# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2005 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Mariusz, Jaremko' _publ_contact_author_address ; Faculty of Chemistry University of Wroclaw 14 Joliot-Curie St 50-383 Wroclaw Poland ; _publ_contact_author_email jaremko@gmail.com _publ_contact_author_fax ? _publ_contact_author_phone +48694267950 _publ_contact_letter ; ; _publ_requested_category Organic #========================================================================= # TITLE AND AUTHOR LIST _publ_section_title ; Crystal-state studies of p-toluenesulfonates of N-oxyimides - the possible structural basis of serine proteases inhibition ; loop_ _publ_author_name _publ_author_address S.Piotr ; Faculty of Chemistry University of Wroclaw 14 Joliot-Curie St 50-383 Wroclaw Poland ; J.Lukasz ; Faculty of Chemistry University of Wroclaw 14 Joliot-Curie St 50-383 Wroclaw Poland ; J.Mariusz ; Faculty of Chemistry University of Wroclaw 14 Joliot-Curie St 50-383 Wroclaw Poland ; L.Tadeusz ; Faculty of Chemistry University of Wroclaw 14 Joliot-Curie St 50-383 Wroclaw Poland ; data_compound_II _database_code_depnum_ccdc_archive 'CCDC 284049' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 401-403K _chemical_formula_moiety 'C19 H18 N2 O7 S' _chemical_formula_sum 'C19 H18 N2 O7 S' _chemical_formula_weight 418.41 _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.900(2) _cell_length_b 10.140(3) _cell_length_c 23.717(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1899.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10788 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 28.39 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Oxford Xcalibur PX \k geometry' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12965 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 28.39 _reflns_number_total 4431 _reflns_number_gt 3822 _reflns_threshold_expression >2sigma(I) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2003)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2003)' _computing_data_reduction CrysAlisRED _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003) ; _computing_publication_material SHELXL97 _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^)+(0.0350P)^2^] 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 0.00(6) _refine_ls_number_reflns 4431 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0677 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.008 _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 S S 1.04006(5) 0.87648(4) 0.253296(18) 0.01466(10) Uani 1 1 d . . . O2 O 1.10036(15) 0.99810(12) 0.23063(5) 0.0174(3) Uani 1 1 d . . . O6 O 0.43080(16) 0.89445(11) 0.16499(5) 0.0166(3) Uani 1 1 d . . . O3 O 1.11857(15) 0.75361(12) 0.23960(5) 0.0190(3) Uani 1 1 d . . . O4 O 0.79396(15) 1.01684(13) 0.13724(5) 0.0202(3) Uani 1 1 d . . . O7 O 0.24619(14) 1.00068(12) 0.10645(5) 0.0167(3) Uani 1 1 d . . . O1 O 0.84666(15) 0.84989(11) 0.22881(5) 0.0163(3) Uani 1 1 d . . . O5 O 0.60196(16) 0.90460(12) 0.31136(5) 0.0199(3) Uani 1 1 d . . . N1 N 0.74709(17) 0.96366(14) 0.23074(6) 0.0135(3) Uani 1 1 d . . . N2 N 0.4408(2) 1.11553(15) 0.15246(6) 0.0151(3) Uani 1 1 d . . . H2N H 0.398(3) 1.1790(19) 0.1425(8) 0.018 Uiso 1 1 d . . . C1 C 0.7181(2) 1.03294(17) 0.18063(7) 0.0141(4) Uani 1 1 d . . . C2 C 0.5750(2) 1.13024(18) 0.19385(7) 0.0138(4) Uani 1 1 d . . . H2 H 0.622(2) 1.2192(19) 0.1901(7) 0.017 Uiso 1 1 d . . . C3 C 0.5234(2) 1.09954(17) 0.25528(8) 0.0156(4) Uani 1 1 d . . . H3A H 0.558(2) 1.1702(19) 0.2796(8) 0.019 Uiso 1 1 d . . . H3B H 0.407(3) 1.0800(17) 0.2590(8) 0.019 Uiso 1 1 d . . . C4 C 0.6204(2) 0.97729(18) 0.27168(7) 0.0154(4) Uani 1 1 d . . . C5 C 0.3748(2) 0.99395(18) 0.14354(7) 0.0146(4) Uani 1 1 d . . . C6 C 0.1602(2) 0.8765(2) 0.09323(7) 0.0183(4) Uani 1 1 d . . . H6A H 0.059(3) 0.8744(19) 0.1169(8) 0.022 Uiso 1 1 d . . . H6B H 0.229(2) 0.7963(19) 0.1055(8) 0.022 Uiso 1 1 d . . . C11 C 1.0094(2) 0.89068(18) 0.32583(7) 0.0158(4) Uani 1 1 d . . . C21 C 0.9593(2) 0.77909(18) 0.35596(8) 0.0183(4) Uani 1 1 d . . . H21 H 0.953(3) 0.6919(19) 0.3366(7) 0.022 Uiso 1 1 d . . . C31 C 0.9352(2) 0.78977(18) 0.41307(8) 0.0206(4) Uani 1 1 d . . . H31 H 0.899(2) 0.7179(19) 0.4350(8) 0.025 Uiso 1 1 d . . . C41 C 0.9618(3) 0.90926(18) 0.44145(7) 0.0210(4) Uani 1 1 d . . . C51 C 1.0089(2) 1.01922(19) 0.41001(8) 0.0236(4) Uani 1 1 d . . . H51 H 1.027(3) 1.102(2) 0.4272(8) 0.028 Uiso 1 1 d . . . C61 C 1.0319(3) 1.01255(18) 0.35242(8) 0.0210(4) Uani 1 1 d . . . H61 H 1.060(3) 1.0854(19) 0.3317(8) 0.025 Uiso 1 1 d . . . C71 C 0.9442(3) 0.9156(2) 0.50469(8) 0.0303(5) Uani 1 1 d . . . H712 H 0.8682 0.8453 0.5175 0.045 Uiso 1 1 calc R . . H711 H 0.8975 1.0014 0.5155 0.045 Uiso 1 1 calc R . . H713 H 1.0557 0.9040 0.5222 0.045 Uiso 1 1 calc R . . C12 C 0.1213(2) 0.87623(18) 0.03100(7) 0.0166(4) Uani 1 1 d . . . C22 C 0.0182(2) 0.97297(19) 0.00688(8) 0.0222(4) Uani 1 1 d . . . H22 H -0.032(3) 1.0362(19) 0.0340(9) 0.027 Uiso 1 1 d . . . C32 C -0.0123(3) 0.9736(2) -0.05033(9) 0.0277(5) Uani 1 1 d . . . H32 H -0.084(3) 1.039(2) -0.0667(8) 0.033 Uiso 1 1 d . . . C42 C 0.0511(3) 0.8745(2) -0.08416(8) 0.0290(5) Uani 1 1 d . . . H42 H 0.027(3) 0.876(2) -0.1241(9) 0.035 Uiso 1 1 d . . . C52 C 0.1500(3) 0.7757(2) -0.06083(8) 0.0271(5) Uani 1 1 d . . . H52 H 0.194(3) 0.706(2) -0.0831(9) 0.033 Uiso 1 1 d . . . C62 C 0.1869(3) 0.77851(19) -0.00362(8) 0.0216(4) Uani 1 1 d . . . H62 H 0.252(3) 0.715(2) 0.0129(8) 0.026 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.0121(2) 0.0154(2) 0.0165(2) -0.00029(19) -0.00040(18) 0.00141(18) O2 0.0154(6) 0.0175(6) 0.0192(7) 0.0029(5) 0.0002(5) 0.0000(5) O6 0.0157(6) 0.0154(6) 0.0186(6) -0.0008(5) -0.0031(5) 0.0010(5) O3 0.0168(6) 0.0182(6) 0.0221(7) -0.0008(5) -0.0001(5) 0.0048(5) O4 0.0173(7) 0.0277(7) 0.0155(7) 0.0000(6) 0.0017(5) 0.0006(6) O7 0.0168(6) 0.0174(6) 0.0160(6) -0.0019(5) -0.0061(5) -0.0002(5) O1 0.0135(6) 0.0155(7) 0.0201(6) -0.0021(5) -0.0043(5) 0.0033(5) O5 0.0200(7) 0.0204(7) 0.0194(7) 0.0045(5) 0.0024(5) -0.0006(6) N1 0.0118(7) 0.0132(7) 0.0156(7) -0.0002(6) -0.0004(6) 0.0030(6) N2 0.0162(8) 0.0131(7) 0.0161(8) -0.0005(6) -0.0059(6) 0.0041(7) C1 0.0111(8) 0.0156(9) 0.0156(9) -0.0014(7) -0.0029(7) -0.0026(7) C2 0.0113(9) 0.0147(9) 0.0154(9) 0.0003(7) -0.0038(6) -0.0015(7) C3 0.0123(8) 0.0195(9) 0.0151(9) -0.0026(8) 0.0008(7) -0.0013(7) C4 0.0136(8) 0.0167(9) 0.0159(9) -0.0062(7) -0.0014(7) -0.0035(7) C5 0.0142(9) 0.0204(9) 0.0092(8) -0.0027(7) 0.0014(7) 0.0007(8) C6 0.0182(9) 0.0197(10) 0.0170(9) -0.0021(8) -0.0023(7) -0.0044(9) C11 0.0158(9) 0.0188(9) 0.0129(8) 0.0004(7) -0.0025(7) 0.0020(7) C21 0.0180(9) 0.0154(9) 0.0216(10) 0.0000(7) -0.0040(8) 0.0016(8) C31 0.0223(10) 0.0180(9) 0.0214(10) 0.0032(8) -0.0012(8) 0.0021(8) C41 0.0183(9) 0.0252(10) 0.0195(10) -0.0023(7) -0.0053(8) 0.0026(9) C51 0.0279(11) 0.0183(10) 0.0245(10) -0.0067(8) -0.0037(8) -0.0009(8) C61 0.0224(9) 0.0177(9) 0.0228(10) 0.0007(8) -0.0035(8) -0.0040(9) C71 0.0344(13) 0.0358(12) 0.0207(11) -0.0004(9) -0.0027(9) 0.0029(10) C12 0.0167(9) 0.0172(9) 0.0158(9) -0.0003(8) -0.0031(7) -0.0056(8) C22 0.0204(10) 0.0183(9) 0.0280(11) -0.0027(8) -0.0069(8) -0.0018(9) C32 0.0268(11) 0.0242(11) 0.0319(12) 0.0074(9) -0.0140(9) -0.0075(9) C42 0.0325(11) 0.0388(12) 0.0158(9) 0.0029(10) -0.0053(9) -0.0137(11) C52 0.0292(12) 0.0328(12) 0.0193(10) -0.0092(9) 0.0039(9) -0.0063(10) C62 0.0216(11) 0.0220(11) 0.0211(10) -0.0005(9) -0.0012(8) 0.0001(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S O2 1.4270(13) . ? S O3 1.4291(13) . ? S O1 1.6567(13) . ? S C11 1.7431(17) . ? O6 C5 1.213(2) . ? O4 C1 1.202(2) . ? O7 C5 1.346(2) . ? O7 C6 1.465(2) . ? O1 N1 1.3970(18) . ? O5 C4 1.204(2) . ? N1 C1 1.399(2) . ? N1 C4 1.401(2) . ? N2 C5 1.355(2) . ? N2 C2 1.452(2) . ? N2 H2N 0.77(2) . ? C1 C2 1.533(2) . ? C2 C3 1.545(2) . ? C2 H2 0.979(19) . ? C3 C4 1.508(3) . ? C3 H3A 0.96(2) . ? C3 H3B 0.94(2) . ? C6 C12 1.507(2) . ? C6 H6A 0.98(2) . ? C6 H6B 1.02(2) . ? C11 C21 1.396(2) . ? C11 C61 1.399(2) . ? C21 C31 1.372(3) . ? C21 H21 0.997(19) . ? C31 C41 1.402(3) . ? C31 H31 0.940(19) . ? C41 C51 1.392(3) . ? C41 C71 1.508(3) . ? C51 C61 1.380(3) . ? C51 H51 0.94(2) . ? C61 H61 0.915(19) . ? C71 H712 0.9800 . ? C71 H711 0.9800 . ? C71 H713 0.9800 . ? C12 C62 1.387(3) . ? C12 C22 1.397(3) . ? C22 C32 1.378(3) . ? C22 H22 0.99(2) . ? C32 C42 1.380(3) . ? C32 H32 0.95(2) . ? C42 C52 1.385(3) . ? C42 H42 0.97(2) . ? C52 C62 1.388(3) . ? C52 H52 0.95(2) . ? C62 H62 0.91(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 O2 S O3 121.52(7) . . ? O2 S O1 108.45(7) . . ? O3 S O1 100.29(7) . . ? O2 S C11 110.28(8) . . ? O3 S C11 110.89(8) . . ? O1 S C11 103.38(7) . . ? C5 O7 C6 116.53(14) . . ? N1 O1 S 111.92(10) . . ? O1 N1 C1 118.61(13) . . ? O1 N1 C4 120.41(14) . . ? C1 N1 C4 114.98(14) . . ? C5 N2 C2 118.67(15) . . ? C5 N2 H2N 123.0(15) . . ? C2 N2 H2N 116.6(15) . . ? O4 C1 N1 125.27(16) . . ? O4 C1 C2 129.06(16) . . ? N1 C1 C2 105.67(14) . . ? N2 C2 C1 109.51(14) . . ? N2 C2 C3 115.09(14) . . ? C1 C2 C3 104.95(13) . . ? N2 C2 H2 108.0(10) . . ? C1 C2 H2 107.2(11) . . ? C3 C2 H2 111.8(10) . . ? C4 C3 C2 105.94(14) . . ? C4 C3 H3A 108.1(11) . . ? C2 C3 H3A 109.9(11) . . ? C4 C3 H3B 107.4(11) . . ? C2 C3 H3B 112.8(11) . . ? H3A C3 H3B 112.4(16) . . ? O5 C4 N1 124.60(17) . . ? O5 C4 C3 130.00(16) . . ? N1 C4 C3 105.39(14) . . ? O6 C5 O7 126.26(16) . . ? O6 C5 N2 123.42(16) . . ? O7 C5 N2 110.27(15) . . ? O7 C6 C12 107.80(14) . . ? O7 C6 H6A 106.0(11) . . ? C12 C6 H6A 113.3(11) . . ? O7 C6 H6B 112.2(10) . . ? C12 C6 H6B 112.7(10) . . ? H6A C6 H6B 104.8(15) . . ? C21 C11 C61 121.42(16) . . ? C21 C11 S 118.54(13) . . ? C61 C11 S 120.02(14) . . ? C31 C21 C11 118.75(17) . . ? C31 C21 H21 121.1(10) . . ? C11 C21 H21 119.8(11) . . ? C21 C31 C41 121.42(18) . . ? C21 C31 H31 121.9(12) . . ? C41 C31 H31 116.7(11) . . ? C51 C41 C31 118.37(17) . . ? C51 C41 C71 121.57(17) . . ? C31 C41 C71 120.03(17) . . ? C61 C51 C41 121.76(18) . . ? C61 C51 H51 116.9(12) . . ? C41 C51 H51 121.3(12) . . ? C51 C61 C11 118.22(17) . . ? C51 C61 H61 121.6(12) . . ? C11 C61 H61 120.1(12) . . ? C41 C71 H712 109.5 . . ? C41 C71 H711 109.5 . . ? H712 C71 H711 109.5 . . ? C41 C71 H713 109.5 . . ? H712 C71 H713 109.5 . . ? H711 C71 H713 109.5 . . ? C62 C12 C22 118.47(17) . . ? C62 C12 C6 120.31(17) . . ? C22 C12 C6 121.21(17) . . ? C32 C22 C12 120.57(18) . . ? C32 C22 H22 124.3(12) . . ? C12 C22 H22 115.1(12) . . ? C22 C32 C42 120.34(19) . . ? C22 C32 H32 120.5(12) . . ? C42 C32 H32 119.0(12) . . ? C32 C42 C52 119.93(19) . . ? C32 C42 H42 119.2(13) . . ? C52 C42 H42 120.9(13) . . ? C42 C52 C62 119.61(19) . . ? C42 C52 H52 121.6(13) . . ? C62 C52 H52 118.8(13) . . ? C12 C62 C52 120.98(18) . . ? C12 C62 H62 117.2(13) . . ? C52 C62 H62 121.8(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 O2 S O1 N1 -44.15(11) . . . . ? O3 S O1 N1 -172.51(10) . . . . ? C11 S O1 N1 72.92(12) . . . . ? S O1 N1 C1 103.35(14) . . . . ? S O1 N1 C4 -105.26(14) . . . . ? O1 N1 C1 O4 -13.4(2) . . . . ? C4 N1 C1 O4 -166.26(16) . . . . ? O1 N1 C1 C2 167.15(13) . . . . ? C4 N1 C1 C2 14.25(19) . . . . ? C5 N2 C2 C1 53.3(2) . . . . ? C5 N2 C2 C3 -64.6(2) . . . . ? O4 C1 C2 N2 53.1(2) . . . . ? N1 C1 C2 N2 -127.43(15) . . . . ? O4 C1 C2 C3 177.18(18) . . . . ? N1 C1 C2 C3 -3.36(17) . . . . ? N2 C2 C3 C4 113.30(16) . . . . ? C1 C2 C3 C4 -7.14(17) . . . . ? O1 N1 C4 O5 10.0(2) . . . . ? C1 N1 C4 O5 162.42(17) . . . . ? O1 N1 C4 C3 -171.32(13) . . . . ? C1 N1 C4 C3 -18.94(19) . . . . ? C2 C3 C4 O5 -166.41(18) . . . . ? C2 C3 C4 N1 15.06(17) . . . . ? C6 O7 C5 O6 3.5(2) . . . . ? C6 O7 C5 N2 -179.08(13) . . . . ? C2 N2 C5 O6 -6.1(2) . . . . ? C2 N2 C5 O7 176.41(14) . . . . ? C5 O7 C6 C12 -140.48(15) . . . . ? O2 S C11 C21 -176.55(14) . . . . ? O3 S C11 C21 -39.03(16) . . . . ? O1 S C11 C21 67.68(15) . . . . ? O2 S C11 C61 4.68(17) . . . . ? O3 S C11 C61 142.20(14) . . . . ? O1 S C11 C61 -111.10(15) . . . . ? C61 C11 C21 C31 -1.3(3) . . . . ? S C11 C21 C31 179.95(14) . . . . ? C11 C21 C31 C41 -0.8(3) . . . . ? C21 C31 C41 C51 1.9(3) . . . . ? C21 C31 C41 C71 -176.34(19) . . . . ? C31 C41 C51 C61 -0.9(3) . . . . ? C71 C41 C51 C61 177.26(19) . . . . ? C41 C51 C61 C11 -1.0(3) . . . . ? C21 C11 C61 C51 2.2(3) . . . . ? S C11 C61 C51 -179.07(14) . . . . ? O7 C6 C12 C62 120.17(19) . . . . ? O7 C6 C12 C22 -60.3(2) . . . . ? C62 C12 C22 C32 -2.3(3) . . . . ? C6 C12 C22 C32 178.15(17) . . . . ? C12 C22 C32 C42 3.5(3) . . . . ? C22 C32 C42 C52 -1.8(3) . . . . ? C32 C42 C52 C62 -1.1(3) . . . . ? C22 C12 C62 C52 -0.6(3) . . . . ? C6 C12 C62 C52 178.95(17) . . . . ? C42 C52 C62 C12 2.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O5 0.77(2) 2.536(19) 3.073(2) 128.6(18) 3_655 C2 H2 O5 0.979(19) 2.581(18) 3.116(2) 114.4(13) 3_655 C3 H3A O6 0.96(2) 2.63(2) 3.556(2) 162.7(15) 3_655 C6 H6A O4 0.98(2) 2.59(2) 3.389(2) 139.2(15) 1_455 _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.209 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.046 data_compound_I _database_code_depnum_ccdc_archive 'CCDC 284050' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 416-417K _chemical_formula_moiety 'C11 H11 N O5 S' _chemical_formula_sum 'C11 H11 N O5 S' _chemical_formula_weight 269.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2003)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2003)' _computing_data_reduction CrysAlisRED _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003) ; _computing_publication_material SHELXL97 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 9.847(3) _cell_length_b 11.791(3) _cell_length_c 11.014(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.58(3) _cell_angle_gamma 90.00 _cell_volume 1197.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 14458 _cell_measurement_theta_min 3.46 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Oxford Xcalibur PX \k geometry' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17314 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3492 _reflns_number_gt 3107 _reflns_threshold_expression >2sigma(I) _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^)+(0.0800P)^2^+0.3570P] 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 3492 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.077 _refine_ls_shift/su_mean 0.002 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 S S 0.18821(3) 0.68568(3) 0.55018(3) 0.02080(11) Uani 1 1 d . . . O1 O 0.18009(10) 0.82075(7) 0.58670(8) 0.01978(19) Uani 1 1 d . . . N1 N 0.18341(11) 0.89420(9) 0.48895(9) 0.0182(2) Uani 1 1 d . . . O4 O -0.06526(10) 0.90425(9) 0.38936(9) 0.0267(2) Uani 1 1 d . . . O2 O 0.08061(11) 0.66587(9) 0.42659(11) 0.0301(2) Uani 1 1 d . . . C1 C 0.05354(13) 0.93947(10) 0.40193(11) 0.0206(2) Uani 1 1 d . . . O3 O 0.18056(12) 0.63522(9) 0.66511(11) 0.0325(2) Uani 1 1 d . . . O5 O 0.41660(10) 0.95288(9) 0.60191(10) 0.0293(2) Uani 1 1 d . . . C2 C 0.09756(15) 1.03741(11) 0.33653(12) 0.0244(2) Uani 1 1 d . . . H2B H 0.047(2) 1.1001(16) 0.3470(17) 0.029 Uiso 1 1 d . . . H2A H 0.070(2) 1.0178(16) 0.2504(18) 0.029 Uiso 1 1 d . . . C3 C 0.26157(16) 1.04982(12) 0.40362(14) 0.0280(3) Uani 1 1 d . . . H3A H 0.311(2) 1.0335(17) 0.3460(19) 0.034 Uiso 1 1 d . . . H3B H 0.291(2) 1.1160(18) 0.4410(18) 0.034 Uiso 1 1 d . . . C4 C 0.30498(13) 0.96435(10) 0.51207(12) 0.0212(2) Uani 1 1 d . . . C11 C 0.36012(13) 0.66859(10) 0.54130(11) 0.0186(2) Uani 1 1 d . . . C21 C 0.47855(14) 0.65613(12) 0.65539(12) 0.0239(2) Uani 1 1 d . . . H21 H 0.469(2) 0.6576(16) 0.7380(18) 0.029 Uiso 1 1 d . . . C31 C 0.61512(14) 0.64317(12) 0.64700(14) 0.0286(3) Uani 1 1 d . . . H31 H 0.693(2) 0.6232(17) 0.7276(19) 0.034 Uiso 1 1 d . . . C41 C 0.63344(15) 0.64133(11) 0.52714(15) 0.0276(3) Uani 1 1 d . . . C51 C 0.51178(16) 0.65002(12) 0.41476(14) 0.0279(3) Uani 1 1 d . . . H51 H 0.517(2) 0.6448(18) 0.3346(19) 0.033 Uiso 1 1 d . . . C61 C 0.37443(15) 0.66474(12) 0.42047(12) 0.0244(2) Uani 1 1 d . . . H61 H 0.289(2) 0.6739(15) 0.3451(19) 0.029 Uiso 1 1 d . . . C71 C 0.78234(18) 0.62987(15) 0.5189(2) 0.0442(4) Uani 1 1 d . . . H711 H 0.7777 0.5793 0.4469 0.066 Uiso 1 1 calc R . . H712 H 0.8491 0.5982 0.6003 0.066 Uiso 1 1 calc R . . H713 H 0.8171 0.7047 0.5041 0.066 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 S 0.01905(17) 0.01872(17) 0.02462(17) 0.00010(9) 0.00765(12) -0.00109(9) O1 0.0221(4) 0.0198(4) 0.0181(4) 0.0003(3) 0.0079(3) 0.0015(3) N1 0.0171(4) 0.0181(4) 0.0179(4) 0.0011(3) 0.0043(3) 0.0009(3) O4 0.0175(4) 0.0335(5) 0.0255(4) -0.0052(4) 0.0031(3) 0.0021(3) O2 0.0204(4) 0.0292(5) 0.0348(5) -0.0101(4) 0.0023(4) -0.0026(4) C1 0.0188(5) 0.0235(5) 0.0173(5) -0.0035(4) 0.0035(4) 0.0054(4) O3 0.0354(5) 0.0298(5) 0.0393(6) 0.0098(4) 0.0220(5) 0.0010(4) O5 0.0199(4) 0.0353(5) 0.0278(5) 0.0000(4) 0.0022(4) -0.0035(4) C2 0.0257(6) 0.0251(6) 0.0216(5) 0.0029(4) 0.0074(4) 0.0093(5) C3 0.0286(6) 0.0224(6) 0.0316(6) 0.0038(5) 0.0088(5) -0.0004(5) C4 0.0199(5) 0.0201(5) 0.0231(5) -0.0023(4) 0.0070(4) -0.0004(4) C11 0.0184(5) 0.0174(5) 0.0191(5) 0.0008(4) 0.0056(4) 0.0016(4) C21 0.0241(6) 0.0251(6) 0.0194(5) 0.0014(4) 0.0040(4) 0.0040(5) C31 0.0205(6) 0.0273(6) 0.0325(6) 0.0012(5) 0.0024(5) 0.0047(5) C41 0.0242(6) 0.0189(6) 0.0426(7) 0.0010(5) 0.0155(5) 0.0030(4) C51 0.0332(7) 0.0256(6) 0.0303(6) 0.0018(5) 0.0180(6) 0.0033(5) C61 0.0268(6) 0.0271(6) 0.0187(5) 0.0011(4) 0.0072(5) 0.0022(5) C71 0.0301(8) 0.0319(8) 0.0789(13) -0.0012(8) 0.0295(8) 0.0034(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 S O2 1.4202(12) . ? S O3 1.4245(11) . ? S O1 1.6515(10) . ? S C11 1.7422(13) . ? O1 N1 1.3910(13) . ? N1 C4 1.4034(16) . ? N1 C1 1.4066(16) . ? O4 C1 1.2032(16) . ? C1 C2 1.5035(19) . ? O5 C4 1.2008(16) . ? C2 C3 1.530(2) . ? C2 H2B 0.919(19) . ? C2 H2A 0.920(18) . ? C3 C4 1.5053(18) . ? C3 H3A 0.95(2) . ? C3 H3B 0.88(2) . ? C11 C61 1.3874(16) . ? C11 C21 1.3898(17) . ? C21 C31 1.3893(19) . ? C21 H21 0.947(19) . ? C31 C41 1.394(2) . ? C31 H31 0.98(2) . ? C41 C51 1.391(2) . ? C41 C71 1.507(2) . ? C51 C61 1.388(2) . ? C51 H51 0.902(19) . ? C61 H61 0.96(2) . ? C71 H711 0.9800 . ? C71 H712 0.9800 . ? C71 H713 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S O3 121.88(7) . . ? O2 S O1 107.96(6) . . ? O3 S O1 99.44(6) . . ? O2 S C11 109.89(7) . . ? O3 S C11 110.96(7) . . ? O1 S C11 104.86(5) . . ? N1 O1 S 113.30(7) . . ? O1 N1 C4 118.51(10) . . ? O1 N1 C1 120.03(10) . . ? C4 N1 C1 114.46(10) . . ? O4 C1 N1 124.24(12) . . ? O4 C1 C2 130.00(11) . . ? N1 C1 C2 105.74(10) . . ? C1 C2 C3 106.01(10) . . ? C1 C2 H2B 107.4(12) . . ? C3 C2 H2B 112.7(12) . . ? C1 C2 H2A 105.8(12) . . ? C3 C2 H2A 113.6(12) . . ? H2B C2 H2A 110.8(16) . . ? C4 C3 C2 106.06(11) . . ? C4 C3 H3A 109.0(12) . . ? C2 C3 H3A 111.4(12) . . ? C4 C3 H3B 105.5(13) . . ? C2 C3 H3B 115.4(13) . . ? H3A C3 H3B 109.2(18) . . ? O5 C4 N1 124.00(12) . . ? O5 C4 C3 130.67(12) . . ? N1 C4 C3 105.32(11) . . ? C61 C11 C21 121.85(12) . . ? C61 C11 S 119.09(10) . . ? C21 C11 S 119.04(10) . . ? C31 C21 C11 118.46(12) . . ? C31 C21 H21 119.4(11) . . ? C11 C21 H21 122.1(11) . . ? C21 C31 C41 121.03(12) . . ? C21 C31 H31 116.0(11) . . ? C41 C31 H31 122.2(11) . . ? C51 C41 C31 118.91(12) . . ? C51 C41 C71 120.35(15) . . ? C31 C41 C71 120.73(15) . . ? C61 C51 C41 121.18(13) . . ? C61 C51 H51 116.1(12) . . ? C41 C51 H51 122.7(12) . . ? C11 C61 C51 118.50(12) . . ? C11 C61 H61 118.4(12) . . ? C51 C61 H61 123.0(12) . . ? C41 C71 H711 109.5 . . ? C41 C71 H712 109.5 . . ? H711 C71 H712 109.5 . . ? C41 C71 H713 109.5 . . ? H711 C71 H713 109.5 . . ? H712 C71 H713 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S O1 N1 -51.10(9) . . . . ? O3 S O1 N1 -179.18(8) . . . . ? C11 S O1 N1 66.03(9) . . . . ? S O1 N1 C4 -112.77(10) . . . . ? S O1 N1 C1 98.12(11) . . . . ? O1 N1 C1 O4 -14.21(18) . . . . ? C4 N1 C1 O4 -164.49(11) . . . . ? O1 N1 C1 C2 164.37(9) . . . . ? C4 N1 C1 C2 14.09(13) . . . . ? O4 C1 C2 C3 173.24(13) . . . . ? N1 C1 C2 C3 -5.23(13) . . . . ? C1 C2 C3 C4 -4.15(14) . . . . ? O1 N1 C4 O5 12.59(18) . . . . ? C1 N1 C4 O5 163.35(12) . . . . ? O1 N1 C4 C3 -167.49(10) . . . . ? C1 N1 C4 C3 -16.72(14) . . . . ? C2 C3 C4 O5 -168.10(13) . . . . ? C2 C3 C4 N1 11.98(14) . . . . ? O2 S C11 C61 14.15(13) . . . . ? O3 S C11 C61 151.89(11) . . . . ? O1 S C11 C61 -101.65(11) . . . . ? O2 S C11 C21 -164.12(10) . . . . ? O3 S C11 C21 -26.39(12) . . . . ? O1 S C11 C21 80.08(11) . . . . ? C61 C11 C21 C31 2.1(2) . . . . ? S C11 C21 C31 -179.67(10) . . . . ? C11 C21 C31 C41 -0.7(2) . . . . ? C21 C31 C41 C51 -1.5(2) . . . . ? C21 C31 C41 C71 178.62(13) . . . . ? C31 C41 C51 C61 2.5(2) . . . . ? C71 C41 C51 C61 -177.65(13) . . . . ? C21 C11 C61 C51 -1.2(2) . . . . ? S C11 C61 C51 -179.40(10) . . . . ? C41 C51 C61 C11 -1.2(2) . . . . ? 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 C2 H2A O3 0.920(18) 2.458(19) 3.0761(17) 124.7(15) 4_575 C3 H3A O5 0.95(2) 2.54(2) 3.193(2) 126.1(15) 3_676 C31 H31 O4 0.98(2) 2.44(2) 3.383(2) 161.6(16) 4_676 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.442 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.077 data_compound_III _database_code_depnum_ccdc_archive 'CCDC 284051' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 410-412K _chemical_formula_moiety 'C14 H16 N2 O7 S' _chemical_formula_sum 'C14 H16 N2 O7 S' _chemical_formula_weight 356.35 _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.764(2) _cell_length_b 10.265(3) _cell_length_c 19.787(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1577.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 14733 _cell_measurement_theta_min 4.47 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Oxford Xcalibur PX \k geometry' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29265 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_sigmaI/netI 0.0534 _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 -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 4.47 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4579 _reflns_number_gt 4096 _reflns_threshold_expression >2sigma(I) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2003)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2003)' _computing_data_reduction CrysAlisRED _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003) ; _computing_publication_material SHELXL97 _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^)+(0.0410P)^2^] 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 0.00(7) _chemical_absolute_configuration ad _refine_ls_number_reflns 4579 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.004 _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 S S 0.97694(6) 0.45399(4) 0.76647(2) 0.01614(10) Uani 1 1 d . . . O1 O 1.17558(15) 0.48113(11) 0.73871(7) 0.0175(3) Uani 1 1 d . . . O2 O 0.91795(16) 0.33598(12) 0.73675(7) 0.0196(3) Uani 1 1 d . . . O3 O 0.89830(16) 0.57602(12) 0.75224(7) 0.0200(3) Uani 1 1 d . . . O4 O 1.22591(17) 0.31429(13) 0.62921(7) 0.0203(3) Uani 1 1 d . . . O5 O 1.42003(18) 0.42070(12) 0.83904(7) 0.0212(3) Uani 1 1 d . . . O6 O 1.59723(16) 0.42770(11) 0.65832(6) 0.0173(3) Uani 1 1 d . . . O7 O 1.76761(17) 0.31593(12) 0.58486(6) 0.0182(3) Uani 1 1 d . . . N1 N 1.27521(19) 0.36802(14) 0.74088(8) 0.0152(3) Uani 1 1 d . . . N2 N 1.5810(2) 0.20832(16) 0.64886(8) 0.0161(3) Uani 1 1 d . . . H2N H 1.616(3) 0.142(2) 0.6334(11) 0.023(6) Uiso 1 1 d . . . C1 C 1.3019(2) 0.29773(17) 0.68092(10) 0.0162(4) Uani 1 1 d . . . C2 C 1.4443(2) 0.19910(17) 0.69784(10) 0.0158(4) Uani 1 1 d . . . H2 H 1.397(3) 0.113(2) 0.6946(10) 0.019 Uiso 1 1 d . . . C3 C 1.4964(2) 0.22935(17) 0.77096(10) 0.0164(4) Uani 1 1 d . . . H3A H 1.458(3) 0.163(2) 0.7991(11) 0.020 Uiso 1 1 d . . . H3B H 1.612(3) 0.245(2) 0.7760(11) 0.020 Uiso 1 1 d . . . C4 C 1.4011(2) 0.35088(17) 0.79072(9) 0.0160(4) Uani 1 1 d . . . C5 C 1.6469(2) 0.32614(18) 0.63293(9) 0.0146(4) Uani 1 1 d . . . C6 C 1.8466(3) 0.43789(19) 0.56390(10) 0.0193(4) Uani 1 1 d . . . H6A H 1.920(3) 0.466(2) 0.6010(11) 0.023 Uiso 1 1 d . . . H6B H 1.756(3) 0.500(2) 0.5565(11) 0.023 Uiso 1 1 d . . . C7 C 1.9459(3) 0.4089(2) 0.50026(10) 0.0241(4) Uani 1 1 d . . . H7A H 1.9946 0.4899 0.4823 0.036 Uiso 1 1 calc R . . H7B H 1.8685 0.3703 0.4667 0.036 Uiso 1 1 calc R . . H7C H 2.0393 0.3477 0.5104 0.036 Uiso 1 1 calc R . . C11 C 1.0092(2) 0.43203(17) 0.85303(9) 0.0168(4) Uani 1 1 d . . . C21 C 1.0280(2) 0.54091(19) 0.89458(9) 0.0183(4) Uani 1 1 d . . . H21 H 1.013(3) 0.623(2) 0.8759(10) 0.022 Uiso 1 1 d . . . C31 C 1.0700(3) 0.52182(18) 0.96166(10) 0.0213(4) Uani 1 1 d . . . H31 H 1.087(3) 0.596(2) 0.9916(11) 0.026 Uiso 1 1 d . . . C41 C 1.0933(3) 0.39664(19) 0.98775(10) 0.0219(4) Uani 1 1 d . . . C51 C 1.0714(3) 0.2902(2) 0.94505(11) 0.0244(5) Uani 1 1 d . . . H51 H 1.078(3) 0.206(2) 0.9633(12) 0.029 Uiso 1 1 d . . . C61 C 1.0298(3) 0.30620(18) 0.87767(10) 0.0214(4) Uani 1 1 d . . . H61 H 1.016(3) 0.232(2) 0.8488(11) 0.026 Uiso 1 1 d . . . C71 C 1.1417(3) 0.3766(2) 1.06090(10) 0.0308(5) Uani 1 1 d . . . H711 H 1.1428 0.2832 1.0711 0.046 Uiso 1 1 calc R . . H712 H 1.0574 0.4204 1.0899 0.046 Uiso 1 1 calc R . . H713 H 1.2564 0.4133 1.0691 0.046 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 S 0.01336(19) 0.0152(2) 0.0199(2) -0.00001(18) 0.00100(18) 0.00103(16) O1 0.0137(6) 0.0146(6) 0.0242(7) 0.0026(5) 0.0035(5) 0.0015(4) O2 0.0153(6) 0.0183(6) 0.0252(7) -0.0016(6) -0.0013(6) 0.0004(5) O3 0.0175(6) 0.0162(7) 0.0263(8) -0.0003(5) 0.0010(5) 0.0042(5) O4 0.0175(7) 0.0253(7) 0.0182(7) 0.0009(6) -0.0005(6) -0.0001(6) O5 0.0224(7) 0.0194(7) 0.0220(7) -0.0031(6) -0.0017(6) -0.0014(5) O6 0.0174(6) 0.0130(6) 0.0215(7) -0.0009(5) 0.0016(6) 0.0004(5) O7 0.0183(7) 0.0157(6) 0.0206(7) 0.0003(5) 0.0056(6) -0.0011(5) N1 0.0129(7) 0.0127(7) 0.0199(8) -0.0008(6) 0.0023(6) 0.0025(5) N2 0.0163(8) 0.0126(8) 0.0195(8) -0.0030(6) 0.0036(7) 0.0007(6) C1 0.0145(9) 0.0154(9) 0.0187(9) 0.0006(7) 0.0016(7) -0.0036(7) C2 0.0139(9) 0.0119(8) 0.0216(9) -0.0011(7) 0.0021(8) -0.0001(7) C3 0.0150(9) 0.0167(8) 0.0175(8) 0.0027(7) 0.0006(8) 0.0016(7) C4 0.0131(9) 0.0166(9) 0.0182(9) 0.0028(7) 0.0039(7) -0.0042(7) C5 0.0134(8) 0.0171(9) 0.0132(8) 0.0006(7) -0.0008(7) 0.0005(7) C6 0.0199(9) 0.0162(10) 0.0219(10) 0.0017(8) 0.0041(8) -0.0020(8) C7 0.0264(11) 0.0251(10) 0.0208(9) 0.0013(8) 0.0069(8) -0.0038(8) C11 0.0139(9) 0.0176(9) 0.0190(8) 0.0009(7) 0.0043(7) -0.0013(7) C21 0.0178(9) 0.0127(8) 0.0245(9) 0.0006(7) 0.0018(8) 0.0004(7) C31 0.0211(10) 0.0187(10) 0.0240(10) -0.0053(8) 0.0043(8) 0.0009(7) C41 0.0222(10) 0.0216(10) 0.0218(10) 0.0009(8) 0.0053(8) 0.0051(8) C51 0.0341(12) 0.0149(9) 0.0242(10) 0.0038(8) 0.0075(9) 0.0030(8) C61 0.0263(10) 0.0153(9) 0.0226(9) -0.0016(8) 0.0079(9) -0.0001(8) C71 0.0385(13) 0.0318(12) 0.0222(11) -0.0006(9) 0.0026(9) 0.0110(10) _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 S O3 1.4217(13) . ? S O2 1.4223(14) . ? S O1 1.6607(14) . ? S C11 1.7455(19) . ? O1 N1 1.3957(18) . ? O4 C1 1.193(2) . ? O5 C4 1.204(2) . ? O6 C5 1.220(2) . ? O7 C5 1.339(2) . ? O7 C6 1.455(2) . ? N1 C4 1.399(2) . ? N1 C1 1.404(2) . ? N2 C5 1.351(2) . ? N2 C2 1.440(2) . ? N2 H2N 0.79(2) . ? C1 C2 1.536(3) . ? C2 C3 1.534(3) . ? C2 H2 0.96(2) . ? C3 C4 1.502(3) . ? C3 H3A 0.93(2) . ? C3 H3B 0.92(2) . ? C6 C7 1.506(3) . ? C6 H6A 0.97(2) . ? C6 H6B 0.96(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C11 C61 1.390(3) . ? C11 C21 1.395(3) . ? C21 C31 1.381(3) . ? C21 H21 0.93(2) . ? C31 C41 1.397(3) . ? C31 H31 0.98(2) . ? C41 C51 1.391(3) . ? C41 C71 1.509(3) . ? C51 C61 1.382(3) . ? C51 H51 0.94(2) . ? C61 H61 0.96(2) . ? C71 H711 0.9800 . ? C71 H712 0.9800 . ? C71 H713 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S O2 122.02(8) . . ? O3 S O1 100.69(7) . . ? O2 S O1 107.77(7) . . ? O3 S C11 111.69(8) . . ? O2 S C11 109.99(8) . . ? O1 S C11 102.31(8) . . ? N1 O1 S 111.41(10) . . ? C5 O7 C6 115.48(14) . . ? O1 N1 C4 120.87(14) . . ? O1 N1 C1 118.90(15) . . ? C4 N1 C1 115.34(15) . . ? C5 N2 C2 119.67(15) . . ? C5 N2 H2N 123.1(17) . . ? C2 N2 H2N 117.2(17) . . ? O4 C1 N1 125.34(17) . . ? O4 C1 C2 129.54(17) . . ? N1 C1 C2 105.11(16) . . ? N2 C2 C3 115.29(15) . . ? N2 C2 C1 109.90(15) . . ? C3 C2 C1 105.18(15) . . ? N2 C2 H2 107.4(13) . . ? C3 C2 H2 110.5(12) . . ? C1 C2 H2 108.4(13) . . ? C4 C3 C2 106.49(15) . . ? C4 C3 H3A 106.9(13) . . ? C2 C3 H3A 109.4(13) . . ? C4 C3 H3B 108.2(13) . . ? C2 C3 H3B 113.3(14) . . ? H3A C3 H3B 112(2) . . ? O5 C4 N1 124.77(17) . . ? O5 C4 C3 129.85(18) . . ? N1 C4 C3 105.36(15) . . ? O6 C5 O7 125.50(16) . . ? O6 C5 N2 123.32(17) . . ? O7 C5 N2 111.15(15) . . ? O7 C6 C7 106.52(15) . . ? O7 C6 H6A 106.8(13) . . ? C7 C6 H6A 113.0(14) . . ? O7 C6 H6B 107.7(14) . . ? C7 C6 H6B 112.3(13) . . ? H6A C6 H6B 110.1(18) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C61 C11 C21 121.71(17) . . ? C61 C11 S 118.73(14) . . ? C21 C11 S 119.33(13) . . ? C31 C21 C11 118.53(18) . . ? C31 C21 H21 122.8(13) . . ? C11 C21 H21 118.7(13) . . ? C21 C31 C41 121.10(18) . . ? C21 C31 H31 120.2(13) . . ? C41 C31 H31 118.6(13) . . ? C51 C41 C31 118.81(19) . . ? C51 C41 C71 120.40(18) . . ? C31 C41 C71 120.79(18) . . ? C61 C51 C41 121.44(19) . . ? C61 C51 H51 119.6(14) . . ? C41 C51 H51 118.8(14) . . ? C51 C61 C11 118.40(18) . . ? C51 C61 H61 120.5(13) . . ? C11 C61 H61 121.1(13) . . ? C41 C71 H711 109.5 . . ? C41 C71 H712 109.5 . . ? H711 C71 H712 109.5 . . ? C41 C71 H713 109.5 . . ? H711 C71 H713 109.5 . . ? H712 C71 H713 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S O1 N1 -173.68(11) . . . . ? O2 S O1 N1 -44.84(13) . . . . ? C11 S O1 N1 71.09(13) . . . . ? S O1 N1 C4 -105.01(15) . . . . ? S O1 N1 C1 100.88(15) . . . . ? O1 N1 C1 O4 -12.0(3) . . . . ? C4 N1 C1 O4 -167.53(17) . . . . ? O1 N1 C1 C2 168.37(13) . . . . ? C4 N1 C1 C2 12.86(19) . . . . ? C5 N2 C2 C3 -69.7(2) . . . . ? C5 N2 C2 C1 48.9(2) . . . . ? O4 C1 C2 N2 52.7(3) . . . . ? N1 C1 C2 N2 -127.68(15) . . . . ? O4 C1 C2 C3 177.42(19) . . . . ? N1 C1 C2 C3 -2.99(18) . . . . ? N2 C2 C3 C4 114.70(17) . . . . ? C1 C2 C3 C4 -6.52(18) . . . . ? O1 N1 C4 O5 9.4(3) . . . . ? C1 N1 C4 O5 164.36(17) . . . . ? O1 N1 C4 C3 -172.12(14) . . . . ? C1 N1 C4 C3 -17.1(2) . . . . ? C2 C3 C4 O5 -167.94(19) . . . . ? C2 C3 C4 N1 13.67(18) . . . . ? C6 O7 C5 O6 1.9(3) . . . . ? C6 O7 C5 N2 179.84(15) . . . . ? C2 N2 C5 O6 0.4(3) . . . . ? C2 N2 C5 O7 -177.63(15) . . . . ? C5 O7 C6 C7 -167.53(16) . . . . ? O3 S C11 C61 158.89(15) . . . . ? O2 S C11 C61 20.13(18) . . . . ? O1 S C11 C61 -94.18(16) . . . . ? O3 S C11 C21 -26.47(18) . . . . ? O2 S C11 C21 -165.23(14) . . . . ? O1 S C11 C21 80.46(16) . . . . ? C61 C11 C21 C31 0.7(3) . . . . ? S C11 C21 C31 -173.77(15) . . . . ? C11 C21 C31 C41 0.0(3) . . . . ? C21 C31 C41 C51 -0.8(3) . . . . ? C21 C31 C41 C71 179.14(19) . . . . ? C31 C41 C51 C61 0.9(3) . . . . ? C71 C41 C51 C61 -179.0(2) . . . . ? C41 C51 C61 C11 -0.3(3) . . . . ? C21 C11 C61 C51 -0.5(3) . . . . ? S C11 C61 C51 173.98(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O5 0.79(2) 2.35(2) 2.962(2) 134(2) 3_846 C2 H2 O3 0.96(2) 2.55(2) 3.106(2) 117.1(15) 3_746 C2 H2 O5 0.96(2) 2.52(2) 3.132(2) 121.5(16) 3_846 C3 H3A O6 0.93(2) 2.59(2) 3.475(2) 158.3(17) 3_846 C71 H712 O6 0.98 2.39 3.345(3) 165.3 2_765 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.325 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.054 #========================================================================= data_compound_IV _database_code_depnum_ccdc_archive 'CCDC 284052' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 428-430K _chemical_formula_moiety 'C15 H11 N O5 S' _chemical_formula_sum 'C15 H11 N O5 S' _chemical_formula_weight 317.31 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 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 14.343 _cell_length_b 6.654(4) _cell_length_c 15.080(2) _cell_angle_alpha 90.000 _cell_angle_beta 108.16(3) _cell_angle_gamma 90.00 _cell_volume 1367.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12174 _cell_measurement_theta_min 4.60 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Oxford Xcalibur PX \k geometry' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23525 _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.60 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3986 _reflns_number_gt 3100 _reflns_threshold_expression >2sigma(I) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2003)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2003)' _computing_data_reduction CrysAlisRED _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003) ; _computing_publication_material SHELXL97 _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^)+(0.0838P)^2^] 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 3986 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1441 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S S 0.86063(3) 0.69981(7) 0.08640(3) 0.02088(16) Uani 1 1 d . . . O1 O 0.87941(10) 0.5534(2) 0.17899(9) 0.0225(3) Uani 1 1 d . . . O5 O 1.05955(10) 0.6234(2) 0.31337(10) 0.0268(3) Uani 1 1 d . . . O2 O 0.77487(10) 0.8160(2) 0.07752(10) 0.0260(3) Uani 1 1 d . . . C11 C 0.96268(13) 0.8573(3) 0.11255(13) 0.0184(4) Uani 1 1 d . . . C2 C 0.86323(14) 0.7244(3) 0.39998(14) 0.0197(4) Uani 1 1 d . . . O4 O 0.72746(10) 0.6444(2) 0.25810(10) 0.0249(3) Uani 1 1 d . . . O3 O 0.86320(10) 0.5529(2) 0.01845(10) 0.0278(3) Uani 1 1 d . . . C61 C 0.95886(14) 1.0422(3) 0.15500(13) 0.0212(4) Uani 1 1 d . . . C21 C 1.04441(14) 0.7973(3) 0.08845(14) 0.0207(4) Uani 1 1 d . . . C41 C 1.12426(14) 1.1086(3) 0.15322(14) 0.0229(4) Uani 1 1 d . . . C3 C 0.96461(14) 0.7168(3) 0.41698(14) 0.0202(4) Uani 1 1 d . . . N1 N 0.89023(12) 0.6611(3) 0.26125(12) 0.0214(4) Uani 1 1 d . . . C31 C 1.12461(14) 0.9259(3) 0.10866(14) 0.0237(4) Uani 1 1 d . . . C1 C 0.81246(14) 0.6737(3) 0.29999(14) 0.0198(4) Uani 1 1 d . . . C4 C 0.98467(14) 0.6622(3) 0.32920(15) 0.0215(4) Uani 1 1 d . . . C51 C 1.04077(15) 1.1656(3) 0.17534(14) 0.0225(4) Uani 1 1 d . . . C13 C 0.82372(16) 0.7666(3) 0.47055(15) 0.0231(4) Uani 1 1 d . . . C14 C 0.88962(16) 0.8002(3) 0.55986(15) 0.0257(4) Uani 1 1 d . . . C16 C 1.02975(15) 0.7496(3) 0.50480(15) 0.0241(4) Uani 1 1 d . . . C15 C 0.99060(16) 0.7905(3) 0.57674(15) 0.0257(4) Uani 1 1 d . . . C71 C 1.21389(16) 1.2420(4) 0.17943(18) 0.0318(5) Uani 1 1 d . . . H16 H 1.094(2) 0.743(4) 0.5098(19) 0.038 Uiso 1 1 d . . . H13 H 0.758(2) 0.764(4) 0.4587(19) 0.038 Uiso 1 1 d . . . H15 H 1.036(2) 0.821(4) 0.639(2) 0.038 Uiso 1 1 d . . . H14 H 0.8631(19) 0.832(4) 0.6113(19) 0.038 Uiso 1 1 d . . . H51 H 1.0382(19) 1.300(4) 0.2021(19) 0.038 Uiso 1 1 d . . . H61 H 0.899(2) 1.077(4) 0.1693(17) 0.038 Uiso 1 1 d . . . H31 H 1.1792(19) 0.892(4) 0.0898(17) 0.038 Uiso 1 1 d . . . H21 H 1.0464(19) 0.669(4) 0.0605(19) 0.038 Uiso 1 1 d . . . H711 H 1.194(2) 1.383(5) 0.1728(19) 0.048 Uiso 1 1 d . . . H712 H 1.249(2) 1.221(4) 0.136(2) 0.048 Uiso 1 1 d . . . H713 H 1.249(2) 1.213(4) 0.242(2) 0.048 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.0169(2) 0.0237(3) 0.0213(3) -0.00160(18) 0.00493(18) -0.00049(17) O1 0.0240(7) 0.0218(7) 0.0235(7) -0.0015(6) 0.0100(6) -0.0001(5) O5 0.0166(7) 0.0322(8) 0.0335(8) 0.0050(6) 0.0105(6) 0.0020(6) O2 0.0157(7) 0.0308(8) 0.0301(8) 0.0003(6) 0.0053(6) -0.0002(5) C11 0.0153(9) 0.0228(9) 0.0172(9) 0.0010(7) 0.0049(7) 0.0001(7) C2 0.0178(9) 0.0169(9) 0.0233(9) 0.0021(7) 0.0048(7) -0.0005(7) O4 0.0154(7) 0.0318(8) 0.0276(8) -0.0003(6) 0.0066(6) -0.0031(6) O3 0.0273(8) 0.0300(8) 0.0270(8) -0.0061(6) 0.0098(6) -0.0040(6) C61 0.0175(9) 0.0253(10) 0.0201(9) 0.0010(8) 0.0049(7) 0.0031(7) C21 0.0212(9) 0.0223(10) 0.0188(9) 0.0003(7) 0.0064(7) 0.0061(7) C41 0.0175(9) 0.0287(11) 0.0200(9) 0.0044(8) 0.0022(7) -0.0003(7) C3 0.0165(9) 0.0173(9) 0.0257(10) 0.0032(7) 0.0049(7) -0.0007(7) N1 0.0160(8) 0.0270(9) 0.0212(8) -0.0013(7) 0.0058(6) 0.0002(6) C31 0.0163(9) 0.0338(11) 0.0221(10) 0.0040(8) 0.0076(7) 0.0048(8) C1 0.0163(9) 0.0203(9) 0.0239(10) 0.0032(7) 0.0079(7) 0.0001(7) C4 0.0161(9) 0.0197(9) 0.0281(10) 0.0049(8) 0.0060(8) 0.0012(7) C51 0.0226(10) 0.0246(10) 0.0189(9) -0.0007(8) 0.0044(7) 0.0012(8) C13 0.0212(10) 0.0238(10) 0.0256(10) 0.0019(8) 0.0091(8) 0.0004(8) C14 0.0301(11) 0.0223(10) 0.0249(10) 0.0013(8) 0.0088(9) 0.0007(8) C16 0.0183(9) 0.0193(10) 0.0308(11) 0.0050(8) 0.0021(8) -0.0002(7) C15 0.0291(11) 0.0193(10) 0.0234(10) 0.0038(8) 0.0008(8) -0.0012(8) C71 0.0200(10) 0.0407(14) 0.0317(12) 0.0010(10) 0.0036(9) -0.0062(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S O2 1.4233(15) . ? S O3 1.4247(16) . ? S O1 1.6542(15) . ? S C11 1.742(2) . ? O1 N1 1.399(2) . ? O5 C4 1.199(2) . ? C11 C21 1.390(3) . ? C11 C61 1.396(3) . ? C2 C13 1.381(3) . ? C2 C3 1.397(3) . ? C2 C1 1.494(3) . ? O4 C1 1.201(2) . ? C61 C51 1.387(3) . ? C61 H61 0.98(3) . ? C21 C31 1.389(3) . ? C21 H21 0.96(3) . ? C41 C31 1.390(3) . ? C41 C51 1.392(3) . ? C41 C71 1.510(3) . ? C3 C16 1.380(3) . ? C3 C4 1.485(3) . ? N1 C1 1.414(3) . ? N1 C4 1.421(3) . ? C31 H31 0.94(3) . ? C51 H51 0.98(3) . ? C13 C14 1.401(3) . ? C13 H13 0.91(3) . ? C14 C15 1.392(3) . ? C14 H14 0.99(3) . ? C16 C15 1.395(3) . ? C16 H16 0.91(3) . ? C15 H15 0.98(3) . ? C71 H711 0.98(3) . ? C71 H712 0.96(3) . ? C71 H713 0.94(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 O2 S O3 121.34(9) . . ? O2 S O1 107.93(9) . . ? O3 S O1 99.75(9) . . ? O2 S C11 109.58(10) . . ? O3 S C11 111.53(9) . . ? O1 S C11 105.00(9) . . ? N1 O1 S 113.00(12) . . ? C21 C11 C61 122.02(18) . . ? C21 C11 S 119.05(16) . . ? C61 C11 S 118.92(14) . . ? C13 C2 C3 121.31(19) . . ? C13 C2 C1 129.45(18) . . ? C3 C2 C1 109.21(17) . . ? C51 C61 C11 118.15(18) . . ? C51 C61 H61 123.5(16) . . ? C11 C61 H61 118.3(16) . . ? C31 C21 C11 118.28(19) . . ? C31 C21 H21 120.7(16) . . ? C11 C21 H21 121.0(16) . . ? C31 C41 C51 119.16(19) . . ? C31 C41 C71 120.65(19) . . ? C51 C41 C71 120.2(2) . . ? C16 C3 C2 121.7(2) . . ? C16 C3 C4 129.28(18) . . ? C2 C3 C4 108.98(17) . . ? O1 N1 C1 120.87(15) . . ? O1 N1 C4 117.36(15) . . ? C1 N1 C4 113.53(16) . . ? C21 C31 C41 121.17(19) . . ? C21 C31 H31 119.7(16) . . ? C41 C31 H31 119.1(16) . . ? O4 C1 N1 125.11(19) . . ? O4 C1 C2 131.50(19) . . ? N1 C1 C2 103.37(15) . . ? O5 C4 N1 124.54(19) . . ? O5 C4 C3 131.67(19) . . ? N1 C4 C3 103.78(16) . . ? C61 C51 C41 121.2(2) . . ? C61 C51 H51 119.3(16) . . ? C41 C51 H51 119.4(16) . . ? C2 C13 C14 117.20(19) . . ? C2 C13 H13 119.9(18) . . ? C14 C13 H13 122.8(18) . . ? C15 C14 C13 121.3(2) . . ? C15 C14 H14 120.0(16) . . ? C13 C14 H14 118.7(16) . . ? C3 C16 C15 117.45(19) . . ? C3 C16 H16 116.2(17) . . ? C15 C16 H16 126.4(18) . . ? C14 C15 C16 121.0(2) . . ? C14 C15 H15 120.7(16) . . ? C16 C15 H15 118.1(16) . . ? C41 C71 H711 110.1(17) . . ? C41 C71 H712 109.0(18) . . ? H711 C71 H712 105(2) . . ? C41 C71 H713 106.3(18) . . ? H711 C71 H713 110(2) . . ? H712 C71 H713 116(3) . . ? 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 O2 S O1 N1 -58.21(13) . . . . ? O3 S O1 N1 174.18(11) . . . . ? C11 S O1 N1 58.61(13) . . . . ? O2 S C11 C21 -154.50(15) . . . . ? O3 S C11 C21 -17.29(19) . . . . ? O1 S C11 C21 89.81(16) . . . . ? O2 S C11 C61 23.92(18) . . . . ? O3 S C11 C61 161.13(15) . . . . ? O1 S C11 C61 -91.77(16) . . . . ? C21 C11 C61 C51 -1.6(3) . . . . ? S C11 C61 C51 179.99(14) . . . . ? C61 C11 C21 C31 0.8(3) . . . . ? S C11 C21 C31 179.12(15) . . . . ? C13 C2 C3 C16 0.4(3) . . . . ? C1 C2 C3 C16 -177.44(18) . . . . ? C13 C2 C3 C4 178.20(18) . . . . ? C1 C2 C3 C4 0.3(2) . . . . ? S O1 N1 C1 102.54(17) . . . . ? S O1 N1 C4 -111.07(16) . . . . ? C11 C21 C31 C41 1.1(3) . . . . ? C51 C41 C31 C21 -1.9(3) . . . . ? C71 C41 C31 C21 176.7(2) . . . . ? O1 N1 C1 O4 -20.3(3) . . . . ? C4 N1 C1 O4 -167.88(19) . . . . ? O1 N1 C1 C2 158.39(16) . . . . ? C4 N1 C1 C2 10.8(2) . . . . ? C13 C2 C1 O4 -5.6(4) . . . . ? C3 C2 C1 O4 172.1(2) . . . . ? C13 C2 C1 N1 175.9(2) . . . . ? C3 C2 C1 N1 -6.5(2) . . . . ? O1 N1 C4 O5 19.7(3) . . . . ? C1 N1 C4 O5 168.44(19) . . . . ? O1 N1 C4 C3 -159.47(15) . . . . ? C1 N1 C4 C3 -10.7(2) . . . . ? C16 C3 C4 O5 4.5(4) . . . . ? C2 C3 C4 O5 -173.1(2) . . . . ? C16 C3 C4 N1 -176.51(19) . . . . ? C2 C3 C4 N1 5.9(2) . . . . ? C11 C61 C51 C41 0.7(3) . . . . ? C31 C41 C51 C61 1.0(3) . . . . ? C71 C41 C51 C61 -177.63(19) . . . . ? C3 C2 C13 C14 -0.4(3) . . . . ? C1 C2 C13 C14 177.03(19) . . . . ? C2 C13 C14 C15 -0.3(3) . . . . ? C2 C3 C16 C15 0.2(3) . . . . ? C4 C3 C16 C15 -177.14(19) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C3 C16 C15 C14 -0.8(3) . . . . ? 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 C16 H16 O2 0.91(3) 2.50(3) 3.369(3) 161(2) 4_676 C21 H21 O3 0.96(3) 2.50(3) 3.334(3) 146(2) 3_765 C61 H61 O4 0.98(3) 2.43(3) 3.392(2) 167(2) 2_655 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.615 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.077