Carboxylate breaks the arene C‒H bond via a hydrogen-atom-transfer mechanism in electrochemical cobalt catalysis
Chen, Xin-Ran; Zhang, Shuo-Qing; Meyer, Tjark H.; Yang, Chun-Hui; Zhang, Qin-Hao; Liu, Ji-Ren; Xu, Hua-Jian; Cao, Fa-He; Ackermann, Lutz; Hong, Xin; Chemical Science 11 (2020) 5790–5796; doi:10.1039/D0SC01898H

data_1558085
_publ_section_title
;
 Carboxylate breaks the arene C--H bond via a hydrogen-atom-transfer
 mechanism in electrochemical cobalt catalysis
;
_journal_issue                   22
_journal_name_full               'Chemical Science'
_journal_page_first              5790
_journal_page_last               5796
_journal_paper_doi               10.1039/D0SC01898H
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         '2(C22 H23 Co N2 O6), C H2 Cl2'
_chemical_formula_sum            'C45 H48 Cl2 Co2 N4 O12'
_chemical_formula_weight         1025.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-02 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.22(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.880(14)
_cell_length_b                   7.915(8)
_cell_length_c                   30.41(6)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.38
_cell_volume                     4498(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_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  0.0762
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            35513
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.121
_diffrn_reflns_theta_min         2.396
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.924
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1241 before and 0.0739 after correction.
The Ratio of minimum to maximum transmission is 0.8212.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       plate
_exptl_crystal_F_000             2120
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.494
_refine_diff_density_min         -1.216
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.279
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.1113
_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^)+134.7771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2499
_refine_ls_wR_factor_ref         0.2562
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4089
_reflns_number_total             4907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01898h2.cif
_cod_data_source_block           191128_cxr_191128_0m
_cod_depositor_comments
;Adding full bibliography for 1558085.cif.

 Adding full bibliography for 1558085.cif.
;
_cod_database_code               1558085
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.844
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H23A(0.5) H23B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C20(H20)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              97278
_olex2_submission_special_instructions 'No special instructions were received'