#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/50/1545039.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_1545039
loop_
_publ_author_name
'Naveen, S.'
'Sudha, A. G.'
'Suresha, E.'
'Lokanath, N. K.'
'Suchetan, P. A.'
'Warad, Ismail'
_publ_section_title
;
 N-(4-Chlorophenylsulfonyl)-4-iodobenzamide
;
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x170025
_journal_paper_doi               10.1107/S2414314617000256
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C13 H9 Cl I N O3 S'
_chemical_formula_moiety         'C13 H9 Cl I N O3 S'
_chemical_formula_sum            'C13 H9 Cl I N O3 S'
_chemical_formula_weight         421.62
_chemical_melting_point          425
_chemical_name_systematic
;
N-(4-Chlorophenylsulfonyl)-4-iodobenzamide
;
_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                 104.223(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.1163(18)
_cell_length_b                   13.3947(13)
_cell_length_c                   12.3002(13)
_cell_measurement_reflns_used    144
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.2
_cell_measurement_theta_min      4.2
_cell_volume                     2893.3(5)
_computing_cell_refinement
;
APEX2 and SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus and XPREP (Bruker, 2009)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13818
_diffrn_reflns_theta_full        64.20
_diffrn_reflns_theta_max         64.20
_diffrn_reflns_theta_min         4.15
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 2
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    20.508
_exptl_absorpt_correction_T_max  0.0796
_exptl_absorpt_correction_T_min  0.0691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.578
_refine_diff_density_min         -1.824
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0638
_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)+(0.1376P)²+0.0790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.1724
_reflns_number_gt                2178
_reflns_number_total             2369
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            su4120sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1545039
_cod_database_fobs_code          1545039
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
_atom_site_symmetry_multiplicity
C C1 0.7762(2) 0.3242(4) 0.7483(4) 0.0274(10) Uani d . 1 1
C C2 0.7821(3) 0.3116(4) 0.6400(4) 0.0361(11) Uani d . 1 1
H H2 0.7548 0.2611 0.5958 0.043 Uiso calc R 1 1
C C3 0.8284(3) 0.3737(5) 0.5966(4) 0.0425(12) Uani d . 1 1
H H3 0.8333 0.3650 0.5237 0.051 Uiso calc R 1 1
C C4 0.8676(3) 0.4492(4) 0.6636(5) 0.0370(12) Uani d . 1 1
C C5 0.8628(3) 0.4624(4) 0.7727(5) 0.0391(12) Uani d . 1 1
H H5 0.8902 0.5128 0.8168 0.047 Uiso calc R 1 1
C C6 0.8161(3) 0.3987(4) 0.8160(5) 0.0336(11) Uani d . 1 1
H H6 0.8119 0.4063 0.8894 0.040 Uiso calc R 1 1
C C7 0.8082(3) 0.0884(4) 0.8118(4) 0.0244(10) Uani d . 1 1
C C8 0.8589(2) 0.0109(3) 0.8799(4) 0.0220(9) Uani d . 1 1
C C9 0.9104(3) -0.0367(4) 0.8302(4) 0.0319(11) Uani d . 1 1
H H9 0.9131 -0.0180 0.7584 0.038 Uiso calc R 1 1
C C10 0.9575(3) -0.1108(4) 0.8851(4) 0.0334(11) Uani d . 1 1
H H10 0.9926 -0.1413 0.8519 0.040 Uiso calc R 1 1
C C11 0.9518(2) -0.1392(4) 0.9901(4) 0.0268(10) Uani d . 1 1
C C12 0.9013(3) -0.0940(4) 1.0412(4) 0.0295(10) Uani d . 1 1
H H12 0.8981 -0.1142 1.1122 0.035 Uiso calc R 1 1
C C13 0.8553(3) -0.0179(3) 0.9861(4) 0.0264(10) Uani d . 1 1
H H13 0.8217 0.0139 1.0210 0.032 Uiso calc R 1 1
O O1 0.69380(19) 0.2958(3) 0.8916(3) 0.0374(8) Uani d . 1 1
O O2 0.66080(18) 0.2040(3) 0.7129(3) 0.0377(8) Uani d . 1 1
O O3 0.79821(18) 0.0931(3) 0.7109(3) 0.0340(8) Uani d . 1 1
S S1 0.71643(8) 0.24483(8) 0.80304(11) 0.0264(4) Uani d . 1 1
Cl Cl1 0.92287(8) 0.52981(13) 0.60795(14) 0.0601(5) Uani d . 1 1
I I1 1.02099(2) -0.25581(3) 1.07348(3) 0.0422(3) Uani d . 1 1
N N1 0.7722(2) 0.1537(3) 0.8684(3) 0.0251(8) Uani d D 1 1
H HN1 0.788(3) 0.169(4) 0.934(3) 0.023(12) Uiso d D 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C2 C1 C6 121.1(5)
C2 C1 S1 119.9(4)
C6 C1 S1 119.0(4)
C1 C2 C3 120.1(5)
C1 C2 H2 119.9
C3 C2 H2 119.9
C2 C3 C4 118.8(5)
C2 C3 H3 120.6
C4 C3 H3 120.6
C5 C4 C3 121.9(5)
C5 C4 Cl1 119.2(4)
C3 C4 Cl1 118.9(4)
C4 C5 C6 118.8(5)
C4 C5 H5 120.6
C6 C5 H5 120.6
C1 C6 C5 119.2(5)
C1 C6 H6 120.4
C5 C6 H6 120.4
O3 C7 N1 121.0(4)
O3 C7 C8 121.7(4)
N1 C7 C8 117.2(4)
C13 C8 C9 118.8(4)
C13 C8 C7 124.0(4)
C9 C8 C7 117.2(4)
C10 C9 C8 121.2(4)
C10 C9 H9 119.4
C8 C9 H9 119.4
C9 C10 C11 118.7(4)
C9 C10 H10 120.6
C11 C10 H10 120.6
C12 C11 C10 121.5(4)
C12 C11 I1 119.3(3)
C10 C11 I1 119.3(3)
C11 C12 C13 119.4(4)
C11 C12 H12 120.3
C13 C12 H12 120.3
C8 C13 C12 120.4(4)
C8 C13 H13 119.8
C12 C13 H13 119.8
O2 S1 O1 120.0(2)
O2 S1 N1 109.1(2)
O1 S1 N1 103.7(2)
O2 S1 C1 108.6(2)
O1 S1 C1 108.7(2)
N1 S1 C1 105.7(2)
C7 N1 S1 121.9(3)
C7 N1 HN1 125(4)
S1 N1 HN1 109(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.374(7)
C1 C6 1.385(8)
C1 S1 1.764(5)
C2 C3 1.379(8)
C2 H2 0.9300
C3 C4 1.385(8)
C3 H3 0.9300
C4 C5 1.377(8)
C4 Cl1 1.725(5)
C5 C6 1.395(8)
C5 H5 0.9300
C6 H6 0.9300
C7 O3 1.211(6)
C7 N1 1.379(6)
C7 C8 1.499(7)
C8 C13 1.379(7)
C8 C9 1.390(6)
C9 C10 1.374(7)
C9 H9 0.9300
C10 C11 1.375(7)
C10 H10 0.9300
C11 C12 1.370(7)
C11 I1 2.105(4)
C12 C13 1.384(7)
C12 H12 0.9300
C13 H13 0.9300
O1 S1 1.429(4)
O2 S1 1.413(4)
S1 N1 1.661(4)
N1 HN1 0.81(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
N1 HN1 O1 7_657 0.81(4) 2.14(4) 2.943(5) 168(6) yes
C12 H12 O3 6_556 0.93 2.43 3.124(6) 131 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
C6 C1 C2 C3 0.0(7)
S1 C1 C2 C3 179.7(4)
C1 C2 C3 C4 -0.9(8)
C2 C3 C4 C5 1.5(8)
C2 C3 C4 Cl1 -177.7(4)
C3 C4 C5 C6 -1.1(7)
Cl1 C4 C5 C6 178.1(4)
C2 C1 C6 C5 0.4(7)
S1 C1 C6 C5 -179.3(4)
C4 C5 C6 C1 0.2(7)
O3 C7 C8 C13 -159.7(5)
N1 C7 C8 C13 19.3(6)
O3 C7 C8 C9 17.9(7)
N1 C7 C8 C9 -163.1(4)
C13 C8 C9 C10 -0.3(7)
C7 C8 C9 C10 -178.0(5)
C8 C9 C10 C11 1.4(8)
C9 C10 C11 C12 -1.1(8)
C9 C10 C11 I1 178.1(4)
C10 C11 C12 C13 -0.2(7)
I1 C11 C12 C13 -179.4(3)
C9 C8 C13 C12 -1.0(7)
C7 C8 C13 C12 176.5(4)
C11 C12 C13 C8 1.3(7)
C2 C1 S1 O2 -22.7(4)
C6 C1 S1 O2 156.9(4)
C2 C1 S1 O1 -155.0(4)
C6 C1 S1 O1 24.7(4)
C2 C1 S1 N1 94.3(4)
C6 C1 S1 N1 -86.1(4)
O3 C7 N1 S1 -2.7(6)
C8 C7 N1 S1 178.3(3)
O2 S1 N1 C7 53.2(4)
O1 S1 N1 C7 -177.7(4)
C1 S1 N1 C7 -63.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 47108736
