#------------------------------------------------------------------------------ #$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006169.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_2006169 loop_ _publ_author_name 'Gallagher, J. F.' 'Ferguson, G.' 'Brouwer, W. G.' _publ_section_title ; 3-(Benzo[b]thien-2-yl)-5,6-dihydro-1,4,2-oxathiazine 4-Oxide ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 823 _journal_page_last 825 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C11 H9 N O2 S2 ' _chemical_formula_sum 'C11 H9 N O2 S2' _chemical_formula_weight 251.31 _chemical_name_systematic ; 3-Benzo[b]thien-2-yl-5,6-dihydro-1,4,2-oxathiazine, 4-oxide ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.4730(11) _cell_length_b 8.2860(11) _cell_length_c 17.527(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 18.30 _cell_measurement_theta_min 10.30 _cell_volume 1085.3(2) _computing_cell_refinement 'SET4 & CELDIM CAD-4-PC' _computing_data_collection 'CAD-4-PC Software (Enraf-Nonius, 1992)' _computing_data_reduction 'DATRD2 in NRCVAX94 (Gabe, Le Page, Charland, Lee & White, 1989)' _computing_molecular_graphics 'NRCVAX94, ORTEPII (Johnson, 1976), PLATON (Spek, 1996a), PLUTON (Spek 1996b)' _computing_publication_material 'NRCVAX94, SHELXL93 and WordPerfect macro PREPCIF (Ferguson, 1996)' _computing_structure_refinement 'NRCVAX94 and SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SOLVER in NRCVAX94' _diffrn_ambient_temperature 294.0(10) _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 10 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min 22 _diffrn_reflns_number 2717 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 2.32 _diffrn_standards_decay_% '0 ; variation 0.5' _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.472 _exptl_absorpt_correction_T_max 0.9054 _exptl_absorpt_correction_T_min 0.8048 _exptl_absorpt_correction_type 'gaussian by integration' _exptl_crystal_colour 'very pale yellow' _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.204 _refine_diff_density_min -0.155 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -0.01(7) _refine_ls_extinction_coef 0.0053(18) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_all 1.060 _refine_ls_goodness_of_fit_obs 1.086 _refine_ls_hydrogen_treatment 'H atoms riding (C-H 0.93-0.97\%A)' _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2393 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_restrained_S_obs 1.086 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_obs 0.0257 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.0452P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.0732 _refine_ls_wR_factor_obs 0.0714 _reflns_number_observed 2186 _reflns_number_total 2393 _reflns_observed_criterion >2\s(I) _[local]_cod_data_source_file ab1427.cif _[local]_cod_data_source_block 96107abs _cod_original_cell_volume 1085.3(3) _cod_database_code 2006169 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 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 S4 0.0477(2) 0.0446(3) 0.0440(2) 0.0079(2) 0.0046(2) 0.0146(2) S11 0.0462(2) 0.0440(2) 0.0365(2) 0.0050(2) -0.0016(2) 0.0066(2) O1 0.0418(7) 0.0461(7) 0.0536(7) 0.0081(6) 0.0056(6) 0.0020(6) O4 0.0847(12) 0.0323(8) 0.0935(12) 0.0089(7) 0.0322(10) 0.0145(7) N2 0.0387(8) 0.0406(7) 0.0417(7) 0.0039(7) -0.0001(6) 0.0021(6) C3 0.0384(8) 0.0273(7) 0.0341(7) -0.0019(7) -0.0029(6) 0.0002(6) C5 0.0606(12) 0.0497(10) 0.0393(9) 0.0034(9) 0.0094(8) 0.0021(8) C6 0.0444(9) 0.0374(9) 0.0566(11) -0.0005(8) 0.0133(8) -0.0034(9) C12 0.0397(8) 0.0297(8) 0.0340(7) -0.0014(7) -0.0040(6) 0.0013(6) C13 0.0401(9) 0.0373(8) 0.0387(8) 0.0011(7) -0.0033(7) 0.0004(6) C13a 0.0386(9) 0.0388(9) 0.0427(9) -0.0037(8) -0.0012(7) -0.0085(7) C14 0.0383(9) 0.0580(12) 0.0634(12) 0.0014(8) -0.0034(8) -0.0175(10) C15 0.0409(11) 0.077(2) 0.0757(15) -0.0101(11) 0.0145(11) -0.0262(12) C16 0.0653(14) 0.077(2) 0.0575(12) -0.0238(13) 0.0243(11) -0.0162(12) C17 0.0666(13) 0.0539(11) 0.0437(10) -0.0165(11) 0.0086(10) -0.0022(8) C17a 0.0421(9) 0.0393(8) 0.0379(8) -0.0053(8) 0.0024(7) -0.0057(7) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol S4 0.32163(7) 0.45232(6) 0.52011(3) 0.04543(14) Uani d . 1 S S11 0.39642(7) 0.67998(6) 0.29598(2) 0.04225(13) Uani d . 1 S O1 -0.0030(2) 0.6754(2) 0.47124(8) 0.0471(3) Uani d . 1 O O4 0.2601(2) 0.2859(2) 0.50278(10) 0.0702(5) Uani d . 1 O N2 0.1437(2) 0.6686(2) 0.42309(9) 0.0403(3) Uani d . 1 N C3 0.2776(2) 0.5759(2) 0.43683(9) 0.0333(3) Uani d . 1 C C5 0.1497(3) 0.5457(3) 0.57608(11) 0.0499(5) Uani d . 1 C C6 -0.0171(3) 0.5529(2) 0.52899(12) 0.0461(4) Uani d . 1 C C12 0.4215(2) 0.5749(2) 0.38139(9) 0.0345(3) Uani d . 1 C C13 0.5830(2) 0.4995(2) 0.38737(10) 0.0387(4) Uani d . 1 C C13a 0.6925(2) 0.5229(2) 0.32122(10) 0.0401(4) Uani d . 1 C C14 0.8631(3) 0.4608(3) 0.30559(13) 0.0532(5) Uani d . 1 C C15 0.9423(3) 0.4948(3) 0.2371(2) 0.0645(7) Uani d . 1 C C16 0.8563(3) 0.5917(3) 0.18349(14) 0.0668(7) Uani d . 1 C C17 0.6901(3) 0.6568(3) 0.19730(12) 0.0547(5) Uani d . 1 C C17a 0.6090(3) 0.6204(2) 0.26669(10) 0.0397(4) Uani d . 1 C H5A 0.1284 0.4834 0.62206 0.060 Uiso calc R 1 H H5B 0.1860 0.6537 0.59080 0.060 Uiso calc R 1 H H6A -0.0373 0.4490 0.50502 0.055 Uiso calc R 1 H H6B -0.1186 0.5761 0.56169 0.055 Uiso calc R 1 H H13 0.6182 0.4397 0.42966 0.046 Uiso calc R 1 H H14 0.9218 0.3972 0.34143 0.064 Uiso calc R 1 H H15 1.0548 0.4527 0.2262 0.077 Uiso calc R 1 H H16 0.9127 0.6129 0.13725 0.080 Uiso calc R 1 H H17 0.6340 0.7227 0.16161 0.066 Uiso calc R 1 H 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 0 8 3 1 5 0 3 -6 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 O4 S4 C3 107.68(9) y O4 S4 C5 106.91(10) y C3 S4 C5 93.83(8) y C12 S11 C17a 90.76(8) y N2 O1 C6 117.29(13) y O1 N2 C3 121.78(14) y S4 C3 N2 129.07(13) y S4 C3 C12 113.69(12) y N2 C3 C12 117.11(14) y S4 C5 C6 108.21(13) y O1 C6 C5 110.9(2) y S11 C12 C3 119.55(12) y S11 C12 C13 112.99(13) y C3 C12 C13 127.46(14) y C12 C13 C13a 112.4(2) ? C13 C13a C14 128.9(2) ? C13 C13a C17a 112.1(2) ? C14 C13a C17a 119.0(2) ? C13a C14 C15 119.3(2) ? C14 C15 C16 120.7(2) ? C15 C16 C17 121.6(2) ? C16 C17 C17a 117.5(2) ? S11 C17a C17 126.4(2) ? S11 C17a C13a 111.68(13) ? C13a C17a C17 121.9(2) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S4 O4 1.485(2) y S4 C3 1.813(2) y S4 C5 1.792(2) y S11 C12 1.742(2) y S11 C17a 1.741(2) y O1 N2 1.385(2) y O1 C6 1.437(2) y N2 C3 1.284(2) y C3 C12 1.450(2) y C5 C6 1.496(3) y C12 C13 1.362(2) y C13 C13a 1.432(2) ? C13a C17a 1.398(3) ? C13a C14 1.402(3) ? C14 C15 1.368(3) ? C15 C16 1.393(4) ? C16 C17 1.376(3) ? C17 C17a 1.392(3) ? 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 C6 O1 N2 C3 -11.9(2) ? O1 N2 C3 C12 178.19(14) ? O1 N2 C3 S4 -6.2(3) y O4 S4 C3 N2 96.6(2) ? C5 S4 C3 N2 -12.5(2) ? O4 S4 C3 C12 -87.72(13) ? C5 S4 C3 C12 163.18(13) ? O4 S4 C5 C6 -62.2(2) ? C3 S4 C5 C6 47.61(14) ? N2 O1 C6 C5 54.0(2) ? S4 C5 C6 O1 -74.0(2) ? N2 C3 C12 C13 172.9(2) ? S4 C3 C12 C13 -3.3(2) ? N2 C3 C12 S11 -6.7(2) ? S4 C3 C12 S11 177.05(9) ? C17a S11 C12 C13 0.33(13) ? C17a S11 C12 C3 -179.99(13) ? C3 C12 C13 C13a 179.43(15) ? S11 C12 C13 C13a -0.9(2) ? C12 C13 C13a C17a 1.2(2) ? C12 C13 C13a C14 -177.9(2) ? C17a C13a C14 C15 -1.1(3) ? C13 C13a C14 C15 178.0(2) ? C13a C14 C15 C16 0.8(3) ? C14 C15 C16 C17 0.2(4) ? C15 C16 C17 C17a -0.9(3) ? C16 C17 C17a C13a 0.7(3) ? C16 C17 C17a S11 -177.0(2) ? C14 C13a C17a C17 0.3(3) ? C13 C13a C17a C17 -178.9(2) ? C14 C13a C17a S11 178.28(13) ? C13 C13a C17a S11 -0.9(2) ? C12 S11 C17a C17 178.2(2) ? C12 S11 C17a C13a 0.36(14) ?