##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
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##############################################################################
data_global
_audit_creation_method     'SHELXL-2018/3'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2023-05-15
_journal_date_accepted     2023-07-07
_journal_name_full     'IUCrData'
_journal_year     2023
_journal_volume     8
_journal_issue      7
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314623005989
_journal_coeditor_code     BT4139
_publ_contact_author_name
;
Dr Sihui Long
;
_publ_contact_author_address
;
School of Chemical Engineering and Pharmacy
Wuhan Institute of Technology
Wuhan, Hubei 430205
People's Republic of China
;
_publ_contact_author_email     'sihuilong@wit.edu.cn'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '86-177-6250-2329'
_publ_section_title
;
4-(3-Chloroanilino)benzoic acid
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Liu, Xiaoting' .
;
School of Chemical Engineering and Pharmacy
Wuhan Institute of Technology
Wuhan, Hubei 430205
People's Republic of China
;
    'Long, Sihui' .
;
School of Chemical Engineering and Pharmacy
Wuhan Institute of Technology
Wuhan, Hubei 430205
People's Republic of China
;
_publ_section_synopsis
;
High quality crystals of 4-(3-chloroanilino)benzoic acid were grown in
acetonitrile and its crystal structure was determined by single-crystal X-ray
diffraction.
;
data_I
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_name_systematic
;
4-(3-Chloroanilino)benzoic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 Cl N O2'
_chemical_formula_sum     'C13 H10 Cl N O2'
_chemical_formula_iupac     'C13 H10 Cl N O2'
_chemical_formula_weight     247.67
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.8865(2)
_cell_length_b     10.31441(18)
_cell_length_c     11.0885(2)
_cell_angle_alpha     90
_cell_angle_beta     113.817(3)
_cell_angle_gamma     90
_cell_volume     1139.08(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5783
_cell_measurement_theta_min     4.2890
_cell_measurement_theta_max     77.1240
_cell_measurement_temperature     288.2(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'clear light colourless'
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.444
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     2.878
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_absorpt_correction_T_min     0.37471
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     288.2(2)
_diffrn_source     'Rotating-anode X-ray tube'
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type
                       'Rigaku Oxford Diffraction, Synergy Custom system, HyPix'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector     'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean     10.0000
_diffrn_reflns_number     7087
_diffrn_reflns_av_R_equivalents     0.0251
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_theta_min     4.439
_diffrn_reflns_theta_max     77.369
_diffrn_reflns_theta_full     67.684
_diffrn_measured_fraction_theta_max     0.946
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     14
_diffrn_radiation_probe     x-ray
_refine_special_details
;
The positions of all H atoms were obtained from the difference Fourier map. H
atoms bonded to N1 and O1 were freely refined. Other H atoms were positioned
geometrically with C---H = 0.93 Å and constraioned to ride on their parent
atoms with Uiso(H) = 1.2Ueq(C).
;
_reflns_number_total     2278
_reflns_number_gt     2045
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0496
_refine_ls_R_factor_gt     0.0466
_refine_ls_wR_factor_gt     0.1388
_refine_ls_wR_factor_ref     0.1426
_refine_ls_goodness_of_fit_ref     1.079
_refine_ls_restrained_S_all     1.079
_refine_ls_number_reflns     2278
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0850P)²+0.1891P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.351
_refine_diff_density_min     -0.367
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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'
    'Cl' 'Cl' 0.3639 0.7018
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlisPro 1.171.41.113a (Rigaku OD, 2022)
;
_computing_cell_refinement
;
CrysAlisPro 1.171.41.113a (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.113a (Rigaku OD, 2022)
;
_computing_structure_solution
;
SHELXS  (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 1.08885(6) 0.18033(6) 0.52451(6) 0.0806(3) Uani d 1 . .
    O O1 0.56772(18) 0.39086(13) 0.91797(17) 0.0746(4) Uani d 1 . .
    H H1 0.553(4) 0.394(4) 0.992(4) 0.150(15) Uiso d 1 . .
    O O2 0.53662(16) 0.60395(13) 0.90499(15) 0.0729(4) Uani d 1 . .
    N N1 0.72634(17) 0.52920(19) 0.43865(17) 0.0663(4) Uani d 1 . .
    C C1 0.69502(16) 0.51613(18) 0.54768(17) 0.0547(4) Uani d 1 . .
    C C2 0.69426(18) 0.39841(17) 0.60907(19) 0.0583(4) Uani d 1 . .
    H H2 0.718984 0.322720 0.579069 0.070 Uiso calc 1 . .
    C C3 0.65700(18) 0.39349(16) 0.71420(19) 0.0566(4) Uani d 1 . .
    H H3 0.658316 0.314588 0.755293 0.068 Uiso calc 1 . .
    C C4 0.61751(16) 0.50519(15) 0.75936(17) 0.0511(4) Uani d 1 . .
    C C5 0.61631(19) 0.62229(17) 0.69628(19) 0.0594(4) Uani d 1 . .
    H H5 0.588815 0.697547 0.724422 0.071 Uiso calc 1 . .
    C C6 0.6552(2) 0.62786(19) 0.5931(2) 0.0634(5) Uani d 1 . .
    H H6 0.655065 0.707079 0.552966 0.076 Uiso calc 1 . .
    C C7 0.57147(17) 0.50230(15) 0.86682(18) 0.0542(4) Uani d 1 . .
    C C8 0.80918(17) 0.4555(2) 0.39658(17) 0.0577(4) Uani d 1 . .
    C C9 0.89546(17) 0.3606(2) 0.47289(16) 0.0573(4) Uani d 1 . .
    H H9 0.897922 0.340034 0.555486 0.069 Uiso calc 1 . .
    C C10 0.97786(19) 0.2970(2) 0.42486(18) 0.0612(5) Uani d 1 . .
    C C11 0.9792(2) 0.3250(2) 0.3038(2) 0.0717(6) Uani d 1 . .
    H H11 1.035995 0.281079 0.273724 0.086 Uiso calc 1 . .
    C C12 0.8938(2) 0.4199(3) 0.22921(19) 0.0781(6) Uani d 1 . .
    H H12 0.893432 0.441247 0.147575 0.094 Uiso calc 1 . .
    C C13 0.8084(2) 0.4843(2) 0.27326(19) 0.0710(5) Uani d 1 . .
    H H13 0.750126 0.547161 0.220491 0.085 Uiso calc 1 . .
    H H1A 0.707(3) 0.599(2) 0.404(2) 0.076(7) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Cl1 C10 . 1.746(2) ?
    O1 H1 . 0.90(4) ?
    O1 C7 . 1.290(2) ?
    O2 C7 . 1.246(2) ?
    N1 C1 . 1.389(2) ?
    N1 C8 . 1.396(3) ?
    N1 H1A . 0.80(3) ?
    C1 C2 . 1.394(3) ?
    C1 C6 . 1.395(3) ?
    C2 H2 . 0.9300 ?
    C2 C3 . 1.381(3) ?
    C3 H3 . 0.9300 ?
    C3 C4 . 1.392(2) ?
    C4 C5 . 1.393(2) ?
    C4 C7 . 1.468(2) ?
    C5 H5 . 0.9300 ?
    C5 C6 . 1.372(3) ?
    C6 H6 . 0.9300 ?
    C8 C9 . 1.383(3) ?
    C8 C13 . 1.396(3) ?
    C9 H9 . 0.9300 ?
    C9 C10 . 1.380(3) ?
    C10 C11 . 1.379(3) ?
    C11 H11 . 0.9300 ?
    C11 C12 . 1.374(3) ?
    C12 H12 . 0.9300 ?
    C12 C13 . 1.383(3) ?
    C13 H13 . 0.9300 ?
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
    C7 O1 H1 . . 115(3) ?
    C1 N1 C8 . . 131.05(18) ?
    C1 N1 H1A . . 113.1(18) ?
    C8 N1 H1A . . 114.2(19) ?
    N1 C1 C2 . . 124.18(17) ?
    N1 C1 C6 . . 117.08(17) ?
    C2 C1 C6 . . 118.66(16) ?
    C1 C2 H2 . . 119.8 ?
    C3 C2 C1 . . 120.39(16) ?
    C3 C2 H2 . . 119.8 ?
    C2 C3 H3 . . 119.6 ?
    C2 C3 C4 . . 120.79(16) ?
    C4 C3 H3 . . 119.6 ?
    C3 C4 C5 . . 118.60(16) ?
    C3 C4 C7 . . 122.12(15) ?
    C5 C4 C7 . . 119.22(15) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 C4 . . 120.76(17) ?
    C6 C5 H5 . . 119.6 ?
    C1 C6 H6 . . 119.6 ?
    C5 C6 C1 . . 120.78(17) ?
    C5 C6 H6 . . 119.6 ?
    O1 C7 C4 . . 117.19(15) ?
    O2 C7 O1 . . 122.19(16) ?
    O2 C7 C4 . . 120.62(15) ?
    C9 C8 N1 . . 123.47(16) ?
    C9 C8 C13 . . 118.95(18) ?
    C13 C8 N1 . . 117.50(19) ?
    C8 C9 H9 . . 120.4 ?
    C10 C9 C8 . . 119.14(16) ?
    C10 C9 H9 . . 120.4 ?
    C9 C10 Cl1 . . 118.36(14) ?
    C11 C10 Cl1 . . 118.92(16) ?
    C11 C10 C9 . . 122.7(2) ?
    C10 C11 H11 . . 121.2 ?
    C12 C11 C10 . . 117.70(19) ?
    C12 C11 H11 . . 121.2 ?
    C11 C12 H12 . . 119.4 ?
    C11 C12 C13 . . 121.21(18) ?
    C13 C12 H12 . . 119.4 ?
    C8 C13 H13 . . 119.8 ?
    C12 C13 C8 . . 120.3(2) ?
    C12 C13 H13 . . 119.8 ?
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
    Cl1 C10 C11 C12 . . . . -178.04(17) ?
    N1 C1 C2 C3 . . . . -177.58(17) ?
    N1 C1 C6 C5 . . . . 176.83(17) ?
    N1 C8 C9 C10 . . . . -177.07(18) ?
    N1 C8 C13 C12 . . . . 176.3(2) ?
    C1 N1 C8 C9 . . . . -10.4(3) ?
    C1 N1 C8 C13 . . . . 172.68(19) ?
    C1 C2 C3 C4 . . . . 1.1(3) ?
    C2 C1 C6 C5 . . . . 0.1(3) ?
    C2 C3 C4 C5 . . . . 0.0(3) ?
    C2 C3 C4 C7 . . . . 177.14(16) ?
    C3 C4 C5 C6 . . . . -1.0(3) ?
    C3 C4 C7 O1 . . . . -0.6(3) ?
    C3 C4 C7 O2 . . . . -179.92(17) ?
    C4 C5 C6 C1 . . . . 0.9(3) ?
    C5 C4 C7 O1 . . . . 176.54(17) ?
    C5 C4 C7 O2 . . . . -2.8(3) ?
    C6 C1 C2 C3 . . . . -1.1(3) ?
    C7 C4 C5 C6 . . . . -178.23(17) ?
    C8 N1 C1 C2 . . . . -28.5(3) ?
    C8 N1 C1 C6 . . . . 155.0(2) ?
    C8 C9 C10 Cl1 . . . . 178.49(14) ?
    C8 C9 C10 C11 . . . . 0.8(3) ?
    C9 C8 C13 C12 . . . . -0.7(3) ?
    C9 C10 C11 C12 . . . . -0.4(3) ?
    C10 C11 C12 C13 . . . . -0.7(3) ?
    C11 C12 C13 C8 . . . . 1.2(3) ?
    C13 C8 C9 C10 . . . . -0.2(3) ?
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
    O1 H1 O2 3_667 0.90(4) 1.78(4) 2.6359(19) 160(4) yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.672
_shelx_estimated_absorpt_T_max     0.782
