data_publication_text _publ_contact_author_name 'Stephan Scheins' _publ_contact_author_address ;738 Natural Science Complex 14260 Buffalo ; _publ_contact_author_email chem9993@buffalo.edu _publ_contact_author_phone '716 6454272' loop_ _publ_author_name _publ_author_address ' Scheins, Stephan' ;738 Natural Science Complex 14260 Buffalo ; _publ_requested_journal 'Private Communication' data_sad _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H19 N O3 S' _chemical_formula_sum 'C14 H19 N O3 S' _chemical_formula_weight 281.37 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 'triclinic' _symmetry_space_group_name_H-M 'P_-1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.34120(10) _cell_length_b 10.8365(3) _cell_length_c 11.3636(3) _cell_angle_alpha 94.3710(10) _cell_angle_beta 91.0270(10) _cell_angle_gamma 91.3550(10) _cell_volume 655.50(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9885 _cell_measurement_theta_min 4.993 _cell_measurement_theta_max 56.694 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.7207 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26669 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.39 _reflns_number_total 3269 _reflns_number_gt 2940 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0386P)^2^+0.3767P] 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 3269 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.98280(5) 0.58463(2) 0.80167(3) 0.01432(9) Uani 1 1 d . . . O1 O 0.11262(15) 1.10544(8) 0.65128(7) 0.01494(17) Uani 1 1 d . . . N1 N 0.86679(18) 0.67376(9) 0.70705(9) 0.01291(19) Uani 1 1 d . . . O2 O 1.08128(18) 0.66151(8) 0.90106(8) 0.0226(2) Uani 1 1 d . . . O3 O 1.14998(16) 0.50347(8) 0.73695(9) 0.0211(2) Uani 1 1 d . . . C5 C 0.44342(19) 1.00102(10) 0.73391(9) 0.0111(2) Uani 1 1 d . . . C10 C 0.6285(2) 0.99186(10) 0.82116(10) 0.0113(2) Uani 1 1 d . . . C11 C 0.8002(2) 0.88201(10) 0.82160(10) 0.0122(2) Uani 1 1 d . . . H11A H 0.9641 0.9054 0.7939 0.015 Uiso 1 1 calc R . . H11B H 0.8200 0.8574 0.9015 0.015 Uiso 1 1 calc R . . C4 C 0.3990(2) 0.90273(10) 0.63322(10) 0.0120(2) Uani 1 1 d . . . H4A H 0.3758 0.9421 0.5601 0.014 Uiso 1 1 calc R . . H4B H 0.2473 0.8554 0.6470 0.014 Uiso 1 1 calc R . . C12 C 0.6914(2) 0.77405(10) 0.74238(10) 0.0115(2) Uani 1 1 d . . . H12 H 0.544(3) 0.7389(13) 0.7792(13) 0.014 Uiso 1 1 calc . . . C7 C 0.3214(2) 1.19948(10) 0.82988(10) 0.0139(2) Uani 1 1 d . . . H7 H 0.2195 1.2680 0.8330 0.017 Uiso 1 1 calc R . . C6 C 0.2899(2) 1.10560(10) 0.73986(10) 0.0119(2) Uani 1 1 d . . . C9 C 0.6596(2) 1.08649(10) 0.91184(10) 0.0135(2) Uani 1 1 d . . . H9 H 0.7825 1.0805 0.9700 0.016 Uiso 1 1 calc R . . C3 C 0.6178(2) 0.81616(10) 0.62169(10) 0.0118(2) Uani 1 1 d . . . H3 H 0.761(3) 0.8606(14) 0.5903(13) 0.014 Uiso 1 1 calc . . . C8 C 0.5089(2) 1.18869(10) 0.91546(10) 0.0141(2) Uani 1 1 d . . . H8 H 0.5327 1.2511 0.9757 0.017 Uiso 1 1 calc R . . C13 C -0.0542(2) 1.20682(11) 0.65524(11) 0.0158(2) Uani 1 1 d . . . H13A H -0.1489 1.2078 0.7263 0.024 Uiso 1 1 calc R . . H13B H -0.1663 1.1977 0.5880 0.024 Uiso 1 1 calc R . . H13C H 0.0407 1.2831 0.6541 0.024 Uiso 1 1 calc R . . C2 C 0.5748(2) 0.69368(10) 0.54767(10) 0.0143(2) Uani 1 1 d . . . H2A H 0.5869 0.7050 0.4641 0.017 Uiso 1 1 calc R . . H2B H 0.4118 0.6573 0.5625 0.017 Uiso 1 1 calc R . . C1 C 0.7861(2) 0.61274(11) 0.58931(10) 0.0166(2) Uani 1 1 d . . . H1A H 0.7256 0.5286 0.5968 0.020 Uiso 1 1 calc R . . H1B H 0.9235 0.6110 0.5346 0.020 Uiso 1 1 calc R . . C14 C 0.7342(2) 0.49379(12) 0.85238(12) 0.0205(2) Uani 1 1 d . . . H14A H 0.7984 0.4389 0.9074 0.031 Uiso 1 1 calc R . . H14B H 0.6551 0.4463 0.7866 0.031 Uiso 1 1 calc R . . H14C H 0.6139 0.5468 0.8907 0.031 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 0.01271(14) 0.01026(13) 0.02007(15) 0.00280(10) -0.00465(10) 0.00044(9) O1 0.0146(4) 0.0140(4) 0.0160(4) -0.0013(3) -0.0037(3) 0.0049(3) N1 0.0136(4) 0.0104(4) 0.0148(4) 0.0010(3) -0.0017(3) 0.0028(3) O2 0.0268(5) 0.0155(4) 0.0249(5) 0.0017(4) -0.0139(4) -0.0001(3) O3 0.0161(4) 0.0150(4) 0.0324(5) 0.0030(4) -0.0009(4) 0.0051(3) C5 0.0111(5) 0.0105(5) 0.0115(5) 0.0007(4) 0.0005(4) -0.0005(4) C10 0.0112(5) 0.0107(5) 0.0122(5) 0.0017(4) 0.0009(4) -0.0007(4) C11 0.0116(5) 0.0117(5) 0.0132(5) 0.0008(4) -0.0017(4) 0.0007(4) C4 0.0119(5) 0.0124(5) 0.0115(5) -0.0002(4) -0.0014(4) 0.0022(4) C12 0.0111(5) 0.0101(5) 0.0136(5) 0.0016(4) -0.0006(4) 0.0012(4) C7 0.0146(5) 0.0109(5) 0.0162(5) 0.0000(4) 0.0019(4) 0.0012(4) C6 0.0104(5) 0.0127(5) 0.0128(5) 0.0021(4) -0.0001(4) -0.0004(4) C9 0.0141(5) 0.0144(5) 0.0117(5) 0.0008(4) -0.0020(4) -0.0014(4) C3 0.0114(5) 0.0120(5) 0.0120(5) 0.0005(4) -0.0006(4) 0.0010(4) C8 0.0168(5) 0.0118(5) 0.0131(5) -0.0017(4) 0.0010(4) -0.0020(4) C13 0.0150(5) 0.0139(5) 0.0186(5) 0.0015(4) -0.0017(4) 0.0044(4) C2 0.0141(5) 0.0138(5) 0.0145(5) -0.0017(4) -0.0011(4) 0.0024(4) C1 0.0201(5) 0.0140(5) 0.0154(5) -0.0013(4) -0.0018(4) 0.0048(4) C14 0.0196(6) 0.0176(6) 0.0252(6) 0.0085(5) -0.0007(5) -0.0017(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 S1 O2 1.4356(9) . ? S1 O3 1.4401(9) . ? S1 N1 1.6234(10) . ? S1 C14 1.7654(13) . ? O1 C6 1.3696(13) . ? O1 C13 1.4293(13) . ? N1 C12 1.4882(13) . ? N1 C1 1.4981(15) . ? C5 C10 1.3982(15) . ? C5 C6 1.4125(15) . ? C5 C4 1.5140(14) . ? C10 C9 1.4020(15) . ? C10 C11 1.5199(15) . ? C11 C12 1.5183(15) . ? C4 C3 1.5171(14) . ? C12 C3 1.5259(15) . ? C7 C6 1.3916(15) . ? C7 C8 1.3966(16) . ? C9 C8 1.3832(16) . ? C3 C2 1.5266(15) . ? C2 C1 1.5357(15) . ? 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 118.58(6) . . ? O2 S1 N1 108.20(5) . . ? O3 S1 N1 106.25(5) . . ? O2 S1 C14 107.44(6) . . ? O3 S1 C14 108.19(6) . . ? N1 S1 C14 107.75(6) . . ? C6 O1 C13 117.04(9) . . ? C12 N1 C1 109.49(8) . . ? C12 N1 S1 122.04(8) . . ? C1 N1 S1 116.58(7) . . ? C10 C5 C6 118.95(10) . . ? C10 C5 C4 122.67(10) . . ? C6 C5 C4 118.38(9) . . ? C5 C10 C9 119.65(10) . . ? C5 C10 C11 122.22(10) . . ? C9 C10 C11 118.13(10) . . ? C12 C11 C10 110.24(9) . . ? C5 C4 C3 111.10(9) . . ? N1 C12 C11 116.27(9) . . ? N1 C12 C3 100.48(8) . . ? C11 C12 C3 110.54(9) . . ? C6 C7 C8 118.68(10) . . ? O1 C6 C7 124.12(10) . . ? O1 C6 C5 114.59(9) . . ? C7 C6 C5 121.29(10) . . ? C8 C9 C10 120.50(10) . . ? C4 C3 C12 110.08(9) . . ? C4 C3 C2 117.28(9) . . ? C12 C3 C2 102.58(9) . . ? C9 C8 C7 120.93(10) . . ? C3 C2 C1 103.51(9) . . ? N1 C1 C2 104.23(9) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.401 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.052