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_4515698
_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_sum            'C13 H22 B N O2'
_chemical_formula_weight         235.12
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-04-20T09:48:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.218(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.204(4)
_cell_length_b                   34.935(19)
_cell_length_c                   11.091(6)
_cell_measurement_reflns_used    2252
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.27
_cell_measurement_theta_min      2.18
_cell_volume                     2789(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5124
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.47
_diffrn_reflns_theta_min         1.166
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.12
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5124
_refine_ls_number_restraints     282
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.0976
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1307P)^2^+3.2471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2671
_refine_ls_wR_factor_ref         0.3043
_reflns_number_gt                2788
_reflns_number_total             5124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01166_si_008.cif
_cod_data_source_block           fin18_15
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4515698
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              6979
_shelx_hkl_checksum              42732