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_4135501
_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         'C50H42N3NiO C2H4O0.5 C2.5H2.5N0.5'
_chemical_formula_sum            'C54.5 H48.5 N3.5 Ni O2.5'
_chemical_formula_weight         851.18
_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            4
_cell_length_a                   10.06432(11)
_cell_length_b                   13.6461(2)
_cell_length_c                   35.0160(4)
_cell_measurement_reflns_used    9484
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.404
_cell_measurement_theta_min      3.476
_cell_volume                     4809.05(10)
_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 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector
;
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0884
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            44188
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        66.586
_diffrn_reflns_theta_max         66.586
_diffrn_reflns_theta_min         4.107
_diffrn_source                   'I/mS microfocus tube'
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_process_details   SADBAS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       needle
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 2399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         7785
_refine_ls_number_restraints     140
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0635
_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^)+(0.1317P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1794
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.872
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                6612
_reflns_number_total             7785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09839_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 4135500--4135503.cif.'
_cod_original_cell_volume        4809.05(11)
_cod_original_formula_sum        'C54.50 H48.50 N3.50 Ni O2.50'
_cod_database_code               4135501
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.6845
_shelx_estimated_absorpt_t_max   0.7509
_shelx_res_checksum              39610
_shelx_hkl_checksum              89997