Diverting C‒H Annulation Pathways: Nickel-Catalyzed Dehydrogenative Homologation of Aromatic Amides
He, Zhiqi; Huang, Yong; ACS Catalysis 6 (2016) 7814–; doi:10.1021/acscatal.6b02477

data_4516716
_publ_section_title
;
 Diverting C--H Annulation Pathways: Nickel-Catalyzed Dehydrogenative
 Homologation of Aromatic Amides
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7814
_journal_paper_doi               10.1021/acscatal.6b02477
_journal_volume                  6
_journal_year                    2016
_chemical_formula_sum            'C33 H22 Cl3 N4 Ni O2'
_chemical_formula_weight         671.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                79.797(7)
_cell_angle_beta                 80.388(7)
_cell_angle_gamma                89.868(6)
_cell_formula_units_Z            2
_cell_length_a                   9.00580(10)
_cell_length_b                   9.30910(10)
_cell_length_c                   17.9195(12)
_cell_measurement_reflns_used    14074
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      6.80
_cell_volume                     1457.21(11)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19127
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.271
_diffrn_reflns_theta_min         6.849
_exptl_absorpt_coefficient_mu    3.810
_exptl_absorpt_correction_T_max  0.470
_exptl_absorpt_correction_T_min  0.346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       prism
_exptl_crystal_F_000             686
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0676
_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^)+(0.1002P)^2^+1.1486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1791
_refine_ls_wR_factor_ref         0.2033
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3639
_reflns_number_total             5204
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02477_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4516716
_shelx_estimated_absorpt_t_min   0.725
_shelx_estimated_absorpt_t_max   0.832
_shelxl_version_number           2014-3
_shelx_res_checksum              89161
_shelx_hkl_checksum              23433