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Acta Cryst. (2018). E74, 505-513
https://doi.org/10.1107/S205698901800364X
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Effect of counter-ion on packing and crystal density of 5,5′-(3,3′-bi[1,2,4-oxa­diazole]-5,5′-di­yl)bis­(1H-tetra­zol-1-olate) with five different cations

I. D. Giles, A. J. DeHope, N. B. Zuckerman, D. A. Parrish and P. F. Pagoria
In energetic materials, the crystal density is an important parameter that affects the performance of the material. When making ionic energetic materials, the choice of counter-ion can have detrimental or beneficial effects on the packing, and therefore the density, of the resulting energetic crystal. Presented herein are a series of five ionic energetic crystals, all containing the 5,5′-(3,3′-bi[1,2,4-oxa­diazole]-5,5′-di­yl)bis­(1H-tetra­zol-1-olate) dianion.
Keywords: crystal structure; tetra­zole; oxa­diazole; tri­amino­guandidinium; hydrazinium; hydroxyl­ammonium; amino­guanidinium; 5-amino-1H-tetra­zol-4-ium; energetic materials.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901800364X/pk2606sup1.cif
Contains datablocks global, 1, 2, 3, 4, 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901800364X/pk26061sup9.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901800364X/pk26062sup10.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901800364X/pk26063sup15.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901800364X/pk26064sup20.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901800364X/pk26065sup8.hkl
Contains datablock 5

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901800364X/pk26061sup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901800364X/pk26062sup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901800364X/pk26063sup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901800364X/pk26064sup10.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901800364X/pk26065sup11.cml
Supplementary material

CCDC references: 1567804; 1567784; 1567783; 1567780; 1567779

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.031
  • wR factor = 0.081
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Datablock: 1



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report


Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O7             105.7 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          5 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              H5 N2
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info


   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check





Datablock: 2



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C6 N12 O4
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info


Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O7             105.7 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              H4 N O
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by .          1 Units


   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check





Datablock: 3



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report


Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O7             106.0 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          8 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info


   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check





Datablock: 4



Alert level B
PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ...          3 Check
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          3 Check


Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.6 Note
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          4 Check


Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          8 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O7             105.7 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O13            105.9 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1S      ..C16              2.99 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O21      ..C6               2.96 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          8 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C H4 N5
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          4 Note
              H2 O
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          5 Note
              H2 O
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          6 Note
              H2 O
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         27 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info


   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check





Datablock: 5



Alert level A
PLAT902_ALERT_1_A No (Interpretable) Reflections Found in FCF ....     Please Check


Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.07 Report
PLAT097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       0.74 eA-3
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13      ..N4A              2.65 Ang.


Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          7 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          5 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        55% Note
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O7             105.8 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  O11A     ..C9               3.00 Ang.
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         63 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note


   1 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  15 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check



checkCIF publication errors


Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 390
              centroid~C6-O7-N8-C9-N10~--centroid~N1A-N2~<i>~A~</i>~-N3~<i>~A~</i>~-\
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~
PUBL022_ALERT_1_A There is a mismatched ~ on line 391
              N4~<i>~A~</i>~-C5~<i>~A~</i> distance of 3.59(2) \%A
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~
PUBL022_ALERT_1_A There is a mismatched ~ on line 392
              [centroid~C6-O7-N8-C9-N10~--centroid~N1~<i>~A~</i>~-N2~<i>~A~</i>~-\
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~
PUBL022_ALERT_1_A There is a mismatched ~ on line 393
              N3~<i>~A~</i>~-N4~<i>~A~</i>~-C5~<i>~A~</i>--N1<i>A</i> angle 65.4(2)\%].
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~


   4 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing
Computing details top

For all structures, data collection: APEX2 (Bruker, 2010); cell refinement: APEX2 (Bruker, 2010); data reduction: SAINT (Bruker, 2014) and XPREP (Bruker, 2014); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis(hydrazinium) 5,5'-(3,3'-bi[1,2,4-oxadiazole]-5,5'-diyl)bis(1H-tetrazol-1-olate) (1) top
Crystal data top
2N2H5+·C6N12O42−F(000) = 380
Mr = 370.30Dx = 1.694 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.7660 (7) ÅCell parameters from 2894 reflections
b = 13.6716 (13) Åθ = 5.3–52.6°
c = 6.8655 (7) ŵ = 0.14 mm−1
β = 95.237 (3)°T = 150 K
V = 725.89 (12) Å3Plate, colorless
Z = 20.16 × 0.15 × 0.02 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		1305 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.021
ω scansθmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		h = −9→9
Tmin = 0.978, Tmax = 0.997k = −17→14
6871 measured reflectionsl = −8→8
1487 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Only H-atom coordinates refined
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0399P)2 + 0.3165P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1487 reflectionsΔρmax = 0.32 e Å−3
133 parametersΔρmin = −0.22 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.91941 (14)0.84680 (8)0.62466 (16)0.0184 (2)
O11.08551 (12)0.84622 (8)0.62286 (14)0.0241 (2)
N20.83787 (15)0.80806 (9)0.77124 (16)0.0235 (3)
N30.67149 (15)0.82236 (9)0.72476 (17)0.0255 (3)
N40.64295 (15)0.86940 (9)0.55408 (17)0.0226 (3)
C50.79919 (17)0.88419 (9)0.49298 (18)0.0180 (3)
C60.83669 (16)0.92874 (9)0.31140 (18)0.0180 (3)
O70.70233 (12)0.96564 (7)0.19724 (13)0.0226 (2)
N80.77323 (15)1.00423 (9)0.03192 (16)0.0221 (3)
C90.93752 (17)0.98533 (9)0.06782 (18)0.0177 (3)
N100.98504 (14)0.93766 (8)0.24049 (15)0.0179 (2)
N1S0.68154 (15)1.18606 (9)0.65235 (17)0.0205 (3)
H1SA0.683 (2)1.1856 (11)0.789 (3)0.025*
H1SB0.782 (2)1.1628 (12)0.614 (2)0.025*
H1SC0.591 (2)1.1482 (12)0.596 (2)0.025*
N2S0.65948 (15)1.28374 (9)0.57262 (16)0.0200 (3)
H2SA0.560 (2)1.3046 (12)0.609 (2)0.024*
H2SB0.740 (2)1.3199 (12)0.636 (2)0.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0201 (5)0.0188 (6)0.0166 (5)−0.0012 (4)0.0029 (4)−0.0017 (4)
O10.0168 (5)0.0353 (6)0.0202 (5)0.0052 (4)0.0013 (4)0.0017 (4)
N20.0282 (6)0.0246 (6)0.0182 (6)−0.0028 (5)0.0046 (5)0.0026 (5)
N30.0232 (6)0.0308 (7)0.0230 (6)−0.0048 (5)0.0045 (5)0.0024 (5)
N40.0212 (6)0.0251 (6)0.0217 (6)−0.0040 (5)0.0033 (4)0.0012 (5)
C50.0194 (6)0.0159 (6)0.0186 (6)−0.0012 (5)0.0014 (5)−0.0015 (5)
C60.0186 (6)0.0159 (6)0.0191 (6)−0.0001 (5)−0.0007 (5)−0.0009 (5)
O70.0184 (5)0.0280 (5)0.0215 (5)0.0003 (4)0.0016 (4)0.0060 (4)
N80.0228 (6)0.0236 (6)0.0200 (6)−0.0005 (5)0.0021 (4)0.0049 (5)
C90.0208 (6)0.0142 (6)0.0178 (6)0.0002 (5)−0.0001 (5)0.0005 (5)
N100.0196 (5)0.0169 (5)0.0172 (5)0.0004 (4)0.0016 (4)0.0014 (4)
N1S0.0172 (6)0.0265 (6)0.0177 (6)−0.0001 (5)0.0013 (4)−0.0002 (5)
N2S0.0178 (6)0.0233 (6)0.0188 (5)−0.0007 (5)0.0015 (5)−0.0025 (5)
Geometric parameters (Å, º) top
N1—O11.2912 (14)N8—C91.3031 (18)
N1—C51.3402 (17)C9—N101.3735 (16)
N1—N21.3455 (16)C9—C9i1.461 (3)
N2—N31.3170 (17)N1S—N2S1.4476 (16)
N3—N41.3373 (17)N1S—H1SA0.939 (17)
N4—C51.3349 (17)N1S—H1SB0.904 (18)
C5—C61.4409 (18)N1S—H1SC0.930 (18)
C6—N101.2968 (17)N2S—H2SA0.883 (18)
C6—O71.3447 (16)N2S—H2SB0.882 (18)
O7—N81.4085 (14)
O1—N1—C5129.12 (11)N8—C9—N10116.02 (12)
O1—N1—N2122.92 (11)N8—C9—C9i121.39 (14)
C5—N1—N2107.96 (11)N10—C9—C9i122.59 (15)
N3—N2—N1106.18 (11)C6—N10—C9100.99 (11)
N2—N3—N4111.36 (11)N2S—N1S—H1SA112.1 (10)
C5—N4—N3105.40 (11)N2S—N1S—H1SB106.9 (11)
N4—C5—N1109.11 (11)H1SA—N1S—H1SB110.7 (15)
N4—C5—C6126.67 (12)N2S—N1S—H1SC107.3 (10)
N1—C5—C6124.16 (12)H1SA—N1S—H1SC110.6 (14)
N10—C6—O7114.49 (11)H1SB—N1S—H1SC109.1 (14)
N10—C6—C5128.41 (12)N1S—N2S—H2SA105.6 (11)
O7—C6—C5117.10 (11)N1S—N2S—H2SB106.0 (11)
C6—O7—N8105.70 (10)H2SA—N2S—H2SB106.4 (15)
C9—N8—O7102.79 (10)
O1—N1—N2—N3179.57 (11)N4—C5—C6—O75.1 (2)
C5—N1—N2—N30.31 (14)N1—C5—C6—O7−177.99 (12)
N1—N2—N3—N4−0.35 (15)N10—C6—O7—N8−0.61 (15)
N2—N3—N4—C50.26 (15)C5—C6—O7—N8179.95 (11)
N3—N4—C5—N1−0.06 (15)C6—O7—N8—C90.25 (13)
N3—N4—C5—C6177.23 (13)O7—N8—C9—N100.14 (15)
O1—N1—C5—N4−179.36 (12)O7—N8—C9—C9i−179.12 (15)
N2—N1—C5—N4−0.16 (15)O7—C6—N10—C90.65 (14)
O1—N1—C5—C63.3 (2)C5—C6—N10—C9−179.98 (13)
N2—N1—C5—C6−177.52 (12)N8—C9—N10—C6−0.48 (15)
N4—C5—C6—N10−174.25 (13)C9i—C9—N10—C6178.77 (15)
N1—C5—C6—N102.6 (2)
Symmetry code: (i) −x+2, −y+2, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1S—H1SA···N2Sii0.939 (17)2.015 (18)2.9353 (16)166.1 (14)
N1S—H1SB···O1iii0.904 (18)2.007 (17)2.7679 (15)141.0 (14)
N1S—H1SC···N4iv0.930 (18)2.018 (18)2.8778 (17)153.0 (14)
N2S—H2SA···N3v0.883 (18)2.227 (18)3.0778 (17)161.6 (15)
N2S—H2SB···O1vi0.882 (18)2.071 (18)2.8752 (15)151.2 (15)
Symmetry codes: (ii) x, −y+5/2, z+1/2; (iii) −x+2, −y+2, −z+1; (iv) −x+1, −y+2, −z+1; (v) −x+1, y+1/2, −z+3/2; (vi) −x+2, y+1/2, −z+3/2.
Bis(hydroxyammonium) 5,5'-(3,3'-bi[1,2,4-oxadiazole]-5,5'-diyl)bis(1H-tetrazol-1-olate) (2) top
Crystal data top
2NH4O+·C6N12O42−F(000) = 380
Mr = 372.26Dx = 1.873 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.1011 (9) ÅCell parameters from 2126 reflections
b = 18.494 (3) Åθ = 4.4–51.8°
c = 7.0044 (13) ŵ = 0.17 mm−1
β = 92.624 (2)°T = 296 K
V = 660.1 (2) Å3Plate, colorless
Z = 20.33 × 0.19 × 0.02 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		1152 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.027
ω scansθmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		h = −6→6
Tmin = 0.948, Tmax = 0.997k = −23→23
5834 measured reflectionsl = −8→8
1358 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.1422P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
1358 reflectionsΔρmax = 0.23 e Å−3
122 parametersΔρmin = −0.25 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.26439 (19)0.64777 (6)0.49548 (14)0.0199 (3)
N10.2362 (2)0.64703 (6)0.30834 (18)0.0170 (3)
N20.3978 (2)0.68219 (7)0.19563 (19)0.0208 (3)
N30.3121 (3)0.66943 (7)0.01809 (19)0.0227 (3)
N40.0995 (2)0.62648 (7)0.01466 (18)0.0204 (3)
C50.0547 (3)0.61257 (8)0.1968 (2)0.0168 (3)
C6−0.1502 (3)0.56752 (8)0.2694 (2)0.0166 (3)
O7−0.2867 (2)0.52656 (6)0.14236 (15)0.0237 (3)
N8−0.4729 (3)0.48950 (7)0.24763 (19)0.0234 (3)
C9−0.4235 (3)0.51234 (8)0.4207 (2)0.0164 (3)
N10−0.2225 (2)0.56162 (7)0.44333 (18)0.0174 (3)
O1S−0.1197 (2)0.72437 (6)0.61500 (17)0.0248 (3)
H1S0.003 (4)0.6930 (12)0.578 (3)0.037*
N1S−0.2862 (2)0.68301 (7)0.72712 (19)0.0187 (3)
H1SA−0.3927600.6564910.6512090.028*
H1SB−0.3811300.7123750.7972320.028*
H1SC−0.1900310.6540380.8037730.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0150 (5)0.0290 (6)0.0157 (6)0.0000 (4)0.0006 (4)−0.0016 (4)
N10.0127 (6)0.0200 (6)0.0185 (7)0.0003 (5)0.0021 (5)0.0014 (5)
N20.0149 (6)0.0237 (7)0.0242 (7)−0.0007 (5)0.0056 (5)0.0018 (5)
N30.0181 (6)0.0263 (7)0.0241 (7)0.0005 (5)0.0056 (5)0.0034 (5)
N40.0168 (6)0.0243 (7)0.0205 (7)0.0009 (5)0.0040 (5)0.0027 (5)
C50.0128 (6)0.0198 (7)0.0178 (8)0.0022 (5)0.0003 (5)0.0005 (5)
C60.0135 (7)0.0182 (7)0.0180 (8)0.0013 (5)−0.0004 (6)0.0001 (6)
O70.0235 (6)0.0295 (6)0.0181 (6)−0.0096 (5)0.0026 (5)−0.0011 (4)
N80.0219 (7)0.0272 (7)0.0213 (7)−0.0092 (5)0.0036 (6)0.0010 (5)
C90.0134 (7)0.0162 (7)0.0196 (8)0.0007 (5)0.0005 (6)0.0010 (6)
N100.0134 (6)0.0198 (6)0.0192 (7)−0.0013 (5)0.0014 (5)0.0008 (5)
O1S0.0181 (5)0.0238 (6)0.0335 (7)−0.0016 (5)0.0127 (5)0.0016 (5)
N1S0.0140 (6)0.0226 (7)0.0199 (7)−0.0015 (5)0.0032 (5)0.0008 (5)
Geometric parameters (Å, º) top
O1—N11.3122 (16)O7—N81.4071 (16)
N1—N21.3361 (18)N8—C91.298 (2)
N1—C51.3443 (19)C9—N101.3755 (19)
N2—N31.3204 (19)C9—C9i1.459 (3)
N3—N41.3436 (18)O1S—N1S1.4087 (16)
N4—C51.332 (2)O1S—H1S0.90 (2)
C5—C61.447 (2)N1S—H1SA0.8900
C6—N101.294 (2)N1S—H1SB0.8900
C6—O71.3391 (18)N1S—H1SC0.8900
O1—N1—N2122.87 (12)C9—N8—O7102.96 (11)
O1—N1—C5128.79 (12)N8—C9—N10115.78 (13)
N2—N1—C5108.33 (12)N8—C9—C9i121.42 (17)
N3—N2—N1106.43 (12)N10—C9—C9i122.79 (17)
N2—N3—N4110.78 (12)C6—N10—C9100.99 (12)
C5—N4—N3105.72 (13)N1S—O1S—H1S104.8 (13)
N4—C5—N1108.74 (13)O1S—N1S—H1SA109.5
N4—C5—C6127.32 (13)O1S—N1S—H1SB109.5
N1—C5—C6123.94 (13)H1SA—N1S—H1SB109.5
N10—C6—O7114.58 (13)O1S—N1S—H1SC109.5
N10—C6—C5128.39 (14)H1SA—N1S—H1SC109.5
O7—C6—C5117.03 (13)H1SB—N1S—H1SC109.5
C6—O7—N8105.68 (11)
O1—N1—N2—N3179.78 (12)N4—C5—C6—O710.8 (2)
C5—N1—N2—N30.58 (15)N1—C5—C6—O7−168.32 (13)
N1—N2—N3—N4−0.30 (15)N10—C6—O7—N80.34 (16)
N2—N3—N4—C5−0.10 (16)C5—C6—O7—N8−179.17 (12)
N3—N4—C5—N10.46 (15)C6—O7—N8—C9−0.35 (15)
N3—N4—C5—C6−178.77 (14)O7—N8—C9—N100.29 (17)
O1—N1—C5—N4−179.80 (13)O7—N8—C9—C9i179.29 (16)
N2—N1—C5—N4−0.66 (16)O7—C6—N10—C9−0.17 (16)
O1—N1—C5—C6−0.5 (2)C5—C6—N10—C9179.28 (14)
N2—N1—C5—C6178.61 (13)N8—C9—N10—C6−0.09 (17)
N4—C5—C6—N10−168.63 (15)C9i—C9—N10—C6−179.08 (17)
N1—C5—C6—N1012.2 (2)
Symmetry code: (i) −x−1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1S—H1S···O10.90 (2)1.70 (2)2.5880 (15)169 (2)
N1S—H1SA···O1ii0.892.022.8234 (17)149
N1S—H1SB···N2iii0.892.352.9713 (19)127
N1S—H1SC···N4iv0.892.102.9425 (19)157
Symmetry codes: (ii) x−1, y, z; (iii) x−1, −y+3/2, z+1/2; (iv) x, y, z+1.
Dimethylammonium 5,5'-(3,3'-bi[1,2,4-oxadiazole]-5,5'-diyl)bis(1H-tetrazol-1-olate) (3) top
Crystal data top
2C2H8N+·C6N12O42−Z = 1
Mr = 396.37F(000) = 206
Triclinic, P1Dx = 1.544 Mg m−3
a = 6.0946 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.5197 (8) ÅCell parameters from 1925 reflections
c = 9.2814 (9) Åθ = 4.8–52.6°
α = 68.259 (3)°µ = 0.12 mm−1
β = 75.957 (3)°T = 150 K
γ = 74.816 (3)°Plate, yellow
V = 426.28 (7) Å30.18 × 0.12 × 0.04 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		1490 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.018
ω scansθmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		h = −7→7
Tmin = 0.978, Tmax = 0.995k = −10→9
4131 measured reflectionsl = −11→11
1737 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0432P)2 + 0.1053P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1737 reflectionsΔρmax = 0.27 e Å−3
129 parametersΔρmin = −0.23 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.59547 (17)0.36241 (13)0.87451 (12)0.0211 (2)
N20.73348 (18)0.44045 (14)0.90588 (12)0.0246 (3)
N30.69908 (19)0.60180 (14)0.81186 (13)0.0259 (3)
N40.54333 (18)0.62953 (14)0.72093 (12)0.0241 (2)
C50.4791 (2)0.47875 (15)0.76160 (14)0.0205 (3)
C60.3133 (2)0.44918 (15)0.69185 (14)0.0201 (3)
O70.25452 (15)0.29342 (11)0.74431 (10)0.0248 (2)
N80.09343 (19)0.30587 (14)0.65217 (13)0.0249 (3)
C90.0765 (2)0.46521 (15)0.55884 (13)0.0201 (3)
N100.20941 (17)0.56041 (13)0.57819 (11)0.0210 (2)
O110.58447 (16)0.20008 (11)0.94750 (10)0.0258 (2)
N1S0.26051 (19)0.04614 (13)0.19850 (12)0.0249 (3)
H1SA0.3446800.1285010.1378830.030*
H1SB0.312665−0.0453060.1628140.030*
C2S0.0164 (3)0.11493 (19)0.1796 (2)0.0399 (4)
H2SA−0.0754720.0266670.2436640.060*
H2SB0.0023620.1473900.0688570.060*
H2SC−0.0395930.2163840.2138100.060*
C3S0.2991 (3)−0.00899 (18)0.36271 (16)0.0326 (3)
H3SA0.2329270.0862120.4048370.049*
H3SB0.464886−0.0421530.3657810.049*
H3SC0.224951−0.1075860.4264030.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0216 (5)0.0208 (5)0.0207 (5)−0.0039 (4)−0.0006 (4)−0.0083 (4)
N20.0227 (5)0.0291 (6)0.0260 (5)−0.0061 (4)−0.0025 (4)−0.0136 (5)
N30.0264 (6)0.0266 (6)0.0270 (6)−0.0078 (4)−0.0014 (4)−0.0116 (5)
N40.0258 (5)0.0245 (5)0.0246 (5)−0.0083 (4)−0.0018 (4)−0.0100 (4)
C50.0214 (6)0.0208 (6)0.0197 (6)−0.0042 (5)−0.0007 (5)−0.0084 (5)
C60.0211 (6)0.0187 (6)0.0205 (6)−0.0047 (5)0.0013 (5)−0.0086 (5)
O70.0293 (5)0.0193 (4)0.0275 (5)−0.0079 (4)−0.0099 (4)−0.0039 (4)
N80.0283 (6)0.0232 (5)0.0263 (5)−0.0073 (4)−0.0093 (4)−0.0068 (4)
C90.0206 (6)0.0208 (6)0.0199 (6)−0.0045 (5)0.0002 (5)−0.0096 (5)
N100.0224 (5)0.0199 (5)0.0219 (5)−0.0056 (4)−0.0027 (4)−0.0077 (4)
O110.0326 (5)0.0183 (4)0.0250 (5)−0.0044 (4)−0.0041 (4)−0.0061 (3)
N1S0.0301 (6)0.0178 (5)0.0254 (5)−0.0062 (4)−0.0009 (4)−0.0068 (4)
C2S0.0344 (8)0.0275 (7)0.0587 (10)−0.0035 (6)−0.0172 (7)−0.0110 (7)
C3S0.0452 (8)0.0251 (7)0.0269 (7)−0.0057 (6)−0.0071 (6)−0.0077 (5)
Geometric parameters (Å, º) top
N1—O111.3071 (13)C9—C9i1.463 (2)
N1—N21.3377 (15)N1S—C2S1.4767 (18)
N1—C51.3440 (16)N1S—C3S1.4780 (17)
N2—N31.3207 (15)N1S—H1SA0.9100
N3—N41.3390 (16)N1S—H1SB0.9100
N4—C51.3334 (16)C2S—H2SA0.9800
C5—C61.4410 (18)C2S—H2SB0.9800
C6—N101.2964 (16)C2S—H2SC0.9800
C6—O71.3460 (14)C3S—H3SA0.9800
O7—N81.4115 (14)C3S—H3SB0.9800
N8—C91.3049 (16)C3S—H3SC0.9800
C9—N101.3671 (16)
O11—N1—N2122.67 (10)C2S—N1S—C3S113.54 (12)
O11—N1—C5129.09 (11)C2S—N1S—H1SA108.9
N2—N1—C5108.24 (10)C3S—N1S—H1SA108.9
N3—N2—N1106.11 (10)C2S—N1S—H1SB108.9
N2—N3—N4111.33 (10)C3S—N1S—H1SB108.9
C5—N4—N3105.34 (10)H1SA—N1S—H1SB107.7
N4—C5—N1108.98 (11)N1S—C2S—H2SA109.5
N4—C5—C6124.29 (11)N1S—C2S—H2SB109.5
N1—C5—C6126.73 (12)H2SA—C2S—H2SB109.5
N10—C6—O7113.91 (11)N1S—C2S—H2SC109.5
N10—C6—C5126.23 (11)H2SA—C2S—H2SC109.5
O7—C6—C5119.86 (11)H2SB—C2S—H2SC109.5
C6—O7—N8105.99 (9)N1S—C3S—H3SA109.5
C9—N8—O7102.47 (10)N1S—C3S—H3SB109.5
N8—C9—N10116.05 (11)H3SA—C3S—H3SB109.5
N8—C9—C9i121.02 (14)N1S—C3S—H3SC109.5
N10—C9—C9i122.94 (13)H3SA—C3S—H3SC109.5
C6—N10—C9101.58 (10)H3SB—C3S—H3SC109.5
O11—N1—N2—N3−179.65 (9)N4—C5—C6—O7−177.99 (10)
C5—N1—N2—N3−0.10 (13)N1—C5—C6—O72.86 (18)
N1—N2—N3—N4−0.09 (13)N10—C6—O7—N80.34 (13)
N2—N3—N4—C50.25 (13)C5—C6—O7—N8−179.34 (10)
N3—N4—C5—N1−0.31 (13)C6—O7—N8—C9−0.33 (12)
N3—N4—C5—C6−179.59 (11)O7—N8—C9—N100.24 (13)
O11—N1—C5—N4179.77 (10)O7—N8—C9—C9i−179.89 (13)
N2—N1—C5—N40.26 (13)O7—C6—N10—C9−0.18 (13)
O11—N1—C5—C6−1.0 (2)C5—C6—N10—C9179.47 (11)
N2—N1—C5—C6179.52 (11)N8—C9—N10—C6−0.05 (14)
N4—C5—C6—N102.38 (19)C9i—C9—N10—C6−179.91 (14)
N1—C5—C6—N10−176.77 (11)
Symmetry code: (i) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1S—H1SA···O11ii0.912.012.8118 (14)146
N1S—H1SB···O11iii0.911.852.7524 (14)169
Symmetry codes: (ii) x, y, z−1; (iii) −x+1, −y, −z+1.
Bis(5-amino-1H-tetrazol-4-ium) 5,5'-(3,3'-bi[1,2,4-oxadiazole]-5,5'-diyl)bis(1H-tetrazol-1-olate) (4) top
Crystal data top
2CH4N5+·C6N12O42−·4H2OF(000) = 1128
Mr = 548.36Dx = 1.701 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 24.783 (2) ÅCell parameters from 5868 reflections
b = 12.7081 (11) Åθ = 5.9–52.2°
c = 6.8396 (6) ŵ = 0.15 mm−1
β = 96.289 (1)°T = 150 K
V = 2141.1 (3) Å3Rod, colorless
Z = 40.28 × 0.04 × 0.04 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		3489 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.027
ω scansθmax = 26.2°, θmin = 0.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		h = −30→29
Tmin = 0.960, Tmax = 0.994k = −15→15
18508 measured reflectionsl = −8→8
4274 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0807P)2 + 0.1085P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max < 0.001
4274 reflectionsΔρmax = 0.37 e Å−3
367 parametersΔρmin = −0.32 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.41199 (5)0.76890 (10)0.63477 (19)0.0175 (3)
N20.46216 (6)0.76711 (11)0.7314 (2)0.0222 (3)
N30.47698 (6)0.66717 (11)0.7465 (2)0.0245 (3)
N40.43777 (6)0.60492 (11)0.6622 (2)0.0223 (3)
C50.39732 (6)0.66827 (12)0.5933 (2)0.0170 (3)
C60.34669 (6)0.63795 (12)0.4870 (2)0.0163 (3)
O70.33906 (4)0.53484 (8)0.44763 (16)0.0201 (3)
N80.28771 (6)0.52728 (10)0.3395 (2)0.0207 (3)
C90.27141 (6)0.62482 (12)0.3281 (2)0.0175 (3)
N100.30649 (5)0.69743 (10)0.41848 (19)0.0176 (3)
C110.21877 (6)0.65335 (12)0.2242 (2)0.0169 (3)
N120.20196 (6)0.75103 (11)0.2139 (2)0.0210 (3)
O130.15057 (4)0.74291 (8)0.10499 (17)0.0205 (3)
C140.14345 (6)0.63995 (12)0.0628 (2)0.0170 (3)
N150.18379 (5)0.58086 (10)0.1320 (2)0.0188 (3)
C160.09360 (6)0.60847 (12)−0.0484 (2)0.0176 (3)
N170.07914 (5)0.50775 (10)−0.08548 (19)0.0184 (3)
N180.02984 (6)0.50893 (11)−0.1896 (2)0.0234 (3)
N190.01537 (6)0.60884 (11)−0.2111 (2)0.0233 (3)
N200.05393 (5)0.67176 (11)−0.1253 (2)0.0214 (3)
O210.38511 (5)0.85499 (9)0.59296 (17)0.0235 (3)
O220.10524 (5)0.42236 (9)−0.03543 (19)0.0280 (3)
C23−0.12543 (7)0.63807 (13)−0.5210 (2)0.0197 (4)
N24−0.12672 (6)0.53320 (10)−0.5150 (2)0.0215 (3)
H24−0.1005930.492838−0.4590910.026*
N25−0.17470 (6)0.49815 (12)−0.6087 (2)0.0283 (4)
N26−0.20249 (6)0.57784 (11)−0.6713 (2)0.0287 (4)
N27−0.17293 (6)0.66536 (11)−0.6197 (2)0.0223 (3)
H27−0.1834560.730349−0.6470160.027*
N28−0.08567 (6)0.70014 (11)−0.4466 (2)0.0270 (4)
H28A−0.0559080.672818−0.3849940.032*
H28B−0.0889250.768859−0.4587450.032*
C290.62509 (7)0.63910 (13)0.9981 (2)0.0208 (4)
N300.62287 (6)0.74382 (11)1.0154 (2)0.0234 (3)
H300.5949690.7832250.9712370.028*
N310.67036 (6)0.78048 (12)1.1116 (2)0.0269 (4)
N320.70102 (6)0.70206 (12)1.1553 (2)0.0277 (4)
N330.67412 (6)0.61364 (11)1.0874 (2)0.0237 (3)
H330.6870710.5492351.1003040.028*
N340.58793 (6)0.57604 (11)0.9108 (2)0.0272 (4)
H34A0.5571550.6020560.8546860.033*
H34B0.5938240.5077860.9084830.033*
O1S−0.05800 (5)0.39192 (10)−0.35612 (19)0.0270 (3)
H1SA−0.0549 (9)0.328 (2)−0.374 (3)0.041*
H1SB−0.0263 (9)0.4142 (18)−0.305 (3)0.041*
O2S0.71190 (6)0.42019 (10)1.1563 (2)0.0282 (3)
H2SA0.7426 (10)0.4009 (18)1.192 (3)0.042*
H2SB0.6979 (10)0.3689 (19)1.103 (3)0.042*
O3S−0.20626 (6)0.85908 (10)−0.6897 (2)0.0330 (3)
H3SA−0.2354 (11)0.8812 (19)−0.736 (4)0.049*
H3SB−0.1880 (11)0.907 (2)−0.639 (4)0.049*
O4S0.44686 (6)0.38490 (11)0.6275 (3)0.0438 (4)
H4SA0.4454 (11)0.447 (3)0.636 (4)0.066*
H4SB0.4770 (11)0.367 (2)0.674 (4)0.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0158 (7)0.0142 (7)0.0216 (7)−0.0010 (5)−0.0014 (5)−0.0011 (5)
N20.0164 (7)0.0201 (7)0.0285 (7)−0.0001 (6)−0.0053 (6)−0.0022 (6)
N30.0177 (7)0.0202 (7)0.0334 (8)0.0007 (6)−0.0069 (6)−0.0038 (6)
N40.0177 (7)0.0178 (7)0.0299 (7)0.0011 (5)−0.0046 (6)−0.0017 (6)
C50.0150 (8)0.0144 (8)0.0210 (8)−0.0006 (6)−0.0007 (6)−0.0003 (6)
C60.0153 (8)0.0122 (7)0.0212 (8)−0.0018 (6)0.0005 (6)−0.0008 (6)
O70.0158 (6)0.0127 (6)0.0302 (6)0.0000 (4)−0.0054 (5)−0.0008 (5)
N80.0148 (7)0.0147 (7)0.0306 (7)−0.0013 (5)−0.0072 (6)−0.0014 (5)
C90.0147 (8)0.0141 (8)0.0229 (8)−0.0020 (6)−0.0017 (6)−0.0006 (6)
N100.0146 (7)0.0140 (7)0.0235 (7)−0.0012 (5)−0.0019 (5)−0.0007 (5)
C110.0142 (8)0.0145 (8)0.0212 (8)−0.0016 (6)−0.0012 (6)−0.0003 (6)
N120.0146 (7)0.0169 (7)0.0295 (7)−0.0011 (5)−0.0077 (6)−0.0003 (6)
O130.0155 (6)0.0129 (6)0.0309 (6)0.0005 (4)−0.0070 (5)−0.0029 (5)
C140.0160 (8)0.0123 (7)0.0222 (8)−0.0013 (6)−0.0004 (6)−0.0006 (6)
N150.0159 (7)0.0130 (7)0.0264 (7)−0.0013 (5)−0.0031 (6)−0.0008 (5)
C160.0155 (8)0.0121 (7)0.0245 (8)−0.0008 (6)−0.0014 (7)0.0001 (6)
N170.0140 (7)0.0130 (7)0.0268 (7)−0.0002 (5)−0.0039 (6)−0.0004 (5)
N180.0166 (7)0.0187 (7)0.0326 (8)−0.0010 (6)−0.0073 (6)−0.0005 (6)
N190.0177 (7)0.0192 (7)0.0310 (8)−0.0008 (6)−0.0059 (6)0.0011 (6)
N200.0163 (7)0.0174 (7)0.0288 (7)0.0004 (5)−0.0046 (6)0.0002 (6)
O210.0212 (6)0.0127 (6)0.0350 (7)0.0028 (5)−0.0046 (5)0.0003 (5)
O220.0229 (7)0.0109 (6)0.0471 (8)0.0019 (5)−0.0096 (6)0.0012 (5)
C230.0210 (8)0.0161 (8)0.0213 (8)0.0023 (7)−0.0008 (7)0.0010 (6)
N240.0200 (7)0.0132 (7)0.0298 (7)0.0014 (6)−0.0043 (6)0.0018 (6)
N250.0233 (8)0.0194 (8)0.0402 (8)−0.0015 (6)−0.0066 (7)0.0003 (6)
N260.0257 (9)0.0171 (7)0.0408 (9)−0.0009 (6)−0.0072 (7)0.0008 (6)
N270.0208 (8)0.0141 (7)0.0304 (7)0.0015 (6)−0.0042 (6)0.0005 (6)
N280.0241 (8)0.0137 (7)0.0400 (8)0.0011 (6)−0.0104 (7)0.0025 (6)
C290.0214 (9)0.0175 (8)0.0231 (8)0.0032 (7)0.0008 (7)0.0005 (6)
N300.0214 (8)0.0164 (7)0.0311 (8)0.0027 (6)−0.0034 (6)−0.0004 (6)
N310.0242 (8)0.0209 (8)0.0341 (8)−0.0001 (6)−0.0039 (6)−0.0025 (6)
N320.0254 (8)0.0199 (8)0.0360 (8)−0.0010 (6)−0.0050 (6)−0.0032 (6)
N330.0233 (8)0.0145 (7)0.0320 (8)0.0033 (6)−0.0033 (6)−0.0006 (6)
N340.0252 (8)0.0143 (7)0.0396 (9)0.0031 (6)−0.0075 (7)−0.0013 (6)
O1S0.0226 (7)0.0135 (6)0.0419 (8)−0.0003 (5)−0.0104 (6)−0.0006 (5)
O2S0.0251 (7)0.0140 (6)0.0428 (8)0.0003 (5)−0.0089 (6)−0.0010 (5)
O3S0.0287 (8)0.0135 (6)0.0527 (9)0.0011 (5)−0.0136 (6)−0.0011 (6)
O4S0.0241 (8)0.0160 (7)0.0854 (12)0.0032 (6)−0.0204 (8)−0.0083 (7)
Geometric parameters (Å, º) top
N1—O211.2964 (17)C23—N271.337 (2)
N1—N21.3429 (19)N24—N251.362 (2)
N1—C51.351 (2)N24—H240.8800
N2—N31.3230 (19)N25—N261.272 (2)
N3—N41.3342 (19)N26—N271.357 (2)
N4—C51.331 (2)N27—H270.8800
C5—C61.432 (2)N28—H28A0.8800
C6—N101.297 (2)N28—H28B0.8800
C6—O71.3468 (18)C29—N341.314 (2)
O7—N81.4033 (16)C29—N301.338 (2)
N8—C91.303 (2)C29—N331.338 (2)
C9—N101.368 (2)N30—N311.366 (2)
C9—C111.461 (2)N30—H300.8800
C11—N121.309 (2)N31—N321.269 (2)
C11—N151.3704 (19)N32—N331.362 (2)
N12—O131.4071 (17)N33—H330.8800
O13—C141.3473 (18)N34—H34A0.8800
C14—N151.298 (2)N34—H34B0.8800
C14—C161.435 (2)O1S—H1SA0.83 (3)
C16—N201.333 (2)O1S—H1SB0.87 (2)
C16—N171.346 (2)O2S—H2SA0.81 (2)
N17—O221.2902 (17)O2S—H2SB0.81 (3)
N17—N181.3450 (19)O3S—H3SA0.81 (2)
N18—N191.3232 (19)O3S—H3SB0.82 (3)
N19—N201.3322 (19)O4S—H4SA0.79 (3)
C23—N281.320 (2)O4S—H4SB0.81 (3)
C23—N241.334 (2)
O21—N1—N2123.26 (12)N18—N19—N20110.74 (13)
O21—N1—C5129.24 (13)N19—N20—C16105.92 (13)
N2—N1—C5107.49 (12)N28—C23—N24127.21 (15)
N3—N2—N1106.79 (12)N28—C23—N27128.20 (15)
N2—N3—N4110.65 (13)N24—C23—N27104.59 (14)
C5—N4—N3106.20 (13)C23—N24—N25109.56 (13)
N4—C5—N1108.87 (14)C23—N24—H24125.2
N4—C5—C6126.93 (14)N25—N24—H24125.2
N1—C5—C6124.17 (14)N26—N25—N24108.08 (14)
N10—C6—O7114.16 (13)N25—N26—N27107.94 (14)
N10—C6—C5128.49 (14)C23—N27—N26109.82 (14)
O7—C6—C5117.34 (13)C23—N27—H27125.1
C6—O7—N8105.75 (11)N26—N27—H27125.1
C9—N8—O7102.93 (12)C23—N28—H28A120.0
N8—C9—N10115.91 (14)C23—N28—H28B120.0
N8—C9—C11121.30 (14)H28A—N28—H28B120.0
N10—C9—C11122.79 (14)N34—C29—N30127.83 (16)
C6—N10—C9101.26 (13)N34—C29—N33128.02 (15)
N12—C11—N15115.54 (14)N30—C29—N33104.15 (14)
N12—C11—C9121.58 (14)C29—N30—N31109.89 (14)
N15—C11—C9122.88 (14)C29—N30—H30125.1
C11—N12—O13102.91 (12)N31—N30—H30125.1
C14—O13—N12105.92 (11)N32—N31—N30107.93 (14)
N15—C14—O13113.96 (13)N31—N32—N33108.03 (14)
N15—C14—C16128.05 (14)C29—N33—N32110.00 (14)
O13—C14—C16117.99 (13)C29—N33—H33125.0
C14—N15—C11101.67 (13)N32—N33—H33125.0
N20—C16—N17109.25 (13)C29—N34—H34A120.0
N20—C16—C14126.58 (14)C29—N34—H34B120.0
N17—C16—C14124.14 (14)H34A—N34—H34B120.0
O22—N17—N18123.35 (13)H1SA—O1S—H1SB106 (2)
O22—N17—C16129.37 (13)H2SA—O2S—H2SB104 (2)
N18—N17—C16107.28 (12)H3SA—O3S—H3SB110 (2)
N19—N18—N17106.80 (12)H4SA—O4S—H4SB107 (3)
O21—N1—N2—N3−179.48 (14)O13—C14—N15—C11−0.16 (18)
C5—N1—N2—N30.14 (17)C16—C14—N15—C11−179.50 (16)
N1—N2—N3—N40.05 (19)N12—C11—N15—C14−0.14 (19)
N2—N3—N4—C5−0.22 (19)C9—C11—N15—C14179.76 (15)
N3—N4—C5—N10.30 (18)N15—C14—C16—N20−176.68 (16)
N3—N4—C5—C6178.57 (15)O13—C14—C16—N204.0 (2)
O21—N1—C5—N4179.30 (15)N15—C14—C16—N175.5 (3)
N2—N1—C5—N4−0.28 (18)O13—C14—C16—N17−173.77 (15)
O21—N1—C5—C61.0 (3)N20—C16—N17—O22−179.06 (15)
N2—N1—C5—C6−178.60 (14)C14—C16—N17—O22−0.9 (3)
N4—C5—C6—N10179.82 (16)N20—C16—N17—N180.78 (18)
N1—C5—C6—N10−2.2 (3)C14—C16—N17—N18178.89 (15)
N4—C5—C6—O7−1.6 (2)O22—N17—N18—N19179.15 (14)
N1—C5—C6—O7176.45 (14)C16—N17—N18—N19−0.70 (18)
N10—C6—O7—N80.35 (18)N17—N18—N19—N200.38 (18)
C5—C6—O7—N8−178.46 (13)N18—N19—N20—C160.10 (18)
C6—O7—N8—C9−0.01 (16)N17—C16—N20—N19−0.54 (18)
O7—N8—C9—N10−0.31 (18)C14—C16—N20—N19−178.59 (15)
O7—N8—C9—C11179.62 (14)N28—C23—N24—N25−179.78 (17)
O7—C6—N10—C9−0.50 (18)N27—C23—N24—N25−0.22 (18)
C5—C6—N10—C9178.15 (16)C23—N24—N25—N260.0 (2)
N8—C9—N10—C60.51 (19)N24—N25—N26—N270.2 (2)
C11—C9—N10—C6−179.43 (15)N28—C23—N27—N26179.88 (17)
N8—C9—C11—N12179.34 (16)N24—C23—N27—N260.33 (18)
N10—C9—C11—N12−0.7 (2)N25—N26—N27—C23−0.3 (2)
N8—C9—C11—N15−0.6 (2)N34—C29—N30—N31−178.26 (17)
N10—C9—C11—N15179.38 (15)N33—C29—N30—N310.79 (18)
N15—C11—N12—O130.36 (18)C29—N30—N31—N32−0.74 (19)
C9—C11—N12—O13−179.54 (14)N30—N31—N32—N330.35 (19)
C11—N12—O13—C14−0.42 (16)N34—C29—N33—N32178.47 (17)
N12—O13—C14—N150.38 (18)N30—C29—N33—N32−0.58 (19)
N12—O13—C14—C16179.79 (13)N31—N32—N33—C290.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N24—H24···O1S0.881.762.6267 (18)169
N27—H27···O3S0.881.742.6241 (19)177
N28—H28A···N190.882.183.054 (2)176
N28—H28B···O22i0.881.992.8656 (19)172
N30—H30···O4Sii0.881.752.605 (2)165
N33—H33···O2S0.881.782.6544 (19)173
N34—H34A···N30.882.203.080 (2)174
N34—H34B···O21iii0.882.012.8882 (19)175
O1S—H1SA···N20iv0.83 (3)1.99 (3)2.8030 (19)170 (2)
O1S—H1SB···N180.87 (2)1.94 (2)2.7758 (19)160 (2)
O2S—H2SA···N12iii0.81 (2)2.39 (2)3.0906 (18)144 (2)
O2S—H2SB···N10iii0.81 (3)2.19 (2)2.9038 (18)148 (2)
O3S—H3SA···N8i0.81 (2)2.33 (2)3.0397 (19)147 (2)
O3S—H3SB···N15i0.82 (3)2.21 (3)2.8915 (19)141 (2)
O4S—H4SA···N40.79 (3)2.03 (3)2.817 (2)177 (3)
O4S—H4SB···N2iii0.81 (3)2.02 (3)2.789 (2)157 (3)
Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2; (iv) −x, y−1/2, −z−1/2.
Bis(aminoguanidinium) 5,5'-(3,3'-bi[1,2,4-oxadiazole]-5,5'-diyl)bis(1H-tetrazol-1-olate) (5) top
Crystal data top
2CH7N4+·C6N12O42−F(000) = 468
Mr = 454.39Dx = 1.673 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.9458 (4) ÅCell parameters from 4111 reflections
b = 5.5586 (2) Åθ = 2.9–26.4°
c = 20.6066 (9) ŵ = 0.14 mm−1
β = 97.647 (2)°T = 150 K
V = 902.05 (7) Å3Rod, yellow
Z = 20.42 × 0.11 × 0.08 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		1633 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.020
ω scansθmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		h = −9→9
Tmin = 0.944, Tmax = 0.989k = −6→6
7786 measured reflectionsl = −25→25
1844 independent reflections
Refinement top
Refinement on F263 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0711P)2 + 0.8763P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1844 reflectionsΔρmax = 0.74 e Å−3
206 parametersΔρmin = −0.24 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.7242 (6)0.6920 (8)0.89476 (16)0.0200 (8)0.907 (5)
N2A0.7542 (4)0.8420 (6)0.84668 (15)0.0249 (7)0.907 (5)
N3A0.6683 (3)0.7570 (6)0.79207 (13)0.0273 (7)0.907 (5)
N4A0.5827 (5)0.5580 (6)0.80370 (19)0.0256 (8)0.907 (5)
C5A0.6185 (8)0.5198 (9)0.8676 (2)0.0197 (10)0.907 (5)
O11A0.7863 (2)0.7262 (3)0.95566 (8)0.0277 (5)0.907 (5)
N1B0.599 (6)0.619 (7)0.809 (2)0.025 (7)0.093 (5)
N2B0.685 (4)0.813 (5)0.8096 (18)0.019 (5)0.093 (5)
N3B0.774 (5)0.878 (6)0.8619 (17)0.021 (5)0.093 (5)
N4B0.744 (6)0.696 (10)0.909 (2)0.020 (6)0.093 (5)
C5B0.635 (10)0.536 (10)0.878 (3)0.023 (8)0.093 (5)
O11B0.483 (2)0.528 (3)0.7672 (8)0.030 (5)0.093 (5)
C60.5571 (2)0.3235 (3)0.90328 (9)0.0191 (4)
O70.44405 (17)0.1736 (2)0.86989 (6)0.0226 (3)
N80.4063 (2)−0.0012 (3)0.91550 (8)0.0222 (4)
C90.5000 (2)0.0668 (3)0.96935 (8)0.0192 (4)
N100.5969 (2)0.2681 (3)0.96468 (7)0.0203 (4)
N120.1089 (3)0.6386 (5)0.79393 (10)0.0481 (6)
H12A0.167 (3)0.578 (5)0.7645 (10)0.058*
H12B0.029 (3)0.723 (5)0.7706 (13)0.058*
N130.0329 (3)0.4421 (4)0.82311 (9)0.0403 (5)
H13−0.04030.34780.79950.048*
C140.0749 (2)0.4033 (4)0.88724 (10)0.0276 (5)
N150.0053 (3)0.2218 (4)0.91527 (10)0.0387 (5)
H15A0.03110.19650.95760.046*
H15B−0.06700.12620.89170.046*
N160.1827 (2)0.5488 (3)0.92093 (8)0.0296 (4)
H16A0.21030.52680.96330.036*
H16B0.22760.66870.90120.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0220 (15)0.0203 (11)0.0168 (18)0.0009 (10)−0.0010 (12)−0.0005 (13)
N2A0.0294 (15)0.0221 (14)0.0221 (17)−0.0029 (10)−0.0001 (14)0.0003 (11)
N3A0.0349 (14)0.0276 (14)0.0182 (13)−0.0039 (10)−0.0012 (10)0.0013 (10)
N4A0.0295 (18)0.0255 (17)0.0210 (13)−0.0052 (12)0.0004 (11)0.0027 (12)
C5A0.019 (2)0.0215 (13)0.018 (2)−0.0001 (11)0.0004 (15)−0.0022 (12)
O11A0.0332 (9)0.0290 (9)0.0185 (10)−0.0056 (7)−0.0054 (7)−0.0019 (6)
N1B0.030 (11)0.023 (9)0.019 (7)−0.006 (8)−0.006 (6)0.008 (5)
N2B0.021 (6)0.019 (6)0.017 (6)−0.002 (3)0.004 (3)0.003 (3)
N3B0.022 (6)0.021 (6)0.021 (6)0.001 (3)0.001 (3)0.001 (3)
N4B0.020 (11)0.022 (8)0.017 (8)−0.006 (7)−0.002 (6)0.005 (6)
C5B0.026 (14)0.027 (9)0.013 (8)−0.005 (10)−0.004 (7)0.007 (6)
O11B0.032 (7)0.036 (8)0.020 (7)−0.008 (6)−0.001 (6)0.002 (5)
C60.0170 (8)0.0210 (9)0.0186 (8)0.0006 (7)0.0000 (6)−0.0025 (7)
O70.0251 (7)0.0244 (7)0.0172 (6)−0.0043 (6)−0.0015 (5)−0.0004 (5)
N80.0256 (8)0.0233 (8)0.0173 (7)−0.0040 (6)0.0010 (6)0.0001 (6)
C90.0196 (8)0.0203 (9)0.0174 (9)−0.0008 (7)0.0015 (6)−0.0019 (7)
N100.0217 (8)0.0215 (8)0.0174 (8)−0.0020 (6)0.0008 (6)−0.0009 (6)
N120.0518 (13)0.0630 (16)0.0285 (10)0.0028 (12)0.0017 (9)0.0059 (10)
N130.0441 (11)0.0451 (12)0.0282 (10)−0.0039 (9)−0.0081 (8)−0.0064 (9)
C140.0225 (9)0.0272 (11)0.0319 (11)0.0016 (8)−0.0007 (8)−0.0078 (9)
N150.0361 (10)0.0349 (11)0.0430 (11)−0.0086 (8)−0.0031 (9)−0.0020 (9)
N160.0304 (9)0.0324 (10)0.0241 (8)−0.0078 (8)−0.0037 (7)−0.0027 (7)
Geometric parameters (Å, º) top
N1A—O11A1.300 (3)O7—N81.411 (2)
N1A—N2A1.341 (5)N8—C91.307 (2)
N1A—C5A1.345 (5)C9—N101.369 (2)
N2A—N3A1.323 (3)C9—C9i1.465 (4)
N3A—N4A1.337 (4)N12—N131.420 (3)
N4A—C5A1.328 (5)N12—H12A0.8800 (11)
C5A—C61.436 (4)N12—H12B0.8801 (11)
N1B—N2B1.28 (5)N13—C141.337 (3)
N1B—O11B1.28 (4)N13—H130.8800
N1B—C5B1.48 (7)C14—N161.309 (3)
N2B—N3B1.26 (4)C14—N151.320 (3)
N3B—N4B1.45 (6)N15—H15A0.8800
N4B—C5B1.34 (7)N15—H15B0.8800
C5B—C61.46 (2)N16—H16A0.8800
C6—N101.300 (2)N16—H16B0.8800
C6—O71.345 (2)
O11A—N1A—N2A122.7 (4)O7—C6—C5B127 (2)
O11A—N1A—C5A129.9 (4)C6—O7—N8105.81 (13)
N2A—N1A—C5A107.4 (3)C9—N8—O7102.65 (14)
N3A—N2A—N1A106.5 (3)N8—C9—N10116.01 (16)
N2A—N3A—N4A111.1 (3)N8—C9—C9i121.4 (2)
C5A—N4A—N3A105.3 (2)N10—C9—C9i122.6 (2)
N4A—C5A—N1A109.8 (3)C6—N10—C9101.30 (15)
N4A—C5A—C6125.9 (3)N13—N12—H12A107 (2)
N1A—C5A—C6124.3 (4)N13—N12—H12B109 (2)
N2B—N1B—O11B132 (4)H12A—N12—H12B104 (3)
N2B—N1B—C5B103 (3)C14—N13—N12118.59 (19)
O11B—N1B—C5B124 (4)C14—N13—H13120.7
N3B—N2B—N1B119 (3)N12—N13—H13120.7
N2B—N3B—N4B105 (3)N16—C14—N15121.5 (2)
C5B—N4B—N3B107 (4)N16—C14—N13119.0 (2)
N4B—C5B—C6129 (5)N15—C14—N13119.5 (2)
N4B—C5B—N1B107 (3)C14—N15—H15A120.0
C6—C5B—N1B124 (4)C14—N15—H15B120.0
N10—C6—O7114.22 (17)H15A—N15—H15B120.0
N10—C6—C5A128.5 (2)C14—N16—H16A120.0
O7—C6—C5A117.3 (2)C14—N16—H16B120.0
N10—C6—C5B119 (2)H16A—N16—H16B120.0
O11A—N1A—N2A—N3A−178.2 (4)N1A—C5A—C6—N10−4.2 (8)
C5A—N1A—N2A—N3A−0.6 (5)N4A—C5A—C6—O7−4.8 (8)
N1A—N2A—N3A—N4A0.6 (4)N1A—C5A—C6—O7176.2 (5)
N2A—N3A—N4A—C5A−0.3 (5)N4B—C5B—C6—N10−2 (10)
N3A—N4A—C5A—N1A0.0 (6)N1B—C5B—C6—N10−179 (5)
N3A—N4A—C5A—C6−179.2 (5)N4B—C5B—C6—O7177 (6)
O11A—N1A—C5A—N4A177.8 (5)N1B—C5B—C6—O70 (10)
N2A—N1A—C5A—N4A0.4 (6)N10—C6—O7—N8−0.1 (2)
O11A—N1A—C5A—C6−3.0 (9)C5A—C6—O7—N8179.5 (4)
N2A—N1A—C5A—C6179.6 (5)C5B—C6—O7—N8−180 (5)
O11B—N1B—N2B—N3B170 (5)C6—O7—N8—C90.14 (18)
C5B—N1B—N2B—N3B2 (6)O7—N8—C9—N10−0.1 (2)
N1B—N2B—N3B—N4B−2 (5)O7—N8—C9—C9i179.9 (2)
N2B—N3B—N4B—C5B1 (6)O7—C6—N10—C90.0 (2)
N3B—N4B—C5B—C6−177 (7)C5A—C6—N10—C9−179.6 (4)
N3B—N4B—C5B—N1B0 (7)C5B—C6—N10—C9180 (4)
N2B—N1B—C5B—N4B−1 (7)N8—C9—N10—C60.1 (2)
O11B—N1B—C5B—N4B−170 (5)C9i—C9—N10—C6−180.0 (2)
N2B—N1B—C5B—C6176 (6)N12—N13—C14—N160.8 (3)
O11B—N1B—C5B—C67 (10)N12—N13—C14—N15179.8 (2)
N4A—C5A—C6—N10174.8 (5)
Symmetry code: (i) −x+1, −y, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12—H12B···N4Aii0.88 (1)2.50 (1)3.314 (4)155 (3)
N13—H13···N3Aiii0.882.082.870 (3)149
N13—H13···N4Aiii0.882.653.405 (4)144
N15—H15A···O11Aiv0.882.192.954 (3)145
N15—H15B···N2Av0.882.243.112 (4)170
N16—H16A···O11Aiv0.882.182.949 (2)146
N16—H16A···N10iv0.882.292.926 (2)129
N16—H16B···N8vi0.882.323.079 (2)145
Symmetry codes: (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+1/2, y−1/2, −z+3/2; (iv) −x+1, −y+1, −z+2; (v) x−1, y−1, z; (vi) x, y+1, z.
Crystal densities of each structure top
Structure IDCationDensity (g cm-1)
1hydrazinium1.694
2hydroxylammonium1.873
3dimethylammonium1.544
45-amino-1H-tetrazol-4-ium1.701
5aminoguanidinium1.673
 

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