Palladium-catalyzed intramolecular Heck dearomative <i>gem</i>-difluorovinylation of indoles.
Wang, Gang; Li, Wenqi; Liu, Tianxiang; Zhang, Yonghong; Wang, Bin; Xue, Fei; Jin, Weiwei; Ma, Caiyan; Xia, Yu; Liu, Chenjiang; Chemical science 13 (2022) 11594–11599; doi:10.1039/d2sc03169h

data_1567630
_publ_section_title
;
 Palladium-catalyzed intramolecular Heck dearomative
 <i>gem</i>-difluorovinylation of indoles.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              11594
_journal_page_last               11599
_journal_paper_doi               10.1039/d2sc03169h
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C22 H13 F2 N O'
_chemical_formula_sum            'C22 H13 F2 N O'
_chemical_formula_weight         345.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-04-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.784(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.1916(17)
_cell_length_b                   9.9649(5)
_cell_length_c                   14.5436(11)
_cell_measurement_reflns_used    3725
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      3.04
_cell_volume                     3232.4(4)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_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  0.0705
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28476
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.465
_diffrn_reflns_theta_min         2.238
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0789 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.4130.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0493P)^2^+1.6768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2614
_reflns_number_total             3311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03169h2.cif
_cod_data_source_block           mo_0428_1_0m
_cod_depositor_comments
'Adding full bibliography for 1567630--1567632.cif.'
_cod_database_code               1567630
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00D(H00D), C00E(H00E), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q)
;
_shelx_res_checksum              91846
_shelx_hkl_checksum              20992
_olex2_submission_special_instructions 'No special instructions were received'