Caesium carbonate promoted regioselective <i>O</i>-functionalization of 4,6-diphenylpyrimidin-2(1<i>H</i>)-ones under mild conditions and mechanistic insight.
Kumar, Vijay; Singh, Praval Pratap; Dwivedi, Ashish Ranjan; Kumar, Naveen; Kumar, Rajesh; Chandra Sahoo, Subash; Chakraborty, Sudip; Kumar, Vinod; RSC advances 13 (2023) 16899–16906; doi:10.1039/d3ra00773a

data_7246992
_publ_section_title
;
 Caesium carbonate promoted regioselective <i>O</i>-functionalization of
 4,6-diphenylpyrimidin-2(1<i>H</i>)-ones under mild conditions and
 mechanistic insight.
;
_journal_issue                   25
_journal_name_full               'RSC advances'
_journal_page_first              16899
_journal_page_last               16906
_journal_paper_doi               10.1039/d3ra00773a
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C21 H18 N2 O3'
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.389
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-05
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-05-14 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.182(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2375(5)
_cell_length_b                   18.6453(12)
_cell_length_c                   17.8444(13)
_cell_measurement_reflns_used    3183
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.7820
_cell_measurement_theta_min      3.4590
_cell_volume                     1742.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-ac5-024 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9703
_diffrn_measured_fraction_theta_max 0.9613
_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    -32.00  -7.00   0.50   20.00    --   -9.32 -83.00-120.00   50
  2  \w    -16.00  31.00   0.50   20.00    --   -9.32  83.00  -0.00   94
  3  \w    -29.00  -2.00   0.50   20.00    --    9.60 -83.00-120.00   54
  4  \w    -16.00   9.00   0.50   20.00    --    9.60  83.00  -0.00   50
  5  \w    -35.00  42.00   0.50   20.00    --   -9.32  77.00  30.00  154
  6  \w    -51.00 -17.00   0.50   20.00    --   -9.32 125.00-120.00   68
  7  \w    -39.00 -13.00   0.50   20.00    --   -9.32 -77.00  60.00   52
  8  \w      7.00  49.00   0.50   20.00    --    9.60-125.00   0.00   84
  9  \w     -1.00  42.00   0.50   20.00    --    9.60  77.00-150.00   86
 10  \w    -12.00  37.00   0.50   20.00    --    9.60  77.00 150.00   98
 11  \w     22.00  47.00   0.50   20.00    --    9.60-125.00 150.00   50
 12  \w    -54.00   7.00   0.50   20.00    --    9.60 -57.00-120.00  122
 13  \w    -28.00  18.00   0.50   20.00    --    9.60 -57.00 -90.00   92
 14  \w    -11.00  12.00   0.50   20.00    --    9.60 -99.00-180.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0581080000
_diffrn_orient_matrix_UB_12      -0.0263422000
_diffrn_orient_matrix_UB_13      -0.0230022000
_diffrn_orient_matrix_UB_21      -0.1026573000
_diffrn_orient_matrix_UB_22      -0.0237936000
_diffrn_orient_matrix_UB_23      0.0072863000
_diffrn_orient_matrix_UB_31      -0.0665032000
_diffrn_orient_matrix_UB_32      0.0136847000
_diffrn_orient_matrix_UB_33      -0.0315897000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1006
_diffrn_reflns_av_unetI/netI     0.1269
_diffrn_reflns_Laue_measured_fraction_full 0.9703
_diffrn_reflns_Laue_measured_fraction_max 0.9613
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16485
_diffrn_reflns_point_group_measured_fraction_full 0.9703
_diffrn_reflns_point_group_measured_fraction_max 0.9613
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
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    1.320
_exptl_crystal_description       needle
_exptl_crystal_F_000             728.481
_exptl_crystal_size_max          0.018
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.6020
_refine_diff_density_min         -0.5872
_refine_diff_density_rms         0.1384
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             6.4459
_refine_ls_goodness_of_fit_ref   0.9745
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9745
_refine_ls_R_factor_all          0.1914
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0677P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                1378
_reflns_number_total             3428
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ra00773a2.cif
_cod_data_source_block           2a
_cod_database_code               7246992
_chemical_oxdiff_formula         'C H N O'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C10(H10), C8(H8), C17(H17), C4(H4), C5(H5), C7(H7),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C9(H9a,H9b,H9c)
2.d :
 C21(H21)
;
_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 2.670
_oxdiff_exptl_absorpt_empirical_full_min 0.326