data_2j _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 N2 O3 S' _chemical_formula_weight 322.42 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 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 10.5533(2) _cell_length_b 14.5967(2) _cell_length_c 10.1764(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.7800(10) _cell_angle_gamma 90.00 _cell_volume 1556.64(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 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.974 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6936 _exptl_absorpt_correction_T_max 0.7177 _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 19566 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.22 _diffrn_reflns_theta_max 66.56 _reflns_number_total 2740 _reflns_number_gt 2418 _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^)+(0.0505P)^2^+0.6831P] 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(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2740 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.44407(4) -0.00380(3) 0.77945(4) 0.01480(15) Uani 1 1 d . . . O1 O 0.32522(11) 0.20860(8) 0.56129(11) 0.0218(3) Uani 1 1 d . . . O2 O 0.35882(11) -0.01347(8) 0.65951(11) 0.0192(3) Uani 1 1 d . . . O3 O 0.45367(12) -0.07875(8) 0.87140(12) 0.0209(3) Uani 1 1 d . . . N1 N 0.39938(13) 0.08573(9) 0.85597(14) 0.0154(3) Uani 1 1 d . . . H1N H 0.440(2) 0.0855(15) 0.931(2) 0.029(6) Uiso 1 1 d . . . N2 N 0.59041(13) 0.02127(9) 0.74785(13) 0.0151(3) Uani 1 1 d . . . C1 C 0.16833(16) 0.16372(13) 0.69911(18) 0.0232(4) Uani 1 1 d . . . H1C H 0.1076 0.1790 0.6218 0.035 Uiso 1 1 calc R . . H1D H 0.1505 0.2014 0.7745 0.035 Uiso 1 1 calc R . . H1E H 0.1598 0.0988 0.7209 0.035 Uiso 1 1 calc R . . C2 C 0.30168(16) 0.18210(11) 0.66852(16) 0.0171(4) Uani 1 1 d . . . C3 C 0.40823(15) 0.17353(11) 0.78415(16) 0.0151(3) Uani 1 1 d . . . H3 H 0.3922 0.2229 0.8482 0.018 Uiso 1 1 calc R . . C4 C 0.64847(16) -0.05828(12) 0.68398(17) 0.0203(4) Uani 1 1 d . . . H4A H 0.6448 -0.0468 0.5877 0.024 Uiso 1 1 calc R . . H4B H 0.5979 -0.1141 0.6964 0.024 Uiso 1 1 calc R . . C5 C 0.78557(16) -0.07452(11) 0.74066(17) 0.0194(4) Uani 1 1 d . . . C6 C 0.88181(18) -0.07559(12) 0.65866(18) 0.0251(4) Uani 1 1 d . . . H6 H 0.8611 -0.0674 0.5660 0.030 Uiso 1 1 calc R . . C7 C 1.00837(18) -0.08859(13) 0.7110(2) 0.0293(4) Uani 1 1 d . . . H7 H 1.0738 -0.0884 0.6544 0.035 Uiso 1 1 calc R . . C8 C 1.03886(18) -0.10179(13) 0.8453(2) 0.0300(4) Uani 1 1 d . . . H8 H 1.1252 -0.1105 0.8813 0.036 Uiso 1 1 calc R . . C9 C 0.94353(18) -0.10230(13) 0.92719(19) 0.0270(4) Uani 1 1 d . . . H9 H 0.9644 -0.1120 1.0195 0.032 Uiso 1 1 calc R . . C10 C 0.81740(17) -0.08864(12) 0.87537(18) 0.0224(4) Uani 1 1 d . . . H10 H 0.7524 -0.0889 0.9325 0.027 Uiso 1 1 calc R . . C11 C 0.59384(15) 0.10970(11) 0.67156(16) 0.0148(3) Uani 1 1 d . . . H11 H 0.5391 0.1028 0.5850 0.018 Uiso 1 1 calc R . . C12 C 0.72998(15) 0.13173(12) 0.64449(16) 0.0186(4) Uani 1 1 d . . . H12A H 0.7649 0.0782 0.6010 0.022 Uiso 1 1 calc R . . H12B H 0.7274 0.1839 0.5821 0.022 Uiso 1 1 calc R . . C13 C 0.81942(16) 0.15548(12) 0.76825(17) 0.0200(4) Uani 1 1 d . . . H13A H 0.8291 0.1017 0.8279 0.024 Uiso 1 1 calc R . . H13B H 0.9046 0.1714 0.7434 0.024 Uiso 1 1 calc R . . C14 C 0.76662(16) 0.23589(12) 0.83975(18) 0.0207(4) Uani 1 1 d . . . H14A H 0.7648 0.2912 0.7832 0.025 Uiso 1 1 calc R . . H14B H 0.8230 0.2486 0.9225 0.025 Uiso 1 1 calc R . . C15 C 0.63243(16) 0.21508(12) 0.87218(17) 0.0189(4) Uani 1 1 d . . . H15A H 0.5984 0.2693 0.9147 0.023 Uiso 1 1 calc R . . H15B H 0.6359 0.1636 0.9359 0.023 Uiso 1 1 calc R . . C16 C 0.54235(15) 0.18999(11) 0.74812(16) 0.0150(3) Uani 1 1 d . . . H16 H 0.5377 0.2445 0.6883 0.018 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 0.0155(2) 0.0130(2) 0.0153(2) 0.00021(15) -0.00096(16) -0.00206(14) O1 0.0191(6) 0.0253(7) 0.0205(6) 0.0035(5) 0.0004(5) 0.0028(5) O2 0.0180(6) 0.0194(6) 0.0191(6) -0.0010(5) -0.0021(5) -0.0029(5) O3 0.0266(6) 0.0150(6) 0.0204(6) 0.0035(5) -0.0006(5) -0.0029(5) N1 0.0167(7) 0.0158(7) 0.0134(7) 0.0001(6) 0.0006(6) -0.0014(5) N2 0.0138(7) 0.0131(7) 0.0177(7) -0.0005(6) -0.0015(5) 0.0010(5) C1 0.0137(8) 0.0269(9) 0.0284(10) -0.0007(8) 0.0009(7) 0.0017(7) C2 0.0162(8) 0.0132(8) 0.0216(9) -0.0025(7) 0.0008(7) 0.0014(6) C3 0.0162(8) 0.0120(8) 0.0170(8) -0.0007(6) 0.0017(6) -0.0003(6) C4 0.0208(9) 0.0170(8) 0.0220(9) -0.0062(7) -0.0018(7) 0.0034(7) C5 0.0204(9) 0.0121(8) 0.0246(9) -0.0037(7) -0.0019(7) 0.0035(6) C6 0.0278(10) 0.0233(9) 0.0239(9) -0.0033(8) 0.0024(8) 0.0100(7) C7 0.0234(9) 0.0288(10) 0.0367(11) -0.0012(9) 0.0074(8) 0.0094(8) C8 0.0199(9) 0.0275(10) 0.0408(11) -0.0011(9) -0.0043(8) 0.0078(8) C9 0.0266(10) 0.0266(10) 0.0260(10) 0.0004(8) -0.0039(8) 0.0058(8) C10 0.0216(9) 0.0193(9) 0.0260(9) 0.0013(7) 0.0015(7) 0.0021(7) C11 0.0154(8) 0.0154(8) 0.0127(7) 0.0012(6) -0.0015(6) 0.0002(6) C12 0.0154(8) 0.0221(9) 0.0181(8) 0.0024(7) 0.0019(7) 0.0016(7) C13 0.0128(8) 0.0229(9) 0.0239(9) 0.0025(7) 0.0001(7) -0.0024(7) C14 0.0157(8) 0.0197(8) 0.0257(9) -0.0015(7) -0.0021(7) -0.0049(7) C15 0.0177(8) 0.0175(8) 0.0209(8) -0.0031(7) -0.0001(7) -0.0026(6) C16 0.0142(8) 0.0122(8) 0.0182(8) 0.0005(7) 0.0001(7) -0.0012(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 S1 O2 1.4351(12) . ? S1 O3 1.4354(12) . ? S1 N1 1.6198(14) . ? S1 N2 1.6552(14) . ? O1 C2 1.211(2) . ? N1 C3 1.484(2) . ? N1 H1N 0.83(2) . ? N2 C4 1.497(2) . ? N2 C11 1.509(2) . ? C1 C2 1.501(2) . ? C1 H1C 0.9800 . ? C1 H1D 0.9800 . ? C1 H1E 0.9800 . ? C2 C3 1.534(2) . ? C3 C16 1.523(2) . ? C3 H3 1.0000 . ? C4 C5 1.512(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.388(3) . ? C5 C6 1.389(3) . ? C6 C7 1.391(3) . ? C6 H6 0.9500 . ? C7 C8 1.380(3) . ? C7 H7 0.9500 . ? C8 C9 1.380(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.529(2) . ? C11 C16 1.541(2) . ? C11 H11 1.0000 . ? C12 C13 1.522(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.521(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.522(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.532(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16 1.0000 . ? 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 117.93(7) . . ? O2 S1 N1 107.42(7) . . ? O3 S1 N1 107.68(7) . . ? O2 S1 N2 111.23(7) . . ? O3 S1 N2 107.43(7) . . ? N1 S1 N2 104.26(7) . . ? C3 N1 S1 114.91(11) . . ? C3 N1 H1N 113.6(15) . . ? S1 N1 H1N 106.8(15) . . ? C4 N2 C11 113.85(13) . . ? C4 N2 S1 110.61(11) . . ? C11 N2 S1 111.63(10) . . ? C2 C1 H1C 109.5 . . ? C2 C1 H1D 109.5 . . ? H1C C1 H1D 109.5 . . ? C2 C1 H1E 109.5 . . ? H1C C1 H1E 109.5 . . ? H1D C1 H1E 109.5 . . ? O1 C2 C1 122.76(15) . . ? O1 C2 C3 120.51(15) . . ? C1 C2 C3 116.53(14) . . ? N1 C3 C16 111.68(13) . . ? N1 C3 C2 111.43(13) . . ? C16 C3 C2 114.87(13) . . ? N1 C3 H3 106.1 . . ? C16 C3 H3 106.1 . . ? C2 C3 H3 106.1 . . ? N2 C4 C5 112.24(13) . . ? N2 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N2 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C10 C5 C6 118.88(16) . . ? C10 C5 C4 120.62(16) . . ? C6 C5 C4 120.50(16) . . ? C5 C6 C7 120.56(17) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 119.98(18) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 119.82(18) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C9 C10 120.32(18) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C5 120.43(17) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? N2 C11 C12 110.66(13) . . ? N2 C11 C16 111.05(13) . . ? C12 C11 C16 109.03(13) . . ? N2 C11 H11 108.7 . . ? C12 C11 H11 108.7 . . ? C16 C11 H11 108.7 . . ? C13 C12 C11 113.76(13) . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 110.19(14) . . ? C14 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C13 C14 C15 110.64(14) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C14 C15 C16 111.81(14) . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C3 C16 C15 110.07(13) . . ? C3 C16 C11 113.26(13) . . ? C15 C16 C11 112.13(13) . . ? C3 C16 H16 107.0 . . ? C15 C16 H16 107.0 . . ? C11 C16 H16 107.0 . . ? 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 C3 -63.18(13) . . . . ? O3 S1 N1 C3 168.86(11) . . . . ? N2 S1 N1 C3 54.94(13) . . . . ? O2 S1 N2 C4 -68.10(12) . . . . ? O3 S1 N2 C4 62.34(12) . . . . ? N1 S1 N2 C4 176.43(11) . . . . ? O2 S1 N2 C11 59.77(12) . . . . ? O3 S1 N2 C11 -169.79(10) . . . . ? N1 S1 N2 C11 -55.70(12) . . . . ? S1 N1 C3 C16 -55.63(16) . . . . ? S1 N1 C3 C2 74.32(15) . . . . ? O1 C2 C3 N1 -134.89(16) . . . . ? C1 C2 C3 N1 50.04(18) . . . . ? O1 C2 C3 C16 -6.6(2) . . . . ? C1 C2 C3 C16 178.30(14) . . . . ? C11 N2 C4 C5 96.61(16) . . . . ? S1 N2 C4 C5 -136.74(13) . . . . ? N2 C4 C5 C10 56.2(2) . . . . ? N2 C4 C5 C6 -123.79(17) . . . . ? C10 C5 C6 C7 -1.4(3) . . . . ? C4 C5 C6 C7 178.62(16) . . . . ? C5 C6 C7 C8 0.9(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 C10 -0.7(3) . . . . ? C8 C9 C10 C5 0.1(3) . . . . ? C6 C5 C10 C9 0.9(3) . . . . ? C4 C5 C10 C9 -179.13(16) . . . . ? C4 N2 C11 C12 -54.30(17) . . . . ? S1 N2 C11 C12 179.58(11) . . . . ? C4 N2 C11 C16 -175.53(12) . . . . ? S1 N2 C11 C16 58.35(15) . . . . ? N2 C11 C12 C13 -67.85(17) . . . . ? C16 C11 C12 C13 54.56(18) . . . . ? C11 C12 C13 C14 -56.97(19) . . . . ? C12 C13 C14 C15 56.11(18) . . . . ? C13 C14 C15 C16 -56.23(18) . . . . ? N1 C3 C16 C15 -72.87(16) . . . . ? C2 C3 C16 C15 159.00(13) . . . . ? N1 C3 C16 C11 53.55(17) . . . . ? C2 C3 C16 C11 -74.59(17) . . . . ? C14 C15 C16 C3 -177.72(13) . . . . ? C14 C15 C16 C11 55.23(18) . . . . ? N2 C11 C16 C3 -55.94(17) . . . . ? C12 C11 C16 C3 -178.12(13) . . . . ? N2 C11 C16 C15 69.38(16) . . . . ? C12 C11 C16 C15 -52.80(17) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 66.56 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.354 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.059