Palladium-catalyzed mono- and double-carbonylation of indoles with amines controllably leading to amides and alpha-ketoamides
Qi Xing; Lijun Shi; Rui Lang; Chungu Xia; Fuwei Li; Chem.Commun. 48 (2012) 11023–; doi:10.1039/c2cc36341k

data_7108547
_publ_section_title
;
 Palladium-catalyzed mono- and double-carbonylation of indoles with amines
 controllably leading to amides and alpha-ketoamides
;
_journal_name_full               Chem.Commun.
_journal_page_first              11023
_journal_paper_doi               10.1039/c2cc36341k
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C18 H22 N2 O'
_chemical_formula_weight         282.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.103(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.449(18)
_cell_length_b                   12.318(15)
_cell_length_c                   8.700(11)
_cell_measurement_reflns_used    1163
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.18
_cell_measurement_theta_min      2.86
_cell_volume                     1524(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7898
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0435P)^2^+0.5290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                1642
_reflns_number_total             2834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36341k.txt
_cod_data_source_block           p21c
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7108547