#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/92/2019296.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_2019296
loop_
_publ_author_name
'Taouss, Christina'
'Jones, Peter G.'
'Tindall, Daniel J.'
_publ_section_title
;
 Imidazolidin-2-one: pseudosymmetry and twinning
;
_journal_coeditor_code           FG3316
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1534
_journal_page_last               1536
_journal_paper_doi               10.1107/S0108270113030746
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C3 H6 N2 O'
_chemical_formula_moiety         'C3 H6 N2 O'
_chemical_formula_sum            'C3 H6 N2 O'
_chemical_formula_weight         86.10
_chemical_name_systematic
;
Imidazolidin-2-one
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.6219(3)
_cell_length_b                   7.6219(3)
_cell_length_c                   13.1632(9)
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.1860
_cell_measurement_theta_min      3.0760
_cell_volume                     764.69(7)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Oxford Xcalibur Eos'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10301
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.90
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     34
_refine_ls_number_reflns         583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0317
_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/[\s^2^(Fo^2^)+(0.0439P)^2^+0.2482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0794
_reflns_number_gt                546
_reflns_number_total             583
_reflns_threshold_expression     I>2\s(I)
_iucr_refine_instructions_details
;
TITL BOXEN in I4(1)/a
REM I4(1)/a (#88 in standard setting)
CELL 0.71073   7.6219   7.6219  13.1632  90.0000  90.0000  90.0000
ZERR    4.00   0.0003   0.0003   0.0009   0.0000   0.0000   0.0000
LATT  2
SYMM -x+1/2,-y, z+1/2
SYMM -y+3/4, x+1/4, z+1/4
SYMM  y+3/4,-x+3/4, z+3/4
SFAC C H N O
UNIT 24 48 16 8
TWIN 0 1 0 1 0 0 0 0 -1
TEMP -173
SIZE 0.2 0.2 0.18
ACTA 60
CONF
EQIV $1 -x+1, -y+1, -z+1
EQIV $2 -y+5/4, x-1/4, z-1/4
HTAB N2 O1_$1
HTAB N2 O1_$2
L.S. 4
FMAP 2
PLAN 10
WGHT    0.043900    0.248200
BASF   0.20827
FVAR       5.97875
O1    4    0.500000    0.750000    0.519605    10.50000    0.01567    0.01806 =
         0.00905    0.00000    0.00000    0.00028
C1    1    0.500000    0.750000    0.425536    10.50000    0.00921    0.01346 =
         0.01146    0.00000    0.00000   -0.00044
N2    3    0.528868    0.607303    0.365123    11.00000    0.01993    0.01134 =
         0.00963    0.00012   -0.00104    0.00086
H02   2    0.513526    0.504402    0.390275    11.00000    0.02380
C3    1    0.491432    0.649397    0.259252    11.00000    0.01927    0.01551 =
         0.00959   -0.00075   -0.00086    0.00012
AFIX  23
H3A   2    0.371729    0.611959    0.239696    11.00000   -1.20000
H3B   2    0.577738    0.594413    0.212933    11.00000   -1.20000
HKLF 4
;
_cod_data_source_file            fg3316.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               2019296
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
O O1 0.5000 0.7500 0.51960(7) 0.0143(2) Uani d S 1 2
C C1 0.5000 0.7500 0.42554(9) 0.0114(3) Uani d S 1 2
N N2 0.52887(11) 0.60730(11) 0.36512(5) 0.0136(2) Uani d . 1 1
H H02 0.5135(18) 0.504(2) 0.3903(10) 0.024(3) Uiso d . 1 1
C C3 0.49143(14) 0.64940(12) 0.25925(6) 0.0148(2) Uani d . 1 1
H H3A 0.3717 0.6120 0.2397 0.018 Uiso calc R 1 1
H H3B 0.5777 0.5944 0.2129 0.018 Uiso calc R 1 1
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 0.0157(4) 0.0181(5) 0.0090(4) 0.0003(4) 0.000 0.000
C1 0.0092(5) 0.0135(6) 0.0115(5) -0.0004(5) 0.000 0.000
N2 0.0199(5) 0.0113(4) 0.0096(3) 0.0009(3) -0.0010(3) 0.0001(3)
C3 0.0193(4) 0.0155(4) 0.0096(4) 0.0001(4) -0.0009(3) -0.0007(3)
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
O1 C1 N2 . . 125.63(5)
O1 C1 N2 . 6_564 125.63(5)
N2 C1 N2 . 6_564 108.75(11)
C1 N2 C3 . . 110.48(8)
N2 C3 C3 . 6_564 101.69(5)
C1 N2 H02 . . 118.7(9)
C3 N2 H02 . . 122.8(9)
N2 C3 H3A . . 111.4
C3 C3 H3A 6_564 . 111.4
N2 C3 H3B . . 111.4
C3 C3 H3B 6_564 . 111.4
H3A C3 H3B . . 109.3
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 C1 . 1.2382(15) y
C1 N2 . 1.3652(11) y
C1 N2 6_564 1.3652(11) ?
N2 C3 . 1.4583(11) y
C3 C3 6_564 1.5391(18) y
N2 H02 . 0.859(16) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
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
N2 H02 O1 9_666 0.859(16) 2.275(15) 3.1253(10) 170.0(12)
N2 H02 O1 7_544 0.859(16) 2.509(15) 3.0076(9) 117.8(10)
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_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 N2 C3 . . . 170.90(5) ?
N2 C1 N2 C3 6_564 . . -9.10(5) y
C1 N2 C3 C3 . . 6_564 21.92(12) y
N2 C3 C3 N2 . 6_564 6_564 -25.20(13) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 8453
