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_4127902
_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_sum            'C28 H26 O3'
_chemical_formula_weight         410.49
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.2020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9247(4)
_cell_length_b                   10.0883(5)
_cell_length_c                   13.7799(7)
_cell_measurement_reflns_used    9289
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.10
_cell_measurement_theta_min      3.25
_cell_volume                     1087.48(9)
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            71472
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.152
_diffrn_reflns_theta_min         3.249
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.7106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 1919 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_coef       0.0123(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4127
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.2017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0669
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4117
_reflns_number_total             4127
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08510_si_004.cif
_cod_data_source_block           I159
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4127902
_shelx_shelxl_version_number     2014/7
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_shelx_res_checksum              57978
_shelx_hkl_checksum              42850