#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235084.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_2235084
loop_
_publ_author_name
'Arshad, Muhammad Nadeem'
'Khan, Islam Ullah'
'Zia-ur-Rehman, Muhammad'
'Ahmed, Waseem'
'Asiri, Abdullah M.'
_publ_section_title
;
 Methyl
 2-butyl-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazine-3-carboxylate
;
_journal_coeditor_code           IM2370
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1663
_journal_paper_doi               10.1107/S1600536812019733
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H17 N O5 S'
_chemical_formula_moiety         'C14 H17 N O5 S'
_chemical_formula_sum            'C14 H17 N O5 S'
_chemical_formula_weight         311.35
_chemical_name_systematic
;
Methyl 2-butyl-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazine-3-carboxylate
;
_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                 91.741(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.173(7)
_cell_length_b                   9.280(2)
_cell_length_c                   12.531(3)
_cell_measurement_reflns_used    5544
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      2.34
_cell_volume                     2926.0(12)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and X-SEED (Barbour, 2001)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker SMART 1K'
_diffrn_measurement_method       'φ and ω 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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12490
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.9419
_exptl_absorpt_correction_T_min  0.9009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.702
_refine_diff_density_min         -0.489
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0695
_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/[σ²(Fo²)+(0.0839P)²+25.4705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2068
_refine_ls_wR_factor_ref         0.2097
_reflns_number_gt                3132
_reflns_number_total             3498
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2370.cif
_cod_data_source_block           I
_cod_original_cell_volume        2926.0(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235084
_cod_database_fobs_code          2235084
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_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 0.39425(3) 0.14891(9) 0.48843(6) 0.0157(2) Uani d . 1
O O1 0.28629(10) 0.2661(3) 0.23550(19) 0.0204(5) Uani d . 1
H H1O 0.3009 0.2796 0.1770 0.024 Uiso calc R 1
O O2 0.39702(10) 0.3001(3) 0.5114(2) 0.0212(5) Uani d . 1
O O3 0.42548(10) 0.0508(3) 0.55284(19) 0.0218(5) Uani d . 1
O O4 0.36673(10) 0.3043(3) 0.11802(19) 0.0222(5) Uani d . 1
O O5 0.44802(10) 0.2584(3) 0.19007(19) 0.0202(5) Uani d . 1
N N1 0.40931(11) 0.1252(3) 0.3631(2) 0.0166(6) Uani d . 1
C C1 0.32710(13) 0.0977(4) 0.4870(3) 0.0164(6) Uani d . 1
C C2 0.30543(14) 0.0261(4) 0.5729(3) 0.0206(7) Uani d . 1
H H2 0.3273 -0.0019 0.6325 0.025 Uiso calc R 1
C C3 0.25114(15) -0.0039(4) 0.5702(3) 0.0231(7) Uani d . 1
H H3 0.2358 -0.0522 0.6286 0.028 Uiso calc R 1
C C4 0.21938(14) 0.0363(4) 0.4828(3) 0.0215(7) Uani d . 1
H H4 0.1824 0.0160 0.4818 0.026 Uiso calc R 1
C C5 0.24152(13) 0.1063(4) 0.3964(3) 0.0191(7) Uani d . 1
H H5 0.2195 0.1339 0.3370 0.023 Uiso calc R 1
C C6 0.29595(13) 0.1362(4) 0.3967(3) 0.0173(6) Uani d . 1
C C7 0.32050(13) 0.2003(4) 0.3037(3) 0.0171(6) Uani d . 1
C C8 0.37370(13) 0.1909(4) 0.2873(2) 0.0167(6) Uani d . 1
C C9 0.39560(13) 0.2557(3) 0.1903(3) 0.0169(6) Uani d . 1
C C10 0.47078(15) 0.3216(5) 0.0957(3) 0.0273(8) Uani d . 1
H H10A 0.4646 0.2573 0.0346 0.041 Uiso calc R 1
H H10B 0.5091 0.3351 0.1081 0.041 Uiso calc R 1
H H10C 0.4540 0.4151 0.0809 0.041 Uiso calc R 1
C C11 0.43520(13) -0.0124(4) 0.3326(3) 0.0182(6) Uani d . 1
H H11A 0.4666 -0.0282 0.3805 0.022 Uiso calc R 1
H H11B 0.4480 -0.0028 0.2590 0.022 Uiso calc R 1
C C12 0.39938(14) -0.1447(4) 0.3374(3) 0.0195(7) Uani d . 1
H H12A 0.3675 -0.1300 0.2906 0.023 Uiso calc R 1
H H12B 0.3876 -0.1584 0.4114 0.023 Uiso calc R 1
C C13 0.42921(15) -0.2787(4) 0.3015(3) 0.0227(7) Uani d . 1
H H13A 0.4631 -0.2864 0.3432 0.027 Uiso calc R 1
H H13B 0.4378 -0.2683 0.2253 0.027 Uiso calc R 1
C C14 0.39715(17) -0.4169(4) 0.3160(4) 0.0340(9) Uani d . 1
H H14A 0.3861 -0.4238 0.3902 0.051 Uiso calc R 1
H H14B 0.4191 -0.5004 0.2989 0.051 Uiso calc R 1
H H14C 0.3656 -0.4149 0.2682 0.051 Uiso calc R 1
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
O2 S1 O3 119.06(15)
O2 S1 N1 108.17(15)
O3 S1 N1 108.32(15)
O2 S1 C1 107.95(15)
O3 S1 C1 110.17(16)
N1 S1 C1 101.78(15)
C7 O1 H1O 109.5
C9 O5 C10 115.4(3)
C8 N1 C11 117.9(3)
C8 N1 S1 114.9(2)
C11 N1 S1 118.5(2)
C2 C1 C6 121.6(3)
C2 C1 S1 121.5(2)
C6 C1 S1 117.0(3)
C1 C2 C3 119.0(3)
C1 C2 H2 120.5
C3 C2 H2 120.5
C4 C3 C2 120.4(3)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 120.3(3)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 120.4(3)
C4 C5 H5 119.8
C6 C5 H5 119.8
C5 C6 C1 118.3(3)
C5 C6 C7 121.1(3)
C1 C6 C7 120.5(3)
O1 C7 C8 123.2(3)
O1 C7 C6 114.4(3)
C8 C7 C6 122.3(3)
C7 C8 N1 121.9(3)
C7 C8 C9 119.3(3)
N1 C8 C9 118.7(3)
O4 C9 O5 124.0(3)
O4 C9 C8 121.9(3)
O5 C9 C8 114.1(3)
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
N1 C11 C12 114.6(3)
N1 C11 H11A 108.6
C12 C11 H11A 108.6
N1 C11 H11B 108.6
C12 C11 H11B 108.6
H11A C11 H11B 107.6
C11 C12 C13 110.3(3)
C11 C12 H12A 109.6
C13 C12 H12A 109.6
C11 C12 H12B 109.6
C13 C12 H12B 109.6
H12A C12 H12B 108.1
C12 C13 C14 112.4(3)
C12 C13 H13A 109.1
C14 C13 H13A 109.1
C12 C13 H13B 109.1
C14 C13 H13B 109.1
H13A C13 H13B 107.8
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 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
S1 O2 1.433(3)
S1 O3 1.435(2)
S1 N1 1.642(3)
S1 C1 1.756(3)
O1 C7 1.341(4)
O1 H1O 0.8400
O4 C9 1.230(4)
O5 C9 1.320(4)
O5 C10 1.453(4)
N1 C8 1.423(4)
N1 C11 1.489(4)
C1 C2 1.390(5)
C1 C6 1.404(4)
C2 C3 1.394(5)
C2 H2 0.9500
C3 C4 1.388(5)
C3 H3 0.9500
C4 C5 1.393(5)
C4 H4 0.9500
C5 C6 1.398(5)
C5 H5 0.9500
C6 C7 1.462(5)
C7 C8 1.364(5)
C8 C9 1.478(5)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.526(5)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.527(5)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.528(6)
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1O O4 0.84 1.85 2.564(4) 142.2
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 C8 -63.0(3)
O3 S1 N1 C8 166.7(2)
C1 S1 N1 C8 50.6(3)
O2 S1 N1 C11 150.0(2)
O3 S1 N1 C11 19.7(3)
C1 S1 N1 C11 -96.5(3)
O2 S1 C1 C2 -102.1(3)
O3 S1 C1 C2 29.5(3)
N1 S1 C1 C2 144.2(3)
O2 S1 C1 C6 76.0(3)
O3 S1 C1 C6 -152.4(2)
N1 S1 C1 C6 -37.7(3)
C6 C1 C2 C3 -2.0(5)
S1 C1 C2 C3 176.0(3)
C1 C2 C3 C4 0.4(5)
C2 C3 C4 C5 0.4(5)
C3 C4 C5 C6 0.3(5)
C4 C5 C6 C1 -1.8(5)
C4 C5 C6 C7 175.6(3)
C2 C1 C6 C5 2.7(5)
S1 C1 C6 C5 -175.4(3)
C2 C1 C6 C7 -174.8(3)
S1 C1 C6 C7 7.1(4)
C5 C6 C7 O1 19.3(5)
C1 C6 C7 O1 -163.4(3)
C5 C6 C7 C8 -159.5(3)
C1 C6 C7 C8 17.9(5)
O1 C7 C8 N1 177.6(3)
C6 C7 C8 N1 -3.8(5)
O1 C7 C8 C9 0.1(5)
C6 C7 C8 C9 178.7(3)
C11 N1 C8 C7 112.4(4)
S1 N1 C8 C7 -34.9(4)
C11 N1 C8 C9 -70.1(4)
S1 N1 C8 C9 142.7(3)
C10 O5 C9 O4 -1.1(5)
C10 O5 C9 C8 -179.9(3)
C7 C8 C9 O4 -8.0(5)
N1 C8 C9 O4 174.3(3)
C7 C8 C9 O5 170.8(3)
N1 C8 C9 O5 -6.8(4)
C8 N1 C11 C12 -76.7(4)
S1 N1 C11 C12 69.3(3)
N1 C11 C12 C13 178.3(3)
C11 C12 C13 C14 174.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657774
2 PubChem 139083833
