Crystal Structures of New Ammonium 5-Aminotetrazolates

Lampl, Martin; Salchner, Robert; Laus, Gerhard; Braun, Doris E.; Kahlenberg, Volker; Wurst, Klaus; Fuhrmann, Gerda; Schottenberger, Herwig; Huppertz, Hubert

doi:10.3390/cryst4040439

Open AccessArticle

Crystal Structures of New Ammonium 5-Aminotetrazolates

by

Martin Lampl

¹,

Robert Salchner

¹,

Gerhard Laus

¹,

Doris E. Braun

²,

Volker Kahlenberg

³,

Klaus Wurst

¹,

Gerda Fuhrmann

¹,

Herwig Schottenberger

¹

and

Hubert Huppertz

^1,*

¹

Institute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, 6020 Innsbruck, Austria

²

Institute of Pharmacy, University of Innsbruck, 6020 Innsbruck, Austria

³

Institute of Mineralogy and Petrography, University of Innsbruck, 6020 Innsbruck, Austria

^*

Author to whom correspondence should be addressed.

Crystals 2014, 4(4), 439-449; https://doi.org/10.3390/cryst4040439

Submission received: 16 September 2014 / Revised: 30 October 2014 / Accepted: 13 November 2014 / Published: 19 November 2014

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Abstract

:

The crystal structures of three salts of anionic 5-aminotetrazole are described. The tetramethylammonium salt (P

\bar{1}

) forms hydrogen-bonded ribbons of anions which accept weak C–H···N contacts from the cations. The cystamine salt (C2/c) shows wave-shaped ribbons of anions linked by hydrogen bonds to screw-shaped dications. The tetramethylguanidine salt (P2₁/c) exhibits layers of anions hydrogen-bonded to the cations.

Keywords:

5-aminotetrazole; cystamine; tetramethylammonium; tetramethylguanidine

Graphical Abstract

1. Introduction

Due to its amphiprotic nature [1,2], 5-aminotetrazole has served as a cation [3,4] or as an anion in energetic salts [5]. Crystal structures of several alkali metal 5-aminotetrazolates have been reported [6]. Organic salts containing 5-aminotetrazole as anion have been first described more than six decades ago [7]. Continuing our interest in nitrogen-rich heterocycles [8,9,10,11], we describe here the preparation and crystal structures of three new 5-aminotetrazolates of organic cations. These salts are of interest as blowing agents [12] and as alternative precursors for nitridosilicates [13,14,15]. Following the structural characterization, the new compounds were examined by DSC and TGA in order to assess their suitability for those purposes.

2. Results and Discussion

Three synthetic methods were employed to generate the required 5-aminotetrazolate anion (Figure 1), i.e., (a) deprotonation of 5-aminotetrazole by an organic hydroxide; (b) ion metathesis of an organic sulfate with barium 5-aminotetrazolate; and (c) direct reaction of 5-aminotetrazole with a strong organic base.

Figure 1. Synthesis of the 5-aminotetrazolates 1–3.

The crystal data and details of the structure refinements for tetramethylammonium 5-aminotetrazolate (1); cystamine bis(5-aminotetrazolate) (2); and 1,1,3,3-tetramethylguanidinium 5-aminotetrazolate (3) are summarized in Table 1.

Table 1. Crystal data and structure refinement details for compounds 1–3.

**Table 1.** Crystal data and structure refinement details for compounds 1–3.
Compound	1	2	3
CCDC No.	1024084	1024085	1024086
Chemical formula	C₄H₁₂N·CH₂N₅	C₄H₁₄N₂S₂·2(CH₂N₅)	C₅H₁₄N₃·CH₂N₅
M_r/g·mol⁻¹	158.22	322.44	200.27
Crystal size/mm³	0.24 × 0.16 × 0.10	0.30 × 0.30 × 0.20	0.40 × 0.40 × 0.40
Crystal system	Triclinic	Monoclinic	Monoclinic
Space group	P $\bar{1}$	C2/c	P2₁/c
a/Å	9.1270(9)	17.4437(3)	7.5109(4)
b/Å	10.129(1)	7.9305(3)	12.4241(4)
c/Å	10.432(2)	11.1625(4)	11.6513(4)
α/°	98.86(1)	–	–
β/°	110.65(2)	110.13(1)	106.82(1)
γ/°	106.77(1)	–	–
V/Å³	828.2(2)	1449.85(8)	1040.72(7)
Z	4	4	4
D_x/g·cm⁻³	1.27	1.48	1.28
η	0.09	0.38	0.09
F(000)/e	344	680	432
Temperature/K	173(2)	233(2)	173(2)
θ_max/°	25.4	26.0	28.6
h, k, l range	−10 ≤ h ≤ 9	−21 ≤ h ≤ 21	−9 ≤ h ≤ 8
	−12 ≤ k ≤ 12	−9 ≤ k ≤ 9	−14 ≤ k ≤ 14
	−12 ≤ l ≤ 11	−13 ≤ l ≤ 13	−14 ≤ l ≤ 12
Absorption correction	multi-scan	–	multi-scan
Measured reflections	5042	4661	6125
Independent reflections (R_int)	3010 (0.030)	1418 (0.026)	1897 (0.021)
Observed reflections (I ≥ 2σ(I))	2317	1285	1718
Restraints/parameters	0/224	5/112	0/148
R₁, wR₂ (I ≥ 2σ(I))	0.042, 0.091	0.031, 0.081	0.033, 0.083
R₁, wR₂ (all data)	0.062, 0.106	0.034, 0.083	0.038, 0.087
Goodness of fit	1.02	1.12	1.06
Δρ_max, Δρ_min/e Å⁻³	0.21, −0.19	0.21, −0.38	0.36, −0.16

2.1. Tetramethylammonium 5-Aminotetrazolate (1)

Two independent ion pairs are observed in the asymmetric unit. The tetrazolate anions arranged in ribbons parallel to the (

\bar{1}

11) plane accept weak C–H···N contacts from the quaternary cations which are aligned in rows parallel to the [1

\bar{1}

1] direction (Figure 2a). The rows of cations are located sideways between the ribbons and above/below the plane of the ribbons, as displayed in Figure 2b. The hydrogen bond parameters are collected in Table 2. Phase purity of the bulk sample was confirmed by Pawley fit between the experimental and the calculated powder patterns (Figure 3 and Table 3).

Figure 2. (a) Interactions in the crystal structure of 1; (b) Packing diagram of 1.

Table 2. Hydrogen bond parameters (Å, °).

**Table 2.** Hydrogen bond parameters (Å, °).
Compound	Interaction	H···A	D···A	D–H···A	Symmetry Operation A
1	N1–H12···N2	2.17(3)	3.043(3)	170(2)	2 − x, 1 − y, 1 − z
	N6–H61···N3	2.25(2)	3.143(2)	173(2)	x, y, z
	N6–H62···N7	2.25(2)	3.150(2)	177(2)	1 − x, 1 − y, −z
	N1–H11···N7	2.51(2)	3.385(2)	159(2)	1 + x, y, 1 + z
	N1–H11···N8	2.61(2)	3.462(3)	155(2)	1 + x, y, 1 + z
	C9–H···N9	2.562	3.511(3)	162.9	1 − x, −y, 1 − z
	C4–H···N3	2.591	3.520(2)	158.3	x, y, z
	C5–H···N4	2.592	3.474(2)	149.7	x, y, z
	C3–H···N4	2.601	3.480(3)	149.3	x, y, z
	C10–H···N5	2.616	3.497(3)	149.6	x, y, z
	C9–H···N10	2.644	3.542(3)	152.5	1 − x, −y, 1 − z
	C7–H···N5	2.652	3.524(3)	148.3	x, y, z
	C6–H···N9	2.652	3.551(2)	152.7	−x, −y, −z
2	N6–H···N4	1.98(2)	2.870(2)	175(2)	x, −y, −1/2 + z
	N6–H···N3	2.05(1)	2.893(2)	162(2)	x, y, z
	N6–H···N5	2.07(1)	2.958(2)	164(1)	1/2 − x, −1/2 + y, 5/2 − z
	N5–H···N2	2.16(2)	3.037(2)	174(2)	x, −y, 1/2 + z
	N5–H···N1	2.20(2)	3.070(2)	173(2)	1 − x, −y, 3 − z
3	N8–H···N2	2.04(2)	2.921(2)	169(1)	1 − x, −y, 1 − z
	N8–H···N4	2.05(2)	2.937(1)	166(1)	1 − x, −1/2 + y, 3/2 − z
	N1–H···N5	2.21(2)	3.080(2)	169(1)	1 − x, 1 − y, 1 − z

Figure 3. Pawley fit (R_wp = 12.11%, R_exp = 5.47%, R_p = 8.66%, gof = 2.21) of the powder X-ray diffraction (PXRD) data of 1 with a model calculated from the structure parameters derived from the single crystal structure. Black dots indicate raw data, while the red line indicates the calculated model. Tick marks (blue) are the 2θ positions for the hkl reflections. The difference curve is shown in green.

Table 3. Comparison of lattice parameters determined at 173 K (single crystal X-ray diffraction data, SCXRD) and 298 K (powder X-ray diffraction data).

**Table 3.** Comparison of lattice parameters determined at 173 K (single crystal X-ray diffraction data, SCXRD) and 298 K (powder X-ray diffraction data).
1	SG	D_x/g·cm⁻³	a/Å	b/Å	c/Å	α/°	β/°	γ/°
SCXRD	P $\bar{1}$	1.27	9.1270(9)	10.129(2)	10.432(2)	98.86(1)	110.65(2)	106.77(1)
PXRD	P $\bar{1}$	1.24	9.2743(5)	10.1495(5)	10.5227(6)	98.72(1)	110.81(1)	106.91(1)

2.2. Cystamine Bis(5-aminotetrazolate) (2)

The fragments of the cystamine cations are completed by a two-fold rotation axis perpendicular to the S1–S1 bond. The resulting dications are screw-shaped with a C–S–S–C dihedral angle of 89.6(1)° (Figure 4a). The anions form hydrogen-bonded wave-shaped ribbons parallel to the ac plane to which the cations are linked by hydrogen bonds (Figure 4b). The Pawley fit is depicted in Figure 5, and the corresponding results are shown in Table 4.

Figure 4. (a) Interactions in the crystal structure of 2; i: −x, y, 3/2 – z; (b) Packing diagram.

Figure 5. Pawley fit (R_wp = 9.04%, R_exp = 7.96%, R_p = 6.89%, gof = 1.14) of the PXRD data of 2 with a model calculated from the structural data of the single crystal structure determination.

Table 4. Comparison of lattice parameters determined at 233 K (single crystal X-ray diffraction data) and 298 K (powder X-ray diffraction data).

**Table 4.** Comparison of lattice parameters determined at 233 K (single crystal X-ray diffraction data) and 298 K (powder X-ray diffraction data).
2	D_x/g·cm⁻³	Space Group	a/Å	b/Å	c/Å	β/°
SCXRD	1.48	C2/c	17.4437(3)	7.9305(3)	11.1625(4)	110.131(2)
PXRD	1.47	C2/c	17.4964(6)	7.9400(3)	11.1614(4)	110.253(3)

2.3. 1,1,3,3-Tetramethylguanidinium 5-Aminotetrazolate (3)

The crystal structure of 3 is composed of hydrogen-bonded layers of anions and cations (Figure 6a) arranged parallel to the bc plane (Figure 6b). The Pawley fit is shown in Figure 7, and the corresponding results are collected in Table 5.

Figure 6. (a) Interactions in the crystal structure of 3; (b) Packing diagram of 3; hydrogen atoms are omitted for clarity.

Figure 7. Pawley fit (R_wp = 10.03%, R_exp = 5.57%, R_p = 7.80%, gof = 1.80) of the PXRD data of 3 with a model calculated from the structural data of the single crystal structure determination.

Table 5. Comparison of lattice parameters determined at 173 K (single crystal X-ray diffraction data) and 298 K (powder X-ray diffraction data).

**Table 5.** Comparison of lattice parameters determined at 173 K (single crystal X-ray diffraction data) and 298 K (powder X-ray diffraction data).
3	D_x/g·cm⁻³	Space Group	a/Å	b/Å	c/Å	β/°
SCXRD	1.28	P2₁/c	7.5109(4)	12.4241(4)	11.6513(4)	106.82(1)
PXRD	1.25	P2₁/c	7.6944(2)	12.5188(5)	11.5183(6)	107.03(1)

2.4. Differential Scanning Calorimetry (DSC) and Thermogravimetric Analysis (TGA)

Thermoanalysis of the 5-aminotetrazolates 1–3 showed an extensive decomposition with loss of mass around the melting temperature. The pertinent thermograms are depicted in Figure 8. Since the decomposition is not exothermic, the new compounds are not “energetic salts” in a strict sense, but appear to be suitable as temperate blowing agents.

Figure 8. Differential Scanning Calorimetry/Thermogravimetric Analysis (DSC/TGA) thermograms of (a) 1; (b) 2; and (c) 3.

3. Experimental Section

Barium 5-aminotetrazolate tetrahydrate was prepared according to a published procedure [16]. All other chemicals were purchased from Sigma-Aldrich, St. Louis, MO, USA (European affiliate, Steinheim, Germany). NMR spectra were recorded with a Bruker Avance DPX 300 spectrometer (Billerica, MA, USA). IR spectra were obtained with an Alpha FT (Bruker) instrument. Elemental analyses were conducted at the University of Vienna, Austria. DSC was performed with a DSC 7 (Perkin-Elmer, Norwalk, CT, USA) applying a heating rate of 10 °C·min⁻¹. TGA was carried out with a TGA 7 system (Perkin-Elmer) at a heating rate of 10 °C·min⁻¹. XRPD patterns were obtained using a X’Pert PRO diffractometer (PANalytical, Almelo, The Netherlands) equipped with a theta/theta coupled goniometer in transmission geometry, programmable XYZ stage with well plate holder, CuKα_1,2 radiation source with a focussing mirror, a 0.5° divergence slit and a 0.02° Soller slit collimator on the incident beam side, a 2 mm antiscattering slit and a 0.02° Soller slit collimator on the diffracted beam side and a 255 channel solid state PIXcel detector. The patterns were recorded, unless stated otherwise, at a tube voltage of 40 kV, tube current of 40 mA, applying a step size of 2θ = 0.013° with 400 s per step in the 2θ range between 2° and 40°. Pawley fits were performed with Topas Academic V5 (Coelho Software, Brisbane, Australia). The background was modelled with Chebyshev polynomials and the modified Thompson-Cox-Hastings pseudo-Voigt (TCHZ) function was used for peak shape fitting. Single crystal diffraction intensity data were recorded by ω scans with an Oxford Diffraction Gemini-R Ultra (Oxford Diffraction Ltd., Abingdon, Oxfordshire, UK) diffractometer (for 1 and 3) or by ϕ and ω scans with a Nonius KappaCCD (Bruker, Billerica, MA, USA) diffractometer (for 2) using MoKα radiation. CCDC reference numbers: 1024084–1024086. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre (Cambridge, UK).

3.1. Tetramethylammonium 5-Aminotetrazolate (1)

5-Aminotetrazole monohydrate (866 mg, 8.40 mmol) was added to a solution of tetramethyl-ammonium hydroxide pentahydrate (1.52 g, 8.40 mmol) in H₂O (10 mL). The mixture was stirred at 50 °C for 20 min to give a clear solution. The solvent was removed under reduced pressure, and the residue was recrystallized from hot MeOH. Yield: 1.11 g (84%). M.p. 223–225 °C (decomposition). ¹H·NMR (DMSO-d₆, 300 MHz): δ 3.10 (s, 12H, CH₃), 3.9 (br s, 2H, NH₂) ppm. ¹³C·NMR (DMSO-d₆, 75 MHz): δ 54.3 (4C, CH₃), 164.1 (tetrazole) ppm. IR (neat):

\tilde{ν}

3346 m, 3144 w, 3030 w, 1508 s, 1486 s (ν C = N), 1447 m, 1198 w, 1118 m, 949 s, 892 m, 750 m·cm⁻¹. C₅H₁₄N₆ (158.20): calculated C 37.96, H 8.92, N 53.12; found C 37.67, H 9.17, N 52.97.

3.2. Cystamine Bis(5-Aminotetrazolate) (2)

Cystamine sulfate monohydrate (320 mg, 1.19 mmol) was added to a solution of barium 5-aminotetrazolate tetrahydrate (450 mg, 1.19 mmol) in H₂O (10 mL). The mixture was stirred for 15 min, and the precipitate was removed by filtration. The filtrate was taken to dryness under reduced pressure, and the residue was recrystallized from hot H₂O/EtOH (1:4) to yield 320 mg (83%) of the colorless product. These crystals were suitable for structure determination. M.p. 165–167 °C (decom-position). ¹H·NMR (DMSO-d₆, 300 MHz): δ 2.77–2.81 and 2.88–2.93 (AA'BB', 8H, CH₂CH₂), 6.3 (br, 10H, NH₂ and NH₃) ppm. ¹³C NMR (DMSO-d₆, 75 MHz): δ 39.4 (CH₂), 39.9 (CH₂), 159.0 (tetrazole) ppm. IR (neat):

\tilde{ν}

3226 w, 3127 w, 2911 w, 2852 w, 2635 w, 2542 w, 2493 w, 1538 m, 1511 s (ν C=N), 1450 m, 1404 m, 1215 w, 1136 m, 1118 m, 900 s, 813 m, 442 s·cm⁻¹. C₆H₁₈N₁₂S₂ (322.42): calculated C 22.35, H 5.63, N 52.13, S 19.89; found C 22.52, H 5.63, N 52.23, S 19.82.

3.3. 1,1,3,3-Tetramethylguanidinium 5-Aminotetrazolate (3)

1,1,3,3-Tetramethylguanidine (1.4 mL, 11.2 mmol) was added to a stirred suspension of 5-aminotetrazole monohydrate (1.0 g, 9.7 mmol) in H₂O (10 mL) to give a clear solution. The solvent was removed under reduced pressure, and the residue was vacuum-dried for 3 h to yield 1.90 g (98%) of the colorless product. Single crystals were obtained by slow evaporation of a solution in MeOH. M.p. 200 °C (decomposition). ¹H NMR (DMSO-d₆, 300 MHz): δ 2.88 (s, 12H, CH₃) ppm. ¹³C·NMR (DMSO-d₆, 75 MHz): δ 40.0 (4C, CH₃), 161.4 (C=NH₂), 163.8 (tetrazole) ppm. IR (neat):

\tilde{ν}

3409 w, 3180 w, 2904 m, 1600 s, 1573 s, 1518 s (ν C=N), 1438 m, 1414 s, 1096 m, 1066 m, 1036 m, 998 w, 768 w, 708 m, 436 m·cm⁻¹. C₆H₁₆N₈ (200.24): calculated C 35.99, H 8.05, N 55.96; found C 36.19, H 8.26, N 55.24.

4. Conclusions

Three new ammonium 5-aminotetrazolates were prepared, and their crystal structures were determined. They appear to be promising candidates as gas-releasing agents, as indicated by thermal analysis.

Acknowledgments

We gratefully acknowledge funding by Die Österreichische Forschungsförderungsgesellschaft (FFG, Project 841104). Doris E. Braun gratefully acknowledges funding by the Hertha Firnberg Program of the Austrian Science Fund (FWF, Project T593-N19).

Author Contributions

Martin Lampl and Robert Salchner carried out experimental work (synthesis, crystallization and characterization). Gerhard Laus prepared the manuscript. Doris E. Braun contributed powder patterns and thermoanalyses. Volker Kahlenberg and Klaus Wurst determined the crystal structures. Gerda Fuhrmann contributed spectroscopic measurements. Herwig Schottenberger and Hubert Huppertz conceived and designed the study.

Conflicts of Interest

The authors declare no conflict of interest.

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Lampl, M.; Salchner, R.; Laus, G.; Braun, D.E.; Kahlenberg, V.; Wurst, K.; Fuhrmann, G.; Schottenberger, H.; Huppertz, H. Crystal Structures of New Ammonium 5-Aminotetrazolates. Crystals 2014, 4, 439-449. https://doi.org/10.3390/cryst4040439

AMA Style

Lampl M, Salchner R, Laus G, Braun DE, Kahlenberg V, Wurst K, Fuhrmann G, Schottenberger H, Huppertz H. Crystal Structures of New Ammonium 5-Aminotetrazolates. Crystals. 2014; 4(4):439-449. https://doi.org/10.3390/cryst4040439

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Lampl, Martin, Robert Salchner, Gerhard Laus, Doris E. Braun, Volker Kahlenberg, Klaus Wurst, Gerda Fuhrmann, Herwig Schottenberger, and Hubert Huppertz. 2014. "Crystal Structures of New Ammonium 5-Aminotetrazolates" Crystals 4, no. 4: 439-449. https://doi.org/10.3390/cryst4040439

APA Style

Lampl, M., Salchner, R., Laus, G., Braun, D. E., Kahlenberg, V., Wurst, K., Fuhrmann, G., Schottenberger, H., & Huppertz, H. (2014). Crystal Structures of New Ammonium 5-Aminotetrazolates. Crystals, 4(4), 439-449. https://doi.org/10.3390/cryst4040439

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Crystal Structures of New Ammonium 5-Aminotetrazolates

Abstract

1. Introduction

2. Results and Discussion

2.1. Tetramethylammonium 5-Aminotetrazolate (1)

2.2. Cystamine Bis(5-aminotetrazolate) (2)

2.3. 1,1,3,3-Tetramethylguanidinium 5-Aminotetrazolate (3)

2.4. Differential Scanning Calorimetry (DSC) and Thermogravimetric Analysis (TGA)

3. Experimental Section

3.1. Tetramethylammonium 5-Aminotetrazolate (1)

3.2. Cystamine Bis(5-Aminotetrazolate) (2)

3.3. 1,1,3,3-Tetramethylguanidinium 5-Aminotetrazolate (3)

4. Conclusions

Acknowledgments

Author Contributions

Conflicts of Interest

References

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