Nickel-Catalyzed Regioselective 1,4-Hydroboration of N-Heteroarenes
Tamang, Sem Raj; Singh, Arpita; Unruh, Daniel K.; Findlater, Michael; ACS Catalysis 8 (2018) 6186–; doi:10.1021/acscatal.8b01166

data_4515702
_publ_section_title
;
 Nickel-Catalyzed Regioselective 1,4-Hydroboration of N-Heteroarenes
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6186
_journal_paper_doi               10.1021/acscatal.8b01166
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C24 H28 N2 Ni O8'
_chemical_formula_sum            'C24 H28 N2 Ni O8'
_chemical_formula_weight         531.19
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                101.952(14)
_cell_angle_beta                 99.095(8)
_cell_angle_gamma                99.806(9)
_cell_formula_units_Z            1
_cell_length_a                   6.736(3)
_cell_length_b                   8.129(3)
_cell_length_c                   11.969(5)
_cell_measurement_reflns_used    7304
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      2.61
_cell_volume                     619.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13805
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.270
_diffrn_reflns_theta_min         1.775
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       blade
_exptl_crystal_F_000             278
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0243
_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^)+(0.0275P)^2^+0.3187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0626
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2598
_reflns_number_total             2780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01166_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4515702
_shelx_estimated_absorpt_t_min   0.688
_shelx_estimated_absorpt_t_max   0.925
_shelxl_version_number           2013-4
_shelx_res_checksum              50923
_shelx_hkl_checksum              70883