# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email songye@iccas.ac.cn _publ_contact_author_name 'Song Ye' loop_ _publ_author_name 'Xiang-Yu Chen' 'Song Ye' 'Ruo-Chen Lin' data_a _database_code_depnum_ccdc_archive 'CCDC 846096' #Trackin1gRef '7357_web_deposit_cif_file_0_SongYe_1317029757.a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 N O4 S' _chemical_formula_sum 'C19 H17 N O4 S' _chemical_formula_weight 355.40 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 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 14.297(3) _cell_length_b 12.116(3) _cell_length_c 10.612(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.217(3) _cell_angle_gamma 90.00 _cell_volume 1725.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5649 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9336 _exptl_absorpt_correction_T_max 0.9690 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007-HF CCD(Saturn 724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15200 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3935 _reflns_number_gt 3496 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _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^)+(0.0893P)^2^+2.2394P] 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_number_reflns 3935 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.2015 _refine_ls_wR_factor_gt 0.1947 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _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 0.62211(5) 0.05027(6) 0.67432(6) 0.0250(2) Uani 1 1 d . . . O1 O 0.65337(19) 0.0656(2) 0.5614(2) 0.0385(6) Uani 1 1 d . . . O2 O 0.52487(16) 0.0859(2) 0.6646(2) 0.0354(5) Uani 1 1 d . . . O3 O 1.01433(18) 0.1389(2) 0.8589(3) 0.0449(7) Uani 1 1 d . . . O4 O 0.96921(19) 0.2442(3) 0.6723(3) 0.0613(9) Uani 1 1 d . . . N1 N 0.70619(18) 0.1069(2) 0.8111(2) 0.0221(5) Uani 1 1 d . . . C1 C 0.6431(2) -0.0847(2) 0.7384(3) 0.0225(6) Uani 1 1 d . . . C2 C 0.6045(2) -0.1807(3) 0.6674(3) 0.0270(6) Uani 1 1 d . . . H2A H 0.5630 -0.1784 0.5756 0.032 Uiso 1 1 calc R . . C3 C 0.6290(2) -0.2796(3) 0.7358(3) 0.0302(7) Uani 1 1 d . . . H3A H 0.6056 -0.3469 0.6899 0.036 Uiso 1 1 calc R . . C4 C 0.6877(2) -0.2815(3) 0.8713(3) 0.0290(6) Uani 1 1 d . . . H4A H 0.7025 -0.3502 0.9171 0.035 Uiso 1 1 calc R . . C5 C 0.7249(2) -0.1846(2) 0.9409(3) 0.0250(6) Uani 1 1 d . . . H5A H 0.7645 -0.1866 1.0335 0.030 Uiso 1 1 calc R . . C6 C 0.7030(2) -0.0846(2) 0.8723(3) 0.0200(5) Uani 1 1 d . . . C7 C 0.7390(2) 0.0282(2) 0.9302(2) 0.0212(6) Uani 1 1 d . . . C8 C 0.8488(2) 0.0571(2) 0.9470(3) 0.0235(6) Uani 1 1 d . . . H8A H 0.8833 0.1030 1.0267 0.028 Uiso 1 1 calc R . . H8B H 0.8898 -0.0074 0.9415 0.028 Uiso 1 1 calc R . . C9 C 0.8073(2) 0.1210(2) 0.8185(3) 0.0225(6) Uani 1 1 d . . . C10 C 0.7036(2) 0.0599(2) 1.0439(3) 0.0230(6) Uani 1 1 d . . . C11 C 0.6105(3) 0.1065(3) 1.0188(3) 0.0352(7) Uani 1 1 d . . . H11A H 0.5687 0.1211 0.9290 0.042 Uiso 1 1 calc R . . C12 C 0.5777(3) 0.1323(3) 1.1248(4) 0.0422(9) Uani 1 1 d . . . H12A H 0.5136 0.1638 1.1070 0.051 Uiso 1 1 calc R . . C13 C 0.6381(3) 0.1120(3) 1.2547(3) 0.0387(8) Uani 1 1 d . . . H13A H 0.6159 0.1299 1.3268 0.046 Uiso 1 1 calc R . . C14 C 0.7300(3) 0.0662(3) 1.2804(3) 0.0362(8) Uani 1 1 d . . . H14A H 0.7713 0.0522 1.3706 0.043 Uiso 1 1 calc R . . C15 C 0.7642(2) 0.0395(3) 1.1754(3) 0.0295(7) Uani 1 1 d . . . H15A H 0.8283 0.0077 1.1941 0.035 Uiso 1 1 calc R . . C16 C 0.8422(2) 0.1748(3) 0.7357(3) 0.0314(7) Uani 1 1 d . . . H16A H 0.7975 0.2091 0.6575 0.038 Uiso 1 1 calc R . . C17 C 0.9496(3) 0.1815(3) 0.7647(4) 0.0398(8) Uani 1 1 d . . . C18 C 1.0741(3) 0.2703(5) 0.6999(5) 0.0685(15) Uani 1 1 d . . . H18A H 1.0845 0.2921 0.6157 0.082 Uiso 1 1 calc R . . H18B H 1.1158 0.2046 0.7367 0.082 Uiso 1 1 calc R . . C19 C 1.1054(3) 0.3686(4) 0.8051(5) 0.0695(15) Uani 1 1 d . . . H19A H 1.1758 0.3868 0.8243 0.104 Uiso 1 1 calc R . . H19B H 1.0955 0.3463 0.8883 0.104 Uiso 1 1 calc R . . H19C H 1.0643 0.4335 0.7677 0.104 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 0.0261(4) 0.0280(4) 0.0172(3) 0.0027(3) 0.0026(3) -0.0019(3) O1 0.0487(14) 0.0466(14) 0.0186(10) 0.0025(9) 0.0097(9) -0.0124(11) O2 0.0246(11) 0.0359(12) 0.0381(12) 0.0045(10) 0.0010(9) 0.0021(9) O3 0.0307(12) 0.0526(16) 0.0505(15) 0.0296(12) 0.0128(11) 0.0058(11) O4 0.0322(14) 0.085(2) 0.0687(19) 0.0507(17) 0.0206(13) 0.0094(14) N1 0.0231(11) 0.0247(12) 0.0178(10) 0.0037(9) 0.0060(9) -0.0006(9) C1 0.0226(13) 0.0250(14) 0.0209(12) -0.0005(10) 0.0088(10) -0.0007(11) C2 0.0248(14) 0.0322(16) 0.0236(13) -0.0070(11) 0.0080(11) -0.0029(12) C3 0.0263(15) 0.0277(15) 0.0359(16) -0.0095(12) 0.0100(12) -0.0049(12) C4 0.0290(15) 0.0240(15) 0.0347(15) -0.0003(12) 0.0119(12) -0.0004(12) C5 0.0254(14) 0.0268(15) 0.0221(13) 0.0004(11) 0.0073(11) 0.0001(11) C6 0.0197(12) 0.0223(13) 0.0198(12) -0.0024(10) 0.0091(10) -0.0013(10) C7 0.0210(13) 0.0245(14) 0.0162(12) 0.0021(10) 0.0042(10) 0.0006(11) C8 0.0222(13) 0.0238(14) 0.0225(13) -0.0001(10) 0.0053(10) -0.0010(11) C9 0.0206(13) 0.0197(13) 0.0256(13) 0.0000(10) 0.0061(10) 0.0000(11) C10 0.0282(14) 0.0194(13) 0.0216(13) -0.0012(10) 0.0088(11) -0.0035(11) C11 0.0333(17) 0.047(2) 0.0270(15) 0.0006(14) 0.0127(13) 0.0064(15) C12 0.046(2) 0.050(2) 0.0383(18) 0.0038(16) 0.0240(16) 0.0137(17) C13 0.061(2) 0.0369(18) 0.0286(16) -0.0026(13) 0.0286(16) -0.0015(16) C14 0.052(2) 0.0369(18) 0.0192(13) 0.0006(12) 0.0114(13) -0.0070(15) C15 0.0358(17) 0.0290(15) 0.0231(14) 0.0028(11) 0.0094(12) -0.0019(13) C16 0.0243(15) 0.0340(17) 0.0347(16) 0.0136(13) 0.0088(12) 0.0027(12) C17 0.0304(17) 0.046(2) 0.0445(19) 0.0226(16) 0.0141(14) 0.0047(15) C18 0.033(2) 0.097(4) 0.078(3) 0.050(3) 0.023(2) 0.009(2) C19 0.042(2) 0.074(3) 0.086(3) 0.049(3) 0.014(2) -0.009(2) _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 1.425(2) . ? S1 O1 1.428(2) . ? S1 N1 1.678(2) . ? S1 C1 1.757(3) . ? O3 C17 1.218(4) . ? O4 C17 1.344(4) . ? O4 C18 1.460(5) . ? N1 C9 1.430(4) . ? N1 C7 1.522(3) . ? C1 C6 1.382(4) . ? C1 C2 1.392(4) . ? C2 C3 1.382(4) . ? C2 H2A 0.9500 . ? C3 C4 1.392(4) . ? C3 H3A 0.9500 . ? C4 C5 1.392(4) . ? C4 H4A 0.9500 . ? C5 C6 1.391(4) . ? C5 H5A 0.9500 . ? C6 C7 1.514(4) . ? C7 C10 1.510(4) . ? C7 C8 1.558(4) . ? C8 C9 1.501(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C16 1.323(4) . ? C10 C11 1.384(4) . ? C10 C15 1.387(4) . ? C11 C12 1.395(4) . ? C11 H11A 0.9500 . ? C12 C13 1.373(5) . ? C12 H12A 0.9500 . ? C13 C14 1.364(5) . ? C13 H13A 0.9500 . ? C14 C15 1.400(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C17 1.460(4) . ? C16 H16A 0.9500 . ? C18 C19 1.588(8) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 O2 S1 O1 118.68(15) . . ? O2 S1 N1 109.17(13) . . ? O1 S1 N1 109.51(13) . . ? O2 S1 C1 109.99(14) . . ? O1 S1 C1 112.65(14) . . ? N1 S1 C1 94.02(12) . . ? C17 O4 C18 115.8(3) . . ? C9 N1 C7 90.8(2) . . ? C9 N1 S1 120.30(18) . . ? C7 N1 S1 112.65(18) . . ? C6 C1 C2 123.1(3) . . ? C6 C1 S1 111.1(2) . . ? C2 C1 S1 125.8(2) . . ? C3 C2 C1 117.3(3) . . ? C3 C2 H2A 121.4 . . ? C1 C2 H2A 121.4 . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3A 119.7 . . ? C4 C3 H3A 119.7 . . ? C5 C4 C3 121.1(3) . . ? C5 C4 H4A 119.4 . . ? C3 C4 H4A 119.4 . . ? C6 C5 C4 118.8(3) . . ? C6 C5 H5A 120.6 . . ? C4 C5 H5A 120.6 . . ? C1 C6 C5 118.9(3) . . ? C1 C6 C7 114.9(2) . . ? C5 C6 C7 126.2(2) . . ? C10 C7 C6 113.2(2) . . ? C10 C7 N1 114.3(2) . . ? C6 C7 N1 105.4(2) . . ? C10 C7 C8 117.0(2) . . ? C6 C7 C8 115.9(2) . . ? N1 C7 C8 87.89(19) . . ? C9 C8 C7 86.9(2) . . ? C9 C8 H8A 114.2 . . ? C7 C8 H8A 114.2 . . ? C9 C8 H8B 114.2 . . ? C7 C8 H8B 114.2 . . ? H8A C8 H8B 111.3 . . ? C16 C9 N1 129.0(3) . . ? C16 C9 C8 137.4(3) . . ? N1 C9 C8 93.6(2) . . ? C11 C10 C15 119.4(3) . . ? C11 C10 C7 121.0(3) . . ? C15 C10 C7 119.6(3) . . ? C10 C11 C12 120.3(3) . . ? C10 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? C13 C12 C11 120.0(3) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C13 C14 C15 120.7(3) . . ? C13 C14 H14A 119.6 . . ? C15 C14 H14A 119.6 . . ? C10 C15 C14 119.5(3) . . ? C10 C15 H15A 120.3 . . ? C14 C15 H15A 120.3 . . ? C9 C16 C17 119.9(3) . . ? C9 C16 H16A 120.1 . . ? C17 C16 H16A 120.1 . . ? O3 C17 O4 123.2(3) . . ? O3 C17 C16 126.5(3) . . ? O4 C17 C16 110.3(3) . . ? O4 C18 C19 108.9(4) . . ? O4 C18 H18A 109.9 . . ? C19 C18 H18A 109.9 . . ? O4 C18 H18B 109.9 . . ? C19 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 C9 -155.8(2) . . . . ? O1 S1 N1 C9 -24.4(3) . . . . ? C1 S1 N1 C9 91.4(2) . . . . ? O2 S1 N1 C7 99.0(2) . . . . ? O1 S1 N1 C7 -129.5(2) . . . . ? C1 S1 N1 C7 -13.8(2) . . . . ? O2 S1 C1 C6 -102.8(2) . . . . ? O1 S1 C1 C6 122.4(2) . . . . ? N1 S1 C1 C6 9.3(2) . . . . ? O2 S1 C1 C2 76.3(3) . . . . ? O1 S1 C1 C2 -58.5(3) . . . . ? N1 S1 C1 C2 -171.6(3) . . . . ? C6 C1 C2 C3 -0.5(4) . . . . ? S1 C1 C2 C3 -179.5(2) . . . . ? C1 C2 C3 C4 1.7(4) . . . . ? C2 C3 C4 C5 -1.3(5) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? C2 C1 C6 C5 -1.2(4) . . . . ? S1 C1 C6 C5 178.0(2) . . . . ? C2 C1 C6 C7 178.8(3) . . . . ? S1 C1 C6 C7 -2.0(3) . . . . ? C4 C5 C6 C1 1.6(4) . . . . ? C4 C5 C6 C7 -178.4(3) . . . . ? C1 C6 C7 C10 118.3(3) . . . . ? C5 C6 C7 C10 -61.7(4) . . . . ? C1 C6 C7 N1 -7.3(3) . . . . ? C5 C6 C7 N1 172.7(3) . . . . ? C1 C6 C7 C8 -102.5(3) . . . . ? C5 C6 C7 C8 77.5(3) . . . . ? C9 N1 C7 C10 125.6(2) . . . . ? S1 N1 C7 C10 -110.8(2) . . . . ? C9 N1 C7 C6 -109.5(2) . . . . ? S1 N1 C7 C6 14.1(3) . . . . ? C9 N1 C7 C8 6.8(2) . . . . ? S1 N1 C7 C8 130.39(18) . . . . ? C10 C7 C8 C9 -122.9(2) . . . . ? C6 C7 C8 C9 99.5(2) . . . . ? N1 C7 C8 C9 -6.5(2) . . . . ? C7 N1 C9 C16 173.8(3) . . . . ? S1 N1 C9 C16 56.7(4) . . . . ? C7 N1 C9 C8 -7.1(2) . . . . ? S1 N1 C9 C8 -124.1(2) . . . . ? C7 C8 C9 C16 -174.0(4) . . . . ? C7 C8 C9 N1 7.0(2) . . . . ? C6 C7 C10 C11 -84.1(3) . . . . ? N1 C7 C10 C11 36.5(4) . . . . ? C8 C7 C10 C11 137.2(3) . . . . ? C6 C7 C10 C15 94.3(3) . . . . ? N1 C7 C10 C15 -145.1(3) . . . . ? C8 C7 C10 C15 -44.4(4) . . . . ? C15 C10 C11 C12 -0.3(5) . . . . ? C7 C10 C11 C12 178.1(3) . . . . ? C10 C11 C12 C13 0.4(6) . . . . ? C11 C12 C13 C14 -0.3(6) . . . . ? C12 C13 C14 C15 0.1(5) . . . . ? C11 C10 C15 C14 0.2(5) . . . . ? C7 C10 C15 C14 -178.3(3) . . . . ? C13 C14 C15 C10 -0.1(5) . . . . ? N1 C9 C16 C17 178.3(3) . . . . ? C8 C9 C16 C17 -0.5(6) . . . . ? C18 O4 C17 O3 -7.2(6) . . . . ? C18 O4 C17 C16 171.8(4) . . . . ? C9 C16 C17 O3 2.1(6) . . . . ? C9 C16 C17 O4 -176.8(3) . . . . ? C17 O4 C18 C19 -79.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.170 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.088 # Attachment '7358_web_deposit_cif_file_1_SongYe_1317029757.a.cif' data_a1 _database_code_depnum_ccdc_archive 'CCDC 846097' #TrackingRef '7358_web_deposit_cif_file_1_SongYe_1317029757.a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 N O4 S' _chemical_formula_sum 'C19 H17 N O4 S' _chemical_formula_weight 355.40 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 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 10.487(2) _cell_length_b 11.695(2) _cell_length_c 14.052(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.66(3) _cell_angle_gamma 90.00 _cell_volume 1651.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5122 _cell_measurement_theta_min 1.5127 _cell_measurement_theta_max 27.4838 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.60 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7400 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7549 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3746 _reflns_number_gt 3595 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^+1.1839P] 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_number_reflns 3746 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1280 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.48744(5) 0.82441(4) 0.13427(4) 0.02612(14) Uani 1 1 d . . . O1 O 0.39086(14) 0.90731(13) 0.08394(12) 0.0359(4) Uani 1 1 d . . . O2 O 0.44429(16) 0.73467(13) 0.18719(12) 0.0369(4) Uani 1 1 d . . . O3 O 0.98504(15) 0.70923(14) 0.10516(11) 0.0374(4) Uani 1 1 d . . . O4 O 0.95157(13) 0.81496(13) -0.03340(10) 0.0289(3) Uani 1 1 d . . . N1 N 0.55968(15) 0.76703(13) 0.05540(11) 0.0230(3) Uani 1 1 d . . . C6 C 0.91195(19) 0.76246(16) 0.03806(14) 0.0251(4) Uani 1 1 d . . . C7 C 0.72580(17) 0.62112(15) 0.13827(13) 0.0218(4) Uani 1 1 d . . . C8 C 0.74301(19) 0.83262(15) 0.19371(13) 0.0227(4) Uani 1 1 d . . . C9 C 0.70555(17) 0.74652(15) 0.10726(13) 0.0214(4) Uani 1 1 d . . . C10 C 0.63347(19) 0.88540(16) 0.21157(14) 0.0260(4) Uani 1 1 d . . . C11 C 0.6785(2) 0.82211(17) -0.05372(15) 0.0284(4) Uani 1 1 d . . . H11A H 0.6995 0.8483 -0.1114 0.034 Uiso 1 1 calc R . . C12 C 0.76775(18) 0.77974(16) 0.02542(14) 0.0236(4) Uani 1 1 d . . . C13 C 0.78979(19) 0.58825(17) 0.23500(14) 0.0263(4) Uani 1 1 d . . . H13A H 0.8262 0.6446 0.2839 0.032 Uiso 1 1 calc R . . C14 C 0.5423(2) 0.82398(18) -0.04223(15) 0.0303(4) Uani 1 1 d . . . H14A H 0.4793 0.7811 -0.0964 0.036 Uiso 1 1 calc R . . H14B H 0.5098 0.9033 -0.0414 0.036 Uiso 1 1 calc R . . C15 C 0.6763(2) 0.53739(17) 0.06687(15) 0.0294(4) Uani 1 1 d . . . H15A H 0.6333 0.5590 0.0002 0.035 Uiso 1 1 calc R . . C16 C 0.8814(2) 0.95433(19) 0.31904(16) 0.0340(5) Uani 1 1 d . . . H16A H 0.9674 0.9787 0.3569 0.041 Uiso 1 1 calc R . . C17 C 0.8696(2) 0.86668(17) 0.24999(14) 0.0272(4) Uani 1 1 d . . . H17A H 0.9467 0.8306 0.2413 0.033 Uiso 1 1 calc R . . C18 C 0.7509(2) 0.39005(18) 0.19005(17) 0.0343(5) Uani 1 1 d . . . H18A H 0.7583 0.3115 0.2079 0.041 Uiso 1 1 calc R . . C19 C 0.8008(2) 0.47280(18) 0.26064(16) 0.0322(4) Uani 1 1 d . . . H19A H 0.8431 0.4510 0.3274 0.039 Uiso 1 1 calc R . . C20 C 1.09114(19) 0.79845(19) -0.02893(15) 0.0310(4) Uani 1 1 d . . . H20A H 1.1061 0.7191 -0.0478 0.037 Uiso 1 1 calc R . . H20B H 1.1488 0.8127 0.0393 0.037 Uiso 1 1 calc R . . C21 C 0.7691(2) 1.00687(19) 0.33356(16) 0.0376(5) Uani 1 1 d . . . H21A H 0.7796 1.0674 0.3803 0.045 Uiso 1 1 calc R . . C22 C 0.6895(2) 0.42254(18) 0.09240(17) 0.0349(5) Uani 1 1 d . . . H22A H 0.6564 0.3659 0.0430 0.042 Uiso 1 1 calc R . . C23 C 1.1231(2) 0.8819(2) -0.10041(18) 0.0410(5) Uani 1 1 d . . . H23A H 1.2164 0.8731 -0.0993 0.061 Uiso 1 1 calc R . . H23B H 1.1081 0.9601 -0.0809 0.061 Uiso 1 1 calc R . . H23C H 1.0655 0.8669 -0.1676 0.061 Uiso 1 1 calc R . . C24 C 0.6426(2) 0.97186(18) 0.28070(16) 0.0343(5) Uani 1 1 d . . . H24A H 0.5654 1.0056 0.2913 0.041 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 0.0237(2) 0.0240(3) 0.0328(3) -0.00085(18) 0.01160(19) -0.00135(17) O1 0.0258(7) 0.0344(8) 0.0477(9) -0.0003(7) 0.0111(6) 0.0054(6) O2 0.0417(8) 0.0321(8) 0.0446(9) -0.0017(7) 0.0249(7) -0.0088(6) O3 0.0298(7) 0.0456(9) 0.0388(8) 0.0168(7) 0.0129(6) 0.0094(7) O4 0.0233(6) 0.0373(8) 0.0280(7) 0.0067(6) 0.0106(5) 0.0005(6) N1 0.0218(7) 0.0223(8) 0.0247(7) 0.0009(6) 0.0066(6) 0.0014(6) C6 0.0268(9) 0.0243(9) 0.0256(9) -0.0007(7) 0.0100(7) -0.0010(7) C7 0.0222(8) 0.0203(8) 0.0250(8) 0.0003(7) 0.0102(7) -0.0004(7) C8 0.0270(9) 0.0199(8) 0.0218(8) 0.0004(7) 0.0081(7) -0.0018(7) C9 0.0205(8) 0.0216(9) 0.0226(8) -0.0010(7) 0.0070(7) -0.0017(6) C10 0.0294(9) 0.0220(9) 0.0278(9) 0.0004(7) 0.0100(7) -0.0008(7) C11 0.0304(10) 0.0298(10) 0.0260(9) 0.0025(8) 0.0099(8) -0.0001(8) C12 0.0257(9) 0.0215(9) 0.0250(9) 0.0001(7) 0.0094(7) -0.0015(7) C13 0.0305(9) 0.0240(9) 0.0253(9) 0.0003(7) 0.0093(7) -0.0005(7) C14 0.0263(9) 0.0354(11) 0.0277(9) 0.0077(8) 0.0052(8) 0.0012(8) C15 0.0324(10) 0.0269(10) 0.0271(9) -0.0031(8) 0.0056(8) -0.0009(8) C16 0.0375(11) 0.0306(11) 0.0310(10) -0.0046(8) 0.0051(8) -0.0089(9) C17 0.0282(9) 0.0250(9) 0.0280(9) -0.0007(7) 0.0072(7) -0.0030(7) C18 0.0350(11) 0.0225(10) 0.0487(12) 0.0061(9) 0.0174(9) 0.0015(8) C19 0.0373(11) 0.0293(10) 0.0320(10) 0.0085(8) 0.0131(9) 0.0031(8) C20 0.0239(9) 0.0397(11) 0.0312(10) 0.0012(9) 0.0111(8) 0.0002(8) C21 0.0521(13) 0.0273(10) 0.0339(11) -0.0110(9) 0.0132(10) -0.0054(9) C22 0.0357(11) 0.0234(10) 0.0442(12) -0.0069(9) 0.0092(9) -0.0035(8) C23 0.0324(11) 0.0504(14) 0.0439(12) 0.0083(11) 0.0170(9) -0.0044(10) C24 0.0408(11) 0.0294(10) 0.0361(11) -0.0025(9) 0.0167(9) 0.0014(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 S1 O2 1.4324(15) . ? S1 O1 1.4336(16) . ? S1 N1 1.6535(16) . ? S1 C10 1.755(2) . ? O3 C6 1.204(2) . ? O4 C6 1.341(2) . ? O4 C20 1.460(2) . ? N1 C14 1.489(2) . ? N1 C9 1.513(2) . ? C6 C12 1.485(3) . ? C7 C13 1.387(3) . ? C7 C15 1.391(3) . ? C7 C9 1.527(3) . ? C8 C10 1.389(3) . ? C8 C17 1.394(3) . ? C8 C9 1.540(2) . ? C9 C12 1.526(2) . ? C10 C24 1.386(3) . ? C11 C12 1.327(3) . ? C11 C14 1.482(3) . ? C11 H11A 0.9500 . ? C13 C19 1.394(3) . ? C13 H13A 0.9500 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C22 1.387(3) . ? C15 H15A 0.9500 . ? C16 C17 1.392(3) . ? C16 C21 1.394(3) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C19 1.377(3) . ? C18 C22 1.391(3) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C23 1.506(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C24 1.384(3) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 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 O1 117.90(10) . . ? O2 S1 N1 108.92(9) . . ? O1 S1 N1 109.78(9) . . ? O2 S1 C10 109.02(10) . . ? O1 S1 C10 113.46(9) . . ? N1 S1 C10 95.37(9) . . ? C6 O4 C20 115.43(15) . . ? C14 N1 C9 110.75(15) . . ? C14 N1 S1 118.54(13) . . ? C9 N1 S1 109.62(12) . . ? O3 C6 O4 123.98(18) . . ? O3 C6 C12 124.19(18) . . ? O4 C6 C12 111.83(16) . . ? C13 C7 C15 119.17(17) . . ? C13 C7 C9 122.30(16) . . ? C15 C7 C9 118.52(16) . . ? C10 C8 C17 118.22(17) . . ? C10 C8 C9 113.33(16) . . ? C17 C8 C9 128.35(17) . . ? N1 C9 C12 100.85(14) . . ? N1 C9 C7 109.16(14) . . ? C12 C9 C7 113.88(15) . . ? N1 C9 C8 105.68(14) . . ? C12 C9 C8 111.13(15) . . ? C7 C9 C8 114.82(15) . . ? C24 C10 C8 123.79(19) . . ? C24 C10 S1 127.08(16) . . ? C8 C10 S1 109.13(14) . . ? C12 C11 C14 112.60(17) . . ? C12 C11 H11A 123.7 . . ? C14 C11 H11A 123.7 . . ? C11 C12 C6 126.91(18) . . ? C11 C12 C9 112.03(16) . . ? C6 C12 C9 121.06(16) . . ? C7 C13 C19 120.19(18) . . ? C7 C13 H13A 119.9 . . ? C19 C13 H13A 119.9 . . ? C11 C14 N1 103.12(15) . . ? C11 C14 H14A 111.1 . . ? N1 C14 H14A 111.1 . . ? C11 C14 H14B 111.1 . . ? N1 C14 H14B 111.1 . . ? H14A C14 H14B 109.1 . . ? C22 C15 C7 120.41(19) . . ? C22 C15 H15A 119.8 . . ? C7 C15 H15A 119.8 . . ? C17 C16 C21 121.1(2) . . ? C17 C16 H16A 119.4 . . ? C21 C16 H16A 119.4 . . ? C16 C17 C8 119.04(19) . . ? C16 C17 H17A 120.5 . . ? C8 C17 H17A 120.5 . . ? C19 C18 C22 119.43(19) . . ? C19 C18 H18A 120.3 . . ? C22 C18 H18A 120.3 . . ? C18 C19 C13 120.55(19) . . ? C18 C19 H19A 119.7 . . ? C13 C19 H19A 119.7 . . ? O4 C20 C23 107.32(17) . . ? O4 C20 H20A 110.2 . . ? C23 C20 H20A 110.2 . . ? O4 C20 H20B 110.2 . . ? C23 C20 H20B 110.2 . . ? H20A C20 H20B 108.5 . . ? C24 C21 C16 120.73(19) . . ? C24 C21 H21A 119.6 . . ? C16 C21 H21A 119.6 . . ? C15 C22 C18 120.2(2) . . ? C15 C22 H22A 119.9 . . ? C18 C22 H22A 119.9 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 C10 117.1(2) . . ? C21 C24 H24A 121.5 . . ? C10 C24 H24A 121.5 . . ? 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 C14 144.68(14) . . . . ? O1 S1 N1 C14 14.21(16) . . . . ? C10 S1 N1 C14 -103.09(15) . . . . ? O2 S1 N1 C9 -86.86(13) . . . . ? O1 S1 N1 C9 142.68(12) . . . . ? C10 S1 N1 C9 25.37(13) . . . . ? C20 O4 C6 O3 3.5(3) . . . . ? C20 O4 C6 C12 -177.60(16) . . . . ? C14 N1 C9 C12 -8.02(19) . . . . ? S1 N1 C9 C12 -140.66(12) . . . . ? C14 N1 C9 C7 -128.22(16) . . . . ? S1 N1 C9 C7 99.13(14) . . . . ? C14 N1 C9 C8 107.78(17) . . . . ? S1 N1 C9 C8 -24.87(16) . . . . ? C13 C7 C9 N1 -126.87(18) . . . . ? C15 C7 C9 N1 52.2(2) . . . . ? C13 C7 C9 C12 121.30(19) . . . . ? C15 C7 C9 C12 -59.6(2) . . . . ? C13 C7 C9 C8 -8.4(2) . . . . ? C15 C7 C9 C8 170.62(17) . . . . ? C10 C8 C9 N1 11.9(2) . . . . ? C17 C8 C9 N1 -164.27(18) . . . . ? C10 C8 C9 C12 120.50(17) . . . . ? C17 C8 C9 C12 -55.7(2) . . . . ? C10 C8 C9 C7 -108.43(18) . . . . ? C17 C8 C9 C7 75.4(2) . . . . ? C17 C8 C10 C24 1.5(3) . . . . ? C9 C8 C10 C24 -175.16(18) . . . . ? C17 C8 C10 S1 -178.19(14) . . . . ? C9 C8 C10 S1 5.2(2) . . . . ? O2 S1 C10 C24 -85.7(2) . . . . ? O1 S1 C10 C24 47.9(2) . . . . ? N1 S1 C10 C24 162.21(19) . . . . ? O2 S1 C10 C8 93.99(15) . . . . ? O1 S1 C10 C8 -132.44(14) . . . . ? N1 S1 C10 C8 -18.15(15) . . . . ? C14 C11 C12 C6 178.18(18) . . . . ? C14 C11 C12 C9 -1.0(2) . . . . ? O3 C6 C12 C11 -169.1(2) . . . . ? O4 C6 C12 C11 12.0(3) . . . . ? O3 C6 C12 C9 10.0(3) . . . . ? O4 C6 C12 C9 -168.92(16) . . . . ? N1 C9 C12 C11 5.5(2) . . . . ? C7 C9 C12 C11 122.27(18) . . . . ? C8 C9 C12 C11 -106.17(19) . . . . ? N1 C9 C12 C6 -173.72(16) . . . . ? C7 C9 C12 C6 -56.9(2) . . . . ? C8 C9 C12 C6 74.6(2) . . . . ? C15 C7 C13 C19 -1.8(3) . . . . ? C9 C7 C13 C19 177.22(18) . . . . ? C12 C11 C14 N1 -4.1(2) . . . . ? C9 N1 C14 C11 7.7(2) . . . . ? S1 N1 C14 C11 135.61(14) . . . . ? C13 C7 C15 C22 0.8(3) . . . . ? C9 C7 C15 C22 -178.32(18) . . . . ? C21 C16 C17 C8 1.0(3) . . . . ? C10 C8 C17 C16 -2.2(3) . . . . ? C9 C8 C17 C16 173.89(18) . . . . ? C22 C18 C19 C13 0.2(3) . . . . ? C7 C13 C19 C18 1.3(3) . . . . ? C6 O4 C20 C23 -168.50(17) . . . . ? C17 C16 C21 C24 1.1(3) . . . . ? C7 C15 C22 C18 0.8(3) . . . . ? C19 C18 C22 C15 -1.3(3) . . . . ? C16 C21 C24 C10 -1.8(3) . . . . ? C8 C10 C24 C21 0.5(3) . . . . ? S1 C10 C24 C21 -179.89(16) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.357 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.054