# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Christopher Moody' 'Alexandra M. Z. Slawin' 'David Willows' _publ_contact_author_name 'Prof Christopher Moody' _publ_contact_author_address ; Chemistry University of Exeter Stocker Road Exeter Devon EX4 4QD UNITED KINGDOM ; _publ_contact_author_email C.J.MOODY@EX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Dirhodium(II) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomunchnones), an approach to analogues of dehydrogliotoxin ; data_10 _database_code_CSD 211109 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N2 O5 S' _chemical_formula_sum 'C20 H20 N2 O5 S' _chemical_formula_weight 400.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.396(3) _cell_length_b 8.9008(18) _cell_length_c 15.043(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.83(3) _cell_angle_gamma 90.00 _cell_volume 1854.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.43 _cell_measurement_theta_max 12.42 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.865 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min .853 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'scintillation counter' _diffrn_measurement_method 'OMEGA SCANS' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.07 _diffrn_reflns_number 2816 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 60.06 _reflns_number_total 2696 _reflns_number_gt 2046 _reflns_threshold_expression >2sigma(I) _computing_data_collection TEXSAN _computing_cell_refinement TEXSAN _computing_data_reduction TEXSAN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0949P)^2^+0.0961P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2696 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.19878(13) 0.4467(3) 0.79048(13) 0.0483(5) Uani 1 1 d . . . S2 S 0.30733(4) 0.38438(8) 0.95511(4) 0.0514(3) Uani 1 1 d . . . C2 C 0.29068(16) 0.3656(3) 0.82867(16) 0.0468(6) Uani 1 1 d . . . C3 C 0.36441(17) 0.4440(3) 0.78563(17) 0.0503(6) Uani 1 1 d . . . C4 C 0.31369(18) 0.5911(3) 0.75271(17) 0.0507(6) Uani 1 1 d . . . C5 C 0.3473(2) 0.7183(3) 0.71834(19) 0.0607(7) Uani 1 1 d . . . H5A H 0.4114 0.7246 0.7172 0.073 Uiso 1 1 calc R . . C6 C 0.2841(2) 0.8363(3) 0.68563(19) 0.0619(7) Uani 1 1 d . . . H6A H 0.3063 0.9217 0.6622 0.074 Uiso 1 1 calc R . . C7 C 0.1900(2) 0.8292(3) 0.68720(19) 0.0618(7) Uani 1 1 d . . . H7A H 0.1495 0.9104 0.6657 0.074 Uiso 1 1 calc R . . C8 C 0.15333(19) 0.7024(3) 0.72050(18) 0.0581(7) Uani 1 1 d . . . H8A H 0.0891 0.6963 0.7212 0.070 Uiso 1 1 calc R . . C9 C 0.21781(17) 0.5861(3) 0.75239(17) 0.0489(6) Uani 1 1 d . . . C10 C 0.13589(18) 0.4270(3) 0.84348(17) 0.0511(6) Uani 1 1 d . . . O10 O 0.05860(13) 0.4888(2) 0.83277(14) 0.0635(5) Uani 1 1 d . . . C11 C 0.18320(17) 0.3132(3) 0.91839(17) 0.0510(6) Uani 1 1 d . . . C12 C 0.19183(16) 0.1640(3) 0.86703(17) 0.0481(6) Uani 1 1 d . . . H12A H 0.1294 0.1346 0.8254 0.058 Uiso 1 1 calc R . . O13 O 0.20276(14) -0.0161(3) 0.99142(15) 0.0736(6) Uani 1 1 d . . . C13 C 0.23486(19) 0.0383(3) 0.93268(18) 0.0541(7) Uani 1 1 d . . . N14 N 0.32080(15) -0.0037(3) 0.91623(15) 0.0562(6) Uani 1 1 d . . . C14 C 0.3796(2) -0.1263(4) 0.9656(2) 0.0730(8) Uani 1 1 d . . . H14A H 0.3461 -0.1755 1.0045 0.109 Uiso 1 1 calc R . . H14B H 0.4398 -0.0872 1.0028 0.109 Uiso 1 1 calc R . . H14C H 0.3918 -0.1971 0.9219 0.109 Uiso 1 1 calc R . . C15 C 0.34830(18) 0.0899(3) 0.85447(17) 0.0517(6) Uani 1 1 d . . . O15 O 0.42617(13) 0.0817(2) 0.83856(14) 0.0654(6) Uani 1 1 d . . . C16 C 0.26647(17) 0.1964(3) 0.81285(16) 0.0477(6) Uani 1 1 d . . . H16A H 0.2391 0.1753 0.7469 0.057 Uiso 1 1 calc R . . C17 C 0.3747(2) 0.3590(3) 0.69958(19) 0.0601(7) Uani 1 1 d . . . H17A H 0.3122 0.3469 0.6566 0.090 Uiso 1 1 calc R . . H17B H 0.4027 0.2620 0.7176 0.090 Uiso 1 1 calc R . . H17C H 0.4157 0.4152 0.6709 0.090 Uiso 1 1 calc R . . C18 C 0.46371(18) 0.4642(3) 0.8549(2) 0.0598(7) Uani 1 1 d . . . H18A H 0.5066 0.5128 0.8251 0.090 Uiso 1 1 calc R . . H18B H 0.4894 0.3676 0.8774 0.090 Uiso 1 1 calc R . . H18C H 0.4573 0.5247 0.9058 0.090 Uiso 1 1 calc R . . O19 O 0.16978(14) 0.3588(2) 1.07064(13) 0.0675(6) Uani 1 1 d . . . C19 C 0.13423(18) 0.3066(3) 0.99476(18) 0.0528(6) Uani 1 1 d . . . O20 O 0.04742(12) 0.2468(2) 0.96594(12) 0.0593(5) Uani 1 1 d . . . C20 C -0.01453(19) 0.2538(4) 1.0287(2) 0.0650(8) Uani 1 1 d . . . H20A H -0.0808 0.2338 0.9942 0.078 Uiso 1 1 calc R . . H20B H -0.0120 0.3544 1.0541 0.078 Uiso 1 1 calc R . . C21 C 0.0153(2) 0.1440(4) 1.1055(2) 0.0773(9) Uani 1 1 d . . . H21A H -0.0265 0.1529 1.1452 0.116 Uiso 1 1 calc R . . H21B H 0.0806 0.1640 1.1402 0.116 Uiso 1 1 calc R . . H21C H 0.0109 0.0441 1.0806 0.116 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 N1 0.0361(11) 0.0617(13) 0.0469(11) 0.0022(10) 0.0110(9) 0.0012(9) S2 0.0453(4) 0.0641(5) 0.0435(4) -0.0045(3) 0.0098(3) -0.0051(3) C2 0.0383(13) 0.0594(15) 0.0409(12) -0.0024(11) 0.0079(10) 0.0016(11) C3 0.0384(13) 0.0630(16) 0.0494(14) 0.0012(12) 0.0119(11) -0.0035(11) C4 0.0465(14) 0.0600(16) 0.0444(13) 0.0002(12) 0.0102(11) -0.0034(11) C5 0.0552(16) 0.0688(18) 0.0576(16) 0.0015(14) 0.0149(13) -0.0137(14) C6 0.0672(18) 0.0589(16) 0.0577(16) 0.0057(14) 0.0139(13) -0.0074(14) C7 0.0671(18) 0.0607(17) 0.0537(15) 0.0052(13) 0.0099(13) 0.0048(14) C8 0.0496(15) 0.0703(18) 0.0509(14) 0.0025(13) 0.0078(12) 0.0014(13) C9 0.0460(14) 0.0563(15) 0.0433(13) 0.0019(11) 0.0103(11) 0.0009(11) C10 0.0419(14) 0.0620(16) 0.0493(14) -0.0064(12) 0.0122(11) -0.0018(12) O10 0.0490(11) 0.0747(13) 0.0714(12) 0.0063(10) 0.0241(9) 0.0121(9) C11 0.0414(13) 0.0666(16) 0.0454(13) -0.0063(12) 0.0126(11) 0.0000(12) C12 0.0404(13) 0.0573(15) 0.0463(13) -0.0062(12) 0.0111(10) -0.0051(11) O13 0.0695(13) 0.0822(14) 0.0739(13) 0.0188(11) 0.0278(11) -0.0006(11) C13 0.0490(15) 0.0598(16) 0.0537(15) -0.0022(13) 0.0141(12) -0.0088(12) N14 0.0544(13) 0.0566(13) 0.0562(13) 0.0049(11) 0.0127(10) 0.0039(10) C14 0.0694(19) 0.073(2) 0.073(2) 0.0112(16) 0.0137(15) 0.0114(15) C15 0.0485(15) 0.0573(15) 0.0490(14) -0.0056(12) 0.0132(12) 0.0005(12) O15 0.0509(11) 0.0756(13) 0.0734(13) 0.0051(10) 0.0231(10) 0.0098(9) C16 0.0453(13) 0.0571(15) 0.0403(12) -0.0031(11) 0.0110(10) -0.0019(11) C17 0.0577(16) 0.0714(18) 0.0564(16) -0.0016(14) 0.0245(13) -0.0010(14) C18 0.0412(14) 0.0718(18) 0.0646(16) 0.0020(14) 0.0111(12) -0.0028(13) O19 0.0687(12) 0.0869(14) 0.0499(11) -0.0150(10) 0.0212(10) -0.0162(11) C19 0.0508(15) 0.0592(16) 0.0508(15) -0.0018(12) 0.0178(12) -0.0010(12) O20 0.0474(10) 0.0855(13) 0.0480(10) -0.0026(9) 0.0178(8) -0.0095(9) C20 0.0531(16) 0.086(2) 0.0612(16) 0.0061(15) 0.0253(13) 0.0030(15) C21 0.0702(19) 0.102(3) 0.0592(18) 0.0091(17) 0.0163(15) -0.0103(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C10 1.371(3) . ? N1 C9 1.424(3) . ? N1 C2 1.479(3) . ? S2 C11 1.834(2) . ? S2 C2 1.859(2) . ? C2 C16 1.550(4) . ? C2 C3 1.552(3) . ? C3 C4 1.515(4) . ? C3 C18 1.533(3) . ? C3 C17 1.541(4) . ? C4 C9 1.380(3) . ? C4 C5 1.386(4) . ? C5 C6 1.389(4) . ? C6 C7 1.362(4) . ? C7 C8 1.396(4) . ? C8 C9 1.386(4) . ? C10 O10 1.212(3) . ? C10 C11 1.530(4) . ? C11 C19 1.504(3) . ? C11 C12 1.558(4) . ? C12 C13 1.509(4) . ? C12 C16 1.543(3) . ? O13 C13 1.205(3) . ? C13 N14 1.378(3) . ? N14 C15 1.383(3) . ? N14 C14 1.455(3) . ? C15 O15 1.210(3) . ? C15 C16 1.509(4) . ? O19 C19 1.209(3) . ? C19 O20 1.318(3) . ? O20 C20 1.466(3) . ? C20 C21 1.484(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 C10 N1 C9 125.1(2) . . ? C10 N1 C2 112.0(2) . . ? C9 N1 C2 109.38(19) . . ? C11 S2 C2 79.49(11) . . ? N1 C2 C16 105.97(19) . . ? N1 C2 C3 105.0(2) . . ? C16 C2 C3 121.6(2) . . ? N1 C2 S2 101.86(15) . . ? C16 C2 S2 101.86(16) . . ? C3 C2 S2 118.33(17) . . ? C4 C3 C18 113.5(2) . . ? C4 C3 C17 107.3(2) . . ? C18 C3 C17 110.1(2) . . ? C4 C3 C2 101.64(19) . . ? C18 C3 C2 112.7(2) . . ? C17 C3 C2 111.3(2) . . ? C9 C4 C5 118.4(3) . . ? C9 C4 C3 111.4(2) . . ? C5 C4 C3 129.9(2) . . ? C4 C5 C6 119.2(3) . . ? C7 C6 C5 121.2(3) . . ? C6 C7 C8 121.3(3) . . ? C9 C8 C7 116.4(3) . . ? C4 C9 C8 123.5(2) . . ? C4 C9 N1 109.2(2) . . ? C8 C9 N1 127.3(2) . . ? O10 C10 N1 126.3(3) . . ? O10 C10 C11 127.3(2) . . ? N1 C10 C11 106.3(2) . . ? C19 C11 C10 112.4(2) . . ? C19 C11 C12 117.6(2) . . ? C10 C11 C12 106.2(2) . . ? C19 C11 S2 113.86(18) . . ? C10 C11 S2 101.21(18) . . ? C12 C11 S2 103.95(16) . . ? C13 C12 C16 105.29(19) . . ? C13 C12 C11 112.4(2) . . ? C16 C12 C11 105.3(2) . . ? O13 C13 N14 124.4(3) . . ? O13 C13 C12 127.4(2) . . ? N14 C13 C12 108.2(2) . . ? C13 N14 C15 113.1(2) . . ? C13 N14 C14 122.6(2) . . ? C15 N14 C14 124.1(2) . . ? O15 C15 N14 123.1(2) . . ? O15 C15 C16 128.0(2) . . ? N14 C15 C16 108.8(2) . . ? C15 C16 C12 103.9(2) . . ? C15 C16 C2 115.4(2) . . ? C12 C16 C2 105.10(19) . . ? O19 C19 O20 125.8(2) . . ? O19 C19 C11 122.7(2) . . ? O20 C19 C11 111.4(2) . . ? C19 O20 C20 117.4(2) . . ? O20 C20 C21 112.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 C2 C16 70.7(2) . . . . ? C9 N1 C2 C16 -146.18(19) . . . . ? C10 N1 C2 C3 -159.4(2) . . . . ? C9 N1 C2 C3 -16.3(3) . . . . ? C10 N1 C2 S2 -35.5(2) . . . . ? C9 N1 C2 S2 107.65(18) . . . . ? C11 S2 C2 N1 50.99(17) . . . . ? C11 S2 C2 C16 -58.36(15) . . . . ? C11 S2 C2 C3 165.5(2) . . . . ? N1 C2 C3 C4 17.6(2) . . . . ? C16 C2 C3 C4 137.6(2) . . . . ? S2 C2 C3 C4 -95.1(2) . . . . ? N1 C2 C3 C18 139.4(2) . . . . ? C16 C2 C3 C18 -100.6(3) . . . . ? S2 C2 C3 C18 26.7(3) . . . . ? N1 C2 C3 C17 -96.4(2) . . . . ? C16 C2 C3 C17 23.6(3) . . . . ? S2 C2 C3 C17 150.86(19) . . . . ? C18 C3 C4 C9 -135.3(2) . . . . ? C17 C3 C4 C9 102.9(2) . . . . ? C2 C3 C4 C9 -14.1(3) . . . . ? C18 C3 C4 C5 49.9(4) . . . . ? C17 C3 C4 C5 -71.9(3) . . . . ? C2 C3 C4 C5 171.2(3) . . . . ? C9 C4 C5 C6 0.5(4) . . . . ? C3 C4 C5 C6 175.0(3) . . . . ? C4 C5 C6 C7 0.3(4) . . . . ? C5 C6 C7 C8 -0.9(5) . . . . ? C6 C7 C8 C9 0.7(4) . . . . ? C5 C4 C9 C8 -0.8(4) . . . . ? C3 C4 C9 C8 -176.3(2) . . . . ? C5 C4 C9 N1 -179.9(2) . . . . ? C3 C4 C9 N1 4.6(3) . . . . ? C7 C8 C9 C4 0.2(4) . . . . ? C7 C8 C9 N1 179.2(2) . . . . ? C10 N1 C9 C4 144.9(2) . . . . ? C2 N1 C9 C4 7.7(3) . . . . ? C10 N1 C9 C8 -34.2(4) . . . . ? C2 N1 C9 C8 -171.4(2) . . . . ? C9 N1 C10 O10 37.9(4) . . . . ? C2 N1 C10 O10 174.1(3) . . . . ? C9 N1 C10 C11 -141.7(2) . . . . ? C2 N1 C10 C11 -5.5(3) . . . . ? O10 C10 C11 C19 -12.9(4) . . . . ? N1 C10 C11 C19 166.7(2) . . . . ? O10 C10 C11 C12 117.0(3) . . . . ? N1 C10 C11 C12 -63.4(2) . . . . ? O10 C10 C11 S2 -134.8(3) . . . . ? N1 C10 C11 S2 44.8(2) . . . . ? C2 S2 C11 C19 -174.9(2) . . . . ? C2 S2 C11 C10 -54.09(16) . . . . ? C2 S2 C11 C12 55.93(17) . . . . ? C19 C11 C12 C13 -51.4(3) . . . . ? C10 C11 C12 C13 -178.24(19) . . . . ? S2 C11 C12 C13 75.5(2) . . . . ? C19 C11 C12 C16 -165.5(2) . . . . ? C10 C11 C12 C16 67.7(2) . . . . ? S2 C11 C12 C16 -38.6(2) . . . . ? C16 C12 C13 O13 175.6(3) . . . . ? C11 C12 C13 O13 61.5(4) . . . . ? C16 C12 C13 N14 -2.8(3) . . . . ? C11 C12 C13 N14 -117.0(2) . . . . ? O13 C13 N14 C15 -171.3(3) . . . . ? C12 C13 N14 C15 7.3(3) . . . . ? O13 C13 N14 C14 3.7(4) . . . . ? C12 C13 N14 C14 -177.8(2) . . . . ? C13 N14 C15 O15 171.9(2) . . . . ? C14 N14 C15 O15 -3.0(4) . . . . ? C13 N14 C15 C16 -8.7(3) . . . . ? C14 N14 C15 C16 176.4(2) . . . . ? O15 C15 C16 C12 -174.4(3) . . . . ? N14 C15 C16 C12 6.2(3) . . . . ? O15 C15 C16 C2 -59.8(3) . . . . ? N14 C15 C16 C2 120.7(2) . . . . ? C13 C12 C16 C15 -2.0(3) . . . . ? C11 C12 C16 C15 117.0(2) . . . . ? C13 C12 C16 C2 -123.7(2) . . . . ? C11 C12 C16 C2 -4.7(2) . . . . ? N1 C2 C16 C15 -174.63(19) . . . . ? C3 C2 C16 C15 65.8(3) . . . . ? S2 C2 C16 C15 -68.5(2) . . . . ? N1 C2 C16 C12 -60.8(2) . . . . ? C3 C2 C16 C12 179.7(2) . . . . ? S2 C2 C16 C12 45.40(19) . . . . ? C10 C11 C19 O19 -106.7(3) . . . . ? C12 C11 C19 O19 129.5(3) . . . . ? S2 C11 C19 O19 7.6(4) . . . . ? C10 C11 C19 O20 69.3(3) . . . . ? C12 C11 C19 O20 -54.5(3) . . . . ? S2 C11 C19 O20 -176.41(19) . . . . ? O19 C19 O20 C20 4.8(4) . . . . ? C11 C19 O20 C20 -171.0(2) . . . . ? C19 O20 C20 C21 -75.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 60.06 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.309 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.051 #===END data_11 _database_code_CSD 211110 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 N O6 S' _chemical_formula_sum 'C19 H17 N O6 S' _chemical_formula_weight 387.40 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 7.8459(7) _cell_length_b 9.6884(9) _cell_length_c 24.179(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.467(2) _cell_angle_gamma 90.00 _cell_volume 1826.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 59 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .15 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.735934 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7637 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 23.21 _reflns_number_total 2589 _reflns_number_gt 1548 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0737P)^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 SHELXL _refine_ls_extinction_coef 0.0020(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2589 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1253 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.925 _refine_ls_shift/su_max 0.029 _refine_ls_shift/su_mean 0.005 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 N1 N 0.7895(3) 0.2024(3) 0.86070(10) 0.0445(7) Uani 1 1 d . . . C2 C 0.7655(4) 0.3386(3) 0.88731(12) 0.0486(8) Uani 1 1 d . . . S2 S 0.98700(10) 0.41213(9) 0.89256(3) 0.0545(3) Uani 1 1 d . . . C3 C 0.6921(5) 0.3044(5) 0.94268(14) 0.0670(11) Uani 1 1 d . . . C4 C 0.7436(5) 0.1549(5) 0.95037(15) 0.0681(11) Uani 1 1 d . . . C5 C 0.7414(6) 0.0696(7) 0.99698(19) 0.1087(19) Uani 1 1 d . . . H5A H 0.7102 0.1053 1.0301 0.130 Uiso 1 1 calc R . . C6 C 0.7852(7) -0.0659(8) 0.9936(3) 0.128(3) Uani 1 1 d . . . H6A H 0.7848 -0.1221 1.0248 0.154 Uiso 1 1 calc R . . C7 C 0.8302(6) -0.1211(5) 0.9447(3) 0.1083(18) Uani 1 1 d . . . H7A H 0.8592 -0.2140 0.9434 0.130 Uiso 1 1 calc R . . C8 C 0.8328(5) -0.0395(4) 0.89713(17) 0.0764(12) Uani 1 1 d . . . H8A H 0.8621 -0.0758 0.8639 0.092 Uiso 1 1 calc R . . C9 C 0.7899(4) 0.0972(4) 0.90200(14) 0.0572(9) Uani 1 1 d . . . C10 C 0.9069(4) 0.2115(4) 0.82277(13) 0.0461(8) Uani 1 1 d . . . O10 O 0.9649(3) 0.1165(3) 0.79803(10) 0.0668(7) Uani 1 1 d . . . C11 C 0.9548(4) 0.3642(3) 0.81829(12) 0.0482(9) Uani 1 1 d . . . C12 C 0.7894(4) 0.4430(3) 0.79617(13) 0.0520(9) Uani 1 1 d . . . H12A H 0.7378 0.4055 0.7605 0.062 Uiso 1 1 calc R . . C13 C 0.8241(6) 0.5962(4) 0.79219(19) 0.0730(11) Uani 1 1 d . . . O13 O 0.9157(4) 0.6571(3) 0.76509(14) 0.1027(11) Uani 1 1 d . . . O14 O 0.7279(4) 0.6663(3) 0.82728(14) 0.0913(9) Uani 1 1 d . . . C15 C 0.6394(6) 0.5770(5) 0.8587(2) 0.0794(12) Uani 1 1 d . . . O15 O 0.5569(4) 0.6202(3) 0.89322(16) 0.1197(13) Uani 1 1 d . . . C16 C 0.6683(4) 0.4289(3) 0.84148(14) 0.0527(9) Uani 1 1 d . . . H16A H 0.5600 0.3854 0.8266 0.063 Uiso 1 1 calc R . . C17 C 0.4933(5) 0.3144(5) 0.93567(18) 0.0977(15) Uani 1 1 d . . . H17A H 0.4595 0.4092 0.9307 0.147 Uiso 1 1 calc R . . H17B H 0.4498 0.2781 0.9683 0.147 Uiso 1 1 calc R . . H17C H 0.4477 0.2620 0.9037 0.147 Uiso 1 1 calc R . . C18 C 0.7652(6) 0.3995(5) 0.99134(15) 0.0952(15) Uani 1 1 d . . . H18A H 0.7266 0.4924 0.9839 0.143 Uiso 1 1 calc R . . H18B H 0.8882 0.3970 0.9948 0.143 Uiso 1 1 calc R . . H18C H 0.7260 0.3680 1.0253 0.143 Uiso 1 1 calc R . . C19 C 1.1121(5) 0.3887(4) 0.78846(16) 0.0672(11) Uani 1 1 d . . . O19 O 1.2481(3) 0.4218(4) 0.81160(12) 0.1048(11) Uani 1 1 d . . . O20 O 1.0746(3) 0.3677(3) 0.73477(11) 0.0905(9) Uani 1 1 d . . . C20 C 1.2180(7) 0.3831(7) 0.6990(2) 0.143(2) Uani 1 1 d . . . H20A H 1.3125 0.4329 0.7192 0.172 Uiso 1 1 calc R . . H20B H 1.2592 0.2927 0.6895 0.172 Uiso 1 1 calc R . . C21 C 1.1631(8) 0.4504(9) 0.6533(2) 0.179(3) Uani 1 1 d . . . H21A H 1.2546 0.4589 0.6304 0.268 Uiso 1 1 calc R . . H21B H 1.1251 0.5407 0.6628 0.268 Uiso 1 1 calc R . . H21C H 1.0694 0.4010 0.6335 0.268 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 N1 0.0453(16) 0.0434(17) 0.0445(15) -0.0017(14) 0.0031(13) -0.0042(12) C2 0.0448(19) 0.054(2) 0.0473(19) -0.0122(17) 0.0051(16) -0.0047(16) S2 0.0450(5) 0.0669(7) 0.0491(5) -0.0038(5) -0.0050(4) -0.0104(4) C3 0.058(2) 0.096(3) 0.049(2) -0.014(2) 0.0142(18) -0.017(2) C4 0.061(2) 0.090(3) 0.052(2) 0.009(2) 0.0020(19) -0.031(2) C5 0.105(4) 0.156(5) 0.064(3) 0.023(4) 0.005(3) -0.069(4) C6 0.129(5) 0.148(6) 0.097(4) 0.062(5) -0.030(4) -0.083(5) C7 0.114(4) 0.082(4) 0.116(4) 0.038(4) -0.042(3) -0.044(3) C8 0.083(3) 0.056(3) 0.083(3) 0.016(2) -0.019(2) -0.020(2) C9 0.057(2) 0.059(3) 0.053(2) 0.012(2) -0.0080(17) -0.0182(19) C10 0.0343(18) 0.059(3) 0.0428(19) 0.0022(18) -0.0034(16) 0.0070(16) O10 0.0639(16) 0.0662(18) 0.0709(15) -0.0066(14) 0.0104(13) 0.0164(13) C11 0.0426(19) 0.055(2) 0.0454(18) 0.0031(16) -0.0006(15) -0.0038(16) C12 0.048(2) 0.051(2) 0.053(2) 0.0006(17) -0.0131(16) -0.0027(16) C13 0.066(3) 0.061(3) 0.085(3) 0.012(3) -0.024(2) -0.004(2) O13 0.098(2) 0.081(2) 0.122(3) 0.0400(19) -0.017(2) -0.0307(18) O14 0.102(2) 0.0460(17) 0.118(2) -0.0059(18) -0.022(2) 0.0043(17) C15 0.066(3) 0.069(3) 0.098(3) -0.025(3) -0.013(2) 0.015(2) O15 0.109(3) 0.095(3) 0.156(3) -0.059(2) 0.021(2) 0.0274(19) C16 0.0400(18) 0.050(2) 0.065(2) -0.0156(18) -0.0043(16) 0.0047(16) C17 0.064(3) 0.144(4) 0.091(3) -0.026(3) 0.033(2) -0.021(3) C18 0.098(3) 0.132(4) 0.060(2) -0.037(3) 0.026(2) -0.030(3) C19 0.050(2) 0.091(3) 0.061(2) 0.010(2) 0.008(2) -0.010(2) O19 0.0472(17) 0.176(3) 0.0906(19) 0.004(2) 0.0036(15) -0.0294(18) O20 0.0685(17) 0.147(3) 0.0583(16) 0.0138(17) 0.0176(14) -0.0250(17) C20 0.089(4) 0.247(7) 0.098(4) 0.065(4) 0.031(3) -0.040(4) C21 0.118(5) 0.327(10) 0.091(4) 0.046(5) 0.014(4) -0.072(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C10 1.374(4) . ? N1 C9 1.426(4) . ? N1 C2 1.489(4) . ? C2 C16 1.545(4) . ? C2 C3 1.552(4) . ? C2 S2 1.869(3) . ? S2 C11 1.844(3) . ? C3 C4 1.510(6) . ? C3 C17 1.553(5) . ? C3 C18 1.553(5) . ? C4 C9 1.381(5) . ? C4 C5 1.399(6) . ? C5 C6 1.362(7) . ? C6 C7 1.380(8) . ? C7 C8 1.398(6) . ? C8 C9 1.375(5) . ? C10 O10 1.213(4) . ? C10 C11 1.534(5) . ? C11 C19 1.516(5) . ? C11 C12 1.548(4) . ? C12 C13 1.514(5) . ? C12 C16 1.535(5) . ? C13 O13 1.183(5) . ? C13 O14 1.377(5) . ? O14 C15 1.388(5) . ? C15 O15 1.189(5) . ? C15 C16 1.518(5) . ? C19 O19 1.192(4) . ? C19 O20 1.314(4) . ? O20 C20 1.502(5) . ? C20 C21 1.312(7) . ? 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 C10 N1 C9 124.4(3) . . ? C10 N1 C2 111.0(3) . . ? C9 N1 C2 108.7(3) . . ? N1 C2 C16 105.6(2) . . ? N1 C2 C3 105.1(3) . . ? C16 C2 C3 122.6(3) . . ? N1 C2 S2 101.87(19) . . ? C16 C2 S2 102.3(2) . . ? C3 C2 S2 117.1(2) . . ? C11 S2 C2 79.26(13) . . ? C4 C3 C17 109.0(3) . . ? C4 C3 C2 101.0(3) . . ? C17 C3 C2 111.0(3) . . ? C4 C3 C18 113.9(3) . . ? C17 C3 C18 109.1(3) . . ? C2 C3 C18 112.7(3) . . ? C9 C4 C5 118.1(5) . . ? C9 C4 C3 112.1(3) . . ? C5 C4 C3 129.7(4) . . ? C6 C5 C4 119.7(5) . . ? C5 C6 C7 121.0(5) . . ? C6 C7 C8 121.0(5) . . ? C9 C8 C7 116.6(4) . . ? C8 C9 C4 123.5(3) . . ? C8 C9 N1 127.5(3) . . ? C4 C9 N1 108.9(3) . . ? O10 C10 N1 126.7(3) . . ? O10 C10 C11 126.0(3) . . ? N1 C10 C11 107.3(3) . . ? C19 C11 C10 113.8(3) . . ? C19 C11 C12 117.0(3) . . ? C10 C11 C12 107.3(2) . . ? C19 C11 S2 113.2(2) . . ? C10 C11 S2 100.5(2) . . ? C12 C11 S2 103.3(2) . . ? C13 C12 C16 105.3(3) . . ? C13 C12 C11 110.8(3) . . ? C16 C12 C11 105.8(2) . . ? O13 C13 O14 120.3(4) . . ? O13 C13 C12 130.5(5) . . ? O14 C13 C12 109.2(4) . . ? C13 O14 C15 111.9(3) . . ? O15 C15 O14 120.7(4) . . ? O15 C15 C16 129.5(5) . . ? O14 C15 C16 109.9(4) . . ? C15 C16 C12 103.6(3) . . ? C15 C16 C2 114.6(3) . . ? C12 C16 C2 105.5(2) . . ? O19 C19 O20 126.4(3) . . ? O19 C19 C11 123.5(3) . . ? O20 C19 C11 110.0(3) . . ? C19 O20 C20 117.1(3) . . ? C21 C20 O20 109.7(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 C2 C16 70.7(3) . . . . ? C9 N1 C2 C16 -149.1(2) . . . . ? C10 N1 C2 C3 -158.4(2) . . . . ? C9 N1 C2 C3 -18.2(3) . . . . ? C10 N1 C2 S2 -35.8(3) . . . . ? C9 N1 C2 S2 104.4(2) . . . . ? N1 C2 S2 C11 51.8(2) . . . . ? C16 C2 S2 C11 -57.3(2) . . . . ? C3 C2 S2 C11 165.8(3) . . . . ? N1 C2 C3 C4 19.8(3) . . . . ? C16 C2 C3 C4 139.9(3) . . . . ? S2 C2 C3 C4 -92.4(3) . . . . ? N1 C2 C3 C17 -95.6(4) . . . . ? C16 C2 C3 C17 24.5(5) . . . . ? S2 C2 C3 C17 152.2(3) . . . . ? N1 C2 C3 C18 141.7(3) . . . . ? C16 C2 C3 C18 -98.1(4) . . . . ? S2 C2 C3 C18 29.5(4) . . . . ? C17 C3 C4 C9 101.0(4) . . . . ? C2 C3 C4 C9 -15.9(4) . . . . ? C18 C3 C4 C9 -137.0(3) . . . . ? C17 C3 C4 C5 -75.2(5) . . . . ? C2 C3 C4 C5 167.8(4) . . . . ? C18 C3 C4 C5 46.8(5) . . . . ? C9 C4 C5 C6 0.3(6) . . . . ? C3 C4 C5 C6 176.4(4) . . . . ? C4 C5 C6 C7 -0.7(8) . . . . ? C5 C6 C7 C8 0.3(8) . . . . ? C6 C7 C8 C9 0.5(7) . . . . ? C7 C8 C9 C4 -0.8(6) . . . . ? C7 C8 C9 N1 177.2(3) . . . . ? C5 C4 C9 C8 0.5(5) . . . . ? C3 C4 C9 C8 -176.3(3) . . . . ? C5 C4 C9 N1 -177.9(3) . . . . ? C3 C4 C9 N1 5.3(4) . . . . ? C10 N1 C9 C8 -36.2(5) . . . . ? C2 N1 C9 C8 -169.8(3) . . . . ? C10 N1 C9 C4 142.1(3) . . . . ? C2 N1 C9 C4 8.5(3) . . . . ? C9 N1 C10 O10 40.3(5) . . . . ? C2 N1 C10 O10 173.1(3) . . . . ? C9 N1 C10 C11 -138.4(3) . . . . ? C2 N1 C10 C11 -5.7(3) . . . . ? O10 C10 C11 C19 -12.1(4) . . . . ? N1 C10 C11 C19 166.7(3) . . . . ? O10 C10 C11 C12 119.0(3) . . . . ? N1 C10 C11 C12 -62.2(3) . . . . ? O10 C10 C11 S2 -133.4(3) . . . . ? N1 C10 C11 S2 45.4(2) . . . . ? C2 S2 C11 C19 -176.1(3) . . . . ? C2 S2 C11 C10 -54.4(2) . . . . ? C2 S2 C11 C12 56.4(2) . . . . ? C19 C11 C12 C13 -52.5(4) . . . . ? C10 C11 C12 C13 178.2(3) . . . . ? S2 C11 C12 C13 72.6(3) . . . . ? C19 C11 C12 C16 -166.1(3) . . . . ? C10 C11 C12 C16 64.6(3) . . . . ? S2 C11 C12 C16 -41.0(3) . . . . ? C16 C12 C13 O13 176.1(4) . . . . ? C11 C12 C13 O13 62.2(5) . . . . ? C16 C12 C13 O14 -3.8(3) . . . . ? C11 C12 C13 O14 -117.7(3) . . . . ? O13 C13 O14 C15 -175.2(3) . . . . ? C12 C13 O14 C15 4.7(4) . . . . ? C13 O14 C15 O15 176.2(4) . . . . ? C13 O14 C15 C16 -3.7(4) . . . . ? O15 C15 C16 C12 -178.7(4) . . . . ? O14 C15 C16 C12 1.1(4) . . . . ? O15 C15 C16 C2 -64.4(5) . . . . ? O14 C15 C16 C2 115.4(3) . . . . ? C13 C12 C16 C15 1.6(3) . . . . ? C11 C12 C16 C15 118.9(3) . . . . ? C13 C12 C16 C2 -119.2(3) . . . . ? C11 C12 C16 C2 -1.8(3) . . . . ? N1 C2 C16 C15 -176.4(3) . . . . ? C3 C2 C16 C15 63.7(4) . . . . ? S2 C2 C16 C15 -70.2(3) . . . . ? N1 C2 C16 C12 -63.1(3) . . . . ? C3 C2 C16 C12 176.9(3) . . . . ? S2 C2 C16 C12 43.1(2) . . . . ? C10 C11 C19 O19 -106.5(4) . . . . ? C12 C11 C19 O19 127.3(4) . . . . ? S2 C11 C19 O19 7.4(5) . . . . ? C10 C11 C19 O20 73.3(4) . . . . ? C12 C11 C19 O20 -52.8(4) . . . . ? S2 C11 C19 O20 -172.8(3) . . . . ? O19 C19 O20 C20 1.7(7) . . . . ? C11 C19 O20 C20 -178.1(4) . . . . ? C19 O20 C20 C21 -137.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 23.21 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.224 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.039 #===END data_18 _database_code_CSD 211111 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H17 N O3 S' _chemical_formula_sum 'C17 H17 N O3 S' _chemical_formula_weight 315.38 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.48(4) _cell_length_b 18.39(9) _cell_length_c 10.41(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.58(5) _cell_angle_gamma 90.00 _cell_volume 1601(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max .15 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.699100 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6390 _diffrn_reflns_av_R_equivalents 0.0977 _diffrn_reflns_av_sigmaI/netI 0.1335 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 23.17 _reflns_number_total 2230 _reflns_number_gt 1079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0813P)^2^+0.9791P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0018(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2230 _refine_ls_number_parameters 200 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1630 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1889 _refine_ls_wR_factor_gt 0.1506 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _refine_ls_shift/su_max 0.093 _refine_ls_shift/su_mean 0.005 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 N1 N -0.0754(6) 0.5896(3) 0.0821(4) 0.0370(13) Uani 1 1 d . . . C2 C 0.0561(8) 0.6154(3) 0.1554(6) 0.0384(16) Uani 1 1 d . . . S2 S 0.1984(2) 0.63719(9) 0.06937(15) 0.0476(6) Uani 1 1 d . . . C3 C 0.0427(7) 0.6168(3) 0.3005(5) 0.0390(16) Uani 1 1 d . . . C4 C -0.1276(7) 0.5892(3) 0.2904(5) 0.0361(15) Uani 1 1 d . . . C5 C -0.2187(8) 0.5780(3) 0.3866(6) 0.0502(18) Uani 1 1 d . . . H5A H -0.1778 0.5887 0.4731 0.060 Uiso 1 1 calc R . . C6 C -0.3745(9) 0.5502(4) 0.3522(7) 0.0541(19) Uani 1 1 d . . . H6A H -0.4362 0.5417 0.4167 0.065 Uiso 1 1 calc R . . C7 C -0.4369(8) 0.5352(3) 0.2233(7) 0.0556(19) Uani 1 1 d . . . H7A H -0.5413 0.5182 0.2022 0.067 Uiso 1 1 calc R . . C8 C -0.3460(8) 0.5453(3) 0.1242(6) 0.0484(18) Uani 1 1 d . . . H8A H -0.3859 0.5341 0.0378 0.058 Uiso 1 1 calc R . . C9 C -0.1934(7) 0.5727(3) 0.1617(5) 0.0363(15) Uani 1 1 d . . . C10 C -0.0738(8) 0.5838(3) -0.0575(6) 0.0396(16) Uani 1 1 d . . . O10 O -0.1894(5) 0.5589(2) -0.1316(4) 0.0563(13) Uani 1 1 d . . . C11 C 0.0786(8) 0.6110(3) -0.0755(6) 0.0414(17) Uani 1 1 d . . . C12 C 0.1354(9) 0.6195(3) -0.1977(6) 0.0478(18) Uani 1 1 d . . . O12 O 0.0634(6) 0.6060(2) -0.3066(4) 0.0588(14) Uani 1 1 d . . . O13 O 0.2867(6) 0.6475(2) -0.1759(4) 0.0531(13) Uani 1 1 d . . . C14 C 0.3590(8) 0.6626(4) -0.2886(6) 0.059(2) Uani 1 1 d . . . H14A H 0.2884 0.6924 -0.3501 0.071 Uiso 1 1 calc R . . H14B H 0.3797 0.6176 -0.3316 0.071 Uiso 1 1 calc R . . C15 C 0.5120(10) 0.7019(4) -0.2427(7) 0.077(3) Uani 1 1 d . . . H15A H 0.4926 0.7415 -0.1856 0.093 Uiso 1 1 calc R . . H15B H 0.5880 0.6689 -0.1931 0.093 Uiso 1 1 calc R . . C16 C 0.5787(11) 0.7306(7) -0.3508(10) 0.152(5) Uani 1 1 d D . . H16A H 0.5112 0.7632 -0.4016 0.182 Uiso 1 1 calc R . . C17 C 0.7162(11) 0.7204(6) -0.3932(10) 0.135(4) Uani 1 1 d D . . H17A H 0.7921 0.6887 -0.3492 0.162 Uiso 1 1 calc R . . H17B H 0.7366 0.7448 -0.4670 0.162 Uiso 1 1 calc R . . C18 C 0.1647(7) 0.5654(4) 0.3784(6) 0.0526(19) Uani 1 1 d . . . H18A H 0.2702 0.5851 0.3822 0.079 Uiso 1 1 calc R . . H18B H 0.1590 0.5187 0.3367 0.079 Uiso 1 1 calc R . . H18C H 0.1416 0.5603 0.4651 0.079 Uiso 1 1 calc R . . C19 C 0.0617(8) 0.6948(3) 0.3553(6) 0.058(2) Uani 1 1 d . . . H19A H 0.1705 0.7102 0.3596 0.086 Uiso 1 1 calc R . . H19B H 0.0341 0.6956 0.4411 0.086 Uiso 1 1 calc R . . H19C H -0.0077 0.7269 0.2994 0.086 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 N1 0.038(3) 0.035(3) 0.036(3) -0.003(2) 0.001(3) -0.004(3) C2 0.036(4) 0.033(4) 0.045(4) -0.001(3) 0.002(3) -0.002(3) S2 0.0460(12) 0.0580(11) 0.0384(10) 0.0004(8) 0.0058(8) -0.0102(10) C3 0.039(4) 0.051(4) 0.026(3) -0.001(3) 0.003(3) -0.012(3) C4 0.033(4) 0.039(4) 0.036(4) -0.003(3) 0.005(3) -0.002(3) C5 0.054(5) 0.051(4) 0.046(4) 0.007(3) 0.010(4) 0.005(4) C6 0.052(5) 0.064(5) 0.051(5) 0.001(4) 0.022(4) 0.000(4) C7 0.036(4) 0.064(5) 0.066(5) 0.002(4) 0.009(4) -0.004(4) C8 0.035(4) 0.065(5) 0.046(4) -0.005(3) 0.007(4) -0.004(4) C9 0.035(4) 0.035(4) 0.040(4) 0.000(3) 0.009(3) -0.003(3) C10 0.048(5) 0.035(4) 0.032(4) -0.003(3) -0.005(3) 0.005(3) O10 0.052(3) 0.077(3) 0.037(3) -0.013(2) -0.001(2) -0.010(3) C11 0.046(5) 0.042(4) 0.035(4) -0.003(3) 0.003(3) -0.004(3) C12 0.062(6) 0.042(4) 0.040(4) 0.001(3) 0.011(4) 0.008(4) O12 0.070(4) 0.075(3) 0.033(3) -0.003(2) 0.011(3) -0.007(3) O13 0.054(3) 0.066(3) 0.042(3) 0.000(2) 0.016(2) -0.010(3) C14 0.060(5) 0.075(5) 0.047(4) -0.006(4) 0.021(4) -0.020(4) C15 0.079(6) 0.099(6) 0.059(5) 0.001(5) 0.026(5) -0.015(5) C16 0.107(10) 0.253(15) 0.099(9) -0.041(9) 0.029(8) -0.074(11) C17 0.101(9) 0.185(12) 0.114(9) -0.052(8) 0.006(8) -0.037(9) C18 0.041(4) 0.075(5) 0.039(4) 0.007(3) 0.000(3) 0.004(4) C19 0.073(6) 0.050(5) 0.049(4) -0.005(3) 0.010(4) -0.011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.331(8) . ? N1 C9 1.436(8) . ? N1 C10 1.459(10) . ? C2 C3 1.533(10) . ? C2 S2 1.667(8) . ? S2 C11 1.741(8) . ? C3 C4 1.518(10) . ? C3 C18 1.530(9) . ? C3 C19 1.542(10) . ? C4 C5 1.379(9) . ? C4 C9 1.396(9) . ? C5 C6 1.407(10) . ? C6 C7 1.385(10) . ? C7 C8 1.399(10) . ? C8 C9 1.383(10) . ? C10 O10 1.230(8) . ? C10 C11 1.427(10) . ? C11 C12 1.441(10) . ? C12 O12 1.220(9) . ? C12 O13 1.368(10) . ? O13 C14 1.438(9) . ? C14 C15 1.493(11) . ? C15 C16 1.441(12) . ? C16 C17 1.328(5) . ? 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 N1 C9 110.2(6) . . ? C2 N1 C10 116.8(5) . . ? C9 N1 C10 133.0(5) . . ? N1 C2 C3 112.2(6) . . ? N1 C2 S2 113.0(6) . . ? C3 C2 S2 134.8(5) . . ? C2 S2 C11 91.6(5) . . ? C4 C3 C18 112.5(6) . . ? C4 C3 C2 98.8(5) . . ? C18 C3 C2 110.9(5) . . ? C4 C3 C19 112.1(5) . . ? C18 C3 C19 111.0(6) . . ? C2 C3 C19 111.0(5) . . ? C5 C4 C9 118.8(7) . . ? C5 C4 C3 129.9(6) . . ? C9 C4 C3 111.3(5) . . ? C4 C5 C6 119.1(7) . . ? C7 C6 C5 120.7(6) . . ? C6 C7 C8 121.2(7) . . ? C9 C8 C7 116.5(6) . . ? C8 C9 C4 123.8(6) . . ? C8 C9 N1 128.8(6) . . ? C4 C9 N1 107.5(6) . . ? O10 C10 C11 133.9(6) . . ? O10 C10 N1 120.8(6) . . ? C11 C10 N1 105.3(5) . . ? C10 C11 C12 126.6(6) . . ? C10 C11 S2 113.3(5) . . ? C12 C11 S2 120.1(6) . . ? O12 C12 O13 122.8(6) . . ? O12 C12 C11 127.5(7) . . ? O13 C12 C11 109.7(6) . . ? C12 O13 C14 117.0(5) . . ? O13 C14 C15 107.3(6) . . ? C16 C15 C14 111.1(7) . . ? C17 C16 C15 133.5(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 C9 N1 C2 C3 1.8(6) . . . . ? C10 N1 C2 C3 -178.1(4) . . . . ? C9 N1 C2 S2 -179.4(4) . . . . ? C10 N1 C2 S2 0.7(6) . . . . ? N1 C2 S2 C11 0.1(5) . . . . ? C3 C2 S2 C11 178.5(6) . . . . ? N1 C2 C3 C4 -2.4(6) . . . . ? S2 C2 C3 C4 179.2(5) . . . . ? N1 C2 C3 C18 115.9(7) . . . . ? S2 C2 C3 C18 -62.5(8) . . . . ? N1 C2 C3 C19 -120.2(6) . . . . ? S2 C2 C3 C19 61.4(8) . . . . ? C18 C3 C4 C5 64.0(8) . . . . ? C2 C3 C4 C5 -178.9(6) . . . . ? C19 C3 C4 C5 -61.9(8) . . . . ? C18 C3 C4 C9 -114.9(6) . . . . ? C2 C3 C4 C9 2.2(6) . . . . ? C19 C3 C4 C9 119.2(6) . . . . ? C9 C4 C5 C6 0.2(9) . . . . ? C3 C4 C5 C6 -178.6(6) . . . . ? C4 C5 C6 C7 -1.0(10) . . . . ? C5 C6 C7 C8 1.9(10) . . . . ? C6 C7 C8 C9 -1.8(9) . . . . ? C7 C8 C9 C4 1.0(9) . . . . ? C7 C8 C9 N1 -178.8(6) . . . . ? C5 C4 C9 C8 -0.3(9) . . . . ? C3 C4 C9 C8 178.8(6) . . . . ? C5 C4 C9 N1 179.6(5) . . . . ? C3 C4 C9 N1 -1.3(6) . . . . ? C2 N1 C9 C8 179.6(6) . . . . ? C10 N1 C9 C8 -0.5(10) . . . . ? C2 N1 C9 C4 -0.3(6) . . . . ? C10 N1 C9 C4 179.6(6) . . . . ? C2 N1 C10 O10 178.3(5) . . . . ? C9 N1 C10 O10 -1.6(9) . . . . ? C2 N1 C10 C11 -1.3(7) . . . . ? C9 N1 C10 C11 178.8(6) . . . . ? O10 C10 C11 C12 3.4(11) . . . . ? N1 C10 C11 C12 -177.1(5) . . . . ? O10 C10 C11 S2 -178.2(6) . . . . ? N1 C10 C11 S2 1.3(6) . . . . ? C2 S2 C11 C10 -0.9(5) . . . . ? C2 S2 C11 C12 177.6(5) . . . . ? C10 C11 C12 O12 1.1(10) . . . . ? S2 C11 C12 O12 -177.2(5) . . . . ? C10 C11 C12 O13 179.6(6) . . . . ? S2 C11 C12 O13 1.3(7) . . . . ? O12 C12 O13 C14 1.4(9) . . . . ? C11 C12 O13 C14 -177.3(5) . . . . ? C12 O13 C14 C15 172.2(6) . . . . ? O13 C14 C15 C16 -169.7(8) . . . . ? C14 C15 C16 C17 -120.3(13) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 23.17 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.568 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.063 #===END