#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202492.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_2202492 loop_ _publ_author_name 'M.Subha Nandhini' R.Banurekha 'R.V. Krishnakumar' A.Mostad 'N. Bhavani' 'S. Perumal' S.Natarajan _publ_section_title ; Ethyl cis-3-(2-methoxyphenyl)-1-4-thiazine-2-carboxylate 1,1-dioxide at 150K ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1400 _journal_page_last o1402 _journal_paper_doi 10.1107/S1600536803018579 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C14 H19 N O5 S' _chemical_formula_moiety 'C14 H19 N O5 S' _chemical_formula_sum 'C14 H19 N O5 S' _chemical_formula_weight 313.37 _chemical_name_systematic ; Ethyl cis-3-(2-methoxyphenyl)-1-4-thiazine-2-carboxylate 1,1-dioxide ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 93.44(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 25.706(5) _cell_length_b 9.7180(19) _cell_length_c 12.245(2) _cell_measurement_reflns_used 1024 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 26.4 _cell_measurement_theta_min 1.6 _cell_volume 3053.4(10) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method '\w scans' _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 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 15899 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 26.40 _diffrn_reflns_theta_min 1.59 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1328 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.419 _refine_diff_density_min -0.270 _refine_ls_extinction_coef 0.0092(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 197 _refine_ls_number_reflns 3132 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.149 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0322 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+2.1671P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.1002 _reflns_number_gt 2870 _reflns_number_total 3132 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file ci6260.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2202492 _cod_database_fobs_code 2202492 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, 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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S 0.322714(12) 0.14726(3) 0.23218(3) 0.01968(13) Uani d . 1 . . S O1 0.35941(4) 0.11629(11) 0.15045(8) 0.0267(2) Uani d . 1 . . O O2 0.27908(4) 0.23532(11) 0.20095(9) 0.0288(3) Uani d . 1 . . O O3 0.41381(4) 0.04073(12) 0.39844(11) 0.0357(3) Uani d . 1 . . O O4 0.44836(4) 0.24755(12) 0.36081(9) 0.0286(3) Uani d . 1 . . O O5 0.33309(4) 0.50833(10) 0.44500(8) 0.0243(2) Uani d . 1 . . O N1 0.30418(5) 0.09722(13) 0.48119(10) 0.0236(3) Uani d . 1 . . N H1N 0.3298(8) 0.043(2) 0.5029(15) 0.029(5) Uiso d . 1 . . H C1 0.35721(5) 0.22912(13) 0.34544(10) 0.0175(3) Uani d . 1 . . C H1 0.3640 0.3247 0.3249 0.021 Uiso calc R 1 . . H C2 0.32297(5) 0.23077(14) 0.44831(11) 0.0191(3) Uani d . 1 . . C H2 0.2923 0.2877 0.4293 0.023 Uiso calc R 1 . . H C3 0.27169(6) 0.02871(15) 0.39572(12) 0.0267(3) Uani d . 1 . . C H3A 0.2419 0.0870 0.3764 0.032 Uiso calc R 1 . . H H3B 0.2586 -0.0562 0.4253 0.032 Uiso calc R 1 . . H C4 0.29924(6) -0.00532(15) 0.29055(12) 0.0252(3) Uani d . 1 . . C H4A 0.2750 -0.0506 0.2385 0.030 Uiso calc R 1 . . H H4B 0.3281 -0.0676 0.3077 0.030 Uiso calc R 1 . . H C5 0.40920(5) 0.15926(15) 0.37093(11) 0.0218(3) Uani d . 1 . . C C6 0.50085(6) 0.1969(2) 0.39315(15) 0.0386(4) Uani d . 1 . . C H6A 0.5261 0.2414 0.3491 0.046 Uiso calc R 1 . . H H6B 0.5025 0.0986 0.3802 0.046 Uiso calc R 1 . . H C7 0.51395(7) 0.2258(2) 0.51068(16) 0.0466(5) Uani d . 1 . . C H7A 0.5483 0.1921 0.5306 0.070 Uiso calc R 1 . . H H7B 0.4892 0.1807 0.5543 0.070 Uiso calc R 1 . . H H7C 0.5128 0.3232 0.5232 0.070 Uiso calc R 1 . . H C8 0.35455(5) 0.30447(14) 0.53943(11) 0.0201(3) Uani d . 1 . . C C9 0.38086(6) 0.23571(16) 0.62550(11) 0.0258(3) Uani d . 1 . . C H9 0.37817 0.136 0.63040 0.031 Uiso calc R 1 . . H C10 0.41106(6) 0.30728(18) 0.70496(12) 0.0312(3) Uani d . 1 . . C H10 0.4293 0.2584 0.7636 0.037 Uiso calc R 1 . . H C11 0.41468(6) 0.44924(17) 0.69896(12) 0.0311(3) Uani d . 1 . . C H11 0.4349 0.4977 0.7531 0.037 Uiso calc R 1 . . H C12 0.38872(6) 0.52107(16) 0.61361(12) 0.0263(3) Uani d . 1 . . C H12 0.39115 0.618 0.61002 0.032 Uiso calc R 1 . . H C13 0.35913(5) 0.44876(15) 0.53350(11) 0.0208(3) Uani d . 1 . . C C14 0.33272(6) 0.65548(15) 0.43815(13) 0.0281(3) Uani d . 1 . . C H14A 0.3132 0.6835 0.3726 0.042 Uiso calc R 1 . . H H14B 0.3678 0.6886 0.4367 0.042 Uiso calc R 1 . . H H14C 0.3168 0.6929 0.5006 0.042 Uiso calc R 1 . . H 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 S 0.0228(2) 0.0165(2) 0.0195(2) -0.00136(12) -0.00074(13) -0.00127(11) O1 0.0362(6) 0.0230(5) 0.0213(5) -0.0020(4) 0.0058(4) -0.0030(4) O2 0.0282(5) 0.0260(5) 0.0310(6) 0.0016(4) -0.0085(4) -0.0006(4) O3 0.0278(6) 0.0274(6) 0.0520(7) 0.0069(4) 0.0021(5) 0.0073(5) O4 0.0177(5) 0.0374(6) 0.0304(6) -0.0038(4) -0.0001(4) 0.0033(4) O5 0.0303(5) 0.0176(5) 0.0242(5) 0.0000(4) -0.0036(4) -0.0005(4) N1 0.0250(6) 0.0203(6) 0.0260(6) -0.0034(5) 0.0053(5) 0.0020(5) C1 0.0189(6) 0.0162(6) 0.0174(6) -0.0015(5) 0.0013(5) 0.0006(5) C2 0.0196(6) 0.0176(6) 0.0203(6) 0.0002(5) 0.0036(5) 0.0004(5) C3 0.0245(7) 0.0230(7) 0.0332(8) -0.0075(5) 0.0072(6) -0.0022(6) C4 0.0285(7) 0.0176(7) 0.0297(7) -0.0054(5) 0.0036(6) -0.0022(5) C5 0.0203(7) 0.0271(7) 0.0182(6) 0.0011(5) 0.0025(5) 0.0000(5) C6 0.0167(7) 0.0545(11) 0.0446(10) 0.0000(7) 0.0007(6) -0.0005(8) C7 0.0304(9) 0.0681(13) 0.0401(10) 0.0037(8) -0.0071(7) 0.0084(9) C8 0.0212(6) 0.0213(7) 0.0183(6) -0.0005(5) 0.0060(5) -0.0018(5) C9 0.0329(8) 0.0254(7) 0.0194(7) 0.0019(6) 0.0041(6) 0.0018(5) C10 0.0381(8) 0.0367(9) 0.0185(7) 0.0048(7) -0.0015(6) 0.0015(6) C11 0.0341(8) 0.0362(9) 0.0225(7) 0.0002(7) -0.0033(6) -0.0087(6) C12 0.0295(7) 0.0241(7) 0.0254(7) -0.0007(6) 0.0024(6) -0.0056(6) C13 0.0211(6) 0.0228(7) 0.0189(6) 0.0008(5) 0.0034(5) -0.0007(5) C14 0.0322(8) 0.0182(7) 0.0332(8) -0.0004(5) -0.0033(6) 0.0020(6) 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 _geom_angle_publ_flag O2 S O1 117.92(7) ? O2 S C4 109.00(7) ? O1 S C4 110.95(7) ? O2 S C1 106.44(6) ? O1 S C1 108.38(6) ? C4 S C1 103.01(7) ? C5 O4 C6 116.47(13) ? C13 O5 C14 118.04(11) ? C2 N1 C3 113.26(11) ? C2 N1 H1N 111.3(13) ? C3 N1 H1N 109.6(13) ? C5 C1 C2 111.56(11) yes C5 C1 S 110.54(9) yes C2 C1 S 110.42(9) yes C5 C1 H1 108.1 ? C2 C1 H1 108.1 ? S C1 H1 108.1 ? N1 C2 C8 112.97(11) yes N1 C2 C1 115.03(11) yes C8 C2 C1 106.95(10) yes N1 C2 H2 107.2 ? C8 C2 H2 107.2 ? C1 C2 H2 107.2 ? N1 C3 C4 115.13(12) ? N1 C3 H3A 108.5 ? C4 C3 H3A 108.5 ? N1 C3 H3B 108.5 ? C4 C3 H3B 108.5 ? H3A C3 H3B 107.5 ? C3 C4 S 110.04(10) ? C3 C4 H4A 109.7 ? S C4 H4A 109.7 ? C3 C4 H4B 109.7 ? S C4 H4B 109.7 ? H4A C4 H4B 108.2 ? O3 C5 O4 125.39(13) ? O3 C5 C1 123.87(13) ? O4 C5 C1 110.73(12) ? O4 C6 C7 110.43(14) ? O4 C6 H6A 109.6 ? C7 C6 H6A 109.6 ? O4 C6 H6B 109.6 ? C7 C6 H6B 109.6 ? H6A C6 H6B 108.1 ? C6 C7 H7A 109.5 ? C6 C7 H7B 109.5 ? H7A C7 H7B 109.5 ? C6 C7 H7C 109.5 ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? C9 C8 C13 118.65(13) yes C9 C8 C2 123.01(13) yes C13 C8 C2 118.28(12) yes C8 C9 C10 121.00(14) ? C8 C9 H9 119.5 ? C10 C9 H9 119.5 ? C11 C10 C9 119.77(14) ? C11 C10 H10 120.1 ? C9 C10 H10 120.1 ? C10 C11 C12 120.54(14) ? C10 C11 H11 119.7 ? C12 C11 H11 119.7 ? C11 C12 C13 119.45(14) ? C11 C12 H12 120.3 ? C13 C12 H12 120.3 ? O5 C13 C12 124.36(13) ? O5 C13 C8 115.06(12) ? C12 C13 C8 120.58(13) ? O5 C14 H14A 109.5 ? O5 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? O5 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S O2 . 1.4440(11) yes S O1 . 1.4476(11) yes S C4 . 1.7678(15) yes S C1 . 1.7874(14) yes O3 C5 . 1.2039(19) yes O4 C5 . 1.3341(18) yes O4 C6 . 1.4682(18) yes O5 C13 . 1.3677(17) yes O5 C14 . 1.4325(17) yes N1 C2 . 1.4501(17) yes N1 C3 . 1.4599(19) yes N1 H1N . 0.87(2) ? C1 C5 . 1.5146(18) ? C1 C2 . 1.5796(18) ? C1 H1 . 0.98 ? C2 C8 . 1.5194(19) ? C2 H2 . 0.98 ? C3 C4 . 1.542(2) ? C3 H3A . 0.97 ? C3 H3B . 0.97 ? C4 H4A . 0.97 ? C4 H4B . 0.97 ? C6 C7 . 1.485(3) ? C6 H6A . 0.97 ? C6 H6B . 0.97 ? C7 H7A . 0.96 ? C7 H7B . 0.96 ? C7 H7C . 0.96 ? C8 C9 . 1.389(2) ? C8 C13 . 1.409(2) ? C9 C10 . 1.394(2) ? C9 H9 . 0.97 ? C10 C11 . 1.385(2) ? C10 H10 . 0.96 ? C11 C12 . 1.393(2) ? C11 H11 . 0.94 ? C12 C13 . 1.395(2) ? C12 H12 . 0.95 ? C14 H14A . 0.96 ? C14 H14B . 0.96 ? C14 H14C . 0.96 ? 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 C7 H7A O3 5_656 0.96 2.59 3.339(2) 135 N1 H1N O1 6_556 0.87(2) 2.47(2) 3.204(2) 142(2) C9 H9 O1 6_556 0.97 2.51 3.481(2) 173 C14 H14A O2 4 0.96 2.54 3.343(2) 142 C1 H1 O5 1 0.98 2.47 3.054(2) 118 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 O2 S C1 C5 -169.33(9) ? O1 S C1 C5 -41.56(11) ? C4 S C1 C5 76.06(10) ? O2 S C1 C2 66.75(10) ? O1 S C1 C2 -165.48(9) ? C4 S C1 C2 -47.87(10) yes C3 N1 C2 C8 177.20(11) ? C3 N1 C2 C1 -59.62(15) yes C5 C1 C2 N1 -68.46(15) ? S C1 C2 N1 54.88(13) yes C5 C1 C2 C8 57.88(14) yes S C1 C2 C8 -178.78(9) ? C2 N1 C3 C4 62.44(16) yes N1 C3 C4 S -59.42(15) yes O2 S C4 C3 -62.81(12) ? O1 S C4 C3 165.73(10) ? C1 S C4 C3 49.94(12) yes C6 O4 C5 O3 -4.2(2) ? C6 O4 C5 C1 174.45(12) ? C2 C1 C5 O3 61.54(18) ? S C1 C5 O3 -61.73(16) ? C2 C1 C5 O4 -117.18(12) ? S C1 C5 O4 119.55(11) ? C5 O4 C6 C7 -90.30(19) ? N1 C2 C8 C9 25.17(18) ? C1 C2 C8 C9 -102.39(14) yes N1 C2 C8 C13 -157.68(12) ? C1 C2 C8 C13 74.76(14) yes C13 C8 C9 C10 0.3(2) ? C2 C8 C9 C10 177.43(13) ? C8 C9 C10 C11 0.6(2) ? C9 C10 C11 C12 -0.5(2) ? C10 C11 C12 C13 -0.3(2) ? C14 O5 C13 C12 -5.0(2) ? C14 O5 C13 C8 175.29(12) ? C11 C12 C13 O5 -178.44(13) ? C11 C12 C13 C8 1.2(2) ? C9 C8 C13 O5 178.50(12) ? C2 C8 C13 O5 1.23(17) ? C9 C8 C13 C12 -1.2(2) ? C2 C8 C13 C12 -178.45(12) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139066054