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_1566540
_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_moiety         'C21 H15 Cl F3 N3 O2'
_chemical_formula_sum            'C21 H15 Cl F3 N3 O2'
_chemical_formula_weight         433.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.523(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.287(5)
_cell_length_b                   15.859(5)
_cell_length_c                   17.629(6)
_cell_measurement_reflns_used    4497
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.10
_cell_measurement_theta_min      2.30
_cell_volume                     3888(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23729
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         1.806
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5022
_reflns_number_total             8818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00546h2.cif
_cod_data_source_block           cfk_0m
_cod_database_code               1566540
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.07) H3(0.074) H6(0.056) H7A(0.065) H7B(0.065) H8(0.07)
 H11A(0.071) H11B(0.071) H14(0.088) H15(0.103) H16(0.093) H19(0.089) H20(0.101)
 H21(0.092) H23(0.073) H24(0.075) H27(0.06) H30A(0.072) H30B(0.072) H31(0.055)
 H32A(0.07) H32B(0.07) H35(0.086) H36(0.103) H37(0.097) H40(0.107) H41(0.122)
 H42(0.107)
 Fixed X: H2(1.053539) H3(0.893286) H6(1.093717) H7A(0.764928) H7B(0.771072)
 H8(0.785596) H11A(0.72311) H11B(0.733585) H14(0.431275) H15(0.269529)
 H16(0.19283) H19(0.451151) H20(0.291407) H21(0.201971) H23(0.34176)
 H24(0.50345) H27(0.297895) H30A(0.632968) H30B(0.590323) H31(0.619133)
 H32A(0.663172) H32B(0.653735) H35(0.959014) H36(1.126577) H37(1.20662)
 H40(1.200574) H41(1.108286) H42(0.941618)
 Fixed Y: H2(0.490649) H3(0.508083) H6(0.360324) H7A(0.336155) H7B(0.411598)
 H8(0.507173) H11A(0.474721) H11B(0.378095) H14(0.429846) H15(0.392655)
 H16(0.341757) H19(0.328219) H20(0.288647) H21(0.29711) H23(0.212482)
 H24(0.230903) H27(0.121247) H30A(0.139384) H30B(0.230513) H31(0.256428)
 H32A(0.146046) H32B(0.081911) H35(0.180597) H36(0.178446) H37(0.129809)
 H40(0.064339) H41(0.017962) H42(0.017761)
 Fixed Z: H2(0.730626) H3(0.644019) H6(0.552628) H7A(0.413665) H7B(0.357775)
 H8(0.453887) H11A(0.548989) H11B(0.536648) H14(0.309746) H15(0.247851)
 H16(0.323703) H19(0.661708) H20(0.606341) H21(0.465732) H23(0.16817)
 H24(0.252584) H27(0.362625) H30A(0.540125) H30B(0.537032) H31(0.42727)
 H32A(0.356179) H32B(0.420025) H35(0.600746) H36(0.657173) H37(0.583128)
 H40(0.450272) H41(0.318059) H42(0.269213)
;
_shelx_res_checksum              70886
_shelx_hkl_checksum              84238
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'