Unexpected Oxidative Ring Opening of Electron-Rich 3-Aminobenzofurans into α-Ketoimines Derivatives.
Khelifi, Ilhem; Zhao, Guangkuan; Ghermani, Nour-Eddine; Provot, Olivier; Alami, Mouad; The Journal of organic chemistry 84 (2019) 1725–1733; doi:10.1021/acs.joc.8b01685

data_4035947
_publ_section_title
;
 Unexpected Oxidative Ring Opening of Electron-Rich 3-Aminobenzofurans
 into \a-Ketoimines Derivatives.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1725
_journal_page_last               1733
_journal_paper_doi               10.1021/acs.joc.8b01685
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C21 H17 N O3'
_chemical_formula_sum            'C21 H17 N O3'
_chemical_formula_weight         331.36
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.122(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6477(4)
_cell_length_b                   16.4230(6)
_cell_length_c                   11.6919(5)
_cell_measurement_reflns_used    10567
_cell_measurement_temperature    110.0(10)
_cell_measurement_theta_max      32.7390
_cell_measurement_theta_min      2.4820
_cell_volume                     1610.31(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4508
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.938
_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    -53.00  50.00   1.00   15.00    --   20.75 -57.00 150.00  103
  2  \w     -9.00  95.00   1.00   15.00    --   20.75  57.00  60.00  104
  3  \w    -13.00  99.00   1.00   15.00    --   20.75  77.00 120.00  112
  4  \w    -13.00  99.00   1.00   15.00    --   20.75  77.00-180.00  112
  5  \w    -58.00  54.00   1.00   15.00    --   20.75 -77.00 -90.00  112
  6  \w     -9.00  95.00   1.00   15.00    --   20.75  57.00 -60.00  104
  7  \w    -53.00  24.00   1.00   15.00    --   20.75 -57.00 -30.00   77
  8  \w    -53.00 -43.00   1.00   15.00    --   20.75 -57.00  60.00   10
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0236077000
_diffrn_orient_matrix_UB_12      -0.0411807000
_diffrn_orient_matrix_UB_13      0.0112383000
_diffrn_orient_matrix_UB_21      -0.0676399000
_diffrn_orient_matrix_UB_22      -0.0128281000
_diffrn_orient_matrix_UB_23      -0.0438466000
_diffrn_orient_matrix_UB_31      0.0449384000
_diffrn_orient_matrix_UB_32      0.0023093000
_diffrn_orient_matrix_UB_33      -0.0431789000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36597
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.034
_diffrn_reflns_theta_min         2.183
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         5715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0547P)^2^+0.5526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4500
_reflns_number_total             5715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01685_si_002.cif
_cod_data_source_block           ik49z
_cod_database_code               4035947
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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:
 C21(H21), C19(H19), C3(H3), C22(H22), C18(H18), C10(H10), C13(H13), C11(H11),
 C4(H4), C7(H7), C12(H12), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O15(H15)
;
_olex2_date_sample_data_collection 2017-07-07
_olex2_date_sample_submission    2017-07-03
_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.626