#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/37/2203790.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_2203790
loop_
_publ_author_name
'Law, Ga-Lai'
'Szeto, Lap'
'Wong, Wing-Tak'
_publ_section_title
;
 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid monohydrate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1072
_journal_page_last               o1074
_journal_paper_doi               10.1107/S1600536804012267
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C5 H4 N2 O4, H2 O'
_chemical_formula_moiety         'C5 H4 N2 O4, H2 O'
_chemical_formula_sum            'C5 H6 N2 O5'
_chemical_formula_weight         174.11
_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'
_cell_angle_alpha                90
_cell_angle_beta                 101.870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.876(2)
_cell_length_b                   20.352(4)
_cell_length_c                   8.664(2)
_cell_measurement_reflns_used    16902
_cell_measurement_temperature    298.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     1359.1(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2001)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'CRYSTALS (Watkin et al., 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.9759
_diffrn_measured_fraction_theta_max 0.9759
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16902
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720.00
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3154
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.0002Fo² + σ(Fo²) + 0.015]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0470
_reflns_number_gt                2050
_reflns_number_total             3154
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            na6327.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2203790
_cod_database_fobs_code          2203790
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_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_occupancy
_atom_site_type_symbol
O1 0.6791(3) 0.48050(9) 0.9239(3) 0.0583(6) Uani d 1.00 O
O2 0.5790(3) 0.38139(9) 0.9597(2) 0.0523(6) Uani d 1.00 O
O3 0.3468(2) 0.32829(8) 0.7142(2) 0.0462(5) Uani d 1.00 O
O4 0.0685(3) 0.46881(9) 0.3413(2) 0.0489(6) Uani d 1.00 O
O5 -0.2338(3) 0.12755(8) 0.1300(3) 0.0567(6) Uani d 1.00 O
O6 -0.2188(3) 0.23545(8) 0.1543(3) 0.0572(6) Uani d 1.00 O
O7 0.0318(3) 0.28639(8) 0.3913(2) 0.0499(6) Uani d 1.00 O
O8 0.3559(2) 0.14159(8) 0.7243(2) 0.0501(6) Uani d 1.00 O
O9 0.8075(3) 0.37734(11) 1.2129(3) 0.0690(7) Uani d 1.00 O
O10 -0.4738(3) 0.23826(12) -0.0720(3) 0.0764(8) Uani d 1.00 O
N1 0.2120(3) 0.39985(10) 0.5327(3) 0.0394(6) Uani d 1.00 N
N2 0.2840(3) 0.50961(10) 0.5339(3) 0.0398(6) Uani d 1.00 N
N3 0.1588(3) 0.10124(11) 0.5164(3) 0.0433(7) Uani d 1.00 N
N4 0.1871(3) 0.21255(10) 0.5544(3) 0.0393(6) Uani d 1.00 N
C1 0.5759(3) 0.43635(11) 0.8811(3) 0.0383(7) Uani d 1.00 C
C2 0.4372(3) 0.44123(11) 0.7380(3) 0.0340(7) Uani d 1.00 C
C3 0.3352(3) 0.38552(11) 0.6669(3) 0.0340(7) Uani d 1.00 C
C4 0.1794(3) 0.46002(12) 0.4600(3) 0.0370(7) Uani d 1.00 C
C5 0.4057(3) 0.50061(12) 0.6665(3) 0.0370(7) Uani d 1.00 C
C6 -0.1677(3) 0.17629(11) 0.1985(3) 0.0380(7) Uani d 1.00 C
C7 -0.0253(3) 0.17176(11) 0.3383(3) 0.0340(7) Uani d 1.00 C
C8 0.0601(3) 0.22800(11) 0.4243(3) 0.0353(7) Uani d 1.00 C
C9 0.2426(3) 0.15126(12) 0.6079(3) 0.0379(7) Uani d 1.00 C
C10 0.0309(3) 0.11097(12) 0.3893(3) 0.0384(7) Uani d 1.00 C
H1 0.687(4) 0.3813(13) 1.072(3) 0.052(8) Uiso c 1.00 H
H2 0.470(3) 0.5395(13) 0.710(3) 0.042(7) Uiso c 1.00 H
H3 0.267(4) 0.548(2) 0.489(4) 0.061(9) Uiso c 1.00 H
H4 0.147(4) 0.3680(10) 0.484(3) 0.052(8) Uiso c 1.00 H
H5 0.896(6) 0.405(2) 1.246(5) 0.12(2) Uiso c 1.00 H
H6 0.848(5) 0.334(2) 1.239(5) 0.100(10) Uiso c 1.00 H
H7 -0.329(4) 0.2338(12) 0.044(3) 0.046(7) Uiso c 1.00 H
H8 -0.016(3) 0.0716(13) 0.331(3) 0.047(8) Uiso c 1.00 H
H9 0.196(4) 0.0640(10) 0.542(3) 0.051(9) Uiso c 1.00 H
H10 0.240(4) 0.244(2) 0.614(4) 0.066(10) Uiso c 1.00 H
H11 -0.494(6) 0.278(2) -0.123(5) 0.12(2) Uiso c 1.00 H
H12 -0.524(5) 0.204(2) -0.141(5) 0.092(12) Uiso c 1.00 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, 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_publ_flag
C1 O2 H1 111.0(10) no
C6 O6 H7 110.0(10) no
H5 O9 H6 108(3) no
H11 O10 H12 109(3) no
C3 N1 C4 127.2(2) no
C3 N1 H4 119.0(10) no
C4 N1 H4 113.0(10) no
C4 N2 C5 123.4(2) no
C4 N2 H3 115.0(10) no
C5 N2 H3 121.0(10) no
C9 N3 C10 123.6(2) no
C9 N3 H9 115.0(10) no
C10 N3 H9 121.0(10) no
C8 N4 C9 127.6(2) no
C8 N4 H10 119(2) no
C9 N4 H10 113(2) no
C2 C1 O1 122.6(2) no
C2 C1 O2 115.2(2) no
O1 C1 O2 122.2(2) no
C3 C2 C5 117.9(2) no
C3 C2 C1 123.6(2) no
C5 C2 C1 118.5(2) no
O3 C3 N1 118.0(2) no
O3 C3 C2 126.9(2) no
N1 C3 C2 115.1(2) no
O4 C4 N1 123.5(2) no
O4 C4 N2 122.9(2) no
N1 C4 N2 113.7(2) no
H2 C5 N2 116.0(10) no
H2 C5 C2 121.0(10) no
N2 C5 C2 122.7(2) no
C7 C6 O5 121.8(2) no
C7 C6 O6 115.9(2) no
O5 C6 O6 122.4(2) no
C8 C7 C10 117.8(2) no
C8 C7 C6 124.4(2) no
C10 C7 C6 117.8(2) no
O7 C8 N4 118.4(2) no
O7 C8 C7 126.8(2) no
N4 C8 C7 114.9(2) no
O8 C9 N3 122.8(2) no
O8 C9 N4 123.8(2) no
N3 C9 N4 113.4(2) no
H8 C10 N3 116.0(10) no
H8 C10 C7 120.0(10) no
N3 C10 C7 122.7(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.217(3) no
O2 C1 1.307(3) no
O2 H1 1.15(3) no
O3 C3 1.232(3) no
O4 C4 1.218(3) no
O5 C6 1.216(3) no
O6 C6 1.302(3) no
O6 H7 1.15(2) no
O7 C8 1.232(3) no
O8 C9 1.217(3) no
O9 H5 0.90(4) no
O9 H6 0.95(4) no
O10 H11 0.93(5) no
O10 H12 0.95(4) no
N1 C3 1.383(3) no
N1 C4 1.377(3) no
N1 H4 0.87(3) no
N2 C4 1.375(3) no
N2 C5 1.349(3) no
N2 H3 0.87(3) no
N3 C9 1.373(3) no
N3 C10 1.345(3) no
N3 H9 0.83(3) no
N4 C8 1.381(3) no
N4 C9 1.371(3) no
N4 H10 0.87(3) no
C1 C2 1.477(3) no
C2 C3 1.452(3) no
C2 C5 1.358(3) no
C5 H2 0.97(3) no
C6 C7 1.475(3) no
C7 C8 1.453(3) no
C7 C10 1.357(3) no
C10 H8 0.98(3) 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
O2 H1 O9 . 1.15(3) 1.39(3) 2.537(3) 175(3)
N2 H3 O5 2_555 0.87(4) 1.91(4) 2.775(3) 174(3)
N1 H4 O7 . 0.88(2) 1.98(2) 2.852(3) 170(2)
O9 H5 O4 1_656 0.90(5) 1.94(4) 2.826(3) 171(4)
O9 H6 O6 1_656 0.95(4) 2.16(4) 2.932(3) 137(3)
O9 H6 O7 1_656 0.95(4) 2.00(4) 2.795(3) 140(3)
O6 H7 O10 . 1.15(3) 1.36(3) 2.502(4) 170(3)
N3 H9 O1 2_646 0.83(2) 1.96(2) 2.768(3) 168(3)
N4 H10 O3 . 0.87(4) 2.03(4) 2.886(3) 169(3)
O10 H11 O2 1_454 0.92(4) 2.26(4) 2.947(3) 131(3)
O10 H11 O3 1_454 0.92(4) 1.97(4) 2.776(3) 145(4)
O10 H12 O8 1_454 0.95(4) 1.85(4) 2.795(3) 174(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 19972966
2 PubChem 139066759
