#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/47/7204795.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_7204795
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
;
(C15 H15 N3 O2) (C7 H4 N2 O6)
;
_chemical_formula_sum            'C22 H19 N5 O8'
_chemical_formula_weight         481.42
_chemical_name_common
;2-(4-(dimethylamino)phenylazo)benzoic acid, 3,5-
dinitrobenzoic acid
;
_chemical_name_systematic
;
2-[4-(dimethylamino)phenylazo]benzoic acid, 3,5-dinitrobenzoic acid
;
_chemical_temperature_decomposition 149.0(10)
_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                101.186(2)
_cell_angle_beta                 97.114(2)
_cell_angle_gamma                101.401(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0051(5)
_cell_length_b                   8.6187(7)
_cell_length_c                   18.5866(15)
_cell_measurement_reflns_used    2368
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.50
_cell_volume                     1063.66(14)
_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 0.907
_diffrn_measured_fraction_theta_max 0.907
_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  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8137
_diffrn_reflns_theta_full        28.21
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.064(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.891
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                2692
_reflns_number_total             4765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b315181f.txt
_cod_data_source_block           1
_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' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as '148-150 (dec)'. The value was changed to '149.0(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               7204795
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 0.2478(2) 0.3052(2) 0.61067(9) 0.0328(4) Uani 1 1 d . . .
C2 C 0.3005(3) 0.3538(2) 0.68838(10) 0.0354(4) Uani 1 1 d . . .
C3 C 0.2852(3) 0.2340(2) 0.72942(10) 0.0403(5) Uani 1 1 d . . .
H3 H 0.3199 0.2647 0.7815 0.048 Uiso 1 1 calc R . .
C4 C 0.2208(3) 0.0723(3) 0.69554(11) 0.0433(5) Uani 1 1 d . . .
H4 H 0.2117 -0.0067 0.7242 0.052 Uiso 1 1 calc R . .
C5 C 0.1692(3) 0.0262(2) 0.61860(11) 0.0408(5) Uani 1 1 d . . .
H5 H 0.1242 -0.0843 0.5951 0.049 Uiso 1 1 calc R . .
C6 C 0.1836(3) 0.1410(2) 0.57680(10) 0.0359(4) Uani 1 1 d . . .
H6 H 0.1498 0.1086 0.5247 0.043 Uiso 1 1 calc R . .
O7 O 0.4225(2) 0.56045(18) 0.79677(8) 0.0620(4) Uani 1 1 d . . .
C7 C 0.3734(3) 0.5257(3) 0.72907(11) 0.0440(5) Uani 1 1 d . . .
O8 O 0.3850(2) 0.64019(17) 0.69175(8) 0.0541(4) Uani 1 1 d . . .
H8 H 0.344(3) 0.582(3) 0.6375(13) 0.065 Uiso 1 1 d . . .
N9 N 0.2639(2) 0.42995(18) 0.57033(8) 0.0325(3) Uani 1 1 d . . .
N10 N 0.2174(2) 0.38124(18) 0.49998(8) 0.0355(4) Uani 1 1 d . . .
C11 C 0.2315(3) 0.5005(2) 0.45928(10) 0.0337(4) Uani 1 1 d . . .
C12 C 0.1799(3) 0.4452(2) 0.38238(10) 0.0381(4) Uani 1 1 d . . .
H12 H 0.1386 0.3329 0.3620 0.046 Uiso 1 1 calc R . .
C13 C 0.1879(3) 0.5502(2) 0.33601(10) 0.0401(5) Uani 1 1 d . . .
H13 H 0.1527 0.5090 0.2843 0.048 Uiso 1 1 calc R . .
C14 C 0.2479(2) 0.7191(2) 0.36414(10) 0.0341(4) Uani 1 1 d . . .
C15 C 0.2991(3) 0.7747(2) 0.44252(10) 0.0386(4) Uani 1 1 d . . .
H15 H 0.3391 0.8868 0.4634 0.046 Uiso 1 1 calc R . .
C16 C 0.2913(3) 0.6677(2) 0.48821(10) 0.0365(4) Uani 1 1 d . . .
H16 H 0.3269 0.7075 0.5400 0.044 Uiso 1 1 calc R . .
N17 N 0.2558(2) 0.82228(19) 0.31752(9) 0.0408(4) Uani 1 1 d . . .
C18 C 0.2041(3) 0.7603(3) 0.23747(11) 0.0502(5) Uani 1 1 d . . .
H18A H 0.2873 0.6873 0.2213 0.075 Uiso 1 1 calc R . .
H18B H 0.2239 0.8502 0.2128 0.075 Uiso 1 1 calc R . .
H18C H 0.0667 0.7022 0.2249 0.075 Uiso 1 1 calc R . .
C19 C 0.3171(3) 0.9977(2) 0.34458(13) 0.0546(6) Uani 1 1 d . . .
H19A H 0.2282 1.0343 0.3767 0.082 Uiso 1 1 calc R . .
H19B H 0.3135 1.0496 0.3027 0.082 Uiso 1 1 calc R . .
H19C H 0.4505 1.0262 0.3724 0.082 Uiso 1 1 calc R . .
C21 C 0.6894(3) 1.0914(2) 0.95849(9) 0.0336(4) Uani 1 1 d . . .
C22 C 0.6803(3) 1.2506(2) 0.96045(10) 0.0379(4) Uani 1 1 d . . .
H22 H 0.6137 1.2785 0.9194 0.045 Uiso 1 1 calc R . .
N23 N 0.7626(3) 1.5386(2) 1.02524(12) 0.0560(5) Uani 1 1 d . . .
C23 C 0.7701(3) 1.3682(2) 1.02340(11) 0.0393(5) Uani 1 1 d . . .
O23 O 0.6839(3) 1.5685(2) 0.96900(11) 0.0821(6) Uani 1 1 d . . .
O24 O 0.8353(3) 1.63903(19) 1.08151(11) 0.0872(6) Uani 1 1 d . . .
C24 C 0.8664(3) 1.3332(2) 1.08520(10) 0.0381(4) Uani 1 1 d . . .
H24 H 0.9256 1.4147 1.1279 0.046 Uiso 1 1 calc R . .
O25 O 1.0259(2) 1.23669(18) 1.20393(8) 0.0656(5) Uani 1 1 d . . .
N25 N 0.9685(2) 1.1311(2) 1.14751(9) 0.0420(4) Uani 1 1 d . . .
C25 C 0.8722(3) 1.1737(2) 1.08165(10) 0.0336(4) Uani 1 1 d . . .
O26 O 0.9858(2) 0.99167(17) 1.14194(7) 0.0502(4) Uani 1 1 d . . .
C26 C 0.7876(2) 1.0520(2) 1.01960(9) 0.0323(4) Uani 1 1 d . . .
H26 H 0.7962 0.9442 1.0186 0.039 Uiso 1 1 calc R . .
O27 O 0.4774(2) 0.99457(17) 0.84181(7) 0.0521(4) Uani 1 1 d . . .
C27 C 0.5846(3) 0.9650(2) 0.89078(10) 0.0378(4) Uani 1 1 d . . .
O28 O 0.6192(2) 0.82275(17) 0.89296(7) 0.0475(4) Uani 1 1 d . . .
H28 H 0.566(3) 0.752(3) 0.8570(12) 0.057 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
C6 C1 C2 119.80(17) . . ?
C6 C1 N9 123.18(16) . . ?
C2 C1 N9 117.02(16) . . ?
C3 C2 C1 118.26(17) . . ?
C3 C2 C7 118.26(17) . . ?
C1 C2 C7 123.47(17) . . ?
C4 C3 C2 121.52(18) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.51(18) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.30(19) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.59(17) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O7 C7 O8 120.22(19) . . ?
O7 C7 C2 120.55(19) . . ?
O8 C7 C2 119.23(17) . . ?
C7 O8 H8 105.5(13) . . ?
N10 N9 C1 115.24(15) . . ?
N9 N10 C11 116.44(15) . . ?
N10 C11 C12 115.73(16) . . ?
N10 C11 C16 126.13(16) . . ?
C12 C11 C16 118.14(17) . . ?
C13 C12 C11 121.52(18) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 121.14(18) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
N17 C14 C13 120.63(17) . . ?
N17 C14 C15 122.28(17) . . ?
C13 C14 C15 117.09(17) . . ?
C16 C15 C14 121.03(18) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 121.08(17) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C14 N17 C18 120.60(16) . . ?
C14 N17 C19 122.19(17) . . ?
C18 N17 C19 117.21(16) . . ?
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 . . ?
N17 C19 H19A 109.5 . . ?
N17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C26 119.85(17) . . ?
C22 C21 C27 118.16(17) . . ?
C26 C21 C27 121.94(17) . . ?
C23 C22 C21 119.05(18) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
O24 N23 O23 124.2(2) . . ?
O24 N23 C23 118.4(2) . . ?
O23 N23 C23 117.4(2) . . ?
C24 C23 C22 122.61(18) . . ?
C24 C23 N23 118.28(19) . . ?
C22 C23 N23 119.11(19) . . ?
C25 C24 C23 116.94(18) . . ?
C25 C24 H24 121.5 . . ?
C23 C24 H24 121.5 . . ?
O25 N25 O26 124.11(17) . . ?
O25 N25 C25 118.10(17) . . ?
O26 N25 C25 117.79(16) . . ?
C24 C25 C26 122.70(17) . . ?
C24 C25 N25 118.40(17) . . ?
C26 C25 N25 118.89(16) . . ?
C25 C26 C21 118.84(17) . . ?
C25 C26 H26 120.6 . . ?
C21 C26 H26 120.6 . . ?
O27 C27 O28 125.55(19) . . ?
O27 C27 C21 122.34(18) . . ?
O28 C27 C21 112.08(17) . . ?
C27 O28 H28 114.9(16) . . ?
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 C6 1.391(2) . ?
C1 C2 1.404(2) . ?
C1 N9 1.420(2) . ?
C2 C3 1.393(3) . ?
C2 C7 1.483(3) . ?
C3 C4 1.372(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.368(3) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
O7 C7 1.224(2) . ?
C7 O8 1.307(2) . ?
O8 H8 1.01(2) . ?
N9 N10 1.2726(19) . ?
N10 C11 1.385(2) . ?
C11 C12 1.393(2) . ?
C11 C16 1.396(2) . ?
C12 C13 1.364(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.406(3) . ?
C13 H13 0.9400 . ?
C14 N17 1.355(2) . ?
C14 C15 1.419(2) . ?
C15 C16 1.367(3) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
N17 C18 1.453(2) . ?
N17 C19 1.455(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C21 C22 1.380(2) . ?
C21 C26 1.388(2) . ?
C21 C27 1.494(3) . ?
C22 C23 1.377(3) . ?
C22 H22 0.9400 . ?
N23 O24 1.202(2) . ?
N23 O23 1.217(2) . ?
N23 C23 1.474(2) . ?
C23 C24 1.374(3) . ?
C24 C25 1.372(2) . ?
C24 H24 0.9400 . ?
O25 N25 1.2125(19) . ?
N25 O26 1.2172(19) . ?
N25 C25 1.468(2) . ?
C25 C26 1.377(2) . ?
C26 H26 0.9400 . ?
O27 C27 1.206(2) . ?
C27 O28 1.303(2) . ?
O28 H28 0.81(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
O28 H28 O7 0.81(2) 1.82(2) 2.6069(19) 163(2) .
O8 H8 N9 1.01(2) 1.58(2) 2.5353(19) 156(2) .
C13 H13 O25 0.94 2.45 3.184(2) 134.6 1_444
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 -0.4(2) . . . . ?
N9 C1 C2 C3 179.70(15) . . . . ?
C6 C1 C2 C7 179.01(16) . . . . ?
N9 C1 C2 C7 -0.9(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C7 C2 C3 C4 -179.36(16) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
N9 C1 C6 C5 -179.37(16) . . . . ?
C3 C2 C7 O7 1.5(3) . . . . ?
C1 C2 C7 O7 -177.89(18) . . . . ?
C3 C2 C7 O8 -178.63(18) . . . . ?
C1 C2 C7 O8 2.0(3) . . . . ?
C6 C1 N9 N10 -0.8(2) . . . . ?
C2 C1 N9 N10 179.08(14) . . . . ?
C1 N9 N10 C11 179.88(14) . . . . ?
N9 N10 C11 C12 -179.93(15) . . . . ?
N9 N10 C11 C16 0.0(3) . . . . ?
N10 C11 C12 C13 -179.80(17) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 N17 179.81(18) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
N17 C14 C15 C16 -179.45(17) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
N10 C11 C16 C15 -179.83(17) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
C13 C14 N17 C18 -0.6(3) . . . . ?
C15 C14 N17 C18 179.35(17) . . . . ?
C13 C14 N17 C19 179.96(16) . . . . ?
C15 C14 N17 C19 -0.1(3) . . . . ?
C26 C21 C22 C23 0.2(3) . . . . ?
C27 C21 C22 C23 177.78(15) . . . . ?
C21 C22 C23 C24 -1.1(3) . . . . ?
C21 C22 C23 N23 179.28(16) . . . . ?
O24 N23 C23 C24 -2.4(3) . . . . ?
O23 N23 C23 C24 177.04(19) . . . . ?
O24 N23 C23 C22 177.29(19) . . . . ?
O23 N23 C23 C22 -3.3(3) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
N23 C23 C24 C25 -179.56(16) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C23 C24 C25 N25 -178.13(16) . . . . ?
O25 N25 C25 C24 5.3(3) . . . . ?
O26 N25 C25 C24 -174.65(16) . . . . ?
O25 N25 C25 C26 -173.21(16) . . . . ?
O26 N25 C25 C26 6.8(3) . . . . ?
C24 C25 C26 C21 -1.1(3) . . . . ?
N25 C25 C26 C21 177.33(15) . . . . ?
C22 C21 C26 C25 0.8(2) . . . . ?
C27 C21 C26 C25 -176.63(15) . . . . ?
C22 C21 C27 O27 -7.6(3) . . . . ?
C26 C21 C27 O27 169.89(17) . . . . ?
C22 C21 C27 O28 174.18(16) . . . . ?
C26 C21 C27 O28 -8.3(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21197930
2 PubChem 139195524
