Catalytically Relevant Intermediates in the Ni-Catalyzed C(sp<sup>2</sup>)-H and C(sp<sup>3</sup>)-H Functionalization of Aminoquinoline Substrates.
Roy, Pronay; Bour, James R.; Kampf, Jeff W.; Sanford, Melanie S.; Journal of the American Chemical Society 141 (2019) 17382–17387; doi:10.1021/jacs.9b09109

data_4127885
_publ_section_title
;
 Catalytically Relevant Intermediates in the Ni-Catalyzed
 C(sp<sup>2</sup>)-H and C(sp<sup>3</sup>)-H Functionalization of
 Aminoquinoline Substrates.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17382
_journal_page_last               17387
_journal_paper_doi               10.1021/jacs.9b09109
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C22 H17 N3 Ni O'
_chemical_formula_sum            'C22 H17 N3 Ni O'
_chemical_formula_weight         398.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90.7060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.36830(10)
_cell_length_b                   9.11630(10)
_cell_length_c                   19.1021(2)
_cell_measurement_reflns_used    18039
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      69.2290
_cell_measurement_theta_min      4.2420
_cell_volume                     1805.40(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Satturn 944+ CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26446
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.476
_diffrn_reflns_theta_min         4.264
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    1.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0569P)^2^+1.1862P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3309
_reflns_number_total             3364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09109_si_002.cif
_cod_data_source_block           2a
_cod_database_code               4127885
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.850
_shelx_estimated_absorpt_t_max   0.906
_shelx_res_checksum              75996
_shelx_hkl_checksum              63728