#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/89/2208931.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_2208931
loop_
_publ_author_name
'Zhi-Hong Nan'
'Jun-De Xing'
_publ_section_title
;
 4-(Tosylamino)benzoic acid
;
_journal_coeditor_code           KP2012
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1978
_journal_page_last               o1979
_journal_paper_doi               10.1107/S1600536806013055
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H13 N O4 S'
_chemical_formula_moiety         'C14 H13 N O4 S'
_chemical_formula_sum            'C14 H13 N O4 S'
_chemical_formula_weight         291.31
_chemical_name_systematic
;
4-(Tosylamino)benzoic 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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.11(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1626(10)
_cell_length_b                   13.178(3)
_cell_length_c                   20.003(4)
_cell_measurement_reflns_used    10798
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      3.09
_cell_volume                     1359.9(5)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_reduction        RAPID-AUTO
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP area-detector'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10798
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_correction_T_min  0.8964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.541
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0386
_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)+(0.0861P)²+0.1493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                2182
_reflns_number_total             2491
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2012.cif
_cod_data_source_block           I
_cod_original_cell_volume        1360.0(5)
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208931
_cod_database_fobs_code          2208931
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
N N1 0.2127(3) 0.53802(10) 0.21023(7) 0.0369(3) Uani d . 1
H H1A 0.0927 0.4943 0.2013 0.044 Uiso calc R 1
S S1 0.40751(7) 0.52607(3) 0.27695(2) 0.03728(18) Uani d . 1
O O1 0.3306(3) 0.43405(10) 0.30837(7) 0.0513(4) Uani d . 1
O O2 0.6664(2) 0.53770(10) 0.25470(7) 0.0504(4) Uani d . 1
O O3 0.2551(3) 0.95783(9) 0.05169(7) 0.0518(4) Uani d . 1
H H3B 0.3107 1.0048 0.0294 0.078 Uiso calc R 1
O O4 0.6109(3) 0.88246(10) 0.01612(7) 0.0516(4) Uani d . 1
C C1 0.0939(6) 0.88795(19) 0.44025(12) 0.0766(7) Uani d . 1
H H1C -0.0389 0.8676 0.4698 0.115 Uiso calc R 1
H H1D 0.0259 0.9382 0.4096 0.115 Uiso calc R 1
H H1E 0.2376 0.9159 0.4659 0.115 Uiso calc R 1
C C2 0.1832(4) 0.79736(16) 0.40178(9) 0.0536(5) Uani d . 1
C C3 0.3763(5) 0.80551(16) 0.35561(11) 0.0618(6) Uani d . 1
H H3A 0.4547 0.8681 0.3492 0.074 Uiso calc R 1
C C4 0.4548(4) 0.72298(16) 0.31901(10) 0.0553(5) Uani d . 1
H H4A 0.5852 0.7297 0.2884 0.066 Uiso calc R 1
C C5 0.3363(3) 0.62963(13) 0.32849(8) 0.0389(4) Uani d . 1
C C6 0.1442(4) 0.61960(15) 0.37465(9) 0.0489(5) Uani d . 1
H H6A 0.0657 0.5571 0.3812 0.059 Uiso calc R 1
C C7 0.0711(4) 0.70281(16) 0.41059(9) 0.0553(5) Uani d . 1
H H7A -0.0572 0.6957 0.4417 0.066 Uiso calc R 1
C C8 0.2500(3) 0.62381(12) 0.16756(8) 0.0340(4) Uani d . 1
C C9 0.0918(3) 0.70790(14) 0.17023(9) 0.0425(4) Uani d . 1
H H9A -0.0460 0.7085 0.1989 0.051 Uiso calc R 1
C C10 0.1375(3) 0.79134(13) 0.13046(9) 0.0431(4) Uani d . 1
H H10A 0.0296 0.8477 0.1321 0.052 Uiso calc R 1
C C11 0.3447(3) 0.79099(12) 0.08809(7) 0.0336(3) Uani d . 1
C C12 0.4995(3) 0.70545(13) 0.08451(8) 0.0413(4) Uani d . 1
H H12A 0.6365 0.7044 0.0556 0.050 Uiso calc R 1
C C13 0.4515(4) 0.62198(13) 0.12350(8) 0.0424(4) Uani d . 1
H H13A 0.5541 0.5643 0.1203 0.051 Uiso calc R 1
C C14 0.4101(3) 0.88239(12) 0.04917(8) 0.0365(4) 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
_geom_angle_publ_flag
C8 N1 S1 117.75(10) ?
C8 N1 H1A 121.1 ?
S1 N1 H1A 121.1 ?
O1 S1 O2 120.33(8) yes
O1 S1 N1 105.43(8) ?
O2 S1 N1 106.66(8) ?
O1 S1 C5 109.49(8) ?
O2 S1 C5 108.47(8) ?
N1 S1 C5 105.44(7) ?
C14 O3 H3B 109.5 ?
C2 C1 H1C 109.5 ?
C2 C1 H1D 109.5 ?
H1C C1 H1D 109.5 ?
C2 C1 H1E 109.5 ?
H1C C1 H1E 109.5 ?
H1D C1 H1E 109.5 ?
C7 C2 C3 117.85(19) ?
C7 C2 C1 120.7(2) ?
C3 C2 C1 121.4(2) yes
C4 C3 C2 121.61(19) ?
C4 C3 H3A 119.2 ?
C2 C3 H3A 119.2 ?
C3 C4 C5 119.06(18) ?
C3 C4 H4A 120.5 ?
C5 C4 H4A 120.5 ?
C6 C5 C4 120.30(18) ?
C6 C5 S1 119.14(14) ?
C4 C5 S1 120.31(13) ?
C7 C6 C5 119.37(17) ?
C7 C6 H6A 120.3 ?
C5 C6 H6A 120.3 ?
C6 C7 C2 121.80(17) ?
C6 C7 H7A 119.1 ?
C2 C7 H7A 119.1 ?
C9 C8 C13 119.83(15) ?
C9 C8 N1 121.18(14) ?
C13 C8 N1 118.99(14) ?
C8 C9 C10 120.19(15) ?
C8 C9 H9A 119.9 ?
C10 C9 H9A 119.9 ?
C9 C10 C11 120.01(15) ?
C9 C10 H10A 120.0 ?
C11 C10 H10A 120.0 ?
C12 C11 C10 119.53(15) ?
C12 C11 C14 119.47(14) yes
C10 C11 C14 120.94(14) ?
C13 C12 C11 120.33(15) ?
C13 C12 H12A 119.8 ?
C11 C12 H12A 119.8 ?
C12 C13 C8 120.04(15) ?
C12 C13 H13A 120.0 ?
C8 C13 H13A 120.0 ?
O4 C14 O3 123.56(15) ?
O4 C14 C11 119.24(14) yes
O3 C14 C11 117.19(14) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C8 1.4340(19) yes
N1 S1 1.6490(15) yes
N1 H1A 0.8600 ?
S1 O1 1.4287(13) yes
S1 O2 1.4323(13) ?
S1 C5 1.7574(18) yes
O3 C14 1.278(2) ?
O3 H3B 0.8200 ?
O4 C14 1.2502(19) yes
C1 C2 1.502(3) ?
C1 H1C 0.9600 ?
C1 H1D 0.9600 ?
C1 H1E 0.9600 ?
C2 C7 1.388(3) ?
C2 C3 1.388(3) ?
C3 C4 1.380(3) ?
C3 H3A 0.9300 ?
C4 C5 1.390(3) ?
C4 H4A 0.9300 ?
C5 C6 1.386(2) ?
C6 C7 1.372(3) ?
C6 H6A 0.9300 ?
C7 H7A 0.9300 ?
C8 C9 1.379(2) ?
C8 C13 1.388(2) ?
C9 C10 1.383(2) ?
C9 H9A 0.9300 ?
C10 C11 1.389(2) ?
C10 H10A 0.9300 ?
C11 C12 1.385(2) yes
C11 C14 1.480(2) ?
C12 C13 1.376(2) ?
C12 H12A 0.9300 ?
C13 H13A 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
N1 H1A O2 1_455 0.86 2.55 2.9882(19) 113
O3 H3B O4 3_675 0.82 1.80 2.6109(18) 171
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
_geom_torsion_publ_flag
C8 N1 S1 O1 -178.53(12) yes
C8 N1 S1 O2 -49.53(13) ?
C8 N1 S1 C5 65.67(13) ?
C7 C2 C3 C4 0.4(3) ?
C1 C2 C3 C4 -178.5(2) yes
C2 C3 C4 C5 0.3(3) ?
C3 C4 C5 C6 -0.7(3) ?
C3 C4 C5 S1 173.52(16) ?
O1 S1 C5 C6 -23.76(16) ?
O2 S1 C5 C6 -156.84(14) ?
N1 S1 C5 C6 89.22(15) ?
O1 S1 C5 C4 161.90(15) yes
O2 S1 C5 C4 28.83(17) yes
N1 S1 C5 C4 -85.11(16) ?
C4 C5 C6 C7 0.4(3) ?
S1 C5 C6 C7 -173.94(15) ?
C5 C6 C7 C2 0.4(3) ?
C3 C2 C7 C6 -0.8(3) ?
C1 C2 C7 C6 178.1(2) ?
S1 N1 C8 C9 -101.33(17) ?
S1 N1 C8 C13 77.89(17) ?
C13 C8 C9 C10 -1.7(3) ?
N1 C8 C9 C10 177.51(15) ?
C8 C9 C10 C11 -0.6(3) ?
C9 C10 C11 C12 2.0(3) ?
C9 C10 C11 C14 -175.01(16) ?
C10 C11 C12 C13 -1.1(3) ?
C14 C11 C12 C13 175.92(15) ?
C11 C12 C13 C8 -1.1(3) ?
C9 C8 C13 C12 2.6(3) ?
N1 C8 C13 C12 -176.66(15) ?
C12 C11 C14 O4 -3.3(2) yes
C10 C11 C14 O4 173.73(16) ?
C12 C11 C14 O3 176.93(15) ?
C10 C11 C14 O3 -6.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 488020
2 PubChem 561385
