Palladium-Catalyzed Triple Successive C-H Functionalization: Direct Synthesis of Functionalized Carbazoles from Indoles.
Verma, Akhilesh K.; Danodia, Abhinandan K.; Saunthwal, Rakesh K.; Patel, Monika; Choudhary, Deepak; Organic letters 17 (2015) 3658–3661; doi:10.1021/acs.orglett.5b01476

data_1523614
_publ_section_title
;
 Palladium-Catalyzed Triple Successive C-H Functionalization: Direct
 Synthesis of Functionalized Carbazoles from Indoles.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3658
_journal_page_last               3661
_journal_paper_doi               10.1021/acs.orglett.5b01476
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C16 H13 N O4'
_chemical_formula_sum            'C16 H13 N O4'
_chemical_formula_weight         283.27
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 131.954(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.4884(13)
_cell_length_b                   7.9625(4)
_cell_length_c                   18.5286(11)
_cell_measurement_reflns_used    2185
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.4
_cell_volume                     2686.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16701
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0458P)^2^+1.6211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                2185
_reflns_number_total             2357
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01476_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 1523614.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1523614