#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224864.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_2224864
loop_
_publ_author_name
'Ashfaq, Muhammad'
'Khan, Islam Ullah'
'Arshad, Muhammad Nadeem'
'Ahmad, Hamad'
'Asghar, Muhammad Nadeem'
_publ_section_title
;
 N-[4-(p-Toluenesulfonamido)phenylsulfonyl]acetamide
;
_journal_coeditor_code           BT5152
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o299
_journal_paper_doi               10.1107/S1600536809055706
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C15 H16 N2 O5 S2'
_chemical_formula_sum            'C15 H16 N2 O5 S2'
_chemical_formula_weight         368.42
_chemical_name_systematic
;
N-[4-(p-Toluenesulfonamido)phenylsulfonyl]acetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.290(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8077(4)
_cell_length_b                   10.0782(4)
_cell_length_c                   17.3081(7)
_cell_measurement_reflns_used    4606
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.35
_cell_volume                     1683.29(12)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16294
_diffrn_reflns_theta_full        27.13
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_min         2.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.8519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.313
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0377
_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)+(0.0603P)²+0.5119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                2787
_reflns_number_total             3715
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5152.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        1683.28(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224864
_cod_database_fobs_code          2224864
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.58372(5) 0.79324(5) 1.04610(3) 0.03142(15) Uani d . 1 . .
S S2 0.91252(5) 0.97819(6) 0.73350(3) 0.03660(16) Uani d . 1 . .
O O1 0.55834(15) 0.82933(16) 1.12253(9) 0.0429(4) Uani d . 1 . .
O O2 0.47119(14) 0.75141(16) 0.98763(9) 0.0422(4) Uani d . 1 . .
O O3 0.82154(16) 0.9285(2) 0.66630(9) 0.0553(5) Uani d . 1 . .
O O4 0.96901(18) 1.10836(16) 0.73294(11) 0.0532(5) Uani d . 1 . .
O O5 1.16225(16) 0.96040(18) 0.85525(9) 0.0501(4) Uani d . 1 . .
N N1 0.65425(17) 0.92526(18) 1.01581(10) 0.0315(4) Uani d . 1 . .
H H1N 0.693(2) 0.971(2) 1.0518(14) 0.038 Uiso d . 1 . .
N N2 1.04204(18) 0.86957(19) 0.74560(10) 0.0341(4) Uani d . 1 . .
H H2N 1.034(2) 0.811(2) 0.7122(14) 0.041 Uiso d . 1 . .
C C1 0.9121(2) 0.4715(2) 1.08120(15) 0.0427(5) Uani d . 1 . .
C C2 0.9326(2) 0.5914(2) 1.12183(15) 0.0470(6) Uani d . 1 . .
H H2 1.0146 0.6052 1.1572 0.056 Uiso calc R 1 . .
C C3 0.8338(2) 0.6893(2) 1.11050(13) 0.0413(5) Uani d . 1 . .
H H3 0.8485 0.7686 1.1382 0.050 Uiso calc R 1 . .
C C4 0.7115(2) 0.6690(2) 1.05720(12) 0.0316(4) Uani d . 1 . .
C C5 0.6907(2) 0.5522(2) 1.01500(13) 0.0382(5) Uani d . 1 . .
H H5 0.6100 0.5395 0.9784 0.046 Uiso calc R 1 . .
C C6 0.7907(2) 0.4546(2) 1.02772(15) 0.0436(5) Uani d . 1 . .
H H6 0.7761 0.3756 0.9997 0.052 Uiso calc R 1 . .
C C7 0.71121(19) 0.93381(19) 0.94715(11) 0.0278(4) Uani d . 1 . .
C C8 0.8064(2) 1.0347(2) 0.94356(13) 0.0404(5) Uani d . 1 . .
H H8 0.8291 1.0927 0.9856 0.048 Uiso calc R 1 . .
C C9 0.8672(2) 1.0495(2) 0.87847(14) 0.0422(5) Uani d . 1 . .
H H9 0.9305 1.1176 0.8764 0.051 Uiso calc R 1 . .
C C10 0.83393(19) 0.9629(2) 0.81628(12) 0.0306(4) Uani d . 1 . .
C C11 0.7379(2) 0.8629(2) 0.81853(12) 0.0330(5) Uani d . 1 . .
H H11 0.7152 0.8055 0.7761 0.040 Uiso calc R 1 . .
C C12 0.6760(2) 0.8483(2) 0.88342(12) 0.0326(5) Uani d . 1 . .
H H12 0.6110 0.7815 0.8847 0.039 Uiso calc R 1 . .
C C13 1.1547(2) 0.8753(2) 0.80521(12) 0.0354(5) Uani d . 1 . .
C C14 1.2619(3) 0.7714(3) 0.80379(15) 0.0567(7) Uani d . 1 . .
H H14A 1.3395 0.8090 0.7847 0.085 Uiso calc R 1 . .
H H14B 1.2234 0.7003 0.7698 0.085 Uiso calc R 1 . .
H H14C 1.2921 0.7377 0.8559 0.085 Uiso calc R 1 . .
C C15 1.0205(3) 0.3644(3) 1.09553(19) 0.0622(8) Uani d . 1 . .
H H15A 1.1045 0.3959 1.0806 0.093 Uiso calc R 1 . .
H H15B 0.9882 0.2876 1.0649 0.093 Uiso calc R 1 . .
H H15C 1.0381 0.3414 1.1502 0.093 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 . . 119.38(9) ?
O2 S1 N1 . . 109.48(9) ?
O1 S1 N1 . . 104.07(9) ?
O2 S1 C4 . . 108.32(10) ?
O1 S1 C4 . . 108.50(9) ?
N1 S1 C4 . . 106.35(9) ?
O3 S2 O4 . . 120.38(11) ?
O3 S2 N2 . . 102.99(10) ?
O4 S2 N2 . . 108.54(10) ?
O3 S2 C10 . . 109.52(10) ?
O4 S2 C10 . . 108.37(10) ?
N2 S2 C10 . . 106.09(9) ?
C7 N1 S1 . . 125.38(15) ?
C7 N1 H1N . . 114.3(17) ?
S1 N1 H1N . . 112.5(17) ?
C13 N2 S2 . . 124.19(16) ?
C13 N2 H2N . . 121.9(17) ?
S2 N2 H2N . . 113.9(17) ?
C6 C1 C2 . . 118.3(2) ?
C6 C1 C15 . . 121.4(2) ?
C2 C1 C15 . . 120.3(2) ?
C3 C2 C1 . . 121.1(2) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 119.5(2) ?
C2 C3 H3 . . 120.2 ?
C4 C3 H3 . . 120.2 ?
C5 C4 C3 . . 120.3(2) ?
C5 C4 S1 . . 120.96(16) ?
C3 C4 S1 . . 118.77(17) ?
C6 C5 C4 . . 119.3(2) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C1 . . 121.5(2) ?
C5 C6 H6 . . 119.3 ?
C1 C6 H6 . . 119.3 ?
C8 C7 C12 . . 119.38(18) ?
C8 C7 N1 . . 117.08(18) ?
C12 C7 N1 . . 123.53(18) ?
C9 C8 C7 . . 120.7(2) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C8 C9 C10 . . 119.6(2) ?
C8 C9 H9 . . 120.2 ?
C10 C9 H9 . . 120.2 ?
C9 C10 C11 . . 120.42(19) ?
C9 C10 S2 . . 120.36(16) ?
C11 C10 S2 . . 119.22(16) ?
C12 C11 C10 . . 120.14(19) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C7 . . 119.76(19) ?
C11 C12 H12 . . 120.1 ?
C7 C12 H12 . . 120.1 ?
O5 C13 N2 . . 120.4(2) ?
O5 C13 C14 . . 123.8(2) ?
N2 C13 C14 . . 115.8(2) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C1 C15 H15A . . 109.5 ?
C1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C1 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 . 1.4215(15) ?
S1 O1 . 1.4359(15) ?
S1 N1 . 1.6289(18) ?
S1 C4 . 1.758(2) ?
S2 O3 . 1.4244(17) ?
S2 O4 . 1.4247(18) ?
S2 N2 . 1.6615(18) ?
S2 C10 . 1.751(2) ?
O5 C13 . 1.211(3) ?
N1 C7 . 1.403(2) ?
N1 H1N . 0.81(2) ?
N2 C13 . 1.372(3) ?
N2 H2N . 0.82(2) ?
C1 C6 . 1.382(3) ?
C1 C2 . 1.394(4) ?
C1 C15 . 1.504(3) ?
C2 C3 . 1.372(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.392(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(3) ?
C5 C6 . 1.379(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.389(3) ?
C7 C12 . 1.394(3) ?
C8 C9 . 1.374(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.379(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.385(3) ?
C11 C12 . 1.377(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.488(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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 O5 3_777 0.81(2) 2.06(2) 2.848(2) 162(2)
N2 H2N O1 4_675 0.82(2) 2.15(2) 2.950(2) 167(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
O2 S1 N1 C7 . . . . -58.48(18) ?
O1 S1 N1 C7 . . . . 172.83(16) ?
C4 S1 N1 C7 . . . . 58.34(18) ?
O3 S2 N2 C13 . . . . -178.58(18) ?
O4 S2 N2 C13 . . . . 52.8(2) ?
C10 S2 N2 C13 . . . . -63.5(2) ?
C6 C1 C2 C3 . . . . 1.4(4) ?
C15 C1 C2 C3 . . . . -178.9(2) ?
C1 C2 C3 C4 . . . . -0.4(4) ?
C2 C3 C4 C5 . . . . -1.1(3) ?
C2 C3 C4 S1 . . . . 177.79(18) ?
O2 S1 C4 C5 . . . . -2.5(2) ?
O1 S1 C4 C5 . . . . 128.50(18) ?
N1 S1 C4 C5 . . . . -120.07(18) ?
O2 S1 C4 C3 . . . . 178.62(17) ?
O1 S1 C4 C3 . . . . -50.4(2) ?
N1 S1 C4 C3 . . . . 61.02(19) ?
C3 C4 C5 C6 . . . . 1.7(3) ?
S1 C4 C5 C6 . . . . -177.20(17) ?
C4 C5 C6 C1 . . . . -0.7(3) ?
C2 C1 C6 C5 . . . . -0.8(4) ?
C15 C1 C6 C5 . . . . 179.4(2) ?
S1 N1 C7 C8 . . . . -158.64(16) ?
S1 N1 C7 C12 . . . . 22.1(3) ?
C12 C7 C8 C9 . . . . -0.9(3) ?
N1 C7 C8 C9 . . . . 179.8(2) ?
C7 C8 C9 C10 . . . . -0.3(4) ?
C8 C9 C10 C11 . . . . 1.2(3) ?
C8 C9 C10 S2 . . . . -178.87(18) ?
O3 S2 C10 C9 . . . . -151.90(18) ?
O4 S2 C10 C9 . . . . -18.8(2) ?
N2 S2 C10 C9 . . . . 97.58(19) ?
O3 S2 C10 C11 . . . . 28.04(19) ?
O4 S2 C10 C11 . . . . 161.13(16) ?
N2 S2 C10 C11 . . . . -82.47(17) ?
C9 C10 C11 C12 . . . . -0.8(3) ?
S2 C10 C11 C12 . . . . 179.30(16) ?
C10 C11 C12 C7 . . . . -0.5(3) ?
C8 C7 C12 C11 . . . . 1.3(3) ?
N1 C7 C12 C11 . . . . -179.41(18) ?
S2 N2 C13 O5 . . . . 2.9(3) ?
S2 N2 C13 C14 . . . . -177.73(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 946722
