The direct synthesis of 5-selenotetrazoles <i>via</i> an electrochemical three-component reaction between isonitriles, diselenides and TMSN<sub>3</sub>.
Wang, Ruizong; Song, Bin; Zhao, Feng; Gao, Pengxiang; Hu, Bingcheng; Zhang, Chong; Organic & biomolecular chemistry 23 (2025) 7588–7592; doi:10.1039/d5ob00893j

data_7160650
_publ_section_title
;
 The direct synthesis of 5-selenotetrazoles <i>via</i> an electrochemical
 three-component reaction between isonitriles, diselenides and
 TMSN<sub>3</sub>.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7588
_journal_page_last               7592
_journal_paper_doi               10.1039/d5ob00893j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C11 H13 Cl1 N4 Se1'
_chemical_formula_sum            'C11 H13 Cl N4 Se'
_chemical_formula_weight         315.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-04-08 deposited with the CCDC.	2025-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.142(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4939(2)
_cell_length_b                   12.5591(6)
_cell_length_c                   14.7813(6)
_cell_measurement_reflns_used    2135
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.798
_cell_measurement_theta_min      4.673
_cell_volume                     1354.73(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.563
_diffrn_reflns_theta_min         4.673
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.441
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1099 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.8023.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.100
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     606
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0777
_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^)+(0.0656P)^2^+4.3394P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1865
_refine_ls_wR_factor_ref         0.1997
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1895
_reflns_number_total             2481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00893j2.cif
_cod_data_source_block           cu_nlg_clph_0m
_cod_depositor_comments          'Adding full bibliography for 7160650.cif.'
_cod_database_code               7160650
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.586
_shelx_estimated_absorpt_t_min   0.538
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Se1 \\sim Cl1 \\sim N1 \\sim N2A \\sim N3 \\sim N4 \\sim C1 \\sim C2 \\sim C3
\\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim
Se1A \\sim Cl1A \\sim N1A \\sim N2 \\sim N3A \\sim N4A \\sim C1A \\sim C2A
\\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim C7A \\sim C8A \\sim C9A \\sim
C10A \\sim C11A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
3. Rigid body (RIGU) restrains
 Se1A, Cl1A, N1A, N2, N3A, N4A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A,
 C10A, C11A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 Se1, Cl1, N1, N2A, N3, N4, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Others
 Sof(Se1A)=Sof(Cl1A)=Sof(N1A)=Sof(N2)=Sof(N3A)=Sof(N4A)=Sof(C1A)=Sof(C2A)=
 Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C4A)=
 Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=Sof(C5A)=Sof(C9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=
 Sof(H11A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=1-FVAR(1)
 Sof(Se1)=Sof(Cl1)=Sof(N1)=Sof(N2A)=Sof(N3)=Sof(N4)=Sof(C1)=Sof(C2)=Sof(H2A)=
 Sof(H2B)=Sof(H2C)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(H4C)=Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(H11)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C10A(H10A), C11A(H11A), C7A(H7A), C8A(H8A)
5.b Fitted hexagon refined as free rotating group:
 C6(C7,C8,C9,C10,C11), C9A(C10A,C11A,C6A,C7A,C8A)
5.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C2A(H2AA,H2AB,H2AC),
 C3A(H3AA,H3AB,H3AC), C4A(H4AA,H4AB,H4AC)
;
_shelx_res_checksum              77013
_olex2_submission_special_instructions 'No special instructions were received'