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_7156713
_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            'C26 H22 Cl N'
_chemical_formula_weight         383.90
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_audit_update_record
;
2019-01-29 deposited with the CCDC.    2019-02-27 downloaded from the CCDC.
;
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_cell_angle_gamma                90.00
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_cell_length_c                   19.267(3)
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_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
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_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.980
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_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
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_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
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_diffrn_reflns_limit_l_max       22
_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         2.27
_exptl_absorpt_coefficient_mu    0.198
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(7)
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_refine_ls_number_reflns         3537
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_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0635P)^2^+0.2789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                3387
_reflns_number_total             3537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00232d2.cif
_cod_data_source_block           Compound9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_cell_volume        2044.2(5)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7156713