#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/47/7204796.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204796
loop_
_publ_author_name
'Christer B. Aakeröy'
'John Desper'
'Brian A. Helfrich'
_publ_section_title
;
 Heteromeric intermolecular interactions as synthetic tools for the
 formation of binary co-crystals
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              19
_journal_page_last               24
_journal_paper_doi               10.1039/b315181f
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety
;
(C7 H5 N O4) (C6 H6 N2 O)
;
_chemical_formula_sum            'C13 H11 N3 O5'
_chemical_formula_weight         289.25
_chemical_melting_point          161.0(10)
_chemical_name_common            '3-nitrobenzoic acid, isonicotinamide'
_chemical_name_systematic
;
3-nitrobenzoic acid, isonicotinamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.149(5)
_cell_angle_beta                 77.407(6)
_cell_angle_gamma                74.927(5)
_cell_formula_units_Z            2
_cell_length_a                   5.9827(4)
_cell_length_b                   9.1713(8)
_cell_length_c                   12.1893(8)
_cell_measurement_reflns_used    1290
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      26.90
_cell_measurement_theta_min      2.30
_cell_volume                     629.54(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.893
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.1158
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4649
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.039(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.787
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.787
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0464
_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)+(0.0450P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                1306
_reflns_number_total             2786
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b315181f.txt
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '160-162' was changed to '161.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204796
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.8592(3) 0.59112(19) 0.80660(14) 0.0321(5) Uani 1 1 d . . .
C12 C 1.0926(4) 0.5508(2) 0.77232(18) 0.0349(6) Uani 1 1 d . . .
H12 H 1.1655 0.6128 0.7176 0.042 Uiso 1 1 calc R . .
C13 C 1.2313(4) 0.4221(2) 0.81358(18) 0.0308(6) Uani 1 1 d . . .
H13 H 1.3957 0.3972 0.7872 0.037 Uiso 1 1 calc R . .
C14 C 1.1282(3) 0.3298(2) 0.89378(17) 0.0264(5) Uani 1 1 d . . .
C15 C 0.8849(3) 0.3702(2) 0.92828(17) 0.0303(6) Uani 1 1 d . . .
H15 H 0.8069 0.3094 0.9818 0.036 Uiso 1 1 calc R . .
C16 C 0.7609(4) 0.5002(2) 0.88299(18) 0.0345(6) Uani 1 1 d . . .
H16 H 0.5959 0.5271 0.9073 0.041 Uiso 1 1 calc R . .
C17 C 1.2851(4) 0.1917(2) 0.93797(17) 0.0291(5) Uani 1 1 d . . .
N17 N 1.1903(3) 0.1080(2) 1.02015(16) 0.0372(5) Uani 1 1 d . . .
H17A H 1.297(4) 0.016(3) 1.0478(17) 0.045 Uiso 1 1 d . . .
H17B H 1.046(4) 0.129(2) 1.0514(18) 0.045 Uiso 1 1 d . . .
O17 O 1.4974(2) 0.15758(17) 0.89518(13) 0.0410(4) Uani 1 1 d . . .
C21 C 0.2980(3) 1.0247(2) 0.69626(17) 0.0275(5) Uani 1 1 d . . .
C22 C 0.4325(3) 1.1001(2) 0.61468(16) 0.0279(5) Uani 1 1 d . . .
H22 H 0.5977 1.0648 0.5965 0.033 Uiso 1 1 calc R . .
C23 C 0.3191(4) 1.2278(2) 0.56080(17) 0.0285(5) Uani 1 1 d . . .
C24 C 0.0777(4) 1.2825(2) 0.58342(18) 0.0348(6) Uani 1 1 d . . .
H24 H 0.0048 1.3698 0.5449 0.042 Uiso 1 1 calc R . .
C25 C -0.0536(4) 1.2061(3) 0.66374(18) 0.0367(6) Uani 1 1 d . . .
H25 H -0.2189 1.2414 0.6811 0.044 Uiso 1 1 calc R . .
C26 C 0.0549(3) 1.0784(2) 0.71898(18) 0.0341(6) Uani 1 1 d . . .
H26 H -0.0375 1.0265 0.7733 0.041 Uiso 1 1 calc R . .
C27 C 0.4115(4) 0.8868(2) 0.75727(17) 0.0299(6) Uani 1 1 d . . .
O27 O 0.6385(3) 0.83941(18) 0.71715(13) 0.0384(4) Uani 1 1 d . . .
H27 H 0.722(4) 0.732(3) 0.7580(17) 0.046 Uiso 1 1 d . . .
O28 O 0.3046(2) 0.82331(16) 0.83563(12) 0.0405(5) Uani 1 1 d . . .
N28 N 0.4617(3) 1.3090(2) 0.47545(15) 0.0358(5) Uani 1 1 d . . .
O29 O 0.6744(3) 1.25240(18) 0.45101(12) 0.0436(5) Uani 1 1 d . . .
O30 O 0.3639(3) 1.42766(18) 0.43232(14) 0.0508(5) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N11 C12 117.29(18) . . ?
C16 N11 H27 123.4(8) . . ?
C12 N11 H27 119.3(8) . . ?
N11 C12 C13 122.65(19) . . ?
N11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C12 C13 C14 119.64(19) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 117.82(19) . . ?
C13 C14 C17 118.18(18) . . ?
C15 C14 C17 124.00(18) . . ?
C16 C15 C14 118.63(19) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N11 C16 C15 123.94(19) . . ?
N11 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
O17 C17 N17 121.9(2) . . ?
O17 C17 C14 119.40(18) . . ?
N17 C17 C14 118.69(18) . . ?
C17 N17 H17A 117.4(12) . . ?
C17 N17 H17B 124.2(15) . . ?
H17A N17 H17B 118.4(19) . . ?
C22 C21 C26 119.0(2) . . ?
C22 C21 C27 120.71(18) . . ?
C26 C21 C27 120.24(19) . . ?
C23 C22 C21 118.50(19) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C22 C23 C24 122.81(19) . . ?
C22 C23 N28 118.55(18) . . ?
C24 C23 N28 118.64(19) . . ?
C25 C24 C23 118.1(2) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C24 C25 C26 120.33(19) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 121.18(19) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
O28 C27 O27 123.49(19) . . ?
O28 C27 C21 123.42(19) . . ?
O27 C27 C21 113.09(17) . . ?
C27 O27 H27 113.7(10) . . ?
O30 N28 O29 123.58(18) . . ?
O30 N28 C23 118.95(18) . . ?
O29 N28 C23 117.47(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.329(2) . ?
N11 C12 1.330(2) . ?
N11 H27 1.48(2) . ?
C12 C13 1.373(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.385(3) . ?
C14 C17 1.495(3) . ?
C15 C16 1.364(3) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 O17 1.234(2) . ?
C17 N17 1.318(2) . ?
N17 H17A 0.99(2) . ?
N17 H17B 0.84(2) . ?
C21 C22 1.384(3) . ?
C21 C26 1.384(3) . ?
C21 C27 1.482(3) . ?
C22 C23 1.374(3) . ?
C22 H22 0.9400 . ?
C23 C24 1.375(3) . ?
C23 N28 1.467(2) . ?
C24 C25 1.370(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.371(3) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C27 O28 1.214(2) . ?
C27 O27 1.311(2) . ?
O27 H27 1.11(2) . ?
N28 O30 1.220(2) . ?
N28 O29 1.225(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O27 H27 N11 1.11(2) 1.48(2) 2.584(2) 173.9(18) .
N17 H17A O17 0.99(2) 1.91(2) 2.907(2) 178.4(19) 2_857
N17 H17B O28 0.84(2) 2.21(2) 3.040(2) 169(2) 2_667
C12 H12 O29 0.94 2.43 3.356(3) 168.0 2_776
C24 H24 O30 0.94 2.47 3.248(3) 140.1 2_586
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 C13 -0.8(3) . . . . ?
N11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C12 C13 C14 C17 -179.2(2) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C17 C14 C15 C16 179.1(2) . . . . ?
C12 N11 C16 C15 0.6(3) . . . . ?
C14 C15 C16 N11 0.4(4) . . . . ?
C13 C14 C17 O17 -6.1(3) . . . . ?
C15 C14 C17 O17 173.6(2) . . . . ?
C13 C14 C17 N17 175.5(2) . . . . ?
C15 C14 C17 N17 -4.8(3) . . . . ?
C26 C21 C22 C23 1.3(3) . . . . ?
C27 C21 C22 C23 -179.8(2) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C21 C22 C23 N28 179.13(19) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
N28 C23 C24 C25 -179.66(19) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C24 C25 C26 C21 0.7(4) . . . . ?
C22 C21 C26 C25 -1.3(3) . . . . ?
C27 C21 C26 C25 179.8(2) . . . . ?
C22 C21 C27 O28 173.8(2) . . . . ?
C26 C21 C27 O28 -7.3(4) . . . . ?
C22 C21 C27 O27 -6.9(3) . . . . ?
C26 C21 C27 O27 172.04(19) . . . . ?
C22 C23 N28 O30 -175.4(2) . . . . ?
C24 C23 N28 O30 4.6(3) . . . . ?
C22 C23 N28 O29 5.0(3) . . . . ?
C24 C23 N28 O29 -174.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149528
2 PubChem 85991832
