# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name "Peter O'Brien" _publ_contact_author_email PAOB1@YORK.AC.UK _publ_section_title ; Lithiation-Electrophilic Trapping of N-Sulfonyl-activated Ethylene Aziridines ; _publ_author_name "Peter O'Brien" # Attachment 'pob0609m.cif' data_pob0609m _database_code_depnum_ccdc_archive 'CCDC 695489' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H35 N O3 S' _chemical_formula_sum 'C25 H35 N O3 S' _chemical_formula_weight 429.60 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.2117(11) _cell_length_b 13.3903(14) _cell_length_c 17.8587(19) _cell_angle_alpha 90.00 _cell_angle_beta 104.642(2) _cell_angle_gamma 90.00 _cell_volume 2362.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 6679 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 24.98 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.863 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18118 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4156 _reflns_number_gt 3546 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+1.4152P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4156 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.25384(19) 0.46799(14) 0.15381(11) 0.0287(4) Uani 1 1 d . . . H1 H 1.3485 0.4564 0.1853 0.034 Uiso 1 1 calc R . . C2 C 1.17382(19) 0.37557(14) 0.13199(11) 0.0269(4) Uani 1 1 d . . . H2 H 1.1037 0.3789 0.0816 0.032 Uiso 1 1 calc R . . C3 C 1.2292(2) 0.27190(15) 0.15559(13) 0.0354(5) Uani 1 1 d . . . H3 H 1.2695 0.2458 0.1139 0.043 Uiso 1 1 calc R . . C4 C 1.11859(19) 0.20002(13) 0.16398(12) 0.0286(4) Uani 1 1 d . . . C5 C 1.0714(2) 0.19878(14) 0.23009(11) 0.0312(5) Uani 1 1 d . . . H5 H 1.1091 0.2430 0.2715 0.037 Uiso 1 1 calc R . . C6 C 0.9695(2) 0.13348(15) 0.23633(13) 0.0362(5) Uani 1 1 d . . . H6 H 0.9377 0.1336 0.2819 0.043 Uiso 1 1 calc R . . C7 C 0.9139(2) 0.06856(15) 0.17727(13) 0.0382(5) Uani 1 1 d . . . H7 H 0.8448 0.0233 0.1820 0.046 Uiso 1 1 calc R . . C8 C 0.9598(3) 0.07007(16) 0.11141(13) 0.0448(6) Uani 1 1 d . . . H8 H 0.9215 0.0259 0.0701 0.054 Uiso 1 1 calc R . . C9 C 1.0606(2) 0.13490(15) 0.10454(12) 0.0394(5) Uani 1 1 d . . . H9 H 1.0909 0.1350 0.0584 0.047 Uiso 1 1 calc R . . C10 C 1.2391(2) 0.55467(15) 0.09876(12) 0.0318(5) Uani 1 1 d . . . H10A H 1.3126 0.5531 0.0726 0.048 Uiso 1 1 calc R . . H10B H 1.2431 0.6173 0.1276 0.048 Uiso 1 1 calc R . . H10C H 1.1519 0.5500 0.0602 0.048 Uiso 1 1 calc R . . C11 C 0.91589(17) 0.43412(12) 0.23424(10) 0.0199(4) Uani 1 1 d . . . C12 C 0.97860(19) 0.42397(13) 0.31422(10) 0.0253(4) Uani 1 1 d . . . C13 C 0.9164(2) 0.36232(14) 0.35769(11) 0.0277(4) Uani 1 1 d . . . H13 H 0.9571 0.3552 0.4115 0.033 Uiso 1 1 calc R . . C14 C 0.79765(19) 0.31087(13) 0.32574(10) 0.0237(4) Uani 1 1 d . . . C15 C 0.73711(18) 0.32552(13) 0.24801(10) 0.0226(4) Uani 1 1 d . . . H15 H 0.6542 0.2921 0.2260 0.027 Uiso 1 1 calc R . . C16 C 0.79131(17) 0.38672(12) 0.20027(10) 0.0200(4) Uani 1 1 d . . . C17 C 1.1092(2) 0.47647(15) 0.35826(11) 0.0354(5) Uani 1 1 d . . . H17 H 1.1500 0.5092 0.3192 0.042 Uiso 1 1 calc R . . C18 C 1.0724(3) 0.5587(2) 0.40868(15) 0.0694(10) Uani 1 1 d . . . H18A H 1.0140 0.6080 0.3757 0.104 Uiso 1 1 calc R . . H18B H 1.1552 0.5915 0.4382 0.104 Uiso 1 1 calc R . . H18C H 1.0245 0.5294 0.4445 0.104 Uiso 1 1 calc R . . C19 C 1.2132(3) 0.4028(2) 0.40446(19) 0.0860(12) Uani 1 1 d . . . H19A H 1.2979 0.4381 0.4275 0.129 Uiso 1 1 calc R . . H19B H 1.2302 0.3502 0.3699 0.129 Uiso 1 1 calc R . . H19C H 1.1782 0.3728 0.4456 0.129 Uiso 1 1 calc R . . C20 C 0.73152(19) 0.24051(14) 0.37214(11) 0.0265(4) Uani 1 1 d . . . H20 H 0.6895 0.1850 0.3367 0.032 Uiso 1 1 calc R . . C21 C 0.8300(2) 0.19303(15) 0.44122(11) 0.0334(5) Uani 1 1 d . . . H21A H 0.9042 0.1615 0.4242 0.050 Uiso 1 1 calc R . . H21B H 0.7827 0.1425 0.4642 0.050 Uiso 1 1 calc R . . H21C H 0.8668 0.2445 0.4798 0.050 Uiso 1 1 calc R . . C22 C 0.6172(2) 0.29350(16) 0.39729(12) 0.0366(5) Uani 1 1 d . . . H22A H 0.6547 0.3483 0.4326 0.055 Uiso 1 1 calc R . . H22B H 0.5714 0.2459 0.4238 0.055 Uiso 1 1 calc R . . H22C H 0.5521 0.3203 0.3517 0.055 Uiso 1 1 calc R . . C23 C 0.71044(17) 0.39324(13) 0.11578(10) 0.0230(4) Uani 1 1 d . . . H23 H 0.7479 0.4499 0.0912 0.028 Uiso 1 1 calc R . . C24 C 0.56106(19) 0.41514(16) 0.10922(12) 0.0337(5) Uani 1 1 d . . . H24A H 0.5150 0.4291 0.0551 0.051 Uiso 1 1 calc R . . H24B H 0.5533 0.4733 0.1411 0.051 Uiso 1 1 calc R . . H24C H 0.5191 0.3571 0.1272 0.051 Uiso 1 1 calc R . . C25 C 0.7276(2) 0.29821(16) 0.07257(11) 0.0356(5) Uani 1 1 d . . . H25A H 0.8236 0.2883 0.0750 0.053 Uiso 1 1 calc R . . H25B H 0.6763 0.3040 0.0184 0.053 Uiso 1 1 calc R . . H25C H 0.6938 0.2411 0.0965 0.053 Uiso 1 1 calc R . . N1 N 1.14690(15) 0.43941(11) 0.19401(9) 0.0237(3) Uani 1 1 d . . . O1 O 0.93588(12) 0.50777(9) 0.09808(7) 0.0259(3) Uani 1 1 d . . . O2 O 1.04195(13) 0.60020(9) 0.21525(8) 0.0282(3) Uani 1 1 d . . . O3 O 1.33425(16) 0.28153(12) 0.22360(12) 0.0542(5) Uani 1 1 d . . . H3A H 1.362(3) 0.227(2) 0.2342(17) 0.072(10) Uiso 1 1 d . . . S1 S 1.00521(4) 0.50518(3) 0.17825(2) 0.01913(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 C1 0.0199(9) 0.0265(10) 0.0400(11) 0.0072(8) 0.0084(8) 0.0010(8) C2 0.0230(9) 0.0244(10) 0.0350(10) 0.0017(8) 0.0106(8) 0.0026(8) C3 0.0281(11) 0.0239(10) 0.0562(14) 0.0041(9) 0.0141(10) 0.0047(8) C4 0.0279(10) 0.0168(9) 0.0425(11) 0.0072(8) 0.0117(9) 0.0072(8) C5 0.0396(11) 0.0189(10) 0.0325(11) 0.0016(8) 0.0043(9) 0.0038(8) C6 0.0484(13) 0.0234(10) 0.0431(12) 0.0092(9) 0.0234(10) 0.0081(9) C7 0.0370(12) 0.0217(10) 0.0554(14) 0.0083(9) 0.0105(10) -0.0023(9) C8 0.0645(16) 0.0259(11) 0.0409(13) -0.0023(9) 0.0077(11) -0.0101(11) C9 0.0595(15) 0.0266(11) 0.0377(12) -0.0005(9) 0.0226(11) 0.0019(10) C10 0.0252(10) 0.0300(11) 0.0413(12) 0.0115(9) 0.0106(9) -0.0007(8) C11 0.0230(9) 0.0137(8) 0.0235(9) -0.0013(7) 0.0067(7) -0.0006(7) C12 0.0306(10) 0.0192(9) 0.0246(9) -0.0030(7) 0.0046(8) -0.0057(7) C13 0.0385(11) 0.0226(9) 0.0209(9) -0.0019(7) 0.0051(8) -0.0062(8) C14 0.0299(10) 0.0165(9) 0.0269(10) -0.0029(7) 0.0112(8) -0.0016(7) C15 0.0208(9) 0.0204(9) 0.0277(9) -0.0036(7) 0.0078(7) -0.0018(7) C16 0.0200(9) 0.0158(8) 0.0248(9) -0.0028(7) 0.0071(7) 0.0016(7) C17 0.0447(12) 0.0306(11) 0.0246(10) 0.0015(8) -0.0028(9) -0.0210(9) C18 0.098(2) 0.0738(19) 0.0485(15) -0.0368(14) 0.0412(15) -0.0658(18) C19 0.0675(19) 0.0608(18) 0.091(2) 0.0384(16) -0.0519(17) -0.0417(15) C20 0.0343(10) 0.0205(9) 0.0260(10) -0.0028(7) 0.0101(8) -0.0076(8) C21 0.0407(12) 0.0277(10) 0.0324(11) 0.0038(8) 0.0101(9) -0.0072(9) C22 0.0431(12) 0.0317(11) 0.0404(12) 0.0026(9) 0.0206(10) -0.0038(9) C23 0.0204(9) 0.0226(9) 0.0247(9) 0.0012(7) 0.0034(7) -0.0032(7) C24 0.0251(10) 0.0347(11) 0.0371(11) -0.0025(9) -0.0002(8) 0.0043(8) C25 0.0372(11) 0.0398(12) 0.0260(10) -0.0044(9) 0.0011(9) 0.0080(9) N1 0.0214(8) 0.0194(8) 0.0292(8) 0.0046(6) 0.0046(6) -0.0017(6) O1 0.0231(6) 0.0262(7) 0.0274(7) 0.0061(5) 0.0044(5) -0.0016(5) O2 0.0306(7) 0.0158(6) 0.0369(8) -0.0010(5) 0.0060(6) -0.0053(5) O3 0.0325(9) 0.0249(9) 0.0914(14) 0.0194(8) -0.0097(8) 0.0024(7) S1 0.0189(2) 0.0139(2) 0.0234(2) 0.00170(16) 0.00321(17) -0.00088(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.480(3) . ? C1 N1 1.500(2) . ? C1 C10 1.504(3) . ? C1 H1 1.0000 . ? C2 N1 1.479(2) . ? C2 C3 1.518(3) . ? C2 H2 1.0000 . ? C3 O3 1.408(3) . ? C3 C4 1.520(3) . ? C3 H3 1.0000 . ? C4 C5 1.384(3) . ? C4 C9 1.386(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.374(3) . ? C6 H6 0.9500 . ? C7 C8 1.372(3) . ? C7 H7 0.9500 . ? C8 C9 1.376(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.414(2) . ? C11 C12 1.416(2) . ? C11 S1 1.7883(17) . ? C12 C13 1.391(3) . ? C12 C17 1.536(3) . ? C13 C14 1.386(3) . ? C13 H13 0.9500 . ? C14 C15 1.383(3) . ? C14 C20 1.521(2) . ? C15 C16 1.394(2) . ? C15 H15 0.9500 . ? C16 C23 1.529(2) . ? C17 C18 1.528(3) . ? C17 C19 1.530(3) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.520(3) . ? C20 C22 1.527(3) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C25 1.521(3) . ? C23 C24 1.528(3) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? N1 S1 1.6560(15) . ? O1 S1 1.4282(13) . ? O2 S1 1.4391(13) . ? O3 H3A 0.79(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 C2 C1 N1 59.49(12) . . ? C2 C1 C10 121.05(17) . . ? N1 C1 C10 123.03(16) . . ? C2 C1 H1 114.2 . . ? N1 C1 H1 114.2 . . ? C10 C1 H1 114.2 . . ? N1 C2 C1 60.94(12) . . ? N1 C2 C3 116.58(16) . . ? C1 C2 C3 123.32(17) . . ? N1 C2 H2 115.0 . . ? C1 C2 H2 115.0 . . ? C3 C2 H2 115.0 . . ? O3 C3 C2 107.75(17) . . ? O3 C3 C4 113.32(18) . . ? C2 C3 C4 111.85(16) . . ? O3 C3 H3 107.9 . . ? C2 C3 H3 107.9 . . ? C4 C3 H3 107.9 . . ? C5 C4 C9 118.19(18) . . ? C5 C4 C3 121.31(18) . . ? C9 C4 C3 120.49(19) . . ? C4 C5 C6 120.47(19) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 120.71(19) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C6 119.0(2) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C9 120.7(2) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C4 120.9(2) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 121.19(16) . . ? C16 C11 S1 121.99(13) . . ? C12 C11 S1 116.77(13) . . ? C13 C12 C11 117.76(16) . . ? C13 C12 C17 116.43(16) . . ? C11 C12 C17 125.79(16) . . ? C14 C13 C12 122.71(17) . . ? C14 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? C15 C14 C13 117.72(16) . . ? C15 C14 C20 119.16(16) . . ? C13 C14 C20 123.13(16) . . ? C14 C15 C16 123.45(16) . . ? C14 C15 H15 118.3 . . ? C16 C15 H15 118.3 . . ? C15 C16 C11 117.05(16) . . ? C15 C16 C23 116.00(15) . . ? C11 C16 C23 126.93(15) . . ? C18 C17 C19 112.8(2) . . ? C18 C17 C12 108.70(19) . . ? C19 C17 C12 112.04(17) . . ? C18 C17 H17 107.7 . . ? C19 C17 H17 107.7 . . ? C12 C17 H17 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C14 114.04(16) . . ? C21 C20 C22 110.72(16) . . ? C14 C20 C22 110.49(15) . . ? C21 C20 H20 107.1 . . ? C14 C20 H20 107.1 . . ? C22 C20 H20 107.1 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C25 C23 C24 111.23(16) . . ? C25 C23 C16 110.51(15) . . ? C24 C23 C16 111.49(15) . . ? C25 C23 H23 107.8 . . ? C24 C23 H23 107.8 . . ? C16 C23 H23 107.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C2 N1 C1 59.57(12) . . ? C2 N1 S1 120.00(12) . . ? C1 N1 S1 119.57(12) . . ? C3 O3 H3A 106(2) . . ? O1 S1 O2 116.39(8) . . ? O1 S1 N1 111.94(8) . . ? O2 S1 N1 106.08(8) . . ? O1 S1 C11 112.32(8) . . ? O2 S1 C11 108.92(8) . . ? N1 S1 C11 99.75(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 N1 -112.56(19) . . . . ? N1 C1 C2 C3 -104.3(2) . . . . ? C10 C1 C2 C3 143.12(19) . . . . ? N1 C2 C3 O3 -46.1(2) . . . . ? C1 C2 C3 O3 25.1(3) . . . . ? N1 C2 C3 C4 79.0(2) . . . . ? C1 C2 C3 C4 150.31(18) . . . . ? O3 C3 C4 C5 41.6(2) . . . . ? C2 C3 C4 C5 -80.5(2) . . . . ? O3 C3 C4 C9 -139.6(2) . . . . ? C2 C3 C4 C9 98.4(2) . . . . ? C9 C4 C5 C6 0.4(3) . . . . ? C3 C4 C5 C6 179.31(18) . . . . ? C4 C5 C6 C7 0.3(3) . . . . ? C5 C6 C7 C8 -0.7(3) . . . . ? C6 C7 C8 C9 0.5(3) . . . . ? C7 C8 C9 C4 0.2(4) . . . . ? C5 C4 C9 C8 -0.7(3) . . . . ? C3 C4 C9 C8 -179.6(2) . . . . ? C16 C11 C12 C13 2.7(3) . . . . ? S1 C11 C12 C13 -174.84(14) . . . . ? C16 C11 C12 C17 -176.33(18) . . . . ? S1 C11 C12 C17 6.1(3) . . . . ? C11 C12 C13 C14 0.4(3) . . . . ? C17 C12 C13 C14 179.52(18) . . . . ? C12 C13 C14 C15 -2.6(3) . . . . ? C12 C13 C14 C20 177.81(17) . . . . ? C13 C14 C15 C16 1.9(3) . . . . ? C20 C14 C15 C16 -178.56(16) . . . . ? C14 C15 C16 C11 1.1(3) . . . . ? C14 C15 C16 C23 179.65(16) . . . . ? C12 C11 C16 C15 -3.4(2) . . . . ? S1 C11 C16 C15 174.02(13) . . . . ? C12 C11 C16 C23 178.22(16) . . . . ? S1 C11 C16 C23 -4.4(2) . . . . ? C13 C12 C17 C18 -72.3(2) . . . . ? C11 C12 C17 C18 106.8(2) . . . . ? C13 C12 C17 C19 53.1(3) . . . . ? C11 C12 C17 C19 -127.9(2) . . . . ? C15 C14 C20 C21 153.12(17) . . . . ? C13 C14 C20 C21 -27.3(3) . . . . ? C15 C14 C20 C22 -81.4(2) . . . . ? C13 C14 C20 C22 98.1(2) . . . . ? C15 C16 C23 C25 -74.8(2) . . . . ? C11 C16 C23 C25 103.6(2) . . . . ? C15 C16 C23 C24 49.4(2) . . . . ? C11 C16 C23 C24 -132.13(18) . . . . ? C3 C2 N1 C1 115.13(19) . . . . ? C1 C2 N1 S1 108.76(14) . . . . ? C3 C2 N1 S1 -136.10(14) . . . . ? C10 C1 N1 C2 109.3(2) . . . . ? C2 C1 N1 S1 -109.48(15) . . . . ? C10 C1 N1 S1 -0.1(2) . . . . ? C2 N1 S1 O1 -12.36(15) . . . . ? C1 N1 S1 O1 57.47(15) . . . . ? C2 N1 S1 O2 -140.30(13) . . . . ? C1 N1 S1 O2 -70.47(15) . . . . ? C2 N1 S1 C11 106.63(13) . . . . ? C1 N1 S1 C11 176.45(13) . . . . ? C16 C11 S1 O1 0.34(17) . . . . ? C12 C11 S1 O1 177.84(13) . . . . ? C16 C11 S1 O2 130.78(14) . . . . ? C12 C11 S1 O2 -51.73(15) . . . . ? C16 C11 S1 N1 -118.37(14) . . . . ? C12 C11 S1 N1 59.13(15) . . . . ? 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 O3 H3A O2 0.79(3) 2.06(3) 2.826(2) 167(3) 2_745 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.461 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.046 # Attachment 'pob0703m.cif' data_pob0703m _database_code_depnum_ccdc_archive 'CCDC 695490' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H40 N2 O6 S' _chemical_formula_sum 'C29 H40 N2 O6 S' _chemical_formula_weight 544.69 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7183(5) _cell_length_b 19.6987(9) _cell_length_c 15.3953(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.6970(10) _cell_angle_gamma 90.00 _cell_volume 2932.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 7494 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'SADABS v2.03;(Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29913 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.29 _reflns_number_total 7272 _reflns_number_gt 5978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+0.6791P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7272 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.55972(15) 0.26359(8) 0.89037(10) 0.0258(3) Uani 1 1 d . . . H1A H 0.6388 0.2607 0.9350 0.039 Uiso 1 1 calc R . . H1B H 0.5929 0.2713 0.8331 0.039 Uiso 1 1 calc R . . H1C H 0.5073 0.2210 0.8892 0.039 Uiso 1 1 calc R . . C2 C 0.46758(14) 0.32161(7) 0.91159(9) 0.0213(3) Uani 1 1 d . . . H2 H 0.5063 0.3676 0.9010 0.026 Uiso 1 1 calc R . . C3 C 0.31450(14) 0.31711(7) 0.89379(8) 0.0193(3) Uani 1 1 d . . . H3 H 0.2770 0.2721 0.8727 0.023 Uiso 1 1 calc R . . C4 C 0.22372(15) 0.37752(7) 0.87081(9) 0.0217(3) Uani 1 1 d . . . H4 H 0.2679 0.4190 0.8988 0.026 Uiso 1 1 calc R . . C5 C 0.07790(16) 0.37036(8) 0.89811(10) 0.0308(3) Uani 1 1 d . . . H5 H 0.0866 0.3602 0.9621 0.037 Uiso 1 1 calc R . . C6 C -0.00309(18) 0.31222(10) 0.85178(13) 0.0445(5) Uani 1 1 d . . . H6A H -0.0152 0.3211 0.7889 0.067 Uiso 1 1 calc R . . H6B H -0.0939 0.3085 0.8740 0.067 Uiso 1 1 calc R . . H6C H 0.0479 0.2696 0.8628 0.067 Uiso 1 1 calc R . . C7 C 0.0001(2) 0.43748(10) 0.88460(12) 0.0461(5) Uani 1 1 d . . . H7A H 0.0517 0.4734 0.9177 0.069 Uiso 1 1 calc R . . H7B H -0.0918 0.4330 0.9050 0.069 Uiso 1 1 calc R . . H7C H -0.0094 0.4491 0.8224 0.069 Uiso 1 1 calc R . . C8 C 0.22395(12) 0.27906(6) 1.10345(8) 0.0156(2) Uani 1 1 d . . . C9 C 0.22759(13) 0.34606(6) 1.13667(8) 0.0160(2) Uani 1 1 d . . . C10 C 0.10341(13) 0.37381(7) 1.15826(8) 0.0169(2) Uani 1 1 d . . . H10 H 0.1034 0.4191 1.1795 0.020 Uiso 1 1 calc R . . C11 C -0.02032(13) 0.33795(7) 1.14991(8) 0.0175(3) Uani 1 1 d . . . C12 C -0.01586(14) 0.27000(7) 1.12647(9) 0.0208(3) Uani 1 1 d . . . H12 H -0.0982 0.2439 1.1253 0.025 Uiso 1 1 calc R . . C13 C 0.10453(14) 0.23843(6) 1.10454(9) 0.0184(3) Uani 1 1 d . . . C14 C 0.35792(13) 0.38882(7) 1.15631(9) 0.0190(3) Uani 1 1 d . . . H14 H 0.4368 0.3640 1.1337 0.023 Uiso 1 1 calc R . . C15 C 0.38822(15) 0.39552(9) 1.25551(10) 0.0311(4) Uani 1 1 d . . . H15A H 0.3104 0.4181 1.2794 0.047 Uiso 1 1 calc R . . H15B H 0.4724 0.4225 1.2691 0.047 Uiso 1 1 calc R . . H15C H 0.4013 0.3503 1.2815 0.047 Uiso 1 1 calc R . . C16 C 0.34703(15) 0.45865(8) 1.11290(12) 0.0322(4) Uani 1 1 d . . . H16A H 0.3213 0.4532 1.0501 0.048 Uiso 1 1 calc R . . H16B H 0.4364 0.4819 1.1224 0.048 Uiso 1 1 calc R . . H16C H 0.2764 0.4856 1.1384 0.048 Uiso 1 1 calc R . . C17 C -0.15476(13) 0.37270(7) 1.16606(9) 0.0195(3) Uani 1 1 d . . . H17 H -0.1317 0.4194 1.1884 0.023 Uiso 1 1 calc R . . C18 C -0.24859(15) 0.37992(9) 1.08062(10) 0.0288(3) Uani 1 1 d . . . H18A H -0.1980 0.4030 1.0372 0.043 Uiso 1 1 calc R . . H18B H -0.3304 0.4066 1.0910 0.043 Uiso 1 1 calc R . . H18C H -0.2774 0.3348 1.0590 0.043 Uiso 1 1 calc R . . C19 C -0.23131(14) 0.33600(8) 1.23461(10) 0.0261(3) Uani 1 1 d . . . H19A H -0.2530 0.2895 1.2150 0.039 Uiso 1 1 calc R . . H19B H -0.3172 0.3602 1.2425 0.039 Uiso 1 1 calc R . . H19C H -0.1727 0.3347 1.2902 0.039 Uiso 1 1 calc R . . C20 C 0.09843(14) 0.16157(7) 1.09072(10) 0.0227(3) Uani 1 1 d . . . H20 H 0.1932 0.1460 1.0799 0.027 Uiso 1 1 calc R . . C21 C 0.00010(17) 0.14219(8) 1.01135(11) 0.0330(4) Uani 1 1 d . . . H21A H -0.0923 0.1602 1.0180 0.049 Uiso 1 1 calc R . . H21B H -0.0045 0.0926 1.0063 0.049 Uiso 1 1 calc R . . H21C H 0.0338 0.1613 0.9586 0.049 Uiso 1 1 calc R . . C22 C 0.06026(17) 0.12661(8) 1.17389(11) 0.0317(3) Uani 1 1 d . . . H22A H 0.1301 0.1373 1.2224 0.048 Uiso 1 1 calc R . . H22B H 0.0567 0.0774 1.1648 0.048 Uiso 1 1 calc R . . H22C H -0.0304 0.1428 1.1878 0.048 Uiso 1 1 calc R . . C23 C 0.26191(13) 0.44303(7) 0.74470(9) 0.0182(3) Uani 1 1 d . . . C24 C 0.22377(13) 0.44922(6) 0.64877(8) 0.0167(2) Uani 1 1 d . . . C25 C 0.14285(14) 0.40078(7) 0.60212(9) 0.0205(3) Uani 1 1 d . . . H25 H 0.1131 0.3615 0.6309 0.025 Uiso 1 1 calc R . . C26 C 0.10556(14) 0.40984(7) 0.51365(9) 0.0221(3) Uani 1 1 d . . . H26 H 0.0493 0.3774 0.4811 0.026 Uiso 1 1 calc R . . C27 C 0.15195(13) 0.46694(7) 0.47400(8) 0.0197(3) Uani 1 1 d . . . C28 C 0.23203(15) 0.51595(7) 0.51866(9) 0.0247(3) Uani 1 1 d . . . H28 H 0.2617 0.5550 0.4895 0.030 Uiso 1 1 calc R . . C29 C 0.26798(15) 0.50674(7) 0.60692(9) 0.0237(3) Uani 1 1 d . . . H29 H 0.3230 0.5397 0.6392 0.028 Uiso 1 1 calc R . . N1 N 0.37831(11) 0.31916(5) 0.98508(7) 0.0170(2) Uani 1 1 d . . . N2 N 0.11029(12) 0.47751(7) 0.38028(8) 0.0257(3) Uani 1 1 d . . . O1 O 0.49257(10) 0.24842(5) 1.10553(6) 0.0218(2) Uani 1 1 d . . . O2 O 0.33006(10) 0.19227(5) 0.99603(6) 0.0212(2) Uani 1 1 d . . . O3 O 0.21254(10) 0.38550(5) 0.77630(6) 0.0221(2) Uani 1 1 d . . . O4 O 0.32778(11) 0.48504(5) 0.78776(6) 0.0275(2) Uani 1 1 d . . . O5 O 0.03077(12) 0.43651(7) 0.34266(7) 0.0382(3) Uani 1 1 d . . . O6 O 0.15624(13) 0.52699(7) 0.34471(7) 0.0387(3) Uani 1 1 d . . . S1 S 0.36693(3) 0.251470(15) 1.04811(2) 0.01572(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0211(7) 0.0315(8) 0.0259(7) 0.0015(6) 0.0084(6) 0.0040(6) C2 0.0220(7) 0.0225(7) 0.0202(6) 0.0031(5) 0.0066(5) 0.0001(5) C3 0.0209(6) 0.0197(6) 0.0174(6) 0.0008(5) 0.0026(5) 0.0025(5) C4 0.0283(7) 0.0216(7) 0.0154(6) 0.0030(5) 0.0027(5) 0.0050(5) C5 0.0293(8) 0.0394(9) 0.0247(7) 0.0134(6) 0.0075(6) 0.0145(6) C6 0.0251(8) 0.0555(12) 0.0538(11) 0.0162(9) 0.0080(8) -0.0012(8) C7 0.0480(10) 0.0564(12) 0.0359(9) 0.0175(8) 0.0140(8) 0.0336(9) C8 0.0141(6) 0.0164(6) 0.0166(6) -0.0009(5) 0.0030(4) 0.0030(5) C9 0.0148(6) 0.0172(6) 0.0158(6) -0.0008(5) 0.0004(4) 0.0002(5) C10 0.0159(6) 0.0162(6) 0.0185(6) -0.0026(5) 0.0009(5) 0.0019(5) C11 0.0145(6) 0.0205(6) 0.0175(6) -0.0017(5) 0.0021(5) 0.0021(5) C12 0.0161(6) 0.0211(6) 0.0257(7) -0.0034(5) 0.0040(5) -0.0025(5) C13 0.0183(6) 0.0168(6) 0.0203(6) -0.0014(5) 0.0027(5) -0.0006(5) C14 0.0130(6) 0.0192(6) 0.0247(7) -0.0049(5) 0.0007(5) 0.0008(5) C15 0.0187(7) 0.0457(10) 0.0283(8) -0.0144(7) -0.0012(6) -0.0008(6) C16 0.0213(7) 0.0200(7) 0.0542(10) 0.0007(7) -0.0018(7) -0.0038(6) C17 0.0136(6) 0.0217(7) 0.0235(7) -0.0024(5) 0.0028(5) 0.0023(5) C18 0.0197(7) 0.0414(9) 0.0251(7) 0.0001(6) 0.0010(6) 0.0064(6) C19 0.0195(7) 0.0318(8) 0.0280(7) -0.0001(6) 0.0077(6) 0.0025(6) C20 0.0215(6) 0.0154(6) 0.0326(8) -0.0043(5) 0.0091(6) -0.0035(5) C21 0.0326(8) 0.0261(8) 0.0403(9) -0.0109(7) 0.0039(7) -0.0055(6) C22 0.0353(8) 0.0205(7) 0.0419(9) 0.0013(6) 0.0164(7) -0.0034(6) C23 0.0160(6) 0.0186(6) 0.0203(6) 0.0002(5) 0.0027(5) 0.0029(5) C24 0.0155(6) 0.0165(6) 0.0183(6) -0.0005(5) 0.0022(5) 0.0012(5) C25 0.0225(6) 0.0173(6) 0.0222(7) 0.0004(5) 0.0044(5) -0.0038(5) C26 0.0212(6) 0.0237(7) 0.0211(7) -0.0054(5) 0.0013(5) -0.0046(5) C27 0.0180(6) 0.0245(7) 0.0167(6) 0.0001(5) 0.0021(5) 0.0025(5) C28 0.0273(7) 0.0223(7) 0.0244(7) 0.0059(5) 0.0021(6) -0.0049(5) C29 0.0253(7) 0.0209(7) 0.0239(7) 0.0005(5) -0.0019(5) -0.0066(5) N1 0.0173(5) 0.0158(5) 0.0181(5) 0.0014(4) 0.0032(4) 0.0005(4) N2 0.0224(6) 0.0362(7) 0.0187(6) 0.0002(5) 0.0036(5) 0.0059(5) O1 0.0165(5) 0.0235(5) 0.0252(5) 0.0034(4) 0.0017(4) 0.0051(4) O2 0.0245(5) 0.0154(5) 0.0248(5) -0.0024(4) 0.0080(4) 0.0008(4) O3 0.0308(5) 0.0187(5) 0.0168(5) 0.0024(4) 0.0024(4) -0.0006(4) O4 0.0297(5) 0.0305(6) 0.0214(5) -0.0012(4) -0.0018(4) -0.0084(4) O5 0.0347(6) 0.0568(8) 0.0222(5) -0.0075(5) -0.0020(5) -0.0060(6) O6 0.0470(7) 0.0450(7) 0.0242(6) 0.0110(5) 0.0041(5) -0.0009(6) S1 0.01499(15) 0.01412(15) 0.01853(16) 0.00081(11) 0.00404(11) 0.00253(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5075(19) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.4883(19) . ? C2 N1 1.4933(16) . ? C2 H2 1.0000 . ? C3 N1 1.4793(16) . ? C3 C4 1.5026(18) . ? C3 H3 1.0000 . ? C4 O3 1.4568(16) . ? C4 C5 1.524(2) . ? C4 H4 1.0000 . ? C5 C6 1.526(3) . ? C5 C7 1.527(2) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C13 1.4112(18) . ? C8 C9 1.4147(18) . ? C8 S1 1.7852(12) . ? C9 C10 1.3947(17) . ? C9 C14 1.5262(17) . ? C10 C11 1.3894(18) . ? C10 H10 0.9500 . ? C11 C12 1.3882(19) . ? C11 C17 1.5172(17) . ? C12 C13 1.3957(18) . ? C12 H12 0.9500 . ? C13 C20 1.5292(18) . ? C14 C16 1.528(2) . ? C14 C15 1.532(2) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.5310(19) . ? C17 C19 1.5316(19) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.523(2) . ? C20 C22 1.532(2) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 O4 1.2041(16) . ? C23 O3 1.3406(16) . ? C23 C24 1.4915(18) . ? C24 C25 1.3903(18) . ? C24 C29 1.3923(19) . ? C25 C26 1.3857(19) . ? C25 H25 0.9500 . ? C26 C27 1.3769(19) . ? C26 H26 0.9500 . ? C27 C28 1.3799(19) . ? C27 N2 1.4740(17) . ? C28 C29 1.381(2) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? N1 S1 1.6593(11) . ? N2 O5 1.2231(17) . ? N2 O6 1.2240(17) . ? O1 S1 1.4358(10) . ? O2 S1 1.4403(10) . ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 N1 59.49(8) . . ? C3 C2 C1 121.29(12) . . ? N1 C2 C1 122.82(12) . . ? C3 C2 H2 114.2 . . ? N1 C2 H2 114.2 . . ? C1 C2 H2 114.2 . . ? N1 C3 C2 60.42(8) . . ? N1 C3 C4 112.52(11) . . ? C2 C3 C4 123.30(12) . . ? N1 C3 H3 116.0 . . ? C2 C3 H3 116.0 . . ? C4 C3 H3 116.0 . . ? O3 C4 C3 107.73(11) . . ? O3 C4 C5 107.83(11) . . ? C3 C4 C5 113.70(12) . . ? O3 C4 H4 109.2 . . ? C3 C4 H4 109.2 . . ? C5 C4 H4 109.2 . . ? C4 C5 C6 113.03(13) . . ? C4 C5 C7 110.09(14) . . ? C6 C5 C7 111.15(15) . . ? C4 C5 H5 107.4 . . ? C6 C5 H5 107.4 . . ? C7 C5 H5 107.4 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 121.06(11) . . ? C13 C8 S1 120.87(10) . . ? C9 C8 S1 117.63(9) . . ? C10 C9 C8 117.42(11) . . ? C10 C9 C14 117.21(11) . . ? C8 C9 C14 125.24(11) . . ? C11 C10 C9 122.69(12) . . ? C11 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C12 C11 C10 117.72(12) . . ? C12 C11 C17 121.81(12) . . ? C10 C11 C17 120.46(12) . . ? C11 C12 C13 122.75(12) . . ? C11 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? C12 C13 C8 117.41(12) . . ? C12 C13 C20 116.93(12) . . ? C8 C13 C20 125.48(12) . . ? C9 C14 C16 112.96(11) . . ? C9 C14 C15 108.58(11) . . ? C16 C14 C15 110.89(12) . . ? C9 C14 H14 108.1 . . ? C16 C14 H14 108.1 . . ? C15 C14 H14 108.1 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C17 C18 110.50(11) . . ? C11 C17 C19 112.65(11) . . ? C18 C17 C19 110.32(11) . . ? C11 C17 H17 107.7 . . ? C18 C17 H17 107.7 . . ? C19 C17 H17 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C13 111.86(12) . . ? C21 C20 C22 111.91(12) . . ? C13 C20 C22 109.76(11) . . ? C21 C20 H20 107.7 . . ? C13 C20 H20 107.7 . . ? C22 C20 H20 107.7 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O4 C23 O3 124.81(12) . . ? O4 C23 C24 123.73(12) . . ? O3 C23 C24 111.45(11) . . ? C25 C24 C29 120.28(12) . . ? C25 C24 C23 121.84(12) . . ? C29 C24 C23 117.84(12) . . ? C26 C25 C24 119.91(12) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C27 C26 C25 118.42(12) . . ? C27 C26 H26 120.8 . . ? C25 C26 H26 120.8 . . ? C26 C27 C28 122.95(12) . . ? C26 C27 N2 118.63(12) . . ? C28 C27 N2 118.39(12) . . ? C27 C28 C29 118.26(13) . . ? C27 C28 H28 120.9 . . ? C29 C28 H28 120.9 . . ? C28 C29 C24 120.18(13) . . ? C28 C29 H29 119.9 . . ? C24 C29 H29 119.9 . . ? C3 N1 C2 60.09(8) . . ? C3 N1 S1 119.18(9) . . ? C2 N1 S1 123.12(9) . . ? O5 N2 O6 123.74(13) . . ? O5 N2 C27 118.00(12) . . ? O6 N2 C27 118.26(12) . . ? C23 O3 C4 117.37(11) . . ? O1 S1 O2 117.27(6) . . ? O1 S1 N1 106.96(6) . . ? O2 S1 N1 110.64(6) . . ? O1 S1 C8 111.93(6) . . ? O2 S1 C8 110.47(6) . . ? N1 S1 C8 97.74(6) . . ? 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 C1 C2 C3 N1 112.21(14) . . . . ? N1 C2 C3 C4 98.86(14) . . . . ? C1 C2 C3 C4 -148.92(13) . . . . ? N1 C3 C4 O3 157.35(10) . . . . ? C2 C3 C4 O3 88.87(15) . . . . ? N1 C3 C4 C5 -83.22(15) . . . . ? C2 C3 C4 C5 -151.69(13) . . . . ? O3 C4 C5 C6 56.03(16) . . . . ? C3 C4 C5 C6 -63.35(16) . . . . ? O3 C4 C5 C7 -68.93(16) . . . . ? C3 C4 C5 C7 171.69(13) . . . . ? C13 C8 C9 C10 -9.35(19) . . . . ? S1 C8 C9 C10 163.06(10) . . . . ? C13 C8 C9 C14 166.49(12) . . . . ? S1 C8 C9 C14 -21.09(17) . . . . ? C8 C9 C10 C11 1.28(19) . . . . ? C14 C9 C10 C11 -174.91(12) . . . . ? C9 C10 C11 C12 5.8(2) . . . . ? C9 C10 C11 C17 -174.13(12) . . . . ? C10 C11 C12 C13 -5.2(2) . . . . ? C17 C11 C12 C13 174.73(13) . . . . ? C11 C12 C13 C8 -2.4(2) . . . . ? C11 C12 C13 C20 172.90(13) . . . . ? C9 C8 C13 C12 9.90(19) . . . . ? S1 C8 C13 C12 -162.27(10) . . . . ? C9 C8 C13 C20 -164.99(13) . . . . ? S1 C8 C13 C20 22.84(19) . . . . ? C10 C9 C14 C16 -56.60(16) . . . . ? C8 C9 C14 C16 127.55(14) . . . . ? C10 C9 C14 C15 66.83(15) . . . . ? C8 C9 C14 C15 -109.02(14) . . . . ? C12 C11 C17 C18 -68.86(17) . . . . ? C10 C11 C17 C18 111.11(14) . . . . ? C12 C11 C17 C19 55.04(17) . . . . ? C10 C11 C17 C19 -124.98(14) . . . . ? C12 C13 C20 C21 65.96(16) . . . . ? C8 C13 C20 C21 -119.12(15) . . . . ? C12 C13 C20 C22 -58.89(17) . . . . ? C8 C13 C20 C22 116.03(15) . . . . ? O4 C23 C24 C25 -177.39(13) . . . . ? O3 C23 C24 C25 2.02(17) . . . . ? O4 C23 C24 C29 0.5(2) . . . . ? O3 C23 C24 C29 179.87(12) . . . . ? C29 C24 C25 C26 -0.2(2) . . . . ? C23 C24 C25 C26 177.58(12) . . . . ? C24 C25 C26 C27 0.8(2) . . . . ? C25 C26 C27 C28 -1.0(2) . . . . ? C25 C26 C27 N2 -178.79(12) . . . . ? C26 C27 C28 C29 0.6(2) . . . . ? N2 C27 C28 C29 178.39(12) . . . . ? C27 C28 C29 C24 0.0(2) . . . . ? C25 C24 C29 C28 -0.2(2) . . . . ? C23 C24 C29 C28 -178.08(13) . . . . ? C4 C3 N1 C2 -116.62(13) . . . . ? C2 C3 N1 S1 -113.63(11) . . . . ? C4 C3 N1 S1 129.75(10) . . . . ? C1 C2 N1 C3 -109.71(15) . . . . ? C3 C2 N1 S1 107.24(11) . . . . ? C1 C2 N1 S1 -2.47(18) . . . . ? C26 C27 N2 O5 3.35(19) . . . . ? C28 C27 N2 O5 -174.54(13) . . . . ? C26 C27 N2 O6 -177.22(13) . . . . ? C28 C27 N2 O6 4.90(19) . . . . ? O4 C23 O3 C4 8.46(19) . . . . ? C24 C23 O3 C4 -170.94(10) . . . . ? C3 C4 O3 C23 -117.61(12) . . . . ? C5 C4 O3 C23 119.29(13) . . . . ? C3 N1 S1 O1 145.98(9) . . . . ? C2 N1 S1 O1 74.50(11) . . . . ? C3 N1 S1 O2 17.17(11) . . . . ? C2 N1 S1 O2 -54.31(11) . . . . ? C3 N1 S1 C8 -98.20(10) . . . . ? C2 N1 S1 C8 -169.68(10) . . . . ? C13 C8 S1 O1 -122.47(11) . . . . ? C9 C8 S1 O1 65.10(11) . . . . ? C13 C8 S1 O2 10.19(13) . . . . ? C9 C8 S1 O2 -162.24(10) . . . . ? C13 C8 S1 N1 125.69(11) . . . . ? C9 C8 S1 N1 -46.74(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.420 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.051