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_4518147
_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         '2(Br4 Mn1), 1(Br), 4(C30 H24 Co1 N6)'
_chemical_formula_sum            'C120 H96 Br9 Co4 Mn2 N24'
_chemical_formula_weight         2938.99
_space_group_crystal_system      hexagonal
_space_group_IT_number           182
_space_group_name_Hall           'P 6c 2c'
_space_group_name_H-M_alt        'P 63 2 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   13.2935(5)
_cell_length_b                   13.2935(5)
_cell_length_c                   40.9000(16)
_cell_measurement_reflns_used    9722
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.372
_cell_measurement_theta_min      2.316
_cell_volume                     6259.4(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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  0.0468
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            37195
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.098
_diffrn_reflns_theta_min         2.030
_diffrn_source_current           31.0
_diffrn_source_power             1.705
_diffrn_source_voltage           55.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.642
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.?wR2(int) was 0.0995 before and 0.0550 after correction.?The Ratio of minimum to maximum transmission is 0.7076.?The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       plate
_exptl_crystal_F_000             2914
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.010(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         6096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+3.3114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                5151
_reflns_number_total             6096
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03903_si_002.cif
_cod_data_source_block           Co-Red
_cod_original_cell_volume        6259.4(5)
_cod_database_code               4518147
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.868
_shelx_estimated_absorpt_t_min   0.274
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.990(11)
 0.010(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              77986
_shelx_hkl_checksum              17112
_shelx_fab_checksum              32425
_olex2_submission_special_instructions 'No special instructions were received'