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_7251338
_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 H5 K2 N9 O5'
_chemical_formula_sum            'C5 H5 K2 N9 O5'
_chemical_formula_weight         349.38
_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   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-06-05
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-10-01 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                66.363(3)
_cell_angle_beta                 86.447(2)
_cell_angle_gamma                75.934(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9975(2)
_cell_length_b                   8.9440(2)
_cell_length_c                   11.0111(3)
_cell_measurement_reflns_used    19519
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.0860
_cell_measurement_theta_min      4.3430
_cell_volume                     611.90(3)
_computing_cell_refinement       'CrysAlisPro 1.171.44.112a (Rigaku OD, 2025)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.44.112a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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    -79.00  26.05   0.55    1.00    --  -44.91  96.00  -9.00  191
  2  \w     -7.00  78.25   0.55    1.00    --   44.91 -96.00-118.00  155
  3  \w   -165.00 -85.25   0.55    5.00    --  -93.75 -96.00-118.00  145
  4  \w    -80.00 -22.80   0.55    5.00    --  -93.75  96.00  -9.00  104
  5  \w     44.00 103.95   0.55    5.00    --  115.25 -96.00-118.00  109
  6  \w    106.00 177.50   0.55    5.00    --  115.25  96.00  -9.00  130
  7  \w    -59.00 -30.95   0.55    1.00    --   12.00 158.00-154.54   51
  8  \w   -118.00 -26.70   0.55    1.00    --  -44.91 -57.00-180.00  166
  9  \w    -43.00  28.50   0.55    1.00    --  -44.91  38.00-180.00  130
 10  \w   -118.00 -26.70   0.55    1.00    --  -44.91 -57.00-180.00  166
 11  \w     19.00 117.45   0.55    1.00    --   44.91  77.00  30.00  179
 12  \w     19.00 117.45   0.55    1.00    --   44.91  77.00-180.00  179
 13  \w     34.00  92.85   0.55    1.00    --   44.91-125.00 -90.00  107
 14  \w     19.00 117.45   0.55    1.00    --   44.91  77.00  30.00  179
 15  \w     24.00 122.45   0.55    1.00    --   44.91  19.00 -60.00  179
 16  \w     27.00 117.20   0.55    1.00    --   44.91  57.00 -90.00  164
 17  \w     27.00 119.40   0.55    1.00    --   44.91  38.00   0.00  168
 18  \w     24.00 122.45   0.55    1.00    --   44.91  19.00 -60.00  179
 19  \w     19.00 117.45   0.55    1.00    --   44.91  77.00  60.00  179
 20  \w     17.00  41.75   0.55    1.00    --   48.00  88.00-154.86   45
 21  \w     16.00  40.75   0.55    1.00    --   48.00  91.00 -78.25   45
 22  \w     15.00  39.75   0.55    1.00    --   48.00  92.00  72.67   45
 23  \w     30.00 128.45   0.55    1.00    --   56.00  77.00-106.03  179
 24  \w     30.00 128.45   0.55    1.00    --   56.00  77.00-106.03  179
 25  \w     31.00 129.45   0.55    1.00    --   56.00  75.00  95.23  179
 26  \w     35.00 132.35   0.55    1.00    --   60.00  75.00 -25.28  177
 27  \w     35.00 132.35   0.55    1.00    --   60.00  76.00-132.57  177
 28  \w     39.00 137.45   0.55    1.00    --   64.00  74.00  25.11  179
 29  \w     39.00 137.45   0.55    1.00    --   64.00  74.00  25.11  179
 30  \w     40.00 137.35   0.55    1.00    --   64.00  72.00 -46.92  177
 31  \w     39.00 137.45   0.55    1.00    --   64.00  76.00 110.92  179
 32  \w   -140.00 -45.95   0.55    1.00    --  -68.00 -70.00 -20.06  171
 33  \w   -140.00 -45.95   0.55    1.00    --  -68.00 -70.00 -20.06  171
 34  \w   -140.00 -47.60   0.55    1.00    --  -68.00 -64.00 100.15  168
 35  \w   -140.00 -47.60   0.55    1.00    --  -68.00 -64.00 118.79  168
 36  \w   -140.00 -48.70   0.55    1.00    --  -68.00 -63.00 137.59  166
 37  \w   -145.00 -53.70   0.55    1.00    --  -72.00 -60.00  10.07  166
 38  \w   -145.00 -50.95   0.55    1.00    --  -72.00 -67.00-116.02  171
 39  \w     46.00 144.45   0.55    1.00    --   72.00  77.00-146.41  179
 40  \w   -145.00 -47.65   0.55    1.00    --  -72.00 -74.00-174.70  177
 41  \w   -145.00 -47.65   0.55    1.00    --  -72.00 -74.00-174.70  177
 42  \w   -145.00 -50.95   0.55    1.00    --  -72.00 -67.00-116.02  171
 43  \w   -149.00 -51.65   0.55    1.00    --  -76.00 -75.00   8.49  177
 44  \w   -149.00 -52.75   0.55    1.00    --  -76.00 -71.00  48.81  175
 45  \w   -149.00 -52.75   0.55    1.00    --  -76.00 -73.00-120.96  175
 46  \w   -153.00 -60.60   0.55    1.00    --  -80.00 -59.00  60.90  168
 47  \w   -153.00 -59.50   0.55    1.00    --  -80.00 -64.00  89.47  170
 48  \w   -153.00 -60.60   0.55    1.00    --  -80.00 -59.00  60.90  168
 49  \w    -93.00 -63.30   0.55    1.00    --  -80.00 -60.00 -22.03   54
 50  \w    -99.00 -62.70   0.55    5.00    --  -84.00 -66.00 128.82   66
 51  \w    -97.00 -70.60   0.55    5.00    --  -88.00 -72.00  53.68   48
 52  \w    -91.00 -64.60   0.55    5.00    --  -88.00 -76.00-125.42   48
 53  \w   -102.00 -69.55   0.55    5.00    --  -93.75 -73.00 -75.64   59
 54  \w   -105.00 -69.80   0.55    5.00    --  -93.75 -75.00 -29.16   64
 55  \w   -123.00 -68.55   0.55    5.00    --  -93.75 -77.00-150.00   99
 56  \w   -107.00 -69.60   0.55    5.00    --  -93.75 -73.00 162.96   68
 57  \w   -125.00 -76.60   0.55    5.00    --  -93.75 -61.00  30.00   88
 58  \w    -95.00 -70.25   0.55    5.00    --  -93.75 -74.00 -18.56   45
 59  \w   -146.00-119.60   0.55    5.00    --  -93.75 -74.00 -18.56   48
 60  \w   -163.00-136.60   0.55    5.00    --  -93.75 -77.00-150.00   48
 61  \w   -119.00 -75.55   0.55    5.00    --  -93.75 -58.00  -9.40   79
 62  \w    -94.00 -69.25   0.55    5.00    --  -93.75 -77.00  90.00   45
 63  \w    -95.00 -70.25   0.55    5.00    --  -93.75 -75.00 -41.78   45
 64  \w   -155.00-129.70   0.55    5.00    --  -93.75 -75.00 -41.78   46
 65  \w   -102.00 -72.30   0.55    5.00    --  -93.75 -70.00 -62.84   54
 66  \w   -160.00-134.70   0.55    5.00    --  -93.75 -70.00 -62.84   46
 67  \w   -103.00 -70.55   0.55    5.00    --  -93.75 -77.00  30.00   59
 68  \w    -97.00 -70.60   0.55    5.00    --  -93.75 -72.00-102.44   48
 69  \w   -130.00 -70.05   0.55    5.00    --  -93.75 -73.00 124.48  109
 70  \w    -96.00 -69.60   0.55    5.00    --  -93.75 -77.00-180.00   48
 71  \w     44.00  68.75   0.55    5.00    --  115.25 -77.00-120.00   45
 72  \w     48.00 109.05   0.55    5.00    --  115.25-125.00 -90.00  111
 73  \w    138.00 164.40   0.55    5.00    --  115.25  77.00  90.00   48
 74  \w     99.00 125.95   0.55    5.00    --  115.25  77.00  90.00   49
 75  \w     93.00 119.40   0.55    5.00    --  115.25  77.00-120.00   48
 76  \w    149.00 175.40   0.55    5.00    --  115.25  61.00 150.00   48
 77  \w     89.00 158.30   0.55    5.00    --  115.25  77.00 -60.00  126
 78  \w    138.00 174.30   0.55    5.00    --  115.25  77.00  60.00   66
 79  \w     98.00 124.40   0.55    5.00    --  115.25  61.00 150.00   48
 80  \w    130.00 174.00   0.55    5.00    --  115.25  45.00 120.00   80
 81  \w     98.00 141.45   0.55    5.00    --  115.25  45.00 -90.00   79
 82  \w     94.00 120.40   0.55    5.00    --  115.25  77.00  60.00   48
 83  \w     73.00  99.40   0.55    5.00    --  115.25-125.00 120.00   48
 84  \w    131.00 160.70   0.55    5.00    --  115.25  77.00 -30.00   54
 85  \w     48.00  82.10   0.55    5.00    --  115.25-125.00   0.00   62
 86  \w     85.00 109.75   0.55    5.00    --  115.25-125.00  60.00   45
 87  \w     90.00 126.30   0.55    5.00    --  115.25  77.00 -30.00   66
 88  \w    123.00 149.40   0.55    5.00    --  115.25  30.00 -30.00   48
 89  \w     57.00  83.40   0.55    5.00    --  115.25-125.00  60.00   48
 90  \w     69.00  95.40   0.55    5.00    --  115.25 -77.00-180.00   48
 91  \w    102.00 174.05   0.55    5.00    --  115.25  61.00   0.00  131
 92  \w     44.00  68.75   0.55    5.00    --  115.25 -61.00 -30.00   45
 93  \w     99.00 125.95   0.55    5.00    --  115.25  61.00  90.00   49
 94  \w    100.00 148.95   0.55    5.00    --  115.25  61.00-180.00   89
 95  \w    119.00 158.05   0.55    5.00    --  115.25  30.00 -90.00   71
 96  \w     44.00  87.45   0.55    5.00    --  115.25 -77.00 150.00   79
 97  \w    152.00 177.30   0.55    5.00    --  115.25  61.00  60.00   46
 98  \w    139.00 165.40   0.55    5.00    --  115.25  45.00 150.00   48
 99  \w     98.00 124.40   0.55    5.00    --  115.25  45.00 150.00   48
100  \w    147.00 173.95   0.55    5.00    --  115.25  77.00 120.00   49
101  \w     89.00 115.95   0.55    5.00    --  115.25  77.00 120.00   49
102  \w     90.00 171.40   0.55    5.00    --  115.25  77.00 -90.00  148
103  \w    141.00 167.40   0.55    5.00    --  115.25  30.00   0.00   48
104  \w     96.00 141.10   0.55    5.00    --  115.25 125.00  90.00   82
105  \w    106.00 132.40   0.55    5.00    --  115.25  30.00   0.00   48
106  \w     44.00  68.75   0.55    5.00    --  115.25 -77.00-150.00   45
107  \w     53.00  99.20   0.55    5.00    --  115.25 -77.00   0.00   84
108  \w     79.00 103.75   0.55    5.00    --  115.25 -95.00  90.00   45
109  \w    105.00 158.35   0.55    5.00    --  115.25  45.00-150.00   97
110  \w     46.00 110.35   0.55    5.00    --  115.25-125.00-180.00  117
111  \w     74.00 103.70   0.55    5.00    --  115.25 -95.00  60.00   54
112  \w     45.00  71.40   0.55    5.00    --  115.25-125.00 120.00   48
113  \w     69.00 101.45   0.55    5.00    --  115.25 -95.00   0.00   59
114  \w    147.00 173.40   0.55    5.00    --  115.25  77.00   0.00   48
115  \w     44.00  70.40   0.55    5.00    --  115.25 -61.00  90.00   48
116  \w     90.00 119.70   0.55    5.00    --  115.25  77.00   0.00   54
117  \w    152.00 177.30   0.55    5.00    --  115.25  77.00-180.00   46
118  \w     43.00  69.40   0.55    5.00    --  115.25 -61.00-180.00   48
119  \w    106.00 150.00   0.55    5.00    --  115.25  30.00-150.00   80
120  \w     98.00 138.15   0.55    5.00    --  115.25  61.00 -90.00   73
121  \w     47.00  71.75   0.55    5.00    --  115.25 -95.00  60.00   45
122  \w     89.00 115.40   0.55    5.00    --  115.25  77.00-180.00   48
123  \w    122.00 172.05   0.55    5.00    --  115.25  77.00  30.00   91
124  \w    141.00 166.30   0.55    5.00    --  115.25  61.00 -60.00   46
125  \w     99.00 130.35   0.55    5.00    --  115.25  61.00 -60.00   57
126  \w     91.00 117.40   0.55    5.00    --  115.25  77.00  30.00   48
127  \w     98.00 151.35   0.55    5.00    --  115.25  45.00  30.00   97
128  \w     97.00 131.10   0.55    5.00    --  115.25  61.00  60.00   62
129  \w    145.00 171.40   0.55    5.00    --  115.25  61.00-120.00   48
130  \w     96.00 140.00   0.55    5.00    --  115.25  61.00-120.00   80
131  \w     43.00  69.40   0.55    5.00    --  115.25 -77.00  30.00   48
132  \w     89.00 115.40   0.55    5.00    --  115.25 -81.00 121.16   48
133  \w     43.00  69.40   0.55    5.00    --  115.25 -77.00 -90.00   48
134  \w     92.00 124.45   0.55    5.00    --  115.25  77.00 150.00   59
135  \w     74.00 103.70   0.55    5.00    --  115.25 -77.00  60.00   54
136  \w    108.00 158.05   0.55    5.00    --  115.25 125.00 -60.00   91
137  \w     43.00  69.40   0.55    5.00    --  115.25 -77.00  60.00   48
138  \w    151.00 176.30   0.55    5.00    --  115.25  45.00-180.00   46
139  \w     99.00 161.15   0.55    5.00    --  115.25  61.00  30.00  113
140  \w    130.00 159.70   0.55    5.00    --  115.25  61.00-150.00   54
141  \w     44.00  98.45   0.55    5.00    --  115.25 -77.00 -60.00   99
142  \w     99.00 123.75   0.55    5.00    --  115.25  61.00-150.00   45
143  \w    142.00 174.45   0.55    5.00    --  115.25  30.00  60.00   59
144  \w    134.00 177.45   0.55    5.00    --  115.25  77.00-150.00   79
145  \w    111.00 137.40   0.55    5.00    --  115.25  45.00  60.00   48
146  \w    105.00 131.40   0.55    5.00    --  115.25  45.00   0.00   48
147  \w    129.00 155.40   0.55    5.00    --  115.25  45.00-120.00   48
148  \w     46.00  72.40   0.55    5.00    --  115.25-125.00  30.00   48
149  \w    136.00 173.40   0.55    5.00    --  115.25  45.00  90.00   68
150  \w     82.00 108.40   0.55    5.00    --  115.25-125.00-150.00   48
151  \w     44.00  70.40   0.55    5.00    --  115.25 -95.00 -30.00   48
152  \w     62.00  96.10   0.55    5.00    --  115.25 -95.00 -60.00   62
153  \w     66.00 102.30   0.55    5.00    --  115.25 -95.00-180.00   66
154  \w     73.00 102.70   0.55    5.00    --  115.25 -77.00-120.00   54
155  \w     45.00  77.45   0.55    5.00    --  115.25-125.00-150.00   59
156  \w     89.00 120.35   0.55    5.00    --  115.25  77.00-150.00   57
157  \w    147.00 176.70   0.55    5.00    --  115.25  45.00 -90.00   54
158  \w     44.00  68.75   0.55    5.00    --  115.25 -77.00  90.00   45
;
_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      -0.1032577000
_diffrn_orient_matrix_UB_12      0.1232054000
_diffrn_orient_matrix_UB_13      0.0626628000
_diffrn_orient_matrix_UB_21      0.0223279000
_diffrn_orient_matrix_UB_22      0.1492532000
_diffrn_orient_matrix_UB_23      -0.1287889000
_diffrn_orient_matrix_UB_31      -0.2010828000
_diffrn_orient_matrix_UB_32      0.0054979000
_diffrn_orient_matrix_UB_33      -0.0533711000
_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  0.0630
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30583
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.176
_diffrn_reflns_theta_min         4.387
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.298
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.112a (Rigaku Oxford Diffraction, 2025)
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    1.896
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0967P)^2^+0.2224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2544
_reflns_number_total             2641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01047k2.cif
_cod_data_source_block           Ris657
_cod_database_code               7251338
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C5 H N9 O3 K'
_chemical_oxdiff_usercomment     Ris657
_shelx_estimated_absorpt_t_max   0.811
_shelx_estimated_absorpt_t_min   0.285
_diffrn_oxdiff_digest_hkl
;
43cc2be48c49d133b0e6e725f673fed6c2a307
;
_diffrn_oxdiff_digest_od_ed
;

;
_olex2_refinement_description
;
;
_shelx_res_checksum              60669
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.568
_oxdiff_exptl_absorpt_empirical_full_min 0.652