Palladium-Catalyzed, Enantioselective α-Arylation of α-Fluorooxindoles.
Jin, Yushu; Chen, Ming; Ge, Shaozhong; Hartwig, John F.; Organic letters 19 (2017) 1390–1393; doi:10.1021/acs.orglett.7b00294

data_1556019
_publ_section_title
;
 Palladium-Catalyzed, Enantioselective \a-Arylation of \a-Fluorooxindoles.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1390
_journal_page_last               1393
_journal_paper_doi               10.1021/acs.orglett.7b00294
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H11 F N2 O'
_chemical_formula_weight         266.27
_chemical_name_common            'compound 3b '
_chemical_name_systematic        'compound 3b '
_space_group.centring_type       primitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4334(7)
_cell_length_b                   9.1934(8)
_cell_length_c                   16.9142(15)
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      2.61
_cell_volume                     1311.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27191
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.484
_diffrn_reflns_theta_min         5.230
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 907 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0398P)^2^+0.5734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1045
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2263
_reflns_number_total             2391
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00294_si_002.cif
_cod_data_source_block           compound_3b
_cod_database_code               1556019
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              22814
_shelx_hkl_checksum              81034