#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225859.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_2225859
loop_
_publ_author_name
'Shah, Tariq Saeed'
'Siddiqui, Waseeq Ahmad'
'Tahir, M. Nawaz'
'Hussain, Ghulam'
_publ_section_title
;
 N-(3-Chlorophenyl)-1,2-benzisothiazol-3-amine 1,1-dioxide
;
_journal_coeditor_code           HB5389
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1220
_journal_paper_doi               10.1107/S1600536810015163
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H9 Cl N2 O2 S'
_chemical_formula_moiety         'C13 H9 Cl N2 O2 S'
_chemical_formula_sum            'C13 H9 Cl N2 O2 S'
_chemical_formula_weight         292.73
_chemical_name_systematic
;
N-(3-Chlorophenyl)-1,2-benzisothiazol-3-amine 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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.178(6)
_cell_angle_beta                 98.840(5)
_cell_angle_gamma                97.574(5)
_cell_formula_units_Z            2
_cell_length_a                   7.2223(10)
_cell_length_b                   7.9138(12)
_cell_length_c                   11.2175(17)
_cell_measurement_reflns_used    1244
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.62
_cell_volume                     622.63(16)
_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 7.60
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0875
_diffrn_reflns_av_sigmaI/netI    0.1214
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10481
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.259
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.1585
_refine_ls_R_factor_gt           0.0560
_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)+(0.0363P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                1244
_reflns_number_total             2700
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5389.cif
_cod_data_source_block           I
_cod_database_code               2225859
_cod_database_fobs_code          2225859
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
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
C C1 1.1663(5) 0.2836(4) 0.4969(3) 0.0380(9) Uani d . 1 . .
C C2 1.2431(5) 0.3741(5) 0.6082(3) 0.0512(11) Uani d . 1 . .
H H2 1.3719 0.4162 0.6278 0.061 Uiso calc R 1 . .
C C3 1.1225(6) 0.4010(5) 0.6905(3) 0.0566(12) Uani d . 1 . .
H H3 1.1705 0.4625 0.7668 0.068 Uiso calc R 1 . .
C C4 0.9329(6) 0.3379(5) 0.6609(4) 0.0557(11) Uani d . 1 . .
H H4 0.8542 0.3572 0.7177 0.067 Uiso calc R 1 . .
C C5 0.8563(5) 0.2460(5) 0.5481(3) 0.0466(10) Uani d . 1 . .
H H5 0.7275 0.2038 0.5289 0.056 Uiso calc R 1 . .
C C6 0.9745(5) 0.2185(4) 0.4651(3) 0.0352(9) Uani d . 1 . .
C C7 0.9368(5) 0.1246(4) 0.3407(3) 0.0374(9) Uani d . 1 . .
C C8 0.6944(4) -0.0592(4) 0.1789(3) 0.0361(9) Uani d . 1 . .
C C9 0.5043(5) -0.1312(5) 0.1558(3) 0.0426(10) Uani d . 1 . .
H H9 0.4257 -0.1074 0.2119 0.051 Uiso calc R 1 . .
C C10 0.4338(5) -0.2380(5) 0.0491(3) 0.0415(10) Uani d . 1 . .
C C11 0.5448(5) -0.2769(5) -0.0357(3) 0.0482(10) Uani d . 1 . .
H H11 0.4944 -0.3497 -0.1073 0.058 Uiso calc R 1 . .
C C12 0.7330(5) -0.2050(5) -0.0116(3) 0.0485(11) Uani d . 1 . .
H H12 0.8109 -0.2302 -0.0677 0.058 Uiso calc R 1 . .
C C13 0.8080(5) -0.0967(5) 0.0939(3) 0.0457(10) Uani d . 1 . .
H H13 0.9353 -0.0485 0.1081 0.055 Uiso calc R 1 . .
Cl Cl1 0.19425(13) -0.32624(14) 0.02129(9) 0.0658(4) Uani d . 1 . .
N N1 0.7608(4) 0.0472(4) 0.2912(3) 0.0417(8) Uani d . 1 . .
H H1 0.6751 0.0650 0.3345 0.050 Uiso calc R 1 . .
N N2 1.0821(4) 0.1190(4) 0.2841(3) 0.0428(8) Uani d . 1 . .
O O1 1.4055(3) 0.1090(3) 0.4010(2) 0.0619(8) Uani d . 1 . .
O O2 1.3450(4) 0.3710(3) 0.3184(2) 0.0645(8) Uani d . 1 . .
S S1 1.27387(13) 0.22471(14) 0.37119(9) 0.0481(3) Uani d . 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 . . 122.5(3) ?
C2 C1 S1 . . 130.4(3) ?
C6 C1 S1 . . 107.1(3) ?
C1 C2 C3 . . 117.7(4) ?
C1 C2 H2 . . 121.2 ?
C3 C2 H2 . . 121.2 ?
C4 C3 C2 . . 120.7(4) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C5 . . 121.3(4) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C6 C5 C4 . . 118.7(4) ?
C6 C5 H5 . . 120.7 ?
C4 C5 H5 . . 120.7 ?
C5 C6 C1 . . 119.2(3) ?
C5 C6 C7 . . 131.3(3) ?
C1 C6 C7 . . 109.5(3) ?
N2 C7 N1 . . 122.9(3) ?
N2 C7 C6 . . 116.9(3) ?
N1 C7 C6 . . 120.2(3) ?
C13 C8 C9 . . 119.3(3) ?
C13 C8 N1 . . 123.8(3) ?
C9 C8 N1 . . 116.9(3) ?
C10 C9 C8 . . 119.1(3) ?
C10 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
C11 C10 C9 . . 122.3(3) ?
C11 C10 Cl1 . . 119.2(3) ?
C9 C10 Cl1 . . 118.5(3) ?
C10 C11 C12 . . 118.0(3) ?
C10 C11 H11 . . 121.0 ?
C12 C11 H11 . . 121.0 ?
C13 C12 C11 . . 121.3(3) ?
C13 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C12 C13 C8 . . 120.0(3) ?
C12 C13 H13 . . 120.0 ?
C8 C13 H13 . . 120.0 ?
C7 N1 C8 . . 130.1(3) ?
C7 N1 H1 . . 115.0 ?
C8 N1 H1 . . 115.0 ?
C7 N2 S1 . . 109.9(2) ?
O2 S1 O1 . . 115.88(17) ?
O2 S1 N2 . . 110.41(16) ?
O1 S1 N2 . . 109.76(16) ?
O2 S1 C1 . . 111.86(17) ?
O1 S1 C1 . . 110.64(17) ?
N2 S1 C1 . . 96.63(15) ?
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
C1 C2 . 1.367(5) ?
C1 C6 . 1.390(4) ?
C1 S1 . 1.760(4) ?
C2 C3 . 1.382(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.371(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.384(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.376(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.477(5) ?
C7 N2 . 1.310(4) ?
C7 N1 . 1.343(4) ?
C8 C13 . 1.384(4) ?
C8 C9 . 1.389(4) ?
C8 N1 . 1.417(4) ?
C9 C10 . 1.374(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.370(5) ?
C10 Cl1 . 1.746(3) ?
C11 C12 . 1.376(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(5) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
N1 H1 . 0.8600 ?
N2 S1 . 1.635(3) ?
O1 S1 . 1.432(3) ?
O2 S1 . 1.428(3) ?
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
C13 H13 N2 . 0.93 2.28 2.901(5) 124 yes
N1 H1 O1 1_455 0.86 2.24 3.084(4) 165 yes
C5 H5 O1 1_455 0.93 2.51 3.396(4) 159 yes
C2 H2 O2 2_866 0.93 2.42 3.302(4) 158 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
C6 C1 C2 C3 . . . . -0.3(6) ?
S1 C1 C2 C3 . . . . -179.8(3) ?
C1 C2 C3 C4 . . . . 0.3(6) ?
C2 C3 C4 C5 . . . . -0.1(6) ?
C3 C4 C5 C6 . . . . 0.0(6) ?
C4 C5 C6 C1 . . . . -0.1(5) ?
C4 C5 C6 C7 . . . . 178.8(4) ?
C2 C1 C6 C5 . . . . 0.2(6) ?
S1 C1 C6 C5 . . . . 179.8(3) ?
C2 C1 C6 C7 . . . . -178.9(3) ?
S1 C1 C6 C7 . . . . 0.8(4) ?
C5 C6 C7 N2 . . . . -179.1(4) ?
C1 C6 C7 N2 . . . . -0.1(4) ?
C5 C6 C7 N1 . . . . -0.2(6) ?
C1 C6 C7 N1 . . . . 178.7(3) ?
C13 C8 C9 C10 . . . . 0.1(5) ?
N1 C8 C9 C10 . . . . -178.8(3) ?
C8 C9 C10 C11 . . . . 0.2(6) ?
C8 C9 C10 Cl1 . . . . -179.6(3) ?
C9 C10 C11 C12 . . . . -0.1(6) ?
Cl1 C10 C11 C12 . . . . 179.7(3) ?
C10 C11 C12 C13 . . . . -0.3(6) ?
C11 C12 C13 C8 . . . . 0.6(6) ?
C9 C8 C13 C12 . . . . -0.5(5) ?
N1 C8 C13 C12 . . . . 178.3(3) ?
N2 C7 N1 C8 . . . . 4.0(6) ?
C6 C7 N1 C8 . . . . -174.8(3) ?
C13 C8 N1 C7 . . . . -3.2(6) ?
C9 C8 N1 C7 . . . . 175.6(3) ?
N1 C7 N2 S1 . . . . -179.4(3) ?
C6 C7 N2 S1 . . . . -0.6(4) ?
C7 N2 S1 O2 . . . . -115.4(3) ?
C7 N2 S1 O1 . . . . 115.7(3) ?
C7 N2 S1 C1 . . . . 0.9(3) ?
C2 C1 S1 O2 . . . . -66.3(4) ?
C6 C1 S1 O2 . . . . 114.1(3) ?
C2 C1 S1 O1 . . . . 64.5(4) ?
C6 C1 S1 O1 . . . . -115.0(3) ?
C2 C1 S1 N2 . . . . 178.6(4) ?
C6 C1 S1 N2 . . . . -1.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 641261
2 PubChem 733976
