Enantioselective C-H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands.
Dong, Yuyang; Lund, Colton J.; Porter, Gerard J.; Clarke, Ryan M.; Zheng, Shao-Liang; Cundari, Thomas R.; Betley, Theodore A.; Journal of the American Chemical Society 143 (2021) 817–829; doi:10.1021/jacs.0c09839

data_4135503
_publ_section_title
;
 Enantioselective C-H Amination Catalyzed by Nickel Iminyl Complexes
 Supported by Anionic Bisoxazoline (BOX) Ligands.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              817
_journal_page_last               829
_journal_paper_doi               10.1021/jacs.0c09839
_journal_volume                  143
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C55 H52 N3 Ni O2'
_chemical_formula_sum            'C55 H52 N3 Ni O2'
_chemical_formula_weight         845.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6441(8)
_cell_length_b                   28.862(2)
_cell_length_c                   42.241(2)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.803
_cell_measurement_theta_min      2.272
_cell_volume                     11757.7(14)
_computing_cell_refinement       'SAINT 8.35A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX3 v2016.1.0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT 8.35A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2083
_diffrn_reflns_av_unetI/netI     0.2318
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            92620
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.119
_diffrn_reflns_theta_max         25.119
_diffrn_reflns_theta_min         2.166
_diffrn_source                   'I/mS microfocus tube'
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_process_details   SADBAS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    0.956
_exptl_crystal_description       needle
_exptl_crystal_F_000             3576
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 2596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1145
_refine_ls_number_reflns         20814
_refine_ls_number_restraints     2080
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.1962
_refine_ls_R_factor_gt           0.0820
_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^)+(0.0857P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.2031
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                9438
_reflns_number_total             20814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09839_si_002.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 4135500--4135503.cif.'
_cod_database_code               4135503
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.6466
_shelx_estimated_absorpt_t_max   0.8012
_shelx_res_checksum              95011
_shelx_hkl_checksum              75663
_shelx_fab_checksum              72143