Enantioselective Cobalt-Catalyzed Reductive Cross-Coupling for the Synthesis of Axially Chiral Phosphine–Olefin Ligands
Zhang, Xi; Wang, Juan; Yang, Shang-Dong; ACS Catalysis 11 (2021) 14008–14015; doi:10.1021/acscatal.1c04128

data_4519167
_publ_section_title
;
 Enantioselective Cobalt-Catalyzed Reductive Cross-Coupling for the
 Synthesis of Axially Chiral Phosphine--Olefin Ligands
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              14008
_journal_page_last               14015
_journal_paper_doi               10.1021/acscatal.1c04128
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C48 H57 O P'
_chemical_formula_sum            'C48 H57 O P'
_chemical_formula_weight         680.90
_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             2021-07-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.5600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.25240(10)
_cell_length_b                   10.02120(10)
_cell_length_c                   19.2295(2)
_cell_measurement_reflns_used    14045
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.3310
_cell_measurement_theta_min      2.2960
_cell_volume                     1975.57(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.958
_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    115.00 158.00   0.50    1.02    --  107.75  57.00 -90.00   86
  2  \w    137.00 175.00   0.50    1.02    --  107.75  57.00 -30.00   76
  3  \w     93.00 132.00   0.50    1.02    --  107.75  57.00 -30.00   78
  4  \w     95.00 132.00   0.50    1.02    --  107.75  37.00   0.00   74
  5  \w    144.00 174.00   0.50    1.02    --  107.75  37.00   0.00   60
  6  \w    101.00 173.00   0.50    1.02    --  107.75  37.00 120.00  144
  7  \w     35.00 116.00   0.50    0.25    --   47.57  19.00 -30.00  162
  8  \w     51.00  94.00   0.50    0.25    --   47.57  37.00-120.00   86
  9  \w    -26.00   1.00   0.50    0.25    --   47.57 -19.00   0.00   54
 10  \w     35.00  60.00   0.50    1.02    --  107.75 -57.00 120.00   50
 11  \w     37.00  63.00   0.50    1.02    --  107.75 -57.00   0.00   52
 12  \w    115.00 141.00   0.50    1.02    --  107.75 101.00 -85.00   52
 13  \w     72.00 102.00   0.50    1.02    --  107.75 -77.00-180.00   60
 14  \w     36.00  62.00   0.50    1.02    --  107.75 -57.00-120.00   52
 15  \w     35.00  60.00   0.50    1.02    --  107.75 -57.00 -60.00   50
 16  \w     41.00 102.00   0.50    1.02    --  107.75 -77.00 -90.00  122
 17  \w     94.00 119.00   0.50    1.02    --  107.75-135.00 -57.92   50
 18  \w     45.00  83.00   0.50    1.02    --  107.75-135.00 -57.92   76
 19  \w     36.00 112.00   0.50    1.02    --  107.75-125.00  30.00  152
 20  \w     75.00 111.00   0.50    1.02    --  107.75-125.00  60.00   72
 21  \w     35.00  70.00   0.50    1.02    --  107.75-125.00  60.00   70
 22  \w      1.00  36.00   0.50    0.25    --   47.57-101.00 170.00   70
 23  \w     40.00  72.00   0.50    0.25    --   47.57-101.00 170.00   64
 24  \w     48.00 100.00   0.50    1.02    --  107.75-101.00 170.00  104
 25  \w     41.00 100.00   0.50    1.02    --  107.75 -99.00  60.00  118
 26  \w    -38.00  20.00   0.50    0.25    --  -47.57  37.00-120.00  116
 27  \w    -45.00  21.00   0.50    0.25    --  -47.57  37.00 150.00  132
 28  \w    -29.00  20.00   0.50    0.25    --  -47.57  19.00 -60.00   98
 29  \w    -29.00  19.00   0.50    0.25    --  -47.57  19.00-150.00   96
 30  \w   -101.00 -71.00   0.50    1.02    -- -100.00 101.00 -85.00   60
 31  \w   -105.00 -70.00   0.50    1.02    -- -100.00 125.00 -90.00   70
 32  \w    -73.00 -31.00   0.50    0.25    --  -47.57 101.00 -85.00   84
 33  \w   -112.00 -49.50   0.50    1.02    -- -100.00 125.00  90.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0931397000
_diffrn_orient_matrix_UB_12      0.1081572000
_diffrn_orient_matrix_UB_13      0.0273427000
_diffrn_orient_matrix_UB_21      0.1145698000
_diffrn_orient_matrix_UB_22      0.0993257000
_diffrn_orient_matrix_UB_23      0.0049058000
_diffrn_orient_matrix_UB_31      -0.0279815000
_diffrn_orient_matrix_UB_32      0.0458070000
_diffrn_orient_matrix_UB_33      -0.0750910000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18276
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.603
_diffrn_reflns_theta_min         2.298
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
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    1.145
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2743 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7299
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0428
_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^)+1.6751P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.851
_reflns_Friedel_fraction_max     0.765
_reflns_number_gt                6975
_reflns_number_total             7299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c04128_si_002.cif
_cod_data_source_block           zhangx_0630-1_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4519167
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.958
_reflns_odcompleteness_completeness 99.23
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C24(H24), C26(H26), C36(H36), C38(H38),
  C40(H40)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C41(H41A,H41B,H41C), C42(H42A,
 H42B,H42C), C43(H43A,H43B,H43C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C),
 C48(H48A,H48B,H48C)
;
_shelx_res_checksum              74483
_shelx_hkl_checksum              82442
_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 1.936
_oxdiff_exptl_absorpt_empirical_full_min 0.310