Palladium-Catalyzed Decarboxylative ortho-Amidation of Indole-3-carboxylic Acids with Isothiocyanates Using Carboxyl as a Deciduous Directing Group.
Tulichala, R. N. Prasad; Shankar, Mallepalli; Swamy, K. C. Kumara; The Journal of organic chemistry 83 (2018) 4375–4383; doi:10.1021/acs.joc.8b00042

data_4034910
_publ_section_title
;
 Palladium-Catalyzed Decarboxylative ortho-Amidation of
 Indole-3-carboxylic Acids with Isothiocyanates Using Carboxyl as a
 Deciduous Directing Group.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4375
_journal_page_last               4383
_journal_paper_doi               10.1021/acs.joc.8b00042
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C17 H13 N3 O'
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_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
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_cell_angle_gamma                90
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_cell_length_b                   5.0990(3)
_cell_length_c                   16.9467(11)
_cell_measurement_reflns_used    2061
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.437
_cell_measurement_theta_min      0.970
_cell_volume                     1395.41(17)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
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_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         2.419
_diffrn_source                   'Bruker APEX-II CCD'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0853
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0733P)^2^+0.2255P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                2061
_reflns_number_total             3047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00042_si_002.cif
_cod_data_source_block           compound3ae
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034910
_shelx_shelxl_version_number     2014/7