Catalytic Oxidation of 3-Arylbenzofuran-2(3 H)-ones with PCC-H<sub>5</sub>IO<sub>6</sub>: Syntheses of 3-Aryl-3-hydroxy/3-amido-3-arylbenzofuran-2(3 H)-ones.
Dhotare, Bhaskar B.; Kumar, Mukesh; Nayak, Sandip K.; The Journal of organic chemistry 83 (2018) 10089–10096; doi:10.1021/acs.joc.8b01395

data_4035050
_publ_section_title
;
 Catalytic Oxidation of 3-Arylbenzofuran-2(3 H)-ones with
 PCC-H<sub>5</sub>IO<sub>6</sub>: Syntheses of
 3-Aryl-3-hydroxy/3-amido-3-arylbenzofuran-2(3 H)-ones.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10089
_journal_page_last               10096
_journal_paper_doi               10.1021/acs.joc.8b01395
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C30 H22 O4'
_chemical_formula_sum            'C30 H22 O4'
_chemical_formula_weight         446.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.992(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7126(2)
_cell_length_b                   20.5098(4)
_cell_length_c                   12.2179(4)
_cell_measurement_reflns_used    6624
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.8790
_cell_measurement_theta_min      4.2830
_cell_volume                     2314.83(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3200
_diffrn_detector_type            Titan
_diffrn_measured_fraction_theta_full 0.999
_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    -24.00  66.00   1.00    1.00    --   43.54 -57.00 -60.00   90
  2  \w     29.00  91.00   1.00    1.06    --  102.90-126.00 -90.00   62
  3  \w     82.00 111.00   1.00    1.06    --  102.90-126.00 -60.00   29
  4  \w     78.00 121.00   1.00    1.06    --  102.90-126.00-150.00   43
  5  \w     49.00 107.00   1.00    1.06    --  102.90 -95.00 -30.00   58
  6  \w     34.00  60.00   1.00    1.06    --  102.90-126.00 -60.00   26
  7  \w     31.00 131.00   1.00    1.06    --  102.90 -77.00  30.00  100
  8  \w     80.00 156.00   1.00    1.06    --  102.90  45.00   0.00   76
  9  \w    133.00 158.00   1.00    1.06    --  102.90 126.00 120.00   25
 10  \w    107.00 136.00   1.00    1.06    --  102.90  45.00 120.00   29
 11  \w     88.00 157.00   1.00    1.06    --  102.90 126.00  30.00   69
 12  \w     90.00 158.00   1.00    1.06    --  102.90  61.00-180.00   68
 13  \w     35.00 125.00   1.00    1.06    --  102.90 -30.00   0.00   90
 14  \w     30.00  56.00   1.00    1.06    --  102.90-126.00-150.00   26
 15  \w     30.00 129.00   1.00    1.06    --  102.90 -30.00-120.00   99
 16  \w     23.00 113.00   1.00    1.00    --   43.54  57.00 -30.00   90
 17  \w     22.00 100.00   1.00    1.00    --   43.54  38.00 120.00   78
 18  \w    -66.00 -30.00   1.00    1.00    --  -43.54  57.00-180.00   36
 19  \w   -114.00 -89.00   1.00    1.00    --  -43.54 -99.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162766000
_diffrn_orient_matrix_UB_12      -0.0731940000
_diffrn_orient_matrix_UB_13      0.0215559000
_diffrn_orient_matrix_UB_21      0.0411954000
_diffrn_orient_matrix_UB_22      0.0130469000
_diffrn_orient_matrix_UB_23      0.1303486000
_diffrn_orient_matrix_UB_31      -0.1607235000
_diffrn_orient_matrix_UB_32      0.0107954000
_diffrn_orient_matrix_UB_33      -0.0112811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17167
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.260
_diffrn_reflns_theta_min         4.311
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.00093(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0554P)^2^+0.3303P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3349
_reflns_number_total             4557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01395_si_001.cif
_cod_data_source_block           skn7_1
_cod_database_code               4035050
_chemical_oxdiff_formula         'C15 H12 O3'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C3(H3), C4(H4), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C29(H29)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C28(H28A,H28B,H28C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-26
_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 2.215
_oxdiff_exptl_absorpt_empirical_full_min 0.497