#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225605.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_2225605
loop_
_publ_author_name
'Khan, Islam Ullah'
'Haider, Zeeshan'
'Arshad, Muhammad Nadeem'
'Ali, Sharafat'
_publ_section_title
;
 N-Ethyl-N-phenyl-p-toluenesulfonamide
;
_journal_coeditor_code           NG2749
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o979
_journal_paper_doi               10.1107/S1600536810011219
_journal_volume                  66
_journal_year                    2010
_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_common
N-Ethyl-4-methyl-N-phenylbenzenesulfonamide
_chemical_name_systematic
;
N-Ethyl-N-phenyl-p-toluenesulfonamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.1248(6)
_cell_length_b                   10.4126(5)
_cell_length_c                   19.7639(10)
_cell_measurement_reflns_used    2488
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.35
_cell_measurement_theta_min      2.64
_cell_volume                     2906.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15016
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9656
_exptl_absorpt_correction_T_min  0.9509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0497
_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)+(0.0707P)²+0.2464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1574
_reflns_number_gt                1759
_reflns_number_total             3599
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2749.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
;
_cod_database_code               2225605
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
S S1 0.12290(5) 0.31259(6) 0.45059(3) 0.0736(3) Uani d . 1 . .
O O1 0.03439(13) 0.34190(19) 0.48260(10) 0.0982(6) Uani d . 1 . .
O O2 0.14610(15) 0.18289(15) 0.43417(9) 0.0940(6) Uani d . 1 . .
N N1 0.12528(13) 0.39272(17) 0.37947(10) 0.0670(5) Uani d . 1 . .
C C1 0.21256(17) 0.3761(2) 0.50190(10) 0.0605(6) Uani d . 1 . .
C C2 0.19340(18) 0.4774(2) 0.54450(11) 0.0678(6) Uani d . 1 . .
H H2 0.1320 0.5089 0.5481 0.081 Uiso calc R 1 . .
C C3 0.2651(2) 0.5321(2) 0.58177(12) 0.0759(7) Uani d . 1 . .
H H3 0.2514 0.6004 0.6105 0.091 Uiso calc R 1 . .
C C4 0.35649(19) 0.4880(3) 0.57751(12) 0.0739(7) Uani d . 1 . .
C C5 0.3742(2) 0.3868(3) 0.53525(15) 0.0852(8) Uani d . 1 . .
H H5 0.4357 0.3554 0.5319 0.102 Uiso calc R 1 . .
C C6 0.3044(2) 0.3305(2) 0.49782(13) 0.0773(7) Uani d . 1 . .
H H6 0.3186 0.2617 0.4696 0.093 Uiso calc R 1 . .
C C7 0.09842(18) 0.5301(2) 0.38163(13) 0.0760(7) Uani d . 1 . .
H H7A 0.1544 0.5825 0.3749 0.091 Uiso calc R 1 . .
H H7B 0.0727 0.5502 0.4259 0.091 Uiso calc R 1 . .
C C8 0.0268(2) 0.5621(3) 0.32876(15) 0.0934(9) Uani d . 1 . .
H H8A -0.0287 0.5106 0.3354 0.140 Uiso calc R 1 . .
H H8B 0.0528 0.5450 0.2848 0.140 Uiso calc R 1 . .
H H8C 0.0103 0.6513 0.3320 0.140 Uiso calc R 1 . .
C C9 0.19267(18) 0.3535(2) 0.32926(11) 0.0625(6) Uani d . 1 . .
C C10 0.2805(2) 0.4097(2) 0.32511(13) 0.0773(7) Uani d . 1 . .
H H10 0.2975 0.4741 0.3554 0.093 Uiso calc R 1 . .
C C11 0.3428(2) 0.3706(3) 0.27619(15) 0.0926(9) Uani d . 1 . .
H H11 0.4022 0.4086 0.2735 0.111 Uiso calc R 1 . .
C C12 0.3186(3) 0.2762(3) 0.23123(15) 0.0975(10) Uani d . 1 . .
H H12 0.3614 0.2502 0.1982 0.117 Uiso calc R 1 . .
C C13 0.2316(3) 0.2209(3) 0.23514(14) 0.0941(9) Uani d . 1 . .
H H13 0.2148 0.1569 0.2046 0.113 Uiso calc R 1 . .
C C14 0.1683(2) 0.2588(2) 0.28389(13) 0.0782(7) Uani d . 1 . .
H H14 0.1090 0.2204 0.2863 0.094 Uiso calc R 1 . .
C C15 0.4350(2) 0.5510(3) 0.61724(16) 0.1138(11) Uani d . 1 . .
H H15A 0.4907 0.4982 0.6154 0.171 Uiso calc R 1 . .
H H15B 0.4156 0.5613 0.6635 0.171 Uiso calc R 1 . .
H H15C 0.4487 0.6337 0.5981 0.171 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 0.0033 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
O2 S1 O1 . . 120.13(12) ?
O2 S1 N1 . . 106.42(10) ?
O1 S1 N1 . . 106.78(12) ?
O2 S1 C1 . . 108.83(12) ?
O1 S1 C1 . . 107.13(11) ?
N1 S1 C1 . . 106.87(10) ?
C9 N1 C7 . . 117.72(19) ?
C9 N1 S1 . . 117.59(15) ?
C7 N1 S1 . . 117.58(16) ?
C2 C1 C6 . . 118.9(2) ?
C2 C1 S1 . . 120.07(19) ?
C6 C1 S1 . . 120.97(19) ?
C3 C2 C1 . . 120.0(2) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C4 C3 C2 . . 121.4(2) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C5 C4 C3 . . 117.9(3) ?
C5 C4 C15 . . 121.2(3) ?
C3 C4 C15 . . 120.9(3) ?
C6 C5 C4 . . 122.0(3) ?
C6 C5 H5 . . 119.0 ?
C4 C5 H5 . . 119.0 ?
C5 C6 C1 . . 119.9(2) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
N1 C7 C8 . . 111.7(2) ?
N1 C7 H7A . . 109.3 ?
C8 C7 H7A . . 109.3 ?
N1 C7 H7B . . 109.3 ?
C8 C7 H7B . . 109.3 ?
H7A C7 H7B . . 107.9 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C14 . . 119.5(3) ?
C10 C9 N1 . . 121.3(2) ?
C14 C9 N1 . . 119.3(2) ?
C11 C10 C9 . . 119.7(3) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C12 C11 C10 . . 120.8(3) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C13 C12 C11 . . 119.5(3) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C13 C14 . . 120.4(3) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C13 C14 C9 . . 120.1(3) ?
C13 C14 H14 . . 120.0 ?
C9 C14 H14 . . 120.0 ?
C4 C15 H15A . . 109.5 ?
C4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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
S1 O2 . 1.4271(18) ?
S1 O1 . 1.4339(19) ?
S1 N1 . 1.635(2) ?
S1 C1 . 1.752(2) ?
N1 C9 . 1.434(3) ?
N1 C7 . 1.481(3) ?
C1 C2 . 1.377(3) ?
C1 C6 . 1.384(3) ?
C2 C3 . 1.375(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.373(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.368(4) ?
C4 C15 . 1.509(4) ?
C5 C6 . 1.365(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.492(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.374(3) ?
C9 C14 . 1.377(3) ?
C10 C11 . 1.370(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.368(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.360(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.372(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
O2 S1 N1 C9 . . . . -33.36(19) ?
O1 S1 N1 C9 . . . . -162.81(16) ?
C1 S1 N1 C9 . . . . 82.81(18) ?
O2 S1 N1 C7 . . . . 176.76(17) ?
O1 S1 N1 C7 . . . . 47.31(19) ?
C1 S1 N1 C7 . . . . -67.08(19) ?
O2 S1 C1 C2 . . . . -155.91(18) ?
O1 S1 C1 C2 . . . . -24.6(2) ?
N1 S1 C1 C2 . . . . 89.5(2) ?
O2 S1 C1 C6 . . . . 27.6(2) ?
O1 S1 C1 C6 . . . . 158.92(19) ?
N1 S1 C1 C6 . . . . -86.9(2) ?
C6 C1 C2 C3 . . . . 0.4(3) ?
S1 C1 C2 C3 . . . . -176.14(18) ?
C1 C2 C3 C4 . . . . 0.1(4) ?
C2 C3 C4 C5 . . . . -0.5(4) ?
C2 C3 C4 C15 . . . . 178.4(2) ?
C3 C4 C5 C6 . . . . 0.3(4) ?
C15 C4 C5 C6 . . . . -178.5(3) ?
C4 C5 C6 C1 . . . . 0.2(4) ?
C2 C1 C6 C5 . . . . -0.6(4) ?
S1 C1 C6 C5 . . . . 175.9(2) ?
C9 N1 C7 C8 . . . . 80.0(3) ?
S1 N1 C7 C8 . . . . -130.2(2) ?
C7 N1 C9 C10 . . . . 56.3(3) ?
S1 N1 C9 C10 . . . . -93.6(2) ?
C7 N1 C9 C14 . . . . -122.9(2) ?
S1 N1 C9 C14 . . . . 87.2(2) ?
C14 C9 C10 C11 . . . . -0.3(4) ?
N1 C9 C10 C11 . . . . -179.5(2) ?
C9 C10 C11 C12 . . . . 0.2(4) ?
C10 C11 C12 C13 . . . . 0.1(5) ?
C11 C12 C13 C14 . . . . -0.2(5) ?
C12 C13 C14 C9 . . . . 0.1(4) ?
C10 C9 C14 C13 . . . . 0.2(4) ?
N1 C9 C14 C13 . . . . 179.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 67146
