New thermally stable and friction-insensitive nitrogen-rich salts: a synergy of 1,2,4-triazole, furoxan and hydroxytetrazole motifs
Stebletsova, Irina; Larin, Alexander; Vinogradov, Dmitry B.; Pivkina, Alla N.; Leonov, Nikita E.; Gazieva, Galina A.; Fershtat, Leonid L.; CrystEngComm  (2025) –; doi:10.1039/D5CE01047K

data_7251337
_publ_section_title
;
 New thermally stable and friction-insensitive nitrogen-rich salts: a
 synergy of 1,2,4-triazole, furoxan and hydroxytetrazole motifs
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE01047K
_journal_year                    2025
_chemical_formula_moiety         'C5 H2 N9 O3, C H6 N3'
_chemical_formula_sum            'C6 H8 N12 O3'
_chemical_formula_weight         296.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-12-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-10-01 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.2871(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.83694(5)
_cell_length_b                   17.9329(2)
_cell_length_c                   16.51337(18)
_cell_measurement_reflns_used    9000
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.6970
_cell_measurement_theta_min      4.9030
_cell_volume                     1133.06(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 1.000
_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   -103.00 -24.90   0.55    0.30    --  -44.89 149.00 -68.00  142
  2  \w   -117.00 -57.05   0.55    0.30    --  -44.89-149.00-115.00  109
  3  \w    -85.00 -11.85   0.55    0.30    --  -44.89 124.00 127.00  133
  4  \w     47.00 109.15   0.55    0.30    --   44.89-149.00-115.00  113
  5  \w   -164.00 -73.80   0.55    1.00    --  -93.75-124.00  48.00  164
  6  \w    -85.00 -22.85   0.55    1.00    --  -93.75 124.00 127.00  113
  7  \w   -150.00 -56.50   0.55    1.00    --  -93.75-149.00-115.00  170
  8  \w     96.00 177.95   0.55    1.00    --  115.25 124.00 127.00  149
  9  \w     45.00 110.45   0.55    1.00    --  115.25-124.00  48.00  119
 10  \w     79.00 167.00   0.55    1.00    --  115.25 149.00 -68.00  160
 11  \w     47.00 128.95   0.55    1.00    --  115.25-149.00-115.00  149
 12  \w    -27.00  32.95   0.55    0.30    --  -44.89  19.00-180.00  109
 13  \w   -117.00 -18.55   0.55    0.30    --  -44.89 -77.00 150.00  179
 14  \w   -105.00 -79.15   0.55    0.30    --  -44.89 -77.00 150.00   47
 15  \w     81.00 116.20   0.55    0.30    --   44.89  57.00 120.00   64
 16  \w     27.00  73.20   0.55    0.30    --   44.89  57.00 120.00   84
 17  \w     28.00  55.50   0.55    0.30    --   44.89  57.00 -60.00   50
 18  \w    -31.00  15.20   0.55    0.30    --   44.89 -19.00 150.00   84
 19  \w     27.00  52.85   0.55    0.30    --   44.89  57.00-180.00   47
 20  \w    -22.00   3.30   0.55    0.30    --   44.89 -19.00  90.00   46
 21  \w     64.00  91.50   0.55    0.30    --   44.89  57.00 -60.00   50
 22  \w     19.00  77.85   0.55    0.30    --   44.89  77.00-150.00  107
 23  \w    -97.00 -72.25   0.55    1.00    --  -93.75 -72.00 160.75   45
 24  \w    -98.00 -72.15   0.55    1.00    --  -93.75 -72.00 153.38   47
 25  \w    -96.00 -68.50   0.55    1.00    --  -93.75 -77.00 150.00   50
 26  \w   -102.00 -70.10   0.55    1.00    --  -93.75 -71.00 131.61   58
 27  \w   -114.00 -75.50   0.55    1.00    --  -93.75 -50.00-141.42   70
 28  \w    -99.00 -74.25   0.55    1.00    --  -93.75 -61.00-150.00   45
 29  \w    -96.00 -70.15   0.55    1.00    --  -93.75 -77.00-150.00   47
 30  \w   -114.00 -70.55   0.55    1.00    --  -93.75 -74.00 -76.02   79
 31  \w    -96.00 -70.15   0.55    1.00    --  -93.75 -72.00 166.22   47
 32  \w    -94.00 -69.80   0.55    1.00    --  -93.75 -73.00 124.19   44
 33  \w   -104.00 -77.05   0.55    1.00    --  -93.75 -46.00 171.79   49
 34  \w    -95.00 -69.15   0.55    1.00    --  -93.75 -77.00-180.00   47
 35  \w    -93.00 -68.25   0.55    1.00    --  -93.75 -77.00 -90.00   45
 36  \w   -153.00-127.15   0.55    1.00    --  -93.75 -73.00 124.19   47
 37  \w    -96.00 -70.15   0.55    1.00    --  -93.75 -73.00 100.75   47
 38  \w    -95.00 -69.15   0.55    1.00    --  -93.75 -77.00 120.00   47
 39  \w    -93.00 -68.25   0.55    1.00    --  -93.75 -77.00  90.00   45
 40  \w    -99.00 -74.25   0.55    1.00    --  -93.75 -61.00-180.00   45
 41  \w    -96.00 -70.15   0.55    1.00    --  -93.75 -74.00-169.21   47
 42  \w    -95.00 -69.70   0.55    1.00    --  -93.75 -73.00 178.25   46
 43  \w    -94.00 -68.70   0.55    1.00    --  -93.75 -76.00-163.15   46
 44  \w   -139.00-113.15   0.55    1.00    --  -93.75 -77.00  90.00   47
 45  \w    -94.00 -68.15   0.55    1.00    --  -93.75 -77.00-120.00   47
 46  \w    -99.00 -73.15   0.55    1.00    --  -93.75 -67.00  86.89   47
 47  \w   -101.00 -75.15   0.55    1.00    --  -93.75 -46.00 178.69   47
 48  \w    -95.00 -70.25   0.55    1.00    --  -93.75 -72.00 107.74   45
 49  \w    138.00 177.60   0.55    1.00    --  115.25  61.00  90.00   72
 50  \w    104.00 130.40   0.55    1.00    --  115.25  61.00  90.00   48
 51  \w     43.00  69.95   0.55    1.00    --  115.25 -61.00   0.00   49
 52  \w    141.00 166.30   0.55    1.00    --  115.25  30.00-150.00   46
 53  \w     56.00  97.25   0.55    1.00    --  115.25 -77.00  90.00   75
 54  \w     47.00  94.85   0.55    1.00    --  115.25 -95.00  60.00   87
 55  \w    136.00 171.20   0.55    1.00    --  115.25  77.00  60.00   64
 56  \w     43.00  69.95   0.55    1.00    --  115.25 -61.00-120.00   49
 57  \w    125.00 151.40   0.55    1.00    --  115.25  77.00 -90.00   48
 58  \w     74.00 110.85   0.55    1.00    --  115.25-125.00 -30.00   67
 59  \w     91.00 120.70   0.55    1.00    --  115.25  77.00 -90.00   54
 60  \w     43.00  70.50   0.55    1.00    --  115.25 -61.00-180.00   50
 61  \w     92.00 129.40   0.55    1.00    --  115.25  77.00  60.00   68
 62  \w    140.00 165.30   0.55    1.00    --  115.25  77.00-120.00   46
 63  \w     43.00  67.75   0.55    1.00    --  115.25 -61.00-150.00   45
 64  \w    114.00 160.20   0.55    1.00    --  115.25 125.00  90.00   84
 65  \w    138.00 164.40   0.55    1.00    --  115.25  77.00-180.00   48
 66  \w    103.00 177.25   0.55    1.00    --  115.25  30.00  30.00  135
 67  \w    132.00 176.00   0.55    1.00    --  115.25  30.00 -30.00   80
 68  \w     48.00 102.45   0.55    1.00    --  115.25 -77.00 150.00   99
 69  \w     95.00 119.75   0.55    1.00    --  115.25  77.00-180.00   45
 70  \w     90.00 115.85   0.55    1.00    --  115.25  77.00-120.00   47
 71  \w     44.00  87.45   0.55    1.00    --  115.25 -77.00  60.00   79
 72  \w     44.00  68.75   0.55    1.00    --  115.25 -77.00-120.00   45
 73  \w    135.00 167.45   0.55    1.00    --  115.25  61.00  60.00   59
 74  \w    148.00 174.95   0.55    1.00    --  115.25  30.00-180.00   49
 75  \w    142.00 167.30   0.55    1.00    --  115.25  15.00 120.00   46
 76  \w     96.00 128.45   0.55    1.00    --  115.25  61.00  60.00   59
 77  \w     97.00 122.85   0.55    1.00    --  115.25  61.00-120.00   47
 78  \w    103.00 132.70   0.55    1.00    --  115.25  61.00-180.00   54
 79  \w     94.00 121.50   0.55    1.00    --  115.25  77.00 150.00   50
 80  \w    150.00 178.05   0.55    1.00    --  115.25  61.00 120.00   51
 81  \w     98.00 140.35   0.55    1.00    --  115.25  30.00-180.00   77
 82  \w    132.00 161.15   0.55    1.00    --  115.25  30.00 -90.00   53
 83  \w     97.00 129.45   0.55    1.00    --  115.25  61.00 -90.00   59
 84  \w    128.00 154.40   0.55    1.00    --  115.25  45.00  60.00   48
 85  \w    143.00 172.70   0.55    1.00    --  115.25  77.00-150.00   54
 86  \w    119.00 145.40   0.55    1.00    --  115.25  45.00-150.00   48
 87  \w     54.00  78.75   0.55    1.00    --  115.25-125.00  90.00   45
 88  \w     96.00 121.85   0.55    1.00    --  115.25  77.00-150.00   47
 89  \w    121.00 147.40   0.55    1.00    --  115.25  61.00 120.00   48
 90  \w     79.00 103.75   0.55    1.00    --  115.25 -77.00   0.00   45
 91  \w     79.00 103.75   0.55    1.00    --  115.25 -77.00-150.00   45
 92  \w    137.00 175.50   0.55    1.00    --  115.25  61.00-150.00   70
 93  \w     97.00 132.20   0.55    1.00    --  115.25  61.00-150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0448978000
_diffrn_orient_matrix_UB_12      -0.0853368000
_diffrn_orient_matrix_UB_13      -0.0036742000
_diffrn_orient_matrix_UB_21      0.0069608000
_diffrn_orient_matrix_UB_22      0.0024837000
_diffrn_orient_matrix_UB_23      -0.0931238000
_diffrn_orient_matrix_UB_31      0.4000255000
_diffrn_orient_matrix_UB_32      -0.0095810000
_diffrn_orient_matrix_UB_33      0.0082439000
_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  0.0331
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12386
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.895
_diffrn_reflns_theta_min         4.932
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(11)
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.4224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0657
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.907
_reflns_number_gt                2328
_reflns_number_total             2351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01047k2.cif
_cod_data_source_block           Ris703
_cod_database_code               7251337
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C6 H8 N12 O3'
_chemical_oxdiff_usercomment     Ris703
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.746
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
;
_shelx_res_checksum              25245
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.808