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_7160291
_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         'C29 H22 N2 O'
_chemical_formula_sum            'C29 H22 N2 O'
_chemical_formula_weight         414.48
_chemical_melting_point          501.0(10)
_chemical_name_systematic
1,3-Dimethyl-6-(naphthalen-1-yl)-7-phenyl-1H-perimidin-2(3H)-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_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                85.449(4)
_cell_angle_beta                 81.551(4)
_cell_angle_gamma                84.968(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2374(3)
_cell_length_b                   10.5850(5)
_cell_length_c                   13.7433(6)
_cell_measurement_reflns_used    9190
_cell_measurement_temperature    100.02(11)
_cell_measurement_theta_max      75.4850
_cell_measurement_theta_min      4.1720
_cell_volume                     1178.06(9)
_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      100.02(11)
_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 0.992
_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   -114.00 -59.00   1.00    5.00    --  -41.35-147.00  94.00   55
  2  \w    -92.00  -2.00   1.00    5.00    --  -41.35 125.00 -21.00   90
  3  \w   -108.00 -13.00   1.00    5.00    --  -41.35 147.00 143.00   95
  4  \w     23.00  97.00   1.00    5.00    --   41.35-125.00-100.00   74
  5  \w     35.00 112.00   1.00    5.00    --   41.35-147.00  94.00   77
  6  \w     39.00 133.00   1.00   20.00    --  112.00-147.00  94.00   94
  7  \w     39.00 118.00   1.00   20.00    --  112.00-125.00-100.00   79
  8  \w     94.00 178.00   1.00   20.00    --  112.00 125.00 -21.00   84
  9  \w     81.00 173.00   1.00   20.00    --  112.00 147.00 143.00   92
 10  \w   -116.00 -17.00   1.00    5.00    --  -41.35 -38.00-150.00   99
 11  \w   -116.00 -17.00   1.00    5.00    --  -41.35 -38.00 -60.00   99
 12  \w     17.00 116.00   1.00    5.00    --   41.35  38.00 150.00   99
 13  \w     23.00  97.00   1.00    5.00    --   41.35-125.00-180.00   74
 14  \w     83.00 178.00   1.00   20.00    --  112.00  61.00 -30.00   95
 15  \w     83.00 178.00   1.00   20.00    --  112.00  61.00-150.00   95
 16  \w     40.00 141.00   1.00   20.00    --  112.00 -61.00  30.00  101
 17  \w     30.00 110.00   1.00   20.00    --  112.00 -95.00 -60.00   80
 18  \w     79.00 178.00   1.00   20.00    --  112.00  77.00-120.00   99
 19  \w     57.00 150.00   1.00   20.00    --  112.00 178.00-120.00   93
 20  \w     57.00 150.00   1.00   20.00    --  112.00 178.00   0.00   93
 21  \w     36.00 113.00   1.00   20.00    --  112.00-111.00 -90.00   77
 22  \w     36.00 113.00   1.00   20.00    --  112.00-111.00   0.00   77
 23  \w     36.00 113.00   1.00   20.00    --  112.00-111.00  90.00   77
 24  \w     40.00 141.00   1.00   20.00    --  112.00 -61.00 -30.00  101
 25  \w     39.00 138.00   1.00   20.00    --  112.00 -45.00-120.00   99
 26  \w     36.00 113.00   1.00   20.00    --  112.00-111.00-180.00   77
 27  \w    100.00 178.00   1.00   20.00    --  112.00 111.00 -30.00   78
 28  \w     36.00 113.00   1.00   20.00    --  112.00-111.00 -30.00   77
 29  \w    100.00 178.00   1.00   20.00    --  112.00 111.00  90.00   78
 30  \w     86.00 178.00   1.00   20.00    --  112.00  45.00-150.00   92
 31  \w     24.00 178.00   1.00   20.00    --  112.00   0.00-150.00  154
 32  \w     57.00 150.00   1.00   20.00    --  112.00 178.00 -30.00   93
 33  \w     36.00 113.00   1.00   20.00    --  112.00-111.00 -60.00   77
 34  \w     36.00 113.00   1.00   20.00    --  112.00-111.00  60.00   77
 35  \w     36.00 113.00   1.00   20.00    --  112.00-111.00 120.00   77
 36  \w    122.00 147.00   1.00   20.00    --  112.00 111.00-180.00   25
 37  \w    101.00 169.00   1.00   20.00    --  112.00 111.00 -60.00   68
 38  \w    144.00 176.00   1.00   20.00    --  112.00 111.00 120.00   32
 39  \w    128.00 155.00   1.00   20.00    --  112.00 111.00 150.00   27
 40  \w     32.00  57.00   1.00   20.00    --  112.00 -95.00-180.00   25
 41  \w     83.00 110.00   1.00   20.00    --  112.00 -95.00-180.00   27
 42  \w     95.00 166.00   1.00   20.00    --  112.00  45.00 120.00   71
 43  \w    120.00 171.00   1.00   20.00    --  112.00  61.00  90.00   51
 44  \w     39.00  71.00   1.00   20.00    --  112.00 -75.00 125.26   32
 45  \w     77.00 104.00   1.00   20.00    --  112.00 -75.00 125.26   27
 46  \w    128.00 176.00   1.00   20.00    --  112.00  15.00  60.00   48
 47  \w     90.00  97.00   1.00   20.00    --  112.00  61.00  90.00    7
;
_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      -0.0838101000
_diffrn_orient_matrix_UB_12      0.1142354000
_diffrn_orient_matrix_UB_13      -0.0550653000
_diffrn_orient_matrix_UB_21      -0.0905050000
_diffrn_orient_matrix_UB_22      0.0449455000
_diffrn_orient_matrix_UB_23      0.0989306000
_diffrn_orient_matrix_UB_31      0.1440375000
_diffrn_orient_matrix_UB_32      0.0798395000
_diffrn_orient_matrix_UB_33      0.0090439000
_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  0.0537
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24649
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.383
_diffrn_reflns_theta_min         4.202
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.555
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.617
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.234
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0933
_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/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2778
_refine_ls_wR_factor_ref         0.2966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3898
_reflns_number_total             4913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01680g2.cif
_cod_data_source_block           d_37_autored
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '500-502' was changed to
'501.0(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               7160291
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C29 H22 N2 O'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.888
_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:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H),
 C00J(H00J), C00K(H00K), C00M(H00M), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W)
2.b Idealised Me refined as rotating group:
 C00L(H00E,H00F,H00I), C00O(H00L,H00N,H00O)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              40673
_shelx_fab_checksum              59098
_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 2.432
_oxdiff_exptl_absorpt_empirical_full_min 0.504