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_7135431
_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         'C29 H31 N O2 Se'
_chemical_formula_sum            'C29 H31 N O2 Se'
_chemical_formula_weight         504.51
_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     dual
_audit_creation_date             2024-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-09-25 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                107.1380(10)
_cell_angle_beta                 90.0070(10)
_cell_angle_gamma                100.8610(10)
_cell_formula_units_Z            2
_cell_length_a                   6.64190(10)
_cell_length_b                   11.9656(3)
_cell_length_c                   17.5698(4)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.68
_cell_measurement_theta_min      2.43
_cell_volume                     1308.14(5)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45066
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.241
_diffrn_reflns_theta_min         2.430
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1136 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.8911.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         6418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.2268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5243
_reflns_number_total             6418
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06757j2.cif
_cod_data_source_block           1
_cod_database_code               7135431
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.789
_shelx_estimated_absorpt_t_min   0.740
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C29(H29), C25(H25), C28(H28), C27(H27), C26(H26), C4(H4), C6(H6),
 C3(H3), C2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C12(H12A,H12B,
 H12C), C10(H10A,H10B,H10C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              26794
_olex2_submission_special_instructions 'No special instructions were received'