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_4134715
_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 rmad
_chemical_formula_moiety         'C23 H20 O5'
_chemical_formula_sum            'C23 H20 O5'
_chemical_formula_weight         376.39
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4534(2)
_cell_length_b                   8.7745(2)
_cell_length_c                   26.1457(6)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      54.853
_cell_measurement_theta_min      4.785
_cell_volume                     1939.34(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      301.97
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18252
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.938
_diffrn_reflns_theta_min         4.783
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1656 before and 0.0789 after correction. The Ratio of minimum to maximum transmission is 0.7365. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1199 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.1793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3284
_reflns_number_total             3670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02686_si_002.cif
_cod_data_source_block           mjr18071_0m
_cod_depositor_comments
'Adding full bibliography for 4134712--4134715.cif.'
_cod_database_code               4134715
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C11(H11), C15(H15), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              53411
_shelx_hkl_checksum              34336
_olex2_submission_special_instructions 'No special instructions were received'