Highly Enantioselective Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters via Nickel-Catalyzed Friedel-Crafts Alkylation Reaction
Jian-Rong Gao; Hao Wu; Bin Xiang; Wu-Bin Yu; Liang Han; Yi-Xia Jia; Journal of the American Chemical Society 135 (2013) 2983–2986; doi:10.1021/ja400650m

data_4119397
_publ_section_title
;
 Highly Enantioselective Construction of Trifluoromethylated All-Carbon
 Quaternary Stereocenters via Nickel-Catalyzed Friedel-Crafts Alkylation
 Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2983
_journal_page_last               2986
_journal_paper_doi               10.1021/ja400650m
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C17 H12 Br F3 N2 O2'
_chemical_formula_weight         413.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.138(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.5992(7)
_cell_length_b                   14.6639(6)
_cell_length_c                   21.9076(9)
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    283(2)
_cell_measurement_theta_max      29.2771
_cell_measurement_theta_min      2.9238
_cell_volume                     3404.3(3)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      283(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17261
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    2.458
_exptl_absorpt_correction_T_max  0.6391
_exptl_absorpt_correction_T_min  0.5259
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     901
_refine_ls_number_reflns         10489
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+2.2903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1516
_reflns_number_gt                5650
_reflns_number_total             10489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja400650m_si_003.cif
_cod_data_source_block           3ae
_cod_database_code               4119397