#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/83/2018388.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_2018388
loop_
_publ_author_name
'Gerhardt, Valeska'
'Tutughamiarso, Maya'
'Bolte, Michael'
_publ_section_title
;
 Conformational studies of hydantoin-5-acetic acid and orotic acid
;
_journal_coeditor_code           SK3419
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o92
_journal_page_last               o98
_journal_paper_doi               10.1107/S0108270112001151
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C5 H4 N2 O4 , C2 H6 O S'
_chemical_formula_moiety         'C5 H4 N2 O4, C2 H6 O S'
_chemical_formula_sum            'C7 H10 N2 O5 S'
_chemical_formula_weight         234.23
_chemical_name_common
;
orotic acid dimethyl sulfoxide monosolvate
;
_chemical_name_systematic
;
2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
dimethyl sulfoxide monosolvate
;
_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                 97.447(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3710(6)
_cell_length_b                   5.9752(3)
_cell_length_c                   17.8433(13)
_cell_measurement_reflns_used    9844
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.945
_cell_measurement_theta_min      3.375
_cell_volume                     990.68(11)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_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  0.0764
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18676
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         3.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.9367
_exptl_absorpt_correction_T_min  0.8929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Blessing, 1995; Spek, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.909
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0321
_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)+(0.0406P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0715
_reflns_number_gt                1383
_reflns_number_total             1865
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3419.cif
_cod_data_source_block           IIa
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018388
_cod_database_fobs_code          2018388
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
_atom_site_symmetry_multiplicity
N N1 0.89572(19) -0.2416(3) 0.51608(8) 0.0217(4) Uani d . 1 1
H H1 0.960(3) -0.319(4) 0.5367(13) 0.038(7) Uiso d . 1 1
C C2 0.8290(2) -0.3166(3) 0.44711(10) 0.0226(4) Uani d . 1 1
O O21 0.86777(16) -0.4924(2) 0.41954(7) 0.0319(4) Uani d . 1 1
C C3 0.7156(2) -0.1743(3) 0.41215(10) 0.0233(4) Uani d . 1 1
H H3 0.6658 -0.2119 0.3640 0.028 Uiso calc R 1 1
C C4 0.68033(19) 0.0119(3) 0.44777(9) 0.0195(4) Uani d . 1 1
C C41 0.5632(2) 0.1634(3) 0.41131(10) 0.0211(4) Uani d . 1 1
O O42 0.50315(17) 0.1265(3) 0.34854(8) 0.0407(4) Uani d . 1 1
O O43 0.53739(16) 0.3326(2) 0.45316(7) 0.0321(4) Uani d . 1 1
H H43 0.465(3) 0.428(5) 0.4243(15) 0.062(8) Uiso d . 1 1
N N5 0.74985(17) 0.0713(3) 0.51739(8) 0.0212(3) Uani d . 1 1
H H5 0.720(3) 0.201(4) 0.5416(13) 0.043(7) Uiso d . 1 1
C C6 0.86277(19) -0.0504(3) 0.55333(9) 0.0199(4) Uani d . 1 1
O O61 0.92976(15) 0.0044(2) 0.61383(7) 0.0271(3) Uani d . 1 1
C C1X 0.1119(3) 0.4769(4) 0.29052(12) 0.0419(6) Uani d . 1 1
H H1X1 0.1014 0.3275 0.3117 0.063 Uiso calc R 1 1
H H1X2 0.0711 0.4776 0.2371 0.063 Uiso calc R 1 1
H H1X3 0.0610 0.5864 0.3182 0.063 Uiso calc R 1 1
S S2X 0.29746(6) 0.54840(9) 0.29868(3) 0.03026(15) Uani d . 1 1
O O21X 0.34198(15) 0.5853(2) 0.38341(7) 0.0321(4) Uani d . 1 1
C C3X 0.2768(2) 0.8194(4) 0.25787(11) 0.0320(5) Uani d . 1 1
H H3X1 0.2198 0.9128 0.2879 0.048 Uiso calc R 1 1
H H3X2 0.2276 0.8075 0.2061 0.048 Uiso calc R 1 1
H H3X3 0.3718 0.8873 0.2570 0.048 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'
S S 0.1246 0.1234 '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 126.55(16)
C6 N1 H1 116.9(17)
C2 N1 H1 116.5(17)
O21 C2 N1 120.57(17)
O21 C2 C3 124.69(16)
N1 C2 C3 114.74(16)
C4 C3 C2 119.84(16)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 N5 121.67(16)
C3 C4 C41 120.30(16)
N5 C4 C41 118.03(15)
O42 C41 O43 125.26(17)
O42 C41 C4 121.16(16)
O43 C41 C4 113.57(15)
C41 O43 H43 108.7(16)
C4 N5 C6 122.19(16)
C4 N5 H5 119.2(14)
C6 N5 H5 118.6(14)
O61 C6 N5 123.24(17)
O61 C6 N1 121.83(17)
N5 C6 N1 114.93(15)
S2X C1X H1X1 109.5
S2X C1X H1X2 109.5
H1X1 C1X H1X2 109.5
S2X C1X H1X3 109.5
H1X1 C1X H1X3 109.5
H1X2 C1X H1X3 109.5
O21X S2X C3X 105.96(9)
O21X S2X C1X 104.71(9)
C3X S2X C1X 97.59(10)
S2X C3X H3X1 109.5
S2X C3X H3X2 109.5
H3X1 C3X H3X2 109.5
S2X C3X H3X3 109.5
H3X1 C3X H3X3 109.5
H3X2 C3X H3X3 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.377(2)
N1 C2 1.381(2)
N1 H1 0.81(3)
C2 O21 1.235(2)
C2 C3 1.438(3)
C3 C4 1.344(3)
C3 H3 0.9500
C4 N5 1.373(2)
C4 C41 1.504(2)
C41 O42 1.207(2)
C41 O43 1.298(2)
O43 H43 0.98(3)
N5 C6 1.372(2)
N5 H5 0.95(3)
C6 O61 1.221(2)
C1X S2X 1.778(2)
C1X H1X1 0.9800
C1X H1X2 0.9800
C1X H1X3 0.9800
S2X O21X 1.5313(12)
S2X C3X 1.775(2)
C3X H3X1 0.9800
C3X H3X2 0.9800
C3X H3X3 0.9800
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 O21 3_746 0.81(3) 2.04(3) 2.846(2) 175(2)
N5 H5 O21X 3_666 0.95(3) 1.99(3) 2.912(2) 164(2)
O43 H43 O21X . 0.98(3) 1.59(3) 2.5675(18) 176(2)
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 O21 -179.51(18)
C6 N1 C2 C3 0.9(3)
O21 C2 C3 C4 178.84(19)
N1 C2 C3 C4 -1.6(3)
C2 C3 C4 N5 -0.1(3)
C2 C3 C4 C41 179.23(17)
C3 C4 C41 O42 -3.2(3)
N5 C4 C41 O42 176.17(18)
C3 C4 C41 O43 177.81(17)
N5 C4 C41 O43 -2.9(2)
C3 C4 N5 C6 2.6(3)
C41 C4 N5 C6 -176.69(16)
C4 N5 C6 O61 176.99(17)
C4 N5 C6 N1 -3.2(3)
C2 N1 C6 O61 -178.73(18)
C2 N1 C6 N5 1.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654358
2 PubChem 139061258
