# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jingsong You' _publ_contact_author_address ; 29 Wangjiang Road Chengdu 610064 Peoples Republic of China Chengdu 610064 ; _publ_contact_author_email jsyou@scu.edu.cn _publ_author_name 'Jingsong You' # Attachment '- 3a.cif' data_100329 _database_code_depnum_ccdc_archive 'CCDC 819088' #TrackingRef '- 3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C17 H15 N O2 S' _chemical_formula_sum 'C17 H15 N O2 S' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _diffrn_ambient_temperature 110(2) _chemical_formula_weight 297.36 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _chemical_absolute_configuration ? 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 6.1135(2) _cell_length_b 7.5230(3) _cell_length_c 30.9381(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1422.90(9) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98336 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15150 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 29.29 _reflns_number_total 3477 _reflns_number_gt 3252 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0580P)^2^+0.6122P] 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 constr _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 -0.01(8) _refine_ls_number_reflns 3477 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 S S 0.96962(8) 0.78787(7) 0.907053(14) 0.01610(12) Uani 1 1 d . . . O1 O 0.1874(2) 0.6086(2) 0.81619(5) 0.0193(3) Uani 1 1 d . . . O2 O 0.1346(2) 0.88371(19) 0.78941(4) 0.0162(3) Uani 1 1 d . . . N N 0.7221(3) 1.0055(2) 0.85468(5) 0.0125(3) Uani 1 1 d . . . C1 C 0.8570(3) 1.1515(3) 0.85709(6) 0.0176(4) Uani 1 1 d . . . H1A H 0.9861 1.1473 0.8742 0.021 Uiso 1 1 calc R . . C2 C 0.8054(3) 1.3008(3) 0.83513(6) 0.0184(4) Uani 1 1 d . . . H2A H 0.8984 1.4018 0.8367 0.022 Uiso 1 1 calc R . . C3 C 0.6120(3) 1.3067(3) 0.80975(6) 0.0193(4) Uani 1 1 d . . . H3A H 0.5751 1.4125 0.7947 0.023 Uiso 1 1 calc R . . C4 C 0.4793(3) 1.1626(3) 0.80686(6) 0.0164(4) Uani 1 1 d . . . H4A H 0.3512 1.1673 0.7895 0.020 Uiso 1 1 calc R . . C5 C 0.5323(3) 1.0050(2) 0.82978(5) 0.0128(4) Uani 1 1 d . . . C6 C 0.7453(3) 0.8408(3) 0.87499(6) 0.0143(4) Uani 1 1 d . . . C7 C 0.5729(3) 0.7376(3) 0.86236(6) 0.0150(4) Uani 1 1 d . . . H7A H 0.5472 0.6187 0.8714 0.018 Uiso 1 1 calc R . . C8 C 0.4390(3) 0.8352(2) 0.83383(6) 0.0138(4) Uani 1 1 d . . . C9 C 0.2451(3) 0.7622(2) 0.81311(6) 0.0130(4) Uani 1 1 d . . . C10 C -0.0542(3) 0.8143(3) 0.76672(6) 0.0171(4) Uani 1 1 d . . . H10A H -0.1248 0.9104 0.7505 0.026 Uiso 1 1 calc R . . H10B H -0.1581 0.7648 0.7876 0.026 Uiso 1 1 calc R . . H10C H -0.0076 0.7208 0.7467 0.026 Uiso 1 1 calc R . . C11 C 0.9159(3) 0.9051(3) 0.95609(6) 0.0134(4) Uani 1 1 d . . . C12 C 1.0847(3) 0.9072(3) 0.98630(6) 0.0144(4) Uani 1 1 d . . . H12A H 1.2208 0.8524 0.9798 0.017 Uiso 1 1 calc R . . C13 C 1.0529(3) 0.9906(3) 1.02623(6) 0.0166(4) Uani 1 1 d . . . H13A H 1.1673 0.9900 1.0470 0.020 Uiso 1 1 calc R . . C14 C 0.8556(3) 1.0745(3) 1.03588(6) 0.0171(4) Uani 1 1 d . . . C15 C 0.6895(3) 1.0708(3) 1.00510(6) 0.0182(4) Uani 1 1 d . . . H15A H 0.5537 1.1266 1.0113 0.022 Uiso 1 1 calc R . . C16 C 0.7182(3) 0.9871(3) 0.96532(6) 0.0171(4) Uani 1 1 d . . . H16A H 0.6032 0.9862 0.9447 0.021 Uiso 1 1 calc R . . C17 C 0.8217(4) 1.1676(3) 1.07838(7) 0.0228(5) Uani 1 1 d . . . H17A H 0.6738 1.2178 1.0794 0.034 Uiso 1 1 calc R . . H17B H 0.9293 1.2634 1.0814 0.034 Uiso 1 1 calc R . . H17C H 0.8398 1.0824 1.1021 0.034 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 0.0137(2) 0.0210(2) 0.0136(2) -0.00076(18) -0.00199(17) 0.00308(19) O1 0.0201(7) 0.0169(7) 0.0208(7) 0.0018(6) -0.0040(6) -0.0058(6) O2 0.0148(6) 0.0141(7) 0.0196(7) 0.0010(5) -0.0061(5) -0.0029(6) N 0.0123(8) 0.0137(8) 0.0115(7) -0.0003(6) -0.0004(6) -0.0013(6) C1 0.0167(9) 0.0192(10) 0.0171(9) -0.0042(7) 0.0003(8) -0.0056(8) C2 0.0193(9) 0.0162(10) 0.0197(9) -0.0021(8) 0.0038(8) -0.0065(8) C3 0.0233(10) 0.0132(10) 0.0214(9) 0.0017(8) 0.0015(8) 0.0005(8) C4 0.0167(9) 0.0155(9) 0.0171(8) 0.0016(7) -0.0004(7) 0.0016(8) C5 0.0123(8) 0.0169(9) 0.0092(7) -0.0021(6) 0.0005(7) -0.0005(8) C6 0.0150(9) 0.0160(9) 0.0118(8) 0.0023(7) -0.0003(7) 0.0019(7) C7 0.0179(9) 0.0139(9) 0.0131(8) -0.0003(7) 0.0002(7) -0.0002(7) C8 0.0153(9) 0.0149(9) 0.0113(8) -0.0003(7) 0.0003(7) -0.0009(7) C9 0.0136(8) 0.0133(9) 0.0123(7) -0.0012(7) 0.0015(7) -0.0006(7) C10 0.0145(9) 0.0193(10) 0.0176(8) -0.0019(7) -0.0053(7) -0.0018(8) C11 0.0159(9) 0.0126(9) 0.0118(8) 0.0028(7) 0.0005(7) -0.0016(7) C12 0.0119(9) 0.0157(9) 0.0156(8) 0.0037(7) 0.0001(7) 0.0015(7) C13 0.0166(9) 0.0180(9) 0.0152(8) 0.0039(7) -0.0023(8) 0.0016(8) C14 0.0222(10) 0.0135(9) 0.0157(9) 0.0029(7) 0.0025(8) -0.0008(8) C15 0.0175(10) 0.0168(10) 0.0202(9) 0.0015(8) 0.0042(8) 0.0038(8) C16 0.0129(9) 0.0194(10) 0.0189(9) 0.0027(8) -0.0007(7) 0.0001(8) C17 0.0287(11) 0.0202(10) 0.0195(9) -0.0011(8) 0.0043(9) 0.0024(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 C6 1.739(2) . ? S C11 1.7852(19) . ? O1 C9 1.212(2) . ? O2 C9 1.352(2) . ? O2 C10 1.448(2) . ? N C1 1.376(3) . ? N C6 1.396(3) . ? N C5 1.393(2) . ? C1 C2 1.350(3) . ? C1 H1A 0.9500 . ? C2 C3 1.420(3) . ? C2 H2A 0.9500 . ? C3 C4 1.357(3) . ? C3 H3A 0.9500 . ? C4 C5 1.419(3) . ? C4 H4A 0.9500 . ? C5 C8 1.404(3) . ? C6 C7 1.367(3) . ? C7 C8 1.410(3) . ? C7 H7A 0.9500 . ? C8 C9 1.456(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.387(3) . ? C11 C12 1.392(3) . ? C12 C13 1.399(3) . ? C12 H12A 0.9500 . ? C13 C14 1.394(3) . ? C13 H13A 0.9500 . ? C14 C15 1.393(3) . ? C14 C17 1.504(3) . ? C15 C16 1.394(3) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 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 C6 S C11 103.10(9) . . ? C9 O2 C10 114.65(15) . . ? C1 N C6 128.56(17) . . ? C1 N C5 122.10(16) . . ? C6 N C5 109.34(16) . . ? C2 C1 N 119.81(18) . . ? C2 C1 H1A 120.1 . . ? N C1 H1A 120.1 . . ? C1 C2 C3 119.93(19) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C4 C3 C2 120.61(19) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 119.87(18) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C8 C5 N 106.94(16) . . ? C8 C5 C4 135.38(18) . . ? N C5 C4 117.67(17) . . ? C7 C6 N 107.29(17) . . ? C7 C6 S 129.90(16) . . ? N C6 S 122.70(15) . . ? C6 C7 C8 109.29(17) . . ? C6 C7 H7A 125.4 . . ? C8 C7 H7A 125.4 . . ? C5 C8 C7 107.11(17) . . ? C5 C8 C9 129.39(17) . . ? C7 C8 C9 123.49(17) . . ? O1 C9 O2 122.80(17) . . ? O1 C9 C8 124.21(18) . . ? O2 C9 C8 112.99(16) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 120.17(18) . . ? C16 C11 S 123.71(15) . . ? C12 C11 S 116.10(15) . . ? C11 C12 C13 119.68(17) . . ? C11 C12 H12A 120.2 . . ? C13 C12 H12A 120.2 . . ? C14 C13 C12 120.81(18) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C15 C14 C13 118.41(18) . . ? C15 C14 C17 120.43(19) . . ? C13 C14 C17 121.16(19) . . ? C14 C15 C16 121.39(19) . . ? C14 C15 H15A 119.3 . . ? C16 C15 H15A 119.3 . . ? C11 C16 C15 119.53(19) . . ? C11 C16 H16A 120.2 . . ? C15 C16 H16A 120.2 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 29.29 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.543 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.061