Deoxygenative Insertion of Carbonyl Carbon into a C(sp<sup>3</sup>)-H Bond: Synthesis of Indolines and Indoles.
Asako, Sobi; Ishihara, Seina; Hirata, Keiya; Takai, Kazuhiko; Journal of the American Chemical Society 141 (2019) 9832–9836; doi:10.1021/jacs.9b05428

data_4128288
_publ_section_title
;
 Deoxygenative Insertion of Carbonyl Carbon into a C(sp<sup>3</sup>)-H
 Bond: Synthesis of Indolines and Indoles.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9832
_journal_page_last               9836
_journal_paper_doi               10.1021/jacs.9b05428
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C19 H21 N'
_chemical_formula_sum            'C19 H21 N'
_chemical_formula_weight         263.38
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.389(16)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   12.887(14)
_cell_length_b                   6.012(6)
_cell_length_c                   18.99(2)
_cell_measurement_reflns_used    4281
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.20
_cell_measurement_theta_min      2.80
_cell_volume                     1467(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1157
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22405
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.171
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568.00
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.396
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.1274
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0266P)^2^+1.8348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1963
_refine_ls_wR_factor_ref         0.2026
_reflns_number_gt                3039
_reflns_number_total             3363
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja9b05428_si_001.cif
_cod_data_source_block           8705-Hirata
_cod_database_code               4128288