#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224846.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_2224846
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Nirmala, P. G.'
'Fuess, Hartmut'
_publ_section_title
;
 N-(3-Chlorophenyl)-4-methylbenzenesulfonamide
;
_journal_coeditor_code           BQ2186
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o278
_journal_paper_doi               10.1107/S1600536809055238
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H12 Cl N O2 S'
_chemical_formula_moiety         'C13 H12 Cl N O2 S'
_chemical_formula_sum            'C13 H12 Cl N O2 S'
_chemical_formula_weight         281.75
_chemical_name_systematic
;
N-(3-Chlorophenyl)-4-methylbenzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 91.952(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7740(10)
_cell_length_b                   13.5890(10)
_cell_length_c                   10.0660(10)
_cell_measurement_reflns_used    2689
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.52
_cell_volume                     1336.2(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur (TM) 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  0.0113
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5167
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  0.9181
_exptl_absorpt_correction_T_min  0.8251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0363
_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)+(0.0580P)²+0.3400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                1957
_reflns_number_total             2445
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2186.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224846
_cod_database_fobs_code          2224846
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 C1 0.18744(19) 1.05082(14) 0.08569(19) 0.0411(4) Uani d . 1 . .
C C2 0.0703(2) 1.05677(18) 0.1578(2) 0.0573(6) Uani d . 1 . .
H H2 0.0517 1.0093 0.2212 0.069 Uiso calc R 1 . .
C C3 -0.0188(2) 1.1340(2) 0.1347(2) 0.0686(7) Uani d . 1 . .
H H3 -0.0975 1.1382 0.1838 0.082 Uiso calc R 1 . .
C C4 0.0059(2) 1.20537(18) 0.0404(2) 0.0589(6) Uani d . 1 . .
C C5 0.1235(2) 1.19686(17) -0.0317(2) 0.0605(6) Uani d . 1 . .
H H5 0.1415 1.2436 -0.0963 0.073 Uiso calc R 1 . .
C C6 0.2143(2) 1.12092(16) -0.0097(2) 0.0513(5) Uani d . 1 . .
H H6 0.2932 1.1167 -0.0585 0.062 Uiso calc R 1 . .
C C7 0.42477(19) 1.05956(14) 0.31752(19) 0.0409(4) Uani d . 1 . .
C C8 0.3351(2) 1.03090(15) 0.41417(19) 0.0440(5) Uani d . 1 . .
H H8 0.2785 0.9765 0.4011 0.053 Uiso calc R 1 . .
C C9 0.3317(2) 1.08485(16) 0.5303(2) 0.0488(5) Uani d . 1 . .
C C10 0.4151(3) 1.16417(17) 0.5545(2) 0.0608(6) Uani d . 1 . .
H H10 0.4118 1.1987 0.6341 0.073 Uiso calc R 1 . .
C C11 0.5039(3) 1.19146(16) 0.4578(3) 0.0648(6) Uani d . 1 . .
H H11 0.5613 1.2452 0.4725 0.078 Uiso calc R 1 . .
C C12 0.5092(2) 1.14039(15) 0.3391(2) 0.0527(5) Uani d . 1 . .
H H12 0.5690 1.1602 0.2743 0.063 Uiso calc R 1 . .
C C13 -0.0920(3) 1.2896(2) 0.0170(3) 0.0881(9) Uani d . 1 . .
H H13A -0.1003 1.3263 0.0978 0.106 Uiso calc R 1 . .
H H13B -0.1801 1.2643 -0.0110 0.106 Uiso calc R 1 . .
H H13C -0.0581 1.3318 -0.0509 0.106 Uiso calc R 1 . .
N N1 0.43675(18) 1.00545(14) 0.19789(17) 0.0474(4) Uani d . 1 . .
H H1N 0.496(2) 1.0277(16) 0.147(2) 0.057 Uiso d . 1 . .
O O1 0.36308(15) 0.92586(11) -0.00834(14) 0.0531(4) Uani d . 1 . .
O O2 0.24646(16) 0.88340(11) 0.19738(15) 0.0590(4) Uani d . 1 . .
Cl Cl1 0.21817(7) 1.04894(6) 0.65092(6) 0.0776(2) Uani d . 1 . .
S S1 0.30698(5) 0.95603(3) 0.11563(5) 0.04334(18) 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 . . 120.4(2) ?
C2 C1 S1 . . 120.76(17) ?
C6 C1 S1 . . 118.84(15) ?
C3 C2 C1 . . 119.1(2) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C2 C3 C4 . . 121.7(2) ?
C2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
C3 C4 C5 . . 117.9(2) ?
C3 C4 C13 . . 121.1(2) ?
C5 C4 C13 . . 121.1(3) ?
C6 C5 C4 . . 121.4(2) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C1 . . 119.4(2) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
C12 C7 C8 . . 119.96(19) ?
C12 C7 N1 . . 118.52(18) ?
C8 C7 N1 . . 121.47(18) ?
C9 C8 C7 . . 118.59(19) ?
C9 C8 H8 . . 120.7 ?
C7 C8 H8 . . 120.7 ?
C10 C9 C8 . . 122.5(2) ?
C10 C9 Cl1 . . 119.08(17) ?
C8 C9 Cl1 . . 118.38(17) ?
C9 C10 C11 . . 118.2(2) ?
C9 C10 H10 . . 120.9 ?
C11 C10 H10 . . 120.9 ?
C10 C11 C12 . . 121.2(2) ?
C10 C11 H11 . . 119.4 ?
C12 C11 H11 . . 119.4 ?
C11 C12 C7 . . 119.5(2) ?
C11 C12 H12 . . 120.2 ?
C7 C12 H12 . . 120.2 ?
C4 C13 H13A . . 109.5 ?
C4 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C4 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C7 N1 S1 . . 123.88(14) ?
C7 N1 H1N . . 114.0(16) ?
S1 N1 H1N . . 112.3(17) ?
O2 S1 O1 . . 118.73(9) ?
O2 S1 N1 . . 108.77(10) ?
O1 S1 N1 . . 104.13(9) ?
O2 S1 C1 . . 108.64(10) ?
O1 S1 C1 . . 109.30(9) ?
N1 S1 C1 . . 106.58(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 . 1.384(3) ?
C1 S1 . 1.758(2) ?
C2 C3 . 1.378(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.384(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(3) ?
C4 C13 . 1.505(3) ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.387(3) ?
C7 C8 . 1.387(3) ?
C7 N1 . 1.419(3) ?
C8 C9 . 1.381(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.368(3) ?
C9 Cl1 . 1.742(2) ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.384(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N1 S1 . 1.6352(18) ?
N1 H1N . 0.84(2) ?
O1 S1 . 1.4396(14) ?
O2 S1 . 1.4263(15) ?
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 3_675 0.84(2) 2.09(2) 2.932(2) 175(2)
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 . . . . -0.7(3) ?
S1 C1 C2 C3 . . . . 177.82(18) ?
C1 C2 C3 C4 . . . . 0.4(4) ?
C2 C3 C4 C5 . . . . 0.4(4) ?
C2 C3 C4 C13 . . . . -179.6(2) ?
C3 C4 C5 C6 . . . . -0.8(4) ?
C13 C4 C5 C6 . . . . 179.2(2) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C2 C1 C6 C5 . . . . 0.3(3) ?
S1 C1 C6 C5 . . . . -178.30(17) ?
C12 C7 C8 C9 . . . . 0.5(3) ?
N1 C7 C8 C9 . . . . 177.84(18) ?
C7 C8 C9 C10 . . . . -1.3(3) ?
C7 C8 C9 Cl1 . . . . 179.61(15) ?
C8 C9 C10 C11 . . . . 1.0(3) ?
Cl1 C9 C10 C11 . . . . -179.88(18) ?
C9 C10 C11 C12 . . . . 0.0(4) ?
C10 C11 C12 C7 . . . . -0.7(3) ?
C8 C7 C12 C11 . . . . 0.5(3) ?
N1 C7 C12 C11 . . . . -176.95(19) ?
C12 C7 N1 S1 . . . . -143.42(17) ?
C8 C7 N1 S1 . . . . 39.2(3) ?
C7 N1 S1 O2 . . . . -62.89(19) ?
C7 N1 S1 O1 . . . . 169.58(16) ?
C7 N1 S1 C1 . . . . 54.08(19) ?
C2 C1 S1 O2 . . . . 12.5(2) ?
C6 C1 S1 O2 . . . . -168.94(16) ?
C2 C1 S1 O1 . . . . 143.48(17) ?
C6 C1 S1 O1 . . . . -37.97(19) ?
C2 C1 S1 N1 . . . . -104.55(18) ?
C6 C1 S1 N1 . . . . 74.00(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 234520
