#------------------------------------------------------------------------------
#$Date: 2022-09-02 09:43:30 +0200 (Fri 02 de Sep de 2022) $
#$Revision: 277585 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/57/8105748.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105748
loop_
_publ_author_name
'Wang, De-Xing'
'Cao, Peng'
_publ_section_title
;
 The crystal structure of 2,5,5-triphenyl-3,5-dihydro-4H-imidazol-4-one,
 C21H16N2O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              555
_journal_page_last               556
_journal_paper_doi               10.1515/ncrs-2022-0082
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C21 H16 N2 O'
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 99.337(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8987(3)
_cell_length_b                   15.0321(5)
_cell_length_c                   8.1727(2)
_cell_measurement_reflns_used    3159
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.4100
_cell_measurement_theta_min      4.3440
_cell_volume                     1684.87(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019) [1]'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019) [1]'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019) [1]'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015) [3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018) [4]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -111.00 -84.00   1.00   13.60    --  -40.80 -57.00  90.00   27
  2  ω    -65.00  31.00   1.00   13.60    --  -40.80  38.00-120.00   96
  3  ω    -62.00  -3.00   1.00   13.60    --  -40.80 125.00 -60.00   59
  4  ω    -57.00 -30.00   1.00   13.60    --  -40.80 -57.00  90.00   27
  5  ω     88.00 121.00   1.00   13.60    --   40.80-169.00  41.00   33
  6  ω     97.00 174.00   1.00   54.38    --  105.27  45.00-180.00   77
  7  ω     33.00  80.00   1.00   54.38    --  105.27-125.00  30.00   47
  8  ω     53.00 109.00   1.00   54.38    --  105.27 -95.00-120.00   56
  9  ω     73.00 149.00   1.00   54.38    --  105.27  77.00 -60.00   76
 10  ω     48.00 108.00   1.00   54.38    --  105.27-125.00-180.00   60
 11  ω    122.00 170.00   1.00   54.38    --  105.27 125.00-150.00   48
 12  ω     30.00 104.00   1.00   54.38    --  105.27 -30.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0869343000
_diffrn_orient_matrix_UB_12      -0.0636520000
_diffrn_orient_matrix_UB_13      -0.0472913000
_diffrn_orient_matrix_UB_21      0.0711726000
_diffrn_orient_matrix_UB_22      -0.0778817000
_diffrn_orient_matrix_UB_23      -0.0074964000
_diffrn_orient_matrix_UB_31      -0.0004842000
_diffrn_orient_matrix_UB_32      -0.0194609000
_diffrn_orient_matrix_UB_33      0.1849678000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6667
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.758
_diffrn_reflns_theta_min         3.222
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.088
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0558P)²+0.1773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2638
_reflns_number_total             3234
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0082_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105748
_chemical_oxdiff_usercomment     'C H N'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.878
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), N2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.752
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.74319(9) 0.51071(10) 0.19701(16) 0.0550(3) Uani 1 1 d . . . . .
C2 C 0.79443(9) 0.42408(11) 0.25976(17) 0.0585(4) Uani 1 1 d . . . . .
C3 C 0.87390(12) 0.42931(14) 0.3870(2) 0.0790(5) Uani 1 1 d . . . . .
H3 H 0.894475 0.484378 0.431399 0.095 Uiso 1 1 calc R U . . .
C4 C 0.92251(14) 0.35267(17) 0.4478(3) 0.0945(6) Uani 1 1 d . . . . .
H4 H 0.976188 0.356759 0.531764 0.113 Uiso 1 1 calc R U . . .
C5 C 0.89227(14) 0.27116(16) 0.3855(3) 0.0905(6) Uani 1 1 d . . . . .
H5 H 0.924707 0.219982 0.427977 0.109 Uiso 1 1 calc R U . . .
C6 C 0.81470(14) 0.26513(14) 0.2614(2) 0.0844(5) Uani 1 1 d . . . . .
H6 H 0.794053 0.209650 0.219178 0.101 Uiso 1 1 calc R U . . .
C7 C 0.76597(12) 0.34139(12) 0.1972(2) 0.0711(4) Uani 1 1 d . . . . .
H7 H 0.713591 0.336517 0.111016 0.085 Uiso 1 1 calc R U . . .
C8 C 0.80142(9) 0.56459(11) 0.08791(16) 0.0583(4) Uani 1 1 d . . . . .
C9 C 0.85309(13) 0.52248(14) -0.0210(2) 0.0813(5) Uani 1 1 d . . . . .
H9 H 0.856568 0.460703 -0.022206 0.098 Uiso 1 1 calc R U . . .
C10 C 0.89977(14) 0.57185(17) -0.1285(2) 0.0930(6) Uani 1 1 d . . . . .
H10 H 0.934812 0.542920 -0.200477 0.112 Uiso 1 1 calc R U . . .
C11 C 0.89456(12) 0.66279(16) -0.1294(2) 0.0842(5) Uani 1 1 d . . . . .
H11 H 0.925942 0.695599 -0.201527 0.101 Uiso 1 1 calc R U . . .
C12 C 0.84314(14) 0.70495(15) -0.0238(2) 0.0859(5) Uani 1 1 d . . . . .
H12 H 0.839005 0.766706 -0.024803 0.103 Uiso 1 1 calc R U . . .
C13 C 0.79686(12) 0.65631(12) 0.0852(2) 0.0714(4) Uani 1 1 d . . . . .
H13 H 0.762391 0.685877 0.157170 0.086 Uiso 1 1 calc R U . . .
C14 C 0.64152(9) 0.49473(10) 0.09496(16) 0.0531(3) Uani 1 1 d . . . . .
C15 C 0.63067(9) 0.56885(9) 0.32955(15) 0.0511(3) Uani 1 1 d . . . . .
C16 C 0.57888(10) 0.60890(9) 0.45479(16) 0.0519(3) Uani 1 1 d . . . . .
C17 C 0.63227(12) 0.63793(12) 0.60360(19) 0.0704(4) Uani 1 1 d . . . . .
H17 H 0.699840 0.632665 0.622415 0.085 Uiso 1 1 calc R U . . .
C18 C 0.58522(14) 0.67448(13) 0.7232(2) 0.0832(5) Uani 1 1 d . . . . .
H18 H 0.621267 0.694001 0.822644 0.100 Uiso 1 1 calc R U . . .
C19 C 0.48535(14) 0.68239(12) 0.6971(2) 0.0784(5) Uani 1 1 d . . . . .
H19 H 0.454207 0.707566 0.778316 0.094 Uiso 1 1 calc R U . . .
C20 C 0.43147(12) 0.65316(12) 0.5510(2) 0.0706(4) Uani 1 1 d . . . . .
H20 H 0.363884 0.658192 0.533594 0.085 Uiso 1 1 calc R U . . .
C21 C 0.47804(10) 0.61620(10) 0.42975(17) 0.0602(3) Uani 1 1 d . . . . .
H21 H 0.441569 0.596173 0.331111 0.072 Uiso 1 1 calc R U . . .
N1 N 0.72346(8) 0.56131(9) 0.34261(13) 0.0577(3) Uani 1 1 d . . . . .
N2 N 0.57870(7) 0.53273(8) 0.18377(13) 0.0536(3) Uani 1 1 d . . . . .
H2 H 0.516390 0.534468 0.155187 0.064 Uiso 1 1 calc R U . . .
O1 O 0.62100(7) 0.45767(8) -0.03928(12) 0.0653(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C14 112.64(12) . .
C8 C1 C2 112.58(10) . .
C8 C1 C14 107.03(10) . .
N1 C1 C2 107.78(11) . .
N1 C1 C8 112.48(12) . .
N1 C1 C14 104.08(10) . .
C3 C2 C1 118.15(15) . .
C7 C2 C1 123.56(13) . .
C7 C2 C3 118.29(16) . .
C2 C3 H3 119.9 . .
C4 C3 C2 120.2(2) . .
C4 C3 H3 119.9 . .
C3 C4 H4 119.7 . .
C5 C4 C3 120.59(18) . .
C5 C4 H4 119.7 . .
C4 C5 H5 120.1 . .
C6 C5 C4 119.81(19) . .
C6 C5 H5 120.1 . .
C5 C6 H6 119.8 . .
C5 C6 C7 120.4(2) . .
C7 C6 H6 119.8 . .
C2 C7 C6 120.72(16) . .
C2 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
C9 C8 C1 120.76(15) . .
C13 C8 C1 120.74(13) . .
C13 C8 C9 118.27(15) . .
C8 C9 H9 119.8 . .
C8 C9 C10 120.45(19) . .
C10 C9 H9 119.8 . .
C9 C10 H10 119.8 . .
C11 C10 C9 120.46(18) . .
C11 C10 H10 119.8 . .
C10 C11 H11 120.2 . .
C12 C11 C10 119.62(17) . .
C12 C11 H11 120.2 . .
C11 C12 H12 119.8 . .
C11 C12 C13 120.4(2) . .
C13 C12 H12 119.8 . .
C8 C13 C12 120.78(17) . .
C8 C13 H13 119.6 . .
C12 C13 H13 119.6 . .
N2 C14 C1 105.06(11) . .
O1 C14 C1 128.15(12) . .
O1 C14 N2 126.77(12) . .
N1 C15 C16 125.24(12) . .
N1 C15 N2 114.22(11) . .
N2 C15 C16 120.52(11) . .
C17 C16 C15 119.04(12) . .
C21 C16 C15 121.73(12) . .
C21 C16 C17 119.21(13) . .
C16 C17 H17 120.0 . .
C18 C17 C16 120.00(15) . .
C18 C17 H17 120.0 . .
C17 C18 H18 119.7 . .
C19 C18 C17 120.54(16) . .
C19 C18 H18 119.7 . .
C18 C19 H19 119.9 . .
C20 C19 C18 120.11(15) . .
C20 C19 H19 119.9 . .
C19 C20 H20 120.1 . .
C19 C20 C21 119.84(15) . .
C21 C20 H20 120.1 . .
C16 C21 H21 119.9 . .
C20 C21 C16 120.30(14) . .
C20 C21 H21 119.9 . .
C15 N1 C1 107.13(11) . .
C14 N2 C15 109.43(10) . .
C14 N2 H2 125.3 . .
C15 N2 H2 125.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.532(2) .
C1 C8 1.5298(19) .
C1 C14 1.5387(17) .
C1 N1 1.4750(17) .
C2 C3 1.391(2) .
C2 C7 1.378(2) .
C3 H3 0.9300 .
C3 C4 1.386(3) .
C4 H4 0.9300 .
C4 C5 1.367(3) .
C5 H5 0.9300 .
C5 C6 1.358(3) .
C6 H6 0.9300 .
C6 C7 1.390(2) .
C7 H7 0.9300 .
C8 C9 1.384(2) .
C8 C13 1.380(2) .
C9 H9 0.9300 .
C9 C10 1.389(3) .
C10 H10 0.9300 .
C10 C11 1.369(3) .
C11 H11 0.9300 .
C11 C12 1.363(3) .
C12 H12 0.9300 .
C12 C13 1.388(2) .
C13 H13 0.9300 .
C14 N2 1.3495(16) .
C14 O1 1.2223(16) .
C15 C16 1.4722(18) .
C15 N1 1.2818(17) .
C15 N2 1.3988(16) .
C16 C17 1.388(2) .
C16 C21 1.3875(19) .
C17 H17 0.9300 .
C17 C18 1.376(2) .
C18 H18 0.9300 .
C18 C19 1.375(3) .
C19 H19 0.9300 .
C19 C20 1.375(3) .
C20 H20 0.9300 .
C20 C21 1.385(2) .
C21 H21 0.9300 .
N2 H2 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 C2 C3 C4 179.97(15) . . . .
C1 C2 C7 C6 -178.99(14) . . . .
C1 C8 C9 C10 175.15(15) . . . .
C1 C8 C13 C12 -174.61(14) . . . .
C1 C14 N2 C15 -0.88(15) . . . .
C2 C1 C8 C9 37.30(18) . . . .
C2 C1 C8 C13 -148.38(14) . . . .
C2 C1 C14 N2 115.66(12) . . . .
C2 C1 C14 O1 -65.88(19) . . . .
C2 C1 N1 C15 -117.48(12) . . . .
C2 C3 C4 C5 -1.0(3) . . . .
C3 C2 C7 C6 0.9(2) . . . .
C3 C4 C5 C6 0.9(3) . . . .
C4 C5 C6 C7 0.1(3) . . . .
C5 C6 C7 C2 -1.0(3) . . . .
C7 C2 C3 C4 0.1(2) . . . .
C8 C1 C2 C3 75.32(16) . . . .
C8 C1 C2 C7 -104.78(15) . . . .
C8 C1 C14 N2 -120.09(12) . . . .
C8 C1 C14 O1 58.4(2) . . . .
C8 C1 N1 C15 117.83(12) . . . .
C8 C9 C10 C11 -0.6(3) . . . .
C9 C8 C13 C12 -0.1(2) . . . .
C9 C10 C11 C12 0.0(3) . . . .
C10 C11 C12 C13 0.6(3) . . . .
C11 C12 C13 C8 -0.5(3) . . . .
C13 C8 C9 C10 0.7(3) . . . .
C14 C1 C2 C3 -163.54(12) . . . .
C14 C1 C2 C7 16.35(18) . . . .
C14 C1 C8 C9 -86.99(16) . . . .
C14 C1 C8 C13 87.33(16) . . . .
C14 C1 N1 C15 2.33(15) . . . .
C15 C16 C17 C18 -179.14(16) . . . .
C15 C16 C21 C20 179.15(14) . . . .
C16 C15 N1 C1 175.15(13) . . . .
C16 C15 N2 C14 -175.69(12) . . . .
C16 C17 C18 C19 0.2(3) . . . .
C17 C16 C21 C20 0.9(2) . . . .
C17 C18 C19 C20 0.4(3) . . . .
C18 C19 C20 C21 -0.4(3) . . . .
C19 C20 C21 C16 -0.3(3) . . . .
C21 C16 C17 C18 -0.8(3) . . . .
N1 C1 C2 C3 -49.31(16) . . . .
N1 C1 C2 C7 130.59(14) . . . .
N1 C1 C8 C9 159.30(13) . . . .
N1 C1 C8 C13 -26.38(17) . . . .
N1 C1 C14 N2 -0.81(15) . . . .
N1 C1 C14 O1 177.66(15) . . . .
N1 C15 C16 C17 -3.1(2) . . . .
N1 C15 C16 C21 178.68(14) . . . .
N1 C15 N2 C14 2.64(17) . . . .
N2 C15 C16 C17 175.07(14) . . . .
N2 C15 C16 C21 -3.2(2) . . . .
N2 C15 N1 C1 -3.10(16) . . . .
O1 C14 N2 C15 -179.37(14) . . . .
