#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226690.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_2226690
loop_
_publ_author_name
'Sheng, Liang-Quan'
'Xu, Hua-Jie'
'Du, Na-Na'
'Jiang, Xue-Yue'
_publ_section_title
;
 (E)-1-[(2-Hydroxy-1-naphthyl)methylideneamino]imidazolidine-2,4-dione
;
_journal_coeditor_code           SU2180
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1601
_journal_paper_doi               10.1107/S1600536810020118
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H11 N3 O3'
_chemical_formula_moiety         'C14 H11 N3 O3'
_chemical_formula_sum            'C14 H11 N3 O3'
_chemical_formula_weight         269.26
_chemical_name_systematic
;
(E)-1-[(2-Hydroxy-1-naphthyl)methylideneamino]imidazolidine-2,4-dione
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.773(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5122(7)
_cell_length_b                   6.0233(3)
_cell_length_c                   17.9955(10)
_cell_measurement_reflns_used    1596
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0109
_cell_measurement_theta_min      3.0491
_cell_volume                     1239.13(12)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S Ultra'
_diffrn_measurement_method       'ω scans'
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0956
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4288
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.56
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_correction_T_min  0.9593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.718
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.718
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0266P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0668
_reflns_number_gt                1053
_reflns_number_total             2136
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2180.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226690
_cod_database_fobs_code          2226690
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.59888(11) 0.25607(18) 0.48396(8) 0.0491(5) Uani . . 1.000
O O2 0.40014(13) 0.1526(2) 0.68676(8) 0.0710(7) Uani . . 1.000
O O3 0.80499(13) 0.8397(2) 0.49453(8) 0.0645(6) Uani . . 1.000
N N1 0.67397(13) 0.6177(2) 0.57838(9) 0.0420(6) Uani . . 1.000
N N2 0.59925(13) 0.4517(2) 0.59460(9) 0.0425(6) Uani . . 1.000
N N3 0.48790(15) 0.1552(3) 0.57835(10) 0.0454(7) Uani . . 1.000
C C1 0.79653(19) 1.2321(3) 0.80751(14) 0.0665(10) Uani . . 1.000
C C2 0.8627(2) 1.4184(4) 0.79511(16) 0.0705(10) Uani . . 1.000
C C3 0.90328(19) 1.4454(3) 0.72772(16) 0.0626(9) Uani . . 1.000
C C4 0.87808(17) 1.2884(3) 0.66974(14) 0.0504(9) Uani . . 1.000
C C5 0.80840(16) 1.1006(3) 0.68128(12) 0.0434(8) Uani . . 1.000
C C6 0.77027(17) 1.0762(3) 0.75298(13) 0.0549(9) Uani . . 1.000
C C7 0.91986(18) 1.3147(3) 0.59955(15) 0.0606(10) Uani . . 1.000
C C8 0.89532(17) 1.1653(4) 0.54362(13) 0.0589(9) Uani . . 1.000
C C9 0.82579(17) 0.9788(3) 0.55419(13) 0.0495(9) Uani . . 1.000
C C10 0.78023(16) 0.9449(3) 0.62117(12) 0.0413(8) Uani . . 1.000
C C11 0.70303(15) 0.7611(3) 0.63076(11) 0.0436(7) Uani . . 1.000
C C12 0.56648(16) 0.2867(3) 0.54520(12) 0.0398(8) Uani . . 1.000
C C13 0.46509(18) 0.2336(3) 0.64613(12) 0.0503(9) Uani . . 1.000
C C14 0.53798(18) 0.4406(3) 0.66051(11) 0.0496(8) Uani . . 1.000
H H1 0.76960 1.21310 0.85380 0.0800 Uiso calc R 1.000
H H2 0.87910 1.52400 0.83260 0.0850 Uiso calc R 1.000
H H3 0.94840 1.56920 0.71970 0.0750 Uiso calc R 1.000
H H3N 0.4590(16) 0.028(3) 0.5590(11) 0.065(7) Uiso . . 1.000
H H4 0.76770 0.73180 0.50630 0.0970 Uiso calc R 1.000
H H6 0.72670 0.95210 0.76300 0.0660 Uiso calc R 1.000
H H7 0.96540 1.43790 0.59150 0.0730 Uiso calc R 1.000
H H8 0.92460 1.18630 0.49810 0.0710 Uiso calc R 1.000
H H11 0.67310 0.74520 0.67630 0.0520 Uiso calc R 1.000
H H14A 0.48920 0.57040 0.66440 0.0600 Uiso calc R 1.000
H H14B 0.59220 0.42690 0.70580 0.0600 Uiso calc R 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O3 H4 . . . 109.00 no
N2 N1 C11 . . . 116.51(16) no
N1 N2 C14 . . . 125.77(14) no
C12 N2 C14 . . . 112.17(15) no
N1 N2 C12 . . . 121.80(16) no
C12 N3 C13 . . . 113.02(17) no
C13 N3 H3N . . . 123.1(13) no
C12 N3 H3N . . . 123.7(13) no
C2 C1 C6 . . . 121.3(2) no
C1 C2 C3 . . . 119.5(2) no
C2 C3 C4 . . . 121.1(2) no
C3 C4 C5 . . . 119.8(2) no
C3 C4 C7 . . . 121.57(18) no
C5 C4 C7 . . . 118.64(19) no
C4 C5 C10 . . . 119.44(19) no
C4 C5 C6 . . . 117.23(19) no
C6 C5 C10 . . . 123.33(17) no
C1 C6 C5 . . . 121.07(18) no
C4 C7 C8 . . . 121.78(19) no
C7 C8 C9 . . . 120.2(2) no
C8 C9 C10 . . . 121.05(19) no
O3 C9 C10 . . . 123.12(17) no
O3 C9 C8 . . . 115.82(19) no
C5 C10 C9 . . . 118.88(17) no
C5 C10 C11 . . . 119.83(18) no
C9 C10 C11 . . . 121.27(18) no
N1 C11 C10 . . . 122.37(18) no
N2 C12 N3 . . . 106.33(17) no
O1 C12 N2 . . . 127.76(17) no
O1 C12 N3 . . . 125.91(18) no
O2 C13 N3 . . . 126.88(18) no
O2 C13 C14 . . . 126.97(19) no
N3 C13 C14 . . . 106.15(17) no
N2 C14 C13 . . . 102.24(15) no
C2 C1 H1 . . . 119.00 no
C6 C1 H1 . . . 119.00 no
C1 C2 H2 . . . 120.00 no
C3 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 119.00 no
C4 C3 H3 . . . 119.00 no
C1 C6 H6 . . . 119.00 no
C5 C6 H6 . . . 119.00 no
C4 C7 H7 . . . 119.00 no
C8 C7 H7 . . . 119.00 no
C7 C8 H8 . . . 120.00 no
C9 C8 H8 . . . 120.00 no
N1 C11 H11 . . . 119.00 no
C10 C11 H11 . . . 119.00 no
N2 C14 H14A . . . 111.00 no
N2 C14 H14B . . . 111.00 no
C13 C14 H14A . . . 111.00 no
C13 C14 H14B . . . 111.00 no
H14A C14 H14B . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . . 1.219(3) no
O2 C13 . . 1.209(3) no
O3 C9 . . 1.361(3) no
O3 H4 . . 0.8200 no
N1 N2 . . 1.3726(19) no
N1 C11 . . 1.293(2) no
N2 C12 . . 1.357(2) no
N2 C14 . . 1.451(3) no
N3 C13 . . 1.362(3) no
N3 C12 . . 1.389(3) no
N3 H3N . . 0.890(18) no
C1 C6 . . 1.366(3) no
C1 C2 . . 1.389(3) no
C2 C3 . . 1.360(4) no
C3 C4 . . 1.413(3) no
C4 C7 . . 1.413(4) no
C4 C5 . . 1.416(3) no
C5 C10 . . 1.440(3) no
C5 C6 . . 1.419(3) no
C7 C8 . . 1.355(3) no
C8 C9 . . 1.405(3) no
C9 C10 . . 1.385(3) no
C10 C11 . . 1.443(3) no
C13 C14 . . 1.508(3) no
C1 H1 . . 0.9300 no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C6 H6 . . 0.9300 no
C7 H7 . . 0.9300 no
C8 H8 . . 0.9300 no
C11 H11 . . 0.9300 no
C14 H14A . . 0.9700 no
C14 H14B . . 0.9700 no
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
_geom_hbond_publ_flag
N3 H3N O1 3_656 0.890(18) 1.962(18) 2.851(2) 177.9(19) yes
O3 H4 N1 . 0.82 1.91 2.622(2) 145 yes
C6 H6 O2 2_656 0.93 2.55 3.469(2) 169 yes
C14 H14B O2 2_656 0.97 2.36 3.038(2) 127 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 N2 C12 . . . . -177.23(16) no
C11 N1 N2 C14 . . . . 9.1(2) no
N2 N1 C11 C10 . . . . -179.57(16) no
N1 N2 C12 O1 . . . . 2.8(3) no
N1 N2 C12 N3 . . . . -177.61(15) no
C14 N2 C12 O1 . . . . 177.26(19) no
C14 N2 C12 N3 . . . . -3.1(2) no
N1 N2 C14 C13 . . . . 176.87(16) no
C12 N2 C14 C13 . . . . 2.7(2) no
C13 N3 C12 O1 . . . . -178.02(19) no
C13 N3 C12 N2 . . . . 2.4(2) no
C12 N3 C13 O2 . . . . 179.8(2) no
C12 N3 C13 C14 . . . . -0.7(2) no
C6 C1 C2 C3 . . . . -0.7(3) no
C2 C1 C6 C5 . . . . -0.9(3) no
C1 C2 C3 C4 . . . . 0.8(3) no
C2 C3 C4 C5 . . . . 0.7(3) no
C2 C3 C4 C7 . . . . -179.9(2) no
C3 C4 C5 C6 . . . . -2.2(3) no
C3 C4 C5 C10 . . . . 178.15(18) no
C7 C4 C5 C6 . . . . 178.47(18) no
C7 C4 C5 C10 . . . . -1.2(3) no
C3 C4 C7 C8 . . . . -179.6(2) no
C5 C4 C7 C8 . . . . -0.2(3) no
C4 C5 C6 C1 . . . . 2.3(3) no
C10 C5 C6 C1 . . . . -178.07(19) no
C4 C5 C10 C9 . . . . 2.3(3) no
C4 C5 C10 C11 . . . . -175.93(17) no
C6 C5 C10 C9 . . . . -177.34(18) no
C6 C5 C10 C11 . . . . 4.4(3) no
C4 C7 C8 C9 . . . . 0.6(3) no
C7 C8 C9 O3 . . . . 179.31(19) no
C7 C8 C9 C10 . . . . 0.6(3) no
O3 C9 C10 C5 . . . . 179.36(17) no
O3 C9 C10 C11 . . . . -2.4(3) no
C8 C9 C10 C5 . . . . -2.1(3) no
C8 C9 C10 C11 . . . . 176.19(18) no
C5 C10 C11 N1 . . . . 179.33(17) no
C9 C10 C11 N1 . . . . 1.1(3) no
O2 C13 C14 N2 . . . . 178.40(19) no
N3 C13 C14 N2 . . . . -1.1(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745196
2 PubChem 135788210
