Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation.
Mills, Leo Reginald; Graham, Joshua; Patel, Purvish; Rousseaux, Sophie A. L.; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b11208

data_4132347
_publ_section_title
;
 Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives
 via Transnitrilation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b11208
_journal_year                    2019
_chemical_formula_moiety         'C17 H15 Br N2 Ni'
_chemical_formula_sum            'C17 H15 Br N2 Ni'
_chemical_formula_weight         385.93
_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-2018/3
_cell_angle_alpha                83.294(3)
_cell_angle_beta                 77.888(3)
_cell_angle_gamma                63.691(3)
_cell_formula_units_Z            4
_cell_length_a                   9.1066(4)
_cell_length_b                   10.0998(4)
_cell_length_c                   18.5656(6)
_cell_measurement_reflns_used    5863
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.12
_cell_measurement_theta_min      4.88
_cell_volume                     1496.07(11)
_computing_cell_refinement       APEX3
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
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_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1517
_diffrn_reflns_av_unetI/netI     0.1372
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_point_group_measured_fraction_full 0.989
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_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.342
_diffrn_reflns_theta_min         2.435
_diffrn_source                   'Bruker ImuS with multi-layer optics'
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_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Bruker, 2012)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.137
_refine_diff_density_min         -1.020
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_refine_ls_extinction_coef       0.00077(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0715
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+10.8669P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1537
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4113
_reflns_number_total             5377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11208_si_003.cif
_cod_data_source_block           d19133_a_5
_cod_database_code               4132347
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.525
_shelx_estimated_absorpt_t_max   0.908
_shelx_res_checksum              10833
_shelx_hkl_checksum              21595