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_4132062
_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         'C64 H57 Cl N2 Ni, C7 H8'
_chemical_formula_sum            'C71 H65 Cl N2 Ni'
_chemical_formula_weight         1040.41
_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                 98.0106(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.34517(16)
_cell_length_b                   21.7875(3)
_cell_length_c                   22.0081(3)
_cell_measurement_reflns_used    19048
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.1100
_cell_measurement_theta_min      4.0190
_cell_volume                     5861.77(14)
_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 0.980
_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    -74.00  36.00   1.00   10.00    --  -43.13  19.00  30.00  110
  2  \w    -14.00  13.00   1.00   10.00    --  -43.13  37.00  60.00   27
  3  \w   -124.00 -81.00   1.00   10.00    --  -43.13 -99.00  90.00   43
  4  \w    -62.00  28.00   1.00   10.00    --  -43.13  37.00 120.00   90
  5  \w     47.00  91.00   1.00   10.00    --   43.13-125.00   0.00   44
  6  \w     32.00  84.00   1.00   10.00    --   43.13-125.00-180.00   52
  7  \w     71.00 107.00   1.00   10.00    --   43.13  37.00-150.00   36
  8  \w     82.00 172.00   1.00   40.00    --  109.26  30.00-120.00   90
  9  \w    105.00 175.00   1.00   40.00    --  109.26  86.00 103.00   70
 10  \w    101.00 175.00   1.00   40.00    --  109.26 111.00  30.00   74
 11  \w     38.00 106.00   1.00   40.00    --  109.26-111.00 -30.00   68
 12  \w     98.00 177.00   1.00   40.00    --  109.26  61.00 150.00   79
 13  \w     34.00 114.00   1.00   40.00    --  109.26-111.00-120.00   80
 14  \w    134.00 173.00   1.00   40.00    --  109.26  30.00-150.00   39
 15  \w     53.00 135.00   1.00   40.00    --  109.26 -30.00  30.00   82
 16  \w     51.00  99.00   1.00   40.00    --  109.26 -94.00 150.00   48
 17  \w     77.00 102.00   1.00   40.00    --  109.26 178.00 120.00   25
 18  \w     48.00  73.00   1.00   40.00    --  109.26 -94.00   0.00   25
 19  \w     51.00 114.00   1.00   40.00    --  109.26-111.00  60.00   63
 20  \w    116.00 142.00   1.00   40.00    --  109.26 111.00   0.00   26
 21  \w     90.00 116.00   1.00   40.00    --  109.26  30.00-150.00   26
 22  \w     27.00 109.00   1.00   40.00    --  109.26 -94.00  90.00   82
;
_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  0.0433
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47552
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.485
_diffrn_reflns_theta_min         3.616
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.213
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.352
_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            red
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       plate
_exptl_crystal_F_000             2200
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 9359 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1341
_refine_ls_number_reflns         23604
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0838P)^2^+0.6493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                21423
_reflns_number_total             23604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01181_si_007.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        5861.77(13)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4132062
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              39934
_shelx_hkl_checksum              57821
_shelx_fab_checksum              15222