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_7135433
_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         'C27 H27 N O2 Se'
_chemical_formula_sum            'C27 H27 N O2 Se'
_chemical_formula_weight         476.480
_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'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-04-24
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7221)
;
_audit_update_record
;
2025-05-28 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.312(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.2397(4)
_cell_length_b                   6.6540(1)
_cell_length_c                   30.0658(4)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    297.0
_cell_volume                     4771.01(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      297.0
_diffrn_measured_fraction_theta_full 0.9949
_diffrn_measured_fraction_theta_max 0.9933
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.9949
_diffrn_reflns_Laue_measured_fraction_max 0.9933
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            26309
_diffrn_reflns_point_group_measured_fraction_full 0.9949
_diffrn_reflns_point_group_measured_fraction_max 0.9933
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         68.33
_diffrn_reflns_theta_min         5.16
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.301
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1299 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.6196.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             1967.077
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.2330
_refine_diff_density_min         -0.2877
_refine_diff_density_rms         0.0571
_refine_ls_d_res_high            0.8295
_refine_ls_d_res_low             8.5640
_refine_ls_goodness_of_fit_ref   1.0429
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0429
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+4.2234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0753
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              28
_reflns_limit_h_min              -28
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              36
_reflns_limit_l_min              0
_reflns_number_gt                4067
_reflns_number_total             4324
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc06757j2.cif
_cod_data_source_block           1_CCDC2
_cod_database_code               7135433
_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:
 C21(H21a,H21b)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C16(H16), C14(H14), C17(H17), C5(H5), C1(H1), C10(H10), C13(H13),
 C12(H12), C4(H4), C3(H3), C2(H2), C11(H11)
2.c Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c), C24(H24a,H24b,H24c), C23(H23a,H23b,H23c), C26(H26a,H26b,
 H26c)
;
_olex2_submission_special_instructions 'No special instructions were received'