#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/17/2221730.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_2221730
loop_
_publ_author_name
'Ashfaq, Muhammad'
'Tahir, M. Nawaz'
'Khan, Islam Ullah'
'Arshad, Muhammad Nadeem'
'Saeed-ul-Hassan, Syed'
_publ_section_title
;
 N-Acetyl-4-(benzenesulfonamido)benzenesulfonamide
;
_journal_coeditor_code           HK2676
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1180
_journal_paper_doi               10.1107/S1600536809015876
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H14 N2 O5 S2'
_chemical_formula_moiety         'C14 H14 N2 O5 S2'
_chemical_formula_sum            'C14 H14 N2 O5 S2'
_chemical_formula_weight         354.39
_chemical_name_systematic
;
N-Acetyl-4-(benzenesulfonamido)benzenesulfonamide
;
_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
_cell_angle_beta                 103.169(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9316(9)
_cell_length_b                   9.4828(8)
_cell_length_c                   17.6490(17)
_cell_measurement_reflns_used    4034
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.37
_cell_volume                     1618.5(3)
_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_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17674
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.359
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0488
_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)+(0.052P)²+0.3831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                2423
_reflns_number_total             4034
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2676.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221730
_cod_database_fobs_code          2221730
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.90183(7) 0.28463(8) -0.04571(4) 0.0407(3) Uani . . 1.000
S S2 0.58491(7) 0.45284(7) 0.26062(4) 0.0374(2) Uani . . 1.000
O O1 0.9231(2) 0.3308(2) -0.11946(11) 0.0530(7) Uani . . 1.000
O O2 1.01569(19) 0.2335(2) 0.01166(11) 0.0546(7) Uani . . 1.000
O O3 0.68083(19) 0.4029(2) 0.32790(10) 0.0564(7) Uani . . 1.000
O O4 0.5257(2) 0.58953(19) 0.26098(11) 0.0510(7) Uani . . 1.000
O O5 0.3371(2) 0.4255(2) 0.13539(11) 0.0560(7) Uani . . 1.000
N N1 0.8361(2) 0.4215(2) -0.01260(12) 0.0384(7) Uani . . 1.000
N N2 0.4595(2) 0.3347(2) 0.24701(12) 0.0387(7) Uani . . 1.000
C C1 0.7705(3) 0.1563(3) -0.06104(15) 0.0396(9) Uani . . 1.000
C C2 0.6519(3) 0.1794(3) -0.11844(17) 0.0518(11) Uani . . 1.000
C C3 0.5482(3) 0.0815(4) -0.1295(2) 0.0703(14) Uani . . 1.000
C C4 0.5621(4) -0.0385(4) -0.0833(3) 0.0759(17) Uani . . 1.000
C C5 0.6797(4) -0.0586(3) -0.0265(2) 0.0729(16) Uani . . 1.000
C C6 0.7849(3) 0.0381(3) -0.01472(18) 0.0545(11) Uani . . 1.000
C C7 0.7799(2) 0.4241(3) 0.05379(14) 0.0315(8) Uani . . 1.000
C C8 0.8129(3) 0.3261(3) 0.11352(15) 0.0417(9) Uani . . 1.000
C C9 0.7502(3) 0.3347(3) 0.17563(14) 0.0389(9) Uani . . 1.000
C C10 0.6584(3) 0.4411(3) 0.17997(14) 0.0321(8) Uani . . 1.000
C C11 0.6272(3) 0.5403(3) 0.12140(17) 0.0472(10) Uani . . 1.000
C C12 0.6873(3) 0.5305(3) 0.05858(16) 0.0446(10) Uani . . 1.000
C C13 0.3439(3) 0.3407(3) 0.18721(15) 0.0393(9) Uani . . 1.000
C C14 0.2314(3) 0.2385(4) 0.19149(18) 0.0655(13) Uani . . 1.000
H H1N 0.83546 0.49926 -0.03774 0.0461 Uiso . . 1.000
H H2 0.64289 0.26019 -0.14902 0.0622 Uiso . . 1.000
H H2N 0.46714 0.26548 0.27920 0.0464 Uiso . . 1.000
H H3 0.46813 0.09538 -0.16798 0.0843 Uiso . . 1.000
H H4 0.49166 -0.10523 -0.09098 0.0910 Uiso . . 1.000
H H5 0.68825 -0.13877 0.00460 0.0874 Uiso . . 1.000
H H6 0.86471 0.02409 0.02393 0.0655 Uiso . . 1.000
H H8 0.87684 0.25522 0.11176 0.0501 Uiso . . 1.000
H H9 0.77038 0.26763 0.21503 0.0467 Uiso . . 1.000
H H11 0.56602 0.61331 0.12432 0.0566 Uiso . . 1.000
H H12 0.66522 0.59658 0.01874 0.0536 Uiso . . 1.000
H H14A 0.19294 0.20141 0.14056 0.0984 Uiso . . 1.000
H H14B 0.16038 0.28576 0.21067 0.0984 Uiso . . 1.000
H H14C 0.26868 0.16277 0.22601 0.0984 Uiso . . 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . . 119.56(12) no
O1 S1 N1 . . . 103.74(11) no
O1 S1 C1 . . . 109.21(12) no
O2 S1 N1 . . . 109.70(11) no
O2 S1 C1 . . . 108.39(13) no
N1 S1 C1 . . . 105.31(12) no
O3 S2 O4 . . . 119.85(12) no
O3 S2 N2 . . . 103.58(11) no
O3 S2 C10 . . . 109.54(13) no
O4 S2 N2 . . . 108.64(11) no
O4 S2 C10 . . . 108.16(13) no
N2 S2 C10 . . . 106.25(12) no
S1 N1 C7 . . . 125.64(18) no
S2 N2 C13 . . . 123.70(18) no
C7 N1 H1N . . . 117.00 no
S1 N1 H1N . . . 117.00 no
S2 N2 H2N . . . 118.00 no
C13 N2 H2N . . . 118.00 no
S1 C1 C2 . . . 118.7(2) no
S1 C1 C6 . . . 120.0(2) no
C2 C1 C6 . . . 121.3(3) no
C1 C2 C3 . . . 119.0(3) no
C2 C3 C4 . . . 120.1(3) no
C3 C4 C5 . . . 119.9(3) no
C4 C5 C6 . . . 120.8(3) no
C1 C6 C5 . . . 118.9(3) no
C8 C7 C12 . . . 119.2(2) no
N1 C7 C8 . . . 123.4(2) no
N1 C7 C12 . . . 117.4(2) no
C7 C8 C9 . . . 119.5(3) no
C8 C9 C10 . . . 120.8(2) no
S2 C10 C9 . . . 119.9(2) no
S2 C10 C11 . . . 120.2(2) no
C9 C10 C11 . . . 119.9(3) no
C10 C11 C12 . . . 119.5(3) no
C7 C12 C11 . . . 121.0(3) no
O5 C13 C14 . . . 123.8(3) no
N2 C13 C14 . . . 116.0(2) no
O5 C13 N2 . . . 120.2(3) no
C1 C2 H2 . . . 121.00 no
C3 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 121.00 no
C5 C6 H6 . . . 121.00 no
C7 C8 H8 . . . 120.00 no
C9 C8 H8 . . . 120.00 no
C8 C9 H9 . . . 120.00 no
C10 C9 H9 . . . 120.00 no
C10 C11 H11 . . . 120.00 no
C12 C11 H11 . . . 120.00 no
C7 C12 H12 . . . 119.00 no
C11 C12 H12 . . . 120.00 no
C13 C14 H14A . . . 109.00 no
C13 C14 H14B . . . 109.00 no
C13 C14 H14C . . . 109.00 no
H14A C14 H14B . . . 109.00 no
H14A C14 H14C . . . 110.00 no
H14B C14 H14C . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . . 1.434(2) no
S1 O2 . . 1.420(2) no
S1 N1 . . 1.621(2) no
S1 C1 . . 1.759(3) no
S2 O3 . . 1.4235(19) no
S2 O4 . . 1.424(2) no
S2 N2 . . 1.652(2) no
S2 C10 . . 1.745(3) no
O5 C13 . . 1.208(3) no
N1 C7 . . 1.408(3) no
N2 C13 . . 1.372(3) no
N1 H1N . . 0.8600 no
N2 H2N . . 0.8600 no
C1 C6 . . 1.375(4) no
C1 C2 . . 1.385(4) no
C2 C3 . . 1.367(5) no
C3 C4 . . 1.388(6) no
C4 C5 . . 1.368(6) no
C5 C6 . . 1.370(5) no
C7 C12 . . 1.381(4) no
C7 C8 . . 1.387(4) no
C8 C9 . . 1.381(4) no
C9 C10 . . 1.374(4) no
C10 C11 . . 1.380(4) no
C11 C12 . . 1.377(4) no
C13 C14 . . 1.494(5) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C8 H8 . . 0.9300 no
C9 H9 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C14 H14A . . 0.9600 no
C14 H14B . . 0.9600 no
C14 H14C . . 0.9600 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 H8 2.8600 . . no
O1 N2 2.922(3) . 4_554 no
O2 C6 3.242(4) . 3_755 no
O2 C5 3.407(4) . 3_755 no
O2 C8 3.116(3) . . no
O2 C14 3.401(4) . 1_655 no
O4 O5 2.992(3) . . no
O4 C8 3.300(3) . 2_655 no
O4 C9 3.237(3) . 2_655 no
O4 C14 3.193(4) . 2_555 no
O5 C11 3.142(4) . . no
O5 N1 2.839(3) . 3_665 no
O5 O4 2.992(3) . . no
O5 C12 3.402(3) . 3_665 no
O5 C10 3.111(4) . . no
O1 H14C 2.8100 . 4_554 no
O1 H2 2.7900 . . no
O1 H2N 2.1400 . 4_554 no
O2 H8 2.4900 . . no
O2 H6 2.8500 . 3_755 no
O2 H6 2.5300 . . no
O2 H1N 2.9200 . 3_765 no
O2 H14A 2.5600 . 1_655 no
O3 H3 2.8400 . 4_555 no
O3 H9 2.6900 . . no
O4 H11 2.5400 . . no
O4 H14B 2.7500 . 2_555 no
O4 H2 2.6900 . 3_665 no
O4 H8 2.7300 . 2_655 no
O4 H9 2.6000 . 2_655 no
O5 H1N 2.2500 . 3_665 no
O5 H12 2.7200 . 3_665 no
N1 O5 2.839(3) . 3_665 no
N2 O1 2.922(3) . 4_455 no
C1 C8 3.416(4) . . no
C4 C5 3.534(6) . 3_655 no
C4 C4 3.515(7) . 3_655 no
C5 O2 3.407(4) . 3_755 no
C5 C4 3.534(6) . 3_655 no
C6 C8 3.517(4) . . no
C6 O2 3.242(4) . 3_755 no
C8 O2 3.116(3) . . no
C8 C1 3.416(4) . . no
C8 O4 3.300(3) . 2_645 no
C8 C6 3.517(4) . . no
C9 O4 3.237(3) . 2_645 no
C10 O5 3.111(4) . . no
C11 O5 3.142(4) . . no
C12 O5 3.402(3) . 3_665 no
C14 O4 3.193(4) . 2_545 no
C14 O2 3.401(4) . 1_455 no
C2 H14B 3.0500 . 4_554 no
C2 H11 2.9100 . 3_665 no
C5 H14A 2.9400 . 3_655 no
C6 H8 3.0200 . . no
H1N H12 2.3400 . . no
H1N O2 2.9200 . 3_765 no
H1N O5 2.2500 . 3_665 no
H2 O1 2.7900 . . no
H2 O4 2.6900 . 3_665 no
H2 H11 2.5200 . 3_665 no
H2 H14B 2.5600 . 4_554 no
H2N H14C 2.2100 . . no
H2N O1 2.1400 . 4_455 no
H3 O3 2.8400 . 4_454 no
H5 H12 2.5400 . 1_545 no
H6 O2 2.5300 . . no
H6 O2 2.8500 . 3_755 no
H8 S1 2.8600 . . no
H8 O2 2.4900 . . no
H8 C6 3.0200 . . no
H8 O4 2.7300 . 2_645 no
H9 O3 2.6900 . . no
H9 O4 2.6000 . 2_645 no
H11 O4 2.5400 . . no
H11 C2 2.9100 . 3_665 no
H11 H2 2.5200 . 3_665 no
H12 H1N 2.3400 . . no
H12 H5 2.5400 . 1_565 no
H12 O5 2.7200 . 3_665 no
H14A O2 2.5600 . 1_455 no
H14A C5 2.9400 . 3_655 no
H14B O4 2.7500 . 2_545 no
H14B C2 3.0500 . 4_455 no
H14B H2 2.5600 . 4_455 no
H14C H2N 2.2100 . . no
H14C O1 2.8100 . 4_455 no
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
_geom_hbond_publ_flag
N1 H1N O5 3_665 0.86 2.25 2.839(3) 126 yes
N2 H2N O1 4_455 0.86 2.14 2.922(3) 151 yes
C8 H8 O2 . 0.93 2.49 3.116(3) 125 yes
C9 H9 O4 2_645 0.93 2.60 3.237(3) 126 yes
C14 H14A O2 1_455 0.96 2.56 3.401(4) 147 yes
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 . . . . 171.1(2) no
O2 S1 N1 C7 . . . . -60.1(2) no
C1 S1 N1 C7 . . . . 56.4(2) no
O1 S1 C1 C2 . . . . -44.2(3) no
O1 S1 C1 C6 . . . . 137.9(2) no
O2 S1 C1 C2 . . . . -176.0(2) no
O2 S1 C1 C6 . . . . 6.1(3) no
N1 S1 C1 C2 . . . . 66.7(3) no
N1 S1 C1 C6 . . . . -111.2(2) no
O3 S2 N2 C13 . . . . -179.6(2) no
O4 S2 N2 C13 . . . . 52.0(2) no
C10 S2 N2 C13 . . . . -64.2(2) no
O3 S2 C10 C9 . . . . 32.2(3) no
O3 S2 C10 C11 . . . . -146.2(2) no
O4 S2 C10 C9 . . . . 164.5(2) no
O4 S2 C10 C11 . . . . -14.0(3) no
N2 S2 C10 C9 . . . . -79.1(3) no
N2 S2 C10 C11 . . . . 102.5(2) no
S1 N1 C7 C8 . . . . 22.2(3) no
S1 N1 C7 C12 . . . . -157.8(2) no
S2 N2 C13 O5 . . . . 9.3(4) no
S2 N2 C13 C14 . . . . -170.4(2) no
S1 C1 C2 C3 . . . . -178.6(2) no
C6 C1 C2 C3 . . . . -0.8(4) no
S1 C1 C6 C5 . . . . 178.4(2) no
C2 C1 C6 C5 . . . . 0.5(5) no
C1 C2 C3 C4 . . . . 0.4(5) no
C2 C3 C4 C5 . . . . 0.1(6) no
C3 C4 C5 C6 . . . . -0.4(6) no
C4 C5 C6 C1 . . . . 0.0(5) no
N1 C7 C8 C9 . . . . -178.4(2) no
C12 C7 C8 C9 . . . . 1.5(4) no
N1 C7 C12 C11 . . . . 179.7(3) no
C8 C7 C12 C11 . . . . -0.2(4) no
C7 C8 C9 C10 . . . . -1.7(4) no
C8 C9 C10 S2 . . . . -177.9(2) no
C8 C9 C10 C11 . . . . 0.5(4) no
S2 C10 C11 C12 . . . . 179.2(2) no
C9 C10 C11 C12 . . . . 0.8(4) no
C10 C11 C12 C7 . . . . -1.0(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3296171
