data_global _publ_contact_author_email CMYU@CHEM.SKKU.AC.KR _publ_contact_author_name 'Prof Chan-Mo Yu' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name C.-M.Yu K.Ji-Min L.Junhee L.Su-Kyung data_yus _database_code_CSD 210261 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 O3 S' _chemical_formula_weight 278.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2348(18) _cell_length_b 23.217(3) _cell_length_c 6.268(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.96(2) _cell_angle_gamma 90.00 _cell_volume 1466.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.92 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'Siemens P4' _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 2779 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.1104 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2532 _reflns_number_gt 1101 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0472P)^2^+1.1106P] 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 2532 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1851 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.1694 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.022 _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 S1 S 0.21320(15) 0.47231(6) 0.1627(3) 0.0807(6) Uani 1 1 d . . . O1 O 0.5825(4) 0.29033(17) -0.1041(7) 0.0843(13) Uani 1 1 d . . . O2 O 0.3847(3) 0.30002(13) -0.0321(5) 0.0629(10) Uani 1 1 d . . . O3 O 0.4035(3) 0.43125(14) -0.0202(6) 0.0718(11) Uani 1 1 d . . . C1 C 0.5171(5) 0.3084(2) 0.0234(10) 0.0585(14) Uani 1 1 d . . . C2 C 0.5740(6) 0.3401(3) 0.2239(10) 0.0627(15) Uani 1 1 d . . . C3 C 0.4794(5) 0.3577(2) 0.3743(9) 0.0600(15) Uani 1 1 d . . . C4 C 0.3412(5) 0.3688(2) 0.2486(8) 0.0527(13) Uani 1 1 d . . . C5 C 0.2935(5) 0.3155(2) 0.1119(9) 0.0536(14) Uani 1 1 d . . . C6 C 0.5349(8) 0.4086(3) 0.5158(13) 0.0772(19) Uani 1 1 d . . . C7 C 0.3323(5) 0.42309(19) 0.1095(8) 0.0507(13) Uani 1 1 d . . . C8 C 0.2340(8) 0.5283(3) -0.0280(13) 0.088(2) Uani 1 1 d . . . C9 C 0.1618(10) 0.5180(5) -0.2535(17) 0.111(3) Uani 1 1 d . . . C10 C 0.1577(3) 0.32079(14) -0.0220(6) 0.0563(13) Uani 1 1 d G . . C11 C 0.1402(4) 0.34409(15) -0.2270(7) 0.0715(16) Uani 1 1 d G . . H11 H 0.2135 0.3556 -0.2860 0.086 Uiso 1 1 calc R . . C12 C 0.0144(5) 0.35041(16) -0.3447(6) 0.101(2) Uani 1 1 d G . . H12 H 0.0026 0.3661 -0.4832 0.121 Uiso 1 1 calc R . . C13 C -0.0940(4) 0.33343(18) -0.2574(9) 0.111(3) Uani 1 1 d G . . H13 H -0.1790 0.3377 -0.3369 0.133 Uiso 1 1 calc R . . C14 C -0.0766(4) 0.31013(17) -0.0524(9) 0.102(2) Uani 1 1 d G . . H14 H -0.1498 0.2987 0.0066 0.122 Uiso 1 1 calc R . . C15 C 0.0493(4) 0.30381(15) 0.0653(7) 0.0717(16) Uani 1 1 d G . . H15 H 0.0611 0.2881 0.2037 0.086 Uiso 1 1 calc R . . H21 H 0.643(5) 0.3142(19) 0.300(8) 0.068(16) Uiso 1 1 d . . . H22 H 0.610(5) 0.373(2) 0.160(8) 0.082(18) Uiso 1 1 d . . . H3 H 0.473(4) 0.3267(18) 0.469(7) 0.052(14) Uiso 1 1 d . . . H4 H 0.279(3) 0.3747(15) 0.336(6) 0.034(11) Uiso 1 1 d . . . H5 H 0.302(3) 0.2858(16) 0.222(6) 0.034(11) Uiso 1 1 d . . . H61 H 0.470(5) 0.4210(19) 0.613(8) 0.069(16) Uiso 1 1 d . . . H62 H 0.549(6) 0.440(3) 0.413(10) 0.11(2) Uiso 1 1 d . . . H63 H 0.620(7) 0.399(3) 0.595(11) 0.13(3) Uiso 1 1 d . . . H81 H 0.203(5) 0.559(3) 0.036(9) 0.09(2) Uiso 1 1 d . . . H82 H 0.348(9) 0.528(4) -0.045(14) 0.22(4) Uiso 1 1 d . . . H91 H 0.214(8) 0.482(3) -0.256(13) 0.16(4) Uiso 1 1 d . . . H92 H 0.170(7) 0.553(4) -0.340(13) 0.16(3) Uiso 1 1 d . . . H93 H 0.083(7) 0.508(3) -0.251(12) 0.14(3) 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 S1 0.0923(11) 0.0683(10) 0.0878(12) -0.0007(9) 0.0333(9) 0.0246(9) O1 0.072(2) 0.093(3) 0.093(3) -0.019(3) 0.028(2) 0.007(2) O2 0.060(2) 0.058(2) 0.070(3) -0.0178(19) 0.0095(19) 0.0037(18) O3 0.075(2) 0.063(2) 0.086(3) 0.011(2) 0.036(2) 0.0061(19) C1 0.049(3) 0.050(3) 0.076(4) -0.003(3) 0.010(3) -0.001(3) C2 0.052(3) 0.057(4) 0.076(4) 0.003(4) 0.005(3) 0.001(3) C3 0.062(4) 0.057(3) 0.057(4) 0.004(3) -0.002(3) -0.005(3) C4 0.054(3) 0.055(3) 0.052(3) -0.003(3) 0.017(3) -0.001(3) C5 0.055(3) 0.047(3) 0.058(4) 0.008(3) 0.005(3) -0.002(2) C6 0.072(5) 0.085(5) 0.071(5) -0.025(4) 0.003(4) -0.002(4) C7 0.055(3) 0.044(3) 0.054(3) -0.004(3) 0.012(3) -0.003(2) C8 0.124(6) 0.052(4) 0.089(6) 0.002(4) 0.019(5) 0.029(4) C9 0.081(6) 0.125(8) 0.121(8) 0.041(6) -0.002(6) 0.005(6) C10 0.053(3) 0.041(3) 0.072(4) 0.002(3) 0.007(3) 0.005(2) C11 0.074(4) 0.071(4) 0.064(4) 0.000(3) -0.005(3) 0.000(3) C12 0.114(6) 0.089(5) 0.086(5) -0.010(4) -0.019(5) 0.025(5) C13 0.076(5) 0.097(5) 0.139(8) -0.037(5) -0.036(5) 0.041(4) C14 0.061(5) 0.090(5) 0.151(7) -0.022(5) 0.007(4) 0.012(3) C15 0.067(4) 0.064(4) 0.085(5) -0.006(3) 0.017(4) 0.000(3) _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 C7 1.744(5) . ? S1 C8 1.804(7) . ? O1 C1 1.204(6) . ? O2 C1 1.353(5) . ? O2 C5 1.451(5) . ? O3 C7 1.198(5) . ? C1 C2 1.485(7) . ? C2 C3 1.520(7) . ? C3 C4 1.518(7) . ? C3 C6 1.526(7) . ? C4 C7 1.526(6) . ? C4 C5 1.536(6) . ? C5 C10 1.500(6) . ? C8 C9 1.496(11) . ? C10 C11 1.377(2) . ? C10 C15 1.377(2) . ? C11 C12 1.377(2) . ? C12 C13 1.377(2) . ? C13 C14 1.377(2) . ? C14 C15 1.377(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 C7 S1 C8 100.3(3) . . ? C1 O2 C5 121.8(4) . . ? O1 C1 O2 115.2(5) . . ? O1 C1 C2 123.5(5) . . ? O2 C1 C2 121.2(5) . . ? C1 C2 C3 117.3(5) . . ? C4 C3 C2 111.1(5) . . ? C4 C3 C6 113.0(5) . . ? C2 C3 C6 110.9(5) . . ? C3 C4 C7 113.2(4) . . ? C3 C4 C5 109.3(4) . . ? C7 C4 C5 111.4(4) . . ? O2 C5 C10 107.8(4) . . ? O2 C5 C4 111.7(4) . . ? C10 C5 C4 114.8(4) . . ? O3 C7 C4 122.4(4) . . ? O3 C7 S1 123.6(4) . . ? C4 C7 S1 114.0(4) . . ? C9 C8 S1 114.5(6) . . ? C11 C10 C15 120.0 . . ? C11 C10 C5 120.8(4) . . ? C15 C10 C5 119.1(4) . . ? C12 C11 C10 120.0 . . ? C13 C12 C11 120.0 . . ? C12 C13 C14 120.0 . . ? C13 C14 C15 120.0 . . ? C14 C15 C10 120.0 . . ? 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 C5 O2 C1 O1 175.3(4) . . . . ? C5 O2 C1 C2 -7.1(7) . . . . ? O1 C1 C2 C3 -177.2(5) . . . . ? O2 C1 C2 C3 5.5(8) . . . . ? C1 C2 C3 C4 -30.3(7) . . . . ? C1 C2 C3 C6 -156.8(6) . . . . ? C2 C3 C4 C7 -70.1(6) . . . . ? C6 C3 C4 C7 55.3(7) . . . . ? C2 C3 C4 C5 54.8(6) . . . . ? C6 C3 C4 C5 -179.9(5) . . . . ? C1 O2 C5 C10 160.1(4) . . . . ? C1 O2 C5 C4 33.0(6) . . . . ? C3 C4 C5 O2 -56.5(6) . . . . ? C7 C4 C5 O2 69.4(5) . . . . ? C3 C4 C5 C10 -179.7(4) . . . . ? C7 C4 C5 C10 -53.8(6) . . . . ? C3 C4 C7 O3 54.1(7) . . . . ? C5 C4 C7 O3 -69.5(6) . . . . ? C3 C4 C7 S1 -124.1(4) . . . . ? C5 C4 C7 S1 112.2(4) . . . . ? C8 S1 C7 O3 1.6(5) . . . . ? C8 S1 C7 C4 179.9(4) . . . . ? C7 S1 C8 C9 82.8(7) . . . . ? O2 C5 C10 C11 -37.8(4) . . . . ? C4 C5 C10 C11 87.5(5) . . . . ? O2 C5 C10 C15 144.4(3) . . . . ? C4 C5 C10 C15 -90.3(4) . . . . ? C15 C10 C11 C12 0.0 . . . . ? C5 C10 C11 C12 -177.8(4) . . . . ? C10 C11 C12 C13 0.0 . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C10 0.0 . . . . ? C11 C10 C15 C14 0.0 . . . . ? C5 C10 C15 C14 177.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.204 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.046