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_7156715
_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            'C32 H24 N2 O4'
_chemical_formula_weight         500.53
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
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_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_hydrogens   geom
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_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                69.647(5)
_cell_angle_beta                 87.597(5)
_cell_angle_gamma                63.669(5)
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_cell_length_b                   10.8487(11)
_cell_length_c                   13.8774(12)
_cell_measurement_reflns_used    3963
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      20.12
_cell_measurement_theta_min      2.25
_cell_volume                     1292.8(2)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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
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_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            43421
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.016(3)
_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_number_parameters     350
_refine_ls_number_reflns         4542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1440
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.185
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+0.0186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1618
_reflns_number_gt                2351
_reflns_number_total             4542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00232d2.cif
_cod_data_source_block           Compound25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156713--7156716.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7156715