#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224158.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_2224158
loop_
_publ_author_name
'Nirmala, P. G.'
'Gowda, B. Thimme'
'Foro, Sabine'
'Fuess, Hartmut'
_publ_section_title
;
 2,4-Dimethyl-N-(2-methylphenyl)benzenesulfonamide
;
_journal_coeditor_code           CI2971
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3210
_journal_paper_doi               10.1107/S1600536809049563
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H17 N O2 S'
_chemical_formula_moiety         'C15 H17 N O2 S'
_chemical_formula_sum            'C15 H17 N O2 S'
_chemical_formula_weight         275.36
_chemical_name_systematic
;
2,4-Dimethyl-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                96.249(9)
_cell_angle_beta                 96.078(9)
_cell_angle_gamma                106.782(9)
_cell_formula_units_Z            2
_cell_length_a                   8.1789(8)
_cell_length_b                   8.2659(9)
_cell_length_c                   11.0050(10)
_cell_measurement_reflns_used    2978
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      2.99
_cell_volume                     700.68(13)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0101
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4894
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_correction_T_min  0.8983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2862
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0392
_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)+(0.0640P)²+0.2128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2446
_reflns_number_total             2862
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2971.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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        700.68(12)
_cod_database_code               2224158
_cod_database_fobs_code          2224158
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 0.1125(2) 0.5794(2) 0.78239(16) 0.0390(4) Uani d . 1 . .
C C2 0.2116(2) 0.6728(2) 0.89249(16) 0.0440(4) Uani d . 1 . .
C C3 0.1243(3) 0.7397(3) 0.97740(17) 0.0496(4) Uani d . 1 . .
H H3 0.1876 0.8030 1.0513 0.060 Uiso calc R 1 . .
C C4 -0.0514(3) 0.7168(2) 0.95762(18) 0.0480(4) Uani d . 1 . .
C C5 -0.1451(2) 0.6234(3) 0.84761(18) 0.0505(4) Uani d . 1 . .
H H5 -0.2633 0.6063 0.8322 0.061 Uiso calc R 1 . .
C C6 -0.0645(2) 0.5551(2) 0.76046(17) 0.0458(4) Uani d . 1 . .
H H6 -0.1287 0.4925 0.6866 0.055 Uiso calc R 1 . .
C C7 0.4102(2) 0.7886(2) 0.61387(14) 0.0380(4) Uani d . 1 . .
C C8 0.3900(2) 0.9481(2) 0.64940(15) 0.0432(4) Uani d . 1 . .
C C9 0.5397(3) 1.0860(3) 0.68291(19) 0.0599(5) Uani d . 1 . .
H H9 0.5304 1.1944 0.7053 0.072 Uiso calc R 1 . .
C C10 0.7000(3) 1.0659(3) 0.6837(2) 0.0693(7) Uani d . 1 . .
H H10 0.7978 1.1600 0.7075 0.083 Uiso calc R 1 . .
C C11 0.7175(3) 0.9075(3) 0.6495(2) 0.0691(7) Uani d . 1 . .
H H11 0.8268 0.8942 0.6511 0.083 Uiso calc R 1 . .
C C12 0.5722(2) 0.7676(3) 0.61251(19) 0.0525(5) Uani d . 1 . .
H H12 0.5831 0.6607 0.5870 0.063 Uiso calc R 1 . .
C C13 0.4036(3) 0.7076(3) 0.9262(2) 0.0642(6) Uani d . 1 . .
H H13A 0.4627 0.7664 0.8654 0.077 Uiso calc R 1 . .
H H13B 0.4287 0.6014 0.9290 0.077 Uiso calc R 1 . .
H H13C 0.4416 0.7771 1.0057 0.077 Uiso calc R 1 . .
C C14 -0.1363(3) 0.7946(3) 1.0542(2) 0.0660(6) Uani d . 1 . .
H H14A -0.0497 0.8623 1.1206 0.079 Uiso calc R 1 . .
H H14B -0.2169 0.7053 1.0855 0.079 Uiso calc R 1 . .
H H14C -0.1960 0.8657 1.0176 0.079 Uiso calc R 1 . .
C C15 0.2154(3) 0.9733(2) 0.6503(2) 0.0583(5) Uani d . 1 . .
H H15A 0.1600 0.9167 0.7135 0.070 Uiso calc R 1 . .
H H15B 0.1462 0.9261 0.5714 0.070 Uiso calc R 1 . .
H H15C 0.2283 1.0932 0.6667 0.070 Uiso calc R 1 . .
N N1 0.26247(19) 0.64126(19) 0.57272(13) 0.0409(3) Uani d D 1 . .
H H1N 0.175(2) 0.659(3) 0.5378(18) 0.049 Uiso d D 1 . .
O O1 0.06289(17) 0.36111(16) 0.58290(13) 0.0527(3) Uani d . 1 . .
O O2 0.35102(17) 0.45144(17) 0.70879(13) 0.0524(3) Uani d . 1 . .
S S1 0.20156(5) 0.49271(5) 0.65960(4) 0.04048(16) 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'
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 . . 120.83(16) ?
C6 C1 S1 . . 115.77(13) ?
C2 C1 S1 . . 123.34(13) ?
C3 C2 C1 . . 116.59(16) ?
C3 C2 C13 . . 117.89(17) ?
C1 C2 C13 . . 125.51(17) ?
C4 C3 C2 . . 123.53(18) ?
C4 C3 H3 . . 118.2 ?
C2 C3 H3 . . 118.2 ?
C5 C4 C3 . . 118.18(17) ?
C5 C4 C14 . . 121.52(18) ?
C3 C4 C14 . . 120.30(19) ?
C6 C5 C4 . . 120.45(17) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 120.42(17) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
C12 C7 C8 . . 121.51(17) ?
C12 C7 N1 . . 117.73(16) ?
C8 C7 N1 . . 120.71(15) ?
C9 C8 C7 . . 117.21(18) ?
C9 C8 C15 . . 120.60(18) ?
C7 C8 C15 . . 122.19(16) ?
C10 C9 C8 . . 121.6(2) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
C9 C10 C11 . . 120.4(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C10 C11 C12 . . 119.9(2) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C11 C12 C7 . . 119.3(2) ?
C11 C12 H12 . . 120.3 ?
C7 C12 H12 . . 120.3 ?
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 ?
C4 C14 H14A . . 109.5 ?
C4 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C4 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C8 C15 H15A . . 109.5 ?
C8 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C8 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C7 N1 S1 . . 121.46(11) ?
C7 N1 H1N . . 116.5(14) ?
S1 N1 H1N . . 108.7(15) ?
O2 S1 O1 . . 118.89(8) ?
O2 S1 N1 . . 108.05(8) ?
O1 S1 N1 . . 104.94(8) ?
O2 S1 C1 . . 109.57(8) ?
O1 S1 C1 . . 107.40(8) ?
N1 S1 C1 . . 107.42(8) ?
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 . 1.394(2) ?
C1 C2 . 1.396(2) ?
C1 S1 . 1.7799(17) ?
C2 C3 . 1.394(3) ?
C2 C13 . 1.510(2) ?
C3 C4 . 1.385(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.381(3) ?
C4 C14 . 1.513(3) ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 C12 . 1.386(2) ?
C7 C8 . 1.395(2) ?
C7 N1 . 1.436(2) ?
C8 C9 . 1.393(3) ?
C8 C15 . 1.503(3) ?
C9 C10 . 1.368(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.375(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.384(3) ?
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 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
N1 S1 . 1.6350(16) ?
N1 H1N . 0.832(15) ?
O1 S1 . 1.4377(13) ?
O2 S1 . 1.4299(13) ?
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_566 0.83(2) 2.19(2) 3.002(2) 165(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 . . . . -0.2(3) ?
S1 C1 C2 C3 . . . . 176.86(13) ?
C6 C1 C2 C13 . . . . -179.88(19) ?
S1 C1 C2 C13 . . . . -2.8(3) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C13 C2 C3 C4 . . . . -179.95(19) ?
C2 C3 C4 C5 . . . . -0.3(3) ?
C2 C3 C4 C14 . . . . -179.61(19) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C14 C4 C5 C6 . . . . 179.35(18) ?
C4 C5 C6 C1 . . . . 0.1(3) ?
C2 C1 C6 C5 . . . . 0.0(3) ?
S1 C1 C6 C5 . . . . -177.30(14) ?
C12 C7 C8 C9 . . . . 0.3(3) ?
N1 C7 C8 C9 . . . . -177.20(15) ?
C12 C7 C8 C15 . . . . 179.46(17) ?
N1 C7 C8 C15 . . . . 1.9(3) ?
C7 C8 C9 C10 . . . . -1.4(3) ?
C15 C8 C9 C10 . . . . 179.47(19) ?
C8 C9 C10 C11 . . . . 0.9(3) ?
C9 C10 C11 C12 . . . . 0.8(4) ?
C10 C11 C12 C7 . . . . -1.8(3) ?
C8 C7 C12 C11 . . . . 1.2(3) ?
N1 C7 C12 C11 . . . . 178.85(17) ?
C12 C7 N1 S1 . . . . 75.97(18) ?
C8 C7 N1 S1 . . . . -106.39(17) ?
C7 N1 S1 O2 . . . . -46.56(15) ?
C7 N1 S1 O1 . . . . -174.35(12) ?
C7 N1 S1 C1 . . . . 71.57(14) ?
C6 C1 S1 O2 . . . . -152.26(13) ?
C2 C1 S1 O2 . . . . 30.51(17) ?
C6 C1 S1 O1 . . . . -21.81(16) ?
C2 C1 S1 O1 . . . . 160.95(14) ?
C6 C1 S1 N1 . . . . 90.60(14) ?
C2 C1 S1 N1 . . . . -86.63(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10011065
