Manganese catalyzed C-H functionalization of indoles with alkynes to synthesize bis/trisubstituted indolylalkenes and carbazoles: the acid is the key to control selectivity
Lijun Shi; Xiang Zhong; Houde She; Ziqiang Lei; Fuwei Li; Chem.Commun. 51 (2015) 7136–; doi:10.1039/C5cc00249D

data_7116990
_publ_section_title
;
 Manganese catalyzed C-H functionalization of indoles with alkynes to
 synthesize bis/trisubstituted indolylalkenes and carbazoles: the acid is
 the key to control selectivity
;
_journal_name_full               Chem.Commun.
_journal_page_first              7136
_journal_paper_doi               10.1039/C5cc00249D
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C28 H19 N3'
_chemical_formula_weight         397.46
_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
_audit_update_record
;
2015-01-07 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.639(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3114(18)
_cell_length_b                   12.9392(15)
_cell_length_c                   10.8302(12)
_cell_measurement_temperature    296(2)
_cell_volume                     2093.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_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 area detector'
_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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10347
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9815
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0412
_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^)+(0.1000P)^2^+0.0900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1428
_reflns_number_gt                2895
_reflns_number_total             3681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00249d2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7116990