#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/86/2228666.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_2228666
loop_
_publ_author_name
'Suchetan, P. A.'
'Foro, Sabine'
'Gowda, B. Thimme'
_publ_section_title
;
 4-Chloro-N-(2-methylbenzoyl)benzenesulfonamide
;
_journal_coeditor_code           BT5427
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o22
_journal_paper_doi               10.1107/S1600536810050087
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H12 Cl N O3 S'
_chemical_formula_moiety         'C14 H12 Cl N O3 S'
_chemical_formula_sum            'C14 H12 Cl N O3 S'
_chemical_formula_weight         309.76
_chemical_name_systematic
;
4-Chloro-N-(2-methylbenzoyl)benzenesulfonamide
;
_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                78.780(10)
_cell_angle_beta                 73.840(10)
_cell_angle_gamma                84.620(10)
_cell_formula_units_Z            2
_cell_length_a                   6.4328(9)
_cell_length_b                   10.3430(10)
_cell_length_c                   11.2070(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      22.50
_cell_measurement_theta_min      4.17
_cell_volume                     701.88(14)
_computing_cell_refinement       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4317
_diffrn_reflns_theta_full        66.94
_diffrn_reflns_theta_max         66.94
_diffrn_reflns_theta_min         4.17
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.864
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.562
_refine_ls_extinction_coef       0.038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2502
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0517
_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)+(0.1004P)²+0.2209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                2283
_reflns_number_total             2502
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bt5427.cif
_cod_data_source_block           I
_cod_original_cell_volume        701.88(13)
_cod_database_code               2228666
_cod_database_fobs_code          2228666
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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 0.2014(3) 0.2235(2) 0.92052(19) 0.0403(5) Uani d . 1 . .
C C2 0.3302(4) 0.1107(2) 0.9031(2) 0.0505(5) Uani d . 1 . .
H H2 0.4576 0.0973 0.9285 0.061 Uiso calc R 1 . .
C C3 0.2687(5) 0.0180(2) 0.8478(3) 0.0605(7) Uani d . 1 . .
H H3 0.3518 -0.0596 0.8373 0.073 Uiso calc R 1 . .
C C4 0.0816(5) 0.0425(2) 0.8083(2) 0.0573(6) Uani d . 1 . .
C C5 -0.0465(4) 0.1555(3) 0.8239(3) 0.0585(6) Uani d . 1 . .
H H5 -0.1709 0.1703 0.7955 0.070 Uiso calc R 1 . .
C C6 0.0124(4) 0.2463(2) 0.8821(2) 0.0512(6) Uani d . 1 . .
H H6 -0.0739 0.3222 0.8955 0.061 Uiso calc R 1 . .
C C7 0.4960(3) 0.4841(2) 0.7696(2) 0.0429(5) Uani d . 1 . .
C C8 0.4849(4) 0.6049(2) 0.6737(2) 0.0439(5) Uani d . 1 . .
C C9 0.3391(4) 0.6163(2) 0.6007(2) 0.0509(6) Uani d . 1 . .
C C10 0.3493(5) 0.7283(3) 0.5067(2) 0.0686(8) Uani d . 1 . .
H H10 0.2534 0.7394 0.4565 0.082 Uiso calc R 1 . .
C C11 0.4987(6) 0.8224(3) 0.4870(3) 0.0790(9) Uani d . 1 . .
H H11 0.5026 0.8959 0.4237 0.095 Uiso calc R 1 . .
C C12 0.6422(6) 0.8090(3) 0.5598(3) 0.0768(9) Uani d . 1 . .
H H12 0.7427 0.8730 0.5460 0.092 Uiso calc R 1 . .
C C13 0.6361(5) 0.7005(3) 0.6529(3) 0.0604(6) Uani d . 1 . .
H H13 0.7331 0.6907 0.7023 0.073 Uiso calc R 1 . .
C C14 0.1835(4) 0.5118(3) 0.6165(3) 0.0661(7) Uani d . 1 . .
H H14A 0.0593 0.5222 0.6857 0.079 Uiso calc R 1 . .
H H14B 0.2528 0.4265 0.6336 0.079 Uiso calc R 1 . .
H H14C 0.1385 0.5197 0.5405 0.079 Uiso calc R 1 . .
N N1 0.3253(3) 0.47376(17) 0.87777(17) 0.0434(4) Uani d D 1 . .
H H1N 0.229(4) 0.532(2) 0.883(2) 0.052 Uiso d D 1 . .
O O1 0.0959(3) 0.38337(16) 1.08307(14) 0.0554(5) Uani d . 1 . .
O O2 0.4730(3) 0.29640(17) 1.02583(16) 0.0581(5) Uani d . 1 . .
O O3 0.6391(3) 0.4000(2) 0.75586(18) 0.0674(5) Uani d . 1 . .
Cl Cl1 0.00535(19) -0.07131(8) 0.73539(8) 0.0981(4) Uani d . 1 . .
S S1 0.27927(8) 0.34281(5) 0.99049(5) 0.0427(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 0.0181 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'
N N 0.0311 0.0180 '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'
Cl Cl 0.3639 0.7018 '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'
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 . . 121.3(2) ?
C2 C1 S1 . . 119.81(17) ?
C6 C1 S1 . . 118.90(17) ?
C3 C2 C1 . . 119.5(2) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C2 C3 C4 . . 118.8(2) ?
C2 C3 H3 . . 120.6 ?
C4 C3 H3 . . 120.6 ?
C5 C4 C3 . . 122.1(2) ?
C5 C4 Cl1 . . 118.6(2) ?
C3 C4 Cl1 . . 119.3(2) ?
C6 C5 C4 . . 119.0(2) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C5 C6 C1 . . 119.3(2) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
O3 C7 N1 . . 121.3(2) ?
O3 C7 C8 . . 123.9(2) ?
N1 C7 C8 . . 114.76(18) ?
C9 C8 C13 . . 121.2(2) ?
C9 C8 C7 . . 120.7(2) ?
C13 C8 C7 . . 118.0(2) ?
C8 C9 C10 . . 117.2(2) ?
C8 C9 C14 . . 122.2(2) ?
C10 C9 C14 . . 120.5(2) ?
C11 C10 C9 . . 121.2(3) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C12 C11 C10 . . 120.7(3) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C13 C12 C11 . . 119.5(3) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C13 C8 . . 120.2(3) ?
C12 C13 H13 . . 119.9 ?
C8 C13 H13 . . 119.9 ?
C9 C14 H14A . . 109.5 ?
C9 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C9 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C7 N1 S1 . . 125.08(16) ?
C7 N1 H1N . . 118.8(19) ?
S1 N1 H1N . . 115.6(19) ?
O2 S1 O1 . . 119.23(11) ?
O2 S1 N1 . . 110.43(10) ?
O1 S1 N1 . . 103.74(10) ?
O2 S1 C1 . . 108.92(10) ?
O1 S1 C1 . . 109.13(11) ?
N1 S1 C1 . . 104.33(9) ?
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 . 1.379(3) ?
C1 C6 . 1.385(3) ?
C1 S1 . 1.760(2) ?
C2 C3 . 1.378(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.381(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.377(4) ?
C4 Cl1 . 1.732(2) ?
C5 C6 . 1.376(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O3 . 1.205(3) ?
C7 N1 . 1.385(3) ?
C7 C8 . 1.491(3) ?
C8 C9 . 1.389(3) ?
C8 C13 . 1.394(3) ?
C9 C10 . 1.399(4) ?
C9 C14 . 1.493(4) ?
C10 C11 . 1.376(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.373(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.371(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
N1 S1 . 1.6489(18) ?
N1 H1N . 0.819(17) ?
O1 S1 . 1.4280(17) ?
O2 S1 . 1.4243(17) ?
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 2_567 0.819(17) 2.15(2) 2.925(3) 157(3)
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 . . . . -0.8(4) ?
S1 C1 C2 C3 . . . . -179.73(18) ?
C1 C2 C3 C4 . . . . 1.6(4) ?
C2 C3 C4 C5 . . . . -0.8(4) ?
C2 C3 C4 Cl1 . . . . 178.54(18) ?
C3 C4 C5 C6 . . . . -0.8(4) ?
Cl1 C4 C5 C6 . . . . 179.78(19) ?
C4 C5 C6 C1 . . . . 1.7(4) ?
C2 C1 C6 C5 . . . . -0.9(4) ?
S1 C1 C6 C5 . . . . 178.06(18) ?
O3 C7 C8 C9 . . . . 105.2(3) ?
N1 C7 C8 C9 . . . . -74.1(3) ?
O3 C7 C8 C13 . . . . -69.9(3) ?
N1 C7 C8 C13 . . . . 110.9(2) ?
C13 C8 C9 C10 . . . . -0.7(3) ?
C7 C8 C9 C10 . . . . -175.5(2) ?
C13 C8 C9 C14 . . . . 176.7(2) ?
C7 C8 C9 C14 . . . . 1.8(3) ?
C8 C9 C10 C11 . . . . 0.5(4) ?
C14 C9 C10 C11 . . . . -176.9(3) ?
C9 C10 C11 C12 . . . . -0.2(5) ?
C10 C11 C12 C13 . . . . 0.0(5) ?
C11 C12 C13 C8 . . . . -0.2(5) ?
C9 C8 C13 C12 . . . . 0.5(4) ?
C7 C8 C13 C12 . . . . 175.5(2) ?
O3 C7 N1 S1 . . . . -7.6(3) ?
C8 C7 N1 S1 . . . . 171.71(15) ?
C7 N1 S1 O2 . . . . 47.7(2) ?
C7 N1 S1 O1 . . . . 176.59(17) ?
C7 N1 S1 C1 . . . . -69.16(19) ?
C2 C1 S1 O2 . . . . -3.0(2) ?
C6 C1 S1 O2 . . . . 178.07(18) ?
C2 C1 S1 O1 . . . . -134.65(18) ?
C6 C1 S1 O1 . . . . 46.4(2) ?
C2 C1 S1 N1 . . . . 114.98(19) ?
C6 C1 S1 N1 . . . . -64.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9441883
