Enantioselective transannular reactions by palladium-catalysed conjugate addition of aryl boronic acids
Prieto, Liher; Rodríguez, Verónica; Vicario, Jose L.; Reyes, Efraim; Hornillos, Valentín; Chemical Communications  (2022) –; doi:10.1039/D2CC01642G

data_7130105
_publ_section_title
;
 Enantioselective transannular reactions by palladium-catalysed conjugate
 addition of aryl boronic acids
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01642G
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H22 O2'
_chemical_formula_sum            'C20 H22 O2'
_chemical_formula_weight         294.38
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-01-14T12:24:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-01-28 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.096(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0597(2)
_cell_length_b                   9.4699(2)
_cell_length_c                   11.8919(3)
_cell_measurement_reflns_used    4725
_cell_measurement_temperature    150.3(3)
_cell_measurement_theta_max      72.71
_cell_measurement_theta_min      3.735
_cell_volume                     782.72(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.3(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -111.00 -20.00   1.00    1.00    --  -42.13 -38.00  90.00   91
  2  \w    -32.00  71.00   1.00    1.00    --   42.13 -77.00 -60.00  103
  3  \w     42.00  67.00   1.00    1.00    --   42.13-125.00-120.00   25
  4  \w     36.00  67.00   1.00    4.00    --  107.93 -45.00 150.00   31
  5  \w     39.00  68.00   1.00    4.00    --  107.93 -30.00  30.00   29
  6  \w     59.00 129.00   1.00    4.00    --  107.93 149.00 -72.00   70
  7  \w     48.00  77.00   1.00    4.00    --  107.93 -45.00 -90.00   29
  8  \w     40.00  69.00   1.00    4.00    --  107.93 -30.00-120.00   29
  9  \w     42.00  69.00   1.00    4.00    --  107.93 -30.00   0.00   27
 10  \w     33.00 139.00   1.00    4.00    --  107.93 -77.00 120.00  106
 11  \w     33.00  60.00   1.00    4.00    --  107.93 -30.00-150.00   27
 12  \w     88.00 151.00   1.00    4.00    --  107.93  45.00-120.00   63
 13  \w     82.00 135.00   1.00    4.00    --  107.93 125.00 -90.00   53
 14  \w   -114.00 -26.00   1.00    1.00    --  -42.13 -38.00-180.00   88
 15  \w      6.00  51.00   1.00    1.00    --   42.13-125.00  90.00   45
 16  \w     55.00  96.00   1.00    1.00    --   42.13-125.00-180.00   41
 17  \w     55.00 118.00   1.00    4.00    --  107.93-125.00 120.00   63
 18  \w    120.00 158.00   1.00    4.00    --  107.93  45.00 -90.00   38
 19  \w     36.00  65.00   1.00    4.00    --  107.93 -30.00  60.00   29
 20  \w     79.00 106.00   1.00    4.00    --  107.93-125.00-120.00   27
 21  \w     37.00  64.00   1.00    4.00    --  107.93 -45.00   0.00   27
 22  \w     45.00  77.00   1.00    4.00    --  107.93 -61.00-120.00   32
 23  \w     99.00 128.00   1.00    4.00    --  107.93 -61.00-120.00   29
 24  \w     77.00 116.00   1.00    4.00    --  107.93-125.00 -30.00   39
 25  \w     44.00  91.00   1.00    4.00    --  107.93-125.00  60.00   47
 26  \w    101.00 149.00   1.00    4.00    --  107.93  77.00-180.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0254735
_diffrn_orient_matrix_UB_12      -0.0273008
_diffrn_orient_matrix_UB_13      -0.1295002
_diffrn_orient_matrix_UB_21      0.1628236
_diffrn_orient_matrix_UB_22      -0.1103025
_diffrn_orient_matrix_UB_23      0.0208343
_diffrn_orient_matrix_UB_31      -0.1481092
_diffrn_orient_matrix_UB_32      -0.1164586
_diffrn_orient_matrix_UB_33      0.0106897
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8452
_diffrn_reflns_theta_full        68.97
_diffrn_reflns_theta_max         68.97
_diffrn_reflns_theta_min         3.78
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.66043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method 'Crystallization in organic solvent'
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.16
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     121
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.1947P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                2667
_reflns_number_total             2909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc01642g2.cif
_cod_data_source_block           a20210296_e487f1
_cod_database_code               7130105