# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Marek Necas' 'Jaromir Marek' 'Josef Novosad' 'StJ. Foreman, Mark R.' 'J. Derek Woollins' _publ_contact_author_name 'Dr J Novosad' _publ_contact_author_address ; Dr J Novosad Department of Inorganic Chemistry Faculty of Science, Masaryk University Kotlarska 2 Brno 611 37 CZECH REPUBLIC ; _publ_contact_author_email 'NOVOSAD@CHEMI.MUNI.CZ' _publ_section_title ; New Mixed-Donor Asymmetrical P-N-P Ligands and their Complexes ; data_1.cif #data_man11 _database_code_CSD 153013 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'Ph2P(S)-NH-P(O)(OPh)2' _chemical_formula_sum 'C24 H21 N O3 P2 S' _chemical_formula_weight 465.42 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' '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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7380(10) _cell_length_b 18.582(2) _cell_length_c 12.5640(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.84(2) _cell_angle_gamma 90.00 _cell_volume 2246.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.313 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8720 _exptl_absorpt_correction_T_max 0.9258 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14139 _diffrn_reflns_av_R_equivalents 0.0726 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 25.55 _reflns_number_total 3566 _reflns_number_gt 2452 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+2.3023P] 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 3566 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.235 _refine_ls_restrained_S_all 1.235 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.17977(10) -0.00165(5) 0.63300(7) 0.0228(2) Uani 1 d . . . O1 O 0.2358(3) -0.05037(13) 0.73269(17) 0.0260(6) Uani 1 d . . . O2 O 0.3022(3) 0.05446(13) 0.64764(18) 0.0304(6) Uani 1 d . . . O3 O 0.1591(2) -0.03862(13) 0.52840(17) 0.0258(6) Uani 1 d . . . N N 0.0347(3) 0.03513(17) 0.6558(2) 0.0236(7) Uani 1 d . . . H0 H -0.016(4) 0.0356(18) 0.607(3) 0.017(11) Uiso 1 d . . . C1 C 0.1545(4) -0.10928(19) 0.7590(3) 0.0268(9) Uani 1 d . . . C2 C 0.1387(4) -0.1690(2) 0.6932(3) 0.0318(9) Uani 1 d . . . H2 H 0.1746 -0.1697 0.6270 0.038 Uiso 1 calc R . . C3 C 0.0688(4) -0.2283(2) 0.7259(3) 0.0371(10) Uani 1 d . . . H3 H 0.0570 -0.2701 0.6820 0.044 Uiso 1 calc R . . C4 C 0.0167(4) -0.2267(2) 0.8217(3) 0.0405(11) Uani 1 d . . . H4 H -0.0298 -0.2677 0.8440 0.049 Uiso 1 calc R . . C5 C 0.0315(5) -0.1660(2) 0.8854(3) 0.0433(11) Uani 1 d . . . H5 H -0.0071 -0.1649 0.9504 0.052 Uiso 1 calc R . . C6 C 0.1026(4) -0.1062(2) 0.8551(3) 0.0363(10) Uani 1 d . . . H6 H 0.1151 -0.0646 0.8993 0.044 Uiso 1 calc R . . C7 C 0.3366(4) 0.0940(2) 0.5597(2) 0.0253(8) Uani 1 d . . . C8 C 0.4727(4) 0.0895(2) 0.5421(3) 0.0301(9) Uani 1 d . . . H8 H 0.5376 0.0597 0.5860 0.036 Uiso 1 calc R . . C9 C 0.5126(5) 0.1298(2) 0.4586(3) 0.0377(10) Uani 1 d . . . H9 H 0.6055 0.1271 0.4443 0.045 Uiso 1 calc R . . C10 C 0.4181(5) 0.1734(2) 0.3967(3) 0.0394(11) Uani 1 d . . . H10 H 0.4465 0.2016 0.3409 0.047 Uiso 1 calc R . . C11 C 0.2828(5) 0.1764(2) 0.4151(3) 0.0410(11) Uani 1 d . . . H11 H 0.2178 0.2062 0.3713 0.049 Uiso 1 calc R . . C12 C 0.2404(4) 0.1360(2) 0.4979(3) 0.0343(10) Uani 1 d . . . H12 H 0.1469 0.1377 0.5110 0.041 Uiso 1 calc R . . P2 P 0.00298(10) 0.09354(5) 0.75215(7) 0.0246(2) Uani 1 d . . . S S 0.15217(11) 0.10010(6) 0.87258(7) 0.0367(3) Uani 1 d . . . C13 C -0.1606(4) 0.0642(2) 0.7865(3) 0.0260(8) Uani 1 d . . . C14 C -0.2301(4) 0.1101(2) 0.8484(3) 0.0378(10) Uani 1 d . . . H14 H -0.1906 0.1556 0.8699 0.045 Uiso 1 calc R . . C15 C -0.3553(5) 0.0906(3) 0.8788(3) 0.0442(11) Uani 1 d . . . H15 H -0.4016 0.1229 0.9200 0.053 Uiso 1 calc R . . C16 C -0.4130(5) 0.0246(3) 0.8496(3) 0.0445(11) Uani 1 d . . . H16 H -0.4991 0.0111 0.8705 0.053 Uiso 1 calc R . . C17 C -0.3446(5) -0.0220(2) 0.7895(3) 0.0456(12) Uani 1 d . . . H17 H -0.3841 -0.0677 0.7697 0.055 Uiso 1 calc R . . C18 C -0.2195(4) -0.0028(2) 0.7578(3) 0.0338(9) Uani 1 d . . . H18 H -0.1738 -0.0353 0.7165 0.041 Uiso 1 calc R . . C19 C -0.0356(4) 0.17747(19) 0.6813(3) 0.0244(8) Uani 1 d . . . C20 C 0.0690(4) 0.2284(2) 0.6819(3) 0.0335(9) Uani 1 d . . . H20 H 0.1581 0.2200 0.7226 0.040 Uiso 1 calc R . . C21 C 0.0434(5) 0.2915(2) 0.6231(3) 0.0405(10) Uani 1 d . . . H21 H 0.1155 0.3260 0.6234 0.049 Uiso 1 calc R . . C22 C -0.0853(4) 0.3047(2) 0.5644(3) 0.0344(10) Uani 1 d . . . H22 H -0.1023 0.3482 0.5250 0.041 Uiso 1 calc R . . C23 C -0.1896(4) 0.2545(2) 0.5631(3) 0.0331(9) Uani 1 d . . . H23 H -0.2786 0.2632 0.5224 0.040 Uiso 1 calc R . . C24 C -0.1645(4) 0.1912(2) 0.6209(3) 0.0326(9) Uani 1 d . . . H24 H -0.2367 0.1567 0.6192 0.039 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0199(5) 0.0276(5) 0.0204(4) 0.0008(4) 0.0015(4) 0.0018(4) O1 0.0241(14) 0.0291(14) 0.0241(12) 0.0053(10) 0.0010(11) 0.0013(12) O2 0.0257(15) 0.0381(16) 0.0266(12) 0.0057(11) 0.0013(11) -0.0093(13) O3 0.0237(14) 0.0305(14) 0.0229(12) -0.0042(10) 0.0023(10) 0.0068(12) N 0.0182(19) 0.0311(18) 0.0194(15) -0.0075(13) -0.0040(14) 0.0039(15) C1 0.020(2) 0.030(2) 0.0293(18) 0.0077(16) 0.0016(16) 0.0046(18) C2 0.027(2) 0.040(2) 0.0289(19) 0.0006(17) 0.0058(17) -0.0002(19) C3 0.037(3) 0.033(2) 0.042(2) 0.0004(18) 0.0082(19) 0.002(2) C4 0.040(3) 0.041(3) 0.042(2) 0.011(2) 0.012(2) 0.000(2) C5 0.049(3) 0.048(3) 0.037(2) 0.009(2) 0.019(2) 0.002(2) C6 0.043(3) 0.040(2) 0.0281(19) 0.0004(17) 0.0113(18) 0.005(2) C7 0.026(2) 0.028(2) 0.0216(17) -0.0020(15) 0.0026(16) -0.0033(18) C8 0.023(2) 0.031(2) 0.0356(19) -0.0030(17) 0.0038(17) -0.0008(19) C9 0.037(3) 0.039(2) 0.040(2) -0.0085(19) 0.017(2) -0.007(2) C10 0.052(3) 0.034(2) 0.035(2) 0.0015(18) 0.016(2) -0.006(2) C11 0.041(3) 0.042(3) 0.040(2) 0.0072(19) 0.005(2) 0.009(2) C12 0.026(2) 0.045(3) 0.033(2) 0.0038(18) 0.0092(18) 0.005(2) P2 0.0225(5) 0.0277(5) 0.0231(4) -0.0053(4) 0.0021(4) 0.0014(5) S 0.0345(6) 0.0439(6) 0.0285(5) -0.0102(4) -0.0057(4) 0.0026(5) C13 0.025(2) 0.031(2) 0.0215(17) -0.0025(15) 0.0026(16) 0.0044(18) C14 0.041(3) 0.037(2) 0.038(2) -0.0054(18) 0.016(2) -0.002(2) C15 0.039(3) 0.054(3) 0.044(2) 0.001(2) 0.019(2) 0.008(2) C16 0.035(3) 0.060(3) 0.041(2) 0.007(2) 0.014(2) -0.008(2) C17 0.047(3) 0.046(3) 0.045(2) -0.004(2) 0.010(2) -0.017(2) C18 0.037(3) 0.033(2) 0.0328(19) -0.0035(18) 0.0100(18) -0.004(2) C19 0.020(2) 0.027(2) 0.0262(18) -0.0074(15) 0.0052(16) -0.0024(17) C20 0.023(2) 0.045(3) 0.032(2) -0.0006(18) -0.0003(17) -0.005(2) C21 0.040(3) 0.042(3) 0.040(2) 0.0016(19) 0.006(2) -0.012(2) C22 0.038(3) 0.033(2) 0.034(2) 0.0022(17) 0.0092(19) -0.002(2) C23 0.026(2) 0.033(2) 0.039(2) 0.0049(17) 0.0027(18) 0.0042(19) C24 0.027(2) 0.032(2) 0.039(2) -0.0010(18) 0.0034(19) -0.0014(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O3 1.469(2) . ? P1 O2 1.573(3) . ? P1 O1 1.573(2) . ? P1 N 1.634(3) . ? O1 C1 1.419(4) . ? O2 C7 1.409(4) . ? N P2 1.689(3) . ? C1 C2 1.379(5) . ? C1 C6 1.379(5) . ? C2 C3 1.389(5) . ? C3 C4 1.377(5) . ? C4 C5 1.377(6) . ? C5 C6 1.392(6) . ? C7 C12 1.366(5) . ? C7 C8 1.380(5) . ? C8 C9 1.392(5) . ? C9 C10 1.374(6) . ? C10 C11 1.373(6) . ? C11 C12 1.396(5) . ? P2 C13 1.798(4) . ? P2 C19 1.806(4) . ? P2 S 1.9337(14) . ? C13 C18 1.395(5) . ? C13 C14 1.397(5) . ? C14 C15 1.380(6) . ? C15 C16 1.375(6) . ? C16 C17 1.385(6) . ? C17 C18 1.386(6) . ? C19 C24 1.387(5) . ? C19 C20 1.390(5) . ? C20 C21 1.389(5) . ? C21 C22 1.374(6) . ? C22 C23 1.377(5) . ? C23 C24 1.384(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 O3 P1 O2 114.32(14) . . ? O3 P1 O1 115.23(14) . . ? O2 P1 O1 97.16(13) . . ? O3 P1 N 110.41(16) . . ? O2 P1 N 111.25(16) . . ? O1 P1 N 107.74(15) . . ? C1 O1 P1 119.5(2) . . ? C7 O2 P1 121.4(2) . . ? P1 N P2 130.7(2) . . ? C2 C1 C6 122.4(4) . . ? C2 C1 O1 119.7(3) . . ? C6 C1 O1 117.7(3) . . ? C1 C2 C3 118.4(3) . . ? C4 C3 C2 120.3(4) . . ? C5 C4 C3 120.4(4) . . ? C4 C5 C6 120.4(4) . . ? C1 C6 C5 118.1(4) . . ? C12 C7 C8 122.3(3) . . ? C12 C7 O2 121.3(3) . . ? C8 C7 O2 116.4(3) . . ? C7 C8 C9 118.4(4) . . ? C10 C9 C8 120.2(4) . . ? C11 C10 C9 120.3(4) . . ? C10 C11 C12 120.3(4) . . ? C7 C12 C11 118.4(4) . . ? N P2 C13 104.11(16) . . ? N P2 C19 104.40(15) . . ? C13 P2 C19 104.75(16) . . ? N P2 S 113.79(13) . . ? C13 P2 S 114.73(12) . . ? C19 P2 S 113.92(12) . . ? C18 C13 C14 118.3(4) . . ? C18 C13 P2 123.5(3) . . ? C14 C13 P2 118.1(3) . . ? C15 C14 C13 121.2(4) . . ? C16 C15 C14 120.2(4) . . ? C15 C16 C17 119.4(4) . . ? C16 C17 C18 120.9(4) . . ? C17 C18 C13 120.0(4) . . ? C24 C19 C20 118.6(3) . . ? C24 C19 P2 122.1(3) . . ? C20 C19 P2 119.2(3) . . ? C21 C20 C19 120.1(4) . . ? C22 C21 C20 120.7(4) . . ? C21 C22 C23 119.8(4) . . ? C22 C23 C24 119.9(4) . . ? C23 C24 C19 121.0(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H0 O3 0.73(3) 2.02(4) 2.752(4) 179(4) 3_556 _diffrn_measured_fraction_theta_max 0.820 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.858 _refine_diff_density_max 0.379 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.078 data_2.cif #data_man13 _database_code_CSD 153014 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'Ph2P(Se)-NH-P(O)(OPh)2' _chemical_formula_sum 'C24 H21 N O3 P2 Se' _chemical_formula_weight 512.32 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' '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' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.745(2) _cell_length_b 18.799(4) _cell_length_c 12.423(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.21(3) _cell_angle_gamma 90.00 _cell_volume 2252.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 1.835 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3598 _exptl_absorpt_correction_T_max 0.4605 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12723 _diffrn_reflns_av_R_equivalents 0.1021 _diffrn_reflns_av_sigmaI/netI 0.0716 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 25.55 _reflns_number_total 3566 _reflns_number_gt 2255 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+13.9817P] 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 SHELXL _refine_ls_extinction_coef 0.0053(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3566 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1120 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.011 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se Se 0.66172(8) 0.08951(4) 0.89413(6) 0.0426(3) Uani 1 d . . . P2 P 0.50371(18) 0.08648(10) 0.76145(15) 0.0290(5) Uani 1 d . . . P1 P 0.67835(18) -0.00542(9) 0.63287(15) 0.0285(5) Uani 1 d . . . O O 0.6555(5) -0.0384(2) 0.5242(4) 0.0329(12) Uani 1 d . . . O1 O 0.8028(5) 0.0497(3) 0.6492(4) 0.0358(12) Uani 1 d . . . C2 C 0.9747(7) 0.0880(4) 0.5467(6) 0.0322(17) Uani 1 d . . . H2 H 1.0387 0.0578 0.5898 0.039 Uiso 1 calc R . . C15 C 0.3183(8) 0.2508(4) 0.5801(6) 0.0371(18) Uani 1 d . . . H15 H 0.2291 0.2615 0.5422 0.044 Uiso 1 calc R . . N N 0.5343(6) 0.0321(3) 0.6612(5) 0.0256(13) Uani 1 d . . . H0 H 0.490(8) 0.025(4) 0.602(6) 0.03(2) Uiso 1 d . . . C6 C 0.7439(8) 0.1333(4) 0.5012(6) 0.0383(18) Uani 1 d . . . H6 H 0.6497 0.1340 0.5129 0.046 Uiso 1 calc R . . C13 C 0.4700(7) 0.1719(4) 0.6930(6) 0.0328(17) Uani 1 d . . . C12 C 0.5982(8) -0.1161(4) 0.8493(6) 0.0380(18) Uani 1 d . . . H12 H 0.6069 -0.0756 0.8956 0.046 Uiso 1 calc R . . C24 C 0.2695(8) 0.1015(4) 0.8592(6) 0.0406(19) Uani 1 d . . . H24 H 0.3105 0.1454 0.8842 0.049 Uiso 1 calc R . . C7 C 0.6526(7) -0.1160(4) 0.7526(6) 0.0322(17) Uani 1 d . . . C21 C 0.1504(8) -0.0268(4) 0.7903(7) 0.046(2) Uani 1 d . . . H21 H 0.1102 -0.0713 0.7673 0.055 Uiso 1 calc R . . C1 C 0.8384(7) 0.0906(4) 0.5633(6) 0.0282(15) Uani 1 d . . . C20 C 0.2773(8) -0.0074(4) 0.7613(6) 0.0389(19) Uani 1 d . . . H20 H 0.3233 -0.0389 0.7184 0.047 Uiso 1 calc R . . C8 C 0.6356(8) -0.1727(4) 0.6811(6) 0.0376(18) Uani 1 d . . . H8 H 0.6702 -0.1705 0.6135 0.045 Uiso 1 calc R . . C16 C 0.4248(8) 0.2988(4) 0.5782(6) 0.0401(19) Uani 1 d . . . H16 H 0.4099 0.3420 0.5384 0.048 Uiso 1 calc R . . C11 C 0.5308(9) -0.1764(4) 0.8771(7) 0.048(2) Uani 1 d . . . H11 H 0.4952 -0.1781 0.9444 0.057 Uiso 1 calc R . . C14 C 0.3389(7) 0.1872(4) 0.6361(6) 0.0361(18) Uani 1 d . . . H14 H 0.2649 0.1543 0.6359 0.043 Uiso 1 calc R . . C18 C 0.5779(8) 0.2194(4) 0.6931(6) 0.0404(19) Uani 1 d . . . H18 H 0.6670 0.2088 0.7316 0.048 Uiso 1 calc R . . C19 C 0.3381(7) 0.0573(4) 0.7940(6) 0.0336(17) Uani 1 d . . . C10 C 0.5145(8) -0.2346(4) 0.8078(7) 0.045(2) Uani 1 d . . . H10 H 0.4671 -0.2758 0.8275 0.053 Uiso 1 calc R . . C4 C 0.9230(9) 0.1741(4) 0.4045(7) 0.047(2) Uani 1 d . . . H4 H 0.9529 0.2035 0.3502 0.056 Uiso 1 calc R . . C23 C 0.1425(9) 0.0821(5) 0.8882(7) 0.048(2) Uani 1 d . . . H23 H 0.0966 0.1126 0.9324 0.057 Uiso 1 calc R . . C17 C 0.5549(8) 0.2830(4) 0.6359(7) 0.045(2) Uani 1 d . . . H17 H 0.6287 0.3161 0.6362 0.054 Uiso 1 calc R . . C5 C 0.7880(9) 0.1755(4) 0.4212(7) 0.048(2) Uani 1 d . . . H5 H 0.7237 0.2054 0.3778 0.057 Uiso 1 calc R . . C9 C 0.5669(8) -0.2329(4) 0.7104(7) 0.043(2) Uani 1 d . . . H9 H 0.5560 -0.2729 0.6632 0.051 Uiso 1 calc R . . C22 C 0.0830(8) 0.0177(5) 0.8520(7) 0.051(2) Uani 1 d . . . H22 H -0.0050 0.0047 0.8702 0.061 Uiso 1 calc R . . C3 C 1.0172(9) 0.1299(4) 0.4666(7) 0.045(2) Uani 1 d . . . H3 H 1.1110 0.1285 0.4538 0.054 Uiso 1 calc R . . O2 O 0.7335(5) -0.0567(2) 0.7292(4) 0.0306(11) Uani 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 Se 0.0348(5) 0.0472(5) 0.0413(5) -0.0103(4) -0.0095(4) 0.0039(4) P2 0.0216(9) 0.0289(9) 0.0354(11) -0.0058(8) 0.0006(8) 0.0013(8) P1 0.0210(9) 0.0290(9) 0.0340(11) 0.0003(8) -0.0016(8) 0.0014(8) O 0.026(3) 0.036(3) 0.036(3) -0.003(2) 0.001(2) 0.007(2) O1 0.023(2) 0.046(3) 0.035(3) 0.004(2) -0.005(2) -0.011(2) C2 0.024(4) 0.025(3) 0.047(5) -0.002(3) 0.001(3) 0.000(3) C15 0.031(4) 0.037(4) 0.045(5) 0.001(3) 0.011(3) 0.007(3) N 0.021(3) 0.029(3) 0.025(3) -0.010(3) -0.002(3) 0.002(2) C6 0.025(4) 0.049(5) 0.041(5) -0.001(4) 0.003(3) 0.005(4) C13 0.025(4) 0.030(4) 0.044(4) -0.007(3) 0.007(3) -0.002(3) C12 0.044(5) 0.032(4) 0.040(5) 0.003(3) 0.012(4) 0.008(3) C24 0.048(5) 0.040(4) 0.035(4) -0.011(3) 0.010(4) -0.003(4) C7 0.026(4) 0.029(4) 0.040(4) 0.005(3) -0.001(3) 0.008(3) C21 0.034(4) 0.042(5) 0.061(6) -0.003(4) 0.006(4) -0.014(4) C1 0.027(4) 0.030(4) 0.028(4) -0.002(3) 0.004(3) -0.007(3) C20 0.042(5) 0.030(4) 0.044(5) -0.008(3) 0.005(4) -0.002(3) C8 0.035(4) 0.032(4) 0.044(5) 0.001(3) 0.000(4) 0.004(3) C16 0.043(5) 0.033(4) 0.045(5) -0.002(3) 0.008(4) -0.004(4) C11 0.059(6) 0.037(5) 0.049(5) 0.008(4) 0.016(4) 0.006(4) C14 0.025(4) 0.031(4) 0.052(5) -0.003(3) 0.003(4) -0.002(3) C18 0.026(4) 0.039(4) 0.053(5) 0.000(4) -0.002(4) -0.011(3) C19 0.027(4) 0.030(4) 0.043(4) 0.001(3) 0.003(3) 0.004(3) C10 0.038(4) 0.037(4) 0.062(6) 0.008(4) 0.019(4) 0.003(4) C4 0.061(6) 0.039(4) 0.044(5) 0.005(4) 0.019(4) -0.004(4) C23 0.043(5) 0.054(5) 0.052(5) -0.004(4) 0.025(4) 0.005(4) C17 0.036(4) 0.044(5) 0.056(5) -0.007(4) 0.009(4) -0.016(4) C5 0.045(5) 0.044(5) 0.055(5) 0.014(4) 0.009(4) 0.005(4) C9 0.037(4) 0.035(4) 0.056(5) -0.005(4) 0.009(4) 0.000(4) C22 0.032(4) 0.056(5) 0.066(6) 0.007(5) 0.006(4) -0.004(4) C3 0.040(5) 0.044(5) 0.054(5) -0.011(4) 0.018(4) -0.011(4) O2 0.024(2) 0.028(2) 0.039(3) 0.007(2) 0.000(2) 0.001(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 Se P2 2.089(2) . ? P2 N 1.671(6) . ? P2 C19 1.804(8) . ? P2 C13 1.825(7) . ? P1 O 1.473(5) . ? P1 O2 1.571(5) . ? P1 O1 1.585(5) . ? P1 N 1.654(6) . ? O1 C1 1.399(8) . ? C2 C1 1.374(9) . ? C2 C3 1.379(11) . ? C15 C16 1.378(10) . ? C15 C14 1.383(10) . ? C6 C1 1.372(10) . ? C6 C5 1.387(11) . ? C13 C18 1.379(10) . ? C13 C14 1.398(10) . ? C12 C11 1.378(11) . ? C12 C7 1.381(10) . ? C24 C23 1.386(11) . ? C24 C19 1.395(10) . ? C7 C8 1.382(10) . ? C7 O2 1.419(8) . ? C21 C22 1.365(12) . ? C21 C20 1.385(11) . ? C20 C19 1.389(10) . ? C8 C9 1.389(11) . ? C16 C17 1.397(11) . ? C11 C10 1.388(11) . ? C18 C17 1.393(11) . ? C10 C9 1.380(11) . ? C4 C5 1.361(11) . ? C4 C3 1.387(11) . ? C23 C22 1.388(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N P2 C19 104.0(3) . . ? N P2 C13 103.3(3) . . ? C19 P2 C13 105.3(3) . . ? N P2 Se 114.5(2) . . ? C19 P2 Se 114.4(3) . . ? C13 P2 Se 114.0(2) . . ? O P1 O2 115.5(3) . . ? O P1 O1 113.9(3) . . ? O2 P1 O1 97.5(3) . . ? O P1 N 110.6(3) . . ? O2 P1 N 108.0(3) . . ? O1 P1 N 110.6(3) . . ? C1 O1 P1 122.0(4) . . ? C1 C2 C3 119.0(7) . . ? C16 C15 C14 121.3(7) . . ? P1 N P2 131.8(4) . . ? C1 C6 C5 119.1(7) . . ? C18 C13 C14 120.6(7) . . ? C18 C13 P2 118.8(5) . . ? C14 C13 P2 120.4(5) . . ? C11 C12 C7 118.3(7) . . ? C23 C24 C19 120.9(7) . . ? C12 C7 C8 122.2(7) . . ? C12 C7 O2 118.2(6) . . ? C8 C7 O2 119.5(7) . . ? C22 C21 C20 120.3(7) . . ? C6 C1 C2 121.5(7) . . ? C6 C1 O1 122.1(6) . . ? C2 C1 O1 116.4(6) . . ? C21 C20 C19 120.9(7) . . ? C7 C8 C9 118.5(8) . . ? C15 C16 C17 118.8(7) . . ? C12 C11 C10 120.7(8) . . ? C15 C14 C13 119.2(7) . . ? C13 C18 C17 119.2(7) . . ? C20 C19 C24 118.1(7) . . ? C20 C19 P2 123.9(6) . . ? C24 C19 P2 117.9(6) . . ? C9 C10 C11 120.1(8) . . ? C5 C4 C3 120.3(8) . . ? C24 C23 C22 119.5(8) . . ? C18 C17 C16 120.8(7) . . ? C4 C5 C6 120.2(8) . . ? C10 C9 C8 120.1(8) . . ? C21 C22 C23 120.2(8) . . ? C2 C3 C4 120.0(7) . . ? C7 O2 P1 119.9(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H0 O 0.81(7) 1.97(7) 2.743(7) 159(7) 3_656 _diffrn_measured_fraction_theta_max 0.820 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.858 _refine_diff_density_max 0.993 _refine_diff_density_min -0.864 _refine_diff_density_rms 0.127 data_4.cif #data_m _database_code_CSD 153015 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'iPr2P(Se)-NH-P(O)(OPh)2' _chemical_formula_sum 'C18 H25 N O3 P2 Se' _chemical_formula_weight 444.29 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' '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' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(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 18.491(4) _cell_length_b 23.200(5) _cell_length_c 9.642(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.59(3) _cell_angle_gamma 90.00 _cell_volume 4089.9(15) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 2.009 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5004 _exptl_absorpt_correction_T_max 0.5840 _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29324 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 28.66 _reflns_number_total 9677 _reflns_number_gt 7729 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0535P)^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 SHELXL _refine_ls_extinction_coef 0.0000(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 9677 _refine_ls_number_parameters 652 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.333 _refine_ls_shift/su_mean 0.021 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.367428(11) 0.633083(9) 0.33652(2) 0.01890(7) Uani 1 d . . . P2 P 0.41773(3) 0.67343(2) 0.18185(5) 0.01360(11) Uani 1 d . . . P1 P 0.53768(3) 0.76091(2) 0.19562(5) 0.01299(11) Uani 1 d . . . O2 O 0.61788(7) 0.75553(6) 0.27723(14) 0.0156(3) Uani 1 d . . . C15 C 0.28541(13) 0.69216(12) 0.0094(3) 0.0256(5) Uani 1 d . . . O3 O 0.53231(8) 0.75656(6) 0.04376(14) 0.0180(3) Uani 1 d . . . C3 C 0.57955(14) 0.95421(10) 0.1148(3) 0.0336(6) Uani 1 d . . . C6 C 0.60242(12) 0.88848(10) 0.3555(2) 0.0214(4) Uani 1 d . . . C13 C 0.35667(11) 0.72189(9) 0.0707(2) 0.0176(4) Uani 1 d . . . N1 N 0.48698(9) 0.71476(7) 0.26269(18) 0.0139(3) Uani 1 d . . . C1 C 0.55481(11) 0.87110(8) 0.2406(2) 0.0171(4) Uani 1 d . . . C7 C 0.65903(11) 0.70495(8) 0.2714(2) 0.0172(4) Uani 1 d . . . O1 O 0.51499(7) 0.82041(6) 0.25316(15) 0.0171(3) Uani 1 d . . . C8 C 0.66319(12) 0.66736(9) 0.3825(2) 0.0225(4) Uani 1 d . . . C14 C 0.33876(14) 0.77422(10) 0.1542(3) 0.0251(5) Uani 1 d . . . C17 C 0.51378(14) 0.58453(10) 0.1665(3) 0.0255(5) Uani 1 d . . . C9 C 0.70597(14) 0.61837(10) 0.3809(3) 0.0305(5) Uani 1 d . . . C11 C 0.73846(14) 0.64712(11) 0.1597(3) 0.0339(6) Uani 1 d . . . C12 C 0.69577(12) 0.69598(10) 0.1595(3) 0.0244(5) Uani 1 d . . . C4 C 0.62747(14) 0.97265(10) 0.2296(3) 0.0333(6) Uani 1 d . . . C16 C 0.46396(12) 0.62523(9) 0.0738(2) 0.0193(4) Uani 1 d . . . C10 C 0.74325(14) 0.60852(11) 0.2700(3) 0.0340(6) Uani 1 d . . . C5 C 0.63836(13) 0.94025(10) 0.3496(3) 0.0290(5) Uani 1 d . . . C2 C 0.54203(13) 0.90259(10) 0.1191(3) 0.0258(5) Uani 1 d . . . Se2 Se 0.122621(13) 0.695490(10) 0.62284(3) 0.03241(8) Uani 1 d . . . P3 P 0.00073(3) 0.57081(2) 0.65868(5) 0.01564(11) Uani 1 d . . . P4 P 0.12128(3) 0.61855(2) 0.51155(6) 0.01829(12) Uani 1 d . . . O6 O -0.04482(8) 0.51906(6) 0.64073(15) 0.0198(3) Uani 1 d . . . O4 O -0.04074(8) 0.62910(6) 0.62461(15) 0.0195(3) Uani 1 d . . . O5 O 0.03721(8) 0.58239(6) 0.81392(15) 0.0193(3) Uani 1 d . . . C19 C -0.08171(12) 0.65695(9) 0.7162(2) 0.0215(4) Uani 1 d . . . C33 C 0.14556(16) 0.66487(12) 0.2617(3) 0.0335(6) Uani 1 d . . . C31 C 0.09284(12) 0.62592(9) 0.3233(2) 0.0220(5) Uani 1 d . . . C30 C 0.14479(13) 0.56735(11) 0.9726(2) 0.0263(5) Uani 1 d . . . N2 N 0.06299(9) 0.56851(7) 0.55696(19) 0.0179(4) Uani 1 d . . . C34 C 0.21014(11) 0.58302(9) 0.5329(2) 0.0215(4) Uani 1 d . . . C26 C 0.06627(13) 0.48634(9) 0.9062(2) 0.0238(5) Uani 1 d . . . C29 C 0.19048(14) 0.53260(12) 1.0619(3) 0.0325(6) Uani 1 d . . . C27 C 0.11240(13) 0.45233(10) 0.9972(3) 0.0275(5) Uani 1 d . . . C21 C -0.19683(16) 0.68016(13) 0.7803(3) 0.0433(7) Uani 1 d . . . C36 C 0.21000(14) 0.52616(11) 0.4563(3) 0.0263(5) Uani 1 d . . . C28 C 0.17447(13) 0.47484(11) 1.0745(3) 0.0316(5) Uani 1 d . . . C24 C -0.04663(14) 0.69258(10) 0.8188(3) 0.0275(5) Uani 1 d . . . C25 C 0.08304(11) 0.54386(9) 0.8965(2) 0.0184(4) Uani 1 d . . . C35 C 0.24211(17) 0.57607(14) 0.6863(3) 0.0375(6) Uani 1 d . . . C32 C 0.01500(15) 0.64800(13) 0.2918(3) 0.0348(6) Uani 1 d . . . C22 C -0.16316(17) 0.71591(11) 0.8832(3) 0.0439(7) Uani 1 d . . . C23 C -0.08873(17) 0.72225(11) 0.9032(3) 0.0387(6) Uani 1 d . . . C18 C 0.41253(15) 0.59244(11) -0.0357(3) 0.0298(5) Uani 1 d . . . C20 C -0.15599(14) 0.65037(12) 0.6948(3) 0.0317(6) Uani 1 d . . . H16 H 0.4914(13) 0.6517(10) 0.030(3) 0.025(6) Uiso 1 d . . . H1N H 0.4912(12) 0.7146(9) 0.346(2) 0.011(5) Uiso 1 d . . . H31 H 0.0963(11) 0.5884(9) 0.287(2) 0.011(5) Uiso 1 d . . . H2 H 0.5064(13) 0.8915(10) 0.045(3) 0.026(6) Uiso 1 d . . . H26 H 0.0254(13) 0.4705(10) 0.852(2) 0.020(6) Uiso 1 d . . . H13 H 0.3840(11) 0.7333(9) -0.002(2) 0.009(5) Uiso 1 d . . . H35C H 0.2133(14) 0.5500(11) 0.726(3) 0.031(7) Uiso 1 d . . . H15C H 0.2587(14) 0.7165(11) -0.043(3) 0.024(6) Uiso 1 d . . . H8 H 0.6381(13) 0.6735(10) 0.460(3) 0.025(6) Uiso 1 d . . . H6 H 0.6091(13) 0.8673(10) 0.433(3) 0.027(7) Uiso 1 d . . . H2N H 0.0565(14) 0.5398(11) 0.506(3) 0.033(7) Uiso 1 d . . . H17C H 0.5424(15) 0.6065(12) 0.237(3) 0.039(8) Uiso 1 d . . . H28 H 0.2068(13) 0.4501(10) 1.133(3) 0.025(6) Uiso 1 d . . . H34 H 0.2376(15) 0.6104(12) 0.491(3) 0.040(7) Uiso 1 d . . . H9 H 0.7068(12) 0.5892(10) 0.461(2) 0.021(6) Uiso 1 d . . . H36C H 0.2575(15) 0.5103(11) 0.460(3) 0.035(7) Uiso 1 d . . . H33C H 0.1307(15) 0.6678(13) 0.168(3) 0.043(8) Uiso 1 d . . . H15B H 0.2594(14) 0.6819(11) 0.083(3) 0.029(7) Uiso 1 d . . . H3 H 0.5695(17) 0.9710(14) 0.032(3) 0.055(9) Uiso 1 d . . . H29 H 0.2332(14) 0.5472(11) 1.118(3) 0.034(7) Uiso 1 d . . . H32C H -0.0221(15) 0.6223(12) 0.327(3) 0.041(8) Uiso 1 d . . . H35B H 0.2409(15) 0.6090(13) 0.728(3) 0.038(8) Uiso 1 d . . . H4 H 0.6490(14) 1.0057(12) 0.228(3) 0.033(7) Uiso 1 d . . . H23 H -0.0644(14) 0.7464(12) 0.972(3) 0.034(7) Uiso 1 d . . . H18C H 0.3797(15) 0.5692(12) 0.003(3) 0.040(8) Uiso 1 d . . . H14C H 0.3133(13) 0.7636(11) 0.236(3) 0.032(7) Uiso 1 d . . . H14B H 0.3071(15) 0.7997(11) 0.093(3) 0.037(7) Uiso 1 d . . . H24 H 0.0013(15) 0.6948(11) 0.830(3) 0.033(7) Uiso 1 d . . . H11 H 0.7643(15) 0.6396(11) 0.086(3) 0.038(8) Uiso 1 d . . . H36B H 0.1812(14) 0.5017(11) 0.495(3) 0.033(7) Uiso 1 d . . . H10 H 0.7736(17) 0.5754(13) 0.263(3) 0.057(9) Uiso 1 d . . . H17B H 0.5415(14) 0.5633(11) 0.105(3) 0.036(7) Uiso 1 d . . . H20 H -0.1742(15) 0.6290(11) 0.630(3) 0.035(8) Uiso 1 d . . . H21 H -0.2519(17) 0.6734(13) 0.759(3) 0.053(9) Uiso 1 d . . . H18B H 0.3859(15) 0.6177(13) -0.112(3) 0.043(8) Uiso 1 d . . . H32B H 0.0130(16) 0.6830(14) 0.331(3) 0.050(9) Uiso 1 d . . . H12 H 0.6941(14) 0.7229(12) 0.084(3) 0.040(7) Uiso 1 d . . . H14A H 0.3806(17) 0.7956(12) 0.188(3) 0.048(9) Uiso 1 d . . . H18A H 0.4395(17) 0.5673(13) -0.080(3) 0.054(9) Uiso 1 d . . . H17A H 0.4875(15) 0.5571(12) 0.208(3) 0.041(8) Uiso 1 d . . . H5 H 0.6716(14) 0.9538(11) 0.432(3) 0.034(7) Uiso 1 d . . . H36A H 0.1907(14) 0.5288(11) 0.359(3) 0.036(7) Uiso 1 d . . . H32A H 0.0043(17) 0.6488(13) 0.200(4) 0.050(9) Uiso 1 d . . . H33B H 0.1925(17) 0.6490(12) 0.265(3) 0.044(8) Uiso 1 d . . . H15A H 0.2945(16) 0.6607(13) -0.044(3) 0.045(8) Uiso 1 d . . . H33A H 0.1485(15) 0.6982(13) 0.307(3) 0.039(8) Uiso 1 d . . . H27 H 0.1017(15) 0.4124(13) 1.004(3) 0.048(8) Uiso 1 d . . . H35A H 0.2912(17) 0.5654(12) 0.689(3) 0.044(8) Uiso 1 d . . . H30 H 0.1542(14) 0.6017(12) 0.960(3) 0.036(8) Uiso 1 d . . . H22 H -0.1973(18) 0.7354(14) 0.940(3) 0.065(10) Uiso 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 Se1 0.02250(12) 0.01738(11) 0.01836(11) 0.00181(8) 0.00807(8) -0.00399(8) P2 0.0166(2) 0.0124(2) 0.0123(2) -0.00129(18) 0.00351(19) -0.00221(19) P1 0.0165(2) 0.0112(2) 0.0115(2) 0.00030(18) 0.00302(19) -0.00154(19) O2 0.0164(7) 0.0130(7) 0.0169(7) -0.0019(5) 0.0006(6) -0.0006(5) C15 0.0195(11) 0.0354(14) 0.0210(12) 0.0002(11) -0.0001(9) -0.0012(10) O3 0.0241(7) 0.0188(7) 0.0117(7) 0.0017(5) 0.0044(6) -0.0018(6) C3 0.0393(14) 0.0203(12) 0.0443(16) 0.0156(11) 0.0166(12) 0.0053(11) C6 0.0203(10) 0.0217(11) 0.0229(11) -0.0038(9) 0.0054(9) -0.0009(9) C13 0.0181(10) 0.0199(10) 0.0155(10) 0.0021(8) 0.0044(8) 0.0002(8) N1 0.0199(9) 0.0129(8) 0.0091(8) -0.0012(6) 0.0030(7) -0.0041(6) C1 0.0173(10) 0.0108(9) 0.0243(11) -0.0003(8) 0.0069(8) 0.0006(7) C7 0.0162(9) 0.0140(9) 0.0211(10) -0.0046(8) 0.0021(8) -0.0020(7) O1 0.0198(7) 0.0106(6) 0.0218(8) -0.0013(5) 0.0059(6) -0.0019(5) C8 0.0230(11) 0.0232(11) 0.0207(11) 0.0017(9) 0.0013(9) 0.0001(9) C14 0.0233(11) 0.0226(11) 0.0290(12) 0.0003(10) 0.0022(10) 0.0073(10) C17 0.0302(12) 0.0174(11) 0.0306(13) -0.0025(10) 0.0097(11) 0.0024(10) C9 0.0313(13) 0.0239(12) 0.0334(13) 0.0061(10) -0.0044(11) 0.0022(10) C11 0.0327(13) 0.0334(13) 0.0378(15) -0.0046(11) 0.0126(12) 0.0097(11) C12 0.0262(11) 0.0229(11) 0.0251(12) 0.0004(9) 0.0074(9) 0.0014(9) C4 0.0335(13) 0.0145(11) 0.0558(17) -0.0026(11) 0.0196(12) -0.0062(10) C16 0.0231(10) 0.0165(10) 0.0196(10) -0.0049(8) 0.0074(9) -0.0037(8) C10 0.0322(13) 0.0218(12) 0.0465(16) -0.0026(11) 0.0010(12) 0.0103(10) C5 0.0261(12) 0.0247(12) 0.0377(14) -0.0122(10) 0.0099(11) -0.0074(9) C2 0.0312(12) 0.0194(11) 0.0268(12) 0.0037(9) 0.0043(10) 0.0023(9) Se2 0.03450(14) 0.01871(13) 0.04847(17) -0.01759(10) 0.02083(12) -0.01203(10) P3 0.0175(3) 0.0132(2) 0.0168(3) -0.00318(19) 0.0045(2) -0.00259(19) P4 0.0200(3) 0.0126(2) 0.0240(3) -0.0043(2) 0.0088(2) -0.0043(2) O6 0.0221(7) 0.0200(7) 0.0185(7) -0.0049(6) 0.0071(6) -0.0071(6) O4 0.0219(7) 0.0175(7) 0.0201(8) -0.0006(6) 0.0061(6) 0.0025(6) O5 0.0242(8) 0.0157(7) 0.0177(7) -0.0032(6) 0.0024(6) 0.0014(6) C19 0.0256(11) 0.0138(10) 0.0275(11) 0.0033(9) 0.0118(9) 0.0055(8) C33 0.0409(16) 0.0279(14) 0.0335(15) 0.0127(12) 0.0113(13) -0.0028(12) C31 0.0274(11) 0.0151(10) 0.0249(11) 0.0027(9) 0.0086(9) 0.0010(9) C30 0.0316(13) 0.0268(13) 0.0200(11) 0.0013(9) 0.0020(9) -0.0067(10) N2 0.0197(9) 0.0126(8) 0.0228(9) -0.0063(7) 0.0079(7) -0.0055(7) C34 0.0178(10) 0.0227(11) 0.0251(11) -0.0022(9) 0.0068(9) -0.0041(9) C26 0.0252(11) 0.0190(11) 0.0269(12) -0.0005(9) 0.0029(9) -0.0009(9) C29 0.0262(12) 0.0452(15) 0.0249(12) 0.0043(11) -0.0005(10) -0.0052(11) C27 0.0331(13) 0.0230(12) 0.0272(12) 0.0043(9) 0.0070(10) 0.0027(10) C21 0.0297(14) 0.0416(16) 0.064(2) 0.0171(14) 0.0232(14) 0.0172(12) C36 0.0243(12) 0.0275(12) 0.0267(13) -0.0045(10) 0.0023(10) 0.0090(10) C28 0.0283(12) 0.0406(14) 0.0261(12) 0.0089(11) 0.0050(10) 0.0074(11) C24 0.0319(13) 0.0199(11) 0.0335(13) -0.0029(9) 0.0141(11) -0.0004(10) C25 0.0218(10) 0.0200(10) 0.0142(9) -0.0020(8) 0.0060(8) 0.0016(8) C35 0.0358(15) 0.0457(17) 0.0285(14) -0.0107(13) -0.0037(12) 0.0029(13) C32 0.0336(14) 0.0314(14) 0.0391(16) 0.0037(12) 0.0042(12) 0.0087(11) C22 0.0541(17) 0.0282(14) 0.0580(19) 0.0086(13) 0.0365(16) 0.0176(13) C23 0.0583(18) 0.0206(12) 0.0430(16) -0.0037(11) 0.0269(14) 0.0043(12) C18 0.0363(14) 0.0264(12) 0.0269(13) -0.0123(11) 0.0050(11) -0.0029(11) C20 0.0244(12) 0.0317(13) 0.0396(15) 0.0073(12) 0.0067(11) 0.0056(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 Se1 P2 2.0929(7) . ? P2 N1 1.6936(17) . ? P2 C13 1.824(2) . ? P2 C16 1.826(2) . ? P1 O3 1.4563(14) . ? P1 O1 1.5680(14) . ? P1 O2 1.5765(15) . ? P1 N1 1.6202(17) . ? O2 C7 1.404(2) . ? C15 C13 1.526(3) . ? C3 C4 1.378(4) . ? C3 C2 1.388(3) . ? C6 C1 1.369(3) . ? C6 C5 1.378(3) . ? C13 C14 1.520(3) . ? C1 C2 1.371(3) . ? C1 O1 1.402(2) . ? C7 C12 1.374(3) . ? C7 C8 1.375(3) . ? C8 C9 1.386(3) . ? C17 C16 1.514(3) . ? C9 C10 1.375(4) . ? C11 C12 1.381(3) . ? C11 C10 1.383(4) . ? C4 C5 1.369(4) . ? C16 C18 1.516(3) . ? Se2 P4 2.0810(7) . ? P3 O6 1.4620(14) . ? P3 O4 1.5651(15) . ? P3 O5 1.5704(15) . ? P3 N2 1.6210(18) . ? P4 N2 1.6858(18) . ? P4 C31 1.821(2) . ? P4 C34 1.822(2) . ? O4 C19 1.404(2) . ? O5 C25 1.396(2) . ? C19 C20 1.367(3) . ? C19 C24 1.375(3) . ? C33 C31 1.514(3) . ? C31 C32 1.515(3) . ? C30 C29 1.374(3) . ? C30 C25 1.375(3) . ? C34 C36 1.512(3) . ? C34 C35 1.517(3) . ? C26 C25 1.376(3) . ? C26 C27 1.378(3) . ? C29 C28 1.382(4) . ? C27 C28 1.375(3) . ? C21 C22 1.370(5) . ? C21 C20 1.383(4) . ? C24 C23 1.390(3) . ? C22 C23 1.369(4) . ? 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 N1 P2 C13 106.30(9) . . ? N1 P2 C16 102.89(9) . . ? C13 P2 C16 110.12(10) . . ? N1 P2 Se1 108.13(6) . . ? C13 P2 Se1 113.10(7) . . ? C16 P2 Se1 115.37(7) . . ? O3 P1 O1 115.79(8) . . ? O3 P1 O2 114.47(8) . . ? O1 P1 O2 100.06(8) . . ? O3 P1 N1 113.51(9) . . ? O1 P1 N1 103.84(8) . . ? O2 P1 N1 107.80(8) . . ? C7 O2 P1 121.40(12) . . ? C4 C3 C2 120.6(2) . . ? C1 C6 C5 118.6(2) . . ? C14 C13 C15 108.80(19) . . ? C14 C13 P2 110.26(15) . . ? C15 C13 P2 111.83(16) . . ? P1 N1 P2 129.29(11) . . ? C6 C1 C2 122.9(2) . . ? C6 C1 O1 117.36(19) . . ? C2 C1 O1 119.68(19) . . ? C12 C7 C8 122.6(2) . . ? C12 C7 O2 119.52(19) . . ? C8 C7 O2 117.79(18) . . ? C1 O1 P1 122.41(12) . . ? C7 C8 C9 118.5(2) . . ? C10 C9 C8 119.9(2) . . ? C12 C11 C10 120.2(2) . . ? C7 C12 C11 118.2(2) . . ? C5 C4 C3 120.2(2) . . ? C17 C16 C18 111.17(19) . . ? C17 C16 P2 109.91(15) . . ? C18 C16 P2 113.99(16) . . ? C9 C10 C11 120.6(2) . . ? C4 C5 C6 120.1(2) . . ? C1 C2 C3 117.5(2) . . ? O6 P3 O4 115.42(9) . . ? O6 P3 O5 114.28(8) . . ? O4 P3 O5 100.34(8) . . ? O6 P3 N2 110.49(9) . . ? O4 P3 N2 105.75(9) . . ? O5 P3 N2 109.85(9) . . ? N2 P4 C31 102.89(10) . . ? N2 P4 C34 105.06(10) . . ? C31 P4 C34 106.04(11) . . ? N2 P4 Se2 114.56(7) . . ? C31 P4 Se2 114.39(7) . . ? C34 P4 Se2 112.87(8) . . ? C19 O4 P3 123.99(13) . . ? C25 O5 P3 124.88(12) . . ? C20 C19 C24 122.1(2) . . ? C20 C19 O4 118.6(2) . . ? C24 C19 O4 119.23(19) . . ? C33 C31 C32 111.6(2) . . ? C33 C31 P4 109.87(18) . . ? C32 C31 P4 110.84(18) . . ? C29 C30 C25 119.1(2) . . ? P3 N2 P4 132.37(11) . . ? C36 C34 C35 110.8(2) . . ? C36 C34 P4 113.81(16) . . ? C35 C34 P4 111.83(17) . . ? C25 C26 C27 118.3(2) . . ? C30 C29 C28 120.3(2) . . ? C28 C27 C26 121.0(2) . . ? C22 C21 C20 120.3(3) . . ? C27 C28 C29 119.5(2) . . ? C19 C24 C23 118.3(2) . . ? C30 C25 C26 121.7(2) . . ? C30 C25 O5 115.84(19) . . ? C26 C25 O5 122.39(19) . . ? C23 C22 C21 120.4(2) . . ? C22 C23 C24 120.2(3) . . ? C19 C20 C21 118.7(3) . . ? _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.511 _refine_diff_density_min -0.644 _refine_diff_density_rms 0.081 data_5.cif #data_man58b _database_code_CSD 153016 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'Ph2P(Se)-NH-P(S)(OPh)2' _chemical_formula_sum 'C24 H21 N O2 P2 S Se' _chemical_formula_weight 528.38 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' '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' 'Se' 'Se' -0.0929 2.2259 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.236(5) _cell_length_b 9.654(2) _cell_length_c 22.026(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.97(3) _cell_angle_gamma 90.00 _cell_volume 4672.5(16) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 1.855 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2880 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 22.67 _reflns_number_total 2789 _reflns_number_gt 2268 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0768P)^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 2789 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.002 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se Se 0.270825(16) 0.76585(4) 0.202641(17) 0.02262(19) Uani 1 d . . . P2 P 0.36178(4) 0.75354(8) 0.25921(4) 0.0141(3) Uani 1 d . . . S S 0.47369(4) 0.53359(8) 0.14809(4) 0.0182(3) Uani 1 d . . . P1 P 0.40396(4) 0.63102(8) 0.15410(4) 0.0132(3) Uani 1 d . . . O2 O 0.39504(10) 0.7858(2) 0.12871(11) 0.0152(5) Uani 1 d . . . O1 O 0.34087(10) 0.5680(2) 0.11226(10) 0.0163(5) Uani 1 d . . . N N 0.40442(14) 0.6517(3) 0.22752(15) 0.0155(7) Uani 1 d . . . H0 H 0.4307(16) 0.619(4) 0.2508(17) 0.004(10) Uiso 1 d . . . C16 C 0.40633(18) 0.5220(4) 0.44979(19) 0.0304(10) Uani 1 d . . . H16 H 0.4176 0.4724 0.4881 0.036 Uiso 1 calc R . . C22 C 0.4588(2) 1.1694(4) 0.3101(2) 0.0370(11) Uani 1 d . . . H22 H 0.4785 1.2540 0.3213 0.044 Uiso 1 calc R . . C21 C 0.49191(18) 1.0480(4) 0.32158(18) 0.0278(9) Uani 1 d . . . H21 H 0.5339 1.0504 0.3409 0.033 Uiso 1 calc R . . C1 C 0.32567(16) 0.4250(3) 0.11077(16) 0.0167(8) Uani 1 d . . . C13 C 0.37698(15) 0.6674(3) 0.33573(16) 0.0163(8) Uani 1 d . . . C17 C 0.37711(19) 0.4566(4) 0.39249(19) 0.0307(10) Uani 1 d . . . H17 H 0.3672 0.3632 0.3922 0.037 Uiso 1 calc R . . C18 C 0.36245(17) 0.5293(4) 0.33557(18) 0.0243(9) Uani 1 d . . . H18 H 0.3427 0.4848 0.2970 0.029 Uiso 1 calc R . . C19 C 0.39985(16) 0.9191(3) 0.27644(16) 0.0169(8) Uani 1 d . . . C23 C 0.3966(2) 1.1652(4) 0.2821(2) 0.0364(11) Uani 1 d . . . H23 H 0.3743 1.2471 0.2743 0.044 Uiso 1 calc R . . C20 C 0.46229(16) 0.9230(4) 0.30420(17) 0.0217(9) Uani 1 d . . . H20 H 0.4845 0.8411 0.3112 0.026 Uiso 1 calc R . . C6 C 0.3416(2) 0.3406(4) 0.0698(2) 0.0384(11) Uani 1 d . . . H6 H 0.3647 0.3742 0.0455 0.046 Uiso 1 calc R . . C15 C 0.41872(17) 0.6616(4) 0.44998(18) 0.0275(10) Uani 1 d . . . H15 H 0.4375 0.7065 0.4887 0.033 Uiso 1 calc R . . C5 C 0.3230(2) 0.2036(5) 0.0646(2) 0.0517(14) Uani 1 d . . . H5 H 0.3338 0.1440 0.0369 0.062 Uiso 1 calc R . . C14 C 0.40367(17) 0.7353(4) 0.39351(18) 0.0198(9) Uani 1 d . . . H14 H 0.4113 0.8299 0.3941 0.024 Uiso 1 calc R . . C3 C 0.27266(18) 0.2435(4) 0.1407(2) 0.0243(9) Uani 1 d . . . H3 H 0.2489 0.2109 0.1644 0.029 Uiso 1 calc R . . C4 C 0.2886(2) 0.1561(4) 0.1003(2) 0.0348(10) Uani 1 d . . . H4 H 0.2761 0.0641 0.0970 0.042 Uiso 1 calc R . . C24 C 0.36734(18) 1.0409(4) 0.26572(18) 0.0254(9) Uani 1 d . . . H24 H 0.3252 1.0387 0.2472 0.030 Uiso 1 calc R . . C2 C 0.29130(16) 0.3800(4) 0.14674(17) 0.0201(8) Uani 1 d . . . H2 H 0.2808 0.4396 0.1746 0.024 Uiso 1 calc R . . C12 C 0.32300(16) 0.8372(3) 0.02569(17) 0.0186(8) Uani 1 d . . . H12 H 0.2914 0.8212 0.0420 0.022 Uiso 1 calc R . . C7 C 0.38247(15) 0.8200(3) 0.06391(16) 0.0140(8) Uani 1 d . . . C9 C 0.41660(18) 0.8852(4) -0.02195(18) 0.0276(10) Uani 1 d . . . H9 H 0.4482 0.9024 -0.0382 0.033 Uiso 1 calc R . . C8 C 0.42982(17) 0.8419(4) 0.04050(17) 0.0240(9) Uani 1 d . . . H8 H 0.4699 0.8279 0.0664 0.029 Uiso 1 calc R . . C11 C 0.31106(18) 0.8779(3) -0.03621(17) 0.0240(9) Uani 1 d . . . H11 H 0.2709 0.8890 -0.0625 0.029 Uiso 1 calc R . . C10 C 0.35793(18) 0.9031(4) -0.06043(18) 0.0254(9) Uani 1 d . . . H10 H 0.3495 0.9320 -0.1027 0.030 Uiso 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 Se 0.0087(3) 0.0306(3) 0.0262(3) -0.00274(15) 0.0024(2) 0.00477(14) P2 0.0102(6) 0.0142(5) 0.0176(6) -0.0011(3) 0.0041(5) 0.0021(3) S 0.0117(5) 0.0190(5) 0.0247(6) -0.0040(4) 0.0071(4) 0.0027(3) P1 0.0084(5) 0.0128(5) 0.0183(5) -0.0009(3) 0.0042(4) -0.0006(3) O2 0.0139(14) 0.0145(12) 0.0165(14) 0.0004(10) 0.0039(11) 0.0003(10) O1 0.0115(13) 0.0151(12) 0.0203(13) -0.0030(9) 0.0025(11) -0.0035(10) N 0.0077(17) 0.0139(15) 0.0220(18) 0.0041(13) 0.0011(15) 0.0076(13) C16 0.032(3) 0.037(2) 0.027(2) 0.0075(18) 0.016(2) 0.0043(19) C22 0.054(3) 0.016(2) 0.040(3) -0.0054(17) 0.014(2) -0.0106(19) C21 0.023(2) 0.023(2) 0.033(2) -0.0033(17) 0.0031(19) -0.0082(17) C1 0.015(2) 0.0146(18) 0.0188(19) -0.0024(14) 0.0035(17) -0.0027(14) C13 0.0079(19) 0.0179(19) 0.025(2) 0.0004(15) 0.0084(16) 0.0060(14) C17 0.041(3) 0.021(2) 0.035(3) 0.0076(18) 0.019(2) -0.0015(17) C18 0.024(2) 0.024(2) 0.027(2) -0.0047(16) 0.0109(18) -0.0029(16) C19 0.019(2) 0.0148(18) 0.0174(19) -0.0018(14) 0.0064(16) 0.0004(15) C23 0.044(3) 0.018(2) 0.043(3) -0.0021(18) 0.009(2) 0.0081(19) C20 0.019(2) 0.019(2) 0.028(2) 0.0005(15) 0.0081(18) 0.0026(15) C6 0.052(3) 0.033(2) 0.045(3) -0.014(2) 0.036(2) -0.020(2) C15 0.023(2) 0.037(2) 0.025(2) -0.0039(17) 0.0117(19) -0.0034(17) C5 0.075(4) 0.032(2) 0.065(3) -0.027(2) 0.048(3) -0.025(3) C14 0.013(2) 0.0242(19) 0.024(2) -0.0010(16) 0.0086(18) -0.0044(14) C3 0.017(2) 0.028(2) 0.031(2) 0.0032(16) 0.013(2) -0.0065(15) C4 0.039(3) 0.023(2) 0.048(3) -0.0070(19) 0.022(2) -0.0151(18) C24 0.021(2) 0.020(2) 0.031(2) 0.0005(16) 0.0045(19) 0.0066(16) C2 0.012(2) 0.023(2) 0.027(2) -0.0013(15) 0.0083(17) 0.0014(15) C12 0.012(2) 0.0166(18) 0.026(2) -0.0011(15) 0.0050(17) -0.0018(14) C7 0.014(2) 0.0111(17) 0.017(2) -0.0012(14) 0.0052(16) -0.0025(14) C9 0.027(3) 0.033(2) 0.026(2) 0.0014(17) 0.013(2) -0.0036(17) C8 0.016(2) 0.032(2) 0.022(2) 0.0014(16) 0.0028(18) -0.0031(16) C11 0.021(2) 0.019(2) 0.023(2) -0.0008(15) -0.0048(18) -0.0003(15) C10 0.037(3) 0.0176(19) 0.020(2) 0.0040(15) 0.007(2) -0.0004(16) _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 Se P2 2.0787(12) . ? P2 N 1.699(3) . ? P2 C19 1.806(3) . ? P2 C13 1.808(3) . ? S P1 1.9148(12) . ? P1 O1 1.578(2) . ? P1 O2 1.586(2) . ? P1 N 1.626(3) . ? O2 C7 1.400(4) . ? O1 C1 1.423(4) . ? C16 C17 1.377(6) . ? C16 C15 1.378(6) . ? C22 C23 1.375(6) . ? C22 C21 1.380(6) . ? C21 C20 1.380(5) . ? C1 C6 1.354(5) . ? C1 C2 1.366(5) . ? C13 C18 1.375(5) . ? C13 C14 1.386(5) . ? C17 C18 1.380(5) . ? C19 C24 1.376(5) . ? C19 C20 1.380(5) . ? C23 C24 1.369(5) . ? C6 C5 1.385(6) . ? C15 C14 1.376(5) . ? C5 C4 1.372(6) . ? C3 C4 1.361(5) . ? C3 C2 1.379(5) . ? C12 C11 1.358(5) . ? C12 C7 1.375(5) . ? C7 C8 1.375(5) . ? C9 C10 1.362(5) . ? C9 C8 1.373(5) . ? C11 C10 1.381(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 N P2 C19 106.70(15) . . ? N P2 C13 98.82(15) . . ? C19 P2 C13 106.10(16) . . ? N P2 Se 113.70(12) . . ? C19 P2 Se 114.11(12) . . ? C13 P2 Se 115.94(12) . . ? O1 P1 O2 99.65(13) . . ? O1 P1 N 109.42(14) . . ? O2 P1 N 101.14(14) . . ? O1 P1 S 114.61(10) . . ? O2 P1 S 117.08(10) . . ? N P1 S 113.37(12) . . ? C7 O2 P1 122.8(2) . . ? C1 O1 P1 124.4(2) . . ? P1 N P2 131.6(2) . . ? C17 C16 C15 119.5(4) . . ? C23 C22 C21 120.0(4) . . ? C22 C21 C20 119.6(4) . . ? C6 C1 C2 122.3(3) . . ? C6 C1 O1 118.6(3) . . ? C2 C1 O1 118.9(3) . . ? C18 C13 C14 119.8(3) . . ? C18 C13 P2 118.0(3) . . ? C14 C13 P2 122.1(3) . . ? C16 C17 C18 120.1(4) . . ? C13 C18 C17 120.2(4) . . ? C24 C19 C20 119.5(3) . . ? C24 C19 P2 121.1(3) . . ? C20 C19 P2 119.4(3) . . ? C24 C23 C22 120.2(4) . . ? C19 C20 C21 120.3(3) . . ? C1 C6 C5 118.9(4) . . ? C14 C15 C16 120.8(4) . . ? C4 C5 C6 119.8(4) . . ? C15 C14 C13 119.4(3) . . ? C4 C3 C2 120.8(4) . . ? C3 C4 C5 120.0(4) . . ? C23 C24 C19 120.4(4) . . ? C1 C2 C3 118.2(3) . . ? C11 C12 C7 119.1(3) . . ? C12 C7 C8 121.3(3) . . ? C12 C7 O2 119.2(3) . . ? C8 C7 O2 119.4(3) . . ? C10 C9 C8 121.0(4) . . ? C9 C8 C7 118.5(3) . . ? C12 C11 C10 120.6(4) . . ? C9 C10 C11 119.5(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H0 S 0.73(4) 2.71(4) 3.432(4) 170(3) 2_655 _diffrn_measured_fraction_theta_max 0.416 _diffrn_reflns_theta_full 22.67 _diffrn_measured_fraction_theta_full 0.416 _refine_diff_density_max 0.686 _refine_diff_density_min -0.980 _refine_diff_density_rms 0.091 data_6.cif #data_man52b _database_code_CSD 153017 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'Ph2P(S)-NH-P(S)(OPh)2' _chemical_formula_sum 'C24 H21 N O2 P2 S2' _chemical_formula_weight 481.48 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' '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.166(5) _cell_length_b 9.633(2) _cell_length_c 22.060(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.23(3) _cell_angle_gamma 90.00 _cell_volume 4648.2(16) _cell_formula_units_Z 8 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 0.389 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4134 _diffrn_reflns_av_R_equivalents 0.0131 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 25.09 _reflns_number_total 4026 _reflns_number_gt 3437 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+5.3652P] 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 4026 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.09611(2) 0.12851(5) 0.84606(2) 0.01597(14) Uani 1 d . . . S1 S 0.02596(2) 0.03163(5) 0.85197(2) 0.02147(14) Uani 1 d . . . P2 P 0.14043(2) 0.24604(5) 0.74175(2) 0.01725(14) Uani 1 d . . . S2 S 0.22516(2) 0.25294(6) 0.79509(3) 0.02617(15) Uani 1 d . . . O2 O 0.10476(6) 0.28406(14) 0.87025(6) 0.0189(3) Uani 1 d . . . O1 O 0.15951(6) 0.06639(14) 0.88851(6) 0.0199(3) Uani 1 d . . . N1 N 0.09573(7) 0.14622(17) 0.77199(8) 0.0178(4) Uani 1 d . . . C18 C 0.14225(11) 0.0230(2) 0.66532(11) 0.0294(5) Uani 1 d . . . C1 C 0.17480(9) -0.0754(2) 0.88978(9) 0.0208(4) Uani 1 d . . . C8 C 0.17675(9) 0.3354(2) 0.97348(10) 0.0244(5) Uani 1 d . . . C6 C 0.20974(9) -0.1189(2) 0.85384(10) 0.0239(5) Uani 1 d . . . C9 C 0.18847(10) 0.3784(2) 1.03613(11) 0.0290(5) Uani 1 d . . . C24 C 0.13906(11) 0.5326(2) 0.73405(11) 0.0307(5) Uani 1 d . . . C21 C 0.01293(11) 0.5494(2) 0.68114(11) 0.0332(5) Uani 1 d . . . C13 C 0.12535(9) 0.1613(2) 0.66516(9) 0.0193(4) Uani 1 d . . . C12 C 0.06903(10) 0.3448(2) 0.95733(10) 0.0279(5) Uani 1 d . . . C4 C 0.21210(13) -0.3464(3) 0.89861(14) 0.0416(6) Uani 1 d . . . C20 C 0.04079(10) 0.4214(2) 0.69814(10) 0.0261(5) Uani 1 d . . . C16 C 0.09660(12) 0.0151(3) 0.55093(12) 0.0372(6) Uani 1 d . . . C11 C 0.08198(11) 0.3891(3) 1.02034(11) 0.0342(5) Uani 1 d . . . C5 C 0.22848(11) -0.2565(2) 0.85900(11) 0.0297(5) Uani 1 d . . . C17 C 0.12785(13) -0.0491(2) 0.60826(12) 0.0392(6) Uani 1 d . . . C7 C 0.11692(9) 0.31989(19) 0.93514(9) 0.0186(4) Uani 1 d . . . C19 C 0.10404(9) 0.4128(2) 0.72451(9) 0.0205(4) Uani 1 d . . . C3 C 0.17687(16) -0.2998(3) 0.93416(16) 0.0560(9) Uani 1 d . . . C23 C 0.11078(13) 0.6590(2) 0.71733(13) 0.0410(6) Uani 1 d . . . C15 C 0.08166(11) 0.1531(3) 0.55031(11) 0.0319(5) Uani 1 d . . . C22 C 0.04837(13) 0.6679(2) 0.69074(12) 0.0397(6) Uani 1 d . . . C2 C 0.15834(13) -0.1622(3) 0.93033(14) 0.0429(7) Uani 1 d . . . C10 C 0.14124(11) 0.4063(2) 1.05929(10) 0.0315(5) Uani 1 d . . . C14 C 0.09615(10) 0.2269(2) 0.60739(10) 0.0239(5) Uani 1 d . . . H6 H 0.2229 -0.0519 0.8231 0.050 Uiso 1 d . . . H5 H 0.2515 -0.2891 0.8260 0.050 Uiso 1 d . . . H9 H 0.2324 0.3902 1.0631 0.050 Uiso 1 d . . . H15 H 0.0563 0.2038 0.5058 0.050 Uiso 1 d . . . H8 H 0.2110 0.3098 0.9533 0.050 Uiso 1 d . . . H24 H 0.1885 0.5233 0.7577 0.050 Uiso 1 d . . . H11 H 0.0457 0.4084 1.0411 0.050 Uiso 1 d . . . H22 H 0.0266 0.7534 0.6809 0.050 Uiso 1 d . . . H20 H 0.0182 0.3252 0.6944 0.050 Uiso 1 d . . . H18 H 0.1660 -0.0245 0.7108 0.050 Uiso 1 d . . . H10 H 0.1530 0.4333 1.1067 0.050 Uiso 1 d . . . H12 H 0.0246 0.3305 0.9257 0.050 Uiso 1 d . . . H21 H -0.0378 0.5442 0.6633 0.050 Uiso 1 d . . . H16 H 0.0842 -0.0489 0.5069 0.050 Uiso 1 d . . . H23 H 0.1367 0.7430 0.7264 0.050 Uiso 1 d . . . H3 H 0.1682 -0.3699 0.9641 0.050 Uiso 1 d . . . H14 H 0.0861 0.3306 0.6059 0.050 Uiso 1 d . . . H17 H 0.1443 -0.1514 0.6089 0.050 Uiso 1 d . . . H2 H 0.1281 -0.1262 0.9545 0.050 Uiso 1 d . . . H4 H 0.2247 -0.4564 0.8974 0.050 Uiso 1 d . . . H0 H 0.0565 0.1018 0.7391 0.050 Uiso 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 0.0158(3) 0.0143(3) 0.0167(3) 0.00140(18) 0.0038(2) 0.00074(18) S1 0.0197(3) 0.0219(3) 0.0230(3) 0.0038(2) 0.0072(2) -0.00258(19) P2 0.0169(3) 0.0163(3) 0.0178(3) 0.00062(19) 0.0045(2) -0.00263(19) S2 0.0171(3) 0.0312(3) 0.0268(3) 0.0029(2) 0.0026(2) -0.0049(2) O2 0.0224(7) 0.0158(7) 0.0164(7) 0.0004(5) 0.0035(5) 0.0004(5) O1 0.0182(7) 0.0173(7) 0.0206(7) 0.0008(5) 0.0017(6) 0.0036(5) N1 0.0171(8) 0.0177(8) 0.0180(9) 0.0006(6) 0.0050(7) -0.0030(6) C18 0.0420(13) 0.0210(11) 0.0272(12) 0.0002(9) 0.0141(10) -0.0003(9) C1 0.0209(10) 0.0187(10) 0.0202(10) 0.0024(8) 0.0033(8) 0.0054(8) C8 0.0228(10) 0.0179(10) 0.0282(11) 0.0003(8) 0.0025(8) -0.0005(8) C6 0.0217(10) 0.0247(11) 0.0253(11) -0.0011(9) 0.0076(8) -0.0003(8) C9 0.0293(12) 0.0219(11) 0.0272(12) -0.0016(9) -0.0021(9) -0.0023(9) C24 0.0384(13) 0.0205(11) 0.0293(12) 0.0016(9) 0.0061(10) -0.0080(9) C21 0.0397(14) 0.0272(12) 0.0317(13) 0.0024(10) 0.0102(10) 0.0094(10) C13 0.0172(9) 0.0202(10) 0.0217(10) -0.0008(8) 0.0080(8) -0.0045(8) C12 0.0243(11) 0.0331(12) 0.0240(11) -0.0023(9) 0.0049(9) 0.0021(9) C4 0.0510(15) 0.0258(12) 0.0540(17) 0.0095(11) 0.0255(13) 0.0165(11) C20 0.0286(11) 0.0202(11) 0.0297(12) 0.0007(9) 0.0096(9) 0.0015(9) C16 0.0504(15) 0.0382(14) 0.0290(13) -0.0099(11) 0.0214(11) -0.0081(12) C11 0.0370(13) 0.0380(14) 0.0284(13) -0.0029(10) 0.0119(10) 0.0042(10) C5 0.0271(12) 0.0288(12) 0.0345(13) -0.0047(10) 0.0118(10) 0.0048(9) C17 0.0623(17) 0.0234(12) 0.0375(14) -0.0054(10) 0.0238(12) -0.0013(11) C7 0.0236(10) 0.0128(9) 0.0169(10) 0.0008(7) 0.0034(8) 0.0006(8) C19 0.0284(11) 0.0164(10) 0.0167(10) -0.0002(8) 0.0077(8) -0.0018(8) C3 0.086(2) 0.0341(15) 0.068(2) 0.0309(14) 0.0525(18) 0.0283(15) C23 0.0584(17) 0.0181(11) 0.0412(15) 0.0011(10) 0.0091(12) -0.0086(11) C15 0.0351(12) 0.0418(14) 0.0211(11) -0.0007(10) 0.0122(9) 0.0023(11) C22 0.0628(17) 0.0190(11) 0.0348(13) 0.0044(10) 0.0126(12) 0.0102(11) C2 0.0628(17) 0.0328(13) 0.0488(16) 0.0168(12) 0.0395(14) 0.0208(12) C10 0.0472(14) 0.0215(11) 0.0202(11) -0.0008(9) 0.0035(10) 0.0024(10) C14 0.0244(11) 0.0277(11) 0.0217(11) 0.0018(9) 0.0104(8) 0.0031(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.5767(14) . ? P1 O2 1.5811(14) . ? P1 N1 1.6400(17) . ? P1 S1 1.9153(8) . ? P2 N1 1.7021(16) . ? P2 C19 1.796(2) . ? P2 C13 1.804(2) . ? P2 S2 1.9288(10) . ? O2 C7 1.408(2) . ? O1 C1 1.409(2) . ? C18 C17 1.379(3) . ? C18 C13 1.388(3) . ? C1 C2 1.367(3) . ? C1 C6 1.372(3) . ? C8 C7 1.373(3) . ? C8 C9 1.382(3) . ? C6 C5 1.388(3) . ? C9 C10 1.378(3) . ? C24 C23 1.375(3) . ? C24 C19 1.386(3) . ? C21 C22 1.381(4) . ? C21 C20 1.385(3) . ? C13 C14 1.383(3) . ? C12 C7 1.373(3) . ? C12 C11 1.389(3) . ? C4 C5 1.369(4) . ? C4 C3 1.380(4) . ? C20 C19 1.390(3) . ? C16 C15 1.373(4) . ? C16 C17 1.379(4) . ? C11 C10 1.369(3) . ? C3 C2 1.387(4) . ? C23 C22 1.372(4) . ? C15 C14 1.387(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 99.76(8) . . ? O1 P1 N1 109.25(8) . . ? O2 P1 N1 101.32(8) . . ? O1 P1 S1 114.83(6) . . ? O2 P1 S1 117.05(6) . . ? N1 P1 S1 113.09(7) . . ? N1 P2 C19 106.53(9) . . ? N1 P2 C13 98.99(9) . . ? C19 P2 C13 105.91(9) . . ? N1 P2 S2 114.12(6) . . ? C19 P2 S2 114.25(7) . . ? C13 P2 S2 115.54(7) . . ? C7 O2 P1 122.43(12) . . ? C1 O1 P1 123.96(12) . . ? P1 N1 P2 130.16(10) . . ? C17 C18 C13 119.9(2) . . ? C2 C1 C6 122.4(2) . . ? C2 C1 O1 118.91(19) . . ? C6 C1 O1 118.49(18) . . ? C7 C8 C9 118.3(2) . . ? C1 C6 C5 118.2(2) . . ? C10 C9 C8 120.7(2) . . ? C23 C24 C19 119.6(2) . . ? C22 C21 C20 119.6(2) . . ? C14 C13 C18 119.51(19) . . ? C14 C13 P2 122.77(16) . . ? C18 C13 P2 117.68(16) . . ? C7 C12 C11 118.5(2) . . ? C5 C4 C3 119.8(2) . . ? C21 C20 C19 120.0(2) . . ? C15 C16 C17 119.8(2) . . ? C10 C11 C12 120.5(2) . . ? C4 C5 C6 120.7(2) . . ? C18 C17 C16 120.5(2) . . ? C12 C7 C8 122.11(19) . . ? C12 C7 O2 119.38(17) . . ? C8 C7 O2 118.43(18) . . ? C24 C19 C20 119.9(2) . . ? C24 C19 P2 120.13(17) . . ? C20 C19 P2 119.91(16) . . ? C4 C3 C2 120.4(2) . . ? C22 C23 C24 120.8(2) . . ? C16 C15 C14 120.1(2) . . ? C23 C22 C21 120.2(2) . . ? C1 C2 C3 118.5(2) . . ? C11 C10 C9 119.9(2) . . ? C13 C14 C15 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.456 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.456 _refine_diff_density_max 0.425 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.065 data_7.cif #data_man89 _database_code_CSD 153018 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'iPr2P(S)-NH-P(S)(OPh)2' _chemical_formula_sum 'C18 H25 N O2 P2 S2' _chemical_formula_weight 413.45 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' 'N' 'N' 0.0061 0.0033 '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' '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.494(2) _cell_length_b 9.173(2) _cell_length_c 13.751(3) _cell_angle_alpha 97.97(3) _cell_angle_beta 104.38(3) _cell_angle_gamma 92.35(3) _cell_volume 1024.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.428 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3764 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3602 _reflns_number_gt 2585 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+3.1152P] 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 3602 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.2127 _refine_ls_wR_factor_gt 0.1908 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 1.306 _refine_ls_shift/su_mean 0.019 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.32126(16) 0.66449(17) 0.58888(11) 0.0529(4) Uani 1 d . . . P2 P 0.64334(17) 0.73491(18) 0.75645(10) 0.0544(5) Uani 1 d . . . S1 S 0.2961(2) 0.6248(2) 0.44314(13) 0.0821(6) Uani 1 d . . . S2 S 0.5567(2) 0.8442(2) 0.85402(13) 0.0846(7) Uani 1 d . . . N1 N 0.5147(6) 0.6485(6) 0.6535(4) 0.0480(12) Uani 1 d . . . O2 O 0.7596(5) 0.6127(5) 0.7950(3) 0.0796(15) Uani 1 d . . . O1 O 0.7631(4) 0.8251(5) 0.7106(3) 0.0626(12) Uani 1 d . . . C31 C 0.1946(7) 0.5359(8) 0.6295(5) 0.0649(17) Uani 1 d . . . C32 C 0.2321(15) 0.3859(9) 0.5998(10) 0.108(3) Uani 1 d . . . C6 C 0.9940(7) 0.9190(8) 0.8516(4) 0.0595(15) Uani 1 d . . . C4 C 1.1131(9) 1.1627(10) 0.8602(6) 0.084(2) Uani 1 d . . . C33 C 0.1914(9) 0.5732(8) 0.7384(6) 0.0664(17) Uani 1 d . . . C3 C 0.9947(11) 1.1813(12) 0.7770(7) 0.111(3) Uani 1 d . . . C1 C 0.8791(6) 0.9386(7) 0.7666(4) 0.0598(16) Uani 1 d . . . C23 C 0.0925(13) 0.8633(12) 0.5749(8) 0.151(5) Uani 1 d . . . H23A H 0.0261 0.7894 0.5928 0.227 Uiso 1 d R . . H23B H 0.0758 0.8497 0.5025 0.227 Uiso 1 d R . . H23C H 0.0629 0.9595 0.5978 0.227 Uiso 1 d R . . C5 C 1.1103(8) 1.0349(10) 0.8980(5) 0.074(2) Uani 1 d . . . C22 C 0.3843(14) 0.9633(10) 0.5957(8) 0.139(4) Uani 1 d . . . H22A H 0.4951 0.9562 0.6322 0.208 Uiso 1 d R . . H22B H 0.3532 1.0611 0.6126 0.208 Uiso 1 d R . . H22C H 0.3749 0.9429 0.5240 0.208 Uiso 1 d R . . C21 C 0.2718(10) 0.8485(8) 0.6249(6) 0.093(2) Uani 1 d . . . H21 H 0.2879 0.8668 0.6988 0.111 Uiso 1 d R . . C2 C 0.8772(10) 1.0693(11) 0.7294(6) 0.111(4) Uani 1 d . . . C7 C 0.700(3) 0.520(2) 0.8534(18) 0.057(6) Uani 0.534(9) d P A 1 C8 C 0.6302(16) 0.399(3) 0.8182(14) 0.084(8) Uani 0.534(9) d P A 1 H8 H 0.5901 0.3767 0.7480 0.100 Uiso 0.534(9) calc PR A 1 C9 C 0.605(2) 0.287(2) 0.8792(17) 0.090(7) Uani 0.534(9) d P A 1 H9 H 0.5243 0.2100 0.8588 0.107 Uiso 0.534(9) calc PR A 1 C10 C 0.7286(17) 0.3141(14) 0.9791(9) 0.067(4) Uani 0.534(9) d P A 1 H10 H 0.7207 0.2513 1.0256 0.080 Uiso 0.534(9) calc PR A 1 C11 C 0.8544(16) 0.4253(12) 1.0085(8) 0.064(3) Uani 0.534(9) d P A 1 H11 H 0.9313 0.4311 1.0705 0.077 Uiso 0.534(9) calc PR A 1 C12 C 0.8644(14) 0.5267(12) 0.9452(7) 0.057(3) Uani 0.534(9) d P A 1 H12 H 0.9552 0.5920 0.9539 0.068 Uiso 0.534(9) calc PR A 1 C7A C 0.746(4) 0.490(4) 0.847(2) 0.065(9) Uani 0.466(9) d P A 2 C8A C 0.713(3) 0.374(2) 0.8158(12) 0.068(4) Uani 0.466(9) d P A 2 H8A H 0.7146 0.3472 0.7482 0.081 Uiso 0.466(9) calc PR A 2 C9A C 0.672(2) 0.263(2) 0.8629(15) 0.069(5) Uani 0.466(9) d P A 2 H9A H 0.7030 0.1698 0.8421 0.083 Uiso 0.466(9) calc PR A 2 C10A C 0.5938(17) 0.2708(14) 0.9337(11) 0.049(3) Uani 0.466(9) d P A 2 H10A H 0.5637 0.1887 0.9596 0.058 Uiso 0.466(9) calc PR A 2 C11A C 0.5603(16) 0.4102(12) 0.9663(9) 0.056(3) Uani 0.466(9) d P A 2 H11A H 0.5052 0.4242 1.0171 0.067 Uiso 0.466(9) calc PR A 2 C12A C 0.6048(15) 0.5320(13) 0.9270(8) 0.051(3) Uani 0.466(9) d P A 2 H12A H 0.5674 0.6248 0.9397 0.062 Uiso 0.466(9) calc PR A 2 H6 H 0.991(7) 0.835(6) 0.872(4) 0.050(16) Uiso 1 d . . . H32A H 0.163(11) 0.308(10) 0.621(6) 0.12(3) Uiso 1 d . . . H5 H 1.174(8) 1.012(7) 0.950(5) 0.08(2) Uiso 1 d . . . H33B H 0.104(9) 0.516(8) 0.745(5) 0.08(2) Uiso 1 d . . . H33C H 0.158(9) 0.678(9) 0.753(5) 0.09(2) Uiso 1 d . . . H32B H 0.243(15) 0.360(13) 0.523(11) 0.19(5) Uiso 1 d . . . H32C H 0.311(4) 0.362(4) 0.648(3) 0.000(9) Uiso 1 d . . . H1 H 0.552(6) 0.605(6) 0.625(4) 0.029(17) Uiso 1 d . . . H33A H 0.303(8) 0.569(7) 0.780(5) 0.071(19) Uiso 1 d . . . H3 H 0.994(11) 1.283(10) 0.751(7) 0.12(3) Uiso 1 d . . . H4 H 1.194(9) 1.239(8) 0.892(6) 0.10(2) Uiso 1 d . . . H2 H 0.787(10) 1.081(9) 0.679(7) 0.11(3) Uiso 1 d . . . H31 H 0.090(9) 0.547(7) 0.588(5) 0.08(2) Uiso 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 0.0372(7) 0.0668(9) 0.0524(8) 0.0221(7) -0.0011(6) 0.0123(6) P2 0.0444(8) 0.0734(10) 0.0438(8) 0.0351(7) -0.0023(6) -0.0160(7) S1 0.0572(10) 0.1319(17) 0.0553(9) 0.0287(10) -0.0006(7) 0.0317(10) S2 0.0928(13) 0.0935(13) 0.0660(10) 0.0035(9) 0.0316(9) -0.0503(11) N1 0.036(2) 0.063(3) 0.048(3) 0.027(2) 0.005(2) 0.002(2) O2 0.053(2) 0.100(3) 0.078(3) 0.060(3) -0.022(2) -0.007(2) O1 0.044(2) 0.098(3) 0.043(2) 0.037(2) -0.0029(16) -0.025(2) C31 0.032(3) 0.082(5) 0.073(4) -0.001(3) 0.008(3) -0.010(3) C32 0.137(9) 0.059(5) 0.132(9) 0.003(5) 0.057(8) -0.032(5) C6 0.053(3) 0.077(4) 0.042(3) 0.012(3) 0.000(2) -0.002(3) C4 0.058(4) 0.109(6) 0.081(5) 0.006(4) 0.023(4) -0.037(4) C33 0.063(4) 0.062(4) 0.078(5) 0.014(3) 0.024(4) 0.001(3) C3 0.087(5) 0.136(8) 0.102(6) 0.055(6) 0.001(5) -0.063(5) C1 0.039(3) 0.098(5) 0.041(3) 0.025(3) 0.003(2) -0.025(3) C23 0.148(9) 0.178(10) 0.145(9) 0.071(8) 0.025(7) 0.131(9) C5 0.050(4) 0.114(6) 0.043(3) -0.007(4) -0.004(3) 0.003(4) C22 0.185(11) 0.089(6) 0.136(8) 0.081(6) -0.007(7) 0.012(6) C21 0.111(6) 0.080(5) 0.089(5) 0.045(4) 0.004(4) 0.050(4) C2 0.076(5) 0.156(8) 0.090(5) 0.082(6) -0.020(4) -0.067(5) C7 0.100(16) 0.021(7) 0.055(9) 0.022(6) 0.018(11) 0.024(10) C8 0.037(7) 0.16(2) 0.096(12) 0.099(14) 0.042(8) 0.064(11) C9 0.063(11) 0.124(14) 0.126(15) 0.093(12) 0.057(11) 0.069(10) C10 0.079(9) 0.082(8) 0.053(7) 0.042(6) 0.025(6) 0.024(7) C11 0.089(9) 0.062(7) 0.044(6) 0.020(5) 0.012(5) 0.019(6) C12 0.076(7) 0.055(6) 0.041(5) 0.019(5) 0.013(5) 0.020(5) C7 0.093(15) 0.09(2) 0.041(9) 0.039(12) 0.045(9) 0.077(14) C8 0.092(16) 0.073(13) 0.048(8) 0.016(8) 0.028(9) 0.026(10) C9 0.056(11) 0.061(10) 0.093(12) 0.038(9) 0.008(9) 0.006(8) C10 0.061(9) 0.046(7) 0.047(7) 0.019(6) 0.020(7) 0.015(6) C11 0.087(9) 0.044(7) 0.046(6) 0.012(5) 0.030(6) 0.004(6) C12 0.063(7) 0.047(7) 0.048(6) 0.019(5) 0.017(5) -0.003(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.686(5) . ? P1 C21 1.789(7) . ? P1 C31 1.800(6) . ? P1 S1 1.942(2) . ? P2 O2 1.584(4) . ? P2 O1 1.585(3) . ? P2 N1 1.636(5) . ? P2 S2 1.877(3) . ? O2 C7 1.41(2) . ? O2 C7 1.43(3) . ? O1 C1 1.401(6) . ? C31 C32 1.451(11) . ? C31 C33 1.496(9) . ? C6 C1 1.362(7) . ? C6 C5 1.388(9) . ? C4 C5 1.349(11) . ? C4 C3 1.358(11) . ? C3 C2 1.373(10) . ? C1 C2 1.366(10) . ? C23 C21 1.528(11) . ? C22 C21 1.552(12) . ? C7 C8 1.21(3) . ? C7 C12 1.63(3) . ? C8 C9 1.45(2) . ? C9 C10 1.49(3) . ? C10 C11 1.389(18) . ? C11 C12 1.373(14) . ? C7 C8 1.09(4) . ? C7 C12 1.83(2) . ? C8 C9 1.36(2) . ? C9 C10 1.30(2) . ? C10 C11 1.360(17) . ? C11 C12 1.385(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 C21 107.8(3) . . ? N1 P1 C31 106.5(3) . . ? C21 P1 C31 109.4(4) . . ? N1 P1 S1 111.2(2) . . ? C21 P1 S1 110.2(3) . . ? C31 P1 S1 111.7(2) . . ? O2 P2 O1 98.8(2) . . ? O2 P2 N1 104.1(3) . . ? O1 P2 N1 101.7(2) . . ? O2 P2 S2 116.2(2) . . ? O1 P2 S2 116.0(2) . . ? N1 P2 S2 117.5(2) . . ? P2 N1 P1 136.5(4) . . ? C7 O2 C7 20.2(11) . . ? C7 O2 P2 115.2(10) . . ? C7 O2 P2 134.8(10) . . ? C1 O1 P2 124.7(3) . . ? C32 C31 C33 114.9(8) . . ? C32 C31 P1 110.0(5) . . ? C33 C31 P1 114.0(5) . . ? C1 C6 C5 118.0(7) . . ? C5 C4 C3 119.2(7) . . ? C4 C3 C2 120.5(8) . . ? C6 C1 C2 120.9(6) . . ? C6 C1 O1 122.2(6) . . ? C2 C1 O1 116.8(5) . . ? C4 C5 C6 121.8(7) . . ? C23 C21 C22 111.2(7) . . ? C23 C21 P1 109.3(7) . . ? C22 C21 P1 110.9(7) . . ? C1 C2 C3 119.6(7) . . ? C8 C7 O2 123.2(19) . . ? C8 C7 C12 116.9(15) . . ? O2 C7 C12 98.2(16) . . ? C7 C8 C9 124(2) . . ? C8 C9 C10 110.2(17) . . ? C11 C10 C9 125.2(11) . . ? C12 C11 C10 119.5(11) . . ? C11 C12 C7 112.5(13) . . ? C8 C7 O2 129(2) . . ? C8 C7 C12 104(2) . . ? O2 C7 C12 108.3(15) . . ? C7 C8 C9 128.2(19) . . ? C10 C9 C8 127.7(19) . . ? C9 C10 C11 114.1(14) . . ? C10 C11 C12 122.7(12) . . ? C11 C12 C7 112.5(14) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.128 _refine_diff_density_min -0.933 _refine_diff_density_rms 0.086 data_9.cif #data_man68d _database_code_CSD 153019 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'Ph2P(S)-NH-P(S)iPr2' _chemical_formula_sum 'C18 H25 N P2 S2' _chemical_formula_weight 381.45 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.154(2) _cell_length_b 17.574(4) _cell_length_c 22.213(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3963.8(14) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.429 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3332 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3332 _reflns_number_gt 3096 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.7138P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.29(8) _refine_ls_number_reflns 3332 _refine_ls_number_parameters 431 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0737 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.004 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.47181(9) 0.02248(4) 1.09100(4) 0.0174(2) Uani 1 d . . . P2 P 0.57875(9) -0.12702(4) 1.03516(3) 0.0168(2) Uani 1 d . . . P3 P 0.55525(8) -0.06472(5) 0.78216(3) 0.0175(2) Uani 1 d . . . P4 P 0.67066(9) 0.06808(4) 0.85439(3) 0.01676(19) Uani 1 d . . . S1 S 0.46032(10) -0.01303(5) 1.17327(3) 0.0271(2) Uani 1 d . . . S2 S 0.60561(10) -0.15118(4) 0.94997(3) 0.0249(2) Uani 1 d . . . S3 S 0.57696(9) -0.00596(5) 0.70882(3) 0.0262(2) Uani 1 d . . . S4 S 0.69986(9) 0.08370(5) 0.94050(3) 0.0226(2) Uani 1 d . . . N1 N 0.5589(3) -0.03261(14) 1.04411(12) 0.0186(6) Uani 1 d . . . H1 H 0.593(3) -0.0114(18) 1.0142(15) 0.012(8) Uiso 1 d . . . N2 N 0.6052(3) -0.01863(15) 0.84372(11) 0.0177(6) Uani 1 d . . . H2 H 0.598(4) -0.045(2) 0.8748(18) 0.032(11) Uiso 1 d . . . C1 C 0.5562(4) 0.11199(17) 1.08221(13) 0.0199(7) Uani 1 d . . . C2 C 0.6892(4) 0.1151(2) 1.09559(16) 0.0292(9) Uani 1 d . . . H2A H 0.7320 0.0719 1.1098 0.035 Uiso 1 calc R . . C3 C 0.7583(4) 0.1818(2) 1.08796(18) 0.0375(10) Uani 1 d . . . H3 H 0.8477 0.1835 1.0970 0.045 Uiso 1 calc R . . C4 C 0.6958(5) 0.2453(2) 1.06719(17) 0.0390(10) Uani 1 d . . . H4 H 0.7432 0.2900 1.0612 0.047 Uiso 1 calc R . . C5 C 0.5628(5) 0.2436(2) 1.05511(18) 0.0386(10) Uani 1 d . . . H5 H 0.5200 0.2874 1.0419 0.046 Uiso 1 calc R . . C6 C 0.4932(4) 0.17714(19) 1.06257(16) 0.0293(9) Uani 1 d . . . H6 H 0.4034 0.1760 1.0544 0.035 Uiso 1 calc R . . C7 C 0.3124(4) 0.03620(17) 1.05627(14) 0.0191(7) Uani 1 d . . . C8 C 0.3038(4) 0.04367(18) 0.99404(14) 0.0227(8) Uani 1 d . . . H8 H 0.3799 0.0428 0.9708 0.027 Uiso 1 calc R . . C9 C 0.1828(3) 0.05238(18) 0.96663(15) 0.0234(8) Uani 1 d . . . H9 H 0.1775 0.0568 0.9250 0.028 Uiso 1 calc R . . C10 C 0.0695(4) 0.05453(19) 1.00118(16) 0.0277(8) Uani 1 d . . . H10 H -0.0122 0.0602 0.9828 0.033 Uiso 1 calc R . . C11 C 0.0783(4) 0.0481(2) 1.06336(16) 0.0311(9) Uani 1 d . . . H11 H 0.0025 0.0505 1.0868 0.037 Uiso 1 calc R . . C12 C 0.1986(4) 0.03825(19) 1.09028(15) 0.0254(8) Uani 1 d . . . H12 H 0.2036 0.0329 1.1319 0.030 Uiso 1 calc R . . C13 C 0.7244(4) -0.15557(19) 1.07830(15) 0.0258(8) Uani 1 d . . . H13 H 0.7450 -0.2079 1.0665 0.031 Uiso 1 calc R . . C14 C 0.8421(4) -0.1067(2) 1.05985(17) 0.0362(9) Uani 1 d . . . H14A H 0.8314 -0.0562 1.0756 0.054 Uiso 1 calc R . . H14B H 0.8474 -0.1046 1.0167 0.054 Uiso 1 calc R . . H14C H 0.9215 -0.1286 1.0756 0.054 Uiso 1 calc R . . C15 C 0.7070(4) -0.1558(2) 1.14632(15) 0.0334(9) Uani 1 d . . . H15A H 0.7846 -0.1763 1.1649 0.050 Uiso 1 calc R . . H15B H 0.6323 -0.1865 1.1568 0.050 Uiso 1 calc R . . H15C H 0.6933 -0.1047 1.1602 0.050 Uiso 1 calc R . . C16 C 0.4354(4) -0.17557(18) 1.06596(15) 0.0241(8) Uani 1 d . . . H16 H 0.4216 -0.1581 1.1074 0.029 Uiso 1 calc R . . C17 C 0.3113(4) -0.1591(2) 1.02963(19) 0.0357(9) Uani 1 d . . . H17A H 0.3250 -0.1738 0.9885 0.054 Uiso 1 calc R . . H17B H 0.2917 -0.1057 1.0315 0.054 Uiso 1 calc R . . H17C H 0.2389 -0.1875 1.0460 0.054 Uiso 1 calc R . . C18 C 0.4635(4) -0.26111(19) 1.06696(17) 0.0354(9) Uani 1 d . . . H18A H 0.3891 -0.2875 1.0835 0.053 Uiso 1 calc R . . H18B H 0.5397 -0.2708 1.0914 0.053 Uiso 1 calc R . . H18C H 0.4794 -0.2787 1.0267 0.053 Uiso 1 calc R . . C19 C 0.3862(3) -0.09188(17) 0.79597(14) 0.0181(7) Uani 1 d . . . C20 C 0.3275(3) -0.08731(18) 0.85200(14) 0.0215(7) Uani 1 d . . . H20 H 0.3747 -0.0685 0.8847 0.026 Uiso 1 calc R . . C21 C 0.1994(4) -0.11058(19) 0.85935(15) 0.0253(8) Uani 1 d . . . H21 H 0.1599 -0.1072 0.8970 0.030 Uiso 1 calc R . . C22 C 0.1292(4) -0.13881(18) 0.81142(15) 0.0241(8) Uani 1 d . . . H22 H 0.0425 -0.1545 0.8167 0.029 Uiso 1 calc R . . C23 C 0.1870(4) -0.14389(18) 0.75584(15) 0.0242(8) Uani 1 d . . . H23 H 0.1394 -0.1631 0.7235 0.029 Uiso 1 calc R . . C24 C 0.3154(4) -0.12064(17) 0.74771(14) 0.0216(8) Uani 1 d . . . H24 H 0.3544 -0.1242 0.7100 0.026 Uiso 1 calc R . . C25 C 0.6436(3) -0.15422(19) 0.78175(14) 0.0202(7) Uani 1 d . . . C26 C 0.5944(4) -0.21798(19) 0.81027(14) 0.0249(8) Uani 1 d . . . H26 H 0.5136 -0.2156 0.8299 0.030 Uiso 1 calc R . . C27 C 0.6643(4) -0.2850(2) 0.80982(15) 0.0336(9) Uani 1 d . . . H27 H 0.6313 -0.3274 0.8298 0.040 Uiso 1 calc R . . C28 C 0.7825(4) -0.2897(2) 0.78007(17) 0.0344(9) Uani 1 d . . . H28 H 0.8293 -0.3351 0.7798 0.041 Uiso 1 calc R . . C29 C 0.8316(4) -0.2269(2) 0.75060(17) 0.0348(9) Uani 1 d . . . H29 H 0.9114 -0.2303 0.7302 0.042 Uiso 1 calc R . . C30 C 0.7630(4) -0.1584(2) 0.75099(16) 0.0283(9) Uani 1 d . . . H30 H 0.7963 -0.1161 0.7310 0.034 Uiso 1 calc R . . C31 C 0.5572(4) 0.13845(18) 0.82245(16) 0.0261(8) Uani 1 d . . . H31 H 0.5702 0.1399 0.7787 0.031 Uiso 1 calc R . . C32 C 0.5850(5) 0.2177(2) 0.8478(2) 0.0451(11) Uani 1 d . . . H32A H 0.5296 0.2543 0.8280 0.068 Uiso 1 calc R . . H32B H 0.6757 0.2305 0.8410 0.068 Uiso 1 calc R . . H32C H 0.5672 0.2181 0.8902 0.068 Uiso 1 calc R . . C33 C 0.4148(4) 0.1166(2) 0.83502(17) 0.0337(9) Uani 1 d . . . H33A H 0.4030 0.1092 0.8775 0.051 Uiso 1 calc R . . H33B H 0.3941 0.0703 0.8141 0.051 Uiso 1 calc R . . H33C H 0.3576 0.1565 0.8214 0.051 Uiso 1 calc R . . C34 C 0.8230(3) 0.06829(18) 0.81072(13) 0.0203(7) Uani 1 d . . . H34 H 0.8009 0.0530 0.7695 0.024 Uiso 1 calc R . . C35 C 0.8883(4) 0.1459(2) 0.80750(19) 0.0387(10) Uani 1 d . . . H35A H 0.9016 0.1651 0.8475 0.058 Uiso 1 calc R . . H35B H 0.8329 0.1803 0.7854 0.058 Uiso 1 calc R . . H35C H 0.9718 0.1414 0.7875 0.058 Uiso 1 calc R . . C36 C 0.9166(4) 0.0088(2) 0.83614(16) 0.0322(9) Uani 1 d . . . H36A H 0.9941 0.0062 0.8114 0.048 Uiso 1 calc R . . H36B H 0.8738 -0.0399 0.8366 0.048 Uiso 1 calc R . . H36C H 0.9411 0.0226 0.8764 0.048 Uiso 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 0.0231(5) 0.0146(4) 0.0146(4) -0.0005(3) 0.0009(4) 0.0021(4) P2 0.0210(5) 0.0133(4) 0.0160(4) -0.0011(3) -0.0025(4) 0.0016(4) P3 0.0166(5) 0.0229(4) 0.0130(3) -0.0003(3) 0.0002(4) 0.0004(4) P4 0.0183(5) 0.0166(4) 0.0153(4) 0.0010(3) 0.0033(4) 0.0005(4) S1 0.0388(6) 0.0269(4) 0.0155(4) 0.0029(3) 0.0018(4) 0.0048(4) S2 0.0392(6) 0.0198(4) 0.0156(4) -0.0024(3) 0.0003(4) 0.0065(4) S3 0.0265(5) 0.0378(5) 0.0143(4) 0.0059(3) 0.0004(4) -0.0034(4) S4 0.0283(5) 0.0225(4) 0.0169(4) -0.0025(3) 0.0028(4) -0.0054(4) N1 0.0232(16) 0.0145(12) 0.0179(13) 0.0022(10) 0.0035(13) -0.0042(13) N2 0.0209(16) 0.0220(13) 0.0100(12) 0.0038(11) -0.0019(12) -0.0004(13) C1 0.029(2) 0.0175(15) 0.0129(14) -0.0039(12) 0.0006(16) 0.0006(16) C2 0.035(2) 0.0233(17) 0.0294(18) -0.0039(15) -0.0074(18) 0.0006(18) C3 0.039(3) 0.033(2) 0.040(2) -0.0081(17) -0.008(2) -0.011(2) C4 0.054(3) 0.0238(19) 0.039(2) -0.0043(16) -0.001(2) -0.016(2) C5 0.055(3) 0.0153(16) 0.046(2) 0.0031(16) -0.004(2) -0.001(2) C6 0.035(2) 0.0201(17) 0.0330(18) -0.0034(14) -0.0008(19) 0.0029(17) C7 0.0215(18) 0.0151(14) 0.0208(16) 0.0001(12) 0.0013(16) 0.0014(15) C8 0.0199(19) 0.0259(17) 0.0223(16) 0.0042(14) 0.0060(16) 0.0037(16) C9 0.0229(19) 0.0257(16) 0.0215(16) 0.0012(14) -0.0004(16) 0.0013(17) C10 0.023(2) 0.0282(17) 0.0320(18) 0.0014(15) -0.0036(17) -0.0019(18) C11 0.024(2) 0.038(2) 0.0315(18) -0.0009(16) 0.0085(18) -0.0007(18) C12 0.030(2) 0.0284(17) 0.0179(16) -0.0016(14) 0.0050(16) -0.0015(17) C13 0.029(2) 0.0210(16) 0.0271(18) -0.0060(14) -0.0102(17) 0.0052(17) C14 0.025(2) 0.045(2) 0.039(2) -0.0131(18) -0.0035(19) 0.0037(19) C15 0.039(2) 0.0312(18) 0.0303(18) -0.0029(16) -0.017(2) 0.0035(19) C16 0.031(2) 0.0204(16) 0.0207(16) -0.0017(13) -0.0023(16) -0.0041(17) C17 0.026(2) 0.0210(17) 0.060(3) -0.0009(18) -0.005(2) -0.0028(17) C18 0.047(2) 0.0210(17) 0.039(2) 0.0046(15) -0.013(2) -0.0084(19) C19 0.0147(17) 0.0177(15) 0.0219(15) 0.0030(12) -0.0021(14) 0.0022(15) C20 0.0200(19) 0.0262(16) 0.0183(15) -0.0018(13) -0.0031(15) -0.0002(17) C21 0.022(2) 0.0281(17) 0.0256(17) 0.0013(14) 0.0050(17) -0.0016(17) C22 0.0142(18) 0.0217(16) 0.0363(19) 0.0074(15) -0.0040(16) -0.0022(16) C23 0.027(2) 0.0205(16) 0.0249(17) 0.0020(14) -0.0109(17) -0.0032(17) C24 0.027(2) 0.0178(15) 0.0196(15) -0.0013(13) -0.0047(16) 0.0039(17) C25 0.0198(19) 0.0272(17) 0.0137(14) -0.0066(13) -0.0041(15) 0.0041(16) C26 0.0226(19) 0.0317(18) 0.0203(16) -0.0033(14) 0.0004(16) 0.0027(17) C27 0.044(3) 0.0303(19) 0.0267(19) -0.0046(15) -0.005(2) 0.007(2) C28 0.031(2) 0.039(2) 0.0333(19) -0.0149(17) -0.013(2) 0.015(2) C29 0.0151(19) 0.046(2) 0.044(2) -0.0229(19) -0.0024(18) 0.005(2) C30 0.022(2) 0.0336(19) 0.0295(18) -0.0122(16) -0.0039(17) -0.0022(18) C31 0.031(2) 0.0222(16) 0.0248(16) 0.0090(14) 0.0065(17) 0.0068(18) C32 0.051(3) 0.0229(18) 0.061(3) 0.0061(18) 0.012(3) 0.012(2) C33 0.027(2) 0.0381(19) 0.0362(19) 0.0142(17) 0.0068(18) 0.0129(19) C34 0.0171(18) 0.0250(16) 0.0188(16) -0.0011(13) 0.0050(15) -0.0001(16) C35 0.031(2) 0.035(2) 0.050(2) -0.0025(19) 0.017(2) -0.011(2) C36 0.020(2) 0.049(2) 0.0275(18) -0.0012(17) 0.0009(17) 0.005(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 N1 1.674(3) . ? P1 C1 1.802(3) . ? P1 C7 1.809(4) . ? P1 S1 1.9348(11) . ? P2 N1 1.683(3) . ? P2 C16 1.821(4) . ? P2 C13 1.832(4) . ? P2 S2 1.9585(11) . ? P3 N2 1.668(3) . ? P3 C19 1.808(3) . ? P3 C25 1.811(3) . ? P3 S3 1.9412(11) . ? P4 N2 1.679(3) . ? P4 C34 1.826(3) . ? P4 C31 1.833(3) . ? P4 S4 1.9550(11) . ? C1 C6 1.382(5) . ? C1 C2 1.383(5) . ? C2 C3 1.376(5) . ? C3 C4 1.365(6) . ? C4 C5 1.377(7) . ? C5 C6 1.375(5) . ? C7 C12 1.381(5) . ? C7 C8 1.391(4) . ? C8 C9 1.379(5) . ? C9 C10 1.384(5) . ? C10 C11 1.389(5) . ? C11 C12 1.371(6) . ? C13 C15 1.521(5) . ? C13 C14 1.528(5) . ? C16 C17 1.524(5) . ? C16 C18 1.531(5) . ? C19 C20 1.382(5) . ? C19 C24 1.386(5) . ? C20 C21 1.373(5) . ? C21 C22 1.374(5) . ? C22 C23 1.370(5) . ? C23 C24 1.378(5) . ? C25 C26 1.381(5) . ? C25 C30 1.394(5) . ? C26 C27 1.375(5) . ? C27 C28 1.373(6) . ? C28 C29 1.377(6) . ? C29 C30 1.390(5) . ? C31 C33 1.521(6) . ? C31 C32 1.529(5) . ? C34 C35 1.519(5) . ? C34 C36 1.522(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 N1 P1 C1 100.73(14) . . ? N1 P1 C7 106.51(14) . . ? C1 P1 C7 105.24(15) . . ? N1 P1 S1 115.65(10) . . ? C1 P1 S1 114.37(10) . . ? C7 P1 S1 113.07(11) . . ? N1 P2 C16 108.76(16) . . ? N1 P2 C13 107.75(15) . . ? C16 P2 C13 108.69(16) . . ? N1 P2 S2 110.16(10) . . ? C16 P2 S2 111.89(11) . . ? C13 P2 S2 109.48(12) . . ? N2 P3 C19 106.13(15) . . ? N2 P3 C25 105.97(14) . . ? C19 P3 C25 104.00(15) . . ? N2 P3 S3 113.26(10) . . ? C19 P3 S3 112.99(11) . . ? C25 P3 S3 113.68(11) . . ? N2 P4 C34 105.19(14) . . ? N2 P4 C31 107.99(16) . . ? C34 P4 C31 109.00(15) . . ? N2 P4 S4 109.00(10) . . ? C34 P4 S4 113.02(11) . . ? C31 P4 S4 112.29(12) . . ? P1 N1 P2 134.97(18) . . ? P3 N2 P4 132.58(16) . . ? C6 C1 C2 119.1(3) . . ? C6 C1 P1 122.5(3) . . ? C2 C1 P1 118.4(3) . . ? C3 C2 C1 120.3(4) . . ? C4 C3 C2 120.1(4) . . ? C3 C4 C5 120.3(4) . . ? C6 C5 C4 119.9(4) . . ? C5 C6 C1 120.2(4) . . ? C12 C7 C8 119.2(3) . . ? C12 C7 P1 121.3(2) . . ? C8 C7 P1 119.5(3) . . ? C9 C8 C7 120.4(3) . . ? C8 C9 C10 119.9(3) . . ? C9 C10 C11 119.8(4) . . ? C12 C11 C10 120.1(4) . . ? C11 C12 C7 120.7(3) . . ? C15 C13 C14 111.0(3) . . ? C15 C13 P2 115.3(3) . . ? C14 C13 P2 109.7(2) . . ? C17 C16 C18 110.4(3) . . ? C17 C16 P2 111.9(2) . . ? C18 C16 P2 108.4(3) . . ? C20 C19 C24 119.6(3) . . ? C20 C19 P3 123.1(3) . . ? C24 C19 P3 117.2(3) . . ? C21 C20 C19 119.9(3) . . ? C20 C21 C22 120.5(3) . . ? C23 C22 C21 120.0(3) . . ? C22 C23 C24 120.3(3) . . ? C23 C24 C19 119.8(3) . . ? C26 C25 C30 119.8(3) . . ? C26 C25 P3 121.6(3) . . ? C30 C25 P3 118.7(3) . . ? C27 C26 C25 120.3(3) . . ? C28 C27 C26 120.4(4) . . ? C27 C28 C29 119.9(3) . . ? C28 C29 C30 120.6(4) . . ? C29 C30 C25 119.0(4) . . ? C33 C31 C32 109.8(3) . . ? C33 C31 P4 110.8(2) . . ? C32 C31 P4 110.8(3) . . ? C35 C34 C36 111.2(3) . . ? C35 C34 P4 113.4(2) . . ? C36 C34 P4 109.3(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S4 0.84(3) 2.58(3) 3.395(3) 165(3) . N2 H2 S2 0.83(4) 2.51(4) 3.316(3) 164(3) . _diffrn_measured_fraction_theta_max 0.852 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.852 _refine_diff_density_max 0.349 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.054 data_10.cif #data_m _database_code_CSD 153020 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'PhC(O)-NH-P(S)(OPh)2' _chemical_formula_sum 'C19 H16 N O3 P S' _chemical_formula_weight 369.36 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' '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.974(2) _cell_length_b 13.675(3) _cell_length_c 15.078(3) _cell_angle_alpha 76.93(3) _cell_angle_beta 70.93(3) _cell_angle_gamma 68.82(3) _cell_volume 1798.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12158 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 28.72 _reflns_number_total 7912 _reflns_number_gt 5947 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0454P)^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 7912 _refine_ls_number_parameters 579 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0780 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _refine_ls_shift/su_max 6.309 _refine_ls_shift/su_mean 0.557 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P2 P 0.13144(5) 0.29587(3) 0.85582(3) 0.01514(10) Uani 1 d . . . S2 S -0.02584(5) 0.41051(4) 0.91482(3) 0.02330(11) Uani 1 d . . . O6 O -0.00725(12) 0.32232(10) 0.70905(9) 0.0209(3) Uani 1 d . . . O4 O 0.28762(12) 0.26569(9) 0.87709(8) 0.0180(3) Uani 1 d . . . N2 N 0.20462(15) 0.30861(11) 0.73796(10) 0.0158(3) Uani 1 d . . . O5 O 0.10075(12) 0.18538(9) 0.87814(9) 0.0196(3) Uani 1 d . . . C20 C 0.29559(17) 0.23666(14) 0.97122(12) 0.0170(3) Uani 1 d . . . C32 C 0.20173(18) 0.33089(13) 0.57343(12) 0.0167(3) Uani 1 d . . . C38 C 0.12419(17) 0.31995(12) 0.67690(12) 0.0159(3) Uani 1 d . . . C27 C -0.1268(2) 0.15049(16) 0.90337(17) 0.0307(5) Uani 1 d . . . C26 C -0.03040(18) 0.16582(13) 0.94129(13) 0.0199(4) Uani 1 d . . . C25 C 0.2760(2) 0.31334(15) 1.02347(13) 0.0233(4) Uani 1 d . . . C23 C 0.3173(2) 0.17738(16) 1.15318(14) 0.0252(4) Uani 1 d . . . C31 C -0.0549(2) 0.15809(16) 1.03732(14) 0.0305(4) Uani 1 d . . . C24 C 0.2863(2) 0.28256(16) 1.11552(14) 0.0259(4) Uani 1 d . . . C33 C 0.35611(19) 0.30915(15) 0.53598(13) 0.0226(4) Uani 1 d . . . C37 C 0.1139(2) 0.36564(16) 0.51150(14) 0.0256(4) Uani 1 d . . . C36 C 0.1795(2) 0.38021(18) 0.41462(14) 0.0318(5) Uani 1 d . . . C34 C 0.4207(2) 0.32343(16) 0.43913(14) 0.0263(4) Uani 1 d . . . C22 C 0.3377(2) 0.10176(16) 1.09921(14) 0.0265(4) Uani 1 d . . . C35 C 0.3322(2) 0.35965(16) 0.37830(14) 0.0271(4) Uani 1 d . . . C21 C 0.32702(19) 0.13101(14) 1.00698(13) 0.0227(4) Uani 1 d . . . C29 C -0.2810(2) 0.11988(17) 1.06209(19) 0.0402(6) Uani 1 d . . . C28 C -0.2545(2) 0.12866(17) 0.9661(2) 0.0428(6) Uani 1 d . . . C30 C -0.1822(2) 0.13456(18) 1.09823(17) 0.0392(5) Uani 1 d . . . P1 P 0.19465(5) 0.83253(3) 0.36435(3) 0.01700(10) Uani 1 d . . . S1 S -0.01610(5) 0.89373(4) 0.38841(4) 0.02431(11) Uani 1 d . . . O3 O 0.49659(12) 0.68396(10) 0.30744(9) 0.0214(3) Uani 1 d . . . O2 O 0.29554(14) 0.90155(10) 0.29637(8) 0.0222(3) Uani 1 d . . . O1 O 0.25916(13) 0.80075(10) 0.45263(8) 0.0198(3) Uani 1 d . . . N1 N 0.25688(15) 0.72526(11) 0.30864(10) 0.0167(3) Uani 1 d . . . C19 C 0.40638(17) 0.66528(13) 0.28183(12) 0.0168(3) Uani 1 d . . . C17 C 0.4094(2) 0.49187(14) 0.11883(13) 0.0209(4) Uani 1 d . . . C1 C 0.19372(18) 0.74950(13) 0.53983(12) 0.0171(3) Uani 1 d . . . C6 C 0.1137(2) 0.80843(16) 0.61408(14) 0.0238(4) Uani 1 d . . . C14 C 0.59185(19) 0.50594(14) 0.21357(14) 0.0228(4) Uani 1 d . . . C13 C 0.44990(17) 0.58012(13) 0.22227(12) 0.0160(3) Uani 1 d . . . C15 C 0.6409(2) 0.42487(15) 0.15869(14) 0.0266(4) Uani 1 d . . . C8 C 0.2964(2) 1.02287(14) 0.39072(13) 0.0214(4) Uani 1 d . . . C11 C 0.6014(2) 0.98055(16) 0.30303(15) 0.0277(4) Uani 1 d . . . C9 C 0.3766(2) 1.07278(15) 0.41310(14) 0.0279(4) Uani 1 d . . . C18 C 0.35876(19) 0.57274(13) 0.17428(12) 0.0175(4) Uani 1 d . . . C7 C 0.37167(18) 0.95220(13) 0.32488(12) 0.0167(3) Uani 1 d . . . C2 C 0.2190(2) 0.64212(15) 0.55017(15) 0.0272(4) Uani 1 d . . . C3 C 0.1605(3) 0.59319(17) 0.63841(17) 0.0367(5) Uani 1 d . . . C12 C 0.52251(19) 0.93051(14) 0.27978(13) 0.0211(4) Uani 1 d . . . C16 C 0.5498(2) 0.41739(15) 0.11132(14) 0.0249(4) Uani 1 d . . . C5 C 0.0558(2) 0.75824(18) 0.70223(15) 0.0339(5) Uani 1 d . . . C4 C 0.0797(2) 0.6502(2) 0.71390(17) 0.0393(6) Uani 1 d . . . C10 C 0.5288(2) 1.05131(17) 0.36966(15) 0.0315(5) Uani 1 d . . . H16 H 0.581(2) 0.3603(19) 0.0732(17) 0.029(7) Uiso 1 d . . . H34 H 0.527(3) 0.3074(18) 0.4144(16) 0.028(7) Uiso 1 d . . . H14 H 0.652(3) 0.5088(18) 0.2472(17) 0.029(7) Uiso 1 d . . . H25 H 0.253(2) 0.3860(19) 0.9986(17) 0.032(7) Uiso 1 d . . . H12 H 0.567(3) 0.8823(19) 0.2344(17) 0.023(7) Uiso 1 d . . . H17 H 0.348(2) 0.4859(18) 0.0855(17) 0.026(7) Uiso 1 d . . . H33 H 0.417(3) 0.2838(18) 0.5743(17) 0.035(7) Uiso 1 d . . . H1N H 0.192(3) 0.7065(18) 0.3007(17) 0.042(7) Uiso 1 d . . . H18 H 0.260(3) 0.6252(18) 0.1769(16) 0.033(7) Uiso 1 d . . . H6 H 0.101(2) 0.879(2) 0.6034(17) 0.033(7) Uiso 1 d . . . H35 H 0.379(2) 0.3716(18) 0.3119(17) 0.027(7) Uiso 1 d . . . H22 H 0.357(3) 0.0307(19) 1.1262(17) 0.035(7) Uiso 1 d . . . H21 H 0.339(2) 0.0783(19) 0.9689(17) 0.036(7) Uiso 1 d . . . H9 H 0.335(2) 1.1215(19) 0.4554(17) 0.033(7) Uiso 1 d . . . H37 H 0.009(3) 0.3813(18) 0.5383(17) 0.035(7) Uiso 1 d . . . H8 H 0.192(3) 1.0337(18) 0.4215(17) 0.029(7) Uiso 1 d . . . H27 H -0.100(2) 0.1532(19) 0.8328(18) 0.046(7) Uiso 1 d . . . H11 H 0.705(3) 0.9669(18) 0.2733(16) 0.042(7) Uiso 1 d . . . H23 H 0.324(3) 0.1574(19) 1.2170(17) 0.036(7) Uiso 1 d . . . H2N H 0.288(3) 0.3125(19) 0.7179(17) 0.035(7) Uiso 1 d . . . H2 H 0.280(3) 0.6030(19) 0.4995(17) 0.044(7) Uiso 1 d . . . H15 H 0.742(3) 0.3738(18) 0.1522(16) 0.046(7) Uiso 1 d . . . H24 H 0.275(3) 0.3341(19) 1.1534(17) 0.038(7) Uiso 1 d . . . H31 H 0.017(2) 0.1663(18) 1.0629(16) 0.053(7) Uiso 1 d . . . H10 H 0.583(2) 1.0843(18) 0.3889(16) 0.043(7) Uiso 1 d . . . H36 H 0.122(3) 0.4047(19) 0.3699(17) 0.043(7) Uiso 1 d . . . H4 H 0.038(2) 0.6187(19) 0.7746(18) 0.050(7) Uiso 1 d . . . H30 H -0.199(3) 0.1263(18) 1.1710(18) 0.050(7) Uiso 1 d . . . H3 H 0.176(2) 0.5165(19) 0.6481(16) 0.057(7) Uiso 1 d . . . H29 H -0.369(3) 0.1034(19) 1.1054(17) 0.053(7) Uiso 1 d . . . H5 H 0.000(3) 0.8023(19) 0.7542(17) 0.043(7) Uiso 1 d . . . H28 H -0.322(3) 0.1174(18) 0.9381(17) 0.058(7) Uiso 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 P2 0.0124(2) 0.0172(2) 0.0161(2) -0.00294(17) -0.00334(17) -0.00477(17) S2 0.0185(2) 0.0219(2) 0.0262(3) -0.00927(19) -0.00365(19) -0.00087(17) O6 0.0140(6) 0.0288(7) 0.0232(7) -0.0070(5) -0.0049(5) -0.0085(5) O4 0.0145(6) 0.0251(6) 0.0157(6) -0.0016(5) -0.0055(5) -0.0069(5) N2 0.0106(7) 0.0213(7) 0.0165(8) -0.0023(6) -0.0036(6) -0.0062(6) O5 0.0163(6) 0.0193(6) 0.0220(7) -0.0038(5) 0.0001(5) -0.0081(5) C20 0.0104(8) 0.0253(9) 0.0149(9) -0.0012(7) -0.0030(6) -0.0063(7) C32 0.0166(8) 0.0173(8) 0.0195(9) -0.0032(7) -0.0056(7) -0.0079(7) C38 0.0138(8) 0.0132(8) 0.0221(9) -0.0037(7) -0.0066(7) -0.0036(6) C27 0.0351(11) 0.0254(10) 0.0392(13) 0.0058(9) -0.0188(10) -0.0160(9) C26 0.0124(8) 0.0172(8) 0.0279(10) -0.0017(7) -0.0016(7) -0.0060(7) C25 0.0266(10) 0.0223(10) 0.0243(10) -0.0007(8) -0.0086(8) -0.0112(8) C23 0.0218(9) 0.0362(11) 0.0192(10) 0.0012(8) -0.0076(8) -0.0119(8) C31 0.0273(10) 0.0384(12) 0.0275(11) -0.0028(9) -0.0022(8) -0.0175(9) C24 0.0299(10) 0.0326(11) 0.0204(10) -0.0054(8) -0.0068(8) -0.0143(9) C33 0.0169(9) 0.0342(10) 0.0206(10) -0.0067(8) -0.0067(8) -0.0092(8) C37 0.0191(9) 0.0363(11) 0.0227(10) -0.0003(8) -0.0084(8) -0.0096(8) C36 0.0290(11) 0.0462(13) 0.0222(11) 0.0051(9) -0.0138(9) -0.0135(9) C34 0.0202(10) 0.0394(11) 0.0232(10) -0.0075(9) -0.0026(8) -0.0143(8) C22 0.0266(10) 0.0231(10) 0.0275(11) 0.0045(8) -0.0112(8) -0.0061(8) C35 0.0315(11) 0.0343(11) 0.0177(10) -0.0002(8) -0.0052(8) -0.0159(9) C21 0.0213(9) 0.0227(9) 0.0242(10) -0.0041(8) -0.0080(8) -0.0045(7) C29 0.0199(10) 0.0278(11) 0.0615(17) 0.0034(11) 0.0028(10) -0.0118(9) C28 0.0298(11) 0.0323(12) 0.0748(19) 0.0096(12) -0.0260(12) -0.0186(10) C30 0.0354(12) 0.0411(13) 0.0340(13) -0.0043(10) 0.0081(10) -0.0194(10) P1 0.0172(2) 0.0200(2) 0.0158(2) -0.00520(18) -0.00329(18) -0.00738(17) S1 0.0176(2) 0.0243(2) 0.0291(3) -0.0112(2) -0.00379(19) -0.00186(18) O3 0.0139(6) 0.0334(7) 0.0217(7) -0.0081(6) -0.0040(5) -0.0107(5) O2 0.0292(7) 0.0288(7) 0.0159(6) -0.0024(5) -0.0060(5) -0.0176(6) O1 0.0210(6) 0.0284(7) 0.0144(6) -0.0019(5) -0.0038(5) -0.0139(5) N1 0.0115(7) 0.0210(7) 0.0204(8) -0.0064(6) -0.0049(6) -0.0055(6) C19 0.0135(8) 0.0222(9) 0.0160(9) -0.0011(7) -0.0037(7) -0.0079(7) C17 0.0225(9) 0.0223(9) 0.0199(9) -0.0028(7) -0.0082(8) -0.0067(7) C1 0.0148(8) 0.0208(9) 0.0185(9) 0.0006(7) -0.0071(7) -0.0080(7) C6 0.0216(9) 0.0219(10) 0.0230(10) -0.0022(8) -0.0057(8) -0.0020(7) C14 0.0167(9) 0.0261(10) 0.0268(10) -0.0044(8) -0.0079(8) -0.0057(7) C13 0.0136(8) 0.0185(8) 0.0156(9) -0.0011(7) -0.0029(7) -0.0065(6) C15 0.0187(9) 0.0258(10) 0.0307(11) -0.0070(8) -0.0057(8) -0.0003(8) C8 0.0213(9) 0.0238(9) 0.0188(10) -0.0042(7) -0.0017(8) -0.0092(8) C11 0.0194(9) 0.0304(11) 0.0329(12) 0.0028(9) -0.0067(8) -0.0115(8) C9 0.0388(11) 0.0259(10) 0.0233(11) -0.0057(8) -0.0063(9) -0.0152(9) C18 0.0148(8) 0.0198(9) 0.0171(9) -0.0025(7) -0.0039(7) -0.0046(7) C7 0.0204(8) 0.0167(8) 0.0157(9) 0.0011(7) -0.0064(7) -0.0092(7) C2 0.0315(10) 0.0201(9) 0.0371(12) -0.0035(9) -0.0195(9) -0.0070(8) C3 0.0474(13) 0.0279(11) 0.0498(15) 0.0149(10) -0.0350(12) -0.0212(10) C12 0.0214(9) 0.0178(9) 0.0198(10) -0.0024(7) -0.0016(7) -0.0045(7) C16 0.0282(10) 0.0219(9) 0.0226(10) -0.0072(8) -0.0055(8) -0.0041(8) C5 0.0228(10) 0.0493(13) 0.0232(11) -0.0016(10) -0.0041(8) -0.0074(9) C4 0.0341(12) 0.0565(15) 0.0332(13) 0.0239(11) -0.0202(10) -0.0288(11) C10 0.0375(12) 0.0365(11) 0.0327(12) 0.0003(9) -0.0142(9) -0.0239(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 P2 O4 1.5816(12) . ? P2 O5 1.5897(12) . ? P2 N2 1.6809(16) . ? P2 S2 1.9109(10) . ? O6 C38 1.2312(19) . ? O4 C20 1.405(2) . ? N2 C38 1.358(2) . ? O5 C26 1.419(2) . ? C20 C25 1.372(2) . ? C20 C21 1.381(2) . ? C32 C37 1.377(2) . ? C32 C33 1.398(2) . ? C32 C38 1.498(2) . ? C27 C26 1.361(3) . ? C27 C28 1.402(3) . ? C26 C31 1.373(3) . ? C25 C24 1.383(3) . ? C23 C22 1.376(3) . ? C23 C24 1.382(3) . ? C31 C30 1.400(3) . ? C33 C34 1.390(3) . ? C37 C36 1.393(3) . ? C36 C35 1.384(3) . ? C34 C35 1.369(3) . ? C22 C21 1.386(3) . ? C29 C30 1.360(3) . ? C29 C28 1.369(4) . ? P1 O1 1.5718(13) . ? P1 O2 1.5902(14) . ? P1 N1 1.6738(15) . ? P1 S1 1.9022(9) . ? O3 C19 1.2090(19) . ? O2 C7 1.4032(19) . ? O1 C1 1.414(2) . ? N1 C19 1.390(2) . ? C19 C13 1.485(2) . ? C17 C18 1.384(2) . ? C17 C16 1.389(3) . ? C1 C2 1.378(2) . ? C1 C6 1.378(3) . ? C6 C5 1.394(3) . ? C14 C15 1.382(3) . ? C14 C13 1.397(2) . ? C13 C18 1.374(2) . ? C15 C16 1.367(3) . ? C8 C9 1.377(3) . ? C8 C7 1.380(2) . ? C11 C12 1.374(3) . ? C11 C10 1.389(3) . ? C9 C10 1.390(3) . ? C7 C12 1.384(2) . ? C2 C3 1.389(3) . ? C3 C4 1.378(3) . ? C5 C4 1.388(3) . ? 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 O4 P2 O5 102.68(7) . . ? O4 P2 N2 93.56(7) . . ? O5 P2 N2 103.50(8) . . ? O4 P2 S2 116.96(5) . . ? O5 P2 S2 116.44(5) . . ? N2 P2 S2 120.08(6) . . ? C20 O4 P2 118.99(10) . . ? C38 N2 P2 122.19(12) . . ? C26 O5 P2 124.70(11) . . ? C25 C20 C21 122.35(17) . . ? C25 C20 O4 119.18(16) . . ? C21 C20 O4 118.45(16) . . ? C37 C32 C33 118.20(17) . . ? C37 C32 C38 117.32(15) . . ? C33 C32 C38 124.48(15) . . ? O6 C38 N2 118.79(16) . . ? O6 C38 C32 124.01(15) . . ? N2 C38 C32 117.19(14) . . ? C26 C27 C28 117.5(2) . . ? C27 C26 C31 121.61(18) . . ? C27 C26 O5 117.62(17) . . ? C31 C26 O5 120.71(16) . . ? C20 C25 C24 118.06(18) . . ? C22 C23 C24 120.14(18) . . ? C26 C31 C30 119.6(2) . . ? C25 C24 C23 120.78(19) . . ? C34 C33 C32 121.58(17) . . ? C32 C37 C36 119.84(18) . . ? C35 C36 C37 121.53(19) . . ? C35 C34 C33 119.74(18) . . ? C23 C22 C21 119.99(19) . . ? C34 C35 C36 119.10(19) . . ? C20 C21 C22 118.67(18) . . ? C30 C29 C28 119.3(2) . . ? C29 C28 C27 122.0(2) . . ? C29 C30 C31 119.9(2) . . ? O1 P1 O2 100.57(7) . . ? O1 P1 N1 107.37(8) . . ? O2 P1 N1 101.79(7) . . ? O1 P1 S1 116.42(6) . . ? O2 P1 S1 117.64(6) . . ? N1 P1 S1 111.45(6) . . ? C7 O2 P1 125.83(11) . . ? C1 O1 P1 123.50(10) . . ? C19 N1 P1 123.75(12) . . ? O3 C19 N1 119.26(15) . . ? O3 C19 C13 122.15(15) . . ? N1 C19 C13 118.59(14) . . ? C18 C17 C16 121.41(17) . . ? C2 C1 C6 121.95(18) . . ? C2 C1 O1 119.72(17) . . ? C6 C1 O1 118.20(15) . . ? C1 C6 C5 119.17(19) . . ? C15 C14 C13 121.11(17) . . ? C18 C13 C14 119.14(16) . . ? C18 C13 C19 123.10(15) . . ? C14 C13 C19 117.74(15) . . ? C16 C15 C14 119.68(17) . . ? C9 C8 C7 117.96(17) . . ? C12 C11 C10 119.80(18) . . ? C8 C9 C10 119.92(19) . . ? C13 C18 C17 119.32(16) . . ? C8 C7 C12 123.21(16) . . ? C8 C7 O2 120.85(15) . . ? C12 C7 O2 115.87(15) . . ? C1 C2 C3 118.2(2) . . ? C4 C3 C2 121.1(2) . . ? C11 C12 C7 118.21(17) . . ? C15 C16 C17 119.34(17) . . ? C4 C5 C6 119.7(2) . . ? C3 C4 C5 119.9(2) . . ? C11 C10 C9 120.87(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O6 0.83(2) 2.07(2) 2.8942(18) 172(2) 2_566 N2 H2N O3 0.80(2) 2.08(2) 2.8661(19) 169(2) 2_666 _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.293 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.048 data_11.cif #data_j _database_code_CSD 153021 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety '[Ph2P(S)-N-P(O)(OPh)2]2Pd' _chemical_formula_sum 'C24 H20 N O3 P2 Pd0.50 S' _chemical_formula_weight 517.61 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' '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' 'Pd' 'Pd' -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.678(2) _cell_length_b 9.294(2) _cell_length_c 23.112(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.24(3) _cell_angle_gamma 90.00 _cell_volume 2263.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.696 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8184 _exptl_absorpt_correction_T_max 0.8734 _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10385 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3913 _reflns_number_gt 3322 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.8296P] 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 3913 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0650 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.150 _refine_ls_shift/su_mean 0.006 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.5000 0.0000 0.0000 0.01117(8) Uani 1 d S . . P2 P 0.69327(5) 0.15083(6) 0.07458(2) 0.01359(13) Uani 1 d . . . S1 S 0.69706(5) 0.10396(6) -0.01067(2) 0.01804(14) Uani 1 d . . . P1 P 0.45309(5) 0.17431(6) 0.11826(2) 0.01471(14) Uani 1 d . . . O2 O 0.35072(13) 0.05673(16) 0.12885(6) 0.0161(3) Uani 1 d . . . O1 O 0.37010(14) 0.27005(16) 0.06975(7) 0.0189(3) Uani 1 d . . . C7 C 0.3831(2) -0.0454(2) 0.17409(10) 0.0148(5) Uani 1 d . . . C19 C 0.8099(2) 0.0491(2) 0.12292(10) 0.0155(5) Uani 1 d . . . N1 N 0.55056(16) 0.09453(18) 0.08150(7) 0.0139(4) Uani 1 d . . . C13 C 0.71773(19) 0.3394(2) 0.09170(10) 0.0156(5) Uani 1 d . . . C10 C 0.4356(2) -0.2507(3) 0.26030(11) 0.0236(5) Uani 1 d . . . H10 H 0.451(2) -0.315(3) 0.2894(11) 0.026(7) Uiso 1 d . . . O3 O 0.51152(15) 0.24853(17) 0.17181(7) 0.0227(4) Uani 1 d . . . C22 C 0.9866(2) -0.1178(3) 0.19526(11) 0.0252(6) Uani 1 d . . . H22 H 1.046(2) -0.173(3) 0.2195(10) 0.020(6) Uiso 1 d . . . C14 C 0.7859(2) 0.3851(3) 0.14515(11) 0.0195(5) Uani 1 d . . . H14 H 0.825(2) 0.320(3) 0.1715(11) 0.025(7) Uiso 1 d . . . C16 C 0.7397(2) 0.6309(3) 0.11778(11) 0.0243(6) Uani 1 d . . . H16 H 0.748(2) 0.724(3) 0.1252(11) 0.024(7) Uiso 1 d . . . C1 C 0.2731(2) 0.3635(2) 0.08102(10) 0.0200(5) Uani 1 d . . . C11 C 0.4896(2) -0.2605(3) 0.21024(11) 0.0252(6) Uani 1 d . . . H11 H 0.543(2) -0.337(3) 0.2047(11) 0.032(7) Uiso 1 d . . . C8 C 0.3288(2) -0.0338(3) 0.22432(11) 0.0226(5) Uani 1 d . . . H8 H 0.277(3) 0.045(3) 0.2276(11) 0.029(7) Uiso 1 d . . . C3 C 0.0538(3) 0.4216(4) 0.06738(13) 0.0369(7) Uani 1 d . . . H3 H -0.026(3) 0.397(3) 0.0513(12) 0.040(8) Uiso 1 d . . . C18 C 0.6606(2) 0.4412(3) 0.05120(11) 0.0214(5) Uani 1 d . . . H18 H 0.618(2) 0.410(2) 0.0170(10) 0.013(6) Uiso 1 d . . . C17 C 0.6718(2) 0.5864(3) 0.06480(12) 0.0260(6) Uani 1 d . . . H17 H 0.637(2) 0.645(3) 0.0380(12) 0.031(7) Uiso 1 d . . . C12 C 0.4628(2) -0.1583(3) 0.16620(10) 0.0206(5) Uani 1 d . . . H12 H 0.493(2) -0.167(2) 0.1301(10) 0.013(6) Uiso 1 d . . . C20 C 0.9227(2) 0.0067(2) 0.10373(11) 0.0208(5) Uani 1 d . . . H20 H 0.936(2) 0.034(2) 0.0640(11) 0.015(6) Uiso 1 d . . . C23 C 0.8750(2) -0.0764(3) 0.21412(11) 0.0229(5) Uani 1 d . . . H23 H 0.859(2) -0.107(2) 0.2496(11) 0.016(6) Uiso 1 d . . . C2 C 0.1490(2) 0.3237(3) 0.06124(12) 0.0284(6) Uani 1 d . . . H2 H 0.133(2) 0.239(3) 0.0453(11) 0.024(7) Uiso 1 d . . . C15 C 0.7969(2) 0.5307(3) 0.15792(11) 0.0240(6) Uani 1 d . . . H15 H 0.845(2) 0.567(3) 0.1927(11) 0.029(7) Uiso 1 d . . . C24 C 0.7867(2) 0.0078(2) 0.17845(10) 0.0192(5) Uani 1 d . . . H24 H 0.708(2) 0.031(2) 0.1911(10) 0.015(6) Uiso 1 d . . . C5 C 0.2074(3) 0.5909(3) 0.11265(14) 0.0354(7) Uani 1 d . . . H5 H 0.230(3) 0.693(4) 0.1293(13) 0.055(9) Uiso 1 d . . . C21 C 1.0106(2) -0.0749(3) 0.14070(12) 0.0271(6) Uani 1 d . . . H21 H 1.081(2) -0.094(2) 0.1289(10) 0.013(6) Uiso 1 d . . . C6 C 0.3042(2) 0.4952(3) 0.10673(12) 0.0256(6) Uani 1 d . . . H6 H 0.390(3) 0.518(3) 0.1200(12) 0.032(8) Uiso 1 d . . . C9 C 0.3560(2) -0.1381(3) 0.26773(11) 0.0269(6) Uani 1 d . . . H9 H 0.323(2) -0.131(3) 0.3023(12) 0.029(7) Uiso 1 d . . . C4 C 0.0833(3) 0.5549(3) 0.09283(14) 0.0369(7) Uani 1 d . . . H4 H 0.015(3) 0.618(3) 0.0950(13) 0.049(9) Uiso 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 Pd1 0.01091(13) 0.01142(13) 0.01088(13) -0.00152(9) 0.00083(9) -0.00028(9) P2 0.0136(3) 0.0136(3) 0.0131(3) -0.0004(2) 0.0006(2) -0.0010(2) S1 0.0160(3) 0.0231(3) 0.0153(3) -0.0013(2) 0.0034(2) -0.0048(2) P1 0.0162(3) 0.0138(3) 0.0143(3) -0.0012(2) 0.0029(2) -0.0006(2) O2 0.0137(8) 0.0159(8) 0.0182(8) 0.0016(7) 0.0006(6) 0.0006(6) O1 0.0206(8) 0.0175(8) 0.0196(8) 0.0025(7) 0.0058(7) 0.0054(7) C7 0.0133(11) 0.0152(11) 0.0147(11) 0.0015(9) -0.0016(9) -0.0028(9) C19 0.0154(11) 0.0106(10) 0.0191(12) -0.0027(9) -0.0017(9) -0.0011(9) N1 0.0151(9) 0.0128(9) 0.0131(9) -0.0016(8) 0.0001(7) -0.0014(7) C13 0.0118(10) 0.0167(12) 0.0188(12) 0.0015(10) 0.0040(9) 0.0004(9) C10 0.0237(13) 0.0232(13) 0.0217(13) 0.0085(11) -0.0028(10) -0.0045(10) O3 0.0248(9) 0.0244(9) 0.0194(8) -0.0072(7) 0.0052(7) -0.0047(7) C22 0.0251(13) 0.0156(12) 0.0306(14) -0.0013(11) -0.0088(11) 0.0026(10) C14 0.0159(12) 0.0203(13) 0.0223(12) -0.0001(11) 0.0029(10) -0.0006(10) C16 0.0270(13) 0.0143(13) 0.0334(15) -0.0034(11) 0.0106(11) -0.0041(10) C1 0.0208(12) 0.0190(12) 0.0225(12) 0.0068(10) 0.0106(10) 0.0047(10) C11 0.0228(13) 0.0208(13) 0.0312(14) 0.0049(11) 0.0014(11) 0.0049(11) C8 0.0204(12) 0.0235(13) 0.0247(13) -0.0005(11) 0.0062(10) 0.0026(10) C3 0.0183(14) 0.056(2) 0.0372(16) 0.0093(15) 0.0066(12) 0.0000(14) C18 0.0225(12) 0.0192(12) 0.0206(13) 0.0010(11) -0.0017(10) -0.0020(10) C17 0.0298(14) 0.0187(13) 0.0294(14) 0.0095(12) 0.0044(12) 0.0043(11) C12 0.0216(12) 0.0229(13) 0.0180(12) 0.0000(11) 0.0054(10) 0.0000(10) C20 0.0196(12) 0.0187(12) 0.0235(13) -0.0047(11) 0.0013(10) -0.0008(10) C23 0.0273(13) 0.0194(13) 0.0192(13) 0.0047(11) -0.0047(11) -0.0040(10) C2 0.0260(14) 0.0288(15) 0.0311(15) 0.0011(13) 0.0066(11) -0.0050(12) C15 0.0209(12) 0.0256(14) 0.0248(13) -0.0061(11) 0.0018(11) -0.0050(10) C24 0.0194(12) 0.0176(12) 0.0194(12) -0.0023(10) -0.0007(10) -0.0002(10) C5 0.0323(15) 0.0209(14) 0.058(2) 0.0034(14) 0.0210(14) 0.0056(12) C21 0.0194(13) 0.0202(13) 0.0392(16) -0.0065(12) -0.0026(12) 0.0050(11) C6 0.0229(13) 0.0175(13) 0.0389(16) 0.0008(12) 0.0122(12) 0.0005(11) C9 0.0329(14) 0.0336(15) 0.0155(12) 0.0026(11) 0.0080(11) -0.0015(12) C4 0.0314(16) 0.0298(15) 0.0527(19) 0.0080(15) 0.0166(14) 0.0106(13) _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 Pd1 N1 2.0699(17) . ? Pd1 N1 2.0699(17) 3_655 ? Pd1 S1 2.3641(7) . ? Pd1 S1 2.3641(7) 3_655 ? Pd1 P2 2.8378(9) . ? Pd1 P2 2.8378(9) 3_655 ? P2 N1 1.6431(18) . ? P2 C19 1.802(2) . ? P2 C13 1.806(2) . ? P2 S1 2.0246(9) . ? P1 O3 1.4659(16) . ? P1 O1 1.5858(16) . ? P1 O2 1.5922(16) . ? P1 N1 1.6245(18) . ? O2 C7 1.414(3) . ? O1 C1 1.408(3) . ? C7 C12 1.381(3) . ? C7 C8 1.383(3) . ? C19 C24 1.399(3) . ? C19 C20 1.405(3) . ? C13 C14 1.396(3) . ? C13 C18 1.400(3) . ? C10 C11 1.376(4) . ? C10 C9 1.376(4) . ? C22 C21 1.385(4) . ? C22 C23 1.387(4) . ? C14 C15 1.385(3) . ? C16 C17 1.383(4) . ? C16 C15 1.386(4) . ? C1 C6 1.378(3) . ? C1 C2 1.381(3) . ? C11 C12 1.388(3) . ? C8 C9 1.392(3) . ? C3 C4 1.385(4) . ? C3 C2 1.388(4) . ? C18 C17 1.386(4) . ? C20 C21 1.388(3) . ? C23 C24 1.391(3) . ? C5 C4 1.372(4) . ? C5 C6 1.388(4) . ? 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 N1 Pd1 N1 180.0 . 3_655 ? N1 Pd1 S1 79.34(6) . . ? N1 Pd1 S1 100.66(6) 3_655 . ? N1 Pd1 S1 100.66(6) . 3_655 ? N1 Pd1 S1 79.34(6) 3_655 3_655 ? S1 Pd1 S1 180.0 . 3_655 ? N1 Pd1 P2 34.88(5) . . ? N1 Pd1 P2 145.12(5) 3_655 . ? S1 Pd1 P2 44.67(2) . . ? S1 Pd1 P2 135.33(2) 3_655 . ? N1 Pd1 P2 145.12(5) . 3_655 ? N1 Pd1 P2 34.88(5) 3_655 3_655 ? S1 Pd1 P2 135.33(2) . 3_655 ? S1 Pd1 P2 44.67(2) 3_655 3_655 ? P2 Pd1 P2 180.0 . 3_655 ? N1 P2 C19 109.39(10) . . ? N1 P2 C13 113.04(9) . . ? C19 P2 C13 108.18(10) . . ? N1 P2 S1 100.95(7) . . ? C19 P2 S1 111.76(8) . . ? C13 P2 S1 113.40(8) . . ? N1 P2 Pd1 46.08(6) . . ? C19 P2 Pd1 118.70(7) . . ? C13 P2 Pd1 132.67(7) . . ? S1 P2 Pd1 55.17(3) . . ? P2 S1 Pd1 80.17(4) . . ? O3 P1 O1 116.53(9) . . ? O3 P1 O2 113.76(9) . . ? O1 P1 O2 100.04(8) . . ? O3 P1 N1 115.77(9) . . ? O1 P1 N1 102.63(9) . . ? O2 P1 N1 106.29(9) . . ? C7 O2 P1 118.85(13) . . ? C1 O1 P1 124.03(14) . . ? C12 C7 C8 121.4(2) . . ? C12 C7 O2 119.7(2) . . ? C8 C7 O2 118.9(2) . . ? C24 C19 C20 120.0(2) . . ? C24 C19 P2 120.38(17) . . ? C20 C19 P2 119.58(18) . . ? P1 N1 P2 125.99(11) . . ? P1 N1 Pd1 125.05(10) . . ? P2 N1 Pd1 99.04(9) . . ? C14 C13 C18 119.7(2) . . ? C14 C13 P2 121.75(17) . . ? C18 C13 P2 118.49(17) . . ? C11 C10 C9 120.4(2) . . ? C21 C22 C23 120.0(2) . . ? C15 C14 C13 120.0(2) . . ? C17 C16 C15 120.2(2) . . ? C6 C1 C2 122.2(2) . . ? C6 C1 O1 119.6(2) . . ? C2 C1 O1 118.0(2) . . ? C10 C11 C12 120.4(2) . . ? C7 C8 C9 118.9(2) . . ? C4 C3 C2 120.6(3) . . ? C17 C18 C13 119.6(2) . . ? C16 C17 C18 120.4(2) . . ? C7 C12 C11 118.8(2) . . ? C21 C20 C19 119.2(2) . . ? C22 C23 C24 120.3(2) . . ? C1 C2 C3 118.1(3) . . ? C14 C15 C16 120.1(2) . . ? C23 C24 C19 119.6(2) . . ? C4 C5 C6 120.3(3) . . ? C22 C21 C20 120.8(3) . . ? C1 C6 C5 118.7(2) . . ? C10 C9 C8 120.1(2) . . ? C5 C4 C3 120.1(3) . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.649 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.062 data_12.cif #data_man70 _database_code_CSD 153022 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety '[iPr2P(S)-N-P(O)(OPh)2]2Pd' _chemical_formula_sum 'C36 H48 N2 O6 P4 Pd S2' _chemical_formula_weight 899.16 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' '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' 'Pd' 'Pd' -0.9988 1.0072 '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 11.605(2) _cell_length_b 12.181(2) _cell_length_c 15.930(3) _cell_angle_alpha 110.77(3) _cell_angle_beta 91.19(3) _cell_angle_gamma 106.59(3) _cell_volume 1999.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.775 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7026 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.1221 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6705 _reflns_number_gt 3988 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^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 6705 _refine_ls_number_parameters 463 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1212 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max 0.007 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.5000 0.5000 0.5000 0.01501(15) Uani 1 d S . . P2 P 0.21776(12) 0.32172(12) 0.46173(9) 0.0182(3) Uani 1 d . . . S1 S 0.52613(11) 0.30793(11) 0.41628(9) 0.0212(3) Uani 1 d . . . P1 P 0.31249(11) 0.57857(12) 0.59026(8) 0.0167(3) Uani 1 d . . . O1 O 0.0951(3) 0.3157(3) 0.4831(2) 0.0244(8) Uani 1 d . . . O2 O 0.2596(3) 0.2095(3) 0.4645(2) 0.0196(8) Uani 1 d . . . N1 N 0.3233(4) 0.4467(4) 0.5216(3) 0.0167(9) Uani 1 d . . . O3 O 0.2379(3) 0.3089(3) 0.3611(2) 0.0219(8) Uani 1 d . . . C7 C 0.1867(4) 0.2043(4) 0.2833(3) 0.0174(11) Uani 1 d . . . C2 C 0.3662(5) 0.1978(5) 0.5890(4) 0.0296(13) Uani 1 d . . . C17 C 0.1809(6) 0.6115(6) 0.4607(4) 0.0336(14) Uani 1 d . . . C1 C 0.2579(5) 0.1820(5) 0.5431(3) 0.0205(11) Uani 1 d . . . C13 C 0.3029(5) 0.5808(5) 0.7044(3) 0.0227(12) Uani 1 d . . . C11 C 0.2069(5) 0.0891(5) 0.1312(4) 0.0281(13) Uani 1 d . . . C12 C 0.2570(5) 0.1882(5) 0.2138(3) 0.0235(12) Uani 1 d . . . C8 C 0.0726(5) 0.1238(5) 0.2743(4) 0.0274(13) Uani 1 d . . . C16 C 0.1851(5) 0.6191(5) 0.5574(3) 0.0210(11) Uani 1 d . . . C14 C 0.4050(5) 0.5422(5) 0.7335(4) 0.0272(12) Uani 1 d . . . C5 C 0.1502(6) 0.1042(6) 0.6446(5) 0.0443(17) Uani 1 d . . . C3 C 0.3646(6) 0.1642(6) 0.6632(4) 0.0354(14) Uani 1 d . . . C10 C 0.0941(5) 0.0094(5) 0.1210(3) 0.0263(13) Uani 1 d . . . C18 C 0.1899(6) 0.7482(6) 0.6238(4) 0.0401(16) Uani 1 d . . . C9 C 0.0271(5) 0.0250(5) 0.1930(4) 0.0313(14) Uani 1 d . . . C6 C 0.1491(5) 0.1336(5) 0.5686(4) 0.0297(13) Uani 1 d . . . C4 C 0.2573(6) 0.1180(6) 0.6913(4) 0.0423(16) Uani 1 d . . . C15 C 0.1798(5) 0.5010(6) 0.7138(4) 0.0388(16) Uani 1 d . . . Pd2 Pd 0.0000 0.5000 0.0000 0.01377(14) Uani 1 d S . . P4 P 0.20142(11) 0.44496(12) 0.05606(8) 0.0151(3) Uani 1 d . . . S2 S 0.04629(11) 0.31825(11) -0.01816(9) 0.0188(3) Uani 1 d . . . P3 P 0.27558(11) 0.69742(12) 0.05903(9) 0.0162(3) Uani 1 d . . . O6 O 0.2467(3) 0.6964(3) -0.0391(2) 0.0204(8) Uani 1 d . . . O5 O 0.2288(3) 0.8084(3) 0.1170(2) 0.0200(8) Uani 1 d . . . N2 N 0.1784(3) 0.5713(4) 0.0563(3) 0.0158(9) Uani 1 d . . . C34 C 0.3316(4) 0.4132(5) 0.0035(3) 0.0183(11) Uani 1 d . . . C24 C 0.1331(5) 0.7847(5) 0.2451(4) 0.0237(12) Uani 1 d . . . C19 C 0.2339(5) 0.8381(5) 0.2115(3) 0.0196(11) Uani 1 d . . . C26 C 0.4173(5) 0.8268(5) -0.0787(4) 0.0241(12) Uani 1 d . . . C25 C 0.2974(5) 0.7952(4) -0.0671(3) 0.0171(11) Uani 1 d . . . C29 C 0.2648(5) 0.9427(6) -0.1206(4) 0.0301(13) Uani 1 d . . . C36 C 0.3252(5) 0.4133(6) -0.0907(4) 0.0321(14) Uani 1 d . . . C28 C 0.3855(5) 0.9780(5) -0.1323(4) 0.0312(13) Uani 1 d . . . C21 C 0.3406(6) 0.9504(6) 0.3602(4) 0.0380(15) Uani 1 d . . . C23 C 0.1386(5) 0.8140(5) 0.3367(4) 0.0300(13) Uani 1 d . . . C31 C 0.2175(5) 0.4454(5) 0.1691(3) 0.0229(12) Uani 1 d . . . C35 C 0.3421(6) 0.2924(6) 0.0040(4) 0.0369(15) Uani 1 d . . . C22 C 0.2406(6) 0.8949(5) 0.3946(4) 0.0305(13) Uani 1 d . . . C33 C 0.1000(5) 0.4502(5) 0.2123(4) 0.0260(12) Uani 1 d . . . C32 C 0.3268(5) 0.5491(6) 0.2300(4) 0.0312(14) Uani 1 d . . . C30 C 0.2205(5) 0.8498(5) -0.0879(4) 0.0266(12) Uani 1 d . . . C27 C 0.4612(5) 0.9192(5) -0.1120(4) 0.0291(13) Uani 1 d . . . C20 C 0.3375(5) 0.9209(5) 0.2682(4) 0.0315(14) Uani 1 d . . . O4 O 0.4014(3) 0.7142(3) 0.0870(2) 0.0204(8) Uani 1 d . . . H15B H 0.1594 0.4239 0.6847 0.050 Uiso 1 d . . . H35C H 0.2773 0.2376 -0.0163 0.050 Uiso 1 d . . . H9 H -0.0570 -0.0420 0.1857 0.050 Uiso 1 d . . . H35B H 0.3605 0.3053 0.0554 0.050 Uiso 1 d . . . H26 H 0.4678 0.7785 -0.0571 0.050 Uiso 1 d . . . H15A H 0.1417 0.5355 0.7154 0.050 Uiso 1 d . . . H17B H 0.1824 0.5335 0.4182 0.050 Uiso 1 d . . . H34 H 0.3918 0.4800 0.0307 0.050 Uiso 1 d . . . H36B H 0.2540 0.3529 -0.1254 0.050 Uiso 1 d . . . H36A H 0.3252 0.4759 -0.0949 0.050 Uiso 1 d . . . H31 H 0.1984 0.3700 0.1593 0.050 Uiso 1 d . . . H17A H 0.2411 0.6656 0.4619 0.050 Uiso 1 d . . . H24 H 0.0712 0.7403 0.2025 0.050 Uiso 1 d . . . H6 H 0.0936 0.1359 0.5414 0.050 Uiso 1 d . . . H27 H 0.5542 0.9598 -0.1154 0.050 Uiso 1 d . . . H35A H 0.4129 0.2680 -0.0352 0.050 Uiso 1 d . . . H18A H 0.2369 0.7979 0.6208 0.050 Uiso 1 d . . . H33C H 0.0257 0.3832 0.1755 0.050 Uiso 1 d . . . H33B H 0.1005 0.5411 0.2288 0.050 Uiso 1 d . . . H8 H 0.0255 0.1285 0.3253 0.050 Uiso 1 d . . . H32B H 0.3392 0.5411 0.2965 0.050 Uiso 1 d . . . H12 H 0.3327 0.2552 0.2324 0.050 Uiso 1 d . . . H28 H 0.4271 1.0405 -0.1531 0.050 Uiso 1 d . . . H32A H 0.3078 0.6369 0.2486 0.050 Uiso 1 d . . . H33A H 0.1068 0.4391 0.2733 0.050 Uiso 1 d . . . H3 H 0.4373 0.1873 0.7002 0.050 Uiso 1 d . . . H15C H 0.1832 0.4950 0.7745 0.050 Uiso 1 d . . . H36C H 0.3838 0.3827 -0.1244 0.050 Uiso 1 d . . . H22 H 0.2429 0.9045 0.4686 0.050 Uiso 1 d . . . H21 H 0.4206 1.0162 0.4025 0.050 Uiso 1 d . . . H30 H 0.1343 0.8332 -0.0811 0.050 Uiso 1 d . . . H4 H 0.2680 0.1133 0.7543 0.050 Uiso 1 d . . . H20 H 0.3816 0.9653 0.2441 0.050 Uiso 1 d . . . H10 H 0.0664 -0.0758 0.0531 0.050 Uiso 1 d . . . H23 H 0.0457 0.7625 0.3530 0.050 Uiso 1 d . . . H2 H 0.4362 0.2337 0.5608 0.050 Uiso 1 d . . . H18C H 0.1216 0.7866 0.5900 0.050 Uiso 1 d . . . H17C H 0.1120 0.6401 0.4438 0.050 Uiso 1 d . . . H29 H 0.1867 0.9585 -0.1503 0.050 Uiso 1 d . . . H13 H 0.3026 0.6582 0.7350 0.050 Uiso 1 d . . . H14C H 0.4803 0.5907 0.7317 0.050 Uiso 1 d . . . H14B H 0.4186 0.5615 0.7965 0.050 Uiso 1 d . . . H14A H 0.3983 0.4565 0.7082 0.050 Uiso 1 d . . . H16 H 0.1110 0.5584 0.5598 0.050 Uiso 1 d . . . H5 H 0.0787 0.0810 0.6706 0.050 Uiso 1 d . . . H32C H 0.3935 0.5632 0.1989 0.050 Uiso 1 d . . . H18B H 0.2429 0.7965 0.7024 0.050 Uiso 1 d . . . H11 H 0.2597 0.0846 0.0843 0.050 Uiso 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 Pd1 0.0148(3) 0.0158(3) 0.0134(3) 0.0036(2) 0.0068(2) 0.0052(2) P2 0.0174(7) 0.0187(7) 0.0166(7) 0.0051(5) 0.0050(5) 0.0045(6) S1 0.0197(7) 0.0176(7) 0.0241(7) 0.0046(5) 0.0109(5) 0.0062(5) P1 0.0173(7) 0.0186(7) 0.0130(7) 0.0039(5) 0.0054(5) 0.0064(5) O1 0.0141(18) 0.024(2) 0.032(2) 0.0082(16) 0.0082(15) 0.0040(15) O2 0.0203(19) 0.0189(19) 0.0208(19) 0.0091(15) 0.0097(15) 0.0054(15) N1 0.018(2) 0.016(2) 0.015(2) 0.0030(17) 0.0073(17) 0.0076(18) O3 0.028(2) 0.021(2) 0.0145(19) 0.0047(15) 0.0067(15) 0.0049(16) C7 0.021(3) 0.017(3) 0.012(2) 0.0016(19) 0.000(2) 0.007(2) C2 0.031(3) 0.026(3) 0.031(3) 0.010(2) 0.007(2) 0.008(3) C17 0.042(4) 0.038(4) 0.029(3) 0.015(3) 0.000(3) 0.022(3) C1 0.027(3) 0.015(3) 0.021(3) 0.007(2) 0.008(2) 0.008(2) C13 0.024(3) 0.026(3) 0.016(3) 0.005(2) 0.006(2) 0.007(2) C11 0.038(3) 0.026(3) 0.020(3) 0.009(2) 0.008(2) 0.009(3) C12 0.027(3) 0.021(3) 0.021(3) 0.009(2) 0.003(2) 0.004(2) C8 0.025(3) 0.026(3) 0.027(3) 0.004(2) 0.007(2) 0.009(2) C16 0.018(3) 0.027(3) 0.018(3) 0.006(2) 0.002(2) 0.011(2) C14 0.025(3) 0.036(3) 0.025(3) 0.017(2) 0.002(2) 0.008(2) C5 0.049(4) 0.046(4) 0.053(4) 0.034(3) 0.030(3) 0.017(3) C3 0.042(4) 0.037(4) 0.031(3) 0.015(3) -0.004(3) 0.014(3) C10 0.039(3) 0.018(3) 0.014(3) 0.001(2) 0.001(2) 0.004(2) C18 0.043(4) 0.033(4) 0.042(4) -0.002(3) -0.005(3) 0.030(3) C9 0.023(3) 0.029(3) 0.036(4) 0.008(3) 0.002(2) 0.003(2) C6 0.032(3) 0.028(3) 0.037(3) 0.018(3) 0.013(3) 0.012(3) C4 0.052(4) 0.051(4) 0.036(4) 0.027(3) 0.013(3) 0.019(3) C15 0.032(3) 0.057(4) 0.025(3) 0.017(3) 0.015(3) 0.007(3) Pd2 0.0127(3) 0.0135(3) 0.0160(3) 0.0061(2) 0.0028(2) 0.0046(2) P4 0.0133(6) 0.0178(7) 0.0167(7) 0.0079(5) 0.0049(5) 0.0066(5) S2 0.0169(6) 0.0145(6) 0.0244(7) 0.0065(5) 0.0021(5) 0.0052(5) P3 0.0155(7) 0.0153(7) 0.0157(7) 0.0050(5) 0.0029(5) 0.0030(5) O6 0.024(2) 0.0180(19) 0.0178(19) 0.0084(15) 0.0044(15) 0.0024(15) O5 0.026(2) 0.0183(19) 0.0152(18) 0.0043(14) 0.0041(15) 0.0082(15) N2 0.014(2) 0.015(2) 0.018(2) 0.0060(17) 0.0040(17) 0.0051(17) C34 0.016(3) 0.021(3) 0.020(3) 0.010(2) 0.005(2) 0.007(2) C24 0.018(3) 0.024(3) 0.030(3) 0.012(2) 0.005(2) 0.007(2) C19 0.029(3) 0.015(3) 0.017(3) 0.006(2) 0.005(2) 0.010(2) C26 0.028(3) 0.025(3) 0.023(3) 0.009(2) 0.004(2) 0.014(2) C25 0.026(3) 0.012(3) 0.014(3) 0.0049(19) 0.005(2) 0.006(2) C29 0.032(3) 0.036(4) 0.030(3) 0.017(3) 0.008(2) 0.017(3) C36 0.034(3) 0.040(4) 0.026(3) 0.014(3) 0.013(3) 0.016(3) C28 0.042(4) 0.020(3) 0.030(3) 0.011(2) 0.007(3) 0.004(3) C21 0.041(4) 0.029(3) 0.029(3) 0.002(3) -0.008(3) 0.001(3) C23 0.035(3) 0.032(3) 0.030(3) 0.014(3) 0.014(3) 0.017(3) C31 0.025(3) 0.028(3) 0.017(3) 0.008(2) 0.008(2) 0.011(2) C35 0.041(4) 0.045(4) 0.042(4) 0.023(3) 0.019(3) 0.031(3) C22 0.052(4) 0.026(3) 0.022(3) 0.012(2) 0.015(3) 0.020(3) C33 0.028(3) 0.033(3) 0.018(3) 0.011(2) 0.008(2) 0.009(2) C32 0.023(3) 0.052(4) 0.019(3) 0.014(3) 0.004(2) 0.012(3) C30 0.031(3) 0.029(3) 0.022(3) 0.009(2) 0.011(2) 0.013(3) C27 0.025(3) 0.029(3) 0.028(3) 0.008(2) 0.009(2) 0.004(2) C20 0.035(3) 0.025(3) 0.025(3) 0.005(2) 0.006(3) -0.001(3) O4 0.0128(17) 0.022(2) 0.023(2) 0.0073(15) 0.0036(14) 0.0014(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 Pd1 N1 2.042(4) 2_666 ? Pd1 N1 2.042(4) . ? Pd1 S1 2.3565(14) 2_666 ? Pd1 S1 2.3565(14) . ? Pd1 P1 2.8393(14) 2_666 ? Pd1 P1 2.8393(14) . ? P2 O1 1.458(4) . ? P2 O3 1.583(3) . ? P2 O2 1.590(4) . ? P2 N1 1.608(4) . ? S1 P1 2.0153(19) 2_666 ? P1 N1 1.633(4) . ? P1 C16 1.809(5) . ? P1 C13 1.815(5) . ? P1 S1 2.0153(19) 2_666 ? O2 C1 1.406(6) . ? O3 C7 1.390(6) . ? C7 C8 1.373(7) . ? C7 C12 1.380(7) . ? C2 C1 1.369(8) . ? C2 C3 1.380(8) . ? C17 C16 1.509(8) . ? C1 C6 1.368(7) . ? C13 C14 1.513(7) . ? C13 C15 1.525(7) . ? C11 C10 1.355(8) . ? C11 C12 1.402(7) . ? C8 C9 1.381(8) . ? C16 C18 1.537(7) . ? C5 C4 1.371(10) . ? C5 C6 1.380(8) . ? C3 C4 1.367(9) . ? C10 C9 1.387(7) . ? Pd2 N2 2.047(4) 2_565 ? Pd2 N2 2.047(4) . ? Pd2 S2 2.3463(13) 2_565 ? Pd2 S2 2.3463(13) . ? Pd2 P4 2.8184(14) 2_565 ? Pd2 P4 2.8184(14) . ? P4 N2 1.633(4) . ? P4 C31 1.805(5) . ? P4 C34 1.813(5) . ? P4 S2 2.013(2) . ? P3 O4 1.453(4) . ? P3 O6 1.587(4) . ? P3 O5 1.590(3) . ? P3 N2 1.611(4) . ? O6 C25 1.408(6) . ? O5 C19 1.414(6) . ? C34 C36 1.501(8) . ? C34 C35 1.514(8) . ? C24 C23 1.369(8) . ? C24 C19 1.384(7) . ? C19 C20 1.376(8) . ? C26 C25 1.368(7) . ? C26 C27 1.384(8) . ? C25 C30 1.354(7) . ? C29 C28 1.381(8) . ? C29 C30 1.383(8) . ? C28 C27 1.379(8) . ? C21 C20 1.376(8) . ? C21 C22 1.394(8) . ? C23 C22 1.366(8) . ? C31 C32 1.520(8) . ? C31 C33 1.547(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Pd1 N1 180.0 2_666 . ? N1 Pd1 S1 101.46(12) 2_666 2_666 ? N1 Pd1 S1 78.54(12) . 2_666 ? N1 Pd1 S1 78.54(12) 2_666 . ? N1 Pd1 S1 101.46(12) . . ? S1 Pd1 S1 180.0 2_666 . ? N1 Pd1 P1 34.43(11) 2_666 2_666 ? N1 Pd1 P1 145.57(11) . 2_666 ? S1 Pd1 P1 135.56(5) 2_666 2_666 ? S1 Pd1 P1 44.44(5) . 2_666 ? N1 Pd1 P1 145.57(11) 2_666 . ? N1 Pd1 P1 34.43(11) . . ? S1 Pd1 P1 44.44(5) 2_666 . ? S1 Pd1 P1 135.56(5) . . ? P1 Pd1 P1 180.0 2_666 . ? O1 P2 O3 115.6(2) . . ? O1 P2 O2 114.4(2) . . ? O3 P2 O2 98.92(19) . . ? O1 P2 N1 115.9(2) . . ? O3 P2 N1 103.0(2) . . ? O2 P2 N1 107.0(2) . . ? P1 S1 Pd1 80.59(6) 2_666 . ? N1 P1 C16 114.8(2) . . ? N1 P1 C13 110.9(2) . . ? C16 P1 C13 107.8(2) . . ? N1 P1 S1 99.49(16) . 2_666 ? C16 P1 S1 112.93(19) . 2_666 ? C13 P1 S1 110.70(19) . 2_666 ? N1 P1 Pd1 45.00(14) . . ? C16 P1 Pd1 134.41(17) . . ? C13 P1 Pd1 117.56(18) . . ? S1 P1 Pd1 54.96(5) 2_666 . ? C1 O2 P2 120.7(3) . . ? P2 N1 P1 129.5(3) . . ? P2 N1 Pd1 127.3(2) . . ? P1 N1 Pd1 100.6(2) . . ? C7 O3 P2 126.2(3) . . ? C8 C7 C12 121.8(5) . . ? C8 C7 O3 122.8(4) . . ? C12 C7 O3 115.4(4) . . ? C1 C2 C3 118.6(5) . . ? C6 C1 C2 121.9(5) . . ? C6 C1 O2 119.6(5) . . ? C2 C1 O2 118.4(5) . . ? C14 C13 C15 111.2(5) . . ? C14 C13 P1 109.8(4) . . ? C15 C13 P1 112.7(4) . . ? C10 C11 C12 120.9(5) . . ? C7 C12 C11 118.0(5) . . ? C7 C8 C9 118.8(5) . . ? C17 C16 C18 111.7(5) . . ? C17 C16 P1 111.6(4) . . ? C18 C16 P1 109.7(4) . . ? C4 C5 C6 120.9(6) . . ? C4 C3 C2 120.8(6) . . ? C11 C10 C9 119.9(5) . . ? C8 C9 C10 120.6(5) . . ? C1 C6 C5 118.3(6) . . ? C3 C4 C5 119.4(6) . . ? N2 Pd2 N2 180.0 2_565 . ? N2 Pd2 S2 79.16(12) 2_565 2_565 ? N2 Pd2 S2 100.84(12) . 2_565 ? N2 Pd2 S2 100.84(12) 2_565 . ? N2 Pd2 S2 79.16(12) . . ? S2 Pd2 S2 180.0 2_565 . ? N2 Pd2 P4 34.88(11) 2_565 2_565 ? N2 Pd2 P4 145.12(11) . 2_565 ? S2 Pd2 P4 44.73(5) 2_565 2_565 ? S2 Pd2 P4 135.27(5) . 2_565 ? N2 Pd2 P4 145.12(11) 2_565 . ? N2 Pd2 P4 34.88(11) . . ? S2 Pd2 P4 135.27(5) 2_565 . ? S2 Pd2 P4 44.73(5) . . ? P4 Pd2 P4 180.0 2_565 . ? N2 P4 C31 111.7(2) . . ? N2 P4 C34 114.8(2) . . ? C31 P4 C34 108.0(2) . . ? N2 P4 S2 100.25(15) . . ? C31 P4 S2 111.46(18) . . ? C34 P4 S2 110.52(17) . . ? N2 P4 Pd2 45.78(14) . . ? C31 P4 Pd2 118.29(17) . . ? C34 P4 Pd2 133.62(17) . . ? S2 P4 Pd2 55.11(5) . . ? P4 S2 Pd2 80.16(6) . . ? O4 P3 O6 115.6(2) . . ? O4 P3 O5 114.0(2) . . ? O6 P3 O5 99.32(19) . . ? O4 P3 N2 115.7(2) . . ? O6 P3 N2 103.0(2) . . ? O5 P3 N2 107.3(2) . . ? C25 O6 P3 125.1(3) . . ? C19 O5 P3 118.0(3) . . ? P3 N2 P4 129.1(2) . . ? P3 N2 Pd2 127.2(2) . . ? P4 N2 Pd2 99.35(19) . . ? C36 C34 C35 111.5(5) . . ? C36 C34 P4 111.0(4) . . ? C35 C34 P4 110.5(4) . . ? C23 C24 C19 118.6(5) . . ? C20 C19 C24 121.5(5) . . ? C20 C19 O5 119.6(5) . . ? C24 C19 O5 118.9(5) . . ? C25 C26 C27 118.3(5) . . ? C30 C25 C26 122.6(5) . . ? C30 C25 O6 116.8(5) . . ? C26 C25 O6 120.4(4) . . ? C28 C29 C30 120.2(5) . . ? C27 C28 C29 119.5(5) . . ? C20 C21 C22 120.0(5) . . ? C22 C23 C24 121.3(5) . . ? C32 C31 C33 110.8(4) . . ? C32 C31 P4 112.8(4) . . ? C33 C31 P4 110.8(4) . . ? C23 C22 C21 119.6(5) . . ? C25 C30 C29 118.9(5) . . ? C28 C27 C26 120.5(5) . . ? C21 C20 C19 119.0(5) . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.751 _refine_diff_density_min -1.226 _refine_diff_density_rms 0.118 data_13.cif #data_man67 _database_code_CSD 153023 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety '[Ph2P(S)-N-P(S)(OPh)2]2Pd' _chemical_formula_sum 'C24 H20 N O2 P2 Pd0.50 S2' _chemical_formula_weight 533.67 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' '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' 'Pd' 'Pd' -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.698(2) _cell_length_b 10.890(2) _cell_length_c 11.220(2) _cell_angle_alpha 108.78(3) _cell_angle_beta 105.07(3) _cell_angle_gamma 95.40(3) _cell_volume 1172.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.757 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6193 _exptl_absorpt_correction_T_max 0.9631 _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4349 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4110 _reflns_number_gt 3361 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+3.6876P] 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 4110 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.0000 0.0000 0.0000 0.01851(15) Uani 1 d S . . S1 S -0.14514(11) -0.20372(10) -0.10290(11) 0.0244(3) Uani 1 d . . . S2 S 0.18116(11) -0.10531(11) 0.02573(11) 0.0247(3) Uani 1 d . . . P1 P -0.10049(11) -0.27891(11) -0.27151(11) 0.0224(3) Uani 1 d . . . P2 P 0.18096(11) -0.18099(11) -0.16285(11) 0.0210(3) Uani 1 d . . . O2 O -0.1706(3) -0.4314(3) -0.3363(3) 0.0261(7) Uani 1 d . . . O1 O -0.1743(3) -0.2262(3) -0.3817(3) 0.0263(7) Uani 1 d . . . C13 C 0.2962(4) -0.2910(4) -0.1644(4) 0.0232(9) Uani 1 d . . . C2 C -0.3983(5) -0.3439(5) -0.5025(5) 0.0303(10) Uani 1 d . . . C7 C -0.1084(4) -0.5281(4) -0.2996(5) 0.0270(10) Uani 1 d . . . C1 C -0.3114(4) -0.2284(5) -0.4158(4) 0.0271(10) Uani 1 d . . . N1 N 0.0452(4) -0.2650(4) -0.2719(4) 0.0261(8) Uani 1 d . . . C3 C -0.5312(5) -0.3416(5) -0.5444(5) 0.0326(11) Uani 1 d . . . C6 C -0.3530(5) -0.1122(5) -0.3699(5) 0.0321(11) Uani 1 d . . . C4 C -0.5752(5) -0.2258(5) -0.5016(5) 0.0372(12) Uani 1 d . . . C16 C 0.4652(5) -0.4677(5) -0.1599(5) 0.0343(11) Uani 1 d . . . C5 C -0.4884(6) -0.1123(5) -0.4151(5) 0.0409(13) Uani 1 d . . . C18 C 0.2641(5) -0.4025(4) -0.1337(5) 0.0287(10) Uani 1 d . . . C15 C 0.4964(5) -0.3589(5) -0.1915(5) 0.0330(11) Uani 1 d . . . C17 C 0.3492(5) -0.4906(5) -0.1324(5) 0.0337(11) Uani 1 d . . . C14 C 0.4123(4) -0.2705(4) -0.1940(4) 0.0254(9) Uani 1 d . . . C19 C 0.2399(4) -0.0502(4) -0.2121(4) 0.0251(9) Uani 1 d . . . C20 C 0.1805(5) -0.0516(5) -0.3384(5) 0.0295(10) Uani 1 d . . . C24 C 0.3452(5) 0.0518(4) -0.1257(4) 0.0265(10) Uani 1 d . . . C8 C -0.0413(5) -0.5982(5) -0.3803(5) 0.0316(11) Uani 1 d . . . C22 C 0.3291(5) 0.1490(5) -0.2918(5) 0.0336(11) Uani 1 d . . . C9 C 0.0189(6) -0.6948(5) -0.3444(5) 0.0405(12) Uani 1 d . . . C23 C 0.3900(5) 0.1513(5) -0.1651(5) 0.0348(11) Uani 1 d . . . C12 C -0.1201(5) -0.5513(5) -0.1900(5) 0.0341(11) Uani 1 d . . . C21 C 0.2263(5) 0.0499(5) -0.3761(5) 0.0359(11) Uani 1 d . . . C10 C 0.0096(6) -0.7200(5) -0.2350(5) 0.0419(13) Uani 1 d . . . C11 C -0.0594(6) -0.6504(5) -0.1571(5) 0.0427(13) Uani 1 d . . . H6 H -0.2812 -0.0296 -0.3113 0.050 Uiso 1 d . . . H18 H 0.1731 -0.4204 -0.1122 0.050 Uiso 1 d . . . H17 H 0.3208 -0.5741 -0.1168 0.050 Uiso 1 d . . . H24 H 0.3868 0.0617 -0.0295 0.050 Uiso 1 d . . . H22 H 0.3716 0.2180 -0.3148 0.050 Uiso 1 d . . . H12 H -0.1750 -0.5058 -0.1391 0.050 Uiso 1 d . . . H8 H -0.0367 -0.5780 -0.4695 0.050 Uiso 1 d . . . H3 H -0.6044 -0.4294 -0.6020 0.050 Uiso 1 d . . . H5 H -0.5029 -0.0199 -0.3851 0.050 Uiso 1 d . . . H2 H -0.3707 -0.4369 -0.5416 0.050 Uiso 1 d . . . H15 H 0.5863 -0.3403 -0.2052 0.050 Uiso 1 d . . . H23 H 0.4692 0.2289 -0.1037 0.050 Uiso 1 d . . . H14 H 0.4320 -0.1965 -0.2158 0.050 Uiso 1 d . . . H20 H 0.0981 -0.1230 -0.3930 0.050 Uiso 1 d . . . H21 H 0.1763 0.0426 -0.4729 0.050 Uiso 1 d . . . H9 H 0.0806 -0.7392 -0.3984 0.050 Uiso 1 d . . . H4 H -0.6796 -0.2246 -0.5257 0.050 Uiso 1 d . . . H16 H 0.5218 -0.5300 -0.1788 0.050 Uiso 1 d . . . H10 H 0.0545 -0.7949 -0.2161 0.050 Uiso 1 d . . . H11 H -0.0645 -0.6459 -0.0618 0.050 Uiso 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 Pd1 0.0208(3) 0.0160(2) 0.0163(2) 0.00476(17) 0.00456(18) -0.00043(17) S1 0.0234(6) 0.0200(5) 0.0259(6) 0.0078(4) 0.0044(4) -0.0022(4) S2 0.0240(6) 0.0240(5) 0.0248(6) 0.0068(4) 0.0079(4) 0.0044(4) P1 0.0240(6) 0.0177(5) 0.0211(6) 0.0069(4) 0.0010(4) 0.0008(4) P2 0.0198(6) 0.0194(5) 0.0220(6) 0.0074(4) 0.0041(4) 0.0026(4) O2 0.0214(15) 0.0192(15) 0.0302(17) 0.0075(13) -0.0011(13) 0.0004(12) O1 0.0236(16) 0.0290(17) 0.0273(16) 0.0147(14) 0.0036(13) 0.0047(13) C13 0.021(2) 0.020(2) 0.028(2) 0.0078(18) 0.0060(18) 0.0073(17) C2 0.025(2) 0.029(2) 0.030(2) 0.010(2) -0.0006(19) 0.0035(19) C7 0.026(2) 0.018(2) 0.031(2) 0.0101(19) -0.0005(19) 0.0003(18) C1 0.025(2) 0.033(3) 0.025(2) 0.013(2) 0.0038(18) 0.011(2) N1 0.028(2) 0.0233(19) 0.0227(19) 0.0047(15) 0.0069(16) 0.0031(16) C3 0.027(2) 0.036(3) 0.034(3) 0.016(2) 0.003(2) 0.005(2) C6 0.039(3) 0.030(3) 0.024(2) 0.008(2) 0.006(2) 0.012(2) C4 0.028(3) 0.047(3) 0.040(3) 0.022(2) 0.007(2) 0.013(2) C16 0.033(3) 0.032(3) 0.032(3) 0.005(2) 0.004(2) 0.014(2) C5 0.052(3) 0.043(3) 0.041(3) 0.022(3) 0.019(3) 0.031(3) C18 0.029(2) 0.022(2) 0.035(3) 0.010(2) 0.010(2) 0.0057(19) C15 0.024(2) 0.037(3) 0.031(3) 0.006(2) 0.005(2) 0.009(2) C17 0.045(3) 0.020(2) 0.031(3) 0.0069(19) 0.005(2) 0.007(2) C14 0.022(2) 0.027(2) 0.027(2) 0.0089(19) 0.0076(18) 0.0053(18) C19 0.025(2) 0.023(2) 0.027(2) 0.0092(18) 0.0070(19) 0.0067(18) C20 0.030(2) 0.030(2) 0.027(2) 0.011(2) 0.004(2) 0.007(2) C24 0.030(2) 0.020(2) 0.024(2) 0.0064(18) 0.0035(19) 0.0006(18) C8 0.042(3) 0.024(2) 0.026(2) 0.0058(19) 0.010(2) 0.005(2) C22 0.051(3) 0.021(2) 0.040(3) 0.015(2) 0.023(2) 0.017(2) C9 0.051(3) 0.026(3) 0.040(3) 0.008(2) 0.011(2) 0.014(2) C23 0.042(3) 0.020(2) 0.040(3) 0.007(2) 0.014(2) 0.001(2) C12 0.036(3) 0.035(3) 0.031(3) 0.012(2) 0.010(2) 0.004(2) C21 0.040(3) 0.042(3) 0.040(3) 0.026(2) 0.018(2) 0.017(2) C10 0.052(3) 0.026(3) 0.042(3) 0.013(2) 0.003(3) 0.009(2) C11 0.062(4) 0.030(3) 0.037(3) 0.016(2) 0.011(3) 0.007(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 Pd1 S1 2.3315(15) . ? Pd1 S1 2.3315(15) 2 ? Pd1 S2 2.3442(13) 2 ? Pd1 S2 2.3442(13) . ? S1 P1 2.0059(17) . ? S2 P2 2.0077(16) . ? P1 N1 1.553(4) . ? P1 O1 1.586(3) . ? P1 O2 1.598(3) . ? P2 N1 1.596(4) . ? P2 C13 1.797(4) . ? P2 C19 1.803(4) . ? O2 C7 1.411(5) . ? O1 C1 1.412(5) . ? C13 C14 1.383(6) . ? C13 C18 1.402(6) . ? C2 C3 1.383(7) . ? C2 C1 1.384(7) . ? C7 C12 1.366(7) . ? C7 C8 1.384(7) . ? C1 C6 1.368(7) . ? C3 C4 1.371(7) . ? C6 C5 1.405(7) . ? C4 C5 1.369(8) . ? C16 C17 1.374(7) . ? C16 C15 1.378(7) . ? C18 C17 1.384(7) . ? C15 C14 1.379(7) . ? C19 C20 1.388(6) . ? C19 C24 1.395(6) . ? C20 C21 1.396(7) . ? C24 C23 1.386(6) . ? C8 C9 1.395(7) . ? C22 C21 1.359(7) . ? C22 C23 1.392(7) . ? C9 C10 1.366(8) . ? C12 C11 1.409(7) . ? C10 C11 1.378(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 S1 Pd1 S1 180.0 . 2 ? S1 Pd1 S2 89.13(5) . 2 ? S1 Pd1 S2 90.87(5) 2 2 ? S1 Pd1 S2 90.87(5) . . ? S1 Pd1 S2 89.13(5) 2 . ? S2 Pd1 S2 180.0 2 . ? P1 S1 Pd1 101.88(6) . . ? P2 S2 Pd1 100.31(6) . . ? N1 P1 O1 105.32(19) . . ? N1 P1 O2 109.70(19) . . ? O1 P1 O2 100.49(17) . . ? N1 P1 S1 120.92(15) . . ? O1 P1 S1 112.04(14) . . ? O2 P1 S1 106.51(14) . . ? N1 P2 C13 106.6(2) . . ? N1 P2 C19 108.3(2) . . ? C13 P2 C19 108.7(2) . . ? N1 P2 S2 117.63(15) . . ? C13 P2 S2 105.67(15) . . ? C19 P2 S2 109.58(16) . . ? C7 O2 P1 121.0(3) . . ? C1 O1 P1 122.6(3) . . ? C14 C13 C18 119.6(4) . . ? C14 C13 P2 123.4(3) . . ? C18 C13 P2 117.0(3) . . ? C3 C2 C1 118.9(4) . . ? C12 C7 C8 123.1(4) . . ? C12 C7 O2 119.3(4) . . ? C8 C7 O2 117.6(4) . . ? C6 C1 C2 122.0(4) . . ? C6 C1 O1 118.2(4) . . ? C2 C1 O1 119.6(4) . . ? P1 N1 P2 132.9(2) . . ? C4 C3 C2 120.1(5) . . ? C1 C6 C5 117.8(5) . . ? C5 C4 C3 120.4(5) . . ? C17 C16 C15 120.5(4) . . ? C4 C5 C6 120.6(5) . . ? C17 C18 C13 119.8(4) . . ? C16 C15 C14 120.3(4) . . ? C16 C17 C18 119.9(4) . . ? C15 C14 C13 119.9(4) . . ? C20 C19 C24 119.4(4) . . ? C20 C19 P2 119.6(3) . . ? C24 C19 P2 121.0(3) . . ? C19 C20 C21 119.4(4) . . ? C23 C24 C19 120.4(4) . . ? C7 C8 C9 117.3(4) . . ? C21 C22 C23 120.2(4) . . ? C10 C9 C8 121.0(5) . . ? C24 C23 C22 119.5(5) . . ? C7 C12 C11 118.2(5) . . ? C22 C21 C20 121.0(5) . . ? C9 C10 C11 120.7(5) . . ? C10 C11 C12 119.6(5) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.777 _refine_diff_density_min -1.286 _refine_diff_density_rms 0.106 data_14.cif #data_m _database_code_CSD 153024 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety '(PhO)2P(O)-NH-P(S)(OPh)2' _chemical_formula_sum 'C24 H21 N O5 P2 S' _chemical_formula_weight 497.42 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' '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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 10.829(2) _cell_length_b 22.400(4) _cell_length_c 10.007(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.22(3) _cell_angle_gamma 90.00 _cell_volume 2402.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2253 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2253 _reflns_number_gt 1999 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0606P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(9) _refine_ls_number_reflns 2253 _refine_ls_number_parameters 301 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.005 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C15 C 0.5652(5) 0.6896(2) 1.3894(5) 0.0406(12) Uani 1 d . . . H15 H 0.6031 0.7237 1.4294 0.049 Uiso 1 d R . . C14 C 0.4388(4) 0.68122(18) 1.3836(4) 0.0284(9) Uani 1 d . . . H14 H 0.3906 0.7086 1.4231 0.034 Uiso 1 d R . . C16 C 0.6376(4) 0.6480(2) 1.3352(5) 0.0353(10) Uani 1 d . . . H16 H 0.7231 0.6533 1.3389 0.042 Uiso 1 d R . . C13 C 0.3857(3) 0.63099(16) 1.3206(4) 0.0188(8) Uani 1 d . . . C17 C 0.5825(4) 0.5982(2) 1.2725(5) 0.0310(9) Uani 1 d . . . H17 H 0.6306 0.5703 1.2344 0.037 Uiso 1 d R . . O3 O 0.2588(2) 0.62112(11) 1.3275(3) 0.0191(6) Uani 1 d . . . C18 C 0.4548(3) 0.58891(17) 1.2657(4) 0.0207(8) Uani 1 d . . . H18 H 0.4175 0.5543 1.2275 0.025 Uiso 1 d R . . P2 P 0.15232(8) 0.61438(4) 1.20217(8) 0.0143(2) Uani 1 d . . . S1 S 0.17494(8) 0.65919(4) 1.04655(9) 0.0209(2) Uani 1 d . . . O4 O 0.0344(2) 0.62729(11) 1.2747(3) 0.0188(6) Uani 1 d . . . N1 N 0.1335(3) 0.54223(14) 1.1727(3) 0.0158(6) Uani 1 d . . . H0 H 0.142(4) 0.532(2) 1.098(5) 0.019 Uiso 1 d . . . C19 C 0.0219(3) 0.68015(16) 1.3467(4) 0.0197(8) Uani 1 d . . . P1 P 0.10235(8) 0.49053(4) 1.27896(8) 0.0125(2) Uani 1 d . . . C24 C -0.0380(4) 0.72822(19) 1.2781(5) 0.0297(9) Uani 1 d . . . H24 H -0.0648 0.7249 1.1859 0.036 Uiso 1 d R . . C20 C 0.0623(4) 0.6822(2) 1.4822(4) 0.0298(9) Uani 1 d . . . H20 H 0.1049 0.6502 1.5266 0.036 Uiso 1 d R . . O1 O 0.1735(2) 0.43343(11) 1.2390(2) 0.0154(5) Uani 1 d . . . O5 O 0.1287(2) 0.50838(11) 1.4203(3) 0.0178(5) Uani 1 d . . . O2 O -0.0367(2) 0.47219(11) 1.2277(2) 0.0178(5) Uani 1 d . . . C23 C -0.0567(4) 0.77837(19) 1.3521(6) 0.0381(11) Uani 1 d . . . H23 H -0.0954 0.8108 1.3055 0.046 Uiso 1 d R . . C21 C 0.0417(4) 0.7326(2) 1.5534(5) 0.0359(10) Uani 1 d . . . H21 H 0.0667 0.7352 1.6461 0.043 Uiso 1 d R . . C1 C 0.3057(3) 0.43527(15) 1.2501(4) 0.0142(7) Uani 1 d . . . C7 C -0.0946(3) 0.42618(17) 1.2926(4) 0.0207(8) Uani 1 d . . . C22 C -0.0176(4) 0.78074(19) 1.4876(5) 0.0370(11) Uani 1 d . . . H22 H -0.0346 0.8153 1.5331 0.044 Uiso 1 d R . . C2 C 0.3553(4) 0.43239(16) 1.1317(4) 0.0191(8) Uani 1 d . . . H2 H 0.3028 0.4290 1.0500 0.023 Uiso 1 d R . . C6 C 0.3768(3) 0.43883(16) 1.3744(4) 0.0184(8) Uani 1 d . . . H6 H 0.3405 0.4408 1.4531 0.022 Uiso 1 d R . . C8 C -0.1282(4) 0.37584(19) 1.2192(5) 0.0329(10) Uani 1 d . . . H8 H -0.1135 0.3708 1.1305 0.039 Uiso 1 d R . . C12 C -0.1206(4) 0.4333(2) 1.4216(4) 0.0296(9) Uani 1 d . . . H12 H -0.0971 0.4690 1.4657 0.036 Uiso 1 d R . . C3 C 0.4845(3) 0.43303(17) 1.1389(4) 0.0219(8) Uani 1 d . . . H3 H 0.5201 0.4316 1.0597 0.026 Uiso 1 d R . . C5 C 0.5058(3) 0.43981(17) 1.3805(4) 0.0220(8) Uani 1 d . . . H5 H 0.5579 0.4416 1.4627 0.026 Uiso 1 d R . . C9 C -0.1886(4) 0.3305(2) 1.2765(7) 0.0477(14) Uani 1 d . . . H9 H -0.2153 0.2952 1.2330 0.057 Uiso 1 d R . . C11 C -0.1801(4) 0.3869(3) 1.4791(5) 0.0431(14) Uani 1 d . . . H11 H -0.1944 0.3925 1.5677 0.052 Uiso 1 d R . . C4 C 0.5590(3) 0.43720(18) 1.2625(4) 0.0221(8) Uani 1 d . . . H4 H 0.6452 0.4385 1.2660 0.026 Uiso 1 d R . . C10 C -0.2132(4) 0.3361(3) 1.4061(7) 0.0505(16) Uani 1 d . . . H10 H -0.2524 0.3071 1.4515 0.061 Uiso 1 d 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 C15 0.042(3) 0.034(2) 0.042(3) 0.007(2) -0.007(2) -0.022(2) C14 0.034(2) 0.021(2) 0.028(2) 0.0007(16) -0.0030(18) -0.0023(17) C16 0.019(2) 0.048(3) 0.038(2) 0.008(2) 0.0023(18) -0.0142(19) C13 0.0179(19) 0.0220(18) 0.0162(18) 0.0059(14) 0.0007(15) -0.0026(14) C17 0.022(2) 0.042(2) 0.029(2) 0.0051(19) 0.0026(18) -0.0031(18) O3 0.0166(13) 0.0240(14) 0.0164(13) -0.0011(11) 0.0012(10) -0.0007(10) C18 0.021(2) 0.0232(19) 0.0182(18) 0.0038(15) 0.0031(16) -0.0030(15) P2 0.0149(4) 0.0155(4) 0.0127(4) 0.0005(4) 0.0027(3) 0.0026(3) S1 0.0239(5) 0.0208(5) 0.0185(4) 0.0067(4) 0.0048(4) 0.0010(4) O4 0.0187(13) 0.0181(13) 0.0207(13) -0.0020(10) 0.0069(11) 0.0023(10) N1 0.0187(15) 0.0212(16) 0.0077(14) -0.0009(12) 0.0030(12) 0.0004(12) C19 0.0130(17) 0.0212(19) 0.027(2) -0.0028(15) 0.0094(15) 0.0005(14) P1 0.0123(4) 0.0154(4) 0.0099(4) 0.0012(3) 0.0020(3) 0.0006(4) C24 0.026(2) 0.029(2) 0.034(2) 0.0003(18) 0.0020(17) 0.0071(17) C20 0.035(2) 0.030(2) 0.027(2) 0.0006(17) 0.0166(18) 0.0037(18) O1 0.0087(12) 0.0184(12) 0.0189(13) 0.0011(10) 0.0013(10) -0.0010(9) O5 0.0170(12) 0.0235(13) 0.0122(13) 0.0019(10) 0.0001(10) 0.0000(11) O2 0.0108(12) 0.0265(13) 0.0161(12) 0.0021(11) 0.0023(9) -0.0007(10) C23 0.034(2) 0.017(2) 0.064(3) -0.005(2) 0.012(2) 0.0080(18) C21 0.043(3) 0.036(2) 0.033(2) -0.013(2) 0.019(2) -0.007(2) C1 0.0099(16) 0.0136(17) 0.0189(19) 0.0024(13) 0.0016(14) 0.0011(13) C7 0.0084(15) 0.027(2) 0.026(2) 0.0086(16) 0.0029(15) 0.0029(14) C22 0.030(2) 0.027(2) 0.057(3) -0.019(2) 0.019(2) -0.0004(19) C2 0.0189(19) 0.0236(18) 0.0143(17) -0.0030(14) 0.0003(14) 0.0020(15) C6 0.0143(17) 0.0225(19) 0.0185(18) 0.0023(14) 0.0025(14) 0.0030(15) C8 0.022(2) 0.032(2) 0.048(3) 0.000(2) 0.0135(19) 0.0053(17) C12 0.0128(19) 0.053(3) 0.023(2) 0.0053(19) 0.0022(16) 0.0018(18) C3 0.0197(19) 0.027(2) 0.0195(19) -0.0011(15) 0.0059(15) 0.0019(15) C5 0.0156(18) 0.028(2) 0.0209(19) 0.0016(15) -0.0023(15) 0.0033(15) C9 0.024(2) 0.029(2) 0.091(4) 0.004(3) 0.010(3) -0.0010(19) C11 0.016(2) 0.081(4) 0.033(3) 0.031(3) 0.0067(18) 0.010(2) C4 0.0124(17) 0.028(2) 0.025(2) 0.0001(16) -0.0010(14) 0.0035(15) C10 0.018(2) 0.049(3) 0.086(4) 0.036(3) 0.013(3) 0.005(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 C15 C14 1.374(7) . ? C15 C16 1.379(7) . ? C14 C13 1.375(6) . ? C16 C17 1.372(7) . ? C13 C18 1.367(5) . ? C13 O3 1.403(5) . ? C17 C18 1.390(5) . ? O3 P2 1.585(3) . ? P2 O4 1.584(3) . ? P2 N1 1.650(3) . ? P2 S1 1.8978(12) . ? O4 C19 1.402(4) . ? N1 P1 1.640(3) . ? C19 C20 1.364(6) . ? C19 C24 1.387(6) . ? P1 O5 1.458(3) . ? P1 O1 1.574(2) . ? P1 O2 1.575(2) . ? C24 C23 1.376(6) . ? C20 C21 1.371(6) . ? O1 C1 1.420(4) . ? O2 C7 1.412(4) . ? C23 C22 1.363(8) . ? C21 C22 1.374(7) . ? C1 C6 1.369(5) . ? C1 C2 1.371(5) . ? C7 C8 1.367(6) . ? C7 C12 1.369(6) . ? C2 C3 1.391(5) . ? C6 C5 1.389(5) . ? C8 C9 1.376(7) . ? C12 C11 1.391(7) . ? C3 C4 1.380(6) . ? C5 C4 1.387(6) . ? C9 C10 1.367(9) . ? C11 C10 1.371(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 C15 C16 120.7(4) . . ? C13 C14 C15 118.7(4) . . ? C17 C16 C15 119.6(4) . . ? C18 C13 C14 122.1(4) . . ? C18 C13 O3 120.5(3) . . ? C14 C13 O3 117.0(3) . . ? C16 C17 C18 120.6(4) . . ? C13 O3 P2 125.6(2) . . ? C13 C18 C17 118.3(4) . . ? O4 P2 O3 99.38(14) . . ? O4 P2 N1 100.01(15) . . ? O3 P2 N1 106.97(15) . . ? O4 P2 S1 119.14(11) . . ? O3 P2 S1 115.75(11) . . ? N1 P2 S1 113.48(12) . . ? C19 O4 P2 122.2(2) . . ? P1 N1 P2 127.4(2) . . ? C20 C19 C24 121.8(4) . . ? C20 C19 O4 119.8(4) . . ? C24 C19 O4 118.3(4) . . ? O5 P1 O1 115.73(14) . . ? O5 P1 O2 115.64(15) . . ? O1 P1 O2 100.69(13) . . ? O5 P1 N1 113.93(16) . . ? O1 P1 N1 104.82(15) . . ? O2 P1 N1 104.41(15) . . ? C23 C24 C19 117.5(4) . . ? C19 C20 C21 119.4(4) . . ? C1 O1 P1 118.8(2) . . ? C7 O2 P1 120.5(2) . . ? C22 C23 C24 121.2(4) . . ? C20 C21 C22 119.8(5) . . ? C6 C1 C2 123.3(3) . . ? C6 C1 O1 120.2(3) . . ? C2 C1 O1 116.5(3) . . ? C8 C7 C12 121.9(4) . . ? C8 C7 O2 117.1(4) . . ? C12 C7 O2 120.9(4) . . ? C23 C22 C21 120.2(4) . . ? C1 C2 C3 118.1(3) . . ? C1 C6 C5 118.2(3) . . ? C7 C8 C9 119.3(5) . . ? C7 C12 C11 118.2(5) . . ? C4 C3 C2 120.1(4) . . ? C4 C5 C6 120.0(3) . . ? C10 C9 C8 119.8(5) . . ? C10 C11 C12 120.1(5) . . ? C3 C4 C5 120.3(3) . . ? C9 C10 C11 120.7(5) . . ? _diffrn_measured_fraction_theta_max 0.499 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.499 _refine_diff_density_max 0.387 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.063