#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/44/2224411.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_2224411
loop_
_publ_author_name
'Sharif, Hafiz Muhammad Adeel'
'Dong, Gui-Ying'
'Arshad, Muhammad Nadeem'
'Khan, Islam Ullah'
_publ_section_title
;
 4-Benzenesulfonamidobenzoic acid
;
_journal_coeditor_code           RK2179
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3086
_journal_paper_doi               10.1107/S1600536809047291
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H11 N O4 S'
_chemical_formula_moiety         'C13 H11 N O4 S'
_chemical_formula_sum            'C13 H11 N O4 S'
_chemical_formula_weight         277.30
_chemical_name_systematic
;
4-Benzenesulfonamidobenzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 117.510(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2050(3)
_cell_length_b                   37.726(2)
_cell_length_c                   7.3781(4)
_cell_measurement_reflns_used    5008
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3.02
_cell_volume                     1284.98(13)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       'φ and 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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13550
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.08
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.9348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.363
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0645
_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)+(0.0878P)²+1.4857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.1985
_reflns_number_gt                2633
_reflns_number_total             3185
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2179.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224411
_cod_database_fobs_code          2224411
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.27263(17) 0.36345(2) 0.53929(12) 0.0443(3) Uani d . 1 . .
O O5 -0.4876(5) 0.48980(7) -0.2675(3) 0.0496(6) Uani d . 1 . .
H H5 -0.5699 0.5003 -0.3768 0.074 Uiso d R 1 . .
O O6 -0.2171(5) 0.47077(6) -0.4087(3) 0.0464(5) Uani d . 1 . .
O O7 0.4834(6) 0.35320(8) 0.7386(4) 0.0693(8) Uani d . 1 . .
O O8 -0.0109(5) 0.37334(7) 0.5034(4) 0.0557(6) Uani d . 1 . .
N N2 0.4098(5) 0.39697(7) 0.4738(4) 0.0408(6) Uani d . 1 . .
H H2 0.5771 0.3942 0.5010 0.049 Uiso d R 1 . .
C C14 0.2360(6) 0.41529(7) 0.2848(4) 0.0344(6) Uani d . 1 . .
C C15 0.2845(6) 0.41056(8) 0.1173(5) 0.0411(7) Uani d . 1 . .
H H15 0.4269 0.3949 0.1242 0.049 Uiso calc R 1 . .
C C16 0.1192(6) 0.42930(8) -0.0615(5) 0.0406(6) Uani d . 1 . .
H H16 0.1543 0.4267 -0.1735 0.049 Uiso calc R 1 . .
C C17 -0.0980(5) 0.45182(7) -0.0728(4) 0.0319(5) Uani d . 1 . .
C C18 -0.1453(6) 0.45608(8) 0.0961(4) 0.0375(6) Uani d . 1 . .
H H18 -0.2921 0.4710 0.0884 0.045 Uiso calc R 1 . .
C C19 0.0239(6) 0.43826(8) 0.2754(4) 0.0386(6) Uani d . 1 . .
H H19 -0.0049 0.4417 0.3895 0.046 Uiso calc R 1 . .
C C20 0.2370(7) 0.32889(8) 0.3691(5) 0.0456(7) Uani d . 1 . .
C C21 0.4682(10) 0.30652(11) 0.4110(8) 0.0731(12) Uani d . 1 . .
H H21 0.6402 0.3090 0.5314 0.088 Uiso calc R 1 . .
C C22 0.4401(13) 0.28042(13) 0.2715(11) 0.0938(18) Uani d . 1 . .
H H22 0.5934 0.2650 0.2995 0.113 Uiso calc R 1 . .
C C23 0.1881(15) 0.27699(14) 0.0918(10) 0.0938(17) Uani d . 1 . .
H H23 0.1703 0.2594 -0.0015 0.113 Uiso calc R 1 . .
C C24 -0.0327(15) 0.29943(14) 0.0524(9) 0.1009(19) Uani d . 1 . .
H H24 -0.2033 0.2972 -0.0692 0.121 Uiso calc R 1 . .
C C25 -0.0115(10) 0.32565(11) 0.1883(7) 0.0724(12) Uani d . 1 . .
H H25 -0.1653 0.3411 0.1574 0.087 Uiso calc R 1 . .
C C26 -0.2763(6) 0.47182(7) -0.2629(4) 0.0340(6) 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
O7 S1 O8 . . 120.12(17) ?
O7 S1 N2 . . 106.43(16) ?
O8 S1 N2 . . 107.42(14) ?
O7 S1 C20 . . 108.24(17) ?
O8 S1 C20 . . 107.64(16) ?
N2 S1 C20 . . 106.21(14) ?
C26 O5 H5 . . 109.5 ?
C14 N2 S1 . . 119.58(19) ?
C14 N2 H2 . . 115.3 ?
S1 N2 H2 . . 113.4 ?
C19 C14 C15 . . 120.5(3) ?
C19 C14 N2 . . 118.7(3) ?
C15 C14 N2 . . 120.7(2) ?
C14 C15 C16 . . 119.6(3) ?
C14 C15 H15 . . 120.2 ?
C16 C15 H15 . . 120.2 ?
C17 C16 C15 . . 119.9(3) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C18 C17 C16 . . 119.7(3) ?
C18 C17 C26 . . 119.9(2) ?
C16 C17 C26 . . 120.4(2) ?
C19 C18 C17 . . 120.4(3) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C14 C19 C18 . . 119.7(3) ?
C14 C19 H19 . . 120.1 ?
C18 C19 H19 . . 120.1 ?
C25 C20 C21 . . 119.8(4) ?
C25 C20 S1 . . 120.2(3) ?
C21 C20 S1 . . 119.9(3) ?
C20 C21 C22 . . 119.1(5) ?
C20 C21 H21 . . 120.4 ?
C22 C21 H21 . . 120.5 ?
C23 C22 C21 . . 120.7(5) ?
C23 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
C24 C23 C22 . . 119.2(5) ?
C24 C23 H23 . . 120.4 ?
C22 C23 H23 . . 120.4 ?
C23 C24 C25 . . 121.4(5) ?
C23 C24 H24 . . 119.3 ?
C25 C24 H24 . . 119.3 ?
C20 C25 C24 . . 119.7(4) ?
C20 C25 H25 . . 120.1 ?
C24 C25 H25 . . 120.1 ?
O6 C26 O5 . . 123.0(3) ?
O6 C26 C17 . . 120.2(2) ?
O5 C26 C17 . . 116.8(2) ?
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 O7 . 1.423(3) ?
S1 O8 . 1.423(2) ?
S1 N2 . 1.632(3) ?
S1 C20 . 1.760(4) ?
O5 C26 . 1.279(3) ?
O5 H5 . 0.8186 ?
O6 C26 . 1.249(3) ?
N2 C14 . 1.440(3) ?
N2 H2 . 0.8048 ?
C14 C19 . 1.380(4) ?
C14 C15 . 1.382(4) ?
C15 C16 . 1.390(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.386(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.386(4) ?
C17 C26 . 1.482(4) ?
C18 C19 . 1.379(4) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 C25 . 1.368(5) ?
C20 C21 . 1.383(5) ?
C21 C22 . 1.383(7) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.374(8) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.347(8) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.376(7) ?
C24 H24 . 0.9300 ?
C25 H25 . 0.9300 ?
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
N2 H2 O8 1_655 0.81 2.28 3.054(4) 162
O5 H5 O6 3_464 0.82 1.82 2.625(3) 168
C18 H18 O5 3_465 0.93 2.58 3.413(4) 150
C19 H19 O6 1_556 0.93 2.48 3.348(4) 155
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 441891
