#------------------------------------------------------------------------------ #$Date: 2016-02-18 15:37:37 +0000 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/77/1507716.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1507716 loop_ _publ_author_name 'Cai, Yunfei' 'Li, Jun' 'Chen, Weiliang' 'Xie, Mingsheng' 'Liu, Xiaohua' 'Lin, Lili' 'Feng, Xiaoming' _publ_section_title ; Catalytic asymmetric sulfenylation of unprotected 3-substituted oxindoles. ; _journal_issue 11 _journal_name_full 'Organic letters' _journal_page_first 2726 _journal_page_last 2729 _journal_paper_doi 10.1021/ol3009446 _journal_volume 14 _journal_year 2012 _chemical_absolute_configuration ad _chemical_formula_moiety 'C19 H15 N O S2' _chemical_formula_sum 'C19 H15 N O S2' _chemical_formula_weight 337.44 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2012-02-13 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _cell_angle_alpha 90.00 _cell_angle_beta 108.188(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.5240(3) _cell_length_b 8.2187(2) _cell_length_c 12.2542(4) _cell_measurement_reflns_used 1756 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.7153 _cell_measurement_theta_min 3.0278 _cell_volume 815.59(5) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; 1 omega -62.00 -35.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -178.0000 -180.0000 27 2 omega -56.00 56.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 19.0000 60.0000 112 3 omega -68.00 -4.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -38.0000 30.0000 64 4 omega -37.00 -10.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 57.0000 150.0000 27 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0214159000 _diffrn_orient_matrix_UB_12 0.0174151000 _diffrn_orient_matrix_UB_13 0.0502512000 _diffrn_orient_matrix_UB_21 0.0784919000 _diffrn_orient_matrix_UB_22 0.0362913000 _diffrn_orient_matrix_UB_23 0.0252113000 _diffrn_orient_matrix_UB_31 -0.0323876000 _diffrn_orient_matrix_UB_32 0.0763368000 _diffrn_orient_matrix_UB_33 -0.0234959000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_unetI/netI 0.0463 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 3698 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.03 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.99193 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.175 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.043 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 216 _refine_ls_number_reflns 2734 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0373 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0301P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0702 _refine_ls_wR_factor_ref 0.0749 _reflns_number_gt 2370 _reflns_number_total 2734 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ol3009446_si_001.cif _cod_data_source_block 120213_s2_cyf _cod_original_cell_volume 815.60(5) _cod_database_code 1507716 #BEGIN Tags that were not found in dictionaries: _chemical_oxdiff_formula C10H12O1N1S2 _reflns_odcompleteness_completeness 99.78 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 #END Tags that were not found in dictionaries loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' 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 S1 S -1.37855(10) -0.31991(11) -0.77157(7) 0.0536(3) Uani 1 1 d . S2 S -0.74837(8) -0.41879(8) -0.67430(6) 0.03604(18) Uani 1 1 d . O1 O -0.9368(2) -0.4204(3) -0.95210(15) 0.0430(5) Uani 1 1 d . N1 N -1.0481(3) -0.6446(2) -0.89292(18) 0.0337(5) Uani 1 1 d . H1 H -1.0625 -0.7040 -0.9530 0.040 Uiso 1 1 calc R C1 C -1.0909(3) -0.6927(3) -0.7961(2) 0.0319(6) Uani 1 1 d . C2 C -1.0514(3) -0.5706(3) -0.7147(2) 0.0273(6) Uani 1 1 d . C3 C -1.0850(4) -0.5881(4) -0.6121(2) 0.0386(7) Uani 1 1 d . H3 H -1.0581 -0.5068 -0.5566 0.046 Uiso 1 1 calc R C4 C -1.1602(4) -0.7310(4) -0.5946(3) 0.0508(8) Uani 1 1 d . H4 H -1.1862 -0.7450 -0.5270 0.061 Uiso 1 1 calc R C5 C -1.1970(4) -0.8526(4) -0.6761(3) 0.0530(9) Uani 1 1 d . H5 H -1.2454 -0.9483 -0.6617 0.064 Uiso 1 1 calc R C6 C -1.1634(4) -0.8353(3) -0.7785(3) 0.0461(8) Uani 1 1 d . H6 H -1.1889 -0.9171 -0.8337 0.055 Uiso 1 1 calc R C7 C -0.9698(3) -0.4357(3) -0.7585(2) 0.0280(6) Uani 1 1 d . C8 C -0.9817(3) -0.4938(3) -0.8808(2) 0.0296(6) Uani 1 1 d . C9 C -0.6900(3) -0.6285(3) -0.6628(2) 0.0338(7) Uani 1 1 d . C10 C -0.6880(4) -0.7157(4) -0.5660(2) 0.0448(8) Uani 1 1 d . H10 H -0.7113 -0.6646 -0.5051 0.054 Uiso 1 1 calc R C11 C -0.6510(4) -0.8798(4) -0.5605(3) 0.0570(9) Uani 1 1 d . H11 H -0.6475 -0.9390 -0.4951 0.068 Uiso 1 1 calc R C12 C -0.6195(4) -0.9557(4) -0.6514(3) 0.0614(10) Uani 1 1 d . H12 H -0.5980 -1.0668 -0.6482 0.074 Uiso 1 1 calc R C13 C -0.6196(4) -0.8679(4) -0.7471(3) 0.0579(10) Uani 1 1 d . H13 H -0.5975 -0.9192 -0.8083 0.070 Uiso 1 1 calc R C14 C -0.6526(4) -0.7036(4) -0.7516(2) 0.0430(7) Uani 1 1 d . H14 H -0.6497 -0.6433 -0.8151 0.052 Uiso 1 1 calc R C15 C -1.0466(4) -0.2666(3) -0.7616(3) 0.0348(7) Uani 1 1 d . C16 C -1.2261(3) -0.2613(3) -0.8288(2) 0.0322(6) Uani 1 1 d . C17 C -1.2962(4) -0.2083(4) -0.9378(2) 0.0467(8) Uani 1 1 d . H17 H -1.2356 -0.1713 -0.9842 0.056 Uiso 1 1 calc R C18 C -1.4705(4) -0.2145(4) -0.9743(3) 0.0547(9) Uani 1 1 d . H18 H -1.5359 -0.1819 -1.0469 0.066 Uiso 1 1 calc R C19 C -1.5319(4) -0.2716(4) -0.8946(3) 0.0501(8) Uani 1 1 d . H19 H -1.6440 -0.2836 -0.9046 0.060 Uiso 1 1 calc R H15A H -1.034(3) -0.230(3) -0.688(2) 0.035(8) Uiso 1 1 d . H15B H -0.991(4) -0.190(3) -0.795(2) 0.042(8) 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 0.0405(5) 0.0714(6) 0.0539(5) 0.0194(5) 0.0219(4) 0.0056(5) S2 0.0325(4) 0.0316(3) 0.0423(4) -0.0046(4) 0.0093(3) -0.0030(4) O1 0.0541(12) 0.0439(10) 0.0391(11) 0.0091(11) 0.0262(10) 0.0023(12) N1 0.0474(15) 0.0264(12) 0.0271(12) -0.0075(10) 0.0114(11) -0.0021(11) C1 0.0334(15) 0.0272(14) 0.0325(14) 0.0012(13) 0.0066(12) 0.0014(12) C2 0.0247(15) 0.0258(13) 0.0308(15) 0.0034(12) 0.0079(13) -0.0024(12) C3 0.0393(17) 0.0464(17) 0.0307(15) 0.0065(14) 0.0121(13) 0.0008(15) C4 0.0440(18) 0.063(2) 0.0476(19) 0.0254(18) 0.0178(16) 0.0035(17) C5 0.0478(19) 0.0380(17) 0.072(2) 0.0236(18) 0.0175(18) -0.0051(15) C6 0.0512(19) 0.0272(15) 0.0556(19) 0.0002(15) 0.0106(16) -0.0059(15) C7 0.0291(13) 0.0256(13) 0.0294(13) 0.0004(12) 0.0093(11) -0.0005(13) C8 0.0297(15) 0.0316(14) 0.0272(14) 0.0041(12) 0.0084(12) 0.0082(13) C9 0.0256(15) 0.0343(15) 0.0395(16) 0.0009(13) 0.0076(13) 0.0021(13) C10 0.0419(18) 0.0548(19) 0.0377(17) 0.0045(16) 0.0124(14) 0.0035(16) C11 0.053(2) 0.050(2) 0.068(2) 0.0262(18) 0.0200(18) 0.0070(17) C12 0.050(2) 0.0354(19) 0.094(3) 0.0052(19) 0.015(2) 0.0087(16) C13 0.058(2) 0.050(2) 0.064(2) -0.0119(18) 0.0170(18) 0.0147(17) C14 0.0433(18) 0.0471(17) 0.0392(16) -0.0006(15) 0.0138(15) 0.0082(15) C15 0.0384(17) 0.0254(15) 0.0419(18) -0.0038(14) 0.0145(15) -0.0031(13) C16 0.0358(16) 0.0230(13) 0.0413(16) -0.0031(12) 0.0170(13) -0.0020(12) C17 0.0393(18) 0.0625(19) 0.0407(17) 0.0070(17) 0.0157(14) -0.0080(17) C18 0.0424(19) 0.074(2) 0.0426(18) 0.0037(18) 0.0063(15) -0.0031(19) C19 0.0340(17) 0.055(2) 0.060(2) 0.0059(17) 0.0141(16) 0.0003(15) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C19 S1 C16 92.42(15) C9 S2 C7 100.48(13) C1 N1 H1 124.0 C8 N1 H1 124.0 C8 N1 C1 112.1(2) C2 C1 N1 109.7(2) C6 C1 N1 128.5(3) C6 C1 C2 121.8(3) C1 C2 C3 120.6(2) C1 C2 C7 108.4(2) C3 C2 C7 131.0(2) C2 C3 H3 121.1 C2 C3 C4 117.8(3) C4 C3 H3 121.1 C3 C4 H4 119.5 C5 C4 C3 120.9(3) C5 C4 H4 119.5 C4 C5 H5 119.3 C4 C5 C6 121.3(3) C6 C5 H5 119.3 C1 C6 C5 117.5(3) C1 C6 H6 121.2 C5 C6 H6 121.2 C2 C7 S2 111.27(18) C2 C7 C8 102.8(2) C2 C7 C15 116.0(2) C8 C7 S2 108.10(18) C15 C7 S2 107.40(18) C15 C7 C8 111.0(2) O1 C8 N1 126.1(2) O1 C8 C7 127.0(3) N1 C8 C7 106.8(2) C10 C9 S2 119.8(2) C14 C9 S2 119.9(2) C14 C9 C10 120.2(3) C9 C10 H10 120.3 C11 C10 C9 119.3(3) C11 C10 H10 120.3 C10 C11 H11 119.9 C12 C11 C10 120.2(3) C12 C11 H11 119.9 C11 C12 H12 119.9 C11 C12 C13 120.3(3) C13 C12 H12 119.9 C12 C13 H13 120.2 C14 C13 C12 119.6(3) C14 C13 H13 120.2 C9 C14 C13 120.3(3) C9 C14 H14 119.8 C13 C14 H14 119.8 C7 C15 H15A 110.7(16) C7 C15 H15B 110.3(17) C16 C15 C7 113.3(2) C16 C15 H15A 108.4(17) C16 C15 H15B 107.7(17) H15A C15 H15B 106(2) C15 C16 S1 122.6(2) C17 C16 S1 109.5(2) C17 C16 C15 127.9(3) C16 C17 H17 123.3 C16 C17 C18 113.4(3) C18 C17 H17 123.3 C17 C18 H18 123.3 C19 C18 C17 113.4(3) C19 C18 H18 123.3 S1 C19 H19 124.4 C18 C19 S1 111.3(2) C18 C19 H19 124.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C16 1.727(3) S1 C19 1.705(3) S2 C7 1.852(3) S2 C9 1.787(3) O1 C8 1.218(3) N1 H1 0.8600 N1 C1 1.403(3) N1 C8 1.351(3) C1 C2 1.380(3) C1 C6 1.373(4) C2 C3 1.382(4) C2 C7 1.495(3) C3 H3 0.9300 C3 C4 1.386(4) C4 H4 0.9300 C4 C5 1.378(4) C5 H5 0.9300 C5 C6 1.379(4) C6 H6 0.9300 C7 C8 1.545(3) C7 C15 1.532(4) C9 C10 1.382(4) C9 C14 1.372(4) C10 H10 0.9300 C10 C11 1.381(4) C11 H11 0.9300 C11 C12 1.375(5) C12 H12 0.9300 C12 C13 1.377(5) C13 H13 0.9300 C13 C14 1.377(4) C14 H14 0.9300 C15 C16 1.495(4) C15 H15A 0.93(3) C15 H15B 0.95(3) C16 C17 1.354(4) C17 H17 0.9300 C17 C18 1.413(4) C18 H18 0.9300 C18 C19 1.329(4) C19 H19 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.86 2.12 2.935(3) 156.9 2_343