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_4035048
_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         'C17 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_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
_audit_creation_date             2016-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.5600(19)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   15.5766(3)
_cell_length_b                   14.06756(19)
_cell_length_c                   21.4444(4)
_cell_measurement_reflns_used    17400
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.0100
_cell_measurement_theta_min      3.8070
_cell_volume                     4504.09(14)
_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 0.986
_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     23.00  50.00   1.00    1.00    --   43.54  57.00  90.00   27
  2  \w     46.00  72.00   1.00    1.00    --   43.54  57.00 120.00   26
  3  \w     72.00 109.00   1.00    1.00    --   43.54 126.00 120.00   37
  4  \w     76.00 102.00   1.00    5.00    --  102.90  61.00  60.00   26
  5  \w    108.00 156.00   1.00    5.00    --  102.90  77.00  60.00   48
  6  \w    118.00 158.00   1.00    5.00    --  102.90  66.00 119.19   40
  7  \w    114.00 157.00   1.00    5.00    --  102.90  77.00  90.00   43
  8  \w     89.00 115.00   1.00    5.00    --  102.90  45.00  60.00   26
  9  \w     83.00 156.00   1.00    5.00    --  102.90  36.00  16.00   73
 10  \w     89.00 121.00   1.00    5.00    --  102.90 -45.00  30.00   32
 11  \w     76.00 156.00   1.00    5.00    --  102.90  30.00 -30.00   80
 12  \w     92.00 148.00   1.00    5.00    --  102.90  45.00-120.00   56
 13  \w     82.00 113.00   1.00    1.00    --   43.54 126.00 -90.00   31
 14  \w     75.00 101.00   1.00    5.00    --  102.90  80.00  68.01   26
 15  \w     78.00 105.00   1.00    5.00    --  102.90  45.00 120.00   27
 16  \w     79.00 105.00   1.00    5.00    --  102.90  45.00  90.00   26
 17  \w     71.00  96.00   1.00    5.00    --  102.90  77.00 120.00   25
 18  \w     76.00 102.00   1.00    5.00    --  102.90  66.00 119.19   26
 19  \w     80.00 105.00   1.00    5.00    --  102.90  45.00 150.00   25
 20  \w     76.00 127.00   1.00    5.00    --  102.90  61.00 165.70   51
 21  \w     76.00 101.00   1.00    5.00    --  102.90  61.00  90.00   25
 22  \w     76.00 102.00   1.00    5.00    --  102.90  61.00 120.00   26
 23  \w     76.00 104.00   1.00    5.00    --  102.90  61.00 150.00   28
 24  \w     71.00  97.00   1.00    5.00    --  102.90  77.00 150.00   26
 25  \w     73.00  99.00   1.00    5.00    --  102.90  70.00 143.46   26
 26  \w     71.00  97.00   1.00    5.00    --  102.90  77.00  90.00   26
 27  \w     71.00  96.00   1.00    5.00    --  102.90  77.00  60.00   25
 28  \w     74.00  99.00   1.00    5.00    --  102.90  72.00 129.98   25
 29  \w     35.00  75.00   1.00    5.00    --  102.90 -45.00  30.00   40
 30  \w     31.00  66.00   1.00    5.00    --  102.90-126.00  90.00   35
 31  \w     10.00  96.00   1.00    1.00    --   43.54-126.00 -90.00   86
 32  \w     48.00 109.00   1.00    5.00    --  102.90 -95.00 -90.00   61
 33  \w     35.00 122.00   1.00    5.00    --  102.90-126.00-150.00   87
 34  \w    -77.00 -23.00   1.00    1.00    --  -43.54 -57.00 120.00   54
 35  \w   -112.00 -82.00   1.00    1.00    --  -43.54 -99.00  30.00   30
 36  \w   -113.00 -20.00   1.00    1.00    --  -43.54 -57.00  60.00   93
 37  \w   -107.00 -75.00   1.00    1.00    --  -43.54-126.00 150.00   32
;
_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      0.0921772000
_diffrn_orient_matrix_UB_12      0.0237925000
_diffrn_orient_matrix_UB_13      -0.0091921000
_diffrn_orient_matrix_UB_21      0.0463437000
_diffrn_orient_matrix_UB_22      -0.0449513000
_diffrn_orient_matrix_UB_23      0.0666180000
_diffrn_orient_matrix_UB_31      0.0010995000
_diffrn_orient_matrix_UB_32      -0.0969260000
_diffrn_orient_matrix_UB_33      -0.0331667000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43443
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.375
_diffrn_reflns_theta_min         2.960
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26499
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         8920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1010P)^2^+0.6337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6560
_reflns_number_total             8920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01395_si_003.cif
_cod_data_source_block           skn8_1
_cod_original_cell_volume        4504.10(14)
_cod_database_code               4035048
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1B(H1B), N1A(H1AA), N1(H1), C3B(H3B), C6B(H6B), C3(H3), C3A(H3A), C15B(H15B),
  C7B(H7B), C11B(H11B), C11A(H11A), C15(H15), C15A(H15A), C13B(H13B), C11(H11),
 C6(H6), C12B(H12B), C14B(H14B), C7(H7), C12A(H12A), C13(H13), C12(H12),
 C13A(H13A), C14(H14), C6A(H6A), C14A(H14A), C7A(H7A)
2.b Idealised Me refined as rotating group:
 C17(H17D,H17E,H17F), C17B(H17A,H17B,H17C), C17A(H17G,H17H,H17I), C1B(H1BA,
 H1BB,H1BC), C1(H1A,H1C,H1D), C1A(H1AB,H1AC,H1AD)
;
_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 3.695
_oxdiff_exptl_absorpt_empirical_full_min 0.317