Base-promoted direct synthesis of functionalized N-arylindoles via the cascade reactions of allenic ketones with indoles.
Li, Shengxiao; Wu, Xin-Xing; Chen, Shufeng; Organic & biomolecular chemistry 17 (2019) 789–793; doi:10.1039/c8ob02921k

data_7156630
_publ_section_title
;
 Base-promoted direct synthesis of functionalized N-arylindoles via the
 cascade reactions of allenic ketones with indoles.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              789
_journal_page_last               793
_journal_paper_doi               10.1039/c8ob02921k
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C28 H20 Br N O S0'
_chemical_formula_weight         466.36
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-11-01 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.243(16)
_cell_angle_gamma                90.00
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_cell_length_b                   7.2255(11)
_cell_length_c                   18.475(3)
_cell_measurement_reflns_used    1375
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.4680
_cell_measurement_theta_min      3.6900
_cell_volume                     2247.3(6)
_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  Eos
_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  0.0861
_diffrn_reflns_av_sigmaI/netI    0.1595
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
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_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.59
_exptl_absorpt_coefficient_mu    1.849
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36325
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1911
_refine_ls_R_factor_gt           0.0768
_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^)+(0.0751P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.2287
_reflns_number_gt                1663
_reflns_number_total             3945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob02921k2.cif
_cod_data_source_block           exp_4847
_cod_depositor_comments          'Adding full bibliography for 7156630.cif.'
_cod_original_cell_volume        2247.2(6)
_cod_database_code               7156630