Enantioselective Cross-Coupling for Axially Chiral Tetra-ortho-Substituted Biaryls and Asymmetric Synthesis of Gossypol.
Yang, He; Sun, Jiawei; Gu, Wei; Tang, Wenjun; Journal of the American Chemical Society 142 (2020) 8036–8043; doi:10.1021/jacs.0c02686

data_4134712
_publ_section_title
;
 Enantioselective Cross-Coupling for Axially Chiral
 Tetra-ortho-Substituted Biaryls and Asymmetric Synthesis of Gossypol.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8036
_journal_page_last               8043
_journal_paper_doi               10.1021/jacs.0c02686
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H17 F O4'
_chemical_formula_sum            'C20 H17 F O4'
_chemical_formula_weight         340.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 107.15(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9632(19)
_cell_length_b                   8.3819(19)
_cell_length_c                   12.045(4)
_cell_measurement_reflns_used    5885
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.85
_cell_volume                     864.7(4)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8222
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.426
_diffrn_reflns_theta_min         3.841
_exptl_absorpt_coefficient_mu    0.815
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2994
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0730P)^2^+0.1676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.903
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                2706
_reflns_number_total             2994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02686_si_003.cif
_cod_data_source_block           t_a
_cod_depositor_comments
'Adding full bibliography for 4134712--4134715.cif.'
_cod_original_cell_volume        864.6(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4134712
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.854
_shelx_estimated_absorpt_t_max   0.881
_shelx_res_checksum              49484
_shelx_hkl_checksum              89960