . ? C10 C5 P1 125.0(3) . . ? C6 C5 P1 116.6(3) . . ? C7 C6 C5 120.9(5) . . ? C8 C7 C6 119.8(5) . . ? C7 C8 C9 120.6(4) . . ? C8 C9 C10 119.5(5) . . ? C5 C10 C9 120.8(4) . . ? C16 C11 C12 117.6(3) . . ? C16 C11 P1 123.7(3) . . ? C12 C11 P1 118.1(3) . . ? C13 C12 C11 120.0(4) . . ? C14 C13 C12 120.7(4) . . ? C15 C14 C13 119.8(4) . . ? C14 C15 C16 120.0(5) . . ? C15 C16 C11 121.9(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.453 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.051 data_el04 _database_code_CSD 169047 _journal_coden_Cambridge 207 _publ_contact_author 'Professor J. S. Field' _publ_contact_author_address ; Professor J. S. Field, School of Chemical and Physical Sciences, University of Natal, Pietermaritzburg 3201, South Africa ; _publ_contact_author_email 'fieldj@nu.ac.za' loop_ _publ_author_name 'John S. Field' 'Raymond J. Haines' 'Elena I. Lakoba' _journal_name_full 'J Chem Soc Perkin Transactions I' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-bis[(5'-diphenylphosphino)-2'-thienyl]pyridine ; _chemical_name_common ? _chemical_melting_point '175 C' _chemical_formula_moiety '[{P(C6H5)2}2(C4H2S)2(C6H3N)2]' _chemical_formula_sum 'C37 H27 N P2 S2' _chemical_formula_weight 611.66 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' 'N' 'N' 0.0061 0.0033 '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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P-1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.032(2) _cell_length_b 13.312(3) _cell_length_c 13.577(3) _cell_angle_alpha 85.853(18) _cell_angle_beta 82.694(19) _cell_angle_gamma 73.772(18) _cell_volume 1553.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2 _cell_measurement_theta_max 12 _exptl_crystal_description 'block' _exptl_crystal_colour 'green' _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type PSI-Scans _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ; Walker, N. & Stuart, D. (1983) Acta. Cryst. A39, 158-166. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius CAD4' _diffrn_measurement_method 'omega-2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '60 minutes' _diffrn_standards_decay_% 0% _diffrn_reflns_number 4946 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 22.97 _reflns_number_total 4301 _reflns_number_gt 3311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius CAD4' _computing_cell_refinement 'CELDIM, CAD4' _computing_data_reduction 'XCAD (McArdle, 2000)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OSCAIL (McArdle 2000)' _computing_publication_material 'ORTEP 3 (Farrugia, 2000)' _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^)+(0.0513P)^2^+0.4329P] 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 4301 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.55289(9) -0.10951(5) -0.21365(5) 0.0516(2) Uani 1 1 d . . . S2 S 0.36435(8) 0.23505(5) -0.12174(5) 0.0491(2) Uani 1 1 d . . . P1 P 0.77994(9) -0.27194(6) -0.35923(6) 0.0526(2) Uani 1 1 d . . . P2 P 0.38622(9) 0.46637(5) -0.15832(6) 0.0500(2) Uani 1 1 d . . . N N 0.3295(2) 0.02498(17) -0.06732(15) 0.0444(5) Uani 1 1 d . . . C1 C 0.6391(3) -0.2352(2) -0.2522(2) 0.0472(7) Uani 1 1 d . . . C2 C 0.5826(4) -0.3046(2) -0.1907(2) 0.0505(7) Uani 1 1 d . . . C3 C 0.4710(3) -0.2580(2) -0.1147(2) 0.0507(7) Uani 1 1 d . . . C4 C 0.4418(3) -0.1521(2) -0.11660(19) 0.0441(6) Uani 1 1 d . . . C5 C 0.3347(3) -0.0763(2) -0.04912(19) 0.0476(7) Uani 1 1 d . . . C6 C 0.2447(4) -0.1094(3) 0.0304(2) 0.0659(9) Uani 1 1 d . . . C7 C 0.1469(4) -0.0362(3) 0.0917(3) 0.0760(10) Uani 1 1 d . . . C8 C 0.1419(4) 0.0671(3) 0.0745(2) 0.0643(9) Uani 1 1 d . . . C9 C 0.2352(3) 0.0955(2) -0.00579(19) 0.0453(6) Uani 1 1 d . . . C10 C 0.2384(3) 0.2043(2) -0.02632(18) 0.0435(6) Uani 1 1 d . . . C11 C 0.1565(3) 0.2916(2) 0.0235(2) 0.0529(7) Uani 1 1 d . . . C12 C 0.1957(3) 0.3823(2) -0.0152(2) 0.0515(7) Uani 1 1 d . . . C13 C 0.3058(3) 0.3659(2) -0.0948(2) 0.0474(7) Uani 1 1 d . . . C14 C 0.5901(3) 0.3939(2) -0.1890(2) 0.0464(7) Uani 1 1 d . . . C15 C 0.6950(4) 0.4026(3) -0.1272(3) 0.0628(9) Uani 1 1 d . . . C16 C 0.8504(5) 0.3495(4) -0.1469(4) 0.0855(13) Uani 1 1 d . . . C17 C 0.9005(5) 0.2887(3) -0.2272(4) 0.0866(13) Uani 1 1 d . . . C18 C 0.7987(4) 0.2800(3) -0.2887(3) 0.0770(10) Uani 1 1 d . . . C19 C 0.6442(4) 0.3318(2) -0.2703(3) 0.0617(8) Uani 1 1 d . . . C20 C 0.3174(3) 0.4836(2) -0.2807(2) 0.0496(7) Uani 1 1 d . . . C21 C 0.2058(4) 0.4421(3) -0.3071(3) 0.0771(11) Uani 1 1 d . . . C22 C 0.1580(6) 0.4631(4) -0.4010(4) 0.0971(15) Uani 1 1 d . . . C23 C 0.2196(5) 0.5243(3) -0.4687(3) 0.0842(11) Uani 1 1 d . . . C24 C 0.3283(4) 0.5678(3) -0.4427(3) 0.0743(10) Uani 1 1 d . . . C25 C 0.3762(4) 0.5474(2) -0.3501(2) 0.0596(8) Uani 1 1 d . . . C26 C 0.6709(3) -0.2062(2) -0.4607(2) 0.0490(7) Uani 1 1 d . . . C27 C 0.5128(4) -0.1910(3) -0.4551(2) 0.0609(8) Uani 1 1 d . . . C28 C 0.4319(4) -0.1530(3) -0.5355(3) 0.0711(9) Uani 1 1 d . . . C29 C 0.5071(5) -0.1295(3) -0.6237(3) 0.0700(9) Uani 1 1 d . . . C30 C 0.6631(5) -0.1435(3) -0.6319(3) 0.0748(10) Uani 1 1 d . . . C31 C 0.7460(4) -0.1821(3) -0.5519(2) 0.0663(9) Uani 1 1 d . . . C32 C 0.9114(3) -0.1925(2) -0.3464(2) 0.0521(7) Uani 1 1 d . . . C33 C 0.8884(4) -0.0883(3) -0.3769(3) 0.0640(8) Uani 1 1 d . . . C34 C 0.9944(5) -0.0354(3) -0.3599(3) 0.0805(11) Uani 1 1 d . . . C35 C 1.1221(5) -0.0855(4) -0.3140(3) 0.0831(12) Uani 1 1 d . . . C36 C 1.1470(4) -0.1874(4) -0.2843(3) 0.0777(10) Uani 1 1 d . . . C37 C 1.0431(4) -0.2413(3) -0.3014(2) 0.0638(9) Uani 1 1 d . . . H1 H 0.619(3) -0.371(2) -0.198(2) 0.056(9) Uiso 1 1 d . . . H2 H 0.420(3) -0.294(2) -0.065(2) 0.059(8) Uiso 1 1 d . . . H3 H 0.248(3) -0.179(2) 0.036(2) 0.070(10) Uiso 1 1 d . . . H4 H 0.079(4) -0.059(3) 0.145(3) 0.097(11) Uiso 1 1 d . . . H5 H 0.075(4) 0.117(2) 0.108(2) 0.069(10) Uiso 1 1 d . . . H6 H 0.086(3) 0.291(2) 0.077(2) 0.063(9) Uiso 1 1 d . . . H7 H 0.145(3) 0.446(2) 0.011(2) 0.063(9) Uiso 1 1 d . . . H8 H 0.664(4) 0.440(3) -0.077(3) 0.079(13) Uiso 1 1 d . . . H9 H 0.905(4) 0.359(3) -0.102(3) 0.086(12) Uiso 1 1 d . . . H10 H 1.004(5) 0.252(3) -0.240(3) 0.098(13) Uiso 1 1 d . . . H11 H 0.830(4) 0.239(3) -0.346(3) 0.096(13) Uiso 1 1 d . . . H12 H 0.580(3) 0.322(2) -0.310(2) 0.058(9) Uiso 1 1 d . . . H13 H 0.160(4) 0.406(3) -0.260(3) 0.081(11) Uiso 1 1 d . . . H14 H 0.094(5) 0.435(3) -0.417(3) 0.106(15) Uiso 1 1 d . . . H15 H 0.190(4) 0.538(3) -0.535(3) 0.086(11) Uiso 1 1 d . . . H16 H 0.371(4) 0.609(3) -0.490(3) 0.095(13) Uiso 1 1 d . . . H17 H 0.456(3) 0.575(2) -0.336(2) 0.056(8) Uiso 1 1 d . . . H18 H 0.458(3) -0.206(2) -0.391(2) 0.061(8) Uiso 1 1 d . . . H19 H 0.322(4) -0.144(3) -0.532(3) 0.087(11) Uiso 1 1 d . . . H20 H 0.450(4) -0.099(3) -0.682(3) 0.093(12) Uiso 1 1 d . . . H21 H 0.721(4) -0.132(3) -0.689(3) 0.079(11) Uiso 1 1 d . . . H22 H 0.858(4) -0.194(2) -0.557(2) 0.065(9) Uiso 1 1 d . . . H23 H 0.796(3) -0.053(2) -0.404(2) 0.054(8) Uiso 1 1 d . . . H24 H 0.978(4) 0.029(3) -0.382(2) 0.074(11) Uiso 1 1 d . . . H25 H 1.190(4) -0.050(3) -0.304(3) 0.086(12) Uiso 1 1 d . . . H26 H 1.239(5) -0.229(3) -0.248(3) 0.121(14) Uiso 1 1 d . . . H27 H 1.056(3) -0.311(2) -0.283(2) 0.062(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0638(5) 0.0416(4) 0.0491(4) 0.0031(3) 0.0035(3) -0.0192(3) S2 0.0589(4) 0.0456(4) 0.0413(4) -0.0030(3) 0.0046(3) -0.0157(3) P1 0.0522(5) 0.0454(4) 0.0577(5) -0.0061(3) -0.0063(4) -0.0081(3) P2 0.0556(5) 0.0424(4) 0.0534(5) -0.0030(3) -0.0078(4) -0.0148(3) N 0.0479(13) 0.0501(13) 0.0388(12) 0.0041(10) -0.0070(10) -0.0196(11) C1 0.0529(16) 0.0440(15) 0.0473(16) 0.0029(13) -0.0123(13) -0.0159(13) C2 0.0622(19) 0.0384(16) 0.0539(18) 0.0045(14) -0.0176(15) -0.0155(14) C3 0.0601(18) 0.0493(17) 0.0481(17) 0.0103(14) -0.0097(15) -0.0253(15) C4 0.0484(16) 0.0458(16) 0.0428(15) 0.0064(12) -0.0106(12) -0.0199(13) C5 0.0505(16) 0.0536(17) 0.0436(16) 0.0067(13) -0.0114(13) -0.0216(13) C6 0.079(2) 0.059(2) 0.062(2) 0.0076(17) 0.0077(17) -0.0304(18) C7 0.091(3) 0.074(2) 0.064(2) 0.0030(19) 0.023(2) -0.039(2) C8 0.071(2) 0.067(2) 0.053(2) -0.0068(17) 0.0154(17) -0.0243(18) C9 0.0476(16) 0.0531(16) 0.0381(15) 0.0010(13) -0.0060(13) -0.0184(13) C10 0.0409(15) 0.0547(17) 0.0359(14) -0.0018(12) -0.0053(12) -0.0142(13) C11 0.0462(17) 0.066(2) 0.0469(17) -0.0064(15) 0.0005(14) -0.0180(15) C12 0.0474(17) 0.0505(18) 0.0563(18) -0.0129(15) -0.0022(14) -0.0115(14) C13 0.0462(16) 0.0491(16) 0.0475(16) -0.0025(13) -0.0086(13) -0.0124(13) C14 0.0528(16) 0.0419(15) 0.0501(17) 0.0089(13) -0.0122(14) -0.0218(13) C15 0.068(2) 0.061(2) 0.071(2) 0.0115(18) -0.0263(19) -0.0335(18) C16 0.070(3) 0.090(3) 0.113(4) 0.029(3) -0.049(3) -0.040(2) C17 0.050(2) 0.077(3) 0.131(4) 0.021(3) -0.011(3) -0.020(2) C18 0.062(2) 0.072(2) 0.088(3) -0.003(2) 0.007(2) -0.0087(18) C19 0.053(2) 0.063(2) 0.067(2) -0.0042(17) -0.0100(17) -0.0119(16) C20 0.0453(16) 0.0408(15) 0.0598(18) -0.0027(13) -0.0110(14) -0.0047(13) C21 0.080(2) 0.072(2) 0.093(3) 0.027(2) -0.044(2) -0.035(2) C22 0.103(3) 0.086(3) 0.121(4) 0.012(3) -0.069(3) -0.035(3) C23 0.098(3) 0.080(3) 0.071(3) 0.003(2) -0.034(2) -0.008(2) C24 0.071(2) 0.079(2) 0.065(2) 0.008(2) -0.011(2) -0.009(2) C25 0.0569(19) 0.065(2) 0.057(2) 0.0048(16) -0.0110(16) -0.0169(16) C26 0.0540(18) 0.0456(16) 0.0466(17) -0.0080(12) -0.0006(13) -0.0130(13) C27 0.056(2) 0.074(2) 0.0496(19) 0.0045(16) -0.0035(16) -0.0161(16) C28 0.063(2) 0.088(3) 0.059(2) 0.0029(18) -0.0149(18) -0.0138(19) C29 0.091(3) 0.063(2) 0.055(2) 0.0011(16) -0.016(2) -0.0157(19) C30 0.102(3) 0.085(3) 0.044(2) -0.0018(18) 0.002(2) -0.042(2) C31 0.064(2) 0.084(2) 0.054(2) -0.0133(17) 0.0045(17) -0.0281(18) C32 0.0418(16) 0.0568(18) 0.0536(17) -0.0099(14) 0.0010(13) -0.0077(13) C33 0.057(2) 0.058(2) 0.078(2) -0.0056(17) -0.0088(18) -0.0157(17) C34 0.087(3) 0.069(3) 0.090(3) -0.008(2) 0.006(2) -0.034(2) C35 0.056(2) 0.110(4) 0.091(3) -0.035(3) 0.009(2) -0.036(3) C36 0.048(2) 0.103(3) 0.081(3) -0.020(2) -0.0024(18) -0.017(2) C37 0.0457(19) 0.072(2) 0.067(2) -0.0104(18) 0.0017(15) -0.0064(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C4 1.714(3) . ? S1 C1 1.725(3) . ? S2 C10 1.717(3) . ? S2 C13 1.725(3) . ? P1 C1 1.804(3) . ? P1 C26 1.823(3) . ? P1 C32 1.827(3) . ? P2 C13 1.810(3) . ? P2 C20 1.824(3) . ? P2 C14 1.834(3) . ? N C9 1.338(3) . ? N C5 1.342(3) . ? C1 C2 1.362(4) . ? C2 C3 1.394(4) . ? C3 C4 1.359(4) . ? C4 C5 1.468(4) . ? C5 C6 1.389(4) . ? C6 C7 1.369(5) . ? C7 C8 1.367(5) . ? C8 C9 1.388(4) . ? C9 C10 1.463(4) . ? C10 C11 1.364(4) . ? C11 C12 1.400(4) . ? C12 C13 1.358(4) . ? C14 C15 1.375(4) . ? C14 C19 1.382(4) . ? C15 C16 1.385(6) . ? C16 C17 1.358(6) . ? C17 C18 1.351(6) . ? C18 C19 1.373(5) . ? C20 C21 1.372(4) . ? C20 C25 1.379(4) . ? C21 C22 1.382(5) . ? C22 C23 1.354(6) . ? C23 C24 1.362(5) . ? C24 C25 1.367(5) . ? C26 C27 1.377(4) . ? C26 C31 1.395(4) . ? C27 C28 1.378(4) . ? C28 C29 1.360(5) . ? C29 C30 1.359(5) . ? C30 C31 1.384(5) . ? C32 C37 1.380(4) . ? C32 C33 1.385(4) . ? C33 C34 1.386(5) . ? C34 C35 1.363(6) . ? C35 C36 1.351(6) . ? C36 C37 1.380(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 C4 S1 C1 92.28(13) . . ? C10 S2 C13 92.28(13) . . ? C1 P1 C26 101.99(12) . . ? C1 P1 C32 101.29(12) . . ? C26 P1 C32 104.05(13) . . ? C13 P2 C20 104.75(13) . . ? C13 P2 C14 101.81(12) . . ? C20 P2 C14 100.93(12) . . ? C9 N C5 118.4(2) . . ? C2 C1 S1 109.9(2) . . ? C2 C1 P1 124.0(2) . . ? S1 C1 P1 126.10(15) . . ? C1 C2 C3 113.9(3) . . ? C4 C3 C2 113.1(3) . . ? C3 C4 C5 129.2(2) . . ? C3 C4 S1 110.8(2) . . ? C5 C4 S1 119.97(19) . . ? N C5 C6 122.1(3) . . ? N C5 C4 117.1(2) . . ? C6 C5 C4 120.8(3) . . ? C7 C6 C5 118.8(3) . . ? C8 C7 C6 119.5(3) . . ? C7 C8 C9 119.1(3) . . ? N C9 C8 122.0(3) . . ? N C9 C10 116.3(2) . . ? C8 C9 C10 121.6(3) . . ? C11 C10 C9 129.2(2) . . ? C11 C10 S2 110.7(2) . . ? C9 C10 S2 120.14(19) . . ? C10 C11 C12 113.0(3) . . ? C13 C12 C11 113.8(3) . . ? C12 C13 S2 110.2(2) . . ? C12 C13 P2 124.4(2) . . ? S2 C13 P2 125.31(16) . . ? C15 C14 C19 118.3(3) . . ? C15 C14 P2 117.7(3) . . ? C19 C14 P2 124.0(2) . . ? C14 C15 C16 120.1(4) . . ? C17 C16 C15 120.5(4) . . ? C18 C17 C16 120.0(4) . . ? C17 C18 C19 120.4(4) . . ? C18 C19 C14 120.7(4) . . ? C21 C20 C25 117.6(3) . . ? C21 C20 P2 124.8(3) . . ? C25 C20 P2 117.5(2) . . ? C20 C21 C22 120.1(4) . . ? C23 C22 C21 121.2(4) . . ? C22 C23 C24 119.2(4) . . ? C23 C24 C25 119.9(4) . . ? C24 C25 C20 121.8(3) . . ? C27 C26 C31 117.0(3) . . ? C27 C26 P1 121.1(2) . . ? C31 C26 P1 121.3(2) . . ? C26 C27 C28 121.7(3) . . ? C29 C28 C27 120.4(4) . . ? C30 C29 C28 119.5(4) . . ? C29 C30 C31 120.7(3) . . ? C30 C31 C26 120.7(3) . . ? C37 C32 C33 118.1(3) . . ? C37 C32 P1 116.5(2) . . ? C33 C32 P1 125.4(2) . . ? C32 C33 C34 119.9(4) . . ? C35 C34 C33 120.5(4) . . ? C36 C35 C34 120.4(4) . . ? C35 C36 C37 119.8(4) . . ? C32 C37 C36 121.3(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.466 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.037 data_el08 _database_code_CSD 169048 _journal_coden_Cambridge 207 _publ_contact_author 'Professor J. S. Field' _publ_contact_author_address ; Professor J. S. Field, School of Chemical and Physical Sciences, University of Natal, Pietermaritzburg 3201, South Africa ; _publ_contact_author_email 'fieldj@nu.ac.za' loop_ _publ_author_name 'John S. Field' 'Raymond J. Haines' 'Elena I. Lakoba' _journal_name_full 'J Chem Soc Perkin Transactions I' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Diphenyl[5-(2'-{6'-diphenylphosphino}pyridyl)-2-thienyl]phosphine ; _chemical_name_common ? _chemical_melting_point '159 C' _chemical_formula_moiety [{P(C6H5)2}2(C4H2S)(C5H3N)] _chemical_formula_sum 'C33 H25 N P2 S' _chemical_formula_weight 529.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 '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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.408(5) _cell_length_b 15.978(6) _cell_length_c 20.402(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.11(4) _cell_angle_gamma 90.00 _cell_volume 2690(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2 _cell_measurement_theta_max 12 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type 'semi-empirical' _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ; Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166 ; _exptl_special_details ; ? ; _exptl-crystal_preparation ; Crystals grown from petroleum ether/ether by slow evaporation ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius CAD4' _diffrn_measurement_method 'omega-2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '60 minutes' _diffrn_standards_decay_% 0% _diffrn_reflns_number 3925 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 1 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 22.98 _reflns_number_total 3616 _reflns_number_gt 2173 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius CAD4' _computing_cell_refinement 'CELDIM, CAD4' _computing_data_reduction 'XCAD (McArdle, 2000)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 (Farrugia, 2000)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0000P)^2^+4.3953P] 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 3616 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1271 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.187 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P -0.39497(19) 1.36499(10) 0.06385(8) 0.0534(4) Uani 1 1 d . . . P2 P 0.17519(18) 0.95797(10) 0.20249(8) 0.0536(4) Uani 1 1 d . . . S S -0.23718(17) 1.19705(10) 0.12305(7) 0.0550(4) Uani 1 1 d . . . N N -0.1134(5) 1.0386(3) 0.18400(19) 0.0454(11) Uani 1 1 d . . . C1 C -0.3938(7) 1.2676(3) 0.1090(2) 0.0484(14) Uani 1 1 d . . . C2 C -0.5197(8) 1.2380(4) 0.1347(3) 0.0599(17) Uani 1 1 d . . . C3 C -0.4907(7) 1.1596(4) 0.1655(3) 0.0556(16) Uani 1 1 d . . . C4 C -0.3423(6) 1.1283(3) 0.1637(2) 0.0462(14) Uani 1 1 d . . . C5 C -0.2685(6) 1.0495(3) 0.1897(2) 0.0435(13) Uani 1 1 d . . . C6 C -0.3516(8) 0.9899(4) 0.2196(3) 0.0575(16) Uani 1 1 d . . . C7 C -0.2745(8) 0.9171(4) 0.2439(3) 0.0603(17) Uani 1 1 d . . . C8 C -0.1178(8) 0.9055(4) 0.2360(3) 0.0578(17) Uani 1 1 d . . . C9 C -0.0409(6) 0.9666(3) 0.2056(2) 0.0464(14) Uani 1 1 d . . . C10 C -0.1835(7) 1.3788(3) 0.0585(3) 0.0509(15) Uani 1 1 d . . . C11 C -0.0999(8) 1.3280(5) 0.0210(3) 0.0667(18) Uani 1 1 d . . . C12 C 0.0609(9) 1.3426(5) 0.0200(4) 0.075(2) Uani 1 1 d . . . C13 C 0.1382(10) 1.4092(5) 0.0556(4) 0.083(2) Uani 1 1 d . . . C14 C 0.0617(10) 1.4601(5) 0.0925(4) 0.083(2) Uani 1 1 d . . . C15 C -0.1004(8) 1.4450(4) 0.0930(3) 0.0670(18) Uani 1 1 d . . . C16 C -0.4856(6) 1.3342(4) -0.0218(3) 0.0520(15) Uani 1 1 d . . . C17 C -0.5040(9) 1.3955(5) -0.0700(3) 0.0693(19) Uani 1 1 d . . . C18 C -0.5812(9) 1.3824(6) -0.1343(4) 0.082(2) Uani 1 1 d . . . C19 C -0.6426(9) 1.3048(7) -0.1519(4) 0.086(2) Uani 1 1 d . . . C20 C -0.6260(11) 1.2414(6) -0.1061(4) 0.093(3) Uani 1 1 d . . . C21 C -0.5485(9) 1.2563(5) -0.0412(4) 0.072(2) Uani 1 1 d . . . C22 C 0.2013(7) 0.8449(4) 0.2026(3) 0.0512(15) Uani 1 1 d . . . C23 C 0.3134(7) 0.8086(5) 0.2526(3) 0.0642(18) Uani 1 1 d . . . C24 C 0.3356(9) 0.7220(6) 0.2540(4) 0.082(2) Uani 1 1 d . . . C25 C 0.2419(11) 0.6727(5) 0.2072(4) 0.086(2) Uani 1 1 d . . . C26 C 0.1297(12) 0.7070(5) 0.1594(4) 0.081(2) Uani 1 1 d . . . C27 C 0.1089(9) 0.7925(4) 0.1569(3) 0.073(2) Uani 1 1 d . . . C28 C 0.1895(6) 0.9865(4) 0.1169(3) 0.0491(14) Uani 1 1 d . . . C29 C 0.2832(8) 0.9408(4) 0.0819(4) 0.0650(18) Uani 1 1 d . . . C30 C 0.3088(10) 0.9665(5) 0.0207(4) 0.081(2) Uani 1 1 d . . . C31 C 0.2434(9) 1.0400(5) -0.0063(4) 0.078(2) Uani 1 1 d . . . C32 C 0.1506(9) 1.0875(5) 0.0272(4) 0.0735(19) Uani 1 1 d . . . C33 C 0.1252(8) 1.0613(4) 0.0890(3) 0.0612(17) Uani 1 1 d . . . H1 H -0.619(7) 1.266(4) 0.130(3) 0.08(2) Uiso 1 1 d . . . H2 H -0.567(7) 1.130(4) 0.188(3) 0.074(19) Uiso 1 1 d . . . H3 H -0.464(7) 1.004(3) 0.219(3) 0.07(2) Uiso 1 1 d . . . H4 H -0.344(8) 0.869(5) 0.262(3) 0.13(3) Uiso 1 1 d . . . H5 H -0.071(6) 0.861(3) 0.251(2) 0.039(15) Uiso 1 1 d . . . H6 H -0.149(6) 1.279(3) 0.005(2) 0.040(15) Uiso 1 1 d . . . H7 H 0.117(8) 1.293(5) -0.007(3) 0.13(3) Uiso 1 1 d . . . H8 H 0.250(10) 1.422(5) 0.053(4) 0.13(3) Uiso 1 1 d . . . H9 H 0.107(9) 1.508(5) 0.119(3) 0.12(3) Uiso 1 1 d . . . H10 H -0.155(5) 1.481(3) 0.116(2) 0.026(13) Uiso 1 1 d . . . H11 H -0.470(6) 1.446(3) -0.056(2) 0.044(16) Uiso 1 1 d . . . H12 H -0.605(10) 1.425(5) -0.166(4) 0.14(3) Uiso 1 1 d . . . H13 H -0.704(6) 1.289(3) -0.192(3) 0.055(16) Uiso 1 1 d . . . H14 H -0.656(9) 1.186(5) -0.118(3) 0.11(3) Uiso 1 1 d . . . H15 H -0.533(7) 1.217(4) -0.010(3) 0.08(2) Uiso 1 1 d . . . H16 H 0.379(7) 0.845(3) 0.282(3) 0.065(19) Uiso 1 1 d . . . H17 H 0.413(8) 0.702(4) 0.285(3) 0.10(3) Uiso 1 1 d . . . H18 H 0.265(7) 0.608(4) 0.211(3) 0.08(2) Uiso 1 1 d . . . H19 H 0.062(9) 0.678(5) 0.130(3) 0.11(3) Uiso 1 1 d . . . H20 H 0.026(6) 0.819(3) 0.126(3) 0.060(17) Uiso 1 1 d . . . H21 H 0.335(6) 0.890(4) 0.099(3) 0.064(18) Uiso 1 1 d . . . H22 H 0.378(8) 0.933(4) 0.002(3) 0.10(3) Uiso 1 1 d . . . H23 H 0.256(7) 1.056(4) -0.048(3) 0.08(2) Uiso 1 1 d . . . H24 H 0.104(6) 1.148(4) 0.013(2) 0.063(17) Uiso 1 1 d . . . H25 H 0.065(8) 1.093(4) 0.111(3) 0.09(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0544(10) 0.0455(9) 0.0600(10) -0.0003(8) 0.0104(7) 0.0082(8) P2 0.0475(9) 0.0502(10) 0.0593(10) -0.0034(8) 0.0009(7) 0.0029(8) S 0.0469(9) 0.0567(10) 0.0628(10) 0.0089(8) 0.0144(7) 0.0082(8) N 0.047(3) 0.045(3) 0.043(3) 0.003(2) 0.006(2) 0.003(2) C1 0.051(3) 0.045(3) 0.048(3) -0.012(3) 0.009(3) 0.007(3) C2 0.047(4) 0.065(5) 0.068(4) 0.006(3) 0.013(3) 0.013(3) C3 0.044(4) 0.067(4) 0.059(4) 0.012(3) 0.018(3) -0.002(3) C4 0.040(3) 0.055(4) 0.046(3) -0.003(3) 0.014(3) -0.005(3) C5 0.045(3) 0.044(3) 0.039(3) -0.004(3) 0.003(2) 0.002(3) C6 0.055(4) 0.062(4) 0.056(4) 0.006(3) 0.010(3) -0.010(4) C7 0.064(5) 0.056(4) 0.064(4) 0.005(3) 0.018(3) -0.003(4) C8 0.063(4) 0.039(4) 0.069(4) 0.010(3) 0.006(3) 0.008(3) C9 0.047(3) 0.046(4) 0.042(3) -0.002(3) 0.001(3) -0.002(3) C10 0.057(4) 0.041(3) 0.053(3) 0.016(3) 0.007(3) 0.000(3) C11 0.058(4) 0.067(5) 0.078(5) -0.010(4) 0.020(4) -0.006(4) C12 0.064(5) 0.078(5) 0.088(5) 0.012(4) 0.027(4) 0.009(4) C13 0.063(5) 0.079(6) 0.105(6) 0.020(5) 0.007(5) -0.008(5) C14 0.080(6) 0.062(5) 0.102(6) -0.002(5) 0.000(5) -0.022(5) C15 0.067(5) 0.052(4) 0.082(5) 0.003(4) 0.015(4) -0.001(4) C16 0.044(3) 0.050(4) 0.060(4) 0.004(3) 0.005(3) 0.006(3) C17 0.085(5) 0.052(5) 0.068(5) 0.002(4) 0.008(4) 0.005(4) C18 0.082(5) 0.096(7) 0.062(5) 0.021(5) -0.002(4) 0.018(5) C19 0.075(5) 0.124(8) 0.051(5) -0.001(5) -0.010(4) 0.003(5) C20 0.116(7) 0.090(7) 0.064(5) -0.014(5) -0.006(4) -0.023(5) C21 0.087(5) 0.059(5) 0.064(5) 0.005(4) 0.002(4) -0.004(4) C22 0.048(3) 0.056(4) 0.049(3) 0.003(3) 0.008(3) 0.002(3) C23 0.046(4) 0.077(5) 0.065(4) 0.015(4) 0.002(3) 0.008(4) C24 0.060(5) 0.096(7) 0.091(6) 0.044(5) 0.016(4) 0.026(5) C25 0.104(7) 0.061(5) 0.100(6) 0.020(5) 0.042(5) 0.025(5) C26 0.122(7) 0.053(5) 0.065(5) 0.005(4) 0.011(5) 0.010(5) C27 0.095(5) 0.053(5) 0.060(4) 0.011(3) -0.010(4) 0.018(4) C28 0.037(3) 0.053(4) 0.056(4) 0.001(3) 0.005(3) -0.003(3) C29 0.057(4) 0.055(4) 0.088(5) -0.003(4) 0.025(4) 0.009(4) C30 0.091(6) 0.075(6) 0.086(6) -0.007(5) 0.042(5) -0.002(5) C31 0.086(6) 0.085(6) 0.065(5) 0.001(5) 0.025(4) -0.020(5) C32 0.074(5) 0.066(5) 0.083(5) 0.013(4) 0.021(4) -0.001(4) C33 0.059(4) 0.058(4) 0.068(4) 0.004(4) 0.015(3) 0.002(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 1.807(6) . ? P1 C10 1.815(6) . ? P1 C16 1.834(6) . ? P2 C22 1.820(6) . ? P2 C28 1.832(5) . ? P2 C9 1.835(5) . ? S C1 1.715(5) . ? S C4 1.720(5) . ? N C9 1.336(6) . ? N C5 1.343(6) . ? C1 C2 1.355(8) . ? C2 C3 1.401(8) . ? C3 C4 1.352(7) . ? C4 C5 1.458(7) . ? C5 C6 1.389(7) . ? C6 C7 1.378(8) . ? C7 C8 1.370(8) . ? C8 C9 1.382(8) . ? C10 C15 1.382(8) . ? C10 C11 1.395(8) . ? C11 C12 1.376(9) . ? C12 C13 1.379(10) . ? C13 C14 1.352(10) . ? C14 C15 1.386(9) . ? C16 C17 1.375(8) . ? C16 C21 1.380(8) . ? C17 C18 1.363(9) . ? C18 C19 1.363(11) . ? C19 C20 1.369(11) . ? C20 C21 1.379(9) . ? C22 C27 1.376(8) . ? C22 C23 1.377(8) . ? C23 C24 1.395(10) . ? C24 C25 1.365(11) . ? C25 C26 1.337(10) . ? C26 C27 1.378(9) . ? C28 C29 1.372(8) . ? C28 C33 1.387(8) . ? C29 C30 1.370(9) . ? C30 C31 1.366(10) . ? C31 C32 1.362(9) . ? C32 C33 1.385(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C10 103.1(3) . . ? C1 P1 C16 102.4(3) . . ? C10 P1 C16 102.0(3) . . ? C22 P2 C28 102.6(3) . . ? C22 P2 C9 101.2(3) . . ? C28 P2 C9 105.2(2) . . ? C1 S C4 93.0(3) . . ? C9 N C5 118.1(5) . . ? C2 C1 S 109.7(5) . . ? C2 C1 P1 124.8(4) . . ? S C1 P1 125.5(3) . . ? C1 C2 C3 113.9(6) . . ? C4 C3 C2 113.6(6) . . ? C3 C4 C5 129.8(5) . . ? C3 C4 S 109.8(5) . . ? C5 C4 S 120.3(4) . . ? N C5 C6 122.0(5) . . ? N C5 C4 115.6(5) . . ? C6 C5 C4 122.4(5) . . ? C7 C6 C5 119.6(6) . . ? C8 C7 C6 117.9(6) . . ? C7 C8 C9 120.1(6) . . ? N C9 C8 122.2(5) . . ? N C9 P2 116.5(4) . . ? C8 C9 P2 120.9(5) . . ? C15 C10 C11 117.7(6) . . ? C15 C10 P1 117.9(5) . . ? C11 C10 P1 124.4(5) . . ? C12 C11 C10 120.7(7) . . ? C11 C12 C13 119.1(8) . . ? C14 C13 C12 122.1(8) . . ? C13 C14 C15 118.2(8) . . ? C10 C15 C14 122.1(7) . . ? C17 C16 C21 117.0(6) . . ? C17 C16 P1 117.3(5) . . ? C21 C16 P1 125.5(5) . . ? C18 C17 C16 123.0(7) . . ? C19 C18 C17 118.7(8) . . ? C18 C19 C20 120.6(7) . . ? C19 C20 C21 119.7(8) . . ? C20 C21 C16 121.0(7) . . ? C27 C22 C23 117.6(6) . . ? C27 C22 P2 123.4(5) . . ? C23 C22 P2 118.9(5) . . ? C22 C23 C24 120.1(7) . . ? C25 C24 C23 120.1(7) . . ? C26 C25 C24 120.3(8) . . ? C25 C26 C27 120.1(8) . . ? C22 C27 C26 121.8(7) . . ? C29 C28 C33 117.6(6) . . ? C29 C28 P2 120.9(5) . . ? C33 C28 P2 120.9(5) . . ? C30 C29 C28 121.4(7) . . ? C31 C30 C29 120.2(8) . . ? C32 C31 C30 120.2(7) . . ? C31 C32 C33 119.4(7) . . ? C32 C33 C28 121.2(7) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 22.98 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.288 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.061