##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# 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 journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.07.31 svn.r3643 for OlexSys, GUI svn.r5859)
;
_chemical_name_systematic
;
2-Chloro-5-nitrobenzoic acid--nicotinamide (1/1)
;
_chemical_name_common     'Nicotinamide benzoic acid'
_chemical_formula_moiety     'C7 H4 Cl N O4, C6 H6 N2 O'
_chemical_formula_sum     'C13 H10 Cl N3 O5'
_chemical_formula_iupac     'C7 H4 Cl N O4, C6 H6 N2 O'
_chemical_formula_weight     323.69
_chemical_melting_point     159.7
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_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     7.48970(10)
_cell_length_b     26.3607(5)
_cell_length_c     7.06230(10)
_cell_angle_alpha     90
_cell_angle_beta     96.3560(10)
_cell_angle_gamma     90
_cell_volume     1385.77(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4123
_cell_measurement_theta_min     1.5
_cell_measurement_theta_max     30.2
_cell_measurement_temperature     123(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.280
_exptl_crystal_size_mid     0.220
_exptl_crystal_size_min     0.150
_exptl_crystal_density_diffrn     1.551
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.305
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_absorpt_correction_T_min     0.874
_exptl_absorpt_correction_T_max     0.908
_diffrn_ambient_temperature     123(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa APEXII DUO'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     29950
_diffrn_reflns_av_R_equivalents     0.0372
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_theta_min     1.545
_diffrn_reflns_theta_max     30.225
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -37
_diffrn_reflns_limit_k_max     37
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     9
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Single-crystal X-ray diffraction data were collected on a Bruker
KAPPA APEX II DUO diffractometer using graphite-monochromated
Mo-Kα radiation (λ = 0.71073Å)(Bruker, 2012). The data collection
was performed at 153(2) K. The temperature was monitored by an Oxford
Cryostream cooling system (Oxford Cryostat). the program SAINT
(Bruker, 2012) were used for cell refinement and data reduction.
The data were scaled and absorption correction performed using
SADABS(Bruker, 2001). The structure was solved by direct methods
using SHELXS-18(Sheldrick, 2015) and refined by full-matrix
least-squares methods based on F2 using SHELXL-2018/3(Sheldrick, 2015).
The computing , Mercury(Macrae et al., 2008) and PLATON (Spek, 2009)
were used for molecular graphics and molecular interactions. All non-hydrogen
atoms were refined anisotropically.
;
_reflns_number_total     4123
_reflns_number_gt     3316
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0500
_refine_ls_R_factor_gt     0.0375
_refine_ls_wR_factor_gt     0.0876
_refine_ls_wR_factor_ref     0.0936
_refine_ls_goodness_of_fit_ref     1.077
_refine_ls_restrained_S_all     1.077
_refine_ls_number_reflns     4123
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0394P)²+0.4303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.302
_refine_diff_density_min     -0.263
_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' 0.0033 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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_structure_solution
;
SHELXS18 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009) and
PLATON (Spek, 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 -0.18141(5) 0.18331(2) 0.33099(6) 0.04137(12) Uani d 1 . .
    O O2 0.39368(12) 0.16413(3) 0.29015(14) 0.0267(2) Uani d 1 . .
    O O1 0.87918(13) 0.45197(3) 1.35865(13) 0.0268(2) Uani d 1 . .
    O O5 0.29333(16) 0.39338(4) 0.38136(16) 0.0381(3) Uani d 1 . .
    O O3 0.16833(14) 0.13103(3) 0.43221(14) 0.0308(2) Uani d 1 . .
    O O4 0.50015(15) 0.34087(4) 0.32242(18) 0.0417(3) Uani d 1 . .
    N N1 0.87836(15) 0.53606(4) 1.29452(16) 0.0226(2) Uani d 1 . .
    N N2 0.57395(14) 0.41744(4) 0.85619(15) 0.0208(2) Uani d 1 . .
    N N3 0.34615(16) 0.35059(4) 0.35149(16) 0.0262(2) Uani d 1 . .
    C C6 0.75383(15) 0.50921(4) 0.89924(17) 0.0189(2) Uani d 1 . .
    C C1 0.83945(15) 0.48801(4) 1.24921(17) 0.0193(2) Uani d 1 . .
    C C2 0.74506(15) 0.47734(4) 1.05512(16) 0.0172(2) Uani d 1 . .
    C C12 0.21719(17) 0.30889(4) 0.35036(17) 0.0209(2) Uani d 1 . .
    C C4 0.59051(17) 0.44720(5) 0.70484(18) 0.0221(2) Uani d 1 . .
    C C13 0.28144(16) 0.25993(4) 0.35032(17) 0.0193(2) Uani d 1 . .
    C C5 0.67736(17) 0.49327(5) 0.72106(18) 0.0217(2) Uani d 1 . .
    C C9 -0.02066(17) 0.23039(5) 0.34499(19) 0.0243(3) Uani d 1 . .
    C C3 0.65244(16) 0.43172(4) 1.02733(17) 0.0201(2) Uani d 1 . .
    C C8 0.16239(16) 0.21927(4) 0.35036(16) 0.0191(2) Uani d 1 . .
    C C10 -0.08225(18) 0.28024(5) 0.3432(2) 0.0291(3) Uani d 1 . .
    C C7 0.24078(17) 0.16659(4) 0.36051(17) 0.0205(2) Uani d 1 . .
    C C11 0.03681(19) 0.32024(5) 0.34746(19) 0.0261(3) Uani d 1 . .
    H H3 0.639(2) 0.4084(6) 1.134(2) 0.022(4) Uiso d 1 . .
    H H6 0.813(2) 0.5415(6) 0.909(2) 0.022(4) Uiso d 1 . .
    H H13 0.404(2) 0.2537(6) 0.352(2) 0.028(4) Uiso d 1 . .
    H H4 0.540(2) 0.4339(6) 0.581(2) 0.025(4) Uiso d 1 . .
    H H5 0.691(2) 0.5138(6) 0.612(2) 0.026(4) Uiso d 1 . .
    H H1A 0.947(2) 0.5426(6) 1.405(3) 0.035(4) Uiso d 1 . .
    H H1B 0.850(2) 0.5613(7) 1.216(3) 0.038(5) Uiso d 1 . .
    H H11 -0.006(2) 0.3550(7) 0.346(3) 0.040(5) Uiso d 1 . .
    H H10 -0.208(3) 0.2870(7) 0.338(3) 0.042(5) Uiso d 1 . .
    H H2 0.462(3) 0.1292(9) 0.326(3) 0.074(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 C9 . 1.7244(13) ?
    O2 C7 . 1.2994(15) ?
    O2 H2 . 1.07(2) ?
    O1 C1 . 1.2399(14) ?
    O5 N3 . 1.2215(15) ?
    O3 C7 . 1.2208(14) ?
    O4 N3 . 1.2209(16) ?
    N1 C1 . 1.3307(16) ?
    N1 H1A . 0.901(19) ?
    N1 H1B . 0.876(18) ?
    N2 C3 . 1.3383(16) ?
    N2 C4 . 1.3426(16) ?
    N3 C12 . 1.4626(16) ?
    C6 C5 . 1.3887(17) ?
    C6 C2 . 1.3922(16) ?
    C6 H6 . 0.959(15) ?
    C1 C2 . 1.4977(16) ?
    C2 C3 . 1.3913(16) ?
    C12 C13 . 1.3774(16) ?
    C12 C11 . 1.3816(18) ?
    C4 C5 . 1.3766(17) ?
    C4 H4 . 0.977(16) ?
    C13 C8 . 1.3941(16) ?
    C13 H13 . 0.932(16) ?
    C5 H5 . 0.957(16) ?
    C9 C10 . 1.3921(19) ?
    C9 C8 . 1.3984(17) ?
    C3 H3 . 0.984(15) ?
    C8 C7 . 1.5064(16) ?
    C10 C11 . 1.379(2) ?
    C10 H10 . 0.955(18) ?
    C11 H11 . 0.971(18) ?
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 O2 H2 . . 111.9(13) ?
    C1 N1 H1A . . 118.6(11) ?
    C1 N1 H1B . . 122.7(12) ?
    H1A N1 H1B . . 118.4(16) ?
    C3 N2 C4 . . 118.98(10) ?
    O4 N3 O5 . . 123.56(12) ?
    O4 N3 C12 . . 118.49(11) ?
    O5 N3 C12 . . 117.95(12) ?
    C5 C6 C2 . . 118.89(11) ?
    C5 C6 H6 . . 118.5(9) ?
    C2 C6 H6 . . 122.6(9) ?
    O1 C1 N1 . . 123.25(11) ?
    O1 C1 C2 . . 118.88(10) ?
    N1 C1 C2 . . 117.87(11) ?
    C3 C2 C6 . . 118.46(11) ?
    C3 C2 C1 . . 117.96(10) ?
    C6 C2 C1 . . 123.47(10) ?
    C13 C12 C11 . . 122.95(11) ?
    C13 C12 N3 . . 118.27(11) ?
    C11 C12 N3 . . 118.78(11) ?
    N2 C4 C5 . . 122.26(11) ?
    N2 C4 H4 . . 116.2(9) ?
    C5 C4 H4 . . 121.6(9) ?
    C12 C13 C8 . . 119.79(11) ?
    C12 C13 H13 . . 120.6(9) ?
    C8 C13 H13 . . 119.6(9) ?
    C4 C5 C6 . . 119.08(11) ?
    C4 C5 H5 . . 121.5(9) ?
    C6 C5 H5 . . 119.4(9) ?
    C10 C9 C8 . . 121.40(11) ?
    C10 C9 Cl1 . . 116.76(10) ?
    C8 C9 Cl1 . . 121.80(10) ?
    N2 C3 C2 . . 122.20(11) ?
    N2 C3 H3 . . 116.1(9) ?
    C2 C3 H3 . . 121.7(9) ?
    C13 C8 C9 . . 117.65(11) ?
    C13 C8 C7 . . 117.57(10) ?
    C9 C8 C7 . . 124.77(11) ?
    C11 C10 C9 . . 120.57(12) ?
    C11 C10 H10 . . 119.3(11) ?
    C9 C10 H10 . . 120.1(11) ?
    O3 C7 O2 . . 124.84(11) ?
    O3 C7 C8 . . 122.60(11) ?
    O2 C7 C8 . . 112.54(10) ?
    C10 C11 C12 . . 117.62(12) ?
    C10 C11 H11 . . 120.6(11) ?
    C12 C11 H11 . . 121.8(11) ?
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
    C5 C6 C2 C3 . . . . -2.96(17) ?
    C5 C6 C2 C1 . . . . 173.20(11) ?
    O1 C1 C2 C3 . . . . 21.57(16) ?
    N1 C1 C2 C3 . . . . -159.19(11) ?
    O1 C1 C2 C6 . . . . -154.61(12) ?
    N1 C1 C2 C6 . . . . 24.63(17) ?
    O4 N3 C12 C13 . . . . 11.29(17) ?
    O5 N3 C12 C13 . . . . -168.81(12) ?
    O4 N3 C12 C11 . . . . -168.07(12) ?
    O5 N3 C12 C11 . . . . 11.83(17) ?
    C3 N2 C4 C5 . . . . -3.55(18) ?
    C11 C12 C13 C8 . . . . -1.03(19) ?
    N3 C12 C13 C8 . . . . 179.64(11) ?
    N2 C4 C5 C6 . . . . 1.33(19) ?
    C2 C6 C5 C4 . . . . 1.97(17) ?
    C4 N2 C3 C2 . . . . 2.47(17) ?
    C6 C2 C3 N2 . . . . 0.78(17) ?
    C1 C2 C3 N2 . . . . -175.60(10) ?
    C12 C13 C8 C9 . . . . 1.77(17) ?
    C12 C13 C8 C7 . . . . -176.93(11) ?
    C10 C9 C8 C13 . . . . -1.15(19) ?
    Cl1 C9 C8 C13 . . . . 176.29(9) ?
    C10 C9 C8 C7 . . . . 177.44(12) ?
    Cl1 C9 C8 C7 . . . . -5.12(18) ?
    C8 C9 C10 C11 . . . . -0.3(2) ?
    Cl1 C9 C10 C11 . . . . -177.83(11) ?
    C13 C8 C7 O3 . . . . 151.23(12) ?
    C9 C8 C7 O3 . . . . -27.36(19) ?
    C13 C8 C7 O2 . . . . -26.97(15) ?
    C9 C8 C7 O2 . . . . 154.44(12) ?
    C9 C10 C11 C12 . . . . 1.0(2) ?
    C13 C12 C11 C10 . . . . -0.4(2) ?
    N3 C12 C11 C10 . . . . 178.92(12) ?
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 H1A O1 375_7 0.90(2) 2.005(19) 2.9004(15) 171.4(14) yes
    N1 H1B O3 365_6 0.873(19) 2.116(19) 2.9715(14) 166.6(16) yes
    O2 H2 N2 155_5 1.07(2) 1.49(2) 2.5543(13) 172(2) yes
    C3 H3 O4 455_5 0.986(15) 2.516(15) 3.4505(16) 158.2(12) yes
    C4 H4 O5 455_4 0.979(14) 2.442(15) 3.3256(17) 149.9(12) yes
    C5 H5 O5 264_5 0.956(15) 2.450(16) 3.0878(17) 124.0(11) yes
    C6 H6 O3 455_4 0.959(15) 2.608(15) 3.4520(10)
                                                147.0(11) yes
    C10 H10 O4 145_5 0.955(15) 2.599(16) 3.5010(18) 157.6(15) 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     0.920
_shelx_estimated_absorpt_T_max     0.956
data_global
_journal_date_recd_electronic     2019-08-20
_journal_date_accepted     2019-10-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2019
_journal_volume     75
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019013859
_journal_coeditor_code     EB2025
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Susanta K. Nayak'
;
Department of Chemistry
Visvesvaraya National Institute of Technology
Nagpur 440010
Maharashtra
India
;
 sknayak@chm.vnit.ac.in
    'K. N. Venugopala'
;
Department of Biotechnology and Food Technology
Durban University of Technology
Durban 4001
South Africa
;
 kvenugopala@kfu.edu.sa
_publ_contact_author_fax      917122223230
_publ_contact_author_phone      917122221610
_publ_section_title
;
Crystal structure of a 1:1 cocrystal of nicotinamide with
2-chloro-5-nitrobenzoic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Bairagi, Keshab M.'
;
Department of Chemistry, Visvesvaraya National Institute of Technology,
Nagpur 440 010, Maharashtra, India
;
    'Pal, Priyanka'
;
Department of Chemistry, Visvesvaraya National Institute of Technology,
Nagpur 440 010, Maharashtra, India
;
    'Bhandary, Subhrajyoti'
;
Department of Chemistry,
Indian Institute of Science Education and Research Bhopal,
Bhauri, Bhopal 462 066, Madhya Pradesh, India
;
    'Venugopala, Katharigatta N.'
;
Department of Pharmaceutical Sciences, College of Clinical Pharmacy,
King Faisal University, Al-Ahsa 31982, Kingdom of Saudi Arabia
Department of Biotechnology and Food Technology,
Durban University of Technology, Durban 4001, South Africa
;
    'Deepak Chopra'
;
Department of Chemistry,
Indian Institute of Science Education and Research Bhopal,
Bhauri, Bhopal 462 066, Madhya Pradesh, India
;
    'Susanta K. Nayak'
;
Department of Chemistry, Visvesvaraya National Institute of Technology,
Nagpur 440 010, Maharashtra, India
;
_publ_section_synopsis
;
In the 1:1 cocrystal of nicotinamide and 2-chloro-5-nitrobenzoic acid, the
molecules form hydrogen bonds through O---H...N, N---H...O, and C---H...O
interactions along with N---H...O dimer hydrogen bonds of nicotinamide.
Further additional weak π--π interactions stabilize the molecular assembly
of this cocrystal.
;
