Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers.
Qiu, Hui; Shuai, Bin; Wang, Yun-Zhao; Liu, Dong; Chen, Yue-Gang; Gao, Pei-Sen; Ma, Hong-Xing; Chen, Song; Mei, Tian-Sheng; Journal of the American Chemical Society 142 (2020) 9872–9878; doi:10.1021/jacs.9b13117

data_4135015
_publ_section_title
;
 Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl
 Atropisomers.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9872
_journal_page_last               9878
_journal_paper_doi               10.1021/jacs.9b13117
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H22 N2 O'
_chemical_formula_weight         318.40
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.72250(10)
_cell_length_b                   8.4948(2)
_cell_length_c                   29.8034(5)
_cell_measurement_reflns_used    6565
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      139.999
_cell_measurement_theta_min      8.901
_cell_volume                     1701.96(6)
_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 0.966
_diffrn_measured_fraction_theta_max 0.969
_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  0.0539
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            10185
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.483
_diffrn_reflns_theta_min         5.415
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
; 
 Flack x determined using 1102 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(17)
_refine_ls_extinction_coef       0.016(5)
_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   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0597
_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^)+(0.1247P)^2^+0.0905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1608
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                2796
_reflns_number_total             2954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b13117_si_005.cif
_cod_data_source_block           cu_d8v19859_0m
_cod_depositor_comments
;Adding full bibliography for 4135012--4135016.cif.

 Adding full bibliography for 4135012--4135016.cif.
;
_cod_database_code               4135015
_shelx_estimated_absorpt_t_min   0.900
_shelx_estimated_absorpt_t_max   0.942
_shelxl_version_number           2013-4
_shelx_res_checksum              9420
_shelx_hkl_checksum              57237