Facile synthesis of 2-arylmethylindoles and 2-vinylic indoles through palladium-catalyzed heteroannulations of 2-(2-propynyl)aniline and 2-(2-propynyl)tosylanilide.
Das, Bimolendu; Kundu, Priyanka; Chowdhury, Chinmay; Organic & biomolecular chemistry 12 (2014) 741–748; doi:10.1039/c3ob41961d

data_7153603
_publ_section_title
;
 Facile synthesis of 2-arylmethylindoles and 2-vinylic indoles through
 palladium-catalyzed heteroannulations of 2-(2-propynyl)aniline and
 2-(2-propynyl)tosylanilide.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              741
_journal_page_last               748
_journal_paper_doi               10.1039/c3ob41961d
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C16 H12 F3 N'
_chemical_formula_sum            'C16 H12 F3 N'
_chemical_formula_weight         275.27
_chemical_melting_point          72
_chemical_name_common            Indoles
_space_group_IT_number           2
_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
_cell_angle_alpha                93.549(9)
_cell_angle_beta                 109.310(9)
_cell_angle_gamma                95.346(10)
_cell_formula_units_Z            4
_cell_length_a                   9.5871(16)
_cell_length_b                   10.4916(18)
_cell_length_c                   14.112(2)
_cell_measurement_reflns_used    7425
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.6443
_cell_measurement_theta_min      2.2680
_cell_volume                     1327.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20553
_diffrn_reflns_theta_full        23.72
_diffrn_reflns_theta_max         23.72
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Reddish
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         3977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0579
_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^)+(0.1000P)^2^+0.3718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1944
_reflns_number_gt                3089
_reflns_number_total             3977
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41961d.txt
_cod_data_source_block           cc_bd_pk132_mar13_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Multi-Scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/current/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153603