#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/45/2224586.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_2224586
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Nirmala, P. G.'
'Fuess, Hartmut'
_publ_section_title
;
 4-Chloro-2-methyl-N-(3-methylphenyl)benzenesulfonamide
;
_journal_coeditor_code           CI2978
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o14
_journal_paper_doi               10.1107/S1600536809051083
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H14 Cl N O2 S'
_chemical_formula_moiety         'C14 H14 Cl N O2 S'
_chemical_formula_sum            'C14 H14 Cl N O2 S'
_chemical_formula_weight         295.77
_chemical_name_systematic
;
4-Chloro-2-methyl-N-(3-methylphenyl)benzenesulfonamide
;
_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                 90.593(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8830(7)
_cell_length_b                   11.6020(10)
_cell_length_c                   15.645(2)
_cell_measurement_reflns_used    2116
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.59
_cell_volume                     1430.8(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ 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  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5563
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.9525
_exptl_absorpt_correction_T_min  0.8277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.438
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0757P)²+0.6262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1564
_reflns_number_gt                1980
_reflns_number_total             2925
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2978.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224586
_cod_database_fobs_code          2224586
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 0.6521(3) 0.1989(2) 0.83780(16) 0.0484(6) Uani d . 1 . .
C C2 0.8133(4) 0.1933(2) 0.87588(18) 0.0552(7) Uani d . 1 . .
C C3 0.9404(4) 0.2588(3) 0.8394(2) 0.0679(8) Uani d . 1 . .
H H3 1.0494 0.2563 0.8627 0.081 Uiso calc R 1 . .
C C4 0.9084(4) 0.3278(3) 0.7692(2) 0.0675(8) Uani d . 1 . .
C C5 0.7500(5) 0.3331(3) 0.7328(2) 0.0725(9) Uani d . 1 . .
H H5 0.7292 0.3802 0.6858 0.087 Uiso calc R 1 . .
C C6 0.6223(4) 0.2679(3) 0.76688(18) 0.0616(8) Uani d . 1 . .
H H6 0.5145 0.2700 0.7421 0.074 Uiso calc R 1 . .
C C7 0.3599(3) 0.2701(2) 0.99538(18) 0.0509(6) Uani d . 1 . .
C C8 0.3539(3) 0.3658(2) 0.94325(19) 0.0584(7) Uani d . 1 . .
H H8 0.4012 0.3622 0.8891 0.070 Uiso calc R 1 . .
C C9 0.2787(4) 0.4672(3) 0.9703(2) 0.0630(8) Uani d . 1 . .
C C10 0.2096(5) 0.4692(3) 1.0506(2) 0.0882(11) Uani d . 1 . .
H H10 0.1577 0.5362 1.0700 0.106 Uiso calc R 1 . .
C C11 0.2159(5) 0.3740(4) 1.1028(2) 0.0929(12) Uani d . 1 . .
H H11 0.1698 0.3776 1.1572 0.111 Uiso calc R 1 . .
C C12 0.2895(4) 0.2737(3) 1.07543(19) 0.0663(8) Uani d . 1 . .
H H12 0.2919 0.2090 1.1105 0.080 Uiso calc R 1 . .
C C13 0.8530(4) 0.1198(3) 0.9571(2) 0.0703(9) Uani d . 1 . .
H H13A 0.8313 0.0400 0.9451 0.084 Uiso calc R 1 . .
H H13B 0.7823 0.1448 1.0032 0.084 Uiso calc R 1 . .
H H13C 0.9701 0.1295 0.9732 0.084 Uiso calc R 1 . .
C C14 0.2762(5) 0.5716(3) 0.9131(3) 0.0857(11) Uani d . 1 . .
H H14A 0.2078 0.5560 0.8634 0.103 Uiso calc R 1 . .
H H14B 0.3898 0.5896 0.8961 0.103 Uiso calc R 1 . .
H H14C 0.2293 0.6359 0.9435 0.103 Uiso calc R 1 . .
N N1 0.4428(4) 0.1662(2) 0.97214(17) 0.0692(8) Uani d . 1 . .
H H1N 0.445(4) 0.118(3) 1.011(2) 0.083 Uiso d . 1 . .
O O1 0.3367(3) 0.1432(2) 0.82291(15) 0.0752(6) Uani d . 1 . .
O O2 0.5297(3) 0.00166(16) 0.88893(14) 0.0708(6) Uani d . 1 . .
Cl Cl1 1.07032(16) 0.41278(11) 0.72879(9) 0.1237(5) Uani d . 1 . .
S S1 0.47841(9) 0.11958(6) 0.87689(5) 0.0572(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 0.0033 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
C6 C1 C2 . . 120.9(3) ?
C6 C1 S1 . . 116.9(2) ?
C2 C1 S1 . . 122.2(2) ?
C3 C2 C1 . . 117.2(3) ?
C3 C2 C13 . . 119.7(3) ?
C1 C2 C13 . . 123.1(3) ?
C4 C3 C2 . . 121.2(3) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C5 C4 C3 . . 121.0(3) ?
C5 C4 Cl1 . . 119.6(3) ?
C3 C4 Cl1 . . 119.3(3) ?
C4 C5 C6 . . 119.0(3) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C5 C6 C1 . . 120.7(3) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
C12 C7 C8 . . 120.2(3) ?
C12 C7 N1 . . 116.7(3) ?
C8 C7 N1 . . 123.0(3) ?
C7 C8 C9 . . 121.0(3) ?
C7 C8 H8 . . 119.5 ?
C9 C8 H8 . . 119.5 ?
C10 C9 C8 . . 117.9(3) ?
C10 C9 C14 . . 121.7(3) ?
C8 C9 C14 . . 120.3(3) ?
C11 C10 C9 . . 121.1(3) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C12 C11 C10 . . 120.6(3) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 C7 . . 119.1(3) ?
C11 C12 H12 . . 120.4 ?
C7 C12 H12 . . 120.4 ?
C2 C13 H13A . . 109.5 ?
C2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
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 . . 127.3(2) ?
C7 N1 H1N . . 114(3) ?
S1 N1 H1N . . 116(3) ?
O1 S1 O2 . . 118.67(14) ?
O1 S1 N1 . . 109.96(14) ?
O2 S1 N1 . . 104.43(13) ?
O1 S1 C1 . . 107.55(13) ?
O2 S1 C1 . . 108.88(13) ?
N1 S1 C1 . . 106.78(14) ?
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 C6 . 1.387(4) ?
C1 C2 . 1.399(4) ?
C1 S1 . 1.764(3) ?
C2 C3 . 1.386(4) ?
C2 C13 . 1.560(4) ?
C3 C4 . 1.380(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.369(5) ?
C4 Cl1 . 1.737(3) ?
C5 C6 . 1.371(4) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 C12 . 1.375(4) ?
C7 C8 . 1.378(4) ?
C7 N1 . 1.420(3) ?
C8 C9 . 1.386(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.375(5) ?
C9 C14 . 1.506(5) ?
C10 C11 . 1.375(5) ?
C10 H10 . 0.93 ?
C11 C12 . 1.371(5) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
N1 S1 . 1.613(3) ?
N1 H1N . 0.82(4) ?
O1 S1 . 1.420(2) ?
O2 S1 . 1.438(2) ?
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 O2 3_657 0.82(4) 2.10(4) 2.925(3) 176(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 . . . . -0.3(4) ?
S1 C1 C2 C3 . . . . 179.6(2) ?
C6 C1 C2 C13 . . . . 178.3(3) ?
S1 C1 C2 C13 . . . . -1.7(4) ?
C1 C2 C3 C4 . . . . 0.8(4) ?
C13 C2 C3 C4 . . . . -177.8(3) ?
C2 C3 C4 C5 . . . . -0.5(5) ?
C2 C3 C4 Cl1 . . . . 177.3(2) ?
C3 C4 C5 C6 . . . . -0.5(5) ?
Cl1 C4 C5 C6 . . . . -178.2(2) ?
C4 C5 C6 C1 . . . . 1.0(4) ?
C2 C1 C6 C5 . . . . -0.5(4) ?
S1 C1 C6 C5 . . . . 179.5(2) ?
C12 C7 C8 C9 . . . . 0.5(4) ?
N1 C7 C8 C9 . . . . -176.8(3) ?
C7 C8 C9 C10 . . . . -0.2(4) ?
C7 C8 C9 C14 . . . . 178.9(3) ?
C8 C9 C10 C11 . . . . 0.5(5) ?
C14 C9 C10 C11 . . . . -178.6(4) ?
C9 C10 C11 C12 . . . . -0.9(6) ?
C10 C11 C12 C7 . . . . 1.1(6) ?
C8 C7 C12 C11 . . . . -0.9(5) ?
N1 C7 C12 C11 . . . . 176.6(3) ?
C12 C7 N1 S1 . . . . 157.2(2) ?
C8 C7 N1 S1 . . . . -25.5(4) ?
C7 N1 S1 O1 . . . . -39.2(3) ?
C7 N1 S1 O2 . . . . -167.5(3) ?
C7 N1 S1 C1 . . . . 77.2(3) ?
C6 C1 S1 O1 . . . . 1.2(2) ?
C2 C1 S1 O1 . . . . -178.8(2) ?
C6 C1 S1 O2 . . . . 130.9(2) ?
C2 C1 S1 O2 . . . . -49.0(3) ?
C6 C1 S1 N1 . . . . -116.8(2) ?
C2 C1 S1 N1 . . . . 63.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744010
