Cobalt-Catalyzed C(sp2)‒CN Bond Activation: Cross-Electrophile Coupling for Biaryl Formation and Mechanistic Insight
Dorval, Céline; Tricoire, Maxime; Begouin, Jeanne-Marie; Gandon, Vincent; Gosmini, Corinne; ACS Catalysis  (2020) 12819–12827; doi:10.1021/acscatal.0c03903

data_4518146
_publ_section_title
;
 Cobalt-Catalyzed C(sp2)--CN Bond Activation: Cross-Electrophile Coupling
 for Biaryl Formation and Mechanistic Insight
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              12819
_journal_page_last               12827
_journal_paper_doi               10.1021/acscatal.0c03903
_journal_year                    2020
_chemical_formula_moiety         'C20 H16 Br2 Co N4'
_chemical_formula_sum            'C20 H16 Br2 Co N4'
_chemical_formula_weight         531.12
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.596(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5670(7)
_cell_length_b                   14.5739(10)
_cell_length_c                   15.6200(11)
_cell_measurement_reflns_used    3860
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      24.2370
_cell_measurement_theta_min      2.6310
_cell_volume                     1933.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT(Sheldrick,2014)
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23711
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.631
_exptl_absorpt_coefficient_mu    5.034
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0274P)^2^+1.8435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3287
_reflns_number_total             4435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03903_si_002.cif
_cod_data_source_block           CoBr2Bipy2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4518146
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.314
_shelx_estimated_absorpt_t_max   0.464
_shelx_res_checksum              98375
_shelx_hkl_checksum              34823