Gold catalysed transformation of 2-arylindoles to terphenyl amines via 3-dienyl indoles and Brønsted acid promoted formation of 2-carboxyindoles to 3-indenylindoles via 3-allenylindoles.
Uruvakili, Anasuyamma; Kumara Swamy, K. C.; Organic & biomolecular chemistry 17 (2019) 3275–3284; doi:10.1039/c9ob00232d

data_7156716
_publ_section_title
;
 Gold catalysed transformation of 2-arylindoles to terphenyl amines via
 3-dienyl indoles and Br\/onsted acid promoted formation of
 2-carboxyindoles to 3-indenylindoles via 3-allenylindoles.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3275
_journal_page_last               3284
_journal_paper_doi               10.1039/c9ob00232d
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C33 H27 N O2'
_chemical_formula_weight         469.56
_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_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
_audit_update_record
;
2019-01-29 deposited with the CCDC.    2019-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                75.145(3)
_cell_angle_beta                 76.297(3)
_cell_angle_gamma                83.645(3)
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_cell_length_c                   16.9935(7)
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_cell_measurement_temperature    293(2)
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_cell_measurement_theta_min      2.2080
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_computing_cell_refinement       'CrysAlisPro 1.171.40.22a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.22a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.22a (Rigaku OD, 2018)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       9
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_diffrn_reflns_limit_k_max       11
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_exptl_crystal_density_method    'not measured'
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_exptl_crystal_size_max          0.24
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_exptl_crystal_size_min          0.18
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_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_parameters     329
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0573P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1425
_reflns_number_gt                2415
_reflns_number_total             4393
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00232d2.cif
_cod_data_source_block           Compound21
_cod_depositor_comments
'Adding full bibliography for 7156713--7156716.cif.'
_cod_database_code               7156716