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_4517367
_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 O2 P S, C H Cl3'
_chemical_formula_sum            'C38 H37 Cl3 Fe N O2 P S'
_chemical_formula_weight         764.91
_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             2019-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.888(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3729(3)
_cell_length_b                   11.5112(2)
_cell_length_c                   15.6134(3)
_cell_measurement_reflns_used    26818
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.2710
_cell_measurement_theta_min      4.4300
_cell_volume                     1783.91(7)
_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 0.996
_diffrn_measured_fraction_theta_max 0.987
_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     62.00  89.00   1.00    1.00    --    0.00  57.00 -90.00   27
  2  \w    -30.00  11.00   1.00    1.00    --    0.00  77.00  90.00   41
  3  \w    -85.00 -60.00   1.00    1.00    --    0.00 -57.00-120.00   25
  4  \w    -23.00  52.00   1.00    1.00    --    0.00  57.00 -90.00   75
  5  \w    -23.00  27.00   1.00    1.00    --    0.00  57.00 -30.00   50
  6  \w     17.00  60.00   1.00    1.00    --    0.00  77.00  90.00   43
  7  \w     29.00  89.00   1.00    1.00    --    0.00  57.00-180.00   60
  8  \w    -18.00  21.00   1.00    1.00    --    0.00 -57.00-120.00   39
  9  \w    -23.00   6.00   1.00    1.00    --    0.00  19.00-180.00   29
 10  \w    -22.00  16.00   1.00    1.00    --    0.00  77.00  30.00   38
 11  \w    -82.00 -36.00   1.00    1.00    --    0.00 -38.00  90.00   46
 12  \w     62.00  87.00   1.00    1.00    --    0.00  38.00  30.00   25
 13  \w     24.00  63.00   1.00    1.00    --    0.00  77.00  30.00   39
 14  \w     19.00  45.00   1.00    1.00    --    0.00  19.00-180.00   26
 15  \w    -18.00  19.00   1.00    1.00    --    0.00  38.00  30.00   37
 16  \w     -7.00  18.00   1.00    1.00    --    0.00 -38.00  90.00   25
 17  \w    -23.00  25.00   1.00    1.00    --    0.00  57.00-180.00   48
 18  \w     37.00  88.00   1.00    1.00    --    0.00  57.00 -30.00   51
 19  \w    141.00 179.00   1.00    1.00    --   95.80  82.00  73.54   38
 20  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  73.54   26
 21  \w     66.00 111.00   1.00    1.00    --   95.80  75.00 -98.69   45
 22  \w    133.00 158.00   1.00    1.00    --   95.80  82.00 -81.60   25
 23  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 24  \w     63.00  92.00   1.00    1.00    --   95.80  82.00 -81.60   29
 25  \w     73.00 104.00   1.00    1.00    --   95.80  61.00 120.00   31
 26  \w     66.00  92.00   1.00    1.00    --   95.80  77.00  30.00   26
 27  \w     63.00  92.00   1.00    1.00    --   95.80  82.00 150.00   29
 28  \w     64.00  95.00   1.00    1.00    --   95.80  82.00-180.00   31
 29  \w     35.00 127.00   1.00    1.00    --   95.80 -82.00-120.00   92
 30  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 31  \w     66.00  92.00   1.00    1.00    --   95.80  76.00  70.88   26
 32  \w     70.00 184.00   1.00    1.00    --   95.80  64.00 -17.39  114
 33  \w      6.00 127.00   1.00    1.00    --   95.80 -82.00 150.00  121
 34  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 35  \w    149.00 175.00   1.00    1.00    --   95.80  79.00-133.60   26
 36  \w     65.00  95.00   1.00    1.00    --   95.80  77.00  90.00   30
 37  \w      6.00 127.00   1.00    1.00    --   95.80 -82.00   0.00  121
 38  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 39  \w     40.00  96.00   1.00    1.00    --   95.80 -82.00 -30.00   56
 40  \w     64.00  89.00   1.00    1.00    --   95.80  79.00-133.60   25
 41  \w    101.00 184.00   1.00    1.00    --   95.80  75.00 135.49   83
 42  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 43  \w     65.00 117.00   1.00    1.00    --   95.80  77.00 150.00   52
 44  \w     26.00 126.00   1.00    1.00    --   95.80 -77.00-180.00  100
 45  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -90.00   26
 46  \w     75.00 171.00   1.00    1.00    --   95.80  45.00 -30.00   96
 47  \w     64.00  90.00   1.00    1.00    --   95.80  82.00   0.00   26
 48  \w     71.00 184.00   1.00    1.00    --   95.80  61.00   0.00  113
 49  \w     70.00  96.00   1.00    1.00    --   95.80  62.00 -24.25   26
 50  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 51  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 52  \w    153.00 178.00   1.00    1.00    --   95.80  69.00  35.04   25
 53  \w     93.00 125.00   1.00    1.00    --   95.80 -82.00  60.00   32
 54  \w     50.00  78.00   1.00    1.00    --   95.80 -82.00  60.00   28
 55  \w    111.00 184.00   1.00    1.00    --   95.80  81.00-122.53   73
 56  \w     75.00 182.00   1.00    1.00    --   95.80  45.00-150.00  107
 57  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 58  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 59  \w     75.00 184.00   1.00    1.00    --   95.80  45.00  60.00  109
 60  \w     76.00 123.00   1.00    1.00    --   95.80  45.00 150.00   47
 61  \w    148.00 173.00   1.00    1.00    --   95.80  45.00 150.00   25
 62  \w     64.00  99.00   1.00    1.00    --   95.80  82.00  30.00   35
 63  \w     11.00  46.00   1.00    1.00    --   95.80 -82.00  60.00   35
 64  \w     75.00 183.00   1.00    1.00    --   95.80  45.00  90.00  108
 65  \w    149.00 174.00   1.00    1.00    --   95.80  82.00 -60.00   25
 66  \w     63.00  97.00   1.00    1.00    --   95.80  81.00-122.53   34
 67  \w     68.00  94.00   1.00    1.00    --   95.80  69.00  35.04   26
 68  \w     67.00  96.00   1.00    1.00    --   95.80  75.00 135.49   29
 69  \w     76.00 169.00   1.00    1.00    --   95.80  41.00 -95.48   93
 70  \w     65.00 173.00   1.00    1.00    --   95.80  78.00-156.85  108
;
_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      -0.0069981000
_diffrn_orient_matrix_UB_12      -0.1230858000
_diffrn_orient_matrix_UB_13      -0.0397835000
_diffrn_orient_matrix_UB_21      0.0053604000
_diffrn_orient_matrix_UB_22      0.0520016000
_diffrn_orient_matrix_UB_23      -0.0897859000
_diffrn_orient_matrix_UB_31      0.1550390000
_diffrn_orient_matrix_UB_32      -0.0073241000
_diffrn_orient_matrix_UB_33      0.0313529000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43891
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.660
_diffrn_reflns_theta_min         4.455
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16293
_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    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.694
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 2976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(6)
_refine_ls_extinction_coef       0.0024(4)
_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   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         7170
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0911P)^2^+4.3172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1537
_refine_ls_wR_factor_ref         0.1546
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                6919
_reflns_number_total             7170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04354_si_004.cif
_cod_data_source_block           exp_736
_cod_depositor_comments
'Adding full bibliography for 4517365--4517367.cif.'
_cod_database_code               4517367
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.320
_shelx_estimated_absorpt_t_min   0.196
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C33(H33), C38(H38)
2.c 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), C18(H18), C19(H19), C20(H20), C21(H21),
  C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              44669
_shelx_hkl_checksum              75336
_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 4.429
_oxdiff_exptl_absorpt_empirical_full_min 0.467