#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/16/2221655.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_2221655
loop_
_publ_author_name
'Shafiq, Muhammad'
'Tahir, M. Nawaz'
'Khan, Islam Ullah'
'Arshad, Muhammad Nadeem'
'Asghar, Muhammad Nadeem'
_publ_section_title
;
 6-Bromo-1-methyl-1H-2,1-benzothiazin-4(3H)-one
 2,2-dioxide
;
_journal_coeditor_code           FB2142
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1182
_journal_paper_doi               10.1107/S1600536809015980
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C9 H8 Br N O3 S'
_chemical_formula_moiety         'C9 H8 Br N O3 S'
_chemical_formula_sum            'C9 H8 Br N O3 S'
_chemical_formula_weight         290.13
_chemical_name_systematic
;
6-Bromo-1-methyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.204(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4577(3)
_cell_length_b                   12.6400(8)
_cell_length_c                   15.1258(10)
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.10
_cell_volume                     1037.35(11)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_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      296(2)
_diffrn_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       '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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11077
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.148
_exptl_absorpt_correction_T_max  0.540
_exptl_absorpt_correction_T_min  0.439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0297
_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/[σ²(Fo²)+(0.0309P)²+0.4349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0719
_reflns_number_gt                1709
_reflns_number_total             2234
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2142.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221655
_cod_database_fobs_code          2221655
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.06150(6) 0.57510(2) 0.36727(2) 0.05871(14) Uani d . 1 . .
S S1 0.74473(12) 0.10243(5) 0.40740(4) 0.03706(17) Uani d . 1 . .
O O1 0.3779(4) 0.23972(17) 0.56688(14) 0.0606(6) Uani d . 1 . .
O O2 0.5116(4) 0.05733(15) 0.37692(14) 0.0529(5) Uani d . 1 . .
O O3 0.9592(4) 0.03989(16) 0.40469(14) 0.0555(6) Uani d . 1 . .
N N1 0.7895(4) 0.21290(17) 0.35343(14) 0.0385(5) Uani d . 1 . .
C C1 0.6129(4) 0.29366(19) 0.35581(16) 0.0326(6) Uani d . 1 . .
C C2 0.5631(5) 0.3622(2) 0.28382(19) 0.0403(6) Uani d . 1 . .
H H2 0.6430 0.3525 0.2332 0.048 Uiso calc R 1 . .
C C3 0.3980(5) 0.4437(2) 0.2866(2) 0.0430(7) Uani d . 1 . .
H H3 0.3650 0.4882 0.2378 0.052 Uiso calc R 1 . .
C C4 0.2814(5) 0.4595(2) 0.36193(19) 0.0409(6) Uani d . 1 . .
C C5 0.3200(5) 0.3919(2) 0.43312(19) 0.0416(6) Uani d . 1 . .
H H5 0.2368 0.4024 0.4829 0.050 Uiso calc R 1 . .
C C6 0.4846(4) 0.3073(2) 0.43087(17) 0.0362(6) Uani d . 1 . .
C C7 0.5129(5) 0.2357(2) 0.50864(18) 0.0407(6) Uani d . 1 . .
C C8 0.7204(5) 0.1553(2) 0.51326(17) 0.0419(6) Uani d . 1 . .
H H8A 0.6884 0.0989 0.5540 0.050 Uiso calc R 1 . .
H H8B 0.8745 0.1891 0.5355 0.050 Uiso calc R 1 . .
C C9 0.9601(4) 0.2116(2) 0.28524(19) 0.0415(6) Uani d . 1 . .
H H9A 0.8798 0.1812 0.2316 0.062 Uiso calc R 1 . .
H H9B 1.1024 0.1701 0.3057 0.062 Uiso calc R 1 . .
H H9C 1.0102 0.2826 0.2737 0.062 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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 S1 O2 . . 118.63(13) ?
O3 S1 N1 . . 106.93(11) ?
O2 S1 N1 . . 110.70(12) ?
O3 S1 C8 . . 112.54(13) ?
O2 S1 C8 . . 107.17(13) ?
N1 S1 C8 . . 99.15(12) ?
C1 N1 C9 . . 121.1(2) ?
C1 N1 S1 . . 117.60(16) ?
C9 N1 S1 . . 118.62(17) ?
C2 C1 N1 . . 120.5(2) ?
C2 C1 C6 . . 118.8(2) ?
N1 C1 C6 . . 120.8(2) ?
C3 C2 C1 . . 121.1(2) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 119.8(3) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C5 C4 C3 . . 120.9(2) ?
C5 C4 Br1 . . 119.3(2) ?
C3 C4 Br1 . . 119.8(2) ?
C4 C5 C6 . . 120.1(2) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C1 . . 119.3(2) ?
C5 C6 C7 . . 117.4(2) ?
C1 C6 C7 . . 123.2(2) ?
O1 C7 C6 . . 122.3(2) ?
O1 C7 C8 . . 120.3(2) ?
C6 C7 C8 . . 117.4(2) ?
C7 C8 S1 . . 110.06(18) ?
C7 C8 H8A . . 109.6 ?
S1 C8 H8A . . 109.6 ?
C7 C8 H8B . . 109.6 ?
S1 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.2 ?
N1 C9 H9A . . 109.5 ?
N1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
N1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 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
Br1 C4 . 1.898(3) ?
S1 O3 . 1.4169(19) ?
S1 O2 . 1.424(2) ?
S1 N1 . 1.649(2) ?
S1 C8 . 1.753(3) ?
O1 C7 . 1.209(3) ?
N1 C1 . 1.407(3) ?
N1 C9 . 1.463(3) ?
C1 C2 . 1.395(3) ?
C1 C6 . 1.407(3) ?
C2 C3 . 1.373(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.379(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.372(4) ?
C5 C6 . 1.400(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.479(4) ?
C7 C8 . 1.518(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
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
_geom_hbond_publ_flag
C3 H3 O3 2_655 0.93 2.5400 3.308(4) 140.00 yes
C8 H8A O2 3_656 0.97 2.5400 3.470(3) 162.00 yes
C9 H9B O3 . 0.96 2.4100 2.824(3) 106.00 yes
C5 H5 Br1 3_566 0.93 2.9440 3.871(3) 175.09 yes
C9 H9A Br1 2_545 0.96 3.0095 3.871(2) 150.03 yes
C9 H9C Cg1 1_655 0.96 2.8300 3.449(3) 123.00 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 S1 N1 C1 . . . . -172.74(19) ?
O2 S1 N1 C1 . . . . 56.7(2) ?
C8 S1 N1 C1 . . . . -55.7(2) ?
O3 S1 N1 C9 . . . . 25.6(2) ?
O2 S1 N1 C9 . . . . -105.0(2) ?
C8 S1 N1 C9 . . . . 142.7(2) ?
C9 N1 C1 C2 . . . . 12.8(4) ?
S1 N1 C1 C2 . . . . -148.4(2) ?
C9 N1 C1 C6 . . . . -166.8(2) ?
S1 N1 C1 C6 . . . . 32.0(3) ?
N1 C1 C2 C3 . . . . -177.5(2) ?
C6 C1 C2 C3 . . . . 2.0(4) ?
C1 C2 C3 C4 . . . . 0.9(4) ?
C2 C3 C4 C5 . . . . -2.8(4) ?
C2 C3 C4 Br1 . . . . 177.9(2) ?
C3 C4 C5 C6 . . . . 1.7(4) ?
Br1 C4 C5 C6 . . . . -179.0(2) ?
C4 C5 C6 C1 . . . . 1.2(4) ?
C4 C5 C6 C7 . . . . -178.3(2) ?
C2 C1 C6 C5 . . . . -3.1(4) ?
N1 C1 C6 C5 . . . . 176.5(2) ?
C2 C1 C6 C7 . . . . 176.5(2) ?
N1 C1 C6 C7 . . . . -3.9(4) ?
C5 C6 C7 O1 . . . . 9.9(4) ?
C1 C6 C7 O1 . . . . -169.7(3) ?
C5 C6 C7 C8 . . . . -170.1(2) ?
C1 C6 C7 C8 . . . . 10.3(4) ?
O1 C7 C8 S1 . . . . 139.9(2) ?
C6 C7 C8 S1 . . . . -40.0(3) ?
O3 S1 C8 C7 . . . . 170.50(19) ?
O2 S1 C8 C7 . . . . -57.3(2) ?
N1 S1 C8 C7 . . . . 57.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10557542
2 PubChem 21816146
