#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226848.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226848
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
'Young, David J.'
_publ_section_title
;
 2-(2,4-Dinitrobenzyl)pyridinium 2-hydroxy-3,5-dinitrobenzoate
;
_journal_coeditor_code           EZ2219
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1895
_journal_paper_doi               10.1107/S1600536810024888
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H10 N3 O4 +, C7 H3 N2 O7 -'
_chemical_formula_moiety         'C12 H10 N3 O4 +, C7 H3 N2 O7 -'
_chemical_formula_sum            'C19 H13 N5 O11'
_chemical_formula_weight         487.34
_chemical_melting_point          383
_chemical_name_systematic
;
2-(2,4-Dinitrobenzyl)pyridinium 2-hydroxy-3,5-dinitrobenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.424(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1550(2)
_cell_length_b                   21.7356(5)
_cell_length_c                   13.2080(4)
_cell_measurement_reflns_used    6248
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      3.11
_cell_volume                     1989.34(10)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S CCD-detector diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13759
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.324
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0513
_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)+(0.0819P)²+0.6730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1534
_reflns_number_gt                2865
_reflns_number_total             3910
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2219.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226848
_cod_database_fobs_code          2226848
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O21 1.2566(3) 0.22969(10) 0.63986(18) 0.0562(8) Uani . . 1.000
O O22 1.1932(4) 0.18930(12) 0.48691(19) 0.0733(10) Uani . . 1.000
O O41 0.7828(4) 0.00564(10) 0.43481(18) 0.0635(9) Uani . . 1.000
O O42 0.6790(3) -0.02169(9) 0.56819(19) 0.0577(8) Uani . . 1.000
N N1 0.6649(3) 0.32238(8) 0.69232(15) 0.0274(6) Uani . . 1.000
N N21 1.1587(3) 0.19783(10) 0.57118(18) 0.0365(7) Uani . . 1.000
N N41 0.7462(3) 0.01652(11) 0.5177(2) 0.0458(8) Uani . . 1.000
C C2 0.7755(3) 0.28074(10) 0.75516(18) 0.0267(7) Uani . . 1.000
C C3 0.7361(4) 0.26743(11) 0.84941(19) 0.0316(7) Uani . . 1.000
C C4 0.5867(4) 0.29735(12) 0.87819(19) 0.0345(8) Uani . . 1.000
C C5 0.4801(4) 0.34101(12) 0.8133(2) 0.0376(8) Uani . . 1.000
C C6 0.5212(4) 0.35297(12) 0.7190(2) 0.0359(8) Uani . . 1.000
C C11 0.8856(3) 0.19180(10) 0.65949(17) 0.0250(7) Uani . . 1.000
C C21 0.9877(3) 0.16655(10) 0.59134(18) 0.0268(7) Uani . . 1.000
C C31 0.9395(3) 0.11127(11) 0.5400(2) 0.0322(8) Uani . . 1.000
C C41 0.7909(4) 0.07812(11) 0.5632(2) 0.0353(8) Uani . . 1.000
C C51 0.6845(4) 0.10000(12) 0.6292(2) 0.0359(8) Uani . . 1.000
C C61 0.7296(3) 0.15746(11) 0.67349(19) 0.0307(7) Uani . . 1.000
C C71 0.9381(3) 0.25231(10) 0.7169(2) 0.0308(7) Uani . . 1.000
O O2A 0.7053(3) 0.51546(8) 0.39374(15) 0.0389(6) Uani . . 1.000
O O11A 0.7728(2) 0.34274(8) 0.51916(13) 0.0363(6) Uani . . 1.000
O O12A 0.6246(3) 0.43376(8) 0.50643(15) 0.0404(6) Uani . . 1.000
O O31A 0.8926(3) 0.60447(8) 0.32114(17) 0.0482(7) Uani . . 1.000
O O32A 1.0404(4) 0.57457(11) 0.20856(19) 0.0703(10) Uani . . 1.000
O O51A 1.4121(3) 0.38998(10) 0.28140(17) 0.0514(7) Uani . . 1.000
O O52A 1.3387(3) 0.32069(9) 0.38239(19) 0.0536(7) Uani . . 1.000
N N31A 0.9667(3) 0.56457(10) 0.28107(17) 0.0388(7) Uani . . 1.000
N N51A 1.3139(3) 0.37048(10) 0.33857(18) 0.0375(7) Uani . . 1.000
C C1A 0.8825(3) 0.42179(10) 0.42470(17) 0.0254(6) Uani . . 1.000
C C2A 0.8508(3) 0.48139(11) 0.38128(18) 0.0276(7) Uani . . 1.000
C C3A 0.9808(4) 0.50221(10) 0.32341(18) 0.0293(7) Uani . . 1.000
C C4A 1.1287(3) 0.46614(11) 0.30776(18) 0.0296(7) Uani . . 1.000
C C5A 1.1555(3) 0.40898(11) 0.35306(18) 0.0278(7) Uani . . 1.000
C C6A 1.0358(3) 0.38671(10) 0.41266(18) 0.0268(7) Uani . . 1.000
C C11A 0.7494(3) 0.39730(11) 0.48798(18) 0.0294(7) Uani . . 1.000
H H1 0.69100 0.32880 0.62900 0.0330 Uiso . R 1.000
H H3 0.80970 0.23840 0.89370 0.0380 Uiso calc R 1.000
H H4 0.55830 0.28790 0.94140 0.0410 Uiso calc R 1.000
H H5 0.38170 0.36210 0.83300 0.0450 Uiso calc R 1.000
H H6 0.44980 0.38210 0.67380 0.0430 Uiso calc R 1.000
H H31 1.00440 0.09700 0.49180 0.0390 Uiso calc R 1.000
H H51 0.58490 0.07680 0.64350 0.0430 Uiso calc R 1.000
H H61 0.65290 0.17380 0.71420 0.0370 Uiso calc R 1.000
H H71 1.04700 0.24550 0.77630 0.0370 Uiso calc R 1.000
H H72 0.97850 0.28120 0.67050 0.0370 Uiso calc R 1.000
H H2A 0.64800 0.49380 0.43920 0.0470 Uiso . R 1.000
H H4A 1.20920 0.48020 0.26720 0.0350 Uiso calc R 1.000
H H6A 1.05890 0.34830 0.44430 0.0320 Uiso calc R 1.000
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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A O2A H2A . . . 106.00 no
C2 N1 C6 . . . 122.9(2) no
O21 N21 C21 . . . 118.4(2) no
O22 N21 C21 . . . 117.5(2) no
O21 N21 O22 . . . 124.1(3) no
O41 N41 O42 . . . 123.9(2) no
O42 N41 C41 . . . 117.8(2) no
O41 N41 C41 . . . 118.3(2) no
C6 N1 H1 . . . 121.00 no
C2 N1 H1 . . . 116.00 no
O31A N31A O32A . . . 122.6(2) no
O31A N31A C3A . . . 119.7(2) no
O32A N31A C3A . . . 117.6(2) no
O51A N51A C5A . . . 117.7(2) no
O52A N51A C5A . . . 118.2(2) no
O51A N51A O52A . . . 124.1(2) no
C3 C2 C71 . . . 124.5(2) no
N1 C2 C3 . . . 118.6(2) no
N1 C2 C71 . . . 116.9(2) no
C2 C3 C4 . . . 119.8(2) no
C3 C4 C5 . . . 120.0(2) no
C4 C5 C6 . . . 119.0(3) no
N1 C6 C5 . . . 119.7(2) no
C61 C11 C71 . . . 120.3(2) no
C21 C11 C71 . . . 123.7(2) no
C21 C11 C61 . . . 116.0(2) no
N21 C21 C11 . . . 121.4(2) no
C11 C21 C31 . . . 123.3(2) no
N21 C21 C31 . . . 115.3(2) no
C21 C31 C41 . . . 117.2(2) no
N41 C41 C51 . . . 118.4(2) no
N41 C41 C31 . . . 119.1(2) no
C31 C41 C51 . . . 122.6(2) no
C41 C51 C61 . . . 118.2(2) no
C11 C61 C51 . . . 122.6(2) no
C2 C71 C11 . . . 113.96(18) no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C6 C5 H5 . . . 121.00 no
C4 C5 H5 . . . 120.00 no
N1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C41 C31 H31 . . . 121.00 no
C21 C31 H31 . . . 121.00 no
C41 C51 H51 . . . 121.00 no
C61 C51 H51 . . . 121.00 no
C11 C61 H61 . . . 119.00 no
C51 C61 H61 . . . 119.00 no
H71 C71 H72 . . . 108.00 no
C2 C71 H72 . . . 109.00 no
C11 C71 H71 . . . 109.00 no
C2 C71 H71 . . . 109.00 no
C11 C71 H72 . . . 109.00 no
C2A C1A C6A . . . 120.9(2) no
C2A C1A C11A . . . 119.2(2) no
C6A C1A C11A . . . 119.9(2) no
O2A C2A C3A . . . 122.1(2) no
C1A C2A C3A . . . 116.8(2) no
O2A C2A C1A . . . 121.0(2) no
N31A C3A C2A . . . 120.7(2) no
C2A C3A C4A . . . 122.2(2) no
N31A C3A C4A . . . 117.0(2) no
C3A C4A C5A . . . 118.7(2) no
N51A C5A C6A . . . 118.9(2) no
C4A C5A C6A . . . 121.7(2) no
N51A C5A C4A . . . 119.4(2) no
C1A C6A C5A . . . 119.6(2) no
O11A C11A C1A . . . 117.7(2) no
O12A C11A C1A . . . 117.3(2) no
O11A C11A O12A . . . 125.0(2) no
C3A C4A H4A . . . 121.00 no
C5A C4A H4A . . . 121.00 no
C1A C6A H6A . . . 120.00 no
C5A C6A H6A . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O21 N21 . . 1.215(3) no
O22 N21 . . 1.213(3) no
O41 N41 . . 1.211(3) no
O42 N41 . . 1.235(3) no
O2A C2A . . 1.321(3) no
O11A C11A . . 1.253(3) no
O12A C11A . . 1.262(3) no
O31A N31A . . 1.206(3) no
O32A N31A . . 1.222(3) no
O51A N51A . . 1.228(3) no
O52A N51A . . 1.219(3) no
O2A H2A . . 0.9300 no
N1 C6 . . 1.343(4) no
N1 C2 . . 1.344(3) no
N21 C21 . . 1.481(3) no
N41 C41 . . 1.470(3) no
N1 H1 . . 0.9100 no
N31A C3A . . 1.460(3) no
N51A C5A . . 1.459(3) no
C2 C71 . . 1.511(3) no
C2 C3 . . 1.374(3) no
C3 C4 . . 1.383(4) no
C4 C5 . . 1.375(4) no
C5 C6 . . 1.374(4) no
C11 C21 . . 1.405(3) no
C11 C61 . . 1.393(3) no
C11 C71 . . 1.518(3) no
C21 C31 . . 1.381(3) no
C31 C41 . . 1.381(4) no
C41 C51 . . 1.377(4) no
C51 C61 . . 1.383(4) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C31 H31 . . 0.9300 no
C51 H51 . . 0.9300 no
C61 H61 . . 0.9300 no
C71 H71 . . 0.9700 no
C71 H72 . . 0.9700 no
C1A C6A . . 1.377(3) no
C1A C11A . . 1.512(3) no
C1A C2A . . 1.412(3) no
C2A C3A . . 1.417(4) no
C3A C4A . . 1.373(4) no
C4A C5A . . 1.372(3) no
C5A C6A . . 1.387(3) no
C4A H4A . . 0.9300 no
C6A H6A . . 0.9300 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O11A . 0.91 1.72 2.627(3) 172 yes
O2A H2A O12A . 0.93 1.61 2.476(3) 152 yes
C3 H3 O11A 4_555 0.93 2.48 3.246(3) 140 yes
C5 H5 O31A 3_666 0.93 2.56 3.051(4) 114 yes
C6 H6 O31A 3_666 0.93 2.48 3.020(4) 117 yes
C51 H51 O51A 4_455 0.93 2.55 3.137(4) 122 yes
C61 H61 O51A 4_455 0.93 2.54 3.141(3) 123 yes
C71 H72 O11A . 0.97 2.55 3.247(3) 129 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . 2.1(3) no
C6 N1 C2 C71 . . . . -177.0(2) no
C2 N1 C6 C5 . . . . -1.4(4) no
O21 N21 C21 C11 . . . . 29.4(3) no
O21 N21 C21 C31 . . . . -149.7(2) no
O22 N21 C21 C11 . . . . -151.4(2) no
O22 N21 C21 C31 . . . . 29.5(3) no
O41 N41 C41 C31 . . . . -27.8(4) no
O41 N41 C41 C51 . . . . 153.4(3) no
O42 N41 C41 C31 . . . . 149.9(2) no
O42 N41 C41 C51 . . . . -28.8(4) no
O31A N31A C3A C2A . . . . 24.4(4) no
O31A N31A C3A C4A . . . . -153.3(2) no
O32A N31A C3A C2A . . . . -159.1(2) no
O32A N31A C3A C4A . . . . 23.2(3) no
O51A N51A C5A C4A . . . . -3.5(3) no
O51A N51A C5A C6A . . . . 176.6(2) no
O52A N51A C5A C4A . . . . 177.6(2) no
O52A N51A C5A C6A . . . . -2.3(3) no
C71 C2 C3 C4 . . . . 178.3(2) no
N1 C2 C71 C11 . . . . -94.0(2) no
C3 C2 C71 C11 . . . . 86.9(3) no
N1 C2 C3 C4 . . . . -0.8(4) no
C2 C3 C4 C5 . . . . -1.1(4) no
C3 C4 C5 C6 . . . . 1.7(4) no
C4 C5 C6 N1 . . . . -0.5(4) no
C61 C11 C21 N21 . . . . -178.8(2) no
C61 C11 C21 C31 . . . . 0.2(3) no
C71 C11 C21 N21 . . . . 0.6(3) no
C71 C11 C21 C31 . . . . 179.6(2) no
C21 C11 C61 C51 . . . . 4.3(3) no
C71 C11 C61 C51 . . . . -175.1(2) no
C21 C11 C71 C2 . . . . 160.2(2) no
C61 C11 C71 C2 . . . . -20.4(3) no
C11 C21 C31 C41 . . . . -4.3(4) no
N21 C21 C31 C41 . . . . 174.8(2) no
C21 C31 C41 N41 . . . . -174.5(2) no
C21 C31 C41 C51 . . . . 4.2(4) no
C31 C41 C51 C61 . . . . 0.0(4) no
N41 C41 C51 C61 . . . . 178.7(2) no
C41 C51 C61 C11 . . . . -4.5(4) no
C6A C1A C2A O2A . . . . -179.2(2) no
C6A C1A C2A C3A . . . . 1.4(3) no
C11A C1A C2A O2A . . . . -1.1(3) no
C11A C1A C2A C3A . . . . 179.5(2) no
C2A C1A C6A C5A . . . . -3.0(3) no
C11A C1A C6A C5A . . . . 178.9(2) no
C2A C1A C11A O11A . . . . 175.0(2) no
C2A C1A C11A O12A . . . . -5.8(3) no
C6A C1A C11A O11A . . . . -6.9(3) no
C6A C1A C11A O12A . . . . 172.3(2) no
O2A C2A C3A N31A . . . . 4.4(4) no
O2A C2A C3A C4A . . . . -178.0(2) no
C1A C2A C3A N31A . . . . -176.2(2) no
C1A C2A C3A C4A . . . . 1.4(3) no
N31A C3A C4A C5A . . . . 175.2(2) no
C2A C3A C4A C5A . . . . -2.5(4) no
C3A C4A C5A N51A . . . . -179.0(2) no
C3A C4A C5A C6A . . . . 0.9(4) no
N51A C5A C6A C1A . . . . -178.2(2) no
C4A C5A C6A C1A . . . . 1.9(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079291
