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_4132059
_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         'C54 H53 Cl N2 Ni, C H2 Cl2'
_chemical_formula_sum            'C55 H55 Cl3 N2 Ni'
_chemical_formula_weight         909.07
_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-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 96.9576(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.46881(19)
_cell_length_b                   23.5381(3)
_cell_length_c                   14.6728(2)
_cell_measurement_reflns_used    17325
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2230
_cell_measurement_theta_min      3.0160
_cell_volume                     4617.47(11)
_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 0.989
_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   -103.00 -13.00   1.00    5.00    --  -40.91 -57.00-150.00   90
  2  \w    -68.00  29.00   1.00    5.00    --  -40.91  57.00  90.00   97
  3  \w   -112.00 -22.00   1.00    5.00    --  -40.91 -57.00  30.00   90
  4  \w   -117.00 -10.00   1.00    5.00    --  -40.91 -77.00 -30.00  107
  5  \w     54.00  97.00   1.00    5.00    --   40.91-125.00 -60.00   43
  6  \w     59.00 121.00   1.00   20.00    --  111.85-125.00  60.00   62
  7  \w     36.00  86.00   1.00   20.00    --  111.85 -77.00  60.00   50
  8  \w     43.00  81.00   1.00   20.00    --  111.85 -45.00  90.00   38
  9  \w     87.00 161.00   1.00   20.00    --  111.85  45.00-150.00   74
 10  \w     79.00 106.00   1.00   20.00    --  111.85 -94.00  90.00   27
 11  \w     37.00 138.00   1.00   20.00    --  111.85 -30.00 -60.00  101
 12  \w     98.00 144.00   1.00   20.00    --  111.85 -77.00  60.00   46
 13  \w     52.00  86.00   1.00   20.00    --  111.85 -94.00 -30.00   34
 14  \w    125.00 178.00   1.00   20.00    --  111.85 125.00  60.00   53
 15  \w    103.00 178.00   1.00   20.00    --  111.85  30.00  30.00   75
 16  \w     40.00 122.00   1.00   20.00    --  111.85-125.00 -90.00   82
 17  \w     88.00 178.00   1.00   20.00    --  111.85  45.00 -90.00   90
 18  \w     98.00 125.00   1.00   20.00    --  111.85 -45.00  90.00   27
 19  \w     39.00 138.00   1.00   20.00    --  111.85 -45.00-150.00   99
 20  \w     97.00 133.00   1.00   20.00    --  111.85 156.00-147.00   36
;
_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_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            35816
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.054
_diffrn_reflns_theta_min         3.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.495
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.401
_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 pale red'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       plate
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.037(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1168
_refine_ls_number_reflns         18586
_refine_ls_number_restraints     123
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.2453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1085
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                16891
_reflns_number_total             18586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01181_si_003.cif
_cod_data_source_block           jdi-1-711
_cod_original_cell_volume        4617.45(12)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4132059
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.514
_shelx_estimated_absorpt_t_max   0.822
_shelx_res_checksum              97310
_shelx_hkl_checksum              18187