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_4128968
_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 H25 Cl Co N5, 5(C H Cl3), Cl'
_chemical_formula_sum            'C28 H30 Cl17 Co N5'
_chemical_formula_weight         1098.15
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 109.4060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6143(7)
_cell_length_b                   18.8932(9)
_cell_length_c                   18.3407(9)
_cell_measurement_reflns_used    6877
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      23.9017
_cell_measurement_theta_min      2.3547
_cell_volume                     4449.5(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2014)'
_computing_data_collection       'Bruker Instrument Service v2015.5.1.3'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'XShell ver. 6.3.1 (Bruker AXS, 2004)'
_computing_publication_material  'Bruker APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL XT-2014/4'
_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 Diffractometer'
_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  0.0606
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37075
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.92
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    1.436
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear light brown-yellow'
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2196
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.110
_refine_diff_density_max         2.710
_refine_diff_density_min         -1.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         8163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0744
_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^)+(0.1220P)^2^+9.6148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1977
_refine_ls_wR_factor_ref         0.2135
_reflns_number_gt                6332
_reflns_number_total             8163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07529_si_002.cif
_cod_data_source_block           PyEtPDICoCl2
_cod_database_code               4128968
_shelx_res_checksum              76474
_shelx_hkl_checksum              16757