Metal-free benzoylation of imidazoheterocycles by oxidative decarboxylation of arylglyoxylic acids.
Jaspal, Sonam; Shinde, Vikki N.; Meena, Neha; Nipate, Dhananjay S.; Rangan, Krishnan; Kumar, Anil; Organic & biomolecular chemistry 18 (2020) 9072–9080; doi:10.1039/d0ob01842b

data_7157737
_publ_section_title
;
 Metal-free benzoylation of imidazoheterocycles by oxidative
 decarboxylation of arylglyoxylic acids.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9072
_journal_page_last               9080
_journal_paper_doi               10.1039/d0ob01842b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-20 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3127(2)
_cell_length_b                   17.1849(3)
_cell_length_c                   20.9916(4)
_cell_measurement_reflns_used    7547
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.1790
_cell_measurement_theta_min      5.1860
_cell_volume                     2998.71(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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     43.00  69.00   0.50    2.72    --    0.00  37.00 150.00   52
  2  \w    -45.00  14.00   0.50    2.72    --    0.00 -37.00-120.00  118
  3  \w    -22.00  65.00   0.50    2.72    --    0.00  57.00  60.00  174
  4  \w    147.00 185.00   0.50   10.92    --  107.20  30.00 -60.00   76
  5  \w     59.00 123.00   0.50   10.92    --  107.20 -61.00-180.00  128
  6  \w     92.00 194.00   0.50   10.92    --  107.20  45.00-150.00  204
  7  \w     19.00  92.00   0.50   10.92    --  107.20 -61.00 -90.00  146
  8  \w     33.00 133.00   0.50   10.92    --  107.20 -15.00  30.00  200
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0249451000
_diffrn_orient_matrix_UB_12      -0.0257324000
_diffrn_orient_matrix_UB_13      0.0695490000
_diffrn_orient_matrix_UB_21      -0.1524062000
_diffrn_orient_matrix_UB_22      0.0506045000
_diffrn_orient_matrix_UB_23      0.0039014000
_diffrn_orient_matrix_UB_31      -0.1024595000
_diffrn_orient_matrix_UB_32      -0.0693689000
_diffrn_orient_matrix_UB_33      -0.0231182000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10545
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.542
_diffrn_reflns_theta_min         4.212
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       Block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0647P)^2^+1.2434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2968
_reflns_number_total             3204
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01842b2.cif
_cod_data_source_block           exp_565_ak-sj-280
_cod_depositor_comments          'Adding full bibliography for 7157737.cif.'
_cod_database_code               7157737
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C16(H16), C4(H4), C2(H2), C3(H3), C17(H17), C9(H9), C13(H13),
 C12(H12), C20(H20), C18(H18), C11(H11), C19(H19), C10(H10)
;
_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 1.373
_oxdiff_exptl_absorpt_empirical_full_min 0.774