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_4514638
_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         'C34 H36 Fe N O3 P S'
_chemical_formula_sum            'C34 H36 Fe N O3 P S'
_chemical_formula_weight         625.52
_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             2019-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.777(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5035(2)
_cell_length_b                   10.7831(2)
_cell_length_c                   13.3149(2)
_cell_measurement_reflns_used    12700
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8540
_cell_measurement_theta_min      4.1120
_cell_volume                     1544.22(5)
_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 0.993
_diffrn_measured_fraction_theta_max 0.988
_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    -32.00   3.00   1.00    1.00    --    0.00  81.00 100.00   35
  2  \w     64.00  97.00   1.00    1.00    --   95.80  81.00 100.00   33
  3  \w     94.00 128.00   1.00    1.00    --   95.80 -81.00 -22.00   34
  4  \w      8.00  80.00   1.00    1.00    --   95.80 -81.00 -22.00   72
  5  \w    -22.00  34.00   1.00    1.00    --    0.00  57.00  30.00   56
  6  \w    -22.00  11.00   1.00    1.00    --    0.00  57.00-150.00   33
  7  \w    -17.00  87.00   1.00    1.00    --    0.00  38.00-180.00  104
  8  \w     15.00  46.00   1.00    1.00    --    0.00  81.00 100.00   31
  9  \w    -19.00  88.00   1.00    1.00    --    0.00  38.00 -60.00  107
 10  \w     37.00  86.00   1.00    1.00    --    0.00  57.00  30.00   49
 11  \w     45.00  81.00   1.00    1.00    --    0.00  82.00 -30.00   36
 12  \w    -14.00  27.00   1.00    1.00    --    0.00 -81.00 -22.00   41
 13  \w     18.00  43.00   1.00    1.00    --    0.00  57.00-150.00   25
 14  \w    -63.00 -29.00   1.00    1.00    --    0.00 -81.00 -22.00   34
 15  \w     42.00  85.00   1.00    1.00    --    0.00  38.00   0.00   43
 16  \w    -18.00   9.00   1.00    1.00    --    0.00  38.00   0.00   27
 17  \w    -27.00  22.00   1.00    1.00    --    0.00  82.00 -30.00   49
 18  \w     63.00  98.00   1.00    1.00    --   95.80  82.00   0.00   35
 19  \w     76.00 184.00   1.00    1.00    --   95.80  45.00  60.00  108
 20  \w     69.00  95.00   1.00    1.00    --   95.80  82.00  30.00   26
 21  \w    137.00 185.00   1.00    1.00    --   95.80  45.00 -90.00   48
 22  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 23  \w     75.00 148.00   1.00    1.00    --   95.80  45.00 -30.00   73
 24  \w    156.00 182.00   1.00    1.00    --   95.80  82.00 -30.00   26
 25  \w     65.00 181.00   1.00    1.00    --   95.80  77.00 120.00  116
 26  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 27  \w     75.00 101.00   1.00    1.00    --   95.80  45.00-180.00   26
 28  \w     75.00 103.00   1.00    1.00    --   95.80  45.00 -90.00   28
 29  \w     75.00 185.00   1.00    1.00    --   95.80  45.00-144.12  110
 30  \w     76.00 114.00   1.00    1.00    --   95.80  45.00   0.00   38
 31  \w     79.00 123.00   1.00    1.00    --   95.80  30.00 -30.00   44
 32  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 33  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 34  \w     63.00  94.00   1.00    1.00    --   95.80  82.00  60.00   31
 35  \w    132.00 185.00   1.00    1.00    --   95.80  66.00  69.82   53
 36  \w     75.00 185.00   1.00    1.00    --   95.80  45.00  30.00  110
 37  \w    160.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   25
 38  \w     69.00  94.00   1.00    1.00    --   95.80  66.00  69.82   25
 39  \w    105.00 130.00   1.00    1.00    --   95.80  82.00 -30.00   25
 40  \w    148.00 173.00   1.00    1.00    --   95.80  75.00 -92.97   25
 41  \w     66.00  94.00   1.00    1.00    --   95.80  75.00 -92.97   28
 42  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 43  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 44  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 45  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 46  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 47  \w     76.00 130.00   1.00    1.00    --   95.80  45.00 120.00   54
 48  \w     64.00  90.00   1.00    1.00    --   95.80  82.00-180.00   26
 49  \w     12.00  37.00   1.00    1.00    --   95.80 -82.00 -60.00   25
 50  \w     43.00 127.00   1.00    1.00    --   95.80 -82.00 -60.00   84
 51  \w    131.00 156.00   1.00    1.00    --   95.80  45.00 -60.00   25
 52  \w     75.00 101.00   1.00    1.00    --   95.80  45.00 -60.00   26
 53  \w     63.00  91.00   1.00    1.00    --   95.80  82.00 -90.00   28
 54  \w     36.00 123.00   1.00    1.00    --   95.80 -82.00  90.00   87
 55  \w      7.00 128.00   1.00    1.00    --   95.80 -82.00  30.00  121
 56  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 57  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 58  \w    106.00 179.00   1.00    1.00    --   95.80  69.00 172.82   73
 59  \w     66.00  92.00   1.00    1.00    --   95.80  77.00  90.00   26
 60  \w     75.00 183.00   1.00    1.00    --   95.80  45.00-120.00  108
 61  \w     68.00  99.00   1.00    1.00    --   95.80  69.00 172.82   31
 62  \w     72.00  98.00   1.00    1.00    --   95.80  61.00  60.00   26
 63  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 64  \w     18.00 125.00   1.00    1.00    --   95.80 -82.00-180.00  107
 65  \w      7.00 107.00   1.00    1.00    --   95.80 -61.00-180.00  100
 66  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -30.00   26
;
_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      0.1324334000
_diffrn_orient_matrix_UB_12      0.0148949000
_diffrn_orient_matrix_UB_13      0.0828692000
_diffrn_orient_matrix_UB_21      -0.0247847000
_diffrn_orient_matrix_UB_22      -0.1057318000
_diffrn_orient_matrix_UB_23      0.0674746000
_diffrn_orient_matrix_UB_31      0.0486185000
_diffrn_orient_matrix_UB_32      -0.0949197000
_diffrn_orient_matrix_UB_33      -0.0623258000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1577
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34735
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.627
_diffrn_reflns_theta_min         4.110
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.312
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19468
_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    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.694
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 2066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(5)
_refine_ls_extinction_coef       0.0036(8)
_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   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6175
_refine_ls_number_restraints     260
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1126P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1673
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                5500
_reflns_number_total             6175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02080_si_005.cif
_cod_data_source_block           exp_905
_cod_database_code               4514638
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.503
_shelx_estimated_absorpt_t_min   0.281
_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
 P1, O3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C23(H23)
4.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C26(H26), C22(H22), C12(H12), C25(H25), C2(H2), C10(H10), C6(H6),
 C16(H16), C29(H29), C15(H15), C18(H18), C20(H20), C11(H11), C19(H19), C4(H4),
 C21(H21), C5(H5), C28(H28), C8(H8), C3(H3), C9(H9)
4.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C30(H30A,H30B,H30C), C32(H32A,H32B,
 H32C)
;
_shelx_res_checksum              77165
_shelx_hkl_checksum              31343
_shelx_fab_checksum              24822
_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 9.415
_oxdiff_exptl_absorpt_empirical_full_min 0.157