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_7160289
_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         'C27 H24 N2 O3'
_chemical_formula_sum            'C27 H24 N2 O3'
_chemical_formula_weight         424.48
_chemical_melting_point          550.0(10)
_chemical_name_systematic
6,7-Di(4-methoxyphenyl)-1,3-dimethyl-1H-perimidin-2(3H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-10-17 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.109(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.32080(10)
_cell_length_b                   28.4887(4)
_cell_length_c                   9.40150(10)
_cell_measurement_reflns_used    9120
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1420
_cell_measurement_theta_min      5.4190
_cell_volume                     2001.20(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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    -81.00  26.00   1.00    1.00    --  -42.10  94.00-127.00  107
  2  \w     -4.00  81.00   1.00    1.00    --   42.10 -94.00 121.00   85
  3  \w     29.00 110.00   1.00    1.00    --  112.00 -94.00 121.00   81
  4  \w    101.00 178.00   1.00    1.00    --  112.00  94.00-127.00   77
  5  \w   -115.00 -14.00   1.00    1.00    --  -42.10 -57.00 120.00  101
  6  \w   -116.00 -18.00   1.00    1.00    --  -42.10 -38.00 -60.00   98
  7  \w     23.00  98.00   1.00    1.00    --   42.10-125.00-150.00   75
  8  \w     84.00 178.00   1.00    1.00    --  112.00  30.00-120.00   94
  9  \w     86.00 178.00   1.00    1.00    --  112.00  47.00  73.25   92
 10  \w     36.00 113.00   1.00    1.00    --  112.00-111.00 120.00   77
 11  \w    100.00 178.00   1.00    1.00    --  112.00 111.00 -60.00   78
 12  \w     30.00 110.00   1.00    1.00    --  112.00 -95.00  90.00   80
 13  \w     30.00 110.00   1.00    1.00    --  112.00 -95.00  60.00   80
 14  \w     57.00 150.00   1.00    1.00    --  112.00 178.00 -90.00   93
 15  \w     84.00 178.00   1.00    1.00    --  112.00  30.00  30.00   94
 16  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00-120.00  101
 17  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00 150.00  101
 18  \w     36.00 113.00   1.00    1.00    --  112.00-111.00-180.00   77
 19  \w     86.00 178.00   1.00    1.00    --  112.00  44.00-106.68   92
 20  \w     36.00 113.00   1.00    1.00    --  112.00-111.00 -30.00   77
 21  \w     36.00 113.00   1.00    1.00    --  112.00-111.00  60.00   77
 22  \w    100.00 178.00   1.00    1.00    --  112.00 111.00 -30.00   78
 23  \w    100.00 178.00   1.00    1.00    --  112.00 111.00-180.00   78
 24  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -60.00   99
 25  \w     36.00 113.00   1.00    1.00    --  112.00-111.00 -60.00   77
 26  \w   -118.00 -10.00   1.00    1.00    --  -42.10 -77.00  60.00  108
 27  \w   -118.00 -10.00   1.00    1.00    --  -42.10 -77.00   0.00  108
 28  \w   -115.00 -14.00   1.00    1.00    --  -42.10 -57.00-150.00  101
 29  \w   -118.00 -76.00   1.00    1.00    --  -42.10 -77.00 -60.00   42
;
_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      -0.0614422000
_diffrn_orient_matrix_UB_12      0.0501471000
_diffrn_orient_matrix_UB_13      -0.0610467000
_diffrn_orient_matrix_UB_21      -0.1435264000
_diffrn_orient_matrix_UB_22      -0.0026398000
_diffrn_orient_matrix_UB_23      0.0614584000
_diffrn_orient_matrix_UB_31      0.1346392000
_diffrn_orient_matrix_UB_32      0.0200829000
_diffrn_orient_matrix_UB_33      0.1605994000
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15438
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.285
_diffrn_reflns_theta_min         5.465
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00196(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0505P)^2^+1.3331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1961
_reflns_number_total             2103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01680g2.cif
_cod_data_source_block           d_38_2_100_autored
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '549-551' was changed to
'550.0(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               7160289
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C27 H24 N2 O3'
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.824
_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:
 C10(H10), C2(H2), C11(H11), C3(H3), C14(H14), C13(H13)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              34880
_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 1.841
_oxdiff_exptl_absorpt_empirical_full_min 0.766