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_7239952
_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         'C17 H17 N'
_chemical_formula_sum            'C17 H17 N'
_chemical_formula_weight         235.31
_chemical_name_common
(E)-N-(2,3-dihydro-1H-inden-2-yl)-1(p-tolyl)methanimine
_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
_atom_sites_solution_primary     direct
_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                103.2590(10)
_cell_angle_beta                 95.0990(10)
_cell_angle_gamma                95.6240(10)
_cell_formula_units_Z            2
_cell_length_a                   5.6742(2)
_cell_length_b                   8.7921(4)
_cell_length_c                   13.5713(5)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.8
_cell_measurement_theta_min      3.37
_cell_volume                     651.48(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP(III)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_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
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21496
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        63.997
_diffrn_reflns_theta_max         63.997
_diffrn_reflns_theta_min         3.368
_diffrn_source                   'Fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  0.9524
_exptl_absorpt_correction_T_min  0.8641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0631P)^2^+0.2041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1995
_reflns_number_total             2166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc03992a2.cif
_cod_data_source_block           24j
_cod_depositor_comments
;Adding full bibliography for 7239951--7239953.cif.

 Adding full bibliography for 7239951--7239953.cif.
;
_cod_database_code               7239952
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              19207