#------------------------------------------------------------------------------ #$Date$ #$Revision$ #$URL$ #------------------------------------------------------------------------------ # # 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_2218182 loop_ _publ_author_name 'Siddiqui, Waseeq Ahmad' 'Ahmad, Saeed' 'Siddiqui, Hamid Latif' 'Parvez, Masood' 'Rashid, Rehana' _publ_section_title ; Methyl 3-oxo-2,3-dihydro-1,2-benzothiazole-2-acetate 1,1-dioxide ; _journal_coeditor_code LH2607 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o859 _journal_volume 64 _journal_year 2008 _chemical_formula_iupac 'C10 H9 N O5 S' _chemical_formula_moiety 'C10 H9 N O5 S' _chemical_formula_sum 'C10 H9 N O5 S' _chemical_formula_weight 255.24 _chemical_name_common ; ; _chemical_name_systematic ; Methyl 3-oxo-2,3-dihydro-1,2-benzothiazole-2-acetate 1,1-dioxide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 104.39(2) _cell_angle_beta 100.58(2) _cell_angle_gamma 94.30(2) _cell_formula_units_Z 2 _cell_length_a 7.765(3) _cell_length_b 8.496(3) _cell_length_c 8.776(4) _cell_measurement_reflns_used 4654 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.4 _cell_measurement_theta_min 3.9 _cell_volume 546.8(4) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SAPI91 (Fan, 1991)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.036 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4654 _diffrn_reflns_theta_full 27.4 _diffrn_reflns_theta_max 27.4 _diffrn_reflns_theta_min 3.9 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.46 _refine_diff_density_min -0.43 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2468 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all 0.053 _refine_ls_R_factor_gt 0.040 _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^)+(0.056P)^2^+0.29P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.103 _refine_ls_wR_factor_ref 0.111 _reflns_number_gt 2040 _reflns_number_total 2468 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh2607.cif _[local]_cod_data_source_block I loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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' S S 0.1246 0.1234 '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' loop_ _atom_site_type_symbol _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_calc_flag _atom_site_refinement_flags _atom_site_occupancy S S1 0.25284(6) 0.37128(6) 1.06522(6) 0.02602(16) Uani d . 1 O O1 -0.07412(18) 0.18372(19) 0.67891(17) 0.0354(3) Uani d . 1 O O2 0.40672(17) 0.29152(17) 1.08988(17) 0.0320(3) Uani d . 1 O O3 0.2727(2) 0.54422(17) 1.13620(18) 0.0372(4) Uani d . 1 O O4 0.3882(2) 0.14876(17) 0.70088(18) 0.0369(4) Uani d . 1 O O5 0.41016(18) 0.33528(17) 0.56027(16) 0.0312(3) Uani d . 1 N N1 0.1635(2) 0.3311(2) 0.87005(18) 0.0275(4) Uani d . 1 C C1 0.0687(2) 0.2676(2) 1.1032(2) 0.0243(4) Uani d . 1 C C2 0.0451(3) 0.2516(2) 1.2517(2) 0.0303(4) Uani d . 1 H H2 0.1321 0.2987 1.3471 0.036 Uiso calc R 1 C C3 -0.1118(3) 0.1633(3) 1.2543(3) 0.0325(4) Uani d . 1 H H3 -0.1321 0.1482 1.3535 0.039 Uiso calc R 1 C C4 -0.2397(3) 0.0968(2) 1.1148(3) 0.0329(5) Uani d . 1 H H4 -0.3467 0.0384 1.1202 0.040 Uiso calc R 1 C C5 -0.2128(3) 0.1147(2) 0.9669(2) 0.0297(4) Uani d . 1 H H5 -0.3005 0.0698 0.8716 0.036 Uiso calc R 1 C C6 -0.0558(2) 0.1990(2) 0.9619(2) 0.0245(4) Uani d . 1 C C7 -0.0003(2) 0.2326(2) 0.8179(2) 0.0263(4) Uani d . 1 C C8 0.2499(3) 0.3960(2) 0.7616(2) 0.0292(4) Uani d . 1 H H8A 0.3291 0.4972 0.8238 0.035 Uiso calc R 1 H H8B 0.1593 0.4256 0.6819 0.035 Uiso calc R 1 C C9 0.3566(2) 0.2757(2) 0.6733(2) 0.0268(4) Uani d . 1 C C10 0.5248(3) 0.2391(3) 0.4726(3) 0.0435(6) Uani d . 1 H H10A 0.5553 0.2910 0.3914 0.052 Uiso calc R 1 H H10B 0.4638 0.1284 0.4195 0.052 Uiso calc R 1 H H10C 0.6329 0.2329 0.5475 0.052 Uiso calc R 1 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 0.0241(3) 0.0292(3) 0.0245(3) 0.00447(18) 0.00385(18) 0.00737(18) O1 0.0311(7) 0.0495(9) 0.0236(7) 0.0080(6) 0.0024(6) 0.0076(6) O2 0.0225(7) 0.0398(8) 0.0339(8) 0.0068(6) 0.0027(6) 0.0117(6) O3 0.0426(9) 0.0266(7) 0.0379(8) 0.0026(6) 0.0035(7) 0.0045(6) O4 0.0472(9) 0.0316(8) 0.0378(8) 0.0101(7) 0.0158(7) 0.0136(6) O5 0.0308(7) 0.0441(8) 0.0252(7) 0.0126(6) 0.0102(6) 0.0158(6) N1 0.0242(8) 0.0376(9) 0.0217(8) 0.0022(7) 0.0048(6) 0.0102(7) C1 0.0226(9) 0.0270(9) 0.0251(9) 0.0069(7) 0.0061(7) 0.0083(7) C2 0.0307(10) 0.0375(11) 0.0241(10) 0.0094(8) 0.0053(8) 0.0095(8) C3 0.0377(11) 0.0375(11) 0.0309(11) 0.0155(9) 0.0161(9) 0.0151(8) C4 0.0269(10) 0.0328(10) 0.0452(12) 0.0065(8) 0.0137(9) 0.0164(9) C5 0.0245(9) 0.0314(10) 0.0328(10) 0.0046(8) 0.0035(8) 0.0095(8) C6 0.0252(9) 0.0248(9) 0.0240(9) 0.0086(7) 0.0042(7) 0.0066(7) C7 0.0261(9) 0.0288(9) 0.0237(10) 0.0051(7) 0.0073(7) 0.0042(7) C8 0.0305(10) 0.0329(10) 0.0297(10) 0.0075(8) 0.0115(8) 0.0135(8) C9 0.0230(9) 0.0325(10) 0.0243(9) 0.0000(7) 0.0032(7) 0.0090(8) C10 0.0436(13) 0.0656(15) 0.0302(11) 0.0250(11) 0.0173(10) 0.0169(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O2 1.4258(15) S1 O3 1.4306(15) S1 N1 1.6640(18) S1 C1 1.7504(19) O1 C7 1.202(2) O4 C9 1.196(2) O5 C9 1.335(2) O5 C10 1.449(2) N1 C7 1.402(3) N1 C8 1.449(2) C1 C2 1.387(3) C1 C6 1.388(3) C2 C3 1.389(3) C2 H2 0.9500 C3 C4 1.389(3) C3 H3 0.9500 C4 C5 1.395(3) C4 H4 0.9500 C5 C6 1.380(3) C5 H5 0.9500 C6 C7 1.492(3) C8 C9 1.517(3) C8 H8A 0.9900 C8 H8B 0.9900 C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O2 S1 O3 116.71(9) O2 S1 N1 110.73(9) O3 S1 N1 109.35(9) O2 S1 C1 112.26(9) O3 S1 C1 112.83(9) N1 S1 C1 92.26(9) C9 O5 C10 115.33(16) C7 N1 C8 122.31(16) C7 N1 S1 116.00(13) C8 N1 S1 121.68(13) C2 C1 C6 122.73(18) C2 C1 S1 126.37(15) C6 C1 S1 110.90(14) C1 C2 C3 116.80(19) C1 C2 H2 121.6 C3 C2 H2 121.6 C2 C3 C4 121.34(19) C2 C3 H3 119.3 C4 C3 H3 119.3 C3 C4 C5 120.73(19) C3 C4 H4 119.6 C5 C4 H4 119.6 C6 C5 C4 118.57(18) C6 C5 H5 120.7 C4 C5 H5 120.7 C5 C6 C1 119.81(18) C5 C6 C7 127.38(17) C1 C6 C7 112.78(17) O1 C7 N1 123.33(18) O1 C7 C6 128.71(18) N1 C7 C6 107.93(16) N1 C8 C9 112.82(16) N1 C8 H8A 109.0 C9 C8 H8A 109.0 N1 C8 H8B 109.0 C9 C8 H8B 109.0 H8A C8 H8B 107.8 O4 C9 O5 125.61(18) O4 C9 C8 125.59(18) O5 C9 C8 108.80(16) O5 C10 H10A 109.5 O5 C10 H10B 109.5 H10A C10 H10B 109.5 O5 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 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 O2 S1 N1 C7 111.37(15) O3 S1 N1 C7 -118.66(15) C1 S1 N1 C7 -3.48(15) O2 S1 N1 C8 -69.24(17) O3 S1 N1 C8 60.73(17) C1 S1 N1 C8 175.91(15) O2 S1 C1 C2 68.07(19) O3 S1 C1 C2 -66.31(19) N1 S1 C1 C2 -178.43(18) O2 S1 C1 C6 -111.44(14) O3 S1 C1 C6 114.19(14) N1 S1 C1 C6 2.07(14) C6 C1 C2 C3 -0.4(3) S1 C1 C2 C3 -179.86(15) C1 C2 C3 C4 -1.0(3) C2 C3 C4 C5 1.0(3) C3 C4 C5 C6 0.4(3) C4 C5 C6 C1 -1.8(3) C4 C5 C6 C7 -179.84(17) C2 C1 C6 C5 1.8(3) S1 C1 C6 C5 -178.65(14) C2 C1 C6 C7 -179.84(17) S1 C1 C6 C7 -0.3(2) C8 N1 C7 O1 6.2(3) S1 N1 C7 O1 -174.37(15) C8 N1 C7 C6 -175.64(16) S1 N1 C7 C6 3.7(2) C5 C6 C7 O1 -5.9(3) C1 C6 C7 O1 175.94(19) C5 C6 C7 N1 176.14(18) C1 C6 C7 N1 -2.0(2) C7 N1 C8 C9 -84.4(2) S1 N1 C8 C9 96.29(18) C10 O5 C9 O4 -3.8(3) C10 O5 C9 C8 175.82(16) N1 C8 C9 O4 -9.1(3) N1 C8 C9 O5 171.21(15) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C2 H2 O5 1_556 0.95 2.53 3.435(3) 160 C4 H4 O4 2_557 0.95 2.54 3.209(3) 128 C8 H8A O2 2_667 0.99 2.49 3.435(3) 159 C10 H10C O1 1_655 0.98 2.47 3.431(3) 167