#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/03/2010306.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_2010306
loop_
_publ_author_name
'Xu, Shimin'
'Gantzel, Peter K.'
'Clark, Leigh B.'
_publ_section_title
;
 Glycoluril
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1988
_journal_page_last               1989
_journal_paper_doi               10.1107/S0108270194006955
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C4 H6 N4 O2'
_chemical_formula_weight         142.12
_chemical_name_common            glycoluril
_chemical_name_systematic
;
tetrahydroimidazo [4,5-d] imidazole-2,5 (1H, 3H)-dione
;
_space_group_IT_number           63
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2c 2'
_symmetry_space_group_name_H-M   'C m c m'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   7.373(2)
_cell_length_b                   7.546(3)
_cell_length_c                   10.579(3)
_cell_measurement_reflns_used    16
_cell_measurement_temperature    299
_cell_measurement_theta_max      13.5
_cell_measurement_theta_min      4
_cell_volume                     588.6(3)
_computing_cell_refinement       SHELXTL-Plus
_computing_data_collection       'SHELXTL-Plus (Sheldrick, year?)'
_computing_data_reduction        SHELXTL-Plus
_computing_molecular_graphics    SHELXTL-Plus
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1994)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      299
_diffrn_measurement_device       'Siemens R3m/V diffractometer'
_diffrn_measurement_method       Wyckoff
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            550
_diffrn_reflns_theta_max         29.94
_diffrn_reflns_theta_min         3.85
_diffrn_standards_decay_%        0.35
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.081
_refine_ls_goodness_of_fit_obs   1.114
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     31
_refine_ls_number_reflns         486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_restrained_S_obs      1.114
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_obs          0.0405
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
; calc w = 1/[\s^2^(F~o~^2^)+(0.0785P)^2^+0.1473P]
  where P = (F~o~^2^+2Fc^2^)/3
;
_refine_ls_wR_factor_all         0.1246
_refine_ls_wR_factor_obs         0.1163
_reflns_number_observed          403
_reflns_number_total             486
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ka1088.cif
_cod_data_source_block           glyc
_cod_database_code               2010306
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z+1/2
-x,y,-z+1/2
x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,-z
-x,-y,-z
x,y,-z-1/2
x,-y,z-1/2
-x,y,z
-x+1/2,-y+1/2,-z
x+1/2,y+1/2,-z-1/2
x+1/2,-y+1/2,z-1/2
-x+1/2,y+1/2,z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0250(6) 0.0651(8) 0.0277(6) 0.000 0.000 -0.0136(5)
N2 0.0189(5) 0.0625(7) 0.0260(5) -0.0012(4) 0.0007(3) -0.0096(4)
C3 0.0227(6) 0.0374(7) 0.0221(6) -0.0028(5) 0.000 0.000
C4 0.0213(6) 0.0414(8) 0.0226(7) 0.000 0.000 -0.0002(6)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.0000 0.2245(2) 0.46658(11) 0.0393(4) Uani d S 1 . O
N2 0.14924(12) 0.3510(2) 0.63534(9) 0.0358(3) Uani d . 1 . N
H2A 0.26281(12) 0.3271(2) 0.60926(9) 0.046(4) Uiso d R 1 . H
C3 0.1059(2) 0.4450(2) 0.7500 0.0274(4) Uani d S 1 . C
H3A 0.1551(2) 0.5628(2) 0.7500 0.031(5) Uiso d SR 1 . H
C4 0.0000 0.3016(2) 0.57014(15) 0.0285(4) Uani d S 1 . C
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N2 C3 . . 112.64(11) yes
N2 C3 N2 10_557 . 114.67(13) yes
N2 C3 C3 10_557 3_556 102.82(7) yes
N2 C3 C3 . 3_556 102.82(7) ?
O1 C4 N2 . . 125.47(7) yes
O1 C4 N2 . 12 125.47(7) ?
N2 C4 N2 . 12 109.05(14) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.241(2) yes
N2 C4 . 1.3512(13) yes
N2 C3 . 1.4409(13) yes
C3 N2 10_557 1.4409(13) ?
C3 C3 3_556 1.561(3) yes
C4 N2 12 1.3512(13) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 62347
