Design and Synthesis of WJ-Phos, and Application in Cu-Catalyzed Enantioselective Boroacylation of 1,1-Disubstituted Allenes
Han, Jie; Zhou, Wei; Zhang, Pei-Chao; Wang, Huamin; Zhang, Ronghua; Wu, Hai-Hong; Zhang, Junliang; ACS Catalysis 9 (2019) 6890–; doi:10.1021/acscatal.9b02080

data_4514640
_publ_section_title
;
 Design and Synthesis of WJ-Phos, and Application in Cu-Catalyzed
 Enantioselective Boroacylation of 1,1-Disubstituted Allenes
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              6890
_journal_paper_doi               10.1021/acscatal.9b02080
_journal_volume                  9
_journal_year                    2019
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.748(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5036(4)
_cell_length_b                   11.7796(4)
_cell_length_c                   15.6619(6)
_cell_measurement_reflns_used    11075
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.8110
_cell_measurement_theta_min      4.7370
_cell_volume                     1855.62(12)
_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 0.994
_diffrn_measured_fraction_theta_max 0.976
_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    -24.00  16.00   1.00    2.00    --    0.00 -38.00-120.00   40
  2  \w    -54.00  19.00   1.00    2.00    --    0.00 -38.00  30.00   73
  3  \w    -17.00  29.00   1.00    2.00    --    0.00  38.00  30.00   46
  4  \w    -19.00  53.00   1.00    2.00    --    0.00  57.00 150.00   72
  5  \w     33.00  86.00   1.00    2.00    --    0.00  38.00  30.00   53
  6  \w    -18.00  26.00   1.00    2.00    --    0.00  38.00 -60.00   44
  7  \w    -65.00  -1.00   1.00    2.00    --    0.00 -38.00 120.00   64
  8  \w    -26.00   7.00   1.00    2.00    --    0.00  82.00-150.00   33
  9  \w     58.00  87.00   1.00    2.00    --    0.00  57.00 150.00   29
 10  \w     31.00  86.00   1.00    2.00    --    0.00  38.00 -60.00   55
 11  \w    -68.00 -42.00   1.00    2.00    --    0.00 -38.00-120.00   26
 12  \w     33.00  84.00   1.00    2.00    --    0.00  57.00  90.00   51
 13  \w     13.00  73.00   1.00    2.00    --    0.00  82.00-150.00   60
 14  \w    -23.00   9.00   1.00    2.00    --    0.00  57.00  90.00   32
 15  \w    156.00 183.00   1.00    2.00    --   95.80  55.00 -13.29   27
 16  \w    106.00 153.00   1.00    2.00    --   95.80  55.00 -13.29   47
 17  \w     72.00 119.00   1.00    2.00    --   95.80  56.00 107.15   47
 18  \w     72.00 101.00   1.00    2.00    --   95.80  55.00 -13.29   29
 19  \w     65.00  91.00   1.00    2.00    --   95.80  80.00 -10.36   26
 20  \w     64.00  89.00   1.00    2.00    --   95.80  79.00 -32.06   25
 21  \w     72.00 146.00   1.00    2.00    --   95.80  57.00-151.53   74
 22  \w     65.00  90.00   1.00    2.00    --   95.80  77.00  60.00   25
 23  \w     87.00 113.00   1.00    2.00    --   95.80 -82.00-150.00   26
 24  \w     65.00  91.00   1.00    2.00    --   95.80  77.00 -60.00   26
 25  \w     64.00 111.00   1.00    2.00    --   95.80  82.00-150.00   47
 26  \w     65.00  91.00   1.00    2.00    --   95.80  77.00 150.00   26
 27  \w    135.00 177.00   1.00    2.00    --   95.80  77.00 150.00   42
 28  \w      6.00 128.00   1.00    2.00    --   95.80 -82.00  60.00  122
 29  \w     64.00  90.00   1.00    2.00    --   95.80  82.00  90.00   26
 30  \w     63.00  96.00   1.00    2.00    --   95.80  82.00 -90.00   33
 31  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 150.00   26
 32  \w    108.00 185.00   1.00    2.00    --   95.80  69.00  35.57   77
 33  \w    156.00 185.00   1.00    2.00    --   95.80  82.00  60.00   29
 34  \w      8.00 125.00   1.00    2.00    --   95.80 -82.00 150.00  117
 35  \w     68.00  93.00   1.00    2.00    --   95.80  69.00  35.57   25
 36  \w     72.00 185.00   1.00    2.00    --   95.80  55.00 -68.89  113
 37  \w    120.00 160.00   1.00    2.00    --   95.80  45.00 -90.00   40
 38  \w     75.00 117.00   1.00    2.00    --   95.80  45.00 -90.00   42
 39  \w     63.00  88.00   1.00    2.00    --   95.80  82.00-180.00   25
 40  \w     63.00  93.00   1.00    2.00    --   95.80  82.00  60.00   30
 41  \w     56.00 127.00   1.00    2.00    --   95.80 -82.00 -30.00   71
 42  \w     65.00  90.00   1.00    2.00    --   95.80  77.00-150.00   25
 43  \w     63.00  88.00   1.00    2.00    --   95.80  82.00 -60.00   25
 44  \w    123.00 185.00   1.00    2.00    --   95.80  45.00  60.00   62
 45  \w     64.00  90.00   1.00    2.00    --   95.80  80.00 -20.66   26
 46  \w     40.00  73.00   1.00    2.00    --   95.80 -82.00-150.00   33
 47  \w     75.00 182.00   1.00    2.00    --   95.80  45.00 -30.00  107
 48  \w     71.00  96.00   1.00    2.00    --   95.80  61.00 -90.00   25
 49  \w     71.00 119.00   1.00    2.00    --   95.80  61.00  60.00   48
 50  \w     65.00  91.00   1.00    2.00    --   95.80  77.00  90.00   26
 51  \w     75.00 185.00   1.00    2.00    --   95.80  45.00 150.00  110
 52  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 -90.00   25
 53  \w     65.00 110.00   1.00    2.00    --   95.80  77.00   0.00   45
 54  \w     63.00  88.00   1.00    2.00    --   95.80  82.00  30.00   25
 55  \w     75.00 100.00   1.00    2.00    --   95.80  45.00  60.00   25
 56  \w     65.00  90.00   1.00    2.00    --   95.80  77.00-120.00   25
 57  \w     63.00  88.00   1.00    2.00    --   95.80  82.00 120.00   25
 58  \w    121.00 185.00   1.00    2.00    --   95.80  82.00 120.00   64
 59  \w     71.00  97.00   1.00    2.00    --   95.80  61.00-180.00   26
 60  \w     63.00  89.00   1.00    2.00    --   95.80  82.00   0.00   26
 61  \w    117.00 177.00   1.00    2.00    --   95.80  82.00   0.00   60
 62  \w     33.00  77.00   1.00    2.00    --   95.80 -82.00  90.00   44
 63  \w     92.00 118.00   1.00    2.00    --   95.80 -82.00  90.00   26
 64  \w     65.00  95.00   1.00    2.00    --   95.80  76.00 119.29   30
 65  \w    122.00 182.00   1.00    2.00    --   95.80  56.00 107.15   60
 66  \w    152.00 178.00   1.00    2.00    --   95.80  57.00-151.53   26
 67  \w     76.00 102.00   1.00    2.00    --   95.80  45.00-180.00   26
 68  \w    121.00 146.00   1.00    2.00    --   95.80  45.00-180.00   25
 69  \w    150.00 178.00   1.00    2.00    --   95.80  52.00-156.91   28
 70  \w     62.00 119.00   1.00    2.00    --   95.80 -82.00 -90.00   57
 71  \w     73.00  98.00   1.00    2.00    --   95.80  52.00-156.91   25
;
_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      0.0196021000
_diffrn_orient_matrix_UB_12      -0.1138350000
_diffrn_orient_matrix_UB_13      0.0504896000
_diffrn_orient_matrix_UB_21      0.0409141000
_diffrn_orient_matrix_UB_22      0.0641730000
_diffrn_orient_matrix_UB_23      0.0894978000
_diffrn_orient_matrix_UB_31      -0.1463320000
_diffrn_orient_matrix_UB_32      0.0026883000
_diffrn_orient_matrix_UB_33      0.0007779000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1231
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_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            41695
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.161
_diffrn_reflns_theta_min         4.396
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.444
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33067
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 2093 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         7417
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0932P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                5859
_reflns_number_total             7417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02080_si_002.cif
_cod_data_source_block           exp_533
_cod_database_code               4514640
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.331
_shelx_estimated_absorpt_t_min   0.156
_reflns_odcompleteness_completeness 99.66
_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:
 C37(H37), C38(H38)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C6(H6), C32(H32), C28(H28), C2(H2), C16(H16), C24(H24), C26(H26),
 C27(H27), C15(H15), C19(H19), C22(H22), C23(H23), C14(H14), C12(H12), C20(H20),
  C8(H8), C21(H21), C10(H10), C11(H11), C25(H25), C5(H5), C4(H4), C3(H3), C9(H9)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              22864
_shelx_hkl_checksum              52711
_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 5.574
_oxdiff_exptl_absorpt_empirical_full_min 0.287