#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/74/2217412.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_2217412
loop_
_publ_author_name
'Kashif, M. Kaleem'
'Hussain, Abid'
'Khawar Rauf, M.'
'Ebihara, Masahiro'
'Hameed, Shahid'
_publ_section_title
;
 5-(4-Fluorophenyl)-5-methylimidazolidine-2,4-dione
;
_journal_coeditor_code           BI2269
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o444
_journal_page_last               o444
_journal_paper_doi               10.1107/S1600536807067803
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H9 F N2 O2'
_chemical_formula_moiety         'C10 H9 F N2 O2'
_chemical_formula_sum            'C10 H9 F N2 O2'
_chemical_formula_weight         208.19
_chemical_name_systematic
;
5-(4-Fluorophenyl)-5-methylimidazolidine-2,4-dione
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.096(2)
_cell_length_b                   11.348(3)
_cell_length_c                   22.661(7)
_cell_measurement_reflns_used    5426
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1824.8(9)
_computing_cell_refinement
'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)'
_computing_data_collection
'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)'
_computing_data_reduction        'TEXSAN (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'SHELXL97 (Sheldrick, 1997) and TEXSAN (Rigaku/MSC, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13516
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.028P)²+1.2798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                2054
_reflns_number_total             2083
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2269.cif
_cod_data_source_block           I
_cod_original_cell_volume        1824.7(10)
_cod_database_code               2217412
_cod_database_fobs_code          2217412
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
C C1 0.13701(19) 0.06340(11) 0.10194(6) 0.0127(3) Uani d . 1
N N1 0.09007(16) 0.16162(10) 0.06286(5) 0.0141(2) Uani d . 1
H H1 -0.025(3) 0.1859(17) 0.0547(9) 0.028(5) Uiso d . 1
C C2 0.23589(19) 0.19597(12) 0.02932(6) 0.0135(3) Uani d . 1
O O1 0.23772(14) 0.27474(9) -0.00808(4) 0.0167(2) Uani d . 1
N N2 0.38961(17) 0.12558(10) 0.04332(5) 0.0151(3) Uani d . 1
H H2 0.504(3) 0.1445(16) 0.0305(8) 0.024(5) Uiso d . 1
C C3 0.34432(19) 0.04077(11) 0.08415(6) 0.0129(3) Uani d . 1
O O2 0.44614(15) -0.03631(8) 0.10246(4) 0.0177(2) Uani d . 1
C C4 0.13117(18) 0.09904(11) 0.16706(6) 0.0118(3) Uani d . 1
C C5 0.08781(19) 0.21387(12) 0.18428(6) 0.0150(3) Uani d . 1
H H5 0.0607 0.2719 0.1553 0.018 Uiso calc R 1
C C6 0.0841(2) 0.24367(12) 0.24395(6) 0.0175(3) Uani d . 1
H H6 0.0542 0.3217 0.2560 0.021 Uiso calc R 1
C C7 0.1246(2) 0.15835(13) 0.28513(6) 0.0170(3) Uani d . 1
C C8 0.1685(2) 0.04404(12) 0.26982(6) 0.0158(3) Uani d . 1
H H8 0.1954 -0.0134 0.2992 0.019 Uiso calc R 1
C C9 0.17244(19) 0.01526(12) 0.21023(6) 0.0139(3) Uani d . 1
H H9 0.2037 -0.0628 0.1987 0.017 Uiso calc R 1
C C10 0.0141(2) -0.04446(12) 0.08893(6) 0.0183(3) Uani d . 1
H H10A -0.1179 -0.0258 0.0975 0.027 Uiso calc R 1
H H10B 0.0549 -0.1105 0.1137 0.027 Uiso calc R 1
H H10C 0.0267 -0.0660 0.0472 0.027 Uiso calc R 1
F F1 0.12297(14) 0.18871(8) 0.34320(4) 0.0258(2) Uani d . 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'
F F 0.0171 0.0103 '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
N1 C1 C4 112.11(11)
N1 C1 C10 111.28(11)
C4 C1 C10 112.42(11)
N1 C1 C3 100.68(10)
C4 C1 C3 108.71(10)
C10 C1 C3 111.03(11)
C2 N1 C1 112.89(11)
C2 N1 H1 120.3(13)
C1 N1 H1 125.2(13)
O1 C2 N1 127.49(13)
O1 C2 N2 124.48(12)
N1 C2 N2 108.02(11)
C3 N2 C2 111.91(11)
C3 N2 H2 127.1(12)
C2 N2 H2 120.3(12)
O2 C3 N2 126.79(13)
O2 C3 C1 126.84(12)
N2 C3 C1 106.37(11)
C5 C4 C9 119.13(12)
C5 C4 C1 121.51(12)
C9 C4 C1 119.35(12)
C6 C5 C4 120.14(13)
C6 C5 H5 119.9
C4 C5 H5 119.9
C7 C6 C5 118.92(13)
C7 C6 H6 120.5
C5 C6 H6 120.5
F1 C7 C6 118.45(13)
F1 C7 C8 118.92(13)
C6 C7 C8 122.62(13)
C7 C8 C9 118.05(12)
C7 C8 H8 121.0
C9 C8 H8 121.0
C8 C9 C4 121.13(12)
C8 C9 H9 119.4
C4 C9 H9 119.4
C1 C10 H10A 109.5
C1 C10 H10B 109.5
H10A C10 H10B 109.5
C1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.4620(17)
C1 C4 1.5306(18)
C1 C10 1.5316(19)
C1 C3 1.5468(19)
N1 C2 1.3417(18)
N1 H1 0.88(2)
C2 O1 1.2320(17)
C2 N2 1.3887(18)
N2 C3 1.3732(17)
N2 H2 0.89(2)
C3 O2 1.2080(17)
C4 C5 1.3946(19)
C4 C9 1.3952(18)
C5 C6 1.394(2)
C5 H5 0.950
C6 C7 1.375(2)
C6 H6 0.950
C7 F1 1.3604(16)
C7 C8 1.378(2)
C8 C9 1.3897(19)
C8 H8 0.950
C9 H9 0.950
C10 H10A 0.980
C10 H10B 0.980
C10 H10C 0.980
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 O1 3_455 0.88(2) 2.04(2) 2.8834(17) 160.5(18)
N2 H2 O1 3 0.89(2) 1.96(2) 2.8318(17) 165.9(17)
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
C4 C1 N1 C2 113.75(13)
C10 C1 N1 C2 -119.38(13)
C3 C1 N1 C2 -1.65(14)
C1 N1 C2 O1 178.84(13)
C1 N1 C2 N2 -0.49(15)
O1 C2 N2 C3 -176.54(13)
N1 C2 N2 C3 2.81(16)
C2 N2 C3 O2 176.10(13)
C2 N2 C3 C1 -3.79(15)
N1 C1 C3 O2 -176.71(13)
C4 C1 C3 O2 65.37(17)
C10 C1 C3 O2 -58.79(17)
N1 C1 C3 N2 3.18(13)
C4 C1 C3 N2 -114.74(12)
C10 C1 C3 N2 121.09(12)
N1 C1 C4 C5 -0.87(17)
C10 C1 C4 C5 -127.12(14)
C3 C1 C4 C5 109.54(14)
N1 C1 C4 C9 179.95(12)
C10 C1 C4 C9 53.70(17)
C3 C1 C4 C9 -69.63(15)
C9 C4 C5 C6 -0.6(2)
C1 C4 C5 C6 -179.82(12)
C4 C5 C6 C7 0.3(2)
C5 C6 C7 F1 179.19(12)
C5 C6 C7 C8 -0.1(2)
F1 C7 C8 C9 -178.99(12)
C6 C7 C8 C9 0.3(2)
C7 C8 C9 C4 -0.7(2)
C5 C4 C9 C8 0.9(2)
C1 C4 C9 C8 -179.95(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 204864
2 PubChem 676692
