Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Prof Hubert Schmidbaur' _publ_contact_author_address ; Anorganisch-chemisches Institut Tecnische Universitaet Muenchen Lichtenbergstrasse 4 Garching 85747 GERMANY ; _publ_contact_author_email H.SCHMIDBAUR@LRZ.TU-MUENCHEN.DE _publ_section_title ; Unsuccessful/Successful Attempts to Produce Penta(heteroaryl)phosphoranes/-arsoranes R5E (E = P, As; R = 2-Furyl, 2-Thienyl) ; loop_ _publ_author_name 'Hubert Schmidbaur' 'Uwe Monkowius' 'Stefan Nogai' data_uwe38 _database_code_depnum_ccdc_archive 'CCDC 230854' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 O3 P' _chemical_formula_weight 232.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.41030(10) _cell_length_b 11.77160(10) _cell_length_c 24.7644(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2160.23(4) _cell_formula_units_Z 8 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 50571 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'NONIUS DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50571 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 25.69 _reflns_number_total 2015 _reflns_number_gt 1989 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+1.0169P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2015 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0848 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 P1 P 0.06440(5) 0.47781(3) 0.102398(13) 0.01980(14) Uani 1 1 d . . . C11 C 0.20441(18) 0.48720(11) 0.16185(5) 0.0213(3) Uani 1 1 d . . . O12 O 0.24646(14) 0.39331(8) 0.19276(4) 0.0274(2) Uani 1 1 d . . . C13 C 0.3576(2) 0.43140(15) 0.23310(6) 0.0325(3) Uani 1 1 d . . . H13 H 0.402(3) 0.3693(16) 0.2563(8) 0.045(5) Uiso 1 1 d . . . C14 C 0.3868(2) 0.54318(15) 0.22854(6) 0.0326(3) Uani 1 1 d . . . H14 H 0.463(3) 0.5875(15) 0.2512(8) 0.039(5) Uiso 1 1 d . . . C15 C 0.28718(19) 0.58017(13) 0.18252(6) 0.0274(3) Uani 1 1 d . . . H15 H 0.277(3) 0.6545(16) 0.1689(8) 0.039(5) Uiso 1 1 d . . . C21 C 0.20538(18) 0.39918(11) 0.05647(5) 0.0210(3) Uani 1 1 d . . . O22 O 0.27185(14) 0.29232(8) 0.06821(4) 0.0273(2) Uani 1 1 d . . . C23 C 0.3814(2) 0.26295(13) 0.02581(6) 0.0301(3) Uani 1 1 d . . . H23 H 0.438(3) 0.1895(17) 0.0289(7) 0.040(5) Uiso 1 1 d . . . C24 C 0.3862(2) 0.34535(13) -0.01138(6) 0.0297(3) Uani 1 1 d . . . H24 H 0.459(3) 0.3444(15) -0.0444(7) 0.039(5) Uiso 1 1 d . . . C25 C 0.2725(2) 0.43390(13) 0.00824(5) 0.0266(3) Uani 1 1 d . . . H25 H 0.248(3) 0.5048(17) -0.0084(8) 0.035(4) Uiso 1 1 d . . . C31 C -0.10539(19) 0.37653(11) 0.12236(5) 0.0208(3) Uani 1 1 d . . . O32 O -0.05879(13) 0.27162(8) 0.14289(4) 0.0250(2) Uani 1 1 d . . . C33 C -0.2172(2) 0.21717(13) 0.15472(6) 0.0290(3) Uani 1 1 d . . . H33 H -0.205(3) 0.1412(16) 0.1697(7) 0.039(5) Uiso 1 1 d . . . C34 C -0.3596(2) 0.28271(14) 0.14267(6) 0.0304(3) Uani 1 1 d . . . H34 H -0.483(3) 0.2647(15) 0.1472(7) 0.039(5) Uiso 1 1 d . . . C35 C -0.28831(19) 0.38599(13) 0.12166(6) 0.0265(3) Uani 1 1 d . . . H35 H -0.353(3) 0.4500(18) 0.1087(7) 0.042(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0200(2) 0.0209(2) 0.0185(2) 0.00099(12) -0.00086(12) 0.00098(12) C11 0.0197(7) 0.0248(7) 0.0193(6) 0.0002(5) 0.0024(5) 0.0000(5) O12 0.0305(5) 0.0300(5) 0.0217(5) 0.0030(4) -0.0057(4) -0.0006(4) C13 0.0266(8) 0.0507(9) 0.0202(6) 0.0001(6) -0.0053(6) 0.0008(7) C14 0.0216(7) 0.0495(9) 0.0266(7) -0.0107(7) -0.0011(6) -0.0056(7) C15 0.0218(7) 0.0309(8) 0.0295(7) -0.0049(6) 0.0024(5) -0.0042(6) C21 0.0205(7) 0.0223(6) 0.0200(6) 0.0004(5) -0.0025(5) -0.0002(5) O22 0.0301(6) 0.0253(5) 0.0265(5) 0.0024(4) 0.0059(4) 0.0050(4) C23 0.0292(8) 0.0303(8) 0.0307(7) -0.0058(6) 0.0052(6) 0.0040(6) C24 0.0279(8) 0.0390(8) 0.0222(7) -0.0064(6) 0.0038(6) -0.0013(6) C25 0.0280(8) 0.0310(8) 0.0207(6) 0.0030(6) 0.0002(5) -0.0002(6) C31 0.0216(7) 0.0223(6) 0.0185(6) -0.0014(5) -0.0010(5) 0.0006(5) O32 0.0217(5) 0.0226(5) 0.0307(5) 0.0028(4) 0.0004(4) -0.0011(4) C33 0.0284(8) 0.0281(7) 0.0305(7) -0.0009(6) 0.0029(6) -0.0085(6) C34 0.0213(8) 0.0389(8) 0.0310(7) -0.0044(6) 0.0028(6) -0.0077(6) C35 0.0217(7) 0.0322(8) 0.0256(7) -0.0020(6) -0.0020(5) 0.0023(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C21 1.8005(14) . ? P1 C31 1.8024(14) . ? P1 C11 1.8045(14) . ? C11 C15 1.355(2) . ? C11 O12 1.3801(16) . ? O12 C13 1.3704(17) . ? C13 C14 1.338(2) . ? C13 H13 0.98(2) . ? C14 C15 1.426(2) . ? C14 H14 0.951(19) . ? C15 H15 0.941(19) . ? C21 C25 1.3570(19) . ? C21 O22 1.3818(16) . ? O22 C23 1.3717(17) . ? C23 C24 1.338(2) . ? C23 H23 0.97(2) . ? C24 C25 1.425(2) . ? C24 H24 0.979(19) . ? C25 H25 0.95(2) . ? C31 C35 1.360(2) . ? C31 O32 1.3794(16) . ? O32 C33 1.3694(17) . ? C33 C34 1.341(2) . ? C33 H33 0.972(19) . ? C34 C35 1.424(2) . ? C34 H34 0.94(2) . ? C35 H35 0.95(2) . ? 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 C21 P1 C31 103.79(6) . . ? C21 P1 C11 102.31(6) . . ? C31 P1 C11 102.60(6) . . ? C15 C11 O12 109.58(12) . . ? C15 C11 P1 128.17(11) . . ? O12 C11 P1 122.22(9) . . ? C13 O12 C11 106.14(11) . . ? C14 C13 O12 110.93(13) . . ? C14 C13 H13 136.5(12) . . ? O12 C13 H13 112.4(12) . . ? C13 C14 C15 106.51(13) . . ? C13 C14 H14 125.9(11) . . ? C15 C14 H14 127.6(11) . . ? C11 C15 C14 106.84(14) . . ? C11 C15 H15 125.3(12) . . ? C14 C15 H15 127.8(12) . . ? C25 C21 O22 109.19(12) . . ? C25 C21 P1 127.88(11) . . ? O22 C21 P1 122.81(9) . . ? C23 O22 C21 106.22(11) . . ? C24 C23 O22 111.08(13) . . ? C24 C23 H23 133.9(11) . . ? O22 C23 H23 115.0(11) . . ? C23 C24 C25 106.26(13) . . ? C23 C24 H24 125.6(11) . . ? C25 C24 H24 128.1(11) . . ? C21 C25 C24 107.24(13) . . ? C21 C25 H25 125.2(11) . . ? C24 C25 H25 127.5(11) . . ? C35 C31 O32 109.12(12) . . ? C35 C31 P1 129.64(11) . . ? O32 C31 P1 121.23(10) . . ? C33 O32 C31 106.46(11) . . ? C34 C33 O32 110.96(13) . . ? C34 C33 H33 133.4(12) . . ? O32 C33 H33 115.7(12) . . ? C33 C34 C35 106.31(13) . . ? C33 C34 H34 127.2(11) . . ? C35 C34 H34 126.4(11) . . ? C31 C35 C34 107.16(14) . . ? C31 C35 H35 125.0(13) . . ? C34 C35 H35 127.9(13) . . ? 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 C21 P1 C11 C15 109.73(13) . . . . ? C31 P1 C11 C15 -142.89(13) . . . . ? C21 P1 C11 O12 -68.27(12) . . . . ? C31 P1 C11 O12 39.11(12) . . . . ? C15 C11 O12 C13 0.02(15) . . . . ? P1 C11 O12 C13 178.35(10) . . . . ? C11 O12 C13 C14 -0.28(16) . . . . ? O12 C13 C14 C15 0.42(17) . . . . ? O12 C11 C15 C14 0.22(16) . . . . ? P1 C11 C15 C14 -177.98(10) . . . . ? C13 C14 C15 C11 -0.39(17) . . . . ? C31 P1 C21 C25 135.88(13) . . . . ? C11 P1 C21 C25 -117.65(13) . . . . ? C31 P1 C21 O22 -48.57(12) . . . . ? C11 P1 C21 O22 57.90(12) . . . . ? C25 C21 O22 C23 0.03(15) . . . . ? P1 C21 O22 C23 -176.25(10) . . . . ? C21 O22 C23 C24 -0.08(16) . . . . ? O22 C23 C24 C25 0.09(17) . . . . ? O22 C21 C25 C24 0.02(16) . . . . ? P1 C21 C25 C24 176.06(10) . . . . ? C23 C24 C25 C21 -0.07(17) . . . . ? C21 P1 C31 C35 -127.98(13) . . . . ? C11 P1 C31 C35 125.77(13) . . . . ? C21 P1 C31 O32 53.31(11) . . . . ? C11 P1 C31 O32 -52.94(11) . . . . ? C35 C31 O32 C33 0.00(15) . . . . ? P1 C31 O32 C33 178.95(10) . . . . ? C31 O32 C33 C34 -0.05(15) . . . . ? O32 C33 C34 C35 0.08(17) . . . . ? O32 C31 C35 C34 0.05(16) . . . . ? P1 C31 C35 C34 -178.78(10) . . . . ? C33 C34 C35 C31 -0.08(16) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.180 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.050 #===END data_uwe16 _database_code_depnum_ccdc_archive 'CCDC 230855' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cl2 N P S3' _chemical_formula_weight 392.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 22.92100(10) _cell_length_b 8.87400(10) _cell_length_c 8.7150(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1772.64(6) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 46842 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.801 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'Nonius DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46842 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.71 _reflns_number_total 3916 _reflns_number_gt 3867 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Structure was refined as racemic twin. Contribution of one specimen to the racemic twin 0.47(6). ; _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^)+(0.0544P)^2^+0.3725P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0108(12) _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 0.47(6) _refine_ls_number_reflns 3916 _refine_ls_number_parameters 204 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0751 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.049 _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 Cl2 Cl -0.13963(2) -0.90784(5) -0.86718(6) 0.02723(12) Uani 1 1 d . . . Cl1 Cl -0.00573(2) -0.60793(5) -0.49097(6) 0.02927(12) Uani 1 1 d . . . P1 P -0.077589(17) -0.48038(5) -0.47356(6) 0.01870(11) Uani 1 1 d . . . S3 S -0.102830(19) -0.24071(5) -0.70851(5) 0.02055(11) Uani 1 1 d . . . S1 S 0.00992(2) -0.23512(5) -0.39142(6) 0.02581(12) Uani 1 1 d . . . S2 S -0.11511(2) -0.69737(6) -0.22210(6) 0.03143(12) Uani 1 1 d . . . C34 C -0.13588(8) -0.2846(2) -0.8768(2) 0.0232(3) Uani 1 1 d . . . H34A H -0.1461 -0.2134 -0.9503 0.028 Uiso 1 1 calc R . . C12 C -0.09222(9) -0.2440(2) -0.2653(2) 0.0231(4) Uani 1 1 d . . . H12A H -0.1296 -0.2743 -0.2378 0.028 Uiso 1 1 calc R . . C32 C -0.12650(8) -0.5204(2) -0.7665(2) 0.0226(4) Uani 1 1 d . . . H32A H -0.1297 -0.6246 -0.7581 0.027 Uiso 1 1 calc R . . C13 C -0.06427(9) -0.1136(2) -0.2074(3) 0.0275(4) Uani 1 1 d . . . H13A H -0.0812 -0.0479 -0.1372 0.033 Uiso 1 1 calc R . . C24 C -0.18616(11) -0.7495(2) -0.2060(3) 0.0332(4) Uani 1 1 d . . . H24A H -0.1999 -0.8140 -0.1300 0.040 Uiso 1 1 calc R . . C31 C -0.10191(8) -0.4284(2) -0.6555(2) 0.0205(3) Uani 1 1 d . . . C11 C -0.05709(7) -0.32069(19) -0.3679(2) 0.0205(3) Uani 1 1 d . . . C21 C -0.13088(8) -0.58855(19) -0.3806(3) 0.0223(3) Uani 1 1 d . . . C14 C -0.00915(10) -0.0957(2) -0.2670(3) 0.0294(4) Uani 1 1 d . . . H14A H 0.0152 -0.0156 -0.2419 0.035 Uiso 1 1 calc R . . C33 C -0.14594(8) -0.4369(2) -0.8930(2) 0.0238(3) Uani 1 1 d . . . H33A H -0.1637 -0.4795 -0.9786 0.029 Uiso 1 1 calc R . . C22 C -0.19022(9) -0.5929(2) -0.4185(3) 0.0277(4) Uani 1 1 d . . . H22A H -0.2071 -0.5410 -0.4999 0.033 Uiso 1 1 calc R . . N1 N -0.23712(10) -0.2788(3) -1.1567(3) 0.0520(6) Uani 1 1 d . . . C1 C -0.28329(11) -0.0513(3) -1.0101(3) 0.0389(5) Uani 1 1 d . . . C2 C -0.25799(10) -0.1798(3) -1.0919(3) 0.0369(5) Uani 1 1 d . . . C23 C -0.22094(10) -0.6873(3) -0.3155(3) 0.0342(5) Uani 1 1 d . . . H23A H -0.2608 -0.7050 -0.3221 0.041 Uiso 1 1 calc R . . H3 H -0.2527(16) 0.008(3) -0.943(4) 0.056(10) Uiso 1 1 d . . . H2 H -0.3132(17) -0.102(3) -0.923(5) 0.055(10) Uiso 1 1 d . . . H1 H -0.3023(14) 0.014(4) -1.071(4) 0.049(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl2 0.0244(2) 0.0207(2) 0.0366(3) 0.00011(17) -0.00177(18) -0.00188(14) Cl1 0.0222(2) 0.0323(2) 0.0334(3) -0.00455(18) -0.00257(18) 0.00912(16) P1 0.01599(19) 0.0192(2) 0.0210(2) 0.00011(17) -0.00086(16) 0.00050(14) S3 0.0217(2) 0.01793(19) 0.0220(2) -0.00031(15) -0.00025(16) -0.00106(14) S1 0.0208(2) 0.0285(2) 0.0281(3) -0.00386(18) 0.00313(18) -0.00598(16) S2 0.0353(3) 0.0295(2) 0.0294(3) 0.0087(2) -0.0058(2) -0.00287(19) C34 0.0231(8) 0.0242(8) 0.0223(9) 0.0026(7) 0.0010(7) 0.0005(7) C12 0.0233(8) 0.0241(9) 0.0220(9) -0.0001(6) 0.0008(7) 0.0006(7) C32 0.0221(8) 0.0219(8) 0.0237(9) -0.0020(7) -0.0004(7) -0.0006(6) C13 0.0305(10) 0.0228(8) 0.0291(10) -0.0034(7) 0.0013(8) 0.0005(7) C24 0.0407(11) 0.0278(10) 0.0309(11) 0.0060(8) 0.0047(9) -0.0073(8) C31 0.0193(8) 0.0202(8) 0.0221(8) -0.0012(7) -0.0001(6) -0.0001(6) C11 0.0185(7) 0.0213(7) 0.0215(8) -0.0012(6) -0.0006(6) -0.0007(6) C21 0.0221(8) 0.0206(8) 0.0240(9) 0.0009(6) -0.0026(7) -0.0011(6) C14 0.0320(10) 0.0244(9) 0.0317(11) -0.0018(7) -0.0016(8) -0.0060(7) C33 0.0234(8) 0.0254(8) 0.0226(9) -0.0028(7) -0.0013(7) -0.0019(6) C22 0.0245(9) 0.0261(9) 0.0324(11) 0.0054(7) 0.0060(8) -0.0026(7) N1 0.0316(11) 0.0707(15) 0.0538(14) -0.0060(12) -0.0085(10) 0.0082(10) C1 0.0364(12) 0.0404(12) 0.0399(13) 0.0013(10) -0.0048(10) -0.0084(9) C2 0.0250(10) 0.0518(13) 0.0339(11) 0.0049(10) -0.0060(8) -0.0047(9) C23 0.0284(10) 0.0365(11) 0.0377(12) 0.0049(9) 0.0057(8) -0.0073(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 P1 2.0043(6) . ? P1 C31 1.743(2) . ? P1 C21 1.752(2) . ? P1 C11 1.7542(18) . ? S3 C34 1.696(2) . ? S3 C31 1.7288(18) . ? S1 C14 1.702(2) . ? S1 C11 1.7256(18) . ? S2 C24 1.699(2) . ? S2 C21 1.724(2) . ? C34 C33 1.378(3) . ? C34 H34A 0.9300 . ? C12 C11 1.382(3) . ? C12 C13 1.415(3) . ? C12 H12A 0.9300 . ? C32 C31 1.385(3) . ? C32 C33 1.402(3) . ? C32 H32A 0.9300 . ? C13 C14 1.375(3) . ? C13 H13A 0.9300 . ? C24 C23 1.361(3) . ? C24 H24A 0.9300 . ? C21 C22 1.400(3) . ? C14 H14A 0.9300 . ? C33 H33A 0.9300 . ? C22 C23 1.415(3) . ? C22 H22A 0.9300 . ? N1 C2 1.149(4) . ? C1 C2 1.464(4) . ? C1 H3 1.05(4) . ? C1 H2 1.12(4) . ? C1 H1 0.90(4) . ? C23 H23A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 P1 C21 110.03(9) . . ? C31 P1 C11 110.47(9) . . ? C21 P1 C11 112.74(9) . . ? C31 P1 Cl1 110.09(7) . . ? C21 P1 Cl1 107.37(6) . . ? C11 P1 Cl1 106.01(6) . . ? C34 S3 C31 90.86(9) . . ? C14 S1 C11 90.90(9) . . ? C24 S2 C21 91.03(10) . . ? C33 C34 S3 112.90(15) . . ? C33 C34 H34A 123.5 . . ? S3 C34 H34A 123.5 . . ? C11 C12 C13 111.68(18) . . ? C11 C12 H12A 124.2 . . ? C13 C12 H12A 124.2 . . ? C31 C32 C33 111.53(17) . . ? C31 C32 H32A 124.2 . . ? C33 C32 H32A 124.2 . . ? C14 C13 C12 112.07(19) . . ? C14 C13 H13A 124.0 . . ? C12 C13 H13A 124.0 . . ? C23 C24 S2 113.14(16) . . ? C23 C24 H24A 123.4 . . ? S2 C24 H24A 123.4 . . ? C32 C31 S3 112.10(14) . . ? C32 C31 P1 127.55(15) . . ? S3 C31 P1 120.12(11) . . ? C12 C11 S1 112.26(14) . . ? C12 C11 P1 125.53(14) . . ? S1 C11 P1 122.11(10) . . ? C22 C21 S2 112.17(15) . . ? C22 C21 P1 125.68(16) . . ? S2 C21 P1 122.09(11) . . ? C13 C14 S1 113.09(15) . . ? C13 C14 H14A 123.5 . . ? S1 C14 H14A 123.5 . . ? C34 C33 C32 112.61(18) . . ? C34 C33 H33A 123.7 . . ? C32 C33 H33A 123.7 . . ? C21 C22 C23 110.49(19) . . ? C21 C22 H22A 124.8 . . ? C23 C22 H22A 124.8 . . ? C2 C1 H3 113.2(19) . . ? C2 C1 H2 105.3(17) . . ? H3 C1 H2 103(3) . . ? C2 C1 H1 114(2) . . ? H3 C1 H1 109(3) . . ? H2 C1 H1 111(3) . . ? N1 C2 C1 178.6(3) . . ? C24 C23 C22 113.2(2) . . ? C24 C23 H23A 123.4 . . ? C22 C23 H23A 123.4 . . ? 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 C31 S3 C34 C33 -0.10(16) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C21 S2 C24 C23 -0.16(19) . . . . ? C33 C32 C31 S3 -0.2(2) . . . . ? C33 C32 C31 P1 174.26(15) . . . . ? C34 S3 C31 C32 0.16(15) . . . . ? C34 S3 C31 P1 -174.75(12) . . . . ? C21 P1 C31 C32 -48.63(19) . . . . ? C11 P1 C31 C32 -173.74(16) . . . . ? Cl1 P1 C31 C32 69.52(18) . . . . ? C21 P1 C31 S3 125.42(12) . . . . ? C11 P1 C31 S3 0.31(14) . . . . ? Cl1 P1 C31 S3 -116.43(10) . . . . ? C13 C12 C11 S1 0.7(2) . . . . ? C13 C12 C11 P1 -175.66(15) . . . . ? C14 S1 C11 C12 -0.83(16) . . . . ? C14 S1 C11 P1 175.67(14) . . . . ? C31 P1 C11 C12 95.14(18) . . . . ? C21 P1 C11 C12 -28.4(2) . . . . ? Cl1 P1 C11 C12 -145.62(16) . . . . ? C31 P1 C11 S1 -80.88(13) . . . . ? C21 P1 C11 S1 155.55(11) . . . . ? Cl1 P1 C11 S1 38.36(13) . . . . ? C24 S2 C21 C22 0.33(17) . . . . ? C24 S2 C21 P1 177.58(14) . . . . ? C31 P1 C21 C22 -19.9(2) . . . . ? C11 P1 C21 C22 103.96(19) . . . . ? Cl1 P1 C21 C22 -139.66(17) . . . . ? C31 P1 C21 S2 163.29(12) . . . . ? C11 P1 C21 S2 -72.91(14) . . . . ? Cl1 P1 C21 S2 43.48(14) . . . . ? C12 C13 C14 S1 -0.5(3) . . . . ? C11 S1 C14 C13 0.76(18) . . . . ? S3 C34 C33 C32 0.0(2) . . . . ? C31 C32 C33 C34 0.1(2) . . . . ? S2 C21 C22 C23 -0.4(2) . . . . ? P1 C21 C22 C23 -177.55(16) . . . . ? S2 C24 C23 C22 -0.1(3) . . . . ? C21 C22 C23 C24 0.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.71 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.342 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.067 data_uwe25 _database_code_depnum_ccdc_archive 'CCDC 230856' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 Br O P S4' _chemical_formula_weight 475.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.05230(10) _cell_length_b 13.4590(2) _cell_length_c 13.56310(10) _cell_angle_alpha 90.00 _cell_angle_beta 114.3240(6) _cell_angle_gamma 90.00 _cell_volume 2004.80(4) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 52435 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 2.549 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'NONIUS DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 52435 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 27.54 _reflns_number_total 4595 _reflns_number_gt 4395 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0678P)^2^+3.9801P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4595 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 Br1 Br 0.79798(3) 0.62206(2) 0.11424(2) 0.02593(11) Uani 1 1 d . . . P1 P 0.30173(7) 0.63344(5) 0.53886(6) 0.02067(16) Uani 1 1 d . . . S1 S 0.05655(7) 0.58554(6) 0.35698(6) 0.02925(18) Uani 1 1 d . . . S3 S 0.52026(8) 0.74024(7) 0.52362(7) 0.0361(2) Uani 1 1 d . . . S2 S 0.30942(7) 0.51483(6) 0.73155(6) 0.03047(18) Uani 1 1 d . . . S4 S 0.22994(9) 0.85002(7) 0.47670(8) 0.0387(2) Uani 1 1 d . . . C32 C 0.3798(3) 0.6149(2) 0.3679(2) 0.0244(6) Uani 1 1 d . . . H32A H 0.3204 0.5673 0.3270 0.029 Uiso 1 1 calc R . . C31 C 0.3972(3) 0.6601(2) 0.4728(2) 0.0228(5) Uani 1 1 d . . . C21 C 0.3840(3) 0.5807(2) 0.6679(2) 0.0235(5) Uani 1 1 d . . . C41 C 0.2299(3) 0.7453(2) 0.5499(2) 0.0225(5) Uani 1 1 d . . . C42 C 0.1582(3) 0.7569(2) 0.6193(3) 0.0317(7) Uani 1 1 d . . . H42A H 0.1467 0.7099 0.6664 0.038 Uiso 1 1 calc R . . C24 C 0.4415(3) 0.5013(2) 0.8447(2) 0.0285(6) Uani 1 1 d . . . H24A H 0.4468 0.4675 0.9080 0.034 Uiso 1 1 calc R . . C11 C 0.1900(3) 0.5472(2) 0.4605(2) 0.0240(6) Uani 1 1 d . . . C22 C 0.5066(3) 0.5901(2) 0.7325(2) 0.0273(6) Uani 1 1 d . . . H22A H 0.5628 0.6234 0.7113 0.033 Uiso 1 1 calc R . . C12 C 0.2036(3) 0.4433(3) 0.4625(3) 0.0372(8) Uani 1 1 d . . . H12A H 0.2716 0.4079 0.5126 0.045 Uiso 1 1 calc R . . C34 C 0.5521(3) 0.7237(2) 0.4159(3) 0.0329(7) Uani 1 1 d . . . H34A H 0.6180 0.7559 0.4079 0.039 Uiso 1 1 calc R . . C23 C 0.5383(3) 0.5440(2) 0.8345(2) 0.0298(6) Uani 1 1 d . . . H23A H 0.6187 0.5430 0.8897 0.036 Uiso 1 1 calc R . . C14 C 0.0170(3) 0.4659(3) 0.3169(3) 0.0310(6) Uani 1 1 d . . . H14A H -0.0563 0.4478 0.2574 0.037 Uiso 1 1 calc R . . C13 C 0.1013(3) 0.3990(3) 0.3789(3) 0.0404(8) Uani 1 1 d . . . H13A H 0.0925 0.3293 0.3674 0.048 Uiso 1 1 calc R . . C33 C 0.4758(3) 0.6604(3) 0.3410(3) 0.0360(7) Uani 1 1 d . . . H33A H 0.4834 0.6461 0.2755 0.043 Uiso 1 1 calc R . . C44 C 0.1431(3) 0.9116(2) 0.5261(3) 0.0329(7) Uani 1 1 d . . . H44A H 0.1180 0.9784 0.5071 0.039 Uiso 1 1 calc R . . C43 C 0.1116(3) 0.8584(3) 0.5955(3) 0.0358(7) Uani 1 1 d . . . H43A H 0.0615 0.8859 0.6272 0.043 Uiso 1 1 calc R . . O1 O 0.7336(3) 0.7428(3) 0.7878(3) 0.0650(10) Uani 1 1 d . . . C1 C 0.8420(4) 0.7025(5) 0.8578(4) 0.0616(13) Uani 1 1 d . . . H1A H 0.8980 0.7559 0.8971 0.092 Uiso 1 1 calc R . . H1B H 0.8776 0.6638 0.8169 0.092 Uiso 1 1 calc R . . H1C H 0.8279 0.6590 0.9094 0.092 Uiso 1 1 calc R . . H1 H 0.752(7) 0.785(6) 0.736(6) 0.11(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02644(17) 0.03015(18) 0.02187(17) 0.00109(10) 0.01062(12) 0.00087(10) P1 0.0200(3) 0.0194(3) 0.0208(3) 0.0015(2) 0.0066(3) -0.0004(2) S1 0.0240(3) 0.0265(4) 0.0301(4) 0.0017(3) 0.0039(3) 0.0008(3) S3 0.0376(4) 0.0377(4) 0.0370(4) -0.0018(3) 0.0193(4) -0.0058(3) S2 0.0250(4) 0.0361(4) 0.0295(4) 0.0108(3) 0.0104(3) 0.0004(3) S4 0.0416(5) 0.0324(4) 0.0466(5) 0.0070(4) 0.0228(4) 0.0055(3) C32 0.0187(12) 0.0375(16) 0.0219(13) 0.0096(11) 0.0133(11) 0.0056(11) C31 0.0220(13) 0.0219(13) 0.0236(13) 0.0001(11) 0.0084(10) -0.0005(10) C21 0.0214(13) 0.0221(13) 0.0238(13) 0.0016(11) 0.0062(11) -0.0015(10) C41 0.0232(13) 0.0216(13) 0.0234(13) 0.0041(10) 0.0102(11) -0.0003(10) C42 0.0250(14) 0.0134(12) 0.0463(18) -0.0008(12) 0.0043(13) 0.0107(10) C24 0.0368(16) 0.0247(14) 0.0209(13) 0.0006(11) 0.0088(12) 0.0006(12) C11 0.0206(12) 0.0218(13) 0.0263(14) 0.0020(11) 0.0062(11) 0.0009(10) C22 0.0250(14) 0.0239(14) 0.0274(15) 0.0035(11) 0.0052(11) -0.0021(11) C12 0.0285(16) 0.0310(16) 0.0365(17) 0.0030(14) -0.0024(13) -0.0060(13) C34 0.0318(16) 0.0269(15) 0.0434(18) 0.0056(13) 0.0189(14) 0.0037(12) C23 0.0308(15) 0.0261(14) 0.0229(14) 0.0017(11) 0.0013(12) -0.0011(12) C14 0.0235(14) 0.0328(16) 0.0300(15) -0.0037(13) 0.0044(12) -0.0035(12) C13 0.0349(18) 0.0214(14) 0.052(2) -0.0030(14) 0.0055(16) -0.0013(13) C33 0.0456(19) 0.0368(17) 0.0353(17) 0.0007(14) 0.0265(15) 0.0028(15) C44 0.0328(16) 0.0242(15) 0.0414(18) 0.0032(13) 0.0150(14) 0.0004(12) C43 0.0363(17) 0.0373(17) 0.0401(19) 0.0025(14) 0.0222(15) 0.0081(14) O1 0.0352(15) 0.093(3) 0.067(2) 0.0399(19) 0.0210(14) -0.0038(15) C1 0.050(2) 0.092(4) 0.049(2) 0.032(3) 0.027(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C31 1.762(3) . ? P1 C11 1.764(3) . ? P1 C21 1.766(3) . ? P1 C41 1.773(3) . ? S1 C14 1.704(3) . ? S1 C11 1.722(3) . ? S3 C34 1.672(4) . ? S3 C31 1.731(3) . ? S2 C24 1.706(3) . ? S2 C21 1.726(3) . ? S4 C44 1.676(4) . ? S4 C41 1.724(3) . ? C32 C33 1.481(4) . ? C32 C31 1.481(4) . ? C32 H32A 0.9500 . ? C21 C22 1.379(4) . ? C41 C42 1.526(5) . ? C42 C43 1.461(4) . ? C42 H42A 0.9500 . ? C24 C23 1.358(5) . ? C24 H24A 0.9500 . ? C11 C12 1.406(4) . ? C22 C23 1.418(4) . ? C22 H22A 0.9500 . ? C12 C13 1.417(5) . ? C12 H12A 0.9500 . ? C34 C33 1.354(5) . ? C34 H34A 0.9500 . ? C23 H23A 0.9500 . ? C14 C13 1.359(5) . ? C14 H14A 0.9500 . ? C13 H13A 0.9500 . ? C33 H33A 0.9500 . ? C44 C43 1.354(5) . ? C44 H44A 0.9500 . ? C43 H43A 0.9500 . ? O1 C1 1.371(6) . ? O1 H1 1.00(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? 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 C31 P1 C11 108.91(14) . . ? C31 P1 C21 111.60(14) . . ? C11 P1 C21 108.05(14) . . ? C31 P1 C41 108.28(13) . . ? C11 P1 C41 109.35(14) . . ? C21 P1 C41 110.62(14) . . ? C14 S1 C11 91.23(15) . . ? C34 S3 C31 92.08(16) . . ? C24 S2 C21 91.13(15) . . ? C44 S4 C41 91.46(16) . . ? C33 C32 C31 104.5(3) . . ? C33 C32 H32A 127.7 . . ? C31 C32 H32A 127.7 . . ? C32 C31 S3 113.4(2) . . ? C32 C31 P1 122.8(2) . . ? S3 C31 P1 123.79(17) . . ? C22 C21 S2 111.8(2) . . ? C22 C21 P1 127.6(2) . . ? S2 C21 P1 120.44(16) . . ? C42 C41 S4 113.9(2) . . ? C42 C41 P1 124.0(2) . . ? S4 C41 P1 121.96(17) . . ? C43 C42 C41 102.9(3) . . ? C43 C42 H42A 128.6 . . ? C41 C42 H42A 128.6 . . ? C23 C24 S2 112.7(2) . . ? C23 C24 H24A 123.7 . . ? S2 C24 H24A 123.7 . . ? C12 C11 S1 112.1(2) . . ? C12 C11 P1 126.1(2) . . ? S1 C11 P1 121.23(17) . . ? C21 C22 C23 111.6(3) . . ? C21 C22 H22A 124.2 . . ? C23 C22 H22A 124.2 . . ? C11 C12 C13 110.3(3) . . ? C11 C12 H12A 124.9 . . ? C13 C12 H12A 124.9 . . ? C33 C34 S3 114.2(3) . . ? C33 C34 H34A 122.9 . . ? S3 C34 H34A 122.9 . . ? C24 C23 C22 112.8(3) . . ? C24 C23 H23A 123.6 . . ? C22 C23 H23A 123.6 . . ? C13 C14 S1 112.9(2) . . ? C13 C14 H14A 123.6 . . ? S1 C14 H14A 123.6 . . ? C14 C13 C12 113.5(3) . . ? C14 C13 H13A 123.2 . . ? C12 C13 H13A 123.2 . . ? C34 C33 C32 115.7(3) . . ? C34 C33 H33A 122.1 . . ? C32 C33 H33A 122.1 . . ? C43 C44 S4 114.6(3) . . ? C43 C44 H44A 122.7 . . ? S4 C44 H44A 122.7 . . ? C44 C43 C42 117.1(3) . . ? C44 C43 H43A 121.4 . . ? C42 C43 H43A 121.4 . . ? C1 O1 H1 107(4) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? 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 C33 C32 C31 S3 -2.5(3) . . . . ? C33 C32 C31 P1 178.0(2) . . . . ? C34 S3 C31 C32 1.7(2) . . . . ? C34 S3 C31 P1 -178.8(2) . . . . ? C11 P1 C31 C32 0.4(3) . . . . ? C21 P1 C31 C32 119.6(2) . . . . ? C41 P1 C31 C32 -118.4(2) . . . . ? C11 P1 C31 S3 -179.02(18) . . . . ? C21 P1 C31 S3 -59.8(2) . . . . ? C41 P1 C31 S3 62.2(2) . . . . ? C24 S2 C21 C22 0.6(3) . . . . ? C24 S2 C21 P1 -175.4(2) . . . . ? C31 P1 C21 C22 23.9(3) . . . . ? C11 P1 C21 C22 143.7(3) . . . . ? C41 P1 C21 C22 -96.7(3) . . . . ? C31 P1 C21 S2 -160.65(17) . . . . ? C11 P1 C21 S2 -40.9(2) . . . . ? C41 P1 C21 S2 78.7(2) . . . . ? C44 S4 C41 C42 -0.3(2) . . . . ? C44 S4 C41 P1 177.0(2) . . . . ? C31 P1 C41 C42 -168.7(2) . . . . ? C11 P1 C41 C42 72.8(3) . . . . ? C21 P1 C41 C42 -46.1(3) . . . . ? C31 P1 C41 S4 14.3(2) . . . . ? C11 P1 C41 S4 -104.3(2) . . . . ? C21 P1 C41 S4 136.84(18) . . . . ? S4 C41 C42 C43 0.9(3) . . . . ? P1 C41 C42 C43 -176.4(2) . . . . ? C21 S2 C24 C23 -0.6(3) . . . . ? C14 S1 C11 C12 0.7(3) . . . . ? C14 S1 C11 P1 172.3(2) . . . . ? C31 P1 C11 C12 84.5(3) . . . . ? C21 P1 C11 C12 -36.9(3) . . . . ? C41 P1 C11 C12 -157.4(3) . . . . ? C31 P1 C11 S1 -85.9(2) . . . . ? C21 P1 C11 S1 152.71(18) . . . . ? C41 P1 C11 S1 32.2(2) . . . . ? S2 C21 C22 C23 -0.6(4) . . . . ? P1 C21 C22 C23 175.2(2) . . . . ? S1 C11 C12 C13 -1.1(4) . . . . ? P1 C11 C12 C13 -172.2(3) . . . . ? C31 S3 C34 C33 -0.2(3) . . . . ? S2 C24 C23 C22 0.3(4) . . . . ? C21 C22 C23 C24 0.2(4) . . . . ? C11 S1 C14 C13 -0.2(3) . . . . ? S1 C14 C13 C12 -0.5(5) . . . . ? C11 C12 C13 C14 1.0(5) . . . . ? S3 C34 C33 C32 -1.4(4) . . . . ? C31 C32 C33 C34 2.5(4) . . . . ? C41 S4 C44 C43 -0.4(3) . . . . ? S4 C44 C43 C42 1.0(5) . . . . ? C41 C42 C43 C44 -1.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.930 _refine_diff_density_min -1.018 _refine_diff_density_rms 0.115 #===END data_uwe36 _database_code_depnum_ccdc_archive 'CCDC 230857' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 N O2 P S4' _chemical_formula_weight 449.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.97530(10) _cell_length_b 9.4288(2) _cell_length_c 24.6522(5) _cell_angle_alpha 94.7514(6) _cell_angle_beta 90.4364(6) _cell_angle_gamma 103.1196(15) _cell_volume 2024.04(6) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 42099 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.563 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'NONIUS DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42099 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 25.28 _reflns_number_total 6939 _reflns_number_gt 6269 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Three thienyl groups are disordered over two sites (by a 180\% rotation around the C-P bond). All hydrogen atoms bonded to carbon atoms neighbouring the ipso carbon (in disordered and not disordered groups) were refined after a riding model. ; _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^)+(0.0415P)^2^+2.1915P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6939 _refine_ls_number_parameters 648 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.28217(7) -0.00818(6) 0.63935(2) 0.01909(14) Uani 1 1 d . A . S1 S 0.20713(7) 0.25023(6) 0.60939(2) 0.02435(14) Uani 1 1 d . . . O1 O 0.0743(2) 0.30886(19) 0.62028(8) 0.0349(4) Uani 1 1 d . . . N1 N 0.2113(2) 0.1315(2) 0.65071(8) 0.0235(4) Uani 1 1 d . . . O2 O 0.2242(2) 0.19832(19) 0.55324(7) 0.0339(4) Uani 1 1 d . . . C11 C 0.1580(3) -0.1578(2) 0.60130(9) 0.0210(5) Uani 1 1 d . . . C13 C 0.0305(3) -0.3981(3) 0.56784(11) 0.0327(6) Uani 1 1 d . . . H13A H 0.000(4) -0.497(4) 0.5656(14) 0.051(9) Uiso 1 1 d . . . C14 C -0.0238(3) -0.3090(3) 0.53677(10) 0.0319(6) Uani 1 1 d . A . H14A H -0.092(3) -0.335(3) 0.5097(12) 0.031(7) Uiso 1 1 d . . . C21 C 0.3090(3) -0.0735(2) 0.70331(9) 0.0210(5) Uani 1 1 d . . . S22 S 0.15568(8) -0.12824(8) 0.74388(3) 0.03309(16) Uani 1 1 d . A . C23 C 0.2683(3) -0.1785(3) 0.79105(10) 0.0295(6) Uani 1 1 d . . . H23A H 0.218(3) -0.218(3) 0.8210(12) 0.037(8) Uiso 1 1 d . . . C24 C 0.4176(3) -0.1532(3) 0.77763(10) 0.0323(6) Uani 1 1 d . A . H24A H 0.498(4) -0.176(3) 0.7975(13) 0.042(8) Uiso 1 1 d . . . C25 C 0.4513(3) -0.0896(3) 0.72618(9) 0.0265(5) Uani 1 1 d . A . H25A H 0.5491 -0.0635 0.7106 0.032 Uiso 1 1 calc R . . C31 C 0.4617(3) 0.0194(3) 0.60755(9) 0.0239(5) Uani 1 1 d . . . C33 C 0.7206(4) 0.1092(4) 0.58545(13) 0.0467(8) Uani 1 1 d . . . H33A H 0.823(5) 0.177(4) 0.5868(16) 0.074(12) Uiso 1 1 d . . . C34 C 0.6728(4) -0.0146(4) 0.55351(12) 0.0457(8) Uani 1 1 d . A . H34A H 0.726(4) -0.048(4) 0.5280(15) 0.054(10) Uiso 1 1 d . . . C41 C 0.3690(3) 0.3937(2) 0.62729(9) 0.0230(5) Uani 1 1 d . . . C42 C 0.4641(3) 0.4545(3) 0.58717(11) 0.0340(6) Uani 1 1 d . . . H42A H 0.442(4) 0.421(4) 0.5515(14) 0.052(9) Uiso 1 1 d . . . C43 C 0.5903(3) 0.5669(3) 0.60204(11) 0.0388(7) Uani 1 1 d . . . H43A H 0.664(4) 0.607(4) 0.5753(15) 0.065(11) Uiso 1 1 d . . . C44 C 0.6243(3) 0.6186(3) 0.65602(11) 0.0306(6) Uani 1 1 d . . . C45 C 0.5275(3) 0.5565(3) 0.69551(10) 0.0292(5) Uani 1 1 d . . . H45A H 0.555(3) 0.589(3) 0.7338(12) 0.038(8) Uiso 1 1 d . . . C46 C 0.3997(3) 0.4445(3) 0.68160(10) 0.0280(5) Uani 1 1 d . . . H46A H 0.325(4) 0.406(3) 0.7086(12) 0.040(8) Uiso 1 1 d . . . C47 C 0.7629(4) 0.7394(4) 0.67177(15) 0.0436(7) Uani 1 1 d . . . H47A H 0.758(4) 0.820(4) 0.6560(15) 0.059(11) Uiso 1 1 d . . . H47B H 0.851(5) 0.716(4) 0.6596(16) 0.070(12) Uiso 1 1 d . . . H47C H 0.770(4) 0.755(4) 0.7095(16) 0.059(11) Uiso 1 1 d . . . S121 S 0.0406(3) -0.1331(3) 0.54795(11) 0.0238(5) Uani 0.612(4) 1 d P A 1 C151 C 0.1417(14) -0.3026(12) 0.6064(4) 0.030(2) Uani 0.612(4) 1 d P A 1 H15A H 0.1976 -0.3390 0.6328 0.037 Uiso 0.612(4) 1 calc PR A 1 S122 S 0.1529(5) -0.3358(5) 0.61725(18) 0.0255(8) Uani 0.388(4) 1 d P A 2 C152 C 0.061(2) -0.1572(18) 0.5606(6) 0.025(4) Uani 0.388(4) 1 d P A 2 H15B H 0.0464 -0.0697 0.5472 0.030 Uiso 0.388(4) 1 calc PR A 2 S321 S 0.4992(5) -0.1050(6) 0.55897(18) 0.0345(8) Uani 0.596(5) 1 d P A 1 C351 C 0.5908(19) 0.1300(16) 0.6183(7) 0.032(3) Uani 0.596(5) 1 d P A 1 H35A H 0.5950 0.2111 0.6443 0.039 Uiso 0.596(5) 1 calc PR A 1 S322 S 0.6113(7) 0.1630(7) 0.6272(3) 0.0315(11) Uani 0.404(5) 1 d P A 2 C352 C 0.513(3) -0.071(3) 0.5668(10) 0.044(8) Uani 0.404(5) 1 d P A 2 H35B H 0.4508 -0.1586 0.5499 0.053 Uiso 0.404(5) 1 calc PR A 2 P2 P 0.66539(7) 0.44375(7) 0.84937(2) 0.02172(14) Uani 1 1 d . B . S2 S 0.86628(7) 0.72250(7) 0.86281(2) 0.02614(15) Uani 1 1 d . . . N2 N 0.7120(2) 0.6146(2) 0.84093(8) 0.0268(4) Uani 1 1 d . . . O3 O 0.9857(2) 0.6472(2) 0.87439(7) 0.0328(4) Uani 1 1 d . . . O4 O 0.9038(2) 0.8371(2) 0.82676(7) 0.0370(4) Uani 1 1 d . . . C51 C 0.7612(3) 0.3347(3) 0.80705(9) 0.0242(5) Uani 1 1 d . . . C53 C 0.8475(4) 0.1320(4) 0.76678(14) 0.0454(8) Uani 1 1 d . . . H53A H 0.874(4) 0.035(4) 0.7603(13) 0.050(9) Uiso 1 1 d . . . C54 C 0.8826(4) 0.2333(4) 0.73135(12) 0.0469(8) Uani 1 1 d . B . H54A H 0.932(5) 0.233(4) 0.6994(17) 0.076(12) Uiso 1 1 d . . . C61 C 0.6811(3) 0.3932(3) 0.91714(9) 0.0245(5) Uani 1 1 d . . . S62 S 0.85098(8) 0.38880(9) 0.94942(3) 0.03937(18) Uani 1 1 d . B . C63 C 0.7629(3) 0.3589(3) 1.00993(11) 0.0355(6) Uani 1 1 d . . . H63A H 0.820(4) 0.350(3) 1.0396(13) 0.045(9) Uiso 1 1 d . . . C64 C 0.6113(3) 0.3498(3) 1.00593(10) 0.0303(6) Uani 1 1 d . B . H64A H 0.547(4) 0.333(3) 1.0335(13) 0.039(8) Uiso 1 1 d . . . C65 C 0.5628(3) 0.3694(3) 0.95304(9) 0.0251(5) Uani 1 1 d . B . H65A H 0.4595 0.3665 0.9432 0.030 Uiso 1 1 calc R . . C71 C 0.4674(3) 0.3910(3) 0.83292(9) 0.0221(5) Uani 1 1 d . . . S72 S 0.35136(8) 0.50997(7) 0.84654(3) 0.03286(16) Uani 1 1 d . B . C73 C 0.1925(3) 0.3801(3) 0.82880(11) 0.0366(6) Uani 1 1 d . . . H73A H 0.104(5) 0.407(4) 0.8303(15) 0.062(11) Uiso 1 1 d . . . C74 C 0.2227(3) 0.2499(3) 0.81235(13) 0.0401(7) Uani 1 1 d . B . H74A H 0.143(5) 0.165(4) 0.8016(15) 0.066(11) Uiso 1 1 d . . . C75 C 0.3834(3) 0.2481(3) 0.81313(10) 0.0241(5) Uani 1 1 d . B . H75A H 0.4256 0.1667 0.8024 0.029 Uiso 1 1 calc R . . C81 C 0.8200(3) 0.8058(3) 0.92565(9) 0.0252(5) Uani 1 1 d . . . C82 C 0.7286(4) 0.9054(3) 0.92572(11) 0.0349(6) Uani 1 1 d . . . H82A H 0.687(4) 0.929(4) 0.8909(14) 0.055(10) Uiso 1 1 d . . . C83 C 0.6937(4) 0.9727(3) 0.97466(12) 0.0398(7) Uani 1 1 d . . . H83A H 0.629(4) 1.041(4) 0.9737(14) 0.056(10) Uiso 1 1 d . . . C84 C 0.7500(3) 0.9417(3) 1.02404(10) 0.0320(6) Uani 1 1 d . . . C85 C 0.8393(4) 0.8411(4) 1.02319(11) 0.0427(7) Uani 1 1 d . . . H85A H 0.879(4) 0.810(4) 1.0564(15) 0.062(11) Uiso 1 1 d . . . C86 C 0.8749(4) 0.7732(4) 0.97439(11) 0.0427(7) Uani 1 1 d . . . H86A H 0.938(4) 0.706(4) 0.9735(14) 0.061(11) Uiso 1 1 d . . . C87 C 0.7126(5) 1.0136(4) 1.07726(13) 0.0443(7) Uani 1 1 d . . . H87C H 0.673(5) 1.092(5) 1.0720(17) 0.082(14) Uiso 1 1 d . . . H87B H 0.634(6) 0.955(5) 1.0909(19) 0.089(15) Uiso 1 1 d . . . H87A H 0.796(6) 1.022(5) 1.102(2) 0.101(16) Uiso 1 1 d . . . S521 S 0.8375(5) 0.3870(4) 0.74626(19) 0.0341(7) Uani 0.645(5) 1 d P B 1 C551 C 0.7764(19) 0.1957(14) 0.8108(6) 0.041(4) Uani 0.645(5) 1 d P B 1 H55A H 0.7412 0.1436 0.8413 0.049 Uiso 0.645(5) 1 calc PR B 1 S522 S 0.7710(8) 0.1625(7) 0.8200(3) 0.0325(11) Uani 0.355(5) 1 d P B 2 C552 C 0.827(3) 0.387(3) 0.7584(11) 0.039(8) Uani 0.355(5) 1 d P B 2 H55B H 0.8375 0.4802 0.7447 0.046 Uiso 0.355(5) 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0186(3) 0.0210(3) 0.0177(3) 0.0029(2) 0.0003(2) 0.0042(2) S1 0.0255(3) 0.0212(3) 0.0259(3) 0.0048(2) -0.0048(2) 0.0036(2) O1 0.0242(10) 0.0293(10) 0.0532(12) 0.0094(8) -0.0049(8) 0.0083(7) N1 0.0257(11) 0.0202(10) 0.0251(10) 0.0033(8) 0.0022(8) 0.0059(8) O2 0.0470(12) 0.0284(9) 0.0235(9) 0.0025(7) -0.0079(8) 0.0028(8) C11 0.0202(13) 0.0222(12) 0.0211(11) 0.0014(9) -0.0009(9) 0.0056(9) C13 0.0453(17) 0.0229(13) 0.0292(13) -0.0027(10) -0.0011(11) 0.0079(11) C14 0.0346(16) 0.0374(15) 0.0231(12) 0.0020(11) -0.0042(11) 0.0071(11) C21 0.0250(13) 0.0198(11) 0.0185(11) 0.0026(8) 0.0002(9) 0.0054(9) S22 0.0329(4) 0.0405(4) 0.0268(3) 0.0093(3) 0.0046(3) 0.0080(3) C23 0.0409(16) 0.0271(13) 0.0207(12) 0.0034(10) 0.0015(10) 0.0079(11) C24 0.0403(17) 0.0348(14) 0.0246(13) 0.0062(10) -0.0028(11) 0.0132(12) C25 0.0501(16) 0.0228(12) 0.0110(10) 0.0026(9) -0.0024(10) 0.0172(11) C31 0.0225(13) 0.0310(13) 0.0187(11) 0.0053(9) 0.0006(9) 0.0059(10) C33 0.0276(17) 0.066(2) 0.0422(17) 0.0208(15) -0.0024(12) -0.0045(14) C34 0.0365(19) 0.077(2) 0.0287(15) 0.0037(15) 0.0081(12) 0.0238(16) C41 0.0238(13) 0.0207(11) 0.0250(12) 0.0045(9) -0.0001(9) 0.0054(9) C42 0.0349(16) 0.0396(15) 0.0231(13) 0.0024(11) 0.0015(10) -0.0002(11) C43 0.0351(17) 0.0427(16) 0.0321(14) 0.0057(12) 0.0080(11) -0.0055(12) C44 0.0279(15) 0.0277(13) 0.0344(14) 0.0005(10) 0.0010(10) 0.0032(10) C45 0.0316(15) 0.0292(13) 0.0252(13) -0.0004(10) -0.0028(10) 0.0049(10) C46 0.0307(15) 0.0278(13) 0.0239(12) 0.0036(10) 0.0024(10) 0.0031(10) C47 0.0308(18) 0.0446(19) 0.0474(19) -0.0041(15) 0.0026(13) -0.0053(13) S121 0.0259(8) 0.0226(11) 0.0227(10) 0.0051(7) -0.0047(6) 0.0040(6) C151 0.037(4) 0.036(6) 0.022(4) 0.002(3) -0.008(3) 0.018(3) S122 0.0312(13) 0.0201(15) 0.0262(17) -0.0005(11) -0.0074(11) 0.0089(10) C152 0.032(7) 0.018(5) 0.028(8) 0.013(4) 0.009(5) 0.009(4) S321 0.0283(14) 0.0466(19) 0.0276(9) -0.0031(11) 0.0052(9) 0.0086(12) C351 0.044(7) 0.023(7) 0.028(5) -0.004(4) -0.001(4) 0.006(5) S322 0.0203(14) 0.029(2) 0.041(2) -0.0035(17) 0.0011(13) -0.0008(13) C352 0.028(6) 0.045(13) 0.052(13) 0.005(9) -0.014(6) -0.004(7) P2 0.0204(3) 0.0272(3) 0.0180(3) 0.0016(2) -0.0003(2) 0.0065(2) S2 0.0260(3) 0.0278(3) 0.0229(3) 0.0017(2) 0.0049(2) 0.0028(2) N2 0.0281(12) 0.0287(11) 0.0229(10) 0.0013(8) -0.0020(8) 0.0054(8) O3 0.0253(10) 0.0372(10) 0.0352(10) -0.0020(8) 0.0033(7) 0.0072(7) O4 0.0449(12) 0.0330(10) 0.0307(10) 0.0095(8) 0.0130(8) 0.0014(8) C51 0.0191(13) 0.0316(13) 0.0221(12) 0.0011(9) -0.0013(9) 0.0069(9) C53 0.0331(18) 0.0404(17) 0.062(2) -0.0151(15) -0.0164(14) 0.0145(13) C54 0.0285(17) 0.084(3) 0.0271(14) -0.0129(15) -0.0011(11) 0.0174(15) C61 0.0230(13) 0.0289(12) 0.0221(11) 0.0017(9) -0.0026(9) 0.0071(9) S62 0.0231(4) 0.0665(5) 0.0294(3) 0.0167(3) -0.0036(3) 0.0077(3) C63 0.0391(17) 0.0433(16) 0.0233(13) 0.0085(11) -0.0061(11) 0.0056(12) C64 0.0369(16) 0.0320(14) 0.0232(12) 0.0034(10) 0.0045(11) 0.0100(11) C65 0.0256(14) 0.0261(12) 0.0247(12) 0.0026(9) 0.0015(9) 0.0078(10) C71 0.0225(13) 0.0281(12) 0.0180(11) 0.0022(9) -0.0011(8) 0.0106(9) S72 0.0324(4) 0.0342(4) 0.0346(3) 0.0010(3) -0.0032(3) 0.0139(3) C73 0.0247(16) 0.0495(17) 0.0396(15) 0.0034(12) -0.0044(11) 0.0170(12) C74 0.0259(16) 0.0389(16) 0.0525(18) -0.0028(13) -0.0113(12) 0.0042(12) C75 0.0135(12) 0.0269(12) 0.0313(13) 0.0030(10) -0.0090(9) 0.0035(9) C81 0.0245(13) 0.0244(12) 0.0235(12) 0.0012(9) 0.0028(9) -0.0008(9) C82 0.0498(18) 0.0307(14) 0.0265(13) 0.0031(11) 0.0007(11) 0.0138(12) C83 0.055(2) 0.0337(15) 0.0347(15) 0.0010(12) 0.0032(13) 0.0183(14) C84 0.0377(16) 0.0279(13) 0.0273(13) -0.0012(10) 0.0030(10) 0.0023(11) C85 0.052(2) 0.0572(19) 0.0228(13) -0.0004(12) -0.0058(12) 0.0229(15) C86 0.050(2) 0.0552(19) 0.0309(14) -0.0002(13) -0.0045(12) 0.0299(15) C87 0.059(2) 0.0411(18) 0.0322(16) -0.0029(13) 0.0054(14) 0.0123(16) S521 0.0374(10) 0.0475(12) 0.0212(17) 0.0049(11) 0.0064(9) 0.0169(9) C551 0.033(4) 0.042(7) 0.045(5) 0.014(4) 0.002(3) 0.000(4) S522 0.0282(15) 0.029(2) 0.040(2) 0.0025(18) 0.0071(13) 0.0067(14) C552 0.039(11) 0.071(12) 0.016(12) -0.026(8) -0.016(8) 0.044(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.594(2) . ? P1 C31 1.773(2) . ? P1 C21 1.774(2) . ? P1 C11 1.778(2) . ? S1 O1 1.4415(19) . ? S1 O2 1.4504(18) . ? S1 N1 1.581(2) . ? S1 C41 1.770(2) . ? C11 C152 1.323(15) . ? C11 C151 1.356(11) . ? C11 S121 1.743(3) . ? C11 S122 1.746(4) . ? C13 C14 1.347(4) . ? C13 C151 1.465(13) . ? C13 S122 1.613(5) . ? C13 H13A 0.90(4) . ? C14 C152 1.528(19) . ? C14 S121 1.628(4) . ? C14 H14A 0.88(3) . ? C21 C25 1.436(3) . ? C21 S22 1.716(2) . ? S22 C23 1.700(3) . ? C23 C24 1.356(4) . ? C23 H23A 0.93(3) . ? C24 C25 1.452(3) . ? C24 H24A 0.95(3) . ? C25 H25A 0.9500 . ? C31 C351 1.378(14) . ? C31 C352 1.41(2) . ? C31 S321 1.695(5) . ? C31 S322 1.711(6) . ? C33 C34 1.334(5) . ? C33 C351 1.464(19) . ? C33 S322 1.560(7) . ? C33 H33A 0.99(4) . ? C34 C352 1.46(3) . ? C34 S321 1.610(6) . ? C34 H34A 0.87(4) . ? C41 C42 1.386(4) . ? C41 C46 1.388(3) . ? C42 C43 1.387(4) . ? C42 H42A 0.91(3) . ? C43 C44 1.386(4) . ? C43 H43A 0.98(4) . ? C44 C45 1.387(4) . ? C44 C47 1.507(4) . ? C45 C46 1.390(4) . ? C45 H45A 0.98(3) . ? C46 H46A 0.98(3) . ? C47 H47A 0.89(4) . ? C47 H47B 0.91(4) . ? C47 H47C 0.93(4) . ? C151 H15A 0.9500 . ? C152 H15B 0.9500 . ? C351 H35A 0.9500 . ? C352 H35B 0.9500 . ? P2 N2 1.601(2) . ? P2 C51 1.767(2) . ? P2 C71 1.768(2) . ? P2 C61 1.788(2) . ? S2 O4 1.4389(18) . ? S2 O3 1.4518(19) . ? S2 N2 1.582(2) . ? S2 C81 1.773(2) . ? C51 C551 1.358(13) . ? C51 C552 1.42(3) . ? C51 S522 1.701(7) . ? C51 S521 1.715(5) . ? C53 C54 1.334(5) . ? C53 C551 1.422(16) . ? C53 S522 1.521(7) . ? C53 H53A 1.00(3) . ? C54 S521 1.606(6) . ? C54 C552 1.73(3) . ? C54 H54A 0.91(4) . ? C61 C65 1.379(3) . ? C61 S62 1.725(2) . ? S62 C63 1.708(3) . ? C63 C64 1.346(4) . ? C63 H63A 0.91(3) . ? C64 C65 1.411(3) . ? C64 H64A 0.90(3) . ? C65 H65A 0.9500 . ? C71 C75 1.430(3) . ? C71 S72 1.711(2) . ? S72 C73 1.683(3) . ? C73 C74 1.347(4) . ? C73 H73A 0.89(4) . ? C74 C75 1.446(4) . ? C74 H74A 0.96(4) . ? C75 H75A 0.9500 . ? C81 C86 1.379(4) . ? C81 C82 1.380(4) . ? C82 C83 1.388(4) . ? C82 H82A 0.99(4) . ? C83 C84 1.392(4) . ? C83 H83A 0.97(4) . ? C84 C85 1.373(4) . ? C84 C87 1.502(4) . ? C85 C86 1.390(4) . ? C85 H85A 0.98(4) . ? C86 H86A 0.94(4) . ? C87 H87C 0.91(5) . ? C87 H87B 0.88(5) . ? C87 H87A 0.95(5) . ? C551 H55A 0.9500 . ? C552 H55B 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 P1 C31 116.83(11) . . ? N1 P1 C21 107.18(10) . . ? C31 P1 C21 106.42(11) . . ? N1 P1 C11 113.93(11) . . ? C31 P1 C11 106.79(11) . . ? C21 P1 C11 104.79(11) . . ? O1 S1 O2 115.95(12) . . ? O1 S1 N1 108.14(11) . . ? O2 S1 N1 113.15(11) . . ? O1 S1 C41 106.64(11) . . ? O2 S1 C41 106.95(11) . . ? N1 S1 C41 105.27(11) . . ? S1 N1 P1 125.57(13) . . ? C152 C11 C151 102.5(9) . . ? C152 C11 S121 7.3(8) . . ? C151 C11 S121 109.8(5) . . ? C152 C11 S122 111.1(8) . . ? C151 C11 S122 8.8(6) . . ? S121 C11 S122 118.4(2) . . ? C152 C11 P1 129.4(7) . . ? C151 C11 P1 128.1(5) . . ? S121 C11 P1 122.09(16) . . ? S122 C11 P1 119.52(19) . . ? C14 C13 C151 106.2(4) . . ? C14 C13 S122 122.1(3) . . ? C151 C13 S122 16.1(4) . . ? C14 C13 H13A 126(2) . . ? C151 C13 H13A 128(2) . . ? S122 C13 H13A 112(2) . . ? C13 C14 C152 102.6(5) . . ? C13 C14 S121 119.0(2) . . ? C152 C14 S121 16.5(4) . . ? C13 C14 H14A 127.2(19) . . ? C152 C14 H14A 130.2(19) . . ? S121 C14 H14A 113.7(19) . . ? C25 C21 S22 113.44(17) . . ? C25 C21 P1 126.31(18) . . ? S22 C21 P1 120.24(14) . . ? C23 S22 C21 91.58(12) . . ? C24 C23 S22 113.0(2) . . ? C24 C23 H23A 131.4(19) . . ? S22 C23 H23A 115.5(19) . . ? C23 C24 C25 114.7(2) . . ? C23 C24 H24A 126(2) . . ? C25 C24 H24A 119(2) . . ? C21 C25 C24 107.2(2) . . ? C21 C25 H25A 126.4 . . ? C24 C25 H25A 126.4 . . ? C351 C31 C352 101.6(13) . . ? C351 C31 S321 109.6(8) . . ? C352 C31 S321 8.0(12) . . ? C351 C31 S322 6.6(9) . . ? C352 C31 S322 108.0(11) . . ? S321 C31 S322 116.0(3) . . ? C351 C31 P1 129.2(7) . . ? C352 C31 P1 129.1(11) . . ? S321 C31 P1 121.1(2) . . ? S322 C31 P1 122.7(2) . . ? C34 C33 C351 106.9(5) . . ? C34 C33 S322 120.7(3) . . ? C351 C33 S322 13.8(6) . . ? C34 C33 H33A 128(2) . . ? C351 C33 H33A 125(2) . . ? S322 C33 H33A 112(2) . . ? C33 C34 C352 105.9(9) . . ? C33 C34 S321 118.0(3) . . ? C352 C34 S321 12.2(10) . . ? C33 C34 H34A 125(2) . . ? C352 C34 H34A 129(3) . . ? S321 C34 H34A 117(2) . . ? C42 C41 C46 120.4(2) . . ? C42 C41 S1 119.99(19) . . ? C46 C41 S1 119.63(18) . . ? C41 C42 C43 119.1(2) . . ? C41 C42 H42A 120(2) . . ? C43 C42 H42A 121(2) . . ? C44 C43 C42 121.6(2) . . ? C44 C43 H43A 117(2) . . ? C42 C43 H43A 121(2) . . ? C43 C44 C45 118.4(2) . . ? C43 C44 C47 121.2(3) . . ? C45 C44 C47 120.5(3) . . ? C44 C45 C46 121.1(2) . . ? C44 C45 H45A 118.1(18) . . ? C46 C45 H45A 120.7(18) . . ? C41 C46 C45 119.4(2) . . ? C41 C46 H46A 118.4(18) . . ? C45 C46 H46A 121.9(18) . . ? C44 C47 H47A 111(2) . . ? C44 C47 H47B 112(3) . . ? H47A C47 H47B 105(3) . . ? C44 C47 H47C 109(2) . . ? H47A C47 H47C 112(3) . . ? H47B C47 H47C 109(3) . . ? C14 S121 C11 90.70(17) . . ? C11 C151 C13 114.3(6) . . ? C11 C151 H15A 122.8 . . ? C13 C151 H15A 122.8 . . ? C13 S122 C11 89.7(2) . . ? C11 C152 C14 114.4(9) . . ? C11 C152 H15B 122.8 . . ? C14 C152 H15B 122.8 . . ? C34 S321 C31 92.5(3) . . ? C31 C351 C33 112.9(9) . . ? C31 C351 H35A 123.6 . . ? C33 C351 H35A 123.6 . . ? C33 S322 C31 92.7(3) . . ? C31 C352 C34 112.7(15) . . ? C31 C352 H35B 123.6 . . ? C34 C352 H35B 123.6 . . ? N2 P2 C51 114.42(11) . . ? N2 P2 C71 104.73(11) . . ? C51 P2 C71 108.68(11) . . ? N2 P2 C61 116.99(11) . . ? C51 P2 C61 106.81(11) . . ? C71 P2 C61 104.51(11) . . ? O4 S2 O3 116.73(12) . . ? O4 S2 N2 108.02(12) . . ? O3 S2 N2 112.84(11) . . ? O4 S2 C81 106.25(11) . . ? O3 S2 C81 107.11(11) . . ? N2 S2 C81 105.05(11) . . ? S2 N2 P2 124.90(14) . . ? C551 C51 C552 109.8(15) . . ? C551 C51 S522 7.4(8) . . ? C552 C51 S522 117.2(13) . . ? C551 C51 S521 106.6(7) . . ? C552 C51 S521 3.7(14) . . ? S522 C51 S521 114.1(3) . . ? C551 C51 P2 130.3(7) . . ? C552 C51 P2 119.8(13) . . ? S522 C51 P2 123.0(2) . . ? S521 C51 P2 122.7(2) . . ? C54 C53 C551 106.2(5) . . ? C54 C53 S522 121.1(4) . . ? C551 C53 S522 15.0(6) . . ? C54 C53 H53A 121.7(19) . . ? C551 C53 H53A 132(2) . . ? S522 C53 H53A 117(2) . . ? C53 C54 S521 117.6(3) . . ? C53 C54 C552 107.7(9) . . ? S521 C54 C552 10.0(10) . . ? C53 C54 H54A 131(3) . . ? S521 C54 H54A 111(3) . . ? C552 C54 H54A 121(3) . . ? C65 C61 S62 110.29(18) . . ? C65 C61 P2 124.77(18) . . ? S62 C61 P2 124.52(14) . . ? C63 S62 C61 91.85(13) . . ? C64 C63 S62 112.3(2) . . ? C64 C63 H63A 129(2) . . ? S62 C63 H63A 119(2) . . ? C63 C64 C65 112.7(2) . . ? C63 C64 H64A 125(2) . . ? C65 C64 H64A 123(2) . . ? C61 C65 C64 112.9(2) . . ? C61 C65 H65A 123.6 . . ? C64 C65 H65A 123.6 . . ? C75 C71 S72 112.47(18) . . ? C75 C71 P2 126.54(18) . . ? S72 C71 P2 120.68(14) . . ? C73 S72 C71 92.23(13) . . ? C74 C73 S72 112.9(2) . . ? C74 C73 H73A 130(3) . . ? S72 C73 H73A 117(2) . . ? C73 C74 C75 114.7(3) . . ? C73 C74 H74A 122(2) . . ? C75 C74 H74A 123(2) . . ? C71 C75 C74 107.7(2) . . ? C71 C75 H75A 126.1 . . ? C74 C75 H75A 126.1 . . ? C86 C81 C82 119.6(2) . . ? C86 C81 S2 120.9(2) . . ? C82 C81 S2 119.48(19) . . ? C81 C82 C83 119.9(3) . . ? C81 C82 H82A 120(2) . . ? C83 C82 H82A 120(2) . . ? C82 C83 C84 121.0(3) . . ? C82 C83 H83A 118(2) . . ? C84 C83 H83A 121(2) . . ? C85 C84 C83 118.3(2) . . ? C85 C84 C87 120.3(3) . . ? C83 C84 C87 121.5(3) . . ? C84 C85 C86 121.1(3) . . ? C84 C85 H85A 123(2) . . ? C86 C85 H85A 116(2) . . ? C81 C86 C85 120.1(3) . . ? C81 C86 H86A 118(2) . . ? C85 C86 H86A 121(2) . . ? C84 C87 H87C 111(3) . . ? C84 C87 H87B 109(3) . . ? H87C C87 H87B 101(4) . . ? C84 C87 H87A 108(3) . . ? H87C C87 H87A 121(4) . . ? H87B C87 H87A 106(4) . . ? C54 S521 C51 92.8(2) . . ? C51 C551 C53 116.8(9) . . ? C51 C551 H55A 121.6 . . ? C53 C551 H55A 121.6 . . ? C53 S522 C51 94.4(4) . . ? C51 C552 C54 99.5(17) . . ? C51 C552 H55B 130.2 . . ? C54 C552 H55B 130.2 . . ? 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 O1 S1 N1 P1 150.37(15) . . . . ? O2 S1 N1 P1 20.5(2) . . . . ? C41 S1 N1 P1 -95.94(16) . . . . ? C31 P1 N1 S1 43.93(19) . . . . ? C21 P1 N1 S1 163.14(15) . . . . ? C11 P1 N1 S1 -81.42(17) . . . . ? N1 P1 C11 C152 37.2(10) . . . . ? C31 P1 C11 C152 -93.3(10) . . . . ? C21 P1 C11 C152 154.0(10) . . . . ? N1 P1 C11 C151 -144.3(7) . . . . ? C31 P1 C11 C151 85.1(7) . . . . ? C21 P1 C11 C151 -27.5(7) . . . . ? N1 P1 C11 S121 38.1(2) . . . . ? C31 P1 C11 S121 -92.4(2) . . . . ? C21 P1 C11 S121 154.98(18) . . . . ? N1 P1 C11 S122 -142.1(2) . . . . ? C31 P1 C11 S122 87.4(2) . . . . ? C21 P1 C11 S122 -25.2(2) . . . . ? C151 C13 C14 C152 -0.8(9) . . . . ? S122 C13 C14 C152 1.3(7) . . . . ? C151 C13 C14 S121 0.2(6) . . . . ? S122 C13 C14 S121 2.3(5) . . . . ? N1 P1 C21 C25 -121.3(2) . . . . ? C31 P1 C21 C25 4.4(2) . . . . ? C11 P1 C21 C25 117.3(2) . . . . ? N1 P1 C21 S22 59.95(16) . . . . ? C31 P1 C21 S22 -174.35(14) . . . . ? C11 P1 C21 S22 -61.43(16) . . . . ? C25 C21 S22 C23 -1.52(19) . . . . ? P1 C21 S22 C23 177.38(15) . . . . ? C21 S22 C23 C24 1.0(2) . . . . ? S22 C23 C24 C25 -0.2(3) . . . . ? S22 C21 C25 C24 1.6(2) . . . . ? P1 C21 C25 C24 -177.23(18) . . . . ? C23 C24 C25 C21 -0.9(3) . . . . ? N1 P1 C31 C351 44.2(10) . . . . ? C21 P1 C31 C351 -75.4(10) . . . . ? C11 P1 C31 C351 173.1(10) . . . . ? N1 P1 C31 C352 -140.0(16) . . . . ? C21 P1 C31 C352 100.4(16) . . . . ? C11 P1 C31 C352 -11.2(16) . . . . ? N1 P1 C31 S321 -140.0(3) . . . . ? C21 P1 C31 S321 100.4(3) . . . . ? C11 P1 C31 S321 -11.2(3) . . . . ? N1 P1 C31 S322 45.3(4) . . . . ? C21 P1 C31 S322 -74.3(3) . . . . ? C11 P1 C31 S322 174.1(3) . . . . ? C351 C33 C34 C352 -0.3(15) . . . . ? S322 C33 C34 C352 1.3(13) . . . . ? C351 C33 C34 S321 -0.9(8) . . . . ? S322 C33 C34 S321 0.7(6) . . . . ? O1 S1 C41 C42 -111.6(2) . . . . ? O2 S1 C41 C42 13.0(2) . . . . ? N1 S1 C41 C42 133.7(2) . . . . ? O1 S1 C41 C46 68.4(2) . . . . ? O2 S1 C41 C46 -166.9(2) . . . . ? N1 S1 C41 C46 -46.3(2) . . . . ? C46 C41 C42 C43 -0.1(4) . . . . ? S1 C41 C42 C43 179.9(2) . . . . ? C41 C42 C43 C44 0.7(5) . . . . ? C42 C43 C44 C45 -0.9(4) . . . . ? C42 C43 C44 C47 179.1(3) . . . . ? C43 C44 C45 C46 0.4(4) . . . . ? C47 C44 C45 C46 -179.6(3) . . . . ? C42 C41 C46 C45 -0.4(4) . . . . ? S1 C41 C46 C45 179.6(2) . . . . ? C44 C45 C46 C41 0.3(4) . . . . ? C13 C14 S121 C11 -0.7(3) . . . . ? C152 C14 S121 C11 3(2) . . . . ? C152 C11 S121 C14 -7(6) . . . . ? C151 C11 S121 C14 1.1(6) . . . . ? S122 C11 S121 C14 -0.8(3) . . . . ? P1 C11 S121 C14 179.04(17) . . . . ? C152 C11 C151 C13 -0.3(11) . . . . ? S121 C11 C151 C13 -1.3(10) . . . . ? S122 C11 C151 C13 168(5) . . . . ? P1 C11 C151 C13 -179.0(4) . . . . ? C14 C13 C151 C11 0.8(9) . . . . ? S122 C13 C151 C11 -173(3) . . . . ? C14 C13 S122 C11 -2.2(4) . . . . ? C151 C13 S122 C11 5(2) . . . . ? C152 C11 S122 C13 2.4(9) . . . . ? C151 C11 S122 C13 -10(4) . . . . ? S121 C11 S122 C13 1.6(3) . . . . ? P1 C11 S122 C13 -178.19(19) . . . . ? C151 C11 C152 C14 -0.3(13) . . . . ? S121 C11 C152 C14 172(7) . . . . ? S122 C11 C152 C14 -2.2(13) . . . . ? P1 C11 C152 C14 178.5(5) . . . . ? C13 C14 C152 C11 0.8(13) . . . . ? S121 C14 C152 C11 -176(4) . . . . ? C33 C34 S321 C31 0.8(4) . . . . ? C352 C34 S321 C31 -2(6) . . . . ? C351 C31 S321 C34 -0.4(9) . . . . ? C352 C31 S321 C34 3(10) . . . . ? S322 C31 S321 C34 -1.9(4) . . . . ? P1 C31 S321 C34 -176.9(2) . . . . ? C352 C31 C351 C33 -0.5(18) . . . . ? S321 C31 C351 C33 0.0(14) . . . . ? S322 C31 C351 C33 168(10) . . . . ? P1 C31 C351 C33 176.1(5) . . . . ? C34 C33 C351 C31 0.5(14) . . . . ? S322 C33 C351 C31 -174(5) . . . . ? C34 C33 S322 C31 -1.7(5) . . . . ? C351 C33 S322 C31 4(4) . . . . ? C351 C31 S322 C33 -10(9) . . . . ? C352 C31 S322 C33 1.4(14) . . . . ? S321 C31 S322 C33 2.2(5) . . . . ? P1 C31 S322 C33 177.1(2) . . . . ? C351 C31 C352 C34 0(2) . . . . ? S321 C31 C352 C34 -176(12) . . . . ? S322 C31 C352 C34 -1(2) . . . . ? P1 C31 C352 C34 -176.3(8) . . . . ? C33 C34 C352 C31 0(2) . . . . ? S321 C34 C352 C31 177(8) . . . . ? O4 S2 N2 P2 151.16(15) . . . . ? O3 S2 N2 P2 20.60(19) . . . . ? C81 S2 N2 P2 -95.75(17) . . . . ? C51 P2 N2 S2 -75.88(17) . . . . ? C71 P2 N2 S2 165.24(14) . . . . ? C61 P2 N2 S2 50.1(2) . . . . ? N2 P2 C51 C551 163.9(10) . . . . ? C71 P2 C51 C551 -79.4(10) . . . . ? C61 P2 C51 C551 32.8(10) . . . . ? N2 P2 C51 C552 -21.3(14) . . . . ? C71 P2 C51 C552 95.3(14) . . . . ? C61 P2 C51 C552 -152.4(14) . . . . ? N2 P2 C51 S522 162.1(3) . . . . ? C71 P2 C51 S522 -81.2(4) . . . . ? C61 P2 C51 S522 31.0(4) . . . . ? N2 P2 C51 S521 -23.9(3) . . . . ? C71 P2 C51 S521 92.8(2) . . . . ? C61 P2 C51 S521 -155.0(2) . . . . ? C551 C53 C54 S521 -0.6(8) . . . . ? S522 C53 C54 S521 -1.5(5) . . . . ? C551 C53 C54 C552 1.2(13) . . . . ? S522 C53 C54 C552 0.3(11) . . . . ? N2 P2 C61 C65 94.8(2) . . . . ? C51 P2 C61 C65 -135.5(2) . . . . ? C71 P2 C61 C65 -20.5(2) . . . . ? N2 P2 C61 S62 -77.02(19) . . . . ? C51 P2 C61 S62 52.67(19) . . . . ? C71 P2 C61 S62 167.74(15) . . . . ? C65 C61 S62 C63 -1.0(2) . . . . ? P2 C61 S62 C63 171.83(18) . . . . ? C61 S62 C63 C64 1.1(2) . . . . ? S62 C63 C64 C65 -0.9(3) . . . . ? S62 C61 C65 C64 0.7(3) . . . . ? P2 C61 C65 C64 -172.14(19) . . . . ? C63 C64 C65 C61 0.2(3) . . . . ? N2 P2 C71 C75 153.4(2) . . . . ? C51 P2 C71 C75 30.7(2) . . . . ? C61 P2 C71 C75 -83.0(2) . . . . ? N2 P2 C71 S72 -33.38(17) . . . . ? C51 P2 C71 S72 -156.07(14) . . . . ? C61 P2 C71 S72 90.17(16) . . . . ? C75 C71 S72 C73 1.24(19) . . . . ? P2 C71 S72 C73 -172.87(16) . . . . ? C71 S72 C73 C74 -0.6(2) . . . . ? S72 C73 C74 C75 -0.1(4) . . . . ? S72 C71 C75 C74 -1.4(3) . . . . ? P2 C71 C75 C74 172.24(19) . . . . ? C73 C74 C75 C71 1.0(3) . . . . ? O4 S2 C81 C86 -136.0(2) . . . . ? O3 S2 C81 C86 -10.6(3) . . . . ? N2 S2 C81 C86 109.6(3) . . . . ? O4 S2 C81 C82 43.5(2) . . . . ? O3 S2 C81 C82 168.9(2) . . . . ? N2 S2 C81 C82 -70.8(2) . . . . ? C86 C81 C82 C83 0.5(4) . . . . ? S2 C81 C82 C83 -179.1(2) . . . . ? C81 C82 C83 C84 0.3(5) . . . . ? C82 C83 C84 C85 -1.0(5) . . . . ? C82 C83 C84 C87 -179.8(3) . . . . ? C83 C84 C85 C86 1.0(5) . . . . ? C87 C84 C85 C86 179.9(3) . . . . ? C82 C81 C86 C85 -0.5(5) . . . . ? S2 C81 C86 C85 179.1(3) . . . . ? C84 C85 C86 C81 -0.3(5) . . . . ? C53 C54 S521 C51 0.7(4) . . . . ? C552 C54 S521 C51 -9(6) . . . . ? C551 C51 S521 C54 -0.5(8) . . . . ? C552 C51 S521 C54 148(21) . . . . ? S522 C51 S521 C54 0.1(4) . . . . ? P2 C51 S521 C54 -174.35(19) . . . . ? C552 C51 C551 C53 -1.7(19) . . . . ? S522 C51 C551 C53 -175(9) . . . . ? S521 C51 C551 C53 0.3(14) . . . . ? P2 C51 C551 C53 173.5(6) . . . . ? C54 C53 C551 C51 0.1(14) . . . . ? S522 C53 C551 C51 177(5) . . . . ? C54 C53 S522 C51 1.3(5) . . . . ? C551 C53 S522 C51 -2(3) . . . . ? C551 C51 S522 C53 4(7) . . . . ? C552 C51 S522 C53 -2.9(14) . . . . ? S521 C51 S522 C53 -0.7(5) . . . . ? P2 C51 S522 C53 173.7(2) . . . . ? C551 C51 C552 C54 2.1(18) . . . . ? S522 C51 C552 C54 3.1(18) . . . . ? S521 C51 C552 C54 -30(20) . . . . ? P2 C51 C552 C54 -173.7(5) . . . . ? C53 C54 C552 C51 -2.1(17) . . . . ? S521 C54 C552 C51 169(8) . . . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 25.28 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.461 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.057 #===END data_uwe19 _database_code_depnum_ccdc_archive 'CCDC 230858' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H22 N O5 P S' _chemical_formula_weight 479.47 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.7150(3) _cell_length_b 14.8630(3) _cell_length_c 18.1350(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4505.37(13) _cell_formula_units_Z 8 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 58111 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 0.253 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'NONIUS DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 58111 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.72 _reflns_number_total 5245 _reflns_number_gt 5036 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+2.1205P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5245 _refine_ls_number_parameters 386 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 P1 P 0.220676(19) 0.41947(2) 0.397578(18) 0.02064(10) Uani 1 1 d . . . S1 S 0.135328(19) 0.29917(2) 0.306953(18) 0.02322(10) Uani 1 1 d . . . O1 O 0.21728(5) 0.52289(6) 0.41523(5) 0.0243(2) Uani 1 1 d . . . O3 O 0.30958(6) 0.40552(7) 0.37345(5) 0.0243(2) Uani 1 1 d . . . O2 O 0.21677(5) 0.36581(7) 0.47194(5) 0.0247(2) Uani 1 1 d . . . O5 O 0.20290(6) 0.23937(7) 0.31428(6) 0.0310(2) Uani 1 1 d . . . O4 O 0.05906(6) 0.26549(8) 0.33126(6) 0.0341(2) Uani 1 1 d . . . C21 C 0.27537(7) 0.37053(9) 0.52879(7) 0.0224(3) Uani 1 1 d . . . C31 C 0.34166(7) 0.43647(9) 0.30545(7) 0.0213(3) Uani 1 1 d . . . C41 C 0.12555(8) 0.32887(8) 0.21300(8) 0.0220(3) Uani 1 1 d . . . C36 C 0.35291(8) 0.37373(9) 0.25022(8) 0.0243(3) Uani 1 1 d . . . C42 C 0.06113(8) 0.38218(9) 0.19178(8) 0.0255(3) Uani 1 1 d . . . C12 C 0.12957(9) 0.62999(10) 0.35881(9) 0.0289(3) Uani 1 1 d . . . C44 C 0.10846(9) 0.37940(9) 0.06558(8) 0.0261(3) Uani 1 1 d . . . C32 C 0.36533(9) 0.52529(10) 0.29874(8) 0.0262(3) Uani 1 1 d . . . C46 C 0.18142(8) 0.29998(9) 0.16125(8) 0.0271(3) Uani 1 1 d . . . C16 C 0.09677(9) 0.56769(10) 0.47832(8) 0.0275(3) Uani 1 1 d . . . C11 C 0.14569(8) 0.57333(9) 0.41726(7) 0.0220(3) Uani 1 1 d . . . C26 C 0.34349(8) 0.31845(9) 0.52327(8) 0.0260(3) Uani 1 1 d . . . C35 C 0.39166(8) 0.40077(10) 0.18615(8) 0.0264(3) Uani 1 1 d . . . C43 C 0.05263(9) 0.40637(10) 0.11834(8) 0.0279(3) Uani 1 1 d . . . N1 N 0.15164(7) 0.39468(8) 0.34467(7) 0.0263(2) Uani 1 1 d . . . C25 C 0.39730(9) 0.31956(10) 0.58172(9) 0.0307(3) Uani 1 1 d . . . C15 C 0.02798(9) 0.62022(10) 0.48063(9) 0.0330(3) Uani 1 1 d . . . C34 C 0.41839(8) 0.48868(10) 0.17870(7) 0.0258(3) Uani 1 1 d . . . C45 C 0.17240(9) 0.32642(10) 0.08798(8) 0.0288(3) Uani 1 1 d . . . C33 C 0.40436(9) 0.55070(10) 0.23422(8) 0.0279(3) Uani 1 1 d . . . C13 C 0.06036(10) 0.68165(10) 0.36177(10) 0.0357(3) Uani 1 1 d . . . C23 C 0.31337(11) 0.42273(11) 0.64786(9) 0.0363(3) Uani 1 1 d . . . C14 C 0.00966(9) 0.67665(10) 0.42191(10) 0.0350(3) Uani 1 1 d . . . C24 C 0.38226(10) 0.37137(11) 0.64386(9) 0.0348(3) Uani 1 1 d . . . C47 C 0.09945(11) 0.40733(13) -0.01360(9) 0.0377(4) Uani 1 1 d . . . C22 C 0.25882(10) 0.42262(10) 0.58991(8) 0.0302(3) Uani 1 1 d . . . H46 H 0.2253(11) 0.2610(13) 0.1764(10) 0.034(5) Uiso 1 1 d . . . H42 H 0.0235(11) 0.4033(12) 0.2286(10) 0.032(4) Uiso 1 1 d . . . H45 H 0.2127(12) 0.3057(14) 0.0526(12) 0.044(5) Uiso 1 1 d . . . H26 H 0.3535(11) 0.2829(13) 0.4805(11) 0.035(5) Uiso 1 1 d . . . H36 H 0.3341(11) 0.3125(12) 0.2579(10) 0.032(4) Uiso 1 1 d . . . H25 H 0.4454(11) 0.2837(13) 0.5789(10) 0.036(5) Uiso 1 1 d . . . H22 H 0.2087(12) 0.4577(14) 0.5919(11) 0.041(5) Uiso 1 1 d . . . H33 H 0.4218(12) 0.6112(13) 0.2288(10) 0.037(5) Uiso 1 1 d . . . H43 H 0.0058(12) 0.4431(14) 0.1026(10) 0.042(5) Uiso 1 1 d . . . H34 H 0.4483(11) 0.5060(13) 0.1360(10) 0.038(5) Uiso 1 1 d . . . H32 H 0.3545(11) 0.5699(13) 0.3380(11) 0.036(5) Uiso 1 1 d . . . H35 H 0.4011(12) 0.3563(14) 0.1489(11) 0.044(5) Uiso 1 1 d . . . H12 H 0.1681(12) 0.6341(13) 0.3190(11) 0.037(5) Uiso 1 1 d . . . H16 H 0.1096(12) 0.5277(13) 0.5182(11) 0.041(5) Uiso 1 1 d . . . H15 H -0.0055(11) 0.6162(13) 0.5234(10) 0.037(5) Uiso 1 1 d . . . H14 H -0.0376(13) 0.7112(14) 0.4241(11) 0.045(5) Uiso 1 1 d . . . H23 H 0.3023(13) 0.4604(14) 0.6918(12) 0.047(6) Uiso 1 1 d . . . H24 H 0.4212(13) 0.3706(15) 0.6852(12) 0.050(6) Uiso 1 1 d . . . H13 H 0.0476(13) 0.7232(15) 0.3198(12) 0.055(6) Uiso 1 1 d . . . H47A H 0.1150(14) 0.4713(17) -0.0208(13) 0.063(7) Uiso 1 1 d . . . H47B H 0.0434(17) 0.4094(17) -0.0288(14) 0.076(8) Uiso 1 1 d . . . H47C H 0.1274(18) 0.365(2) -0.0455(17) 0.093(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01944(17) 0.02267(18) 0.01980(17) 0.00109(11) 0.00021(11) 0.00250(11) S1 0.02259(17) 0.02067(17) 0.02640(18) 0.00223(11) -0.00192(12) -0.00035(11) O1 0.0199(4) 0.0243(5) 0.0288(5) -0.0018(4) -0.0008(3) 0.0020(4) O3 0.0222(5) 0.0304(5) 0.0203(4) 0.0058(4) 0.0033(4) 0.0050(4) O2 0.0214(4) 0.0302(5) 0.0225(5) 0.0045(4) -0.0004(3) -0.0008(4) O5 0.0318(5) 0.0215(5) 0.0396(6) 0.0023(4) -0.0065(4) 0.0052(4) O4 0.0287(5) 0.0382(6) 0.0355(6) 0.0093(5) 0.0019(4) -0.0088(4) C21 0.0217(6) 0.0234(6) 0.0220(6) 0.0051(5) -0.0007(5) -0.0005(5) C31 0.0184(6) 0.0267(6) 0.0188(6) 0.0038(5) 0.0013(4) 0.0033(5) C41 0.0201(6) 0.0192(6) 0.0267(6) -0.0025(5) -0.0003(5) -0.0020(4) C36 0.0214(6) 0.0239(6) 0.0277(7) -0.0007(5) 0.0000(5) 0.0008(5) C42 0.0221(6) 0.0274(7) 0.0270(7) 0.0012(5) 0.0036(5) 0.0030(5) C12 0.0293(7) 0.0264(7) 0.0310(7) 0.0052(5) -0.0011(6) -0.0018(5) C44 0.0282(7) 0.0252(6) 0.0251(6) -0.0013(5) 0.0017(5) -0.0065(5) C32 0.0325(7) 0.0249(6) 0.0214(6) -0.0015(5) 0.0011(5) 0.0029(5) C46 0.0221(6) 0.0275(7) 0.0316(7) -0.0060(5) -0.0008(5) 0.0032(5) C16 0.0274(7) 0.0288(7) 0.0263(7) 0.0006(5) 0.0016(5) 0.0016(5) C11 0.0200(6) 0.0202(6) 0.0257(6) -0.0018(5) -0.0015(5) 0.0001(5) C26 0.0256(6) 0.0244(6) 0.0279(7) 0.0037(5) 0.0023(5) 0.0030(5) C35 0.0256(6) 0.0306(7) 0.0229(6) -0.0054(5) 0.0005(5) 0.0018(5) C43 0.0253(7) 0.0294(7) 0.0291(7) 0.0032(5) 0.0006(5) 0.0039(5) N1 0.0277(6) 0.0238(6) 0.0275(6) -0.0031(4) -0.0052(5) 0.0042(4) C25 0.0257(7) 0.0299(7) 0.0365(8) 0.0100(6) -0.0024(6) 0.0008(6) C15 0.0263(7) 0.0315(7) 0.0414(8) -0.0080(6) 0.0060(6) 0.0001(6) C34 0.0256(6) 0.0321(7) 0.0199(6) 0.0023(5) 0.0002(5) 0.0007(5) C45 0.0260(7) 0.0318(7) 0.0285(7) -0.0073(5) 0.0052(5) -0.0009(6) C33 0.0333(7) 0.0247(6) 0.0256(6) 0.0025(5) 0.0011(5) -0.0007(5) C13 0.0333(8) 0.0251(7) 0.0486(9) 0.0091(6) -0.0095(7) 0.0002(6) C23 0.0446(9) 0.0375(8) 0.0268(7) -0.0018(6) -0.0023(6) 0.0004(7) C14 0.0247(7) 0.0220(6) 0.0583(10) -0.0060(6) -0.0055(7) 0.0031(5) C24 0.0356(8) 0.0380(8) 0.0306(7) 0.0081(6) -0.0094(6) -0.0063(6) C47 0.0423(9) 0.0432(9) 0.0275(7) 0.0033(6) 0.0019(7) -0.0070(7) C22 0.0321(7) 0.0328(7) 0.0257(7) 0.0012(5) 0.0024(6) 0.0062(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.5453(12) . ? P1 O3 1.5630(10) . ? P1 O2 1.5680(10) . ? P1 O1 1.5712(10) . ? S1 O4 1.4387(10) . ? S1 O5 1.4434(10) . ? S1 N1 1.5993(12) . ? S1 C41 1.7677(14) . ? O1 C11 1.4126(15) . ? O3 C31 1.4211(15) . ? O2 C21 1.4238(15) . ? C21 C22 1.380(2) . ? C21 C26 1.3804(18) . ? C31 C36 1.3813(19) . ? C31 C32 1.3835(19) . ? C41 C42 1.3912(18) . ? C41 C46 1.3918(19) . ? C36 C35 1.390(2) . ? C36 H36 0.972(18) . ? C42 C43 1.387(2) . ? C42 H42 0.969(18) . ? C12 C11 1.3803(19) . ? C12 C13 1.390(2) . ? C12 H12 0.97(2) . ? C44 C45 1.388(2) . ? C44 C43 1.395(2) . ? C44 C47 1.502(2) . ? C32 C33 1.3920(19) . ? C32 H32 0.99(2) . ? C46 C45 1.394(2) . ? C46 H46 0.974(18) . ? C16 C11 1.3792(19) . ? C16 C15 1.390(2) . ? C16 H16 0.96(2) . ? C26 C25 1.390(2) . ? C26 H26 0.95(2) . ? C35 C34 1.388(2) . ? C35 H35 0.96(2) . ? C43 H43 1.00(2) . ? C25 C24 1.388(2) . ? C25 H25 0.966(19) . ? C15 C14 1.390(2) . ? C15 H15 0.959(19) . ? C34 C33 1.3851(19) . ? C34 H34 0.958(19) . ? C45 H45 0.98(2) . ? C33 H33 0.951(19) . ? C13 C14 1.383(3) . ? C13 H13 1.00(2) . ? C23 C24 1.383(2) . ? C23 C22 1.391(2) . ? C23 H23 0.99(2) . ? C14 H14 0.94(2) . ? C24 H24 0.99(2) . ? C47 H47A 0.99(3) . ? C47 H47B 0.98(3) . ? C47 H47C 0.97(3) . ? C22 H22 0.99(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 O3 120.30(6) . . ? N1 P1 O2 112.44(6) . . ? O3 P1 O2 102.30(5) . . ? N1 P1 O1 109.44(6) . . ? O3 P1 O1 102.78(5) . . ? O2 P1 O1 108.71(6) . . ? O4 S1 O5 116.80(7) . . ? O4 S1 N1 109.20(7) . . ? O5 S1 N1 111.95(6) . . ? O4 S1 C41 107.48(6) . . ? O5 S1 C41 108.35(6) . . ? N1 S1 C41 101.91(6) . . ? C11 O1 P1 123.72(8) . . ? C31 O3 P1 123.97(8) . . ? C21 O2 P1 124.68(8) . . ? C22 C21 C26 122.55(13) . . ? C22 C21 O2 118.12(12) . . ? C26 C21 O2 119.17(12) . . ? C36 C31 C32 122.78(12) . . ? C36 C31 O3 117.52(12) . . ? C32 C31 O3 119.54(12) . . ? C42 C41 C46 120.57(13) . . ? C42 C41 S1 118.71(10) . . ? C46 C41 S1 120.72(10) . . ? C31 C36 C35 118.33(13) . . ? C31 C36 H36 118.9(11) . . ? C35 C36 H36 122.7(11) . . ? C43 C42 C41 119.51(13) . . ? C43 C42 H42 120.7(11) . . ? C41 C42 H42 119.8(11) . . ? C11 C12 C13 118.04(14) . . ? C11 C12 H12 118.7(12) . . ? C13 C12 H12 123.1(12) . . ? C45 C44 C43 118.50(13) . . ? C45 C44 C47 120.90(14) . . ? C43 C44 C47 120.60(14) . . ? C31 C32 C33 117.83(13) . . ? C31 C32 H32 121.6(11) . . ? C33 C32 H32 120.6(11) . . ? C41 C46 C45 118.90(13) . . ? C41 C46 H46 119.9(11) . . ? C45 C46 H46 121.2(11) . . ? C11 C16 C15 118.71(14) . . ? C11 C16 H16 120.7(12) . . ? C15 C16 H16 120.6(12) . . ? C16 C11 C12 122.54(13) . . ? C16 C11 O1 119.40(12) . . ? C12 C11 O1 117.98(12) . . ? C21 C26 C25 118.15(13) . . ? C21 C26 H26 121.0(11) . . ? C25 C26 H26 120.8(11) . . ? C34 C35 C36 120.26(13) . . ? C34 C35 H35 121.9(12) . . ? C36 C35 H35 117.8(12) . . ? C42 C43 C44 121.03(13) . . ? C42 C43 H43 119.8(11) . . ? C44 C43 H43 119.1(11) . . ? P1 N1 S1 127.19(8) . . ? C24 C25 C26 120.55(14) . . ? C24 C25 H25 120.0(11) . . ? C26 C25 H25 119.5(11) . . ? C14 C15 C16 119.87(15) . . ? C14 C15 H15 121.9(11) . . ? C16 C15 H15 118.2(11) . . ? C33 C34 C35 120.09(13) . . ? C33 C34 H34 119.9(11) . . ? C35 C34 H34 120.0(11) . . ? C44 C45 C46 121.48(13) . . ? C44 C45 H45 121.1(12) . . ? C46 C45 H45 117.5(12) . . ? C34 C33 C32 120.66(13) . . ? C34 C33 H33 120.2(11) . . ? C32 C33 H33 119.2(11) . . ? C14 C13 C12 120.72(14) . . ? C14 C13 H13 120.0(13) . . ? C12 C13 H13 119.2(13) . . ? C24 C23 C22 120.34(15) . . ? C24 C23 H23 120.6(12) . . ? C22 C23 H23 119.0(12) . . ? C13 C14 C15 120.11(14) . . ? C13 C14 H14 121.1(12) . . ? C15 C14 H14 118.8(13) . . ? C23 C24 C25 119.98(14) . . ? C23 C24 H24 120.8(13) . . ? C25 C24 H24 119.2(13) . . ? C44 C47 H47A 111.3(14) . . ? C44 C47 H47B 112.0(16) . . ? H47A C47 H47B 101(2) . . ? C44 C47 H47C 110.0(18) . . ? H47A C47 H47C 115(2) . . ? H47B C47 H47C 108(2) . . ? C21 C22 C23 118.43(14) . . ? C21 C22 H22 119.6(11) . . ? C23 C22 H22 121.9(11) . . ? 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 P1 O1 C11 30.66(12) . . . . ? O3 P1 O1 C11 159.61(10) . . . . ? O2 P1 O1 C11 -92.49(11) . . . . ? N1 P1 O3 C31 49.85(13) . . . . ? O2 P1 O3 C31 175.28(10) . . . . ? O1 P1 O3 C31 -72.01(11) . . . . ? N1 P1 O2 C21 175.65(10) . . . . ? O3 P1 O2 C21 45.21(11) . . . . ? O1 P1 O2 C21 -63.01(11) . . . . ? P1 O2 C21 C22 101.58(14) . . . . ? P1 O2 C21 C26 -82.90(14) . . . . ? P1 O3 C31 C36 -102.87(13) . . . . ? P1 O3 C31 C32 81.58(15) . . . . ? O4 S1 C41 C42 49.16(12) . . . . ? O5 S1 C41 C42 176.20(11) . . . . ? N1 S1 C41 C42 -65.60(12) . . . . ? O4 S1 C41 C46 -131.22(11) . . . . ? O5 S1 C41 C46 -4.18(13) . . . . ? N1 S1 C41 C46 114.02(11) . . . . ? C32 C31 C36 C35 1.8(2) . . . . ? O3 C31 C36 C35 -173.56(12) . . . . ? C46 C41 C42 C43 0.2(2) . . . . ? S1 C41 C42 C43 179.81(11) . . . . ? C36 C31 C32 C33 -2.1(2) . . . . ? O3 C31 C32 C33 173.16(12) . . . . ? C42 C41 C46 C45 0.9(2) . . . . ? S1 C41 C46 C45 -178.71(11) . . . . ? C15 C16 C11 C12 0.9(2) . . . . ? C15 C16 C11 O1 177.71(12) . . . . ? C13 C12 C11 C16 -1.3(2) . . . . ? C13 C12 C11 O1 -178.11(12) . . . . ? P1 O1 C11 C16 78.30(15) . . . . ? P1 O1 C11 C12 -104.75(13) . . . . ? C22 C21 C26 C25 -0.4(2) . . . . ? O2 C21 C26 C25 -175.75(12) . . . . ? C31 C36 C35 C34 0.3(2) . . . . ? C41 C42 C43 C44 -1.2(2) . . . . ? C45 C44 C43 C42 1.0(2) . . . . ? C47 C44 C43 C42 -178.92(14) . . . . ? O3 P1 N1 S1 56.42(12) . . . . ? O2 P1 N1 S1 -64.11(11) . . . . ? O1 P1 N1 S1 174.97(8) . . . . ? O4 S1 N1 P1 118.20(10) . . . . ? O5 S1 N1 P1 -12.73(12) . . . . ? C41 S1 N1 P1 -128.32(10) . . . . ? C21 C26 C25 C24 0.4(2) . . . . ? C11 C16 C15 C14 0.3(2) . . . . ? C36 C35 C34 C33 -2.0(2) . . . . ? C43 C44 C45 C46 0.2(2) . . . . ? C47 C44 C45 C46 -179.94(14) . . . . ? C41 C46 C45 C44 -1.1(2) . . . . ? C35 C34 C33 C32 1.7(2) . . . . ? C31 C32 C33 C34 0.3(2) . . . . ? C11 C12 C13 C14 0.5(2) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C16 C15 C14 C13 -1.0(2) . . . . ? C22 C23 C24 C25 0.1(2) . . . . ? C26 C25 C24 C23 -0.2(2) . . . . ? C26 C21 C22 C23 0.4(2) . . . . ? O2 C21 C22 C23 175.72(13) . . . . ? C24 C23 C22 C21 -0.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.72 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.188 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.059 #===END data_uwe42 _database_code_depnum_ccdc_archive 'CCDC 230859' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H20 N O2 P S' _chemical_formula_weight 429.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.9435(2) _cell_length_b 12.24260(10) _cell_length_c 18.7133(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4110.85(9) _cell_formula_units_Z 8 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 70695 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.258 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'NONIUS DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 70695 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.020 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.39 _reflns_number_total 3719 _reflns_number_gt 3604 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+2.8002P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3719 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 S1 S 0.08554(2) 0.68790(3) 0.102717(19) 0.01939(11) Uani 1 1 d . . . P1 P 0.12303(2) 0.75089(3) -0.04051(2) 0.01653(11) Uani 1 1 d . . . O1 O 0.03495(6) 0.73380(9) 0.15441(6) 0.0259(3) Uani 1 1 d . . . N1 N 0.07712(7) 0.75870(11) 0.03215(7) 0.0205(3) Uani 1 1 d . . . O2 O 0.07927(6) 0.57217(9) 0.08885(6) 0.0261(3) Uani 1 1 d . . . C11 C 0.22176(8) 0.77401(12) -0.03499(8) 0.0188(3) Uani 1 1 d . . . C12 C 0.25908(9) 0.85679(13) 0.00085(8) 0.0230(3) Uani 1 1 d . . . H12 H 0.2305(10) 0.9163(15) 0.0253(9) 0.024(4) Uiso 1 1 d . . . C13 C 0.33672(9) 0.85459(15) 0.00246(9) 0.0289(4) Uani 1 1 d . . . H13 H 0.3629(12) 0.9095(18) 0.0276(11) 0.038(5) Uiso 1 1 d . . . C14 C 0.37497(9) 0.77148(17) -0.03217(10) 0.0322(4) Uani 1 1 d . . . H14 H 0.4293(13) 0.7719(18) -0.0296(12) 0.044(6) Uiso 1 1 d . . . C15 C 0.33778(9) 0.68927(15) -0.06878(9) 0.0281(4) Uani 1 1 d . . . H15 H 0.3646(11) 0.6343(16) -0.0937(10) 0.031(5) Uiso 1 1 d . . . C16 C 0.26017(8) 0.68956(13) -0.07001(8) 0.0207(3) Uani 1 1 d . . . C21 C 0.13426(8) 0.62542(12) -0.08888(8) 0.0197(3) Uani 1 1 d . . . C22 C 0.07953(10) 0.55515(14) -0.11490(9) 0.0249(3) Uani 1 1 d . . . H22 H 0.0272(12) 0.5656(17) -0.1019(11) 0.037(5) Uiso 1 1 d . . . C23 C 0.10139(11) 0.46702(14) -0.15667(9) 0.0305(4) Uani 1 1 d . . . H23 H 0.0637(12) 0.4171(19) -0.1752(12) 0.043(6) Uiso 1 1 d . . . C24 C 0.17611(11) 0.45007(14) -0.17186(9) 0.0319(4) Uani 1 1 d . . . H24 H 0.1923(12) 0.3893(18) -0.2004(12) 0.044(6) Uiso 1 1 d . . . C25 C 0.23085(10) 0.51920(13) -0.14514(9) 0.0269(4) Uani 1 1 d . . . H25 H 0.2829(11) 0.5064(15) -0.1552(10) 0.027(5) Uiso 1 1 d . . . C26 C 0.21015(9) 0.60759(13) -0.10313(8) 0.0205(3) Uani 1 1 d . . . C31 C 0.08003(8) 0.84902(12) -0.09889(8) 0.0180(3) Uani 1 1 d . . . C32 C 0.10329(9) 0.85834(13) -0.16979(8) 0.0218(3) Uani 1 1 d . . . H32 H 0.1395(10) 0.8127(15) -0.1868(10) 0.023(5) Uiso 1 1 d . . . C33 C 0.07241(9) 0.93829(13) -0.21349(8) 0.0242(3) Uani 1 1 d . . . H33 H 0.0893(10) 0.9425(15) -0.2649(11) 0.029(5) Uiso 1 1 d . . . C34 C 0.01873(9) 1.00867(13) -0.18663(9) 0.0236(3) Uani 1 1 d . . . H34 H -0.0013(11) 1.0638(17) -0.2159(11) 0.035(5) Uiso 1 1 d . . . C35 C -0.00554(9) 0.99844(13) -0.11668(9) 0.0239(3) Uani 1 1 d . . . H35 H -0.0425(11) 1.0490(16) -0.0985(10) 0.028(5) Uiso 1 1 d . . . C36 C 0.02484(9) 0.91833(13) -0.07264(8) 0.0213(3) Uani 1 1 d . . . H36 H 0.0083(10) 0.9106(14) -0.0244(10) 0.022(4) Uiso 1 1 d . . . C41 C 0.17702(8) 0.71005(13) 0.13499(8) 0.0204(3) Uani 1 1 d . . . C42 C 0.19386(10) 0.80473(14) 0.17294(9) 0.0259(3) Uani 1 1 d . . . H42 H 0.1542(11) 0.8574(17) 0.1848(11) 0.036(5) Uiso 1 1 d . . . C43 C 0.26681(10) 0.82439(15) 0.19341(9) 0.0287(4) Uani 1 1 d . . . H43 H 0.2781(12) 0.8919(18) 0.2197(11) 0.039(5) Uiso 1 1 d . . . C44 C 0.32385(9) 0.75117(14) 0.17701(9) 0.0259(4) Uani 1 1 d . . . C45 C 0.30554(9) 0.65614(14) 0.14058(9) 0.0270(4) Uani 1 1 d . . . H45 H 0.3449(11) 0.6030(17) 0.1293(11) 0.037(5) Uiso 1 1 d . . . C46 C 0.23266(9) 0.63508(13) 0.11949(9) 0.0237(3) Uani 1 1 d . . . H46 H 0.2191(11) 0.5698(17) 0.0931(10) 0.031(5) Uiso 1 1 d . . . C47 C 0.40297(11) 0.77528(19) 0.19819(13) 0.0379(5) Uani 1 1 d . . . H47C H 0.4078(14) 0.780(2) 0.2485(16) 0.067(8) Uiso 1 1 d . . . H47B H 0.4199(13) 0.844(2) 0.1790(13) 0.054(7) Uiso 1 1 d . . . H47A H 0.4364(17) 0.726(3) 0.1812(17) 0.079(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0180(2) 0.0205(2) 0.0198(2) 0.00200(14) 0.00157(14) 0.00149(14) P1 0.0143(2) 0.0171(2) 0.0181(2) -0.00020(14) 0.00049(14) 0.00080(13) O1 0.0238(6) 0.0313(6) 0.0227(6) 0.0025(5) 0.0070(5) 0.0052(5) N1 0.0171(6) 0.0247(7) 0.0198(7) 0.0026(5) 0.0019(5) 0.0033(5) O2 0.0245(6) 0.0202(6) 0.0335(6) 0.0007(5) -0.0006(5) -0.0022(4) C11 0.0172(7) 0.0208(8) 0.0183(7) 0.0035(6) 0.0009(6) -0.0002(6) C12 0.0237(8) 0.0238(8) 0.0214(7) 0.0040(6) -0.0008(6) -0.0050(6) C13 0.0245(8) 0.0344(10) 0.0276(9) 0.0089(7) -0.0046(7) -0.0103(7) C14 0.0163(8) 0.0443(11) 0.0358(10) 0.0137(8) -0.0005(7) -0.0035(7) C15 0.0185(8) 0.0357(10) 0.0299(9) 0.0079(7) 0.0061(7) 0.0062(7) C16 0.0196(7) 0.0226(8) 0.0198(7) 0.0052(6) 0.0023(6) 0.0018(6) C21 0.0222(8) 0.0178(8) 0.0190(7) 0.0019(6) -0.0005(6) 0.0012(6) C22 0.0272(9) 0.0213(8) 0.0264(8) 0.0031(6) -0.0048(7) -0.0027(6) C23 0.0449(10) 0.0215(9) 0.0252(9) 0.0001(7) -0.0078(8) -0.0056(7) C24 0.0547(12) 0.0192(8) 0.0219(8) -0.0011(7) 0.0031(8) 0.0042(8) C25 0.0345(9) 0.0235(8) 0.0228(8) 0.0030(6) 0.0070(7) 0.0077(7) C26 0.0239(8) 0.0190(8) 0.0188(7) 0.0038(6) 0.0022(6) 0.0033(6) C31 0.0166(7) 0.0173(7) 0.0202(7) -0.0013(6) -0.0020(6) -0.0013(5) C32 0.0223(8) 0.0219(8) 0.0213(8) -0.0021(6) 0.0018(6) 0.0013(6) C33 0.0285(8) 0.0248(8) 0.0192(8) -0.0005(6) -0.0020(6) -0.0030(7) C34 0.0271(8) 0.0197(8) 0.0241(8) 0.0019(6) -0.0070(6) -0.0006(6) C35 0.0240(8) 0.0212(8) 0.0267(8) -0.0006(7) -0.0016(6) 0.0045(6) C36 0.0221(8) 0.0221(8) 0.0197(8) -0.0013(6) 0.0007(6) 0.0015(6) C41 0.0212(7) 0.0222(8) 0.0177(7) 0.0029(6) 0.0005(6) 0.0010(6) C42 0.0284(8) 0.0258(9) 0.0236(8) -0.0041(7) 0.0011(7) 0.0040(7) C43 0.0329(9) 0.0285(9) 0.0247(8) -0.0057(7) -0.0021(7) -0.0021(7) C44 0.0259(8) 0.0294(9) 0.0223(8) 0.0026(6) -0.0032(7) -0.0024(7) C45 0.0229(8) 0.0266(9) 0.0314(9) 0.0009(7) -0.0026(7) 0.0049(7) C46 0.0249(8) 0.0206(8) 0.0255(8) -0.0008(6) -0.0025(6) 0.0030(6) C47 0.0280(10) 0.0417(12) 0.0441(12) -0.0030(9) -0.0088(8) -0.0031(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4406(11) . ? S1 O2 1.4449(12) . ? S1 N1 1.5867(13) . ? S1 C41 1.7700(16) . ? P1 N1 1.5927(13) . ? P1 C21 1.7942(16) . ? P1 C11 1.7969(15) . ? P1 C31 1.7979(15) . ? C11 C12 1.388(2) . ? C11 C16 1.405(2) . ? C12 C13 1.394(2) . ? C12 H12 1.001(18) . ? C13 C14 1.388(3) . ? C13 H13 0.95(2) . ? C14 C15 1.388(3) . ? C14 H14 0.98(2) . ? C15 C16 1.393(2) . ? C15 H15 0.95(2) . ? C16 C26 1.482(2) . ? C21 C22 1.393(2) . ? C21 C26 1.405(2) . ? C22 C23 1.389(2) . ? C22 H22 0.98(2) . ? C23 C24 1.386(3) . ? C23 H23 0.97(2) . ? C24 C25 1.390(3) . ? C24 H24 0.96(2) . ? C25 C26 1.388(2) . ? C25 H25 0.965(19) . ? C31 C36 1.393(2) . ? C31 C32 1.396(2) . ? C32 C33 1.391(2) . ? C32 H32 0.915(19) . ? C33 C34 1.387(2) . ? C33 H33 1.01(2) . ? C34 C35 1.385(2) . ? C34 H34 0.94(2) . ? C35 C36 1.392(2) . ? C35 H35 0.969(19) . ? C36 H36 0.955(18) . ? C41 C46 1.387(2) . ? C41 C42 1.392(2) . ? C42 C43 1.385(2) . ? C42 H42 0.99(2) . ? C43 C44 1.395(2) . ? C43 H43 0.98(2) . ? C44 C45 1.388(2) . ? C44 C47 1.503(2) . ? C45 C46 1.390(2) . ? C45 H45 0.98(2) . ? C46 H46 0.97(2) . ? C47 H47C 0.95(3) . ? C47 H47B 0.96(3) . ? C47 H47A 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 117.00(7) . . ? O1 S1 N1 106.60(7) . . ? O2 S1 N1 112.25(7) . . ? O1 S1 C41 107.19(7) . . ? O2 S1 C41 106.48(7) . . ? N1 S1 C41 106.77(7) . . ? N1 P1 C21 122.69(7) . . ? N1 P1 C11 116.84(7) . . ? C21 P1 C11 93.05(7) . . ? N1 P1 C31 104.87(7) . . ? C21 P1 C31 108.28(7) . . ? C11 P1 C31 110.66(7) . . ? S1 N1 P1 128.94(8) . . ? C12 C11 C16 121.75(14) . . ? C12 C11 P1 128.21(12) . . ? C16 C11 P1 109.94(11) . . ? C11 C12 C13 118.60(16) . . ? C11 C12 H12 120.4(10) . . ? C13 C12 H12 121.0(10) . . ? C14 C13 C12 119.90(16) . . ? C14 C13 H13 120.5(13) . . ? C12 C13 H13 119.6(13) . . ? C13 C14 C15 121.61(15) . . ? C13 C14 H14 117.8(13) . . ? C15 C14 H14 120.5(13) . . ? C14 C15 C16 119.13(16) . . ? C14 C15 H15 120.9(12) . . ? C16 C15 H15 120.0(12) . . ? C15 C16 C11 118.99(15) . . ? C15 C16 C26 127.64(15) . . ? C11 C16 C26 113.34(13) . . ? C22 C21 C26 121.39(15) . . ? C22 C21 P1 128.74(13) . . ? C26 C21 P1 109.73(11) . . ? C23 C22 C21 118.51(16) . . ? C23 C22 H22 120.8(12) . . ? C21 C22 H22 120.6(12) . . ? C24 C23 C22 120.33(16) . . ? C24 C23 H23 120.3(13) . . ? C22 C23 H23 119.4(13) . . ? C23 C24 C25 121.24(16) . . ? C23 C24 H24 121.5(13) . . ? C25 C24 H24 117.2(13) . . ? C26 C25 C24 119.31(16) . . ? C26 C25 H25 119.7(11) . . ? C24 C25 H25 121.0(11) . . ? C25 C26 C21 119.21(15) . . ? C25 C26 C16 127.06(15) . . ? C21 C26 C16 113.73(13) . . ? C36 C31 C32 119.86(14) . . ? C36 C31 P1 119.85(12) . . ? C32 C31 P1 120.26(12) . . ? C33 C32 C31 119.83(15) . . ? C33 C32 H32 120.5(11) . . ? C31 C32 H32 119.6(11) . . ? C34 C33 C32 120.07(15) . . ? C34 C33 H33 121.5(11) . . ? C32 C33 H33 118.5(11) . . ? C35 C34 C33 120.31(15) . . ? C35 C34 H34 119.7(12) . . ? C33 C34 H34 120.0(12) . . ? C34 C35 C36 120.00(15) . . ? C34 C35 H35 119.3(11) . . ? C36 C35 H35 120.7(11) . . ? C35 C36 C31 119.91(15) . . ? C35 C36 H36 120.6(11) . . ? C31 C36 H36 119.5(11) . . ? C46 C41 C42 120.09(15) . . ? C46 C41 S1 119.66(12) . . ? C42 C41 S1 120.19(12) . . ? C43 C42 C41 119.40(15) . . ? C43 C42 H42 120.4(12) . . ? C41 C42 H42 120.2(12) . . ? C42 C43 C44 121.40(16) . . ? C42 C43 H43 118.7(12) . . ? C44 C43 H43 119.9(12) . . ? C45 C44 C43 118.24(15) . . ? C45 C44 C47 121.18(16) . . ? C43 C44 C47 120.58(16) . . ? C44 C45 C46 121.18(16) . . ? C44 C45 H45 119.3(12) . . ? C46 C45 H45 119.5(12) . . ? C41 C46 C45 119.67(15) . . ? C41 C46 H46 118.1(12) . . ? C45 C46 H46 122.2(12) . . ? C44 C47 H47C 111.1(16) . . ? C44 C47 H47B 111.8(14) . . ? H47C C47 H47B 107(2) . . ? C44 C47 H47A 113.5(19) . . ? H47C C47 H47A 109(2) . . ? H47B C47 H47A 104(2) . . ? 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 O1 S1 N1 P1 175.37(10) . . . . ? O2 S1 N1 P1 -55.29(13) . . . . ? C41 S1 N1 P1 61.04(12) . . . . ? C21 P1 N1 S1 52.57(14) . . . . ? C11 P1 N1 S1 -60.73(13) . . . . ? C31 P1 N1 S1 176.35(10) . . . . ? N1 P1 C11 C12 -46.11(16) . . . . ? C21 P1 C11 C12 -175.38(14) . . . . ? C31 P1 C11 C12 73.77(15) . . . . ? N1 P1 C11 C16 130.27(10) . . . . ? C21 P1 C11 C16 1.00(11) . . . . ? C31 P1 C11 C16 -109.85(11) . . . . ? C16 C11 C12 C13 -0.7(2) . . . . ? P1 C11 C12 C13 175.28(12) . . . . ? C11 C12 C13 C14 0.8(2) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C13 C14 C15 C16 -0.8(3) . . . . ? C14 C15 C16 C11 0.9(2) . . . . ? C14 C15 C16 C26 -177.25(15) . . . . ? C12 C11 C16 C15 -0.2(2) . . . . ? P1 C11 C16 C15 -176.81(12) . . . . ? C12 C11 C16 C26 178.26(13) . . . . ? P1 C11 C16 C26 1.60(15) . . . . ? N1 P1 C21 C22 56.00(17) . . . . ? C11 P1 C21 C22 -179.15(15) . . . . ? C31 P1 C21 C22 -66.22(16) . . . . ? N1 P1 C21 C26 -128.26(11) . . . . ? C11 P1 C21 C26 -3.41(12) . . . . ? C31 P1 C21 C26 109.52(11) . . . . ? C26 C21 C22 C23 -1.0(2) . . . . ? P1 C21 C22 C23 174.28(13) . . . . ? C21 C22 C23 C24 0.0(2) . . . . ? C22 C23 C24 C25 0.9(3) . . . . ? C23 C24 C25 C26 -0.8(2) . . . . ? C24 C25 C26 C21 -0.3(2) . . . . ? C24 C25 C26 C16 179.89(15) . . . . ? C22 C21 C26 C25 1.2(2) . . . . ? P1 C21 C26 C25 -174.90(12) . . . . ? C22 C21 C26 C16 -178.97(14) . . . . ? P1 C21 C26 C16 4.92(16) . . . . ? C15 C16 C26 C25 -6.3(3) . . . . ? C11 C16 C26 C25 175.44(14) . . . . ? C15 C16 C26 C21 173.88(15) . . . . ? C11 C16 C26 C21 -4.37(18) . . . . ? N1 P1 C31 C36 6.58(14) . . . . ? C21 P1 C31 C36 139.13(12) . . . . ? C11 P1 C31 C36 -120.25(13) . . . . ? N1 P1 C31 C32 -175.40(12) . . . . ? C21 P1 C31 C32 -42.85(14) . . . . ? C11 P1 C31 C32 57.78(14) . . . . ? C36 C31 C32 C33 1.4(2) . . . . ? P1 C31 C32 C33 -176.66(12) . . . . ? C31 C32 C33 C34 0.1(2) . . . . ? C32 C33 C34 C35 -1.3(2) . . . . ? C33 C34 C35 C36 1.0(2) . . . . ? C34 C35 C36 C31 0.4(2) . . . . ? C32 C31 C36 C35 -1.6(2) . . . . ? P1 C31 C36 C35 176.39(12) . . . . ? O1 S1 C41 C46 148.25(13) . . . . ? O2 S1 C41 C46 22.29(15) . . . . ? N1 S1 C41 C46 -97.82(14) . . . . ? O1 S1 C41 C42 -34.70(15) . . . . ? O2 S1 C41 C42 -160.66(13) . . . . ? N1 S1 C41 C42 79.23(14) . . . . ? C46 C41 C42 C43 1.6(2) . . . . ? S1 C41 C42 C43 -175.47(13) . . . . ? C41 C42 C43 C44 -0.2(3) . . . . ? C42 C43 C44 C45 -1.3(3) . . . . ? C42 C43 C44 C47 178.54(18) . . . . ? C43 C44 C45 C46 1.4(3) . . . . ? C47 C44 C45 C46 -178.44(17) . . . . ? C42 C41 C46 C45 -1.5(2) . . . . ? S1 C41 C46 C45 175.58(13) . . . . ? C44 C45 C46 C41 0.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.261 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.045 #===END data_uwe34 _database_code_depnum_ccdc_archive 'CCDC 230860' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 As O3' _chemical_formula_weight 276.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.79090(10) _cell_length_b 8.16180(10) _cell_length_c 17.2498(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1096.88(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 29571 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 3.086 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.634 _exptl_absorpt_correction_T_max 0.892 _exptl_absorpt_process_details ; Platon Delabs (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'NONIUS DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29571 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 26.73 _reflns_number_total 2263 _reflns_number_gt 2243 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0248P)^2^+0.1032P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.026(8) _refine_ls_number_reflns 2263 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0178 _refine_ls_R_factor_gt 0.0177 _refine_ls_wR_factor_ref 0.0468 _refine_ls_wR_factor_gt 0.0467 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.128 _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 As1 As 0.20565(2) 0.192668(19) 0.050398(9) 0.02061(7) Uani 1 1 d . . . C11 C 0.0668(2) 0.0809(2) 0.12711(10) 0.0223(3) Uani 1 1 d . . . O12 O 0.14017(18) -0.00783(18) 0.18599(8) 0.0346(3) Uani 1 1 d . . . C13 C 0.0065(3) -0.0664(3) 0.23041(12) 0.0365(5) Uani 1 1 d . . . H13 H 0.037(4) -0.125(4) 0.2707(19) 0.062(10) Uiso 1 1 d . . . C14 C -0.1433(3) -0.0198(3) 0.20127(11) 0.0317(4) Uani 1 1 d . . . H14 H -0.250(4) -0.041(3) 0.2197(15) 0.045(7) Uiso 1 1 d . . . C15 C -0.1050(3) 0.0756(2) 0.13351(10) 0.0275(4) Uani 1 1 d . . . H15 H -0.181(3) 0.126(3) 0.1012(14) 0.036(6) Uiso 1 1 d . . . C21 C 0.3616(2) 0.3089(2) 0.11804(10) 0.0220(3) Uani 1 1 d . . . O21 O 0.44550(19) 0.22897(16) 0.17683(8) 0.0300(3) Uani 1 1 d . . . C23 C 0.5569(3) 0.3402(3) 0.20876(12) 0.0317(4) Uani 1 1 d . . . H23 H 0.619(3) 0.297(3) 0.2525(14) 0.033(6) Uiso 1 1 d . . . C24 C 0.5457(3) 0.4847(3) 0.17212(12) 0.0319(4) Uani 1 1 d . . . H24 H 0.610(4) 0.571(4) 0.1835(15) 0.041(7) Uiso 1 1 d . . . C25 C 0.4180(3) 0.4651(2) 0.11301(12) 0.0290(4) Uani 1 1 d . . . H25 H 0.380(3) 0.540(3) 0.0785(13) 0.026(5) Uiso 1 1 d . . . C31 C 0.3617(2) 0.0174(2) 0.02368(10) 0.0227(3) Uani 1 1 d . . . O32 O 0.3821(2) -0.01367(18) -0.05385(8) 0.0374(3) Uani 1 1 d . . . C33 C 0.5050(4) -0.1347(3) -0.05964(16) 0.0442(6) Uani 1 1 d . . . H33 H 0.534(4) -0.158(4) -0.1104(18) 0.054(8) Uiso 1 1 d . . . C34 C 0.5600(3) -0.1767(3) 0.00988(17) 0.0437(5) Uani 1 1 d . . . H34 H 0.640(4) -0.250(4) 0.0178(17) 0.053(8) Uiso 1 1 d . . . C35 C 0.4700(3) -0.0785(2) 0.06555(11) 0.0288(4) Uani 1 1 d D . . H35 H 0.481(4) -0.076(4) 0.1176(11) 0.068(10) Uiso 1 1 d 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 As1 0.02097(10) 0.02122(9) 0.01964(9) 0.00236(6) -0.00133(6) -0.00080(6) C11 0.0228(9) 0.0227(8) 0.0215(7) -0.0001(7) 0.0005(6) -0.0017(7) O12 0.0226(7) 0.0482(9) 0.0329(7) 0.0182(6) 0.0013(5) 0.0006(6) C13 0.0323(11) 0.0470(13) 0.0301(10) 0.0174(10) 0.0060(8) -0.0016(10) C14 0.0281(11) 0.0369(10) 0.0303(10) 0.0017(8) 0.0085(8) -0.0042(8) C15 0.0226(9) 0.0329(9) 0.0269(9) 0.0015(8) -0.0011(7) 0.0011(8) C21 0.0212(9) 0.0237(8) 0.0210(8) -0.0021(7) 0.0010(6) -0.0019(7) O21 0.0306(8) 0.0307(7) 0.0287(7) 0.0030(5) -0.0088(5) -0.0058(6) C23 0.0250(10) 0.0410(11) 0.0292(10) -0.0088(8) -0.0024(8) -0.0046(8) C24 0.0271(10) 0.0306(10) 0.0379(11) -0.0133(8) 0.0026(8) -0.0072(8) C25 0.0284(11) 0.0234(8) 0.0353(10) -0.0029(8) 0.0020(7) -0.0020(7) C31 0.0234(9) 0.0220(7) 0.0226(8) -0.0011(6) 0.0013(7) -0.0039(7) O32 0.0390(8) 0.0445(8) 0.0288(7) -0.0091(6) 0.0031(7) -0.0056(6) C33 0.0441(14) 0.0403(12) 0.0483(14) -0.0171(10) 0.0186(11) -0.0100(9) C34 0.0316(12) 0.0271(10) 0.0722(16) 0.0020(10) 0.0128(11) 0.0054(9) C35 0.0268(10) 0.0281(9) 0.0315(9) 0.0079(8) 0.0027(7) 0.0050(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag As1 C31 1.9330(19) . ? As1 C21 1.9332(18) . ? As1 C11 1.9374(18) . ? C11 C15 1.344(3) . ? C11 O12 1.372(2) . ? O12 C13 1.379(2) . ? C13 C14 1.326(3) . ? C13 H13 0.88(3) . ? C14 C15 1.435(3) . ? C14 H14 0.91(3) . ? C15 H15 0.91(3) . ? C21 C25 1.351(3) . ? C21 O21 1.372(2) . ? O21 C23 1.371(2) . ? C23 C24 1.341(3) . ? C23 H23 0.97(2) . ? C24 C25 1.434(3) . ? C24 H24 0.88(3) . ? C25 H25 0.91(2) . ? C31 C35 1.359(3) . ? C31 O32 1.370(2) . ? O32 C33 1.379(3) . ? C33 C34 1.319(4) . ? C33 H33 0.92(3) . ? C34 C35 1.434(3) . ? C34 H34 0.87(3) . ? C35 H35 0.902(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 C31 As1 C21 96.43(8) . . ? C31 As1 C11 99.55(8) . . ? C21 As1 C11 99.77(8) . . ? C15 C11 O12 109.70(17) . . ? C15 C11 As1 128.89(15) . . ? O12 C11 As1 121.41(13) . . ? C11 O12 C13 106.22(15) . . ? C14 C13 O12 110.77(17) . . ? C14 C13 H13 134(2) . . ? O12 C13 H13 115(2) . . ? C13 C14 C15 106.36(17) . . ? C13 C14 H14 128.2(18) . . ? C15 C14 H14 125.4(18) . . ? C11 C15 C14 106.94(17) . . ? C11 C15 H15 125.6(17) . . ? C14 C15 H15 127.4(16) . . ? C25 C21 O21 109.96(16) . . ? C25 C21 As1 128.96(15) . . ? O21 C21 As1 120.80(13) . . ? C23 O21 C21 106.47(15) . . ? C24 C23 O21 110.60(18) . . ? C24 C23 H23 136.2(15) . . ? O21 C23 H23 113.1(15) . . ? C23 C24 C25 106.40(17) . . ? C23 C24 H24 123.8(18) . . ? C25 C24 H24 129.8(18) . . ? C21 C25 C24 106.57(17) . . ? C21 C25 H25 125.3(15) . . ? C24 C25 H25 128.1(15) . . ? C35 C31 O32 109.87(17) . . ? C35 C31 As1 133.63(14) . . ? O32 C31 As1 116.28(13) . . ? C31 O32 C33 106.49(18) . . ? C34 C33 O32 110.3(2) . . ? C34 C33 H33 137(2) . . ? O32 C33 H33 112.6(19) . . ? C33 C34 C35 107.7(2) . . ? C33 C34 H34 123(2) . . ? C35 C34 H34 129(2) . . ? C31 C35 C34 105.66(19) . . ? C31 C35 H35 125(2) . . ? C34 C35 H35 129(2) . . ? 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 C31 As1 C11 C15 -132.42(19) . . . . ? C21 As1 C11 C15 129.29(19) . . . . ? C31 As1 C11 O12 48.04(16) . . . . ? C21 As1 C11 O12 -50.26(16) . . . . ? C15 C11 O12 C13 -1.1(2) . . . . ? As1 C11 O12 C13 178.49(15) . . . . ? C11 O12 C13 C14 0.7(2) . . . . ? O12 C13 C14 C15 -0.1(3) . . . . ? O12 C11 C15 C14 1.1(2) . . . . ? As1 C11 C15 C14 -178.49(14) . . . . ? C13 C14 C15 C11 -0.6(2) . . . . ? C31 As1 C21 C25 121.85(18) . . . . ? C11 As1 C21 C25 -137.26(18) . . . . ? C31 As1 C21 O21 -51.36(15) . . . . ? C11 As1 C21 O21 49.52(15) . . . . ? C25 C21 O21 C23 0.0(2) . . . . ? As1 C21 O21 C23 174.41(13) . . . . ? C21 O21 C23 C24 -0.2(2) . . . . ? O21 C23 C24 C25 0.3(2) . . . . ? O21 C21 C25 C24 0.2(2) . . . . ? As1 C21 C25 C24 -173.63(14) . . . . ? C23 C24 C25 C21 -0.3(2) . . . . ? C21 As1 C31 C35 45.3(2) . . . . ? C11 As1 C31 C35 -55.8(2) . . . . ? C21 As1 C31 O32 -128.71(13) . . . . ? C11 As1 C31 O32 130.21(14) . . . . ? C35 C31 O32 C33 1.1(2) . . . . ? As1 C31 O32 C33 176.48(14) . . . . ? C31 O32 C33 C34 -0.5(2) . . . . ? O32 C33 C34 C35 -0.2(3) . . . . ? O32 C31 C35 C34 -1.2(2) . . . . ? As1 C31 C35 C34 -175.48(16) . . . . ? C33 C34 C35 C31 0.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.500 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.056 #===END data_uwe35 _database_code_depnum_ccdc_archive 'CCDC 230861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 As O5' _chemical_formula_weight 410.24 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' As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.3740(2) _cell_length_b 8.64050(10) _cell_length_c 12.6277(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.7230(10) _cell_angle_gamma 90.00 _cell_volume 1721.91(4) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 23736 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 2.003 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'NONIUS DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23736 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 26.85 _reflns_number_total 1790 _reflns_number_gt 1780 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One of the furyl groups is intersected by a twofold axis. Therefore O32 and C32 in this group had to be refined with an s.o.f. of 0.5. The hydrogen atoms H32A and H33A were refined after a riding model. ; _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^)+(0.0692P)^2^+1.8622P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1790 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0913 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 As1 As 0.0000 0.35470(3) 0.2500 0.02020(14) Uani 1 2 d S . . C11 C 0.06062(12) 0.2494(2) 0.39706(16) 0.0227(4) Uani 1 1 d . . . O12 O 0.14670(9) 0.2292(2) 0.43563(13) 0.0323(4) Uani 1 1 d . . . C13 C 0.17326(16) 0.1520(3) 0.5396(2) 0.0300(5) Uani 1 1 d . . . H13 H 0.235(2) 0.137(3) 0.576(3) 0.035(9) Uiso 1 1 d . . . C14 C 0.10800(15) 0.1233(3) 0.56689(19) 0.0263(4) Uani 1 1 d . . . H14 H 0.113(2) 0.073(4) 0.631(3) 0.045(8) Uiso 1 1 d . . . C15 C 0.03463(13) 0.1871(3) 0.47524(18) 0.0255(4) Uani 1 1 d . . . H15 H -0.018(2) 0.190(4) 0.473(3) 0.044(8) Uiso 1 1 d . . . C31 C 0.0000 0.5789(3) 0.2500 0.0260(6) Uani 1 2 d S . . O32 O -0.0619(7) 0.6692(12) 0.1706(8) 0.046(4) Uani 0.50 1 d P A 1 C32 C -0.0638(13) 0.6593(13) 0.1677(16) 0.046(6) Uani 0.50 1 d P A 2 H32A H -0.1131 0.6224 0.1043 0.055 Uiso 0.50 1 calc PR A 2 C33 C -0.0357(4) 0.8212(5) 0.2034(4) 0.092(2) Uani 1 1 d . . . H33A H -0.0654 0.9111 0.1639 0.110 Uiso 1 1 calc R A 1 C41 C 0.10462(14) 0.3584(2) 0.2135(2) 0.0228(4) Uani 1 1 d . . . O42 O 0.14696(9) 0.22167(18) 0.21579(13) 0.0268(3) Uani 1 1 d . A . C43 C 0.20455(13) 0.2550(3) 0.17049(19) 0.0303(5) Uani 1 1 d . . . H43 H 0.241(2) 0.171(4) 0.175(3) 0.041(8) Uiso 1 1 d . . . C44 C 0.20008(15) 0.4043(3) 0.1404(2) 0.0346(5) Uani 1 1 d . A . H44 H 0.234(2) 0.457(5) 0.111(3) 0.057(10) Uiso 1 1 d . . . C45 C 0.13510(14) 0.4719(3) 0.16740(19) 0.0283(5) Uani 1 1 d . A . H45 H 0.118(2) 0.573(4) 0.156(3) 0.039(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 As1 0.01984(19) 0.0180(2) 0.02083(19) 0.000 0.00656(13) 0.000 C11 0.0201(8) 0.0222(10) 0.0231(9) 0.0008(7) 0.0064(7) -0.0006(7) O12 0.0206(7) 0.0470(10) 0.0271(7) 0.0135(7) 0.0079(6) 0.0015(6) C13 0.0245(11) 0.0369(14) 0.0247(11) 0.0086(7) 0.0064(9) 0.0022(7) C14 0.0278(11) 0.0268(11) 0.0222(10) 0.0029(8) 0.0085(8) -0.0008(8) C15 0.0233(9) 0.0271(10) 0.0249(10) 0.0013(8) 0.0091(8) -0.0004(8) C31 0.0292(14) 0.0235(16) 0.0267(13) 0.000 0.0131(11) 0.000 O32 0.039(5) 0.078(9) 0.028(4) 0.022(3) 0.020(4) 0.021(4) C32 0.066(11) 0.009(5) 0.066(11) 0.014(4) 0.030(8) 0.014(4) C33 0.187(6) 0.0324(18) 0.129(4) 0.040(2) 0.138(4) 0.050(3) C41 0.0201(10) 0.0230(12) 0.0237(10) 0.0000(6) 0.0077(8) 0.0004(6) O42 0.0245(7) 0.0247(8) 0.0311(8) 0.0010(6) 0.0115(6) 0.0026(5) C43 0.0232(9) 0.0384(13) 0.0282(10) -0.0022(9) 0.0096(8) 0.0014(9) C44 0.0304(11) 0.0434(14) 0.0333(11) 0.0044(10) 0.0165(9) -0.0027(10) C45 0.0278(10) 0.0269(12) 0.0300(11) 0.0037(8) 0.0118(8) -0.0017(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag As1 C11 1.9364(19) 2 ? As1 C11 1.9364(19) . ? As1 C31 1.937(3) . ? As1 C41 2.054(2) . ? As1 C41 2.054(2) 2 ? C11 C15 1.357(3) . ? C11 O12 1.377(2) . ? O12 C13 1.370(3) . ? C13 C14 1.339(3) . ? C13 H13 0.98(3) . ? C14 C15 1.426(3) . ? C14 H14 0.90(4) . ? C15 H15 0.91(3) . ? C31 C32 1.352(17) 2 ? C31 C32 1.352(17) . ? C31 O32 1.367(10) 2 ? C31 O32 1.367(10) . ? O32 C33 1.395(12) . ? C32 C33 1.488(14) . ? C32 H32A 0.9500 . ? C33 C33 1.306(12) 2 ? C33 H33A 0.9500 . ? C41 C45 1.356(3) . ? C41 O42 1.386(2) . ? O42 C43 1.375(3) . ? C43 C44 1.337(4) . ? C43 H43 0.94(3) . ? C44 C45 1.433(3) . ? C44 H44 0.94(4) . ? C45 H45 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 As1 C11 123.94(12) 2 . ? C11 As1 C31 118.03(6) 2 . ? C11 As1 C31 118.03(6) . . ? C11 As1 C41 88.26(8) 2 . ? C11 As1 C41 92.59(8) . . ? C31 As1 C41 89.10(5) . . ? C11 As1 C41 92.59(8) 2 2 ? C11 As1 C41 88.26(8) . 2 ? C31 As1 C41 89.10(5) . 2 ? C41 As1 C41 178.20(10) . 2 ? C15 C11 O12 109.58(17) . . ? C15 C11 As1 132.16(15) . . ? O12 C11 As1 118.26(14) . . ? C13 O12 C11 106.35(17) . . ? C14 C13 O12 110.8(2) . . ? C14 C13 H13 137.1(19) . . ? O12 C13 H13 112.0(19) . . ? C13 C14 C15 106.6(2) . . ? C13 C14 H14 124(2) . . ? C15 C14 H14 129(2) . . ? C11 C15 C14 106.70(18) . . ? C11 C15 H15 127(2) . . ? C14 C15 H15 126(2) . . ? C32 C31 C32 118.2(14) 2 . ? C32 C31 O32 3.9(11) 2 2 ? C32 C31 O32 114.3(5) . 2 ? C32 C31 O32 114.3(5) 2 . ? C32 C31 O32 3.9(11) . . ? O32 C31 O32 110.4(10) 2 . ? C32 C31 As1 120.9(7) 2 . ? C32 C31 As1 120.9(7) . . ? O32 C31 As1 124.8(5) 2 . ? O32 C31 As1 124.8(5) . . ? C31 O32 C33 105.1(8) . . ? C31 C32 C33 101.0(13) . . ? C31 C32 H32A 129.5 . . ? C33 C32 H32A 129.5 . . ? C33 C33 O32 109.7(4) 2 . ? C33 C33 C32 109.9(8) 2 . ? O32 C33 C32 0.4(10) . . ? C33 C33 H33A 125.2 2 . ? O32 C33 H33A 125.2 . . ? C32 C33 H33A 124.9 . . ? C45 C41 O42 109.03(19) . . ? C45 C41 As1 130.47(16) . . ? O42 C41 As1 119.59(13) . . ? C43 O42 C41 106.55(17) . . ? C44 C43 O42 110.76(19) . . ? C44 C43 H43 136(2) . . ? O42 C43 H43 113(2) . . ? C43 C44 C45 106.5(2) . . ? C43 C44 H44 127(2) . . ? C45 C44 H44 126(2) . . ? C41 C45 C44 107.2(2) . . ? C41 C45 H45 127(2) . . ? C44 C45 H45 126(2) . . ? 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 C11 As1 C11 C15 -82.9(2) 2 . . . ? C31 As1 C11 C15 97.1(2) . . . . ? C41 As1 C11 C15 -172.5(2) . . . . ? C41 As1 C11 C15 9.1(2) 2 . . . ? C11 As1 C11 O12 97.09(16) 2 . . . ? C31 As1 C11 O12 -82.91(16) . . . . ? C41 As1 C11 O12 7.45(17) . . . . ? C41 As1 C11 O12 -170.96(17) 2 . . . ? C15 C11 O12 C13 0.3(2) . . . . ? As1 C11 O12 C13 -179.67(15) . . . . ? C11 O12 C13 C14 0.2(3) . . . . ? O12 C13 C14 C15 -0.5(3) . . . . ? O12 C11 C15 C14 -0.6(3) . . . . ? As1 C11 C15 C14 179.35(17) . . . . ? C13 C14 C15 C11 0.7(3) . . . . ? C11 As1 C31 C32 -153.8(9) 2 . . 2 ? C11 As1 C31 C32 26.2(9) . . . 2 ? C41 As1 C31 C32 -66.3(9) . . . 2 ? C41 As1 C31 C32 113.7(9) 2 . . 2 ? C11 As1 C31 C32 26.2(9) 2 . . . ? C11 As1 C31 C32 -153.8(9) . . . . ? C41 As1 C31 C32 113.7(9) . . . . ? C41 As1 C31 C32 -66.3(9) 2 . . . ? C11 As1 C31 O32 -153.5(5) 2 . . 2 ? C11 As1 C31 O32 26.5(5) . . . 2 ? C41 As1 C31 O32 -65.9(5) . . . 2 ? C41 As1 C31 O32 114.1(5) 2 . . 2 ? C11 As1 C31 O32 26.5(5) 2 . . . ? C11 As1 C31 O32 -153.5(5) . . . . ? C41 As1 C31 O32 114.1(5) . . . . ? C41 As1 C31 O32 -65.9(5) 2 . . . ? C32 C31 O32 C33 0.7(15) 2 . . . ? C32 C31 O32 C33 -175(17) . . . . ? O32 C31 O32 C33 0.4(3) 2 . . . ? As1 C31 O32 C33 -179.6(3) . . . . ? C32 C31 C32 C33 0.2(4) 2 . . . ? O32 C31 C32 C33 -0.1(16) 2 . . . ? O32 C31 C32 C33 4(16) . . . . ? As1 C31 C32 C33 -179.8(4) . . . . ? C31 O32 C33 C33 -1.0(8) . . . 2 ? C31 O32 C33 C32 129(100) . . . . ? C31 C32 C33 C33 -0.6(12) . . . 2 ? C31 C32 C33 O32 -51(100) . . . . ? C11 As1 C41 C45 97.6(2) 2 . . . ? C11 As1 C41 C45 -138.5(2) . . . . ? C31 As1 C41 C45 -20.4(2) . . . . ? C41 As1 C41 C45 -20.4(2) 2 . . . ? C11 As1 C41 O42 -70.18(17) 2 . . . ? C11 As1 C41 O42 53.73(17) . . . . ? C31 As1 C41 O42 171.75(16) . . . . ? C41 As1 C41 O42 171.75(16) 2 . . . ? C45 C41 O42 C43 0.4(2) . . . . ? As1 C41 O42 C43 170.62(15) . . . . ? C41 O42 C43 C44 0.0(2) . . . . ? O42 C43 C44 C45 -0.3(3) . . . . ? O42 C41 C45 C44 -0.6(3) . . . . ? As1 C41 C45 C44 -169.39(17) . . . . ? C43 C44 C45 C41 0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 26.85 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.416 _refine_diff_density_min -1.084 _refine_diff_density_rms 0.096