Oxidative Recyclization of 1H-Indoles for Synthesis of 2-Indolylbenzoxazinones via Cleavage of the C2-C3 Bond with AIBN under Air.
Liu, Xing-Xing; Luo, Xin-Liang; Wu, Zhao-Yang; Cui, Xin-Feng; Zhou, Xiao-Qiang; He, Yong-Qin; Huang, Guo-Sheng; The Journal of organic chemistry 82 (2017) 2107–2113; doi:10.1021/acs.joc.6b02893

data_4032174
_publ_section_title
;
 Oxidative Recyclization of 1H-Indoles for Synthesis of
 2-Indolylbenzoxazinones via Cleavage of the C2-C3 Bond with AIBN under
 Air.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2107
_journal_page_last               2113
_journal_paper_doi               10.1021/acs.joc.6b02893
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H10 N2 O2'
_chemical_formula_sum            'C16 H10 N2 O2'
_chemical_formula_weight         262.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.815(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.3587(13)
_cell_length_b                   5.2827(4)
_cell_length_c                   26.4239(15)
_cell_measurement_reflns_used    1095
_cell_measurement_temperature    176(6)
_cell_measurement_theta_max      28.3660
_cell_measurement_theta_min      3.9260
_cell_volume                     2417.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      176(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -40.00    8.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000  120.0000 40

  2 omega  -17.00   10.60   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -60.0000 23

  3 omega  -47.00   55.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000 -150.0000 85

  4 omega   61.00   95.80   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  178.0000  -60.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0304549000
_diffrn_orient_matrix_UB_12      0.0296458000
_diffrn_orient_matrix_UB_13      0.0156397000
_diffrn_orient_matrix_UB_21      0.0157428000
_diffrn_orient_matrix_UB_22      0.1226257000
_diffrn_orient_matrix_UB_23      0.0043036000
_diffrn_orient_matrix_UB_31      -0.0224091000
_diffrn_orient_matrix_UB_32      0.0459688000
_diffrn_orient_matrix_UB_33      -0.0214552000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            4141
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.76
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.6989P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                1596
_reflns_number_total             2386
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02893_si_002.cif
_cod_data_source_block           liuxx0316
_cod_depositor_comments          'Adding full bibliography for 4032174.cif.'
_cod_database_code               4032174
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16)
;
_olex2_date_sample_data_collection 2015-03-18
_olex2_submission_special_instructions 'No special instructions were received'