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_4135012
_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            'C12 H18 Br2 N2 Ni O2'
_chemical_formula_weight         440.81
_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   mixed
_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                   9.3332(14)
_cell_length_b                   12.1683(18)
_cell_length_c                   14.396(2)
_cell_measurement_reflns_used    2753
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.248
_cell_measurement_theta_min      4.383
_cell_volume                     1634.9(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9780
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_min         2.191
_exptl_absorpt_coefficient_mu    6.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
; 
 Flack x determined using 1016 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.021(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0252P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0643
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2704
_reflns_number_total             3207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b13117_si_004.cif
_cod_data_source_block           cd17437
_cod_depositor_comments
;Adding full bibliography for 4135012--4135016.cif.

 Adding full bibliography for 4135012--4135016.cif.
;
_cod_database_code               4135012
_shelx_estimated_absorpt_t_min   0.408
_shelx_estimated_absorpt_t_max   0.582
_shelxl_version_number           2013-4
_shelx_res_checksum              85672
_shelx_hkl_checksum              5411