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_7251115
_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         '0.16(C14 H12 N6 O)'
_chemical_formula_sum            'C2.24 H1.92 N0.96 O0.16'
_chemical_formula_weight         44.85
_chemical_name_systematic
2-(4-isocyanophenyl)-5-morpholino-2H-1,2,3-triazole-4-carbonitrile
_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             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                65.216(3)
_cell_angle_beta                 82.064(3)
_cell_angle_gamma                79.392(3)
_cell_formula_units_Z            25
_cell_length_a                   7.4527(2)
_cell_length_b                   14.1001(4)
_cell_length_c                   14.2337(4)
_cell_measurement_reflns_used    15340
_cell_measurement_temperature    99.96(16)
_cell_measurement_theta_max      78.1960
_cell_measurement_theta_min      3.3880
_cell_volume                     1331.65(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.949
_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    -72.00  25.00   0.50    0.50    --  -47.30  82.00 163.00  194
  2  \w    -24.00  72.00   0.50    0.50    --   47.30 -82.00  42.00  192
  3  \w    -24.00  72.00   0.50    0.50    --   47.30 -82.00  42.00  192
  4  \w   -177.00 -81.00   0.50    1.00    -- -106.00 -82.00  42.00  192
  5  \w     88.00 178.00   0.50    1.00    --  113.25  82.00 163.00  180
  6  \w     42.00 138.00   0.50    1.00    --  113.25 -82.00  42.00  192
  7  \w    -26.00  28.00   0.50    0.50    --  -47.30  19.00 -30.00  108
  8  \w     25.00 119.00   0.50    0.50    --   47.30  77.00-150.00  188
  9  \w    -26.00  42.00   0.50    0.50    --   47.30 -37.00 -30.00  136
 10  \w    -26.00  42.00   0.50    0.50    --   47.30 -37.00  90.00  136
 11  \w     35.00 121.00   0.50    0.50    --   47.30  37.00 150.00  172
 12  \w    -27.00  26.00   0.50    0.50    --   47.30 -19.00-180.00  106
 13  \w     35.00 121.00   0.50    0.50    --   47.30  37.00 150.00  172
 14  \w   -112.00 -36.00   0.50    1.00    -- -106.00 125.00  90.00  152
 15  \w   -177.00 -83.00   0.50    1.00    -- -106.00 -94.00 150.00  188
 16  \w   -112.00 -36.00   0.50    1.00    -- -106.00 125.00 -90.00  152
 17  \w   -112.00 -36.00   0.50    1.00    -- -106.00 125.00 -60.00  152
 18  \w   -112.00 -36.00   0.50    1.00    -- -106.00 125.00   0.00  152
 19  \w   -156.00-105.00   0.50    1.00    -- -106.00 -48.00-109.94  102
 20  \w   -175.00-148.00   0.50    1.00    -- -106.00 -52.00  -3.17   54
 21  \w   -169.00 -93.00   0.50    1.00    -- -106.00 -53.00  90.86  152
 22  \w   -121.00 -69.00   0.50    1.00    -- -106.00 139.00 -52.89  104
 23  \w   -106.00 -37.00   0.50    1.00    -- -106.00 125.00-180.00  138
 24  \w   -174.00-119.00   0.50    1.00    -- -106.00 -45.00-180.00  110
 25  \w   -110.00 -83.00   0.50    1.00    -- -106.00 -82.00  42.00   54
 26  \w   -142.00 -93.00   0.50    1.00    -- -106.00 -52.00  -3.17   98
 27  \w   -119.00 -84.00   0.50    1.00    -- -106.00 137.00 121.40   70
 28  \w   -112.00 -81.00   0.50    1.00    -- -106.00 125.00 -60.00   62
 29  \w   -131.00 -99.00   0.50    1.00    -- -106.00  82.00 163.00   64
 30  \w    -68.00 -37.00   0.50    1.00    -- -106.00  61.00-180.00   62
 31  \w    -69.00 -34.00   0.50    1.00    -- -106.00  61.00 120.00   70
 32  \w   -107.00 -63.00   0.50    1.00    -- -106.00 112.00  93.87   88
 33  \w   -122.00 -71.00   0.50    1.00    -- -106.00 141.00-134.87  102
 34  \w   -107.00 -71.00   0.50    1.00    -- -106.00 112.00  34.17   72
 35  \w    -97.00 -35.00   0.50    1.00    -- -106.00  77.00-150.00  124
 36  \w    -70.00 -35.00   0.50    1.00    -- -106.00  61.00 -90.00   70
 37  \w    112.00 145.00   0.50    1.00    --  113.25  45.00 -60.00   66
 38  \w     98.00 175.00   0.50    1.00    --  113.25  61.00  60.00  154
 39  \w     60.00  87.00   0.50    1.00    --  113.25 -94.00-120.00   54
 40  \w     68.00  95.00   0.50    1.00    --  113.25 -94.00   0.00   54
 41  \w     74.00 108.00   0.50    1.00    --  113.25-106.00-163.89   68
 42  \w    144.00 171.00   0.50    1.00    --  113.25  45.00 -90.00   54
 43  \w     80.00 106.00   0.50    1.00    --  113.25 -77.00-180.00   52
 44  \w     43.00  70.00   0.50    1.00    --  113.25 -61.00 -60.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22199
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.148
_diffrn_reflns_theta_min         3.428
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_preparation
'Prepared starting from 4-nitroaniline according with 7 steps synthetic scheme'
_exptl_crystal_recrystallization_method
'Crystals were prepared by evaporation of dichloromethane solution in losely closed vial'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0617P)^2^+0.6613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5051
_reflns_number_total             5527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00888c2.cif
_cod_data_source_block           008-005_a551_auto
_cod_depositor_comments
'Adding full bibliography for 7251113--7251115.cif.'
_cod_database_code               7251115
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C N H O'
_cell_oxdiff_angle_alpha         65.216(3)
_cell_oxdiff_angle_beta          82.064(3)
_cell_oxdiff_angle_gamma         79.392(3)
_cell_oxdiff_length_a            7.4527(2)
_cell_oxdiff_length_b            14.1001(4)
_cell_oxdiff_length_c            14.2337(4)
_cell_oxdiff_measurement_reflns_used 15340
_cell_oxdiff_volume              1331.65(7)
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.898
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.029) H4(0.028) H6(0.026) H7(0.027) H11A(0.029) H11B(0.029)
 H01A(0.032) H01B(0.032) H01C(0.032) H01D(0.032) H14C(0.029) H14D(0.029)
 H3A(0.028) H4A(0.027) H6A(0.029) H7A(0.029) H00A(0.029) H00B(0.029) H12A(0.03)
 H12B(0.03) H13A(0.03) H13B(0.03) H14A(0.029) H14B(0.029)
 Fixed X: H3(0.32541) H4(0.247776) H6(0.286623) H7(0.366576) H11A(0.005231)
 H11B(0.179695) H01A(-0.070313) H01B(-0.192107) H01C(-0.124714) H01D(0.042666)
 H14C(0.254239) H14D(0.121568) H3A(1.002497) H4A(0.844345) H6A(0.765435)
 H7A(0.925333) H00A(0.320334) H00B(0.488484) H12A(0.698094) H12B(0.573206)
 H13A(0.478073) H13B(0.641368) H14A(0.394798) H14B(0.259272)
 Fixed Y: H3(0.587446) H4(0.441637) H6(0.598354) H7(0.743591) H11A(0.208968)
 H11B(0.120285) H01A(0.038952) H01B(0.09097) H01C(0.033098) H01D(-0.05827)
 H14C(0.056765) H14D(0.109797) H3A(0.234621) H4A(0.388732) H6A(0.518964)
 H7A(0.365647) H00A(0.862198) H00B(0.770141) H12A(0.883618) H12B(0.937396)
 H13A(1.037768) H13B(0.944264) H14A(0.871331) H14B(0.926272)
 Fixed Z: H3(1.188866) H4(1.172166) H6(0.85818) H7(0.874991) H11A(1.236638)
 H11B(1.246883) H01A(1.349026) H01B(1.250737) H01C(1.115425) H01D(1.121922)
 H14C(1.098208) H14D(1.004329) H3A(0.625054) H4A(0.639268) H6A(0.330938)
 H7A(0.316393) H00A(0.250317) H00B(0.260173) H12A(0.242229) H12B(0.145132)
 H13A(0.37076) H13B(0.377291) H14A(0.490493) H14B(0.398155)
;
_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 1.810
_oxdiff_exptl_absorpt_empirical_full_min 0.554