#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/12/2221295.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_2221295
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Nirmala, P. G.'
'Terao, Hiromitsu'
'Fuess, Hartmut'
_publ_section_title
;
 4-Chloro-2-methyl-N-(2-methylphenyl)benzenesulfonamide
;
_journal_coeditor_code           BT2900
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o800
_journal_paper_doi               10.1107/S1600536809009623
_journal_volume                  65
_journal_year                    2009
_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-(2-methylphenyl)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                95.810(10)
_cell_angle_beta                 96.920(10)
_cell_angle_gamma                106.820(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1200(8)
_cell_length_b                   8.1832(8)
_cell_length_c                   10.9850(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      25.21
_cell_measurement_theta_min      5.71
_cell_volume                     686.46(12)
_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 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2572
_diffrn_reflns_theta_full        66.94
_diffrn_reflns_theta_max         66.94
_diffrn_reflns_theta_min         4.10
_diffrn_standards_decay_%        2.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.863
_exptl_absorpt_correction_T_max  0.4996
_exptl_absorpt_correction_T_min  0.2284
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.630
_refine_ls_extinction_coef       0.020(4)
_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   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0715
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1867P)²+0.2192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2069
_refine_ls_wR_factor_ref         0.2346
_reflns_number_gt                2194
_reflns_number_total             2366
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2900.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Psi-scan' changed to 'psi-scan'
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:

'_exptl_absorpt_correction_type' value 'Psi-scan' changed to
'psi-scan' 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_cell_volume        686.46(11)
_cod_database_code               2221295
_cod_database_fobs_code          2221295
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
Cl Cl1 0.35649(13) 0.29943(14) 0.56281(9) 0.0698(5) Uani d . 1 . .
S S1 0.70711(9) -0.00610(8) 0.15793(6) 0.0388(4) Uani d . 1 . .
O O1 0.8587(3) -0.0468(3) 0.2078(2) 0.0511(6) Uani d . 1 . .
O O2 0.5669(3) -0.1383(3) 0.0812(2) 0.0518(7) Uani d . 1 . .
N N1 0.7667(3) 0.1454(3) 0.0718(2) 0.0408(6) Uani d . 1 . .
H H1N 0.678(5) 0.160(5) 0.026(3) 0.049 Uiso d . 1 . .
C C1 0.6176(4) 0.0795(4) 0.2802(3) 0.0381(7) Uani d . 1 . .
C C2 0.7184(4) 0.1738(4) 0.3914(3) 0.0446(8) Uani d . 1 . .
C C3 0.6322(5) 0.2414(4) 0.4757(3) 0.0492(8) Uani d . 1 . .
H H3 0.6954 0.3075 0.5496 0.059 Uiso calc R 1 . .
C C4 0.4541(5) 0.2123(4) 0.4518(3) 0.0471(8) Uani d . 1 . .
C C5 0.3557(4) 0.1194(4) 0.3436(3) 0.0483(8) Uani d . 1 . .
H H5 0.2361 0.1015 0.3284 0.058 Uiso calc R 1 . .
C C6 0.4388(4) 0.0529(4) 0.2572(3) 0.0445(7) Uani d . 1 . .
H H6 0.3743 -0.0105 0.1828 0.053 Uiso calc R 1 . .
C C7 0.9159(4) 0.2918(4) 0.1137(2) 0.0370(7) Uani d . 1 . .
C C8 0.8982(4) 0.4545(4) 0.1516(3) 0.0417(7) Uani d . 1 . .
C C9 1.0502(6) 0.5921(4) 0.1866(3) 0.0580(9) Uani d . 1 . .
H H9 1.0420 0.7016 0.2100 0.070 Uiso calc R 1 . .
C C10 1.2117(6) 0.5710(5) 0.1876(4) 0.0654(11) Uani d . 1 . .
H H10 1.3113 0.6648 0.2132 0.078 Uiso calc R 1 . .
C C11 1.2262(5) 0.4090(6) 0.1501(4) 0.0655(11) Uani d . 1 . .
H H11 1.3357 0.3943 0.1511 0.079 Uiso calc R 1 . .
C C12 1.0791(5) 0.2706(5) 0.1118(3) 0.0516(8) Uani d . 1 . .
H H12 1.0889 0.1629 0.0846 0.062 Uiso calc R 1 . .
C C13 0.9139(5) 0.2097(6) 0.4271(3) 0.0607(10) Uani d . 1 . .
H H13A 0.9401 0.1025 0.4258 0.073 Uiso calc R 1 . .
H H13B 0.9513 0.2741 0.5088 0.073 Uiso calc R 1 . .
H H13C 0.9736 0.2753 0.3691 0.073 Uiso calc R 1 . .
C C14 0.7233(5) 0.4810(4) 0.1522(4) 0.0570(10) Uani d . 1 . .
H H14A 0.6460 0.4174 0.0787 0.068 Uiso calc R 1 . .
H H14B 0.7352 0.6015 0.1546 0.068 Uiso calc R 1 . .
H H14C 0.6767 0.4410 0.2239 0.068 Uiso calc R 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'
Cl Cl 0.3639 0.7018 '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'
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
O1 S1 O2 . . 119.17(14) ?
O1 S1 N1 . . 108.06(14) ?
O2 S1 N1 . . 105.21(14) ?
O1 S1 C1 . . 109.71(14) ?
O2 S1 C1 . . 106.93(14) ?
N1 S1 C1 . . 107.12(13) ?
C7 N1 S1 . . 121.1(2) ?
C7 N1 H1N . . 118(2) ?
S1 N1 H1N . . 112(3) ?
C6 C1 C2 . . 121.0(3) ?
C6 C1 S1 . . 115.7(2) ?
C2 C1 S1 . . 123.3(2) ?
C3 C2 C1 . . 116.9(3) ?
C3 C2 C13 . . 117.4(3) ?
C1 C2 C13 . . 125.6(3) ?
C4 C3 C2 . . 121.3(3) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C5 C4 C3 . . 121.7(3) ?
C5 C4 Cl1 . . 120.0(3) ?
C3 C4 Cl1 . . 118.3(3) ?
C4 C5 C6 . . 118.1(3) ?
C4 C5 H5 . . 120.9 ?
C6 C5 H5 . . 120.9 ?
C5 C6 C1 . . 120.9(3) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
C12 C7 C8 . . 121.0(3) ?
C12 C7 N1 . . 118.0(3) ?
C8 C7 N1 . . 121.0(3) ?
C9 C8 C7 . . 117.4(3) ?
C9 C8 C14 . . 120.8(3) ?
C7 C8 C14 . . 121.9(3) ?
C10 C9 C8 . . 121.9(3) ?
C10 C9 H9 . . 119.1 ?
C8 C9 H9 . . 119.1 ?
C9 C10 C11 . . 119.8(3) ?
C9 C10 H10 . . 120.1 ?
C11 C10 H10 . . 120.1 ?
C12 C11 C10 . . 120.1(4) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C7 . . 119.8(3) ?
C11 C12 H12 . . 120.1 ?
C7 C12 H12 . . 120.1 ?
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 ?
C8 C14 H14A . . 109.5 ?
C8 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C8 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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
Cl1 C4 . 1.734(3) ?
S1 O1 . 1.427(2) ?
S1 O2 . 1.431(2) ?
S1 N1 . 1.633(3) ?
S1 C1 . 1.778(3) ?
N1 C7 . 1.424(4) ?
N1 H1N . 0.87(4) ?
C1 C6 . 1.392(5) ?
C1 C2 . 1.400(4) ?
C2 C3 . 1.389(5) ?
C2 C13 . 1.522(5) ?
C3 C4 . 1.383(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.366(5) ?
C5 C6 . 1.383(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.388(5) ?
C7 C8 . 1.407(4) ?
C8 C9 . 1.390(5) ?
C8 C14 . 1.498(5) ?
C9 C10 . 1.370(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.391(7) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.373(5) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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 2_655 0.87(4) 2.14(4) 2.993(4) 167(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
O1 S1 N1 C7 . . . . -45.5(2) ?
O2 S1 N1 C7 . . . . -173.8(2) ?
C1 S1 N1 C7 . . . . 72.7(2) ?
O1 S1 C1 C6 . . . . -152.0(2) ?
O2 S1 C1 C6 . . . . -21.4(3) ?
N1 S1 C1 C6 . . . . 90.9(2) ?
O1 S1 C1 C2 . . . . 30.4(3) ?
O2 S1 C1 C2 . . . . 161.0(3) ?
N1 S1 C1 C2 . . . . -86.6(3) ?
C6 C1 C2 C3 . . . . -1.1(5) ?
S1 C1 C2 C3 . . . . 176.3(2) ?
C6 C1 C2 C13 . . . . 179.4(3) ?
S1 C1 C2 C13 . . . . -3.1(5) ?
C1 C2 C3 C4 . . . . 1.8(5) ?
C13 C2 C3 C4 . . . . -178.7(3) ?
C2 C3 C4 C5 . . . . -1.5(5) ?
C2 C3 C4 Cl1 . . . . 179.3(2) ?
C3 C4 C5 C6 . . . . 0.5(5) ?
Cl1 C4 C5 C6 . . . . 179.7(2) ?
C4 C5 C6 C1 . . . . 0.2(5) ?
C2 C1 C6 C5 . . . . 0.2(5) ?
S1 C1 C6 C5 . . . . -177.4(2) ?
S1 N1 C7 C12 . . . . 75.9(3) ?
S1 N1 C7 C8 . . . . -106.4(3) ?
C12 C7 C8 C9 . . . . 0.1(4) ?
N1 C7 C8 C9 . . . . -177.5(3) ?
C12 C7 C8 C14 . . . . 178.9(3) ?
N1 C7 C8 C14 . . . . 1.3(4) ?
C7 C8 C9 C10 . . . . -1.6(5) ?
C14 C8 C9 C10 . . . . 179.5(3) ?
C8 C9 C10 C11 . . . . 1.5(6) ?
C9 C10 C11 C12 . . . . 0.3(6) ?
C10 C11 C12 C7 . . . . -1.8(5) ?
C8 C7 C12 C11 . . . . 1.6(5) ?
N1 C7 C12 C11 . . . . 179.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741978
