Metal-Free C–C Cross Coupling: Electrosynthesis of Azaheterocycles through Anodic Oxidation Cyclization of 1,6-Enynes
Cai, Chen; Lu, Yi; Yuan, Chengcheng; Fang, Zheng; Yang, Xiaobing; Liu, Chengkou; Guo, Kai; ACS Sustainable Chemistry & Engineering 10 (2022) 3288–3294; doi:10.1021/acssuschemeng.1c07933

data_4519426
_publ_section_title
;
 Metal-Free C--C Cross Coupling: Electrosynthesis of Azaheterocycles
 through Anodic Oxidation Cyclization of 1,6-Enynes
;
_journal_issue                   10
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_page_first              3288
_journal_page_last               3294
_journal_paper_doi               10.1021/acssuschemeng.1c07933
_journal_volume                  10
_journal_year                    2022
_chemical_formula_sum            'C25 H15 N O4'
_chemical_formula_weight         393.38
_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-2014/7
_cell_angle_alpha                62.407(4)
_cell_angle_beta                 72.632(4)
_cell_angle_gamma                84.054(4)
_cell_formula_units_Z            2
_cell_length_a                   8.6432(4)
_cell_length_b                   11.0448(5)
_cell_length_c                   11.1069(4)
_cell_measurement_reflns_used    6448
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1280
_cell_measurement_theta_min      4.5140
_cell_volume                     896.10(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8857
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.328
_diffrn_reflns_theta_min         4.521
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71168
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       solid
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0417
_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^)+(0.1000P)^2^+0.1380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3272
_reflns_number_total             3487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc1c07933_si_002.cif
_cod_data_source_block           X
_cod_database_code               4519426
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.854
_shelx_estimated_absorpt_t_max   0.923
_shelx_res_checksum              70472
_shelx_hkl_checksum              32887