Enantioselective Pd-Catalyzed Dearomative Reductive Heck and Domino Heck-Suzuki Reactions of 2-CF3-Indoles
Liang, Ren-Xiao; Chen, Jian-Fei; Huang, Ying-Ying; Yu, Ya-Ping; Zhang, Han-Yue; Song, Yu-Feng; Tsui, Gavin Chit; Jia, Yi-Xia; Chemical Communications  (2022) –; doi:10.1039/D2CC01435A

data_7130038
_publ_section_title
;
 Enantioselective Pd-Catalyzed Dearomative Reductive Heck and Domino
 Heck-Suzuki Reactions of 2-CF3-Indoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01435A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H9 F6 N O'
_chemical_formula_sum            'C17 H9 F6 N O'
_chemical_formula_weight         357.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-08 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.532(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5776(5)
_cell_length_b                   6.1725(3)
_cell_length_c                   12.0797(6)
_cell_measurement_reflns_used    9802
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.13
_cell_measurement_theta_min      3.84
_cell_volume                     752.05(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11014
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.124
_diffrn_reflns_theta_min         3.837
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.329
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1828 before and 0.0991 after correction.
The Ratio of minimum to maximum transmission is 0.7820.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0350P)^2^+0.1522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2694
_reflns_number_total             2740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01435a2.cif
_cod_data_source_block           cu_210317_cjf_1_4_cf3_0m
_cod_database_code               7130038
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.691
_shelx_estimated_absorpt_t_min   0.625
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C14(H14), C15(H15)
;
_shelx_res_checksum              19955
_shelx_hkl_checksum              80799
_olex2_submission_special_instructions 'No special instructions were received'