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_4517365
_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_absolute_configuration ad
_chemical_formula_moiety         'C37 H36 Fe N O P S'
_chemical_formula_sum            'C37 H36 Fe N O P S'
_chemical_formula_weight         629.55
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.5860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.99970(10)
_cell_length_b                   10.51620(10)
_cell_length_c                   14.12450(10)
_cell_measurement_reflns_used    27141
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      74.2910
_cell_measurement_theta_min      4.1660
_cell_volume                     1565.87(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_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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     54.00  84.00   1.00    1.00    --    0.00  57.00  30.00   30
  2  \w    -87.00 -36.00   1.00    1.00    --    0.00 -57.00  30.00   51
  3  \w    -88.00 -63.00   1.00    1.00    --    0.00 -38.00-150.00   25
  4  \w    -18.00  33.00   1.00    1.00    --    0.00  38.00 120.00   51
  5  \w    -24.00  22.00   1.00    1.00    --    0.00 -57.00  30.00   46
  6  \w    -27.00  22.00   1.00    1.00    --    0.00  77.00-150.00   49
  7  \w    -19.00  85.00   1.00    1.00    --    0.00  38.00 -90.00  104
  8  \w    -36.00 -10.00   1.00    1.00    --    0.00 -38.00-150.00   26
  9  \w    -20.00  13.00   1.00    1.00    --    0.00  57.00   0.00   33
 10  \w     53.00  89.00   1.00    1.00    --    0.00  38.00  90.00   36
 11  \w    -24.00  66.00   1.00    1.00    --    0.00  19.00-150.00   90
 12  \w     49.00  87.00   1.00    1.00    --    0.00  38.00 120.00   38
 13  \w     36.00  62.00   1.00    1.00    --    0.00  77.00-150.00   26
 14  \w     28.00  70.00   1.00    1.00    --    0.00  57.00   0.00   42
 15  \w    -20.00  34.00   1.00    1.00    --    0.00  57.00  30.00   54
 16  \w    -18.00   8.00   1.00    1.00    --    0.00  38.00  90.00   26
 17  \w     42.00  70.00   1.00    1.00    --   95.80 -82.00 -30.00   28
 18  \w     69.00 177.00   1.00    1.00    --   95.80  65.00  -3.29  108
 19  \w    136.00 163.00   1.00    1.00    --   95.80  74.00  53.32   27
 20  \w    135.00 183.00   1.00    1.00    --   95.80  79.00 163.51   48
 21  \w     75.00 184.00   1.00    1.00    --   95.80  61.00 150.00  109
 22  \w     64.00  90.00   1.00    1.00    --   95.80  79.00 163.51   26
 23  \w     66.00  91.00   1.00    1.00    --   95.80  74.00  53.32   25
 24  \w     63.00  92.00   1.00    1.00    --   95.80  82.00  60.00   29
 25  \w    150.00 176.00   1.00    1.00    --   95.80  82.00  60.00   26
 26  \w     25.00 128.00   1.00    1.00    --   95.80 -82.00 150.00  103
 27  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 28  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 29  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 30  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 31  \w    128.00 177.00   1.00    1.00    --   95.80  66.00 -18.11   49
 32  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 33  \w     65.00 114.00   1.00    1.00    --   95.80  77.00-120.00   49
 34  \w     66.00 140.00   1.00    1.00    --   95.80  74.00 116.86   74
 35  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 36  \w     71.00 183.00   1.00    1.00    --   95.80  61.00-120.00  112
 37  \w     67.00 110.00   1.00    1.00    --   95.80  72.00 -96.61   43
 38  \w    137.00 167.00   1.00    1.00    --   95.80  73.00  24.41   30
 39  \w     63.00 101.00   1.00    1.00    --   95.80  82.00-180.00   38
 40  \w     71.00 143.00   1.00    1.00    --   95.80  61.00  30.00   72
 41  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 42  \w     70.00  96.00   1.00    1.00    --   95.80  63.00 -48.41   26
 43  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 44  \w     69.00 126.00   1.00    1.00    --   95.80 -82.00   0.00   57
 45  \w     71.00  96.00   1.00    1.00    --   95.80  61.00-180.00   25
 46  \w     71.00 161.00   1.00    1.00    --   95.80  61.00  60.00   90
 47  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 48  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 173.46   25
 49  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 50  \w     64.00  90.00   1.00    1.00    --   95.80  82.00-120.00   26
 51  \w     75.00 183.00   1.00    1.00    --   95.80  45.00-180.00  108
 52  \w     76.00 101.00   1.00    1.00    --   95.80  45.00-120.00   25
 53  \w     75.00 184.00   1.00    1.00    --   95.80  45.00 120.00  109
 54  \w     72.00  98.00   1.00    1.00    --   95.80  61.00 -30.00   26
 55  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 56  \w     76.00 111.00   1.00    1.00    --   95.80  45.00 -30.00   35
 57  \w    104.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   81
 58  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 59  \w     28.00 126.00   1.00    1.00    --   95.80 -77.00 -60.00   98
 60  \w      8.00 122.00   1.00    1.00    --   95.80 -77.00  90.00  114
 61  \w    117.00 183.00   1.00    1.00    --   95.80  77.00  30.00   66
 62  \w     82.00 107.00   1.00    1.00    --   95.80 -82.00 -30.00   25
 63  \w     67.00  93.00   1.00    1.00    --   95.80  72.00  -6.43   26
 64  \w     68.00  94.00   1.00    1.00    --   95.80  73.00  24.41   26
 65  \w     69.00  95.00   1.00    1.00    --   95.80  66.00 -18.11   26
 66  \w     55.00 126.00   1.00    1.00    --   95.80 -82.00-120.00   71
 67  \w     72.00 174.00   1.00    1.00    --   95.80  57.00 -70.86  102
;
_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      0.0897065000
_diffrn_orient_matrix_UB_12      -0.0506386000
_diffrn_orient_matrix_UB_13      0.0973197000
_diffrn_orient_matrix_UB_21      -0.1052660000
_diffrn_orient_matrix_UB_22      0.0177754000
_diffrn_orient_matrix_UB_23      0.0510291000
_diffrn_orient_matrix_UB_31      -0.0470970000
_diffrn_orient_matrix_UB_32      -0.1363863000
_diffrn_orient_matrix_UB_33      -0.0295128000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37559
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.425
_diffrn_reflns_theta_min         4.194
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11907
_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    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 2585 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(4)
_refine_ls_extinction_coef       0.0103(9)
_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   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6175
_refine_ls_number_restraints     86
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0866P)^2^+0.4513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                6004
_reflns_number_total             6175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04354_si_003.cif
_cod_data_source_block           exp_650
_cod_depositor_comments
'Adding full bibliography for 4517365--4517367.cif.'
_cod_database_code               4517365
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.345
_shelx_estimated_absorpt_t_min   0.189
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C10, C11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C11 \\sim C10: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
Uanis(C7) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C19) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C26) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C10) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C25) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C11) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C4) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C22) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(N1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C13) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C31) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C32) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C29) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4.a Ternary CH refined with riding coordinates:
 C37(H37)
4.b 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), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21),
  C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
4.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              97623
_shelx_hkl_checksum              77672
_shelx_fab_checksum              69485
_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 4.583
_oxdiff_exptl_absorpt_empirical_full_min 0.506