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_4127903
_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_formula_moiety         'C20 H18 O3'
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.34
_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                 90.079(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9855(13)
_cell_length_b                   7.8837(9)
_cell_length_c                   16.3210(18)
_cell_measurement_reflns_used    18510
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.669
_cell_measurement_theta_min      2.707
_cell_volume                     1542.2(3)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX v2014.11.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX v2014.11.0.'
_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 0.984
_diffrn_measured_fraction_theta_max 0.980
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10098
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.669
_diffrn_reflns_theta_min         2.707
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.561
_exptl_crystal_size_mid          0.488
_exptl_crystal_size_min          0.206
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(7)
_refine_ls_extinction_coef       0.0004(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5199
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0657P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                5194
_reflns_number_total             5199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08510_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C40 H36 O6'
_cod_original_formula_sum        'C40 H36 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     612.69
_cod_database_code               4127903
_shelx_estimated_absorpt_t_min   0.693
_shelx_estimated_absorpt_t_max   0.868
_shelxl_version_number           2014/6
_shelx_res_checksum              23536
_shelx_hkl_checksum              88036