Controllable access to trifluoromethyl-containing indoles and indolines: Palladium-catalyzed regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides
Yang, Hefei; Wang, Le-Cheng; Zhang, Yu; Zheng, Dongling; Chen, Zhengkai; Wu, Xiao-Feng; Chemical Science  (2022) –; doi:10.1039/D2SC00546H

data_1566541
_publ_section_title
;
 Controllable access to trifluoromethyl-containing indoles and indolines:
 Palladium-catalyzed regioselective functionalization of unactivated
 alkenes with trifluoroacetimidoyl chlorides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00546H
_journal_year                    2022
_chemical_formula_sum            'C22 H15 F3 N3 O'
_chemical_formula_weight         394.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.651(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.6657(19)
_cell_length_b                   33.014(4)
_cell_length_c                   7.2436(9)
_cell_measurement_reflns_used    2132
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.83
_cell_measurement_theta_min      2.27
_cell_volume                     3703.7(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL(Sheldrick, 2015)'
_computing_publication_material  'WINGX (Farrugia,2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       '\f and \w 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  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0798
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            23881
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.911
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1678
_refine_ls_R_factor_gt           0.0789
_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^)+(0.1387P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2188
_refine_ls_wR_factor_ref         0.2743
_reflns_number_gt                3645
_reflns_number_total             7525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2sc00546h2.cif
_cod_data_source_block           1_a
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1566541