#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/44/2224437.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_2224437
loop_
_publ_author_name
'Galas, Henry'
'Viirre, Russell D.'
'Lough, Alan J.'
_publ_section_title
;
 meso-4,5-Diphenylimidazolidin-2-one
;
_journal_coeditor_code           SJ2668
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3087
_journal_paper_doi               10.1107/S1600536809046133
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H14 N2 O'
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28
_chemical_name_systematic
;
meso-4,5-Diphenylimidazolidin-2-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                86.147(3)
_cell_angle_beta                 76.094(3)
_cell_angle_gamma                82.718(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3539(4)
_cell_length_b                   8.6159(4)
_cell_length_c                   11.3211(7)
_cell_measurement_reflns_used    6535
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     596.32(6)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       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  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6535
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SORTAV; Blessing, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.253
_refine_ls_extinction_coef       0.043(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Version 6.1; Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0787P)²+0.1078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1564
_reflns_number_gt                1771
_reflns_number_total             2685
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2668.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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               2224437
_cod_database_fobs_code          2224437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5277(2) 0.41749(16) 0.65182(13) 0.0402(4) Uani d . 1 . .
N N1 0.2254(3) 0.55213(18) 0.59441(15) 0.0298(4) Uani d . 1 . .
N N2 0.2105(3) 0.50802(19) 0.79050(15) 0.0310(4) Uani d . 1 . .
C C1 0.0274(3) 0.6470(2) 0.65473(17) 0.0264(4) Uani d . 1 . .
H H1A -0.0938 0.6328 0.6156 0.032 Uiso calc R 1 . .
C C2 0.3394(3) 0.4852(2) 0.67556(18) 0.0308(5) Uani d . 1 . .
C C3 -0.0134(3) 0.5630(2) 0.78442(17) 0.0283(5) Uani d . 1 . .
H H3A -0.0926 0.4701 0.7831 0.034 Uiso calc R 1 . .
C C4 0.0525(3) 0.8203(2) 0.65330(16) 0.0243(4) Uani d . 1 . .
C C5 0.2551(3) 0.8742(2) 0.63592(17) 0.0288(5) Uani d . 1 . .
H H5A 0.3829 0.8014 0.6267 0.035 Uiso calc R 1 . .
C C6 0.2724(3) 1.0331(2) 0.63194(18) 0.0315(5) Uani d . 1 . .
H H6A 0.4118 1.0687 0.6195 0.038 Uiso calc R 1 . .
C C7 0.0879(3) 1.1399(2) 0.64589(18) 0.0318(5) Uani d . 1 . .
H H7A 0.1004 1.2489 0.6430 0.038 Uiso calc R 1 . .
C C8 -0.1151(3) 1.0882(2) 0.66414(17) 0.0317(5) Uani d . 1 . .
H H8A -0.2426 1.1614 0.6741 0.038 Uiso calc R 1 . .
C C9 -0.1316(3) 0.9287(2) 0.66781(17) 0.0278(5) Uani d . 1 . .
H H9A -0.2713 0.8934 0.6805 0.033 Uiso calc R 1 . .
C C10 -0.1371(3) 0.6618(2) 0.88918(16) 0.0259(4) Uani d . 1 . .
C C11 -0.0311(3) 0.7520(2) 0.94856(17) 0.0297(5) Uani d . 1 . .
H H11A 0.1228 0.7514 0.9233 0.036 Uiso calc R 1 . .
C C12 -0.1480(3) 0.8430(2) 1.04446(18) 0.0338(5) Uani d . 1 . .
H H12A -0.0735 0.9030 1.0852 0.041 Uiso calc R 1 . .
C C13 -0.3712(3) 0.8468(2) 1.08089(18) 0.0339(5) Uani d . 1 . .
H H13A -0.4510 0.9103 1.1459 0.041 Uiso calc R 1 . .
C C14 -0.4787(3) 0.7580(2) 1.02265(19) 0.0364(5) Uani d . 1 . .
H H14A -0.6328 0.7603 1.0479 0.044 Uiso calc R 1 . .
C C15 -0.3626(3) 0.6652(2) 0.92714(17) 0.0307(5) Uani d . 1 . .
H H15A -0.4376 0.6039 0.8878 0.037 Uiso calc R 1 . .
H H2N 0.248(3) 0.441(3) 0.846(2) 0.035(6) Uiso d . 1 . .
H H1N 0.297(3) 0.569(2) 0.514(2) 0.040(6) Uiso 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'
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
C2 N1 C1 . . 111.46(16) ?
C2 N1 H1N . . 119.9(13) ?
C1 N1 H1N . . 123.4(13) ?
C2 N2 C3 . . 110.27(16) ?
C2 N2 H2N . . 113.6(14) ?
C3 N2 H2N . . 124.9(14) ?
N1 C1 C4 . . 113.60(15) ?
N1 C1 C3 . . 99.73(14) ?
C4 C1 C3 . . 114.88(14) ?
N1 C1 H1A . . 109.4 ?
C4 C1 H1A . . 109.4 ?
C3 C1 H1A . . 109.4 ?
O1 C2 N1 . . 126.79(18) ?
O1 C2 N2 . . 125.27(18) ?
N1 C2 N2 . . 107.93(17) ?
N2 C3 C10 . . 113.62(16) ?
N2 C3 C1 . . 100.24(14) ?
C10 C3 C1 . . 116.28(14) ?
N2 C3 H3A . . 108.8 ?
C10 C3 H3A . . 108.8 ?
C1 C3 H3A . . 108.8 ?
C9 C4 C5 . . 118.61(16) ?
C9 C4 C1 . . 119.26(16) ?
C5 C4 C1 . . 122.12(16) ?
C6 C5 C4 . . 120.56(18) ?
C6 C5 H5A . . 119.7 ?
C4 C5 H5A . . 119.7 ?
C7 C6 C5 . . 120.26(18) ?
C7 C6 H6A . . 119.9 ?
C5 C6 H6A . . 119.9 ?
C6 C7 C8 . . 119.96(17) ?
C6 C7 H7A . . 120.0 ?
C8 C7 H7A . . 120.0 ?
C7 C8 C9 . . 119.57(18) ?
C7 C8 H8A . . 120.2 ?
C9 C8 H8A . . 120.2 ?
C4 C9 C8 . . 121.04(17) ?
C4 C9 H9A . . 119.5 ?
C8 C9 H9A . . 119.5 ?
C11 C10 C15 . . 118.79(18) ?
C11 C10 C3 . . 121.43(17) ?
C15 C10 C3 . . 119.77(17) ?
C12 C11 C10 . . 120.59(18) ?
C12 C11 H11A . . 119.7 ?
C10 C11 H11A . . 119.7 ?
C13 C12 C11 . . 120.32(19) ?
C13 C12 H12A . . 119.8 ?
C11 C12 H12A . . 119.8 ?
C12 C13 C14 . . 119.72(19) ?
C12 C13 H13A . . 120.1 ?
C14 C13 H13A . . 120.1 ?
C13 C14 C15 . . 120.36(19) ?
C13 C14 H14A . . 119.8 ?
C15 C14 H14A . . 119.8 ?
C10 C15 C14 . . 120.20(18) ?
C10 C15 H15A . . 119.9 ?
C14 C15 H15A . . 119.9 ?
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 C2 . 1.238(2) ?
N1 C2 . 1.358(3) ?
N1 C1 . 1.456(2) ?
N1 H1N . 0.93(2) ?
N2 C2 . 1.373(3) ?
N2 C3 . 1.458(3) ?
N2 H2N . 0.87(2) ?
C1 C4 . 1.520(2) ?
C1 C3 . 1.571(3) ?
C1 H1A . 1.0000 ?
C3 C10 . 1.506(3) ?
C3 H3A . 1.0000 ?
C4 C9 . 1.386(3) ?
C4 C5 . 1.389(3) ?
C5 C6 . 1.384(3) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.379(3) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.382(3) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.389(3) ?
C8 H8A . 0.9500 ?
C9 H9A . 0.9500 ?
C10 C11 . 1.389(3) ?
C10 C15 . 1.391(3) ?
C11 C12 . 1.387(3) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.375(3) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.380(3) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.392(3) ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9500 ?
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 H1N O1 2_666 0.93(2) 1.94(2) 2.864(2) 173(2)
N2 H2N Cg1 2_567 0.87(2) 2.46(2) 3.322(2) 165(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 238402
