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_4127776
_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            'C21 H20 O'
_chemical_formula_weight         288.37
_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            4
_cell_length_a                   5.67890(10)
_cell_length_b                   14.8057(3)
_cell_length_c                   19.0477(4)
_cell_measurement_reflns_used    4088
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.294
_cell_measurement_theta_min      11.046
_cell_volume                     1601.53(5)
_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 0.962
_diffrn_measured_fraction_theta_max 0.980
_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  0.1163
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8508
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.494
_diffrn_reflns_theta_min         4.643
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 896 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.043(10)
_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   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0587
_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^)+(0.1053P)^2^+0.0756P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2442
_reflns_number_total             2765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13524_si_004.cif
_cod_data_source_block           cu_d8v19065_0m
_cod_database_code               4127776
_shelx_estimated_absorpt_t_min   0.898
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2013-4
_shelx_res_checksum              98400
_shelx_hkl_checksum              1966