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_4035049
_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         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33
_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             2016-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.136(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4322(3)
_cell_length_b                   21.4954(7)
_cell_length_c                   9.3861(2)
_cell_measurement_reflns_used    4858
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.9070
_cell_measurement_theta_min      4.1160
_cell_volume                     1691.52(9)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1600
_diffrn_detector_type            Titan
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.979
_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     20.00 109.00   1.00    1.54    --   43.54  38.00   0.00   89
  2  \w     76.00 154.00   1.00    6.17    --  102.90  61.00 -60.00   78
  3  \w     96.00 122.00   1.00    6.17    --  102.90  45.00  30.00   26
  4  \w     86.00 118.00   1.00    6.17    --  102.90  30.00  30.00   32
  5  \w     76.00 158.00   1.00    6.17    --  102.90  30.00  90.00   82
  6  \w     77.00 129.00   1.00    6.17    --  102.90  30.00 -90.00   52
  7  \w     80.00 143.00   1.00    6.17    --  102.90  30.00-150.00   63
  8  \w     49.00 112.00   1.00    6.17    --  102.90 -61.00  60.00   63
  9  \w     75.00 100.00   1.00    6.17    --  102.90 -95.00  60.00   25
 10  \w     36.00 127.00   1.00    6.17    --  102.90 -61.00 -30.00   91
 11  \w     92.00 118.00   1.00    6.17    --  102.90-126.00-150.00   26
 12  \w     38.00 133.00   1.00    6.17    --  102.90 -77.00-180.00   95
 13  \w     29.00  62.00   1.00    6.17    --  102.90-126.00-150.00   33
 14  \w    -14.00  68.00   1.00    1.54    --   43.54 -57.00-180.00   82
 15  \w     30.00 117.00   1.00    6.17    --  102.90-130.00  21.00   87
 16  \w    -61.00  26.00   1.00    1.54    --  -43.54  57.00  90.00   87
 17  \w    -67.00 -41.00   1.00    1.54    --  -43.54 130.00  93.00   26
 18  \w   -121.00 -83.00   1.00    1.54    --  -43.54 -99.00   0.00   38
;
_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      -0.1500299000
_diffrn_orient_matrix_UB_12      -0.0388015000
_diffrn_orient_matrix_UB_13      0.0187645000
_diffrn_orient_matrix_UB_21      0.0986240000
_diffrn_orient_matrix_UB_22      -0.0601952000
_diffrn_orient_matrix_UB_23      -0.0039848000
_diffrn_orient_matrix_UB_31      0.0394253000
_diffrn_orient_matrix_UB_32      0.0029762000
_diffrn_orient_matrix_UB_33      0.1638824000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12010
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.392
_diffrn_reflns_theta_min         4.113
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.207
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.782
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0822
_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^)+(0.1320P)^2^+0.3608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2153
_refine_ls_wR_factor_ref         0.2497
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2391
_reflns_number_total             3334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01395_si_004.cif
_cod_data_source_block           bhaskar1_1
_cod_database_code               4035049
_chemical_oxdiff_formula         'C19 H17 N O3'
_reflns_odcompleteness_completeness 99.94
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C9 \\sim C10 \\sim C11 \\sim C12 \\sim C14 \\sim C15: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C14(H14), C15(H15),
  C18(H18)
3.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-28
_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 2.184
_oxdiff_exptl_absorpt_empirical_full_min 0.206