Reversal of Regioselectivity in Catalytic Arene-Ynamide Cyclization: Direct Synthesis of Valuable Azepino[4,5-b]indoles and β-Carbolines and DFT Calculations
Li, Long; Chen, Xiu-Mei; Wang, Ze-Shu; Zhou, Bo; Liu, Xin; Lu, Xin; Ye, Long-Wu; ACS Catalysis 7 (2017) 4004–; doi:10.1021/acscatal.7b01038

data_4516734
_publ_section_title
;
 Reversal of Regioselectivity in Catalytic Arene-Ynamide Cyclization:
 Direct Synthesis of Valuable Azepino[4,5-b]indoles and \b-Carbolines and
 DFT Calculations
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              4004
_journal_paper_doi               10.1021/acscatal.7b01038
_journal_volume                  7
_journal_year                    2017
_chemical_formula_sum            'C20 H20 N2 O2 S'
_chemical_formula_weight         352.44
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                91.22(3)
_cell_angle_beta                 96.68(3)
_cell_angle_gamma                91.44(3)
_cell_formula_units_Z            2
_cell_length_a                   5.3524(11)
_cell_length_b                   9.849(2)
_cell_length_c                   16.789(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      3.24
_cell_volume                     878.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6577
_diffrn_reflns_theta_full        24.50
_diffrn_reflns_theta_max         24.50
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.5492
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            clourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.571
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.453
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.453
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0844
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2318
_refine_ls_wR_factor_ref         0.3499
_reflns_number_gt                2086
_reflns_number_total             2914
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs7b01038_si_002.cif
_cod_data_source_block           lr
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4516734