#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/24/4502401.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_4502401
loop_
_publ_author_name
'Seaton, Colin C.'
'Chadwick, Keith'
'Sadiq, Ghazala'
'Guo, Kun'
'Davey, Roger J.'
_publ_section_title
;
 Designing Acid/Acid Co-Crystals through the Application of Hammett
 Substituent Constants
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              726
_journal_paper_doi               10.1021/cg9011235
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C7 H9 N2 O2, C7 H3 N2 O6'
_chemical_formula_sum            'C14 H12 N4 O8'
_chemical_formula_weight         364.28
_chemical_name_systematic
; 
 3,5-diaminobenzoic acid 3,5-dinitrobenozate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.669(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0409(5)
_cell_length_b                   14.9622(11)
_cell_length_c                   13.8320(10)
_cell_measurement_reflns_used    3502
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5021
_cell_measurement_theta_min      2.7120
_cell_volume                     1427.05(18)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_molecular_graphics    CrystalMaker
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3367
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device_type  'Oxford Diffraction XCalibur 2'
_diffrn_measurement_method       'ω 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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9932
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         28.62
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.753
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.753
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0598P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                2083
_reflns_number_total             3246
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9011235_si_007.cif
_cod_data_source_block           35dnba_35dba
_cod_database_code               4502401
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O O 0.16241(16) 0.21607(7) 0.51744(8) 0.0161(3) Uani 1 1 d .
O0AA O 0.23732(18) -0.14052(8) 0.78398(9) 0.0256(3) Uani 1 1 d .
O1AA O -0.10937(16) 0.26146(8) 0.56158(8) 0.0188(3) Uani 1 1 d .
O2AA O -0.01291(18) 0.22287(8) 0.92731(8) 0.0229(3) Uani 1 1 d .
N N 0.0417(2) 0.14566(10) 0.92164(10) 0.0175(3) Uani 1 1 d .
O3AA O 0.23514(19) -0.11469(8) 0.62986(9) 0.0287(3) Uani 1 1 d .
C C 0.0392(2) 0.17440(11) 0.74723(11) 0.0132(3) Uani 1 1 d .
H H -0.0020 0.2323 0.7560 0.016 Uiso 1 1 calc R
N0AA N 0.2130(2) -0.09125(9) 0.71141(11) 0.0192(3) Uani 1 1 d .
O4AA O 0.07280(18) 0.09297(8) 0.99142(8) 0.0243(3) Uani 1 1 d .
C1AA C 0.1549(2) 0.00167(10) 0.72384(12) 0.0148(3) Uani 1 1 d .
C2AA C 0.0700(2) 0.14652(10) 0.65568(11) 0.0130(3) Uani 1 1 d .
C3AA C 0.1319(2) 0.05983(11) 0.64425(12) 0.0136(3) Uani 1 1 d .
H3AA H 0.1575 0.0410 0.5841 0.016 Uiso 1 1 calc R
C4AA C 0.1255(2) 0.02748(11) 0.81560(12) 0.0153(4) Uani 1 1 d .
H4AA H 0.1417 -0.0122 0.8684 0.018 Uiso 1 1 calc R
C5AA C 0.0710(2) 0.11465(11) 0.82480(11) 0.0142(3) Uani 1 1 d .
C0AA C 0.0352(2) 0.21260(11) 0.57109(11) 0.0137(3) Uani 1 1 d .
O5AA O 0.20508(17) 0.57962(8) 0.06640(8) 0.0186(3) Uani 1 1 d .
H5AA H 0.2472 0.6264 0.0482 0.028 Uiso 1 1 calc R
C6AA C 0.2192(2) 0.58164(11) 0.16314(11) 0.0131(3) Uani 1 1 d .
N1AA N 0.0503(2) 0.26102(9) 0.13514(10) 0.0134(3) Uani 1 1 d .
O6AA O 0.28697(18) 0.64432(8) 0.21415(8) 0.0212(3) Uani 1 1 d .
C7AA C 0.0577(2) 0.34149(11) 0.29066(11) 0.0125(3) Uani 1 1 d .
H7AA H 0.0262 0.2884 0.3187 0.015 Uiso 1 1 calc R
N2AA N 0.0686(2) 0.41890(11) 0.44415(10) 0.0183(3) Uani 1 1 d .
C8AA C 0.0892(2) 0.41953(11) 0.34702(11) 0.0128(3) Uani 1 1 d .
C9AA C 0.1517(2) 0.49851(10) 0.20402(11) 0.0128(3) Uani 1 1 d .
C0BA C 0.1383(2) 0.49786(11) 0.30314(11) 0.0136(3) Uani 1 1 d .
H0BA H 0.1622 0.5500 0.3403 0.016 Uiso 1 1 calc R
C1BA C 0.0738(2) 0.34391(11) 0.19324(11) 0.0126(3) Uani 1 1 d .
C2BA C 0.1169(2) 0.42116(11) 0.14738(11) 0.0123(3) Uani 1 1 d .
H2BA H 0.1225 0.4215 0.0808 0.015 Uiso 1 1 calc R
H2AA H 0.058(3) 0.3686(13) 0.4735(13) 0.022(5) Uiso 1 1 d .
H1BB H -0.069(3) 0.2650(13) 0.0896(15) 0.033(6) Uiso 1 1 d .
H2AB H 0.122(3) 0.4651(14) 0.4800(14) 0.030(6) Uiso 1 1 d .
H1BC H 0.169(3) 0.2551(14) 0.1026(17) 0.052(7) Uiso 1 1 d .
H1BA H 0.055(3) 0.2078(14) 0.1797(15) 0.040(6) 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
O2AA N O4AA 124.20(14)
O2AA N C5AA 117.35(13)
O4AA N C5AA 118.45(14)
C5AA C C2AA 118.88(15)
C5AA C H 120.6
C2AA C H 120.6
O3AA N0AA O0AA 124.01(15)
O3AA N0AA C1AA 118.07(14)
O0AA N0AA C1AA 117.91(14)
C4AA C1AA C3AA 122.58(15)
C4AA C1AA N0AA 117.97(14)
C3AA C1AA N0AA 119.44(14)
C3AA C2AA C 119.62(15)
C3AA C2AA C0AA 121.88(14)
C C2AA C0AA 118.50(14)
C1AA C3AA C2AA 119.03(15)
C1AA C3AA H3AA 120.5
C2AA C3AA H3AA 120.5
C5AA C4AA C1AA 116.58(15)
C5AA C4AA H4AA 121.7
C1AA C4AA H4AA 121.7
C4AA C5AA C 123.22(15)
C4AA C5AA N 118.52(14)
C C5AA N 118.25(15)
O1AA C0AA O 124.99(15)
O1AA C0AA C2AA 117.95(14)
O C0AA C2AA 116.99(14)
C6AA O5AA H5AA 109.5
O6AA C6AA O5AA 123.16(15)
O6AA C6AA C9AA 123.07(14)
O5AA C6AA C9AA 113.72(13)
C1BA N1AA H1BB 107.3(12)
C1BA N1AA H1BC 107.4(12)
H1BB N1AA H1BC 114.1(17)
C1BA N1AA H1BA 110.3(11)
H1BB N1AA H1BA 111.7(16)
H1BC N1AA H1BA 105.9(16)
C1BA C7AA C8AA 119.32(14)
C1BA C7AA H7AA 120.3
C8AA C7AA H7AA 120.3
C8AA N2AA H2AA 120.0(12)
C8AA N2AA H2AB 115.0(13)
H2AA N2AA H2AB 118.8(18)
N2AA C8AA C7AA 120.11(14)
N2AA C8AA C0BA 120.88(15)
C7AA C8AA C0BA 119.00(14)
C2BA C9AA C0BA 120.61(14)
C2BA C9AA C6AA 121.08(14)
C0BA C9AA C6AA 118.13(14)
C9AA C0BA C8AA 120.40(14)
C9AA C0BA H0BA 119.8
C8AA C0BA H0BA 119.8
C7AA C1BA C2BA 122.76(14)
C7AA C1BA N1AA 119.43(14)
C2BA C1BA N1AA 117.78(13)
C1BA C2BA C9AA 117.87(14)
C1BA C2BA H2BA 121.1
C9AA C2BA H2BA 121.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C0AA 1.2743(18)
O0AA N0AA 1.2291(18)
O1AA C0AA 1.2387(19)
O2AA N 1.2249(17)
N O4AA 1.2311(17)
N C5AA 1.471(2)
O3AA N0AA 1.2210(18)
C C5AA 1.380(2)
C C2AA 1.391(2)
C H 0.9300
N0AA C1AA 1.469(2)
C1AA C4AA 1.382(2)
C1AA C3AA 1.387(2)
C2AA C3AA 1.387(2)
C2AA C0AA 1.513(2)
C3AA H3AA 0.9300
C4AA C5AA 1.373(2)
C4AA H4AA 0.9300
O5AA C6AA 1.3220(18)
O5AA H5AA 0.8200
C6AA O6AA 1.2120(19)
C6AA C9AA 1.484(2)
N1AA C1BA 1.469(2)
N1AA H1BB 0.95(2)
N1AA H1BC 1.03(2)
N1AA H1BA 1.00(2)
C7AA C1BA 1.375(2)
C7AA C8AA 1.397(2)
C7AA H7AA 0.9300
N2AA C8AA 1.3802(19)
N2AA H2AA 0.866(19)
N2AA H2AB 0.89(2)
C8AA C0BA 1.395(2)
C9AA C2BA 1.391(2)
C9AA C0BA 1.393(2)
C0BA H0BA 0.9300
C1BA C2BA 1.381(2)
C2BA H2BA 0.9300
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
O5AA H5AA O 0.82 1.81 2.6117(15) 167.1 2
N2AA H2AA O 0.866(19) 2.438(19) 3.2253(19) 151.5(16) .
N2AA H2AA O1AA 0.866(19) 2.45(2) 3.2529(19) 154.0(16) .
N1AA H1BB O 0.95(2) 1.97(2) 2.9034(19) 168.4(17) 4_565
N2AA H2AB N2AA 0.89(2) 2.55(2) 3.133(3) 124.2(15) 3_566
N1AA H1BC O1AA 1.03(2) 1.78(2) 2.8062(18) 172.4(19) 4_665
N1AA H1BA O6AA 1.00(2) 1.91(2) 2.7821(19) 143.8(17) 2_545
N1AA H1BA O0AA 1.00(2) 2.43(2) 3.0856(19) 122.3(15) 3_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144942
