Axially Chiral Biaryl Monophosphine Oxides Enabled by Palladium/WJ-Phos-Catalyzed Asymmetric Suzuki–Miyaura Cross-coupling
Ji, Wangqin; Wu, Hai-Hong; Zhang, Junliang; ACS Catalysis 10 (2020) 1548–1554; doi:10.1021/acscatal.9b04354

data_4517366
_publ_section_title
;
 Axially Chiral Biaryl Monophosphine Oxides Enabled by
 Palladium/WJ-Phos-Catalyzed Asymmetric Suzuki--Miyaura Cross-coupling
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1548
_journal_page_last               1554
_journal_paper_doi               10.1021/acscatal.9b04354
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C32 H23 O P'
_chemical_formula_sum            'C32 H23 O P'
_chemical_formula_weight         454.47
_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
_audit_creation_date             2018-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.7220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.50520(10)
_cell_length_b                   11.44810(10)
_cell_length_c                   11.03120(10)
_cell_measurement_reflns_used    22190
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1330
_cell_measurement_theta_min      3.9290
_cell_volume                     1197.84(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -52.00  21.00   1.00    1.00    --    0.00   8.00 -30.00   73
  2  \w    152.00 179.00   1.00    1.00    --   95.80   8.00 -30.00   27
  3  \w     92.00 125.00   1.00    1.00    --   95.80   8.00 -30.00   33
  4  \w     43.00  80.00   1.00    1.00    --   95.80  -8.00 154.00   37
  5  \w    -30.00  41.00   1.00    1.00    --    0.00  82.00-180.00   71
  6  \w    -85.00 -19.00   1.00    1.00    --    0.00  -8.00 154.00   66
  7  \w    -19.00  39.00   1.00    1.00    --    0.00  38.00 -30.00   58
  8  \w     43.00  77.00   1.00    1.00    --    0.00  57.00  60.00   34
  9  \w    -48.00  18.00   1.00    1.00    --    0.00 -38.00  60.00   66
 10  \w    -81.00 -55.00   1.00    1.00    --    0.00 -38.00  60.00   26
 11  \w     47.00  73.00   1.00    1.00    --    0.00  82.00-180.00   26
 12  \w     -5.00  40.00   1.00    1.00    --    0.00  57.00  90.00   45
 13  \w    -23.00  49.00   1.00    1.00    --    0.00  19.00 120.00   72
 14  \w    -44.00  10.00   1.00    1.00    --    0.00 -57.00  90.00   54
 15  \w    -16.00  19.00   1.00    1.00    --    0.00 -38.00   0.00   35
 16  \w    -43.00  17.00   1.00    1.00    --    0.00 -38.00-150.00   60
 17  \w     45.00  86.00   1.00    1.00    --    0.00  38.00 -30.00   41
 18  \w     45.00  70.00   1.00    1.00    --    0.00  57.00  90.00   25
 19  \w     -4.00  34.00   1.00    1.00    --    0.00  57.00  60.00   38
 20  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 21  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  30.00   25
 22  \w     75.00 185.00   1.00    1.00    --   95.80  45.00-150.00  110
 23  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 24  \w     67.00  99.00   1.00    1.00    --   95.80  73.00  51.52   32
 25  \w    137.00 163.00   1.00    1.00    --   95.80  77.00  71.72   26
 26  \w     86.00 112.00   1.00    1.00    --   95.80 -82.00  30.00   26
 27  \w      6.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00  122
 28  \w    102.00 128.00   1.00    1.00    --   95.80  73.00  51.52   26
 29  \w     74.00 100.00   1.00    1.00    --   95.80  61.00-150.00   26
 30  \w      8.00  33.00   1.00    1.00    --   95.80 -82.00  90.00   25
 31  \w     36.00 119.00   1.00    1.00    --   95.80 -82.00  90.00   83
 32  \w     67.00  93.00   1.00    1.00    --   95.80  78.00-103.56   26
 33  \w     97.00 185.00   1.00    1.00    --   95.80  78.00-103.56   88
 34  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 35  \w     71.00  96.00   1.00    1.00    --   95.80  61.00-120.00   25
 36  \w     71.00 114.00   1.00    1.00    --   95.80  61.00 120.00   43
 37  \w    136.00 173.00   1.00    1.00    --   95.80  54.00 143.36   37
 38  \w    102.00 128.00   1.00    1.00    --   95.80  82.00 -30.00   26
 39  \w     65.00 123.00   1.00    1.00    --   95.80  77.00   0.00   58
 40  \w     65.00 115.00   1.00    1.00    --   95.80  77.00  71.72   50
 41  \w     69.00  95.00   1.00    1.00    --   95.80  66.00 -48.38   26
 42  \w     70.00  96.00   1.00    1.00    --   95.80  65.00-111.64   26
 43  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 44  \w     73.00 105.00   1.00    1.00    --   95.80  54.00 143.36   32
 45  \w     63.00  97.00   1.00    1.00    --   95.80  82.00 -30.00   34
 46  \w     65.00 102.00   1.00    1.00    --   95.80  77.00  60.00   37
 47  \w    119.00 182.00   1.00    1.00    --   95.80  77.00 -35.07   63
 48  \w    145.00 171.00   1.00    1.00    --   95.80  61.00-120.00   26
 49  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 50  \w    120.00 183.00   1.00    1.00    --   95.80  77.00  30.00   63
 51  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -35.07   25
 52  \w    140.00 169.00   1.00    1.00    --   95.80  67.00 158.89   29
 53  \w    115.00 182.00   1.00    1.00    --   95.80  82.00 -60.00   67
 54  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 55  \w     15.00  41.00   1.00    1.00    --   95.80 -82.00 -30.00   26
 56  \w     69.00 104.00   1.00    1.00    --   95.80  67.00 158.89   35
 57  \w     71.00 133.00   1.00    1.00    --   95.80  61.00 -60.00   62
 58  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 59  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 60  \w     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 61  \w    121.00 185.00   1.00    1.00    --   95.80  82.00   0.00   64
 62  \w     78.00 107.00   1.00    1.00    --   95.80  38.00  -4.58   29
 63  \w    153.00 179.00   1.00    1.00    --   95.80  38.00  -4.58   26
 64  \w     79.00 105.00   1.00    1.00    --   95.80  45.00  60.00   26
 65  \w     71.00 103.00   1.00    1.00    --   95.80  61.00 -90.00   32
 66  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 67  \w     79.00 182.00   1.00    1.00    --   95.80  30.00 120.00  103
 68  \w     66.00 128.00   1.00    1.00    --   95.80 -82.00 150.00   62
 69  \w     17.00  43.00   1.00    1.00    --   95.80 -82.00 150.00   26
 70  \w    141.00 166.00   1.00    1.00    --   95.80  82.00-180.00   25
 71  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 72  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 73  \w     45.00 102.00   1.00    1.00    --   95.80 -82.00 -30.00   57
 74  \w     81.00 181.00   1.00    1.00    --   95.80  30.00-180.00  100
 75  \w     42.00 128.00   1.00    1.00    --   95.80 -82.00-150.00   86
 76  \w     49.00  77.00   1.00    1.00    --   95.80 -82.00  30.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0505196000
_diffrn_orient_matrix_UB_12      0.0065046000
_diffrn_orient_matrix_UB_13      0.1296964000
_diffrn_orient_matrix_UB_21      0.1538323000
_diffrn_orient_matrix_UB_22      0.0129018000
_diffrn_orient_matrix_UB_23      0.0513083000
_diffrn_orient_matrix_UB_31      -0.0124211000
_diffrn_orient_matrix_UB_32      0.1338342000
_diffrn_orient_matrix_UB_33      -0.0112793000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26960
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.047
_diffrn_reflns_theta_max         67.047
_diffrn_reflns_theta_min         4.016
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1718 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(12)
_refine_ls_extinction_coef       0.0131(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0748P)^2^+0.0019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.891
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                3994
_reflns_number_total             4056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04354_si_002.cif
_cod_data_source_block           exp_586
_cod_depositor_comments
'Adding full bibliography for 4517365--4517367.cif.'
_cod_database_code               4517366
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.662
_shelx_estimated_absorpt_t_min   0.601
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24),
  C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31)
;
_shelx_res_checksum              42822
_shelx_hkl_checksum              36351
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.471
_oxdiff_exptl_absorpt_empirical_full_min 0.436