#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/41/7054104.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_7054104
loop_
_publ_author_name
'Ding, Xue-Hua'
'Cui, Lin-Fang'
'Li, Yong-Hua'
'Wang, Shi'
'Huang, Wei'
_publ_section_title
;
 Proton-transfer supramolecular salts resulting from 3,5-dinitrobenzoic
 acid and aminomethyl pyridine
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1884
_journal_paper_doi               10.1039/c2nj40252a
_journal_volume                  36
_journal_year                    2012
_chemical_formula_moiety         'C26 H24 N8 O12'
_chemical_formula_sum            'C26 H24 N8 O12'
_chemical_formula_weight         640.53
_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                102.99(3)
_cell_angle_beta                 100.52(3)
_cell_angle_gamma                101.26(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4234(15)
_cell_length_b                   11.738(2)
_cell_length_c                   17.698(4)
_cell_measurement_reflns_used    14831
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1431.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      293(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0834
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14831
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0616
_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)+(0.0656P)²+0.0277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                3674
_reflns_number_total             6511
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2nj40252a_3.txt
_cod_data_source_block           3-check
_cod_original_cell_volume        1431.8(5)
_cod_database_code               7054104
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
C1 C 0.4188(4) 0.3197(2) 0.32498(17) 0.0453(7) Uani 1 1 d .
O1 O 0.4020(3) 0.25954(18) 0.37464(13) 0.0740(7) Uani 1 1 d .
O2 O 0.3309(3) 0.29186(16) 0.25386(11) 0.0587(5) Uani 1 1 d .
C2 C 0.5646(3) 0.4411(2) 0.35684(15) 0.0379(6) Uani 1 1 d .
C3 C 0.6644(4) 0.4775(2) 0.43678(15) 0.0442(6) Uani 1 1 d .
H3A H 0.6417 0.4287 0.4705 0.053 Uiso 1 1 calc R
C4 C 0.7978(4) 0.5874(2) 0.46510(15) 0.0424(6) Uani 1 1 d .
C5 C 0.8375(3) 0.6621(2) 0.41701(15) 0.0444(6) Uani 1 1 d .
H5A H 0.9289 0.7349 0.4368 0.053 Uiso 1 1 calc R
C6 C 0.7366(4) 0.6248(2) 0.33864(15) 0.0403(6) Uani 1 1 d .
C7 C 0.6015(3) 0.5153(2) 0.30724(15) 0.0399(6) Uani 1 1 d .
H7A H 0.5367 0.4920 0.2539 0.048 Uiso 1 1 calc R
N1 N 0.9048(4) 0.6248(2) 0.54898(15) 0.0630(7) Uani 1 1 d .
O3 O 1.0156(4) 0.7240(2) 0.57372(14) 0.1068(10) Uani 1 1 d .
O4 O 0.8785(3) 0.5555(2) 0.58959(13) 0.0823(7) Uani 1 1 d .
N2 N 0.7754(4) 0.7041(2) 0.28647(15) 0.0542(6) Uani 1 1 d .
O5 O 0.8976(3) 0.79856(19) 0.31507(14) 0.0796(7) Uani 1 1 d .
O6 O 0.6817(4) 0.6725(2) 0.21757(14) 0.0902(8) Uani 1 1 d .
C8 C -0.0415(3) 0.1933(2) -0.02807(15) 0.0352(6) Uani 1 1 d .
C9 C 0.0662(3) 0.32356(19) 0.01693(14) 0.0335(5) Uani 1 1 d .
C10 C 0.0562(3) 0.3689(2) 0.09554(14) 0.0376(6) Uani 1 1 d .
H10A H -0.0099 0.3198 0.1210 0.045 Uiso 1 1 calc R
C11 C 0.1464(3) 0.4884(2) 0.13521(14) 0.0392(6) Uani 1 1 d .
C12 C 0.2497(3) 0.5652(2) 0.10111(16) 0.0429(6) Uani 1 1 d .
H12A H 0.3106 0.6447 0.1289 0.051 Uiso 1 1 calc R
C13 C 0.2574(3) 0.5167(2) 0.02312(15) 0.0372(6) Uani 1 1 d .
C14 C 0.1661(3) 0.3981(2) -0.02013(14) 0.0357(6) Uani 1 1 d .
H14A H 0.1719 0.3695 -0.0729 0.043 Uiso 1 1 calc R
O7 O -0.0898(2) 0.12561(14) 0.01445(10) 0.0444(4) Uani 1 1 d .
O8 O -0.0762(3) 0.16538(15) -0.10228(10) 0.0506(5) Uani 1 1 d .
O9 O 0.2208(4) 0.6372(2) 0.25409(14) 0.1077(10) Uani 1 1 d .
O10 O 0.0025(4) 0.4781(2) 0.24011(13) 0.0826(7) Uani 1 1 d .
N3 N 0.1224(4) 0.5382(2) 0.21613(14) 0.0572(6) Uani 1 1 d .
N4 N 0.3622(3) 0.5964(2) -0.01656(16) 0.0488(6) Uani 1 1 d .
O11 O 0.4472(3) 0.69897(17) 0.02339(14) 0.0789(7) Uani 1 1 d .
O12 O 0.3618(3) 0.55644(19) -0.08643(14) 0.0678(6) Uani 1 1 d .
N5 N 0.7390(3) -0.0678(2) 0.48526(13) 0.0481(6) Uani 1 1 d .
C15 C 0.5683(4) -0.1433(2) 0.46410(15) 0.0450(6) Uani 1 1 d .
H15A H 0.5446 -0.2000 0.4926 0.054 Uiso 1 1 calc R
C16 C 0.4239(4) -0.1430(2) 0.40257(15) 0.0419(6) Uani 1 1 d .
H16A H 0.3078 -0.1987 0.3903 0.050 Uiso 1 1 calc R
C17 C 0.4539(3) -0.0585(2) 0.35914(14) 0.0375(6) Uani 1 1 d .
C18 C 0.6323(3) 0.0193(2) 0.37966(15) 0.0441(6) Uani 1 1 d .
H18A H 0.6599 0.0767 0.3521 0.053 Uiso 1 1 calc R
C19 C 0.7692(4) 0.0110(2) 0.44153(16) 0.0473(7) Uani 1 1 d .
H19A H 0.8887 0.0629 0.4535 0.057 Uiso 1 1 calc R
C20 C 0.2965(4) -0.0498(2) 0.29523(15) 0.0490(7) Uani 1 1 d .
H20A H 0.3493 -0.0210 0.2547 0.059 Uiso 1 1 calc R
H20B H 0.2126 -0.1292 0.2699 0.059 Uiso 1 1 calc R
N6 N 0.1870(3) 0.03424(17) 0.32977(12) 0.0413(5) Uani 1 1 d .
H6A H 0.0951 0.0383 0.2912 0.062 Uiso 1 1 calc R
H6B H 0.2637 0.1073 0.3524 0.062 Uiso 1 1 calc R
H6C H 0.1368 0.0071 0.3663 0.062 Uiso 1 1 calc R
N7 N 0.8651(3) 0.05395(19) 0.21731(12) 0.0444(5) Uani 1 1 d .
C21 C 0.7237(4) -0.0353(2) 0.16739(16) 0.0473(7) Uani 1 1 d .
H21A H 0.7350 -0.1142 0.1609 0.057 Uiso 1 1 calc R
C22 C 0.5622(3) -0.0161(2) 0.12514(15) 0.0425(6) Uani 1 1 d .
H22A H 0.4678 -0.0810 0.0912 0.051 Uiso 1 1 calc R
C23 C 0.5412(3) 0.1009(2) 0.13355(13) 0.0340(5) Uani 1 1 d .
C24 C 0.6874(3) 0.1937(2) 0.18484(14) 0.0393(6) Uani 1 1 d .
H24A H 0.6800 0.2735 0.1922 0.047 Uiso 1 1 calc R
C25 C 0.8443(3) 0.1664(2) 0.22495(15) 0.0424(6) Uani 1 1 d .
H25A H 0.9410 0.2297 0.2592 0.051 Uiso 1 1 calc R
C26 C 0.3663(3) 0.1250(2) 0.08805(14) 0.0376(6) Uani 1 1 d .
H26A H 0.3909 0.2096 0.0889 0.045 Uiso 1 1 calc R
H26B H 0.3370 0.0778 0.0328 0.045 Uiso 1 1 calc R
N8 N 0.2001(2) 0.09393(16) 0.12264(11) 0.0341(5) Uani 1 1 d .
H8A H 0.0997 0.1091 0.0944 0.051 Uiso 1 1 calc R
H8B H 0.2255 0.1382 0.1730 0.051 Uiso 1 1 calc R
H8C H 0.1758 0.0160 0.1211 0.051 Uiso 1 1 calc R
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
O2 C1 O1 127.5(2) 1 .
O2 C1 O1 127.5(2) . .
O2 C1 O1 127.5(2) 1 1
O2 C1 O1 127.5(2) . 1
O2 C1 C2 117.3(2) 1 .
O2 C1 C2 117.3(2) . .
O1 C1 C2 115.2(2) . .
O1 C1 C2 115.2(2) 1 .
C7 C2 C3 119.6(2) . .
C7 C2 C1 121.0(2) . .
C3 C2 C1 119.4(2) . .
C4 C3 C2 119.1(2) . .
C4 C3 H3A 120.5 . .
C2 C3 H3A 120.5 . .
C5 C4 C3 122.4(2) . .
C5 C4 N1 118.5(2) . .
C3 C4 N1 119.0(2) . .
C6 C5 C4 117.4(2) . .
C6 C5 H5A 121.3 . .
C4 C5 H5A 121.3 . .
C5 C6 C7 122.4(2) . .
C5 C6 N2 118.3(2) . .
C7 C6 N2 119.3(2) . .
C6 C7 C2 119.1(2) . .
C6 C7 H7A 120.4 . .
C2 C7 H7A 120.4 . .
O4 N1 O3 123.6(3) . .
O4 N1 C4 118.3(2) . .
O3 N1 C4 118.1(3) . .
O6 N2 O5 123.7(2) . .
O6 N2 C6 118.2(2) . .
O5 N2 C6 118.1(2) . .
O8 C8 O7 126.4(2) . 1
O8 C8 O7 126.4(2) . .
O8 C8 C9 117.6(2) . .
O7 C8 C9 116.0(2) 1 .
O7 C8 C9 116.0(2) . .
C14 C9 C10 119.6(2) . .
C14 C9 C8 121.3(2) . .
C10 C9 C8 119.0(2) . .
C11 C10 C9 119.1(2) . .
C11 C10 H10A 120.4 . .
C9 C10 H10A 120.4 . .
C12 C11 C10 123.2(2) . .
C12 C11 N3 118.1(2) . .
C10 C11 N3 118.6(2) . .
C11 C12 C13 116.1(2) . .
C11 C12 H12A 122.0 . .
C13 C12 H12A 122.0 . .
C12 C13 C14 123.1(2) . .
C12 C13 N4 118.0(2) . .
C14 C13 N4 118.8(2) . .
C9 C14 C13 118.8(2) . .
C9 C14 H14A 120.6 . .
C13 C14 H14A 120.6 . .
O9 N3 O10 124.2(3) . .
O9 N3 C11 117.8(3) . .
O10 N3 C11 118.0(2) . .
O12 N4 O11 123.8(2) . .
O12 N4 C13 118.5(2) . .
O11 N4 C13 117.7(2) . .
C15 N5 C19 116.1(2) . .
N5 C15 C16 124.3(2) . .
N5 C15 H15A 117.9 . .
C16 C15 H15A 117.9 . .
C15 C16 C17 119.4(2) . .
C15 C16 H16A 120.3 . .
C17 C16 H16A 120.3 . .
C18 C17 C16 116.9(2) . .
C18 C17 C20 122.0(2) . .
C16 C17 C20 121.1(2) . .
C19 C18 C17 119.6(2) . .
C19 C18 H18A 120.2 . .
C17 C18 H18A 120.2 . .
N5 C19 C18 123.7(2) . .
N5 C19 H19A 118.1 . .
C18 C19 H19A 118.1 . .
N6 C20 C17 110.8(2) . .
N6 C20 H20A 109.5 . .
C17 C20 H20A 109.5 . .
N6 C20 H20B 109.5 . .
C17 C20 H20B 109.5 . .
H20A C20 H20B 108.1 . .
C20 N6 H6A 109.5 . .
C20 N6 H6B 109.5 . .
H6A N6 H6B 109.5 . .
C20 N6 H6C 109.5 . .
H6A N6 H6C 109.5 . .
H6B N6 H6C 109.5 . .
C25 N7 C21 116.7(2) . .
N7 C21 C22 123.4(2) . .
N7 C21 H21A 118.3 . .
C22 C21 H21A 118.3 . .
C21 C22 C23 119.7(2) . .
C21 C22 H22A 120.2 . .
C23 C22 H22A 120.2 . .
C24 C23 C22 117.3(2) . .
C24 C23 C26 121.7(2) . .
C22 C23 C26 121.0(2) . .
C25 C24 C23 119.3(2) . .
C25 C24 H24A 120.4 . .
C23 C24 H24A 120.4 . .
N7 C25 C24 123.7(2) . .
N7 C25 H25A 118.1 . .
C24 C25 H25A 118.1 . .
N8 C26 C23 111.90(18) . .
N8 C26 H26A 109.2 . .
C23 C26 H26A 109.2 . .
N8 C26 H26B 109.2 . .
C23 C26 H26B 109.2 . .
H26A C26 H26B 107.9 . .
C26 N8 H8A 109.5 . .
C26 N8 H8B 109.5 . .
H8A N8 H8B 109.5 . .
C26 N8 H8C 109.5 . .
H8A N8 H8C 109.5 . .
H8B N8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.245(3) 1
C1 O2 1.245(3) .
C1 O1 1.254(3) .
C1 O1 1.254(3) 1
C1 C2 1.527(3) .
C2 C7 1.394(3) .
C2 C3 1.398(3) .
C3 C4 1.388(3) .
C3 H3A 0.9300 .
C4 C5 1.381(3) .
C4 N1 1.472(3) .
C5 C6 1.377(3) .
C5 H5A 0.9300 .
C6 C7 1.392(3) .
C6 N2 1.477(3) .
C7 H7A 0.9300 .
N1 O4 1.212(3) .
N1 O3 1.221(3) .
N2 O6 1.222(3) .
N2 O5 1.223(3) .
C8 O8 1.244(3) .
C8 O7 1.258(3) 1
C8 O7 1.258(3) .
C8 C9 1.534(3) .
C9 C14 1.389(3) .
C9 C10 1.394(3) .
C10 C11 1.388(3) .
C10 H10A 0.9300 .
C11 C12 1.381(4) .
C11 N3 1.477(3) .
C12 C13 1.386(3) .
C12 H12A 0.9300 .
C13 C14 1.395(3) .
C13 N4 1.478(3) .
C14 H14A 0.9300 .
O9 N3 1.214(3) .
O10 N3 1.224(3) .
N4 O12 1.219(3) .
N4 O11 1.227(3) .
N5 C15 1.331(3) .
N5 C19 1.345(3) .
C15 C16 1.383(3) .
C15 H15A 0.9300 .
C16 C17 1.394(3) .
C16 H16A 0.9300 .
C17 C18 1.387(3) .
C17 C20 1.507(3) .
C18 C19 1.386(3) .
C18 H18A 0.9300 .
C19 H19A 0.9300 .
C20 N6 1.494(3) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
N6 H6A 0.8900 .
N6 H6B 0.8900 .
N6 H6C 0.8900 .
N7 C25 1.338(3) .
N7 C21 1.340(3) .
C21 C22 1.379(3) .
C21 H21A 0.9300 .
C22 C23 1.390(3) .
C22 H22A 0.9300 .
C23 C24 1.387(3) .
C23 C26 1.509(3) .
C24 C25 1.382(3) .
C24 H24A 0.9300 .
C25 H25A 0.9300 .
C26 N8 1.494(3) .
C26 H26A 0.9700 .
C26 H26B 0.9700 .
N8 H8A 0.8900 .
N8 H8B 0.8900 .
N8 H8C 0.8900 .
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
N6 H6A N7 0.89 2.02 2.900(3) 171.0 1_455
N6 H6B O1 0.89 1.80 2.668(3) 166.2 1
N6 H6C O5 0.89 2.59 3.080(3) 115.9 1_445
N6 H6C N5 0.89 2.51 3.139(3) 128.6 2_656
N8 H8C O7 0.89 2.48 2.973(3) 115.2 2
N8 H8C O8 0.89 2.04 2.921(3) 169.4 2
N8 H8A O7 0.89 1.88 2.750(3) 166.5 1
N8 H8B O2 0.89 1.95 2.757(3) 150.5 1
C15 H15A O1 0.93 2.58 3.419(4) 149.8 2_656
C22 H22A O11 0.93 2.55 3.282(3) 135.6 1_545
C26 H26B O7 0.97 2.57 3.168(3) 120.1 2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139176745
