Palladium(II)-Catalyzed Tandem Cyclization/C-H Functionalization of Alkynes for the Synthesis of Functionalized Indoles
Xiao-Feng Xia; Ning Wang; Lu-Lu Zhang; Xian-Rong Song; Xue-Yuan Liu; Yong-Min Liang; Journal of Organic Chemistry 77 (2012) 9163–9170; doi:10.1021/jo301741j

data_4027606
_publ_section_title
;
 Palladium(II)-Catalyzed Tandem Cyclization/C-H Functionalization of
 Alkynes for the Synthesis of Functionalized Indoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9163
_journal_page_last               9170
_journal_paper_doi               10.1021/jo301741j
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C29 H21 N'
_chemical_formula_weight         383.47
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.523(6)
_cell_angle_beta                 72.003(6)
_cell_angle_gamma                72.640(6)
_cell_formula_units_Z            2
_cell_length_a                   9.689(6)
_cell_length_b                   10.771(7)
_cell_length_c                   10.909(7)
_cell_measurement_reflns_used    1620
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.92
_cell_measurement_theta_min      2.58
_cell_volume                     1033.2(11)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6988
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0542P)^2^+0.0248P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                2351
_reflns_number_total             3768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301741j_si_002.cif
_cod_data_source_block           p-1
_cod_original_cell_volume        1033.3(11)
_cod_database_code               4027606