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_4134713
_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         'C82 H106 Cl O14 P2 Pd2 [+ solvent]'
_chemical_formula_sum            'C82 H106 Cl O14 P2 Pd2'
_chemical_formula_weight         1625.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 113.055(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.794(2)
_cell_length_b                   19.1363(13)
_cell_length_c                   16.7518(11)
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      68.43
_cell_measurement_theta_min      2.82
_cell_volume                     8788.1(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      288(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_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  0.0626
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36547
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.444
_diffrn_reflns_theta_min         2.816
_exptl_absorpt_coefficient_mu    4.374
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             3396
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.1665
_exptl_transmission_factor_min   0.0574
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.123(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     929
_refine_ls_number_reflns         14467
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+10.1042P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1619
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                10672
_reflns_number_total             14467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02686_si_005.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 4134712--4134715.cif.'
_cod_original_cell_volume        8788.2(10)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4134713
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.475
_shelx_estimated_absorpt_t_max   0.560
_shelx_res_checksum              83074
_shelx_hkl_checksum              28522
_shelx_fab_checksum              7611