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_4034911
_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            'C26 H21 N3 O2'
_chemical_formula_weight         407.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        '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                 99.023(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   17.005(3)
_cell_length_b                   15.917(2)
_cell_length_c                   30.298(5)
_cell_measurement_reflns_used    5987
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.356
_cell_measurement_theta_min      0.974
_cell_volume                     8099(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            38496
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3424
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     573
_refine_ls_number_reflns         7120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0759
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0735P)^2^+5.9936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1822
_reflns_number_gt                4851
_reflns_number_total             7120
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00042_si_002.cif
_cod_data_source_block           compd7
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C52 H42 N6 O4'
_cod_original_formula_weight         814.92
_cod_original_formula_units_Z            8
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4034911