Divergent α-functionalization of cyclic amines via ring construction by molecular O2 oxidized dearomatization and ring deconstruction by aromatization-driven C–C σ-bond cleavage
Hu, Fangzhi; Wang, Liang; Ge, Chunyan; Li, Xinyao; Ding, Zhanshuai; Xu, Lubin; Li, Shuai-Shuai; Green Chemistry 23 (2021) 5535–5541; doi:10.1039/D1GC00941A

data_7243088
_publ_section_title
;
 Divergent \a-functionalization of cyclic amines via ring construction by
 molecular O2 oxidized dearomatization and ring deconstruction by
 aromatization-driven C--C \s-bond cleavage
;
_journal_issue                   15
_journal_name_full               'Green Chemistry'
_journal_page_first              5535
_journal_page_last               5541
_journal_paper_doi               10.1039/D1GC00941A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C24 H27.5 N2 O'
_chemical_formula_weight         359.98
_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-2018/3
_audit_update_record
;
2021-01-21 deposited with the CCDC.	2021-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                75.136(9)
_cell_angle_beta                 78.644(10)
_cell_angle_gamma                89.902(6)
_cell_formula_units_Z            4
_cell_length_a                   11.9297(10)
_cell_length_b                   12.9240(9)
_cell_length_c                   13.666(2)
_cell_measurement_reflns_used    2319
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.1790
_cell_measurement_theta_min      3.7950
_cell_volume                     1994.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13345
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.235
_diffrn_reflns_theta_max         67.235
_diffrn_reflns_theta_min         3.417
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       block
_exptl_crystal_F_000             774
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
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_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7100
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1753
_refine_ls_R_factor_gt           0.1157
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2884
_refine_ls_wR_factor_ref         0.3647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3517
_reflns_number_total             7100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc00941a2.cif
_cod_data_source_block           exp_11355
_cod_depositor_comments
;
Adding full bibliography for 7243088--7243090.cif.

2024-10-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H55 N4 O2'
_cod_original_formula_weight         719.96
_cod_original_formula_units_Z            2
_cod_database_code               7243088
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.961
_shelx_res_checksum              5464