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_7130104
_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 H20 O2'
_chemical_formula_sum            'C20 H20 O2'
_chemical_formula_weight         292.36
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-01-18T22:01:41-00:00
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.82822(4)
_cell_length_b                   13.81370(9)
_cell_length_c                   18.94391(13)
_cell_measurement_reflns_used    16736
_cell_measurement_temperature    150.99(13)
_cell_measurement_theta_max      72.547
_cell_measurement_theta_min      3.923
_cell_volume                     1525.161(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.99(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_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    -69.00  41.00   1.00    1.00    --  -37.50  38.00-150.00  110
  2  \w   -124.00 -80.00   1.00    1.00    --  -37.50 -99.00 -60.00   44
  3  \w    -63.00   5.00   1.00    1.00    --  -37.50  38.00   0.00   68
  4  \w    -99.00  -9.00   1.00    1.00    --  -37.50 -38.00  30.00   90
  5  \w    -91.00 -39.00   1.00    1.00    --  -37.50 -38.00 -90.00   52
  6  \w   -116.00 -19.00   1.00    1.00    --  -37.50 -38.00-150.00   97
  7  \w     81.00 108.00   1.00    1.00    --   37.50 125.00  30.00   27
  8  \w     38.00  65.00   1.00    1.00    --   37.50  57.00 -30.00   27
  9  \w     45.00  77.00   1.00    1.00    --  110.55 -45.00-150.00   32
 10  \w     25.00  76.00   1.00    1.00    --  110.55-111.00 150.00   51
 11  \w     29.00  75.00   1.00    1.00    --  110.55 -45.00  90.00   46
 12  \w     36.00  64.00   1.00    1.00    --  110.55 -30.00 -30.00   28
 13  \w    123.00 157.00   1.00    1.00    --  110.55  61.00-120.00   34
 14  \w     82.00 108.00   1.00    1.00    --  110.55 -94.00 -30.00   26
 15  \w     64.00 149.00   1.00    1.00    --  110.55   0.00-150.00   85
 16  \w     71.00  98.00   1.00    1.00    --  110.55  77.00-120.00   27
 17  \w    115.00 149.00   1.00    1.00    --  110.55  61.00-150.00   34
 18  \w     38.00  63.00   1.00    1.00    --  110.55 -45.00  60.00   25
 19  \w     74.00 105.00   1.00    1.00    --  110.55  61.00-150.00   31
 20  \w     34.00  61.00   1.00    1.00    --  110.55 -30.00 -60.00   27
 21  \w     39.00  77.00   1.00    1.00    --  110.55 -45.00-120.00   38
 22  \w     76.00 101.00   1.00    1.00    --  110.55  61.00 -90.00   25
 23  \w     76.00 147.00   1.00    1.00    --  110.55  61.00  90.00   71
 24  \w    100.00 127.00   1.00    1.00    --  110.55  77.00 -90.00   27
 25  \w     40.00  67.00   1.00    1.00    --  110.55 -30.00-180.00   27
 26  \w     78.00 105.00   1.00    1.00    --  110.55  61.00-120.00   27
 27  \w     76.00 103.00   1.00    1.00    --  110.55  45.00 -90.00   27
 28  \w     74.00 153.00   1.00    1.00    --  110.55  61.00 -60.00   79
 29  \w     72.00  99.00   1.00    1.00    --  110.55  77.00 -90.00   27
 30  \w     29.00 148.00   1.00    1.00    --  110.55 -61.00 -60.00  119
 31  \w     28.00  55.00   1.00    1.00    --  110.55   0.00-150.00   27
 32  \w     66.00  93.00   1.00    1.00    --  110.55  30.00 -90.00   27
 33  \w     80.00 105.00   1.00    1.00    --  110.55  30.00 -60.00   25
 34  \w     67.00  92.00   1.00    1.00    --  110.55  30.00 -30.00   25
 35  \w    120.00 155.00   1.00    1.00    --  110.55  30.00 -30.00   35
 36  \w     72.00  99.00   1.00    1.00    --  110.55  36.00 -48.46   27
 37  \w    -94.00 -26.00   1.00    1.00    --  -37.50 125.00-180.00   68
 38  \w    -38.00  26.00   1.00    1.00    --   37.50 -77.00-150.00   64
 39  \w      5.00  99.00   1.00    1.00    --   37.50-125.00  60.00   94
 40  \w     45.00  77.00   1.00    1.00    --  110.55 -45.00 120.00   32
 41  \w     60.00 101.00   1.00    1.00    --  110.55 -94.00  60.00   41
 42  \w     63.00 110.00   1.00    1.00    --  110.55-111.00-180.00   47
 43  \w     53.00  80.00   1.00    1.00    --  110.55-111.00 -90.00   27
 44  \w     55.00 112.00   1.00    1.00    --  110.55-111.00 -30.00   57
 45  \w     51.00 109.00   1.00    1.00    --  110.55 -94.00-150.00   58
 46  \w   -129.00   2.00   1.00    1.00    --  -37.50 -77.00   0.00  131
 47  \w   -129.00   2.00   1.00    1.00    --  -37.50 -77.00-180.00  131
 48  \w   -100.00  -2.00   1.00    1.00    --  -37.50 125.00  30.00   98
 49  \w   -121.00 -73.00   1.00    1.00    --  -37.50-125.00 120.00   48
 50  \w     -2.00  99.00   1.00    1.00    --   37.50  77.00 150.00  101
 51  \w     73.00 121.00   1.00    1.00    --   37.50 125.00-180.00   48
 52  \w   -126.00 -79.00   1.00    1.00    --  -37.50 -99.00  90.00   47
 53  \w   -129.00   2.00   1.00    1.00    --  -37.50 -77.00 120.00  131
 54  \w   -129.00   2.00   1.00    1.00    --  -37.50 -77.00-120.00  131
 55  \w   -122.00   0.00   1.00    1.00    --  -37.50 -38.00   0.00  122
 56  \w    -77.00  54.00   1.00    1.00    --  -37.50  77.00 -30.00  131
 57  \w   -122.00  -1.00   1.00    1.00    --  -37.50 -56.00  22.00  121
 58  \w   -122.00   0.00   1.00    1.00    --  -37.50 -38.00 120.00  122
 59  \w   -122.00  -1.00   1.00    1.00    --  -37.50 -57.00   0.00  121
 60  \w   -126.00  46.00   1.00    1.00    --  -37.50 -19.00-150.00  172
 61  \w   -100.00  -2.00   1.00    1.00    --  -37.50 125.00-150.00   98
 62  \w    -71.00  47.00   1.00    1.00    --  -37.50  38.00 -60.00  118
 63  \w   -122.00  -1.00   1.00    1.00    --  -37.50 -57.00 120.00  121
 64  \w   -122.00   0.00   1.00    1.00    --  -37.50 -38.00-180.00  122
 65  \w   -126.00 -79.00   1.00    1.00    --  -37.50 -99.00  60.00   47
 66  \w     -2.00 129.00   1.00    1.00    --   37.50  77.00  30.00  131
 67  \w    -58.00 133.00   1.00    1.00    --   37.50   0.00-180.00  191
 68  \w      1.00 122.00   1.00    1.00    --   37.50  57.00  30.00  121
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319057
_diffrn_orient_matrix_UB_12      0.0457356
_diffrn_orient_matrix_UB_13      0.0735425
_diffrn_orient_matrix_UB_21      -0.0621706
_diffrn_orient_matrix_UB_22      0.1000019
_diffrn_orient_matrix_UB_23      -0.0305142
_diffrn_orient_matrix_UB_31      -0.2548195
_diffrn_orient_matrix_UB_32      -0.0186723
_diffrn_orient_matrix_UB_33      0.0166457
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27285
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.996
_diffrn_reflns_theta_min         3.961
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details
;
  Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The Friedel pair coverage of the experiment is almost complete 
 (100%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=-0.06(8)
;
_refine_ls_abs_structure_Flack   0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.2760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0957
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2695
_reflns_number_total             2818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01642g2.cif
_cod_data_source_block           a20210346_iiq
_cod_original_cell_volume        1525.159(19)
_cod_database_code               7130104