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_4132063
_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 Au Cl N2, 2(C H2 Cl2)'
_chemical_formula_sum            'C51 H52 Au Cl5 N2'
_chemical_formula_weight         1067.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 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                 114.290(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.8368(6)
_cell_length_b                   11.3047(3)
_cell_length_c                   14.2276(5)
_cell_measurement_reflns_used    17076
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      75.4510
_cell_measurement_theta_min      3.3890
_cell_volume                     2321.68(15)
_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      99.9(3)
_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     12.00  38.00   1.00    1.00    --   46.00  81.00  10.77   26
  2  \w     30.00  72.00   1.00    1.00    --   62.00  77.00 -20.89   42
  3  \w     78.00 138.00   1.00    1.00    --   62.00  77.00 -20.89   60
  4  \w    106.00 132.00   1.00    1.00    --   62.00  77.00  38.47   26
  5  \w    108.00 144.00   1.00    1.00    --   70.00  77.00  61.31   36
  6  \w    150.00 176.00   1.00    4.00    --  112.00  77.00 150.00   26
  7  \w    123.00 166.00   1.00    4.00    --  112.00  61.00 150.00   43
  8  \w    130.00 163.00   1.00    4.00    --  112.00  77.00   0.00   33
  9  \w    123.00 166.00   1.00    4.00    --  112.00  61.00 -30.00   43
 10  \w    146.00 178.00   1.00    4.00    --  112.00 111.00 -90.00   32
 11  \w    127.00 154.00   1.00    4.00    --  112.00  77.00-180.00   27
 12  \w    113.00 159.00   1.00    4.00    --  112.00  77.00-120.00   46
 13  \w    108.00 173.00   1.00    4.00    --  112.00 111.00 -30.00   65
 14  \w    107.00 143.00   1.00    4.00    --  112.00 111.00 -90.00   36
 15  \w     92.00 120.00   1.00    1.00    --   58.00  75.00 -47.65   28
 16  \w     83.00 140.00   1.00    1.00    --   66.00  76.00-168.20   57
 17  \w     83.00 110.00   1.00    4.00    --  112.00  61.00-120.00   27
 18  \w     84.00 157.00   1.00    4.00    --  112.00  61.00 -90.00   73
 19  \w     87.00 128.00   1.00    4.00    --  112.00  61.00  30.00   41
 20  \w     85.00 128.00   1.00    4.00    --  112.00  61.00   0.00   43
 21  \w     80.00 178.00   1.00    4.00    --  112.00  77.00  90.00   98
 22  \w     86.00 113.00   1.00    1.00    --   70.00  75.00 141.15   27
 23  \w     79.00 112.00   1.00    4.00    --  112.00  77.00 150.00   33
 24  \w     85.00 111.00   1.00    4.00    --  112.00  61.00 150.00   26
 25  \w     79.00 177.00   1.00    4.00    --  112.00  77.00 120.00   98
 26  \w     80.00 105.00   1.00    4.00    --  112.00  77.00 -30.00   25
 27  \w     84.00 119.00   1.00    4.00    --  112.00  61.00 -30.00   35
 28  \w     79.00 106.00   1.00    4.00    --  112.00  77.00-120.00   27
 29  \w     79.00 178.00   1.00    4.00    --  112.00  77.00-150.00   99
 30  \w     80.00 105.00   1.00    4.00    --  112.00  77.00-180.00   25
 31  \w     84.00 177.00   1.00    4.00    --  112.00  61.00-180.00   93
 32  \w     79.00 176.00   1.00    4.00    --  112.00  77.00  30.00   97
 33  \w     79.00 178.00   1.00    4.00    --  112.00  77.00  60.00   99
 34  \w     83.00 124.00   1.00    4.00    --  112.00  61.00  90.00   41
 35  \w     79.00 105.00   1.00    4.00    --  112.00  77.00   0.00   26
 36  \w     79.00 177.00   1.00    4.00    --  112.00  77.00 -60.00   98
 37  \w     79.00 120.00   1.00    4.00    --  112.00  77.00 -90.00   41
 38  \w     42.00  82.00   1.00    1.00    --   74.00  77.00  87.94   40
 39  \w     38.00  69.00   1.00    1.00    --   70.00  75.00 141.15   31
 40  \w     37.00  62.00   1.00    1.00    --   70.00  77.00  61.31   25
 41  \w     29.00  55.00   1.00    1.00    --   62.00  77.00  38.47   26
 42  \w     12.00  43.00   1.00    1.00    --   46.00  82.00 118.23   31
 43  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 174.19   25
 44  \w      5.00  30.00   1.00    1.00    --   42.00  90.00 157.82   25
 45  \w     26.00  52.00   1.00    1.00    --   58.00  75.00 -47.65   26
 46  \w     37.00  76.00   1.00    1.00    --   70.00  77.00 -55.89   39
 47  \w     38.00  76.00   1.00    1.00    --   70.00  76.00-121.12   38
 48  \w     34.00  67.00   1.00    1.00    --   66.00  76.00-168.20   33
 49  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 -98.86   25
 50  \w     20.00  45.00   1.00    1.00    --   54.00  81.00-143.78   25
 51  \w      0.00  25.00   1.00    1.00    --   38.00  92.00 -66.26   25
 52  \w     73.00 117.00   1.00    4.00    --  112.00 -61.00-150.00   44
 53  \w     60.00 115.00   1.00    4.00    --  112.00-111.00 -30.00   55
 54  \w     82.00 107.00   1.00    4.00    --  112.00 -94.00  60.00   25
 55  \w     49.00  75.00   1.00    4.00    --  112.00 -94.00  60.00   26
 56  \w     48.00 144.00   1.00    4.00    --  112.00 -77.00 -30.00   96
 57  \w     54.00 116.00   1.00    4.00    --  112.00-111.00-150.00   62
 58  \w     43.00 106.00   1.00    4.00    --  112.00 -94.00-120.00   63
 59  \w     25.00  77.00   1.00    1.00    --   40.91-125.00 -90.00   52
 60  \w      2.00  80.00   1.00    1.00    --   40.91 -99.00   0.00   78
 61  \w     39.00 110.00   1.00    4.00    --  112.00-111.00 150.00   71
 62  \w      1.00  71.00   1.00    1.00    --   40.91 -99.00 120.00   70
 63  \w    -74.00 -17.00   1.00    1.00    --  -40.91 -38.00 -90.00   57
 64  \w   -115.00 -76.00   1.00    1.00    --  -40.91 -38.00 -90.00   39
 65  \w   -111.00 -20.00   1.00    1.00    --  -40.91 -38.00  30.00   91
 66  \w   -109.00 -13.00   1.00    1.00    --  -40.91 -57.00 150.00   96
;
_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  0.0000
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6816
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.214
_diffrn_reflns_theta_min         3.408
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.878
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.087
_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    1.527
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.551
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.086
_refine_diff_density_max         2.365
_refine_diff_density_min         -2.089
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.009(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         6816
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0531
_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^)+(0.1210P)^2^+8.5379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1463
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                6816
_reflns_number_total             6816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01181_si_005.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        2321.70(15)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4132063
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              8856
_shelx_hkl_checksum              41241