Selective C(sp3)–H Cleavage of Enamides for Synthesis of 2-Pyridones via Ligand-Enabled Ni–Al Bimetallic Catalysis
Wang, Rong-Hua; Li, Jiang-Fei; Li, Yue; Qi, Shao-Long; Zhang, Tao; Luan, Yu-Xin; Ye, Mengchun; ACS Catalysis 11 (2021) 858–864; doi:10.1021/acscatal.0c04585

data_4518468
_publ_section_title
;
 Selective C(sp3)--H Cleavage of Enamides for Synthesis of 2-Pyridones via
 Ligand-Enabled Ni--Al Bimetallic Catalysis
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              858
_journal_page_last               864
_journal_paper_doi               10.1021/acscatal.0c04585
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C18 H17 N O S2'
_chemical_formula_sum            'C18 H17 N O S2'
_chemical_formula_weight         327.44
_chemical_name_systematic        2-pyridone
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 99.18(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5910(11)
_cell_length_b                   21.778(4)
_cell_length_c                   12.608(3)
_cell_measurement_reflns_used    3998
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9624
_cell_measurement_theta_min      1.8702
_cell_volume                     1515.5(6)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17963
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.879
_diffrn_reflns_theta_min         1.870
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7166
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             688
_exptl_crystal_preparation       'in DCM'
_exptl_crystal_recrystallization_method
'keep stationary for slow evaporation for one week'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1145P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.1787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2821
_reflns_number_total             3601
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04585_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1515.5(5)
_cod_database_code               4518468
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.933
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              63572
_shelx_hkl_checksum              40245
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_original_sample_id wrh-pyridone
_olex2_submission_special_instructions 'No special instructions were received'