#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/64/2206477.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_2206477
loop_
_publ_author_name
'Ju-Zhen Yuan'
'Yang-Gen Hu'
'Jia-Jia Wei'
'Ming-Wu Ding'
_publ_section_title
;
 (E)-3-Isopropyl-5,5-dimethyl-2-(phenylimino)imidazolidin-4-one
;
_journal_coeditor_code           KP6052
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2640
_journal_page_last               o2641
_journal_paper_doi               10.1107/S1600536805022749
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H19 N3 O'
_chemical_formula_moiety         'C14 H19 N3 O'
_chemical_formula_sum            'C14 H19 N3 O'
_chemical_formula_weight         245.32
_chemical_melting_point          442
_chemical_name_systematic
;
(E)-3-Isopropyl-5,5-dimethyl-2-(phenylimino)imidazolidin-4-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   10.2783(11)
_cell_length_b                   11.4013(11)
_cell_length_c                   11.5930(12)
_cell_measurement_reflns_used    2657
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      22.92
_cell_measurement_theta_min      2.51
_cell_volume                     1358.5(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL-NT (Siemens, 1995)'
_computing_publication_material  SHELXTL-NT
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7376
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.182
_refine_ls_abs_structure_details 'Flack (1983), 0000 Friedel pairs'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0389
_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)+(0.065P)²+0.0483P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                1406
_reflns_number_total             1539
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp6052.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2206477
_cod_database_fobs_code          2206477
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_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_type_symbol
C1 0.6646(2) 0.5652(2) -0.0969(2) 0.0547(6) Uani d . 1 C
H1 0.6030 0.5266 -0.1417 0.066 Uiso calc R 1 H
C2 0.7795(3) 0.6032(2) -0.1469(2) 0.0636(7) Uani d . 1 C
H2 0.7945 0.5895 -0.2248 0.076 Uiso calc R 1 H
C3 0.8714(3) 0.6608(2) -0.0822(3) 0.0664(7) Uani d . 1 C
H3 0.9483 0.6862 -0.1162 0.080 Uiso calc R 1 H
C4 0.8492(3) 0.6807(2) 0.0325(3) 0.0670(7) Uani d . 1 C
H4 0.9114 0.7196 0.0765 0.080 Uiso calc R 1 H
C5 0.7347(2) 0.6432(2) 0.0833(2) 0.0549(6) Uani d . 1 C
H5 0.7203 0.6575 0.1613 0.066 Uiso calc R 1 H
C6 0.6407(2) 0.58434(16) 0.0191(2) 0.0449(5) Uani d . 1 C
C7 0.46911(19) 0.45581(17) 0.06060(16) 0.0375(4) Uani d . 1 C
C8 0.42016(19) 0.25966(17) 0.02323(17) 0.0390(5) Uani d . 1 C
C9 0.4882(2) 0.1711(2) 0.1020(2) 0.0551(6) Uani d . 1 C
H9A 0.5604 0.1367 0.0619 0.083 Uiso calc R 1 H
H9B 0.4278 0.1107 0.1236 0.083 Uiso calc R 1 H
H9C 0.5190 0.2103 0.1700 0.083 Uiso calc R 1 H
C10 0.3696(2) 0.2014(2) -0.08570(19) 0.0533(6) Uani d . 1 C
H10A 0.3198 0.2570 -0.1295 0.080 Uiso calc R 1 H
H10B 0.3154 0.1360 -0.0653 0.080 Uiso calc R 1 H
H10C 0.4417 0.1743 -0.1312 0.080 Uiso calc R 1 H
C11 0.31129(19) 0.31808(17) 0.09114(17) 0.0382(4) Uani d . 1 C
C12 0.2797(2) 0.51475(18) 0.18787(17) 0.0418(5) Uani d . 1 C
H12 0.3387 0.5811 0.2001 0.050 Uiso calc R 1 H
C13 0.2513(3) 0.4632(2) 0.3049(2) 0.0666(8) Uani d . 1 C
H13A 0.1861 0.4035 0.2976 0.100 Uiso calc R 1 H
H13B 0.2204 0.5238 0.3554 0.100 Uiso calc R 1 H
H13C 0.3294 0.4296 0.3361 0.100 Uiso calc R 1 H
C14 0.1602(3) 0.5625(2) 0.1286(2) 0.0643(7) Uani d . 1 C
H14A 0.1841 0.5941 0.0548 0.096 Uiso calc R 1 H
H14B 0.1225 0.6233 0.1751 0.096 Uiso calc R 1 H
H14C 0.0981 0.5005 0.1180 0.096 Uiso calc R 1 H
N2 0.50252(17) 0.35963(13) -0.00149(16) 0.0452(4) Uani d . 1 N
H2A 0.5656 0.3582 -0.0502 0.054 Uiso calc R 1 H
N3 0.34933(16) 0.42970(14) 0.11434(14) 0.0399(4) Uani d . 1 N
N1 0.52320(17) 0.55533(15) 0.07566(16) 0.0453(4) Uani d . 1 N
O1 0.21018(15) 0.27146(13) 0.12095(13) 0.0491(4) Uani d . 1 O
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C2 C1 C6 120.6(2)
C2 C1 H1 119.7
C6 C1 H1 119.7
C3 C2 C1 120.5(3)
C3 C2 H2 119.7
C1 C2 H2 119.7
C4 C3 C2 119.7(3)
C4 C3 H3 120.2
C2 C3 H3 120.2
C3 C4 C5 120.3(3)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 120.8(2)
C4 C5 H5 119.6
C6 C5 H5 119.6
C1 C6 C5 118.2(2)
C1 C6 N1 124.4(2)
C5 C6 N1 117.2(2)
N1 C7 N2 132.97(19)
N1 C7 N3 120.49(18)
N2 C7 N3 106.54(16)
N2 C8 C10 112.31(17)
N2 C8 C11 100.82(15)
C10 C8 C11 111.72(17)
N2 C8 C9 111.73(17)
C10 C8 C9 111.34(17)
C11 C8 C9 108.41(17)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O1 C11 N3 126.8(2)
O1 C11 C8 125.70(18)
N3 C11 C8 107.51(17)
N3 C12 C13 110.95(17)
N3 C12 C14 111.61(17)
C13 C12 C14 113.2(2)
N3 C12 H12 106.9
C13 C12 H12 106.9
C14 C12 H12 106.9
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 N2 C8 112.54(16)
C7 N2 H2A 123.7
C8 N2 H2A 123.7
C11 N3 C7 111.18(17)
C11 N3 C12 126.18(17)
C7 N3 C12 122.62(16)
C7 N1 C6 121.14(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.384(3)
C1 C6 1.385(3)
C1 H1 0.9300
C2 C3 1.374(4)
C2 H2 0.9300
C3 C4 1.368(4)
C3 H3 0.9300
C4 C5 1.385(4)
C4 H4 0.9300
C5 C6 1.391(3)
C5 H5 0.9300
C6 N1 1.414(3)
C7 N1 1.276(3)
C7 N2 1.356(2)
C7 N3 1.412(3)
C8 N2 1.448(2)
C8 C10 1.519(3)
C8 C11 1.522(3)
C8 C9 1.530(3)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 O1 1.217(2)
C11 N3 1.358(3)
C12 N3 1.476(2)
C12 C13 1.506(3)
C12 C14 1.509(3)
C12 H12 0.9800
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N2 H2A 0.8600
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 C1 C2 C3 -0.3(4)
C1 C2 C3 C4 0.1(4)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 C6 0.3(4)
C2 C1 C6 C5 0.4(3)
C2 C1 C6 N1 175.86(19)
C4 C5 C6 C1 -0.5(3)
C4 C5 C6 N1 -176.2(2)
N2 C8 C11 O1 171.6(2)
C10 C8 C11 O1 52.1(3)
C9 C8 C11 O1 -70.9(3)
N2 C8 C11 N3 -9.9(2)
C10 C8 C11 N3 -129.35(17)
C9 C8 C11 N3 107.59(19)
N1 C7 N2 C8 170.4(2)
N3 C7 N2 C8 -9.9(2)
C10 C8 N2 C7 131.2(2)
C11 C8 N2 C7 12.2(2)
C9 C8 N2 C7 -102.8(2)
O1 C11 N3 C7 -176.70(19)
C8 C11 N3 C7 4.8(2)
O1 C11 N3 C12 4.8(3)
C8 C11 N3 C12 -173.72(17)
N1 C7 N3 C11 -177.48(18)
N2 C7 N3 C11 2.8(2)
N1 C7 N3 C12 1.1(3)
N2 C7 N3 C12 -178.59(17)
C13 C12 N3 C11 53.0(3)
C14 C12 N3 C11 -74.2(2)
C13 C12 N3 C7 -125.4(2)
C14 C12 N3 C7 107.4(2)
N2 C7 N1 C6 2.0(4)
N3 C7 N1 C6 -177.67(17)
C1 C6 N1 C7 46.3(3)
C5 C6 N1 C7 -138.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129101
2 PubChem 139068154
