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_4132058
_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         'C19 H17 N O'
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.33
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 104.805(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3598(5)
_cell_length_b                   8.1021(3)
_cell_length_c                   14.4042(5)
_cell_measurement_reflns_used    7601
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.1540
_cell_measurement_theta_min      4.1600
_cell_volume                     1394.55(9)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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      2.00  27.00   1.00    5.00    --   38.00  87.00   2.84   25
  2  \w      5.00  30.00   1.00    5.00    --   42.00  90.00 157.91   25
  3  \w   -131.00  45.00   1.00    5.00    --  -43.13   0.00  30.00  176
  4  \w    -43.00 -16.00   1.00    5.00    --  -43.13 -57.00 -90.00   27
  5  \w    -70.00  29.00   1.00    5.00    --  -43.13  57.00-180.00   99
  6  \w    -85.00 -58.00   1.00    5.00    --  -43.13 -57.00 -90.00   27
  7  \w    -99.00 -21.00   1.00    5.00    --  -43.13 -37.00-180.00   78
  8  \w    -57.00 -19.00   1.00    5.00    --  -43.13 -37.00 -60.00   38
  9  \w     29.00  99.00   1.00    5.00    --   43.13-125.00  30.00   70
 10  \w     12.00  39.00   1.00    5.00    --   46.00  81.00   7.36   27
 11  \w     16.00  43.00   1.00    5.00    --   50.00  82.00 136.19   27
 12  \w     18.00  43.00   1.00    5.00    --   50.00  80.00  57.41   25
 13  \w     17.00  42.00   1.00    5.00    --   50.00  80.00-128.86   25
 14  \w     20.00  45.00   1.00    5.00    --   54.00  81.00 -62.24   25
 15  \w     35.00  62.00   1.00    5.00    --   62.00  75.00 170.31   27
 16  \w     31.00  58.00   1.00    5.00    --   62.00  75.00-110.69   27
 17  \w     31.00  58.00   1.00    5.00    --   62.00  76.00 -31.58   27
 18  \w     34.00  61.00   1.00    5.00    --   66.00  76.00  14.48   27
 19  \w     38.00  69.00   1.00    5.00    --   70.00  75.00 -85.39   31
 20  \w     38.00  65.00   1.00    5.00    --   70.00  76.00  77.56   27
 21  \w    125.00 150.00   1.00    5.00    --   74.00  77.00  37.12   25
 22  \w     43.00  70.00   1.00    5.00    --   74.00  77.00  37.12   27
 23  \w     43.00  72.00   1.00    5.00    --   74.00  76.00 103.57   29
 24  \w     43.00  69.00   1.00    5.00    --   74.00  76.00  21.14   26
 25  \w    125.00 150.00   1.00    5.00    --   74.00  76.00  21.14   25
 26  \w    108.00 149.00   1.00    5.00    --   74.00  76.00-164.27   41
 27  \w     43.00  72.00   1.00    5.00    --   74.00  76.00-164.27   29
 28  \w     41.00  74.00   1.00    5.00    --   74.00  77.00 -29.55   33
 29  \w     47.00  77.00   1.00   20.00    --   78.00  70.00 146.78   30
 30  \w    132.00 157.00   1.00   20.00    --   82.00  74.00-127.05   25
 31  \w     50.00  76.00   1.00   20.00    --   82.00  74.00-127.05   26
 32  \w     52.00  79.00   1.00   20.00    --   82.00  67.00  69.77   27
 33  \w     61.00  88.00   1.00   20.00    --   86.00  61.00-112.32   27
 34  \w     59.00  85.00   1.00   20.00    --   86.00  49.00  52.20   26
 35  \w     58.00  95.00   1.00   20.00    --   90.00  74.00 -74.45   37
 36  \w     63.00  98.00   1.00   20.00    --   94.00  69.00  73.90   35
 37  \w     70.00  96.00   1.00   20.00    --   98.00  61.00 -13.56   26
 38  \w    149.00 176.00   1.00   20.00    --  102.00  70.00-122.78   27
 39  \w     71.00  98.00   1.00   20.00    --  102.00  70.00-122.78   27
 40  \w     77.00 135.00   1.00   20.00    --  109.26  77.00-180.00   58
 41  \w     34.00 112.00   1.00   20.00    --  109.26 -77.00 150.00   78
 42  \w     78.00 169.00   1.00   20.00    --  109.26  77.00   0.00   91
 43  \w     50.00 107.00   1.00   20.00    --  109.26-111.00  30.00   57
 44  \w    112.00 168.00   1.00   20.00    --  109.26  77.00 120.00   56
 45  \w     77.00 103.00   1.00   20.00    --  109.26  77.00 120.00   26
 46  \w     77.00 157.00   1.00   20.00    --  109.26  77.00 -60.00   80
 47  \w     77.00 148.00   1.00   20.00    --  109.26  77.00-120.00   71
 48  \w     80.00 114.00   1.00   20.00    --  109.26  61.00-180.00   34
 49  \w     33.00  91.00   1.00   20.00    --  109.26 -94.00 -60.00   58
 50  \w     83.00 110.00   1.00   20.00    --  109.26  61.00 150.00   27
 51  \w     80.00 175.00   1.00   20.00    --  109.26  61.00-150.00   95
 52  \w    119.00 169.00   1.00   20.00    --  109.26 111.00-180.00   50
 53  \w     87.00 149.00   1.00   20.00    --  109.26  77.00  60.00   62
 54  \w     78.00 169.00   1.00   20.00    --  109.26  77.00 -30.00   91
 55  \w    118.00 178.00   1.00   20.00    --  109.26  77.00 150.00   60
 56  \w     77.00 104.00   1.00   20.00    --  109.26  77.00 150.00   27
 57  \w     77.00 178.00   1.00   20.00    --  109.26  77.00  30.00  101
 58  \w     77.00 178.00   1.00   20.00    --  109.26  77.00  90.00  101
 59  \w     63.00 104.00   1.00   20.00    --  109.26 -94.00-120.00   41
 60  \w     79.00 171.00   1.00   20.00    --  109.26  77.00 -90.00   92
 61  \w     48.00 116.00   1.00   20.00    --  109.26-111.00 120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_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_R_equivalents  0.1051
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23938
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.353
_diffrn_reflns_theta_min         3.699
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.445
_exptl_crystal_size_min          0.217
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5613
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0756P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                4424
_reflns_number_total             5613
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01181_si_004.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4132058
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              38261
_shelx_hkl_checksum              34413