#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/00/2240071.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_2240071
loop_
_publ_author_name
'Kathikeyan, Ammasai'
'Thomas Muthiah, Packianathan'
'Perdih, Franc'
_publ_section_title
;
 Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium
 3-hydroxypyridine-2-carboxylate
;
_journal_coeditor_code           TK5344
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              328
_journal_page_last               330
_journal_paper_doi               10.1107/S1600536814021898
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C4 H5 F N3 O +, C6 H4 N O3 -'
_chemical_formula_moiety         'C4 H5 F N3 O +, C6 H4 N O3 -'
_chemical_formula_sum            'C10 H9 F N4 O4'
_chemical_formula_weight         268.21
_chemical_name_common
;
5-fluoro-cytosinium 3-hydroxypicolinate
;
_chemical_name_systematic
;
4-Amino-5-fluoro-2-oxo-2,3-dihydropyrimidin-1-ium 3-hydroxypicolinate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.6487(4)
_cell_length_b                   7.0786(2)
_cell_length_c                   23.7200(6)
_cell_measurement_reflns_used    3551
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.6770
_cell_measurement_theta_min      3.7100
_cell_volume                     2123.77(10)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2011)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Agilent SuperNova (Dual, Cu at zero, Atlas)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8914
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.194
_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     173
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0424
_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)+(0.0458P)²+0.8599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                1955
_reflns_number_total             2437
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5344sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               2240071
_cod_database_fobs_code          2240071
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_symmetry_multiplicity
F F1 -0.04979(8) 0.58078(18) 0.39473(5) 0.0483(3) Uani d . 1 1
N N1 0.10109(11) 0.8014(2) 0.50442(6) 0.0335(3) Uani d . 1 1
H H1 0.0909 0.8491 0.5373 0.040 Uiso calc R 1 1
N N3 0.21136(11) 0.7249(2) 0.42943(6) 0.0312(3) Uani d . 1 1
H H3 0.2733 0.7239 0.4145 0.037 Uiso calc R 1 1
N N4 0.14821(12) 0.5828(2) 0.34880(6) 0.0392(4) Uani d . 1 1
H H4A 0.2108 0.5846 0.3347 0.047 Uiso calc R 1 1
H H4B 0.0966 0.5360 0.3298 0.047 Uiso calc R 1 1
O O2 0.27785(10) 0.8667(2) 0.50714(5) 0.0446(4) Uani d . 1 1
C C2 0.20128(14) 0.8021(3) 0.48270(7) 0.0317(4) Uani d . 1 1
C C4 0.13147(14) 0.6513(2) 0.39922(7) 0.0296(4) Uani d . 1 1
C C5 0.03071(13) 0.6548(3) 0.42474(7) 0.0332(4) Uani d . 1 1
C C6 0.01722(14) 0.7286(3) 0.47624(7) 0.0346(4) Uani d . 1 1
H H6 -0.0496 0.7299 0.4926 0.041 Uiso calc R 1 1
O O1 0.49981(11) 0.4529(2) 0.24635(5) 0.0430(4) Uani d . 1 1
H H1A 0.4410 0.4833 0.2578 0.064 Uiso calc R 1 1
O O3 0.36400(10) 0.5738(2) 0.31741(5) 0.0408(3) Uani d . 1 1
O O4 0.41321(10) 0.6570(2) 0.40413(5) 0.0416(3) Uani d . 1 1
N N2 0.61308(11) 0.5297(2) 0.38561(6) 0.0296(3) Uani d . 1 1
C C7 0.43231(13) 0.5915(3) 0.35634(7) 0.0301(4) Uani d . 1 1
C C8 0.54219(13) 0.5251(2) 0.34318(7) 0.0274(4) Uani d . 1 1
C C9 0.56959(14) 0.4572(3) 0.28970(7) 0.0306(4) Uani d . 1 1
C C10 0.67182(14) 0.3927(3) 0.28059(7) 0.0347(4) Uani d . 1 1
H H10 0.6918 0.3464 0.2455 0.042 Uiso calc R 1 1
C C11 0.74279(14) 0.3982(3) 0.32407(7) 0.0339(4) Uani d . 1 1
H H11 0.8118 0.3565 0.3189 0.041 Uiso calc R 1 1
C C12 0.71035(14) 0.4669(3) 0.37608(7) 0.0332(4) Uani d . 1 1
H H12 0.7589 0.4690 0.4055 0.040 Uiso calc R 1 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'
F F 0.0171 0.0103 '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
C6 N1 C2 122.73(15)
C6 N1 H1 118.6
C2 N1 H1 118.6
C4 N3 C2 124.84(15)
C4 N3 H3 117.6
C2 N3 H3 117.6
C4 N4 H4A 120.0
C4 N4 H4B 120.0
H4A N4 H4B 120.0
O2 C2 N1 123.98(16)
O2 C2 N3 120.68(16)
N1 C2 N3 115.34(15)
N4 C4 N3 120.63(16)
N4 C4 C5 123.02(16)
N3 C4 C5 116.34(15)
C6 C5 F1 122.47(16)
C6 C5 C4 120.85(16)
F1 C5 C4 116.68(15)
C5 C6 N1 119.89(16)
C5 C6 H6 120.1
N1 C6 H6 120.1
C9 O1 H1A 109.5
C12 N2 C8 118.75(14)
O4 C7 O3 124.40(16)
O4 C7 C8 118.99(15)
O3 C7 C8 116.60(15)
N2 C8 C9 121.32(15)
N2 C8 C7 116.96(14)
C9 C8 C7 121.70(15)
O1 C9 C10 118.77(15)
O1 C9 C8 122.25(16)
C10 C9 C8 118.98(15)
C11 C10 C9 118.99(16)
C11 C10 H10 120.5
C9 C10 H10 120.5
C10 C11 C12 119.08(16)
C10 C11 H11 120.5
C12 C11 H11 120.5
N2 C12 C11 122.87(16)
N2 C12 H12 118.6
C11 C12 H12 118.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C5 1.348(2)
N1 C6 1.356(2)
N1 C2 1.368(2)
N1 H1 0.8600
N3 C4 1.344(2)
N3 C2 1.383(2)
N3 H3 0.8600
N4 C4 1.308(2)
N4 H4A 0.8600
N4 H4B 0.8600
O2 C2 1.218(2)
C4 C5 1.411(2)
C5 C6 1.340(2)
C6 H6 0.9300
O1 C9 1.355(2)
O1 H1A 0.8200
O3 C7 1.271(2)
O4 C7 1.248(2)
N2 C12 1.328(2)
N2 C8 1.348(2)
C7 C8 1.500(2)
C8 C9 1.400(2)
C9 C10 1.388(2)
C10 C11 1.368(2)
C10 H10 0.9300
C11 C12 1.388(2)
C11 H11 0.9300
C12 H12 0.9300
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
N1 H1 N2 3_466 0.86 2.04 2.873(2) 163
N3 H3 O4 . 0.86 1.85 2.6665(18) 158
N4 H4A O3 . 0.86 1.98 2.830(2) 169
N4 H4B O1 6_556 0.86 2.26 3.076(2) 159
N4 H4B F1 . 0.86 2.43 2.7312(18) 101
O1 H1A O3 . 0.82 1.83 2.5542(18) 146
C6 H6 O2 3_466 0.93 2.29 3.127(2) 150
C10 H10 O3 4_645 0.93 2.54 3.272(2) 136
C12 H12 O2 3_566 0.93 2.39 3.129(2) 137
Cll H11 Cg1 7_755 0.93 2.88 3.426(2) 119
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
C6 N1 C2 O2 179.95(18)
C6 N1 C2 N3 0.7(3)
C4 N3 C2 O2 -179.68(17)
C4 N3 C2 N1 -0.4(3)
C2 N3 C4 N4 179.33(17)
C2 N3 C4 C5 0.0(3)
N4 C4 C5 C6 -179.16(18)
N3 C4 C5 C6 0.2(3)
N4 C4 C5 F1 0.8(3)
N3 C4 C5 F1 -179.85(15)
F1 C5 C6 N1 -179.86(16)
C4 C5 C6 N1 0.1(3)
C2 N1 C6 C5 -0.5(3)
C12 N2 C8 C9 -0.5(3)
C12 N2 C8 C7 178.04(16)
O4 C7 C8 N2 4.0(2)
O3 C7 C8 N2 -174.95(16)
O4 C7 C8 C9 -177.49(17)
O3 C7 C8 C9 3.6(3)
N2 C8 C9 O1 -179.39(16)
C7 C8 C9 O1 2.2(3)
N2 C8 C9 C10 0.3(3)
C7 C8 C9 C10 -178.17(16)
O1 C9 C10 C11 179.43(17)
C8 C9 C10 C11 -0.3(3)
C9 C10 C11 C12 0.4(3)
C8 N2 C12 C11 0.7(3)
C10 C11 C12 N2 -0.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139087013
