#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/73/2237328.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_2237328
loop_
_publ_author_name
'Naz, Syeda Sohaila'
'Islam, Nazar Ul'
'Tahir, M. Nawaz'
'Shah, Muhammad Raza'
_publ_section_title
;
 Methyl 2,4-dihydroxy-5-(4-nitrobenzamido)benzoate
;
_journal_coeditor_code           HB7022
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o207
_journal_paper_doi               10.1107/S160053681300024X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C15 H12 N2 O7'
_chemical_formula_moiety         'C15 H12 N2 O7'
_chemical_formula_sum            'C15 H12 N2 O7'
_chemical_formula_weight         332.27
_chemical_name_systematic
;
Methyl 2,4-dihydroxy-5-(4-nitrobenzamido)benzoate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 111.737(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.412(6)
_cell_length_b                   6.9325(15)
_cell_length_c                   14.936(3)
_cell_measurement_reflns_used    1519
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.44
_cell_volume                     2925.1(11)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       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  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0727
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10681
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.240
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0517
_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)+(0.0575P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                1519
_reflns_number_total             2885
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7022.cif
_cod_data_source_block           I
_cod_original_cell_volume        2925.0(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2237328
_cod_database_fobs_code          2237328
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-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_thermal_displace_type
_atom_site_occupancy
_atom_site_disorder_group
O O1 0.10274(6) 0.1155(3) 0.32019(12) 0.0472(7) Uani 1.000 -16
O O2 0.05741(6) 0.1342(3) 0.40795(13) 0.0569(8) Uani 1.000 -16
O O3 0.09767(6) 0.1238(3) 0.59618(13) 0.0556(8) Uani 1.000 -16
O O4 0.26255(6) 0.0020(3) 0.72631(12) 0.0551(8) Uani 1.000 -16
O O5 0.25654(6) -0.0216(3) 0.39997(11) 0.0441(7) Uani 1.000 -16
O O6 0.49252(7) -0.2190(4) 0.50312(16) 0.0817(10) Uani 1.000 -16
O O7 0.50869(7) -0.1537(4) 0.65151(16) 0.0963(12) Uani 1.000 -16
N N1 0.26968(7) -0.0090(3) 0.55853(14) 0.0378(8) Uani 1.000 -16
N N2 0.48095(8) -0.1732(4) 0.56944(19) 0.0571(10) Uani 1.000 -16
C C1 0.13985(9) 0.0859(4) 0.48802(17) 0.0319(9) Uani 1.000 -16
C C2 0.13784(9) 0.0904(4) 0.58047(19) 0.0364(9) Uani 1.000 -16
C C3 0.17868(9) 0.0616(4) 0.66047(18) 0.0415(10) Uani 1.000 -16
C C4 0.22102(9) 0.0301(4) 0.65078(17) 0.0371(9) Uani 1.000 -16
C C5 0.22394(8) 0.0249(3) 0.55857(17) 0.0303(9) Uani 1.000 -16
C C6 0.18331(8) 0.0531(3) 0.47889(16) 0.0314(9) Uani 1.000 -16
C C7 0.09636(10) 0.1146(4) 0.40347(18) 0.0390(10) Uani 1.000 -16
C C8 0.06012(10) 0.1408(5) 0.23493(19) 0.0624(13) Uani 1.000 -16
C C9 0.28430(8) -0.0313(3) 0.48462(17) 0.0298(9) Uani 1.000 -16
C C10 0.33614(8) -0.0680(3) 0.51086(16) 0.0301(8) Uani 1.000 -16
C C11 0.36749(9) -0.1024(4) 0.60418(17) 0.0425(10) Uani 1.000 -16
C C12 0.41477(9) -0.1343(4) 0.62442(19) 0.0448(10) Uani 1.000 -16
C C13 0.43065(9) -0.1345(4) 0.54982(19) 0.0382(9) Uani 1.000 -16
C C14 0.40103(9) -0.1016(4) 0.45639(19) 0.0482(10) Uani 1.000 -16
C C15 0.35354(9) -0.0687(4) 0.43751(18) 0.0425(10) Uani 1.000 -16
H H1 0.29169 -0.01664 0.61475 0.0453 Uiso 1.000 -16
H H3 0.17730 0.06358 0.72164 0.0499 Uiso 1.000 -16
H H3A 0.07616 0.14790 0.54484 0.0833 Uiso 1.000 -16
H H4 0.25843 0.01839 0.77701 0.0826 Uiso 1.000 -16
H H6 0.18481 0.05032 0.41783 0.0377 Uiso 1.000 -16
H H8A 0.06788 0.13162 0.17835 0.0937 Uiso 1.000 -16
H H8B 0.04667 0.26521 0.23692 0.0937 Uiso 1.000 -16
H H8C 0.03765 0.04218 0.23315 0.0937 Uiso 1.000 -16
H H11 0.35623 -0.10400 0.65419 0.0511 Uiso 1.000 -16
H H12 0.43554 -0.15519 0.68741 0.0538 Uiso 1.000 -16
H H14 0.41260 -0.10127 0.40680 0.0578 Uiso 1.000 -16
H H15 0.33301 -0.04676 0.37444 0.0509 Uiso 1.000 -16
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'
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
C7 O1 C8 115.4(2) no
C2 O3 H3A 109.00 no
C4 O4 H4 109.00 no
C5 N1 C9 130.3(2) no
O6 N2 C13 118.7(2) no
O6 N2 O7 123.6(3) no
O7 N2 C13 117.7(2) no
C9 N1 H1 115.00 no
C5 N1 H1 115.00 no
C6 C1 C7 121.5(2) no
C2 C1 C7 119.4(3) no
C2 C1 C6 119.1(2) no
O3 C2 C3 117.2(2) no
C1 C2 C3 119.6(3) no
O3 C2 C1 123.2(2) no
C2 C3 C4 120.8(2) no
O4 C4 C3 123.9(2) no
O4 C4 C5 115.5(2) no
C3 C4 C5 120.6(2) no
N1 C5 C4 115.0(2) no
C4 C5 C6 118.6(2) no
N1 C5 C6 126.4(2) no
C1 C6 C5 121.2(2) no
O1 C7 O2 122.2(2) no
O1 C7 C1 114.2(3) no
O2 C7 C1 123.6(2) no
N1 C9 C10 116.2(2) no
O5 C9 N1 121.8(2) no
O5 C9 C10 122.1(2) no
C9 C10 C15 117.9(2) no
C11 C10 C15 118.3(2) no
C9 C10 C11 123.8(2) no
C10 C11 C12 121.5(2) no
C11 C12 C13 118.5(2) no
N2 C13 C12 119.5(2) no
C12 C13 C14 122.1(3) no
N2 C13 C14 118.4(2) no
C13 C14 C15 118.5(3) no
C10 C15 C14 121.1(2) no
C2 C3 H3 120.00 no
C4 C3 H3 120.00 no
C1 C6 H6 119.00 no
C5 C6 H6 119.00 no
O1 C8 H8A 109.00 no
O1 C8 H8B 109.00 no
O1 C8 H8C 109.00 no
H8A C8 H8B 109.00 no
H8A C8 H8C 109.00 no
H8B C8 H8C 109.00 no
C10 C11 H11 119.00 no
C12 C11 H11 119.00 no
C11 C12 H12 121.00 no
C13 C12 H12 121.00 no
C13 C14 H14 121.00 no
C15 C14 H14 121.00 no
C10 C15 H15 119.00 no
C14 C15 H15 119.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.328(3) no
O1 C8 1.453(3) no
O2 C7 1.219(4) no
O3 C2 1.347(4) no
O4 C4 1.360(3) no
O5 C9 1.235(3) no
O6 N2 1.210(4) no
O7 N2 1.211(3) no
O3 H3A 0.8200 no
O4 H4 0.8200 no
N1 C9 1.343(3) no
N1 C5 1.411(3) no
N2 C13 1.472(4) no
N1 H1 0.8600 no
C1 C7 1.465(4) no
C1 C6 1.397(4) no
C1 C2 1.405(4) no
C2 C3 1.382(4) no
C3 C4 1.366(4) no
C4 C5 1.413(3) no
C5 C6 1.376(3) no
C9 C10 1.499(4) no
C10 C15 1.382(4) no
C10 C11 1.387(3) no
C11 C12 1.373(4) no
C12 C13 1.369(4) no
C13 C14 1.371(4) no
C14 C15 1.384(4) no
C3 H3 0.9300 no
C6 H6 0.9300 no
C8 H8A 0.9600 no
C8 H8B 0.9600 no
C8 H8C 0.9600 no
C11 H11 0.9300 no
C12 H12 0.9300 no
C14 H14 0.9300 no
C15 H15 0.9300 no
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 H1 O4 . 0.86 2.16 2.595(3) 111 yes
O3 H3A O2 . 0.82 1.91 2.619(3) 144 yes
O4 H4 O5 4_555 0.82 1.86 2.670(2) 170 yes
C8 H8A O3 4_554 0.96 2.51 3.274(4) 137 yes
C12 H12 O7 2_656 0.93 2.38 3.297(4) 171 yes
C15 H15 O4 4_554 0.93 2.46 3.370(3) 165 yes
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 O1 C7 O2 -0.2(4) no
C8 O1 C7 C1 179.1(2) no
C9 N1 C5 C4 176.6(2) no
C9 N1 C5 C6 -3.7(4) no
C5 N1 C9 O5 0.8(4) no
C5 N1 C9 C10 -179.3(2) no
O6 N2 C13 C12 162.4(3) no
O6 N2 C13 C14 -17.0(4) no
O7 N2 C13 C12 -19.0(4) no
O7 N2 C13 C14 161.7(3) no
C6 C1 C2 O3 179.0(2) no
C6 C1 C2 C3 -0.3(4) no
C7 C1 C2 O3 -1.3(4) no
C7 C1 C2 C3 179.4(3) no
C2 C1 C6 C5 0.1(4) no
C7 C1 C6 C5 -179.5(2) no
C2 C1 C7 O1 177.3(2) no
C2 C1 C7 O2 -3.4(4) no
C6 C1 C7 O1 -3.0(4) no
C6 C1 C7 O2 176.3(3) no
O3 C2 C3 C4 -178.9(3) no
C1 C2 C3 C4 0.4(4) no
C2 C3 C4 O4 179.6(3) no
C2 C3 C4 C5 -0.5(4) no
O4 C4 C5 N1 0.1(3) no
O4 C4 C5 C6 -179.7(2) no
C3 C4 C5 N1 -179.9(2) no
C3 C4 C5 C6 0.3(4) no
N1 C5 C6 C1 -179.9(2) no
C4 C5 C6 C1 -0.1(3) no
O5 C9 C10 C11 -172.1(2) no
O5 C9 C10 C15 7.5(3) no
N1 C9 C10 C11 8.0(3) no
N1 C9 C10 C15 -172.4(2) no
C9 C10 C11 C12 -179.7(2) no
C15 C10 C11 C12 0.8(4) no
C9 C10 C15 C14 -180.0(2) no
C11 C10 C15 C14 -0.4(4) no
C10 C11 C12 C13 -1.0(4) no
C11 C12 C13 N2 -178.5(3) no
C11 C12 C13 C14 0.8(4) no
N2 C13 C14 C15 178.8(3) no
C12 C13 C14 C15 -0.5(4) no
C13 C14 C15 C10 0.3(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139085153
