Efficient Cobalt Catalyst for Ambient-Temperature Nitrile Dihydroboration, the Elucidation of a Chelate-Assisted Borylation Mechanism, and a New Synthetic Route to Amides.
Ghosh, Chandrani; Kim, Suyeon; Mena, Matthew R.; Kim, Jun-Hyeong; Pal, Raja; Rock, Christopher L.; Groy, Thomas L.; Baik, Mu-Hyun; Trovitch, Ryan J.; Journal of the American Chemical Society 141 (2019) 15327–15337; doi:10.1021/jacs.9b07529

data_4128969
_publ_section_title
;
 Efficient Cobalt Catalyst for Ambient-Temperature Nitrile
 Dihydroboration, the Elucidation of a Chelate-Assisted Borylation
 Mechanism, and a New Synthetic Route to Amides.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15327
_journal_page_last               15337
_journal_paper_doi               10.1021/jacs.9b07529
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C23 H26 Co N5'
_chemical_formula_sum            'C23 H26 Co N5'
_chemical_formula_weight         431.42
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                105.192(2)
_cell_angle_beta                 92.884(2)
_cell_angle_gamma                107.735(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6432(10)
_cell_length_b                   11.3302(13)
_cell_length_c                   11.4891(14)
_cell_measurement_reflns_used    1180
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      23.6975
_cell_measurement_theta_min      2.2805
_cell_volume                     1023.8(2)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection
'Bruker Instrument Service v2010, 9, 0, 0 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'XShell ver. 6.3.1 (Bruker AXS, 2004)'
_computing_publication_material  'Bruker APEX2 v2010.9-1 (Bruker AXS, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3751
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         1.86
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS Version 2008/4 (Bruker AXS, 2008)'
_exptl_crystal_colour            'dark bronze'
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.331
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0510P)^2^+0.4006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                3214
_reflns_number_total             3751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07529_si_003.cif
_cod_data_source_block           PyEtPDICoH
_cod_database_code               4128969
_shelx_res_checksum              25083
_shelx_hkl_checksum              2560