Synthesis of oxindole from acetanilide via Ir(iii)-catalyzed C-H carbenoid functionalization.
Patel, Pitambar; Borah, Gongutri; Chemical communications (Cambridge, England) 53 (2016) 443–446; doi:10.1039/c6cc08788d

data_7119200
_publ_section_title
;
 Synthesis of oxindole from acetanilide via Ir(iii)-catalyzed C-H
 carbenoid functionalization.
;
_journal_issue                   2
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              443
_journal_page_last               446
_journal_paper_doi               10.1039/c6cc08788d
_journal_volume                  53
_journal_year                    2016
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18
_chemical_melting_point          399
_chemical_name_common            N-acetyoxyindole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-10-06 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.494(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4444(8)
_cell_length_b                   8.2789(9)
_cell_length_c                   13.8475(15)
_cell_measurement_reflns_used    6073
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.46
_cell_volume                     851.86(16)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21338
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.868
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9200
_exptl_absorpt_correction_T_min  0.8307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0453
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1300
_reflns_number_total             1505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc08788d2.cif
_cod_data_source_block           aa
_cod_database_code               7119200
_shelxl_version_number           2014-3
_shelx_res_checksum              23927