#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/49/2224919.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_2224919
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Suchetan, P. A.'
'Fuess, Hartmut'
_publ_section_title
;
 2-Methyl-N-(3-methylbenzoyl)benzenesulfonamide
;
_journal_coeditor_code           CI5020
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o433
_journal_paper_doi               10.1107/S1600536810002254
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H15 N O3 S'
_chemical_formula_moiety         'C15 H15 N O3 S'
_chemical_formula_sum            'C15 H15 N O3 S'
_chemical_formula_weight         289.34
_chemical_name_systematic
;
2-Methyl-N-(3-methylbenzoyl)benzenesulfonamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 127.670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.023(4)
_cell_length_b                   12.045(3)
_cell_length_c                   17.335(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      20.46
_cell_measurement_theta_min      4.81
_cell_volume                     2978.7(13)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0720
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10158
_diffrn_reflns_theta_full        67.02
_diffrn_reflns_theta_max         67.02
_diffrn_reflns_theta_min         4.61
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.991
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.281
_refine_ls_extinction_coef       0.0016(2)
_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   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0835P)²+3.6838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1756
_reflns_number_gt                2219
_reflns_number_total             2654
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5020.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_cell_volume        2978.7(12)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2224919
_cod_database_fobs_code          2224919
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
S S1 0.39278(5) 0.37414(6) 0.48527(5) 0.0536(3) Uani d . 1 . .
O O1 0.41777(17) 0.48868(19) 0.50971(18) 0.0718(7) Uani d . 1 . .
O O2 0.39810(16) 0.3050(2) 0.55495(15) 0.0708(7) Uani d . 1 . .
O O3 0.41415(18) 0.15139(19) 0.4361(2) 0.0767(7) Uani d . 1 . .
N N1 0.46572(18) 0.3289(2) 0.4653(2) 0.0586(7) Uani d D 1 . .
H H1N 0.499(2) 0.381(2) 0.472(3) 0.070 Uiso d D 1 . .
C C1 0.2810(2) 0.3633(2) 0.3733(2) 0.0499(7) Uani d . 1 . .
C C2 0.2518(2) 0.4330(2) 0.2951(2) 0.0592(8) Uani d . 1 . .
C C3 0.1604(3) 0.4177(3) 0.2116(3) 0.0777(10) Uani d . 1 . .
H H3 0.1381 0.4625 0.1578 0.093 Uiso calc R 1 . .
C C4 0.1016(3) 0.3391(3) 0.2053(3) 0.0773(10) Uani d . 1 . .
H H4 0.0407 0.3319 0.1480 0.093 Uiso calc R 1 . .
C C5 0.1322(2) 0.2713(3) 0.2829(3) 0.0715(9) Uani d . 1 . .
H H5 0.0924 0.2182 0.2787 0.086 Uiso calc R 1 . .
C C6 0.2223(2) 0.2827(3) 0.3672(2) 0.0590(8) Uani d . 1 . .
H H6 0.2440 0.2364 0.4200 0.071 Uiso calc R 1 . .
C C7 0.4670(2) 0.2184(3) 0.4415(2) 0.0600(8) Uani d . 1 . .
C C8 0.5356(2) 0.1891(3) 0.4240(2) 0.0605(8) Uani d . 1 . .
C C9 0.5736(2) 0.2662(3) 0.3972(2) 0.0674(9) Uani d . 1 . .
H H9 0.5589 0.3411 0.3933 0.081 Uiso calc R 1 . .
C C10 0.6332(3) 0.2327(4) 0.3764(3) 0.0878(12) Uani d . 1 . .
C C11 0.6549(4) 0.1236(5) 0.3850(5) 0.1154(19) Uani d . 1 . .
H H11 0.6935 0.1000 0.3695 0.138 Uiso calc R 1 . .
C C12 0.6215(4) 0.0456(4) 0.4160(5) 0.1150(18) Uani d . 1 . .
H H12 0.6407 -0.0280 0.4251 0.138 Uiso calc R 1 . .
C C13 0.5602(3) 0.0787(3) 0.4328(3) 0.0810(11) Uani d . 1 . .
H H13 0.5348 0.0266 0.4503 0.097 Uiso calc R 1 . .
C C14 0.3103(3) 0.5223(3) 0.2966(3) 0.0810(11) Uani d . 1 . .
H H14A 0.3714 0.4934 0.3237 0.097 Uiso calc R 1 . .
H H14B 0.3161 0.5831 0.3357 0.097 Uiso calc R 1 . .
H H14C 0.2809 0.5476 0.2313 0.097 Uiso calc R 1 . .
C C15 0.6712(4) 0.3156(5) 0.3441(4) 0.1154(17) Uani d . 1 . .
H H15A 0.7328 0.3381 0.3991 0.138 Uiso calc R 1 . .
H H15B 0.6308 0.3793 0.3168 0.138 Uiso calc R 1 . .
H H15C 0.6744 0.2826 0.2958 0.138 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'
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
O2 S1 O1 . . 117.85(15) ?
O2 S1 N1 . . 109.70(15) ?
O1 S1 N1 . . 103.55(14) ?
O2 S1 C1 . . 109.46(14) ?
O1 S1 C1 . . 109.93(14) ?
N1 S1 C1 . . 105.55(14) ?
C7 N1 S1 . . 122.6(2) ?
C7 N1 H1N . . 128(3) ?
S1 N1 H1N . . 109(3) ?
C6 C1 C2 . . 121.9(3) ?
C6 C1 S1 . . 116.3(2) ?
C2 C1 S1 . . 121.9(2) ?
C3 C2 C1 . . 115.8(3) ?
C3 C2 C14 . . 119.3(3) ?
C1 C2 C14 . . 124.9(3) ?
C4 C3 C2 . . 122.7(3) ?
C4 C3 H3 . . 118.6 ?
C2 C3 H3 . . 118.6 ?
C5 C4 C3 . . 120.3(3) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 119.3(3) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C5 C6 C1 . . 120.0(3) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
O3 C7 N1 . . 120.2(3) ?
O3 C7 C8 . . 122.8(3) ?
N1 C7 C8 . . 117.0(3) ?
C13 C8 C9 . . 119.3(3) ?
C13 C8 C7 . . 117.2(3) ?
C9 C8 C7 . . 123.4(3) ?
C10 C9 C8 . . 120.7(4) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C11 C10 C9 . . 118.2(4) ?
C11 C10 C15 . . 121.4(4) ?
C9 C10 C15 . . 120.4(4) ?
C10 C11 C12 . . 122.4(4) ?
C10 C11 H11 . . 118.8 ?
C12 C11 H11 . . 118.8 ?
C13 C12 C11 . . 119.0(4) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C12 C13 C8 . . 120.3(4) ?
C12 C13 H13 . . 119.8 ?
C8 C13 H13 . . 119.8 ?
C2 C14 H14A . . 109.5 ?
C2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C10 C15 H15A . . 109.5 ?
C10 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C10 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 . 1.421(2) ?
S1 O1 . 1.433(2) ?
S1 N1 . 1.643(3) ?
S1 C1 . 1.750(3) ?
O3 C7 . 1.209(4) ?
N1 C7 . 1.398(4) ?
N1 H1N . 0.83(2) ?
C1 C6 . 1.392(4) ?
C1 C2 . 1.396(4) ?
C2 C3 . 1.388(5) ?
C2 C14 . 1.494(5) ?
C3 C4 . 1.376(6) ?
C3 H3 . 0.93 ?
C4 C5 . 1.368(5) ?
C4 H4 . 0.93 ?
C5 C6 . 1.375(5) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 C8 . 1.484(4) ?
C8 C13 . 1.381(5) ?
C8 C9 . 1.391(5) ?
C9 C10 . 1.386(5) ?
C9 H9 . 0.93 ?
C10 C11 . 1.353(7) ?
C10 C15 . 1.499(6) ?
C11 C12 . 1.387(7) ?
C11 H11 . 0.93 ?
C12 C13 . 1.364(6) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
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 5_666 0.83(2) 2.06(2) 2.884(4) 179(4)
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 C7 . . . . 51.6(3) ?
O1 S1 N1 C7 . . . . 178.3(3) ?
C1 S1 N1 C7 . . . . -66.2(3) ?
O2 S1 C1 C6 . . . . -7.5(3) ?
O1 S1 C1 C6 . . . . -138.4(2) ?
N1 S1 C1 C6 . . . . 110.5(2) ?
O2 S1 C1 C2 . . . . 171.3(2) ?
O1 S1 C1 C2 . . . . 40.4(3) ?
N1 S1 C1 C2 . . . . -70.7(3) ?
C6 C1 C2 C3 . . . . 0.8(5) ?
S1 C1 C2 C3 . . . . -178.0(2) ?
C6 C1 C2 C14 . . . . 179.1(3) ?
S1 C1 C2 C14 . . . . 0.4(5) ?
C1 C2 C3 C4 . . . . 0.0(5) ?
C14 C2 C3 C4 . . . . -178.5(4) ?
C2 C3 C4 C5 . . . . -0.3(6) ?
C3 C4 C5 C6 . . . . 0.0(6) ?
C4 C5 C6 C1 . . . . 0.7(5) ?
C2 C1 C6 C5 . . . . -1.1(5) ?
S1 C1 C6 C5 . . . . 177.6(3) ?
S1 N1 C7 O3 . . . . -1.1(5) ?
S1 N1 C7 C8 . . . . 179.1(2) ?
O3 C7 C8 C13 . . . . -20.9(5) ?
N1 C7 C8 C13 . . . . 158.9(3) ?
O3 C7 C8 C9 . . . . 157.4(3) ?
N1 C7 C8 C9 . . . . -22.8(5) ?
C13 C8 C9 C10 . . . . 2.1(5) ?
C7 C8 C9 C10 . . . . -176.3(3) ?
C8 C9 C10 C11 . . . . -1.5(6) ?
C8 C9 C10 C15 . . . . 177.8(4) ?
C9 C10 C11 C12 . . . . -1.6(8) ?
C15 C10 C11 C12 . . . . 179.1(5) ?
C10 C11 C12 C13 . . . . 4.1(9) ?
C11 C12 C13 C8 . . . . -3.3(8) ?
C9 C8 C13 C12 . . . . 0.4(6) ?
C7 C8 C13 C12 . . . . 178.8(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14320500
