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_4515696
_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            'C20 H26 N O4 Zn'
_chemical_formula_weight         409.79
_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             2018-04-20T16:05:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 101.668(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.811(3)
_cell_length_b                   16.451(4)
_cell_length_c                   11.445(3)
_cell_measurement_reflns_used    5309
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.39
_cell_measurement_theta_min      2.20
_cell_volume                     1993.5(9)
_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 1
_diffrn_measured_fraction_theta_max 0.998
_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  0.0969
_diffrn_reflns_av_unetI/netI     0.1172
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4535
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.358
_diffrn_reflns_theta_min         2.199
_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       plate
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.958
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.09
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4535
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.1841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                3519
_reflns_number_total             4535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01166_si_006.cif
_cod_data_source_block           fin18_16
_cod_original_cell_volume        1993.6(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4515696
_shelx_estimated_absorpt_t_min   0.584
_shelx_estimated_absorpt_t_max   0.934
_shelx_res_checksum              55994
_shelx_hkl_checksum              71595