#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/02/2200223.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2200223 loop_ _publ_author_name 'Coustard, Jean-Marie' 'Le Toquin, Ronan' 'Leo, Roland' 'Paulus, Werner' 'Cousson, Alain' _publ_section_title ; (E)-3-Methoxy-3-methylsulfanylisothiochroman-4-one oxime ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o256 _journal_page_last o257 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety ' C11 H13 N1 O2 S2 ' _chemical_formula_sum 'C11 H13 N O2 S2' _chemical_formula_weight 255.35 _chemical_name_systematic ; (E)-3-methoxy-3-methylsulfanylisothiochroman-4-one oxime ; _chemical_temperature_decomposition 138.5 _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.3725(2) _cell_length_b 10.7012(2) _cell_length_c 23.0919(4) _cell_measurement_reflns_used 16060 _cell_measurement_temperature 120 _cell_measurement_theta_max 28 _cell_measurement_theta_min 1 _cell_volume 2316.05(8) _computing_cell_refinement ; DENZO ; _computing_data_collection ; DENZO (Otwinowski & Minor, 1997), COLLECT (Nonius, 1998) ; _computing_data_reduction ; DENZO ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _computing_publication_material ; CRYSTALS ; _computing_structure_refinement ; CRYSTALS (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 120 _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f rotation scans with 2\% steps' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .044 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 16060 _diffrn_reflns_theta_max 28.0 _diffrn_reflns_theta_min 1.00 _diffrn_standards_decay_% .00 _exptl_absorpt_coefficient_mu .44 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.46 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1073.97 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .20 _refine_diff_density_max .86 _refine_diff_density_min -.48 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment refU _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2317 _refine_ls_R_factor_gt .036 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979): 0.668, 0.599, 0.382 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .043 _reflns_number_gt 2317 _reflns_number_total 2823 _reflns_threshold_expression I>3\s(I) _[local]_cod_data_source_file tk6001.cif _[local]_cod_data_source_block II _[local]_cod_chemical_formula_sum_orig ' C11 H13 N1 O2 S2 ' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_temperature_decomposition' since the value had been '138.5 (dec.)'. The value '138.5 (dec.)' was changed to '138.5'. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_temperature_decomposition' since the value had been '138.5 (dec.)'. The value '138.5 (dec.)' was changed to '138.5'. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 2316.0 _cod_database_code 2200223 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 loop_ _atom_site_label _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 S1 .05819(5) -.11183(4) .389587(17) .0258 Uani 1.0000 S2 -.22159(4) -.21074(4) .373388(16) .0231 Uani 1.0000 O1 .05499(12) -.55520(10) .43741(4) .0229 Uani 1.0000 O2 -.09002(13) -.22320(10) .47471(5) .0219 Uani 1.0000 N1 -.00388(13) -.43753(12) .44816(5) .0183 Uani 1.0000 C1 .05424(15) -.39098(13) .34967(6) .0176 Uani 1.0000 C2 .00356(16) -.49106(14) .31756(6) .0199 Uani 1.0000 C3 .05603(17) -.50977(16) .26373(7) .0253 Uani 1.0000 C4 .1594(2) -.43021(17) .24260(7) .0292 Uani 1.0000 C5 .21119(19) -.33152(18) .27437(7) .0300 Uani 1.0000 C6 .15805(17) -.31031(15) .32804(6) .0222 Uani 1.0000 C7 .20824(18) -.20566(17) .36504(7) .0270 Uani 1.0000 C8 -.06304(16) -.23405(14) .41668(6) .0188 Uani 1.0000 C9 -.00210(15) -.36337(14) .40602(6) .0167 Uani 1.0000 C10 -.1580(2) -.11057(16) .49207(7) .0278 Uani 1.0000 C11 -.34419(19) -.31788(17) .40594(8) .0309 Uani 1.0000 H1 .0514 -.5889 .4709 .0376(19) Uiso 1.0000 H21 -.0705 -.5485 .3339 .0476(19) Uiso 1.0000 H31 .0201 -.5807 .2394 .0476(19) Uiso 1.0000 H41 .1982 -.4452 .2028 .0476(19) Uiso 1.0000 H51 .2870 -.2763 .2581 .0476(19) Uiso 1.0000 H71 .2654 -.2297 .3993 .0376(19) Uiso 1.0000 H72 .2696 -.1475 .3454 .0376(19) Uiso 1.0000 H101 -.1728 -.1114 .5349 .0476(19) Uiso 1.0000 H102 -.2524 -.1037 .4721 .0476(19) Uiso 1.0000 H103 -.0969 -.0377 .4811 .0476(19) Uiso 1.0000 H111 -.4376 -.3138 .3855 .0476(19) Uiso 1.0000 H112 -.3575 -.2954 .4477 .0476(19) Uiso 1.0000 H113 -.3046 -.4047 .4033 .0476(19) Uiso 1.0000 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 .0324(2) .0201(2) .02511(19) -.00553(15) .00588(15) -.00090(13) S2 .0247(2) .0227(2) .02191(18) .00285(13) -.00431(13) .00188(14) O1 .0327(6) .0199(5) .0161(4) .0080(4) .0035(4) .0022(4) O2 .0295(6) .0211(5) .0152(5) .0037(4) .0009(4) .0005(4) N1 .0211(6) .0184(6) .0152(5) .0039(5) .0010(4) .0002(4) C1 .0180(6) .0205(7) .0142(6) .0022(5) .0010(5) .0008(5) C2 .0217(6) .0211(7) .0170(6) .0016(5) -.0005(5) .0012(5) C3 .0303(8) .0288(8) .0169(6) .0041(7) -.0023(5) -.0028(5) C4 .0341(8) .0350(8) .0184(7) .0037(7) .0058(6) -.0005(6) C5 .0326(8) .0345(9) .0230(7) -.0026(7) .0109(6) .0012(7) C6 .0214(7) .0271(7) .0180(6) -.0018(6) .0018(5) .0013(5) C7 .0229(7) .0325(8) .0254(7) -.0087(6) .0050(6) -.0041(6) C8 .0230(7) .0198(7) .0134(6) .0008(5) .0007(5) .0007(5) C9 .0164(6) .0194(7) .0144(6) -.0003(5) .0000(5) .0005(5) C10 .0359(9) .0244(8) .0229(7) .0035(7) .0041(6) -.0058(6) C11 .0245(8) .0322(9) .0360(9) -.0028(7) .0001(7) -.0007(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C7 . . 1.8186(18) no S1 C8 . . 1.8420(15) no S2 C8 . . 1.8083(15) no S2 C11 . . 1.7888(19) no O1 N1 . . 1.3971(16) no O1 H1 . . .8540(10) no O2 C8 . . 1.3684(17) no O2 C10 . . 1.4212(19) no N1 C9 . . 1.2559(19) no C1 C2 . . 1.387(2) no C1 C6 . . 1.393(2) no C1 C9 . . 1.4348(19) no C2 C3 . . 1.352(2) no C2 H21 . . 1.0009(15) no C3 C4 . . 1.379(2) no C3 H31 . . 1.0028(16) no C4 C5 . . 1.374(3) no C4 H41 . . 1.0011(15) no C5 C6 . . 1.355(2) no C5 H51 . . .9979(17) no C6 C7 . . 1.485(2) no C7 H71 . . .9901(18) no C7 H72 . . .9614(16) no C8 C9 . . 1.517(2) no C10 H101 . . .9976(16) no C10 H102 . . 1.0008(18) no C10 H103 . . .9999(18) no C11 H111 . . .9951(19) no C11 H112 . . 1.0028(19) no C11 H113 . . 1.0021(19) no loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C ' .0020 .0020 International_Tables_Vol_IV_Table_2.2B 'N ' .0040 .0030 International_Tables_Vol_IV_Table_2.2B 'S ' .1100 .1240 International_Tables_Vol_IV_Table_2.2B 'O ' .0080 .0060 International_Tables_Vol_IV_Table_2.2B 'H ' .0000 .0000 International_Tables_Vol_IV_Table_2.2B loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C7 S1 C8 101.00(7) no C8 S2 C11 101.96(8) no N1 O1 H1 101.80(10) no C8 O2 C10 115.54(12) no O1 N1 C9 115.25(12) no C2 C1 C6 121.74(14) no C2 C1 C9 121.20(13) no C6 C1 C9 117.03(13) no C1 C2 C3 118.79(15) no C1 C2 H21 120.65(14) no C3 C2 H21 120.56(15) no C2 C3 C4 119.31(15) no C2 C3 H31 120.35(16) no C4 C3 H31 120.34(15) no C3 C4 C5 122.26(15) no C3 C4 H41 118.76(17) no C5 C4 H41 118.98(17) no C4 C5 C6 119.15(16) no C4 C5 H51 120.33(16) no C6 C5 H51 120.52(18) no C1 C6 C5 118.74(15) no C1 C6 C7 118.83(14) no C5 C6 C7 122.42(15) no C6 C7 H71 115.81(16) no C6 C7 H72 113.97(15) no H71 C7 H72 102.84(15) no O2 C8 C9 107.81(11) no N1 C9 C1 125.27(14) no N1 C9 C8 116.46(12) no C1 C9 C8 118.27(12) no O2 C10 H101 109.51(15) no O2 C10 H102 109.19(14) no H101 C10 H102 109.60(17) no O2 C10 H103 109.43(15) no H101 C10 H103 109.68(16) no H102 C10 H103 109.42(16) no H111 C11 H112 109.65(17) no H111 C11 H113 109.71(17) no H112 C11 H113 109.09(18) no 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_publ_flag C9 C8 S1 C7 -3.4(2) no C9 C1 C6 C7 2.7(4) no C11 S2 C8 S1 -173.65(8) no N1 C9 C8 S2 -114.67(13) no O2 C8 C9 C1 -171.08(12) no C11 S2 C8 S1 -173.65(8) no C2 C1 C9 N1 57.3(4) no C1 C9 N1 O1 .1(3) no _journal_paper_doi 10.1107/S1600536801002707