I<sub>2</sub>-DMSO-mediated [4 + 2] cyclization of methyl ketone with 2-aminobenzimidazole to construct 2,4-disubstituted benzo[4,5]imidazo[1,2-<i>a</i>] pyrimidines.
Guo, Qian; Guo, Mengyi; Cheng, Luoteng; Song, Yifan; Ma, Wanqian; Song, Yibo; Li, Suzhen; Deng, Xiaoqiong; Jia, Xinxin; Yuan, Jianyong; Organic & biomolecular chemistry 23 (2025) 5154–5158; doi:10.1039/d5ob00314h

data_7160519
_publ_section_title
;
 I<sub>2</sub>-DMSO-mediated [4 + 2] cyclization of methyl ketone with
 2-aminobenzimidazole to construct 2,4-disubstituted
 benzo[4,5]imidazo[1,2-<i>a</i>] pyrimidines.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5154
_journal_page_last               5158
_journal_paper_doi               10.1039/d5ob00314h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H15 N3 O'
_chemical_formula_sum            'C23 H15 N3 O'
_chemical_formula_weight         349.38
_chemical_melting_point          499(7)
_chemical_name_systematic
phenyl(4-phenylbenzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)methanonee
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2024-04-13
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-11-16 deposited with the CCDC.	2025-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.2930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.66990(10)
_cell_length_b                   17.9820(2)
_cell_length_c                   12.15830(10)
_cell_measurement_reflns_used    9247
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.1180
_cell_measurement_theta_min      4.3870
_cell_volume                     1674.11(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_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     30.00  68.00   0.50    0.15    --   99.00 -61.00-120.00   76
  2  \w     36.00  73.00   0.50    0.15    --   99.00 -61.00 -60.00   74
  3  \w     35.00  61.00   0.50    0.15    --   99.00 -61.00 -30.00   52
  4  \w     35.00  66.00   0.50    0.15    --   99.00 -61.00 -90.00   62
  5  \w     28.00  53.00   0.50    0.15    --   99.00 -45.00 -90.00   50
  6  \w     36.00  72.00   0.50    0.15    --   99.00 -61.00   0.00   72
  7  \w     27.00  52.00   0.50    0.15    --   99.00 -45.00  60.00   50
  8  \w     36.00  70.00   0.50    0.15    --   99.00 -61.00  90.00   68
  9  \w     26.00  72.00   0.50    0.15    --   99.00 -61.00 120.00   92
 10  \w     27.00  53.00   0.50    0.15    --   99.00 -45.00 150.00   52
 11  \w     28.00  53.00   0.50    0.15    --   99.00 -45.00 120.00   50
 12  \w     27.00  53.00   0.50    0.15    --   99.00 -45.00 -30.00   52
 13  \w     28.00  53.00   0.50    0.15    --   99.00 -45.00-120.00   50
 14  \w     -2.00  31.00   0.50    0.10    --   45.87-103.00  89.00   66
 15  \w     36.00  76.00   0.50    0.10    --   45.87-103.00  89.00   80
 16  \w     38.00 106.00   0.50    0.15    --   99.00-103.00  89.00  136
 17  \w    -28.00  29.00   0.50    0.10    --   45.87 -19.00 150.00  114
 18  \w    -27.00  -2.00   0.50    0.10    --   45.87 -37.00 -30.00   50
 19  \w      6.00  43.00   0.50    0.10    --   45.87 -37.00 -30.00   74
 20  \w    110.00 135.00   0.50    0.15    --   99.00 103.00-167.00   50
 21  \w    -22.00  27.00   0.50    0.10    --  -45.87  19.00  30.00   98
 22  \w    -24.00  24.00   0.50    0.10    --  -45.87  19.00 -90.00   96
 23  \w    -68.00 -40.00   0.50    0.15    --  -99.00  61.00 150.00   56
 24  \w    -61.00 -35.00   0.50    0.15    --  -99.00  61.00-180.00   52
 25  \w   -107.00 -66.00   0.50    0.15    --  -99.00 103.00-167.00   82
 26  \w   -104.00 -78.00   0.50    0.15    --  -99.00 125.00-150.00   52
 27  \w    -62.00 -29.00   0.50    0.15    --  -99.00 125.00-150.00   66
 28  \w    -38.00  -3.00   0.50    0.10    --  -45.87 103.00-167.00   70
 29  \w   -170.00 -86.00   0.50    0.15    --  -99.00-103.00  89.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0288112000
_diffrn_orient_matrix_UB_12      0.0637740000
_diffrn_orient_matrix_UB_13      -0.0817520000
_diffrn_orient_matrix_UB_21      -0.0524046000
_diffrn_orient_matrix_UB_22      -0.0520722000
_diffrn_orient_matrix_UB_23      -0.0969047000
_diffrn_orient_matrix_UB_31      -0.1920298000
_diffrn_orient_matrix_UB_32      0.0237036000
_diffrn_orient_matrix_UB_33      0.0065555000
_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  0.0210
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11799
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.178
_diffrn_reflns_theta_min         4.395
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ????'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0037(2)
_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   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0364P)^2^+0.6798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3049
_reflns_number_total             3264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00314h2.cif
_cod_data_source_block           chongqin
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '218.7-232.7 \%C' was
changed to '499(7)' -- it was converted from degrees Celsius (C) to
kelvins (K), 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 7160519.cif.
;
_cod_database_code               7160519
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C20(H20), C21(H21), C22(H22), C23(H23)
;
_shelx_res_checksum              41643
_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 1.207
_oxdiff_exptl_absorpt_empirical_full_min 0.681