Nickel-Catalyzed Enantioselective Pyridone C-H Functionalizations Enabled by a Bulky N-Heterocyclic Carbene Ligand.
Diesel, Johannes; Finogenova, Anastasiia M.; Cramer, Nicolai; Journal of the American Chemical Society 140 (2018) 4489–4493; doi:10.1021/jacs.8b01181

data_4132061
_publ_section_title
;
 Nickel-Catalyzed Enantioselective Pyridone C-H Functionalizations Enabled
 by a Bulky N-Heterocyclic Carbene Ligand.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4489
_journal_page_last               4493
_journal_paper_doi               10.1021/jacs.8b01181
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C59 H52 Au Cl N2'
_chemical_formula_sum            'C59 H52 Au Cl N2'
_chemical_formula_weight         1021.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.77519(18)
_cell_length_b                   19.4896(2)
_cell_length_c                   16.16113(19)
_cell_measurement_reflns_used    36556
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5820
_cell_measurement_theta_min      3.3650
_cell_volume                     5598.72(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Mercury 3.9 (CCDC, 2016)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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     17.00  44.00   1.00    3.00    --   50.00  82.00 -21.96   27
  2  \w     20.00  45.00   1.00    3.00    --   54.00  81.00  28.25   25
  3  \w     38.00  64.00   1.00    3.00    --   70.00  75.00  -1.89   26
  4  \w     37.00  64.00   1.00    3.00    --   70.00  77.00  56.79   27
  5  \w     37.00  69.00   1.00    3.00    --   70.00  77.00  91.89   32
  6  \w     80.00 146.00   1.00    3.00    --   70.00  77.00 167.92   66
  7  \w    121.00 146.00   1.00    3.00    --   70.00  77.00  91.89   25
  8  \w    113.00 140.00   1.00   12.00    --  111.23  77.00  60.00   27
  9  \w    117.00 177.00   1.00   12.00    --  111.23  77.00  30.00   60
 10  \w    129.00 157.00   1.00   12.00    --  111.23  61.00 -30.00   28
 11  \w    105.00 132.00   1.00    3.00    --   70.00  76.00 -81.97   27
 12  \w     94.00 142.00   1.00    3.00    --   66.00  77.00-147.65   48
 13  \w    127.00 177.00   1.00   12.00    --  111.23  77.00-180.00   50
 14  \w    121.00 178.00   1.00   12.00    --  111.23  77.00-150.00   57
 15  \w    101.00 150.00   1.00    3.00    --   74.00  76.00  28.44   49
 16  \w    119.00 147.00   1.00   12.00    --  111.23  77.00 150.00   28
 17  \w     82.00 145.00   1.00   12.00    --  111.23  61.00  90.00   63
 18  \w     79.00 164.00   1.00   12.00    --  111.23  77.00  90.00   85
 19  \w     82.00 109.00   1.00   12.00    --  111.23  61.00 -30.00   27
 20  \w     82.00 143.00   1.00   12.00    --  111.23  61.00   0.00   61
 21  \w     84.00 120.00   1.00   12.00    --  111.23  61.00-120.00   36
 22  \w     79.00 106.00   1.00   12.00    --  111.23  77.00 -90.00   27
 23  \w     79.00 174.00   1.00   12.00    --  111.23  77.00 -60.00   95
 24  \w     80.00 177.00   1.00   12.00    --  111.23  77.00 120.00   97
 25  \w     83.00 108.00   1.00   12.00    --  111.23  61.00 150.00   25
 26  \w     83.00 108.00   1.00   12.00    --  111.23  61.00 120.00   25
 27  \w     83.00 114.00   1.00   12.00    --  111.23  61.00  60.00   31
 28  \w     79.00 177.00   1.00   12.00    --  111.23  77.00   0.00   98
 29  \w     83.00 109.00   1.00   12.00    --  111.23  61.00 -60.00   26
 30  \w     83.00 160.00   1.00   12.00    --  111.23  61.00 -90.00   77
 31  \w     82.00 145.00   1.00   12.00    --  111.23  61.00-180.00   63
 32  \w     79.00 105.00   1.00   12.00    --  111.23  77.00-180.00   26
 33  \w     83.00 110.00   1.00   12.00    --  111.23  61.00-150.00   27
 34  \w     79.00 105.00   1.00   12.00    --  111.23  77.00-120.00   26
 35  \w     79.00 105.00   1.00   12.00    --  111.23  77.00-150.00   26
 36  \w     79.00 105.00   1.00   12.00    --  111.23  77.00 -30.00   26
 37  \w     79.00 105.00   1.00   12.00    --  111.23  77.00  30.00   26
 38  \w     79.00 105.00   1.00   12.00    --  111.23  77.00  60.00   26
 39  \w     80.00 105.00   1.00   12.00    --  111.23  77.00 150.00   25
 40  \w     42.00  84.00   1.00    3.00    --   74.00  76.00  28.44   42
 41  \w     42.00  69.00   1.00    3.00    --   74.00  76.00 -52.26   27
 42  \w     38.00  64.00   1.00    3.00    --   70.00  76.00 -81.97   26
 43  \w     37.00  73.00   1.00    3.00    --   70.00  77.00-135.51   36
 44  \w     33.00  61.00   1.00    3.00    --   66.00  77.00-147.65   28
 45  \w     20.00  45.00   1.00    3.00    --   54.00  81.00 -95.13   25
 46  \w     21.00  46.00   1.00    3.00    --   54.00  78.00-153.16   25
 47  \w      0.00  25.00   1.00    3.00    --   38.00  92.00   1.91   25
 48  \w     20.00  45.00   1.00    3.00    --   54.00  81.00  91.88   25
 49  \w     21.00  46.00   1.00    3.00    --   54.00  79.00 135.28   25
 50  \w     33.00  59.00   1.00    3.00    --   66.00  77.00 139.20   26
 51  \w     37.00  71.00   1.00    3.00    --   70.00  77.00 167.92   34
 52  \w      0.00  25.00   1.00    3.00    --   38.00  91.00 124.18   25
 53  \w    -32.00  67.00   1.00    3.00    --   40.91 -77.00 150.00   99
 54  \w     24.00  73.00   1.00    3.00    --   40.91-125.00 150.00   49
 55  \w     29.00 102.00   1.00   12.00    --  111.23 -94.00  30.00   73
 56  \w     43.00  89.00   1.00   12.00    --  111.23 -94.00 -30.00   46
 57  \w     38.00 120.00   1.00   12.00    --  111.23-125.00 -30.00   82
 58  \w     38.00 121.00   1.00   12.00    --  111.23-125.00 150.00   83
 59  \w     29.00  89.00   1.00   12.00    --  111.23 -94.00 150.00   60
 60  \w     29.00 101.00   1.00   12.00    --  111.23 -94.00-150.00   72
 61  \w    -78.00 -18.00   1.00    3.00    --  -40.91 -38.00-150.00   60
 62  \w    -75.00 -13.00   1.00    3.00    --  -40.91 -57.00 -90.00   62
 63  \w   -105.00 -13.00   1.00    3.00    --  -40.91 -57.00 120.00   92
 64  \w   -113.00 -21.00   1.00    3.00    --  -40.91 -38.00   0.00   92
 65  \w   -108.00 -82.00   1.00    3.00    --  -40.91 -38.00-150.00   26
 66  \w    -95.00  -5.00   1.00    3.00    --  -40.91 125.00 -90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9642
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.765
_diffrn_reflns_theta_min         3.365
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.632
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.367
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       prism
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.034(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         9642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0230
_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^)+(0.0437P)^2^+0.5572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0599
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                9400
_reflns_number_total             9642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01181_si_006.cif
_cod_data_source_block           jdi-1-706_sq
_cod_database_code               4132061
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.158
_shelx_estimated_absorpt_t_max   0.661
_shelx_res_checksum              37158
_shelx_hkl_checksum              74406
_shelx_fab_checksum              8042