# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 186/1495 data_mald3b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H25 N2 O2 P' _chemical_formula_weight 488.50 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.2523(16) _cell_length_b 10.0350(19) _cell_length_c 16.500(5) _cell_angle_alpha 97.27(2) _cell_angle_beta 99.19(2) _cell_angle_gamma 108.358(16) _cell_volume 1257.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'blocks' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4412 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 24.97 _reflns_number_total 4412 _reflns_number_gt 2576 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.9790P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4412 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1221 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.925 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.02317(13) 0.78741(10) 0.08058(6) 0.0377(3) Uani 1 1 d . . . N1 N 0.5074(4) 1.4194(3) 0.33730(18) 0.0389(7) Uani 1 1 d . . . N2 N 0.6449(4) 1.5113(3) 0.37983(19) 0.0406(8) Uani 1 1 d . . . O1 O 0.5845(3) 1.3733(3) 0.50679(14) 0.0385(6) Uani 1 1 d . . . O2 O 0.8202(4) 1.3150(3) 0.50126(19) 0.0629(9) Uani 1 1 d . . . H3 H 0.439(4) 1.112(3) 0.517(2) 0.034(9) Uiso 1 1 d . . . H4 H 0.261(4) 0.918(4) 0.408(2) 0.040(10) Uiso 1 1 d . . . H5 H 0.130(5) 0.822(4) 0.267(2) 0.043(10) Uiso 1 1 d . . . H7 H 0.208(4) 1.079(4) 0.093(2) 0.039(10) Uiso 1 1 d . . . H8 H 0.375(5) 1.269(4) 0.197(2) 0.058(12) Uiso 1 1 d . . . H12 H 0.453(5) 1.615(4) 0.275(2) 0.053(12) Uiso 1 1 d . . . H13 H 0.509(6) 1.843(4) 0.253(3) 0.069(14) Uiso 1 1 d . . . H15 H 0.978(5) 1.965(4) 0.423(2) 0.059(12) Uiso 1 1 d . . . H16 H 0.905(5) 1.725(4) 0.435(2) 0.052(12) Uiso 1 1 d . . . H17A H 0.706(8) 2.086(6) 0.272(4) 0.11(2) Uiso 1 1 d . . . H17B H 0.904(8) 2.116(6) 0.313(4) 0.12(2) Uiso 1 1 d . . . H17C H 0.782(8) 2.137(7) 0.371(4) 0.14(3) Uiso 1 1 d . . . H19 H 0.172(6) 0.575(4) 0.081(3) 0.061(13) Uiso 1 1 d . . . H20 H 0.136(7) 0.368(6) 0.136(3) 0.10(2) Uiso 1 1 d . . . H21 H -0.071(6) 0.288(5) 0.209(3) 0.071(14) Uiso 1 1 d . . . H22 H -0.241(6) 0.427(5) 0.234(3) 0.081(16) Uiso 1 1 d . . . H23 H -0.207(5) 0.642(4) 0.184(2) 0.040(10) Uiso 1 1 d . . . H25 H -0.134(5) 0.997(4) 0.138(3) 0.059(13) Uiso 1 1 d . . . H26 H -0.397(6) 1.018(5) 0.111(3) 0.073(15) Uiso 1 1 d . . . H27 H -0.639(5) 0.832(4) 0.018(2) 0.051(11) Uiso 1 1 d . . . H28 H -0.579(6) 0.632(5) -0.040(3) 0.069(14) Uiso 1 1 d . . . H29 H -0.313(5) 0.616(4) -0.015(2) 0.049(12) Uiso 1 1 d . . . H31A H 0.797(9) 1.601(8) 0.582(4) 0.16(3) Uiso 1 1 d . . . H31B H 0.799(6) 1.525(5) 0.640(3) 0.077(17) Uiso 1 1 d . . . H31C H 0.965(9) 1.550(6) 0.605(4) 0.12(2) Uiso 1 1 d . . . C1 C 0.4619(5) 1.2841(4) 0.3609(2) 0.0347(8) Uani 1 1 d . . . C2 C 0.4903(5) 1.2605(4) 0.4410(2) 0.0349(8) Uani 1 1 d . . . C3 C 0.4161(5) 1.1264(4) 0.4600(2) 0.0386(9) Uani 1 1 d . . . C4 C 0.3172(5) 1.0124(4) 0.3982(2) 0.0385(9) Uani 1 1 d . . . C5 C 0.1818(5) 0.9142(4) 0.2499(2) 0.0345(8) Uani 1 1 d . . . C6 C 0.1511(4) 0.9305(4) 0.1684(2) 0.0362(9) Uani 1 1 d . . . C7 C 0.2293(5) 1.0672(4) 0.1503(2) 0.0407(9) Uani 1 1 d . . . C8 C 0.3260(5) 1.1811(4) 0.2112(2) 0.0419(10) Uani 1 1 d . . . C9 C 0.3574(4) 1.1669(4) 0.2951(2) 0.0333(8) Uani 1 1 d . . . C10 C 0.2857(5) 1.0304(4) 0.3148(2) 0.0356(9) Uani 1 1 d . . . C11 C 0.6739(5) 1.6505(4) 0.3595(2) 0.0368(9) Uani 1 1 d . . . C12 C 0.5552(5) 1.6840(4) 0.3041(2) 0.0417(10) Uani 1 1 d . . . C13 C 0.5936(6) 1.8231(4) 0.2912(3) 0.0444(10) Uani 1 1 d . . . C14 C 0.7482(5) 1.9286(4) 0.3329(2) 0.0420(9) Uani 1 1 d . . . C15 C 0.8631(5) 1.8931(4) 0.3876(3) 0.0454(10) Uani 1 1 d . . . C16 C 0.8289(5) 1.7548(4) 0.4009(3) 0.0434(10) Uani 1 1 d . . . C17 C 0.7876(9) 2.0807(5) 0.3207(4) 0.0620(14) Uani 1 1 d . . . C18 C -0.0121(5) 0.6279(4) 0.1266(2) 0.0355(9) Uani 1 1 d . . . C19 C 0.0910(7) 0.5468(5) 0.1122(3) 0.0543(11) Uani 1 1 d . . . C20 C 0.0708(8) 0.4227(5) 0.1428(3) 0.0680(15) Uani 1 1 d . . . C21 C -0.0536(7) 0.3781(5) 0.1883(3) 0.0609(13) Uani 1 1 d . . . C22 C -0.1557(7) 0.4571(5) 0.2037(3) 0.0577(12) Uani 1 1 d . . . C23 C -0.1369(6) 0.5814(4) 0.1736(2) 0.0456(10) Uani 1 1 d . . . C24 C -0.1914(5) 0.8057(4) 0.0672(2) 0.0361(9) Uani 1 1 d . . . C25 C -0.2241(6) 0.9232(5) 0.1021(3) 0.0506(11) Uani 1 1 d . . . C26 C -0.3896(6) 0.9331(6) 0.0844(3) 0.0605(13) Uani 1 1 d . . . C27 C -0.5230(6) 0.8256(6) 0.0316(3) 0.0621(13) Uani 1 1 d . . . C28 C -0.4927(6) 0.7076(6) -0.0039(3) 0.0603(13) Uani 1 1 d . . . C29 C -0.3288(5) 0.6979(5) 0.0131(3) 0.0476(10) Uani 1 1 d . . . C30 C 0.7562(5) 1.3961(4) 0.5300(2) 0.0411(9) Uani 1 1 d . . . C31 C 0.8465(7) 1.5281(6) 0.5932(3) 0.0589(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0380(6) 0.0362(5) 0.0372(6) 0.0067(4) 0.0070(4) 0.0109(4) N1 0.0407(19) 0.0334(16) 0.0392(18) 0.0057(14) 0.0092(15) 0.0080(14) N2 0.0390(19) 0.0392(18) 0.0463(19) 0.0080(15) 0.0128(15) 0.0154(15) O1 0.0359(15) 0.0441(15) 0.0356(14) 0.0017(11) 0.0092(11) 0.0153(12) O2 0.0464(18) 0.071(2) 0.067(2) -0.0112(16) -0.0026(15) 0.0300(16) C1 0.033(2) 0.0344(19) 0.041(2) 0.0110(16) 0.0091(16) 0.0144(16) C2 0.033(2) 0.038(2) 0.035(2) 0.0042(16) 0.0069(16) 0.0156(17) C3 0.039(2) 0.045(2) 0.034(2) 0.0119(18) 0.0061(17) 0.0162(18) C4 0.040(2) 0.035(2) 0.038(2) 0.0114(17) 0.0061(17) 0.0090(18) C5 0.033(2) 0.0325(19) 0.037(2) 0.0115(16) 0.0053(16) 0.0093(16) C6 0.031(2) 0.038(2) 0.040(2) 0.0097(16) 0.0071(16) 0.0112(16) C7 0.048(2) 0.042(2) 0.031(2) 0.0120(17) 0.0061(18) 0.0129(19) C8 0.045(2) 0.035(2) 0.042(2) 0.0121(18) 0.0061(18) 0.0095(19) C9 0.030(2) 0.0329(19) 0.037(2) 0.0083(15) 0.0063(15) 0.0102(15) C10 0.033(2) 0.038(2) 0.040(2) 0.0130(17) 0.0075(16) 0.0141(17) C11 0.037(2) 0.0353(19) 0.040(2) 0.0065(16) 0.0128(17) 0.0135(17) C12 0.036(2) 0.038(2) 0.044(2) 0.0049(18) 0.0042(18) 0.0056(18) C13 0.049(3) 0.046(2) 0.041(2) 0.0139(19) 0.0110(19) 0.018(2) C14 0.050(3) 0.038(2) 0.040(2) 0.0076(17) 0.0179(19) 0.0136(19) C15 0.040(2) 0.038(2) 0.052(3) 0.0028(19) 0.014(2) 0.0057(19) C16 0.041(2) 0.045(2) 0.042(2) 0.0059(19) 0.0095(19) 0.013(2) C17 0.080(4) 0.040(2) 0.065(4) 0.012(2) 0.021(3) 0.015(3) C18 0.039(2) 0.0330(19) 0.032(2) 0.0031(15) 0.0033(16) 0.0123(17) C19 0.068(3) 0.056(3) 0.052(3) 0.017(2) 0.025(2) 0.031(2) C20 0.103(4) 0.058(3) 0.062(3) 0.016(2) 0.022(3) 0.050(3) C21 0.096(4) 0.043(3) 0.042(3) 0.010(2) 0.009(3) 0.024(3) C22 0.067(3) 0.056(3) 0.047(3) 0.018(2) 0.016(2) 0.011(2) C23 0.050(3) 0.045(2) 0.046(2) 0.0133(19) 0.018(2) 0.017(2) C24 0.040(2) 0.036(2) 0.033(2) 0.0095(16) 0.0058(16) 0.0140(17) C25 0.049(3) 0.058(3) 0.045(3) 0.005(2) 0.006(2) 0.023(2) C26 0.060(3) 0.071(3) 0.064(3) 0.018(3) 0.015(3) 0.039(3) C27 0.041(3) 0.084(4) 0.074(3) 0.039(3) 0.017(2) 0.026(3) C28 0.044(3) 0.065(3) 0.066(3) 0.021(3) 0.003(2) 0.010(2) C29 0.045(3) 0.046(2) 0.051(3) 0.009(2) 0.007(2) 0.015(2) C30 0.040(2) 0.050(2) 0.036(2) 0.0077(18) 0.0081(17) 0.0187(19) C31 0.042(3) 0.069(3) 0.049(3) -0.014(2) 0.005(2) 0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C6 1.818(4) . ? P1 C24 1.819(4) . ? P1 C18 1.819(4) . ? N1 N2 1.246(4) . ? N1 C1 1.413(4) . ? N2 C11 1.433(4) . ? O1 C30 1.345(4) . ? O1 C2 1.389(4) . ? O2 C30 1.192(4) . ? C1 C2 1.369(5) . ? C1 C9 1.429(5) . ? C2 C3 1.391(5) . ? C3 C4 1.366(5) . ? C4 C10 1.404(5) . ? C5 C6 1.369(5) . ? C5 C10 1.415(5) . ? C6 C7 1.412(5) . ? C7 C8 1.353(5) . ? C8 C9 1.402(5) . ? C9 C10 1.413(5) . ? C11 C16 1.377(5) . ? C11 C12 1.381(5) . ? C12 C13 1.382(5) . ? C13 C14 1.381(5) . ? C14 C15 1.364(5) . ? C14 C17 1.504(6) . ? C15 C16 1.380(5) . ? C18 C19 1.377(5) . ? C18 C23 1.386(5) . ? C19 C20 1.375(6) . ? C20 C21 1.362(7) . ? C21 C22 1.358(7) . ? C22 C23 1.373(6) . ? C24 C25 1.368(5) . ? C24 C29 1.383(5) . ? C25 C26 1.388(6) . ? C26 C27 1.357(7) . ? C27 C28 1.366(7) . ? C28 C29 1.373(6) . ? C30 C31 1.475(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 P1 C24 102.80(17) . . ? C6 P1 C18 103.06(16) . . ? C24 P1 C18 101.84(17) . . ? N2 N1 C1 115.7(3) . . ? N1 N2 C11 113.2(3) . . ? C30 O1 C2 116.5(3) . . ? C2 C1 N1 125.5(3) . . ? C2 C1 C9 119.0(3) . . ? N1 C1 C9 114.9(3) . . ? C1 C2 O1 120.4(3) . . ? C1 C2 C3 121.5(3) . . ? O1 C2 C3 117.9(3) . . ? C4 C3 C2 120.6(4) . . ? C3 C4 C10 120.2(3) . . ? C6 C5 C10 121.6(3) . . ? C5 C6 C7 117.9(3) . . ? C5 C6 P1 124.8(3) . . ? C7 C6 P1 117.2(3) . . ? C8 C7 C6 121.9(4) . . ? C7 C8 C9 121.0(4) . . ? C8 C9 C10 118.4(3) . . ? C8 C9 C1 122.6(3) . . ? C10 C9 C1 119.0(3) . . ? C4 C10 C9 119.7(3) . . ? C4 C10 C5 121.2(3) . . ? C9 C10 C5 119.1(3) . . ? C16 C11 C12 120.0(4) . . ? C16 C11 N2 116.0(3) . . ? C12 C11 N2 124.0(3) . . ? C11 C12 C13 119.3(4) . . ? C14 C13 C12 121.1(4) . . ? C15 C14 C13 118.6(4) . . ? C15 C14 C17 120.3(4) . . ? C13 C14 C17 121.0(4) . . ? C14 C15 C16 121.5(4) . . ? C11 C16 C15 119.5(4) . . ? C19 C18 C23 118.1(4) . . ? C19 C18 P1 117.2(3) . . ? C23 C18 P1 124.7(3) . . ? C20 C19 C18 121.2(5) . . ? C21 C20 C19 119.8(5) . . ? C22 C21 C20 119.8(5) . . ? C21 C22 C23 121.0(5) . . ? C22 C23 C18 120.0(4) . . ? C25 C24 C29 117.6(4) . . ? C25 C24 P1 124.6(3) . . ? C29 C24 P1 117.6(3) . . ? C24 C25 C26 121.2(4) . . ? C27 C26 C25 120.3(5) . . ? C26 C27 C28 119.3(5) . . ? C27 C28 C29 120.4(5) . . ? C28 C29 C24 121.1(4) . . ? O2 C30 O1 121.4(4) . . ? O2 C30 C31 126.8(4) . . ? O1 C30 C31 111.8(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.442 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.046 data_mold4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H23 N2 O P' _chemical_formula_weight 446.46 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.0770(10) _cell_length_b 22.366(3) _cell_length_c 25.317(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4573.5(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9356 _diffrn_reflns_av_R_equivalents 0.1376 _diffrn_reflns_av_sigmaI/netI 0.1895 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3457 _reflns_number_gt 1358 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3457 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2136 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.1665 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.911 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.4259(3) 0.33042(6) 0.60222(5) 0.0356(5) Uani 1 1 d . . . N1 N 0.9632(8) 0.34628(18) 0.39704(18) 0.0329(16) Uani 1 1 d . . . N2 N 1.0448(9) 0.3456(2) 0.35250(19) 0.0330(17) Uani 1 1 d . . . O1 O 0.8031(6) 0.29529(15) 0.30795(13) 0.0338(12) Uani 1 1 d . . . C1 C 0.8144(9) 0.3215(2) 0.3978(2) 0.0288(16) Uani 1 1 d . . . C2 C 0.7336(10) 0.2955(2) 0.3526(2) 0.0325(19) Uani 1 1 d . . . C3 C 0.5727(11) 0.2693(2) 0.3595(2) 0.037(2) Uani 1 1 d . . . H3 H 0.5196 0.2513 0.3310 0.045 Uiso 1 1 calc R . . C4 C 0.4995(9) 0.2707(2) 0.4065(2) 0.0358(18) Uani 1 1 d . . . H4 H 0.3952 0.2536 0.4097 0.043 Uiso 1 1 calc R . . C5 C 0.4908(9) 0.2987(2) 0.5002(2) 0.0329(17) Uani 1 1 d . . . H5 H 0.3874 0.2807 0.5029 0.040 Uiso 1 1 calc R . . C6 C 0.5563(9) 0.3260(2) 0.54423(19) 0.0270(15) Uani 1 1 d . . . C7 C 0.7150(10) 0.3495(2) 0.5400(2) 0.0345(19) Uani 1 1 d . . . H7 H 0.7643 0.3668 0.5695 0.041 Uiso 1 1 calc R . . C8 C 0.8000(9) 0.3479(2) 0.49329(18) 0.0278(16) Uani 1 1 d . . . H8 H 0.9064 0.3637 0.4916 0.033 Uiso 1 1 calc R . . C9 C 0.7295(9) 0.3228(2) 0.44799(19) 0.0248(16) Uani 1 1 d . . . C10 C 0.5718(10) 0.2970(2) 0.45216(19) 0.0279(16) Uani 1 1 d . . . C11 C 1.2008(10) 0.3720(2) 0.3494(2) 0.0300(17) Uani 1 1 d . . . C12 C 1.2793(10) 0.3690(3) 0.3011(2) 0.037(2) Uani 1 1 d . . . H12 H 1.2301 0.3487 0.2732 0.044 Uiso 1 1 calc R . . C13 C 1.4288(10) 0.3959(2) 0.2944(2) 0.0382(19) Uani 1 1 d . . . H13 H 1.4784 0.3950 0.2613 0.046 Uiso 1 1 calc R . . C14 C 1.5088(10) 0.4243(2) 0.3355(2) 0.0298(17) Uani 1 1 d . . . C15 C 1.4294(10) 0.4254(2) 0.3833(2) 0.0343(18) Uani 1 1 d . . . H15 H 1.4805 0.4446 0.4115 0.041 Uiso 1 1 calc R . . C16 C 1.2795(10) 0.3996(2) 0.3912(2) 0.0348(19) Uani 1 1 d . . . H16 H 1.2303 0.4006 0.4244 0.042 Uiso 1 1 calc R . . C17 C 1.6743(10) 0.4526(2) 0.3278(2) 0.044(2) Uani 1 1 d . . . H17A H 1.6994 0.4776 0.3575 0.066 Uiso 1 1 calc R . . H17B H 1.6729 0.4763 0.2962 0.066 Uiso 1 1 calc R . . H17C H 1.7571 0.4220 0.3246 0.066 Uiso 1 1 calc R . . C18 C 0.3012(10) 0.3954(2) 0.5850(2) 0.0339(17) Uani 1 1 d . . . C19 C 0.1548(10) 0.4045(3) 0.6124(2) 0.046(2) Uani 1 1 d . . . H19 H 0.1264 0.3780 0.6393 0.055 Uiso 1 1 calc R . . C20 C 0.0496(10) 0.4515(3) 0.6011(3) 0.053(2) Uani 1 1 d . . . H20 H -0.0484 0.4565 0.6199 0.063 Uiso 1 1 calc R . . C21 C 0.0918(12) 0.4901(3) 0.5622(3) 0.060(3) Uani 1 1 d . . . H21 H 0.0224 0.5221 0.5545 0.072 Uiso 1 1 calc R . . C22 C 0.2334(11) 0.4829(3) 0.5342(2) 0.051(2) Uani 1 1 d . . . H22 H 0.2600 0.5096 0.5074 0.061 Uiso 1 1 calc R . . C23 C 0.3387(9) 0.4357(2) 0.5458(2) 0.0390(19) Uani 1 1 d . . . H23 H 0.4362 0.4312 0.5267 0.047 Uiso 1 1 calc R . . C24 C 0.5675(9) 0.3592(2) 0.65166(19) 0.0320(17) Uani 1 1 d . . . C25 C 0.6382(9) 0.3180(2) 0.6862(2) 0.0403(19) Uani 1 1 d . . . H25 H 0.6116 0.2777 0.6830 0.048 Uiso 1 1 calc R . . C26 C 0.7460(10) 0.3356(3) 0.7249(2) 0.055(2) Uani 1 1 d . . . H26 H 0.7954 0.3071 0.7465 0.066 Uiso 1 1 calc R . . C27 C 0.7816(10) 0.3950(3) 0.7318(2) 0.053(2) Uani 1 1 d . . . H27 H 0.8520 0.4071 0.7589 0.063 Uiso 1 1 calc R . . C28 C 0.7118(9) 0.4365(3) 0.6984(2) 0.043(2) Uani 1 1 d . . . H28 H 0.7374 0.4768 0.7024 0.052 Uiso 1 1 calc R . . C29 C 0.6049(9) 0.4190(2) 0.6594(2) 0.036(2) Uani 1 1 d . . . H29 H 0.5568 0.4477 0.6377 0.043 Uiso 1 1 calc R . . H2 H 0.992(8) 0.330(2) 0.323(2) 0.049(19) 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 0.0378(13) 0.0347(8) 0.0343(8) 0.0018(7) 0.0069(10) -0.0062(10) N1 0.037(5) 0.030(3) 0.032(3) 0.001(2) 0.001(3) -0.002(3) N2 0.037(6) 0.036(3) 0.026(3) -0.005(2) 0.000(3) 0.001(3) O1 0.030(4) 0.043(2) 0.028(2) -0.0039(17) 0.002(2) 0.000(2) C1 0.032(5) 0.024(3) 0.031(3) 0.000(3) 0.001(4) -0.001(3) C2 0.039(7) 0.025(3) 0.034(3) 0.001(3) 0.003(4) 0.008(3) C3 0.050(7) 0.029(3) 0.032(3) 0.002(2) -0.013(4) -0.001(4) C4 0.039(6) 0.033(3) 0.036(3) 0.002(3) -0.013(3) -0.003(3) C5 0.035(5) 0.027(3) 0.037(3) 0.002(3) 0.004(3) -0.004(3) C6 0.024(5) 0.024(3) 0.033(3) -0.008(2) 0.004(3) 0.005(3) C7 0.031(6) 0.039(3) 0.034(3) 0.003(3) -0.006(4) -0.004(3) C8 0.026(5) 0.032(3) 0.025(3) -0.002(2) 0.001(3) -0.005(3) C9 0.023(5) 0.019(3) 0.032(3) 0.005(2) 0.003(3) 0.004(3) C10 0.034(5) 0.024(3) 0.026(3) 0.001(2) -0.004(4) 0.001(3) C11 0.030(6) 0.028(3) 0.031(3) 0.006(3) 0.001(4) 0.002(3) C12 0.029(6) 0.047(4) 0.033(3) -0.005(3) -0.003(4) 0.007(4) C13 0.039(6) 0.045(4) 0.031(3) -0.002(3) 0.007(4) 0.001(4) C14 0.027(5) 0.027(3) 0.035(3) 0.005(3) -0.001(3) 0.004(3) C15 0.041(6) 0.031(3) 0.031(3) -0.004(2) -0.005(4) -0.003(4) C16 0.049(7) 0.033(3) 0.022(3) -0.004(3) 0.002(4) 0.004(4) C17 0.032(6) 0.047(4) 0.052(4) -0.005(3) 0.005(4) -0.003(4) C18 0.035(6) 0.039(3) 0.028(3) -0.005(3) -0.004(3) 0.000(4) C19 0.036(6) 0.053(4) 0.048(4) -0.013(3) -0.001(4) -0.004(4) C20 0.028(6) 0.067(5) 0.064(4) -0.022(4) -0.004(5) 0.006(4) C21 0.049(8) 0.069(5) 0.064(5) -0.012(4) -0.021(5) 0.016(5) C22 0.049(8) 0.058(4) 0.047(4) 0.005(3) -0.006(4) 0.011(4) C23 0.037(6) 0.044(4) 0.036(3) -0.004(3) 0.001(3) -0.002(4) C24 0.037(5) 0.037(3) 0.022(3) 0.001(2) 0.003(3) 0.001(4) C25 0.036(6) 0.038(4) 0.047(4) 0.004(3) -0.001(4) -0.003(3) C26 0.060(7) 0.061(5) 0.045(4) 0.012(3) -0.008(4) 0.011(5) C27 0.047(7) 0.070(5) 0.042(4) -0.006(3) -0.010(4) 0.007(5) C28 0.042(7) 0.050(4) 0.037(3) -0.011(3) -0.006(4) -0.010(4) C29 0.045(6) 0.032(3) 0.030(3) 0.001(2) 0.005(4) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C6 1.809(6) . ? P1 C24 1.813(6) . ? P1 C18 1.821(6) . ? N1 N2 1.306(6) . ? N1 C1 1.323(8) . ? N2 C11 1.394(8) . ? O1 C2 1.262(6) . ? C1 C2 1.440(8) . ? C1 C9 1.445(7) . ? C2 C3 1.436(9) . ? C3 C4 1.329(8) . ? C4 C10 1.422(7) . ? C5 C6 1.376(7) . ? C5 C10 1.382(7) . ? C6 C7 1.390(8) . ? C7 C8 1.368(7) . ? C8 C9 1.398(7) . ? C9 C10 1.403(8) . ? C11 C12 1.379(8) . ? C11 C16 1.379(8) . ? C12 C13 1.359(9) . ? C13 C14 1.380(8) . ? C14 C15 1.370(8) . ? C14 C17 1.491(8) . ? C15 C16 1.356(9) . ? C18 C23 1.376(7) . ? C18 C19 1.385(9) . ? C19 C20 1.382(9) . ? C20 C21 1.354(9) . ? C21 C22 1.355(9) . ? C22 C23 1.387(8) . ? C24 C29 1.385(7) . ? C24 C25 1.394(7) . ? C25 C26 1.367(8) . ? C26 C27 1.371(8) . ? C27 C28 1.377(8) . ? C28 C29 1.370(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 P1 C24 102.3(3) . . ? C6 P1 C18 99.9(3) . . ? C24 P1 C18 103.3(3) . . ? N2 N1 C1 117.7(5) . . ? N1 N2 C11 120.0(5) . . ? N1 C1 C2 124.8(6) . . ? N1 C1 C9 115.8(5) . . ? C2 C1 C9 119.4(6) . . ? O1 C2 C3 120.7(6) . . ? O1 C2 C1 120.7(7) . . ? C3 C2 C1 118.6(6) . . ? C4 C3 C2 120.1(6) . . ? C3 C4 C10 123.8(7) . . ? C6 C5 C10 123.0(6) . . ? C5 C6 C7 117.4(6) . . ? C5 C6 P1 117.3(6) . . ? C7 C6 P1 125.3(4) . . ? C8 C7 C6 121.3(6) . . ? C7 C8 C9 121.0(6) . . ? C8 C9 C10 118.3(5) . . ? C8 C9 C1 122.4(6) . . ? C10 C9 C1 119.3(5) . . ? C5 C10 C9 119.0(5) . . ? C5 C10 C4 122.3(7) . . ? C9 C10 C4 118.8(6) . . ? C12 C11 C16 119.3(7) . . ? C12 C11 N2 116.4(6) . . ? C16 C11 N2 124.3(6) . . ? C13 C12 C11 119.9(6) . . ? C12 C13 C14 121.7(6) . . ? C15 C14 C13 117.0(7) . . ? C15 C14 C17 121.9(6) . . ? C13 C14 C17 121.1(6) . . ? C16 C15 C14 122.7(6) . . ? C15 C16 C11 119.3(6) . . ? C23 C18 C19 116.9(6) . . ? C23 C18 P1 125.0(6) . . ? C19 C18 P1 118.0(5) . . ? C20 C19 C18 122.2(7) . . ? C21 C20 C19 118.8(8) . . ? C20 C21 C22 121.1(8) . . ? C21 C22 C23 119.9(7) . . ? C18 C23 C22 121.1(7) . . ? C29 C24 C25 117.4(5) . . ? C29 C24 P1 125.3(5) . . ? C25 C24 P1 117.2(4) . . ? C26 C25 C24 121.3(5) . . ? C25 C26 C27 120.3(6) . . ? C26 C27 C28 119.2(6) . . ? C29 C28 C27 120.6(6) . . ? C28 C29 C24 121.0(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.92(6) 1.75(7) 2.520(7) 139(5) . _diffrn_measured_fraction_theta_max 0.858 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.858 _refine_diff_density_max 0.215 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.054 data_mald6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H25 N2 O2 P S' _chemical_formula_weight 520.56 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.865(2) _cell_length_b 12.054(3) _cell_length_c 13.935(3) _cell_angle_alpha 107.558(17) _cell_angle_beta 94.483(18) _cell_angle_gamma 108.463(16) _cell_volume 1321.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4969 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 24.97 _reflns_number_total 4640 _reflns_number_gt 3501 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.4784P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4640 _refine_ls_number_parameters 412 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.25124(8) 0.68422(6) 0.03971(5) 0.03844(18) Uani 1 1 d . . . N1 N 0.7071(2) 0.6003(2) 0.51672(16) 0.0383(5) Uani 1 1 d . . . N2 N 0.7437(2) 0.53841(19) 0.56383(17) 0.0398(5) Uani 1 1 d . . . P1 P 0.36650(7) 0.79525(5) 0.17744(4) 0.02805(16) Uani 1 1 d . . . O1 O 0.83410(19) 0.41169(15) 0.39707(13) 0.0353(4) Uani 1 1 d . . . O2 O 0.6093(2) 0.25312(16) 0.38608(13) 0.0413(4) Uani 1 1 d . . . H3 H 0.776(3) 0.375(2) 0.2104(19) 0.035(7) Uiso 1 1 d . . . H4 H 0.631(3) 0.457(2) 0.1232(19) 0.029(6) Uiso 1 1 d . . . H5 H 0.492(3) 0.601(2) 0.1253(19) 0.030(6) Uiso 1 1 d . . . H7 H 0.438(3) 0.820(2) 0.3923(19) 0.039(7) Uiso 1 1 d . . . H8 H 0.554(3) 0.725(2) 0.476(2) 0.042(7) Uiso 1 1 d . . . H12 H 0.678(4) 0.727(3) 0.692(2) 0.061(10) Uiso 1 1 d . . . H13 H 0.709(4) 0.805(3) 0.865(2) 0.060(9) Uiso 1 1 d . . . H15 H 0.914(3) 0.552(2) 0.876(2) 0.045(7) Uiso 1 1 d . . . H16 H 0.871(3) 0.475(3) 0.693(2) 0.056(8) Uiso 1 1 d . . . H19 H 0.379(3) 1.030(2) 0.3210(18) 0.036(7) Uiso 1 1 d . . . H20 H 0.199(4) 1.094(3) 0.410(2) 0.064(10) Uiso 1 1 d . . . H21 H -0.049(4) 0.955(3) 0.407(2) 0.058(9) Uiso 1 1 d . . . H22 H -0.120(4) 0.756(3) 0.305(2) 0.059(9) Uiso 1 1 d . . . H23 H 0.053(3) 0.685(3) 0.205(2) 0.050(8) Uiso 1 1 d . . . H25 H 0.379(4) 0.994(3) 0.105(2) 0.056(8) Uiso 1 1 d . . . H26 H 0.600(4) 1.158(3) 0.089(2) 0.063(9) Uiso 1 1 d . . . H27 H 0.864(4) 1.185(3) 0.146(2) 0.063(9) Uiso 1 1 d . . . H28 H 0.921(4) 1.055(3) 0.222(2) 0.068(10) Uiso 1 1 d . . . H29 H 0.710(3) 0.897(3) 0.244(2) 0.047(8) Uiso 1 1 d . . . C1 C 0.6844(3) 0.5498(2) 0.40777(17) 0.0290(5) Uani 1 1 d . . . C2 C 0.7428(3) 0.4630(2) 0.35070(18) 0.0311(5) Uani 1 1 d . . . C3 C 0.7264(3) 0.4306(2) 0.24449(19) 0.0352(6) Uani 1 1 d . . . C4 C 0.6464(3) 0.4815(2) 0.19371(19) 0.0337(5) Uani 1 1 d . . . C5 C 0.5066(3) 0.6284(2) 0.19603(18) 0.0290(5) Uani 1 1 d . . . C6 C 0.4555(3) 0.7207(2) 0.24827(17) 0.0275(5) Uani 1 1 d . . . C7 C 0.4775(3) 0.7573(2) 0.35589(18) 0.0306(5) Uani 1 1 d . . . C8 C 0.5474(3) 0.7013(2) 0.40771(19) 0.0305(5) Uani 1 1 d . . . C9 C 0.6052(3) 0.6077(2) 0.35565(17) 0.0272(5) Uani 1 1 d . . . C10 C 0.5842(3) 0.5711(2) 0.24730(17) 0.0276(5) Uani 1 1 d . . . C11 C 0.7681(3) 0.5967(2) 0.67369(18) 0.0360(6) Uani 1 1 d . . . C12 C 0.7177(3) 0.6931(3) 0.7207(2) 0.0444(7) Uani 1 1 d . . . C13 C 0.7394(3) 0.7385(3) 0.8279(2) 0.0469(7) Uani 1 1 d . . . C14 C 0.8100(3) 0.6858(3) 0.88625(18) 0.0398(6) Uani 1 1 d . . . C15 C 0.8596(3) 0.5904(2) 0.8360(2) 0.0388(6) Uani 1 1 d . . . C16 C 0.8382(3) 0.5454(3) 0.7311(2) 0.0387(6) Uani 1 1 d . . . C17 C 0.8286(4) 0.7305(4) 1.0014(2) 0.0720(10) Uani 1 1 d . . . H17A H 0.8402 0.6663 1.0266 0.108 Uiso 1 1 calc R . . H17B H 0.7335 0.7482 1.0203 0.108 Uiso 1 1 calc R . . H17C H 0.9240 0.8056 1.0313 0.108 Uiso 1 1 calc R . . C18 C 0.2353(3) 0.8531(2) 0.25566(17) 0.0285(5) Uani 1 1 d . . . C19 C 0.2803(3) 0.9756(3) 0.3194(2) 0.0412(6) Uani 1 1 d . . . C20 C 0.1738(4) 1.0138(3) 0.3759(2) 0.0504(7) Uani 1 1 d . . . C21 C 0.0237(3) 0.9306(3) 0.3697(2) 0.0469(7) Uani 1 1 d . . . C22 C -0.0207(3) 0.8086(3) 0.3078(2) 0.0447(7) Uani 1 1 d . . . C23 C 0.0834(3) 0.7696(2) 0.2496(2) 0.0369(6) Uani 1 1 d . . . C24 C 0.5311(3) 0.9292(2) 0.17750(18) 0.0313(5) Uani 1 1 d . . . C25 C 0.4973(3) 1.0090(2) 0.1324(2) 0.0406(6) Uani 1 1 d . . . C26 C 0.6208(4) 1.1052(3) 0.1228(2) 0.0469(7) Uani 1 1 d . . . C27 C 0.7789(4) 1.1229(3) 0.1572(2) 0.0503(8) Uani 1 1 d . . . C28 C 0.8136(4) 1.0463(3) 0.2029(3) 0.0543(8) Uani 1 1 d . . . C29 C 0.6903(3) 0.9496(3) 0.2137(2) 0.0440(7) Uani 1 1 d . . . C30 C 0.7520(3) 0.3055(2) 0.41415(19) 0.0352(6) Uani 1 1 d . . . C31 C 0.8647(3) 0.2676(3) 0.4706(2) 0.0505(7) Uani 1 1 d . . . H31A H 0.8033 0.1953 0.4866 0.076 Uiso 1 1 calc R . . H31B H 0.9236 0.3357 0.5337 0.076 Uiso 1 1 calc R . . H31C H 0.9406 0.2471 0.4283 0.076 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0446(4) 0.0388(4) 0.0270(3) 0.0093(3) 0.0012(3) 0.0118(3) N1 0.0288(11) 0.0484(13) 0.0395(12) 0.0237(11) 0.0043(9) 0.0085(10) N2 0.0355(12) 0.0369(12) 0.0451(13) 0.0166(10) 0.0052(10) 0.0088(10) P1 0.0288(3) 0.0274(3) 0.0275(3) 0.0114(2) 0.0048(2) 0.0078(3) O1 0.0268(9) 0.0352(9) 0.0442(10) 0.0171(8) 0.0024(7) 0.0093(7) O2 0.0348(11) 0.0425(10) 0.0446(10) 0.0177(8) 0.0054(8) 0.0094(8) C1 0.0240(11) 0.0296(12) 0.0283(12) 0.0113(10) 0.0038(9) 0.0022(10) C2 0.0246(12) 0.0293(12) 0.0385(13) 0.0153(10) 0.0021(10) 0.0060(10) C3 0.0345(13) 0.0327(13) 0.0374(14) 0.0085(11) 0.0079(11) 0.0139(11) C4 0.0377(14) 0.0333(13) 0.0257(13) 0.0065(10) 0.0058(10) 0.0107(11) C5 0.0305(12) 0.0287(12) 0.0250(12) 0.0116(10) 0.0060(10) 0.0044(10) C6 0.0251(11) 0.0246(11) 0.0288(12) 0.0110(10) 0.0039(9) 0.0021(9) C7 0.0330(13) 0.0280(12) 0.0294(12) 0.0069(10) 0.0069(10) 0.0116(11) C8 0.0307(13) 0.0318(13) 0.0250(12) 0.0085(10) 0.0048(10) 0.0073(10) C9 0.0237(11) 0.0244(11) 0.0302(12) 0.0108(9) 0.0059(9) 0.0030(9) C10 0.0244(11) 0.0260(11) 0.0273(11) 0.0081(9) 0.0050(9) 0.0032(9) C11 0.0305(13) 0.0361(14) 0.0347(13) 0.0123(11) 0.0069(10) 0.0030(11) C12 0.0358(15) 0.0495(17) 0.0494(17) 0.0295(14) -0.0023(12) 0.0082(13) C13 0.0449(16) 0.0453(16) 0.0500(17) 0.0127(14) 0.0067(13) 0.0195(14) C14 0.0346(14) 0.0493(16) 0.0316(13) 0.0136(12) 0.0039(11) 0.0108(12) C15 0.0296(13) 0.0454(15) 0.0408(15) 0.0202(12) 0.0029(11) 0.0084(12) C16 0.0300(13) 0.0415(15) 0.0396(14) 0.0132(12) 0.0051(11) 0.0072(12) C17 0.073(2) 0.108(3) 0.0353(16) 0.0165(18) 0.0088(15) 0.041(2) C18 0.0260(12) 0.0326(12) 0.0272(12) 0.0134(10) 0.0026(9) 0.0086(10) C19 0.0288(14) 0.0395(15) 0.0432(15) 0.0066(12) 0.0081(12) 0.0035(12) C20 0.0455(17) 0.0452(17) 0.0465(17) -0.0020(14) 0.0114(13) 0.0140(14) C21 0.0340(15) 0.068(2) 0.0360(14) 0.0108(14) 0.0096(12) 0.0212(14) C22 0.0252(14) 0.0578(18) 0.0454(16) 0.0196(14) 0.0076(12) 0.0056(13) C23 0.0326(14) 0.0345(14) 0.0388(14) 0.0135(12) 0.0050(11) 0.0052(11) C24 0.0312(13) 0.0297(12) 0.0338(13) 0.0126(10) 0.0116(10) 0.0091(10) C25 0.0427(16) 0.0369(14) 0.0433(15) 0.0191(12) 0.0071(12) 0.0111(12) C26 0.0578(19) 0.0359(15) 0.0479(16) 0.0219(13) 0.0133(14) 0.0104(14) C27 0.0500(18) 0.0338(15) 0.0655(19) 0.0195(14) 0.0270(15) 0.0067(13) C28 0.0318(15) 0.0458(17) 0.085(2) 0.0252(16) 0.0149(15) 0.0106(13) C29 0.0355(15) 0.0367(15) 0.0638(18) 0.0253(14) 0.0100(13) 0.0105(12) C30 0.0350(15) 0.0369(14) 0.0341(13) 0.0125(11) 0.0087(11) 0.0127(12) C31 0.0477(17) 0.0535(17) 0.0585(18) 0.0282(15) 0.0052(14) 0.0216(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9484(10) . ? N1 N2 1.227(3) . ? N1 C1 1.426(3) . ? N2 C11 1.445(3) . ? P1 C24 1.801(2) . ? P1 C6 1.807(2) . ? P1 C18 1.811(2) . ? O1 C30 1.358(3) . ? O1 C2 1.390(3) . ? O2 C30 1.192(3) . ? C1 C2 1.378(3) . ? C1 C9 1.429(3) . ? C2 C3 1.395(3) . ? C3 C4 1.356(4) . ? C4 C10 1.408(3) . ? C5 C6 1.362(3) . ? C5 C10 1.409(3) . ? C6 C7 1.408(3) . ? C7 C8 1.361(3) . ? C8 C9 1.412(3) . ? C9 C10 1.418(3) . ? C11 C16 1.369(4) . ? C11 C12 1.377(4) . ? C12 C13 1.401(4) . ? C13 C14 1.392(4) . ? C14 C15 1.375(4) . ? C14 C17 1.508(4) . ? C15 C16 1.370(4) . ? C18 C23 1.381(3) . ? C18 C19 1.381(3) . ? C19 C20 1.377(4) . ? C20 C21 1.367(4) . ? C21 C22 1.370(4) . ? C22 C23 1.375(4) . ? C24 C29 1.379(4) . ? C24 C25 1.388(3) . ? C25 C26 1.369(4) . ? C26 C27 1.373(4) . ? C27 C28 1.362(4) . ? C28 C29 1.378(4) . ? C30 C31 1.486(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 116.0(2) . . ? N1 N2 C11 112.8(2) . . ? C24 P1 C6 105.69(11) . . ? C24 P1 C18 106.99(11) . . ? C6 P1 C18 105.29(10) . . ? C24 P1 S1 112.78(8) . . ? C6 P1 S1 113.06(8) . . ? C18 P1 S1 112.45(8) . . ? C30 O1 C2 117.01(18) . . ? C2 C1 N1 127.5(2) . . ? C2 C1 C9 118.4(2) . . ? N1 C1 C9 113.7(2) . . ? C1 C2 O1 121.5(2) . . ? C1 C2 C3 121.9(2) . . ? O1 C2 C3 116.3(2) . . ? C4 C3 C2 120.2(2) . . ? C3 C4 C10 120.8(2) . . ? C6 C5 C10 121.6(2) . . ? C5 C6 C7 119.0(2) . . ? C5 C6 P1 118.89(17) . . ? C7 C6 P1 122.05(18) . . ? C8 C7 C6 121.0(2) . . ? C7 C8 C9 121.1(2) . . ? C8 C9 C10 118.1(2) . . ? C8 C9 C1 122.7(2) . . ? C10 C9 C1 119.2(2) . . ? C4 C10 C5 121.4(2) . . ? C4 C10 C9 119.3(2) . . ? C5 C10 C9 119.2(2) . . ? C16 C11 C12 120.3(2) . . ? C16 C11 N2 115.7(2) . . ? C12 C11 N2 123.9(2) . . ? C11 C12 C13 119.3(3) . . ? C14 C13 C12 120.3(3) . . ? C15 C14 C13 118.3(2) . . ? C15 C14 C17 120.8(3) . . ? C13 C14 C17 120.9(3) . . ? C16 C15 C14 121.7(3) . . ? C11 C16 C15 120.1(3) . . ? C23 C18 C19 119.5(2) . . ? C23 C18 P1 117.51(19) . . ? C19 C18 P1 123.02(18) . . ? C20 C19 C18 120.0(3) . . ? C21 C20 C19 120.2(3) . . ? C20 C21 C22 120.0(3) . . ? C21 C22 C23 120.5(3) . . ? C22 C23 C18 119.8(3) . . ? C29 C24 C25 119.0(2) . . ? C29 C24 P1 122.07(19) . . ? C25 C24 P1 118.72(19) . . ? C26 C25 C24 120.2(3) . . ? C25 C26 C27 120.2(3) . . ? C28 C27 C26 120.2(3) . . ? C27 C28 C29 120.3(3) . . ? C28 C29 C24 120.2(3) . . ? O2 C30 O1 122.7(2) . . ? O2 C30 C31 126.9(2) . . ? O1 C30 C31 110.5(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.551 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.043