#------------------------------------------------------------------------------
#$Date: 2022-04-08 05:03:31 +0300 (Fri, 08 Apr 2022) $
#$Revision: 274427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244070.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_2244070
loop_
_publ_author_name
'Bookwala, Mustafa'
'Patel, Saloni'
'Flaherty, Patrick T.'
'Wildfong, Peter L. D.'
_publ_section_title
;
 Crystal structure of 4-bromo-N-(propylcarbamoyl)benzenesulfonamide
;
_journal_coeditor_code           MW2187
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022003723
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C10 H13 Br N2 O3 S'
_chemical_formula_moiety         'C10 H13 Br N2 O3 S'
_chemical_formula_sum            'C10 H13 Br N2 O3 S'
_chemical_formula_weight         321.19
_chemical_melting_point          411
_chemical_name_common            Bromopropamide
_chemical_name_systematic
;
4-Bromo-N-(propylcarbamoyl)benzenesulfonamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 116.211(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.0939(12)
_cell_length_b                   9.2520(6)
_cell_length_c                   15.0283(10)
_cell_measurement_reflns_used    2918
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.173
_cell_measurement_theta_min      2.152
_cell_volume                     2631.4(3)
_computing_cell_refinement
;
SMART and SAINT (Bruker, 1998)
;
_computing_data_collection
;
SMART and SAINT (Bruker, 1998)
;
_computing_data_reduction
;
SMART and SAINT (Bruker, 1998)
;
_computing_molecular_graphics
;
CrystalMaker (Palmer, 2014)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       'φ and ω Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15567
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.173
_diffrn_reflns_theta_min         2.152
_diffrn_source                   'Fine-focus Sealed Tube'
_exptl_absorpt_coefficient_mu    3.281
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_description       'Rectangular Plate'
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0397P)²+0.7765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                1776
_reflns_number_total             2918
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mw2187sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2244070
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.494
_shelx_estimated_absorpt_t_max   0.853
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.62045(2) 0.74137(4) 0.56073(3) 0.0982(2) Uani d 1 . .
S S1 0.33290(3) 0.91269(7) 0.18667(5) 0.0519(2) Uani d 1 . .
O O1 0.34641(11) 1.0325(2) 0.13838(14) 0.0677(5) Uani d 1 . .
N N1 0.28060(11) 0.9785(2) 0.23075(16) 0.0525(6) Uani d 1 . .
H H1 0.267634 1.067206 0.217972 0.063 Uiso calc 1 . .
C C1 0.53543(14) 0.7926(3) 0.4505(2) 0.0576(7) Uani d 1 . .
O O2 0.30317(11) 0.7841(2) 0.13234(14) 0.0629(5) Uani d 1 . .
N N2 0.22679(11) 0.9777(2) 0.33323(17) 0.0579(6) Uani d 1 . .
H H2 0.223806 1.069690 0.323849 0.069 Uiso calc 1 . .
C C7 0.25586(12) 0.8997(3) 0.2876(2) 0.0486(6) Uani d 1 . .
C C2 0.52538(15) 0.9312(3) 0.4162(2) 0.0664(8) Uani d 1 . .
H H2A 0.560352 1.000298 0.446974 0.080 Uiso calc 1 . .
O O3 0.26161(11) 0.76750(17) 0.29256(16) 0.0612(5) Uani d 1 . .
C C3 0.46344(14) 0.9687(3) 0.3360(2) 0.0599(7) Uani d 1 . .
H H3 0.456463 1.062947 0.312127 0.072 Uiso calc 1 . .
C C4 0.41168(13) 0.8659(3) 0.29115(18) 0.0460(6) Uani d 1 . .
C C5 0.42201(15) 0.7269(3) 0.3267(2) 0.0608(8) Uani d 1 . .
H H5 0.386886 0.657922 0.296706 0.073 Uiso calc 1 . .
C C6 0.48436(15) 0.6894(3) 0.4068(2) 0.0658(8) Uani d 1 . .
H H6 0.491670 0.595259 0.430921 0.079 Uiso calc 1 . .
C C8 0.19943(17) 0.9163(4) 0.3988(2) 0.0726(9) Uani d 1 . .
H H8A 0.215639 0.974924 0.458349 0.087 Uiso calc 1 . .
H H8B 0.218898 0.820113 0.418427 0.087 Uiso calc 1 . .
C C9 0.12066(19) 0.9070(4) 0.3534(3) 0.0960(12) Uani d 1 . .
H H9A 0.103998 0.849364 0.293370 0.115 Uiso calc 1 . .
H H9B 0.100819 1.003157 0.335194 0.115 Uiso calc 1 . .
C C10 0.0955(3) 0.8407(5) 0.4230(4) 0.1239(17) Uani d 1 . .
H H10A 0.044787 0.836946 0.391608 0.186 Uiso calc 1 . .
H H10B 0.111388 0.898207 0.482141 0.186 Uiso calc 1 . .
H H10C 0.114123 0.744633 0.439896 0.186 Uiso calc 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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 119.76(13) ?
O1 S1 N1 . . 103.90(12) ?
O2 S1 N1 . . 109.80(12) ?
O1 S1 C4 . . 108.87(12) ?
O2 S1 C4 . . 108.00(12) ?
N1 S1 C4 . . 105.65(11) ?
C7 N1 S1 . . 123.94(17) ?
C7 N1 H1 . . 118.0 ?
S1 N1 H1 . . 118.0 ?
C2 C1 C6 . . 121.1(3) ?
C2 C1 Br1 . . 119.8(2) ?
C6 C1 Br1 . . 119.1(2) ?
C7 N2 C8 . . 123.5(2) ?
C7 N2 H2 . . 118.3 ?
C8 N2 H2 . . 118.3 ?
O3 C7 N2 . . 124.7(3) ?
O3 C7 N1 . . 120.4(3) ?
N2 C7 N1 . . 114.8(2) ?
C1 C2 C3 . . 119.8(3) ?
C1 C2 H2A . . 120.1 ?
C3 C2 H2A . . 120.1 ?
C2 C3 C4 . . 119.7(3) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C5 C4 C3 . . 120.0(2) ?
C5 C4 S1 . . 120.1(2) ?
C3 C4 S1 . . 119.8(2) ?
C4 C5 C6 . . 120.1(3) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 119.2(3) ?
C1 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
N2 C8 C9 . . 113.9(3) ?
N2 C8 H8A . . 108.8 ?
C9 C8 H8A . . 108.8 ?
N2 C8 H8B . . 108.8 ?
C9 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
C8 C9 C10 . . 111.7(3) ?
C8 C9 H9A . . 109.3 ?
C10 C9 H9A . . 109.3 ?
C8 C9 H9B . . 109.3 ?
C10 C9 H9B . . 109.3 ?
H9A C9 H9B . . 107.9 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 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 C1 . 1.887(3) ?
S1 O1 . 1.4207(19) ?
S1 O2 . 1.4225(19) ?
S1 N1 . 1.634(2) ?
S1 C4 . 1.763(3) ?
N1 C7 . 1.388(3) ?
N1 H1 . 0.8600 ?
C1 C2 . 1.363(4) ?
C1 C6 . 1.371(4) ?
N2 C7 . 1.319(3) ?
N2 C8 . 1.460(4) ?
N2 H2 . 0.8600 ?
C7 O3 . 1.228(3) ?
C2 C3 . 1.374(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.378(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.372(3) ?
C5 C6 . 1.379(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 C9 . 1.494(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.498(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 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
N1 H1 O3 4 0.86 1.94 2.791(3) 171.9 yes
N2 H2 O2 4 0.86 2.24 2.998(3) 146.8 yes
N2 H2 O3 4 0.86 2.64 3.351(3) 140.6 yes

_cod_database_fobs_code 2244070
