#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/49/2104910.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_2104910
loop_
_publ_author_name
'Gryl, Marlena'
'Krawczuk-Pantula, Anna'
'Stadnicka, Katarzyna'
_publ_section_title
;
 Charge-density analysis in polymorphs of urea--barbituric acid
 co-crystals
;
_journal_coeditor_code           GW5010
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              144
_journal_page_last               154
_journal_paper_doi               10.1107/S0108768111002412
_journal_volume                  67
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C4 H4 N2 O3, C H4 N2 O '
_chemical_formula_sum            'C5 H8 N4 O4'
_chemical_formula_weight         188.15
_chemical_name_common            'barbituric acid urea addition compound'
_chemical_name_systematic
; 
2,4,6(1H,3H,5H)-Pyrimidinetrione urea addition compound
;
_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                 96.727(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8123(1)
_cell_length_b                   6.9384(1)
_cell_length_c                   14.1179(3)
_cell_measurement_reflns_used    6744
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      47.60
_cell_measurement_theta_min      0.998
_cell_measurement_wavelength     0.71073
_cell_volume                     759.99(2)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction
'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
  PLATON (Spek, 2003); ORTEP-3 for Windows (Farrugia, 1997); MERCURY (Version
  1.4; Macrae et al., 2006)
;
_computing_publication_material  'Volkov et al, (2006)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'ω scans atχ=55°'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13521
_diffrn_reflns_reduction_process
;
 Merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        47.60
_diffrn_reflns_theta_max         47.60
_diffrn_source                   'Nonius KappaCCD'
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        HKL DENZO and Scalepack (Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.05
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.358
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         5793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.029
_reflns_number_gt                5793
_reflns_number_total             7049
_reflns_threshold_expression     >2/s(I)
_cod_data_source_file            gw5010.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2104910
_cod_database_fobs_code          2104910
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_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(2) C(2) Z O(2) N(3) Y
O(4) C(6) Z O(4) N(3) Y
O(6) C(4) Z O(6) N(1) Y
O(1) C(1) Z O(1) N(4) Y
N(1) H(1) Z N(1) C(2) Y
N(3) H(3) Z N(3) C(6) Y
N(2) H(2B) Z N(2) H(2A) Y
N(4) H(4A) Z N(4) H(4B) Y
C(2) O(2) Z C(2) N(1) Y
C(4) O(6) Z C(4) N(1) Y
C(5) H(5A) Z C(5) H(5B) Y
C(6) O(4) Z C(6) N(3) Y
C(1) O(1) Z C(1) N(4) Y
H(5A) C(5) Z H(5A) H(5B) Y
H(5B) C(5) Z H(5B) H(5A) Y
H(1) N(1) Z H(1) C(2) Y
H(3) N(3) Z H(3) C(6) Y
H(2A) N(2) Z H(2A) H(2B) Y
H(2B) N(2) Z H(2B) H(2A) Y
H(4A) N(4) Z H(4A) H(4B) Y
H(4B) N(4) Z H(4B) H(4A) Y
loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
O(2) 6.088(19) 0 0.00(2) -0.06(2) -0.22(4) -0.14(3) 0.02(2) 0.00(2) -0.18(2)
-0.052(19) -0.03(3) 0.03(3) -0.11(3) 0.04(2) -0.02(2) 0.042(18) -0.008(17) 0 0 0
0 0 0 0 0 0 0.984052 0.45(3) 0.450205 0.450205 0.450205 0.450205 2 4.466 2 4.466
2 4.466 3 4.466 4 4.466
O(4) 6.045(14) 0 -0.016(8) 0.008(7) -0.054(9) -0.052(9) -0.001(8) -0.003(7)
-0.100(7) -0.010(7) 0.010(7) 0.010(7) 0.003(6) 0.016(6) -0.006(6) 0.026(6)
0.032(6) 0 0 0 0 0 0 0 0 0 0.983683 0.88(5) 0.876276 0.876276 0.876276 0.876276
2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(6) 6.0445 0 -0.0157 0.0079 -0.0537 -0.0517 -0.0014 -0.0034 -0.0999 -0.0095
0.0099 0.0099 0.0029 0.0158 -0.006 0.026 0.0322 0 0 0 0 0 0 0 0 0 0.983683
0.88(5) 0.876276 0.876276 0.876276 0.876276 2 4.466 2 4.466 2 4.466 3 4.466 4
4.466
O(1) 6.164(18) 0 -0.04(5) 0.10(5) -1.05(13) -0.67(8) -0.23(4) -0.12(4) -0.25(4)
0.04(3) -0.11(8) -0.11(6) -0.09(5) 0.14(6) 0.08(5) 0.02(5) -0.08(4) 0 0 0 0 0 0
0 0 0 0.983787 0.299(11) 0.29886 0.29886 0.29886 0.29886 2 4.466 2 4.466 2 4.466
3 4.466 4 4.466
N(1) 5.149(18) 0 -0.044(8) -0.003(8) 0.026(11) 0.035(10) -0.074(7) -0.011(7)
-0.018(9) 0.000(8) 0.261(14) -0.121(8) 0.002(8) 0.178(11) -0.006(8) -0.008(8)
0.006(7) 0 0 0 0 0 0 0 0 0 0.98094 0.777(17) 0.777368 0.777368 0.777368 0.777368
2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(3) 5.1487 0 -0.0436 -0.0031 0.0264 0.0345 -0.0735 -0.0105 -0.0183 0.0003
0.2607 -0.1212 0.0017 0.1777 -0.0064 -0.0084 0.0057 0 0 0 0 0 0 0 0 0 0.98094
0.777(17) 0.777368 0.777368 0.777368 0.777368 2 3.83936 2 3.83936 2 3.83936 3
3.83936 4 3.83936
N(2) 5.231(18) 0 0.023(8) -0.025(11) -0.007(8) -0.001(9) -0.007(7) -0.003(8)
-0.005(9) 0.013(7) 0.229(13) 0.004(7) 0.023(8) 0.143(10) -0.023(7) -0.022(7)
-0.023(7) 0 0 0 0 0 0 0 0 0 0.981057 0.82(2) 0.823911 0.823911 0.823911 0.823911
2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(4) 5.2311 0 0.0229 -0.0251 -0.0071 -0.0007 -0.0071 -0.003 -0.005 0.0134 0.2291
0.0041 0.0231 0.1425 -0.0228 -0.0224 -0.0234 0 0 0 0 0 0 0 0 0 0.981057 0.82(2)
0.823911 0.823911 0.823911 0.823911 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4
3.83936
C(2) 4.10(5) 0 -0.024(13) -0.001(12) 0.134(16) 0.227(13) -0.015(11) -0.002(11)
-0.169(11) 0.019(9) 0.233(17) -0.016(11) -0.007(11) 0.203(14) -0.014(11)
0.002(10) 0.002(9) 0 0 0 0 0 0 0 0 0 0.973987 1.01(3) 1.011279 1.011279 1.011279
1.011279 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(4) 3.96(2) 0 0.012(7) -0.046(9) 0.100(10) 0.233(10) 0.006(7) 0.032(8)
-0.179(8) 0.000(7) 0.261(14) 0.008(8) 0.001(9) 0.192(11) -0.008(8) -0.001(7)
0.007(7) 0 0 0 0 0 0 0 0 0 0.982467 1.00(2) 1.000649 1.000649 1.000649 1.000649
2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(5) 4.17(3) 0 -0.014(10) 0.074(13) -0.016(12) 0.021(11) -0.019(10) 0.011(10)
-0.050(12) -0.020(9) 0.164(17) -0.005(11) 0.027(10) -0.053(11) -0.004(10)
0.027(10) -0.205(17) 0 0 0 0 0 0 0 0 0 0.978642 0.95(3) 0.945714 0.945714
0.945714 0.945714 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(6) 3.955 0 0.012 -0.0455 0.1003 0.2331 0.0062 0.0321 -0.1792 0 0.2605 0.0075
0.0013 0.1923 -0.0077 -0.0007 0.007 0 0 0 0 0 0 0 0 0 0.982467 1.00(2) 1.000649
1.000649 1.000649 1.000649 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(1) 4.43(5) 0 -0.015(11) 0.004(9) 0.076(12) 0.159(10) -0.013(9) 0.023(8)
-0.165(11) -0.018(8) 0.193(15) -0.006(8) -0.016(10) 0.158(13) -0.005(8) 0.003(9)
0.019(8) 0 0 0 0 0 0 0 0 0 0.97621 1.12(4) 1.11758 1.11758 1.11758 1.11758 2
3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
H(5A) 0.889(15) 0 0 0 0.104(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13
1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(5B) 0.8886 0 0 0 0.104 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29
1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(1) 0.665(14) 0 0 0 0.118(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13
1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(3) 0.6646 0 0 0 0.1178 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29
1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(2A) 0.795(10) 0 0 0 0.155(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13
1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(2B) 0.7947 0 0 0 0.1549 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29
1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(4A) 0.7947 0 0 0 0.1549 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29
1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(4B) 0.7947 0 0 0 0.1549 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29
1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 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_occupancy
_atom_site_symmetry_multiplicity
O(2) 0.12430(3) -0.26341(4) 0.58557(2) 0.015 1 4
O(4) 0.48066(4) 0.08484(5) 0.79397(3) 0.015 1 4
O(6) -0.07456(5) 0.31444(5) 0.67347(3) 0.017 1 4
O(1) 0.29486(3) 0.08165(3) 0.456716(18) 0.013 1 4
N(1) 0.02955(4) 0.03185(4) 0.62473(2) 0.011 1 4
N(3) 0.30929(4) -0.07636(4) 0.68093(2) 0.011 1 4
N(2) 0.49881(4) 0.26216(5) 0.54367(3) 0.015 1 4
N(4) 0.22515(4) 0.38318(5) 0.50054(3) 0.016 1 4
C(2) 0.15181(5) -0.11043(5) 0.62796(3) 0.011 1 4
C(4) 0.04467(4) 0.20053(5) 0.67655(2) 0.011 1 4
C(5) 0.21388(5) 0.23512(6) 0.73637(3) 0.013 1 4
C(6) 0.34490(4) 0.07729(5) 0.74016(2) 0.011 1 4
C(1) 0.33815(5) 0.23719(6) 0.49898(3) 0.011 1 4
H(5A) 0.27128 0.365152 0.710028 0.028 1 4
H(5B) 0.187412 0.26475 0.809216 0.03 1 4
H(1) -0.08065 0.01112 0.581024 0.027 1 4
H(3) 0.404729 -0.172295 0.675519 0.027 1 4
H(2A) 0.58414 0.152843 0.544491 0.028 1 4
H(2B) 0.528515 0.382294 0.58242 0.028 1 4
H(4A) 0.104336 0.362376 0.468322 0.029 1 4
H(4B) 0.259089 0.511527 0.530696 0.029 1 4
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(2) N(1) C(4) 125.31(3) 1_555 1_555 1_555 yes
C(2) N(3) C(6) 124.74(3) 1_555 1_555 1_555 yes
O(2) C(2) N(1) 121.74(3) 1_555 1_555 1_555 yes
O(2) C(2) N(3) 120.41(3) 1_555 1_555 1_555 yes
N(1) C(2) N(3) 117.85(3) 1_555 1_555 1_555 yes
O(6) C(4) N(1) 120.95(3) 1_555 1_555 1_555 yes
O(6) C(4) C(5) 122.35(3) 1_555 1_555 1_555 yes
N(1) C(4) C(5) 116.69(3) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 117.17(3) 1_555 1_555 1_555 yes
O(4) C(6) N(3) 120.71(3) 1_555 1_555 1_555 yes
O(4) C(6) C(5) 121.83(3) 1_555 1_555 1_555 yes
N(3) C(6) C(5) 117.45(3) 1_555 1_555 1_555 yes
O(1) C(1) N(2) 121.01(3) 1_555 1_555 1_555 yes
O(1) C(1) N(4) 120.82(4) 1_555 1_555 1_555 yes
N(2) C(1) N(4) 118.17(3) 1_555 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(2) C(2) 1.2250(4) 1_555 1_555 yes
O(4) C(6) 1.2312(4) 1_555 1_555 yes
O(6) C(4) 1.2185(5) 1_555 1_555 yes
O(1) C(1) 1.2601(4) 1_555 1_555 yes
N(1) C(2) 1.3706(5) 1_555 1_555 yes
N(1) C(4) 1.3780(4) 1_555 1_555 yes
N(1) H(1) 1.0090 1_555 1_555 yes
N(3) C(2) 1.3832(5) 1_555 1_555 yes
N(3) C(6) 1.3634(5) 1_555 1_555 yes
N(3) H(3) 1.0090 1_555 1_555 yes
N(2) C(1) 1.3483(5) 1_555 1_555 yes
N(2) H(2A) 1.0090 1_555 1_555 yes
N(2) H(2B) 1.0090 1_555 1_555 yes
N(4) C(1) 1.3455(5) 1_555 1_555 yes
N(4) H(4A) 1.0090 1_555 1_555 yes
N(4) H(4B) 1.0090 1_555 1_555 yes
C(4) C(5) 1.5023(5) 1_555 1_555 yes
C(5) C(6) 1.4956(5) 1_555 1_555 yes
C(5) H(5A) 1.0920 1_555 1_555 yes
C(5) H(5B) 1.0920 1_555 1_555 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 66604723
