# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef 'Gesamtcif.cif' _audit_creation_method 'manual editing of form.cif' _publ_contact_author_phone '049 228 73-5345' _publ_contact_author_fax '049 228 73-9616' _publ_contact_author_email r.streubel@uni-bonn.de _publ_contact_author_name 'Streubel, Rainer' _publ_contact_author_address ; Institut f\"ur Anorganische Chemie Rheinische Friedrich-Wilhelms-University of Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Germany ; _publ_section_title ; Synthesis, structure and reactivity of 4-phosphanylated 1,3-dialkyl-imidazole-2-thiones ; loop_ _publ_author_address ; Institut f\"ur Anorganische Chemie Rheinische Friedrich-Wilhelms-University of Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Germany ; ; Institut f\"ur Anorganische Chemie Rheinische Friedrich-Wilhelms-University of Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Germany ; ; Institut f\"ur Anorganische Chemie Rheinische Friedrich-Wilhelms-University of Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Germany ; ; Institut f\"ur Anorganische Chemie Rheinische Friedrich-Wilhelms-University of Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Germany ; ; Department of Chemistry The University of Alabama Tuscaloosa AL 35487 USA ; ; Institut f\"ur Anorganische Chemie Rheinische Friedrich-Wilhelms-University of Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Germany ; _publ_author_name R.Streubel #------------------------------------------------------------------------------ data_3a-GSTR058 _database_code_depnum_ccdc_archive 'CCDC 859623' #TrackingRef 'Gesamtcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H17 N2 P S' _chemical_formula_sum 'C17 H17 N2 P S' _chemical_formula_weight 312.36 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 9.7040(6) _cell_length_b 9.7271(5) _cell_length_c 17.0059(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.674(3) _cell_angle_gamma 90.00 _cell_volume 1559.72(16) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3830 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 29.13 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.94648 _exptl_absorpt_correction_T_max 0.99331 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13970 _diffrn_reflns_av_R_equivalents 0.0712 _diffrn_reflns_av_sigmaI/netI 0.1183 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 29.12 _reflns_number_total 4121 _reflns_number_gt 2350 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0215P)^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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4121 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_restrained_S_all 0.869 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6855(2) 0.88968(17) -0.03247(10) 0.0186(4) Uani 1 1 d . . . C2 C 0.5254(2) 0.76254(18) 0.01117(11) 0.0179(4) Uani 1 1 d . . . H2 H 0.436(2) 0.7278(17) 0.0091(10) 0.021 Uiso 1 1 d . . . C3 C 0.6507(2) 0.74210(17) 0.06445(10) 0.0171(4) Uani 1 1 d . . . C4 C 0.8984(2) 0.8363(2) 0.07691(13) 0.0289(5) Uani 1 1 d . . . H4A H 0.949(2) 0.888(2) 0.0439(12) 0.043 Uiso 1 1 d . . . H4B H 0.946(2) 0.750(2) 0.0865(12) 0.043 Uiso 1 1 d . . . H4C H 0.909(2) 0.888(2) 0.1307(12) 0.043 Uiso 1 1 d . . . C5 C 0.4375(2) 0.9037(2) -0.11541(12) 0.0233(5) Uani 1 1 d . . . H5A H 0.467(2) 0.8864(19) -0.1666(11) 0.035 Uiso 1 1 d . . . H5B H 0.423(2) 1.003(2) -0.1104(11) 0.035 Uiso 1 1 d . . . H5C H 0.359(2) 0.857(2) -0.1180(11) 0.035 Uiso 1 1 d . . . C6 C 0.78783(19) 0.49998(18) 0.13805(10) 0.0179(4) Uani 1 1 d . . . C7 C 0.7902(2) 0.4587(2) 0.05990(11) 0.0235(5) Uani 1 1 d . . . H7 H 0.739(2) 0.5076(18) 0.0133(11) 0.028 Uiso 1 1 d . . . C8 C 0.8646(2) 0.3416(2) 0.04812(12) 0.0281(5) Uani 1 1 d . . . H8 H 0.865(2) 0.3166(18) -0.0048(11) 0.034 Uiso 1 1 d . . . C9 C 0.9362(2) 0.2645(2) 0.11298(12) 0.0249(5) Uani 1 1 d . . . H9 H 0.987(2) 0.1883(18) 0.1045(11) 0.030 Uiso 1 1 d . . . C10 C 0.9343(2) 0.3043(2) 0.19080(12) 0.0239(5) Uani 1 1 d . . . H10 H 0.987(2) 0.2512(18) 0.2360(11) 0.029 Uiso 1 1 d . . . C11 C 0.8621(2) 0.42207(19) 0.20340(11) 0.0217(5) Uani 1 1 d . . . H11 H 0.8604(19) 0.4531(17) 0.2579(11) 0.026 Uiso 1 1 d . . . C12 C 0.51994(19) 0.59172(18) 0.16356(10) 0.0168(4) Uani 1 1 d . . . C13 C 0.4171(2) 0.68868(19) 0.17047(10) 0.0193(4) Uani 1 1 d . . . H13 H 0.4374(19) 0.7839(19) 0.1718(10) 0.023 Uiso 1 1 d . . . C14 C 0.2825(2) 0.6482(2) 0.17407(11) 0.0224(4) Uani 1 1 d . . . H14 H 0.212(2) 0.7155(18) 0.1774(10) 0.027 Uiso 1 1 d . . . C15 C 0.2478(2) 0.5094(2) 0.17251(11) 0.0262(5) Uani 1 1 d . . . H15 H 0.159(2) 0.4807(18) 0.1740(11) 0.031 Uiso 1 1 d . . . C16 C 0.3494(2) 0.4119(2) 0.16764(11) 0.0252(5) Uani 1 1 d . . . H16 H 0.325(2) 0.3197(19) 0.1685(11) 0.030 Uiso 1 1 d . . . C17 C 0.4837(2) 0.45245(19) 0.16299(11) 0.0225(5) Uani 1 1 d . . . H17 H 0.551(2) 0.3868(18) 0.1597(10) 0.027 Uiso 1 1 d . . . N1 N 0.74961(16) 0.82224(14) 0.03652(8) 0.0173(3) Uani 1 1 d . . . N2 N 0.54616(16) 0.85275(14) -0.04756(8) 0.0171(3) Uani 1 1 d . . . P1 P 0.69671(5) 0.65463(5) 0.16166(3) 0.01816(13) Uani 1 1 d . . . S1 S 0.75944(6) 0.99656(5) -0.08857(3) 0.02687(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0206(12) 0.0144(9) 0.0221(10) -0.0009(8) 0.0076(9) 0.0012(8) C2 0.0175(12) 0.0141(9) 0.0237(10) -0.0006(8) 0.0080(9) -0.0032(8) C3 0.0172(11) 0.0124(9) 0.0236(10) -0.0011(8) 0.0085(9) -0.0012(8) C4 0.0152(13) 0.0338(13) 0.0367(12) 0.0086(11) 0.0041(10) -0.0022(10) C5 0.0220(13) 0.0237(11) 0.0229(10) 0.0035(10) 0.0027(10) 0.0011(9) C6 0.0140(11) 0.0170(9) 0.0237(10) 0.0019(9) 0.0064(8) -0.0019(8) C7 0.0230(13) 0.0263(11) 0.0208(10) 0.0017(9) 0.0046(9) 0.0035(9) C8 0.0308(14) 0.0293(12) 0.0248(11) -0.0062(10) 0.0078(10) 0.0030(10) C9 0.0210(13) 0.0198(10) 0.0343(12) -0.0037(10) 0.0075(10) 0.0030(9) C10 0.0171(12) 0.0253(11) 0.0289(11) 0.0058(9) 0.0049(9) 0.0045(9) C11 0.0213(13) 0.0237(11) 0.0212(10) 0.0023(9) 0.0071(9) 0.0015(9) C12 0.0170(12) 0.0201(10) 0.0131(8) 0.0016(8) 0.0033(8) 0.0017(8) C13 0.0215(13) 0.0178(10) 0.0192(9) 0.0002(9) 0.0062(8) 0.0013(9) C14 0.0201(12) 0.0267(11) 0.0217(10) -0.0001(9) 0.0080(9) 0.0044(9) C15 0.0192(12) 0.0352(12) 0.0258(10) 0.0007(10) 0.0084(9) -0.0064(10) C16 0.0298(14) 0.0189(10) 0.0284(11) 0.0002(9) 0.0098(10) -0.0059(10) C17 0.0252(14) 0.0182(10) 0.0249(10) -0.0001(9) 0.0076(9) 0.0000(9) N1 0.0136(9) 0.0158(8) 0.0227(8) 0.0020(7) 0.0049(7) -0.0005(7) N2 0.0162(10) 0.0164(8) 0.0184(8) 0.0024(7) 0.0036(7) -0.0012(7) P1 0.0190(3) 0.0168(2) 0.0195(2) 0.0011(2) 0.0062(2) 0.0000(2) S1 0.0247(3) 0.0256(3) 0.0328(3) 0.0109(2) 0.0117(2) -0.0006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.360(2) . ? C1 N2 1.363(2) . ? C1 S1 1.6821(18) . ? C2 C3 1.349(2) . ? C2 N2 1.380(2) . ? C2 H2 0.927(19) . ? C3 N1 1.403(2) . ? C3 P1 1.8185(18) . ? C4 N1 1.452(2) . ? C4 H4A 0.97(2) . ? C4 H4B 0.95(2) . ? C4 H4C 1.03(2) . ? C5 N2 1.453(2) . ? C5 H5A 0.995(19) . ? C5 H5B 0.981(19) . ? C5 H5C 0.88(2) . ? C6 C7 1.394(2) . ? C6 C11 1.396(2) . ? C6 P1 1.8368(18) . ? C7 C8 1.389(3) . ? C7 H7 0.958(18) . ? C8 C9 1.378(3) . ? C8 H8 0.934(18) . ? C9 C10 1.383(3) . ? C9 H9 0.918(18) . ? C10 C11 1.386(3) . ? C10 H10 0.966(18) . ? C11 H11 0.978(17) . ? C12 C13 1.398(2) . ? C12 C17 1.399(2) . ? C12 P1 1.8287(19) . ? C13 C14 1.380(3) . ? C13 H13 0.946(18) . ? C14 C15 1.390(3) . ? C14 H14 0.956(18) . ? C15 C16 1.385(3) . ? C15 H15 0.911(19) . ? C16 C17 1.382(3) . ? C16 H16 0.929(18) . ? C17 H17 0.928(18) . ? 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 C1 N2 105.45(14) . . ? N1 C1 S1 128.17(15) . . ? N2 C1 S1 126.38(14) . . ? C3 C2 N2 108.48(17) . . ? C3 C2 H2 131.4(11) . . ? N2 C2 H2 120.1(11) . . ? C2 C3 N1 105.73(15) . . ? C2 C3 P1 131.92(15) . . ? N1 C3 P1 121.81(13) . . ? N1 C4 H4A 110.9(12) . . ? N1 C4 H4B 112.4(13) . . ? H4A C4 H4B 105.8(18) . . ? N1 C4 H4C 110.4(12) . . ? H4A C4 H4C 107.7(16) . . ? H4B C4 H4C 109.4(16) . . ? N2 C5 H5A 109.3(11) . . ? N2 C5 H5B 111.0(11) . . ? H5A C5 H5B 108.7(15) . . ? N2 C5 H5C 108.6(13) . . ? H5A C5 H5C 107.3(16) . . ? H5B C5 H5C 111.9(18) . . ? C7 C6 C11 118.74(17) . . ? C7 C6 P1 124.17(14) . . ? C11 C6 P1 117.06(13) . . ? C8 C7 C6 120.03(18) . . ? C8 C7 H7 118.4(11) . . ? C6 C7 H7 121.5(11) . . ? C9 C8 C7 120.79(19) . . ? C9 C8 H8 120.9(11) . . ? C7 C8 H8 118.3(11) . . ? C8 C9 C10 119.68(19) . . ? C8 C9 H9 120.0(12) . . ? C10 C9 H9 120.3(12) . . ? C9 C10 C11 120.07(18) . . ? C9 C10 H10 119.2(11) . . ? C11 C10 H10 120.7(11) . . ? C10 C11 C6 120.67(18) . . ? C10 C11 H11 121.6(10) . . ? C6 C11 H11 117.7(10) . . ? C13 C12 C17 118.07(18) . . ? C13 C12 P1 117.84(14) . . ? C17 C12 P1 124.00(15) . . ? C14 C13 C12 120.90(18) . . ? C14 C13 H13 118.2(11) . . ? C12 C13 H13 120.9(11) . . ? C13 C14 C15 120.26(19) . . ? C13 C14 H14 120.2(11) . . ? C15 C14 H14 119.6(11) . . ? C16 C15 C14 119.6(2) . . ? C16 C15 H15 118.9(12) . . ? C14 C15 H15 121.5(12) . . ? C17 C16 C15 120.16(19) . . ? C17 C16 H16 121.6(12) . . ? C15 C16 H16 118.2(12) . . ? C16 C17 C12 121.01(19) . . ? C16 C17 H17 119.9(12) . . ? C12 C17 H17 119.1(12) . . ? C1 N1 C3 110.49(15) . . ? C1 N1 C4 124.32(16) . . ? C3 N1 C4 125.14(15) . . ? C1 N2 C2 109.85(15) . . ? C1 N2 C5 124.08(15) . . ? C2 N2 C5 126.06(17) . . ? C3 P1 C12 98.22(8) . . ? C3 P1 C6 102.23(8) . . ? C12 P1 C6 103.40(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C3 N1 -0.20(19) . . . . ? N2 C2 C3 P1 171.21(13) . . . . ? C11 C6 C7 C8 0.4(3) . . . . ? P1 C6 C7 C8 178.60(16) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C9 C10 C11 C6 1.5(3) . . . . ? C7 C6 C11 C10 -1.3(3) . . . . ? P1 C6 C11 C10 -179.67(15) . . . . ? C17 C12 C13 C14 -2.0(3) . . . . ? P1 C12 C13 C14 -178.56(13) . . . . ? C12 C13 C14 C15 1.3(3) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? C14 C15 C16 C17 -1.1(3) . . . . ? C15 C16 C17 C12 0.4(3) . . . . ? C13 C12 C17 C16 1.2(3) . . . . ? P1 C12 C17 C16 177.50(14) . . . . ? N2 C1 N1 C3 0.44(18) . . . . ? S1 C1 N1 C3 -179.57(13) . . . . ? N2 C1 N1 C4 -177.24(17) . . . . ? S1 C1 N1 C4 2.8(3) . . . . ? C2 C3 N1 C1 -0.15(19) . . . . ? P1 C3 N1 C1 -172.64(12) . . . . ? C2 C3 N1 C4 177.50(17) . . . . ? P1 C3 N1 C4 5.0(2) . . . . ? N1 C1 N2 C2 -0.57(18) . . . . ? S1 C1 N2 C2 179.44(13) . . . . ? N1 C1 N2 C5 178.79(15) . . . . ? S1 C1 N2 C5 -1.2(2) . . . . ? C3 C2 N2 C1 0.5(2) . . . . ? C3 C2 N2 C5 -178.85(16) . . . . ? C2 C3 P1 C12 3.28(19) . . . . ? N1 C3 P1 C12 173.54(14) . . . . ? C2 C3 P1 C6 109.00(18) . . . . ? N1 C3 P1 C6 -80.74(15) . . . . ? C13 C12 P1 C3 -67.67(14) . . . . ? C17 C12 P1 C3 115.99(16) . . . . ? C13 C12 P1 C6 -172.41(13) . . . . ? C17 C12 P1 C6 11.25(17) . . . . ? C7 C6 P1 C3 -10.45(19) . . . . ? C11 C6 P1 C3 167.78(15) . . . . ? C7 C6 P1 C12 91.21(17) . . . . ? C11 C6 P1 C12 -90.56(15) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 29.12 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.305 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.069 #------------------------------------------------------------------------------ data_3-GSTR080 _database_code_depnum_ccdc_archive 'CCDC 859624' #TrackingRef 'Gesamtcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H21 N2 P S' _chemical_formula_sum 'C27 H21 N2 P S' _chemical_formula_weight 436.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 5.88510(10) _cell_length_b 21.3076(6) _cell_length_c 17.9758(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.1495(16) _cell_angle_gamma 90.00 _cell_volume 2231.35(10) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5207 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 28.70 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.89179 _exptl_absorpt_correction_T_max 0.99350 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24110 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5244 _reflns_number_gt 4071 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.7253P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5244 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8839(2) 0.33478(7) 0.12547(9) 0.0210(3) Uani 1 1 d . . . C2 C 0.9426(3) 0.24879(7) 0.05616(9) 0.0218(3) Uani 1 1 d . . . H2A H 0.9945 0.2232 0.0187 0.026 Uiso 1 1 calc R . . C3 C 0.8140(2) 0.22940(7) 0.10844(9) 0.0204(3) Uani 1 1 d . . . C4 C 0.6495(2) 0.28265(7) 0.21340(8) 0.0214(3) Uani 1 1 d . . . C5 C 0.4563(3) 0.32041(8) 0.21100(9) 0.0243(3) Uani 1 1 d . . . H5A H 0.4153 0.3486 0.1704 0.029 Uiso 1 1 calc R . . C6 C 0.3240(3) 0.31632(9) 0.26884(9) 0.0302(4) Uani 1 1 d . . . H6A H 0.1920 0.3421 0.2680 0.036 Uiso 1 1 calc R . . C7 C 0.3832(3) 0.27496(9) 0.32777(9) 0.0324(4) Uani 1 1 d . . . H7A H 0.2908 0.2720 0.3669 0.039 Uiso 1 1 calc R . . C8 C 0.5766(3) 0.23794(9) 0.32967(10) 0.0325(4) Uani 1 1 d . . . H8A H 0.6168 0.2096 0.3702 0.039 Uiso 1 1 calc R . . C9 C 0.7127(3) 0.24196(8) 0.27268(9) 0.0261(3) Uani 1 1 d . . . H9A H 0.8473 0.2171 0.2744 0.031 Uiso 1 1 calc R . . C10 C 1.1269(3) 0.34717(7) 0.02195(9) 0.0220(3) Uani 1 1 d . . . C11 C 1.0539(3) 0.40425(8) -0.01013(9) 0.0285(4) Uani 1 1 d . . . H11A H 0.9120 0.4220 -0.0013 0.034 Uiso 1 1 calc R . . C12 C 1.1911(3) 0.43507(9) -0.05536(11) 0.0362(4) Uani 1 1 d . . . H12A H 1.1443 0.4746 -0.0768 0.043 Uiso 1 1 calc R . . C13 C 1.3956(3) 0.40855(10) -0.06942(11) 0.0390(5) Uani 1 1 d . . . H13A H 1.4876 0.4297 -0.1009 0.047 Uiso 1 1 calc R . . C14 C 1.4664(3) 0.35143(9) -0.03778(10) 0.0330(4) Uani 1 1 d . . . H14A H 1.6062 0.3332 -0.0479 0.040 Uiso 1 1 calc R . . C15 C 1.3328(3) 0.32065(8) 0.00881(9) 0.0252(3) Uani 1 1 d . . . H15A H 1.3823 0.2818 0.0315 0.030 Uiso 1 1 calc R . . C16 C 0.8836(3) 0.10931(8) 0.17745(9) 0.0230(3) Uani 1 1 d . . . C17 C 1.1039(3) 0.13051(8) 0.20523(10) 0.0271(4) Uani 1 1 d . . . H17A H 1.1517 0.1711 0.1921 0.033 Uiso 1 1 calc R . . C18 C 1.2539(3) 0.09221(9) 0.25218(10) 0.0317(4) Uani 1 1 d . . . H18A H 1.4026 0.1071 0.2716 0.038 Uiso 1 1 calc R . . C19 C 1.1867(3) 0.03271(9) 0.27047(10) 0.0344(4) Uani 1 1 d . . . H19A H 1.2896 0.0067 0.3022 0.041 Uiso 1 1 calc R . . C20 C 0.9698(3) 0.01095(8) 0.24259(10) 0.0345(4) Uani 1 1 d . . . H20A H 0.9248 -0.0302 0.2546 0.041 Uiso 1 1 calc R . . C21 C 0.8179(3) 0.04916(8) 0.19712(10) 0.0290(4) Uani 1 1 d . . . H21A H 0.6679 0.0344 0.1792 0.035 Uiso 1 1 calc R . . C22 C 0.6731(3) 0.12251(8) 0.02518(9) 0.0247(3) Uani 1 1 d . . . C23 C 0.4776(3) 0.13045(9) -0.02801(10) 0.0333(4) Uani 1 1 d . . . H23A H 0.3506 0.1533 -0.0148 0.040 Uiso 1 1 calc R . . C24 C 0.4662(3) 0.10548(10) -0.09968(11) 0.0385(4) Uani 1 1 d . . . H24A H 0.3333 0.1119 -0.1355 0.046 Uiso 1 1 calc R . . C25 C 0.6489(3) 0.07124(9) -0.11876(11) 0.0369(4) Uani 1 1 d . . . H25A H 0.6406 0.0534 -0.1675 0.044 Uiso 1 1 calc R . . C26 C 0.8441(3) 0.06289(9) -0.06680(11) 0.0366(4) Uani 1 1 d . . . H26A H 0.9696 0.0395 -0.0802 0.044 Uiso 1 1 calc R . . C27 C 0.8577(3) 0.08847(8) 0.00494(10) 0.0292(4) Uani 1 1 d . . . H27A H 0.9925 0.0828 0.0401 0.035 Uiso 1 1 calc R . . N1 N 0.7804(2) 0.28302(6) 0.15141(7) 0.0200(3) Uani 1 1 d . . . N2 N 0.9861(2) 0.31244(6) 0.06640(7) 0.0207(3) Uani 1 1 d . . . P1 P 0.66531(6) 0.155769(19) 0.11886(2) 0.02198(11) Uani 1 1 d . . . S1 S 0.88884(7) 0.407634(19) 0.15965(2) 0.02692(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0213(7) 0.0215(8) 0.0196(8) 0.0019(6) 0.0014(5) 0.0020(6) C2 0.0232(7) 0.0201(8) 0.0225(8) -0.0001(6) 0.0047(6) 0.0016(6) C3 0.0212(7) 0.0187(8) 0.0215(8) 0.0002(6) 0.0043(6) 0.0028(6) C4 0.0227(7) 0.0242(8) 0.0177(8) -0.0024(6) 0.0040(6) -0.0003(6) C5 0.0265(8) 0.0274(9) 0.0183(8) -0.0007(6) 0.0004(6) 0.0045(6) C6 0.0266(8) 0.0408(11) 0.0233(9) -0.0040(7) 0.0042(6) 0.0083(7) C7 0.0319(9) 0.0469(12) 0.0200(9) -0.0005(8) 0.0093(7) 0.0043(7) C8 0.0376(9) 0.0399(11) 0.0201(9) 0.0060(7) 0.0045(7) 0.0055(7) C9 0.0265(8) 0.0291(9) 0.0227(8) 0.0007(7) 0.0032(6) 0.0057(6) C10 0.0226(7) 0.0247(8) 0.0180(8) 0.0018(6) 0.0006(5) -0.0046(6) C11 0.0293(8) 0.0279(9) 0.0274(9) 0.0062(7) 0.0015(6) -0.0018(6) C12 0.0403(10) 0.0321(10) 0.0352(10) 0.0127(8) 0.0019(8) -0.0068(8) C13 0.0360(10) 0.0513(12) 0.0304(10) 0.0100(9) 0.0073(7) -0.0156(8) C14 0.0222(8) 0.0487(12) 0.0281(9) 0.0018(8) 0.0030(6) -0.0065(7) C15 0.0235(8) 0.0311(9) 0.0197(8) 0.0021(7) -0.0012(6) -0.0031(6) C16 0.0270(8) 0.0201(8) 0.0238(8) 0.0009(6) 0.0106(6) 0.0019(6) C17 0.0264(8) 0.0240(9) 0.0327(9) 0.0035(7) 0.0105(6) 0.0013(6) C18 0.0275(8) 0.0354(10) 0.0332(10) 0.0019(8) 0.0075(7) 0.0068(7) C19 0.0430(10) 0.0335(10) 0.0292(10) 0.0064(8) 0.0131(7) 0.0164(8) C20 0.0513(11) 0.0212(9) 0.0349(10) 0.0063(7) 0.0197(8) 0.0042(7) C21 0.0353(9) 0.0235(9) 0.0308(9) 0.0006(7) 0.0131(7) -0.0027(7) C22 0.0272(8) 0.0194(8) 0.0289(9) -0.0015(7) 0.0091(6) -0.0035(6) C23 0.0272(8) 0.0356(10) 0.0372(10) -0.0070(8) 0.0050(7) -0.0018(7) C24 0.0377(10) 0.0440(12) 0.0325(10) -0.0061(8) 0.0010(8) -0.0078(8) C25 0.0543(11) 0.0306(10) 0.0279(10) -0.0067(8) 0.0132(8) -0.0110(8) C26 0.0489(11) 0.0277(10) 0.0370(11) -0.0013(8) 0.0195(8) 0.0032(8) C27 0.0327(9) 0.0267(9) 0.0299(9) 0.0015(7) 0.0101(7) 0.0040(7) N1 0.0221(6) 0.0194(7) 0.0191(7) 0.0001(5) 0.0046(5) 0.0016(5) N2 0.0225(6) 0.0200(7) 0.0201(7) 0.0020(5) 0.0043(5) 0.0000(5) P1 0.0216(2) 0.0205(2) 0.0253(2) -0.00045(16) 0.00799(15) -0.00061(15) S1 0.0339(2) 0.0187(2) 0.0279(2) -0.00238(16) 0.00364(16) 0.00023(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.373(2) . ? C1 N2 1.3773(19) . ? C1 S1 1.6683(16) . ? C2 C3 1.352(2) . ? C2 N2 1.388(2) . ? C2 H2A 0.9500 . ? C3 N1 1.4087(19) . ? C3 P1 1.8190(15) . ? C4 C9 1.383(2) . ? C4 C5 1.389(2) . ? C4 N1 1.4419(19) . ? C5 C6 1.387(2) . ? C5 H5A 0.9500 . ? C6 C7 1.384(3) . ? C6 H6A 0.9500 . ? C7 C8 1.381(2) . ? C7 H7A 0.9500 . ? C8 C9 1.389(2) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C15 1.387(2) . ? C10 C11 1.388(2) . ? C10 N2 1.4354(19) . ? C11 C12 1.390(2) . ? C11 H11A 0.9500 . ? C12 C13 1.385(3) . ? C12 H12A 0.9500 . ? C13 C14 1.383(3) . ? C13 H13A 0.9500 . ? C14 C15 1.391(2) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C17 1.397(2) . ? C16 C21 1.398(2) . ? C16 P1 1.8318(16) . ? C17 C18 1.395(2) . ? C17 H17A 0.9500 . ? C18 C19 1.382(3) . ? C18 H18A 0.9500 . ? C19 C20 1.384(3) . ? C19 H19A 0.9500 . ? C20 C21 1.387(2) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C27 1.396(2) . ? C22 C23 1.398(2) . ? C22 P1 1.8337(17) . ? C23 C24 1.387(3) . ? C23 H23A 0.9500 . ? C24 C25 1.382(3) . ? C24 H24A 0.9500 . ? C25 C26 1.385(3) . ? C25 H25A 0.9500 . ? C26 C27 1.392(3) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 104.32(13) . . ? N1 C1 S1 127.43(12) . . ? N2 C1 S1 128.24(12) . . ? C3 C2 N2 108.50(13) . . ? C3 C2 H2A 125.7 . . ? N2 C2 H2A 125.7 . . ? C2 C3 N1 105.61(13) . . ? C2 C3 P1 131.30(12) . . ? N1 C3 P1 122.42(11) . . ? C9 C4 C5 121.10(14) . . ? C9 C4 N1 118.95(13) . . ? C5 C4 N1 119.86(14) . . ? C6 C5 C4 118.97(15) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? C7 C6 C5 120.46(15) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C8 C7 C6 119.97(15) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? C7 C8 C9 120.37(16) . . ? C7 C8 H8A 119.8 . . ? C9 C8 H8A 119.8 . . ? C4 C9 C8 119.11(15) . . ? C4 C9 H9A 120.4 . . ? C8 C9 H9A 120.4 . . ? C15 C10 C11 120.85(15) . . ? C15 C10 N2 118.15(14) . . ? C11 C10 N2 120.92(14) . . ? C10 C11 C12 119.06(16) . . ? C10 C11 H11A 120.5 . . ? C12 C11 H11A 120.5 . . ? C13 C12 C11 120.41(18) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C14 C13 C12 120.20(16) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C13 C14 C15 119.98(16) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C10 C15 C14 119.47(16) . . ? C10 C15 H15A 120.3 . . ? C14 C15 H15A 120.3 . . ? C17 C16 C21 118.80(15) . . ? C17 C16 P1 124.78(12) . . ? C21 C16 P1 116.37(12) . . ? C18 C17 C16 120.18(16) . . ? C18 C17 H17A 119.9 . . ? C16 C17 H17A 119.9 . . ? C19 C18 C17 120.19(17) . . ? C19 C18 H18A 119.9 . . ? C17 C18 H18A 119.9 . . ? C18 C19 C20 120.13(16) . . ? C18 C19 H19A 119.9 . . ? C20 C19 H19A 119.9 . . ? C19 C20 C21 120.07(16) . . ? C19 C20 H20A 120.0 . . ? C21 C20 H20A 120.0 . . ? C20 C21 C16 120.61(16) . . ? C20 C21 H21A 119.7 . . ? C16 C21 H21A 119.7 . . ? C27 C22 C23 118.67(16) . . ? C27 C22 P1 124.17(13) . . ? C23 C22 P1 117.12(12) . . ? C24 C23 C22 121.04(16) . . ? C24 C23 H23A 119.5 . . ? C22 C23 H23A 119.5 . . ? C25 C24 C23 119.74(18) . . ? C25 C24 H24A 120.1 . . ? C23 C24 H24A 120.1 . . ? C24 C25 C26 120.03(17) . . ? C24 C25 H25A 120.0 . . ? C26 C25 H25A 120.0 . . ? C25 C26 C27 120.49(17) . . ? C25 C26 H26A 119.8 . . ? C27 C26 H26A 119.8 . . ? C26 C27 C22 120.02(17) . . ? C26 C27 H27A 120.0 . . ? C22 C27 H27A 120.0 . . ? C1 N1 C3 111.21(12) . . ? C1 N1 C4 125.33(13) . . ? C3 N1 C4 123.45(12) . . ? C1 N2 C2 110.34(12) . . ? C1 N2 C10 126.91(13) . . ? C2 N2 C10 122.70(13) . . ? C3 P1 C16 102.53(7) . . ? C3 P1 C22 99.42(7) . . ? C16 P1 C22 102.26(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C3 N1 -0.23(16) . . . . ? N2 C2 C3 P1 170.31(12) . . . . ? C9 C4 C5 C6 -0.8(2) . . . . ? N1 C4 C5 C6 175.77(14) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C5 C4 C9 C8 1.6(2) . . . . ? N1 C4 C9 C8 -175.03(15) . . . . ? C7 C8 C9 C4 -1.2(3) . . . . ? C15 C10 C11 C12 -0.6(3) . . . . ? N2 C10 C11 C12 -177.31(15) . . . . ? C10 C11 C12 C13 1.3(3) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? C11 C10 C15 C14 -0.7(2) . . . . ? N2 C10 C15 C14 176.14(14) . . . . ? C13 C14 C15 C10 1.2(3) . . . . ? C21 C16 C17 C18 -0.5(2) . . . . ? P1 C16 C17 C18 177.18(13) . . . . ? C16 C17 C18 C19 1.1(3) . . . . ? C17 C18 C19 C20 -0.3(3) . . . . ? C18 C19 C20 C21 -1.0(3) . . . . ? C19 C20 C21 C16 1.6(3) . . . . ? C17 C16 C21 C20 -0.8(2) . . . . ? P1 C16 C21 C20 -178.68(13) . . . . ? C27 C22 C23 C24 -0.3(3) . . . . ? P1 C22 C23 C24 -178.36(15) . . . . ? C22 C23 C24 C25 1.1(3) . . . . ? C23 C24 C25 C26 -1.1(3) . . . . ? C24 C25 C26 C27 0.4(3) . . . . ? C25 C26 C27 C22 0.4(3) . . . . ? C23 C22 C27 C26 -0.4(3) . . . . ? P1 C22 C27 C26 177.44(13) . . . . ? N2 C1 N1 C3 -0.98(16) . . . . ? S1 C1 N1 C3 -179.66(11) . . . . ? N2 C1 N1 C4 -179.78(12) . . . . ? S1 C1 N1 C4 1.5(2) . . . . ? C2 C3 N1 C1 0.78(16) . . . . ? P1 C3 N1 C1 -170.81(11) . . . . ? C2 C3 N1 C4 179.60(13) . . . . ? P1 C3 N1 C4 8.01(19) . . . . ? C9 C4 N1 C1 -124.21(17) . . . . ? C5 C4 N1 C1 59.1(2) . . . . ? C9 C4 N1 C3 57.1(2) . . . . ? C5 C4 N1 C3 -119.51(16) . . . . ? N1 C1 N2 C2 0.83(16) . . . . ? S1 C1 N2 C2 179.49(12) . . . . ? N1 C1 N2 C10 -176.73(13) . . . . ? S1 C1 N2 C10 1.9(2) . . . . ? C3 C2 N2 C1 -0.38(17) . . . . ? C3 C2 N2 C10 177.30(13) . . . . ? C15 C10 N2 C1 132.47(16) . . . . ? C11 C10 N2 C1 -50.7(2) . . . . ? C15 C10 N2 C2 -44.8(2) . . . . ? C11 C10 N2 C2 132.03(16) . . . . ? C2 C3 P1 C16 90.43(16) . . . . ? N1 C3 P1 C16 -100.37(13) . . . . ? C2 C3 P1 C22 -14.48(17) . . . . ? N1 C3 P1 C22 154.72(12) . . . . ? C17 C16 P1 C3 0.95(16) . . . . ? C21 C16 P1 C3 178.66(12) . . . . ? C17 C16 P1 C22 103.65(15) . . . . ? C21 C16 P1 C22 -78.64(13) . . . . ? C27 C22 P1 C3 84.79(15) . . . . ? C23 C22 P1 C3 -97.31(14) . . . . ? C27 C22 P1 C16 -20.35(16) . . . . ? C23 C22 P1 C16 157.55(13) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.299 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.050 #------------------------------------------------------------------------------ data_4b-GSTR156 _database_code_depnum_ccdc_archive 'CCDC 859625' #TrackingRef 'Gesamtcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H21 N2 O P S' _chemical_formula_sum 'C27 H21 N2 O P S' _chemical_formula_weight 452.49 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 6.1718(5) _cell_length_b 11.5856(10) _cell_length_c 17.6005(16) _cell_angle_alpha 90.656(4) _cell_angle_beta 91.442(5) _cell_angle_gamma 100.489(6) _cell_volume 1236.92(18) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4088 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 28.70 _exptl_crystal_description needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9177 _exptl_absorpt_correction_T_max 0.9857 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14155 _diffrn_reflns_av_R_equivalents 0.0998 _diffrn_reflns_av_sigmaI/netI 0.1569 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4850 _reflns_number_gt 2491 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0237P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4850 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1082 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 0.825 _refine_ls_restrained_S_all 0.825 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0273(4) 0.1022(2) 0.19128(15) 0.0238(7) Uani 1 1 d . . . C2 C 0.1980(4) 0.2743(2) 0.24859(15) 0.0205(6) Uani 1 1 d . . . C3 C 0.0614(4) 0.2989(2) 0.19243(15) 0.0250(7) Uani 1 1 d . . . H3A H 0.0396 0.3752 0.1792 0.030 Uiso 1 1 calc R . . C4 C 0.2791(4) 0.0824(2) 0.30012(15) 0.0241(7) Uani 1 1 d . . . C5 C 0.4739(4) 0.0474(3) 0.28163(17) 0.0333(8) Uani 1 1 d . . . H5A H 0.5420 0.0697 0.2349 0.040 Uiso 1 1 calc R . . C6 C 0.5683(5) -0.0211(3) 0.3327(2) 0.0423(9) Uani 1 1 d . . . H6A H 0.7017 -0.0464 0.3208 0.051 Uiso 1 1 calc R . . C7 C 0.4696(5) -0.0520(3) 0.39994(19) 0.0447(9) Uani 1 1 d . . . H7A H 0.5358 -0.0982 0.4348 0.054 Uiso 1 1 calc R . . C8 C 0.2743(5) -0.0169(3) 0.41777(18) 0.0440(9) Uani 1 1 d . . . H8A H 0.2063 -0.0395 0.4645 0.053 Uiso 1 1 calc R . . C9 C 0.1780(5) 0.0511(3) 0.36782(17) 0.0345(8) Uani 1 1 d . . . H9A H 0.0442 0.0759 0.3798 0.041 Uiso 1 1 calc R . . C10 C -0.2072(4) 0.1892(2) 0.09794(15) 0.0216(6) Uani 1 1 d . . . C11 C -0.1830(5) 0.1339(2) 0.02944(16) 0.0277(7) Uani 1 1 d . . . H11A H -0.0561 0.1003 0.0210 0.033 Uiso 1 1 calc R . . C12 C -0.3447(5) 0.1281(3) -0.02613(16) 0.0350(8) Uani 1 1 d . . . H12A H -0.3303 0.0895 -0.0731 0.042 Uiso 1 1 calc R . . C13 C -0.5284(5) 0.1780(3) -0.01433(17) 0.0359(8) Uani 1 1 d . . . H13A H -0.6400 0.1736 -0.0530 0.043 Uiso 1 1 calc R . . C14 C -0.5484(4) 0.2341(3) 0.05395(17) 0.0339(8) Uani 1 1 d . . . H14A H -0.6750 0.2681 0.0621 0.041 Uiso 1 1 calc R . . C15 C -0.3880(4) 0.2416(2) 0.11042(16) 0.0270(7) Uani 1 1 d . . . H15A H -0.4010 0.2818 0.1570 0.032 Uiso 1 1 calc R . . C16 C 0.2989(4) 0.3481(2) 0.40318(15) 0.0259(7) Uani 1 1 d . . . C17 C 0.4606(5) 0.3565(2) 0.46048(16) 0.0308(7) Uani 1 1 d . . . H17A H 0.6117 0.3760 0.4481 0.037 Uiso 1 1 calc R . . C18 C 0.4039(6) 0.3370(3) 0.53513(18) 0.0420(8) Uani 1 1 d . . . H18A H 0.5154 0.3434 0.5739 0.050 Uiso 1 1 calc R . . C19 C 0.1868(6) 0.3083(3) 0.55308(18) 0.0500(10) Uani 1 1 d . . . H19A H 0.1479 0.2935 0.6044 0.060 Uiso 1 1 calc R . . C20 C 0.0227(6) 0.3007(3) 0.49689(19) 0.0505(10) Uani 1 1 d . . . H20A H -0.1278 0.2815 0.5100 0.061 Uiso 1 1 calc R . . C21 C 0.0773(5) 0.3208(3) 0.42175(17) 0.0348(8) Uani 1 1 d . . . H21A H -0.0350 0.3161 0.3833 0.042 Uiso 1 1 calc R . . C22 C 0.3466(4) 0.5140(2) 0.27869(15) 0.0223(6) Uani 1 1 d . . . C23 C 0.5208(5) 0.5843(3) 0.24374(19) 0.0429(9) Uani 1 1 d . . . H23A H 0.6534 0.5555 0.2363 0.052 Uiso 1 1 calc R . . C24 C 0.5047(5) 0.6958(3) 0.2195(2) 0.0574(11) Uani 1 1 d . . . H24A H 0.6244 0.7429 0.1951 0.069 Uiso 1 1 calc R . . C25 C 0.3131(5) 0.7374(3) 0.23114(19) 0.0438(9) Uani 1 1 d . . . H25A H 0.3008 0.8140 0.2151 0.053 Uiso 1 1 calc R . . C26 C 0.1396(5) 0.6691(3) 0.26579(17) 0.0393(8) Uani 1 1 d . . . H26A H 0.0078 0.6987 0.2732 0.047 Uiso 1 1 calc R . . C27 C 0.1543(5) 0.5571(3) 0.29011(16) 0.0313(7) Uani 1 1 d . . . H27A H 0.0337 0.5105 0.3144 0.038 Uiso 1 1 calc R . . N1 N 0.1752(3) 0.15128(19) 0.24716(12) 0.0226(5) Uani 1 1 d . . . N2 N -0.0408(3) 0.1964(2) 0.15753(12) 0.0230(5) Uani 1 1 d . . . O O 0.6231(3) 0.35610(16) 0.29940(10) 0.0285(5) Uani 1 1 d . . . P P 0.39072(11) 0.37149(7) 0.30761(4) 0.0234(2) Uani 1 1 d . . . S S -0.05137(12) -0.04074(7) 0.17122(4) 0.0328(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0250(15) 0.0214(17) 0.0254(17) -0.0011(13) 0.0003(13) 0.0053(13) C2 0.0179(14) 0.0184(16) 0.0254(16) 0.0010(13) -0.0023(12) 0.0043(12) C3 0.0261(16) 0.0162(17) 0.0320(18) -0.0050(14) 0.0017(14) 0.0022(13) C4 0.0255(15) 0.0227(17) 0.0242(17) 0.0001(13) -0.0085(13) 0.0060(13) C5 0.0329(18) 0.0295(19) 0.0375(19) -0.0012(15) -0.0054(14) 0.0069(15) C6 0.0378(19) 0.040(2) 0.053(2) -0.0080(18) -0.0146(17) 0.0204(17) C7 0.062(2) 0.027(2) 0.045(2) -0.0001(17) -0.0242(19) 0.0138(18) C8 0.061(2) 0.039(2) 0.032(2) 0.0073(16) -0.0051(17) 0.0089(18) C9 0.0403(18) 0.0302(19) 0.0332(19) 0.0010(15) -0.0035(15) 0.0080(15) C10 0.0196(14) 0.0231(17) 0.0205(16) 0.0004(13) -0.0056(12) 0.0005(12) C11 0.0290(16) 0.0250(18) 0.0281(18) -0.0012(14) 0.0006(14) 0.0025(13) C12 0.0428(19) 0.035(2) 0.0241(18) -0.0039(15) -0.0030(15) -0.0015(16) C13 0.0323(17) 0.041(2) 0.0324(19) 0.0039(16) -0.0099(14) 0.0029(16) C14 0.0230(16) 0.044(2) 0.0345(19) 0.0046(16) -0.0010(14) 0.0068(15) C15 0.0266(16) 0.0285(18) 0.0256(17) 0.0024(14) 0.0002(13) 0.0047(14) C16 0.0310(16) 0.0213(17) 0.0268(17) 0.0005(13) -0.0014(14) 0.0085(13) C17 0.0369(17) 0.0268(18) 0.0297(19) -0.0005(14) -0.0057(15) 0.0094(14) C18 0.057(2) 0.043(2) 0.030(2) -0.0030(16) -0.0082(16) 0.0202(18) C19 0.074(3) 0.059(3) 0.027(2) 0.0086(17) 0.0113(19) 0.037(2) C20 0.048(2) 0.071(3) 0.043(2) 0.0225(19) 0.0180(18) 0.034(2) C21 0.0336(18) 0.042(2) 0.0324(19) 0.0094(15) 0.0017(14) 0.0146(16) C22 0.0235(15) 0.0177(16) 0.0241(16) -0.0006(13) -0.0050(13) 0.0002(13) C23 0.0301(18) 0.038(2) 0.060(2) 0.0125(18) -0.0006(16) 0.0048(16) C24 0.038(2) 0.035(2) 0.095(3) 0.030(2) 0.002(2) -0.0044(17) C25 0.054(2) 0.024(2) 0.052(2) 0.0089(17) -0.0130(18) 0.0032(17) C26 0.050(2) 0.034(2) 0.037(2) 0.0003(16) -0.0024(16) 0.0183(17) C27 0.0378(18) 0.0302(19) 0.0278(18) 0.0042(14) 0.0055(14) 0.0102(15) N1 0.0196(12) 0.0230(15) 0.0249(14) -0.0026(11) -0.0028(10) 0.0040(10) N2 0.0248(13) 0.0231(14) 0.0215(13) -0.0033(11) -0.0026(10) 0.0061(11) O 0.0188(10) 0.0307(12) 0.0358(12) -0.0022(9) -0.0010(9) 0.0043(9) P 0.0215(4) 0.0223(5) 0.0260(4) -0.0019(3) -0.0035(3) 0.0036(3) S 0.0376(5) 0.0214(5) 0.0381(5) -0.0034(4) -0.0082(4) 0.0037(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.370(3) . ? C1 N2 1.375(3) . ? C1 S 1.670(3) . ? C2 C3 1.349(3) . ? C2 N1 1.407(3) . ? C2 P 1.785(3) . ? C3 N2 1.370(3) . ? C3 H3A 0.9500 . ? C4 C9 1.381(4) . ? C4 C5 1.381(3) . ? C4 N1 1.446(3) . ? C5 C6 1.391(4) . ? C5 H5A 0.9500 . ? C6 C7 1.367(4) . ? C6 H6A 0.9500 . ? C7 C8 1.383(4) . ? C7 H7A 0.9500 . ? C8 C9 1.381(4) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.383(4) . ? C10 C15 1.384(3) . ? C10 N2 1.440(3) . ? C11 C12 1.372(4) . ? C11 H11A 0.9500 . ? C12 C13 1.382(4) . ? C12 H12A 0.9500 . ? C13 C14 1.379(4) . ? C13 H13A 0.9500 . ? C14 C15 1.376(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C17 1.391(4) . ? C16 C21 1.395(4) . ? C16 P 1.796(3) . ? C17 C18 1.379(4) . ? C17 H17A 0.9500 . ? C18 C19 1.366(4) . ? C18 H18A 0.9500 . ? C19 C20 1.388(4) . ? C19 H19A 0.9500 . ? C20 C21 1.385(4) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.387(4) . ? C22 C27 1.387(3) . ? C22 P 1.799(3) . ? C23 C24 1.385(4) . ? C23 H23A 0.9500 . ? C24 C25 1.375(4) . ? C24 H24A 0.9500 . ? C25 C26 1.371(4) . ? C25 H25A 0.9500 . ? C26 C27 1.388(4) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? O P 1.4875(17) . ? 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 C1 N2 104.5(2) . . ? N1 C1 S 126.7(2) . . ? N2 C1 S 128.9(2) . . ? C3 C2 N1 105.1(2) . . ? C3 C2 P 129.7(2) . . ? N1 C2 P 124.96(18) . . ? C2 C3 N2 109.3(2) . . ? C2 C3 H3A 125.3 . . ? N2 C3 H3A 125.3 . . ? C9 C4 C5 121.5(3) . . ? C9 C4 N1 118.8(2) . . ? C5 C4 N1 119.8(2) . . ? C4 C5 C6 118.8(3) . . ? C4 C5 H5A 120.6 . . ? C6 C5 H5A 120.6 . . ? C7 C6 C5 120.1(3) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C6 C7 C8 120.6(3) . . ? C6 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? C9 C8 C7 120.1(3) . . ? C9 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? C4 C9 C8 118.9(3) . . ? C4 C9 H9A 120.5 . . ? C8 C9 H9A 120.5 . . ? C11 C10 C15 121.2(2) . . ? C11 C10 N2 120.5(2) . . ? C15 C10 N2 118.3(2) . . ? C12 C11 C10 119.1(3) . . ? C12 C11 H11A 120.4 . . ? C10 C11 H11A 120.4 . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H12A 119.7 . . ? C13 C12 H12A 119.7 . . ? C14 C13 C12 119.5(3) . . ? C14 C13 H13A 120.2 . . ? C12 C13 H13A 120.2 . . ? C15 C14 C13 121.0(3) . . ? C15 C14 H14A 119.5 . . ? C13 C14 H14A 119.5 . . ? C14 C15 C10 118.5(3) . . ? C14 C15 H15A 120.7 . . ? C10 C15 H15A 120.7 . . ? C17 C16 C21 119.5(3) . . ? C17 C16 P 117.1(2) . . ? C21 C16 P 123.4(2) . . ? C18 C17 C16 120.7(3) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C19 C18 C17 119.8(3) . . ? C19 C18 H18A 120.1 . . ? C17 C18 H18A 120.1 . . ? C18 C19 C20 120.5(3) . . ? C18 C19 H19A 119.8 . . ? C20 C19 H19A 119.8 . . ? C21 C20 C19 120.3(3) . . ? C21 C20 H20A 119.8 . . ? C19 C20 H20A 119.8 . . ? C20 C21 C16 119.2(3) . . ? C20 C21 H21A 120.4 . . ? C16 C21 H21A 120.4 . . ? C23 C22 C27 119.1(3) . . ? C23 C22 P 116.4(2) . . ? C27 C22 P 124.5(2) . . ? C24 C23 C22 121.1(3) . . ? C24 C23 H23A 119.4 . . ? C22 C23 H23A 119.4 . . ? C25 C24 C23 119.1(3) . . ? C25 C24 H24A 120.5 . . ? C23 C24 H24A 120.5 . . ? C26 C25 C24 120.5(3) . . ? C26 C25 H25A 119.8 . . ? C24 C25 H25A 119.8 . . ? C25 C26 C27 120.8(3) . . ? C25 C26 H26A 119.6 . . ? C27 C26 H26A 119.6 . . ? C22 C27 C26 119.4(3) . . ? C22 C27 H27A 120.3 . . ? C26 C27 H27A 120.3 . . ? C1 N1 C2 111.0(2) . . ? C1 N1 C4 123.0(2) . . ? C2 N1 C4 125.8(2) . . ? C3 N2 C1 110.1(2) . . ? C3 N2 C10 124.3(2) . . ? C1 N2 C10 125.5(2) . . ? O P C2 113.79(11) . . ? O P C16 112.32(12) . . ? C2 P C16 106.09(13) . . ? O P C22 112.70(12) . . ? C2 P C22 102.83(12) . . ? C16 P C22 108.45(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.2(3) . . . . ? P C2 C3 N2 173.90(18) . . . . ? C9 C4 C5 C6 0.2(4) . . . . ? N1 C4 C5 C6 -178.6(3) . . . . ? C4 C5 C6 C7 -0.4(4) . . . . ? C5 C6 C7 C8 0.6(5) . . . . ? C6 C7 C8 C9 -0.6(5) . . . . ? C5 C4 C9 C8 -0.2(4) . . . . ? N1 C4 C9 C8 178.6(3) . . . . ? C7 C8 C9 C4 0.4(5) . . . . ? C15 C10 C11 C12 -1.9(4) . . . . ? N2 C10 C11 C12 179.8(3) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? C11 C12 C13 C14 0.1(5) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C13 C14 C15 C10 -1.4(4) . . . . ? C11 C10 C15 C14 2.2(4) . . . . ? N2 C10 C15 C14 -179.4(3) . . . . ? C21 C16 C17 C18 0.7(4) . . . . ? P C16 C17 C18 -178.4(2) . . . . ? C16 C17 C18 C19 0.4(4) . . . . ? C17 C18 C19 C20 -1.1(5) . . . . ? C18 C19 C20 C21 0.7(5) . . . . ? C19 C20 C21 C16 0.4(5) . . . . ? C17 C16 C21 C20 -1.1(4) . . . . ? P C16 C21 C20 178.0(2) . . . . ? C27 C22 C23 C24 -0.7(5) . . . . ? P C22 C23 C24 -179.8(3) . . . . ? C22 C23 C24 C25 0.7(5) . . . . ? C23 C24 C25 C26 -0.5(5) . . . . ? C24 C25 C26 C27 0.4(5) . . . . ? C23 C22 C27 C26 0.5(4) . . . . ? P C22 C27 C26 179.5(2) . . . . ? C25 C26 C27 C22 -0.4(5) . . . . ? N2 C1 N1 C2 0.4(3) . . . . ? S C1 N1 C2 -178.78(18) . . . . ? N2 C1 N1 C4 176.3(2) . . . . ? S C1 N1 C4 -2.8(4) . . . . ? C3 C2 N1 C1 -0.1(3) . . . . ? P C2 N1 C1 -174.58(18) . . . . ? C3 C2 N1 C4 -175.9(2) . . . . ? P C2 N1 C4 9.6(4) . . . . ? C9 C4 N1 C1 -90.4(3) . . . . ? C5 C4 N1 C1 88.4(3) . . . . ? C9 C4 N1 C2 85.0(3) . . . . ? C5 C4 N1 C2 -96.2(3) . . . . ? C2 C3 N2 C1 0.5(3) . . . . ? C2 C3 N2 C10 176.2(2) . . . . ? N1 C1 N2 C3 -0.5(3) . . . . ? S C1 N2 C3 178.63(19) . . . . ? N1 C1 N2 C10 -176.2(2) . . . . ? S C1 N2 C10 2.9(4) . . . . ? C11 C10 N2 C3 125.7(3) . . . . ? C15 C10 N2 C3 -52.7(4) . . . . ? C11 C10 N2 C1 -59.2(4) . . . . ? C15 C10 N2 C1 122.5(3) . . . . ? C3 C2 P O -118.3(2) . . . . ? N1 C2 P O 54.7(2) . . . . ? C3 C2 P C16 117.7(3) . . . . ? N1 C2 P C16 -69.3(2) . . . . ? C3 C2 P C22 3.9(3) . . . . ? N1 C2 P C22 176.9(2) . . . . ? C17 C16 P O 19.9(3) . . . . ? C21 C16 P O -159.2(2) . . . . ? C17 C16 P C2 144.9(2) . . . . ? C21 C16 P C2 -34.3(3) . . . . ? C17 C16 P C22 -105.3(2) . . . . ? C21 C16 P C22 75.6(3) . . . . ? C23 C22 P O 8.2(3) . . . . ? C27 C22 P O -170.8(2) . . . . ? C23 C22 P C2 -114.7(2) . . . . ? C27 C22 P C2 66.3(3) . . . . ? C23 C22 P C16 133.2(2) . . . . ? C27 C22 P C16 -45.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.253 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.060 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.014 0.500 1.000 159 54 ' ' _platon_squeeze_details ; ; #------------------------------------------------------------------------------ data_4d-GSTR181 _database_code_depnum_ccdc_archive 'CCDC 859626' #TrackingRef 'Gesamtcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 N2 O P S' _chemical_formula_sum 'C19 H21 N2 O P S' _chemical_formula_weight 356.41 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 'P 21/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 10.9872(5) _cell_length_b 17.9986(8) _cell_length_c 9.5368(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.234(3) _cell_angle_gamma 90.00 _cell_volume 1874.79(14) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4618 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 29.13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9012 _exptl_absorpt_correction_T_max 0.9587 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17455 _diffrn_reflns_av_R_equivalents 0.1074 _diffrn_reflns_av_sigmaI/netI 0.0910 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4494 _reflns_number_gt 2925 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4494 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -1.05586(17) -0.09136(10) -0.91756(19) 0.0225(4) Uani 1 1 d . . . C2 C -0.88024(17) -0.15327(10) -0.93023(18) 0.0232(4) Uani 1 1 d . . . H2A H -0.8181 -0.1817 -0.9671 0.028 Uiso 1 1 calc R . . C3 C -0.87752(17) -0.12796(9) -0.79691(18) 0.0207(4) Uani 1 1 d . . . C4 C -1.02849(19) -0.14866(11) -1.15250(19) 0.0295(5) Uani 1 1 d . . . H4A H -1.0883 -0.1098 -1.1901 0.035 Uiso 1 1 calc R . . C5 C -1.0942(2) -0.22294(13) -1.1599(2) 0.0451(6) Uani 1 1 d . . . H5A H -1.1221 -0.2347 -1.2585 0.068 Uiso 1 1 calc R . . H5B H -1.1649 -0.2203 -1.1057 0.068 Uiso 1 1 calc R . . H5C H -1.0381 -0.2617 -1.1204 0.068 Uiso 1 1 calc R . . C6 C -0.9211(2) -0.14672(12) -1.2393(2) 0.0368(5) Uani 1 1 d . . . H6A H -0.8770 -0.0997 -1.2227 0.055 Uiso 1 1 calc R . . H6B H -0.9511 -0.1510 -1.3396 0.055 Uiso 1 1 calc R . . H6C H -0.8659 -0.1882 -1.2119 0.055 Uiso 1 1 calc R . . C7 C -1.02962(19) -0.05746(11) -0.66290(19) 0.0290(5) Uani 1 1 d . . . H7A H -1.1193 -0.0564 -0.6724 0.043 Uiso 1 1 calc R . . H7B H -0.9979 -0.0067 -0.6509 0.043 Uiso 1 1 calc R . . H7C H -0.9995 -0.0874 -0.5805 0.043 Uiso 1 1 calc R . . C8 C -0.63337(17) -0.17394(10) -0.74328(18) 0.0228(4) Uani 1 1 d . . . C9 C -0.57833(19) -0.24171(11) -0.7044(2) 0.0313(5) Uani 1 1 d . . . H9A H -0.6123 -0.2726 -0.6378 0.038 Uiso 1 1 calc R . . C10 C -0.4745(2) -0.26402(13) -0.7625(2) 0.0408(6) Uani 1 1 d . . . H10A H -0.4371 -0.3101 -0.7352 0.049 Uiso 1 1 calc R . . C11 C -0.4249(2) -0.22004(13) -0.8595(2) 0.0401(6) Uani 1 1 d . . . H11A H -0.3534 -0.2358 -0.8989 0.048 Uiso 1 1 calc R . . C12 C -0.47894(19) -0.15258(12) -0.8999(2) 0.0329(5) Uani 1 1 d . . . H12A H -0.4443 -0.1221 -0.9666 0.039 Uiso 1 1 calc R . . C13 C -0.58335(18) -0.12990(10) -0.8430(2) 0.0268(4) Uani 1 1 d . . . H13A H -0.6212 -0.0841 -0.8718 0.032 Uiso 1 1 calc R . . C14 C -0.72023(16) -0.05627(10) -0.57631(18) 0.0213(4) Uani 1 1 d . . . C15 C -0.73161(18) 0.01009(10) -0.6520(2) 0.0253(4) Uani 1 1 d . . . H15A H -0.7649 0.0099 -0.7482 0.030 Uiso 1 1 calc R . . C16 C -0.69428(18) 0.07634(11) -0.5866(2) 0.0304(5) Uani 1 1 d . . . H16A H -0.7026 0.1216 -0.6381 0.036 Uiso 1 1 calc R . . C17 C -0.64503(18) 0.07693(11) -0.4468(2) 0.0316(5) Uani 1 1 d . . . H17A H -0.6189 0.1224 -0.4029 0.038 Uiso 1 1 calc R . . C18 C -0.6338(2) 0.01143(11) -0.3712(2) 0.0325(5) Uani 1 1 d . . . H18A H -0.6003 0.0120 -0.2751 0.039 Uiso 1 1 calc R . . C19 C -0.67125(18) -0.05524(11) -0.4349(2) 0.0269(4) Uani 1 1 d . . . H19A H -0.6636 -0.1002 -0.3824 0.032 Uiso 1 1 calc R . . N1 N -0.98837(14) -0.13088(8) -1.00345(15) 0.0223(4) Uani 1 1 d . . . N2 N -0.98812(14) -0.09010(8) -0.78926(15) 0.0214(3) Uani 1 1 d . . . O O -0.79482(12) -0.19939(7) -0.54812(13) 0.0267(3) Uani 1 1 d . . . P P -0.76145(4) -0.14483(2) -0.65445(5) 0.02064(13) Uani 1 1 d . . . S S -1.19404(5) -0.05214(3) -0.95979(5) 0.03164(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0225(10) 0.0234(9) 0.0214(9) 0.0013(8) 0.0016(8) -0.0019(8) C2 0.0216(10) 0.0233(9) 0.0243(10) -0.0002(8) 0.0017(8) 0.0009(8) C3 0.0206(10) 0.0190(8) 0.0225(10) -0.0008(7) 0.0023(8) 0.0005(8) C4 0.0326(12) 0.0341(11) 0.0200(10) -0.0042(8) -0.0055(8) 0.0092(9) C5 0.0389(14) 0.0511(14) 0.0430(13) -0.0175(11) -0.0055(11) -0.0045(11) C6 0.0474(14) 0.0394(12) 0.0238(10) 0.0014(9) 0.0057(10) 0.0090(10) C7 0.0282(11) 0.0362(11) 0.0230(10) -0.0023(8) 0.0056(8) 0.0057(9) C8 0.0206(10) 0.0250(9) 0.0217(10) -0.0060(8) -0.0028(8) 0.0000(8) C9 0.0303(12) 0.0303(10) 0.0331(12) -0.0003(9) 0.0023(9) 0.0045(9) C10 0.0373(14) 0.0434(13) 0.0417(13) -0.0014(11) 0.0043(11) 0.0178(11) C11 0.0260(12) 0.0560(14) 0.0382(13) -0.0145(11) 0.0026(10) 0.0101(11) C12 0.0269(12) 0.0433(12) 0.0286(11) -0.0079(10) 0.0036(9) -0.0062(10) C13 0.0255(11) 0.0280(10) 0.0266(10) -0.0035(8) 0.0016(8) -0.0013(8) C14 0.0179(10) 0.0242(9) 0.0224(9) -0.0012(8) 0.0048(7) 0.0001(8) C15 0.0263(11) 0.0257(9) 0.0238(10) -0.0003(8) 0.0017(8) -0.0031(8) C16 0.0273(11) 0.0248(10) 0.0393(12) 0.0015(9) 0.0049(9) -0.0026(8) C17 0.0272(12) 0.0316(11) 0.0365(12) -0.0112(9) 0.0054(9) -0.0037(9) C18 0.0302(12) 0.0400(12) 0.0261(10) -0.0089(9) -0.0016(9) -0.0020(9) C19 0.0253(11) 0.0313(10) 0.0239(10) -0.0009(8) 0.0021(8) -0.0008(9) N1 0.0216(9) 0.0253(8) 0.0192(8) -0.0018(6) -0.0008(7) 0.0022(7) N2 0.0195(8) 0.0239(8) 0.0209(8) -0.0011(7) 0.0032(6) 0.0017(7) O 0.0306(8) 0.0249(7) 0.0245(7) 0.0042(5) 0.0021(6) -0.0027(6) P 0.0211(3) 0.0203(2) 0.0201(2) 0.00045(19) 0.00055(19) 0.0000(2) S 0.0229(3) 0.0425(3) 0.0291(3) 0.0012(2) 0.0006(2) 0.0082(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.362(2) . ? C1 N1 1.363(2) . ? C1 S 1.6831(19) . ? C2 C3 1.348(2) . ? C2 N1 1.372(2) . ? C2 H2A 0.9500 . ? C3 N2 1.402(2) . ? C3 P 1.7857(18) . ? C4 N1 1.477(2) . ? C4 C6 1.513(3) . ? C4 C5 1.518(3) . ? C4 H4A 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N2 1.458(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.394(3) . ? C8 C13 1.395(3) . ? C8 P 1.798(2) . ? C9 C10 1.381(3) . ? C9 H9A 0.9500 . ? C10 C11 1.375(3) . ? C10 H10A 0.9500 . ? C11 C12 1.388(3) . ? C11 H11A 0.9500 . ? C12 C13 1.383(3) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.394(2) . ? C14 C19 1.397(2) . ? C14 P 1.7966(18) . ? C15 C16 1.387(3) . ? C15 H15A 0.9500 . ? C16 C17 1.383(3) . ? C16 H16A 0.9500 . ? C17 C18 1.381(3) . ? C17 H17A 0.9500 . ? C18 C19 1.387(3) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? O P 1.4858(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 105.58(15) . . ? N2 C1 S 126.80(14) . . ? N1 C1 S 127.62(13) . . ? C3 C2 N1 108.07(17) . . ? C3 C2 H2A 126.0 . . ? N1 C2 H2A 126.0 . . ? C2 C3 N2 106.43(15) . . ? C2 C3 P 126.94(15) . . ? N2 C3 P 126.48(13) . . ? N1 C4 C6 110.65(16) . . ? N1 C4 C5 109.07(16) . . ? C6 C4 C5 112.96(17) . . ? N1 C4 H4A 108.0 . . ? C6 C4 H4A 108.0 . . ? C5 C4 H4A 108.0 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 119.14(18) . . ? C9 C8 P 117.95(15) . . ? C13 C8 P 122.81(14) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C11 C10 C9 120.5(2) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C10 C11 C12 120.1(2) . . ? C10 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C13 C12 C11 119.8(2) . . ? C13 C12 H12A 120.1 . . ? C11 C12 H12A 120.1 . . ? C12 C13 C8 120.32(18) . . ? C12 C13 H13A 119.8 . . ? C8 C13 H13A 119.8 . . ? C15 C14 C19 119.46(16) . . ? C15 C14 P 122.76(13) . . ? C19 C14 P 117.75(13) . . ? C16 C15 C14 119.90(17) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C17 C16 C15 120.36(18) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C18 C17 C16 120.03(18) . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C17 C18 C19 120.30(19) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C18 C19 C14 119.95(18) . . ? C18 C19 H19A 120.0 . . ? C14 C19 H19A 120.0 . . ? C1 N1 C2 110.18(14) . . ? C1 N1 C4 124.49(15) . . ? C2 N1 C4 125.30(16) . . ? C1 N2 C3 109.72(15) . . ? C1 N2 C7 124.06(15) . . ? C3 N2 C7 126.14(14) . . ? O P C3 115.02(8) . . ? O P C14 111.90(8) . . ? C3 P C14 106.96(8) . . ? O P C8 113.14(8) . . ? C3 P C8 102.82(8) . . ? C14 P C8 106.21(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 0.8(2) . . . . ? N1 C2 C3 P 176.70(13) . . . . ? C13 C8 C9 C10 1.0(3) . . . . ? P C8 C9 C10 -175.49(16) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C11 C12 C13 C8 1.1(3) . . . . ? C9 C8 C13 C12 -1.4(3) . . . . ? P C8 C13 C12 174.95(14) . . . . ? C19 C14 C15 C16 0.1(3) . . . . ? P C14 C15 C16 -177.83(15) . . . . ? C14 C15 C16 C17 0.4(3) . . . . ? C15 C16 C17 C18 -0.6(3) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? C17 C18 C19 C14 0.2(3) . . . . ? C15 C14 C19 C18 -0.4(3) . . . . ? P C14 C19 C18 177.63(16) . . . . ? N2 C1 N1 C2 -0.48(19) . . . . ? S C1 N1 C2 179.58(14) . . . . ? N2 C1 N1 C4 177.79(16) . . . . ? S C1 N1 C4 -2.1(3) . . . . ? C3 C2 N1 C1 -0.2(2) . . . . ? C3 C2 N1 C4 -178.49(17) . . . . ? C6 C4 N1 C1 144.01(18) . . . . ? C5 C4 N1 C1 -91.1(2) . . . . ? C6 C4 N1 C2 -38.0(2) . . . . ? C5 C4 N1 C2 86.9(2) . . . . ? N1 C1 N2 C3 1.00(19) . . . . ? S C1 N2 C3 -179.06(14) . . . . ? N1 C1 N2 C7 -175.90(16) . . . . ? S C1 N2 C7 4.0(3) . . . . ? C2 C3 N2 C1 -1.2(2) . . . . ? P C3 N2 C1 -177.06(13) . . . . ? C2 C3 N2 C7 175.66(17) . . . . ? P C3 N2 C7 -0.2(3) . . . . ? C2 C3 P O -104.75(18) . . . . ? N2 C3 P O 70.32(17) . . . . ? C2 C3 P C14 130.31(17) . . . . ? N2 C3 P C14 -54.62(18) . . . . ? C2 C3 P C8 18.68(19) . . . . ? N2 C3 P C8 -166.25(15) . . . . ? C15 C14 P O -154.24(16) . . . . ? C19 C14 P O 27.85(18) . . . . ? C15 C14 P C3 -27.43(19) . . . . ? C19 C14 P C3 154.65(15) . . . . ? C15 C14 P C8 81.85(17) . . . . ? C19 C14 P C8 -96.06(16) . . . . ? C9 C8 P O -0.89(17) . . . . ? C13 C8 P O -177.27(13) . . . . ? C9 C8 P C3 -125.56(15) . . . . ? C13 C8 P C3 58.06(16) . . . . ? C9 C8 P C14 122.24(15) . . . . ? C13 C8 P C14 -54.13(16) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.299 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.064 #------------------------------------------------------------------------------ data_5b-GSTR079 _database_code_depnum_ccdc_archive 'CCDC 859627' #TrackingRef 'Gesamtcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C27 H21 N2 P S2), C7 H8' _chemical_formula_sum 'C61 H50 N4 P2 S4' _chemical_formula_weight 1029.23 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4324(4) _cell_length_b 13.1652(5) _cell_length_c 17.5344(6) _cell_angle_alpha 92.807(3) _cell_angle_beta 90.312(2) _cell_angle_gamma 99.283(2) _cell_volume 2601.17(16) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9109 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.83107 _exptl_absorpt_correction_T_max 0.95431 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30756 _diffrn_reflns_av_R_equivalents 0.0821 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 26.00 _reflns_number_total 10096 _reflns_number_gt 7172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.6725P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10096 _refine_ls_number_parameters 641 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1134(2) 0.25226(17) -0.20025(12) 0.0226(5) Uani 1 1 d . . . C2 C -0.3123(2) 0.21785(17) -0.18462(13) 0.0219(5) Uani 1 1 d . . . H2A H -0.3889 0.2204 -0.1645 0.026 Uiso 1 1 calc R . . C3 C -0.2877(2) 0.15876(17) -0.24579(13) 0.0220(5) Uani 1 1 d . . . C4 C -0.0945(2) 0.13185(19) -0.30979(14) 0.0271(6) Uani 1 1 d . . . C5 C -0.0661(2) 0.0365(2) -0.29531(16) 0.0360(6) Uani 1 1 d . . . H5A H -0.0941 0.0019 -0.2510 0.043 Uiso 1 1 calc R . . C6 C 0.0053(3) -0.0077(2) -0.3478(2) 0.0502(9) Uani 1 1 d . . . H6A H 0.0263 -0.0732 -0.3392 0.060 Uiso 1 1 calc R . . C7 C 0.0449(3) 0.0426(3) -0.41116(19) 0.0554(10) Uani 1 1 d . . . H7A H 0.0936 0.0121 -0.4462 0.066 Uiso 1 1 calc R . . C8 C 0.0150(3) 0.1368(3) -0.42463(17) 0.0551(9) Uani 1 1 d . . . H8A H 0.0424 0.1709 -0.4692 0.066 Uiso 1 1 calc R . . C9 C -0.0557(2) 0.1830(2) -0.37302(15) 0.0379(7) Uani 1 1 d . . . H9A H -0.0763 0.2485 -0.3818 0.045 Uiso 1 1 calc R . . C10 C -0.1934(2) 0.34813(17) -0.09231(12) 0.0220(5) Uani 1 1 d . . . C11 C -0.1432(2) 0.3237(2) -0.02519(13) 0.0287(6) Uani 1 1 d . . . H11A H -0.1211 0.2577 -0.0205 0.034 Uiso 1 1 calc R . . C12 C -0.1255(2) 0.3964(2) 0.03503(14) 0.0360(6) Uani 1 1 d . . . H12A H -0.0914 0.3803 0.0815 0.043 Uiso 1 1 calc R . . C13 C -0.1570(2) 0.4919(2) 0.02804(15) 0.0368(7) Uani 1 1 d . . . H13A H -0.1422 0.5423 0.0691 0.044 Uiso 1 1 calc R . . C14 C -0.2100(3) 0.5147(2) -0.03839(16) 0.0391(7) Uani 1 1 d . . . H14A H -0.2342 0.5799 -0.0425 0.047 Uiso 1 1 calc R . . C15 C -0.2282(2) 0.44207(19) -0.09947(14) 0.0321(6) Uani 1 1 d . . . H15A H -0.2643 0.4575 -0.1455 0.039 Uiso 1 1 calc R . . C16 C -0.3602(2) 0.09149(18) -0.40143(12) 0.0223(5) Uani 1 1 d . . . C17 C -0.3530(3) 0.1907(2) -0.42556(14) 0.0354(6) Uani 1 1 d . . . H17A H -0.3589 0.2459 -0.3896 0.042 Uiso 1 1 calc R . . C18 C -0.3369(3) 0.2097(2) -0.50229(16) 0.0427(7) Uani 1 1 d . . . H18A H -0.3318 0.2779 -0.5188 0.051 Uiso 1 1 calc R . . C19 C -0.3284(2) 0.1290(2) -0.55504(15) 0.0368(6) Uani 1 1 d . . . H19A H -0.3171 0.1421 -0.6075 0.044 Uiso 1 1 calc R . . C20 C -0.3363(2) 0.0305(2) -0.53136(14) 0.0332(6) Uani 1 1 d . . . H20A H -0.3308 -0.0246 -0.5675 0.040 Uiso 1 1 calc R . . C21 C -0.3524(2) 0.01102(19) -0.45433(14) 0.0287(5) Uani 1 1 d . . . H21A H -0.3580 -0.0574 -0.4381 0.034 Uiso 1 1 calc R . . C22 C -0.5323(2) 0.09099(17) -0.27758(12) 0.0222(5) Uani 1 1 d . . . C23 C -0.6182(2) 0.01001(19) -0.25709(13) 0.0284(6) Uani 1 1 d . . . H23A H -0.5987 -0.0571 -0.2540 0.034 Uiso 1 1 calc R . . C24 C -0.7324(2) 0.0269(2) -0.24120(14) 0.0329(6) Uani 1 1 d . . . H24A H -0.7911 -0.0288 -0.2280 0.040 Uiso 1 1 calc R . . C25 C -0.7611(2) 0.1243(2) -0.24454(14) 0.0321(6) Uani 1 1 d . . . H25A H -0.8392 0.1359 -0.2333 0.039 Uiso 1 1 calc R . . C26 C -0.6761(2) 0.2049(2) -0.26429(13) 0.0287(6) Uani 1 1 d . . . H26A H -0.6960 0.2720 -0.2661 0.034 Uiso 1 1 calc R . . C27 C -0.5621(2) 0.18943(19) -0.28160(13) 0.0269(5) Uani 1 1 d . . . H27A H -0.5046 0.2453 -0.2961 0.032 Uiso 1 1 calc R . . C28 C 0.0864(2) 0.25597(17) 0.19978(13) 0.0226(5) Uani 1 1 d . . . C29 C 0.2864(2) 0.28685(17) 0.18972(13) 0.0219(5) Uani 1 1 d . . . H29A H 0.3639 0.2838 0.1715 0.026 Uiso 1 1 calc R . . C30 C 0.25896(19) 0.34386(17) 0.25157(12) 0.0203(5) Uani 1 1 d . . . C31 C 0.0646(2) 0.36830(18) 0.31405(13) 0.0258(5) Uani 1 1 d . . . C32 C 0.0279(2) 0.4616(2) 0.30217(16) 0.0335(6) Uani 1 1 d . . . H32A H 0.0500 0.4977 0.2575 0.040 Uiso 1 1 calc R . . C33 C -0.0424(2) 0.5012(2) 0.35757(19) 0.0462(8) Uani 1 1 d . . . H33A H -0.0677 0.5655 0.3508 0.055 Uiso 1 1 calc R . . C34 C -0.0752(2) 0.4481(3) 0.42151(18) 0.0508(9) Uani 1 1 d . . . H34A H -0.1234 0.4757 0.4586 0.061 Uiso 1 1 calc R . . C35 C -0.0386(3) 0.3551(3) 0.43220(17) 0.0496(8) Uani 1 1 d . . . H35A H -0.0614 0.3188 0.4766 0.060 Uiso 1 1 calc R . . C36 C 0.0318(2) 0.3143(2) 0.37777(15) 0.0353(6) Uani 1 1 d . . . H36A H 0.0568 0.2499 0.3846 0.042 Uiso 1 1 calc R . . C37 C 0.1722(2) 0.16262(17) 0.09197(12) 0.0225(5) Uani 1 1 d . . . C38 C 0.1191(2) 0.18697(19) 0.02581(13) 0.0279(5) Uani 1 1 d . . . H38A H 0.0908 0.2507 0.0230 0.034 Uiso 1 1 calc R . . C39 C 0.1077(2) 0.1167(2) -0.03649(14) 0.0337(6) Uani 1 1 d . . . H39A H 0.0711 0.1321 -0.0823 0.040 Uiso 1 1 calc R . . C40 C 0.1494(2) 0.0245(2) -0.03209(14) 0.0348(6) Uani 1 1 d . . . H40A H 0.1406 -0.0237 -0.0746 0.042 Uiso 1 1 calc R . . C41 C 0.2039(2) 0.0023(2) 0.03400(15) 0.0343(6) Uani 1 1 d . . . H41A H 0.2334 -0.0609 0.0365 0.041 Uiso 1 1 calc R . . C42 C 0.2161(2) 0.07152(19) 0.09688(14) 0.0297(6) Uani 1 1 d . . . H42A H 0.2538 0.0564 0.1424 0.036 Uiso 1 1 calc R . . C43 C 0.3393(2) 0.39782(19) 0.40702(13) 0.0244(5) Uani 1 1 d . . . C44 C 0.3503(2) 0.4733(2) 0.46601(14) 0.0323(6) Uani 1 1 d . . . H44A H 0.3646 0.5441 0.4548 0.039 Uiso 1 1 calc R . . C45 C 0.3404(3) 0.4453(3) 0.54122(15) 0.0456(8) Uani 1 1 d . . . H45A H 0.3469 0.4968 0.5816 0.055 Uiso 1 1 calc R . . C46 C 0.3212(3) 0.3434(3) 0.55714(17) 0.0615(10) Uani 1 1 d . . . H46A H 0.3157 0.3245 0.6088 0.074 Uiso 1 1 calc R . . C47 C 0.3098(3) 0.2674(3) 0.49890(17) 0.0599(10) Uani 1 1 d . . . H47A H 0.2959 0.1968 0.5107 0.072 Uiso 1 1 calc R . . C48 C 0.3187(3) 0.2940(2) 0.42313(15) 0.0387(7) Uani 1 1 d . . . H48A H 0.3109 0.2422 0.3830 0.046 Uiso 1 1 calc R . . C49 C 0.5023(2) 0.42318(17) 0.27896(12) 0.0220(5) Uani 1 1 d . . . C50 C 0.5541(2) 0.3381(2) 0.29767(14) 0.0303(6) Uani 1 1 d . . . H50A H 0.5109 0.2850 0.3259 0.036 Uiso 1 1 calc R . . C51 C 0.6682(2) 0.3316(2) 0.27507(15) 0.0349(6) Uani 1 1 d . . . H51A H 0.7033 0.2740 0.2880 0.042 Uiso 1 1 calc R . . C52 C 0.7317(2) 0.4080(2) 0.23394(15) 0.0366(7) Uani 1 1 d . . . H52A H 0.8099 0.4024 0.2182 0.044 Uiso 1 1 calc R . . C53 C 0.6817(2) 0.4926(2) 0.21561(16) 0.0386(7) Uani 1 1 d . . . H53A H 0.7260 0.5456 0.1879 0.046 Uiso 1 1 calc R . . C54 C 0.5666(2) 0.5001(2) 0.23769(14) 0.0311(6) Uani 1 1 d . . . H54A H 0.5320 0.5579 0.2245 0.037 Uiso 1 1 calc R . . C55 C 0.4480(2) 0.7907(2) -0.04094(15) 0.0374(6) Uani 1 1 d . . . C56 C 0.4609(3) 0.6890(3) -0.0504(2) 0.0577(9) Uani 1 1 d U . . H56A H 0.4208 0.6469 -0.0911 0.069 Uiso 1 1 calc R . . C57 C 0.5331(4) 0.6481(3) 0.0000(3) 0.0849(13) Uani 1 1 d U . . H57A H 0.5416 0.5775 -0.0061 0.102 Uiso 1 1 calc R . . C58 C 0.5928(3) 0.7095(3) 0.0590(2) 0.0696(10) Uani 1 1 d U . . H58A H 0.6431 0.6816 0.0928 0.084 Uiso 1 1 calc R . . C59 C 0.5789(3) 0.8092(3) 0.06796(17) 0.0490(8) Uani 1 1 d . . . H59A H 0.6185 0.8517 0.1087 0.059 Uiso 1 1 calc R . . C60 C 0.5077(3) 0.8491(2) 0.01847(15) 0.0431(7) Uani 1 1 d . . . H60A H 0.4992 0.9195 0.0254 0.052 Uiso 1 1 calc R . . C61 C 0.3729(3) 0.8366(3) -0.09637(19) 0.0688(10) Uani 1 1 d . . . H61C H 0.3620 0.9054 -0.0768 0.103 Uiso 1 1 calc R . . H61B H 0.2954 0.7925 -0.1026 0.103 Uiso 1 1 calc R . . H61A H 0.4122 0.8418 -0.1459 0.103 Uiso 1 1 calc R . . N1 N -0.16404(16) 0.18008(14) -0.25448(10) 0.0223(4) Uani 1 1 d . . . N2 N -0.20694(16) 0.27393(14) -0.15635(10) 0.0218(4) Uani 1 1 d . . . N3 N 0.13512(16) 0.32508(14) 0.25672(10) 0.0219(4) Uani 1 1 d . . . N4 N 0.18192(16) 0.23391(14) 0.15780(10) 0.0213(4) Uani 1 1 d . . . P1 P -0.38605(5) 0.06238(4) -0.30178(3) 0.02141(15) Uani 1 1 d . . . P2 P 0.35490(5) 0.43889(4) 0.31000(3) 0.01981(14) Uani 1 1 d . . . S1 S 0.02901(5) 0.30418(5) -0.19037(4) 0.03141(17) Uani 1 1 d . . . S2 S -0.36889(6) -0.07917(5) -0.28197(4) 0.02979(16) Uani 1 1 d . . . S3 S -0.05665(5) 0.20951(5) 0.18519(4) 0.02990(16) Uani 1 1 d . . . S4 S 0.32212(6) 0.57836(4) 0.30013(4) 0.02852(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0262(13) 0.0197(12) 0.0224(11) -0.0003(9) -0.0027(9) 0.0059(10) C2 0.0216(12) 0.0156(12) 0.0275(12) 0.0031(9) -0.0016(9) -0.0010(9) C3 0.0218(12) 0.0177(12) 0.0255(12) 0.0004(9) -0.0037(9) 0.0007(9) C4 0.0216(12) 0.0277(14) 0.0305(13) -0.0115(11) -0.0047(10) 0.0035(10) C5 0.0268(14) 0.0313(15) 0.0482(16) -0.0118(12) -0.0085(12) 0.0040(11) C6 0.0358(16) 0.0450(19) 0.069(2) -0.0329(17) -0.0195(15) 0.0159(14) C7 0.0340(17) 0.080(3) 0.0509(19) -0.0383(19) -0.0090(14) 0.0197(17) C8 0.0389(17) 0.092(3) 0.0336(15) -0.0089(16) 0.0046(13) 0.0114(18) C9 0.0330(15) 0.0489(18) 0.0321(14) -0.0042(13) -0.0001(11) 0.0095(13) C10 0.0214(12) 0.0204(12) 0.0224(11) -0.0029(9) 0.0004(9) -0.0005(9) C11 0.0282(13) 0.0298(14) 0.0278(12) -0.0006(10) -0.0027(10) 0.0041(11) C12 0.0331(14) 0.0487(18) 0.0231(12) -0.0042(12) -0.0039(10) -0.0004(13) C13 0.0359(15) 0.0369(16) 0.0311(14) -0.0144(12) 0.0067(11) -0.0091(12) C14 0.0507(17) 0.0241(14) 0.0414(16) -0.0052(12) 0.0054(13) 0.0048(12) C15 0.0431(16) 0.0260(14) 0.0268(13) -0.0008(11) -0.0027(11) 0.0051(12) C16 0.0210(12) 0.0217(13) 0.0227(11) -0.0008(9) -0.0032(9) -0.0003(9) C17 0.0569(18) 0.0216(14) 0.0275(13) 0.0006(10) 0.0048(12) 0.0062(12) C18 0.067(2) 0.0260(15) 0.0354(15) 0.0066(12) 0.0061(14) 0.0073(14) C19 0.0478(17) 0.0360(16) 0.0258(13) 0.0031(11) 0.0009(11) 0.0040(13) C20 0.0389(15) 0.0311(15) 0.0292(13) -0.0066(11) -0.0030(11) 0.0072(12) C21 0.0333(14) 0.0221(13) 0.0311(13) -0.0005(10) -0.0029(11) 0.0061(11) C22 0.0254(12) 0.0191(12) 0.0208(11) 0.0017(9) -0.0045(9) -0.0007(10) C23 0.0345(14) 0.0226(13) 0.0264(12) 0.0005(10) -0.0018(10) -0.0001(11) C24 0.0314(14) 0.0303(15) 0.0327(13) 0.0005(11) 0.0037(11) -0.0082(11) C25 0.0246(13) 0.0401(16) 0.0296(13) -0.0013(11) -0.0008(10) -0.0002(12) C26 0.0293(14) 0.0286(14) 0.0293(13) 0.0043(10) -0.0030(10) 0.0069(11) C27 0.0256(13) 0.0252(13) 0.0288(12) 0.0050(10) -0.0029(10) -0.0006(10) C28 0.0247(12) 0.0178(12) 0.0243(11) -0.0014(9) -0.0010(9) 0.0011(10) C29 0.0218(12) 0.0164(12) 0.0260(11) 0.0007(9) -0.0017(9) -0.0007(9) C30 0.0199(12) 0.0162(12) 0.0240(11) 0.0023(9) -0.0018(9) -0.0002(9) C31 0.0201(12) 0.0242(13) 0.0304(12) -0.0103(10) -0.0001(10) -0.0008(10) C32 0.0260(13) 0.0282(15) 0.0445(15) -0.0097(12) -0.0049(11) 0.0030(11) C33 0.0303(15) 0.0435(18) 0.064(2) -0.0271(16) -0.0104(14) 0.0139(13) C34 0.0294(15) 0.071(2) 0.0501(18) -0.0315(17) -0.0012(13) 0.0133(15) C35 0.0395(17) 0.072(2) 0.0357(15) -0.0064(15) 0.0095(13) 0.0057(16) C36 0.0337(15) 0.0365(16) 0.0345(14) -0.0039(12) 0.0033(11) 0.0041(12) C37 0.0223(12) 0.0194(12) 0.0231(11) -0.0031(9) -0.0001(9) -0.0030(9) C38 0.0293(13) 0.0254(13) 0.0282(12) 0.0013(10) -0.0016(10) 0.0015(10) C39 0.0321(14) 0.0404(16) 0.0248(12) 0.0001(11) -0.0037(10) -0.0048(12) C40 0.0382(15) 0.0310(15) 0.0298(13) -0.0110(11) 0.0044(11) -0.0069(12) C41 0.0430(16) 0.0212(14) 0.0373(14) -0.0055(11) 0.0034(12) 0.0030(11) C42 0.0346(14) 0.0278(14) 0.0265(12) -0.0001(10) -0.0001(10) 0.0044(11) C43 0.0212(12) 0.0280(14) 0.0251(12) 0.0014(10) 0.0007(9) 0.0071(10) C44 0.0278(13) 0.0386(15) 0.0299(13) -0.0074(11) -0.0018(10) 0.0062(11) C45 0.0421(17) 0.071(2) 0.0263(14) -0.0053(14) -0.0036(12) 0.0211(16) C46 0.078(2) 0.093(3) 0.0277(15) 0.0200(17) 0.0143(15) 0.053(2) C47 0.095(3) 0.054(2) 0.0455(18) 0.0287(16) 0.0271(17) 0.047(2) C48 0.0552(18) 0.0311(15) 0.0343(14) 0.0071(12) 0.0144(13) 0.0189(13) C49 0.0234(12) 0.0189(12) 0.0218(11) -0.0042(9) -0.0057(9) -0.0008(10) C50 0.0307(14) 0.0295(14) 0.0302(13) 0.0000(11) -0.0009(11) 0.0045(11) C51 0.0291(14) 0.0425(17) 0.0345(14) -0.0046(12) -0.0067(11) 0.0127(12) C52 0.0235(13) 0.0483(18) 0.0348(14) -0.0126(13) -0.0012(11) 0.0010(12) C53 0.0327(15) 0.0374(16) 0.0422(15) -0.0032(13) 0.0092(12) -0.0035(12) C54 0.0312(14) 0.0280(14) 0.0326(13) 0.0007(11) 0.0028(11) 0.0003(11) C55 0.0335(15) 0.0429(17) 0.0335(14) -0.0012(12) 0.0047(11) -0.0001(12) C56 0.0412(17) 0.0458(19) 0.081(2) -0.0226(17) 0.0047(16) -0.0018(15) C57 0.075(3) 0.043(2) 0.141(3) 0.009(2) 0.021(2) 0.0216(19) C58 0.051(2) 0.084(3) 0.079(2) 0.029(2) 0.0089(18) 0.0206(19) C59 0.0401(17) 0.064(2) 0.0411(17) 0.0107(15) 0.0030(13) 0.0003(16) C60 0.0551(19) 0.0362(16) 0.0336(15) -0.0003(12) 0.0025(13) -0.0050(14) C61 0.072(2) 0.093(3) 0.0427(19) 0.0037(19) -0.0077(17) 0.016(2) N1 0.0208(10) 0.0198(10) 0.0254(10) -0.0027(8) -0.0032(8) 0.0020(8) N2 0.0237(10) 0.0177(10) 0.0228(9) -0.0016(8) -0.0033(8) 0.0007(8) N3 0.0200(10) 0.0189(10) 0.0250(10) -0.0041(8) -0.0005(8) -0.0003(8) N4 0.0228(10) 0.0155(10) 0.0241(10) -0.0035(8) -0.0015(8) 0.0004(8) P1 0.0243(3) 0.0155(3) 0.0232(3) 0.0002(2) -0.0046(2) -0.0001(2) P2 0.0216(3) 0.0146(3) 0.0220(3) -0.0010(2) -0.0025(2) 0.0000(2) S1 0.0215(3) 0.0344(4) 0.0356(3) -0.0107(3) -0.0034(3) 0.0002(3) S2 0.0389(4) 0.0169(3) 0.0332(3) 0.0016(3) -0.0084(3) 0.0038(3) S3 0.0213(3) 0.0295(4) 0.0356(3) -0.0083(3) -0.0023(3) -0.0027(3) S4 0.0315(3) 0.0156(3) 0.0379(3) 0.0008(3) -0.0051(3) 0.0026(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.368(3) . ? C1 N2 1.379(3) . ? C1 S1 1.666(2) . ? C2 C3 1.352(3) . ? C2 N2 1.383(3) . ? C2 H2A 0.9500 . ? C3 N1 1.407(3) . ? C3 P1 1.801(2) . ? C4 C9 1.364(4) . ? C4 C5 1.381(4) . ? C4 N1 1.444(3) . ? C5 C6 1.399(4) . ? C5 H5A 0.9500 . ? C6 C7 1.364(5) . ? C6 H6A 0.9500 . ? C7 C8 1.369(5) . ? C7 H7A 0.9500 . ? C8 C9 1.398(4) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C15 1.370(3) . ? C10 C11 1.381(3) . ? C10 N2 1.443(3) . ? C11 C12 1.382(3) . ? C11 H11A 0.9500 . ? C12 C13 1.373(4) . ? C12 H12A 0.9500 . ? C13 C14 1.378(4) . ? C13 H13A 0.9500 . ? C14 C15 1.392(3) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C17 1.382(3) . ? C16 C21 1.388(3) . ? C16 P1 1.822(2) . ? C17 C18 1.388(4) . ? C17 H17A 0.9500 . ? C18 C19 1.390(4) . ? C18 H18A 0.9500 . ? C19 C20 1.370(4) . ? C19 H19A 0.9500 . ? C20 C21 1.395(4) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.391(3) . ? C22 C27 1.397(3) . ? C22 P1 1.820(2) . ? C23 C24 1.387(4) . ? C23 H23A 0.9500 . ? C24 C25 1.378(4) . ? C24 H24A 0.9500 . ? C25 C26 1.377(4) . ? C25 H25A 0.9500 . ? C26 C27 1.383(3) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C28 N3 1.370(3) . ? C28 N4 1.382(3) . ? C28 S3 1.665(2) . ? C29 C30 1.356(3) . ? C29 N4 1.383(3) . ? C29 H29A 0.9500 . ? C30 N3 1.402(3) . ? C30 P2 1.799(2) . ? C31 C36 1.375(4) . ? C31 C32 1.384(4) . ? C31 N3 1.444(3) . ? C32 C33 1.399(4) . ? C32 H32A 0.9500 . ? C33 C34 1.372(5) . ? C33 H33A 0.9500 . ? C34 C35 1.377(5) . ? C34 H34A 0.9500 . ? C35 C36 1.395(4) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? C37 C42 1.379(3) . ? C37 C38 1.382(3) . ? C37 N4 1.444(3) . ? C38 C39 1.388(3) . ? C38 H38A 0.9500 . ? C39 C40 1.378(4) . ? C39 H39A 0.9500 . ? C40 C41 1.379(4) . ? C40 H40A 0.9500 . ? C41 C42 1.387(3) . ? C41 H41A 0.9500 . ? C42 H42A 0.9500 . ? C43 C44 1.390(3) . ? C43 C48 1.392(4) . ? C43 P2 1.811(2) . ? C44 C45 1.387(4) . ? C44 H44A 0.9500 . ? C45 C46 1.366(5) . ? C45 H45A 0.9500 . ? C46 C47 1.385(5) . ? C46 H46A 0.9500 . ? C47 C48 1.391(4) . ? C47 H47A 0.9500 . ? C48 H48A 0.9500 . ? C49 C54 1.388(3) . ? C49 C50 1.400(3) . ? C49 P2 1.814(2) . ? C50 C51 1.380(4) . ? C50 H50A 0.9500 . ? C51 C52 1.378(4) . ? C51 H51A 0.9500 . ? C52 C53 1.382(4) . ? C52 H52A 0.9500 . ? C53 C54 1.392(4) . ? C53 H53A 0.9500 . ? C54 H54A 0.9500 . ? C55 C56 1.373(4) . ? C55 C60 1.373(4) . ? C55 C61 1.504(4) . ? C56 C57 1.391(6) . ? C56 H56A 0.9500 . ? C57 C58 1.386(6) . ? C57 H57A 0.9500 . ? C58 C59 1.350(5) . ? C58 H58A 0.9500 . ? C59 C60 1.365(4) . ? C59 H59A 0.9500 . ? C60 H60A 0.9500 . ? C61 H61C 0.9800 . ? C61 H61B 0.9800 . ? C61 H61A 0.9800 . ? P1 S2 1.9526(8) . ? P2 S4 1.9478(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 N1 C1 N2 104.61(19) . . ? N1 C1 S1 127.73(17) . . ? N2 C1 S1 127.65(16) . . ? C3 C2 N2 108.2(2) . . ? C3 C2 H2A 125.9 . . ? N2 C2 H2A 125.9 . . ? C2 C3 N1 106.04(19) . . ? C2 C3 P1 128.95(18) . . ? N1 C3 P1 124.78(16) . . ? C9 C4 C5 122.1(2) . . ? C9 C4 N1 119.3(2) . . ? C5 C4 N1 118.5(2) . . ? C4 C5 C6 118.0(3) . . ? C4 C5 H5A 121.0 . . ? C6 C5 H5A 121.0 . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C6 C7 C8 120.5(3) . . ? C6 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? C7 C8 C9 120.2(3) . . ? C7 C8 H8A 119.9 . . ? C9 C8 H8A 119.9 . . ? C4 C9 C8 118.6(3) . . ? C4 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? C15 C10 C11 121.2(2) . . ? C15 C10 N2 119.7(2) . . ? C11 C10 N2 119.1(2) . . ? C10 C11 C12 119.1(2) . . ? C10 C11 H11A 120.4 . . ? C12 C11 H11A 120.4 . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C14 120.1(2) . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C10 C15 C14 119.1(2) . . ? C10 C15 H15A 120.4 . . ? C14 C15 H15A 120.4 . . ? C17 C16 C21 119.7(2) . . ? C17 C16 P1 121.55(17) . . ? C21 C16 P1 118.71(19) . . ? C16 C17 C18 120.1(2) . . ? C16 C17 H17A 120.0 . . ? C18 C17 H17A 120.0 . . ? C17 C18 C19 120.1(3) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C20 C19 C18 120.0(2) . . ? C20 C19 H19A 120.0 . . ? C18 C19 H19A 120.0 . . ? C19 C20 C21 120.2(2) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C16 C21 C20 120.0(2) . . ? C16 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C23 C22 C27 119.3(2) . . ? C23 C22 P1 117.96(18) . . ? C27 C22 P1 122.70(18) . . ? C24 C23 C22 120.2(2) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C25 C24 C23 120.2(2) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? C26 C25 C24 119.7(2) . . ? C26 C25 H25A 120.1 . . ? C24 C25 H25A 120.1 . . ? C25 C26 C27 121.0(2) . . ? C25 C26 H26A 119.5 . . ? C27 C26 H26A 119.5 . . ? C26 C27 C22 119.5(2) . . ? C26 C27 H27A 120.3 . . ? C22 C27 H27A 120.3 . . ? N3 C28 N4 104.73(18) . . ? N3 C28 S3 127.16(17) . . ? N4 C28 S3 128.11(16) . . ? C30 C29 N4 108.1(2) . . ? C30 C29 H29A 126.0 . . ? N4 C29 H29A 126.0 . . ? C29 C30 N3 106.32(19) . . ? C29 C30 P2 128.78(18) . . ? N3 C30 P2 124.43(16) . . ? C36 C31 C32 121.5(2) . . ? C36 C31 N3 119.4(2) . . ? C32 C31 N3 119.1(2) . . ? C31 C32 C33 118.3(3) . . ? C31 C32 H32A 120.9 . . ? C33 C32 H32A 120.9 . . ? C34 C33 C32 120.7(3) . . ? C34 C33 H33A 119.7 . . ? C32 C33 H33A 119.7 . . ? C33 C34 C35 120.3(3) . . ? C33 C34 H34A 119.9 . . ? C35 C34 H34A 119.9 . . ? C34 C35 C36 120.0(3) . . ? C34 C35 H35A 120.0 . . ? C36 C35 H35A 120.0 . . ? C31 C36 C35 119.2(3) . . ? C31 C36 H36A 120.4 . . ? C35 C36 H36A 120.4 . . ? C42 C37 C38 121.6(2) . . ? C42 C37 N4 119.0(2) . . ? C38 C37 N4 119.4(2) . . ? C37 C38 C39 118.8(2) . . ? C37 C38 H38A 120.6 . . ? C39 C38 H38A 120.6 . . ? C40 C39 C38 120.2(2) . . ? C40 C39 H39A 119.9 . . ? C38 C39 H39A 119.9 . . ? C39 C40 C41 120.1(2) . . ? C39 C40 H40A 120.0 . . ? C41 C40 H40A 120.0 . . ? C40 C41 C42 120.6(2) . . ? C40 C41 H41A 119.7 . . ? C42 C41 H41A 119.7 . . ? C37 C42 C41 118.6(2) . . ? C37 C42 H42A 120.7 . . ? C41 C42 H42A 120.7 . . ? C44 C43 C48 120.2(2) . . ? C44 C43 P2 118.06(19) . . ? C48 C43 P2 121.71(18) . . ? C45 C44 C43 120.0(3) . . ? C45 C44 H44A 120.0 . . ? C43 C44 H44A 120.0 . . ? C46 C45 C44 119.9(3) . . ? C46 C45 H45A 120.1 . . ? C44 C45 H45A 120.1 . . ? C45 C46 C47 120.8(3) . . ? C45 C46 H46A 119.6 . . ? C47 C46 H46A 119.6 . . ? C46 C47 C48 120.2(3) . . ? C46 C47 H47A 119.9 . . ? C48 C47 H47A 119.9 . . ? C47 C48 C43 119.0(3) . . ? C47 C48 H48A 120.5 . . ? C43 C48 H48A 120.5 . . ? C54 C49 C50 119.4(2) . . ? C54 C49 P2 118.49(18) . . ? C50 C49 P2 122.06(18) . . ? C51 C50 C49 119.8(2) . . ? C51 C50 H50A 120.1 . . ? C49 C50 H50A 120.1 . . ? C52 C51 C50 120.7(3) . . ? C52 C51 H51A 119.7 . . ? C50 C51 H51A 119.7 . . ? C51 C52 C53 120.0(2) . . ? C51 C52 H52A 120.0 . . ? C53 C52 H52A 120.0 . . ? C52 C53 C54 120.1(3) . . ? C52 C53 H53A 120.0 . . ? C54 C53 H53A 120.0 . . ? C49 C54 C53 120.0(3) . . ? C49 C54 H54A 120.0 . . ? C53 C54 H54A 120.0 . . ? C56 C55 C60 118.4(3) . . ? C56 C55 C61 120.0(3) . . ? C60 C55 C61 121.5(3) . . ? C55 C56 C57 119.5(3) . . ? C55 C56 H56A 120.2 . . ? C57 C56 H56A 120.2 . . ? C58 C57 C56 120.5(3) . . ? C58 C57 H57A 119.8 . . ? C56 C57 H57A 119.8 . . ? C59 C58 C57 119.4(4) . . ? C59 C58 H58A 120.3 . . ? C57 C58 H58A 120.3 . . ? C58 C59 C60 119.9(3) . . ? C58 C59 H59A 120.0 . . ? C60 C59 H59A 120.0 . . ? C59 C60 C55 122.2(3) . . ? C59 C60 H60A 118.9 . . ? C55 C60 H60A 118.9 . . ? C55 C61 H61C 109.5 . . ? C55 C61 H61B 109.5 . . ? H61C C61 H61B 109.5 . . ? C55 C61 H61A 109.5 . . ? H61C C61 H61A 109.5 . . ? H61B C61 H61A 109.5 . . ? C1 N1 C3 110.82(17) . . ? C1 N1 C4 122.29(19) . . ? C3 N1 C4 126.84(18) . . ? C1 N2 C2 110.27(18) . . ? C1 N2 C10 123.31(18) . . ? C2 N2 C10 126.38(18) . . ? C28 N3 C30 110.69(18) . . ? C28 N3 C31 122.66(18) . . ? C30 N3 C31 126.63(18) . . ? C28 N4 C29 110.15(17) . . ? C28 N4 C37 124.06(18) . . ? C29 N4 C37 125.76(18) . . ? C3 P1 C22 103.22(10) . . ? C3 P1 C16 106.42(10) . . ? C22 P1 C16 107.50(10) . . ? C3 P1 S2 114.17(8) . . ? C22 P1 S2 112.54(8) . . ? C16 P1 S2 112.32(8) . . ? C30 P2 C43 106.33(11) . . ? C30 P2 C49 103.56(10) . . ? C43 P2 C49 107.48(10) . . ? C30 P2 S4 113.21(8) . . ? C43 P2 S4 112.58(8) . . ? C49 P2 S4 113.01(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C3 N1 0.0(3) . . . . ? N2 C2 C3 P1 174.64(17) . . . . ? C9 C4 C5 C6 0.2(4) . . . . ? N1 C4 C5 C6 -177.5(2) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? C6 C7 C8 C9 0.6(4) . . . . ? C5 C4 C9 C8 0.1(4) . . . . ? N1 C4 C9 C8 177.7(2) . . . . ? C7 C8 C9 C4 -0.5(4) . . . . ? C15 C10 C11 C12 -1.4(4) . . . . ? N2 C10 C11 C12 177.2(2) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? C11 C12 C13 C14 2.1(4) . . . . ? C12 C13 C14 C15 -2.1(4) . . . . ? C11 C10 C15 C14 1.4(4) . . . . ? N2 C10 C15 C14 -177.2(2) . . . . ? C13 C14 C15 C10 0.4(4) . . . . ? C21 C16 C17 C18 -0.5(4) . . . . ? P1 C16 C17 C18 -178.0(2) . . . . ? C16 C17 C18 C19 0.1(4) . . . . ? C17 C18 C19 C20 0.3(4) . . . . ? C18 C19 C20 C21 -0.3(4) . . . . ? C17 C16 C21 C20 0.5(4) . . . . ? P1 C16 C21 C20 178.05(19) . . . . ? C19 C20 C21 C16 -0.1(4) . . . . ? C27 C22 C23 C24 0.3(3) . . . . ? P1 C22 C23 C24 -177.32(18) . . . . ? C22 C23 C24 C25 -0.9(4) . . . . ? C23 C24 C25 C26 0.5(4) . . . . ? C24 C25 C26 C27 0.6(4) . . . . ? C25 C26 C27 C22 -1.2(4) . . . . ? C23 C22 C27 C26 0.7(3) . . . . ? P1 C22 C27 C26 178.27(18) . . . . ? N4 C29 C30 N3 -0.3(3) . . . . ? N4 C29 C30 P2 -172.53(17) . . . . ? C36 C31 C32 C33 1.0(4) . . . . ? N3 C31 C32 C33 178.7(2) . . . . ? C31 C32 C33 C34 -0.8(4) . . . . ? C32 C33 C34 C35 0.4(4) . . . . ? C33 C34 C35 C36 -0.2(4) . . . . ? C32 C31 C36 C35 -0.9(4) . . . . ? N3 C31 C36 C35 -178.5(2) . . . . ? C34 C35 C36 C31 0.5(4) . . . . ? C42 C37 C38 C39 1.3(4) . . . . ? N4 C37 C38 C39 -178.5(2) . . . . ? C37 C38 C39 C40 -0.3(4) . . . . ? C38 C39 C40 C41 -0.8(4) . . . . ? C39 C40 C41 C42 0.8(4) . . . . ? C38 C37 C42 C41 -1.3(4) . . . . ? N4 C37 C42 C41 178.5(2) . . . . ? C40 C41 C42 C37 0.2(4) . . . . ? C48 C43 C44 C45 -0.2(4) . . . . ? P2 C43 C44 C45 -179.2(2) . . . . ? C43 C44 C45 C46 0.8(4) . . . . ? C44 C45 C46 C47 -0.9(5) . . . . ? C45 C46 C47 C48 0.5(5) . . . . ? C46 C47 C48 C43 0.1(5) . . . . ? C44 C43 C48 C47 -0.2(4) . . . . ? P2 C43 C48 C47 178.8(2) . . . . ? C54 C49 C50 C51 0.0(3) . . . . ? P2 C49 C50 C51 -177.60(18) . . . . ? C49 C50 C51 C52 -0.2(4) . . . . ? C50 C51 C52 C53 0.6(4) . . . . ? C51 C52 C53 C54 -0.9(4) . . . . ? C50 C49 C54 C53 -0.3(3) . . . . ? P2 C49 C54 C53 177.41(19) . . . . ? C52 C53 C54 C49 0.7(4) . . . . ? C60 C55 C56 C57 0.1(5) . . . . ? C61 C55 C56 C57 178.3(3) . . . . ? C55 C56 C57 C58 -0.7(6) . . . . ? C56 C57 C58 C59 1.0(6) . . . . ? C57 C58 C59 C60 -0.9(5) . . . . ? C58 C59 C60 C55 0.4(5) . . . . ? C56 C55 C60 C59 0.0(4) . . . . ? C61 C55 C60 C59 -178.1(3) . . . . ? N2 C1 N1 C3 1.4(2) . . . . ? S1 C1 N1 C3 -177.51(18) . . . . ? N2 C1 N1 C4 -176.2(2) . . . . ? S1 C1 N1 C4 4.8(3) . . . . ? C2 C3 N1 C1 -0.9(3) . . . . ? P1 C3 N1 C1 -175.86(17) . . . . ? C2 C3 N1 C4 176.6(2) . . . . ? P1 C3 N1 C4 1.7(3) . . . . ? C9 C4 N1 C1 -80.8(3) . . . . ? C5 C4 N1 C1 97.0(3) . . . . ? C9 C4 N1 C3 101.9(3) . . . . ? C5 C4 N1 C3 -80.3(3) . . . . ? N1 C1 N2 C2 -1.4(2) . . . . ? S1 C1 N2 C2 177.49(18) . . . . ? N1 C1 N2 C10 -179.2(2) . . . . ? S1 C1 N2 C10 -0.3(3) . . . . ? C3 C2 N2 C1 1.0(3) . . . . ? C3 C2 N2 C10 178.6(2) . . . . ? C15 C10 N2 C1 105.0(3) . . . . ? C11 C10 N2 C1 -73.7(3) . . . . ? C15 C10 N2 C2 -72.4(3) . . . . ? C11 C10 N2 C2 108.9(3) . . . . ? N4 C28 N3 C30 -1.5(2) . . . . ? S3 C28 N3 C30 178.51(18) . . . . ? N4 C28 N3 C31 -180.0(2) . . . . ? S3 C28 N3 C31 0.0(3) . . . . ? C29 C30 N3 C28 1.1(3) . . . . ? P2 C30 N3 C28 173.81(17) . . . . ? C29 C30 N3 C31 179.5(2) . . . . ? P2 C30 N3 C31 -7.8(3) . . . . ? C36 C31 N3 C28 84.3(3) . . . . ? C32 C31 N3 C28 -93.4(3) . . . . ? C36 C31 N3 C30 -93.9(3) . . . . ? C32 C31 N3 C30 88.4(3) . . . . ? N3 C28 N4 C29 1.3(2) . . . . ? S3 C28 N4 C29 -178.68(19) . . . . ? N3 C28 N4 C37 179.2(2) . . . . ? S3 C28 N4 C37 -0.8(3) . . . . ? C30 C29 N4 C28 -0.7(3) . . . . ? C30 C29 N4 C37 -178.5(2) . . . . ? C42 C37 N4 C28 -111.7(3) . . . . ? C38 C37 N4 C28 68.1(3) . . . . ? C42 C37 N4 C29 65.9(3) . . . . ? C38 C37 N4 C29 -114.3(3) . . . . ? C2 C3 P1 C22 17.7(3) . . . . ? N1 C3 P1 C22 -168.53(19) . . . . ? C2 C3 P1 C16 130.7(2) . . . . ? N1 C3 P1 C16 -55.5(2) . . . . ? C2 C3 P1 S2 -104.8(2) . . . . ? N1 C3 P1 S2 69.0(2) . . . . ? C23 C22 P1 C3 -130.88(18) . . . . ? C27 C22 P1 C3 51.6(2) . . . . ? C23 C22 P1 C16 116.88(18) . . . . ? C27 C22 P1 C16 -60.7(2) . . . . ? C23 C22 P1 S2 -7.3(2) . . . . ? C27 C22 P1 S2 175.14(16) . . . . ? C17 C16 P1 C3 -45.9(2) . . . . ? C21 C16 P1 C3 136.55(19) . . . . ? C17 C16 P1 C22 64.1(2) . . . . ? C21 C16 P1 C22 -113.40(19) . . . . ? C17 C16 P1 S2 -171.57(19) . . . . ? C21 C16 P1 S2 10.9(2) . . . . ? C29 C30 P2 C43 -124.0(2) . . . . ? N3 C30 P2 C43 65.0(2) . . . . ? C29 C30 P2 C49 -10.9(2) . . . . ? N3 C30 P2 C49 178.14(19) . . . . ? C29 C30 P2 S4 111.9(2) . . . . ? N3 C30 P2 S4 -59.1(2) . . . . ? C44 C43 P2 C30 -147.64(18) . . . . ? C48 C43 P2 C30 33.3(2) . . . . ? C44 C43 P2 C49 101.96(19) . . . . ? C48 C43 P2 C49 -77.1(2) . . . . ? C44 C43 P2 S4 -23.1(2) . . . . ? C48 C43 P2 S4 157.83(19) . . . . ? C54 C49 P2 C30 109.69(19) . . . . ? C50 C49 P2 C30 -72.7(2) . . . . ? C54 C49 P2 C43 -138.03(18) . . . . ? C50 C49 P2 C43 39.6(2) . . . . ? C54 C49 P2 S4 -13.2(2) . . . . ? C50 C49 P2 S4 164.47(16) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.413 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.059 #------------------------------------------------------------------------------ data_6d-GSTR117 _database_code_depnum_ccdc_archive 'CCDC 859628' #TrackingRef 'Gesamtcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 N2 P S Se' _chemical_formula_sum 'C19 H21 N2 P S Se' _chemical_formula_weight 419.37 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/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 49.257(2) _cell_length_b 8.8837(4) _cell_length_c 27.5328(13) _cell_angle_alpha 90.00 _cell_angle_beta 105.1780(10) _cell_angle_gamma 90.00 _cell_volume 11627.8(9) _cell_formula_units_Z 24 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9160 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 37.32 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5136 _exptl_absorpt_coefficient_mu 2.131 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.4828 _exptl_absorpt_correction_T_max 0.8152 _exptl_absorpt_process_details 'Sadabs 2008/2' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker X8-KappaApexII' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35352 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -62 _diffrn_reflns_limit_h_max 64 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 28.00 _reflns_number_total 14008 _reflns_number_gt 11080 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+21.5038P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14008 _refine_ls_number_parameters 658 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.31443(5) 0.4892(3) 0.09606(8) 0.0154(5) Uani 1 1 d . . . C2 C 0.27164(5) 0.5915(3) 0.08951(8) 0.0141(5) Uani 1 1 d . . . C3 C 0.29019(5) 0.7056(3) 0.09197(8) 0.0152(5) Uani 1 1 d . . . H3A H 0.2860 0.8101 0.0913 0.018 Uiso 1 1 calc R . . C4 C 0.34325(5) 0.7242(3) 0.10022(9) 0.0192(5) Uani 1 1 d . . . H4A H 0.3585 0.6667 0.1241 0.023 Uiso 1 1 calc R . . C5 C 0.34209(5) 0.8802(3) 0.12185(10) 0.0253(6) Uani 1 1 d . . . H5A H 0.3288 0.9427 0.0973 0.038 Uiso 1 1 calc R . . H5B H 0.3608 0.9259 0.1295 0.038 Uiso 1 1 calc R . . H5C H 0.3358 0.8728 0.1528 0.038 Uiso 1 1 calc R . . C6 C 0.35007(5) 0.7281(3) 0.04933(10) 0.0248(6) Uani 1 1 d . . . H6A H 0.3685 0.7753 0.0531 0.037 Uiso 1 1 calc R . . H6B H 0.3356 0.7863 0.0254 0.037 Uiso 1 1 calc R . . H6C H 0.3505 0.6251 0.0368 0.037 Uiso 1 1 calc R . . C7 C 0.27591(5) 0.3045(3) 0.09051(10) 0.0212(5) Uani 1 1 d . . . H7A H 0.2717 0.2815 0.1226 0.032 Uiso 1 1 calc R . . H7B H 0.2900 0.2334 0.0849 0.032 Uiso 1 1 calc R . . H7C H 0.2587 0.2957 0.0631 0.032 Uiso 1 1 calc R . . C8 C 0.23000(5) 0.5183(3) 0.14024(8) 0.0143(5) Uani 1 1 d . . . C9 C 0.20404(5) 0.4579(3) 0.14163(9) 0.0183(5) Uani 1 1 d . . . H9A H 0.1885 0.4629 0.1126 0.022 Uiso 1 1 calc R . . C10 C 0.20081(5) 0.3904(3) 0.18531(9) 0.0207(5) Uani 1 1 d . . . H10A H 0.1831 0.3491 0.1861 0.025 Uiso 1 1 calc R . . C11 C 0.22342(5) 0.3833(3) 0.22778(9) 0.0223(5) Uani 1 1 d . . . H11A H 0.2213 0.3354 0.2574 0.027 Uiso 1 1 calc R . . C12 C 0.24915(5) 0.4463(3) 0.22691(9) 0.0213(5) Uani 1 1 d . . . H12A H 0.2644 0.4431 0.2563 0.026 Uiso 1 1 calc R . . C13 C 0.25264(5) 0.5138(3) 0.18332(9) 0.0178(5) Uani 1 1 d . . . H13A H 0.2702 0.5565 0.1828 0.021 Uiso 1 1 calc R . . C14 C 0.22728(5) 0.7995(3) 0.08449(8) 0.0154(5) Uani 1 1 d . . . C15 C 0.22842(7) 0.8726(3) 0.12980(10) 0.0343(7) Uani 1 1 d . . . H15A H 0.2339 0.8186 0.1606 0.041 Uiso 1 1 calc R . . C16 C 0.22152(8) 1.0244(3) 0.13000(11) 0.0405(8) Uani 1 1 d . . . H16A H 0.2223 1.0740 0.1609 0.049 Uiso 1 1 calc R . . C17 C 0.21353(6) 1.1031(3) 0.08529(10) 0.0247(6) Uani 1 1 d . . . H17A H 0.2084 1.2062 0.0854 0.030 Uiso 1 1 calc R . . C18 C 0.21294(7) 1.0327(3) 0.04057(10) 0.0315(7) Uani 1 1 d . . . H18A H 0.2079 1.0877 0.0099 0.038 Uiso 1 1 calc R . . C19 C 0.21969(7) 0.8812(3) 0.04026(10) 0.0301(6) Uani 1 1 d . . . H19A H 0.2191 0.8329 0.0092 0.036 Uiso 1 1 calc R . . C20 C 0.48227(5) 0.9761(3) 0.42973(8) 0.0167(5) Uani 1 1 d . . . C21 C 0.43839(5) 1.0689(3) 0.41822(8) 0.0160(5) Uani 1 1 d . . . C22 C 0.45630(5) 1.1865(3) 0.42198(8) 0.0175(5) Uani 1 1 d . . . H22A H 0.4513 1.2900 0.4204 0.021 Uiso 1 1 calc R . . C23 C 0.50952(5) 1.2164(3) 0.43463(10) 0.0229(5) Uani 1 1 d . . . H23A H 0.5247 1.1635 0.4603 0.027 Uiso 1 1 calc R . . C24 C 0.51798(6) 1.2183(4) 0.38514(11) 0.0328(7) Uani 1 1 d . . . H24A H 0.5365 1.2655 0.3904 0.049 Uiso 1 1 calc R . . H24B H 0.5041 1.2758 0.3600 0.049 Uiso 1 1 calc R . . H24C H 0.5188 1.1149 0.3732 0.049 Uiso 1 1 calc R . . C25 C 0.50652(6) 1.3724(3) 0.45397(11) 0.0300(6) Uani 1 1 d . . . H25A H 0.4935 1.4308 0.4278 0.045 Uiso 1 1 calc R . . H25B H 0.5249 1.4220 0.4630 0.045 Uiso 1 1 calc R . . H25C H 0.4992 1.3659 0.4838 0.045 Uiso 1 1 calc R . . C26 C 0.44470(5) 0.7833(3) 0.42124(10) 0.0242(6) Uani 1 1 d . . . H26A H 0.4608 0.7146 0.4297 0.036 Uiso 1 1 calc R . . H26B H 0.4331 0.7608 0.3873 0.036 Uiso 1 1 calc R . . H26C H 0.4335 0.7703 0.4455 0.036 Uiso 1 1 calc R . . C27 C 0.39577(5) 0.9894(3) 0.46567(9) 0.0169(5) Uani 1 1 d . . . C28 C 0.41614(5) 1.0131(3) 0.51086(9) 0.0205(5) Uani 1 1 d . . . H28A H 0.4327 1.0690 0.5113 0.025 Uiso 1 1 calc R . . C29 C 0.41207(5) 0.9544(3) 0.55523(9) 0.0243(6) Uani 1 1 d . . . H29A H 0.4260 0.9696 0.5861 0.029 Uiso 1 1 calc R . . C30 C 0.38784(6) 0.8738(3) 0.55477(10) 0.0256(6) Uani 1 1 d . . . H30A H 0.3852 0.8337 0.5852 0.031 Uiso 1 1 calc R . . C31 C 0.36756(6) 0.8517(3) 0.51011(10) 0.0272(6) Uani 1 1 d . . . H31A H 0.3509 0.7976 0.5100 0.033 Uiso 1 1 calc R . . C32 C 0.37140(5) 0.9083(3) 0.46542(10) 0.0235(6) Uani 1 1 d . . . H32A H 0.3575 0.8921 0.4347 0.028 Uiso 1 1 calc R . . C33 C 0.39074(5) 1.2625(3) 0.40634(9) 0.0209(5) Uani 1 1 d . . . C34 C 0.37300(8) 1.3095(4) 0.43494(12) 0.0439(9) Uani 1 1 d . . . H34A H 0.3683 1.2432 0.4585 0.053 Uiso 1 1 calc R . . C35 C 0.36218(9) 1.4551(4) 0.42866(15) 0.0599(12) Uani 1 1 d . . . H35A H 0.3496 1.4871 0.4474 0.072 Uiso 1 1 calc R . . C36 C 0.36959(8) 1.5538(4) 0.39538(13) 0.0464(9) Uani 1 1 d . . . H36A H 0.3629 1.6545 0.3926 0.056 Uiso 1 1 calc R . . C37 C 0.38658(6) 1.5059(3) 0.36659(10) 0.0269(6) Uani 1 1 d . . . H37A H 0.3914 1.5729 0.3432 0.032 Uiso 1 1 calc R . . C38 C 0.39695(5) 1.3598(3) 0.37125(9) 0.0228(5) Uani 1 1 d . . . H38A H 0.4083 1.3263 0.3504 0.027 Uiso 1 1 calc R . . C39 C 0.39564(5) 0.4121(3) 0.24008(8) 0.0153(5) Uani 1 1 d . . . C40 C 0.37717(5) 0.2997(3) 0.24116(8) 0.0159(5) Uani 1 1 d . . . H40A H 0.3813 0.1951 0.2434 0.019 Uiso 1 1 calc R . . C41 C 0.35323(5) 0.5167(3) 0.23559(8) 0.0154(5) Uani 1 1 d . . . C42 C 0.32496(5) 0.2836(3) 0.23785(9) 0.0189(5) Uani 1 1 d . . . H42A H 0.3090 0.3432 0.2166 0.023 Uiso 1 1 calc R . . C43 C 0.32113(5) 0.2772(3) 0.29102(10) 0.0255(6) Uani 1 1 d . . . H43A H 0.3364 0.2179 0.3126 0.038 Uiso 1 1 calc R . . H43B H 0.3030 0.2301 0.2902 0.038 Uiso 1 1 calc R . . H43C H 0.3215 0.3795 0.3045 0.038 Uiso 1 1 calc R . . C44 C 0.32449(5) 0.1296(3) 0.21419(10) 0.0254(6) Uani 1 1 d . . . H44A H 0.3057 0.0860 0.2085 0.038 Uiso 1 1 calc R . . H44B H 0.3382 0.0642 0.2367 0.038 Uiso 1 1 calc R . . H44C H 0.3293 0.1389 0.1820 0.038 Uiso 1 1 calc R . . C45 C 0.39168(5) 0.6987(3) 0.23541(9) 0.0199(5) Uani 1 1 d . . . H45A H 0.3987 0.7101 0.2054 0.030 Uiso 1 1 calc R . . H45B H 0.4071 0.7152 0.2656 0.030 Uiso 1 1 calc R . . H45C H 0.3768 0.7725 0.2344 0.030 Uiso 1 1 calc R . . C46 C 0.43679(5) 0.4804(3) 0.18782(9) 0.0149(5) Uani 1 1 d . . . C47 C 0.41452(5) 0.4741(3) 0.14438(9) 0.0196(5) Uani 1 1 d . . . H47A H 0.3973 0.4275 0.1453 0.023 Uiso 1 1 calc R . . C48 C 0.41766(5) 0.5362(3) 0.09973(9) 0.0219(5) Uani 1 1 d . . . H48A H 0.4026 0.5311 0.0700 0.026 Uiso 1 1 calc R . . C49 C 0.44274(5) 0.6056(3) 0.09864(9) 0.0231(5) Uani 1 1 d . . . H49A H 0.4447 0.6502 0.0684 0.028 Uiso 1 1 calc R . . C50 C 0.46500(5) 0.6100(3) 0.14153(10) 0.0222(5) Uani 1 1 d . . . H50A H 0.4822 0.6564 0.1404 0.027 Uiso 1 1 calc R . . C51 C 0.46221(5) 0.5466(3) 0.18612(9) 0.0187(5) Uani 1 1 d . . . H51A H 0.4776 0.5483 0.2154 0.022 Uiso 1 1 calc R . . C52 C 0.43996(5) 0.2020(3) 0.24508(9) 0.0169(5) Uani 1 1 d . . . C53 C 0.45011(8) 0.1254(3) 0.28938(10) 0.0404(8) Uani 1 1 d . . . H53A H 0.4521 0.1764 0.3204 0.048 Uiso 1 1 calc R . . C54 C 0.45746(8) -0.0253(3) 0.28958(11) 0.0428(9) Uani 1 1 d . . . H54A H 0.4643 -0.0766 0.3206 0.051 Uiso 1 1 calc R . . C55 C 0.45488(6) -0.0996(3) 0.24557(10) 0.0292(6) Uani 1 1 d . . . H55A H 0.4605 -0.2019 0.2459 0.035 Uiso 1 1 calc R . . C56 C 0.44404(10) -0.0268(4) 0.20046(12) 0.0568(12) Uani 1 1 d . . . H56A H 0.4417 -0.0797 0.1697 0.068 Uiso 1 1 calc R . . C57 C 0.43649(8) 0.1238(4) 0.20003(11) 0.0479(10) Uani 1 1 d . . . H57A H 0.4289 0.1737 0.1689 0.057 Uiso 1 1 calc R . . N1 N 0.31632(4) 0.6433(2) 0.09569(7) 0.0152(4) Uani 1 1 d . . . N2 N 0.28683(4) 0.4575(2) 0.09196(7) 0.0159(4) Uani 1 1 d . . . N3 N 0.48310(4) 1.1296(2) 0.42850(7) 0.0168(4) Uani 1 1 d . . . N4 N 0.45473(4) 0.9382(2) 0.42310(7) 0.0172(4) Uani 1 1 d . . . N5 N 0.35142(4) 0.3639(2) 0.23841(7) 0.0159(4) Uani 1 1 d . . . N6 N 0.38047(4) 0.5470(2) 0.23663(7) 0.0157(4) Uani 1 1 d . . . P1 P 0.234469(12) 0.59991(7) 0.08239(2) 0.01343(12) Uani 1 1 d . . . P2 P 0.400887(12) 1.06701(7) 0.40780(2) 0.01604(13) Uani 1 1 d . . . P3 P 0.432640(12) 0.40186(7) 0.24624(2) 0.01433(12) Uani 1 1 d . . . S1 S 0.340435(13) 0.36362(7) 0.10024(2) 0.02055(13) Uani 1 1 d . . . S2 S 0.509472(13) 0.85653(8) 0.43731(2) 0.02265(14) Uani 1 1 d . . . S3 S 0.327195(12) 0.64286(7) 0.23208(2) 0.02018(13) Uani 1 1 d . . . Se1 Se 0.210607(5) 0.49118(3) 0.017038(9) 0.01951(7) Uani 1 1 d . . . Se2 Se 0.379886(5) 0.94908(3) 0.342148(9) 0.02267(7) Uani 1 1 d . . . Se3 Se 0.456920(5) 0.51128(3) 0.311157(9) 0.01908(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0172(11) 0.0168(12) 0.0128(10) -0.0019(9) 0.0048(9) 0.0008(9) C2 0.0167(11) 0.0147(12) 0.0117(10) -0.0006(8) 0.0049(8) 0.0025(9) C3 0.0179(11) 0.0154(12) 0.0128(10) 0.0015(9) 0.0045(8) 0.0021(9) C4 0.0170(11) 0.0196(13) 0.0215(12) 0.0042(10) 0.0057(9) -0.0014(10) C5 0.0227(13) 0.0241(14) 0.0283(13) 0.0008(11) 0.0053(11) -0.0072(11) C6 0.0230(13) 0.0295(15) 0.0256(13) 0.0073(11) 0.0127(10) 0.0010(11) C7 0.0177(12) 0.0136(13) 0.0317(14) -0.0015(10) 0.0057(10) -0.0007(9) C8 0.0165(11) 0.0130(12) 0.0141(10) 0.0010(8) 0.0053(9) 0.0021(9) C9 0.0160(11) 0.0204(13) 0.0183(11) 0.0003(10) 0.0044(9) 0.0004(9) C10 0.0193(12) 0.0201(13) 0.0255(13) 0.0025(10) 0.0110(10) -0.0025(10) C11 0.0272(13) 0.0232(14) 0.0193(12) 0.0058(10) 0.0113(10) 0.0036(11) C12 0.0211(12) 0.0279(14) 0.0140(11) 0.0037(10) 0.0030(9) 0.0024(11) C13 0.0171(11) 0.0201(13) 0.0166(11) 0.0019(9) 0.0050(9) 0.0002(9) C14 0.0133(10) 0.0162(12) 0.0168(11) 0.0002(9) 0.0038(9) 0.0016(9) C15 0.063(2) 0.0207(15) 0.0197(13) 0.0020(11) 0.0126(13) 0.0083(14) C16 0.078(3) 0.0231(16) 0.0234(14) -0.0015(12) 0.0190(15) 0.0087(15) C17 0.0304(14) 0.0168(13) 0.0283(14) 0.0026(11) 0.0103(11) 0.0031(11) C18 0.0538(19) 0.0185(14) 0.0198(13) 0.0056(11) 0.0053(12) 0.0028(13) C19 0.0539(19) 0.0198(14) 0.0159(12) -0.0003(10) 0.0078(12) 0.0045(13) C20 0.0173(11) 0.0199(13) 0.0135(10) 0.0000(9) 0.0048(9) 0.0020(9) C21 0.0163(11) 0.0166(12) 0.0151(10) 0.0015(9) 0.0044(8) 0.0029(9) C22 0.0175(11) 0.0184(13) 0.0167(11) 0.0020(9) 0.0046(9) 0.0018(9) C23 0.0166(12) 0.0224(14) 0.0292(13) 0.0057(11) 0.0051(10) -0.0025(10) C24 0.0258(14) 0.0369(18) 0.0415(17) 0.0140(14) 0.0190(13) 0.0033(12) C25 0.0258(14) 0.0236(15) 0.0390(16) 0.0015(12) 0.0059(12) -0.0085(11) C26 0.0190(12) 0.0170(13) 0.0337(14) -0.0019(11) 0.0014(10) -0.0007(10) C27 0.0157(11) 0.0167(12) 0.0183(11) 0.0046(9) 0.0047(9) 0.0027(9) C28 0.0184(12) 0.0230(14) 0.0206(12) 0.0009(10) 0.0058(10) -0.0009(10) C29 0.0234(13) 0.0318(15) 0.0182(12) 0.0022(11) 0.0062(10) 0.0008(11) C30 0.0278(14) 0.0293(15) 0.0220(12) 0.0077(11) 0.0108(11) 0.0047(11) C31 0.0218(13) 0.0274(15) 0.0348(15) 0.0099(12) 0.0114(11) -0.0015(11) C32 0.0170(12) 0.0288(15) 0.0226(12) 0.0056(11) 0.0014(10) -0.0016(10) C33 0.0210(12) 0.0204(14) 0.0221(12) 0.0057(10) 0.0072(10) 0.0042(10) C34 0.066(2) 0.0332(18) 0.0468(19) 0.0157(15) 0.0398(17) 0.0182(16) C35 0.097(3) 0.040(2) 0.064(2) 0.0196(19) 0.060(2) 0.035(2) C36 0.072(2) 0.0233(17) 0.055(2) 0.0133(15) 0.0365(19) 0.0198(17) C37 0.0377(15) 0.0206(14) 0.0210(13) 0.0047(11) 0.0054(11) -0.0026(12) C38 0.0259(13) 0.0251(14) 0.0171(11) 0.0011(10) 0.0051(10) -0.0003(11) C39 0.0167(11) 0.0176(13) 0.0123(10) 0.0001(9) 0.0050(8) 0.0029(9) C40 0.0165(11) 0.0171(12) 0.0141(10) 0.0009(9) 0.0038(9) 0.0029(9) C41 0.0146(11) 0.0185(13) 0.0133(10) 0.0002(9) 0.0040(8) 0.0006(9) C42 0.0144(11) 0.0195(13) 0.0240(12) 0.0048(10) 0.0070(9) -0.0009(9) C43 0.0243(13) 0.0280(15) 0.0282(13) 0.0053(11) 0.0138(11) -0.0009(11) C44 0.0221(13) 0.0239(15) 0.0301(14) 0.0014(11) 0.0064(11) -0.0053(11) C45 0.0173(12) 0.0169(13) 0.0252(12) 0.0022(10) 0.0046(10) -0.0019(10) C46 0.0156(11) 0.0136(12) 0.0163(11) 0.0022(9) 0.0056(9) 0.0021(9) C47 0.0173(11) 0.0212(14) 0.0203(12) 0.0018(10) 0.0051(9) 0.0007(10) C48 0.0196(12) 0.0270(15) 0.0173(11) 0.0035(10) 0.0019(9) 0.0034(10) C49 0.0273(13) 0.0245(14) 0.0206(12) 0.0070(10) 0.0120(10) 0.0058(11) C50 0.0196(12) 0.0224(14) 0.0269(13) 0.0035(11) 0.0102(10) -0.0007(10) C51 0.0168(11) 0.0202(13) 0.0192(11) 0.0008(10) 0.0050(9) -0.0008(10) C52 0.0142(11) 0.0181(13) 0.0187(11) 0.0001(9) 0.0050(9) 0.0012(9) C53 0.080(2) 0.0232(16) 0.0179(13) 0.0012(11) 0.0128(14) 0.0106(16) C54 0.081(3) 0.0224(17) 0.0213(14) 0.0059(12) 0.0076(15) 0.0095(16) C55 0.0409(16) 0.0165(14) 0.0308(14) 0.0024(11) 0.0105(12) 0.0047(12) C56 0.119(4) 0.0247(18) 0.0243(16) -0.0020(13) 0.0141(19) 0.018(2) C57 0.090(3) 0.0276(17) 0.0197(14) 0.0007(12) 0.0028(15) 0.0146(18) N1 0.0154(9) 0.0172(11) 0.0139(9) 0.0012(8) 0.0052(7) -0.0003(8) N2 0.0150(9) 0.0153(10) 0.0174(9) -0.0019(8) 0.0040(8) 0.0009(8) N3 0.0148(9) 0.0196(11) 0.0166(9) 0.0020(8) 0.0051(7) -0.0004(8) N4 0.0146(9) 0.0186(11) 0.0179(9) -0.0014(8) 0.0034(7) 0.0014(8) N5 0.0133(9) 0.0185(11) 0.0166(9) 0.0013(8) 0.0050(7) -0.0004(8) N6 0.0149(9) 0.0168(10) 0.0157(9) 0.0013(8) 0.0049(7) 0.0006(8) P1 0.0133(3) 0.0147(3) 0.0122(3) 0.0005(2) 0.0032(2) 0.0010(2) P2 0.0140(3) 0.0173(3) 0.0168(3) 0.0034(2) 0.0040(2) 0.0010(2) P3 0.0127(3) 0.0161(3) 0.0144(3) 0.0020(2) 0.0039(2) 0.0006(2) S1 0.0162(3) 0.0215(3) 0.0238(3) -0.0020(2) 0.0050(2) 0.0050(2) S2 0.0181(3) 0.0246(4) 0.0243(3) -0.0028(3) 0.0039(2) 0.0064(2) S3 0.0165(3) 0.0208(3) 0.0234(3) -0.0008(2) 0.0056(2) 0.0046(2) Se1 0.02205(13) 0.01963(14) 0.01394(11) -0.00084(9) -0.00048(9) -0.00090(10) Se2 0.02216(13) 0.02348(14) 0.01871(12) 0.00322(10) -0.00117(9) -0.00166(10) Se3 0.01913(12) 0.02036(14) 0.01572(12) 0.00034(9) 0.00095(9) -0.00147(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 C1 N2 1.364(3) . ? C1 N1 1.372(3) . ? C1 S1 1.680(2) . ? C2 C3 1.355(3) . ? C2 N2 1.398(3) . ? C2 P1 1.791(2) . ? C3 N1 1.380(3) . ? C3 H3A 0.9500 . ? C4 N1 1.485(3) . ? C4 C5 1.515(4) . ? C4 C6 1.524(3) . ? C4 H4A 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N2 1.459(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.397(3) . ? C8 C13 1.400(3) . ? C8 P1 1.815(2) . ? C9 C10 1.390(3) . ? C9 H9A 0.9500 . ? C10 C11 1.389(3) . ? C10 H10A 0.9500 . ? C11 C12 1.392(4) . ? C11 H11A 0.9500 . ? C12 C13 1.392(3) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C19 1.382(3) . ? C14 C15 1.395(3) . ? C14 P1 1.812(3) . ? C15 C16 1.392(4) . ? C15 H15A 0.9500 . ? C16 C17 1.380(4) . ? C16 H16A 0.9500 . ? C17 C18 1.374(4) . ? C17 H17A 0.9500 . ? C18 C19 1.387(4) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 N4 1.363(3) . ? C20 N3 1.365(3) . ? C20 S2 1.679(2) . ? C21 C22 1.354(3) . ? C21 N4 1.399(3) . ? C21 P2 1.794(2) . ? C22 N3 1.380(3) . ? C22 H22A 0.9500 . ? C23 N3 1.484(3) . ? C23 C25 1.506(4) . ? C23 C24 1.526(4) . ? C23 H23A 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N4 1.459(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.395(3) . ? C27 C32 1.398(3) . ? C27 P2 1.813(2) . ? C28 C29 1.390(3) . ? C28 H28A 0.9500 . ? C29 C30 1.390(4) . ? C29 H29A 0.9500 . ? C30 C31 1.380(4) . ? C30 H30A 0.9500 . ? C31 C32 1.388(4) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? C33 C34 1.384(4) . ? C33 C38 1.389(3) . ? C33 P2 1.805(3) . ? C34 C35 1.393(5) . ? C34 H34A 0.9500 . ? C35 C36 1.385(5) . ? C35 H35A 0.9500 . ? C36 C37 1.362(4) . ? C36 H36A 0.9500 . ? C37 C38 1.389(4) . ? C37 H37A 0.9500 . ? C38 H38A 0.9500 . ? C39 C40 1.357(3) . ? C39 N6 1.402(3) . ? C39 P3 1.788(2) . ? C40 N5 1.375(3) . ? C40 H40A 0.9500 . ? C41 N6 1.361(3) . ? C41 N5 1.364(3) . ? C41 S3 1.687(2) . ? C42 N5 1.482(3) . ? C42 C44 1.513(4) . ? C42 C43 1.526(3) . ? C42 H42A 1.0000 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 N6 1.460(3) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 C51 1.395(3) . ? C46 C47 1.396(3) . ? C46 P3 1.813(2) . ? C47 C48 1.393(3) . ? C47 H47A 0.9500 . ? C48 C49 1.388(4) . ? C48 H48A 0.9500 . ? C49 C50 1.386(3) . ? C49 H49A 0.9500 . ? C50 C51 1.390(3) . ? C50 H50A 0.9500 . ? C51 H51A 0.9500 . ? C52 C53 1.372(4) . ? C52 C57 1.393(4) . ? C52 P3 1.814(3) . ? C53 C54 1.386(4) . ? C53 H53A 0.9500 . ? C54 C55 1.356(4) . ? C54 H54A 0.9500 . ? C55 C56 1.378(4) . ? C55 H55A 0.9500 . ? C56 C57 1.388(4) . ? C56 H56A 0.9500 . ? C57 H57A 0.9500 . ? P1 Se1 2.1083(6) . ? P2 Se2 2.1108(7) . ? P3 Se3 2.1096(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 105.9(2) . . ? N2 C1 S1 126.47(19) . . ? N1 C1 S1 127.65(18) . . ? C3 C2 N2 106.8(2) . . ? C3 C2 P1 129.13(19) . . ? N2 C2 P1 124.04(18) . . ? C2 C3 N1 107.9(2) . . ? C2 C3 H3A 126.1 . . ? N1 C3 H3A 126.1 . . ? N1 C4 C5 110.5(2) . . ? N1 C4 C6 109.9(2) . . ? C5 C4 C6 112.4(2) . . ? N1 C4 H4A 107.9 . . ? C5 C4 H4A 107.9 . . ? C6 C4 H4A 107.9 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 119.8(2) . . ? C9 C8 P1 119.98(17) . . ? C13 C8 P1 120.16(18) . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C11 C10 C9 120.0(2) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C10 C11 C12 120.0(2) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C11 C12 C13 120.4(2) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C12 C13 C8 119.5(2) . . ? C12 C13 H13A 120.3 . . ? C8 C13 H13A 120.3 . . ? C19 C14 C15 118.8(2) . . ? C19 C14 P1 119.73(19) . . ? C15 C14 P1 121.44(19) . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C17 C16 C15 120.0(3) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C18 C17 C16 120.2(3) . . ? C18 C17 H17A 119.9 . . ? C16 C17 H17A 119.9 . . ? C17 C18 C19 119.9(3) . . ? C17 C18 H18A 120.1 . . ? C19 C18 H18A 120.1 . . ? C14 C19 C18 120.9(2) . . ? C14 C19 H19A 119.5 . . ? C18 C19 H19A 119.5 . . ? N4 C20 N3 106.1(2) . . ? N4 C20 S2 126.49(19) . . ? N3 C20 S2 127.37(19) . . ? C22 C21 N4 106.6(2) . . ? C22 C21 P2 130.00(19) . . ? N4 C21 P2 123.39(18) . . ? C21 C22 N3 108.0(2) . . ? C21 C22 H22A 126.0 . . ? N3 C22 H22A 126.0 . . ? N3 C23 C25 110.8(2) . . ? N3 C23 C24 109.9(2) . . ? C25 C23 C24 112.4(2) . . ? N3 C23 H23A 107.9 . . ? C25 C23 H23A 107.9 . . ? C24 C23 H23A 107.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N4 C26 H26A 109.5 . . ? N4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C32 119.9(2) . . ? C28 C27 P2 119.55(18) . . ? C32 C27 P2 120.54(18) . . ? C29 C28 C27 119.4(2) . . ? C29 C28 H28A 120.3 . . ? C27 C28 H28A 120.3 . . ? C30 C29 C28 120.4(2) . . ? C30 C29 H29A 119.8 . . ? C28 C29 H29A 119.8 . . ? C31 C30 C29 120.1(2) . . ? C31 C30 H30A 120.0 . . ? C29 C30 H30A 120.0 . . ? C30 C31 C32 120.2(2) . . ? C30 C31 H31A 119.9 . . ? C32 C31 H31A 119.9 . . ? C31 C32 C27 119.9(2) . . ? C31 C32 H32A 120.0 . . ? C27 C32 H32A 120.0 . . ? C34 C33 C38 119.7(3) . . ? C34 C33 P2 119.3(2) . . ? C38 C33 P2 120.3(2) . . ? C33 C34 C35 119.1(3) . . ? C33 C34 H34A 120.4 . . ? C35 C34 H34A 120.4 . . ? C36 C35 C34 120.8(3) . . ? C36 C35 H35A 119.6 . . ? C34 C35 H35A 119.6 . . ? C37 C36 C35 119.7(3) . . ? C37 C36 H36A 120.1 . . ? C35 C36 H36A 120.1 . . ? C36 C37 C38 120.3(3) . . ? C36 C37 H37A 119.8 . . ? C38 C37 H37A 119.8 . . ? C37 C38 C33 120.2(3) . . ? C37 C38 H38A 119.9 . . ? C33 C38 H38A 119.9 . . ? C40 C39 N6 106.4(2) . . ? C40 C39 P3 129.28(19) . . ? N6 C39 P3 124.19(18) . . ? C39 C40 N5 107.9(2) . . ? C39 C40 H40A 126.0 . . ? N5 C40 H40A 126.0 . . ? N6 C41 N5 105.9(2) . . ? N6 C41 S3 126.86(19) . . ? N5 C41 S3 127.20(18) . . ? N5 C42 C44 110.7(2) . . ? N5 C42 C43 109.7(2) . . ? C44 C42 C43 112.8(2) . . ? N5 C42 H42A 107.8 . . ? C44 C42 H42A 107.8 . . ? C43 C42 H42A 107.8 . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C42 C44 H44A 109.5 . . ? C42 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C42 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? N6 C45 H45A 109.5 . . ? N6 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? N6 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C51 C46 C47 119.9(2) . . ? C51 C46 P3 120.16(17) . . ? C47 C46 P3 119.89(18) . . ? C48 C47 C46 119.7(2) . . ? C48 C47 H47A 120.1 . . ? C46 C47 H47A 120.1 . . ? C49 C48 C47 120.0(2) . . ? C49 C48 H48A 120.0 . . ? C47 C48 H48A 120.0 . . ? C50 C49 C48 120.3(2) . . ? C50 C49 H49A 119.8 . . ? C48 C49 H49A 119.8 . . ? C49 C50 C51 120.1(2) . . ? C49 C50 H50A 119.9 . . ? C51 C50 H50A 119.9 . . ? C50 C51 C46 119.8(2) . . ? C50 C51 H51A 120.1 . . ? C46 C51 H51A 120.1 . . ? C53 C52 C57 118.4(3) . . ? C53 C52 P3 119.9(2) . . ? C57 C52 P3 121.7(2) . . ? C52 C53 C54 121.1(3) . . ? C52 C53 H53A 119.5 . . ? C54 C53 H53A 119.5 . . ? C55 C54 C53 120.2(3) . . ? C55 C54 H54A 119.9 . . ? C53 C54 H54A 119.9 . . ? C54 C55 C56 120.0(3) . . ? C54 C55 H55A 120.0 . . ? C56 C55 H55A 120.0 . . ? C55 C56 C57 120.0(3) . . ? C55 C56 H56A 120.0 . . ? C57 C56 H56A 120.0 . . ? C56 C57 C52 120.2(3) . . ? C56 C57 H57A 119.9 . . ? C52 C57 H57A 119.9 . . ? C1 N1 C3 109.7(2) . . ? C1 N1 C4 122.9(2) . . ? C3 N1 C4 127.4(2) . . ? C1 N2 C2 109.7(2) . . ? C1 N2 C7 123.2(2) . . ? C2 N2 C7 127.10(19) . . ? C20 N3 C22 109.6(2) . . ? C20 N3 C23 123.2(2) . . ? C22 N3 C23 127.2(2) . . ? C20 N4 C21 109.6(2) . . ? C20 N4 C26 123.6(2) . . ? C21 N4 C26 126.8(2) . . ? C41 N5 C40 110.1(2) . . ? C41 N5 C42 123.3(2) . . ? C40 N5 C42 126.6(2) . . ? C41 N6 C39 109.7(2) . . ? C41 N6 C45 124.0(2) . . ? C39 N6 C45 126.30(19) . . ? C2 P1 C14 103.90(11) . . ? C2 P1 C8 104.04(10) . . ? C14 P1 C8 107.05(11) . . ? C2 P1 Se1 113.56(8) . . ? C14 P1 Se1 113.92(8) . . ? C8 P1 Se1 113.42(8) . . ? C21 P2 C33 105.20(12) . . ? C21 P2 C27 103.72(11) . . ? C33 P2 C27 106.50(11) . . ? C21 P2 Se2 113.26(8) . . ? C33 P2 Se2 112.82(8) . . ? C27 P2 Se2 114.46(8) . . ? C39 P3 C46 104.18(10) . . ? C39 P3 C52 104.52(11) . . ? C46 P3 C52 106.98(11) . . ? C39 P3 Se3 113.24(8) . . ? C46 P3 Se3 113.81(8) . . ? C52 P3 Se3 113.25(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C3 N1 0.2(2) . . . . ? P1 C2 C3 N1 -177.86(16) . . . . ? C13 C8 C9 C10 -1.4(4) . . . . ? P1 C8 C9 C10 177.65(19) . . . . ? C8 C9 C10 C11 0.2(4) . . . . ? C9 C10 C11 C12 1.2(4) . . . . ? C10 C11 C12 C13 -1.4(4) . . . . ? C11 C12 C13 C8 0.1(4) . . . . ? C9 C8 C13 C12 1.3(4) . . . . ? P1 C8 C13 C12 -177.8(2) . . . . ? C19 C14 C15 C16 1.1(5) . . . . ? P1 C14 C15 C16 -177.0(3) . . . . ? C14 C15 C16 C17 0.0(5) . . . . ? C15 C16 C17 C18 -1.4(5) . . . . ? C16 C17 C18 C19 1.7(5) . . . . ? C15 C14 C19 C18 -0.9(4) . . . . ? P1 C14 C19 C18 177.3(2) . . . . ? C17 C18 C19 C14 -0.5(5) . . . . ? N4 C21 C22 N3 0.6(3) . . . . ? P2 C21 C22 N3 -178.17(17) . . . . ? C32 C27 C28 C29 0.6(4) . . . . ? P2 C27 C28 C29 179.5(2) . . . . ? C27 C28 C29 C30 -0.5(4) . . . . ? C28 C29 C30 C31 -0.2(4) . . . . ? C29 C30 C31 C32 0.8(4) . . . . ? C30 C31 C32 C27 -0.7(4) . . . . ? C28 C27 C32 C31 0.0(4) . . . . ? P2 C27 C32 C31 -178.9(2) . . . . ? C38 C33 C34 C35 -1.4(5) . . . . ? P2 C33 C34 C35 -171.4(3) . . . . ? C33 C34 C35 C36 -1.8(7) . . . . ? C34 C35 C36 C37 3.2(7) . . . . ? C35 C36 C37 C38 -1.4(5) . . . . ? C36 C37 C38 C33 -1.9(4) . . . . ? C34 C33 C38 C37 3.2(4) . . . . ? P2 C33 C38 C37 173.2(2) . . . . ? N6 C39 C40 N5 0.0(2) . . . . ? P3 C39 C40 N5 175.81(17) . . . . ? C51 C46 C47 C48 -1.1(4) . . . . ? P3 C46 C47 C48 179.2(2) . . . . ? C46 C47 C48 C49 -0.7(4) . . . . ? C47 C48 C49 C50 1.7(4) . . . . ? C48 C49 C50 C51 -0.8(4) . . . . ? C49 C50 C51 C46 -0.9(4) . . . . ? C47 C46 C51 C50 1.9(4) . . . . ? P3 C46 C51 C50 -178.4(2) . . . . ? C57 C52 C53 C54 1.7(5) . . . . ? P3 C52 C53 C54 -176.1(3) . . . . ? C52 C53 C54 C55 0.4(6) . . . . ? C53 C54 C55 C56 -2.1(6) . . . . ? C54 C55 C56 C57 1.8(6) . . . . ? C55 C56 C57 C52 0.3(7) . . . . ? C53 C52 C57 C56 -2.0(5) . . . . ? P3 C52 C57 C56 175.7(3) . . . . ? N2 C1 N1 C3 0.7(2) . . . . ? S1 C1 N1 C3 -179.73(17) . . . . ? N2 C1 N1 C4 179.07(19) . . . . ? S1 C1 N1 C4 -1.3(3) . . . . ? C2 C3 N1 C1 -0.6(3) . . . . ? C2 C3 N1 C4 -178.9(2) . . . . ? C5 C4 N1 C1 -154.4(2) . . . . ? C6 C4 N1 C1 81.0(3) . . . . ? C5 C4 N1 C3 23.7(3) . . . . ? C6 C4 N1 C3 -100.9(3) . . . . ? N1 C1 N2 C2 -0.5(2) . . . . ? S1 C1 N2 C2 179.86(17) . . . . ? N1 C1 N2 C7 179.4(2) . . . . ? S1 C1 N2 C7 -0.2(3) . . . . ? C3 C2 N2 C1 0.2(2) . . . . ? P1 C2 N2 C1 178.40(16) . . . . ? C3 C2 N2 C7 -179.8(2) . . . . ? P1 C2 N2 C7 -1.6(3) . . . . ? N4 C20 N3 C22 1.0(3) . . . . ? S2 C20 N3 C22 -179.54(18) . . . . ? N4 C20 N3 C23 179.7(2) . . . . ? S2 C20 N3 C23 -0.8(3) . . . . ? C21 C22 N3 C20 -1.0(3) . . . . ? C21 C22 N3 C23 -179.7(2) . . . . ? C25 C23 N3 C20 -155.2(2) . . . . ? C24 C23 N3 C20 80.0(3) . . . . ? C25 C23 N3 C22 23.3(3) . . . . ? C24 C23 N3 C22 -101.5(3) . . . . ? N3 C20 N4 C21 -0.6(3) . . . . ? S2 C20 N4 C21 179.92(17) . . . . ? N3 C20 N4 C26 179.0(2) . . . . ? S2 C20 N4 C26 -0.5(3) . . . . ? C22 C21 N4 C20 0.0(3) . . . . ? P2 C21 N4 C20 178.86(16) . . . . ? C22 C21 N4 C26 -179.6(2) . . . . ? P2 C21 N4 C26 -0.7(3) . . . . ? N6 C41 N5 C40 0.0(3) . . . . ? S3 C41 N5 C40 -179.49(17) . . . . ? N6 C41 N5 C42 -179.35(19) . . . . ? S3 C41 N5 C42 1.2(3) . . . . ? C39 C40 N5 C41 0.0(3) . . . . ? C39 C40 N5 C42 179.3(2) . . . . ? C44 C42 N5 C41 149.7(2) . . . . ? C43 C42 N5 C41 -85.1(3) . . . . ? C44 C42 N5 C40 -29.5(3) . . . . ? C43 C42 N5 C40 95.7(3) . . . . ? N5 C41 N6 C39 0.1(2) . . . . ? S3 C41 N6 C39 179.53(17) . . . . ? N5 C41 N6 C45 -178.7(2) . . . . ? S3 C41 N6 C45 0.8(3) . . . . ? C40 C39 N6 C41 -0.1(2) . . . . ? P3 C39 N6 C41 -176.10(16) . . . . ? C40 C39 N6 C45 178.7(2) . . . . ? P3 C39 N6 C45 2.6(3) . . . . ? C3 C2 P1 C14 -4.7(2) . . . . ? N2 C2 P1 C14 177.54(18) . . . . ? C3 C2 P1 C8 -116.6(2) . . . . ? N2 C2 P1 C8 65.6(2) . . . . ? C3 C2 P1 Se1 119.6(2) . . . . ? N2 C2 P1 Se1 -58.2(2) . . . . ? C19 C14 P1 C2 92.2(2) . . . . ? C15 C14 P1 C2 -89.7(2) . . . . ? C19 C14 P1 C8 -158.1(2) . . . . ? C15 C14 P1 C8 20.0(3) . . . . ? C19 C14 P1 Se1 -31.9(2) . . . . ? C15 C14 P1 Se1 146.2(2) . . . . ? C9 C8 P1 C2 -157.6(2) . . . . ? C13 C8 P1 C2 21.5(2) . . . . ? C9 C8 P1 C14 92.8(2) . . . . ? C13 C8 P1 C14 -88.1(2) . . . . ? C9 C8 P1 Se1 -33.7(2) . . . . ? C13 C8 P1 Se1 145.37(18) . . . . ? C22 C21 P2 C33 -3.1(3) . . . . ? N4 C21 P2 C33 178.32(19) . . . . ? C22 C21 P2 C27 -114.8(2) . . . . ? N4 C21 P2 C27 66.6(2) . . . . ? C22 C21 P2 Se2 120.6(2) . . . . ? N4 C21 P2 Se2 -58.0(2) . . . . ? C34 C33 P2 C21 -131.2(3) . . . . ? C38 C33 P2 C21 58.8(2) . . . . ? C34 C33 P2 C27 -21.5(3) . . . . ? C38 C33 P2 C27 168.5(2) . . . . ? C34 C33 P2 Se2 104.8(2) . . . . ? C38 C33 P2 Se2 -65.1(2) . . . . ? C28 C27 P2 C21 30.1(2) . . . . ? C32 C27 P2 C21 -151.0(2) . . . . ? C28 C27 P2 C33 -80.7(2) . . . . ? C32 C27 P2 C33 98.3(2) . . . . ? C28 C27 P2 Se2 153.96(18) . . . . ? C32 C27 P2 Se2 -27.1(2) . . . . ? C40 C39 P3 C46 120.4(2) . . . . ? N6 C39 P3 C46 -64.5(2) . . . . ? C40 C39 P3 C52 8.3(2) . . . . ? N6 C39 P3 C52 -176.66(18) . . . . ? C40 C39 P3 Se3 -115.4(2) . . . . ? N6 C39 P3 Se3 59.6(2) . . . . ? C51 C46 P3 C39 154.1(2) . . . . ? C47 C46 P3 C39 -26.2(2) . . . . ? C51 C46 P3 C52 -95.6(2) . . . . ? C47 C46 P3 C52 84.1(2) . . . . ? C51 C46 P3 Se3 30.3(2) . . . . ? C47 C46 P3 Se3 -150.02(18) . . . . ? C53 C52 P3 C39 -97.5(2) . . . . ? C57 C52 P3 C39 84.8(3) . . . . ? C53 C52 P3 C46 152.4(2) . . . . ? C57 C52 P3 C46 -25.3(3) . . . . ? C53 C52 P3 Se3 26.2(3) . . . . ? C57 C52 P3 Se3 -151.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.367 _refine_diff_density_min -0.567 _refine_diff_density_rms 0.089 #END--------------------------------------------------------------------------- #------------------------------------------------------------------------------ data_Greg1159 _database_code_depnum_ccdc_archive 'CCDC 859812' #TrackingRef 'Gesamtcif-New.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H17 N2 P S Se' _chemical_formula_sum 'C17 H17 N2 P S Se' _chemical_formula_weight 391.32 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'F d d 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+3/4, -y+5/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+5/4, -y+3/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+5/4, -y+5/4, z+1/4' _cell_length_a 19.7156(9) _cell_length_b 35.6210(16) _cell_length_c 9.8574(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6922.7(6) _cell_formula_units_Z 16 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7346 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description stick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3168 _exptl_absorpt_coefficient_mu 2.380 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.79187 _exptl_absorpt_correction_T_max 0.82296 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9161 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3077 _reflns_number_gt 2669 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000102(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.013(7) _refine_ls_number_reflns 3077 _refine_ls_number_parameters 202 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0519 _refine_ls_wR_factor_gt 0.0499 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.934 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.36919(13) 0.08552(8) 0.8336(4) 0.0206(6) Uani 1 1 d . . . C2 C 0.27083(15) 0.07369(8) 0.7290(3) 0.0196(7) Uani 1 1 d . . . H2A H 0.2234 0.0719 0.7129 0.024 Uiso 1 1 calc R . . C3 C 0.32050(15) 0.06325(8) 0.6416(3) 0.0189(7) Uani 1 1 d . . . C4 C 0.26522(16) 0.10342(9) 0.9608(3) 0.0287(7) Uani 1 1 d . . . H4A H 0.2726 0.1306 0.9627 0.034 Uiso 1 1 calc R . . H4B H 0.2828 0.0922 1.0445 0.034 Uiso 1 1 calc R . . H4C H 0.2165 0.0983 0.9534 0.034 Uiso 1 1 calc R . . C5 C 0.44960(16) 0.06330(9) 0.6566(3) 0.0310(8) Uani 1 1 d . . . H5C H 0.4501 0.0673 0.5582 0.037 Uiso 1 1 calc R . . H5B H 0.4620 0.0372 0.6766 0.037 Uiso 1 1 calc R . . H5A H 0.4823 0.0803 0.6996 0.037 Uiso 1 1 calc R . . C6 C 0.35306(14) 0.00459(8) 0.4554(3) 0.0205(7) Uani 1 1 d . . . C7 C 0.38429(16) -0.00550(9) 0.3344(4) 0.0319(8) Uani 1 1 d . . . H7A H 0.3840 0.0113 0.2594 0.038 Uiso 1 1 calc R . . C8 C 0.41582(17) -0.04015(9) 0.3236(4) 0.0365(8) Uani 1 1 d . . . H8A H 0.4371 -0.0471 0.2408 0.044 Uiso 1 1 calc R . . C9 C 0.41668(17) -0.06459(9) 0.4314(4) 0.0318(8) Uani 1 1 d . . . H9A H 0.4384 -0.0883 0.4226 0.038 Uiso 1 1 calc R . . C10 C 0.38601(15) -0.05476(8) 0.5527(3) 0.0268(8) Uani 1 1 d . . . H10A H 0.3866 -0.0717 0.6271 0.032 Uiso 1 1 calc R . . C11 C 0.35437(14) -0.01999(8) 0.5652(3) 0.0242(7) Uani 1 1 d . . . H11A H 0.3337 -0.0130 0.6486 0.029 Uiso 1 1 calc R . . C12 C 0.22215(15) 0.04334(8) 0.4516(3) 0.0215(7) Uani 1 1 d . . . C13 C 0.19124(16) 0.00884(8) 0.4746(3) 0.0245(7) Uani 1 1 d . . . H13A H 0.2182 -0.0125 0.4960 0.029 Uiso 1 1 calc R . . C14 C 0.12124(16) 0.00529(9) 0.4667(3) 0.0290(8) Uani 1 1 d . . . H14A H 0.1006 -0.0185 0.4793 0.035 Uiso 1 1 calc R . . C15 C 0.08149(17) 0.03662(9) 0.4403(3) 0.0301(8) Uani 1 1 d . . . H15A H 0.0335 0.0344 0.4379 0.036 Uiso 1 1 calc R . . C16 C 0.11200(17) 0.07113(9) 0.4174(3) 0.0291(8) Uani 1 1 d . . . H16A H 0.0849 0.0925 0.3978 0.035 Uiso 1 1 calc R . . C17 C 0.18132(16) 0.07448(8) 0.4230(3) 0.0278(8) Uani 1 1 d . . . H17A H 0.2018 0.0982 0.4073 0.033 Uiso 1 1 calc R . . N1 N 0.30048(11) 0.08727(6) 0.8442(3) 0.0199(5) Uani 1 1 d . . . N2 N 0.38187(12) 0.07094(7) 0.7090(3) 0.0212(6) Uani 1 1 d . . . P1 P 0.31279(4) 0.05017(2) 0.46779(8) 0.02194(19) Uani 1 1 d . . . S1 S 0.42591(4) 0.09819(2) 0.95210(9) 0.0290(2) Uani 1 1 d . . . Se1 Se 0.353031(18) 0.089767(10) 0.33189(4) 0.03528(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0267(17) 0.0137(14) 0.0215(15) -0.0001(15) -0.0058(19) -0.0023(13) C2 0.0177(17) 0.0180(15) 0.0232(17) 0.0006(14) -0.0053(14) -0.0018(13) C3 0.0170(18) 0.0158(15) 0.0239(17) -0.0014(13) -0.0067(14) -0.0006(13) C4 0.0294(19) 0.0348(18) 0.0220(17) -0.0068(17) 0.0030(15) -0.0012(15) C5 0.0217(19) 0.0365(19) 0.0347(19) -0.0033(16) 0.0004(15) 0.0015(15) C6 0.0222(17) 0.0211(16) 0.0181(17) -0.0029(15) -0.0030(15) 0.0011(13) C7 0.041(2) 0.0309(18) 0.0239(18) -0.0022(18) -0.0008(19) 0.0048(15) C8 0.045(2) 0.039(2) 0.0256(18) -0.0067(18) 0.0079(19) 0.0119(17) C9 0.035(2) 0.0230(16) 0.037(2) -0.0057(17) -0.0021(18) 0.0087(16) C10 0.0314(19) 0.0224(16) 0.026(2) 0.0023(15) -0.0072(16) 0.0060(14) C11 0.0279(18) 0.0253(16) 0.0194(17) -0.0030(15) 0.0010(16) 0.0018(14) C12 0.0244(17) 0.0246(16) 0.0154(16) -0.0031(14) -0.0028(14) 0.0000(14) C13 0.0307(19) 0.0214(15) 0.0216(16) -0.0018(15) -0.0030(15) 0.0021(14) C14 0.032(2) 0.0268(18) 0.0277(19) -0.0063(16) -0.0007(16) -0.0060(16) C15 0.0256(18) 0.0385(19) 0.0263(18) -0.0075(17) -0.0052(16) -0.0012(16) C16 0.030(2) 0.0287(19) 0.0283(19) -0.0041(16) -0.0099(15) 0.0042(15) C17 0.032(2) 0.0233(17) 0.0282(19) -0.0002(15) -0.0066(16) -0.0007(15) N1 0.0184(13) 0.0196(12) 0.0216(14) -0.0012(12) 0.0011(13) 0.0001(11) N2 0.0180(14) 0.0206(13) 0.0250(14) -0.0008(12) -0.0004(12) 0.0005(11) P1 0.0243(5) 0.0200(4) 0.0214(4) 0.0001(4) -0.0016(4) 0.0017(3) S1 0.0282(5) 0.0292(4) 0.0296(5) -0.0026(4) -0.0096(4) -0.0045(4) Se1 0.0384(2) 0.03122(18) 0.03619(19) 0.01170(17) 0.00185(19) -0.00208(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.357(5) . ? C1 N1 1.360(3) . ? C1 S1 1.679(3) . ? C2 C3 1.356(4) . ? C2 N1 1.366(4) . ? C2 H2A 0.9500 . ? C3 N2 1.407(4) . ? C3 P1 1.782(3) . ? C4 N1 1.461(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N2 1.458(4) . ? C5 H5C 0.9800 . ? C5 H5B 0.9800 . ? C5 H5A 0.9800 . ? C6 C7 1.390(4) . ? C6 C11 1.393(4) . ? C6 P1 1.811(3) . ? C7 C8 1.386(4) . ? C7 H7A 0.9500 . ? C8 C9 1.373(5) . ? C8 H8A 0.9500 . ? C9 C10 1.385(5) . ? C9 H9A 0.9500 . ? C10 C11 1.392(4) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C12 C13 1.391(4) . ? C12 C17 1.399(4) . ? C12 P1 1.811(3) . ? C13 C14 1.388(4) . ? C13 H13A 0.9500 . ? C14 C15 1.388(4) . ? C14 H14A 0.9500 . ? C15 C16 1.387(4) . ? C15 H15A 0.9500 . ? C16 C17 1.373(4) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? P1 Se1 2.1008(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 N2 C1 N1 105.7(3) . . ? N2 C1 S1 127.6(2) . . ? N1 C1 S1 126.7(3) . . ? C3 C2 N1 108.5(3) . . ? C3 C2 H2A 125.8 . . ? N1 C2 H2A 125.8 . . ? C2 C3 N2 105.5(2) . . ? C2 C3 P1 128.4(2) . . ? N2 C3 P1 125.3(2) . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 H5C 109.5 . . ? N2 C5 H5B 109.5 . . ? H5C C5 H5B 109.5 . . ? N2 C5 H5A 109.5 . . ? H5C C5 H5A 109.5 . . ? H5B C5 H5A 109.5 . . ? C7 C6 C11 119.8(3) . . ? C7 C6 P1 118.9(2) . . ? C11 C6 P1 121.3(2) . . ? C8 C7 C6 119.6(3) . . ? C8 C7 H7A 120.2 . . ? C6 C7 H7A 120.2 . . ? C9 C8 C7 120.7(3) . . ? C9 C8 H8A 119.6 . . ? C7 C8 H8A 119.6 . . ? C8 C9 C10 120.2(3) . . ? C8 C9 H9A 119.9 . . ? C10 C9 H9A 119.9 . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? C10 C11 C6 119.9(3) . . ? C10 C11 H11A 120.1 . . ? C6 C11 H11A 120.1 . . ? C13 C12 C17 118.8(3) . . ? C13 C12 P1 122.5(2) . . ? C17 C12 P1 118.6(2) . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C16 C15 C14 119.9(3) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C16 C17 C12 120.8(3) . . ? C16 C17 H17A 119.6 . . ? C12 C17 H17A 119.6 . . ? C1 N1 C2 110.2(3) . . ? C1 N1 C4 123.5(3) . . ? C2 N1 C4 126.1(2) . . ? C1 N2 C3 110.1(2) . . ? C1 N2 C5 124.1(2) . . ? C3 N2 C5 125.7(3) . . ? C3 P1 C12 101.78(14) . . ? C3 P1 C6 105.17(14) . . ? C12 P1 C6 107.83(13) . . ? C3 P1 Se1 113.91(10) . . ? C12 P1 Se1 114.00(10) . . ? C6 P1 Se1 113.16(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 0.2(3) . . . . ? N1 C2 C3 P1 -169.9(2) . . . . ? C11 C6 C7 C8 0.7(4) . . . . ? P1 C6 C7 C8 179.5(2) . . . . ? C6 C7 C8 C9 -0.2(5) . . . . ? C7 C8 C9 C10 -0.2(5) . . . . ? C8 C9 C10 C11 -0.1(5) . . . . ? C9 C10 C11 C6 0.7(5) . . . . ? C7 C6 C11 C10 -1.0(4) . . . . ? P1 C6 C11 C10 -179.7(2) . . . . ? C17 C12 C13 C14 1.3(5) . . . . ? P1 C12 C13 C14 177.2(2) . . . . ? C12 C13 C14 C15 -2.3(5) . . . . ? C13 C14 C15 C16 2.2(5) . . . . ? C14 C15 C16 C17 -1.1(5) . . . . ? C15 C16 C17 C12 0.1(5) . . . . ? C13 C12 C17 C16 -0.2(5) . . . . ? P1 C12 C17 C16 -176.3(2) . . . . ? N2 C1 N1 C2 0.6(3) . . . . ? S1 C1 N1 C2 -178.4(2) . . . . ? N2 C1 N1 C4 -176.4(3) . . . . ? S1 C1 N1 C4 4.6(4) . . . . ? C3 C2 N1 C1 -0.5(3) . . . . ? C3 C2 N1 C4 176.4(3) . . . . ? N1 C1 N2 C3 -0.4(3) . . . . ? S1 C1 N2 C3 178.6(2) . . . . ? N1 C1 N2 C5 -178.4(3) . . . . ? S1 C1 N2 C5 0.6(4) . . . . ? C2 C3 N2 C1 0.1(3) . . . . ? P1 C3 N2 C1 170.7(2) . . . . ? C2 C3 N2 C5 178.0(3) . . . . ? P1 C3 N2 C5 -11.4(4) . . . . ? C2 C3 P1 C12 -13.4(3) . . . . ? N2 C3 P1 C12 178.2(2) . . . . ? C2 C3 P1 C6 -125.8(3) . . . . ? N2 C3 P1 C6 65.9(3) . . . . ? C2 C3 P1 Se1 109.7(3) . . . . ? N2 C3 P1 Se1 -58.6(3) . . . . ? C13 C12 P1 C3 -90.1(3) . . . . ? C17 C12 P1 C3 85.8(3) . . . . ? C13 C12 P1 C6 20.2(3) . . . . ? C17 C12 P1 C6 -163.8(2) . . . . ? C13 C12 P1 Se1 146.8(2) . . . . ? C17 C12 P1 Se1 -37.3(3) . . . . ? C7 C6 P1 C3 -149.6(2) . . . . ? C11 C6 P1 C3 29.1(3) . . . . ? C7 C6 P1 C12 102.4(2) . . . . ? C11 C6 P1 C12 -78.9(3) . . . . ? C7 C6 P1 Se1 -24.6(3) . . . . ? C11 C6 P1 Se1 154.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.279 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.056 #END---------------------------------------------------------------------------