5-Pentyl-1H-tetra­zole

Thorsten Rieth; Dieter Schollmeyer; Heiner Detert

doi:10.1107/S1600536810052244

. 2010 Dec 18;67(Pt 1):o156. doi: 10.1107/S1600536810052244

5-Pentyl-1H-tetrazole

Thorsten Rieth ^a, Dieter Schollmeyer ^a, Heiner Detert ^a,^*

PMCID: PMC3050224 PMID: 21522663

Abstract

The title compound C₆H₁₂N₄, is one of a few known tetrazoles with an alkyl chain in the 5-position. The asymmetric unit contains two independent molecules. The molecules are linked by N—H⋯N interactions into chains with graph-set notation D(2) and C ₂ ²(8) along [010]. The two independent molecules form a layered structure, the layers being composed of interdigitating strands of alternatingly oriented and nearly identical molecules.

Related literature

For synthetic methods see: Mihina & Herbst (1950 ▶); Steven et al. (1993 ▶); Detert & Schollmeyer (1999 ▶); Sugiono & Detert (2001 ▶); Glang et al. (2008 ▶); Borchmann et al. (2010 ▶). For the properties of tetrazole, see: Huisgen et al. (1960a ▶,b ▶, 1961 ▶); Singh (1980 ▶); Pernice et al. (1988 ▶); Huff et al. (1996 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₆H₁₂N₄
M _r = 140.20
Triclinic,
a = 8.7812 (14) Å
b = 9.6770 (12) Å
c = 11.614 (2) Å
α = 93.136 (10)°
β = 112.059 (9)°
γ = 116.389 (7)°
V = 789.6 (2) Å³
Z = 4
Cu Kα radiation
μ = 0.63 mm⁻¹
T = 193 K
0.50 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
3182 measured reflections
2991 independent reflections
2764 reflections with I > 2σ(I)
R _int = 0.070
3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.109
S = 1.04
2991 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052244/bx2337sup1.cif

e-67-0o156-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052244/bx2337Isup2.hkl

e-67-0o156-Isup2.hkl^{(146.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯N4B	0.96	1.82	2.7773 (14)	175
N1B—H1B⋯N4Aⁱ	0.95	1.84	2.7779 (14)	170

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The title compound (I), is formed by the addition of triethylammonium azide to capronitrile in refluxing toluene and acidic work-up. In the crystal, molecules are linked by N— H··· N interactions into chains with graph-set notation D(2) a C²₂(8) along [010] (Bernstein et al., 1995), Table 1. Both molecules of the title compound have very similar geometries. The heterocycles and alkyl chains are coplanar with the molecules A oriented to the opposite site of the molecules B. These strands form layers via interdigitation of the alkyl chains.

Experimental

The title compound was prepared as follows: Triethyl ammonium chloride (8.95 g, 0.06 mol) and sodium azide (3.90 g, 0.06 mol) were added to a solution of hexanoic acid nitrile (4.36 g, 0.045 mol) in toluene (35 ml) and the mixture was stirred under reflux for 72 h. The mixture was filtered, the solvent evaporated and the residue dissolved in water. Hydrochloric acid (6M, 15 ml) was added and the product was extracted with ether/petroleum ether (1/1, 3*30 ml). The cooled organic solutions were dried with sodium sulfate. The solvents were evaporated and the residue crystallized upon standing at ambient temperature within 5 days. Recrystallization from toluene yielded 5-pentyltetrazole in 78% yield as colorless needles.