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_4035051
_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_absolute_configuration unk
_chemical_formula_moiety         'C15 H12 O4'
_chemical_formula_sum            'C15 H12 O4'
_chemical_formula_weight         256.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.4632(10)
_cell_length_b                   6.3155(2)
_cell_length_c                   7.9800(3)
_cell_measurement_reflns_used    3025
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.8980
_cell_measurement_theta_min      3.6270
_cell_volume                     1232.89(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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 4.1600
_diffrn_detector_type            Titan
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.967
_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    -62.00  13.00   1.00    1.00    --  -43.29  38.00 -60.00   75
  2  \w     19.00  90.00   1.00    1.00    --   43.29  38.00 150.00   71
  3  \w     92.00 139.00   1.00    1.00    --  102.90  45.00  30.00   47
  4  \w     86.00 152.00   1.00    1.00    --  102.90  61.00 -90.00   66
  5  \w     75.00 101.00   1.00    1.00    --  102.90 -95.00-120.00   26
  6  \w     47.00 121.00   1.00    1.00    --  102.90-126.00   0.00   74
  7  \w     73.00  99.00   1.00    1.00    --  102.90 -95.00  90.00   26
  8  \w     20.00  46.00   1.00    1.00    --  102.90 -95.00-120.00   26
  9  \w     28.00 133.00   1.00    1.00    --  102.90 -15.00-180.00  105
;
_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      -0.0504262000
_diffrn_orient_matrix_UB_12      0.0298591000
_diffrn_orient_matrix_UB_13      -0.1132980000
_diffrn_orient_matrix_UB_21      0.0375948000
_diffrn_orient_matrix_UB_22      0.0617527000
_diffrn_orient_matrix_UB_23      -0.1470213000
_diffrn_orient_matrix_UB_31      0.0034608000
_diffrn_orient_matrix_UB_32      -0.2339595000
_diffrn_orient_matrix_UB_33      -0.0532716000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3926
_diffrn_reflns_point_group_measured_fraction_full 0.815
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.038
_diffrn_reflns_theta_min         3.614
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.381
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.702
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 495 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_coef       0.017(6)
_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   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1955
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0821P)^2^+0.6140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1714
_reflns_Friedel_coverage         0.518
_reflns_Friedel_fraction_full    0.615
_reflns_Friedel_fraction_max     0.584
_reflns_number_gt                1730
_reflns_number_total             1955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01395_si_002.cif
_cod_data_source_block           bhaskar2_1
_cod_original_cell_volume        1232.90(8)
_cod_database_code               4035051
_chemical_oxdiff_formula         'C15 H12 O4'
_reflns_odcompleteness_completeness 98.43
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2018-01-12
_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 4.372
_oxdiff_exptl_absorpt_empirical_full_min 0.346