#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/08/2230884.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_2230884
loop_
_publ_author_name
'Sharif, Shahzad'
'Khan, Islam Ullah'
'Mahmood, Tariq'
'Kang, Sung Kwon'
_publ_section_title
;
 2-(4-Acetamidobenzenesulfonamido)benzoic acid
;
_journal_coeditor_code           TK2747
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1570
_journal_paper_doi               10.1107/S1600536811020307
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H14 N2 O5 S'
_chemical_formula_moiety         'C15 H14 N2 O5 S'
_chemical_formula_sum            'C15 H14 N2 O5 S'
_chemical_formula_weight         334.34
_chemical_name_systematic
;
2-(4-Acetamidobenzenesulfonamido)benzoic acid
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.47(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3721(19)
_cell_length_b                   13.036(3)
_cell_length_c                   13.132(3)
_cell_measurement_reflns_used    1295
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.72
_cell_measurement_theta_min      2.78
_cell_volume                     1512.7(6)
_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)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2926
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.82
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.82
_refine_ls_R_factor_all          0.111
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0338P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                1470
_reflns_number_total             2926
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2747.cif
_cod_data_source_block           I
_cod_original_cell_volume        1512.7(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2230884
_cod_database_fobs_code          2230884
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
C C1 0.9116(7) 0.1951(5) 0.4462(5) 0.0489(17) Uani d . 1 . .
C C2 0.8856(6) 0.1876(4) 0.3361(5) 0.0378(15) Uani d . 1 . .
C C3 0.9664(8) 0.2491(5) 0.2895(6) 0.069(2) Uani d . 1 . .
H H3 0.9489 0.2433 0.2157 0.082 Uiso calc R 1 . .
C C4 1.0705(8) 0.3179(6) 0.3474(7) 0.068(2) Uani d . 1 . .
H H4 1.124 0.3585 0.3143 0.081 Uiso calc R 1 . .
C C5 1.0948(8) 0.3260(6) 0.4565(7) 0.078(2) Uani d . 1 . .
H H5 1.1645 0.3736 0.4972 0.094 Uiso calc R 1 . .
C C6 1.0181(8) 0.2652(6) 0.5064(6) 0.0547(18) Uani d . 1 . .
H H6 1.0374 0.271 0.5804 0.066 Uiso calc R 1 . .
C C7 0.8274(7) 0.1297(5) 0.4990(5) 0.0444(16) Uani d . 1 . .
O O8 0.7297(6) 0.0692(4) 0.4533(4) 0.0761(16) Uani d . 1 . .
O O9 0.8716(5) 0.1415(4) 0.6050(4) 0.0753(14) Uani d . 1 . .
H H9 0.8211 0.1043 0.63 0.113 Uiso calc R 1 . .
N N10 0.7746(6) 0.1191(4) 0.2728(4) 0.0556(15) Uani d . 1 . .
H H10 0.7657 0.0613 0.3017 0.067 Uiso calc R 1 . .
S S11 0.6629(2) 0.13965(13) 0.15141(13) 0.0496(5) Uani d . 1 . .
O O12 0.5537(5) 0.0600(3) 0.1345(3) 0.0650(13) Uani d . 1 . .
O O13 0.7415(4) 0.1479(3) 0.0766(3) 0.0601(12) Uani d . 1 . .
C C14 0.5771(6) 0.2586(5) 0.1545(5) 0.0409(16) Uani d . 1 . .
C C15 0.5660(7) 0.3302(5) 0.0747(5) 0.0505(18) Uani d . 1 . .
H H15 0.6111 0.3183 0.0225 0.061 Uiso calc R 1 . .
C C16 0.4882(7) 0.4181(5) 0.0734(5) 0.0523(19) Uani d . 1 . .
H H16 0.48 0.4663 0.0196 0.063 Uiso calc R 1 . .
C C17 0.4204(6) 0.4379(5) 0.1504(5) 0.0374(15) Uani d . 1 . .
C C18 0.4315(7) 0.3678(5) 0.2282(5) 0.0485(18) Uani d . 1 . .
H H18 0.3873 0.3809 0.2806 0.058 Uiso calc R 1 . .
C C19 0.5082(7) 0.2768(5) 0.2307(5) 0.0479(17) Uani d . 1 . .
H H19 0.5134 0.228 0.2834 0.057 Uiso calc R 1 . .
N N20 0.3395(5) 0.5312(4) 0.1386(4) 0.0434(13) Uani d . 1 . .
H H20 0.3362 0.5668 0.0827 0.052 Uiso calc R 1 . .
C C21 0.2673(6) 0.5729(5) 0.2010(5) 0.0411(16) Uani d . 1 . .
O O22 0.2672(5) 0.5316(3) 0.2864(3) 0.0580(13) Uani d . 1 . .
C C23 0.1884(7) 0.6728(4) 0.1635(5) 0.059(2) Uani d . 1 . .
H H23A 0.2015 0.6925 0.0967 0.088 Uiso calc R 1 . .
H H23B 0.2307 0.7246 0.217 0.088 Uiso calc R 1 . .
H H23C 0.0825 0.6653 0.1527 0.088 Uiso calc R 1 . .
C C24 -0.0124(7) 0.9059(5) 0.1004(5) 0.0449(16) Uani d . 1 . .
C C25 0.0910(7) 0.9800(5) 0.1592(5) 0.0437(17) Uani d . 1 . .
C C26 0.1722(7) 1.0380(5) 0.1075(6) 0.061(2) Uani d . 1 . .
H H26 0.2361 1.09 0.1449 0.074 Uiso calc R 1 . .
C C27 0.1581(7) 1.0185(6) 0.0021(6) 0.064(2) Uani d . 1 . .
H H27 0.2137 1.0569 -0.0312 0.077 Uiso calc R 1 . .
C C28 0.0617(8) 0.9422(6) -0.0555(6) 0.071(2) Uani d . 1 . .
H H28 0.0553 0.9272 -0.1261 0.085 Uiso calc R 1 . .
C C29 -0.0240(7) 0.8892(5) -0.0065(6) 0.0510(18) Uani d . 1 . .
H H29 -0.0924 0.8405 -0.0463 0.061 Uiso calc R 1 . .
C C30 -0.1013(7) 0.8458(5) 0.1504(6) 0.0479(17) Uani d . 1 . .
O O31 -0.1843(5) 0.7725(4) 0.0872(4) 0.0677(14) Uani d . 1 . .
H H31 -0.2313 0.7413 0.12 0.101 Uiso calc R 1 . .
O O32 -0.1066(5) 0.8583(4) 0.2407(4) 0.0691(15) Uani d . 1 . .
N N33 0.1094(5) 0.9963(4) 0.2685(4) 0.0555(15) Uani d . 1 . .
H H33 0.0295 0.9965 0.2869 0.067 Uiso calc R 1 . .
S S34 0.2731(2) 1.01499(13) 0.36347(14) 0.0574(5) Uani d . 1 . .
O O35 0.3439(5) 1.1036(3) 0.3377(4) 0.0690(14) Uani d . 1 . .
O O36 0.2365(5) 1.0137(4) 0.4614(3) 0.0713(13) Uani d . 1 . .
C C37 0.3874(7) 0.9084(5) 0.3622(5) 0.0471(17) Uani d . 1 . .
C C38 0.4644(7) 0.9058(5) 0.2911(6) 0.059(2) Uani d . 1 . .
H H38 0.4576 0.9616 0.2457 0.07 Uiso calc R 1 . .
C C39 0.5520(7) 0.8235(6) 0.2842(6) 0.0584(19) Uani d . 1 . .
H H39 0.6053 0.8234 0.2358 0.07 Uiso calc R 1 . .
C C40 0.5584(7) 0.7408(5) 0.3516(5) 0.0498(18) Uani d . 1 . .
C C41 0.4833(7) 0.7435(5) 0.4263(5) 0.0540(19) Uani d . 1 . .
H H41 0.4912 0.6889 0.4733 0.065 Uiso calc R 1 . .
C C42 0.3979(7) 0.8271(5) 0.4301(5) 0.0530(18) Uani d . 1 . .
H H42 0.3462 0.8289 0.4794 0.064 Uiso calc R 1 . .
N N43 0.6463(5) 0.6529(4) 0.3513(4) 0.0563(15) Uani d . 1 . .
H H43 0.6701 0.6161 0.4089 0.068 Uiso calc R 1 . .
C C44 0.6993(7) 0.6179(6) 0.2710(6) 0.0548(19) Uani d . 1 . .
O O45 0.6655(5) 0.6604(4) 0.1829(4) 0.0682(14) Uani d . 1 . .
C C46 0.7926(7) 0.5216(6) 0.2971(5) 0.071(2) Uani d . 1 . .
H H46A 0.8045 0.5004 0.3695 0.106 Uiso calc R 1 . .
H H46B 0.8903 0.5345 0.291 0.106 Uiso calc R 1 . .
H H46C 0.7426 0.4684 0.2475 0.106 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 0 '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 0.006 '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
C2 C1 C6 . . 118.9(7) ?
C2 C1 C7 . . 120.8(6) ?
C6 C1 C7 . . 120.3(7) ?
C3 C2 C1 . . 119.3(6) ?
C3 C2 N10 . . 120.8(6) ?
C1 C2 N10 . . 119.8(6) ?
C4 C3 C2 . . 122.3(7) ?
C4 C3 H3 . . 118.9 ?
C2 C3 H3 . . 118.9 ?
C3 C4 C5 . . 118.2(8) ?
C3 C4 H4 . . 120.9 ?
C5 C4 H4 . . 120.9 ?
C6 C5 C4 . . 121.3(7) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C1 . . 119.9(7) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
O8 C7 O9 . . 121.3(6) ?
O8 C7 C1 . . 125.3(6) ?
O9 C7 C1 . . 113.4(6) ?
C7 O9 H9 . . 109.5 ?
C2 N10 S11 . . 125.8(4) ?
C2 N10 H10 . . 117.1 ?
S11 N10 H10 . . 117.1 ?
O13 S11 O12 . . 117.5(3) ?
O13 S11 N10 . . 112.5(3) ?
O12 S11 N10 . . 103.2(3) ?
O13 S11 C14 . . 107.3(3) ?
O12 S11 C14 . . 109.7(3) ?
N10 S11 C14 . . 106.0(3) ?
C19 C14 C15 . . 119.9(6) ?
C19 C14 S11 . . 119.9(5) ?
C15 C14 S11 . . 119.9(5) ?
C16 C15 C14 . . 119.0(6) ?
C16 C15 H15 . . 120.5 ?
C14 C15 H15 . . 120.5 ?
C15 C16 C17 . . 121.7(6) ?
C15 C16 H16 . . 119.2 ?
C17 C16 H16 . . 119.2 ?
C18 C17 C16 . . 119.2(6) ?
C18 C17 N20 . . 124.7(5) ?
C16 C17 N20 . . 116.1(5) ?
C17 C18 C19 . . 120.5(6) ?
C17 C18 H18 . . 119.7 ?
C19 C18 H18 . . 119.7 ?
C14 C19 C18 . . 119.7(6) ?
C14 C19 H19 . . 120.1 ?
C18 C19 H19 . . 120.1 ?
C21 N20 C17 . . 130.0(5) ?
C21 N20 H20 . . 115 ?
C17 N20 H20 . . 115 ?
O22 C21 N20 . . 121.9(6) ?
O22 C21 C23 . . 121.6(6) ?
N20 C21 C23 . . 116.5(6) ?
C21 C23 H23A . . 109.5 ?
C21 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C21 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C29 C24 C25 . . 118.1(6) ?
C29 C24 C30 . . 120.7(7) ?
C25 C24 C30 . . 121.2(6) ?
C26 C25 N33 . . 120.9(6) ?
C26 C25 C24 . . 119.5(6) ?
N33 C25 C24 . . 119.6(6) ?
C27 C26 C25 . . 120.4(6) ?
C27 C26 H26 . . 119.8 ?
C25 C26 H26 . . 119.8 ?
C26 C27 C28 . . 120.7(7) ?
C26 C27 H27 . . 119.7 ?
C28 C27 H27 . . 119.7 ?
C29 C28 C27 . . 118.8(7) ?
C29 C28 H28 . . 120.6 ?
C27 C28 H28 . . 120.6 ?
C28 C29 C24 . . 122.4(7) ?
C28 C29 H29 . . 118.8 ?
C24 C29 H29 . . 118.8 ?
O32 C30 O31 . . 120.0(6) ?
O32 C30 C24 . . 125.8(7) ?
O31 C30 C24 . . 114.2(6) ?
C30 O31 H31 . . 109.5 ?
C25 N33 S34 . . 124.4(4) ?
C25 N33 H33 . . 117.8 ?
S34 N33 H33 . . 117.8 ?
O35 S34 O36 . . 119.3(3) ?
O35 S34 N33 . . 109.3(3) ?
O36 S34 N33 . . 103.7(3) ?
O35 S34 C37 . . 107.7(3) ?
O36 S34 C37 . . 109.1(3) ?
N33 S34 C37 . . 107.1(3) ?
C38 C37 C42 . . 119.3(6) ?
C38 C37 S34 . . 119.4(6) ?
C42 C37 S34 . . 121.2(5) ?
C37 C38 C39 . . 122.1(6) ?
C37 C38 H38 . . 118.9 ?
C39 C38 H38 . . 118.9 ?
C38 C39 C40 . . 117.8(6) ?
C38 C39 H39 . . 121.1 ?
C40 C39 H39 . . 121.1 ?
C39 C40 C41 . . 120.6(7) ?
C39 C40 N43 . . 122.2(6) ?
C41 C40 N43 . . 117.2(6) ?
C42 C41 C40 . . 119.3(6) ?
C42 C41 H41 . . 120.3 ?
C40 C41 H41 . . 120.3 ?
C41 C42 C37 . . 120.8(6) ?
C41 C42 H42 . . 119.6 ?
C37 C42 H42 . . 119.6 ?
C44 N43 C40 . . 128.8(6) ?
C44 N43 H43 . . 115.6 ?
C40 N43 H43 . . 115.6 ?
O45 C44 N43 . . 121.7(7) ?
O45 C44 C46 . . 122.7(7) ?
N43 C44 C46 . . 115.5(6) ?
C44 C46 H46A . . 109.5 ?
C44 C46 H46B . . 109.5 ?
H46A C46 H46B . . 109.5 ?
C44 C46 H46C . . 109.5 ?
H46A C46 H46C . . 109.5 ?
H46B C46 H46C . . 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
C1 C2 . 1.387(8) ?
C1 C6 . 1.389(9) ?
C1 C7 . 1.482(8) ?
C2 C3 . 1.379(8) ?
C2 N10 . 1.412(7) ?
C3 C4 . 1.356(9) ?
C3 H3 . 0.93 ?
C4 C5 . 1.378(9) ?
C4 H4 . 0.93 ?
C5 C6 . 1.374(9) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 O8 . 1.206(7) ?
C7 O9 . 1.322(7) ?
O9 H9 . 0.82 ?
N10 S11 . 1.611(5) ?
N10 H10 . 0.86 ?
S11 O13 . 1.415(4) ?
S11 O12 . 1.423(4) ?
S11 C14 . 1.754(6) ?
C14 C19 . 1.380(7) ?
C14 C15 . 1.382(8) ?
C15 C16 . 1.355(8) ?
C15 H15 . 0.93 ?
C16 C17 . 1.386(7) ?
C16 H16 . 0.93 ?
C17 C18 . 1.348(8) ?
C17 N20 . 1.414(7) ?
C18 C19 . 1.382(8) ?
C18 H18 . 0.93 ?
C19 H19 . 0.93 ?
N20 C21 . 1.340(7) ?
N20 H20 . 0.86 ?
C21 O22 . 1.244(6) ?
C21 C23 . 1.497(8) ?
C23 H23A . 0.96 ?
C23 H23B . 0.96 ?
C23 H23C . 0.96 ?
C24 C29 . 1.389(8) ?
C24 C25 . 1.403(8) ?
C24 C30 . 1.450(8) ?
C25 C26 . 1.399(8) ?
C25 N33 . 1.402(7) ?
C26 C27 . 1.370(8) ?
C26 H26 . 0.93 ?
C27 C28 . 1.386(9) ?
C27 H27 . 0.93 ?
C28 C29 . 1.372(9) ?
C28 H28 . 0.93 ?
C29 H29 . 0.93 ?
C30 O32 . 1.215(7) ?
C30 O31 . 1.332(8) ?
O31 H31 . 0.82 ?
N33 S34 . 1.641(5) ?
N33 H33 . 0.86 ?
S34 O35 . 1.429(4) ?
S34 O36 . 1.438(4) ?
S34 C37 . 1.758(7) ?
C37 C38 . 1.358(8) ?
C37 C42 . 1.366(8) ?
C38 C39 . 1.371(9) ?
C38 H38 . 0.93 ?
C39 C40 . 1.383(8) ?
C39 H39 . 0.93 ?
C40 C41 . 1.385(8) ?
C40 N43 . 1.412(7) ?
C41 C42 . 1.363(8) ?
C41 H41 . 0.93 ?
C42 H42 . 0.93 ?
N43 C44 . 1.385(8) ?
N43 H43 . 0.86 ?
C44 O45 . 1.224(7) ?
C44 C46 . 1.503(9) ?
C46 H46A . 0.96 ?
C46 H46B . 0.96 ?
C46 H46C . 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
O9 H9 O22 2_646 0.82 1.84 2.649(6) 168
N10 H10 O8 . 0.86 2.13 2.624(7) 116
N20 H20 O13 2_655 0.86 2.24 3.073(6) 164
O31 H31 O45 1_455 0.82 1.81 2.623(6) 174
N33 H33 O32 . 0.86 2.17 2.641(7) 114
N43 H43 O36 2_646 0.86 2.11 2.958(7) 168
C23 H23B Cg1 . 0.96 2.74 3.6110(15) 151
C46 H46C Cg2 . 0.96 2.71 3.5821(13) 151
