Regioselective electrochemical 7-<i>endo-dig</i> selenocyclization of <i>N</i>-benzyl propiolamides to access selenated benzo[<i>c</i>]azepinones.
Luo, Xian-Bing; Wu, Xia-Die; Wang, Lei; Li, Zhifang; Hou, Zhong-Wei; Chemical communications (Cambridge, England) 62 (2026) 4346–4349; doi:10.1039/d5cc06757j

data_7135432
_publ_section_title
;
 Regioselective electrochemical 7-<i>endo-dig</i> selenocyclization of
 <i>N</i>-benzyl propiolamides to access selenated
 benzo[<i>c</i>]azepinones.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4346
_journal_page_last               4349
_journal_paper_doi               10.1039/d5cc06757j
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C35 H23 N O Se'
_chemical_formula_sum            'C35 H23 N O Se'
_chemical_formula_weight         552.50
_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     iterative
_audit_creation_date             2025-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-07-08 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.372(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.5813(4)
_cell_length_b                   8.5064(2)
_cell_length_c                   32.0053(6)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      4.56
_cell_volume                     5274.20(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      299.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            33875
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.458
_diffrn_reflns_theta_min         4.565
_exptl_absorpt_coefficient_mu    2.145
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4425
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1239 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.5876.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+6.4183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4571
_reflns_number_total             4803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06757j2.cif
_cod_data_source_block           1_CCDC1
_cod_database_code               7135432
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.674
_shelx_estimated_absorpt_t_min   0.650
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C28(H28), C19(H19), C24(H24), C25(H25), C33(H33), C30(H30), C27(H27), C1(H1),
 C18(H18), C26(H26), C16(H16), C14(H14), C10(H10), C0AA(H0AA), C32(H32),
 C13(H13), C17(H17), C2(H2), C5(H5), C12(H12), C11(H11), C3(H3), C4(H4)
;
_shelx_res_checksum              17318
_olex2_submission_special_instructions 'No special instructions were received'