A dual biomimetic process for the selective aerobic oxidative coupling of primary amines using pyrogallol as a precatalyst. Isolation of the [5 + 2] cycloaddition redox intermediates
Largeron, Martine; Deschamps, Patrick; Hammad, Karim; Fleury, Maurice-Bernard; Green Chemistry 22 (2020) 1894–1905; doi:10.1039/C9GC03992A

data_7239953
_publ_section_title
;
 A dual biomimetic process for the selective aerobic oxidative coupling of
 primary amines using pyrogallol as a precatalyst. Isolation of the [5 +
 2] cycloaddition redox intermediates
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              1894
_journal_page_last               1905
_journal_paper_doi               10.1039/C9GC03992A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C16 H14 N2'
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_chemical_name_systematic        2-cyclopropyl-1-phenyl-1H-benzoimidazole
_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-2016/6
_audit_update_record
;
2020-02-04 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                103.3680(10)
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_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      59.0
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_cell_volume                     1214.77(8)
_computing_cell_refinement       'Bruker SAINT'
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_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS ICMMO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
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_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
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_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        59.042
_diffrn_reflns_theta_max         59.042
_diffrn_reflns_theta_min         4.106
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.9516
_exptl_absorpt_correction_T_min  0.8840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0380P)^2^+0.4114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3328
_reflns_number_total             3491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc03992a2.cif
_cod_data_source_block           25d
_cod_depositor_comments
;Adding full bibliography for 7239951--7239953.cif.

 Adding full bibliography for 7239951--7239953.cif.
;
_cod_database_code               7239953
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.943
_shelx_res_checksum              81729