data_2f _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H18 N2 O3 S' _chemical_formula_sum 'C13 H18 N2 O3 S' _chemical_formula_weight 282.35 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 10.1217(2) _cell_length_b 5.26760(10) _cell_length_c 25.2607(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.6910(10) _cell_angle_gamma 90.00 _cell_volume 1331.36(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 2.226 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6645 _exptl_absorpt_correction_T_max 0.7313 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'BRUKER SMART APEXII CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12939 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 66.59 _reflns_number_total 2342 _reflns_number_gt 2076 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _publ_section_references ; Bruker AXS. (2010). APEX2 Bruker AXS, Inc. Madison, Wisconsin, USA. Bruker AXS. (2009). SAINT Bruker AXS, Inc. Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _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^)+(0.0532P)^2^+0.4504P] 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 0.0031(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2342 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 S1 S 0.21302(4) 0.37715(8) 0.037797(16) 0.01346(17) Uani 1 1 d . . . O1 O 0.50021(13) -0.2052(3) 0.14796(5) 0.0221(3) Uani 1 1 d . . . O2 O 0.13228(13) 0.3014(2) -0.01075(5) 0.0188(3) Uani 1 1 d . . . O3 O 0.28125(13) 0.6169(2) 0.04098(5) 0.0193(3) Uani 1 1 d . . . N1 N 0.32864(15) 0.1608(3) 0.05256(6) 0.0140(3) Uani 1 1 d . . . H1N H 0.292(2) 0.017(5) 0.0448(9) 0.019(6) Uiso 1 1 d . . . N2 N 0.12169(15) 0.3734(3) 0.08651(6) 0.0148(3) Uani 1 1 d . . . C1 C 0.50187(17) -0.0479(3) 0.11305(7) 0.0159(4) Uani 1 1 d . . . C2 C 0.40463(17) 0.1777(3) 0.10783(7) 0.0146(4) Uani 1 1 d . . . H2 H 0.4589 0.3370 0.1101 0.018 Uiso 1 1 calc R . . C3 C 0.02457(18) 0.1589(3) 0.08279(7) 0.0177(4) Uani 1 1 d . . . H3A H 0.0734 -0.0045 0.0846 0.021 Uiso 1 1 calc R . . H3B H -0.0355 0.1664 0.0481 0.021 Uiso 1 1 calc R . . C4 C -0.05675(18) 0.1743(3) 0.12804(7) 0.0167(4) Uani 1 1 d . . . C5 C -0.14835(19) 0.3703(4) 0.12974(8) 0.0200(4) Uani 1 1 d . . . H5 H -0.1594 0.4949 0.1022 0.024 Uiso 1 1 calc R . . C6 C -0.22340(19) 0.3856(4) 0.17114(8) 0.0214(4) Uani 1 1 d . . . H6 H -0.2864 0.5190 0.1717 0.026 Uiso 1 1 calc R . . C7 C -0.20671(19) 0.2061(4) 0.21191(8) 0.0223(4) Uani 1 1 d . . . H7 H -0.2577 0.2172 0.2405 0.027 Uiso 1 1 calc R . . C8 C 0.59579(19) -0.0663(4) 0.07252(8) 0.0244(4) Uani 1 1 d . . . H8A H 0.6832 -0.1259 0.0901 0.037 Uiso 1 1 calc R . . H8B H 0.6056 0.1013 0.0567 0.037 Uiso 1 1 calc R . . H8C H 0.5599 -0.1862 0.0443 0.037 Uiso 1 1 calc R . . C9 C 0.31553(18) 0.1888(3) 0.15158(7) 0.0148(4) Uani 1 1 d . . . H9 H 0.2692 0.0219 0.1532 0.018 Uiso 1 1 calc R . . C10 C 0.39730(19) 0.2457(4) 0.20614(7) 0.0200(4) Uani 1 1 d . . . H10A H 0.4640 0.1116 0.2154 0.030 Uiso 1 1 calc R . . H10B H 0.3378 0.2524 0.2333 0.030 Uiso 1 1 calc R . . H10C H 0.4426 0.4094 0.2048 0.030 Uiso 1 1 calc R . . C11 C 0.21039(17) 0.3989(3) 0.13888(7) 0.0146(4) Uani 1 1 d . . . H11A H 0.1540 0.4018 0.1677 0.018 Uiso 1 1 calc R . . H11B H 0.2571 0.5643 0.1395 0.018 Uiso 1 1 calc R . . C12 C -0.11538(19) 0.0108(4) 0.21079(8) 0.0235(4) Uani 1 1 d . . . H12 H -0.1036 -0.1123 0.2386 0.028 Uiso 1 1 calc R . . C13 C -0.04113(18) -0.0048(3) 0.16896(8) 0.0206(4) Uani 1 1 d . . . H13 H 0.0211 -0.1394 0.1683 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0159(2) 0.0119(3) 0.0124(2) 0.00117(14) 0.00152(16) 0.00180(15) O1 0.0234(7) 0.0197(7) 0.0227(7) 0.0035(5) 0.0018(5) 0.0044(5) O2 0.0206(7) 0.0210(7) 0.0139(6) 0.0010(5) -0.0002(5) 0.0024(5) O3 0.0226(7) 0.0137(7) 0.0216(7) 0.0024(5) 0.0038(5) -0.0002(5) N1 0.0169(8) 0.0109(8) 0.0143(8) -0.0006(5) 0.0026(6) 0.0010(6) N2 0.0139(7) 0.0147(8) 0.0157(8) -0.0007(5) 0.0017(6) 0.0013(6) C1 0.0134(8) 0.0171(9) 0.0158(9) -0.0030(7) -0.0017(7) 0.0014(7) C2 0.0152(8) 0.0135(9) 0.0149(9) -0.0003(6) 0.0015(7) -0.0010(6) C3 0.0160(9) 0.0155(9) 0.0215(9) -0.0025(7) 0.0022(7) -0.0014(7) C4 0.0136(9) 0.0169(9) 0.0189(9) -0.0027(7) 0.0005(7) -0.0028(7) C5 0.0194(9) 0.0184(10) 0.0219(10) 0.0025(7) 0.0019(7) 0.0008(7) C6 0.0180(9) 0.0202(10) 0.0259(10) -0.0020(7) 0.0033(8) 0.0027(7) C7 0.0196(10) 0.0253(11) 0.0233(10) -0.0016(8) 0.0074(7) -0.0034(8) C8 0.0201(10) 0.0280(11) 0.0254(10) -0.0007(8) 0.0049(8) 0.0073(8) C9 0.0161(9) 0.0136(9) 0.0147(9) -0.0003(6) 0.0021(7) 0.0008(7) C10 0.0216(9) 0.0235(10) 0.0144(9) -0.0008(7) 0.0012(7) 0.0038(7) C11 0.0162(9) 0.0150(9) 0.0125(8) -0.0019(6) 0.0022(7) 0.0001(7) C12 0.0243(10) 0.0223(11) 0.0242(10) 0.0061(8) 0.0042(8) -0.0018(8) C13 0.0172(9) 0.0169(10) 0.0279(10) 0.0013(7) 0.0036(7) 0.0018(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4242(13) . ? S1 O3 1.4361(13) . ? S1 N1 1.6357(15) . ? S1 N2 1.6472(15) . ? O1 C1 1.212(2) . ? N1 C2 1.491(2) . ? N1 H1N 0.85(2) . ? N2 C11 1.488(2) . ? N2 C3 1.491(2) . ? C1 C8 1.502(3) . ? C1 C2 1.536(2) . ? C2 C9 1.529(2) . ? C2 H2 1.0000 . ? C3 C4 1.508(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C13 1.391(3) . ? C4 C5 1.393(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.389(3) . ? C6 H6 0.9500 . ? C7 C12 1.386(3) . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.526(2) . ? C9 C11 1.535(2) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.389(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 S1 O3 120.22(8) . . ? O2 S1 N1 107.38(8) . . ? O3 S1 N1 106.17(8) . . ? O2 S1 N2 109.04(8) . . ? O3 S1 N2 106.74(8) . . ? N1 S1 N2 106.52(7) . . ? C2 N1 S1 114.95(11) . . ? C2 N1 H1N 114.4(15) . . ? S1 N1 H1N 107.2(15) . . ? C11 N2 C3 115.32(14) . . ? C11 N2 S1 109.37(11) . . ? C3 N2 S1 113.63(11) . . ? O1 C1 C8 122.12(16) . . ? O1 C1 C2 120.82(15) . . ? C8 C1 C2 117.05(15) . . ? N1 C2 C9 113.69(14) . . ? N1 C2 C1 105.50(13) . . ? C9 C2 C1 114.06(14) . . ? N1 C2 H2 107.8 . . ? C9 C2 H2 107.8 . . ? C1 C2 H2 107.8 . . ? N2 C3 C4 109.97(14) . . ? N2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? N2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C13 C4 C5 118.79(17) . . ? C13 C4 C3 120.86(16) . . ? C5 C4 C3 120.35(17) . . ? C6 C5 C4 120.66(17) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.08(17) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C12 C7 C6 119.78(17) . . ? C12 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C2 111.20(14) . . ? C10 C9 C11 108.15(14) . . ? C2 C9 C11 110.03(14) . . ? C10 C9 H9 109.1 . . ? C2 C9 H9 109.1 . . ? C11 C9 H9 109.1 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C9 115.26(14) . . ? N2 C11 H11A 108.5 . . ? C9 C11 H11A 108.5 . . ? N2 C11 H11B 108.5 . . ? C9 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C7 C12 C13 119.91(18) . . ? C7 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C4 120.77(17) . . ? C12 C13 H13 119.6 . . ? C4 C13 H13 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N1 C2 -167.42(12) . . . . ? O3 S1 N1 C2 62.80(13) . . . . ? N2 S1 N1 C2 -50.71(14) . . . . ? O2 S1 N2 C11 168.23(11) . . . . ? O3 S1 N2 C11 -60.49(12) . . . . ? N1 S1 N2 C11 52.63(13) . . . . ? O2 S1 N2 C3 37.79(14) . . . . ? O3 S1 N2 C3 169.07(12) . . . . ? N1 S1 N2 C3 -77.81(13) . . . . ? S1 N1 C2 C9 52.01(18) . . . . ? S1 N1 C2 C1 177.72(11) . . . . ? O1 C1 C2 N1 -122.24(17) . . . . ? C8 C1 C2 N1 56.51(19) . . . . ? O1 C1 C2 C9 3.2(2) . . . . ? C8 C1 C2 C9 -178.01(15) . . . . ? C11 N2 C3 C4 54.00(19) . . . . ? S1 N2 C3 C4 -178.59(12) . . . . ? N2 C3 C4 C13 -111.23(18) . . . . ? N2 C3 C4 C5 68.2(2) . . . . ? C13 C4 C5 C6 -0.6(3) . . . . ? C3 C4 C5 C6 179.97(17) . . . . ? C4 C5 C6 C7 0.8(3) . . . . ? C5 C6 C7 C12 -0.4(3) . . . . ? N1 C2 C9 C10 -171.49(15) . . . . ? C1 C2 C9 C10 67.47(19) . . . . ? N1 C2 C9 C11 -51.70(19) . . . . ? C1 C2 C9 C11 -172.73(14) . . . . ? C3 N2 C11 C9 69.52(19) . . . . ? S1 N2 C11 C9 -60.00(16) . . . . ? C10 C9 C11 N2 179.69(14) . . . . ? C2 C9 C11 N2 58.06(19) . . . . ? C6 C7 C12 C13 -0.1(3) . . . . ? C7 C12 C13 C4 0.3(3) . . . . ? C5 C4 C13 C12 0.1(3) . . . . ? C3 C4 C13 C12 179.51(17) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.389 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.057