Nickel-Catalyzed Directed C6-Selective C-H Alkylation of 2-Pyridones with Dienes and Activated Alkenes.
Miura, Wataru; Hirano, Koji; Miura, Masahiro; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b00682

data_4032489
_publ_section_title
;
 Nickel-Catalyzed Directed C6-Selective C-H Alkylation of 2-Pyridones with
 Dienes and Activated Alkenes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00682
_journal_year                    2017
_chemical_formula_moiety         'C17 H16 N2 O'
_chemical_formula_sum            'C17 H16 N2 O'
_chemical_formula_weight         264.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                104.25(3)
_cell_angle_beta                 93.336(19)
_cell_angle_gamma                90.50(4)
_cell_formula_units_Z            4
_cell_length_a                   9.036(18)
_cell_length_b                   12.31(3)
_cell_length_c                   12.72(3)
_cell_measurement_reflns_used    1757
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     1369(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 13.653
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14518
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_min         3.013
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560.00
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2225
_refine_ls_R_factor_gt           0.1011
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1194P)^2^+0.2394P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2282
_refine_ls_wR_factor_ref         0.3059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2490
_reflns_number_total             6255
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo7b00682_si_003.cif
_cod_data_source_block           963-6
_cod_database_code               4032489
_shelx_res_checksum              20785
_shelx_hkl_checksum              81647