Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade.
Lu, Shenci; Ong, Jun-Yang; Yang, Hui; Poh, Si Bei; Liew, Xi; Seow, Chwee San Deborah; Wong, Ming Wah; Zhao, Yu; Journal of the American Chemical Society 141 (2019) 17062–17067; doi:10.1021/jacs.9b08510

data_4127904
_publ_section_title
;
 Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an
 Eight-Membered Lactone through an Organocatalytic Cascade.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17062
_journal_page_last               17067
_journal_paper_doi               10.1021/jacs.9b08510
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H25 N O4 S'
_chemical_formula_sum            'C27 H25 N O4 S'
_chemical_formula_weight         459.54
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 93.3480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1622(4)
_cell_length_b                   7.4452(3)
_cell_length_c                   18.6526(8)
_cell_measurement_reflns_used    1429
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.369
_cell_measurement_theta_min      2.373
_cell_volume                     1131.57(9)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2015.5.2'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2015.5.2'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23933
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.369
_diffrn_reflns_theta_min         2.373
_exptl_absorpt_coefficient_mu    1.556
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       rod
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.554
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.082(5)
_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     300
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0286P)^2^+0.2771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0641
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                4324
_reflns_number_total             4390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08510_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4127904
_shelx_estimated_absorpt_t_min   0.479
_shelx_estimated_absorpt_t_max   0.917
_shelxl_version_number           2014/6
_shelx_res_checksum              39117
_shelx_hkl_checksum              77064