#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/67/2226783.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_2226783
loop_
_publ_author_name
'Suchetan, P. A.'
'Gowda, B. Thimme'
'Foro, Sabine'
'Fuess, Hartmut'
_publ_section_title
;
 2-Methyl-N-(2-methylbenzoyl)benzenesulfonamide
;
_journal_coeditor_code           BT5290
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1992
_journal_paper_doi               10.1107/S1600536810026735
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H15 N O3 S'
_chemical_formula_moiety         'C15 H15 N O3 S'
_chemical_formula_sum            'C15 H15 N O3 S'
_chemical_formula_weight         289.34
_chemical_name_systematic
;
2-Methyl-N-(2-methylbenzoyl)benzenesulfonamide
;
_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                 96.955(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.9970(10)
_cell_length_b                   14.1650(10)
_cell_length_c                   14.395(2)
_cell_measurement_reflns_used    2699
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.59
_cell_volume                     2833.1(5)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega and phi 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  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5920
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9245
_exptl_absorpt_correction_T_min  0.9120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0373
_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)+(0.0707P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                2281
_reflns_number_total             2895
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bt5290.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226783
_cod_database_fobs_code          2226783
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_disorder_assembly
_atom_site_disorder_group
C C1A 0.1586(2) 0.3862(2) 0.2895(2) 0.0392(7) Uani d PD 0.75 A 1
C C1B 0.1568(6) 0.3398(6) 0.2942(6) 0.0354(18) Uani d PD 0.25 A 2
C C2A 0.13372(16) 0.3021(2) 0.2415(2) 0.0506(6) Uani d PD 0.75 A 1
C C2B 0.1299(5) 0.3961(6) 0.2180(5) 0.0528(18) Uani d PD 0.25 A 2
C C3A 0.0925(6) 0.3103(4) 0.1473(4) 0.0680(17) Uani d PD 0.75 A 1
H H3A 0.0726 0.2567 0.1131 0.082 Uiso calc PR 0.75 A 1
C C3B 0.0951(16) 0.3438(9) 0.1388(10) 0.041(3) Uani d PD 0.25 A 2
H H3B 0.0742 0.3779 0.0849 0.050 Uiso calc PR 0.25 A 2
C C4A 0.0817(2) 0.3986(3) 0.1061(2) 0.0712(8) Uani d PD 0.75 A 1
H H4A 0.0543 0.4029 0.0441 0.085 Uiso calc PR 0.75 A 1
C C4B 0.0886(6) 0.2496(8) 0.1325(6) 0.066(2) Uani d PD 0.25 A 2
H H4B 0.0648 0.2220 0.0758 0.079 Uiso calc PR 0.25 A 2
C C5A 0.1093(2) 0.4781(2) 0.1523(2) 0.0650(8) Uani d PD 0.75 A 1
H H5A 0.1024 0.5363 0.1223 0.078 Uiso calc PR 0.75 A 1
C C5B 0.1164(7) 0.1931(7) 0.2084(7) 0.079(3) Uani d PD 0.25 A 2
H H5B 0.1133 0.1276 0.2056 0.095 Uiso calc PR 0.25 A 2
C C6A 0.1483(3) 0.4725(3) 0.2459(3) 0.0505(8) Uani d PD 0.75 A 1
H H6A 0.1675 0.5272 0.2788 0.061 Uiso calc PR 0.75 A 1
C C6B 0.1493(10) 0.2411(8) 0.2890(9) 0.050(3) Uani d PD 0.25 A 2
H H6B 0.1675 0.2062 0.3430 0.060 Uiso calc PR 0.25 A 2
C C7 0.38609(11) 0.39162(11) 0.36903(10) 0.0396(3) Uani d . 1 . .
C C8 0.47917(10) 0.33980(11) 0.37729(10) 0.0390(3) Uani d . 1 . .
C C9 0.56650(11) 0.38885(13) 0.38842(11) 0.0496(4) Uani d . 1 . .
C C10 0.65018(12) 0.33451(18) 0.39523(14) 0.0675(6) Uani d . 1 . .
H H10 0.7094 0.3651 0.4045 0.081 Uiso calc R 1 . .
C C11 0.64890(13) 0.23848(17) 0.38881(14) 0.0712(6) Uani d . 1 . .
H H11 0.7064 0.2050 0.3933 0.085 Uiso calc R 1 . .
C C12 0.56284(14) 0.19138(15) 0.37571(13) 0.0614(5) Uani d . 1 . .
H H12 0.5614 0.1260 0.3699 0.074 Uiso calc R 1 . .
C C13 0.47861(12) 0.24202(12) 0.37119(11) 0.0479(4) Uani d . 1 . .
H H13 0.4201 0.2101 0.3639 0.057 Uiso calc R 1 . .
C C14A 0.1486(5) 0.2049(3) 0.2834(5) 0.0866(18) Uani d PD 0.75 A 1
H H14A 0.1053 0.1957 0.3295 0.104 Uiso calc PR 0.75 A 1
H H14B 0.2138 0.1989 0.3124 0.104 Uiso calc PR 0.75 A 1
H H14C 0.1362 0.1583 0.2351 0.104 Uiso calc PR 0.75 A 1
C C14B 0.1351(11) 0.4964(9) 0.2142(8) 0.062(3) Uani d PD 0.25 A 2
H H14D 0.1919 0.5176 0.2526 0.074 Uiso calc PR 0.25 A 2
H H14E 0.0792 0.5231 0.2368 0.074 Uiso calc PR 0.25 A 2
H H14F 0.1376 0.5160 0.1508 0.074 Uiso calc PR 0.25 A 2
C C15 0.57390(14) 0.49465(14) 0.39237(14) 0.0687(6) Uani d . 1 . .
H H15C 0.6380 0.5125 0.4176 0.082 Uiso calc R 1 . .
H H15B 0.5288 0.5190 0.4316 0.082 Uiso calc R 1 . .
H H15A 0.5596 0.5201 0.3304 0.082 Uiso calc R 1 . .
N N1 0.31537(9) 0.34845(10) 0.41437(9) 0.0439(3) Uani d D 1 A .
H H1N 0.3279(12) 0.2983(8) 0.4467(11) 0.053 Uiso d D 1 . .
O O1 0.15903(8) 0.32012(10) 0.46446(9) 0.0645(4) Uani d . 1 A .
O O2 0.20209(10) 0.48187(10) 0.43476(10) 0.0743(4) Uani d . 1 A .
O O3 0.36933(9) 0.46426(9) 0.32707(9) 0.0609(4) Uani d . 1 . .
S S1 0.20355(3) 0.38584(3) 0.40857(3) 0.04381(16) Uani d 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'
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
C6A C1A C2A . . 121.7(3) ?
C6A C1A S1 . . 117.0(3) ?
C2A C1A S1 . . 121.2(2) ?
C2B C1B C6B . . 121.7(9) ?
C2B C1B S1 . . 123.3(7) ?
C6B C1B S1 . . 115.0(7) ?
C1A C2A C3A . . 116.9(3) ?
C1A C2A C14A . . 124.4(3) ?
C3A C2A C14A . . 118.7(4) ?
C1B C2B C3B . . 112.2(9) ?
C1B C2B C14B . . 126.9(8) ?
C3B C2B C14B . . 120.9(8) ?
C4A C3A C2A . . 119.8(5) ?
C4A C3A H3A . . 120.1 ?
C2A C3A H3A . . 120.1 ?
C4B C3B C2B . . 126.7(12) ?
C4B C3B H3B . . 116.6 ?
C2B C3B H3B . . 116.6 ?
C5A C4A C3A . . 122.5(4) ?
C5A C4A H4A . . 118.8 ?
C3A C4A H4A . . 118.8 ?
C3B C4B C5B . . 121.1(9) ?
C3B C4B H4B . . 119.5 ?
C5B C4B H4B . . 119.5 ?
C4A C5A C6A . . 119.2(3) ?
C4A C5A H5A . . 120.4 ?
C6A C5A H5A . . 120.4 ?
C4B C5B C6B . . 114.7(9) ?
C4B C5B H5B . . 122.6 ?
C6B C5B H5B . . 122.6 ?
C1A C6A C5A . . 119.9(4) ?
C1A C6A H6A . . 120.0 ?
C5A C6A H6A . . 120.0 ?
C5B C6B C1B . . 123.5(10) ?
C5B C6B H6B . . 118.3 ?
C1B C6B H6B . . 118.3 ?
O3 C7 N1 . . 120.35(14) ?
O3 C7 C8 . . 125.34(14) ?
N1 C7 C8 . . 114.30(13) ?
C13 C8 C9 . . 120.09(15) ?
C13 C8 C7 . . 119.29(13) ?
C9 C8 C7 . . 120.59(15) ?
C10 C9 C8 . . 116.66(17) ?
C10 C9 C15 . . 119.61(16) ?
C8 C9 C15 . . 123.72(16) ?
C11 C10 C9 . . 122.80(17) ?
C11 C10 H10 . . 118.6 ?
C9 C10 H10 . . 118.6 ?
C10 C11 C12 . . 119.96(17) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C11 C12 C13 . . 119.16(19) ?
C11 C12 H12 . . 120.4 ?
C13 C12 H12 . . 120.4 ?
C12 C13 C8 . . 121.29(17) ?
C12 C13 H13 . . 119.4 ?
C8 C13 H13 . . 119.4 ?
C2B C14B H14D . . 109.5 ?
C2B C14B H14E . . 109.5 ?
H14D C14B H14E . . 109.5 ?
C2B C14B H14F . . 109.5 ?
H14D C14B H14F . . 109.5 ?
H14E C14B H14F . . 109.5 ?
C9 C15 H15C . . 109.5 ?
C9 C15 H15B . . 109.5 ?
H15C C15 H15B . . 109.5 ?
C9 C15 H15A . . 109.5 ?
H15C C15 H15A . . 109.5 ?
H15B C15 H15A . . 109.5 ?
C7 N1 S1 . . 124.14(11) ?
C7 N1 H1N . . 120.6(12) ?
S1 N1 H1N . . 115.2(12) ?
O2 S1 O1 . . 117.24(9) ?
O2 S1 N1 . . 109.94(8) ?
O1 S1 N1 . . 103.88(7) ?
O2 S1 C1A . . 104.07(11) ?
O1 S1 C1A . . 115.14(11) ?
N1 S1 C1A . . 106.11(10) ?
O2 S1 C1B . . 124.9(3) ?
O1 S1 C1B . . 98.2(3) ?
N1 S1 C1B . . 99.6(2) ?
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
C1A C6A . 1.374(4) ?
C1A C2A . 1.400(3) ?
C1A S1 . 1.753(3) ?
C1B C2B . 1.372(10) ?
C1B C6B . 1.403(10) ?
C1B S1 . 1.817(8) ?
C2A C3A . 1.412(7) ?
C2A C14A . 1.507(5) ?
C2B C3B . 1.397(13) ?
C2B C14B . 1.423(13) ?
C3A C4A . 1.384(5) ?
C3A H3A . 0.9300 ?
C3B C4B . 1.340(13) ?
C3B H3B . 0.9300 ?
C4A C5A . 1.341(5) ?
C4A H4A . 0.9300 ?
C4B C5B . 1.372(12) ?
C4B H4B . 0.9300 ?
C5A C6A . 1.393(4) ?
C5A H5A . 0.9300 ?
C5B C6B . 1.375(13) ?
C5B H5B . 0.9300 ?
C6A H6A . 0.9300 ?
C6B H6B . 0.9300 ?
C7 O3 . 1.2018(18) ?
C7 N1 . 1.3915(19) ?
C7 C8 . 1.488(2) ?
C8 C13 . 1.388(2) ?
C8 C9 . 1.398(2) ?
C9 C10 . 1.395(3) ?
C9 C15 . 1.503(3) ?
C10 C11 . 1.363(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.370(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(2) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14A H14A . 0.9600 ?
C14A H14B . 0.9600 ?
C14A H14C . 0.9600 ?
C14B H14D . 0.9600 ?
C14B H14E . 0.9600 ?
C14B H14F . 0.9600 ?
C15 H15C . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15A . 0.9600 ?
N1 S1 . 1.6449(13) ?
N1 H1N . 0.856(9) ?
O1 S1 . 1.4226(12) ?
O2 S1 . 1.4123(14) ?
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
N1 H1N O1 7_556 0.856(9) 2.104(10) 2.9531(17) 171.7(17)
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
C6A C1A C2A C3A . . . . -3.5(6) ?
S1 C1A C2A C3A . . . . 176.1(4) ?
C6A C1A C2A C14A . . . . 176.2(4) ?
S1 C1A C2A C14A . . . . -4.2(5) ?
C6B C1B C2B C3B . . . . 0.4(16) ?
S1 C1B C2B C3B . . . . -179.1(12) ?
C6B C1B C2B C14B . . . . -179.3(12) ?
S1 C1B C2B C14B . . . . 1.2(13) ?
C1A C2A C3A C4A . . . . 2.3(9) ?
C14A C2A C3A C4A . . . . -177.4(6) ?
C1B C2B C3B C4B . . . . -1(3) ?
C14B C2B C3B C4B . . . . 178.4(18) ?
C2A C3A C4A C5A . . . . 0.1(9) ?
C2B C3B C4B C5B . . . . 1(3) ?
C3A C4A C5A C6A . . . . -1.5(6) ?
C3B C4B C5B C6B . . . . 1(2) ?
C2A C1A C6A C5A . . . . 2.2(5) ?
S1 C1A C6A C5A . . . . -177.4(3) ?
C4A C5A C6A C1A . . . . 0.3(5) ?
C4B C5B C6B C1B . . . . -1.7(18) ?
C2B C1B C6B C5B . . . . 1.1(18) ?
S1 C1B C6B C5B . . . . -179.4(10) ?
O3 C7 C8 C13 . . . . -139.43(17) ?
N1 C7 C8 C13 . . . . 39.97(19) ?
O3 C7 C8 C9 . . . . 38.8(2) ?
N1 C7 C8 C9 . . . . -141.84(14) ?
C13 C8 C9 C10 . . . . -1.6(2) ?
C7 C8 C9 C10 . . . . -179.76(14) ?
C13 C8 C9 C15 . . . . 177.84(16) ?
C7 C8 C9 C15 . . . . -0.3(2) ?
C8 C9 C10 C11 . . . . 1.9(3) ?
C15 C9 C10 C11 . . . . -177.57(19) ?
C9 C10 C11 C12 . . . . -0.4(3) ?
C10 C11 C12 C13 . . . . -1.4(3) ?
C11 C12 C13 C8 . . . . 1.6(3) ?
C9 C8 C13 C12 . . . . -0.1(2) ?
C7 C8 C13 C12 . . . . 178.09(14) ?
O3 C7 N1 S1 . . . . 5.0(2) ?
C8 C7 N1 S1 . . . . -174.44(10) ?
C7 N1 S1 O2 . . . . -54.19(15) ?
C7 N1 S1 O1 . . . . 179.57(13) ?
C7 N1 S1 C1A . . . . 57.78(17) ?
C7 N1 S1 C1B . . . . 78.5(3) ?
C6A C1A S1 O2 . . . . 10.4(3) ?
C2A C1A S1 O2 . . . . -169.2(2) ?
C6A C1A S1 O1 . . . . 140.2(2) ?
C2A C1A S1 O1 . . . . -39.5(3) ?
C6A C1A S1 N1 . . . . -105.6(3) ?
C2A C1A S1 N1 . . . . 74.8(2) ?
C6A C1A S1 C1B . . . . 179.8(10) ?
C2A C1A S1 C1B . . . . 0.2(7) ?
C2B C1B S1 O2 . . . . 11.0(8) ?
C6B C1B S1 O2 . . . . -168.6(7) ?
C2B C1B S1 O1 . . . . 142.7(6) ?
C6B C1B S1 O1 . . . . -36.9(8) ?
C2B C1B S1 N1 . . . . -111.7(7) ?
C6B C1B S1 N1 . . . . 68.8(8) ?
C2B C1B S1 C1A . . . . -1.6(5) ?
C6B C1B S1 C1A . . . . 178.9(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15656443
