6-Aryl- and 6,7-diaryl-1,3-dimethyl-1<i>H</i>-perimidin-2(3<i>H</i>)-ones: synthesis, conformational stability, crystal structure and optical properties.
Dyatlov, Andrey L.; Filatova, Ekaterina A.; Pozharskii, Alexander F.; Marchenko, Sergey S.; Demidov, Oleg P.; Chernyshev, Anatoly V.; Metelitsa, Anatoly V.; Brig, Sergei S.; Medvedev, Michael G.; Bekmansurov, Danis R.; Morozov, Pavel G.; Gulevskaya, Anna V.; Organic & biomolecular chemistry 23 (2025) 948–959; doi:10.1039/d4ob01680g

data_7160292
_publ_section_title
;
 6-Aryl- and
 6,7-diaryl-1,3-dimethyl-1<i>H</i>-perimidin-2(3<i>H</i>)-ones: synthesis,
 conformational stability, crystal structure and optical properties.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              948
_journal_page_last               959
_journal_paper_doi               10.1039/d4ob01680g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C25 H20 N2 O'
_chemical_formula_sum            'C25 H20 N2 O'
_chemical_formula_weight         364.43
_chemical_melting_point          511.0(10)
_chemical_name_systematic
1,3-Dimethyl-6,7-diphenyl-1H-perimidin-2(3H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2024-10-17 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.4300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1969(2)
_cell_length_b                   7.43360(10)
_cell_length_c                   26.0222(4)
_cell_measurement_reflns_used    8316
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6670
_cell_measurement_theta_min      3.4270
_cell_volume                     3626.38(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -129.00  47.00   1.00    4.90    --  -40.82   0.00-120.00  176
  2  \w    -87.00  -6.00   1.00    4.90    --  -40.82 125.00  60.00   81
  3  \w     27.00  97.00   1.00    4.90    --   40.82-125.00   0.00   70
  4  \w     36.00 109.00   1.00   19.60    --  112.00-111.00  60.00   73
  5  \w    104.00 178.00   1.00   19.60    --  112.00 111.00-180.00   74
  6  \w     36.00 109.00   1.00   19.60    --  112.00-111.00 120.00   73
  7  \w     36.00 109.00   1.00   19.60    --  112.00-111.00 -90.00   73
  8  \w    104.00 178.00   1.00   19.60    --  112.00 111.00  30.00   74
  9  \w     30.00 106.00   1.00   19.60    --  112.00 -95.00 150.00   76
 10  \w     61.00 146.00   1.00   19.60    --  112.00 178.00  30.00   85
 11  \w     36.00 109.00   1.00   19.60    --  112.00-111.00  90.00   73
 12  \w     61.00 146.00   1.00   19.60    --  112.00 178.00  90.00   85
 13  \w     40.00 141.00   1.00   19.60    --  112.00 -61.00  18.62  101
 14  \w     36.00 140.00   1.00   19.60    --  112.00 -30.00  60.00  104
 15  \w     30.00 106.00   1.00   19.60    --  112.00 -95.00 -60.00   76
 16  \w     36.00 145.00   1.00   19.60    --  112.00 -77.00   0.00  109
 17  \w     30.00 106.00   1.00   19.60    --  112.00 -95.00   0.00   76
 18  \w     59.00 178.00   1.00   19.60    --  112.00  15.00 -90.00  119
 19  \w    104.00 178.00   1.00   19.60    --  112.00 111.00-120.00   74
 20  \w     36.00 139.00   1.00   19.60    --  112.00 -31.00-141.83  103
 21  \w   -113.00 -50.00   1.00    4.90    --  -40.82 -57.00  90.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0225473000
_diffrn_orient_matrix_UB_12      0.1698636000
_diffrn_orient_matrix_UB_13      0.0333495000
_diffrn_orient_matrix_UB_21      -0.0059589000
_diffrn_orient_matrix_UB_22      0.1117068000
_diffrn_orient_matrix_UB_23      -0.0505906000
_diffrn_orient_matrix_UB_31      -0.0788281000
_diffrn_orient_matrix_UB_32      0.0402972000
_diffrn_orient_matrix_UB_33      -0.0002203000
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19330
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.100
_diffrn_reflns_theta_min         3.478
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+1.1812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3169
_reflns_number_total             3775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01680g2.cif
_cod_data_source_block           d_3_autored
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '510-512' was changed to
'511.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160289--7160292.cif.
;
_cod_database_code               7160292
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H20 N2 O'
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.841
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C11(H11), C21(H21), C10(H10), C19(H19), C25(H25), C24(H24),
 C15(H15), C22(H22), C18(H18), C23(H23), C17(H17), C16(H16)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              46020
_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 1.267
_oxdiff_exptl_absorpt_empirical_full_min 0.768