Divergent noncovalent interactions of isomeric nitrile and isocyanide groups in selenodiazole–triazole cocrystals: σ-hole chalcogen bonding versus π–π stacking
Smirnov, Andrey S.; Katlenok, Eugene A.; Vakhrushev, Aleksandr Yu.; Krasilnikov, Vitalii A.; Belskaya, Nataliya P.; Katkova, Svetlana A.; Bokach, Nadezhda A.; CrystEngComm 27 (2025) 7390–7398; doi:10.1039/D5CE00888C

data_7251114
_publ_section_title
;
 Divergent noncovalent interactions of isomeric nitrile and isocyanide
 groups in selenodiazole--triazole cocrystals: \s-hole chalcogen bonding
 versus \p--\p stacking
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7390
_journal_page_last               7398
_journal_paper_doi               10.1039/D5CE00888C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C4 N4 Se, C14 H12 N6 O'
_chemical_formula_sum            'C18 H12 N10 O Se'
_chemical_formula_weight         463.34
_chemical_name_systematic
'Cocryastals of 2-(4-isocyanophenyl)-5-morpholino-2H-1,2,3-triazole-4-carbonitrile with 1,2,5-selenadiazole-3,4-dicarbonitrile'
_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             2025-08-28
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-08-29 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.3180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0474(2)
_cell_length_b                   21.2353(2)
_cell_length_c                   8.10380(10)
_cell_measurement_reflns_used    12917
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.2280
_cell_measurement_theta_min      3.9680
_cell_volume                     1895.71(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00  12.00   0.50    0.08    --  -47.38  86.00-145.00  162
  2  \w    -20.00  59.00   0.50    0.08    --   47.38 -86.00  96.00  158
  3  \w    -65.00 -39.00   0.50    0.34    -- -106.00  86.00-145.00   52
  4  \w   -170.00-140.00   0.50    0.34    -- -106.00 -86.00  96.00   60
  5  \w   -106.00 -81.00   0.50    0.34    -- -106.00 -86.00  96.00   50
  6  \w     88.00 176.00   0.50    0.34    --  113.25  86.00-145.00  176
  7  \w    -15.00  11.00   0.50    0.08    --  -47.38  19.00   0.00   52
  8  \w   -110.00 -84.00   0.50    0.08    --  -47.38-125.00-180.00   52
  9  \w    -99.00 -73.00   0.50    0.08    --  -47.38-125.00-120.00   52
 10  \w   -105.00 -73.00   0.50    0.08    --  -47.38-125.00   0.00   64
 11  \w     76.00 103.00   0.50    0.08    --   47.38 125.00  60.00   54
 12  \w    -70.00 -34.00   0.50    0.34    -- -106.00  61.00   0.00   72
 13  \w    -71.00 -39.00   0.50    0.34    -- -106.00  61.00 -30.00   64
 14  \w    -65.00 -38.00   0.50    0.34    -- -106.00  61.00-180.00   54
 15  \w   -116.00 -90.00   0.50    0.34    -- -106.00 -61.00-180.00   52
 16  \w    -72.00 -34.00   0.50    0.34    -- -106.00  77.00  30.00   76
 17  \w    -64.00 -34.00   0.50    0.34    -- -106.00  61.00-150.00   60
 18  \w    -69.00 -44.00   0.50    0.34    -- -106.00  61.00  60.00   50
 19  \w   -176.00-115.00   0.50    0.34    -- -106.00 -15.00  30.00  122
 20  \w     42.00  67.00   0.50    0.34    --  113.25 -61.00-120.00   50
 21  \w     42.00 106.00   0.50    0.34    --  113.25-125.00  90.00  128
 22  \w     51.00 103.00   0.50    0.34    --  113.25-125.00  60.00  104
 23  \w     53.00 105.00   0.50    0.34    --  113.25 -77.00 -60.00  104
 24  \w     45.00  70.00   0.50    0.34    --  113.25 -61.00 120.00   50
 25  \w    103.00 175.00   0.50    0.34    --  113.25  15.00-180.00  144
 26  \w     57.00 127.00   0.50    0.34    --  113.25 -86.00  96.00  140
 27  \w   -124.00 -98.00   0.50    0.34    -- -106.00  86.00-145.00   52
 28  \w    -26.00  -1.00   0.50    0.08    --  -47.38  19.00   0.00   50
 29  \w    -14.00  25.00   0.50    0.08    --   47.38 -19.00 150.00   78
 30  \w     -2.00  25.00   0.50    0.08    --   47.38 -19.00 -90.00   54
 31  \w      8.00  37.00   0.50    0.08    --   47.38 -37.00 120.00   58
 32  \w    -25.00  26.00   0.50    0.08    --   47.38 -19.00-150.00  102
 33  \w     -1.00  31.00   0.50    0.08    --   47.38 -37.00-180.00   64
 34  \w     90.00 118.00   0.50    0.08    --   47.38  37.00 -30.00   56
 35  \w     52.00  77.00   0.50    0.08    --   47.38  37.00 -30.00   50
 36  \w    -23.00   4.00   0.50    0.08    --   47.38 -37.00 120.00   54
 37  \w   -141.00 -95.00   0.50    0.34    -- -106.00 -30.00 -60.00   92
 38  \w   -111.00 -85.00   0.50    0.34    -- -106.00 125.00  90.00   52
 39  \w    -66.00 -34.00   0.50    0.34    -- -106.00 125.00  90.00   64
 40  \w   -114.00 -89.00   0.50    0.34    -- -106.00 -61.00 150.00   50
 41  \w   -176.00-150.00   0.50    0.34    -- -106.00 -30.00 -60.00   52
 42  \w    -71.00 -46.00   0.50    0.34    -- -106.00  61.00  90.00   50
 43  \w   -177.00 -94.00   0.50    0.34    -- -106.00 -30.00   0.00  166
 44  \w   -108.00 -83.00   0.50    0.34    -- -106.00 -77.00 150.00   50
 45  \w   -126.00 -93.00   0.50    0.34    -- -106.00 -30.00 -30.00   66
 46  \w    -64.00 -37.00   0.50    0.34    -- -106.00  61.00 -60.00   54
 47  \w    -65.00 -40.00   0.50    0.34    -- -106.00 125.00 120.00   50
 48  \w   -173.00 -86.00   0.50    0.34    -- -106.00 -94.00 120.00  174
 49  \w   -177.00-148.00   0.50    0.34    -- -106.00 -30.00 -90.00   58
 50  \w   -173.00-136.00   0.50    0.34    -- -106.00 -30.00 -30.00   74
 51  \w     71.00 111.00   0.50    0.34    --  113.25-125.00 -90.00   80
 52  \w     49.00  93.00   0.50    0.34    --  113.25 -94.00-120.00   88
 53  \w    118.00 144.00   0.50    0.34    --  113.25  77.00 150.00   52
 54  \w     91.00 116.00   0.50    0.34    --  113.25  77.00 150.00   50
 55  \w    124.00 176.00   0.50    0.34    --  113.25  45.00 -30.00  104
 56  \w     76.00 102.00   0.50    0.34    --  113.25 -94.00  60.00   52
 57  \w     43.00  69.00   0.50    0.34    --  113.25-125.00 150.00   52
 58  \w     45.00  78.00   0.50    0.34    --  113.25-125.00-120.00   66
 59  \w    131.00 177.00   0.50    0.34    --  113.25  45.00 -90.00   92
 60  \w    101.00 127.00   0.50    0.34    --  113.25  45.00 -90.00   52
 61  \w    130.00 143.50   0.50    0.34    --  113.25  45.00 -60.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0392826000
_diffrn_orient_matrix_UB_12      0.0589297000
_diffrn_orient_matrix_UB_13      0.1013046000
_diffrn_orient_matrix_UB_21      0.1299047000
_diffrn_orient_matrix_UB_22      -0.0264245000
_diffrn_orient_matrix_UB_23      0.0263193000
_diffrn_orient_matrix_UB_31      0.0336919000
_diffrn_orient_matrix_UB_32      0.0330459000
_diffrn_orient_matrix_UB_33      -0.1593807000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            28150
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.063
_diffrn_reflns_theta_min         4.013
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.988
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method
'Evaporation the mixture of two components in dichloromethane'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0368
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3591
_reflns_number_total             4045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00888c2.cif
_cod_data_source_block           073-002_a564_auto
_cod_depositor_comments
'Adding full bibliography for 7251113--7251115.cif.'
_cod_database_code               7251114
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C18 H13 n1o O Se '
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C13(H13A,H13B)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3), C7(H7)
;
_shelx_res_checksum              3969
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.095
_oxdiff_exptl_absorpt_empirical_full_min 0.424