Nickel-catalyzed Enantioselective Hydroarylation and Hydroalkenylation of Styrenes.
Chen, Yue-Gang; Shuai, Bin; Xu, Xue-Tao; Li, Yi-Qian; Yang, Qi-Liang; Qiu, Hui; Zhang, Kun; Fang, Ping; Mei, Tian-Sheng; Journal of the American Chemical Society 141 (2019) 3395–3399; doi:10.1021/jacs.8b13524

data_4127777
_publ_section_title
;
 Nickel-catalyzed Enantioselective Hydroarylation and Hydroalkenylation of
 Styrenes.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3395
_journal_page_last               3399
_journal_paper_doi               10.1021/jacs.8b13524
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H22 Cl N O'
_chemical_formula_weight         291.80
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.4416(3)
_cell_length_b                   10.2487(4)
_cell_length_c                   49.282(3)
_cell_measurement_reflns_used    3957
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.636
_cell_measurement_theta_min      5.735
_cell_volume                     3253.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.997
_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  0.0860
_diffrn_reflns_av_unetI/netI     0.1091
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14457
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.342
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details
; 
 Flack x determined using 1131 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.09(9)
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0811
_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^)+(0.1216P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1946
_refine_ls_wR_factor_ref         0.2244
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3638
_reflns_number_total             5685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13524_si_003.cif
_cod_data_source_block           mo_d8v19059_0m
_cod_database_code               4127777
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2013-4
_shelx_res_checksum              80296
_shelx_hkl_checksum              95725