Palladium-Catalyzed Asymmetric α-Arylation of Alkylnitriles.
Jiao, Zhiwei; Chee, Kwok Wei; Zhou, Jianrong Steve; Journal of the American Chemical Society 138 (2016) 16240–16243; doi:10.1021/jacs.6b11610

data_4131209
_publ_section_title
;
 Palladium-Catalyzed Asymmetric \a-Arylation of Alkylnitriles.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16240
_journal_page_last               16243
_journal_paper_doi               10.1021/jacs.6b11610
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 N'
_chemical_formula_sum            'C21 H20 N'
_chemical_formula_weight         286.38
_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
_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                   6.8167(3)
_cell_length_b                   14.7936(6)
_cell_length_c                   15.5874(6)
_cell_measurement_reflns_used    3529
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.008
_cell_measurement_theta_min      4.120
_cell_volume                     1571.89(11)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2016.6.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.6.0'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution
'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19472
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.008
_diffrn_reflns_theta_min         4.120
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       rod
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.866
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.153
_refine_ls_abs_structure_details
;
 Flack x determined using 1409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0949P)^2^+0.1178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3358
_reflns_number_total             3390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b11610_si_003.cif
_cod_data_source_block           g525
_cod_database_code               4131209
_shelx_estimated_absorpt_t_min   0.658
_shelx_estimated_absorpt_t_max   0.920
_shelx_res_checksum              81118
_shelx_hkl_checksum              90941