Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_is38ued _database_code_CSD 146344 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name _publ_author_address 'Schlemminger, Imre' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; 'Lutzen, Arne' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; 'Willecke, Andreas' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; 'Maison, Wolfgang' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; 'Koch, Rainer' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; 'Martens, Jurgen' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; _publ_contact_author_name 'Prof Jurgen Marten' _publ_contact_author_address ; Department of Chemistry University of Oldenburgh P O Box 2503 Oldenburg 26111 GERMANY ; _publ_contact_author_email 'JUERGEN.MARTENS@UNI-OLDENBURG.DE' _publ_section_title ; Diastereoselective Lewis Acid Mediated Hydrophosphonylation of Heterocyclic Imines: a Stereoselective Approach towards a-Aminophosphonates ; _publ_contact_author_phone '049 441 798-3837' _publ_contact_author_fax '049 441 798-3757' _publ_contact_author_email juergen.martens@uni-oldenburg.de _publ_requested_journal 'Perkin Transactions 1' _publ_requested_coeditor_name ? _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H26 N O3 P S' _chemical_formula_weight 475.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2388(5) _cell_length_b 11.8642(7) _cell_length_c 13.3079(9) _cell_angle_alpha 93.249(8) _cell_angle_beta 102.941(8) _cell_angle_gamma 109.029(7) _cell_volume 1186.55(13) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8536 _exptl_absorpt_correction_T_max 0.9614 _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Stoe IPDS' _diffrn_measurement_method 'imaging plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14439 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 26.07 _reflns_number_total 4303 _reflns_number_gt 3502 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1997)' _computing_cell_refinement 'IPDS (Stoe, 1997)' _computing_data_reduction 'XRED (Stoe, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSTEP (Stoe, 1997)' _computing_publication_material 'SHELX-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 w==1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.1155P] 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 4303 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0822 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.35002(5) 0.15928(4) 0.32567(3) 0.03867(13) Uani 1 d . . . P1 P 0.05477(5) 0.33763(4) 0.61170(3) 0.02576(11) Uani 1 d . . . O1 O 0.12505(15) 0.46332(11) 0.59725(9) 0.0378(3) Uani 1 d . . . O2 O 0.00554(14) 0.32839(11) 0.72120(8) 0.0325(3) Uani 1 d . . . O3 O 0.18934(13) 0.26511(10) 0.61731(7) 0.0263(2) Uani 1 d . . . N1 N -0.26479(16) 0.30985(13) 0.50143(9) 0.0235(3) Uani 1 d . . . H1N H -0.217(2) 0.3757(17) 0.4810(14) 0.026(4) Uiso 1 d . . . C1 C -0.42589(18) 0.23843(14) 0.42203(11) 0.0266(3) Uani 1 d . . . C2 C -0.5153(2) 0.32057(17) 0.36844(13) 0.0360(4) Uani 1 d . . . H2A H -0.4315 0.3794 0.3387 0.054 Uiso 1 calc R . . H2B H -0.5527 0.3629 0.4193 0.054 Uiso 1 calc R . . H2C H -0.6195 0.2723 0.3127 0.054 Uiso 1 calc R . . C3 C -0.5516(2) 0.14544(16) 0.46924(14) 0.0371(4) Uani 1 d . . . H3A H -0.4907 0.0937 0.5029 0.056 Uiso 1 calc R . . H3B H -0.6561 0.0962 0.4142 0.056 Uiso 1 calc R . . H3C H -0.5889 0.1865 0.5210 0.056 Uiso 1 calc R . . C4 C -0.14151(18) 0.24325(14) 0.51407(11) 0.0237(3) Uani 1 d . . . H4 H -0.190(2) 0.1708(16) 0.5443(12) 0.023(4) Uiso 1 d . . . C5 C -0.12015(18) 0.20178(15) 0.40606(11) 0.0273(3) Uani 1 d . . . C6 C -0.0666(2) 0.09001(17) 0.40771(14) 0.0407(4) Uani 1 d . . . H6A H -0.1488 0.0277 0.4356 0.061 Uiso 1 calc R . . H6B H 0.0545 0.1110 0.4519 0.061 Uiso 1 calc R . . H6C H -0.0710 0.0597 0.3367 0.061 Uiso 1 calc R . . C7 C 0.0040(2) 0.30134(17) 0.36364(13) 0.0377(4) Uani 1 d . . . H7A H -0.0336 0.3717 0.3638 0.057 Uiso 1 calc R . . H7B H 0.0001 0.2729 0.2923 0.057 Uiso 1 calc R . . H7C H 0.1255 0.3237 0.4075 0.057 Uiso 1 calc R . . C8 C -0.0119(2) 0.22269(16) 0.76631(11) 0.0322(4) Uani 1 d . . . C9 C -0.1841(2) 0.1522(2) 0.77022(13) 0.0478(5) Uani 1 d . . . H9 H -0.2823 0.1772 0.7449 0.057 Uiso 1 calc R . . C10 C -0.2067(3) 0.0475(2) 0.81095(14) 0.0578(6) Uani 1 d . . . H10 H -0.3219 -0.0001 0.8153 0.069 Uiso 1 calc R . . C11 C -0.0630(3) 0.00796(19) 0.84698(13) 0.0506(5) Uani 1 d . . . C12 C -0.0875(4) -0.1054(2) 0.88241(16) 0.0742(8) Uani 1 d . . . H12 H -0.2034 -0.1550 0.8839 0.089 Uiso 1 calc R . . C13 C 0.0501(5) -0.1448(2) 0.91416(17) 0.0819(10) Uani 1 d . . . H13 H 0.0301 -0.2207 0.9384 0.098 Uiso 1 calc R . . C14 C 0.2220(4) -0.0736(2) 0.91126(15) 0.0669(7) Uani 1 d . . . H14 H 0.3177 -0.1022 0.9326 0.080 Uiso 1 calc R . . C15 C 0.2530(3) 0.03707(18) 0.87779(13) 0.0468(5) Uani 1 d . . . H15 H 0.3701 0.0845 0.8764 0.056 Uiso 1 calc R . . C16 C 0.1122(2) 0.08126(16) 0.84532(12) 0.0374(4) Uani 1 d . . . C17 C 0.1368(2) 0.19405(15) 0.80603(11) 0.0291(3) Uani 1 d . . . C18 C 0.31372(19) 0.27532(14) 0.79967(11) 0.0257(3) Uani 1 d . . . C19 C 0.4608(2) 0.32854(15) 0.88928(11) 0.0290(3) Uani 1 d . . . C20 C 0.4463(2) 0.31288(18) 0.99210(12) 0.0387(4) Uani 1 d . . . H20 H 0.3367 0.2633 1.0029 0.046 Uiso 1 calc R . . C21 C 0.5878(3) 0.3680(2) 1.07610(14) 0.0493(5) Uani 1 d . . . H21 H 0.5758 0.3553 1.1443 0.059 Uiso 1 calc R . . C22 C 0.7502(3) 0.4431(2) 1.06267(15) 0.0529(5) Uani 1 d . . . H22 H 0.8476 0.4809 1.1215 0.063 Uiso 1 calc R . . C23 C 0.7684(2) 0.4619(2) 0.96506(15) 0.0470(5) Uani 1 d . . . H23 H 0.8783 0.5139 0.9566 0.056 Uiso 1 calc R . . C24 C 0.6251(2) 0.40485(17) 0.87550(13) 0.0344(4) Uani 1 d . . . C25 C 0.6421(2) 0.42647(17) 0.77437(13) 0.0376(4) Uani 1 d . . . H25 H 0.7538 0.4742 0.7650 0.045 Uiso 1 calc R . . C26 C 0.4997(2) 0.37956(16) 0.69015(12) 0.0319(4) Uani 1 d . . . H26 H 0.5104 0.3959 0.6224 0.038 Uiso 1 calc R . . C27 C 0.33772(19) 0.30699(14) 0.70518(11) 0.0251(3) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.02208(19) 0.0605(3) 0.0268(2) -0.01564(18) -0.00273(14) 0.0152(2) P1 0.02062(19) 0.0294(2) 0.02276(19) -0.00143(14) -0.00162(14) 0.00840(17) O1 0.0295(6) 0.0301(7) 0.0428(7) 0.0014(5) -0.0055(5) 0.0063(5) O2 0.0279(5) 0.0446(7) 0.0237(5) -0.0052(5) 0.0010(4) 0.0162(5) O3 0.0220(5) 0.0356(6) 0.0193(5) -0.0004(4) 0.0004(4) 0.0111(5) N1 0.0174(6) 0.0264(8) 0.0235(6) 0.0001(5) 0.0027(5) 0.0058(6) C1 0.0164(6) 0.0329(9) 0.0256(7) -0.0047(6) 0.0028(5) 0.0055(7) C2 0.0228(7) 0.0463(11) 0.0358(9) 0.0010(7) -0.0004(6) 0.0139(8) C3 0.0258(8) 0.0344(10) 0.0450(10) -0.0034(7) 0.0107(7) 0.0027(8) C4 0.0195(6) 0.0270(9) 0.0215(7) -0.0007(6) 0.0015(5) 0.0072(7) C5 0.0192(7) 0.0364(10) 0.0236(7) -0.0046(6) 0.0005(5) 0.0107(7) C6 0.0378(9) 0.0426(11) 0.0396(9) -0.0097(7) -0.0006(7) 0.0209(9) C7 0.0300(8) 0.0505(12) 0.0328(8) 0.0006(7) 0.0122(7) 0.0125(8) C8 0.0253(7) 0.0440(11) 0.0202(7) -0.0062(6) 0.0044(6) 0.0054(8) C9 0.0273(8) 0.0743(16) 0.0260(8) -0.0089(9) 0.0060(7) 0.0001(9) C10 0.0396(10) 0.0756(17) 0.0274(9) -0.0116(9) 0.0109(8) -0.0189(11) C11 0.0637(12) 0.0422(12) 0.0214(8) -0.0079(7) 0.0147(8) -0.0141(10) C12 0.114(2) 0.0421(14) 0.0300(10) -0.0057(9) 0.0252(12) -0.0239(15) C13 0.159(3) 0.0312(13) 0.0333(11) 0.0031(9) 0.0287(15) 0.0021(18) C14 0.129(2) 0.0419(13) 0.0318(10) 0.0057(9) 0.0176(12) 0.0346(16) C15 0.0749(14) 0.0395(11) 0.0262(8) 0.0042(7) 0.0113(8) 0.0212(11) C16 0.0509(10) 0.0325(10) 0.0190(7) -0.0030(6) 0.0094(7) 0.0024(9) C17 0.0293(8) 0.0328(9) 0.0192(7) -0.0022(6) 0.0058(6) 0.0040(7) C18 0.0238(7) 0.0291(9) 0.0237(7) 0.0016(6) 0.0030(6) 0.0110(7) C19 0.0263(7) 0.0346(9) 0.0248(7) 0.0014(6) 0.0010(6) 0.0130(7) C20 0.0379(9) 0.0502(12) 0.0252(8) 0.0026(7) 0.0038(7) 0.0149(9) C21 0.0484(11) 0.0702(15) 0.0245(8) -0.0012(8) -0.0020(7) 0.0233(11) C22 0.0368(10) 0.0740(16) 0.0346(10) -0.0099(9) -0.0124(7) 0.0191(11) C23 0.0247(8) 0.0613(14) 0.0448(11) -0.0017(9) -0.0051(7) 0.0127(9) C24 0.0217(7) 0.0449(11) 0.0334(8) 0.0009(7) -0.0005(6) 0.0132(8) C25 0.0205(7) 0.0490(12) 0.0406(9) 0.0077(8) 0.0068(6) 0.0091(8) C26 0.0258(7) 0.0438(11) 0.0282(8) 0.0088(7) 0.0078(6) 0.0134(8) C27 0.0209(7) 0.0308(9) 0.0220(7) 0.0008(6) 0.0006(5) 0.0107(7) _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 C5 1.8422(14) . ? S1 C1 1.8767(14) . ? P1 O1 1.4544(13) . ? P1 O2 1.5981(11) . ? P1 O3 1.6023(10) . ? P1 C4 1.8084(15) . ? O2 C8 1.400(2) . ? O3 C27 1.4165(17) . ? N1 C1 1.4605(18) . ? N1 C4 1.4650(17) . ? C1 C3 1.520(2) . ? C1 C2 1.521(2) . ? C4 C5 1.5584(19) . ? C5 C7 1.519(2) . ? C5 C6 1.528(2) . ? C8 C17 1.378(2) . ? C8 C9 1.407(2) . ? C9 C10 1.357(3) . ? C10 C11 1.409(3) . ? C11 C12 1.417(3) . ? C11 C16 1.428(3) . ? C12 C13 1.355(4) . ? C13 C14 1.403(4) . ? C14 C15 1.374(3) . ? C15 C16 1.415(3) . ? C16 C17 1.434(2) . ? C17 C18 1.486(2) . ? C18 C27 1.370(2) . ? C18 C19 1.434(2) . ? C19 C20 1.417(2) . ? C19 C24 1.420(2) . ? C20 C21 1.369(2) . ? C21 C22 1.401(3) . ? C22 C23 1.363(3) . ? C23 C24 1.425(2) . ? C24 C25 1.413(2) . ? C25 C26 1.362(2) . ? C26 C27 1.397(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 C5 S1 C1 95.03(6) . . ? O1 P1 O2 109.91(7) . . ? O1 P1 O3 115.68(6) . . ? O2 P1 O3 103.65(5) . . ? O1 P1 C4 116.23(7) . . ? O2 P1 C4 106.61(7) . . ? O3 P1 C4 103.66(6) . . ? C8 O2 P1 119.70(9) . . ? C27 O3 P1 113.99(9) . . ? C1 N1 C4 108.15(11) . . ? N1 C1 C3 110.79(13) . . ? N1 C1 C2 110.06(13) . . ? C3 C1 C2 111.23(13) . . ? N1 C1 S1 105.58(9) . . ? C3 C1 S1 109.27(11) . . ? C2 C1 S1 109.75(10) . . ? N1 C4 C5 110.36(11) . . ? N1 C4 P1 105.61(10) . . ? C5 C4 P1 118.43(10) . . ? C7 C5 C6 111.44(13) . . ? C7 C5 C4 113.37(13) . . ? C6 C5 C4 111.67(13) . . ? C7 C5 S1 110.29(11) . . ? C6 C5 S1 108.69(11) . . ? C4 C5 S1 100.83(9) . . ? C17 C8 O2 119.63(14) . . ? C17 C8 C9 123.49(18) . . ? O2 C8 C9 116.87(15) . . ? C10 C9 C8 118.47(19) . . ? C9 C10 C11 121.45(17) . . ? C10 C11 C12 121.8(2) . . ? C10 C11 C16 119.87(19) . . ? C12 C11 C16 118.3(2) . . ? C13 C12 C11 121.7(2) . . ? C12 C13 C14 120.1(2) . . ? C15 C14 C13 120.5(3) . . ? C14 C15 C16 120.7(2) . . ? C15 C16 C11 118.69(18) . . ? C15 C16 C17 122.71(16) . . ? C11 C16 C17 118.53(17) . . ? C8 C17 C16 117.96(15) . . ? C8 C17 C18 119.55(14) . . ? C16 C17 C18 122.32(14) . . ? C27 C18 C19 117.38(14) . . ? C27 C18 C17 119.43(13) . . ? C19 C18 C17 123.10(13) . . ? C20 C19 C24 118.33(14) . . ? C20 C19 C18 122.50(15) . . ? C24 C19 C18 119.09(14) . . ? C21 C20 C19 120.99(18) . . ? C20 C21 C22 120.77(18) . . ? C23 C22 C21 119.94(16) . . ? C22 C23 C24 121.05(18) . . ? C25 C24 C19 119.87(14) . . ? C25 C24 C23 121.18(17) . . ? C19 C24 C23 118.91(16) . . ? C26 C25 C24 120.62(15) . . ? C25 C26 C27 118.83(14) . . ? C18 C27 C26 123.98(13) . . ? C18 C27 O3 118.32(13) . . ? C26 C27 O3 117.69(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 O1 P1 O2 C8 -160.44(10) . . . . ? O3 P1 O2 C8 -36.24(12) . . . . ? C4 P1 O2 C8 72.79(12) . . . . ? O1 P1 O3 C27 65.40(11) . . . . ? O2 P1 O3 C27 -54.96(11) . . . . ? C4 P1 O3 C27 -166.17(10) . . . . ? C4 N1 C1 C3 84.05(14) . . . . ? C4 N1 C1 C2 -152.52(12) . . . . ? C4 N1 C1 S1 -34.14(14) . . . . ? C5 S1 C1 N1 9.61(11) . . . . ? C5 S1 C1 C3 -109.58(11) . . . . ? C5 S1 C1 C2 128.20(12) . . . . ? C1 N1 C4 C5 50.10(16) . . . . ? C1 N1 C4 P1 179.23(10) . . . . ? O1 P1 C4 N1 -48.42(12) . . . . ? O2 P1 C4 N1 74.47(11) . . . . ? O3 P1 C4 N1 -176.50(9) . . . . ? O1 P1 C4 C5 75.79(13) . . . . ? O2 P1 C4 C5 -161.32(11) . . . . ? O3 P1 C4 C5 -52.30(13) . . . . ? N1 C4 C5 C7 78.83(15) . . . . ? P1 C4 C5 C7 -43.00(16) . . . . ? N1 C4 C5 C6 -154.30(13) . . . . ? P1 C4 C5 C6 83.87(16) . . . . ? N1 C4 C5 S1 -39.02(14) . . . . ? P1 C4 C5 S1 -160.85(8) . . . . ? C1 S1 C5 C7 -104.53(11) . . . . ? C1 S1 C5 C6 133.03(12) . . . . ? C1 S1 C5 C4 15.55(11) . . . . ? P1 O2 C8 C17 70.66(16) . . . . ? P1 O2 C8 C9 -110.68(14) . . . . ? C17 C8 C9 C10 -3.1(2) . . . . ? O2 C8 C9 C10 178.31(14) . . . . ? C8 C9 C10 C11 -1.2(3) . . . . ? C9 C10 C11 C12 -175.21(18) . . . . ? C9 C10 C11 C16 2.8(3) . . . . ? C10 C11 C12 C13 178.04(19) . . . . ? C16 C11 C12 C13 0.0(3) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? C14 C15 C16 C11 -0.7(2) . . . . ? C14 C15 C16 C17 -177.54(16) . . . . ? C10 C11 C16 C15 -177.34(15) . . . . ? C12 C11 C16 C15 0.8(2) . . . . ? C10 C11 C16 C17 -0.3(2) . . . . ? C12 C11 C16 C17 177.79(15) . . . . ? O2 C8 C17 C16 -175.95(12) . . . . ? C9 C8 C17 C16 5.5(2) . . . . ? O2 C8 C17 C18 -0.5(2) . . . . ? C9 C8 C17 C18 -179.06(14) . . . . ? C15 C16 C17 C8 173.25(15) . . . . ? C11 C16 C17 C8 -3.6(2) . . . . ? C15 C16 C17 C18 -2.1(2) . . . . ? C11 C16 C17 C18 -178.96(13) . . . . ? C8 C17 C18 C27 -53.6(2) . . . . ? C16 C17 C18 C27 121.69(16) . . . . ? C8 C17 C18 C19 122.95(16) . . . . ? C16 C17 C18 C19 -61.8(2) . . . . ? C27 C18 C19 C20 173.14(15) . . . . ? C17 C18 C19 C20 -3.4(2) . . . . ? C27 C18 C19 C24 -3.6(2) . . . . ? C17 C18 C19 C24 179.81(14) . . . . ? C24 C19 C20 C21 -1.2(3) . . . . ? C18 C19 C20 C21 -177.94(17) . . . . ? C19 C20 C21 C22 1.0(3) . . . . ? C20 C21 C22 C23 0.0(3) . . . . ? C21 C22 C23 C24 -0.9(3) . . . . ? C20 C19 C24 C25 -177.41(15) . . . . ? C18 C19 C24 C25 -0.5(2) . . . . ? C20 C19 C24 C23 0.3(2) . . . . ? C18 C19 C24 C23 177.16(15) . . . . ? C22 C23 C24 C25 178.42(18) . . . . ? C22 C23 C24 C19 0.8(3) . . . . ? C19 C24 C25 C26 3.2(3) . . . . ? C23 C24 C25 C26 -174.38(17) . . . . ? C24 C25 C26 C27 -1.7(3) . . . . ? C19 C18 C27 C26 5.4(2) . . . . ? C17 C18 C27 C26 -177.88(14) . . . . ? C19 C18 C27 O3 -173.79(12) . . . . ? C17 C18 C27 O3 2.9(2) . . . . ? C25 C26 C27 C18 -2.8(2) . . . . ? C25 C26 C27 O3 176.40(14) . . . . ? P1 O3 C27 C18 77.20(15) . . . . ? P1 O3 C27 C26 -102.05(13) . . . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 0.263 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.041 #=========================================================================== #========================================================================== #===== _eof # End of Crystallographic Information File data_is1984 _database_code_CSD 146351 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name _publ_author_address 'Schlemminger, Imre' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; 'Lutzen, Arne' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; 'Willecke, Andreas' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; 'Maison, Wolfgang' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; 'Koch, Rainer' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; 'Martens, Jurgen' ; Fachbereich Chemie Universitat Oldenburg Carl von Ossietzky Strasse 9-11 26129 Oldenburg Bundesrepublik Deutschland ; _publ_contact_author_name 'Prof Jurgen Marten' _publ_contact_author_address ; Department of Chemistry University of Oldenburgh P O Box 2503 Oldenburg 26111 GERMANY ; _publ_contact_author_email 'JUERGEN.MARTENS@UNI-OLDENBURG.DE' _publ_section_title ; Diastereoselective Lewis Acid Mediated Hydrophosphonylation of Heterocyclic Imines: a Stereoselective Approach towards a-Aminophosphonates ; _publ_contact_author_phone '049 441 798-3837' _publ_contact_author_fax '049 441 798-3757' _publ_contact_author_email juergen.martens@uni-oldenburg.de _publ_requested_journal 'Perkin Transactions 1' _publ_requested_coeditor_name ? _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H36 N O8 P S' _chemical_formula_weight 493.54 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' '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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.8581(6) _cell_length_b 10.6386(4) _cell_length_c 24.4742(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2566.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description quader _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8736 _exptl_absorpt_correction_T_max 0.9617 _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Stoe IPDS' _diffrn_measurement_method 'imaging plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18617 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 26.02 _reflns_number_total 4699 _reflns_number_gt 3915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1997)' _computing_cell_refinement 'IPDS (Stoe,1997)' _computing_data_reduction 'XRED (Stoe, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSTEP (Stoe, 1997)' _computing_publication_material 'SHELX-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 w==1/[\s^2^(Fo^2^)+(0.0382P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(6) _refine_ls_number_reflns 4699 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0672 _refine_ls_wR_factor_gt 0.0634 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.84814(5) 0.14775(6) 0.23591(2) 0.02999(13) Uani 1 d . . . P1 P 0.52368(5) -0.12118(5) 0.19879(2) 0.02327(12) Uani 1 d . . . O1 O 0.66628(12) 0.24831(14) 0.09465(5) 0.0233(3) Uani 1 d . . . O2 O 0.85324(17) 0.42671(15) 0.15369(6) 0.0360(4) Uani 1 d . . . O3 O 0.84144(17) 0.46954(15) 0.06264(6) 0.0363(4) Uani 1 d . . . O4 O 0.91751(13) 0.14841(16) 0.02644(5) 0.0280(3) Uani 1 d . . . O5 O 0.69335(14) 0.10090(15) 0.02568(6) 0.0333(4) Uani 1 d . . . O6 O 0.48924(13) -0.13657(15) 0.13628(5) 0.0292(3) Uani 1 d . . . O7 O 0.39369(13) -0.06164(15) 0.22569(6) 0.0285(4) Uani 1 d . . . O8 O 0.56111(14) -0.24028(16) 0.22454(6) 0.0344(4) Uani 1 d . . . N1 N 0.60316(15) 0.11996(17) 0.19158(6) 0.0220(3) Uani 1 d . . . H1N H 0.5165 0.1386 0.1889 0.026 Uiso 1 calc R . . C1 C 0.77447(18) 0.2158(2) 0.13130(7) 0.0200(4) Uani 1 d . . . H1 H 0.8111 0.1314 0.1209 0.024 Uiso 1 calc R . . C2 C 0.88733(19) 0.3129(2) 0.12678(8) 0.0221(4) Uani 1 d . . . H2 H 0.9732 0.2780 0.1424 0.027 Uiso 1 calc R . . C3 C 0.91079(19) 0.3535(2) 0.06734(8) 0.0257(4) Uani 1 d . . . H3 H 1.0098 0.3646 0.0599 0.031 Uiso 1 calc R . . C4 C 0.8476(2) 0.2658(2) 0.02597(8) 0.0263(5) Uani 1 d . . . H4 H 0.8522 0.3041 -0.0113 0.032 Uiso 1 calc R . . C5 C 0.7008(2) 0.2301(2) 0.03968(7) 0.0251(5) Uani 1 d . . . H5 H 0.6374 0.2792 0.0160 0.030 Uiso 1 calc R . . C6 C 0.8320(2) 0.5251(2) 0.11532(9) 0.0351(5) Uani 1 d . . . C7 C 0.6914(3) 0.5771(4) 0.12216(14) 0.0730(11) Uani 1 d . . . H7A H 0.6832 0.6163 0.1583 0.110 Uiso 1 calc R . . H7B H 0.6251 0.5088 0.1189 0.110 Uiso 1 calc R . . H7C H 0.6741 0.6401 0.0938 0.110 Uiso 1 calc R . . C8 C 0.9428(3) 0.6212(3) 0.12301(12) 0.0601(8) Uani 1 d . . . H8A H 0.9347 0.6590 0.1594 0.090 Uiso 1 calc R . . H8B H 0.9343 0.6867 0.0951 0.090 Uiso 1 calc R . . H8C H 1.0314 0.5802 0.1196 0.090 Uiso 1 calc R . . C9 C 0.8232(2) 0.0562(2) 0.00795(8) 0.0311(5) Uani 1 d . . . C10 C 0.8246(3) 0.0466(3) -0.05394(9) 0.0481(7) Uani 1 d . . . H10A H 0.7592 -0.0174 -0.0657 0.072 Uiso 1 calc R . . H10B H 0.9156 0.0229 -0.0663 0.072 Uiso 1 calc R . . H10C H 0.7998 0.1280 -0.0698 0.072 Uiso 1 calc R . . C11 C 0.8549(3) -0.0670(3) 0.03523(10) 0.0477(6) Uani 1 d . . . H11A H 0.7907 -0.1311 0.0227 0.071 Uiso 1 calc R . . H11B H 0.8472 -0.0573 0.0749 0.071 Uiso 1 calc R . . H11C H 0.9474 -0.0927 0.0259 0.071 Uiso 1 calc R . . C12 C 0.7140(2) 0.2079(2) 0.18871(7) 0.0232(4) Uani 1 d . . . H12 H 0.6831 0.2930 0.2008 0.028 Uiso 1 calc R . . C13 C 0.65944(19) -0.00534(18) 0.19971(7) 0.0207(4) Uani 1 d . . . H13 H 0.7160 -0.0229 0.1667 0.025 Uiso 1 calc R . . C14 C 0.7591(2) -0.0029(2) 0.24841(8) 0.0269(5) Uani 1 d . . . C15 C 0.8607(2) -0.1098(2) 0.24659(10) 0.0412(6) Uani 1 d . . . H15A H 0.9069 -0.1099 0.2111 0.062 Uiso 1 calc R . . H15B H 0.8132 -0.1899 0.2516 0.062 Uiso 1 calc R . . H15C H 0.9276 -0.0989 0.2758 0.062 Uiso 1 calc R . . C16 C 0.6852(2) 0.0015(2) 0.30327(8) 0.0382(6) Uani 1 d . . . H16A H 0.6207 0.0715 0.3033 0.057 Uiso 1 calc R . . H16B H 0.7513 0.0133 0.3327 0.057 Uiso 1 calc R . . H16C H 0.6363 -0.0776 0.3090 0.057 Uiso 1 calc R . . C17 C 0.4092(2) -0.0389(2) 0.10927(9) 0.0351(6) Uani 1 d . . . H17A H 0.3946 -0.0618 0.0705 0.042 Uiso 1 calc R . . H17B H 0.4591 0.0419 0.1104 0.042 Uiso 1 calc R . . C18 C 0.2732(2) -0.0242(2) 0.13779(10) 0.0348(5) Uani 1 d . . . C19 C 0.2959(2) 0.0169(2) 0.19660(10) 0.0351(5) Uani 1 d . . . H19A H 0.3285 0.1049 0.1968 0.042 Uiso 1 calc R . . H19B H 0.2082 0.0146 0.2163 0.042 Uiso 1 calc R . . C20 C 0.1932(3) 0.0810(3) 0.10919(13) 0.0590(8) Uani 1 d . . . H20A H 0.1759 0.0571 0.0711 0.089 Uiso 1 calc R . . H20B H 0.2461 0.1590 0.1101 0.089 Uiso 1 calc R . . H20C H 0.1067 0.0939 0.1281 0.089 Uiso 1 calc R . . C21 C 0.1927(2) -0.1465(3) 0.13482(11) 0.0460(6) Uani 1 d . . . H21A H 0.1795 -0.1701 0.0965 0.069 Uiso 1 calc R . . H21B H 0.1042 -0.1348 0.1523 0.069 Uiso 1 calc R . . H21C H 0.2427 -0.2132 0.1537 0.069 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0330(3) 0.0348(4) 0.0222(2) 0.0024(2) -0.0060(2) -0.0095(2) P1 0.0243(2) 0.0194(3) 0.0261(2) 0.0021(2) 0.0034(2) -0.0015(2) O1 0.0193(6) 0.0297(9) 0.0208(6) 0.0020(6) -0.0016(5) 0.0009(6) O2 0.0536(10) 0.0206(10) 0.0339(8) -0.0033(6) 0.0066(7) -0.0073(7) O3 0.0507(9) 0.0230(10) 0.0354(8) 0.0066(6) -0.0001(8) 0.0010(8) O4 0.0269(7) 0.0307(10) 0.0265(7) -0.0027(6) 0.0012(6) 0.0023(6) O5 0.0305(8) 0.0356(11) 0.0338(8) -0.0100(7) 0.0005(6) -0.0049(6) O6 0.0294(7) 0.0290(10) 0.0292(7) -0.0037(6) -0.0005(6) -0.0017(7) O7 0.0258(7) 0.0293(10) 0.0303(8) 0.0052(6) 0.0065(6) 0.0006(6) O8 0.0356(8) 0.0239(10) 0.0436(9) 0.0078(7) 0.0034(6) -0.0013(7) N1 0.0196(7) 0.0207(10) 0.0256(8) 0.0011(7) 0.0020(6) 0.0009(7) C1 0.0202(9) 0.0200(12) 0.0199(9) 0.0011(8) -0.0011(7) 0.0000(8) C2 0.0226(10) 0.0177(12) 0.0261(10) -0.0003(8) -0.0010(8) -0.0015(8) C3 0.0247(10) 0.0230(14) 0.0293(10) 0.0045(9) 0.0043(8) -0.0019(9) C4 0.0301(10) 0.0276(14) 0.0213(9) 0.0055(8) 0.0040(8) 0.0025(10) C5 0.0275(10) 0.0295(14) 0.0183(9) 0.0005(8) -0.0035(8) 0.0013(9) C6 0.0366(12) 0.0231(14) 0.0455(13) -0.0027(10) -0.0053(10) -0.0014(10) C7 0.0551(18) 0.081(3) 0.082(2) -0.0271(18) -0.0101(16) 0.0343(17) C8 0.081(2) 0.0312(19) 0.0680(18) 0.0116(14) -0.0222(15) -0.0256(15) C9 0.0350(12) 0.0331(15) 0.0253(10) -0.0067(9) -0.0003(9) 0.0025(9) C10 0.0589(16) 0.060(2) 0.0258(11) -0.0109(11) -0.0013(11) 0.0068(14) C11 0.0636(17) 0.0334(17) 0.0460(14) -0.0028(11) -0.0068(13) 0.0037(13) C12 0.0287(10) 0.0196(13) 0.0213(9) -0.0006(8) 0.0024(8) -0.0026(8) C13 0.0251(9) 0.0199(12) 0.0172(8) 0.0020(8) 0.0032(8) 0.0019(8) C14 0.0303(10) 0.0281(14) 0.0223(10) 0.0040(8) -0.0019(8) -0.0034(9) C15 0.0365(12) 0.0363(17) 0.0507(14) 0.0099(11) -0.0083(10) 0.0047(11) C16 0.0459(13) 0.0471(17) 0.0215(10) 0.0051(10) 0.0018(10) -0.0083(11) C17 0.0373(12) 0.0350(16) 0.0328(12) 0.0074(10) -0.0042(10) -0.0092(11) C18 0.0270(11) 0.0309(15) 0.0465(13) 0.0127(11) -0.0052(10) -0.0024(10) C19 0.0248(10) 0.0299(15) 0.0507(13) 0.0060(11) 0.0019(10) 0.0015(9) C20 0.0478(15) 0.050(2) 0.079(2) 0.0269(15) -0.0144(14) 0.0039(13) C21 0.0346(12) 0.0490(19) 0.0544(14) 0.0091(13) -0.0075(11) -0.0154(12) _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 C14 1.852(2) . ? S1 C12 1.869(2) . ? P1 O8 1.4625(17) . ? P1 O7 1.5738(14) . ? P1 O6 1.5755(14) . ? P1 C13 1.819(2) . ? O1 C5 1.401(2) . ? O1 C1 1.436(2) . ? O2 C2 1.419(3) . ? O2 C6 1.422(3) . ? O3 C3 1.416(3) . ? O3 C6 1.421(3) . ? O4 C9 1.426(3) . ? O4 C4 1.427(3) . ? O5 C5 1.419(3) . ? O5 C9 1.433(3) . ? O6 C17 1.463(3) . ? O7 C19 1.461(3) . ? N1 C12 1.441(3) . ? N1 C13 1.458(3) . ? C1 C2 1.522(3) . ? C1 C12 1.528(3) . ? C2 C3 1.535(3) . ? C3 C4 1.511(3) . ? C4 C5 1.534(3) . ? C6 C7 1.501(4) . ? C6 C8 1.508(4) . ? C9 C11 1.503(4) . ? C9 C10 1.518(3) . ? C13 C14 1.545(3) . ? C14 C15 1.517(3) . ? C14 C16 1.528(3) . ? C17 C18 1.520(3) . ? C18 C19 1.521(3) . ? C18 C21 1.525(4) . ? C18 C20 1.538(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 C14 S1 C12 93.62(9) . . ? O8 P1 O7 111.95(9) . . ? O8 P1 O6 112.51(9) . . ? O7 P1 O6 105.82(8) . . ? O8 P1 C13 113.32(9) . . ? O7 P1 C13 108.73(9) . . ? O6 P1 C13 103.94(8) . . ? C5 O1 C1 112.71(14) . . ? C2 O2 C6 110.89(16) . . ? C3 O3 C6 108.69(16) . . ? C9 O4 C4 106.58(16) . . ? C5 O5 C9 110.41(16) . . ? C17 O6 P1 118.76(14) . . ? C19 O7 P1 124.29(13) . . ? C12 N1 C13 108.19(15) . . ? O1 C1 C2 109.50(15) . . ? O1 C1 C12 107.31(14) . . ? C2 C1 C12 112.88(16) . . ? O2 C2 C1 111.86(16) . . ? O2 C2 C3 103.62(16) . . ? C1 C2 C3 111.71(16) . . ? O3 C3 C4 106.54(16) . . ? O3 C3 C2 104.46(16) . . ? C4 C3 C2 113.55(17) . . ? O4 C4 C3 109.63(16) . . ? O4 C4 C5 103.70(17) . . ? C3 C4 C5 113.28(16) . . ? O1 C5 O5 110.69(17) . . ? O1 C5 C4 113.88(15) . . ? O5 C5 C4 103.65(17) . . ? O3 C6 O2 106.46(18) . . ? O3 C6 C7 108.4(2) . . ? O2 C6 C7 109.5(2) . . ? O3 C6 C8 110.3(2) . . ? O2 C6 C8 108.04(19) . . ? C7 C6 C8 113.9(3) . . ? O4 C9 O5 104.95(16) . . ? O4 C9 C11 108.87(18) . . ? O5 C9 C11 109.91(19) . . ? O4 C9 C10 110.93(19) . . ? O5 C9 C10 109.41(18) . . ? C11 C9 C10 112.5(2) . . ? N1 C12 C1 112.10(15) . . ? N1 C12 S1 106.49(13) . . ? C1 C12 S1 108.12(13) . . ? N1 C13 C14 109.37(15) . . ? N1 C13 P1 109.74(13) . . ? C14 C13 P1 119.27(13) . . ? C15 C14 C16 111.29(18) . . ? C15 C14 C13 112.60(18) . . ? C16 C14 C13 112.06(16) . . ? C15 C14 S1 109.35(15) . . ? C16 C14 S1 110.17(16) . . ? C13 C14 S1 100.88(13) . . ? O6 C17 C18 109.94(17) . . ? C17 C18 C19 109.50(17) . . ? C17 C18 C21 110.5(2) . . ? C19 C18 C21 111.55(19) . . ? C17 C18 C20 108.5(2) . . ? C19 C18 C20 107.3(2) . . ? C21 C18 C20 109.4(2) . . ? O7 C19 C18 113.19(19) . . ? 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 O8 P1 O6 C17 160.27(13) . . . . ? O7 P1 O6 C17 37.72(16) . . . . ? C13 P1 O6 C17 -76.75(15) . . . . ? O8 P1 O7 C19 -149.69(17) . . . . ? O6 P1 O7 C19 -26.79(19) . . . . ? C13 P1 O7 C19 84.34(18) . . . . ? C5 O1 C1 C2 71.1(2) . . . . ? C5 O1 C1 C12 -166.10(16) . . . . ? C6 O2 C2 C1 -110.74(18) . . . . ? C6 O2 C2 C3 9.7(2) . . . . ? O1 C1 C2 O2 75.70(19) . . . . ? C12 C1 C2 O2 -43.8(2) . . . . ? O1 C1 C2 C3 -39.9(2) . . . . ? C12 C1 C2 C3 -159.42(17) . . . . ? C6 O3 C3 C4 145.28(17) . . . . ? C6 O3 C3 C2 24.8(2) . . . . ? O2 C2 C3 O3 -20.8(2) . . . . ? C1 C2 C3 O3 99.76(19) . . . . ? O2 C2 C3 C4 -136.49(17) . . . . ? C1 C2 C3 C4 -15.9(2) . . . . ? C9 O4 C4 C3 153.88(16) . . . . ? C9 O4 C4 C5 32.62(18) . . . . ? O3 C3 C4 O4 177.01(14) . . . . ? C2 C3 C4 O4 -68.6(2) . . . . ? O3 C3 C4 C5 -67.7(2) . . . . ? C2 C3 C4 C5 46.7(2) . . . . ? C1 O1 C5 O5 77.9(2) . . . . ? C1 O1 C5 C4 -38.4(2) . . . . ? C9 O5 C5 O1 -119.38(17) . . . . ? C9 O5 C5 C4 3.10(19) . . . . ? O4 C4 C5 O1 98.71(19) . . . . ? C3 C4 C5 O1 -20.1(3) . . . . ? O4 C4 C5 O5 -21.63(18) . . . . ? C3 C4 C5 O5 -140.41(17) . . . . ? C3 O3 C6 O2 -19.2(2) . . . . ? C3 O3 C6 C7 -136.9(2) . . . . ? C3 O3 C6 C8 97.7(2) . . . . ? C2 O2 C6 O3 5.0(2) . . . . ? C2 O2 C6 C7 121.9(2) . . . . ? C2 O2 C6 C8 -113.5(2) . . . . ? C4 O4 C9 O5 -31.06(19) . . . . ? C4 O4 C9 C11 -148.69(18) . . . . ? C4 O4 C9 C10 87.0(2) . . . . ? C5 O5 C9 O4 16.7(2) . . . . ? C5 O5 C9 C11 133.60(18) . . . . ? C5 O5 C9 C10 -102.4(2) . . . . ? C13 N1 C12 C1 84.09(18) . . . . ? C13 N1 C12 S1 -33.96(16) . . . . ? O1 C1 C12 N1 56.5(2) . . . . ? C2 C1 C12 N1 177.24(16) . . . . ? O1 C1 C12 S1 173.58(13) . . . . ? C2 C1 C12 S1 -65.69(19) . . . . ? C14 S1 C12 N1 8.07(14) . . . . ? C14 S1 C12 C1 -112.57(14) . . . . ? C12 N1 C13 C14 51.39(18) . . . . ? C12 N1 C13 P1 -176.02(11) . . . . ? O8 P1 C13 N1 -160.26(12) . . . . ? O7 P1 C13 N1 -35.09(14) . . . . ? O6 P1 C13 N1 77.30(13) . . . . ? O8 P1 C13 C14 -33.02(18) . . . . ? O7 P1 C13 C14 92.15(16) . . . . ? O6 P1 C13 C14 -155.46(14) . . . . ? N1 C13 C14 C15 -157.77(17) . . . . ? P1 C13 C14 C15 74.8(2) . . . . ? N1 C13 C14 C16 75.9(2) . . . . ? P1 C13 C14 C16 -51.5(2) . . . . ? N1 C13 C14 S1 -41.32(16) . . . . ? P1 C13 C14 S1 -168.73(10) . . . . ? C12 S1 C14 C15 136.68(15) . . . . ? C12 S1 C14 C16 -100.70(15) . . . . ? C12 S1 C14 C13 17.85(13) . . . . ? P1 O6 C17 C18 -58.5(2) . . . . ? O6 C17 C18 C19 62.0(2) . . . . ? O6 C17 C18 C21 -61.3(2) . . . . ? O6 C17 C18 C20 178.8(2) . . . . ? P1 O7 C19 C18 36.1(3) . . . . ? C17 C18 C19 O7 -50.7(2) . . . . ? C21 C18 C19 O7 71.9(2) . . . . ? C20 C18 C19 O7 -168.32(19) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.391 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.043 #=========================================================================== #========================================================================== #===== _eof # End of Crystallographic Information File