#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202492.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 'Subha Nandhini, M.' 'Banurekha, R.' 'Krishnakumar, R. V.' 'Mostad, A.' 'Bhavani, N.' 'Perumal, S.' 'Natarajan, S.' _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_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)' _[local]_cod_data_source_file ci6260.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_database_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_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_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) ?