#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/47/7204799.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_7204799
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) (C9 H11 N O2)
;
_chemical_formula_sum            'C16 H16 N2 O6'
_chemical_formula_weight         332.31
_chemical_melting_point          164.0(10)
_chemical_name_common
'4-nitrobenzoic acid, 3-(dimethylamino)benzoic acid'
_chemical_name_systematic
;
4-nitrobenzoic acid, 3-(dimethylamino)benzoic acid
;
_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                91.111(3)
_cell_angle_beta                 91.483(4)
_cell_angle_gamma                111.582(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1538(13)
_cell_length_b                   7.9978(15)
_cell_length_c                   14.315(3)
_cell_measurement_reflns_used    966
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      3.00
_cell_volume                     761.0(3)
_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      153(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0151
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4919
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.859
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0412
_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)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                1669
_reflns_number_total             3060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b315181f.txt
_cod_data_source_block           5
_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 '163-165' was changed to '164.0(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_cell_volume        761.0(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204799
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
C1 C 0.5013(2) 0.1289(2) 0.60959(12) 0.0308(4) Uani 1 1 d . . .
C2 C 0.3948(3) 0.0354(2) 0.68360(13) 0.0383(5) Uani 1 1 d . . .
H2 H 0.2590 0.0243 0.6905 0.046 Uiso 1 1 calc R . .
C3 C 0.4837(3) -0.0416(2) 0.74718(13) 0.0379(5) Uani 1 1 d . . .
H3 H 0.4112 -0.1063 0.7980 0.046 Uiso 1 1 calc R . .
C4 C 0.6804(2) -0.0224(2) 0.73518(12) 0.0330(4) Uani 1 1 d . . .
C5 C 0.7905(3) 0.0688(2) 0.66235(13) 0.0339(4) Uani 1 1 d . . .
H5 H 0.9262 0.0793 0.6559 0.041 Uiso 1 1 calc R . .
C6 C 0.6991(2) 0.1445(2) 0.59900(13) 0.0325(4) Uani 1 1 d . . .
H6 H 0.7719 0.2077 0.5479 0.039 Uiso 1 1 calc R . .
O7 O 0.6773(2) -0.1881(2) 0.86675(10) 0.0568(4) Uani 1 1 d . . .
N7 N 0.7775(2) -0.1015(2) 0.80407(11) 0.0393(4) Uani 1 1 d . . .
O8 O 0.95535(18) -0.07684(18) 0.79568(10) 0.0492(4) Uani 1 1 d . . .
O9 O 0.22312(17) 0.18968(18) 0.54844(9) 0.0468(4) Uani 1 1 d . . .
C9 C 0.4027(3) 0.2105(2) 0.54174(13) 0.0339(4) Uani 1 1 d . . .
O10 O 0.51357(17) 0.29929(17) 0.47647(9) 0.0392(3) Uani 1 1 d . . .
H10 H 0.441(3) 0.341(2) 0.4279(13) 0.047 Uiso 1 1 d . . .
C11 C 0.0512(2) 0.4733(2) 0.28487(12) 0.0327(4) Uani 1 1 d . . .
C12 C 0.1585(3) 0.5478(2) 0.20762(13) 0.0356(5) Uani 1 1 d . . .
H12 H 0.2883 0.5435 0.2004 0.043 Uiso 1 1 calc R . .
C13 C 0.0798(3) 0.6295(3) 0.13973(14) 0.0392(5) Uani 1 1 d . . .
C14 C -0.1123(3) 0.6312(3) 0.15360(15) 0.0451(5) Uani 1 1 d . . .
H14 H -0.1703 0.6861 0.1090 0.054 Uiso 1 1 calc R . .
C15 C -0.2188(3) 0.5551(3) 0.23038(15) 0.0462(5) Uani 1 1 d . . .
H15 H -0.3495 0.5575 0.2375 0.055 Uiso 1 1 calc R . .
C16 C -0.1398(3) 0.4752(3) 0.29750(14) 0.0414(5) Uani 1 1 d . . .
H16 H -0.2140 0.4232 0.3506 0.050 Uiso 1 1 calc R . .
C17 C 0.1084(3) 0.7885(3) -0.00776(15) 0.0613(6) Uani 1 1 d . . .
H17A H 0.1958 0.8140 -0.0614 0.092 Uiso 1 1 calc R . .
H17B H 0.1021 0.9011 0.0174 0.092 Uiso 1 1 calc R . .
H17C H -0.0271 0.7067 -0.0277 0.092 Uiso 1 1 calc R . .
N17 N 0.1885(3) 0.7054(3) 0.06380(13) 0.0684(6) Uani 1 1 d . . .
C18 C 0.3849(3) 0.6995(3) 0.05131(15) 0.0653(7) Uani 1 1 d . . .
H18A H 0.3803 0.5772 0.0615 0.098 Uiso 1 1 calc R . .
H18B H 0.4813 0.7833 0.0963 0.098 Uiso 1 1 calc R . .
H18C H 0.4269 0.7338 -0.0124 0.098 Uiso 1 1 calc R . .
C19 C 0.1469(2) 0.3967(2) 0.35561(13) 0.0334(4) Uani 1 1 d . . .
O19 O 0.32448(17) 0.40725(17) 0.34839(9) 0.0395(3) Uani 1 1 d . . .
O20 O 0.03899(19) 0.3193(2) 0.42451(10) 0.0536(4) Uani 1 1 d . . .
H20 H 0.110(3) 0.271(3) 0.4667(15) 0.064 Uiso 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
C2 C1 C6 119.84(17) . . ?
C2 C1 C9 119.75(15) . . ?
C6 C1 C9 120.40(16) . . ?
C3 C2 C1 120.56(16) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 118.17(17) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 122.87(17) . . ?
C3 C4 N7 118.37(16) . . ?
C5 C4 N7 118.76(15) . . ?
C4 C5 C6 118.30(16) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 120.25(17) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O7 N7 O8 123.17(16) . . ?
O7 N7 C4 118.65(15) . . ?
O8 N7 C4 118.18(15) . . ?
O9 C9 O10 123.47(17) . . ?
O9 C9 C1 120.60(16) . . ?
O10 C9 C1 115.92(15) . . ?
C9 O10 H10 114.5(10) . . ?
C12 C11 C16 121.14(17) . . ?
C12 C11 C19 118.27(15) . . ?
C16 C11 C19 120.56(16) . . ?
C11 C12 C13 121.21(16) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
N17 C13 C12 120.87(16) . . ?
N17 C13 C14 122.09(18) . . ?
C12 C13 C14 117.03(17) . . ?
C15 C14 C13 121.31(18) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 121.40(17) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C11 117.91(18) . . ?
C15 C16 H16 121.0 . . ?
C11 C16 H16 121.0 . . ?
N17 C17 H17A 109.5 . . ?
N17 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N17 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 N17 C18 120.56(17) . . ?
C13 N17 C17 121.61(17) . . ?
C18 N17 C17 117.80(17) . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O19 C19 O20 122.21(16) . . ?
O19 C19 C11 120.92(15) . . ?
O20 C19 C11 116.87(15) . . ?
C19 O20 H20 112.0(12) . . ?
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
C1 C2 1.384(2) . ?
C1 C6 1.387(2) . ?
C1 C9 1.482(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(2) . ?
C4 N7 1.472(2) . ?
C5 C6 1.378(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O7 N7 1.2210(18) . ?
N7 O8 1.2235(17) . ?
O9 C9 1.2398(18) . ?
C9 O10 1.2869(19) . ?
O10 H10 0.99(2) . ?
C11 C12 1.379(2) . ?
C11 C16 1.388(2) . ?
C11 C19 1.472(2) . ?
C12 C13 1.398(3) . ?
C12 H12 0.9500 . ?
C13 N17 1.370(2) . ?
C13 C14 1.399(2) . ?
C14 C15 1.374(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N17 1.448(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N17 C18 1.438(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O19 1.2489(19) . ?
C19 O20 1.2899(19) . ?
O20 H20 0.95(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
O10 H10 O19 0.99(2) 1.60(2) 2.5941(18) 179.5(16) .
O20 H20 O9 0.95(2) 1.68(2) 2.6288(18) 174.9(19) .
C18 H18C O7 0.98 2.44 3.340(2) 151.9 1_564
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
C6 C1 C2 C3 0.3(3) . . . . ?
C9 C1 C2 C3 179.87(17) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C3 C4 N7 178.81(16) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
N7 C4 C5 C6 -179.07(15) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C9 C1 C6 C5 179.86(16) . . . . ?
C3 C4 N7 O7 3.3(2) . . . . ?
C5 C4 N7 O7 -177.34(17) . . . . ?
C3 C4 N7 O8 -176.57(17) . . . . ?
C5 C4 N7 O8 2.8(2) . . . . ?
C2 C1 C9 O9 -2.9(3) . . . . ?
C6 C1 C9 O9 176.61(17) . . . . ?
C2 C1 C9 O10 178.16(16) . . . . ?
C6 C1 C9 O10 -2.3(2) . . . . ?
C16 C11 C12 C13 0.7(3) . . . . ?
C19 C11 C12 C13 -177.31(17) . . . . ?
C11 C12 C13 N17 179.11(18) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
N17 C13 C14 C15 -179.7(2) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
C19 C11 C16 C15 177.55(17) . . . . ?
C12 C13 N17 C18 1.2(3) . . . . ?
C14 C13 N17 C18 -179.4(2) . . . . ?
C12 C13 N17 C17 179.20(19) . . . . ?
C14 C13 N17 C17 -1.4(3) . . . . ?
C12 C11 C19 O19 3.7(3) . . . . ?
C16 C11 C19 O19 -174.30(17) . . . . ?
C12 C11 C19 O20 -176.32(16) . . . . ?
C16 C11 C19 O20 5.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149525
2 PubChem 85991845
