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_4132060
_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         'C49 H48 N2'
_chemical_formula_sum            'C49 H48 N2'
_chemical_formula_weight         664.89
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6720(4)
_cell_length_b                   18.1421(5)
_cell_length_c                   18.3663(5)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    140.01(10)
_cell_measurement_theta_max      74.2790
_cell_measurement_theta_min      4.4050
_cell_volume                     3889.1(2)
_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      140.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1333
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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      5.00  32.00   1.00    7.50    --   42.00  89.00 108.61   27
  2  \w      5.00  30.00   1.00    7.50    --   42.00  89.00 -60.22   25
  3  \w   -112.00 -15.00   1.00    7.50    --  -42.01 -57.00-150.00   97
  4  \w   -115.00 -14.00   1.00    7.50    --  -42.01 -57.00  60.00  101
  5  \w   -116.00 -18.00   1.00    7.50    --  -42.01 -37.00 -60.00   98
  6  \w    -70.00  30.00   1.00    7.50    --  -42.01  57.00   0.00  100
  7  \w     23.00  98.00   1.00    7.50    --   42.01-125.00-180.00   75
  8  \w     11.00  36.00   1.00    7.50    --   46.00  84.00  72.03   25
  9  \w     11.00  36.00   1.00    7.50    --   46.00  84.00-134.42   25
 10  \w     21.00  46.00   1.00    7.50    --   54.00  79.00   8.60   25
 11  \w     20.00  45.00   1.00    7.50    --   54.00  81.00 -92.18   25
 12  \w     20.00  46.00   1.00    7.50    --   54.00  81.00  64.01   26
 13  \w     20.00  45.00   1.00    7.50    --   54.00  81.00 146.20   25
 14  \w     21.00  46.00   1.00    7.50    --   54.00  79.00-131.34   25
 15  \w     31.00  58.00   1.00    7.50    --   62.00  76.00 154.38   27
 16  \w    114.00 141.00   1.00    7.50    --   66.00  75.00 -50.88   27
 17  \w     34.00  60.00   1.00    7.50    --   66.00  75.00 -50.88   26
 18  \w     34.00  60.00   1.00    7.50    --   66.00  75.00  55.11   26
 19  \w     34.00  59.00   1.00    7.50    --   66.00  77.00 -14.69   25
 20  \w     38.00  64.00   1.00    7.50    --   70.00  76.00-170.60   26
 21  \w     96.00 140.00   1.00    7.50    --   70.00  77.00-115.30   44
 22  \w     37.00  64.00   1.00    7.50    --   70.00  77.00-115.30   27
 23  \w     42.00  68.00   1.00    7.50    --   74.00  76.00  75.47   26
 24  \w     41.00  75.00   1.00    7.50    --   74.00  77.00 110.43   34
 25  \w     42.00  68.00   1.00    7.50    --   74.00  75.00  12.37   26
 26  \w     42.00  76.00   1.00    7.50    --   74.00  75.00 -41.23   34
 27  \w     42.00  74.00   1.00    7.50    --   74.00  76.00 164.67   32
 28  \w     46.00  72.00   1.00   20.00    --   78.00  75.00 -97.00   26
 29  \w     46.00  71.00   1.00   20.00    --   78.00  77.00-147.87   25
 30  \w     98.00 146.00   1.00   20.00    --   82.00  74.00  27.89   48
 31  \w     51.00  84.00   1.00   20.00    --   82.00  74.00  27.89   33
 32  \w    127.00 159.00   1.00   20.00    --   86.00  69.00-174.68   32
 33  \w     55.00  85.00   1.00   20.00    --   86.00  69.00-174.68   30
 34  \w     59.00  85.00   1.00   20.00    --   90.00  71.00 -10.48   26
 35  \w     58.00  91.00   1.00   20.00    --   90.00  76.00-107.60   33
 36  \w     58.00  84.00   1.00   20.00    --   90.00  76.00-144.95   26
 37  \w     58.00  84.00   1.00   20.00    --   90.00  76.00  89.33   26
 38  \w     62.00  88.00   1.00   20.00    --   94.00  74.00 -63.88   26
 39  \w     69.00 110.00   1.00   20.00    --   98.00  68.00  94.82   41
 40  \w     65.00 174.00   1.00   20.00    --   98.00  77.00 -19.01  109
 41  \w     85.00 162.00   1.00   20.00    --  109.26  61.00 -90.00   77
 42  \w     81.00 143.00   1.00   20.00    --  109.26  61.00 150.00   62
 43  \w    110.00 174.00   1.00   20.00    --  109.26  77.00  90.00   64
 44  \w     78.00 104.00   1.00   20.00    --  109.26  77.00  90.00   26
 45  \w    111.00 146.00   1.00   20.00    --  109.26 178.00-150.00   35
 46  \w     77.00 169.00   1.00   20.00    --  109.26  77.00 -60.00   92
 47  \w    135.00 161.00   1.00   20.00    --  109.26  61.00 120.00   26
 48  \w     81.00 107.00   1.00   20.00    --  109.26  61.00 120.00   26
 49  \w     77.00 173.00   1.00   20.00    --  109.26  77.00 150.00   96
 50  \w     77.00 178.00   1.00   20.00    --  109.26  77.00-150.00  101
 51  \w    109.00 170.00   1.00   20.00    --  109.26  77.00   0.00   61
 52  \w     77.00 105.00   1.00   20.00    --  109.26  77.00   0.00   28
 53  \w     81.00 176.00   1.00   20.00    --  109.26  61.00  60.00   95
 54  \w     77.00 103.00   1.00   20.00    --  109.26  77.00 120.00   26
 55  \w    116.00 178.00   1.00   20.00    --  109.26  77.00-120.00   62
 56  \w     77.00 103.00   1.00   20.00    --  109.26  77.00-120.00   26
 57  \w     35.00 142.00   1.00   20.00    --  109.26 -77.00-180.00  107
 58  \w     79.00 144.00   1.00   20.00    --  109.26  77.00-180.00   65
 59  \w    116.00 173.00   1.00   20.00    --  109.26  77.00  30.00   57
 60  \w     77.00 103.00   1.00   20.00    --  109.26  77.00  30.00   26
 61  \w     30.00 109.00   1.00   20.00    --  109.26 -94.00   0.00   79
 62  \w     29.00  77.00   1.00   20.00    --  109.26 -94.00  60.00   48
 63  \w     34.00 111.00   1.00   20.00    --  109.26-111.00-180.00   77
 64  \w     87.00 115.00   1.00   20.00    --  109.26-111.00 -60.00   28
;
_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  0.0000
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9646
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.578
_diffrn_reflns_theta_max         66.578
_diffrn_reflns_theta_min         3.424
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.642
_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            colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1830 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         9646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.896
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0595P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6486
_reflns_number_total             9646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01181_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4132060
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              16820
_shelx_hkl_checksum              92211