#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/51/2215188.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_2215188
loop_
_publ_author_name
'Zhong-Lu You'
'Wei-Min Dai'
'Yi-Qiao Hu'
_publ_section_title
;
 2-Hydroxypyridinium 2,4,6-trinitrophenolate
;
_journal_coeditor_code           KP2123
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3735
_journal_page_last               o3735
_journal_paper_doi               10.1107/S160053680703872X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H6 N O +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C5 H6 N O +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C11 H8 N4 O8'
_chemical_formula_weight         324.21
_chemical_name_systematic
;
2-Hydroxypyridinium 2,4,6-trinitrophenolate
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.128(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.360(3)
_cell_length_b                   3.7323(10)
_cell_length_c                   27.575(7)
_cell_measurement_reflns_used    718
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.37
_cell_measurement_theta_min      2.22
_cell_volume                     1270.2(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0812
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            9449
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.280
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0665
_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)+(0.0695P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                1468
_reflns_number_total             2633
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2123.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215188
_cod_database_fobs_code          2215188
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.08847(19) 0.7094(8) 0.47182(8) 0.0498(7) Uani d D 1
O O2 0.19824(18) 0.3631(7) 0.41230(8) 0.0510(7) Uani d . 1
O O3 0.02968(19) 0.7159(7) 0.36716(9) 0.0560(8) Uani d . 1
O O4 -0.01971(19) 0.4424(8) 0.30070(9) 0.0646(9) Uani d . 1
O O5 0.2730(2) 0.3254(9) 0.19155(9) 0.0718(10) Uani d . 1
O O6 0.4134(2) 0.0296(8) 0.21813(9) 0.0625(9) Uani d . 1
O O7 0.4813(2) -0.1360(8) 0.38769(9) 0.0628(8) Uani d . 1
O O8 0.3973(2) 0.1652(9) 0.43928(9) 0.0698(9) Uani d . 1
N N1 0.2547(2) 0.5368(8) 0.50557(9) 0.0375(7) Uani d D 1
N N2 0.0490(2) 0.5260(8) 0.33235(10) 0.0401(8) Uani d . 1
N N3 0.3295(2) 0.1891(9) 0.22435(10) 0.0445(8) Uani d . 1
N N4 0.4074(2) 0.0611(8) 0.39779(10) 0.0396(7) Uani d . 1
C C1 0.1554(3) 0.6779(9) 0.51021(11) 0.0333(8) Uani d . 1
C C2 0.1262(3) 0.7854(9) 0.55578(11) 0.0385(9) Uani d . 1
H H2 0.0580 0.8824 0.5599 0.046 Uiso calc R 1
C C3 0.1985(3) 0.7474(9) 0.59448(12) 0.0450(10) Uani d . 1
H H3 0.1792 0.8195 0.6251 0.054 Uiso calc R 1
C C4 0.3011(3) 0.6021(10) 0.58887(12) 0.0451(10) Uani d . 1
H H4 0.3503 0.5773 0.6154 0.054 Uiso calc R 1
C C5 0.3270(3) 0.4985(9) 0.54424(12) 0.0426(9) Uani d . 1
H H5 0.3948 0.3999 0.5398 0.051 Uiso calc R 1
C C6 0.2276(2) 0.3217(9) 0.36964(11) 0.0316(8) Uani d . 1
C C7 0.1595(2) 0.3997(9) 0.32664(11) 0.0316(8) Uani d . 1
C C8 0.1906(2) 0.3560(9) 0.28060(11) 0.0332(8) Uani d . 1
H H8 0.1437 0.4126 0.2542 0.040 Uiso calc R 1
C C9 0.2940(3) 0.2251(9) 0.27358(11) 0.0338(8) Uani d . 1
C C10 0.3629(3) 0.1285(9) 0.31213(11) 0.0343(8) Uani d . 1
H H10 0.4308 0.0340 0.3068 0.041 Uiso calc R 1
C C11 0.3303(2) 0.1730(9) 0.35853(11) 0.0331(8) Uani d . 1
H H1A 0.271(3) 0.451(11) 0.4762(7) 0.080 Uiso d D 1
H H1 0.123(3) 0.645(12) 0.4472(9) 0.080 Uiso d D 1
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
C1 O1 H1 107(3)
C1 N1 C5 121.9(3)
C1 N1 H1A 118(3)
C5 N1 H1A 119(3)
O4 N2 O3 123.2(3)
O4 N2 C7 117.2(3)
O3 N2 C7 119.6(3)
O6 N3 O5 123.8(3)
O6 N3 C9 118.7(3)
O5 N3 C9 117.5(3)
O7 N4 O8 121.5(3)
O7 N4 C11 118.0(3)
O8 N4 C11 120.4(3)
O1 C1 N1 119.7(3)
O1 C1 C2 121.4(3)
N1 C1 C2 118.9(3)
C3 C2 C1 119.3(3)
C3 C2 H2 120.4
C1 C2 H2 120.4
C2 C3 C4 121.0(3)
C2 C3 H3 119.5
C4 C3 H3 119.5
C5 C4 C3 118.4(3)
C5 C4 H4 120.8
C3 C4 H4 120.8
C4 C5 N1 120.5(3)
C4 C5 H5 119.7
N1 C5 H5 119.7
O2 C6 C11 123.4(3)
O2 C6 C7 123.8(3)
C11 C6 C7 112.7(3)
C8 C7 C6 124.1(3)
C8 C7 N2 117.0(3)
C6 C7 N2 118.8(3)
C7 C8 C9 118.8(3)
C7 C8 H8 120.6
C9 C8 H8 120.6
C10 C9 C8 121.3(3)
C10 C9 N3 119.5(3)
C8 C9 N3 119.2(3)
C11 C10 C9 119.3(3)
C11 C10 H10 120.4
C9 C10 H10 120.4
C10 C11 C6 123.6(3)
C10 C11 N4 116.3(3)
C6 C11 N4 120.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.313(4)
O1 H1 0.86(3)
O2 C6 1.260(3)
O3 N2 1.227(3)
O4 N2 1.224(3)
O5 N3 1.223(4)
O6 N3 1.216(3)
O7 N4 1.217(3)
O8 N4 1.221(3)
N1 C1 1.348(4)
N1 C5 1.361(4)
N1 H1A 0.906(10)
N2 C7 1.462(4)
N3 C9 1.456(4)
N4 C11 1.463(4)
C1 C2 1.385(4)
C2 C3 1.361(4)
C2 H2 0.9300
C3 C4 1.395(5)
C3 H3 0.9300
C4 C5 1.345(4)
C4 H4 0.9300
C5 H5 0.9300
C6 C11 1.434(4)
C6 C7 1.446(4)
C7 C8 1.356(4)
C8 C9 1.391(4)
C8 H8 0.9300
C9 C10 1.373(4)
C10 C11 1.372(4)
C10 H10 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
O1 H1 O3 0.86(3) 2.45(3) 2.937(3) 117(3)
O1 H1 O2 0.86(3) 1.73(2) 2.539(3) 157(4)
N1 H1A O8 0.906(10) 2.18(3) 2.953(4) 142(3)
N1 H1A O2 0.906(10) 1.96(3) 2.707(4) 138(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21626592
2 PubChem 139072964
