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_7251113
_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         '0.5(C4 N4 Se), 0.5(C15 H14 N6)'
_chemical_formula_sum            'C9.5 H7 N5 Se0.5'
_chemical_formula_weight         229.677
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-29
_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                75.122(2)
_cell_angle_beta                 77.773(2)
_cell_angle_gamma                80.977(2)
_cell_formula_units_Z            4
_cell_length_a                   8.1680(2)
_cell_length_b                   10.9027(2)
_cell_length_c                   11.8936(2)
_cell_measurement_reflns_used    8416
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.5120
_cell_measurement_theta_min      3.9010
_cell_volume                     994.53(4)
_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  'olex2.refine 1.5 (Bourhis et al., 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 0.9989
_diffrn_measured_fraction_theta_max 0.9605
_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     53.00 120.00   0.50    0.50    --   47.38  57.00  60.00  134
  2  \w    104.00 176.00   0.50    0.50    --  113.25  61.00 150.00  144
  3  \w    109.00 173.00   0.50    0.50    --  113.25  15.00  90.00  128
  4  \w    106.00 134.00   0.50    0.50    --  113.25  45.00  60.00   56
  5  \w    137.00 172.00   0.50    0.50    --  113.25  45.00  60.00   70
  6  \w    153.00 178.00   0.50    0.50    --  113.25  30.00   0.00   50
  7  \w    113.00 138.00   0.50    0.50    --  113.25  30.00   0.00   50
  8  \w    -26.00  22.00   0.50    0.50    --  -47.38  19.00 -60.00   96
  9  \w    -69.00 -44.00   0.50    0.50    -- -106.00  61.00 -90.00   50
 10  \w    -71.00 -46.00   0.50    0.50    -- -106.00  61.00   0.00   50
 11  \w    -71.00 -33.00   0.50    0.50    -- -106.00  61.00-120.00   76
 12  \w    -67.00 -41.00   0.50    0.50    -- -106.00  61.00 120.00   52
 13  \w    -61.00 -35.00   0.50    0.50    -- -106.00  77.00 150.00   52
 14  \w   -106.00 -70.00   0.50    0.50    -- -106.00  77.00 150.00   72
 15  \w    -25.00  41.00   0.50    0.50    --   47.38 -37.00 -90.00  132
 16  \w     68.00 109.00   0.50    0.50    --  113.25-125.00 -30.00   82
 17  \w     52.00  94.00   0.50    0.50    --  113.25-125.00   0.00   84
 18  \w     58.00  84.00   0.50    0.50    --  113.25-125.00 -60.00   52
 19  \w     77.00 102.00   0.50    0.50    --  113.25-125.00-120.00   50
 20  \w     13.00  77.00   0.50    0.50    --   47.38-125.00  60.00  128
 21  \w    -21.00  60.00   0.50    0.50    --   47.38 -57.00 150.00  162
 22  \w      6.00  61.00   0.50    0.50    --   47.38-111.00 171.00  110
 23  \w     51.00  76.00   0.50    0.50    --  113.25-111.00 171.00   50
 24  \w     42.00  94.00   0.50    0.50    --  113.25 -94.00  90.00  104
 25  \w     77.00 106.00   0.50    0.50    --  113.25 -94.00  30.00   58
 26  \w     83.00 178.00   0.50    0.50    --  113.25 111.00 -95.00  190
 27  \w     43.00  71.00   0.50    0.50    --  113.25 -61.00-120.00   56
 28  \w     45.00 106.00   0.50    0.50    --  113.25 -77.00-180.00  122
 29  \w     46.00  71.00   0.50    0.50    --  113.25 -61.00   0.00   50
 30  \w     45.00  71.00   0.50    0.50    --  113.25 -61.00  30.00   52
 31  \w     45.00  70.00   0.50    0.50    --  113.25 -61.00 150.00   50
 32  \w    -64.00 -33.00   0.50    0.50    -- -106.00 110.00  84.69   62
 33  \w   -124.00 -87.00   0.50    0.50    -- -106.00 142.00  89.81   74
 34  \w   -110.00 -69.00   0.50    0.50    -- -106.00 125.00 150.00   82
 35  \w    -62.00 -33.00   0.50    0.50    -- -106.00 125.00 150.00   58
 36  \w   -120.00 -76.00   0.50    0.50    -- -106.00 137.00 157.69   88
 37  \w   -112.00 -66.00   0.50    0.50    -- -106.00 125.00   0.00   92
 38  \w    -62.00 -33.00   0.50    0.50    -- -106.00 125.00   0.00   58
 39  \w   -112.00 -43.00   0.50    0.50    -- -106.00 125.00 -30.00  138
 40  \w   -112.00 -87.00   0.50    0.50    -- -106.00 125.00-120.00   50
 41  \w   -108.00 -81.00   0.50    0.50    -- -106.00 111.00 -95.00   54
 42  \w    -76.00 -33.00   0.50    0.50    -- -106.00 125.00-120.00   86
 43  \w    -65.00 -38.00   0.50    0.50    -- -106.00 111.00 -95.00   54
 44  \w    -27.00  -2.00   0.50    0.50    --  -47.38 111.00 -95.00   50
 45  \w    -81.00 -46.00   0.50    0.50    --  -47.38 111.00 -95.00   70
 46  \w   -107.00 -81.00   0.50    0.50    -- -106.00 110.00  84.69   52
 47  \w   -126.00 -98.00   0.50    0.50    -- -106.00 -30.00-180.00   56
 48  \w   -161.00-134.00   0.50    0.50    -- -106.00 -30.00-180.00   54
 49  \w   -175.00-103.00   0.50    0.50    -- -106.00 -30.00-120.00  144
 50  \w   -154.00 -84.00   0.50    0.50    -- -106.00 -77.00   0.00  140
 51  \w   -120.00 -85.00   0.50    0.50    --  -47.38-125.00-150.00   70
 52  \w   -126.00 -92.00   0.50    0.50    -- -106.00-111.00 171.00   68
;
_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      -0.1389667000
_diffrn_orient_matrix_UB_12      -0.0899868000
_diffrn_orient_matrix_UB_13      0.0518401000
_diffrn_orient_matrix_UB_21      -0.0737032000
_diffrn_orient_matrix_UB_22      0.0484021000
_diffrn_orient_matrix_UB_23      -0.1144795000
_diffrn_orient_matrix_UB_31      0.1137716000
_diffrn_orient_matrix_UB_32      -0.1057786000
_diffrn_orient_matrix_UB_33      -0.0526130000
_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  0.0410
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.9989
_diffrn_reflns_Laue_measured_fraction_max 0.9605
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13871
_diffrn_reflns_point_group_measured_fraction_full 0.9989
_diffrn_reflns_point_group_measured_fraction_max 0.9605
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.84
_diffrn_reflns_theta_min         3.91
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91228
_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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       prism
_exptl_crystal_F_000             461.813
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.4180
_refine_diff_density_min         -0.8327
_refine_diff_density_rms         0.0768
_refine_ls_d_res_high            0.7832
_refine_ls_d_res_low             11.3078
_refine_ls_goodness_of_fit_ref   1.0260
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0260
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3818
_reflns_number_total             4159
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00888c2.cif
_cod_data_source_block           073-006_A585
_cod_depositor_comments
'Adding full bibliography for 7251113--7251115.cif.'
_cod_database_code               7251113
_chemical_oxdiff_formula         'C19 H15 N10 Se'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C11(H11a,H11b), C12(H12a,H12b), C14(H14a,H14b), C13(H13a,H13b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C4(H4)
;
_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 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.668