One-Pot Trifluoromethylative Functionalization of Amides: Synthesis of Trifluoromethylated Bis(indolyl)arylmethanes and Triarylmethanes.
Pandey, Vinay Kumar; Anbarasan, Pazhamalai; The Journal of organic chemistry 82 (2017) 12328–12336; doi:10.1021/acs.joc.7b02161

data_4033183
_publ_section_title
;
 One-Pot Trifluoromethylative Functionalization of Amides: Synthesis of
 Trifluoromethylated Bis(indolyl)arylmethanes and Triarylmethanes.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12328
_journal_page_last               12336
_journal_paper_doi               10.1021/acs.joc.7b02161
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C28  H25  F3  N2  O2'
_chemical_formula_sum            'C28 H25 F3 N2 O2'
_chemical_formula_weight         478.5
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_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2016-10-07T15:34:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                81.8483(13)
_cell_angle_beta                 72.4104(12)
_cell_angle_gamma                71.5178(11)
_cell_formula_units_Z            2
_cell_length_a                   10.0940(3)
_cell_length_b                   10.1679(3)
_cell_length_c                   12.6813(3)
_cell_measurement_reflns_used    5359
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.37
_cell_measurement_theta_min      2.21
_cell_measurement_wavelength     0.71073
_cell_volume                     1175.17(6)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16842
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.687
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0971P)^2^+0.6461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1846
_reflns_Friedel_coverage         0
_reflns_number_gt                3095
_reflns_number_total             4127
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02161_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 4033183.cif.'
_cod_database_code               4033183
_shelx_estimated_absorpt_t_min   0.97
_shelx_estimated_absorpt_t_max   0.975